Six closely related 4,6-disubstituted 2-amino-5-formylpyrimidines: Different ring conformations, polarized electronic structures, and hydrogen-bonded assembly in zero, one, two and three dimensions

organic compounds

Acta Crystallographica Section C

Crystal Structure

Communications

Comment

When heterocyclic species are covalently linked to biomol-

ecules such as amino acids and peptides, carbohydrates, DNA

or steroids, this type of combination can enhance the bio-

activity of both components. For example, pyrimidine deri-

vatives have been used in this way, particularly when linked to

essential amino acids, in searches for new potentially bioactive

agents, including anti-inﬂammatory agents (Bruno et al., 1999),

antimicrobials (Ghorab et al., 2004), antidiabetic agents

(Cantin et al., 2006) and agents for the treatment of urinary

tract disease (Murata et al., 2004). Such combinations have

also been investigated as potential intermediates for the

synthesis of poly-fused pyrimidines of possible biological

value (Min et al., 2008). Here, we report the molecular and

supramolecular structures of six compounds of this type, (I)–

(VI) (Fig. 1 and Scheme), all having a simple amino substi-

tuent at position 6 of the pyrimidine ring, while position 4 of

said ring carries, in each case, an amino substituent derived

from a simple amino acid derivative. The present work is a

development of an earlier study (Cobo et al., 2008) which

reported the structures of 12 N⁶-substituted 2-amino-4-chloro-

5-formylpyrimidines.

ISSN 0108-2701

Six closely related 4,6-disubstituted

2-amino-5-formylpyrimidines:

different ring conformations,

polarized electronic structures, and

hydrogen-bonded assembly in zero,

one, two and three dimensions

a

b

´

Lina M. Acosta, ‡Andres F. Yepes, ‡ Alirio Palma, Justo

Cobo^aand Christopher Glidewell^c*

a

´

Departamento de Quımica Inorganica y Organica, Universidad de Jaen, 23071

b

´

Jaen, Spain, Laboratorio de Sıntesis Organica, Escuela de Quımica, Universidad

Industrial de Santander, AA 678 Bucaramanga, Colombia, and ^cSchool of Chemistry,

University of St Andrews, Fife KY16 9ST, Scotland

Correspondence e-mail: cg@st-andrews.ac.uk

Received 20 November 2012

Accepted 17 December 2012

Online 8 January 2013

In each of ethyl N-{2-amino-5-formyl-6-[methyl(phenyl)-

amino]pyrimidin-4-yl}glycinate, C₁₆H₁₉N₅O₃, (I), N-{2-am

ino-5-formyl-6-[methyl(phenyl)amino]pyrimidin-4-yl}glycin-

amide, C₁₄H₁₆N₆O₂, (II), and ethyl 3-amino-N-{2-amino-5-

formyl-6-[methyl(phenyl)amino]pyrimidin-4-yl}propionate,

C₁₇H₂₁N₅O₃, (III), the pyrimidine ring is effectively planar,

but in each of methyl N-{2-amino-6-[benzyl(methyl)amino]-

5-formylpyrimidin-4-yl}glycinate, C₁₆H₁₉N₅O₃, (IV), ethyl

3-amino-N-{2-amino-6-[benzyl(methyl)amino]-5-formyl-

pyrimidin-4-yl}propionate, C₁₈H₂₃N₅O₃, (V), and ethyl 3-am-

ino-N-[2-amino-5-formyl-6-(piperidin-4-yl)pyrimidin-4-yl]-

propionate, C₁₅H₂₃N₅O₃, (VI), the pyrimidine ring is folded

into a boat conformation. The bond lengths in each of (I)–(VI)

provide evidence for signiﬁcant polarization of the electronic

structure. The molecules of (I) are linked by paired N—HÁ Á ÁN

hydrogen bonds to form isolated dimeric aggregates, and those

of (III) are linked by a combination of N—HÁ Á ÁN and N—

HÁ Á ÁO hydrogen bonds into a chain of edge-fused rings. In the

structure of (IV), molecules are linked into sheets by means of

two hydrogen bonds, both of N—HÁ Á ÁO type, in the structure

of (V) by three hydrogen bonds, two of N—HÁ Á ÁN type and

one of C—HÁ Á ÁO type, and in the structure of (VI) by four

hydrogen bonds, all of N—HÁ Á ÁO type. Molecules of (II) are

linked into a three-dimensional framework structure by a

combination of three N—HÁ Á ÁO hydrogen bonds and one C—

HÁ Á ÁO hydrogen bond.

Minor variations in one or other of the substituents at

positions 4 and 6 in these compounds can lead to signiﬁcant

´

‡ Permanent address: Laboratorio de Sıntesis Organica, Escuela de Quımica,

Universidad Industrial de Santander, AA 678 Bucaramanga, Colombia.

´

162 # 2013 International Union of Crystallography

doi:10.1107/S0108270112051049

Acta Cryst. (2013). C69, 162–171

organic compounds

Figure 1

The molecular structures of compounds (I)–(VI), showing the atom-labelling schemes: (a) (I), (b) (II), (c) (III), (d) (IV), (e) (V) and (f) (VI).

Displacement ellipsoids are drawn at the 20% probability level for (I) and at the 30% probability level for (II)–(VI).

differences, in both the molecular conformations and the

hydrogen-bonded supramolecular assemblies. None of the

molecules of (I)–(VI) exhibits any internal symmetry and they

are all conformationally chiral, although all of them crystallize

in centrosymmetric space groups. The reference molecules

were selected so that all have the same sign for the torsion

ꢀ

Acta Cryst. (2013). C69, 162–171

Acosta et al.

C₁₆H₁₉N₅O₃, C₁₄H₁₆N₆O₂, C₁₇H₂₁N₅O₃, C₁₈H₂₃N₅O₃and C₁₅H₂₃N₅O₃163

organic compounds

angle C4—C5—C51—O51 (Table 1). In each structure, formyl

atom O51 is involved in an intramolecular N—HÁ Á ÁO

hydrogen bond (Table 2), forming an S(6) motif (Bernstein et

al., 1995).

tronic structure, in addition to the classical aromatic form (B).

Within the formyl fragments, the C—O distance is, in every

˚

case, long for its type [reference mean = 1.192 A and upper

˚

quartile = 1.197 A; Allen et al. (1987, 2006)], while the C5—

C51 bond between the formyl group and the pyrimidine ring is

Compounds (I)–(III) (Fig. 1) all have an N-methyl-N-

phenyl substituent at position 6 of the pyrimidine ring with

slightly different substituents at position 4 (Fig. 1), viz. a

glycinate ester and a glycinamide substituent in (I) and (II),

respectively, and a 3-aminopropionate ester substituent in

(III), and in each of (I)–(III) the pyrimidine ring is effectively

planar. Compounds (IV) and (V) both have an N-benzyl-N-

methyl substituent at position 6, with different amino acid

ester substituents at position 4; the orientation of the

6-substituent is different, as indicated by the torsion angles

C5—C6—N61—C67 and C5—C6—N61—C68 (Table 1 and

Fig. 1). In addition, the pyrimidine ring in each of (IV)–(VI) is

slightly distorted from planarity into a boat conformation, as

indicated by the ring-puckering parameters (Cremer & Pople,

1975) for the atom sequence N1–C2–N3–C4–C5–C6 (Table 1).

Thus, the ring-puckering parameters for compounds (IV)–

(VI) are all very similar, and in each case the boat confor-

mation has atoms C2 and C5 as the prow and stern of the boat,

respectively, displaced to one side of the mean plane through

the ring atoms, with atoms N1, N3, C4 and C6 all displaced to

the opposite side of this plane, indicated schematically as (A)

in the Scheme. Where three substituents are present at the 4-,

5- and 6-positions in pyrimidines, the ring is often found to be

quite markedly nonplanar, leading to boat (Quesada et al.,

2004; Low et al., 2007; Trilleras et al., 2007; Cobo et al., 2008),

twist-boat (Melguizo et al., 2003; Quesada et al., 2003; Cobo et

al., 2008) or screw-boat (Low et al., 2007) conformations, as

well as a variety of intermediate forms (Cobo et al., 2008). The

conformations of (IV)–(VI) reported here are thus fully

consistent with some of the examples reported earlier.

However, even when the pyrimidine ring is effectively planar,

as in (I)–(III), the ring substituent atoms are not always

coplanar with the ring, with atom C51 always markedly

displaced from the mean plane (Table 1).

˚

short for its type (reference mean = 1.470 A and lower

˚

quartile = 1.463 A). The N21—C2, C2—N3, N3—C4 and

C4—N41 bond lengths (Fig. 1) are all very similar in each

compound, despite the fact that the C2—N3 and N3—C4

bonds are formally of heteroaromatic type, while the exocyclic

N21—C2 and C4—N41 bonds are formally single bonds. It

may also be noted here that the N1—C2 bond is usually the

longest of the ring N—C bonds, while the C6—N61 bond is

consistently longer than the C4—N41 bond, and this may be

associated with the fact that, in general, the substituents at

N61 are usually displaced well away from the mean pyrimidine

plane by a rotation about the C6—N61 bond. Moreover, the

geometry at N61 is always slightly pyramidal, with a mean sum

˚

of the bond angles of 353.6 (2) A, while atom N41 is always

effectively planar.

The supramolecular assembly is dominated by N—HÁ Á ÁN

and N—HÁ Á ÁO hydrogen bonds, with C—HÁ Á ÁO hydrogen

bonds also present in the structures of (II) and (V) and a C—

HÁ Á ÁN hydrogen bond present in the structure of (VI). C—

HÁ Á ÁO interactions involving C—H bonds in methyl groups,

and those having D—HÁ Á ÁA angles signiﬁcantly less than 140^ꢁ,

have been discounted (cf. Wood et al., 2009). However, N—

HÁ Á Áꢀ(arene) and C—HÁ Á Áꢀ(arene) hydrogen bonds are

absent, while the polarized pyrimidine rings are far from being

aromatic. Despite the rather similar constitutions of (I)–(VI),

the patterns of their hydrogen-bonded supramolecular

assemblies vary widely, from simple dimeric units in (I), via

chains and sheets, to a three-dimensional framework structure

While the glycinate ester side chains at position 4 in (I) and

(IV) both adopt all-transoid extended-chain conformations, as

demonstrated by the relevant torsion angles, which all lie

within 10^ꢁof 180^ꢁ, the corresponding aminopropionate

substituents in (III), (V) and (VI) show a considerable

variation in their conformations (Table 1 and Fig. 1). In

particular, the values of the three torsion angles C4—N41—

C42—C43, N41—C42—C43—C44 and C42—C43—C44—O45

show wide variations among these compounds. While it is

tempting to associate these variations with the different

patterns of hydrogen bonds involving this substituent in (III),

(V) and (VI), such an approach cannot readily be reconciled

with the similarity in the conformations of the 4-substituent in

(I) and (IV), where the hydrogen bonds involving the

4-substituent are also different, with no involvement at all in

(I), but participation of atom O43 in (IV) (Table 2).

Figure 2

Part of the crystal structure of (I), showing the formation of a

centrosymmetric hydrogen-bonded (dashed lines) R²₂(8) dimer. For the

sake of clarity, H atoms other than those bonded to atom N21 have been

omitted. Atoms marked with an asterisk (*) are at the symmetry position

(Àx, Ày + 1, Àz + 1).

There are some interesting patterns in the bond lengths in

(I)–(VI) (Table 1) which suggest that the polarized form (C)

(see Scheme) is a signiﬁcant contributor to the overall elec-

ꢀ

164 Acosta et al.

C₁₆H₁₉N₅O₃, C₁₄H₁₆N₆O₂, C₁₇H₂₁N₅O₃, C₁₈H₂₃N₅O₃and C₁₅H₂₃N₅O₃

Acta Cryst. (2013). C69, 162–171

organic compounds

Figure 3

Figure 4

A stereoview of part of the crystal structure of (III), showing the

formation of a hydrogen-bonded (dashed lines) chain of R²₂(8) and R₂²(20)

rings along [001]. For the sake of clarity, H atoms other than those bonded

to atom N21 have been omitted.

A stereoview of part of the crystal structure of (IV), showing the

formation of a hydrogen-bonded (dashed lines) sheet of R⁴₄(28) rings

lying parallel to (100). For the sake of clarity, H atoms other than those

bonded to atom N21 have been omitted.

in (II). It is convenient to consider the hydrogen-bonded

structures in order of increasing complexity.

The combination of these two chain motifs generates a sheet

lying parallel to (100), in the form of a (4,4) net containing a

single type of R⁴₄(28) ring (Fig. 4).

In the structure of (I), there is only a single intermolecular

hydrogen bond, of N—HÁ Á ÁN type, and pairs of such bonds

link inversion-related pairs of molecules into dimers char-

acterized by a centrosymmetric R²₂(8) (Bernstein et al., 1995)

motif (Fig. 2).

While the sheet in (IV) is built from two N—HÁ Á ÁO

hydrogen bonds, intermolecular hydrogen bonds of this type

are absent from the structure of (V). Instead, the supra-

molecular assembly depends upon two hydrogen bonds of N—

HÁ Á ÁN type and one of C—HÁ Á ÁO type (Table 2), and the

formation of the sheet is most readily analysed in terms of two

one-dimensional substructures (Ferguson et al., 1998a,b;

Gregson et al., 2000). In the ﬁrst substructure, the two N—

HÁ Á ÁN hydrogen bonds, acting in isolation, each forms a C(4)

chain running parallel to the [010] direction, and in combi-

nation they generate a chain of edge-fused rings containing

The molecules of (III) are linked into a chain of edge-fused

rings by a combination of N—HÁ Á ÁN and N—HÁ Á ÁO hydrogen

bonds. A pair of molecules related by the twofold rotation axis

1

along (¹₂, y, ) are linked by symmetry-related N—HÁ Á ÁN

4

hydrogen bonds, using the same donor and acceptor as in (I)

and forming an R²₂(8) ring, while a pair of molecules related by

inversion are linked by symmetry-related N—HÁ Á ÁO hydro-

1

3

4

gen bonds to form an R₂²(20) motif centred at (¹₂, , ). The

molecules related by the 2₁screw axis along (³₄, y, ) (Fig. 5).

2

combination of these two motifs, propagated by rotation and

inversion, generates a chain of edge-fused rings running

parallel to the [001] direction, with R²₂(20) rings centred at

The C—HÁ Á ÁO hydrogen bond links inversion-related pairs of

molecules to form a centrosymmetric R²₂(22) motif. The mol-

ecule at (x, y, z) lies in the chain of edge-fused rings along

1

n

(¹₂, , ), where n represents an integer, alternating with R²₂(8)

2

rings lying across the twofold axes along (¹₂, y, ₄¹+ ⁿ), where n

again represents an integer (Fig. 3).

2

Compounds (IV), (V) and (VI) all form sheets of increasing

complexity and built using two, three and four hydrogen

bonds, respectively (Table 2). There is no obvious correlation

between the complexity of the supramolecular assemblies and

the complexity, speciﬁcally the number of symmetry operators,

of the space groups concerned, P2₁/c, C2/c and P1, respec-

tively. In (IV), amino atom N21 in the molecule at (x, y, z) acts

as hydrogen-bond donor, via atom H21A, to formyl atom O51

3

1

in the molecule at (x, Ày + , z + ), so forming a C(9) chain

2

running parallel to the [001] direction and built from mol-

3

ecules related by the 2₁screw axis along (0, , z). This same

atom, N21, also acts as hydrogen-bond donor, this time via

4

Figure 5

A stereoview of part of the crystal structure of (V), showing the

formation of a hydrogen-bonded (dashed lines) chain of edge-fused R²₂(8)

rings along [010]. For the sake of clarity, H atoms other than those bonded

to atom N21 have been omitted.

1

atom H21B, to ester atom O43 in the molecule at (x, Ày + ,

2

z + ¹₂), forming a C(9) chain, also parallel to [001] and

containing molecules related by the 2₁screw axis along (0, ¹₄, z).

ꢀ

Acta Cryst. (2013). C69, 162–171

Acosta et al.

C₁₆H₁₉N₅O₃, C₁₄H₁₆N₆O₂, C₁₇H₂₁N₅O₃, C₁₈H₂₃N₅O₃and C₁₅H₂₃N₅O₃165

organic compounds

Hydrogen bonds of N—HÁ Á ÁN type are absent from the

structure of (VI), where the sheet structure is generated by

N—HÁ Á ÁO hydrogen bonds (Table 2). As for (V), it is

convenient to describe the formation of the sheet structure in

(VI) in terms of two one-dimensional substructures. In one

substructure, amino atom N21 acts as hydrogen-bond donor,

via atoms H21A and H21B, to ester atoms O44 in the mol-

ecules at (x, y + 1, z) and (Àx, Ày + 1, Àz), respectively, and

these interactions generate a chain of edge-fused centrosym-

metric rings running parallel to the [010] direction, within

which R²₄(8) rings centred at (0, n, 0) alternate with R²₂(20)

rings centred at (0, ¹₂+ n, 0), where n represents an integer in

both cases (Fig. 7). There is an intermolecular C—HÁ Á ÁN

contact in the structure, involving the ꢁ-CH₂group of the

carboxylate unit as donor. If this is regarded as structurally

signiﬁcant, its role is modestly to reinforce the chain along

[010]. Amino atom N41 participates in a planar three-centre

N—HÁ Á Á(O)₂hydrogen bond, where the acceptors are two

formyl O51 atoms at (x, y, z) and (Àx, Ày + 1, Àz + 1)

(Table 2), forming, respectively, S(6) and R²₂(4) motifs. The

combination of these motifs with the R²₂(20) motif produces a

second substructure in the form of a chain of rings running

parallel to the [001] direction, with R²₂(20) rings centred at

Figure 6

A stereoview of part of the crystal structure of (V), showing the

formation of a hydrogen-bonded (dashed lines) chain of alternating R²₂(8)

and R²₂(22) rings along [111]. For the sake of clarity, H atoms other than

those bonded to atoms N21 and C46 have been omitted.

(³₄, y, ³₄), while that at (Àx + 1, Ày + 1, Àz + 1) forms part of a

similar chain along (¹₄, y, ). The combination of all three

1

4

hydrogen bonds generates a chain of rings running parallel to

the [111] direction in which R²₂(8) and R²₂(22) rings alternate

(Fig. 6). The combination of the [101] and [111] substructural

chains then generates a complex sheet lying parallel to (101).

1

1 1

(0, , n) alternating with R₂²(4) rings centred at (0, , + n),

2

2 2

Figure 7

Part of the crystal structure of compound (VI), showing the formation of

a hydrogen-bonded (dashed lines) chain of alternating R²₄(8) and R₂²(20)

rings along [010]. For the sake of clarity, H atoms other than those bonded

to atom N21 have been omitted. Atoms marked with an asterisk (*), a

hash symbol (#), a dollar sign ($) or an ampersand (&) are at the

symmetry positions (x, y + 1, z), (x, y À 1, z), (Àx, Ày + 1, Àz) and (Àx,

Ày, Àz), respectively.

Figure 8

Part of the crystal structure of (VI), showing the formation of a hydrogen-

bonded (dashed lines) chain of alternating R²₂(4) and R₂²(20) rings along

[001]. For the sake of clarity, H atoms other than those bonded to atoms

N21 and N41 have been omitted. Atoms marked with an asterisk (*), a

hash symbol (#) or a dollar sign ($) are at the symmetry positions (Àx,

Ày + 1, Àz + 1), (x, y, z + 1) and (Àx, Ày + 1, Àz + 2), respectively.

ꢀ

166 Acosta et al.

C₁₆H₁₉N₅O₃, C₁₄H₁₆N₆O₂, C₁₇H₂₁N₅O₃, C₁₈H₂₃N₅O₃and C₁₅H₂₃N₅O₃

Acta Cryst. (2013). C69, 162–171

organic compounds

the form of chains. In the simpler of the two chain motifs

comprising the sheet, molecules related by translation are

linked into a C(9) chain running parallel to the [010] direction

(Fig. 10). It is interesting to note that only one of the N—H

bonds in the amide unit containing atom N21 participates in

the hydrogen bonding.

The second chain motif in (II) involves the two N—H bonds

of the amide unit containing atom N44. This atom, in the

reference molecule at (x, y, z), acts as hydrogen-bond donor,

via atom H44A, to formyl atom O51 at (Àx + 1, y, Àz + ¹₂), so

forming an R²₂(18) ring containing two molecules related by

the twofold rotation axis along (¹₂, y, ₄¹). Atom N44 at (x, y, z)

also acts as donor, this time via atom H44B, to amide atom

Figure 9

A stereoview of part of the crystal structure of (VI), showing the

formation of a hydrogen-bonded (dashed lines) sheet lying parallel to

(100). For the sake of clarity, H atoms other than those bonded to atoms

N21 and N41 have been omitted.

3

1

O43 at (Àx + , Ày + , Àz + 1), so forming an R²₂(8) ring

2

1

4

1

2

containing two molecules related by inversion across (³₄, , ).

The combination of these two motifs generates a chain of

edge-fused rings running parallel to the [101] direction, with

n

2

1 n

4 2

R²₂(8) rings centred at (₄¹+ , , ) alternating with R²₂(8) rings

where n represents an integer (Fig. 8). The combination of the

substructures parallel to [010] and [001] generates a sheet

lying parallel to (100) (Fig. 9).

Compound (II) is the only example amongst those

discussed here in which the hydrogen-bonded supramolecular

assembly is three-dimensional. The formation of this three-

dimensional framework is most conveniently analysed in

terms of the linking of sheets generated solely by N—HÁ Á ÁO

hydrogen bonds, and the formation of the sheet structure in

turn is most readily analysed in terms of two substructures in

lying across the twofold rotation axes along (ⁿ₂, y,

1

n

À + ), where n represents an integer in each case (Fig. 11).

4

2

The combination of the simple chain along [010] and the

chain of rings along [101] generates a sheet lying parallel to

(101). Two sheets of this type, related to one another by

inversion, pass through each unit cell, and adjacent sheets are

linked by the third substructural motif, so generating a three-

dimensional framework structure. Aryl atom C62 in the mol-

ecule at (x, y, z) acts as hydrogen-bond donor to amide atom

O43 at (Àx + 1, Ày + 1, Àz + 1), so forming a centrosymmetric

R²₂(22) ring (Fig. 12) in which the two component molecules lie

in different (101) sheets. Propagation of this interaction by the

space-group symmetry operators serves to link all of the

sheets into a single continuous structure.

In summary, we have shown that the hydrogen-bonded

assembly of six very closely related pyrimidine derivatives

varies widely, emcompassing a simple dimeric unit, chains,

sheets and a three-dimensional framework structure.

Figure 10

Part of the crystal structure of (II), showing the formation of a hydrogen-

bonded (dashed lines) C(9) chain along [010]. For the sake of clarity, H

atoms other than those bonded to atoms N21 and N44 have been omitted.

Atoms marked with an asterisk (*) or a hash symbol (#) are at the

symmetry positions (x, y + 1, z) and (x, y À 1, z), respectively.

Figure 11

A stereoview of part of the crystal structure of (II), showing the

formation of a hydrogen-bonded (dashed lines) chain of alternating R²₂(8)

and R²₂(18) rings along [101]. For the sake of clarity, H atoms other than

those bonded to atoms N21 and N44 have been omitted.

ꢀ

Acta Cryst. (2013). C69, 162–171

Acosta et al.

C₁₆H₁₉N₅O₃, C₁₄H₁₆N₆O₂, C₁₇H₂₁N₅O₃, C₁₈H₂₃N₅O₃and C₁₅H₂₃N₅O₃167

organic compounds

found: C 60.7, H 6.2, N 19.2%; C₁₈H₂₃N₅O₃requires: C 60.5, H 6.5, N

19.6%.

Compound (VI), from 2-amino-4-chloro-6-(piperidin-1-yl)pyrimi-

dine-5-carbaldehyde and ꢂ-alanine ethyl ester hydrochloride. Reac-

tion time 21 h, yield 99%, colourless, m.p. 378 K. MS (EI, 70 eV) m/z

(%): 321 (M⁺, 42), 304 (100), 276 (25), 230 (18), 216 (26). Analysis

found: C 55.7, H 7.4, N 21.7%; C₁₅H₂₃N₅O₃requires: C 56.1, H 7.2, N

21.8%.

For the synthesis of (II), a sample of (I) (0.3 mmol) was added to a

methanol ammonia solution (5 ml of 7 M), and this mixture was then

held at 313 K for 6 h. The solvent and the excess ammonia were

removed under reduced pressure at ambient temperature and the

product was crystallized from methanol [yield 75%, colourless, m.p.

>413 K (decomposition)]. MS (EI, 70 eV) m/z (%): 300 (M⁺, 65),

299 (100), 283 (17), 256 (92), 254 (67), 238 (44), 226 (56), 212 (34),

200 (22), 106 (20). HRMS found: 300.1331; C₁₄H₁₆N₆O₂requires

300.1335.

Figure 12

Part of the crystal structure of (II), showing the formation of the

centrosymmetric R²₂(22) motif which links the (101) sheets. Hydrogen

bonds are shown as dashed lines. For the sake of clarity, H atoms not

involved in the motif shown have been omitted. Atoms marked with an

asterisk (*) are at the symmetry position (Àx + 1, Ày + 1, Àz + 1).

Compound (I)

Crystal data

C₁₆H₁₉N₅O₃

M_r= 329.36

Triclinic, P1

ꢃ = 72.693 (13)^ꢁ

3

˚

V = 808.5 (3) A

Z = 2

˚

a = 7.3990 (5) A

Mo Kꢁ radiation

ꢄ = 0.10 mm^À1

T = 293 K

0.41 Â 0.25 Â 0.22 mm

˚

b = 9.609 (3) A

˚

c = 12.449 (3) A

Experimental

ꢁ = 73.30 (2)^ꢁ

For the synthesis of the esters (I) and (III)–(VI), the appropriate

amino ester hydrochloride (1.3 mmol) and anhydrous potassium

carbonate (6.5 mmol) were added to a suspension of the appropriate

N⁴-substituted 2,4-diamino-6-chloropyrimidine-5-carbaldehyde in dry

acetonitrile (10 ml). The mixtures were then heated under reﬂux until

thin-layer chromatography (TLC) indicated that the starting

pyrimidine had all been consumed. The mixtures were then cooled to

ambient temperature and the solvent was removed under reduced

pressure. The resulting products were then puriﬁed by ﬂash chro-

matography on silica gel using dichloromethane/acetone mixtures

(95:5 to 90:10 v/v) as eluent. Finally, crystals suitable for single-crystal

X-ray diffraction were grown by slow evaporation of solutions in

methanol at ambient temperature and in air.

ꢂ = 82.680 (14)^ꢁ

Data collection

Bruker–Nonius KappaCCD area-

detector diffractometer

Absorption correction: multi-scan

(SADABS; Sheldrick, 2003)

T_min= 0.885, T_max= 0.936

18365 measured reﬂections

3006 independent reﬂections

2054 reﬂections with I > 2ꢅ(I)

R_int= 0.042

Reﬁnement

R[F²> 2ꢅ(F²)] = 0.045

wR(F²) = 0.120

S = 1.02

220 parameters

H-atom paramete_Àrs₃constrained

˚

Áꢆ_max= 0.19 e A

À3

˚

3006 reﬂections

Áꢆ_min= À0.17 e A

Compound (I), from 2-amino-4-chloro-6-[methyl(phenyl)amino]-

pyrimidine-5-carbaldehyde and glycine ethyl ester hydrochloride.

Reaction time 24 h, yield 83%, pale yellow, m.p. 394 K (decomposi-

tion). MS (EI, 70 eV) m/z (%): 329 (M⁺, 92), 328 (100), 312 (51),

200 (41), 254 (68), 238 (43), 226 (66). Analysis found: C 58.1, H 5.9,

N 20.9%; C₁₆H₁₉N₅O₃requires: C 58.3, H 5.8, N 21.3%.

Compound (II)

Crystal data

3

˚

V = 2860.3 (8) A

Z = 8

C₁₄H₁₆N₆O₂

M_r= 300.33

Compound (III), from 2-amino-4-chloro-6-[methyl(phenyl)amino]-

pyrimidine-5-carbaldehyde and ꢂ-alanine ethyl ester hydrochloride.

Reaction time 20 h, yield 78%, colourless, m.p. >433 K (decomposi-

tion). MS (EI, 70 eV) m/z (%): 3443 (M⁺, 79), 342 (100), 254 (62),

214 (40). Analysis found: C 59.5, H 5.9, N 19.9%; C₁₇H₂₁N₅O₃

requires: C 59.5, H 6.2, N 20.4%.

Monoclinic, C2=c

Mo Kꢁ radiation

ꢄ = 0.10 mm^À1

T = 120 K

0.32 Â 0.20 Â 0.11 mm

˚

a = 20.045 (4) A

˚

b = 8.6868 (7) A

˚

c = 17.990 (3) A

ꢂ = 114.064 (11)^ꢁ

Data collection

Compound (IV), from 2-amino-6-[benzyl(methyl)amino]-4-chloro-

pyrimidine-5-carbaldehyde and glycine ethyl ester hydrochloride.

Reaction time 4 d, yield 87%, colourless, m.p. 388 K (decomposition).

MS (EI, 70 eV) m/z (%): 329 (M⁺, 77), 313 (20), 312 (100), 300 (31),

270 (21), 259 (29), 120 (73), 91 (65).

Bruker–Nonius KappaCCD area-

detector diffractometer

Absorption correction: multi-scan

(SADABS; Sheldrick, 2003)

T_min= 0.969, T_max= 0.989

32858 measured reﬂections

2657 independent reﬂections

1993 reﬂections with I > 2ꢅ(I)

R_int= 0.068

Compound (V), from 2-amino-6-[benzyl(methyl)amino]-4-chloro-

pyrimidine-5-carbaldehyde and ꢂ-alanine ethyl ester hydrochloride.

Reaction time 24 h, yield 88%, colourless, m.p. 388 K (decomposi-

tion). MS (EI, 70 eV) m/z (%): 357 (M⁺, 53), 340 (72), 328 (20),

312 (26), 270 (13), 266 (26), 252 (31), 192 (82), 91 (100). Analysis

Reﬁnement

R[F²> 2ꢅ(F²)] = 0.049

wR(F²) = 0.119

S = 1.12

200 parameters

H-atom paramete_Àrs₃constrained

˚

Áꢆ_max= 0.34 e A

À3

˚

2657 reﬂections

Áꢆ_min= À0.26 e A

ꢀ

168 Acosta et al.

C₁₆H₁₉N₅O₃, C₁₄H₁₆N₆O₂, C₁₇H₂₁N₅O₃, C₁₈H₂₃N₅O₃and C₁₅H₂₃N₅O₃

Acta Cryst. (2013). C69, 162–171

organic compounds

Table 1

Selected geometric parameters (A, ) for compounds (I)–(VI).

ꢁ

˚

(i) Bond lengths

Parameter

(I)

(II)

(III)

(IV)

(V)

(VI)

N1—C2

C2—N3

N3—C4

C4—C5

C5—C6

C6—N1

C2—N21

C4—N41

C5—C51

C51—O51

C6—N61

1.353 (2)

1.340 (2)

1.335 (2)

1.430 (2)

1.418 (2)

1.335 (2)

1.342 (2)

1.336 (2)

1.426 (3)

1.232 (2)

1.380 (2)

1.350 (3)

1.352 (3)

1.336 (3)

1.436 (3)

1.438 (3)

1.336 (3)

1.337 (3)

1.352 (3)

1.426 (3)

1.247 (3)

1.371 (3)

1.361 (2)

1.341 (2)

1.346 (2)

1.433 (2)

1.428 (2)

1.339 (2)

1.340 (2)

1.343 (2)

1.432 (3)

1.239 (2)

1.381 (2)

1.353 (3)

1.342 (3)

1.339 (3)

1.436 (3)

1.429 (3)

1.331 (3)

1.340 (3)

1.334 (3)

1.420 (3)

1.239 (3)

1.381 (3)

1.346 (2)

1.441 (3)

1.430 (3)

1.351 (2)

1.345 (2)

1.343 (2)

1.426 (3)

1.241 (2)

1.359 (2)

1.353 (3)

1.344 (2)

1.335 (3)

1.434 (3)

1.421 (3)

1.324 (3)

1.336 (3)

1.339 (3)

1.409 (3)

1.234 (2)

1.378 (3)

(ii) Torsion angles

N3—C4—N41—C42

C4—N41—C42—C43

N41—C42—C43—C44

N41—C42—C43—N44

À4.8 (2)

7.0 (3)

À88.6 (3)

3.2 (3)

114.35 (19)

74.4 (2)

À2.4 (3)

11.0 (3)

À138.69 (18)

À63.1 (2)

À0.9 (3)

78.2 (2)

81.2 (2)

À196.15 (17)

À178.5 (2)

1.3 (3)

N41—C42—C43—O44 À172.71 (17)

170.47 (19)

C42—C43—C44—O45

C43—C44—O45—C46

C44—O45—C46—C47

À68.3 (2)

179.43 (16)

À174.16 (16)

À174.63 (16)

À177.40 (16)

À147.25 (18)

À109.4 (2)

À179.55 (17)

171.90 (18)

C42—C43—O44—C45

C43—O44—C45—C46

C4—C5—C51—O51

C5—C6—N61—C61

C5—C6—N61—C62

C5—C6—N61—C66

C5—C6—N61—C67

C5—C6—C61—C68

178.29 (17)

170.04 (19)

13.1 (3)

177.2 (2)

15.3 (4)

8.3 (4)

35.4 (3)

13.2 (3)

39.4 (2)

11.5 (3)

14.9 (3)

42.6 (3)

À174.97 (18)

43.4 (3)

À161.27 (18)

À175.8 (2)

À171.57 (16)

46.0 (3)

À169.3 (2)

À170.05 (17)

22.5 (3)

(iii) Substituent displacement from mean pyrimidine plane

Compound

N21

N41

C51

O51

N61

(I)

0.077 (2)

0.132 (2)

0.106 (2)

0.161 (2)

0.300 (2)

0.245 (2)

À0.015 (2)

À0.035 (2)

À0.162 (2)

À0.037 (2)

À0.172 (2)

À0.104 (2)

0.319 (2)

0.321 (2)

0.353 (2)

0.444 (3)

0.493 (2)

0.564 (2)

0.334 (2)

0.391 (2)

0.331 (2)

0.487 (2)

0.548 (2)

0.670 (2)

À0.071 (2)

À0.101 (2)

À0.084 (2)

À0.190 (2)

À0.256 (2)

À0.251 (2)

(II)

(III)

(IV)

(V)

(VI)

(iv) Ring-puckering parameters

Compound

Q

ꢇ

’

(IV)

(V)

(VI)

Idealized boat

0.100 (3)

0.156 (3)

0.149 (2)

97.0 (17)

98.5 (7)

96.9 (8)

90.0

76.9 (14)

59.8 (7)

71.8 (8)

60n

Compound (III)

Reﬁnement

R[F²> 2ꢅ(F²)] = 0.044

wR(F²) = 0.095

S = 1.09

3160 reﬂections

228 parameters

H-atom paramete_Àrs₃constrained

Crystal data

˚

Áꢆ_max= 0.17 e A

3

À3

˚

C₁₇H₂₁N₅O₃

M_r= 343.39

Monoclinic, C2=c

a = 16.707 (6) A

b = 10.218 (2) A

V = 3403.5 (16) A

Z = 8

Áꢆ_min= À0.23 e A

Mo Kꢁ radiation

ꢄ = 0.10 mm^À1

T = 120 K

˚

Compound (IV)

c = 20.733 (5) A

ꢂ = 105.929 (19)^ꢁ

0.29 Â 0.22 Â 0.10 mm

Crystal data

3

˚

V = 1633.3 (8) A

Z = 4

C₁₆H₁₉N₅O₃

M_r= 329.36

Data collection

Bruker–Nonius KappaCCD area-

detector diffractometer

Absorption correction: multi-scan

(SADABS; Sheldrick, 2003)

T_min= 0.973, T_max= 0.991

21914 measured reﬂections

3160 independent reﬂections

2239 reﬂections with I > 2ꢅ(I)

R_int= 0.063

Monoclinic, P2₁=c

Mo Kꢁ radiation

ꢄ = 0.10 mm^À1

T = 120 K

0.29 Â 0.27 Â 0.15 mm

˚

a = 15.636 (4) A

˚

b = 6.5674 (18) A

˚

c = 17.336 (5) A

ꢂ = 113.440 (18)^ꢁ

ꢀ

Acta Cryst. (2013). C69, 162–171

Acosta et al.

C₁₆H₁₉N₅O₃, C₁₄H₁₆N₆O₂, C₁₇H₂₁N₅O₃, C₁₈H₂₃N₅O₃and C₁₅H₂₃N₅O₃169

organic compounds

Table 2

Hydrogen bonds and short intramolecular contacts (A, ) for compounds

(I)–(VI).

Data collection

ꢁ

˚

Bruker–Nonius KappaCCD area-

detector diffractometer

Absorption correction: multi-scan

(SADABS; Sheldrick, 2003)

T_min= 0.973, T_max= 0.986

21188 measured reﬂections

3013 independent reﬂections

2209 reﬂections with I > 2ꢅ(I)

R_int= 0.072

Compound D—HÁ Á ÁA

D—H HÁ Á ÁA DÁ Á ÁA

D—HÁ Á ÁA

(I)

N21—H21AÁ Á ÁN1ⁱ

0.92

0.94

2.22

1.90

3.125 (2) 167

2.675 (2) 138

N41—H41Á Á ÁO51

Reﬁnement

(II)

N21—H21AÁ Á ÁO43ⁱⁱ

N44—H44AÁ Á ÁO51ⁱⁱⁱ

N44—H44BÁ Á ÁO43^iv

C62—H62Á Á ÁO43^v

0.94

0.90

0.95

0.98

0.95

2.02

1.98

2.14

2.05

2.45

2.933 (2) 166

2.689 (2) 135

2.949 (2) 143

3.006 (3) 164

3.280 (3) 146

R[F²> 2ꢅ(F²)] = 0.059

wR(F²) = 0.165

S = 1.09

219 parameters

H-atom paramete_Àrs₃constrained

N41—H41Á Á ÁO51

˚

Áꢆ_max= 0.35 e A

Áꢆ_min= À0.36 e A

À3

˚

3013 reﬂections

(III)

(IV)

(V)

N21—H21AÁ Á ÁN1ⁱⁱⁱ

N21—H21BÁ Á ÁO44^v

N41—H41Á Á ÁO51

0.90

0.97

0.96

2.14

1.95

3.027 (2) 169

3.054 (2) 158

2.683 (2) 131

Compound (V)

Crystal data

N21—H21AÁ Á ÁO51^vi

1.00

N21—H21BÁ Á ÁO43^vii0.89

1.89

2.38

1.92

2.860 (3) 163

3.085 (3) 136

2.682 (3) 135

3

˚

V = 3505.0 (8) A

Z = 8

C₁₈H₂₃N₅O₃

M_r= 357.41

N41—H41Á Á ÁO51

0.96

Monoclinic, C2=c

Mo Kꢁ radiation

ꢄ = 0.10 mm^À1

T = 120 K

0.26 Â 0.21 Â 0.14 mm

N21—H21AÁ Á ÁN3^viii

N21—H21BÁ Á ÁN1^ix

N41—H41Á Á ÁO44

N41—H41Á Á ÁO51

C46—H46AÁ Á ÁO51^x

0.96

0.95

1.01

0.99

2.07

2.30

2.27

1.92

2.54

3.008 (2) 168

3.199 (2) 158

2.891 (2) 119

2.666 (2) 128

3.528 (3) 172

˚

a = 24.8226 (5) A

˚

b = 7.1379 (14) A

˚

c = 20.601 (2) A

ꢂ = 106.213 (8)^ꢁ

N21—H21AÁ Á ÁO44ⁱⁱ

N21—H21BÁ Á ÁO44^xi

N41—H41Á Á ÁO51

N41—H41Á Á ÁO51ⁱ

C43—H43AÁ Á ÁN3^xi

0.88

0.89

0.94

0.99

2.15

2.20

2.05

2.21

2.55

2.951 (3) 150

3.036 (3) 156

2.700 (3) 125

2.909 (3) 131

3.524 (4) 169

Data collection

(VI)

Bruker–Nonius KappaCCD area-

detector diffractometer

Absorption correction: multi-scan

(SADABS; Sheldrick, 2003)

T_min= 0.976, T_max= 0.987

22384 measured reﬂections

3269 independent reﬂections

2276 reﬂections with I > 2ꢅ(I)

R_int= 0.073

Symmetry codes: (i) Àx, Ày + 1, Àz + 1; (ii) x, y + 1, z; (iii) Àx + 1, y, Àz + ¹₂; (iv) Àx + ₂³,

Ày + ₂¹, Àz + 1; (v) Àx + 1, Ày + 1, Àz + 1; (vi) x, Ày + ₂³, z + ¹₂; (vii) x, Ày + ₂¹, z + ¹₂; (viii)

Àx + ³₂, y + ₂¹, Àz + ₂³; (ix) Àx + ³₂, y À , Àz + ³₂; (x) Àx + 1, Ày, Àz + 1; (xi) Àx, Ày + 1,

1

2

Reﬁnement

Àz.

R[F²> 2ꢅ(F²)] = 0.045

wR(F²) = 0.104

S = 1.06

237 parameters

H-atom paramete_Àrs₃constrained

˚

Áꢆ_max= 0.21 e A

Áꢆ_min= À0.25 e A

À3

˚

1.5 for the methyl groups, which were permitted to rotate but not to

tilt, and 1.2 for all other C-bound H atoms. N-bound H atoms were

permitted to ride at the positions deduced from the difference maps,

with U_iso(H) = 1.2U_eq(N), giving N—H distances in the range 0.77–

3269 reﬂections

Compound (VI)

˚

1.01 A (see Table 2).

Crystal data

For all compounds, data collection: COLLECT (Nonius, 1999); cell

reﬁnement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction:

EVALCCD (Duisenberg et al., 2003); program(s) used to solve

structure: SIR2004 (Burla et al., 2005); program(s) used to reﬁne

structure: SHELXL97 (Sheldrick, 2008); molecular graphics:

PLATON (Spek, 2009); software used to prepare material for

publication: SHELXL97 and PLATON.

C₁₅H₂₃N₅O₃

M_r= 321.38

Triclinic, P1

ꢃ = 103.10 (3)^ꢁ

3

˚

V = 781.2 (8) A

Z = 2

˚

a = 8.040 (4) A

Mo Kꢁ radiation

ꢄ = 0.10 mm^À1

T = 120 K

0.41 Â 0.25 Â 0.22 mm

˚

b = 10.391 (3) A

˚

c = 10.458 (8) A

ꢁ = 109.16 (3)^ꢁ

ꢂ = 98.19 (5)^ꢁ

´

The authors thank the Centro de Instrumentacion Cientı-

ﬁco-Tecnica of the Universidad de Jaen and the staff for the

Data collection

´

Bruker–Nonius KappaCCD area-

detector diffractometer

Absorption correction: multi-scan

(SADABS; Sheldrick, 2003)

T_min= 0.885, T_max= 0.936

17622 measured reﬂections

3227 independent reﬂections

2384 reﬂections with I > 2ꢅ(I)

R_int= 0.059

´

data collection. JC thanks the Consejerıa de Innovacion,

Ciencia y Empresa (Junta de Andalucıa, Spain), the Univer-

´

sidad de Jaen (UJA) and the Ministerio de Ciencia e Inno-

vacion (project No. SAF2008-04685-C02-02) for ﬁnancial

´

support. AP, LMA and AFY thank the Colombian Institute

for Science and Research (COLCIENCIAS, grant No. 1102-

Reﬁnement

R[F²> 2ꢅ(F²)] = 0.051

wR(F²) = 0.134

S = 1.05

209 parameters

H-atom paramete_Àrs₃constrained

´

521-28229). AFY and LMA both also thank the Associacion

˚

Áꢆ_max= 0.25 e A

Universitaria Iberoamericana de Postgrado (AUIP) for

supporting a research stage at UJA.

À3

˚

3227 reﬂections

Áꢆ_min= À0.32 e A

Supplementary data for this paper are available from the IUCr electronic

archives (Reference: YF3022). Services for accessing these data are

described at the back of the journal.

All H atoms were located in difference maps. C-bound H atoms

were subsequently treated as riding atoms in geometrically idealized

˚

positions, with C—H = 0.93–0.99 A and U_iso(H) = kU_eq(C), where k =

ꢀ

170 Acosta et al.

C₁₆H₁₉N₅O₃, C₁₄H₁₆N₆O₂, C₁₇H₂₁N₅O₃, C₁₈H₂₃N₅O₃and C₁₅H₂₃N₅O₃

Acta Cryst. (2013). C69, 162–171

organic compounds

Ferguson, G., Glidewell, C., Gregson, R. M. & Meehan, P . R . (1998 b ). Acta

Cryst. B 54 , 139–150.

References

Ghorab, M. M., Ismail, Z. H., Abdel-Gawad, S. M. & Aziem, A. A. (2004).

Heteroatom Chem. 15 , 57–62.

Gregson, R. M., Glidewell, C., Ferguson, G. & Lough, A. J. (2000). Acta Cryst.

B 56 , 39–57.

Low, J. N., Trilleras, J., Cobo, J., Marchal, A. & Glidewell, C. (2007). Acta Cryst.

C 63 , o681–o684.

Allen, F . H ., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor,

R. (1987). J. Chem. Soc. Perkin Trans. 2 , pp. S1–19.

Allen, F . H ., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (2006).

International Tables for Crystallography , Vol. C, ch. 9, pp. 790–811.

Heidelberg: Springer.

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.

Int. Ed. Engl. 34 , 1555–1573.

Melguizo, M., Quesada, A., Low, J. N. & Glidewell, C. (2003). Acta Cryst. B 59 ,

263–276.

Bruno, D., Schenone, S., Ranise, A., Bondavalli, F ., Filippelli, W ., Falcone, G.,

Motola, G. & Mazzeo, F . (1999). Il Farmaco , 54 , 95–100.

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De

Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38 ,

381–388.

Cantin, D., et al. (2006). PCT Int. Appl. WO 2006034512, A2, 20060330.

Cobo, J., Trilleras, J., Quiroga, J., Marchal, A., Nogueras, M., Low, J. N. &

Glidewell, C. (2008). Acta Cryst. B 64 , 596–609.

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97 , 1354–1358.

Duisenberg, A. J. M., Hooft, R. W . W ., Schreurs, A. M. M. & Kroon, J. (2000).

J. Appl. Cryst. 33 , 893–898.

Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003).

J. Appl. Cryst. 36 , 220–229.

Min, B. J., Gu, X., Yamamoto, T., Petrov, R. R., Qu, H., Lee, Y . S. & Hruby, V . J.

(2008). Tetrahedron Lett. 49 , 2316–2319.

Murata, T., Umeda, M., Yoshikawa, S., Urbahns, K., Gupta, J. & Sakurai, O.

(2004). PCT Int. Appl. WO 2004043926, A1, 20040527.

Nonius (1999). COLLECT . Nonius B V , D elft, The Netherlands.

Quesada, A., Marchal, A., Low, J. N. & Glidewell, C. (2003). Acta Cryst. C 59 ,

o102–o104.

Quesada, A., Marchal, A., Melguizo, M., Low, J. N. & Glidewell, C. (2004).

Acta Cryst. B 60 , 76–89.

¨

Sheldrick, G. M. (2003). SADABS . University of Gottingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A 64 , 112–122.

Spek, A. L. (2009). Acta Cryst. D 65 , 148–155.

T r illeras, J., Quiroga, J., Low, J. N., Cobo, J. & Glidewell, C. (2007). Acta Cryst.

C 63 , o758–o760.

Wood, P . A ., Allen, F . H . & Pidcock, E. (2009). CrystEngComm , 11 , 1563–1571.

Ferguson, G., Glidewell, C., Gregson, R. M. & Meehan, P . R . (1998 a ). Acta

Cryst. B 54 , 129–138.

ꢀ

Acta Cryst. (2013). C69, 162–171

Acosta et al.

C₁₆H₁₉N₅O₃, C₁₄H₁₆N₆O₂, C₁₇H₂₁N₅O₃, C₁₈H₂₃N₅O₃and C₁₅H₂₃N₅O₃171

supplementary materials

Acta Cryst. (2013). C69, 162-171 [doi:10.1107/S0108270112051049]

Six closely related 4,6-disubstituted 2-amino-5-formylpyrimidines: different ring

conformations, polarized electronic structures, and hydrogen-bonded assembly

in zero, one, two and three dimensions

Lina M. Acosta, Andrés F. Yepes, Alirio Palma, Justo Cobo and Christopher Glidewell

(I) Ethyl N-{2-amino-5-formyl-6-[methyl(phenyl)amino]pyrimidin-4-yl}glycinate

Crystal data

C₁₆H₁₉N₅O₃

Z = 2

M_r= 329.36

Triclinic, P1

F(000) = 348

D_x= 1.353 Mg m⁻³

Mo Kα radiation, λ = 0.71073 Å

Cell parameters from 3718 reflections

θ = 3.2–27.5°

Hall symbol: -P 1

a = 7.3990 (5) Å

b = 9.609 (3) Å

c = 12.449 (3) Å

α = 73.30 (2)°

β = 82.680 (14)°

γ = 72.693 (13)°

V = 808.5 (3) Å³

µ = 0.10 mm⁻¹

T = 293 K

Block, pale yellow

0.41 × 0.25 × 0.22 mm

Data collection

Bruker Nonius KappaCCD area-detector

diffractometer

Radiation source: Bruker Nonius FR591

rotating anode

Graphite monochromator

Detector resolution: 9.091 pixels mm^-1

φ and ω scans

T_min= 0.885, T_max= 0.936

18365 measured reflections

3006 independent reflections

2054 reflections with I > 2σ(I)

R_int= 0.042

θ

_max= 25.5°, θ_min= 3.2°

h = −8→8

Absorption correction: multi-scan

(SADABS; Sheldrick, 2003)

k = −11→11

l = −15→15

Refinement

Refinement on F²

Least-squares matrix: full

R[F²> 2σ(F²)] = 0.045

wR(F²) = 0.120

Hydrogen site location: inferred from

neighbouring sites

H-atom parameters constrained

w = 1/[σ²(F_o²) + (0.0562P)²+ 0.2215P]

where P = (F_o²+ 2F_c²)/3

S = 1.02

3006 reflections

220 parameters

0 restraints

(Δ/σ)_max= 0.001

Δρ_max= 0.19 e Å⁻³

Δρ_min= −0.17 e Å⁻³

Primary atom site location: structure-invariant

direct methods

Secondary atom site location: difference Fourier

map

Extinction correction: SHELXL97 (Sheldrick,

2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4

Extinction coefficient: 0.033 (4)

Acta Cryst. (2013). C69, 162-171

sup-1

supplementary materials

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

x

y

z

U_iso*/U_eq

N1

0.1832 (2)

0.2237 (2)

0.3581 (2)

0.4570 (2)

0.4235 (2)

0.2866 (2)

0.1191 (2)

0.0412

0.62253 (17)

0.6088 (2)

0.65340 (17)

0.7269 (2)

0.7561 (2)

0.6925 (2)

0.5411 (2)

0.4884

0.41032 (12)

0.51649 (15)

0.54930 (12)

0.46709 (15)

0.35103 (15)

0.32890 (14)

0.59954 (13)

0.5872

0.0370 (4)

0.0358 (4)

0.0372 (4)

0.0343 (4)

0.0348 (4)

0.0341 (4)

0.0488 (5)

0.059*

C2

N3

C4

C5

C6

N21

H21A

H21B

N41

H41

C42

H42A

H42B

C43

O43

O44

C45

H45A

H45B

C46

H46A

H46B

H46C

C51

H51

O51

N61

C61

C62

H62

C63

H63

C64

H64

C65

H65

C66

H66

C67

H67A

H67B

H67C

0.1525

0.5227

0.6757

0.059*

0.5891 (2)

0.6471

0.77684 (18)

0.8364

0.49610 (13)

0.4363

0.0415 (4)

0.050*

0.6239 (3)

0.6666

0.7672 (2)

0.6623

0.60966 (15)

0.6520

0.0414 (5)

0.050*

0.5087

0.8157

0.6465

0.050*

0.7738 (3)

0.8323 (2)

0.83342 (19)

0.9843 (3)

0.9497

0.8457 (2)

0.9156 (2)

0.82899 (16)

0.8998 (3)

1.0036

0.60362 (16)

0.51776 (13)

0.70415 (11)

0.70299 (19)

0.6575

0.0417 (5)

0.0728 (5)

0.0464 (4)

0.0534 (6)

0.064*

1.1011

0.8458

0.6708

0.064*

1.0116 (4)

1.0490

0.8957 (3)

0.7926

0.8196 (2)

0.8636

0.0657 (7)

0.099*

0.8951

0.9484

0.8511

0.099*

1.1086

0.9435

0.8198

0.099*

0.5014 (3)

0.4535

0.8607 (2)

0.8904

0.26646 (16)

0.1954

0.0421 (5)

0.050*

0.6259 (2)

0.2488 (2)

0.3994 (3)

0.5608 (3)

0.5737

0.91568 (17)

0.70546 (19)

0.6844 (2)

0.5669 (2)

0.5000

0.27831 (11)

0.22015 (12)

0.13638 (15)

0.16096 (17)

0.2322

0.0533 (4)

0.0406 (4)

0.0387 (5)

0.0474 (5)

0.057*

0.7041 (3)

0.8151

0.5488 (3)

0.4711

0.0788 (2)

0.0958

0.0614 (6)

0.074*

0.6842 (4)

0.7807

0.6443 (3)

0.6305

−0.0276 (2)

−0.0825

0.0664 (7)

0.080*

0.5227 (4)

0.5089

0.7593 (3)

0.8240

−0.05232 (18)

−0.1243

0.0615 (6)

0.074*

0.3798 (3)

0.2696

0.7799 (2)

0.8584

0.02895 (16)

0.0116

0.0502 (5)

0.060*

0.0719 (3)

−0.0287

0.0864

0.6819 (3)

0.7235

0.19802 (18)

0.2462

0.0557 (6)

0.084*

0.5756

0.2123

0.084*

0.0422

0.7311

0.1210

0.084*

Acta Cryst. (2013). C69, 162-171

sup-2

supplementary materials

Atomic displacement parameters (Å²)

U¹¹

U²²

U³³

U¹²

U¹³

U²³

N1

0.0371 (9)

0.0368 (10)

0.0398 (9)

0.0341 (10)

0.0347 (10)

0.0330 (10)

0.0562 (11)

0.0466 (9)

0.0466 (11)

0.0468 (11)

0.0944 (12)

0.0491 (8)

0.0486 (12)

0.0748 (16)

0.0453 (11)

0.0593 (9)

0.0369 (9)

0.0444 (11)

0.0532 (13)

0.0535 (14)

0.0729 (17)

0.0825 (18)

0.0589 (13)

0.0478 (13)

0.0447 (9)

0.0343 (9)

0.0340 (10)

0.0325 (8)

0.0352 (10)

0.0332 (10)

0.0329 (10)

0.0347 (9)

0.0330 (9)

0.0326 (10)

0.0346 (11)

0.0418 (9)

0.0375 (8)

0.0591 (14)

0.0639 (15)

0.0382 (11)

0.0450 (8)

0.0320 (8)

0.0331 (10)

0.0433 (12)

0.0703 (16)

0.0557 (15)

0.0341 (12)

0.0368 (11)

0.0412 (12)

−0.0186 (7)

−0.0141 (9)

−0.0206 (7)

−0.0123 (8)

−0.0147 (8)

−0.0103 (8)

−0.0392 (9)

−0.0302 (8)

−0.0234 (10)

−0.0245 (10)

−0.0740 (11)

−0.0324 (7)

−0.0320 (11)

−0.0337 (13)

−0.0205 (10)

−0.0386 (8)

−0.0202 (8)

−0.0212 (9)

−0.0176 (10)

−0.0134 (12)

−0.0365 (15)

−0.0394 (15)

−0.0195 (11)

−0.0326 (12)

0.0011 (7)

−0.0121 (7)

−0.0115 (8)

−0.0108 (7)

−0.0119 (8)

−0.0093 (8)

−0.0130 (8)

−0.0104 (7)

−0.0118 (9)

−0.0108 (9)

−0.0027 (9)

−0.0161 (7)

−0.0242 (11)

−0.0136 (13)

−0.0094 (9)

−0.0046 (7)

−0.0115 (7)

−0.0113 (9)

−0.0084 (9)

−0.0243 (13)

−0.0319 (14)

−0.0109 (11)

−0.0065 (10)

−0.0116 (11)

C2

0.0391 (11)

0.0449 (9)

0.0028 (8)

N3

0.0019 (7)

C4

0.0363 (10)

0.0391 (11)

0.0370 (10)

0.0683 (12)

0.0544 (11)

0.0520 (12)

0.0502 (12)

0.1037 (14)

0.0653 (9)

0.0004 (8)

C5

−0.0005 (8)

−0.0014 (8)

0.0040 (8)

C6

N21

N41

C42

C43

O43

O44

C45

C46

C51

O51

N61

C61

C62

C63

C64

C65

C66

C67

0.0009 (7)

−0.0010 (8)

0.0006 (9)

−0.0048 (8)

−0.0011 (6)

−0.0013 (10)

−0.0236 (13)

−0.0031 (9)

−0.0019 (7)

−0.0030 (7)

−0.0015 (8)

−0.0015 (10)

0.0068 (12)

0.0245 (13)

0.0075 (11)

−0.0059 (10)

−0.0075 (9)

0.0679 (15)

0.0708 (16)

0.0471 (12)

0.0638 (10)

0.0580 (11)

0.0453 (11)

0.0459 (12)

0.0606 (15)

0.0821 (19)

0.0749 (17)

0.0549 (13)

0.0859 (17)

Geometric parameters (Å, º)

N1—C6

1.335 (2)

C45—H45B

C46—H46A

C46—H46B

C46—H46C

C51—O51

C51—H51

N61—C61

N61—C67

C61—C62

C61—C66

C62—C63

C62—H62

C63—C64

C63—H63

C64—C65

C64—H64

C65—C66

C65—H65

C66—H66

C67—H67A

0.9700

N1—C2

1.353 (2)

1.340 (2)

1.342 (2)

1.335 (2)

1.336 (2)

1.430 (2)

1.418 (2)

1.426 (3)

1.380 (2)

0.9242

0.9600

C2—N3

0.9600

C2—N21

N3—C4

0.9600

1.232 (2)

0.9300

C4—N41

C4—C5

1.436 (2)

1.464 (2)

1.374 (3)

1.385 (3)

1.384 (3)

0.9300

C5—C6

C5—C51

C6—N61

N21—H21A

N21—H21B

N41—C42

N41—H41

C42—C43

C42—H42A

C42—H42B

C43—O43

C43—O44

O44—C45

0.9636

1.441 (2)

0.9409

1.375 (3)

0.9300

1.500 (3)

0.9700

1.362 (3)

0.9300

0.9700

1.378 (3)

0.9300

1.193 (2)

1.330 (2)

1.467 (2)

0.9300

0.9600

Acta Cryst. (2013). C69, 162-171

sup-3

supplementary materials

C45—C46

1.479 (3)

0.9700

C67—H67B

C67—H67C

0.9600

C45—H45A

C6—N1—C2

115.75 (15)

115.54 (16)

127.77 (16)

116.68 (16)

115.82 (15)

117.83 (16)

122.50 (16)

119.66 (16)

122.78 (17)

115.27 (16)

121.27 (16)

116.45 (16)

122.59 (16)

120.92 (16)

122.3

C45—C46—H46A

C45—C46—H46B

109.5

N3—C2—N21

N3—C2—N1

H46A—C46—H46B

C45—C46—H46C

H46A—C46—H46C

H46B—C46—H46C

O51—C51—C5

109.5

N21—C2—N1

109.5

C4—N3—C2

109.5

N3—C4—N41

109.5

N3—C4—C5

126.41 (18)

116.8

N41—C4—C5

O51—C51—H51

C5—C51—H51

C6—C5—C51

116.8

C6—C5—C4

C6—N61—C61

120.97 (15)

119.49 (15)

115.42 (15)

119.58 (19)

120.45 (17)

119.93 (18)

119.4 (2)

120.3

C51—C5—C4

C6—N61—C67

N1—C6—N61

C61—N61—C67

C62—C61—C66

C62—C61—N61

C66—C61—N61

C61—C62—C63

C61—C62—H62

C63—C62—H62

C64—C63—C62

C64—C63—H63

C62—C63—H63

C65—C64—C63

C65—C64—H64

C63—C64—H64

C64—C65—C66

C64—C65—H65

C66—C65—H65

C65—C66—C61

C65—C66—H66

C61—C66—H66

N61—C67—H67A

N61—C67—H67B

H67A—C67—H67B

N61—C67—H67C

H67A—C67—H67C

H67B—C67—H67C

N1—C6—C5

N61—C6—C5

C2—N21—H21A

C2—N21—H21B

H21A—N21—H21B

C4—N41—C42

C4—N41—H41

C42—N41—H41

N41—C42—C43

N41—C42—H42A

C43—C42—H42A

N41—C42—H42B

C43—C42—H42B

H42A—C42—H42B

O43—C43—O44

O43—C43—C42

O44—C43—C42

C43—O44—C45

O44—C45—C46

O44—C45—H45A

C46—C45—H45A

O44—C45—H45B

C46—C45—H45B

H45A—C45—H45B

118.0

117.4

124.86 (15)

115.3

120.3

120.7 (2)

119.6

119.0

107.29 (15)

110.3

119.6

119.7 (2)

120.1

110.3

120.1

110.3

120.2 (2)

119.9

108.5

124.00 (18)

123.37 (18)

112.62 (15)

114.96 (15)

108.72 (17)

109.9

119.9

120.3 (2)

119.9

109.5

109.9

109.5

109.9

109.5

109.9

109.5

108.3

109.5

C6—N1—C2—N3

C6—N1—C2—N21

N21—C2—N3—C4

N1—C2—N3—C4

C2—N3—C4—N41

C2—N3—C4—C5

N3—C4—C5—C6

N41—C4—C5—C6

N3—C4—C5—C51

−1.9 (3)

O43—C43—O44—C45

C42—C43—O44—C45

C43—O44—C45—C46

C6—C5—C51—O51

C4—C5—C51—O51

N1—C6—N61—C61

C5—C6—N61—C61

N1—C6—N61—C67

C5—C6—N61—C67

−1.9 (3)

178.89 (16)

−177.11 (16)

3.7 (3)

178.29 (17)

170.04 (19)

−176.82 (19)

13.1 (3)

178.29 (16)

−0.3 (3)

−139.74 (18)

42.6 (3)

−4.1 (3)

177.27 (16)

166.67 (17)

16.4 (3)

−161.27 (18)

Acta Cryst. (2013). C69, 162-171

sup-4

supplementary materials

N41—C4—C5—C51

C2—N1—C6—N61

C2—N1—C6—C5

−11.9 (3)

C6—N61—C61—C62

43.8 (3)

179.10 (16)

−3.3 (3)

C67—N61—C61—C62

C6—N61—C61—C66

C67—N61—C61—C66

C66—C61—C62—C63

N61—C61—C62—C63

C61—C62—C63—C64

C62—C63—C64—C65

C63—C64—C65—C66

C64—C65—C66—C61

C62—C61—C66—C65

N61—C61—C66—C65

−113.3 (2)

−138.31 (19)

64.7 (2)

C51—C5—C6—N1

C4—C5—C6—N1

−164.61 (18)

6.1 (3)

2.1 (3)

C51—C5—C6—N61

C4—C5—C6—N61

N3—C4—N41—C42

C5—C4—N41—C42

C4—N41—C42—C43

N41—C42—C43—O43

N41—C42—C43—O44

12.9 (3)

180.00 (19)

−1.8 (3)

−176.44 (16)

−4.8 (3)

0.8 (4)

173.87 (18)

−176.15 (17)

7.4 (3)

0.1 (4)

0.2 (3)

−1.3 (3)

−172.71 (17)

−179.20 (18)

Hydrogen-bond geometry (Å, º)

D—H···A

D—H

H···A

D···A

D—H···A

N21—H21A···N1ⁱ

N41—H41···O51

0.92

0.94

2.22

1.90

3.125 (2)

2.675 (2)

167

138

Symmetry code: (i) −x, −y+1, −z+1.

(II) N-{2-Amino-5-formyl-6-[methyl(phenyl)amino]pyrimidin-4-yl}glycinamide

Crystal data

C₁₄H₁₆N₆O₂

M_r= 300.33

F(000) = 1264

D_x= 1.395 Mg m⁻³

Monoclinic, C2/c

Hall symbol: -C 2yc

a = 20.045 (4) Å

b = 8.6868 (7) Å

c = 17.990 (3) Å

β = 114.064 (11)°

V = 2860.3 (8) Å³

Z = 8

Mo Kα radiation, λ = 0.71073 Å

Cell parameters from 3290 reflections

θ = 2.6–27.5°

µ = 0.10 mm⁻¹

T = 120 K

Plate, colourless

0.32 × 0.20 × 0.11 mm

Data collection

Bruker Nonius KappaCCD area-detector

diffractometer

Radiation source: Bruker Nonius FR591

rotating anode

Graphite monochromator

Detector resolution: 9.091 pixels mm^-1

φ and ω scans

Absorption correction: multi-scan

(SADABS; Sheldrick, 2003)

T_min= 0.969, T_max= 0.989

32858 measured reflections

2657 independent reflections

1993 reflections with I > 2σ(I)

R_int= 0.068

θ

_max= 25.5°, θ_min= 2.6°

h = −24→24

k = −10→10

l = −21→21

Refinement

Refinement on F²

Least-squares matrix: full

R[F²> 2σ(F²)] = 0.049

wR(F²) = 0.119

0 restraints

Primary atom site location: structure-invariant

direct methods

Secondary atom site location: difference Fourier

map

S = 1.12

2657 reflections

200 parameters

Hydrogen site location: inferred from

neighbouring sites

Acta Cryst. (2013). C69, 162-171

sup-5

supplementary materials

H-atom parameters constrained

w = 1/[σ²(F_o²) + (0.0427P)²+ 5.1608P]

where P = (F_o²+ 2F_c²)/3

(Δ/σ)_max= 0.001

Δρ_max= 0.34 e Å⁻³

Δρ_min= −0.26 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

x

y

z

U_iso*/U_eq

N1

0.53486 (10)

0.58234 (12)

0.57839 (10)

0.52481 (12)

0.47362 (11)

0.48010 (11)

0.63877 (11)

0.6428

0.9198 (2)

0.8233 (2)

0.6681 (2)

0.6035 (2)

0.6906 (2)

0.8548 (2)

0.8895 (2)

0.9964

0.40896 (11)

0.46413 (13)

0.46616 (11)

0.40211 (13)

0.33536 (13)

0.34637 (12)

0.52450 (11)

0.5215

0.0177 (4)

0.0176 (5)

0.0191 (4)

0.0161 (5)

0.0157 (5)

0.0264 (5)

0.032*

C2

N3

C4

C5

C6

N21

H21A

H21B

N41

H41

C42

H42A

H42B

C43

O43

N44

H44A

H44B

C51

H51

O51

N61

C61

C62

H62

C63

H63

C64

H64

C65

H65

C66

H66

C67

H67A

H67B

H67C

0.6728

0.8302

0.5639

0.032*

0.52083 (10)

0.4833

0.4481 (2)

0.4064

0.40089 (11)

0.3586

0.0199 (4)

0.024*

0.56561 (12)

0.5371

0.3514 (3)

0.2578

0.46820 (13)

0.4674

0.0200 (5)

0.024*

0.5742

0.4071

0.5193

0.024*

0.63942 (12)

0.67776 (9)

0.66162 (11)

0.6306

0.3004 (2)

0.21582 (17)

0.3466 (2)

0.4195

0.47167 (13)

0.52914 (9)

0.41535 (11)

0.3782

0.0179 (5)

0.0228 (4)

0.0240 (5)

0.029*

0.7127

0.3321

0.4232

0.029*

0.42654 (11)

0.3990

0.6197 (2)

0.6859

0.26089 (13)

0.2171

0.0163 (5)

0.020*

0.41838 (8)

0.43222 (10)

0.35514 (12)

0.31485 (12)

0.3384

0.47834 (17)

0.9555 (2)

0.9229 (2)

0.8653 (3)

0.8384

0.24825 (9)

0.29196 (11)

0.24847 (13)

0.28957 (13)

0.3455

0.0208 (4)

0.0171 (4)

0.0161 (5)

0.0199 (5)

0.024*

0.23939 (13)

0.2114

0.8474 (3)

0.8079

0.24764 (14)

0.2752

0.0246 (5)

0.030*

0.20517 (13)

0.1537

0.8868 (3)

0.8767

0.16633 (14)

0.1384

0.0243 (5)

0.029*

0.24613 (12)

0.2226

0.9412 (3)

0.9658

0.12547 (14)

0.0692

0.0228 (5)

0.027*

0.32116 (12)

0.3490

0.9600 (2)

0.9978

0.16621 (13)

0.1382

0.0186 (5)

0.022*

0.44708 (12)

0.4990

1.1210 (2)

1.1405

0.30632 (14)

0.3208

0.0219 (5)

0.033*

0.4344

1.1546

0.3509

0.033*

0.4177

1.1783

0.2568

0.033*

Atomic displacement parameters (Å²)

U¹¹

U²²

U³³

U¹²

U¹³

0.0021 (8)

U²³

N1

0.0172 (10)

0.0147 (9)

0.0164 (9)

−0.0011 (7)

−0.0015 (7)

Acta Cryst. (2013). C69, 162-171

sup-6

supplementary materials

C2

0.0183 (12)

0.0186 (10)

0.0179 (11)

0.0143 (11)

0.0166 (11)

0.0270 (11)

0.0207 (10)

0.0274 (13)

0.0227 (12)

0.0245 (9)

0.0239 (11)

0.0127 (11)

0.0193 (8)

0.0169 (12)

0.0167 (10)

0.0140 (11)

0.0154 (11)

0.0167 (11)

0.0141 (10)

0.0155 (10)

0.0134 (11)

0.0112 (11)

0.0186 (8)

0.0256 (11)

0.0172 (12)

0.0163 (8)

0.0118 (9)

0.0136 (11)

0.0156 (9)

0.0146 (11)

0.0160 (11)

0.0135 (11)

0.0209 (10)

0.0166 (9)

0.0162 (11)

0.0146 (11)

0.0184 (8)

0.0187 (10)

0.0177 (11)

0.0209 (8)

0.0185 (9)

0.0178 (11)

0.0161 (11)

0.0243 (12)

0.0260 (13)

0.0163 (11)

0.0185 (11)

0.0244 (12)

−0.0004 (9)

−0.0009 (8)

−0.0002 (9)

0.0006 (9)

0.0023 (9)

0.0003 (8)

0.0047 (9)

0.0059 (9)

−0.0080 (9)

0.0006 (8)

0.0059 (10)

0.0023 (9)

0.0017 (7)

0.0047 (8)

0.0048 (9)

0.0022 (7)

0.0015 (8)

0.0025 (9)

0.0047 (9)

0.0111 (10)

0.0007 (10)

−0.0027 (9)

0.0052 (9)

0.0019 (10)

−0.0003 (9)

−0.0004 (8)

−0.0017 (8)

0.0003 (9)

−0.0013 (9)

0.0008 (8)

−0.0008 (8)

0.0015 (9)

−0.0025 (9)

0.0024 (7)

0.0043 (8)

−0.0011 (9)

−0.0052 (6)

−0.0002 (7)

−0.0023 (8)

−0.0007 (9)

−0.0029 (10)

−0.0044 (10)

0.0005 (9)

0.0020 (9)

0.0006 (9)

N3

C4

C5

C6

−0.0001 (9)

−0.0020 (8)

−0.0029 (8)

−0.0022 (9)

−0.0046 (9)

0.0004 (7)

N21

N41

C42

C43

O43

N44

C51

O51

N61

C61

C62

C63

C64

C65

C66

C67

0.0048 (9)

0.0017 (9)

−0.0025 (7)

−0.0005 (7)

0.0014 (8)

0.0156 (9)

0.0148 (11)

0.0213 (12)

0.0221 (13)

0.0151 (12)

0.0229 (13)

0.0205 (12)

0.0197 (12)

0.0116 (11)

0.0195 (12)

0.0290 (13)

0.0244 (13)

0.0188 (12)

0.0142 (11)

0.0146 (12)

0.0016 (9)

−0.0034 (10)

−0.0009 (10)

0.0034 (10)

0.0012 (9)

−0.0013 (9)

Geometric parameters (Å, º)

N1—C6

1.336 (3)

N44—H44B

0.9820

N1—C2

1.350 (3)

1.337 (3)

1.352 (3)

1.336 (3)

1.352 (3)

1.436 (3)

1.426 (3)

1.438 (3)

1.371 (3)

0.9359

C51—O51

C51—H51

N61—C61

N61—C67

C61—C66

C61—C62

C62—C63

C62—H62

C63—C64

C63—H63

C64—C65

C64—H64

C65—C66

C65—H65

C66—H66

C67—H67A

C67—H67B

C67—H67C

1.247 (3)

0.9500

C2—N21

C2—N3

1.447 (3)

1.469 (3)

1.391 (3)

1.397 (3)

0.9500

N3—C4

C4—N41

C4—C5

C5—C51

C5—C6

C6—N61

N21—H21A

N21—H21B

N41—C42

N41—H41

C42—C43

C42—H42A

C42—H42B

C43—O43

C43—N44

N44—H44A

1.382 (3)

0.9500

0.9156

1.390 (3)

0.9500

1.446 (3)

0.8995

1.388 (3)

0.9500

1.521 (3)

0.9900

0.9500

0.9900

0.9800

1.246 (3)

1.324 (3)

0.9463

0.9800

C6—N1—C2

N21—C2—N1

N21—C2—N3

N1—C2—N3

C4—N3—C2

116.60 (18)

116.09 (19)

116.49 (19)

127.4 (2)

H44A—N44—H44B

O51—C51—C5

O51—C51—H51

C5—C51—H51

C6—N61—C61

122.3

125.7 (2)

117.1

115.49 (18)

122.89 (18)

Acta Cryst. (2013). C69, 162-171

sup-7

supplementary materials

N3—C4—N41

117.01 (19)

123.3 (2)

119.69 (19)

122.08 (19)

123.08 (19)

114.43 (19)

115.29 (19)

122.18 (19)

122.49 (19)

116.4

C6—N61—C67

C61—N61—C67

C66—C61—C62

C66—C61—N61

C62—C61—N61

C61—C62—C63

C61—C62—H62

C63—C62—H62

C64—C63—C62

C64—C63—H63

C62—C63—H63

C63—C64—C65

C63—C64—H64

C65—C64—H64

C66—C65—C64

C66—C65—H65

C64—C65—H65

C65—C66—C61

C65—C66—H66

C61—C66—H66

N61—C67—H67A

N61—C67—H67B

117.80 (17)

112.46 (17)

120.7 (2)

118.8 (2)

120.42 (19)

119.2 (2)

120.4

N3—C4—C5

N41—C4—C5

C51—C5—C4

C51—C5—C6

C4—C5—C6

N1—C6—N61

N1—C6—C5

120.4

N61—C6—C5

120.3 (2)

119.8

C2—N21—H21A

C2—N21—H21B

H21A—N21—H21B

C4—N41—C42

C4—N41—H41

C42—N41—H41

N41—C42—C43

N41—C42—H42A

C43—C42—H42A

N41—C42—H42B

C43—C42—H42B

H42A—C42—H42B

O43—C43—N44

O43—C43—C42

N44—C43—C42

C43—N44—H44A

C43—N44—H44B

120.2

119.8

123.2

119.9 (2)

120.0

123.65 (19)

116.1

120.0

119.6

120.5 (2)

119.8

117.69 (19)

107.9

119.8

107.9

119.3 (2)

120.3

107.9

120.3

107.2

109.5

121.9 (2)

117.8 (2)

120.34 (19)

114.4

109.5

H67A—C67—H67B

N61—C67—H67C

H67A—C67—H67C

H67B—C67—H67C

109.5

120.4

C6—N1—C2—N21

C6—N1—C2—N3

N21—C2—N3—C4

N1—C2—N3—C4

C2—N3—C4—N41

C2—N3—C4—C5

N3—C4—C5—C51

N41—C4—C5—C51

N3—C4—C5—C6

N41—C4—C5—C6

C2—N1—C6—N61

C2—N1—C6—C5

C51—C5—C6—N1

C4—C5—C6—N1

C51—C5—C6—N61

C4—C5—C6—N61

N3—C4—N41—C42

C5—C4—N41—C42

C4—N41—C42—C43

N41—C42—C43—O43

177.1 (2)

−4.5 (3)

N41—C42—C43—N44

C4—C5—C51—O51

C6—C5—C51—O51

N1—C6—N61—C61

C5—C6—N61—C61

N1—C6—N61—C67

C5—C6—N61—C67

C6—N61—C61—C66

C67—N61—C61—C66

C6—N61—C61—C62

C67—N61—C61—C62

C66—C61—C62—C63

N61—C61—C62—C63

C61—C62—C63—C64

C62—C63—C64—C65

C63—C64—C65—C66

C64—C65—C66—C61

C62—C61—C66—C65

N61—C61—C66—C65

1.3 (3)

8.3 (4)

−175.1 (2)

6.4 (3)

−179.4 (2)

−146.9 (2)

35.4 (3)

1.9 (3)

177.8 (2)

−0.8 (3)

167.3 (2)

−11.3 (3)

−5.7 (3)

−175.8 (2)

−137.5 (2)

72.2 (3)

46.9 (3)

−103.4 (2)

−1.1 (3)

174.5 (2)

−0.1 (3)

1.5 (4)

175.8 (2)

179.15 (19)

−3.2 (3)

−165.2 (2)

7.7 (3)

12.4 (3)

−174.8 (2)

7.0 (3)

−1.6 (4)

0.4 (3)

−174.3 (2)

−88.6 (3)

−179.29 (19)

1.0 (3)

−174.65 (19)

Acta Cryst. (2013). C69, 162-171

sup-8

supplementary materials

Hydrogen-bond geometry (Å, º)

D—H···A

D—H

H···A

D···A

D—H···A

N21—H21A···O43ⁱ

N41—H41···O51

N44—H44A···O51ⁱⁱ

N44—H44B···O43ⁱⁱⁱ

C62—H62···O43^iv

0.94

0.90

0.95

0.98

0.95

2.02

1.98

2.14

2.05

2.45

2.933 (2)

2.689 (2)

2.949 (2)

3.006 (3)

3.280 (3)

166

135

143

164

146

Symmetry codes: (i) x, y+1, z; (ii) −x+1, y, −z+1/2; (iii) −x+3/2, −y+1/2, −z+1; (iv) −x+1, −y+1, −z+1.

(III) Ethyl 3-amino-N-{2-amino-5-formyl-6-[methyl(phenyl)amino]pyrimidin- 4-yl}propionate

Crystal data

C₁₇H₂₁N₅O₃

M_r= 343.39

F(000) = 1456

D_x= 1.340 Mg m⁻³

Mo Kα radiation, λ = 0.71073 Å

Cell parameters from 3916 reflections

θ = 2.7–27.5°

Monoclinic, C2/c

Hall symbol: -C 2yc

a = 16.707 (6) Å

b = 10.218 (2) Å

c = 20.733 (5) Å

β = 105.929 (19)°

V = 3403.5 (16) Å³

Z = 8

µ = 0.10 mm⁻¹

T = 120 K

Plate, colourless

0.29 × 0.22 × 0.10 mm

Data collection

Bruker Nonius KappaCCD area-detector

diffractometer

Radiation source: Bruker Nonius FR591

rotating anode

Graphite monochromator

Detector resolution: 9.091 pixels mm^-1

φ and ω scans

Absorption correction: multi-scan

(SADABS; Sheldrick, 2003)

T_min= 0.973, T_max= 0.991

21914 measured reflections

3160 independent reflections

2239 reflections with I > 2σ(I)

R_int= 0.063

θ

_max= 25.5°, θ_min= 2.7°

h = −20→20

k = −12→12

l = −25→25

Refinement

Refinement on F²

Least-squares matrix: full

R[F²> 2σ(F²)] = 0.044

wR(F²) = 0.095

Secondary atom site location: difference Fourier

map

Hydrogen site location: inferred from

neighbouring sites

S = 1.09

3160 reflections

228 parameters

0 restraints

Primary atom site location: structure-invariant

direct methods

H-atom parameters constrained

w = 1/[σ²(F_o²) + (0.0345P)²+ 2.178P]

where P = (F_o²+ 2F_c²)/3

(Δ/σ)_max= 0.001

Δρ_max= 0.17 e Å⁻³

Δρ_min= −0.23 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

x

y

z

U_iso*/U_eq

N1

C2

N3

C4

0.40872 (10)

0.46275 (11)

0.44497 (9)

0.36591 (11)

0.17214 (14)

0.23317 (17)

0.28871 (14)

0.27637 (17)

0.28821 (7)

0.34084 (8)

0.39387 (7)

0.39697 (8)

0.0177 (3)

0.0168 (4)

0.0171 (3)

0.0163 (4)

Acta Cryst. (2013). C69, 162-171

sup-9

supplementary materials

C5

0.30520 (11)

0.33077 (12)

0.54146 (9)

0.5558

0.20093 (17)

0.15698 (17)

0.24174 (15)

0.2094

0.34921 (9)

0.29255 (9)

0.33734 (7)

0.3016

0.0174 (4)

0.0177 (4)

0.0222 (4)

0.027*

C6

N21

H21A

H21B

N41

0.5819

0.2860

0.3731

0.027*

0.34415 (10)

0.2882

0.33671 (15)

0.3264

0.44718 (7)

0.4506

0.0200 (4)

0.024*

H41

C42

0.39948 (12)

0.4561

0.42037 (18)

0.4159

0.49688 (9)

0.4908

0.0219 (4)

0.026*

H42A

H42B

C43

0.4024

0.3869

0.5423

0.026*

0.37086 (12)

0.4176

0.56410 (18)

0.6195

0.49202 (9)

0.5174

0.0238 (5)

0.029*

H43A

H43B

C44

0.3565

0.5919

0.4445

0.029*

0.29701 (12)

0.29875 (9)

0.22837 (8)

0.15224 (12)

0.1341

0.58623 (18)

0.64666 (14)

0.52993 (13)

0.5431 (2)

0.6357

0.51876 (9)

0.56953 (7)

0.48012 (6)

0.50101 (10)

0.4983

0.0224 (4)

0.0312 (4)

0.0233 (3)

0.0268 (5)

0.032*

O44

O45

C46

H46A

H46B

C47

0.1612

0.5124

0.5477

0.032*

0.08790 (13)

0.0789

0.4597 (2)

0.4926

0.45338 (10)

0.4075

0.0309 (5)

0.046*

H47A

H47B

H47C

C51

0.0355

0.4633

0.4659

0.046*

0.1075

0.3690

0.4557

0.046*

0.22888 (12)

0.1971

0.16081 (18)

0.0960

0.36199 (9)

0.3332

0.0223 (4)

0.027*

H51

O51

0.20072 (8)

0.27576 (10)

0.30784 (13)

0.3126

0.20319 (13)

0.09496 (14)

0.0352 (2)

0.1025

0.40731 (6)

0.23933 (7)

0.18652 (9)

0.1541

0.0281 (3)

0.0198 (4)

0.0259 (5)

0.039*

N61

C67

H67A

H67B

H67C

C61

0.2695

−0.0333

0.1636

0.039*

0.3627

−0.0032

0.2069

0.039*

0.19051 (12)

0.17252 (13)

0.2162

0.13782 (18)

0.2689 (2)

0.3310

0.21516 (9)

0.19992 (10)

0.2059

0.0208 (4)

0.0298 (5)

0.036*

C62

H62

C63

0.09012 (14)

0.0776

0.3083 (2)

0.3980

0.17591 (11)

0.1660

0.0379 (6)

0.045*

H63

C64

0.02607 (14)

−0.0302

0.2183 (2)

0.2461

0.16628 (10)

0.1505

0.0332 (5)

0.040*

H64

C65

0.04448 (13)

0.0008

0.0876 (2)

0.0251

0.17972 (10)

0.1723

0.0286 (5)

0.034*

H65

C66

0.12634 (13)

0.1386

0.04734 (19)

−0.0427

0.20402 (9)

0.2131

0.0243 (5)

0.029*

H66

Atomic displacement parameters (Å²)

U¹¹

U²²

U³³

U¹²

U¹³

U²³

N1

C2

N3

C4

0.0166 (9)

0.0157 (11)

0.0158 (9)

0.0173 (10)

0.0197 (8)

0.0172 (9)

0.0198 (8)

0.0153 (9)

0.0161 (8)

0.0165 (9)

0.0158 (8)

0.0161 (9)

−0.0019 (7)

0.0023 (8)

0.0005 (7)

0.0016 (8)

0.0032 (7)

0.0027 (8)

0.0042 (7)

0.0043 (8)

−0.0008 (6)

0.0029 (8)

−0.0007 (6)

0.0035 (8)

Acta Cryst. (2013). C69, 162-171

sup-10

supplementary materials

C5

0.0177 (11)

0.0191 (11)

0.0154 (9)

0.0169 (9)

0.0162 (11)

0.0206 (11)

0.0229 (12)

0.0261 (9)

0.0171 (8)

0.0200 (12)

0.0220 (12)

0.0227 (11)

0.0227 (8)

0.0194 (9)

0.0253 (12)

0.0198 (11)

0.0275 (13)

0.0366 (14)

0.0252 (13)

0.0239 (12)

0.0256 (12)

0.0167 (9)

0.0137 (9)

0.0330 (9)

0.0256 (9)

0.0292 (11)

0.0264 (11)

0.0200 (10)

0.0387 (9)

0.0299 (7)

0.0330 (12)

0.0389 (12)

0.0246 (10)

0.0387 (8)

0.0221 (8)

0.0315 (11)

0.0251 (11)

0.0260 (11)

0.0264 (12)

0.0342 (13)

0.0310 (12)

0.0213 (10)

0.0174 (9)

0.0184 (9)

0.0185 (8)

0.0184 (8)

0.0200 (10)

0.0249 (10)

0.0229 (10)

0.0284 (8)

0.0231 (7)

0.0289 (11)

0.0325 (12)

0.0185 (10)

0.0256 (7)

0.0173 (8)

0.0216 (10)

0.0155 (9)

0.0290 (11)

0.0392 (13)

0.0325 (12)

0.0280 (11)

0.0243 (10)

−0.0010 (8)

−0.0012 (8)

0.0004 (8)

0.0040 (8)

0.0019 (8)

0.0050 (7)

0.0064 (7)

0.0047 (8)

0.0071 (9)

0.0039 (9)

0.0069 (6)

0.0057 (6)

0.0091 (9)

0.0088 (10)

0.0038 (9)

0.0114 (6)

0.0042 (7)

0.0075 (9)

0.0017 (8)

−0.0036 (9)

−0.0086 (11)

−0.0048 (10)

0.0022 (9)

0.0039 (9)

−0.0003 (7)

0.0016 (7)

C6

N21

N41

C42

C43

C44

O44

O45

C46

C47

C51

O51

N61

C67

C61

C62

C63

C64

C65

C66

−0.0074 (7)

−0.0059 (7)

−0.0071 (8)

−0.0073 (9)

−0.0021 (8)

−0.0152 (7)

−0.0063 (6)

−0.0043 (9)

−0.0035 (10)

−0.0016 (8)

−0.0071 (6)

−0.0050 (7)

−0.0091 (9)

−0.0023 (8)

−0.0001 (9)

0.0008 (10)

−0.0041 (10)

−0.0057 (9)

−0.0044 (8)

−0.0036 (7)

−0.0025 (9)

−0.0054 (9)

−0.0003 (9)

−0.0022 (7)

−0.0034 (6)

0.0026 (10)

−0.0034 (10)

−0.0053 (9)

−0.0064 (7)

−0.0024 (7)

−0.0059 (10)

−0.0030 (9)

−0.0064 (10)

0.0024 (11)

0.0044 (11)

−0.0068 (10)

−0.0031 (9)

Geometric parameters (Å, º)

N1—C6

1.339 (2)

C46—H46A

C46—H46B

C47—H47A

C47—H47B

C47—H47C

C51—O51

C51—H51

N61—C61

N61—C67

C67—H67A

C67—H67B

C67—H67C

C61—C66

C61—C62

C62—C63

C62—H62

C63—C64

C63—H63

C64—C65

C64—H64

C65—C66

C65—H65

C66—H66

0.9900

N1—C2

1.361 (2)

1.340 (2)

1.341 (2)

1.346 (2)

1.343 (2)

1.433 (2)

1.428 (2)

1.432 (3)

1.381 (2)

0.9013

0.9900

C2—N21

C2—N3

0.9800

N3—C4

0.9800

C4—N41

C4—C5

1.239 (2)

0.9500

C5—C6

1.442 (2)

1.477 (2)

0.9800

C5—C51

C6—N61

N21—H21A

N21—H21B

N41—C42

N41—H41

C42—C43

C42—H42A

C42—H42B

C43—C44

C43—H43A

C43—H43B

C44—O44

C44—O45

O45—C46

C46—C47

0.9800

0.9681

0.9800

1.458 (2)

0.9621

1.386 (3)

1.390 (3)

1.389 (3)

0.9500

1.539 (3)

0.9900

1.384 (3)

0.9500

1.502 (3)

0.9900

1.381 (3)

0.9500

0.9900

1.214 (2)

1.336 (2)

1.458 (2)

1.508 (3)

1.384 (3)

0.9500

C6—N1—C2

116.26 (15)

O45—C46—H46B

110.5

Acta Cryst. (2013). C69, 162-171

sup-11

supplementary materials

N21—C2—N3

117.27 (16)

115.56 (15)

127.13 (17)

116.14 (15)

118.17 (16)

119.46 (16)

122.37 (16)

123.02 (17)

115.02 (16)

121.59 (16)

116.47 (16)

122.34 (17)

121.18 (17)

120.5

C47—C46—H46B

110.5

N21—C2—N1

H46A—C46—H46B

C46—C47—H47A

C46—C47—H47B

H47A—C47—H47B

C46—C47—H47C

H47A—C47—H47C

H47B—C47—H47C

O51—C51—C5

108.7

N3—C2—N1

109.5

C2—N3—C4

109.5

N41—C4—N3

109.5

N41—C4—C5

109.5

N3—C4—C5

109.5

C6—C5—C51

109.5

C6—C5—C4

125.68 (18)

117.2

C51—C5—C4

O51—C51—H51

C5—C51—H51

N1—C6—N61

117.2

N1—C6—C5

C6—N61—C61

121.03 (15)

119.00 (16)

113.12 (15)

109.5

N61—C6—C5

C6—N61—C67

C2—N21—H21A

C2—N21—H21B

H21A—N21—H21B

C4—N41—C42

C4—N41—H41

C42—N41—H41

N41—C42—C43

N41—C42—H42A

C43—C42—H42A

N41—C42—H42B

C43—C42—H42B

H42A—C42—H42B

C44—C43—C42

C44—C43—H43A

C42—C43—H43A

C44—C43—H43B

C42—C43—H43B

H43A—C43—H43B

O44—C44—O45

O44—C44—C43

O45—C44—C43

C44—O45—C46

O45—C46—C47

O45—C46—H46A

C47—C46—H46A

C61—N61—C67

N61—C67—H67A

N61—C67—H67B

H67A—C67—H67B

N61—C67—H67C

H67A—C67—H67C

H67B—C67—H67C

C66—C61—C62

C66—C61—N61

C62—C61—N61

C63—C62—C61

C63—C62—H62

C61—C62—H62

C64—C63—C62

C64—C63—H63

C62—C63—H63

C65—C64—C63

C65—C64—H64

C63—C64—H64

C64—C65—C66

C64—C65—H65

C66—C65—H65

C65—C66—C61

C65—C66—H66

C61—C66—H66

118.6

120.9

109.5

124.28 (16)

118.8

109.5

116.9

109.5

112.82 (16)

109.0

109.5

119.71 (19)

120.02 (17)

120.20 (17)

119.50 (19)

120.2

109.0

107.8

113.03 (16)

109.0

120.2

120.7 (2)

119.7

109.0

119.7

109.0

119.5 (2)

120.2

107.8

123.48 (18)

124.76 (18)

111.76 (16)

117.21 (14)

106.03 (15)

110.5

120.2

120.27 (19)

119.9

120.27 (19)

119.9

110.5

119.9

C6—N1—C2—N21

C6—N1—C2—N3

N21—C2—N3—C4

N1—C2—N3—C4

C2—N3—C4—N41

C2—N3—C4—C5

N41—C4—C5—C6

N3—C4—C5—C6

N41—C4—C5—C51

N3—C4—C5—C51

176.77 (15)

−5.7 (3)

O44—C44—O45—C46

C43—C44—O45—C46

C44—O45—C46—C47

C6—C5—C51—O51

C4—C5—C51—O51

N1—C6—N61—C61

C5—C6—N61—C61

N1—C6—N61—C67

C5—C6—N61—C67

C6—N61—C61—C66

0.0 (3)

179.43 (16)

−174.16 (16)

−174.25 (18)

13.2 (3)

−178.63 (15)

3.8 (3)

−176.31 (15)

4.2 (2)

−141.21 (17)

39.4 (2)

171.17 (16)

−9.3 (2)

7.8 (2)

−15.7 (3)

163.79 (17)

−171.57 (16)

−131.94 (18)

Acta Cryst. (2013). C69, 162-171

sup-12

supplementary materials

C2—N1—C6—N61

C2—N1—C6—C5

−179.91 (15)

−0.5 (2)

C67—N61—C61—C66

77.4 (2)

51.1 (2)

−99.6 (2)

2.3 (3)

C6—N61—C61—C62

C67—N61—C61—C62

C66—C61—C62—C63

N61—C61—C62—C63

C61—C62—C63—C64

C62—C63—C64—C65

C63—C64—C65—C66

C64—C65—C66—C61

C62—C61—C66—C65

N61—C61—C66—C65

C51—C5—C6—N1

C4—C5—C6—N1

−165.64 (17)

7.4 (2)

C51—C5—C6—N61

C4—C5—C6—N61

N3—C4—N41—C42

C5—C4—N41—C42

C4—N41—C42—C43

N41—C42—C43—C44

C42—C43—C44—O44

C42—C43—C44—O45

13.7 (3)

179.22 (17)

−0.8 (3)

−1.0 (3)

1.4 (3)

−173.28 (16)

3.2 (3)

−177.28 (16)

114.35 (19)

74.4 (2)

0.1 (3)

−1.9 (3)

−178.87 (16)

111.1 (2)

−68.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A

D—H

H···A

D···A

D—H···A

N21—H21A···N1ⁱ

N21—H21B···O44ⁱⁱ

N41—H41···O51

0.90

0.97

0.96

2.14

1.95

3.027 (2)

3.054 (2)

2.683 (2)

169

158

131

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1, −y+1, −z+1.

(IV) Methyl N-{2-amino-6-[benzyl(methyl)amino]-5-formylpyrimidin-4-yl}glycinate

Crystal data

C₁₆H₁₉N₅O₃

M_r= 329.36

F(000) = 696

D_x= 1.339 Mg m⁻³

Mo Kα radiation, λ = 0.71073 Å

Cell parameters from 3733 reflections

θ = 2.8–27.5°

Monoclinic, P2₁/c

Hall symbol: -P 2ybc

a = 15.636 (4) Å

b = 6.5674 (18) Å

c = 17.336 (5) Å

β = 113.440 (18)°

V = 1633.3 (8) Å³

Z = 4

µ = 0.10 mm⁻¹

T = 120 K

Block, colourless

0.29 × 0.27 × 0.15 mm

Data collection

Bruker Nonius KappaCCD area-detector

diffractometer

Radiation source: Bruker Nonius FR591

rotating anode

Graphite monochromator

Detector resolution: 9.091 pixels mm^-1

φ and ω scans

Absorption correction: multi-scan

(SADABS; Sheldrick, 2003)

T_min= 0.973, T_max= 0.986

21188 measured reflections

3013 independent reflections

2209 reflections with I > 2σ(I)

R_int= 0.072

θ

_max= 25.5°, θ_min= 2.8°

h = −18→18

k = −7→7

l = −20→20

Refinement

Refinement on F²

Least-squares matrix: full

R[F²> 2σ(F²)] = 0.059

wR(F²) = 0.165

219 parameters

0 restraints

Primary atom site location: structure-invariant

direct methods

S = 1.09

3013 reflections

Secondary atom site location: difference Fourier

map

Acta Cryst. (2013). C69, 162-171

sup-13

supplementary materials

Hydrogen site location: inferred from

neighbouring sites

H-atom parameters constrained

w = 1/[σ²(F_o²) + (0.0897P)²+ 1.0498P]

where P = (F_o²+ 2F_c²)/3

(Δ/σ)_max= 0.001

Δρ_max= 0.35 e Å⁻³

Δρ_min= −0.36 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

x

y

z

U_iso*/U_eq

N1

0.76191 (13)

0.82036 (15)

0.85110 (13)

0.83019 (15)

0.77674 (15)

0.73816 (16)

0.84767 (14)

0.8254

0.7943 (3)

0.6345 (4)

0.5052 (3)

0.5560 (4)

0.7337 (4)

0.8387 (4)

0.5969 (3)

0.6764

0.53404 (12)

0.56416 (14)

0.52088 (11)

0.44062 (13)

0.40234 (14)

0.45326 (14)

0.64650 (12)

0.6840

0.0198 (5)

0.0182 (5)

0.0186 (5)

0.0170 (5)

0.0191 (5)

0.0184 (5)

0.0227 (5)

0.027*

C2

N3

C4

C5

C6

N21

H21A

H21B

N41

H41

C42

H42A

H42B

C43

O43

O44

C45

H45A

H45B

H45C

C51

H51

O51

N61

C67

H67A

H67B

C61

C62

H62

C63

H63

C64

H64

C65

H65

C66

H66

C68

H68A

0.8675

0.4707

0.6640

0.027*

0.86339 (14)

0.8525

0.4372 (3)

0.4819

0.39645 (12)

0.3409

0.0216 (5)

0.026*

0.92283 (16)

0.8894

0.2643 (4)

0.1646

0.43330 (14)

0.4540

0.0206 (5)

0.025*

0.9793

0.3093

0.4816

0.025*

0.94983 (16)

0.91642 (11)

1.01581 (12)

1.04556 (18)

1.0646

0.1673 (4)

0.2078 (3)

0.0275 (3)

−0.0855 (4)

0.0098

0.36808 (14)

0.29407 (10)

0.40347 (10)

0.34677 (16)

0.3131

0.0193 (5)

0.0231 (4)

0.0258 (4)

0.0268 (6)

0.040*

0.9939

−0.1696

−0.1731

0.8161 (4)

0.9504

0.3095

0.040*

1.0983

0.3794

0.040*

0.77698 (15)

0.7535

0.32669 (14)

0.3121

0.0200 (5)

0.024*

0.80517 (12)

0.67418 (14)

0.59484 (17)

0.6164

0.7278 (3)

0.9937 (3)

0.9692 (4)

0.8947

0.27814 (10)

0.42083 (12)

0.33873 (15)

0.3001

0.0262 (4)

0.0220 (5)

0.0246 (6)

0.029*

0.5735

1.1055

0.3143

0.029*

0.51365 (17)

0.52537 (18)

0.5858

0.8562 (4)

0.6637 (4)

0.6047

0.34467 (15)

0.38099 (16)

0.4040

0.0221 (5)

0.0285 (6)

0.034*

0.45071 (19)

0.4601

0.5564 (5)

0.4251

0.38425 (17)

0.4093

0.0320 (6)

0.038*

0.36207 (18)

0.3106

0.6408 (5)

0.5678

0.35094 (17)

0.3531

0.0327 (7)

0.039*

0.34922 (18)

0.2886

0.8310 (5)

0.8891

0.31483 (18)

0.2919

0.0360 (7)

0.043*

0.42394 (17)

0.4140

0.9384 (5)

1.0698

0.31163 (16)

0.2866

0.0292 (6)

0.035*

0.65143 (18)

0.7090

1.1154 (4)

1.1536

0.48056 (16)

0.5280

0.0283 (6)

0.042*

Acta Cryst. (2013). C69, 162-171

sup-14

supplementary materials

H68B

H68C

0.6119

0.6181

1.0356

1.2386

0.5012

0.4526

0.042*

Atomic displacement parameters (Å²)

U¹¹

U²²

U³³

U¹²

U¹³

U²³

N1

0.0178 (10)

0.0139 (11)

0.0181 (10)

0.0122 (11)

0.0132 (11)

0.0156 (11)

0.0268 (11)

0.0231 (11)

0.0201 (12)

0.0191 (12)

0.0254 (9)

0.0224 (11)

0.0219 (13)

0.0218 (11)

0.0216 (13)

0.0233 (13)

0.0196 (13)

0.0249 (12)

0.0256 (12)

0.0231 (13)

0.0175 (13)

0.0269 (10)

0.0291 (10)

0.0291 (15)

0.0251 (14)

0.0332 (11)

0.0239 (12)

0.0276 (15)

0.0270 (14)

0.0313 (16)

0.0346 (16)

0.0464 (19)

0.054 (2)

0.0180 (10)

0.0185 (11)

0.0152 (10)

0.0153 (11)

0.0187 (11)

0.0186 (11)

0.0166 (10)

0.0156 (9)

0.0168 (11)

0.0206 (12)

0.0166 (8)

0.0190 (8)

0.0238 (12)

0.0194 (11)

0.0195 (8)

0.0202 (10)

0.0210 (12)

0.0164 (11)

0.0293 (13)

0.0292 (13)

0.0289 (14)

0.0329 (15)

0.0267 (13)

0.0286 (13)

0.0019 (8)

0.0059 (8)

0.0062 (9)

0.0061 (8)

0.0037 (9)

0.0043 (9)

0.0052 (9)

0.0090 (8)

0.0071 (8)

0.0052 (9)

0.0072 (10)

0.0079 (7)

0.0102 (11)

0.0031 (9)

0.0121 (7)

0.0037 (8)

0.0039 (10)

0.0040 (9)

0.0054 (11)

0.0078 (11)

0.0111 (11)

0.0051 (11)

0.0057 (11)

0.0061 (11)

0.0006 (8)

C2

−0.0020 (10)

0.0001 (8)

−0.0016 (10)

−0.0007 (8)

−0.0005 (9)

0.0004 (10)

−0.0009 (9)

0.0016 (8)

N3

C4

−0.0016 (9)

−0.0012 (10)

−0.0025 (9)

0.0053 (9)

C5

C6

N21

N41

C42

C43

O43

O44

C45

C51

O51

N61

C67

C61

C62

C63

C64

C65

C66

C68

0.0056 (9)

0.0023 (8)

0.0016 (10)

−0.0016 (10)

0.0016 (7)

−0.0011 (10)

−0.0007 (9)

−0.0002 (7)

0.0003 (7)

0.0280 (10)

0.0275 (13)

0.0125 (11)

0.0284 (10)

0.0182 (10)

0.0209 (13)

0.0199 (12)

0.0206 (13)

0.0286 (14)

0.0235 (14)

0.0167 (13)

0.0227 (13)

0.0239 (13)

0.0097 (8)

0.0077 (11)

0.0003 (10)

0.0013 (8)

−0.0031 (11)

0.0021 (10)

0.0041 (8)

0.0030 (9)

−0.0002 (8)

0.0057 (10)

−0.0020 (10)

0.0013 (12)

−0.0005 (12)

−0.0123 (13)

−0.0084 (14)

0.0017 (11)

−0.0033 (11)

0.0059 (11)

0.0012 (10)

0.0005 (11)

−0.0062 (12)

−0.0103 (13)

0.0023 (12)

0.0076 (11)

0.0077 (11)

0.0344 (16)

0.0282 (15)

Geometric parameters (Å, º)

N1—C6

1.331 (3)

C45—H45C

0.9800

N1—C2

1.353 (3)

1.340 (3)

1.342 (3)

1.339 (3)

1.334 (3)

1.436 (3)

1.420 (3)

1.429 (3)

1.381 (3)

0.9984

C51—O51

C51—H51

N61—C68

N61—C67

C67—C61

C67—H67A

C67—H67B

C61—C62

C61—C66

C62—C63

C62—H62

C63—C64

C63—H63

C64—C65

C64—H64

C65—C66

1.239 (3)

0.9500

C2—N21

C2—N3

1.459 (3)

1.479 (3)

1.509 (4)

0.9900

N3—C4

C4—N41

C4—C5

C5—C51

C5—C6

0.9900

1.392 (4)

1.396 (4)

1.383 (4)

0.9500

C6—N61

N21—H21A

N21—H21B

N41—C42

N41—H41

C42—C43

C42—H42A

C42—H42B

0.8951

1.445 (3)

0.9547

1.387 (4)

0.9500

1.497 (3)

0.9900

1.376 (5)

0.9500

0.9900

1.385 (4)

Acta Cryst. (2013). C69, 162-171

sup-15

supplementary materials

C43—O43

C43—O44

O44—C45

C45—H45A

C45—H45B

1.207 (3)

1.334 (3)

1.448 (3)

0.9800

C65—H65

C66—H66

C68—H68A

C68—H68B

C68—H68C

0.9500

0.9800

C6—N1—C2

116.0 (2)

116.5 (2)

115.7 (2)

127.8 (2)

115.4 (2)

117.4 (2)

119.9 (2)

122.7 (2)

122.9 (2)

121.5 (2)

114.7 (2)

116.3 (2)

122.3 (2)

121.3 (2)

123.5

O51—C51—C5

O51—C51—H51

C5—C51—H51

C6—N61—C68

C6—N61—C67

C68—N61—C67

N61—C67—C61

N61—C67—H67A

C61—C67—H67A

N61—C67—H67B

C61—C67—H67B

125.5 (2)

117.2

N21—C2—N3

N21—C2—N1

117.2

N3—C2—N1

117.2 (2)

120.4 (2)

113.3 (2)

113.2 (2)

108.9

C4—N3—C2

N41—C4—N3

N41—C4—C5

N3—C4—C5

C51—C5—C6

108.9

C51—C5—C4

108.9

C6—C5—C4

108.9

N1—C6—N61

H67A—C67—H67B

C62—C61—C66

C62—C61—C67

C66—C61—C67

C63—C62—C61

C63—C62—H62

C61—C62—H62

C62—C63—C64

C62—C63—H63

C64—C63—H63

C65—C64—C63

C65—C64—H64

C63—C64—H64

C64—C65—C66

C64—C65—H65

C66—C65—H65

C65—C66—C61

C65—C66—H66

C61—C66—H66

N61—C68—H68A

N61—C68—H68B

H68A—C68—H68B

N61—C68—H68C

H68A—C68—H68C

H68B—C68—H68C

107.7

N1—C6—C5

117.8 (2)

121.0 (2)

121.1 (2)

121.3 (3)

119.3

N61—C6—C5

C2—N21—H21A

C2—N21—H21B

H21A—N21—H21B

C4—N41—C42

C4—N41—H41

C42—N41—H41

N41—C42—C43

N41—C42—H42A

C43—C42—H42A

N41—C42—H42B

C43—C42—H42B

H42A—C42—H42B

O43—C43—O44

O43—C43—C42

O44—C43—C42

C43—O44—C45

O44—C45—H45A

O44—C45—H45B

H45A—C45—H45B

O44—C45—H45C

H45A—C45—H45C

H45B—C45—H45C

116.9

115.2

122.29 (19)

116.4

119.3

119.9 (3)

120.0

120.8

108.99 (18)

109.9

120.0

119.5 (3)

120.2

109.9

120.2

109.9

120.5 (3)

119.7

108.3

124.7 (2)

125.2 (2)

110.13 (19)

116.03 (18)

109.5

119.7

120.8 (3)

119.6

109.5

C6—N1—C2—N21

C6—N1—C2—N3

N21—C2—N3—C4

N1—C2—N3—C4

C2—N3—C4—N41

C2—N3—C4—C5

176.8 (2)

−6.0 (4)

−174.1 (2)

8.8 (4)

O43—C43—O44—C45

C42—C43—O44—C45

C6—C5—C51—O51

C4—C5—C51—O51

N1—C6—N61—C68

C5—C6—N61—C68

−2.2 (4)

177.2 (2)

−176.2 (2)

15.3 (4)

176.7 (2)

−1.4 (3)

10.2 (3)

−169.3 (2)

Acta Cryst. (2013). C69, 162-171

sup-16

supplementary materials

N41—C4—C5—C51

N3—C4—C5—C51

N41—C4—C5—C6

N3—C4—C5—C6

−15.8 (3)

162.2 (2)

174.8 (2)

−7.2 (3)

N1—C6—N61—C67

−134.4 (2)

46.0 (3)

83.0 (3)

−63.0 (3)

−55.3 (3)

126.7 (2)

0.1 (4)

C5—C6—N61—C67

C6—N61—C67—C61

C68—N61—C67—C61

N61—C67—C61—C62

N61—C67—C61—C66

C66—C61—C62—C63

C67—C61—C62—C63

C61—C62—C63—C64

C62—C63—C64—C65

C63—C64—C65—C66

C64—C65—C66—C61

C62—C61—C66—C65

C67—C61—C66—C65

C2—N1—C6—N61

C2—N1—C6—C5

176.2 (2)

−4.2 (3)

C51—C5—C6—N1

C4—C5—C6—N1

−159.1 (2)

10.1 (3)

−177.9 (2)

−0.1 (4)

0.0 (4)

C51—C5—C6—N61

C4—C5—C6—N61

N3—C4—N41—C42

C5—C4—N41—C42

C4—N41—C42—C43

N41—C42—C43—O43

N41—C42—C43—O44

20.4 (4)

−170.3 (2)

−2.4 (3)

−0.1 (4)

0.2 (4)

175.7 (2)

−178.5 (2)

−10.1 (3)

170.47 (19)

−0.2 (4)

177.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A

D—H

H···A

D···A

D—H···A

N21—H21A···O51ⁱ

N21—H21B···O43ⁱⁱ

N41—H41···O51

1.00

0.89

0.96

1.89

2.38

1.92

2.860 (3)

3.085 (3)

2.682 (3)

163

136

135

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+1/2, z+1/2.

(V) Ethyl 3-amino-N-{2-amino-6-[benzyl(methyl)amino]-5-formylpyrimidin- 4-yl}propionate

Crystal data

C₁₈H₂₃N₅O₃

M_r= 357.41

F(000) = 1520

D_x= 1.355 Mg m⁻³

Mo Kα radiation, λ = 0.71073 Å

Cell parameters from 4039 reflections

θ = 3.0–27.5°

Monoclinic, C2/c

Hall symbol: -C 2yc

a = 24.8226 (5) Å

b = 7.1379 (14) Å

c = 20.601 (2) Å

β = 106.213 (8)°

V = 3505.0 (8) Å³

Z = 8

µ = 0.10 mm⁻¹

T = 120 K

Block, colourless

0.26 × 0.21 × 0.14 mm

Data collection

Bruker Nonius KappaCCD area-detector

diffractometer

Radiation source: Bruker Nonius FR591

rotating anode

Graphite monochromator

Detector resolution: 9.091 pixels mm^-1

φ and ω scans

Absorption correction: multi-scan

(SADABS; Sheldrick, 2003)

T_min= 0.976, T_max= 0.987

22384 measured reflections

3269 independent reflections

2276 reflections with I > 2σ(I)

R_int= 0.073

θ

_max= 25.5°, θ_min= 3.0°

h = −30→30

k = −8→8

l = −24→24

Acta Cryst. (2013). C69, 162-171

sup-17

supplementary materials

Refinement

Refinement on F²

Least-squares matrix: full

R[F²> 2σ(F²)] = 0.045

wR(F²) = 0.104

Secondary atom site location: difference Fourier

map

Hydrogen site location: inferred from

neighbouring sites

S = 1.06

3269 reflections

237 parameters

0 restraints

Primary atom site location: structure-invariant

direct methods

H-atom parameters constrained

w = 1/[σ²(F_o²) + (0.039P)²+ 2.9368P]

where P = (F_o²+ 2F_c²)/3

(Δ/σ)_max= 0.001

Δρ_max= 0.21 e Å⁻³

Δρ_min= −0.25 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

x

y

z

U_iso*/U_eq

N1

0.69278 (6)

0.70537 (8)

0.67234 (6)

0.62542 (8)

0.61274 (8)

0.64576 (8)

0.75599 (6)

0.7798

0.7477 (2)

0.6127 (3)

0.4705 (2)

0.4445 (3)

0.5559 (3)

0.7221 (3)

0.6237 (2)

0.7296

0.66478 (8)

0.71219 (10)

0.72058 (8)

0.66962 (10)

0.60889 (10)

0.61344 (9)

0.75782 (8)

0.7585

0.0163 (4)

0.0154 (4)

0.0166 (4)

0.0159 (4)

0.0169 (4)

0.0157 (4)

0.0188 (4)

0.023*

C2

N3

C4

C5

C6

N21

H21A

H21B

N41

H41

C42

0.7679

0.5267

0.7903

0.023*

0.59084 (7)

0.5572

0.3046 (2)

0.2751

0.67526 (8)

0.6363

0.0200 (4)

0.024*

0.59488 (8)

0.5670

0.1981 (3)

0.2466

0.73683 (10)

0.7588

0.0202 (5)

0.024*

H42A

H42B

C43

0.6326

0.2161

0.7685

0.024*

0.58472 (8)

0.6123

−0.0093 (3)

−0.0571

0.72265 (10)

0.7001

0.0202 (5)

0.024*

H43A

H43B

C44

0.5907

−0.0769

0.7660

0.024*

0.52655 (8)

0.49263 (6)

0.51667 (6)

0.46236 (9)

0.4650

−0.0493 (3)

0.0690 (2)

−0.23223 (19)

−0.2905 (3)

−0.3114

0.67878 (10)

0.65309 (9)

0.67155 (7)

0.62757 (11)

0.5810

0.0191 (5)

0.0387 (4)

0.0267 (4)

0.0288 (5)

0.035*

O44

O45

C46

H46A

H46B

C47

0.4339

−0.1924

0.6262

0.035*

0.44631 (9)

0.4763

−0.4687 (3)

−0.5613

0.65593 (12)

0.6606

0.0328 (6)

0.049*

H47A

H47B

H47C

C51

0.4115

−0.5174

0.6254

0.049*

0.4406

−0.4438

0.7003

0.049*

0.57391 (8)

0.5723

0.4903 (3)

0.5570

0.54831 (10)

0.5079

0.0210 (5)

0.025*

H51

O51

N61

C67

0.54207 (6)

0.63127 (6)

0.67035 (8)

0.7071

0.35380 (19)

0.8638 (2)

1.0176 (3)

0.9885

0.54367 (7)

0.56785 (8)

0.56761 (10)

0.5999

0.0249 (4)

0.0173 (4)

0.0199 (5)

0.024*

H67A

H67B

C61

0.6560

1.1337

0.5831

0.024*

0.67824 (8)

1.0504 (3)

0.49824 (10)

0.0197 (5)

Acta Cryst. (2013). C69, 162-171

sup-18

supplementary materials

C62

0.68991 (9)

0.6899

0.9001 (3)

0.7762

0.46137 (11)

0.4782

0.0258 (5)

0.031*

H62

C63

0.70159 (9)

0.7097

0.9299 (4)

0.8266

0.40034 (11)

0.3756

0.0333 (6)

0.040*

H63

C64

0.70148 (9)

0.7095

1.1090 (4)

1.1290

0.37540 (11)

0.3335

0.0343 (6)

0.041*

H64

C65

0.68969 (9)

0.6894

1.2590 (3)

1.3824

0.41123 (11)

0.3939

0.0318 (6)

0.038*

H65

C66

0.67813 (8)

0.6701

1.2301 (3)

1.3338

0.47289 (11)

0.4976

0.0243 (5)

0.029*

H66

C68

0.57405 (8)

0.5714

0.8987 (3)

0.8621

0.52501 (10)

0.4784

0.0215 (5)

0.032*

H68A

H68B

H68C

0.5653

1.0323

0.5264

0.032*

0.5474

0.8251

0.5417

0.032*

Atomic displacement parameters (Å²)

U¹¹

U²²

U³³

U¹²

U¹³

U²³

N1

0.0162 (8)

0.0154 (10)

0.0153 (8)

0.0151 (10)

0.0163 (10)

0.0164 (10)

0.0172 (9)

0.0197 (9)

0.0221 (11)

0.0194 (10)

0.0239 (11)

0.0252 (8)

0.0260 (8)

0.0284 (12)

0.0292 (12)

0.0218 (11)

0.0244 (8)

0.0167 (8)

0.0217 (10)

0.0138 (10)

0.0259 (11)

0.0277 (12)

0.0243 (12)

0.0211 (11)

0.0180 (10)

0.0193 (11)

0.0174 (9)

0.0149 (10)

0.0175 (9)

0.0141 (10)

0.0163 (10)

0.0174 (11)

0.0170 (9)

0.0184 (9)

0.0207 (11)

0.0214 (11)

0.0160 (11)

0.0215 (8)

0.0172 (8)

0.0281 (13)

0.0231 (13)

0.0167 (11)

0.0170 (8)

0.0172 (9)

0.0201 (11)

0.0246 (12)

0.0276 (13)

0.0487 (15)

0.0607 (18)

0.0412 (15)

0.0260 (12)

0.0190 (11)

0.0144 (9)

0.0005 (7)

0.0028 (7)

0.0042 (9)

0.0024 (7)

0.0054 (9)

0.0037 (8)

0.0064 (8)

−0.0008 (7)

0.0010 (7)

0.0057 (9)

0.0063 (9)

0.0092 (9)

−0.0059 (8)

0.0002 (7)

0.0018 (10)

0.0057 (11)

0.0017 (9)

−0.0040 (7)

0.0021 (7)

0.0032 (9)

0.0006 (8)

0.0069 (10)

0.0102 (10)

0.0076 (10)

0.0034 (10)

0.0040 (9)

0.0012 (9)

0.0001 (8)

−0.0031 (9)

0.0005 (7)

−0.0038 (9)

0.0007 (9)

−0.0017 (9)

0.0034 (8)

0.0029 (8)

0.0007 (9)

0.0022 (9)

0.0002 (9)

0.0012 (8)

0.0003 (7)

−0.0015 (11)

0.0028 (11)

0.0019 (10)

−0.0007 (7)

0.0032 (8)

−0.0006 (9)

0.0036 (10)

0.0003 (10)

−0.0055 (12)

0.0082 (12)

0.0187 (12)

0.0054 (10)

0.0023 (9)

C2

0.0159 (11)

0.0157 (9)

0.0190 (11)

0.0174 (10)

0.0147 (10)

0.0187 (9)

0.0192 (9)

0.0179 (11)

0.0201 (11)

0.0192 (11)

0.0587 (12)

0.0320 (9)

0.0265 (13)

0.0433 (15)

0.0217 (11)

0.0266 (9)

0.0164 (9)

0.0167 (11)

0.0184 (11)

0.0239 (12)

0.0252 (13)

0.0190 (12)

0.0309 (13)

0.0274 (12)

0.0234 (12)

0.0020 (8)

N3

0.0010 (7)

C4

0.0031 (8)

C5

0.0016 (8)

C6

0.0022 (8)

N21

N41

C42

C43

C44

O44

O45

C46

C47

C51

O51

N61

C67

C61

C62

C63

C64

C65

C66

C68

−0.0023 (7)

−0.0027 (7)

−0.0028 (9)

0.0007 (9)

−0.0015 (9)

0.0003 (7)

−0.0039 (6)

−0.0098 (10)

−0.0040 (10)

0.0049 (9)

−0.0045 (6)

−0.0020 (7)

−0.0035 (9)

−0.0025 (9)

0.0003 (10)

−0.0016 (11)

−0.0039 (12)

−0.0026 (11)

−0.0004 (9)

0.0011 (9)

Geometric parameters (Å, º)

N1—C2

N1—C6

C2—N21

1.346 (2)

C46—H46B

0.9900

1.351 (2)

1.345 (2)

C47—H47A

C47—H47B

0.9800

Acta Cryst. (2013). C69, 162-171

sup-19

supplementary materials

C2—N3

1.346 (2)

1.343 (2)

1.441 (3)

1.426 (3)

1.430 (3)

1.359 (2)

0.9568

C47—H47C

C51—O51

C51—H51

N61—C67

N61—C68

C67—C61

C67—H67A

C67—H67B

C61—C66

C61—C62

C62—C63

C62—H62

C63—C64

C63—H63

C64—C65

C64—H64

C65—C66

C65—H65

C66—H66

C68—H68A

C68—H68B

C68—H68C

0.9800

N3—C4

1.241 (2)

0.9500

C4—N41

C4—C5

1.466 (2)

1.469 (2)

1.514 (3)

0.9900

C5—C51

C5—C6

C6—N61

N21—H21A

N21—H21B

N41—C42

N41—H41

C42—C43

C42—H42A

C42—H42B

C43—C44

C43—H43A

C43—H43B

C44—O44

C44—O45

O45—C46

C46—C47

C46—H46A

0.9900

0.9506

1.384 (3)

1.391 (3)

1.383 (3)

0.9500

1.458 (2)

1.0067

1.516 (3)

0.9900

1.377 (3)

0.9500

0.9900

1.501 (3)

0.9900

1.378 (3)

0.9500

0.9900

1.394 (3)

0.9500

1.205 (2)

1.330 (2)

1.459 (2)

1.499 (3)

0.9900

0.9500

0.9800

C2—N1—C6

116.49 (16)

116.59 (17)

115.99 (17)

127.38 (17)

115.43 (16)

118.03 (17)

119.71 (17)

122.21 (17)

124.40 (18)

120.58 (18)

114.74 (17)

116.39 (17)

121.19 (17)

122.41 (17)

120.6

C46—C47—H47A

C46—C47—H47B

109.5

N21—C2—N1

N21—C2—N3

N1—C2—N3

H47A—C47—H47B

C46—C47—H47C

H47A—C47—H47C

H47B—C47—H47C

O51—C51—C5

109.5

C4—N3—C2

109.5

N41—C4—N3

N41—C4—C5

N3—C4—C5

109.5

125.83 (19)

117.1

O51—C51—H51

C5—C51—H51

C51—C5—C6

117.1

C51—C5—C4

C6—N61—C67

120.81 (16)

124.49 (16)

113.63 (15)

112.29 (16)

109.1

C6—C5—C4

C6—N61—C68

N1—C6—N61

N1—C6—C5

C67—N61—C68

N61—C67—C61

N61—C67—H67A

C61—C67—H67A

N61—C67—H67B

C61—C67—H67B

H67A—C67—H67B

C66—C61—C62

C66—C61—C67

C62—C61—C67

C63—C62—C61

C63—C62—H62

C61—C62—H62

C64—C63—C62

C64—C63—H63

N61—C6—C5

C2—N21—H21A

C2—N21—H21B

H21A—N21—H21B

C4—N41—C42

C4—N41—H41

C42—N41—H41

N41—C42—C43

N41—C42—H42A

C43—C42—H42A

N41—C42—H42B

C43—C42—H42B

H42A—C42—H42B

109.1

119.7

109.1

119.8

109.1

124.93 (17)

119.7

107.9

119.17 (19)

120.82 (19)

119.84 (18)

120.4 (2)

119.8

115.2

111.95 (16)

109.2

119.8

109.2

120.2 (2)

119.9

107.9

Acta Cryst. (2013). C69, 162-171

sup-20

Article Doi

Six closely related 4,6-disubstituted 2-amino-5-formylpyrimidines: Different ring conformations, polarized electronic structures, and hydrogen-bonded assembly in zero, one, two and three dimensions

DOI: 10.1107/S0108270112051049

Source and publish data:

Authors:

Article abstract of DOI:10.1107/S0108270112051049

Full text of DOI:10.1107/S0108270112051049

Products guided by the article

R&D Labs maybe for 1431987-96-0

Relevant to this article

Hot Product