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

The asymmetric unit of the title compound, C(10)H(11)ClN(2)O, contains two mol-ecules. The non-H atoms of each mol-ecule lie approximately on a plane (r.m.s. deviations = 0.062 and 0.110 Å), and the C=N double bond has a Z-configuration in both independent mol-ecules. In the crystal, adjacent mol-ecules are linked by N-H⋯O(carbon-yl) hydrogen bonds, forming chains 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

C10H11ClN2O

M = 210.66

Monoclinic,

a = 11.0572 (3) Å

b = 7.6570 (2) Å

c = 12.4613 (3) Å

β = 105.063 (3)°

V = 1018.79 (5) Å3

Z = 4

Cu Kα radiation

μ = 3.06 mm−1

T = 100 K

0.20 × 0.02 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.580, T max = 0.941

3467 measured reflections

2667 independent reflections

2516 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.125

S = 1.06

2667 reflections

266 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.42 e Å−3

Absolute structure: Flack (1983 ▶), 533 Friedel pairs

Flack parameter: 0.17 (2)

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/S1600536811026419/xu5262sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026419/xu5262Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026419/xu5262Isup3.cml

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

C10H11ClN2O	F(000) = 440
Mr = 210.66	Dx = 1.373 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 1695 reflections
a = 11.0572 (3) Å	θ = 3.7–74.0°
b = 7.6570 (2) Å	µ = 3.06 mm−1
c = 12.4613 (3) Å	T = 100 K
β = 105.063 (3)°	Prism, yellow
V = 1018.79 (5) Å3	0.20 × 0.02 × 0.02 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2667 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2516 reflections with I > 2σ(I)
Mirror	Rint = 0.021
Detector resolution: 10.4041 pixels mm-1	θmax = 74.2°, θmin = 3.7°
ω scan	h = −13→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −9→9
Tmin = 0.580, Tmax = 0.941	l = −13→15
3467 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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0867P)2 + 0.3419P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2667 reflections	Δρmax = 0.31 e Å−3
266 parameters	Δρmin = −0.42 e Å−3
1 restraint	Absolute structure: Flack (1983), 533 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.17 (2)

	x	y	z	Uiso*/Ueq
Cl1	0.22799 (7)	0.50001 (13)	0.90675 (6)	0.0252 (2)
Cl2	0.75288 (7)	0.52179 (14)	1.00248 (6)	0.0252 (2)
N1	0.2864 (2)	0.4827 (4)	1.1276 (2)	0.0187 (6)
N2	0.3920 (3)	0.4043 (4)	1.1235 (2)	0.0195 (6)
H2	0.416 (4)	0.391 (7)	1.062 (4)	0.035 (13)*
N3	0.7037 (2)	0.4842 (4)	0.7819 (2)	0.0193 (6)
N4	0.8068 (3)	0.5762 (4)	0.7850 (2)	0.0201 (6)
H4	0.853 (5)	0.615 (7)	0.844 (4)	0.035 (13)*
O1	0.0213 (2)	0.6872 (4)	0.9612 (2)	0.0297 (7)
O2	0.5199 (3)	0.3196 (4)	0.9474 (2)	0.0281 (6)
C1	0.0693 (3)	0.6493 (6)	1.1582 (3)	0.0253 (8)
H1A	0.0074	0.7420	1.1556	0.038*
H1B	0.1477	0.6800	1.2125	0.038*
H1C	0.0373	0.5391	1.1800	0.038*
C2	0.0928 (3)	0.6290 (6)	1.0454 (3)	0.0225 (8)
C3	0.2071 (3)	0.5347 (5)	1.0390 (3)	0.0207 (7)
C4	0.4745 (3)	0.3415 (5)	1.2216 (3)	0.0177 (7)
C5	0.5915 (3)	0.2783 (5)	1.2169 (3)	0.0207 (7)
H5	0.6156	0.2824	1.1491	0.025*
C6	0.6723 (3)	0.2097 (5)	1.3117 (3)	0.0212 (7)
H6	0.7515	0.1664	1.3077	0.025*
C7	0.6406 (3)	0.2026 (5)	1.4124 (3)	0.0200 (7)
C8	0.5243 (3)	0.2683 (5)	1.4160 (3)	0.0205 (8)
H8	0.5011	0.2654	1.4842	0.025*
C9	0.4416 (3)	0.3377 (5)	1.3228 (3)	0.0190 (7)
H9	0.3630	0.3825	1.3274	0.023*
C10	0.7273 (3)	0.1199 (6)	1.5139 (3)	0.0255 (8)
H10A	0.7083	0.1659	1.5810	0.038*
H10B	0.8143	0.1473	1.5154	0.038*
H10C	0.7155	−0.0070	1.5108	0.038*
C11	0.4814 (4)	0.2920 (5)	0.7503 (3)	0.0240 (8)
H11A	0.4059	0.2297	0.7562	0.036*
H11B	0.5335	0.2139	0.7190	0.036*
H11C	0.4573	0.3938	0.7019	0.036*
C12	0.5538 (3)	0.3510 (5)	0.8636 (3)	0.0203 (8)
C13	0.6703 (3)	0.4509 (5)	0.8711 (3)	0.0194 (7)
C14	0.8352 (3)	0.6173 (5)	0.6841 (3)	0.0176 (7)
C15	0.9434 (3)	0.7145 (5)	0.6877 (3)	0.0206 (7)
H15	0.9979	0.7478	0.7569	0.025*
C16	0.9699 (3)	0.7618 (5)	0.5883 (3)	0.0220 (8)
H16	1.0423	0.8302	0.5907	0.026*
C17	0.8940 (3)	0.7123 (5)	0.4861 (3)	0.0204 (7)
C18	0.7876 (3)	0.6112 (5)	0.4846 (3)	0.0209 (7)
H18	0.7349	0.5739	0.4154	0.025*
C19	0.7581 (3)	0.5651 (5)	0.5822 (3)	0.0195 (7)
H19	0.6853	0.4977	0.5796	0.023*
C20	0.9210 (4)	0.7668 (6)	0.3778 (3)	0.0263 (8)
H20A	0.8425	0.7988	0.3241	0.040*
H20B	0.9602	0.6695	0.3484	0.040*
H20C	0.9778	0.8673	0.3910	0.040*

	U11	U22	U33	U12	U13	U23
Cl1	0.0246 (4)	0.0350 (5)	0.0168 (4)	−0.0019 (4)	0.0070 (3)	0.0016 (4)
Cl2	0.0246 (4)	0.0320 (5)	0.0193 (4)	−0.0022 (4)	0.0065 (3)	−0.0005 (4)
N1	0.0137 (12)	0.0207 (17)	0.0231 (13)	−0.0041 (12)	0.0074 (11)	−0.0008 (13)
N2	0.0191 (14)	0.0255 (17)	0.0158 (13)	−0.0014 (13)	0.0082 (12)	0.0000 (12)
N3	0.0170 (13)	0.0199 (17)	0.0230 (13)	0.0019 (12)	0.0089 (11)	0.0016 (13)
N4	0.0201 (14)	0.0242 (16)	0.0176 (14)	−0.0045 (12)	0.0079 (12)	−0.0019 (13)
O1	0.0162 (12)	0.046 (2)	0.0253 (14)	−0.0022 (12)	0.0019 (11)	0.0054 (13)
O2	0.0251 (13)	0.0375 (17)	0.0263 (14)	−0.0004 (12)	0.0146 (11)	0.0041 (12)
C1	0.0190 (16)	0.034 (2)	0.0246 (18)	0.0011 (16)	0.0089 (15)	0.0000 (17)
C2	0.0163 (15)	0.030 (2)	0.0212 (17)	−0.0053 (16)	0.0053 (14)	−0.0001 (16)
C3	0.0189 (15)	0.025 (2)	0.0194 (15)	−0.0068 (16)	0.0079 (13)	−0.0007 (15)
C4	0.0165 (16)	0.0152 (17)	0.0218 (17)	−0.0030 (14)	0.0057 (14)	−0.0003 (14)
C5	0.0194 (17)	0.0233 (19)	0.0217 (17)	0.0007 (15)	0.0096 (14)	−0.0010 (15)
C6	0.0189 (16)	0.0219 (17)	0.0245 (18)	−0.0011 (15)	0.0088 (14)	−0.0003 (15)
C7	0.0195 (16)	0.0182 (17)	0.0206 (17)	−0.0037 (14)	0.0024 (14)	0.0001 (14)
C8	0.0214 (17)	0.0245 (19)	0.0181 (16)	−0.0041 (15)	0.0099 (14)	−0.0036 (15)
C9	0.0172 (16)	0.0243 (18)	0.0172 (16)	−0.0021 (14)	0.0072 (14)	−0.0012 (14)
C10	0.0229 (17)	0.027 (2)	0.0252 (18)	0.0014 (16)	0.0043 (15)	0.0060 (16)
C11	0.0217 (18)	0.028 (2)	0.0217 (18)	−0.0005 (16)	0.0042 (15)	−0.0003 (16)
C12	0.0199 (17)	0.0193 (18)	0.0255 (18)	0.0056 (15)	0.0129 (15)	0.0032 (15)
C13	0.0219 (17)	0.0207 (18)	0.0167 (15)	0.0034 (14)	0.0068 (14)	0.0020 (13)
C14	0.0174 (15)	0.0181 (18)	0.0185 (16)	0.0023 (14)	0.0067 (13)	0.0013 (14)
C15	0.0196 (16)	0.0199 (17)	0.0223 (17)	0.0014 (14)	0.0057 (14)	0.0016 (15)
C16	0.0149 (15)	0.0212 (19)	0.032 (2)	0.0006 (15)	0.0104 (15)	0.0019 (16)
C17	0.0218 (17)	0.0204 (17)	0.0220 (17)	0.0023 (15)	0.0108 (14)	0.0014 (15)
C18	0.0198 (16)	0.0244 (19)	0.0186 (16)	0.0049 (15)	0.0050 (14)	0.0002 (14)
C19	0.0171 (15)	0.0189 (18)	0.0245 (16)	0.0000 (13)	0.0087 (14)	−0.0015 (14)
C20	0.0234 (18)	0.035 (2)	0.0237 (18)	0.0013 (17)	0.0109 (15)	0.0076 (17)

Cl1—C3	1.743 (3)	C8—C9	1.384 (5)
Cl2—C13	1.742 (4)	C8—H8	0.9500
N1—C3	1.281 (4)	C9—H9	0.9500
N1—N2	1.326 (4)	C10—H10A	0.9800
N2—C4	1.407 (5)	C10—H10B	0.9800
N2—H2	0.88 (5)	C10—H10C	0.9800
N3—C13	1.283 (4)	C11—C12	1.500 (5)
N3—N4	1.332 (4)	C11—H11A	0.9800
N4—C14	1.409 (4)	C11—H11B	0.9800
N4—H4	0.83 (5)	C11—H11C	0.9800
O1—C2	1.221 (5)	C12—C13	1.480 (5)
O2—C12	1.222 (4)	C14—C19	1.391 (5)
C1—C2	1.502 (5)	C14—C15	1.399 (5)
C1—H1A	0.9800	C15—C16	1.393 (5)
C1—H1B	0.9800	C15—H15	0.9500
C1—H1C	0.9800	C16—C17	1.383 (5)
C2—C3	1.477 (5)	C16—H16	0.9500
C4—C5	1.397 (5)	C17—C18	1.404 (5)
C4—C9	1.399 (5)	C17—C20	1.515 (5)
C5—C6	1.386 (5)	C18—C19	1.385 (5)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.389 (5)	C19—H19	0.9500
C6—H6	0.9500	C20—H20A	0.9800
C7—C8	1.391 (5)	C20—H20B	0.9800
C7—C10	1.513 (5)	C20—H20C	0.9800
C3—N1—N2	121.3 (3)	H10A—C10—H10B	109.5
N1—N2—C4	120.0 (3)	C7—C10—H10C	109.5
N1—N2—H2	123 (3)	H10A—C10—H10C	109.5
C4—N2—H2	117 (3)	H10B—C10—H10C	109.5
C13—N3—N4	121.1 (3)	C12—C11—H11A	109.5
N3—N4—C14	118.7 (3)	C12—C11—H11B	109.5
N3—N4—H4	123 (3)	H11A—C11—H11B	109.5
C14—N4—H4	118 (3)	C12—C11—H11C	109.5
C2—C1—H1A	109.5	H11A—C11—H11C	109.5
C2—C1—H1B	109.5	H11B—C11—H11C	109.5
H1A—C1—H1B	109.5	O2—C12—C13	120.2 (3)
C2—C1—H1C	109.5	O2—C12—C11	122.5 (3)
H1A—C1—H1C	109.5	C13—C12—C11	117.3 (3)
H1B—C1—H1C	109.5	N3—C13—C12	119.3 (3)
O1—C2—C3	120.3 (3)	N3—C13—Cl2	123.6 (3)
O1—C2—C1	122.3 (3)	C12—C13—Cl2	117.1 (3)
C3—C2—C1	117.4 (3)	C19—C14—C15	119.9 (3)
N1—C3—C2	120.6 (3)	C19—C14—N4	121.6 (3)
N1—C3—Cl1	122.6 (3)	C15—C14—N4	118.5 (3)
C2—C3—Cl1	116.8 (3)	C16—C15—C14	119.0 (3)
C5—C4—C9	119.4 (3)	C16—C15—H15	120.5
C5—C4—N2	118.7 (3)	C14—C15—H15	120.5
C9—C4—N2	121.9 (3)	C17—C16—C15	122.0 (3)
C6—C5—C4	119.6 (3)	C17—C16—H16	119.0
C6—C5—H5	120.2	C15—C16—H16	119.0
C4—C5—H5	120.2	C16—C17—C18	118.0 (3)
C5—C6—C7	121.8 (3)	C16—C17—C20	122.1 (3)
C5—C6—H6	119.1	C18—C17—C20	119.9 (3)
C7—C6—H6	119.1	C19—C18—C17	121.1 (3)
C6—C7—C8	117.8 (3)	C19—C18—H18	119.5
C6—C7—C10	121.1 (3)	C17—C18—H18	119.5
C8—C7—C10	121.0 (3)	C18—C19—C14	120.0 (3)
C9—C8—C7	121.8 (3)	C18—C19—H19	120.0
C9—C8—H8	119.1	C14—C19—H19	120.0
C7—C8—H8	119.1	C17—C20—H20A	109.5
C8—C9—C4	119.6 (3)	C17—C20—H20B	109.5
C8—C9—H9	120.2	H20A—C20—H20B	109.5
C4—C9—H9	120.2	C17—C20—H20C	109.5
C7—C10—H10A	109.5	H20A—C20—H20C	109.5
C7—C10—H10B	109.5	H20B—C20—H20C	109.5
C3—N1—N2—C4	−177.1 (3)	N2—C4—C9—C8	177.5 (4)
C13—N3—N4—C14	−176.5 (3)	N4—N3—C13—C12	178.9 (3)
N2—N1—C3—C2	−177.1 (3)	N4—N3—C13—Cl2	0.6 (5)
N2—N1—C3—Cl1	2.5 (5)	O2—C12—C13—N3	−179.3 (3)
O1—C2—C3—N1	175.7 (4)	C11—C12—C13—N3	0.7 (5)
C1—C2—C3—N1	−4.4 (5)	O2—C12—C13—Cl2	−0.9 (5)
O1—C2—C3—Cl1	−3.9 (5)	C11—C12—C13—Cl2	179.1 (3)
C1—C2—C3—Cl1	176.0 (3)	N3—N4—C14—C19	0.4 (5)
N1—N2—C4—C5	−172.5 (3)	N3—N4—C14—C15	179.8 (3)
N1—N2—C4—C9	8.7 (5)	C19—C14—C15—C16	1.9 (5)
C9—C4—C5—C6	1.3 (6)	N4—C14—C15—C16	−177.5 (3)
N2—C4—C5—C6	−177.6 (3)	C14—C15—C16—C17	−1.5 (6)
C4—C5—C6—C7	−0.4 (6)	C15—C16—C17—C18	0.0 (6)
C5—C6—C7—C8	−0.5 (6)	C15—C16—C17—C20	178.7 (4)
C5—C6—C7—C10	177.2 (4)	C16—C17—C18—C19	1.1 (5)
C6—C7—C8—C9	0.5 (6)	C20—C17—C18—C19	−177.6 (4)
C10—C7—C8—C9	−177.2 (4)	C17—C18—C19—C14	−0.7 (5)
C7—C8—C9—C4	0.5 (6)	C15—C14—C19—C18	−0.9 (5)
C5—C4—C9—C8	−1.3 (6)	N4—C14—C19—C18	178.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.88 (5)	2.12 (5)	2.975 (4)	162 (4)
N4—H4···O1i	0.83 (5)	2.12 (5)	2.909 (4)	159 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.88 (5)	2.12 (5)	2.975 (4)	162 (4)
N4—H4⋯O1i	0.83 (5)	2.12 (5)	2.909 (4)	159 (4)

Symmetry code: (i) .