(Z)-Ethyl 3-(4-chloro­benzamido)-2-cyano-3-(4-fluoro­phen­yl)acrylate

Zhang, D.; Zhang, X.; Guo, L.

doi:10.1107/S1600536808041469

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o90

doi:10.1107/S1600536808041469

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(Z)-Ethyl 3-(4-chlorobenzamido)-2-cyano-3-(4-fluorophenyl)acrylate

Dehua Zhang,^a ^* Xiaoyan Zhang ^b and Lijuan Guo ^c

^aDepartment of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002, People's Republic of China, ^bSchool of Mathematics and Physics, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China, and ^cDepartment of Chemistry, Changsha Medical University, Changsha 410219, People's Republic of China
^*Correspondence e-mail: zhangdehua200@163.com

(Received 2 December 2008; accepted 8 December 2008; online 10 December 2008)

The title compound, C₁₉H₁₄ClFN₂O₃, was prepared by the reaction of ethyl (Z)-3-amino-2-cyano-3-(4-fluorophenyl)acrylate and 4-chlorobenzoyl chloride. The dihedral angle between the chlorobenzene and fluorobenzene rings is 66.18 (19)°. In addition to an intramolecular N—H⋯O hydrogen bond, there are intermolecular C—H⋯O and C—H⋯N hydrogen bonding interactions, which stabilize the crystal structure.

Related literature

For the agrochemical activity of the title compound, see: Heller et al. (2004 ); Ibers & Hamilton (1964 ).

Experimental

Crystal data

C₁₉H₁₄ClFN₂O₃
M_r = 372.77
Monoclinic, P 2₁ /c
a = 6.1429 (5) Å
b = 13.1555 (6) Å
c = 22.9263 (10) Å
β = 92.280 (4)°
V = 1851.27 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 (2) K
0.40 × 0.20 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: none
23332 measured reflections
3259 independent reflections
2138 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.140
S = 1.07
3259 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	2.00	2.668 (3)	134
C3—H3⋯N2ⁱ	0.93	2.53	3.314 (5)	143
C6—H6⋯O1ⁱⁱ	0.93	2.41	3.170 (4)	140
C14—H14⋯N2ⁱⁱⁱ	0.93	2.55	3.463 (5)	169
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z; (iii) x+1, y, z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808041469/rz2277sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808041469/rz2277Isup2.hkl

checkCIF report

Comment top

Recently, 2-cyanoacrylates have been extensively used as agrochemicals because of their unique mechanism of action and good environmental profiles. The title compound is useful as an inhibitor of Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea and Gibberella zeae (Heller et al., 2004; Ibers & Hamilton, 1964).

In the title compound (Fig.1), all bond lengths and angles are unexcepional. The aromatic rings of the chlorobenzene and fluorobenzene groups form a dihedral angle of 66.18 (19)°. The molecular conformation is stabilized by an intramolecular N—H···O hydrogen bond (Table 1). The crystal packing is governed by C—H···O and C—H···N hydrogen interactions (Fig.2) resulting in a three-dimensional network.

Related literature top

For the agrochemical activity of the title compound, see: Heller et al. (2004); Ibers & Hamilton (1964).

Experimental top

To a solution of ethyl (2Z)-3-amino-2-cyano-3-(4-fluorophenyl)acrylate (1.17 g, 0.0050 mol) in CH₂Cl₂ (18 ml), 4-chlorobenzoyl chloride (2.63 g, 0.015 mol) was added. Subsequently, Et₃N (1.52 g, 0.015 mol) was dropped into the solution under stirring. The reaction mixture was then heated to reflux, stirred for 4 h and cooled to room temperature. The reaction solution was filtered off and some white solid was separated. The organic phase was washed with water and then dried over Na₂SO₄. After removal of the solvent, a brown dope was obtained. The title compound was isolated by column chromatography using ethyl acetate/light petroleum (1:6 v/v) as eluent. Single crystals suitable for X-ray analysis were obtained by slow evaporation at room temperature of an ethyl acetate/petroleum ether (3:1 v/v) solution after 45 days.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of The title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Packing diagram of the title compound, viewed approximately along the a axis. Hydrogen bonds are shown as dashed lines.

(Z)-Ethyl 3-(4-chlorobenzamido)-2-cyano-3-(4-fluorophenyl)acrylate top

Crystal data top

C₁₉H₁₄ClFN₂O₃	F(000) = 768
M_r = 372.77	D_x = 1.337 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1253 reflections
a = 6.1429 (5) Å	θ = 3.1–20.3°
b = 13.1555 (6) Å	µ = 0.24 mm⁻¹
c = 22.9263 (10) Å	T = 298 K
β = 92.280 (4)°	Block, colourless
V = 1851.27 (19) Å³	0.40 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2138 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.053
Graphite monochromator	θ_max = 25.0°, θ_min = 1.8°
phi and ω scans	h = −7→7
23332 measured reflections	k = −15→15
3259 independent reflections	l = −24→27

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0335P)² + 1.3651P] where P = (F_o² + 2F_c²)/3
3259 reflections	(Δ/σ)_max = 0.001
236 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₉H₁₄ClFN₂O₃	V = 1851.27 (19) Å³
M_r = 372.77	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.1429 (5) Å	µ = 0.24 mm⁻¹
b = 13.1555 (6) Å	T = 298 K
c = 22.9263 (10) Å	0.40 × 0.20 × 0.10 mm
β = 92.280 (4)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2138 reflections with I > 2σ(I)
23332 measured reflections	R_int = 0.053
3259 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.07	Δρ_max = 0.25 e Å⁻³
3259 reflections	Δρ_min = −0.23 e Å⁻³
236 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.4513 (5)	0.4421 (2)	0.11848 (12)	0.0510 (7)
C2	0.4752 (5)	0.3939 (2)	0.17187 (14)	0.0613 (9)
H2	0.3761	0.4064	0.2006	0.074*
C3	0.6452 (6)	0.3273 (3)	0.18272 (14)	0.0670 (9)
H3	0.6599	0.2942	0.2185	0.080*
C4	0.7924 (5)	0.3099 (2)	0.14056 (15)	0.0626 (9)
C5	0.7716 (6)	0.3559 (3)	0.08732 (15)	0.0696 (9)
H5	0.8718	0.3431	0.0589	0.084*
C6	0.6006 (6)	0.4213 (2)	0.07632 (14)	0.0673 (9)
H6	0.5848	0.4523	0.0399	0.081*
C7	0.2778 (5)	0.5173 (2)	0.10220 (14)	0.0582 (8)
C8	−0.0191 (5)	0.6171 (2)	0.14507 (13)	0.0531 (8)
C9	−0.0435 (5)	0.6899 (2)	0.09582 (13)	0.0557 (8)
C10	−0.2251 (6)	0.6897 (3)	0.05965 (16)	0.0790 (11)
H10	−0.3308	0.6400	0.0642	0.095*
C11	−0.2547 (7)	0.7618 (3)	0.01659 (16)	0.0873 (12)
H11	−0.3779	0.7598	−0.0083	0.105*
C12	−0.1070 (8)	0.8340 (3)	0.01079 (16)	0.0870 (13)
C13	0.0819 (9)	0.8367 (3)	0.04453 (19)	0.1072 (16)
H13	0.1867	0.8863	0.0388	0.129*
C14	0.1124 (7)	0.7635 (3)	0.08740 (17)	0.0879 (12)
H14	0.2395	0.7638	0.1108	0.106*
C15	−0.1571 (5)	0.6200 (2)	0.18996 (13)	0.0539 (8)
C16	−0.3251 (6)	0.6945 (3)	0.18956 (14)	0.0667 (9)
C17	−0.1424 (5)	0.5506 (2)	0.24042 (13)	0.0561 (8)
C18	−0.3118 (6)	0.4975 (3)	0.32660 (15)	0.0742 (10)
H18A	−0.1840	0.5102	0.3518	0.089*
H18B	−0.3126	0.4264	0.3155	0.089*
C19	−0.5130 (7)	0.5229 (4)	0.35748 (17)	0.1065 (15)
H19A	−0.5114	0.5937	0.3677	0.160*
H19B	−0.5193	0.4826	0.3923	0.160*
H19C	−0.6383	0.5088	0.3324	0.160*
Cl1	1.00991 (17)	0.22922 (8)	0.15591 (5)	0.0969 (4)
F1	−0.1365 (6)	0.90693 (18)	−0.03083 (11)	0.1356 (11)
N1	0.1499 (4)	0.54859 (19)	0.14698 (10)	0.0595 (7)
H1	0.1799	0.5216	0.1805	0.071*
N2	−0.4597 (6)	0.7536 (3)	0.19023 (14)	0.0981 (12)
O1	0.2500 (5)	0.5501 (2)	0.05344 (10)	0.0940 (9)
O2	0.0048 (4)	0.49015 (17)	0.24988 (10)	0.0701 (6)
O3	−0.3085 (4)	0.56200 (16)	0.27479 (9)	0.0628 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0583 (19)	0.0492 (16)	0.0460 (17)	−0.0001 (14)	0.0068 (15)	0.0007 (14)
C2	0.065 (2)	0.064 (2)	0.056 (2)	0.0058 (17)	0.0166 (17)	0.0054 (16)
C3	0.076 (2)	0.070 (2)	0.055 (2)	0.0070 (19)	0.0057 (18)	0.0142 (17)
C4	0.066 (2)	0.0532 (18)	0.069 (2)	0.0047 (16)	0.0076 (18)	0.0025 (16)
C5	0.077 (2)	0.073 (2)	0.061 (2)	0.0152 (19)	0.0198 (18)	0.0022 (18)
C6	0.085 (3)	0.066 (2)	0.0522 (19)	0.0133 (19)	0.0115 (18)	0.0070 (16)
C7	0.069 (2)	0.0603 (19)	0.0460 (19)	0.0017 (16)	0.0124 (16)	0.0019 (15)
C8	0.060 (2)	0.0509 (17)	0.0482 (18)	0.0018 (15)	−0.0006 (15)	−0.0051 (14)
C9	0.064 (2)	0.0523 (18)	0.0514 (18)	0.0036 (16)	0.0030 (16)	−0.0038 (15)
C10	0.083 (3)	0.086 (3)	0.067 (2)	−0.013 (2)	−0.011 (2)	0.013 (2)
C11	0.093 (3)	0.099 (3)	0.067 (2)	0.003 (3)	−0.025 (2)	0.008 (2)
C12	0.137 (4)	0.056 (2)	0.066 (2)	0.008 (2)	−0.021 (3)	0.0120 (19)
C13	0.150 (4)	0.066 (2)	0.102 (3)	−0.032 (3)	−0.038 (3)	0.026 (2)
C14	0.109 (3)	0.069 (2)	0.083 (3)	−0.014 (2)	−0.032 (2)	0.012 (2)
C15	0.060 (2)	0.0543 (17)	0.0471 (18)	0.0084 (15)	0.0011 (15)	−0.0003 (14)
C16	0.073 (2)	0.077 (2)	0.050 (2)	0.019 (2)	0.0033 (17)	0.0008 (17)
C17	0.057 (2)	0.0577 (19)	0.0537 (19)	0.0008 (16)	0.0027 (16)	−0.0077 (16)
C18	0.086 (3)	0.076 (2)	0.060 (2)	−0.013 (2)	0.0093 (19)	0.0138 (18)
C19	0.095 (3)	0.155 (4)	0.072 (3)	0.002 (3)	0.028 (2)	0.021 (3)
Cl1	0.0849 (7)	0.0965 (7)	0.1095 (8)	0.0329 (6)	0.0085 (6)	0.0214 (6)
F1	0.226 (3)	0.0791 (16)	0.0970 (18)	0.0063 (18)	−0.0458 (19)	0.0293 (14)
N1	0.0694 (18)	0.0653 (16)	0.0443 (14)	0.0139 (14)	0.0072 (13)	0.0055 (12)
N2	0.105 (3)	0.122 (3)	0.068 (2)	0.053 (2)	0.0133 (19)	0.0078 (19)
O1	0.110 (2)	0.119 (2)	0.0542 (15)	0.0513 (17)	0.0204 (14)	0.0236 (15)
O2	0.0746 (16)	0.0726 (14)	0.0636 (14)	0.0142 (13)	0.0100 (12)	0.0111 (12)
O3	0.0666 (14)	0.0682 (13)	0.0543 (13)	0.0006 (11)	0.0105 (11)	0.0010 (11)

Geometric parameters (Å, º) top

C1—C2	1.381 (4)	C11—C12	1.324 (5)
C1—C6	1.386 (4)	C11—H11	0.9300
C1—C7	1.491 (4)	C12—F1	1.361 (4)
C2—C3	1.378 (4)	C12—C13	1.369 (6)
C2—H2	0.9300	C13—C14	1.383 (5)
C3—C4	1.369 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.364 (4)	C15—C16	1.423 (5)
C4—Cl1	1.732 (3)	C15—C17	1.473 (4)
C5—C6	1.374 (4)	C16—N2	1.135 (4)
C5—H5	0.9300	C17—O2	1.217 (4)
C6—H6	0.9300	C17—O3	1.322 (4)
C7—O1	1.204 (4)	C18—O3	1.461 (4)
C7—N1	1.380 (4)	C18—C19	1.487 (5)
C8—C15	1.360 (4)	C18—H18A	0.9700
C8—N1	1.374 (4)	C18—H18B	0.9700
C8—C9	1.484 (4)	C19—H19A	0.9600
C9—C10	1.363 (4)	C19—H19B	0.9600
C9—C14	1.381 (5)	C19—H19C	0.9600
C10—C11	1.376 (5)	N1—H1	0.8600
C10—H10	0.9300

C2—C1—C6	118.5 (3)	C11—C12—F1	120.2 (4)
C2—C1—C7	125.2 (3)	C11—C12—C13	122.1 (4)
C6—C1—C7	116.3 (3)	F1—C12—C13	117.7 (4)
C3—C2—C1	120.4 (3)	C12—C13—C14	118.1 (4)
C3—C2—H2	119.8	C12—C13—H13	121.0
C1—C2—H2	119.8	C14—C13—H13	121.0
C4—C3—C2	119.7 (3)	C9—C14—C13	120.8 (4)
C4—C3—H3	120.2	C9—C14—H14	119.6
C2—C3—H3	120.2	C13—C14—H14	119.6
C5—C4—C3	121.2 (3)	C8—C15—C16	119.2 (3)
C5—C4—Cl1	119.9 (3)	C8—C15—C17	123.8 (3)
C3—C4—Cl1	119.0 (3)	C16—C15—C17	117.0 (3)
C4—C5—C6	119.1 (3)	N2—C16—C15	178.8 (4)
C4—C5—H5	120.5	O2—C17—O3	123.6 (3)
C6—C5—H5	120.5	O2—C17—C15	124.5 (3)
C5—C6—C1	121.2 (3)	O3—C17—C15	111.9 (3)
C5—C6—H6	119.4	O3—C18—C19	107.2 (3)
C1—C6—H6	119.4	O3—C18—H18A	110.3
O1—C7—N1	121.3 (3)	C19—C18—H18A	110.3
O1—C7—C1	122.9 (3)	O3—C18—H18B	110.3
N1—C7—C1	115.7 (3)	C19—C18—H18B	110.3
C15—C8—N1	119.2 (3)	H18A—C18—H18B	108.5
C15—C8—C9	120.7 (3)	C18—C19—H19A	109.5
N1—C8—C9	120.1 (3)	C18—C19—H19B	109.5
C10—C9—C14	118.1 (3)	H19A—C19—H19B	109.5
C10—C9—C8	121.1 (3)	C18—C19—H19C	109.5
C14—C9—C8	120.6 (3)	H19A—C19—H19C	109.5
C9—C10—C11	121.1 (4)	H19B—C19—H19C	109.5
C9—C10—H10	119.4	C8—N1—C7	128.6 (3)
C11—C10—H10	119.4	C8—N1—H1	115.7
C12—C11—C10	119.7 (4)	C7—N1—H1	115.7
C12—C11—H11	120.2	C17—O3—C18	117.1 (3)
C10—C11—H11	120.2

C6—C1—C2—C3	0.5 (5)	C10—C11—C12—C13	3.4 (7)
C7—C1—C2—C3	−178.5 (3)	C11—C12—C13—C14	−2.7 (7)
C1—C2—C3—C4	0.8 (5)	F1—C12—C13—C14	179.3 (4)
C2—C3—C4—C5	−1.3 (5)	C10—C9—C14—C13	1.9 (6)
C2—C3—C4—Cl1	177.9 (3)	C8—C9—C14—C13	−174.7 (4)
C3—C4—C5—C6	0.6 (5)	C12—C13—C14—C9	0.0 (7)
Cl1—C4—C5—C6	−178.6 (3)	N1—C8—C15—C16	176.6 (3)
C4—C5—C6—C1	0.7 (5)	C9—C8—C15—C16	−0.5 (5)
C2—C1—C6—C5	−1.3 (5)	N1—C8—C15—C17	−2.5 (5)
C7—C1—C6—C5	177.8 (3)	C9—C8—C15—C17	−179.7 (3)
C2—C1—C7—O1	−172.5 (3)	C8—C15—C17—O2	7.0 (5)
C6—C1—C7—O1	8.5 (5)	C16—C15—C17—O2	−172.2 (3)
C2—C1—C7—N1	8.1 (5)	C8—C15—C17—O3	−173.4 (3)
C6—C1—C7—N1	−170.9 (3)	C16—C15—C17—O3	7.4 (4)
C15—C8—C9—C10	−64.0 (4)	C15—C8—N1—C7	164.6 (3)
N1—C8—C9—C10	118.9 (4)	C9—C8—N1—C7	−18.2 (5)
C15—C8—C9—C14	112.5 (4)	O1—C7—N1—C8	0.0 (5)
N1—C8—C9—C14	−64.7 (4)	C1—C7—N1—C8	179.4 (3)
C14—C9—C10—C11	−1.2 (6)	O2—C17—O3—C18	−0.1 (4)
C8—C9—C10—C11	175.4 (3)	C15—C17—O3—C18	−179.7 (3)
C9—C10—C11—C12	−1.4 (6)	C19—C18—O3—C17	−179.3 (3)
C10—C11—C12—F1	−178.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.00	2.668 (3)	134
C3—H3···N2ⁱ	0.93	2.53	3.314 (5)	143
C6—H6···O1ⁱⁱ	0.93	2.41	3.170 (4)	140
C14—H14···N2ⁱⁱⁱ	0.93	2.55	3.463 (5)	169

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄ClFN₂O₃
M_r	372.77
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	6.1429 (5), 13.1555 (6), 22.9263 (10)
β (°)	92.280 (4)
V (Å³)	1851.27 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	23332, 3259, 2138
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.140, 1.07
No. of reflections	3259
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.23

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.00	2.668 (3)	133.9
C3—H3···N2ⁱ	0.93	2.53	3.314 (5)	142.8
C6—H6···O1ⁱⁱ	0.93	2.41	3.170 (4)	139.5
C14—H14···N2ⁱⁱⁱ	0.93	2.55	3.463 (5)	169.1

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

References

Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Heller, D., Drexler, H. J., You, J. & Zhang, S. L. (2004). WO Patent 011 414. Google Scholar
Ibers, J. A. & Hamilton, W. C. (1964). Acta Cryst. 17, 781–782. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o90

doi:10.1107/S1600536808041469

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