Five related N′-(2,2,2-trichloroethanimidoyl)benzene-1- carboximidamides

Article abstract of DOI:10.1107/S0108270111023985

In the solid state, 4-meth-oxy-N′-(2,2,2-trichloroethanimidoyl) benzene-1-carboximidamide, C₁₀H₁₀Cl₃N ₃O, (I), N′-(2,2,2-trichloroethanimidoyl)benzene-1- carboximidamide, C₉H₈Cl₃N₃, (II), 4-chloro-N′-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamide, C ₉H₇Cl₄N₃, (III), 4-bromo-N′-(2,2,2-trichloroethanimidoyl)benzene-1-carboximidamide, C ₉H₇BrCl₃N₃, (IV), and 4-trifluoromethyl-N′-(2,2,2-trichloroethanimidoyl)benzene-1- carboximidamide, C₁₀H₇Cl₃F₃N ₃, (V), display strong intramolecular N - H...N hydrogen bonding across the chelate ring and also intramolecular N - H...Cl contacts. Additional intermolecular hydrogen bonds link the molecules into chains, double chains or sheets in all cases except for compound (V). For compound (II), there are three independent molecules per asymmetric unit.

Full text of DOI:10.1107/S0108270111023985

organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
ylovich & Pombeiro, 2011). Crystal structure reports of neutral
primary N-imidoylamidines are rare. We recently reported the
synthesis and crystal structures of a number of aryltrifluoro-
´
ISSN 0108-2701
methyl N-imidoylamidines (Boere et al., 2011). We report here
the crystal structures of five new trichloromethyl analogues,
(I)–(V), bearing electron-releasing and electron-withdrawing
substituents on the aryl rings.
Five related N0-(2,2,2-trichloro-
ethanimidoyl)benzene-1-carbox-
imidamides
a
a
´
´
Rene T. Boere, * Tracey L. Roemmele, Savini Suduweli
Kondage,a Jiamin Zhoua and Masood Parvezb
aDepartment of Chemistry and Biochemistry, University of Lethbridge, Lethbridge,
Alberta, Canada T1K 3M4, and bDepartment of Chemistry, University of Calgary,
Calgary, Alberta, Canada
The molecular structures of (I)–(V) are remarkably similar
and displacement ellipsoid plots are shown in Figs. 1, 3, 5, 7
and 8, respectively.. The same atom-numbering scheme is used
for all five structures [modified in the case of (II) by suffixes
‘A’, ‘B’ and ‘C’ to identify the three crystallographically
Correspondence e-mail: boere@uleth.ca
Received 29 May 2011
Accepted 19 June 2011
Online 5 July 2011
independent molecules in the asymetric unit]. Average bond
. . . . . . . . . . . .
lengths and angles for the N C N C N cores have been
compiled, along with s.u. values, and are listed in Table 6.
In the solid state, 4-methoxy-N0-(2,2,2-trichloroethanimidoyl)-
benzene-1-carboximidamide, C10H10Cl3N3O, (I), N0-(2,2,2-tri-
chloroethanimidoyl)benzene-1-carboximidamide, C9H8Cl3N3,
(II), 4-chloro-N0-(2,2,2-trichloroethanimidoyl)benzene-1-car-
boximidamide, C9H7Cl4N3, (III), 4-bromo-N0-(2,2,2-trichloro-
ethanimidoyl)benzene-1-carboximidamide, C9H7BrCl3N3, (IV),
and 4-trifluoromethyl-N0-(2,2,2-trichloroethanimidoyl)benzene-
1-carboximidamide, C10H7Cl3F3N3, (V), display strong intra-
molecular N—Hꢀ ꢀ ꢀN hydrogen bonding across the chelate
ring and also intramolecular N—Hꢀ ꢀ ꢀCl contacts. Additional
intermolecular hydrogen bonds link the molecules into chains,
double chains or sheets in all cases except for compound (V).
For compound (II), there are three independent molecules per
asymmetric unit.
. . .
. . .
The average bond lengths show that C1 N1 and C1 N2
are of intermediate length between single and double bonds,
as is characteristic of delocalized amidines, and are identical
within their s.u. values. The C2 N3 bonds are short and more
characteristic of imines, while the N2—C2 bonds are longer
and approximate to single bonds. By contrast, the two C—N
bonds to which the –CCl3 group is attached in (Z)-2,2,2-
trichloro-N2-cyanoacetamidine differ in length by only
˚
´
0.008 A (Baker & Boere, 2009). The averaged bond lengths
are nearly identical, within their s.u. values, to the recently
´
reported trifluoromethyl series (Boere et al., 2011). Other
known structures of primary imidoylamidines include an
unusual chloroimidoylamidinium salt and two biguanides
Comment
N-Imidoylamidines (i.e. N0-imidoylcarboximidamides) are tri-
nitrogen analogues of pentadienes containing unsaturated
. . . . . . . . . . . .
N
C N C N chains which may have different degrees of
substitution at nitrogen. If the substituents at carbon are
further N-containing groups, the familiar biguanides are
obtained; imidoylamidines have carbon substituents on the
backbone C atoms. Primary N-imidoylamidines have three
ionizable H atoms on N atoms with the possibility of several
tautomeric structures. Tertiary exemplars retain a single
ionizable H atom. Both primary and, more commonly, tertiary
imidoylamidines are potent chelating ligands as deprotonated
monoanions. Applications of metal complexes of this ligand
type include the development of molecular magnets (Zheng et
al., 2007) and switches (Atkinson et al., 2002), and ꢀ-activation
agents for alkynes (Dias et al., 2009), as well as applications in
catalysis (Flores et al., 2009). Both the chemistry of the neutral
molecules and the coordination chemistry of the deprotonated
anions have recently been comprehensively reviewed (Kop-
Figure 1
Displacement ellipsoid plot (drawn at the 30% probability level) of (I) at
173 (2) K. The same atom-numbering scheme is used for (I)–(V), except
that in (II) the three independent molecules in the asymmetric unit have
suffixes A, B and C. All seven independent molecules display intra-
molecular N1ꢀ ꢀ ꢀN3 and N3ꢀ ꢀ ꢀCl2 hydrogen bonding within the crystal
structure, indicated by dotted lines.
Acta Cryst. (2011). C67, o273–o277
doi:10.1107/S0108270111023985
# 2011 International Union of Crystallography o273

organic compounds
[Cambridge Structural Database (Allen, 2002) refcodes
HDCADPZ (Privett et al., 1987); BIGUAN (Pinkerton &
Schwarzenbach, 1978) and BIGUAN01 (Ernst & Cagle, 1977);
NIWCAY (Zheng et al., 2007)]. The molecular structure of the
new compounds (I)–(V) is reminiscent of diiminoisoindoline
(Zhang, Njus et al., 2004), including the observation of the
amino tautomer in the solid state. Furthermore, the hydrogen-
bonding pattern in the new compounds is similar to that in di-
iminoisoindoline and 1-amino-3-phenyliminoisoindoline (Zhang,
Uth et al., 2004).
Figure 4
The intermolecular N1—H1ꢀ ꢀ ꢀN2 hydrogen bonds in (II) (dotted lines),
linking the three unique molecules into a threefold helix in the [100]
direction with a noncrystallographic threefold screw axis. The three
unique molecules A, B and C are shown, along with the adjacent
triazapenta-1,3-diene cores at either end. The view is approximately
perpendicular to the bc diagonal. Ellipsoids are shown at the 30%
probability level. [Symmetry codes: (i) x + 1, y, z; (iii) x ꢂ 1, y, z.]
The pentaazadiene cores of (I)–(V) are close to being
planar and form six-membered rings through N1—H2ꢀ ꢀ ꢀN3
Figure 5
Displacement ellipsoid plot (drawn at the 30% probability level) of (III)
at 173 (2) K.
Figure 2
The intermolecular N1—H1ꢀ ꢀ ꢀO1 hydrogen bonds in (I) (dotted lines),
linking the molecules into a twofold helix in the [010] direction. The two
(equivalent) linked molecules are viewed approximately down the b axis;
extension of the chain to the N1—H1 unit above and to atom O1 below is
also shown. Ellipsoids are shown at the 30% probability level. [Symmetry
hydrogen bonding [labelled Á in Scheme 2, which shows a
summary of the intra- (labelled Á and È) and intermolecular
(labelled À, Ã and Å) hydrogen bonds present in compounds
(I)–(V)]. Donor–acceptor Nꢀ ꢀ ꢀN distances for the Á inter-
1
1
1
1
codes: (i) ꢂx, y + , ꢂz ꢂ ; (iii) x, y + 1, z; (iv) ꢂx, y + , z ꢂ .]
2
2
2
2
˚
action are in the range 2.616 (2)–2.657 (4) A. The average
˚
distance in all seven independent molecules is 2.638 (14) A.
The related trifluoromethyl series displays a very similar
˚
´
Nꢀ ꢀ ꢀN distance of [2.66 (2) A] (Boere et al., 2011). Each
example also shows short N3—H3ꢀ ꢀ ꢀCl2 contacts (È in
Scheme 2), with an average donor–acceptor distance of
˚
2.984 (18) A. This weak contact is sufficient to orient atom Cl2
so that it is close to being coplanar with the pentaazadiene
core in all seven independent molecules.
The intermolecular hydrogen bonding is also very note-
worthy. Within the crystal structure, molecules of (I) are
linked by N1—H1ꢀ ꢀ ꢀO1i,iii hydrogen bonds that form a
twofold helix along the [010] direction (see Fig. 2 and Table 1
for symmetry codes). N3—H3ꢀ ꢀ ꢀCl3ii hydrogen bond (Å in
Scheme 2) serves to link the chains thus formed into two-
Figure 3
Displacement ellipsoid plot (drawn at the 30% probability level) of
molecule A of (II) at 173 (2) K.
ꢁ
´
o274 Boere et al. C10H10Cl3N3O and four analogues
Acta Cryst. (2011). C67, o273–o277

organic compounds
(V) does not display intermolecular hydrogen bonding,
presumably a consequence of the rather bulky CF3 group on
the aryl ring. In (II), (III) and (IV), hydrogen bonds of the
type N1—H1ꢀ ꢀ ꢀN2i,iii link a terminal NH2 group on one
molecule with the central (backbone) N atom of a neigh-
bouring molecule (Ã in Scheme 2). The average donor–
˚
acceptor distance for this interaction is 3.12 (3) A, which is
also, within the s.u. values, equal to such bonds in the
˚
trifluoromethyl series at 3.09 (9) A. While complete atom
Figure 6
The intermolecular N1—H1ꢀ ꢀ ꢀN2 hydrogen bonds in (III) (dotted lines),
forming chains of equivalent molecules aligned exactly with the ac
diagonal of the unit cell, resulting in a twofold helix along the [101]
direction. Compound (IV) is isomorphous with (III). Ellipsoids are
transfer would generate a diimine tautomer, all seven exam-
´
ples here and from the trifluoromethyl series (Boere et al.,
2011) show the single tautomeric form in the solid-state
structure. The terminal NH2 group is typically involved in ring-
forming (H2) and chain-forming (H1) interactions, while the
terminal NH group has contacts to atom Cl2 and, except in
(V), displays additional intermolecular interactions with other
Cl or Br atoms (À in Scheme 2). In molecule C of (II), there is
an additional intermolecular hydrogen bond between the
N1C—H1C group and atom Cl1B of a neighbouring CCl3
group (Ã in Scheme 2).
1
1
shown at the 30% probability level. [Symmetry codes: (i) x ꢂ , ꢂy + ,
2
2
1
2
1
2
1
2
1
2
z ꢂ ; (iii) x + , ꢂy + , z + ; (iv) x + 1, y, z + 1.]
Experimental
Compounds (I)–(V) were prepared using a modification of a litera-
ture procedure (Peters & Schaefer, 1964) by addition of trichloro-
acetonitrile to the corresponding para-substituted benzamidines in
acetonitrile. Crystals suitable for X-ray diffraction were grown by
vacuum sublimation in a three-zone tube furnace, or by slow cooling
of acetonitrile solutions [m.p. 377–379 K for (I), 341–342 K for (II),
384–386 K for (III), 371–372 K for (IV) and 369–370 K for (V)]. A
full hemisphere of data was collected for all five structures at low
temperature (173 K) using molybdenum radiation.
Figure 7
Displacement ellipsoid plot (drawn at the 30% probability level) of (IV)
at 173 (2) K.
Compound (I)
Crystal data
3
˚
C10H10Cl3N3O
Mr = 294.56
V = 1217.23 (17) A
Z = 4
Monoclinic, P21=c
Mo Kꢂ radiation
ꢃ = 0.74 mmꢂ1
T = 173 K
0.21 ꢄ 0.19 ꢄ 0.07 mm
˚
a = 12.0988 (10) A
˚
b = 8.6425 (7) A
˚
c = 12.2023 (10) A
ꢁ = 107.445 (1)ꢃ
Figure 8
Displacement ellipsoid plot (drawn at the 30% probability level) of (V) at
173 (2) K.
Data collection
Bruker APEXII CCD area-detector
diffractometer
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
Tmin = 0.697, Tmax = 0.746
17246 measured reflections
2812 independent reflections
2448 reflections with I > 2ꢄ(I)
Rint = 0.026
dimensional sheets that run parallel to (101) planes. More
significantly, the three independent molecules of (II) form
threefold helices along the [100] direction, defining a
noncrystallographic threefold screw axis through N1—H1ꢀ ꢀ ꢀ
N2i,iii contacts (see Fig. 4 and Table 2 for symmetry codes).
This helix is associated to a second related by inversion by the
N3B—H3Bꢀ ꢀ ꢀCl1Aii hydrogen bond (Å in Scheme 2), which
occurs only once in the asymmetric unit. In both (III) and
isomorphous (IV), there are twofold helices in the [100]
direction, also through N1—H1ꢀ ꢀ ꢀN2i,iii contacts (see Fig. 6 for
symmetry codes). This helical chain is expanded into a layer
along the (040) plane through the N3—H3ꢀ ꢀ ꢀCl4ii hydrogen
bond in (III) or N3—H3ꢀ ꢀ ꢀBr1ii in (IV) (Å in Scheme 2). Only
Table 1
Hydrogen-bond geometry (A, ) for (I).
ꢃ
˚
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
N1—H2ꢀ ꢀ ꢀN3
N3—H3ꢀ ꢀ ꢀCl2
N1—H1ꢀ ꢀ ꢀO1i
N3—H3ꢀ ꢀ ꢀCl3ii
0.86 (1)
0.86 (2)
0.85 (1)
0.86 (2)
2.00 (2)
2.43 (2)
2.20 (2)
2.76 (2)
2.647 (2)
132 (2)
123 (2)
166 (2)
134 (2)
2.9791 (15)
3.0315 (17)
3.4077 (15)
1
2
1
2
1
1
Symmetry codes: (i) ꢂx; y þ ; ꢂz ꢂ ; (ii) ꢂx þ 1; y þ ; ꢂz þ .
2
2
ꢁ
´
Acta Cryst. (2011). C67, o273–o277
Boere et al.
C10H10Cl3N3O and four analogues o275

organic compounds
Table 2
Hydrogen-bond geometry (A, ) for (II).
Table 5
Hydrogen-bond geometry (A, ) for (V).
ꢃ
ꢃ
˚
˚
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
N1A—H2Aꢀ ꢀ ꢀN3A
N3A—H3Aꢀ ꢀ ꢀCl2A
N1A—H1Aꢀ ꢀ ꢀN2Ci
N1B—H1Bꢀ ꢀ ꢀN2A
N3B—H3Bꢀ ꢀ ꢀCl2B
N1B—H2Bꢀ ꢀ ꢀN3B
N3B—H3Bꢀ ꢀ ꢀCl1Aii
N1C—H2Cꢀ ꢀ ꢀN3C
N3C—H3Cꢀ ꢀ ꢀCl2C
N1C—H1Cꢀ ꢀ ꢀN2B
N1C—H1Cꢀ ꢀ ꢀCl1B
0.89 (2)
0.88 (2)
0.88 (2)
0.87 (2)
0.88 (2)
0.89 (2)
0.88 (2)
0.89 (2)
0.87 (2)
0.87 (2)
0.87 (2)
1.99 (3)
2.38 (3)
2.26 (2)
2.28 (2)
2.41 (3)
1.94 (3)
2.91 (3)
1.91 (3)
2.47 (3)
2.24 (2)
2.90 (3)
2.657 (4)
2.969 (3)
3.126 (4)
3.136 (4)
2.978 (3)
2.646 (4)
3.383 (3)
2.644 (4)
3.023 (3)
3.072 (3)
3.511 (3)
130 (3)
125 (3)
172 (3)
171 (3)
122 (3)
135 (3)
115 (3)
138 (3)
122 (3)
160 (3)
128 (3)
N1—H2ꢀ ꢀ ꢀN3
N3—H3ꢀ ꢀ ꢀCl2
0.87 (2)
0.87 (2)
1.96 (2)
2.45 (2)
2.628 (2)
2.9779 (17)
133 (2)
119 (2)
Table 6
ꢃ
˚
Average bond lengths (A) and angles ( ) for compounds (I)–(V), and
comparison with the averages in two biguanides [CSD refcodes
BIGUAN01 (Ernst & Cagle, 1977) and NIWCAY (Zheng et al., 2007)].
Bond
Average
in (I)–(V)
Average in
biguanides
Angle
Average
in (I)–(V)
Average in
biguanides
Symmetry codes: (i) x þ 1; y; z; (ii) ꢂx þ 1; ꢂy þ 2; ꢂz.
N1—C1
C1—N2
N2—C2
C2—N3
C2—C3
C1—C4
1.327 (5)
1.323 (7)
1.370 (3)
1.278 (3)
1.552 (7)
1.488 (5)
1.325 (2)
1.329 (2)
1.382 (2)
1.295 (2)
N1—C1—N2
N1—C1—C4
C4—C1—N2
C1—N2—C2
N2—C2—N3
N2—C2—C3
N3—C2—C3
125.6 (2)
117.8 (4)
116.7 (3)
120.1 (2)
127.3 (3)
110.0 (4)
122.7 (4)
128.6 (2)
Table 3
Hydrogen-bond geometry (A, ) for (III).
ꢃ
˚
118.1 (2)
128.1 (2)
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
N1—H2ꢀ ꢀ ꢀN3
N3—H3ꢀ ꢀ ꢀCl2
N1—H1ꢀ ꢀ ꢀN2i
N1—H1ꢀ ꢀ ꢀCl1i
N3—H3ꢀ ꢀ ꢀCl4ii
0.87 (2)
0.88 (2)
0.87 (2)
0.87 (2)
0.88 (2)
1.92 (3)
2.42 (4)
2.68 (4)
2.95 (3)
2.85 (3)
2.628 (4)
2.982 (3)
3.125 (4)
3.507 (3)
3.585 (3)
137 (3)
122 (3)
113 (3)
124 (3)
143 (3)
Refinement
R[F2 > 2ꢄ(F2)] = 0.055
wR(F2) = 0.151
S = 0.97
7908 reflections
434 parameters
9 restraints
H atoms treated by a mixture of
independent and constrained
refinement
1
1
1
2
3
2
1
2
1
2
Symmetry codes: (i) x ꢂ ; ꢂy þ ; z ꢂ ; (ii) x ꢂ ; ꢂy þ ; z ꢂ .
2
2
ꢂ3
˚
Áꢅmax = 0.47 e A
ꢂ3
˚
Table 4
Hydrogen-bond geometry (A, ) for (IV).
Áꢅmin = ꢂ0.49 e A
ꢃ
˚
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
Compound (III)
N1—H2ꢀ ꢀ ꢀN3
N3—H3ꢀ ꢀ ꢀCl2
N1—H1ꢀ ꢀ ꢀN2i
N3—H3ꢀ ꢀ ꢀBr1ii
0.88 (2)
0.85 (2)
0.85 (2)
0.85 (2)
1.93 (2)
2.42 (2)
2.56 (2)
2.95 (2)
2.616 (2)
135 (2)
124 (2)
124 (2)
141 (2)
2.9809 (19)
3.116 (2)
3.6523 (18)
Crystal data
3
˚
V = 1221.7 (8) A
Z = 4
C9H7Cl4N3
Mr = 298.98
1
2
1
2
1
2
3
2
1
1
Symmetry codes: (i) x þ ; ꢂy þ ; z þ ; (ii) x þ ; ꢂy þ ; z þ .
Monoclinic, P21=n
Mo Kꢂ radiation
ꢃ = 0.94 mmꢂ1
T = 173 K
0.32 ꢄ 0.10 ꢄ 0.08 mm
2
2
˚
a = 5.762 (2) A
˚
b = 22.711 (8) A
˚
c = 9.713 (4) A
ꢁ = 106.031 (4)ꢃ
Refinement
R[F2 > 2ꢄ(F2)] = 0.026
wR(F2) = 0.064
S = 1.05
2812 reflections
164 parameters
3 restraints
H atoms treated by a mixture of
independent and constrained
refinement
Data collection
Bruker APEXII CCD area-detector
diffractometer
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
Tmin = 0.613, Tmax = 0.746
16666 measured reflections
2803 independent reflections
2248 reflections with I > 2ꢄ(I)
Rint = 0.041
ꢂ3
˚
Áꢅmax = 0.30 e A
ꢂ3
˚
Áꢅmin = ꢂ0.25 e A
Refinement
Compound (II)
R[F2 > 2ꢄ(F2)] = 0.050
wR(F2) = 0.122
S = 1.21
2803 reflections
154 parameters
3 restraints
H atoms treated by a mixture of
independent and constrained
refinement
Crystal data
C9H8Cl3N3
Mr = 264.53
Triclinic, P1
a = 10.2999 (3) A
b = 10.9423 (3) A
ꢆ = 81.5436 (11)ꢃ
ꢂ3
˚
Áꢅmax = 0.50 e A
3
˚
V = 1741.67 (8) A
Z = 6
ꢂ3
˚
Áꢅmin = ꢂ0.35 e A
˚
˚
˚
Mo Kꢂ radiation
ꢃ = 0.76 mmꢂ1
T = 173 K
0.18 ꢄ 0.15 ꢄ 0.10 mm
c = 15.6902 (4) A
Compound (IV)
ꢂ = 85.5518 (12)ꢃ
ꢁ = 86.5092 (12)ꢃ
Crystal data
3
˚
V = 1259.7 (6) A
Z = 4
C9H7BrCl3N3
Mr = 343.44
Data collection
Nonius KappaCCD area-detector
diffractometer
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
Tmin = 0.876, Tmax = 0.928
14588 measured reflections
7908 independent reflections
4900 reflections with I > 2ꢄ(I)
Rint = 0.076
Monoclinic, P21=n
Mo Kꢂ radiation
ꢃ = 3.87 mmꢂ1
T = 173 K
0.22 ꢄ 0.20 ꢄ 0.11 mm
˚
a = 5.8124 (17) A
˚
b = 23.379 (7) A
˚
c = 9.715 (3) A
ꢁ = 107.407 (3)ꢃ
ꢁ
´
o276 Boere et al. C10H10Cl3N3O and four analogues
Acta Cryst. (2011). C67, o273–o277

organic compounds
For all five compounds, data collection: APEX2 (Bruker, 2006);
cell refinement: SAINT-Plus (Bruker, 2006); data reduction: SAINT-
Plus; program(s) used to solve structure: SHELXS97 (Sheldrick,
2008); program(s) used to refine structure: SHELXTL (Sheldrick,
2008); molecular graphics: Mercury (Macrae et al., 2008); software
used to prepare material for publication: publCIF (Westrip, 2010).
Data collection
Bruker APEXII CCD area-detector
diffractometer
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
Tmin = 0.483, Tmax = 0.684
17762 measured reflections
2898 independent reflections
2563 reflections with I > 2ꢄ(I)
Rint = 0.068
Refinement
The authors acknowledge the University of Lethbridge, the
University of Calgary and the Natural Sciences and Engi-
neering Research Council for support, and NSERC and the
Canada Foundation for Innovation for the diffractometers.
R[F2 > 2ꢄ(F2)] = 0.024
wR(F2) = 0.062
S = 1.08
2898 reflections
157 parameters
H atoms treated by a mixture of
independent and constrained
refinement
ꢂ3
˚
Áꢅmax = 0.61 e A
ꢂ3
˚
Áꢅmin = ꢂ0.36 e A
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: YP3005). Services for accessing these data are
described at the back of the journal.
Compound (V)
Crystal data
3
References
˚
V = 1274.0 (3) A
Z = 4
C10H7Cl3F3N3
Mr = 332.54
Allen, F. H. (2002). Acta Cryst. B58, 380–388.
Atkinson, I. M., Bishop, M. M., Lindoy, L. F., Mahadev, S. & Turner, P. (2002).
Chem. Commun. pp. 2818–2819.
Monoclinic, P21=n
Mo Kꢂ radiation
ꢃ = 0.74 mmꢂ1
T = 173 K
0.25 ꢄ 0.25 ꢄ 0.12 mm
˚
a = 11.2939 (17) A
˚
b = 8.3914 (13) A
´
Baker, A. E. & Boere, R. T. (2009). Acta Cryst. E65, o2134–o2135.
Boere, R. T., Roemmele, T. L. & Yu, X. (2011). Inorg. Chem. 50, 5123–5136.
˚
c = 13.505 (2) A
´
ꢁ = 95.505 (2)ꢃ
Bruker (2006). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc.,
Madison, Wisconsin, USA.
Data collection
Dias, H. V. R., Flores, J. A., Wu, J. & Kroll, P. (2009). J. Am. Chem. Soc. 131,
11249–11255.
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(2009). J. Organomet. Chem. 694, 7648–7652.
Bruker APEXII CCD area-detector
diffractometer
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
Tmin = 0.699, Tmax = 0.746
18460 measured reflections
3191 independent reflections
2862 reflections with I > 2ꢄ(I)
Rint = 0.018
Kopylovich, M. N. & Pombeiro, A. J. L. (2011). Coord. Chem. Rev. 255, 339–
355.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P.,
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P. A. (2008). J. Appl. Cryst. 41, 466–470.
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Pinkerton, A. A. & Schwarzenbach, D. (1978). J. Chem. Soc. Dalton Trans. pp.
989–996.
Refinement
R[F2 > 2ꢄ(F2)] = 0.036
wR(F2) = 0.098
S = 1.06
3191 reflections
181 parameters
3 restraints
H atoms treated by a mixture of
independent and constrained
refinement
ꢂ3
˚
Áꢅmax = 0.90 e A
ꢂ3
˚
Privett, A. J., Craig, S. L., Jeter, D. Y., Cordes, A. W., Oakley, R. T. & Reed,
R. W. (1987). Acta Cryst. C43, 2023–2025.
Áꢅmin = ꢂ0.58 e A
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
Zhang, Z.-Q., Njus, J. M., Sandman, D. J., Guo, C., Foxman, B. M., Erk, P. &
van Gelder, R. (2004). Chem. Commun. pp. 886–887.
Zhang, Z.-Q., Uth, S., Sandman, D. J. & Foxman, B. M. (2004). J. Phys. Org.
Chem. 17, 769–776.
˚
C-bound H atoms were treated as riding, with C—H = 0.98 A and
˚
Uiso(H) = 1.5Ueq(C) for methyl and C—H = 0.95–0.96 A and Uiso(H) =
1.2Ueq(C) for all other H atoms. The three N-bound H-atom positions
˚
were refined using a distance restraint of 0.88 A and with Uiso(H) =
1.2Ueq(N).
Zheng, L.-L., Zhang, W.-X., Qin, L.-J., Leng, J.-D., Lu, J.-X. & Tong, M.-L.
(2007). Inorg. Chem. 46, 9548–9557.
ꢁ
´
Acta Cryst. (2011). C67, o273–o277
Boere et al.
C10H10Cl3N3O and four analogues o277