Dibenzylammonium hydrogen maleate and a redetermination at 120K of bis(dibenzylamino)methane

Article abstract of DOI:10.1107/S010827011301651X

In dibenzylammonium hydrogen maleate [or dibenzylammonium (2Z)-3-carboxyprop-2-enoate], C₁₄H₁₆N⁺· C₄H₃O₄ ^-, (I), the anion contains a fairly short and nearly linear O - H...O hyd

Full text of DOI:10.1107/S010827011301651X

organic compounds
Acta Crystallographica Section C
Crystal Structure
amines and using a four-component strategy mediated by a
´
Mannich-type reaction (Abonıa et al., 2013). In order to
Communications
confirm the role of (II) in this route, it has been prepared from
the reaction of dibenzylamine with paraformaldehyde in
acetonitrile and then used to obtain the ꢀ-aminoethers, thus
confirming its intermediacy. As a model for the crystallization
and characterization of new secondary benzylamine deriva-
tives needed in this synthetic route we have prepared and
crystallized the dibenzylammonium hydrogen maleate salt,
(I).
ISSN 0108-2701
Dibenzylammonium hydrogen
maleate and a redetermination at
120 K of bis(dibenzylamino)methane
a
a
b
´
Juan C. Castillo, Rodrigo Abonıa, Justo Cobo and
Christopher Glidewellc*
a
´
Departamento de Quımica, Universidad de Valle, AA 25360 Cali, Colombia,
b
´
´
´
´
Departamento de Quımica Inorganica y Organica, Universidad de Jaen, 23071
Jaen, Spain, and cSchool of Chemistry, University of St Andrews, Fife KY16 9ST,
´
Scotland
Correspondence e-mail: cg@st-andrews.ac.uk
Received 28 May 2013
Accepted 13 June 2013
In dibenzylammonium hydrogen maleate [or dibenzylam-
ꢁ
monium (2Z)-3-carboxyprop-2-enoate], C14H16N+ꢀC4H3O4
,
(I), the anion contains a fairly short and nearly linear O—
Hꢀ ꢀ ꢀO hydrogen bond, with an Oꢀ ꢀ ꢀꢀO distance of
˚
2.4603 (16) A, but with the H atom clearly offset from the
mid-point of the Oꢀ ꢀ ꢀO vector. The counter-ions in (I) are
linked by two N—Hꢀ ꢀ ꢀO hydrogen bonds to form C22(6) chains
and these chains are weakly linked into sheets by a C—Hꢀ ꢀ ꢀO
hydrogen bond. Bis(dibenzylamino)methane, C29H30N2, (II),
crystallizes with two independent molecules lying across
twofold rotation axes in the space group C2/c, and the
molecules are conformationally chiral; there are no direction-
specific intermolecular interactions in the crystal structure
of (II).
The structure of compound (II) has been reported
previously using diffraction data collected at 298 K
[Cambridge Structural Database (CSD; Allen, 2002) refcode
MIKQON (Lu et al., 2007)], but the refinement converged to a
rather high R1 value of 0.0794, while the value of wR2 was also
quoted as 0.0794, suggesting that unweighted data were used
Comment
We report here the molecular and supramolecular structures
of dibenzylammonium hydrogen maleate, (I) (Fig. 1), and a
redetermination of bis(dibenzylamino)methane, (II) (Fig. 2).
Aminoethers are valuable building blocks in organic synthesis
as they are important precursors in the synthesis of a wide
range of pharmaceutical products (Pinder & Wieringa, 1993;
Franchini et al., 2003; Cavalluzzi et al., 2007; Huang et al.,
2009). In recent years, a series of selective serotonin (5-HT)-
reuptake inhibitor antidepressants (e.g. Fluexetine and
Paroxetine) and selective norepinephrine-reuptake inhibitor
antidepressants (e.g. Tomoxetine and Viloxazine) have been
developed (Pinder & Wieringa, 1993), and several of these
compounds contain a ꢀ-aminoether functionality, which could
be related to their biological activity. Continuing with our
current studies on the synthetic utility of benzylamines
´
(Castillo et al., 2009; Abonıa et al., 2010), the aminal (II) was
isolated as a possible intermediate in a synthetic route to novel
ꢀ-aminoether derivatives starting from secondary benzyl-
Figure 1
The ionic components of salt (I), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 30% probability level.
798 # 2013 International Union of Crystallography
doi:10.1107/S010827011301651X
Acta Cryst. (2013). C69, 798–802

organic compounds
1995) (Fig. 1 and Table 2); however, despite the short Oꢀ ꢀ ꢀO
distance, the hydroxy H atom is clearly offset from the mid-
point of the Oꢀ ꢀ ꢀO vector. The C—O distances in the anion
(Table 1) are fully consistent with the location of the hydroxy
H atom as deduced from a difference map. Similarly short and
nearly linear O—Hꢀ ꢀ ꢀO hydrogen bonds are found in the
hydrogen maleate salts formed with both 1,2-bis(pyridin-4-
yl)ethane and 4,40-bipyridyl, where the Oꢀ ꢀ ꢀO distances are
˚
2.4528 (18) and 2.463 (2) A, respectively, with O—Hꢀ ꢀ ꢀO
angles of 178 and 176ꢁ, respectively (Bowes et al., 2003); in
both of these salts, the H atom in the O—Hꢀ ꢀ ꢀO hydrogen
bond is clearly offset from the mid-point of the Oꢀ ꢀ ꢀO vector,
just as in salt (I).
The C—C—C—O torsion angles in the anion of (I) (Table 1)
show that both of the carboxyl fragments are rotated slightly
away from the plane defined by atoms C31–C34, such that
atoms O31 and O34 (those involved in the intra-anion
hydrogen bond) are both displaced to one side of the C31–C34
˚
plane, by 0.143 (2) and 0.134 (2) A, respectively, while atoms
O32 and O33 are displaced to the other side of this plane, by
˚
0.117 (2) and 0.115 (2) A, respectively, corresponding to a
disrotatory motion of the carboxyl groups around the C31—
C32 and C33—C34 bonds. By contrast, the anions in the salts
formed with 1,2-bis(pyridin-4-yl)ethane and 4,40-bipyridyl are
both effectively planar, with maximum deviations from the
mean plane of the eight non-H atoms of the anions of
˚
˚
0.041 (2) A in the former salt and only 0.013 (2) A in the latter
(Bowes et al., 2003).
In the asymmetric unit selected for salt (I) (Fig. 1), the two
ions are linked by an N—Hꢀ ꢀ ꢀO hydrogen bond (Table 2),
while a second N—Hꢀ ꢀ ꢀO hydrogen bond links such ion pairs
Figure 2
The independent molecular components of compound (II), showing the
atom-labelling scheme for (a) a type 1 molecule and (b) a type 2 molecule.
Displacement ellipsoids are drawn at the 30% probability level.
1
2
3
2
[Symmetry codes: (a) ꢃx + 1, y, ꢃz + ; (b) ꢃx + 1, y, ꢃz + .]
in the final refinements. Alongside the high R index is the
rather low precision, with s.u. values for the bonded C—C
˚
distances ranging from 0.006 to 0.014 A, with a mean s.u. of
˚
0.009 A. Accordingly, we have now taken the opportunity to
reinvestigate compound (II) using diffraction data collected at
120 K, resulting in a lower R value and significantly better
precision, with s.u. values for the bonded C—C distances
˚
typically equal to 0.002 A.
In the cation of salt (I), the central backbone between
atoms C11 and C21 (Fig. 1) is almost planar, as indicated by
the relevant torsion angles (Table 1), while the two indepen-
dent phenyl rings are almost orthogonal to this central plane.
The anion of (I) contains a rather short and almost linear O—
Hꢀ ꢀ ꢀO hydrogen bond, forming an S(7) motif (Bernstein et al.,
Figure 3
Part of the crystal structure of salt (I), showing the formation of a
hydrogen-bonded chain along [100]. For the sake of clarity, H atoms
bonded to C atoms have all been omitted. Atoms marked with an asterisk
(*) or a hash (#) are at the symmetry positions (x + 1, y, z) and (x ꢃ 1, y,
z), respectively.
C14H16N+ꢀC4H3O4 and C29H30N2 799
ꢃ
ꢂ
Acta Cryst. (2013). C69, 798–802
Castillo et al.

organic compounds
Figure 4
A stereoview of part of the crystal structure of salt (I), showing the
formation of a hydrogen-bonded sheet parallel to (010). For the sake of
clarity, H atoms not involved in the motifs shown have been omitted
which are related by translation to form a C22(6) (Bernstein et
al., 1995) chain running parallel to the [100] direction (Fig. 3).
There are also two short intermolecular C—Hꢀ ꢀ ꢀO contacts
present in the structure of (I) (Table 2). One of these inter-
actions, having a C—Hꢀ ꢀ ꢀO angle of 153ꢁ, weakly links the
chains along [100] into a sheet parallel to (010) and built from
S(7) and R67(25) rings (Fig. 4). In the other such interaction,
which lies within the (010) sheet, the C—Hꢀ ꢀ ꢀO angle is only
131ꢁ, so that this contact is probably not structurally significant
(Wood et al., 2009). It is notable that the strong and nearly
linear O—Hꢀ ꢀ ꢀO and N—Hꢀ ꢀ ꢀO hydrogen bonds in the
structure of (I) all involve the negatively charged O atoms of
the carboxylate group, whereas the C—Hꢀ ꢀ ꢀO contacts
involve the formally neutral O32 atom of the carboxylic acid
unit.
Figure 5
Projections of the molecular structures in compound (II) along the Nꢀ ꢀ ꢀN
vectors, showing the molecular conformations for (a) a type 1 molecule
and (b) a type 2 molecule. For the sake of clarity, H atoms have all been
omitted. [Symmetry codes: (a) ꢃx + 1, y, ꢃz + 12; (b) ꢃx + 1, y, ꢃz + .]
Compound (II) crystallizes in the space group C2/c with two
independent molecules both lying across twofold rotation
axes. Comparison of the unit-cell dimensions at 298 K (Lu et
al., 2007) and at 120 K indicates that no phase change has
occurred between these two temperatures. The molecules of
(II) exhibit no internal symmetry other than the twofold
rotation axis and hence they are conformationally chiral,
although the space group accommodates equal numbers of the
two conformational enantiomers. There is thus considerable
flexibility available in the choice of the asymmetric unit, but
that selected here contains two independent molecules of the
same enantiomeric form, as indicated by the general similarity
of corresponding torsion angles (Table 3). On this basis, the
type 1 molecule containing atom C1 lies across the rotation
axis along (12, y, 14), while the type 2 molecule containing atom
3
2
ceptional, and the C—N bond lengths involving atoms C1 and
C2 are typical of their type [mean value (Allen et al., 1987)
˚
1.469 A]. Both of the N atoms in compound (II) are markedly
pyramidal, with the sum of the interbond angles being
332.4 (2)ꢁ at N1 and 330.4 (2)ꢁ at N2. Despite this, there are no
C—Hꢀ ꢀ ꢀN hydrogen bonds within the crystal structure of (II);
indeed, there are no direction-specific interactions of any type,
as both C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen bonds and aromatic ꢀ–ꢀ
stacking interactions are also absent.
3
Experimental
C2 lies across the axis along (12, y, ).
4
For the synthesis of salt (I), a mixture of dibenzylamine (80 mg) and
an excess of maleic acid (161 mg, 2.5 equivalents) in ethyl acetate
(2 ml) was stirred at ambient temperature for 1 h. The resulting solid
product was collected by filtration, washed with cold ethyl acetate
(2 ꢄ 1 ml) and dried at ambient temperature to provide product (I) as
colourless crystals (yield 86%, m.p. 482 K). FT–IR (KBr): 3032,
2828, 2751, 2636, 1705 (C O), 1629 (C C), 1384, 1361, 1214, 1086
(C—O) cmꢃ1. Crystals suitable for single-crystal X-ray diffraction
were grown by slow evaporation, at ambient temperature and in air,
from a solution in ethyl acetate. For the synthesis of compound (II), a
mixture of dibenzylamine (201 mg, 2.0 mmol) and paraformaldehyde
(15 mg, 1.0 mmol) in acetonitrile (2 ml) was stirred at ambient
temperature for 3 h. The resulting solid product was collected by
In each molecule of (II), the arrangement of the benzyl
groups is probably dominated by a combination of steric
factors and the mutual repulsion of the lone pairs on the two N
atoms, which adopt an anticlinal conformation relative to the
Nꢀ ꢀ ꢀN direction (Fig. 5). The projections along the Nꢀ ꢀ ꢀN
vectors, together with the detailed comparison of the relevant
torsion angles (Table 3) confirm that there are sufficient
conformational differences between the two independent
molecules to preclude the possibility of any additional crys-
tallographic symmetry.
Despite the bulk of the dibenzylamino group, the interbond
angles (Table 3) at the central C1 and C2 atoms are unex-
C14H16N+ꢀC4H3O4 and C29H30N2
Acta Cryst. (2013). C69, 798–802
ꢃ
ꢂ
800 Castillo et al.

organic compounds
filtration, washed with acetonitrile (1 ml) and dried at ambient
temperature to provide aminal (II) (yield 93%, m.p. 372 K). FT–IR
(KBr): 3058, 2925, 2877, 1599, 739, 697 cmꢃ1. Colourless crystals
suitable for single-crystal X-ray diffraction were grown by slow
evaporation, at ambient temperature and in air, from a solution in
ethanol.
Table 1
Selected geometric parameters (A, ) for (I).
ꢁ
˚
C31—O31
C31—O32
1.3120 (19)
1.220 (2)
C34—O33
C34—O34
1.2402 (18)
1.2842 (18)
C27—N1—C17—C11 ꢃ177.63 (12)
N1—C17—C11—C12
ꢃ85.51 (18)
C33—C32—C31—O31
6.5 (3)
C33—C32—C31—O32 ꢃ174.08 (19)
C17—N1—C27—C21 ꢃ179.37 (12)
C32—C33—C34—O33
C32—C33—C34—O34
173.64 (17)
ꢃ7.5 (3)
Compound (I)
N1—C27—C21—C22
C31—C32—C33—C34
90.51 (17)
0.9 (3)
Crystal data
C14H16N+ꢀC4H3O4
ꢃ
3
˚
V = 1585.0 (3) A
Z = 4
Mr = 313.34
Monoclinic, P21=c
Table 2
Hydrogen-bond geometry (A, ) for (I).
Mo Kꢂ radiation
ꢃ = 0.09 mmꢃ1
T = 120 K
0.32 ꢄ 0.30 ꢄ 0.26 mm
ꢁ
˚
˚
a = 5.7551 (5) A
b = 16.1579 (19) A
˚
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
˚
c = 17.1230 (19) A
ꢁ = 95.464 (8)ꢁ
N1—H1Aꢀ ꢀ ꢀO33
N1—H1Bꢀ ꢀ ꢀO34i
O31—H31ꢀ ꢀ ꢀO34
C27—H27Aꢀ ꢀ ꢀO32ii
C27—H27Bꢀ ꢀ ꢀO32iii
0.91
0.90
0.98
0.99
0.99
1.94
1.96
1.48
2.55
2.54
2.8412 (16)
2.8582 (16)
2.4603 (16)
3.290 (2)
171
175
177
131
153
Data collection
Bruker–Nonius KappaCCD
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.971, Tmax = 0.976
22681 measured reflections
3639 independent reflections
2621 reflections with I > 2ꢄ(I)
Rint = 0.058
3.452 (2)
1
2
1
2
1
2
1
2
Symmetry codes: (i) x þ 1; y; z; (ii) x; ꢃy þ ; z ꢃ ; (iii) x þ 1; ꢃy þ ; z ꢃ .
Table 3
Selected geometric parameters (A, ) for (II).
ꢁ
˚
Refinement
R[F2 > 2ꢄ(F2)] = 0.046
wR(F2) = 0.110
S = 1.08
208 parameters
H-atom parameteꢃrs3 constrained
C1—N1
1.4612 (17)
110.27 (17)
C2—N2
1.4678 (17)
˚
Áꢅmax = 0.18 e A
ꢃ3
˚
N1—C1—N1i
N2—C2—N2ii
110.83 (17)
3639 reflections
Áꢅmin = ꢃ0.25 e A
N1i—C1—N1—C117
N1i—C1—N1—C127
C1—N1—C117—C111
ꢃ70.90 (10)
165.41 (12)
163.10 (13)
N2ii—C2—N2—C217
N2ii—C2—N2—C227
C2—N2—C217—C211
ꢃ64.21 (10)
174.01 (12)
169.98 (13)
Compound (II)
Crystal data
N1—C117—C111—C112 ꢃ39.3 (2)
C1—N1—C127—C121 ꢃ68.89 (15)
N1—C127—C121—C122 ꢃ50.98 (19)
N2—C217—C211—C212 ꢃ29.9 (2)
C2—N2—C227—C221 ꢃ63.51 (15)
N2—C227—C221—C222 ꢃ37.5 (2)
3
˚
V = 4670.4 (16) A
Z = 8
C29H30N2
Mr = 406.55
1
2
3
2
Monoclinic, C2=c
Mo Kꢂ radiation
ꢃ = 0.07 mmꢃ1
T = 120 K
0.42 ꢄ 0.24 ꢄ 0.23 mm
Symmetry codes: (i) ꢃx þ 1; y; ꢃz þ ; (ii) ꢃx þ 1; y; ꢃz þ .
˚
a = 25.548 (6) A
˚
b = 12.9426 (16) A
˚
c = 18.555 (3) A
ꢁ = 130.428 (11)ꢁ
tion: 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.
Data collection
Bruker–Nonius KappaCCD
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.972, Tmax = 0.985
18316 measured reflections
5366 independent reflections
3223 reflections with I > 2ꢄ(I)
Rint = 0.055
´
´
The authors thank ‘Centro de Instrumentacion Cientıfico-
Tecnica of Universidad de Jaen’ and the staff for data collec-
´
´
Refinement
tion. JCC and RA thank COLCIENCIAS and Universidad del
´
R[F2 > 2ꢄ(F2)] = 0.050
wR(F2) = 0.115
S = 1.01
281 parameters
H-atom parameteꢃrs3 constrained
Valle for financial support. JC thanks the Consejerıa de
´ ´
Innovacion, Ciencia y Empresa (Junta de Andalucıa, Spain)
˚
Áꢅmax = 0.25 e A
ꢃ3
˚
5366 reflections
Áꢅmin = ꢃ0.23 e A
´
and the Universidad de Jaen for financial support.
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: YF3037). Services for accessing these data are
described at the back of the journal.
All H atoms were located in difference maps. H atoms bonded to C
atoms were then treated as riding atoms in geometrically idealized
˚
positions, with C—H = 0.95 (aromatic and alkene) or 0.99 A (CH2)
and Uiso(H) = 1.2Ueq(C). H atoms bonded to N or O atoms were
permitted to ride at the positions deduced from difference maps, with
Uiso(H) = 1.2Ueq(N) or 1.5Ueq(O), giving the N—H and O—H
distances shown in Table 2.
References
´
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(2013). ACS Comb. Sci. 15, 2–9.
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cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduc-
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ꢃ
ꢂ
Acta Cryst. (2013). C69, 798–802
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C14H16N+ꢀC4H3O4 and C29H30N2
Acta Cryst. (2013). C69, 798–802
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802 Castillo et al.

supplementary materials
supplementary materials
Acta Cryst. (2013). C69, 798-802 [doi:10.1107/S010827011301651X]
Dibenzylammonium hydrogen maleate and a redetermination at 120 K of bis-
(dibenzylamino)methane
Juan C. Castillo, Rodrigo Abonía, Justo Cobo and Christopher Glidewell
Computing details
For both compounds, data collection: COLLECT (Hooft, 1998); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).
(I) Dibenzylammonium (2Z)-3-carboxyprop-2-enoate
Crystal data
C14H16N+·C4H3O4−
Mr = 313.34
F(000) = 664
Dx = 1.313 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 3639 reflections
θ = 2.8–27.5°
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 5.7551 (5) Å
b = 16.1579 (19) Å
c = 17.1230 (19) Å
β = 95.464 (8)°
V = 1585.0 (3) Å3
Z = 4
µ = 0.09 mm−1
T = 120 K
Block, colourless
0.32 × 0.30 × 0.26 mm
Data collection
Bruker–Nonius KappaCCD
diffractometer
Radiation source: Bruker–Nonius FR591
rotating anode
Graphite monochromator
Detector resolution: 9.091 pixels mm-1
φ & ω scans
Tmin = 0.971, Tmax = 0.976
22681 measured reflections
3639 independent reflections
2621 reflections with I > 2σ(I)
Rint = 0.058
θ
max = 27.5°, θmin = 2.8°
h = −7→7
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = −20→20
l = −22→22
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.046
wR(F2) = 0.110
S = 1.08
3639 reflections
208 parameters
0 restraints
Primary atom site location: structure-invariant
direct methods
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
H-atom parameters constrained
Acta Cryst. (2013). C69, 798-802
sup-1

supplementary materials
w = 1/[σ2(Fo2) + (0.0391P)2 + 0.5921P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.18 e Å−3
Δρmin = −0.25 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
N1
0.5366 (2)
0.3868
0.29720 (8)
0.2977
0.32397 (7)
0.3365
0.0191 (3)
0.023*
H1A
H1B
C17
H17A
H17B
C11
C12
H12
C13
H13
C14
H14
C15
H15
C16
H16
C27
H27A
H27B
C21
C22
H22
C23
H23
C24
H24
C25
H25
C26
H26
C31
C32
H32
C33
H33
C34
O31
H31
O32
O33
O34
0.6253
0.2914
0.3695
0.023*
0.5742 (3)
0.7414
0.22299 (10)
0.2192
0.27401 (9)
0.2652
0.0257 (4)
0.031*
0.4832
0.2296
0.2223
0.031*
0.5009 (3)
0.6548 (3)
0.8073
0.14446 (10)
0.10306 (10)
0.1246
0.31198 (9)
0.36598 (10)
0.3788
0.0228 (3)
0.0271 (4)
0.033*
0.5884 (3)
0.6947
0.03080 (11)
0.0033
0.40131 (11)
0.4385
0.0336 (4)
0.040*
0.3674 (3)
0.3218
−0.00141 (11)
−0.0510
0.38249 (11)
0.4066
0.0344 (4)
0.041*
0.2136 (3)
0.0623
0.03868 (11)
0.0164
0.32862 (11)
0.3153
0.0343 (4)
0.041*
0.2788 (3)
0.1712
0.11154 (11)
0.1391
0.29361 (10)
0.2569
0.0283 (4)
0.034*
0.5999 (3)
0.5025
0.37606 (10)
0.3821
0.28506 (9)
0.2345
0.0225 (3)
0.027*
0.7653
0.3736
0.2738
0.027*
0.5641 (3)
0.7442 (3)
0.8900
0.45008 (10)
0.47900 (10)
0.4510
0.33596 (9)
0.38888 (9)
0.3940
0.0209 (3)
0.0251 (4)
0.030*
0.7124 (3)
0.8362
0.54831 (11)
0.5677
0.43418 (10)
0.4702
0.0318 (4)
0.038*
0.5000 (3)
0.4783
0.58949 (11)
0.6370
0.42711 (11)
0.4583
0.0336 (4)
0.040*
0.3199 (3)
0.1746
0.56126 (11)
0.5896
0.37469 (11)
0.3696
0.0323 (4)
0.039*
0.3511 (3)
0.2262
0.49167 (10)
0.4721
0.32962 (10)
0.2941
0.0267 (4)
0.032*
0.0391 (3)
0.2231 (3)
0.3669
0.19287 (11)
0.19375 (10)
0.1696
0.62431 (10)
0.56848 (9)
0.5888
0.0265 (4)
0.0235 (3)
0.028*
0.2229 (3)
0.3650
0.22217 (10)
0.2140
0.49537 (9)
0.4724
0.0224 (3)
0.027*
0.0356 (3)
−0.17349 (18)
−0.1673
0.26483 (10)
0.21716 (8)
0.2373
0.44335 (9)
0.60052 (7)
0.5466
0.0204 (3)
0.0306 (3)
0.046*
0.0899 (2)
0.08704 (18)
−0.17021 (17)
0.16877 (10)
0.29195 (7)
0.27045 (7)
0.69127 (7)
0.37947 (6)
0.46603 (6)
0.0472 (4)
0.0273 (3)
0.0243 (3)
Acta Cryst. (2013). C69, 798-802
sup-2

supplementary materials
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
N1
0.0174 (6)
0.0295 (9)
0.0237 (8)
0.0249 (8)
0.0409 (10)
0.0419 (10)
0.0255 (9)
0.0255 (8)
0.0233 (8)
0.0213 (8)
0.0216 (8)
0.0290 (9)
0.0376 (10)
0.0245 (9)
0.0215 (8)
0.0213 (8)
0.0166 (7)
0.0163 (7)
0.0177 (7)
0.0203 (6)
0.0293 (7)
0.0230 (6)
0.0170 (5)
0.0214 (7)
0.0243 (9)
0.0210 (8)
0.0245 (9)
0.0260 (10)
0.0231 (9)
0.0310 (10)
0.0273 (9)
0.0231 (8)
0.0196 (8)
0.0251 (9)
0.0314 (10)
0.0213 (9)
0.0249 (9)
0.0253 (9)
0.0328 (10)
0.0270 (9)
0.0272 (9)
0.0206 (8)
0.0458 (8)
0.0836 (11)
0.0354 (7)
0.0314 (7)
0.0185 (6)
0.0242 (8)
0.0243 (8)
0.0319 (9)
0.0334 (10)
0.0404 (10)
0.0475 (11)
0.0318 (9)
0.0213 (8)
0.0220 (8)
0.0283 (9)
0.0346 (9)
0.0440 (10)
0.0488 (11)
0.0330 (9)
0.0252 (8)
0.0267 (8)
0.0242 (8)
0.0227 (8)
0.0264 (6)
0.0290 (7)
0.0239 (6)
0.0245 (6)
0.0016 (5)
0.0014 (7)
0.0021 (6)
0.0000 (7)
0.0036 (8)
−0.0051 (8)
−0.0050 (7)
0.0038 (7)
−0.0026 (6)
−0.0013 (6)
0.0000 (7)
−0.0048 (7)
−0.0028 (7)
0.0047 (7)
−0.0007 (7)
−0.0006 (7)
0.0030 (6)
0.0031 (6)
0.0004 (6)
0.0057 (5)
0.0082 (7)
0.0043 (5)
0.0032 (5)
0.0018 (5)
0.0076 (7)
0.0055 (6)
0.0021 (7)
0.0011 (8)
0.0161 (8)
0.0084 (8)
0.0012 (7)
0.0030 (6)
0.0036 (6)
0.0008 (7)
0.0011 (7)
0.0145 (8)
0.0105 (8)
0.0012 (7)
0.0012 (6)
0.0003 (6)
0.0038 (6)
0.0011 (6)
0.0057 (5)
0.0044 (5)
0.0050 (5)
0.0025 (4)
0.0008 (5)
−0.0042 (7)
−0.0056 (6)
−0.0053 (7)
−0.0004 (8)
−0.0040 (8)
−0.0142 (9)
−0.0075 (7)
0.0021 (6)
0.0034 (6)
0.0002 (7)
−0.0053 (8)
−0.0061 (8)
0.0041 (8)
0.0043 (7)
0.0032 (7)
0.0017 (7)
0.0000 (7)
−0.0037 (6)
0.0092 (5)
0.0217 (7)
0.0064 (5)
0.0019 (5)
C17
C11
C12
C13
C14
C15
C16
C27
C21
C22
C23
C24
C25
C26
C31
C32
C33
C34
O31
O32
O33
O34
Geometric parameters (Å, º)
N1—C27
1.4987 (19)
C21—C26
1.393 (2)
N1—C17
1.501 (2)
0.9085
C22—C23
C22—H22
C23—C24
C23—H23
C24—C25
C24—H24
C25—C26
C25—H25
C26—H26
C31—O31
C31—O32
C31—C32
C32—C33
C32—H32
C33—C34
C33—H33
C34—O33
C34—O34
O31—H31
O34—H31
1.384 (2)
0.9500
N1—H1A
N1—H1B
C17—C11
C17—H17A
C17—H17B
C11—C12
C11—C16
C12—C13
C12—H12
C13—C14
C13—H13
C14—C15
C14—H14
C15—C16
C15—H15
C16—H16
C27—C21
C27—H27A
C27—H27B
0.8954
1.387 (2)
0.9500
1.504 (2)
0.9900
1.382 (3)
0.9500
0.9900
1.390 (2)
1.393 (2)
1.385 (2)
0.9500
1.385 (2)
0.9500
0.9500
1.3120 (19)
1.220 (2)
1.493 (2)
1.333 (2)
0.9500
1.384 (3)
0.9500
1.378 (3)
0.9500
1.389 (3)
0.9500
1.499 (2)
0.9500
0.9500
1.2402 (18)
1.2842 (18)
0.9822
1.506 (2)
0.9900
0.9900
1.4792
Acta Cryst. (2013). C69, 798-802
sup-3

supplementary materials
C21—C22
1.391 (2)
C27—N1—C17
C27—N1—H1A
C17—N1—H1A
C27—N1—H1B
C17—N1—H1B
H1A—N1—H1B
N1—C17—C11
N1—C17—H17A
C11—C17—H17A
N1—C17—H17B
C11—C17—H17B
H17A—C17—H17B
C12—C11—C16
C12—C11—C17
C16—C11—C17
C13—C12—C11
C13—C12—H12
C11—C12—H12
C14—C13—C12
C14—C13—H13
C12—C13—H13
C15—C14—C13
C15—C14—H14
C13—C14—H14
C14—C15—C16
C14—C15—H15
C16—C15—H15
C15—C16—C11
C15—C16—H16
C11—C16—H16
N1—C27—C21
N1—C27—H27A
C21—C27—H27A
N1—C27—H27B
111.82 (11)
112.0
C21—C27—H27B
109.3
H27A—C27—H27B
C22—C21—C26
C22—C21—C27
C26—C21—C27
C23—C22—C21
C23—C22—H22
C21—C22—H22
C22—C23—C24
C22—C23—H23
C24—C23—H23
C25—C24—C23
C25—C24—H24
C23—C24—H24
C24—C25—C26
C24—C25—H25
C26—C25—H25
C25—C26—C21
C25—C26—H26
C21—C26—H26
O32—C31—O31
O32—C31—C32
O31—C31—C32
C33—C32—C31
C33—C32—H32
C31—C32—H32
C32—C33—C34
C32—C33—H33
C34—C33—H33
O33—C34—O34
O33—C34—C33
O34—C34—C33
C31—O31—H31
C34—O34—H31
108.0
109.5
118.97 (15)
120.64 (14)
120.37 (14)
120.44 (15)
119.8
109.5
108.1
105.6
111.48 (12)
109.3
119.8
109.3
120.12 (16)
119.9
109.3
109.3
119.9
108.0
119.90 (17)
120.0
118.67 (16)
120.42 (14)
120.91 (15)
120.74 (16)
119.6
120.0
120.04 (16)
120.0
120.0
119.6
120.52 (16)
119.7
120.08 (17)
120.0
119.7
120.0
121.36 (15)
118.92 (15)
119.71 (14)
131.85 (15)
114.1
119.77 (17)
120.1
120.1
120.33 (16)
119.8
114.1
119.8
130.74 (14)
114.6
120.40 (16)
119.8
114.6
119.8
123.11 (14)
117.90 (13)
118.98 (14)
105.9
111.45 (12)
109.3
109.3
109.3
109.1
C27—N1—C17—C11
N1—C17—C11—C12
N1—C17—C11—C16
C16—C11—C12—C13
C17—C11—C12—C13
C11—C12—C13—C14
C12—C13—C14—C15
C13—C14—C15—C16
C14—C15—C16—C11
C12—C11—C16—C15
C17—C11—C16—C15
C17—N1—C27—C21
−177.63 (12)
−85.51 (18)
94.80 (17)
−0.4 (2)
C26—C21—C22—C23
C27—C21—C22—C23
C21—C22—C23—C24
C22—C23—C24—C25
C23—C24—C25—C26
C24—C25—C26—C21
C22—C21—C26—C25
C27—C21—C26—C25
C31—C32—C33—C34
C33—C32—C31—O31
C33—C32—C31—O32
C32—C33—C34—O33
−0.4 (2)
178.40 (15)
0.0 (3)
0.0 (3)
179.86 (15)
0.6 (3)
0.4 (3)
−0.7 (3)
0.7 (2)
−0.1 (3)
−0.5 (3)
−178.07 (15)
0.9 (3)
0.6 (3)
−0.2 (2)
6.5 (3)
179.54 (15)
−179.37 (12)
−174.08 (19)
173.64 (17)
Acta Cryst. (2013). C69, 798-802
sup-4

supplementary materials
N1—C27—C21—C22
N1—C27—C21—C26
90.51 (17)
C32—C33—C34—O34
−7.5 (3)
−90.76 (17)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
N1—H1A···O33
0.91
0.90
0.98
0.99
0.99
1.94
1.96
1.48
2.55
2.54
2.8412 (16)
2.8582 (16)
2.4603 (16)
3.290 (2)
171
175
177
131
153
N1—H1B···O34i
O31—H31···O34
C27—H27A···O32ii
C27—H27B···O32iii
3.452 (2)
Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z−1/2; (iii) x+1, −y+1/2, z−1/2.
(II) Bis(dibenzylamino)methane
Crystal data
C29H30N2
Mr = 406.55
F(000) = 1744
Dx = 1.156 Mg m−3
Monoclinic, C2/c
Hall symbol: -C 2yc
a = 25.548 (6) Å
b = 12.9426 (16) Å
c = 18.555 (3) Å
β = 130.428 (11)°
V = 4670.4 (16) Å3
Z = 8
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 5366 reflections
θ = 2.8–27.5°
µ = 0.07 mm−1
T = 120 K
Block, colourless
0.42 × 0.24 × 0.23 mm
Data collection
Bruker–Nonius KappaCCD
diffractometer
Radiation source: Bruker–Nonius FR591
rotating anode
Graphite monochromator
Detector resolution: 9.091 pixels mm-1
φ & ω scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.972, Tmax = 0.985
18316 measured reflections
5366 independent reflections
3223 reflections with I > 2σ(I)
Rint = 0.055
θ
max = 27.5°, θmin = 2.8°
h = −33→33
k = −16→16
l = −24→24
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.050
wR(F2) = 0.115
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.01
5366 reflections
281 parameters
0 restraints
Primary atom site location: structure-invariant
direct methods
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0482P)2 + 1.028P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.25 e Å−3
Δρmin = −0.23 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
Occ. (<1)
C1
0.5000
0.50145 (17)
0.2500
0.0307 (5)
Acta Cryst. (2013). C69, 798-802
sup-5

supplementary materials
H1A
H1B
0.5412
0.4566
0.2885
0.037*
0.50
0.50
0.4588
0.4566
0.2115
0.037*
N1
0.49758 (6)
0.56415 (8)
0.5818
0.56599 (9)
0.61702 (12)
0.6415
0.31241 (9)
0.38317 (11)
0.3519
0.0276 (3)
0.0320 (4)
0.038*
C117
H11A
H11B
C111
C112
H112
C113
H113
C114
H114
C115
H115
C116
H116
C127
H12A
H12B
C121
C122
H122
C123
H123
C124
H124
C125
H125
C126
H126
C2
0.5973
0.5658
0.4319
0.038*
0.56044 (8)
0.50511 (8)
0.4674
0.70735 (12)
0.77576 (12)
0.7637
0.43112 (10)
0.38141 (11)
0.3163
0.0266 (4)
0.0298 (4)
0.036*
0.50456 (8)
0.4661
0.86085 (13)
0.9061
0.42574 (11)
0.3911
0.0335 (4)
0.040*
0.55938 (9)
0.5590
0.88093 (13)
0.9402
0.51999 (12)
0.5499
0.0349 (4)
0.042*
0.61455 (9)
0.6526
0.81410 (13)
0.8275
0.57019 (11)
0.6349
0.0362 (4)
0.043*
0.61463 (8)
0.6523
0.72733 (13)
0.6807
0.52643 (11)
0.5621
0.0337 (4)
0.040*
0.47741 (8)
0.4843
0.50487 (13)
0.5469
0.35771 (11)
0.4078
0.0315 (4)
0.038*
0.5076
0.4435
0.3882
0.038*
0.40329 (8)
0.35101 (8)
0.3622
0.46988 (12)
0.54050 (13)
0.6111
0.28810 (10)
0.22746 (11)
0.2298
0.0276 (4)
0.0315 (4)
0.038*
0.28296 (9)
0.2479
0.50947 (14)
0.5587
0.16380 (11)
0.1229
0.0367 (4)
0.044*
0.26594 (9)
0.2193
0.40668 (14)
0.3851
0.15969 (12)
0.1160
0.0373 (4)
0.045*
0.31716 (9)
0.3058
0.33627 (14)
0.2657
0.21932 (12)
0.2167
0.0398 (4)
0.048*
0.38526 (9)
0.4201
0.36730 (12)
0.3178
0.28316 (12)
0.3241
0.0343 (4)
0.041*
0.5000
0.97739 (17)
1.0223
0.7500
0.0296 (5)
0.035*
H2A
H2B
0.4848
0.7765
0.50
0.50
0.5152
1.0223
0.7235
0.035*
N2
0.44225 (6)
0.46209 (8)
0.5069
0.91302 (10)
0.85271 (12)
0.8190
0.67439 (9)
0.62851 (12)
0.6780
0.0279 (3)
0.0325 (4)
0.039*
C217
H21A
H21B
C211
C212
H212
C213
H213
C214
H214
C215
H215
C216
H216
0.4684
0.9004
0.5929
0.039*
0.41026 (8)
0.36882 (8)
0.3710
0.77066 (12)
0.72257 (12)
0.7436
0.56140 (11)
0.57501 (11)
0.6259
0.0287 (4)
0.0342 (4)
0.041*
0.32439 (9)
0.2963
0.64434 (13)
0.6121
0.51542 (13)
0.5257
0.0443 (5)
0.053*
0.32050 (10)
0.2901
0.61278 (15)
0.5586
0.44124 (13)
0.4007
0.0492 (5)
0.059*
0.36114 (10)
0.3587
0.66048 (15)
0.6392
0.42603 (12)
0.3749
0.0469 (5)
0.056*
0.40538 (9)
0.4327
0.73944 (13)
0.7726
0.48572 (11)
0.4746
0.0366 (4)
0.044*
Acta Cryst. (2013). C69, 798-802
sup-6

supplementary materials
C227
H22A
H22B
C221
C222
H222
C223
H223
C224
H224
C225
H225
C226
H226
0.38256 (8)
0.3456
0.97856 (12)
0.9347
0.60460 (11)
0.5514
0.0304 (4)
0.036*
0.3959
1.0292
0.5790
0.036*
0.35458 (7)
0.35201 (8)
0.3692
1.03623 (12)
0.99267 (13)
0.9247
0.64375 (10)
0.71004 (11)
0.7326
0.0273 (4)
0.0311 (4)
0.037*
0.32499 (8)
0.3245
1.04652 (14)
1.0160
0.74361 (11)
0.7897
0.0370 (4)
0.044*
0.29869 (8)
0.2800
1.14460 (14)
1.1817
0.71023 (12)
0.7331
0.0400 (4)
0.048*
0.29975 (8)
0.2809
1.18829 (13)
1.2552
0.64341 (12)
0.6194
0.0397 (4)
0.048*
0.32808 (8)
0.3295
1.13546 (12)
1.1671
0.61092 (11)
0.5660
0.0335 (4)
0.040*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
C1
0.0330 (13)
0.0252 (7)
0.0220 (8)
0.0227 (8)
0.0230 (8)
0.0281 (9)
0.0406 (10)
0.0333 (10)
0.0256 (9)
0.0295 (9)
0.0309 (9)
0.0319 (9)
0.0315 (9)
0.0327 (9)
0.0459 (11)
0.0387 (10)
0.0235 (12)
0.0199 (7)
0.0291 (9)
0.0266 (8)
0.0328 (9)
0.0384 (11)
0.0339 (10)
0.0448 (11)
0.0383 (10)
0.0248 (9)
0.0185 (8)
0.0244 (8)
0.0261 (9)
0.0234 (9)
0.0287 (9)
0.0282 (9)
0.0289 (12)
0.0311 (7)
0.0381 (9)
0.0317 (9)
0.0338 (9)
0.0334 (9)
0.0341 (9)
0.0449 (10)
0.0411 (10)
0.0349 (9)
0.0320 (9)
0.0295 (9)
0.0455 (11)
0.0517 (11)
0.0368 (10)
0.0325 (9)
0.0298 (12)
0.0326 (7)
0.0361 (9)
0.0290 (9)
0.0359 (9)
0.0351 (10)
0.0385 (11)
0.0533 (12)
0.0402 (10)
0.0371 (9)
0.0305 (9)
0.0333 (9)
0.0512 (11)
0.0495 (11)
0.0291 (9)
0.0298 (9)
0.0330 (12)
0.0289 (7)
0.0330 (9)
0.0269 (8)
0.0250 (8)
0.0348 (9)
0.0374 (10)
0.0226 (8)
0.0271 (8)
0.0304 (9)
0.0283 (8)
0.0335 (9)
0.0323 (9)
0.0314 (9)
0.0442 (10)
0.0395 (10)
0.0308 (12)
0.0279 (7)
0.0375 (9)
0.0289 (8)
0.0357 (9)
0.0556 (12)
0.0467 (11)
0.0318 (10)
0.0351 (9)
0.0262 (8)
0.0259 (8)
0.0320 (9)
0.0315 (9)
0.0363 (10)
0.0440 (10)
0.0317 (9)
0.000
0.0227 (11)
0.0187 (6)
0.0166 (8)
0.0167 (7)
0.0122 (7)
0.0185 (8)
0.0285 (9)
0.0147 (8)
0.0137 (8)
0.0196 (8)
0.0230 (8)
0.0214 (8)
0.0203 (8)
0.0226 (8)
0.0325 (10)
0.0289 (9)
0.0156 (11)
0.0139 (6)
0.0239 (8)
0.0172 (7)
0.0230 (8)
0.0287 (10)
0.0135 (9)
0.0200 (9)
0.0255 (8)
0.0151 (7)
0.0112 (7)
0.0167 (8)
0.0178 (8)
0.0146 (8)
0.0158 (9)
0.0146 (8)
0.000
N1
−0.0022 (6)
−0.0009 (6)
0.0001 (7)
0.0035 (7)
0.0026 (7)
0.0047 (7)
−0.0011 (8)
−0.0006 (8)
0.0061 (8)
0.0055 (7)
0.0006 (7)
0.0009 (7)
0.0062 (8)
−0.0017 (8)
−0.0015 (8)
0.0055 (8)
0.000
C117
C111
C112
C113
C114
C115
C116
C127
C121
C122
C123
C124
C125
C126
C2
0.0009 (7)
−0.0009 (7)
−0.0001 (7)
0.0033 (7)
−0.0026 (8)
−0.0055 (8)
0.0046 (8)
0.0034 (8)
−0.0004 (7)
0.0004 (8)
0.0034 (8)
−0.0101 (9)
−0.0102 (9)
0.0026 (8)
0.000
N2
0.0012 (6)
−0.0005 (8)
0.0047 (7)
−0.0023 (8)
−0.0058 (9)
−0.0010 (9)
0.0126 (10)
0.0067 (8)
0.0027 (7)
−0.0040 (7)
0.0026 (7)
−0.0004 (8)
0.0019 (8)
0.0036 (8)
−0.0011 (7)
−0.0042 (6)
−0.0032 (8)
0.0029 (7)
−0.0011 (8)
−0.0014 (9)
−0.0123 (9)
−0.0065 (9)
0.0044 (8)
0.0019 (7)
−0.0049 (7)
0.0032 (7)
−0.0035 (8)
−0.0115 (9)
−0.0046 (8)
0.0003 (7)
C217
C211
C212
C213
C214
C215
C216
C227
C221
C222
C223
C224
C225
C226
Acta Cryst. (2013). C69, 798-802
sup-7

supplementary materials
Geometric parameters (Å, º)
C1—N1i
1.4612 (17)
1.4612 (17)
0.9900
C2—N2
1.4678 (17)
1.4678 (17)
0.9900
C1—N1
C2—N2ii
C1—H1A
C2—H2A
C1—H1B
0.9900
C2—H2B
0.9900
N1—C117
1.4685 (19)
1.4694 (19)
1.509 (2)
0.9900
N2—C217
1.4663 (19)
1.4700 (19)
1.514 (2)
0.9900
N1—C127
N2—C227
C117—C111
C117—H11A
C117—H11B
C111—C116
C111—C112
C112—C113
C112—H112
C113—C114
C113—H113
C114—C115
C114—H114
C115—C116
C115—H115
C116—H116
C127—C121
C127—H12A
C127—H12B
C121—C126
C121—C122
C122—C123
C122—H122
C123—C124
C123—H123
C124—C125
C124—H124
C125—C126
C125—H125
C126—H126
C217—C211
C217—H21A
C217—H21B
C211—C212
C211—C216
C212—C213
C212—H212
C213—C214
C213—H213
C214—C215
C214—H214
C215—C216
C215—H215
C216—H216
C227—C221
C227—H22A
C227—H22B
C221—C222
C221—C226
C222—C223
C222—H222
C223—C224
C223—H223
C224—C225
C224—H224
C225—C226
C225—H225
C226—H226
0.9900
0.9900
1.391 (2)
1.393 (2)
1.380 (2)
0.9500
1.385 (2)
1.387 (2)
1.381 (2)
0.9500
1.382 (2)
0.9500
1.376 (3)
0.9500
1.378 (2)
0.9500
1.385 (3)
0.9500
1.387 (2)
0.9500
1.387 (2)
0.9500
0.9500
0.9500
1.512 (2)
0.9900
1.506 (2)
0.9900
0.9900
0.9900
1.389 (2)
1.391 (2)
1.384 (2)
0.9500
1.393 (2)
1.394 (2)
1.381 (2)
0.9500
1.386 (2)
0.9500
1.381 (2)
0.9500
1.374 (2)
0.9500
1.379 (2)
0.9500
1.385 (2)
0.9500
1.386 (2)
0.9500
0.9500
0.9500
N1—C1—N1i
110.27 (17)
109.6
N2—C2—N2ii
110.83 (17)
109.5
N1i—C1—H1A
N1—C1—H1A
N1i—C1—H1B
N1—C1—H1B
N2—C2—H2A
N2ii—C2—H2A
N2—C2—H2B
N2ii—C2—H2B
H2A—C2—H2B
C217—N2—C2
C217—N2—C227
C2—N2—C227
N2—C217—C211
N2—C217—H21A
109.6
109.5
109.6
109.5
109.6
109.5
H1A—C1—H1B
C1—N1—C117
C1—N1—C127
C117—N1—C127
N1—C117—C111
N1—C117—H11A
C111—C117—H11A
N1—C117—H11B
108.1
108.1
110.24 (11)
110.87 (12)
111.29 (12)
113.35 (13)
108.9
110.21 (11)
110.33 (12)
109.87 (12)
113.81 (13)
108.8
108.9
C211—C217—H21A
N2—C217—H21B
108.8
108.8
108.9
Acta Cryst. (2013). C69, 798-802
sup-8

supplementary materials
C111—C117—H11B
H11A—C117—H11B
C116—C111—C112
C116—C111—C117
C112—C111—C117
C113—C112—C111
C113—C112—H112
C111—C112—H112
C112—C113—C114
C112—C113—H113
C114—C113—H113
C115—C114—C113
C115—C114—H114
C113—C114—H114
C114—C115—C116
C114—C115—H115
C116—C115—H115
C115—C116—C111
C115—C116—H116
C111—C116—H116
N1—C127—C121
108.9
C211—C217—H21B
108.8
107.7
H21A—C217—H21B
C212—C211—C216
C212—C211—C217
C216—C211—C217
C213—C212—C211
C213—C212—H212
C211—C212—H212
C214—C213—C212
C214—C213—H213
C212—C213—H213
C213—C214—C215
C213—C214—H214
C215—C214—H214
C214—C215—C216
C214—C215—H215
C216—C215—H215
C211—C216—C215
C211—C216—H216
C215—C216—H216
N2—C227—C221
107.7
118.00 (15)
120.15 (14)
121.78 (14)
120.70 (14)
119.7
118.43 (15)
121.96 (15)
119.57 (15)
120.79 (17)
119.6
119.7
119.6
120.70 (16)
119.6
120.46 (18)
119.8
119.6
119.8
119.34 (16)
120.3
119.60 (17)
120.2
120.3
120.2
120.12 (15)
119.9
119.72 (17)
120.1
119.9
120.1
121.11 (15)
119.4
120.98 (17)
119.5
119.4
119.5
112.46 (12)
109.1
114.00 (12)
108.8
N1—C127—H12A
C121—C127—H12A
N1—C127—H12B
C121—C127—H12B
H12A—C127—H12B
C126—C121—C122
C126—C121—C127
C122—C121—C127
C123—C122—C121
C123—C122—H122
C121—C122—H122
C122—C123—C124
C122—C123—H123
C124—C123—H123
C125—C124—C123
C125—C124—H124
C123—C124—H124
C124—C125—C126
C124—C125—H125
C126—C125—H125
C125—C126—C121
C125—C126—H126
C121—C126—H126
N2—C227—H22A
C221—C227—H22A
N2—C227—H22B
C221—C227—H22B
H22A—C227—H22B
C222—C221—C226
C222—C221—C227
C226—C221—C227
C223—C222—C221
C223—C222—H222
C221—C222—H222
C224—C223—C222
C224—C223—H223
C222—C223—H223
C225—C224—C223
C225—C224—H224
C223—C224—H224
C224—C225—C226
C224—C225—H225
C226—C225—H225
C225—C226—C221
C225—C226—H226
C221—C226—H226
109.1
108.8
109.1
108.8
109.1
108.8
107.8
107.6
118.12 (15)
121.38 (14)
120.50 (14)
121.02 (16)
119.5
118.11 (15)
122.29 (14)
119.57 (14)
121.17 (15)
119.4
119.5
119.4
120.06 (16)
120.0
120.12 (17)
119.9
120.0
119.9
119.42 (16)
120.3
119.51 (17)
120.2
120.3
120.2
120.55 (16)
119.7
120.61 (16)
119.7
119.7
119.7
120.83 (16)
119.6
120.45 (16)
119.8
119.6
119.8
N1i—C1—N1—C117
N1i—C1—N1—C127
C1—N1—C117—C111
C127—N1—C117—C111
−70.90 (10)
165.41 (12)
163.10 (13)
−73.45 (16)
N2ii—C2—N2—C217
N2ii—C2—N2—C227
C2—N2—C217—C211
C227—N2—C217—C211
−64.21 (10)
174.01 (12)
169.98 (13)
−68.51 (17)
Acta Cryst. (2013). C69, 798-802
sup-9

supplementary materials
N1—C117—C111—C116
N1—C117—C111—C112
C116—C111—C112—C113
C117—C111—C112—C113
C111—C112—C113—C114
C112—C113—C114—C115
C113—C114—C115—C116
C114—C115—C116—C111
C112—C111—C116—C115
C117—C111—C116—C115
C1—N1—C127—C121
143.96 (15)
−39.3 (2)
0.2 (2)
N2—C217—C211—C212
−29.9 (2)
152.47 (14)
0.9 (2)
N2—C217—C211—C216
C216—C211—C212—C213
C217—C211—C212—C213
C211—C212—C213—C214
C212—C213—C214—C215
C213—C214—C215—C216
C212—C211—C216—C215
C217—C211—C216—C215
C214—C215—C216—C211
C217—N2—C227—C221
C2—N2—C227—C221
−176.60 (15)
1.1 (2)
−176.75 (15)
0.0 (3)
−1.0 (2)
−0.5 (3)
−0.4 (2)
0.1 (3)
1.7 (3)
−1.3 (2)
−1.6 (2)
176.41 (15)
0.8 (3)
175.26 (15)
−68.89 (15)
168.02 (13)
129.53 (15)
−50.98 (19)
−0.2 (2)
174.78 (13)
−63.51 (15)
−37.5 (2)
144.65 (14)
−1.0 (2)
C117—N1—C127—C121
N1—C127—C121—C126
N1—C127—C121—C122
C126—C121—C122—C123
C127—C121—C122—C123
C121—C122—C123—C124
C122—C123—C124—C125
C123—C124—C125—C126
C124—C125—C126—C121
C122—C121—C126—C125
C127—C121—C126—C125
N2—C227—C221—C222
N2—C227—C221—C226
C226—C221—C222—C223
C227—C221—C222—C223
C221—C222—C223—C224
C222—C223—C224—C225
C223—C224—C225—C226
C224—C225—C226—C221
C222—C221—C226—C225
C227—C221—C226—C225
−179.67 (14)
0.0 (2)
−178.85 (14)
1.2 (2)
0.1 (3)
−0.1 (2)
0.1 (3)
−1.2 (2)
−0.2 (3)
1.5 (2)
0.3 (2)
−0.4 (2)
179.78 (15)
177.57 (14)
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1, y, −z+3/2.
Acta Cryst. (2013). C69, 798-802
sup-10