1-Chloro-1-[(4-chloro-phen-yl)hydrazinyl-idene]propan-2-one.

The non-H atoms of the title compound, C(9)H(8)Cl(2)N(2)O, lie nearly on a plane (r.m.s. deviation = 0.110 Å), and the C=N double bond has a Z configuration. In the crystal, adjacent mol-ecules are linked by an N-H⋯O(carbon-yl) hydrogen bond, forming a chain running along [100].

Related literature

For the synthesis, see: Benincori et al. (1990 ▶); Sayed et al. (2002 ▶). For background to the title compound, see: Asiri et al. (2010 ▶).

Experimental

Crystal data

C9H8Cl2N2O

M = 231.07

Monoclinic,

a = 5.7558 (4) Å

b = 23.3282 (17) Å

c = 7.4107 (6) Å

β = 96.976 (7)°

V = 987.69 (13) Å3

Z = 4

Cu Kα radiation

μ = 5.65 mm−1

T = 100 K

0.35 × 0.05 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.243, T max = 0.849

3486 measured reflections

1939 independent reflections

1640 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.208

S = 1.17

1939 reflections

133 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.28 e Å−3

Δρmin = −0.54 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026390/xu5260sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026390/xu5260Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026390/xu5260Isup3.cml

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

C9H8Cl2N2O	F(000) = 472
Mr = 231.07	Dx = 1.554 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 1477 reflections
a = 5.7558 (4) Å	θ = 3.8–74.1°
b = 23.3282 (17) Å	µ = 5.65 mm−1
c = 7.4107 (6) Å	T = 100 K
β = 96.976 (7)°	Prism, yellow
V = 987.69 (13) Å3	0.35 × 0.05 × 0.03 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	1939 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1640 reflections with I > 2σ(I)
Mirror	Rint = 0.036
Detector resolution: 10.4041 pixels mm-1	θmax = 74.3°, θmin = 3.8°
ω scans	h = −6→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −27→28
Tmin = 0.243, Tmax = 0.849	l = −9→9
3486 measured reflections

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)] = 0.070	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.208	w = 1/[σ2(Fo2) + (0.0903P)2 + 4.1934P] where P = (Fo2 + 2Fc2)/3
S = 1.17	(Δ/σ)max = 0.002
1939 reflections	Δρmax = 1.28 e Å−3
133 parameters	Δρmin = −0.54 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: 0.0015 (7)

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.

	x	y	z	Uiso*/Ueq
Cl1	0.2378 (2)	0.21916 (5)	0.50652 (16)	0.0233 (4)
Cl2	0.7056 (2)	0.56866 (5)	0.85227 (16)	0.0253 (4)
O1	−0.2165 (6)	0.23416 (15)	0.2828 (5)	0.0272 (8)
N1	0.1754 (7)	0.33248 (18)	0.5054 (5)	0.0194 (9)
N2	0.3787 (7)	0.33782 (18)	0.6093 (5)	0.0204 (9)
H2	0.464 (14)	0.308 (3)	0.632 (10)	0.05 (2)*
C1	−0.2428 (9)	0.3362 (2)	0.2694 (8)	0.0290 (12)
H1A	−0.3553	0.3296	0.1612	0.044*
H1B	−0.1229	0.3634	0.2402	0.044*
H1C	−0.3244	0.3520	0.3669	0.044*
C2	−0.1284 (9)	0.2803 (2)	0.3310 (7)	0.0215 (10)
C3	0.0947 (9)	0.2835 (2)	0.4510 (6)	0.0193 (10)
C4	0.4510 (8)	0.3930 (2)	0.6690 (6)	0.0197 (10)
C5	0.6761 (9)	0.4003 (2)	0.7582 (7)	0.0235 (11)
H5	0.7773	0.3682	0.7794	0.028*
C6	0.7533 (9)	0.4543 (2)	0.8162 (6)	0.0226 (10)
H6	0.9070	0.4595	0.8768	0.027*
C7	0.6036 (9)	0.5004 (2)	0.7845 (6)	0.0195 (10)
C8	0.3792 (9)	0.4940 (2)	0.6972 (7)	0.0221 (10)
H8	0.2789	0.5263	0.6771	0.027*
C9	0.3016 (8)	0.4404 (2)	0.6392 (6)	0.0209 (10)
H9	0.1474	0.4356	0.5793	0.025*

	U11	U22	U33	U12	U13	U23
Cl1	0.0260 (7)	0.0181 (6)	0.0248 (6)	0.0025 (4)	−0.0012 (5)	0.0005 (4)
Cl2	0.0281 (7)	0.0178 (6)	0.0279 (6)	−0.0023 (5)	−0.0050 (5)	−0.0019 (4)
O1	0.0274 (19)	0.0194 (18)	0.033 (2)	−0.0044 (15)	−0.0023 (15)	−0.0029 (15)
N1	0.019 (2)	0.021 (2)	0.0179 (18)	−0.0010 (16)	−0.0002 (15)	0.0004 (16)
N2	0.021 (2)	0.018 (2)	0.021 (2)	−0.0031 (17)	−0.0028 (16)	−0.0005 (16)
C1	0.024 (3)	0.025 (3)	0.036 (3)	−0.003 (2)	−0.007 (2)	0.002 (2)
C2	0.021 (2)	0.020 (2)	0.024 (2)	−0.0049 (19)	0.0022 (19)	−0.0011 (19)
C3	0.021 (2)	0.018 (2)	0.019 (2)	0.0010 (18)	0.0013 (18)	0.0013 (18)
C4	0.024 (2)	0.020 (2)	0.016 (2)	−0.0012 (19)	0.0014 (18)	0.0006 (18)
C5	0.022 (2)	0.023 (3)	0.024 (2)	0.005 (2)	−0.0008 (19)	0.000 (2)
C6	0.018 (2)	0.027 (3)	0.021 (2)	0.003 (2)	−0.0032 (18)	−0.001 (2)
C7	0.024 (2)	0.015 (2)	0.019 (2)	−0.0017 (18)	−0.0001 (18)	−0.0013 (17)
C8	0.020 (2)	0.020 (2)	0.025 (2)	0.0015 (19)	−0.0023 (19)	−0.0008 (19)
C9	0.018 (2)	0.023 (2)	0.021 (2)	0.0008 (19)	−0.0002 (18)	−0.0001 (19)

Cl1—C3	1.737 (5)	C2—C3	1.472 (7)
Cl2—C7	1.749 (5)	C4—C5	1.392 (7)
O1—C2	1.225 (6)	C4—C9	1.401 (7)
N1—C3	1.280 (6)	C5—C6	1.386 (7)
N1—N2	1.326 (6)	C5—H5	0.9500
N2—C4	1.407 (6)	C6—C7	1.382 (7)
N2—H2	0.85 (8)	C6—H6	0.9500
C1—C2	1.506 (7)	C7—C8	1.381 (7)
C1—H1A	0.9800	C8—C9	1.379 (7)
C1—H1B	0.9800	C8—H8	0.9500
C1—H1C	0.9800	C9—H9	0.9500
C3—N1—N2	121.8 (4)	C5—C4—N2	119.0 (4)
N1—N2—C4	118.4 (4)	C9—C4—N2	121.3 (4)
N1—N2—H2	119 (5)	C6—C5—C4	120.2 (5)
C4—N2—H2	123 (5)	C6—C5—H5	119.9
C2—C1—H1A	109.5	C4—C5—H5	119.9
C2—C1—H1B	109.5	C7—C6—C5	119.1 (5)
H1A—C1—H1B	109.5	C7—C6—H6	120.5
C2—C1—H1C	109.5	C5—C6—H6	120.5
H1A—C1—H1C	109.5	C6—C7—C8	121.5 (4)
H1B—C1—H1C	109.5	C6—C7—Cl2	118.7 (4)
O1—C2—C3	121.3 (5)	C8—C7—Cl2	119.8 (4)
O1—C2—C1	121.5 (4)	C9—C8—C7	119.6 (5)
C3—C2—C1	117.2 (4)	C9—C8—H8	120.2
N1—C3—C2	119.4 (4)	C7—C8—H8	120.2
N1—C3—Cl1	123.6 (4)	C8—C9—C4	119.8 (4)
C2—C3—Cl1	117.0 (4)	C8—C9—H9	120.1
C5—C4—C9	119.7 (5)	C4—C9—H9	120.1
C3—N1—N2—C4	−177.6 (4)	N2—C4—C5—C6	179.0 (4)
N2—N1—C3—C2	−178.0 (4)	C4—C5—C6—C7	0.1 (8)
N2—N1—C3—Cl1	0.4 (7)	C5—C6—C7—C8	0.2 (8)
O1—C2—C3—N1	−176.7 (5)	C5—C6—C7—Cl2	−178.2 (4)
C1—C2—C3—N1	3.6 (7)	C6—C7—C8—C9	−0.2 (8)
O1—C2—C3—Cl1	4.8 (7)	Cl2—C7—C8—C9	178.1 (4)
C1—C2—C3—Cl1	−174.9 (4)	C7—C8—C9—C4	−0.1 (7)
N1—N2—C4—C5	−171.9 (4)	C5—C4—C9—C8	0.5 (7)
N1—N2—C4—C9	7.6 (7)	N2—C4—C9—C8	−179.0 (4)
C9—C4—C5—C6	−0.5 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.85 (8)	2.26 (8)	3.029 (6)	150 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.85 (8)	2.26 (8)	3.029 (6)	150 (7)

Symmetry code: (i) .