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

The non-H atoms of the title compound, C(10)H(11)ClN(2)O(2), lie nearly on a plane (r.m.s. deviation = 0.150 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 [201].

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

C10H11ClN2O2

M = 226.66

Monoclinic,

a = 5.8873 (3) Å

b = 25.0467 (10) Å

c = 7.3041 (3) Å

β = 99.016 (4)°

V = 1063.74 (8) Å3

Z = 4

Cu Kα radiation

μ = 3.05 mm−1

T = 100 K

0.35 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.415, T max = 0.863

3802 measured reflections

2090 independent reflections

1776 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.102

S = 1.05

2090 reflections

142 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.30 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/S1600536811026389/xu5259sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026389/xu5259Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026389/xu5259Isup3.cml

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

C10H11ClN2O2	F(000) = 472
Mr = 226.66	Dx = 1.415 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 1678 reflections
a = 5.8873 (3) Å	θ = 3.5–74.0°
b = 25.0467 (10) Å	µ = 3.05 mm−1
c = 7.3041 (3) Å	T = 100 K
β = 99.016 (4)°	Prism, yellow
V = 1063.74 (8) Å3	0.35 × 0.10 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2090 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1776 reflections with I > 2σ(I)
Mirror	Rint = 0.026
Detector resolution: 10.4041 pixels mm-1	θmax = 74.2°, θmin = 3.5°
ω scan	h = −5→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −20→31
Tmin = 0.415, Tmax = 0.863	l = −8→7
3802 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0508P)2 + 0.2595P] where P = (Fo2 + 2Fc2)/3
2090 reflections	(Δ/σ)max = 0.001
142 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.79949 (8)	0.222023 (16)	0.49001 (6)	0.02053 (15)
O1	0.3432 (2)	0.23571 (5)	0.2668 (2)	0.0248 (3)
O2	1.2583 (2)	0.53251 (5)	0.8487 (2)	0.0247 (3)
N1	0.7372 (3)	0.32750 (6)	0.4928 (2)	0.0162 (3)
N2	0.9408 (3)	0.33231 (6)	0.5974 (2)	0.0165 (3)
H2	1.023 (4)	0.3046 (10)	0.634 (4)	0.038 (7)*
C1	0.3119 (3)	0.33074 (8)	0.2551 (3)	0.0240 (4)
H1A	0.3295	0.3380	0.1263	0.036*
H1B	0.3820	0.3597	0.3348	0.036*
H1C	0.1481	0.3282	0.2646	0.036*
C2	0.4288 (3)	0.27892 (7)	0.3161 (3)	0.0184 (4)
C3	0.6546 (3)	0.28185 (7)	0.4355 (3)	0.0168 (4)
C4	1.0117 (3)	0.38372 (7)	0.6642 (2)	0.0155 (4)
C5	1.2413 (3)	0.39119 (7)	0.7442 (3)	0.0182 (4)
H5	1.3455	0.3620	0.7566	0.022*
C6	1.3153 (3)	0.44152 (7)	0.8052 (3)	0.0202 (4)
H6	1.4710	0.4467	0.8599	0.024*
C7	1.1642 (3)	0.48447 (7)	0.7872 (3)	0.0179 (4)
C8	0.9350 (3)	0.47698 (7)	0.7091 (3)	0.0185 (4)
H8	0.8307	0.5062	0.6972	0.022*
C9	0.8601 (3)	0.42636 (7)	0.6485 (3)	0.0186 (4)
H9	0.7037	0.4210	0.5960	0.022*
C10	1.1081 (4)	0.57745 (7)	0.8382 (3)	0.0242 (4)
H10A	1.1951	0.6090	0.8875	0.036*
H10B	0.9851	0.5704	0.9112	0.036*
H10C	1.0408	0.5838	0.7086	0.036*

	U11	U22	U33	U12	U13	U23
Cl1	0.0247 (3)	0.0108 (2)	0.0250 (3)	0.00228 (17)	0.00048 (18)	0.00008 (17)
O1	0.0238 (7)	0.0152 (7)	0.0340 (8)	−0.0046 (6)	−0.0002 (6)	−0.0032 (6)
O2	0.0255 (7)	0.0124 (6)	0.0348 (8)	−0.0011 (6)	0.0000 (6)	−0.0050 (6)
N1	0.0174 (7)	0.0134 (7)	0.0174 (8)	−0.0007 (6)	0.0016 (6)	0.0004 (6)
N2	0.0169 (8)	0.0101 (7)	0.0211 (8)	−0.0006 (6)	−0.0010 (6)	−0.0004 (6)
C1	0.0216 (10)	0.0160 (9)	0.0321 (11)	0.0011 (8)	−0.0032 (8)	−0.0006 (8)
C2	0.0185 (9)	0.0147 (9)	0.0214 (9)	−0.0011 (7)	0.0018 (7)	−0.0002 (7)
C3	0.0179 (9)	0.0107 (9)	0.0220 (9)	0.0013 (7)	0.0035 (7)	0.0007 (7)
C4	0.0190 (9)	0.0113 (8)	0.0162 (9)	−0.0007 (7)	0.0033 (7)	−0.0003 (7)
C5	0.0181 (9)	0.0120 (9)	0.0241 (10)	0.0018 (7)	0.0020 (7)	−0.0006 (7)
C6	0.0167 (9)	0.0172 (9)	0.0260 (10)	0.0009 (7)	0.0014 (7)	−0.0022 (8)
C7	0.0241 (10)	0.0116 (9)	0.0180 (9)	−0.0014 (7)	0.0035 (7)	−0.0014 (7)
C8	0.0207 (9)	0.0127 (9)	0.0221 (9)	0.0044 (7)	0.0029 (7)	0.0014 (7)
C9	0.0172 (9)	0.0169 (9)	0.0213 (9)	0.0018 (7)	0.0019 (7)	−0.0006 (8)
C10	0.0355 (11)	0.0102 (9)	0.0268 (11)	0.0010 (8)	0.0047 (9)	−0.0005 (8)

Cl1—C3	1.7395 (18)	C4—C9	1.385 (2)
O1—C2	1.224 (2)	C4—C5	1.398 (3)
O2—C7	1.371 (2)	C5—C6	1.384 (3)
O2—C10	1.426 (2)	C5—H5	0.9500
N1—C3	1.287 (2)	C6—C7	1.389 (3)
N1—N2	1.322 (2)	C6—H6	0.9500
N2—C4	1.417 (2)	C7—C8	1.393 (3)
N2—H2	0.87 (3)	C8—C9	1.392 (3)
C1—C2	1.503 (2)	C8—H8	0.9500
C1—H1A	0.9800	C9—H9	0.9500
C1—H1B	0.9800	C10—H10A	0.9800
C1—H1C	0.9800	C10—H10B	0.9800
C2—C3	1.473 (3)	C10—H10C	0.9800
C7—O2—C10	117.36 (15)	C6—C5—H5	120.3
C3—N1—N2	122.09 (16)	C4—C5—H5	120.3
N1—N2—C4	118.27 (15)	C5—C6—C7	120.67 (18)
N1—N2—H2	121.2 (18)	C5—C6—H6	119.7
C4—N2—H2	120.3 (18)	C7—C6—H6	119.7
C2—C1—H1A	109.5	O2—C7—C6	115.38 (17)
C2—C1—H1B	109.5	O2—C7—C8	124.65 (17)
H1A—C1—H1B	109.5	C6—C7—C8	119.96 (17)
C2—C1—H1C	109.5	C9—C8—C7	119.43 (17)
H1A—C1—H1C	109.5	C9—C8—H8	120.3
H1B—C1—H1C	109.5	C7—C8—H8	120.3
O1—C2—C3	120.66 (17)	C4—C9—C8	120.53 (18)
O1—C2—C1	121.88 (18)	C4—C9—H9	119.7
C3—C2—C1	117.45 (16)	C8—C9—H9	119.7
N1—C3—C2	119.81 (16)	O2—C10—H10A	109.5
N1—C3—Cl1	122.97 (15)	O2—C10—H10B	109.5
C2—C3—Cl1	117.21 (13)	H10A—C10—H10B	109.5
C9—C4—C5	119.98 (17)	O2—C10—H10C	109.5
C9—C4—N2	121.38 (17)	H10A—C10—H10C	109.5
C5—C4—N2	118.63 (16)	H10B—C10—H10C	109.5
C6—C5—C4	119.42 (17)
C3—N1—N2—C4	−175.92 (16)	C4—C5—C6—C7	−0.2 (3)
N2—N1—C3—C2	−178.79 (16)	C10—O2—C7—C6	−178.14 (16)
N2—N1—C3—Cl1	0.3 (3)	C10—O2—C7—C8	2.5 (3)
O1—C2—C3—N1	−176.92 (18)	C5—C6—C7—O2	−178.62 (17)
C1—C2—C3—N1	4.3 (3)	C5—C6—C7—C8	0.8 (3)
O1—C2—C3—Cl1	3.9 (3)	O2—C7—C8—C9	178.87 (17)
C1—C2—C3—Cl1	−174.89 (14)	C6—C7—C8—C9	−0.5 (3)
N1—N2—C4—C9	10.9 (3)	C5—C4—C9—C8	1.1 (3)
N1—N2—C4—C5	−167.94 (16)	N2—C4—C9—C8	−177.73 (17)
C9—C4—C5—C6	−0.7 (3)	C7—C8—C9—C4	−0.5 (3)
N2—C4—C5—C6	178.08 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.87 (3)	2.22 (3)	3.021 (2)	153 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.87 (3)	2.22 (3)	3.021 (2)	153 (2)

Symmetry code: (i) .