(E)-Methyl 2,6-dichloro-N-cyano-benzimidate.

The mol-ecule of the title compound, C(9)H(6)Cl(2)N(2)O, displays an E conformation about the C=N double bond. The N-cyano-imidate fragment is substanti-ally planar [maximum deviation 0.010 (4) Å] and perpendicular to the benzene ring [dihedral angle = 88.50 (14)°]. In the crystal packing, inter-molecular Cl⋯Cl inter-actions [3.490 (2) Å] are observed.

Related literature

For the synthesis of substituted cyano­imidates, see: Huffman & Schaefer (1963 ▶). For the crystal structures of compounds containing the N-cyano­imidate fragment, see: Zöllinger et al. (2006 ▶); Ponomareva et al. (1995 ▶); Jäger et al. (1996 ▶). For details of halogen⋯halogen inter­actions, see: Desiraju & Parthasarathy (1989 ▶).

Experimental

Crystal data

C9H6Cl2N2O

M = 229.06

Monoclinic,

a = 21.199 (4) Å

b = 8.548 (3) Å

c = 15.005 (4) Å

β = 128.49 (4)°

V = 2128.2 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.58 mm−1

T = 291 K

0.52 × 0.46 × 0.28 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: spherical (WinGX; Farrugia, 1999 ▶) T min = 0.754, T max = 0.855

2116 measured reflections

1948 independent reflections

1167 reflections with I > 2σ(I)

R int = 0.016

3 standard reflections every 120 reflections intensity decay: 3.8%

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.170

S = 1.04

1948 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.32 e Å−3

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026452/rz2343sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026452/rz2343Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H6Cl2N2O	F(000) = 928
Mr = 229.06	Dx = 1.430 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 28 reflections
a = 21.199 (4) Å	θ = 4.8–9.2°
b = 8.548 (3) Å	µ = 0.58 mm−1
c = 15.005 (4) Å	T = 291 K
β = 128.49 (4)°	Block, colourless
V = 2128.2 (16) Å3	0.52 × 0.46 × 0.28 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	1167 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
graphite	θmax = 25.5°, θmin = 2.5°
ω/2θ scans	h = −25→17
Absorption correction: for a sphere (WinGX; Farrugia, 1999)	k = 0→10
Tmin = 0.754, Tmax = 0.855	l = −18→18
2116 measured reflections	3 standard reflections every 120 reflections
1948 independent reflections	intensity decay: 3.8%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054	H-atom parameters constrained
wR(F2) = 0.170	w = 1/[σ2(Fo2) + (0.1053P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1948 reflections	Δρmax = 0.30 e Å−3
129 parameters	Δρmin = −0.32 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0069 (15)

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.

	x	y	z	Uiso*/Ueq
Cl1	0.54862 (5)	0.67130 (14)	0.65350 (8)	0.0881 (5)
Cl2	0.24528 (6)	0.72469 (18)	0.26898 (9)	0.1121 (6)
O1	0.36902 (14)	0.4760 (2)	0.5066 (2)	0.0672 (7)
N1	0.35148 (15)	0.7020 (3)	0.5663 (2)	0.0563 (7)
N2	0.3600 (2)	0.9913 (4)	0.5784 (3)	0.0866 (10)
C1	0.40050 (16)	0.7037 (3)	0.4547 (2)	0.0472 (7)
C2	0.48117 (18)	0.7300 (3)	0.5135 (3)	0.0545 (8)
C3	0.5094 (2)	0.8077 (4)	0.4632 (3)	0.0675 (9)
H3	0.5642	0.8259	0.5039	0.081*
C4	0.4550 (3)	0.8571 (4)	0.3523 (3)	0.0745 (10)
H4	0.4735	0.9086	0.3179	0.089*
C5	0.3742 (2)	0.8318 (4)	0.2917 (3)	0.0750 (10)
H5	0.3379	0.8664	0.2169	0.090*
C6	0.3471 (2)	0.7542 (4)	0.3432 (3)	0.0613 (9)
C7	0.37157 (16)	0.6295 (3)	0.5129 (2)	0.0486 (7)
C8	0.3474 (3)	0.3932 (4)	0.5685 (4)	0.0930 (13)
H8A	0.3881	0.4102	0.6487	0.139*
H8B	0.3433	0.2833	0.5525	0.139*
H8C	0.2966	0.4312	0.5453	0.139*
C9	0.3568 (2)	0.8581 (4)	0.5699 (3)	0.0619 (8)

	U11	U22	U33	U12	U13	U23
Cl1	0.0583 (5)	0.1217 (9)	0.0646 (6)	0.0019 (5)	0.0285 (5)	0.0127 (5)
Cl2	0.0589 (6)	0.1721 (13)	0.0731 (7)	−0.0024 (6)	0.0252 (5)	0.0231 (7)
O1	0.0903 (16)	0.0367 (12)	0.0958 (17)	0.0011 (10)	0.0684 (15)	0.0009 (10)
N1	0.0733 (17)	0.0436 (14)	0.0707 (16)	−0.0010 (11)	0.0540 (15)	0.0000 (11)
N2	0.129 (3)	0.0544 (18)	0.122 (3)	−0.0121 (17)	0.100 (3)	−0.0177 (17)
C1	0.0566 (16)	0.0401 (14)	0.0550 (16)	0.0025 (12)	0.0397 (14)	−0.0008 (12)
C2	0.0587 (17)	0.0537 (17)	0.0574 (17)	0.0016 (13)	0.0393 (15)	−0.0039 (13)
C3	0.0639 (19)	0.070 (2)	0.087 (2)	−0.0075 (16)	0.056 (2)	−0.0115 (18)
C4	0.103 (3)	0.069 (2)	0.090 (3)	0.000 (2)	0.079 (2)	0.0017 (19)
C5	0.096 (3)	0.078 (2)	0.066 (2)	0.013 (2)	0.058 (2)	0.0132 (18)
C6	0.0620 (18)	0.068 (2)	0.0564 (18)	0.0022 (15)	0.0382 (16)	0.0003 (15)
C7	0.0502 (15)	0.0413 (15)	0.0535 (16)	0.0004 (12)	0.0319 (13)	−0.0001 (12)
C8	0.123 (3)	0.050 (2)	0.144 (4)	−0.004 (2)	0.101 (3)	0.014 (2)
C9	0.080 (2)	0.055 (2)	0.076 (2)	−0.0076 (16)	0.0612 (19)	−0.0101 (16)

Cl1—C2	1.724 (3)	C2—C3	1.389 (4)
Cl2—C6	1.724 (4)	C3—C4	1.374 (5)
O1—C7	1.314 (3)	C3—H3	0.9300
O1—C8	1.451 (4)	C4—C5	1.367 (5)
N1—C7	1.278 (4)	C4—H4	0.9300
N1—C9	1.338 (4)	C5—C6	1.385 (5)
N2—C9	1.143 (4)	C5—H5	0.9300
C1—C2	1.370 (4)	C8—H8A	0.9600
C1—C6	1.382 (4)	C8—H8B	0.9600
C1—C7	1.486 (4)	C8—H8C	0.9600
C7—O1—C8	117.2 (3)	C4—C5—H5	120.4
C7—N1—C9	117.1 (3)	C6—C5—H5	120.4
C2—C1—C6	118.8 (3)	C1—C6—C5	120.9 (3)
C2—C1—C7	119.9 (3)	C1—C6—Cl2	119.2 (3)
C6—C1—C7	121.3 (3)	C5—C6—Cl2	119.8 (3)
C1—C2—C3	121.1 (3)	N1—C7—O1	121.0 (3)
C1—C2—Cl1	119.5 (2)	N1—C7—C1	125.6 (2)
C3—C2—Cl1	119.4 (2)	O1—C7—C1	113.4 (2)
C4—C3—C2	119.0 (3)	O1—C8—H8A	109.5
C4—C3—H3	120.5	O1—C8—H8B	109.5
C2—C3—H3	120.5	H8A—C8—H8B	109.5
C5—C4—C3	121.1 (3)	O1—C8—H8C	109.5
C5—C4—H4	119.5	H8A—C8—H8C	109.5
C3—C4—H4	119.5	H8B—C8—H8C	109.5
C4—C5—C6	119.2 (3)	N2—C9—N1	174.8 (4)
C6—C1—C2—C3	0.8 (4)	C7—C1—C6—Cl2	−2.1 (4)
C7—C1—C2—C3	−176.1 (3)	C4—C5—C6—C1	0.6 (5)
C6—C1—C2—Cl1	178.8 (2)	C4—C5—C6—Cl2	178.7 (3)
C7—C1—C2—Cl1	1.9 (4)	C9—N1—C7—O1	179.2 (3)
C1—C2—C3—C4	−0.6 (5)	C9—N1—C7—C1	0.2 (4)
Cl1—C2—C3—C4	−178.6 (3)	C8—O1—C7—N1	−3.7 (4)
C2—C3—C4—C5	0.4 (5)	C8—O1—C7—C1	175.4 (3)
C3—C4—C5—C6	−0.4 (5)	C2—C1—C7—N1	89.7 (4)
C2—C1—C6—C5	−0.8 (5)	C6—C1—C7—N1	−87.1 (4)
C7—C1—C6—C5	176.0 (3)	C2—C1—C7—O1	−89.4 (3)
C2—C1—C6—Cl2	−178.9 (2)	C6—C1—C7—O1	93.8 (3)