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

The non-H atoms of the title compound, C(9)H(8)ClN(3)O(3), lie approximately on a plane (r.m.s. deviation = 0.111 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 [101].

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

C9H8ClN3O3

M = 241.63

Monoclinic,

a = 7.0628 (3) Å

b = 13.4182 (5) Å

c = 11.2884 (5) Å

β = 95.589 (4)°

V = 1064.72 (8) Å3

Z = 4

Cu Kα radiation

μ = 3.19 mm−1

T = 100 K

0.20 × 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 = 0.568, T max = 0.857

4113 measured reflections

2105 independent reflections

1839 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.152

S = 1.09

2105 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.21 e Å−3

Δρmin = −0.48 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/S1600536811026407/xu5261sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026407/xu5261Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026407/xu5261Isup3.cml

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

C9H8ClN3O3	F(000) = 496
Mr = 241.63	Dx = 1.507 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 1647 reflections
a = 7.0628 (3) Å	θ = 3.3–74.3°
b = 13.4182 (5) Å	µ = 3.19 mm−1
c = 11.2884 (5) Å	T = 100 K
β = 95.589 (4)°	Prism, yellow
V = 1064.72 (8) Å3	0.20 × 0.10 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2105 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1839 reflections with I > 2σ(I)
Mirror	Rint = 0.020
Detector resolution: 10.4041 pixels mm-1	θmax = 74.4°, θmin = 5.1°
ω scans	h = −8→5
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −16→16
Tmin = 0.568, Tmax = 0.857	l = −14→14
4113 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0849P)2 + 0.8946P] where P = (Fo2 + 2Fc2)/3
2105 reflections	(Δ/σ)max = 0.001
150 parameters	Δρmax = 1.21 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.63780 (10)	0.29860 (4)	0.39614 (6)	0.0299 (2)
O1	0.4446 (3)	0.25504 (13)	0.15943 (16)	0.0275 (4)
O2	0.8827 (3)	−0.34157 (14)	0.6658 (2)	0.0369 (5)
O3	1.0132 (3)	−0.25969 (16)	0.81885 (18)	0.0383 (5)
N1	0.6623 (3)	0.10048 (16)	0.37953 (18)	0.0213 (5)
N2	0.7385 (3)	0.09908 (17)	0.49160 (19)	0.0226 (5)
H2	0.753 (5)	0.154 (3)	0.528 (3)	0.042 (10)*
N3	0.9267 (3)	−0.26356 (18)	0.7182 (2)	0.0300 (5)
C1	0.5294 (4)	0.0846 (2)	0.1360 (2)	0.0304 (6)
H1A	0.4572	0.0912	0.0578	0.046*
H1B	0.4743	0.0311	0.1808	0.046*
H1C	0.6622	0.0686	0.1258	0.046*
C2	0.5211 (4)	0.1804 (2)	0.2026 (2)	0.0251 (6)
C3	0.6129 (4)	0.18280 (19)	0.3275 (2)	0.0224 (5)
C4	0.7818 (3)	0.00828 (19)	0.5472 (2)	0.0209 (5)
C5	0.8644 (4)	0.0084 (2)	0.6644 (2)	0.0246 (5)
H5	0.8885	0.0696	0.7054	0.030*
C6	0.9115 (4)	−0.0816 (2)	0.7210 (2)	0.0250 (5)
H6	0.9677	−0.0825	0.8009	0.030*
C7	0.8754 (4)	−0.16926 (19)	0.6594 (2)	0.0237 (5)
C8	0.7916 (4)	−0.17086 (19)	0.5427 (2)	0.0241 (5)
H8	0.7668	−0.2324	0.5026	0.029*
C9	0.7449 (4)	−0.08185 (19)	0.4860 (2)	0.0229 (5)
H9	0.6882	−0.0815	0.4061	0.027*

	U11	U22	U33	U12	U13	U23
Cl1	0.0424 (4)	0.0166 (4)	0.0299 (4)	0.0005 (2)	0.0002 (3)	0.0006 (2)
O1	0.0353 (10)	0.0225 (9)	0.0246 (9)	0.0050 (8)	0.0026 (8)	0.0069 (7)
O2	0.0469 (12)	0.0195 (10)	0.0448 (12)	0.0028 (9)	0.0070 (10)	0.0060 (9)
O3	0.0513 (13)	0.0354 (11)	0.0272 (10)	0.0140 (10)	−0.0015 (9)	0.0142 (9)
N1	0.0244 (10)	0.0193 (10)	0.0202 (10)	0.0008 (8)	0.0019 (8)	0.0023 (8)
N2	0.0300 (11)	0.0183 (10)	0.0195 (10)	0.0001 (9)	0.0014 (8)	−0.0007 (9)
N3	0.0329 (12)	0.0262 (12)	0.0322 (12)	0.0067 (10)	0.0099 (10)	0.0094 (10)
C1	0.0410 (15)	0.0266 (14)	0.0233 (12)	0.0013 (12)	0.0021 (11)	−0.0004 (11)
C2	0.0279 (12)	0.0229 (12)	0.0253 (13)	0.0009 (10)	0.0066 (10)	0.0058 (10)
C3	0.0265 (12)	0.0169 (11)	0.0244 (12)	0.0022 (10)	0.0062 (10)	0.0026 (10)
C4	0.0214 (11)	0.0179 (12)	0.0242 (12)	0.0006 (9)	0.0060 (9)	0.0034 (10)
C5	0.0291 (12)	0.0206 (13)	0.0245 (12)	−0.0018 (10)	0.0046 (10)	−0.0028 (10)
C6	0.0259 (12)	0.0297 (14)	0.0193 (11)	0.0032 (10)	0.0016 (9)	0.0044 (10)
C7	0.0266 (12)	0.0197 (13)	0.0254 (13)	0.0052 (10)	0.0059 (10)	0.0097 (10)
C8	0.0287 (12)	0.0186 (12)	0.0259 (13)	−0.0007 (10)	0.0071 (10)	−0.0007 (10)
C9	0.0275 (12)	0.0198 (12)	0.0214 (12)	−0.0009 (10)	0.0027 (9)	0.0002 (10)

Cl1—C3	1.737 (3)	C1—H1C	0.9800
O1—C2	1.217 (3)	C2—C3	1.494 (4)
O2—N3	1.227 (3)	C4—C5	1.393 (4)
O3—N3	1.238 (3)	C4—C9	1.405 (4)
N1—C3	1.283 (3)	C5—C6	1.391 (4)
N1—N2	1.326 (3)	C5—H5	0.9500
N2—C4	1.391 (3)	C6—C7	1.377 (4)
N2—H2	0.85 (4)	C6—H6	0.9500
N3—C7	1.458 (3)	C7—C8	1.391 (4)
C1—C2	1.493 (4)	C8—C9	1.380 (4)
C1—H1A	0.9800	C8—H8	0.9500
C1—H1B	0.9800	C9—H9	0.9500
C3—N1—N2	121.0 (2)	N2—C4—C5	118.7 (2)
N1—N2—C4	119.6 (2)	N2—C4—C9	120.7 (2)
N1—N2—H2	118 (3)	C5—C4—C9	120.6 (2)
C4—N2—H2	122 (3)	C6—C5—C4	119.6 (2)
O2—N3—O3	123.9 (2)	C6—C5—H5	120.2
O2—N3—C7	118.7 (2)	C4—C5—H5	120.2
O3—N3—C7	117.4 (2)	C7—C6—C5	119.1 (2)
C2—C1—H1A	109.5	C7—C6—H6	120.5
C2—C1—H1B	109.5	C5—C6—H6	120.5
H1A—C1—H1B	109.5	C6—C7—C8	122.1 (2)
C2—C1—H1C	109.5	C6—C7—N3	119.1 (2)
H1A—C1—H1C	109.5	C8—C7—N3	118.8 (2)
H1B—C1—H1C	109.5	C9—C8—C7	119.1 (2)
O1—C2—C1	123.0 (2)	C9—C8—H8	120.4
O1—C2—C3	119.7 (2)	C7—C8—H8	120.4
C1—C2—C3	117.3 (2)	C8—C9—C4	119.5 (2)
N1—C3—C2	119.1 (2)	C8—C9—H9	120.2
N1—C3—Cl1	123.7 (2)	C4—C9—H9	120.2
C2—C3—Cl1	117.12 (18)
C3—N1—N2—C4	176.8 (2)	C5—C6—C7—C8	−0.6 (4)
N2—N1—C3—C2	−177.8 (2)	C5—C6—C7—N3	179.3 (2)
N2—N1—C3—Cl1	−0.4 (3)	O2—N3—C7—C6	175.2 (2)
O1—C2—C3—N1	167.5 (2)	O3—N3—C7—C6	−4.9 (4)
C1—C2—C3—N1	−12.9 (4)	O2—N3—C7—C8	−4.9 (4)
O1—C2—C3—Cl1	−10.0 (3)	O3—N3—C7—C8	175.0 (2)
C1—C2—C3—Cl1	169.63 (19)	C6—C7—C8—C9	0.8 (4)
N1—N2—C4—C5	179.0 (2)	N3—C7—C8—C9	−179.1 (2)
N1—N2—C4—C9	−0.3 (3)	C7—C8—C9—C4	−0.3 (4)
N2—C4—C5—C6	−179.0 (2)	N2—C4—C9—C8	179.2 (2)
C9—C4—C5—C6	0.3 (4)	C5—C4—C9—C8	−0.2 (4)
C4—C5—C6—C7	0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.85 (4)	2.26 (4)	3.000 (3)	145 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.85 (4)	2.26 (4)	3.000 (3)	145 (3)

Symmetry code: (i) .