2,6-Dichloro-benzaldehyde oxime.

In the title compound, C(7)H(5)Cl(2)NO, there are two mol-ecules in the asymmetric unit. The mol-ecules are essentially identical. Each mol-ecule is connected to a symmetry-related mol-ecule through an inversion center by O-H⋯N hydrogen bonds, building an R(2) (2)(6) graph-set motif.

Related literature

For related literature, see: Xu & Jin (1999 ▶). For graph-set notation, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H5Cl2NO

M = 190.02

Triclinic,

a = 3.8074 (1) Å

b = 14.3712 (2) Å

c = 14.3835 (3) Å

α = 89.108 (1)°

β = 88.545 (1)°

γ = 85.296 (1)°

V = 784.04 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.76 mm−1

T = 296 (2) K

0.26 × 0.24 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.818, T max = 0.884

11107 measured reflections

3235 independent reflections

2809 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.06

3235 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033217/dn2391sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033217/dn2391Isup2.hkl

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

C7H5Cl2NO	Z = 4
Mr = 190.02	F(000) = 384
Triclinic, P1	Dx = 1.610 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.8074 (1) Å	Cell parameters from 5529 reflections
b = 14.3712 (2) Å	θ = 2.8–27.4°
c = 14.3835 (3) Å	µ = 0.76 mm−1
α = 89.108 (1)°	T = 296 K
β = 88.545 (1)°	Block, colourless
γ = 85.296 (1)°	0.26 × 0.24 × 0.16 mm
V = 784.04 (3) Å3

Bruker SMART CCD area-detector diffractometer	3235 independent reflections
Radiation source: fine-focus sealed tube	2809 reflections with I > 2σ(I)
graphite	Rint = 0.018
ω scans	θmax = 26.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −4→4
Tmin = 0.818, Tmax = 0.884	k = −17→17
11107 measured reflections	l = −18→18

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0352P)2 + 0.3155P] where P = (Fo2 + 2Fc2)/3
3235 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.16981 (16)	0.12516 (3)	1.04669 (4)	0.06328 (16)
Cl2	−0.28140 (15)	0.39071 (3)	0.79443 (4)	0.05813 (16)
N1	−0.0849 (4)	0.39836 (10)	0.99884 (10)	0.0430 (3)
O1	−0.2185 (4)	0.44211 (9)	1.07941 (9)	0.0574 (4)
H1	−0.1779	0.4973	1.0774	0.086*
C1	−0.0441 (4)	0.25470 (11)	0.91699 (11)	0.0371 (4)
C2	0.1056 (5)	0.16371 (12)	0.93282 (13)	0.0426 (4)
C3	0.2132 (6)	0.10360 (13)	0.86200 (16)	0.0551 (5)
H3	0.3128	0.0437	0.8752	0.066*
C4	0.1703 (7)	0.13390 (15)	0.77145 (16)	0.0653 (6)
H4	0.2431	0.0943	0.7229	0.078*
C5	0.0202 (6)	0.22243 (15)	0.75209 (14)	0.0599 (5)
H5	−0.0105	0.2422	0.6908	0.072*
C6	−0.0839 (5)	0.28136 (12)	0.82397 (13)	0.0434 (4)
C7	−0.1573 (5)	0.31429 (12)	0.99624 (12)	0.0416 (4)
H7	−0.2847	0.2895	1.0454	0.050*
Cl3	0.60840 (16)	0.62545 (3)	0.44764 (4)	0.06139 (16)
Cl4	0.35612 (19)	0.88605 (4)	0.71520 (4)	0.07117 (19)
N2	0.4237 (4)	0.89871 (10)	0.50330 (10)	0.0429 (3)
O2	0.2629 (4)	0.94385 (9)	0.42708 (9)	0.0538 (3)
H2	0.3079	0.9987	0.4256	0.081*
C8	0.5024 (4)	0.75283 (11)	0.58413 (11)	0.0384 (4)
C9	0.6303 (5)	0.66160 (12)	0.56212 (13)	0.0421 (4)
C10	0.7785 (5)	0.59945 (13)	0.62661 (16)	0.0546 (5)
H10	0.8605	0.5393	0.6093	0.065*
C11	0.8035 (6)	0.62748 (15)	0.71651 (16)	0.0618 (6)
H11	0.9070	0.5864	0.7604	0.074*
C12	0.6773 (6)	0.71567 (15)	0.74256 (14)	0.0612 (6)
H12	0.6931	0.7340	0.8039	0.073*
C13	0.5265 (5)	0.77725 (12)	0.67727 (13)	0.0477 (4)
C14	0.3507 (5)	0.81491 (11)	0.51094 (12)	0.0406 (4)
H14	0.1973	0.7919	0.4693	0.049*

	U11	U22	U33	U12	U13	U23
Cl1	0.0848 (4)	0.0441 (3)	0.0602 (3)	0.0013 (2)	−0.0151 (3)	0.0096 (2)
Cl2	0.0817 (4)	0.0398 (3)	0.0525 (3)	0.0009 (2)	−0.0155 (2)	0.0047 (2)
N1	0.0565 (9)	0.0348 (7)	0.0375 (8)	−0.0012 (6)	−0.0006 (6)	−0.0057 (6)
O1	0.0891 (11)	0.0393 (7)	0.0429 (7)	−0.0001 (7)	0.0089 (7)	−0.0099 (6)
C1	0.0395 (9)	0.0296 (8)	0.0428 (9)	−0.0062 (6)	−0.0018 (7)	−0.0032 (7)
C2	0.0440 (10)	0.0329 (8)	0.0514 (10)	−0.0052 (7)	−0.0040 (8)	−0.0010 (7)
C3	0.0587 (12)	0.0330 (9)	0.0729 (14)	0.0009 (8)	0.0011 (10)	−0.0095 (9)
C4	0.0859 (16)	0.0477 (12)	0.0617 (13)	−0.0014 (11)	0.0098 (12)	−0.0206 (10)
C5	0.0861 (16)	0.0497 (11)	0.0445 (11)	−0.0080 (10)	0.0018 (10)	−0.0081 (9)
C6	0.0516 (10)	0.0331 (8)	0.0462 (10)	−0.0065 (7)	−0.0038 (8)	−0.0026 (7)
C7	0.0480 (10)	0.0349 (9)	0.0417 (9)	−0.0035 (7)	0.0023 (7)	0.0002 (7)
Cl3	0.0811 (4)	0.0450 (3)	0.0574 (3)	0.0006 (2)	0.0000 (3)	−0.0139 (2)
Cl4	0.1140 (5)	0.0476 (3)	0.0511 (3)	−0.0031 (3)	0.0111 (3)	−0.0128 (2)
N2	0.0526 (9)	0.0351 (7)	0.0403 (8)	−0.0002 (6)	−0.0031 (6)	0.0031 (6)
O2	0.0744 (9)	0.0380 (7)	0.0486 (7)	0.0001 (6)	−0.0127 (7)	0.0071 (6)
C8	0.0419 (9)	0.0317 (8)	0.0422 (9)	−0.0069 (7)	0.0001 (7)	0.0022 (7)
C9	0.0444 (10)	0.0337 (8)	0.0488 (10)	−0.0068 (7)	−0.0008 (8)	−0.0002 (7)
C10	0.0569 (12)	0.0343 (9)	0.0728 (14)	−0.0048 (8)	−0.0082 (10)	0.0080 (9)
C11	0.0744 (15)	0.0481 (11)	0.0644 (13)	−0.0124 (10)	−0.0206 (11)	0.0208 (10)
C12	0.0871 (16)	0.0552 (12)	0.0443 (11)	−0.0219 (11)	−0.0113 (10)	0.0082 (9)
C13	0.0630 (12)	0.0371 (9)	0.0441 (10)	−0.0105 (8)	0.0017 (8)	−0.0001 (7)
C14	0.0451 (10)	0.0346 (9)	0.0422 (9)	−0.0027 (7)	−0.0020 (7)	−0.0020 (7)

Cl1—C2	1.7376 (19)	Cl3—C9	1.7403 (19)
Cl2—C6	1.7370 (18)	Cl4—C13	1.7336 (19)
N1—C7	1.262 (2)	N2—C14	1.261 (2)
N1—O1	1.3919 (19)	N2—O2	1.3945 (18)
O1—H1	0.8200	O2—H2	0.8200
C1—C6	1.394 (2)	C8—C13	1.397 (2)
C1—C2	1.401 (2)	C8—C9	1.399 (2)
C1—C7	1.471 (2)	C8—C14	1.468 (2)
C2—C3	1.378 (3)	C9—C10	1.377 (3)
C3—C4	1.376 (3)	C10—C11	1.368 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.379 (3)	C11—C12	1.372 (3)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.376 (3)	C12—C13	1.383 (3)
C5—H5	0.9300	C12—H12	0.9300
C7—H7	0.9300	C14—H14	0.9300
C7—N1—O1	111.93 (15)	C14—N2—O2	111.98 (15)
N1—O1—H1	109.5	N2—O2—H2	109.5
C6—C1—C2	115.78 (16)	C13—C8—C9	115.73 (16)
C6—C1—C7	124.33 (15)	C13—C8—C14	124.76 (16)
C2—C1—C7	119.86 (15)	C9—C8—C14	119.50 (15)
C3—C2—C1	123.02 (18)	C10—C9—C8	122.98 (18)
C3—C2—Cl1	118.10 (15)	C10—C9—Cl3	118.38 (15)
C1—C2—Cl1	118.86 (14)	C8—C9—Cl3	118.63 (14)
C4—C3—C2	118.71 (18)	C11—C10—C9	119.02 (19)
C4—C3—H3	120.6	C11—C10—H10	120.5
C2—C3—H3	120.6	C9—C10—H10	120.5
C3—C4—C5	120.56 (19)	C10—C11—C12	120.62 (19)
C3—C4—H4	119.7	C10—C11—H11	119.7
C5—C4—H4	119.7	C12—C11—H11	119.7
C6—C5—C4	119.7 (2)	C11—C12—C13	119.8 (2)
C6—C5—H5	120.2	C11—C12—H12	120.1
C4—C5—H5	120.2	C13—C12—H12	120.1
C5—C6—C1	122.23 (17)	C12—C13—C8	121.80 (18)
C5—C6—Cl2	117.14 (15)	C12—C13—Cl4	117.71 (16)
C1—C6—Cl2	120.61 (13)	C8—C13—Cl4	120.46 (14)
N1—C7—C1	121.30 (16)	N2—C14—C8	121.45 (16)
N1—C7—H7	119.4	N2—C14—H14	119.3
C1—C7—H7	119.4	C8—C14—H14	119.3

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	2.14	2.854 (2)	145
O2—H2···N2ii	0.82	2.15	2.850 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	2.14	2.854 (2)	145
O2—H2⋯N2ii	0.82	2.15	2.850 (2)	144

Symmetry codes: (i) ; (ii) .