N-(4-chloro­benzo­yl)-N-(2-chloro­phen­yl)-O-[2-(2-nitro­phen­yl)acet­yl]hydroxyl­amine

Ma, J.; Ma, Y.; He, D.

doi:10.1107/S1600536812040883

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3067

doi:10.1107/S1600536812040883

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N-(4-chlorobenzoyl)-N-(2-chlorophenyl)-O-[2-(2-nitrophenyl)acetyl]hydroxylamine

Jing Ma,^a ^* Yi Ma ^b and Dian He ^a

^aInstitute of Medicinal Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 730000, Gansu Province, People's Republic of China, and ^bGansu College of Traditional Chinese Medicine, Lanzhou 730000, Gansu Province, People's Republic of China
^*Correspondence e-mail: majing.1988.ok@163.com

(Received 20 September 2012; accepted 28 September 2012; online 3 October 2012)

In the title hydroxamic acid derivate, C₂₁H₁₄N₂O₅Cl₂, the nitro-substituted benzene ring forms dihedral angles of 66.0 (2) and 59.6 (2)°, with the p-chloro and o-chloro-substituted benzene rings, respectively. The dihedral angle between the two chloro-substituted benzene rings is 64.2 (2) Å. In the crystal, weak C—H⋯O hydrogen bonds link the molecules along [010]. The crystal studied was an inversion twin with refined components in the ratio 0.60 (7):0.40 (7).

Related literature

For applications of hydroxamic acid derivatives, see: Noh et al. (2009 ); Zeng et al. (2003 ). For the synthesis, see: Ayyangark et al. (1986 ). For a related structure, see: Zhang et al. (2012 ).

Experimental

Crystal data

C₂₁H₁₄Cl₂N₂O₅
M_r = 445.24
Monoclinic, P 2₁
a = 12.366 (14) Å
b = 6.789 (8) Å
c = 12.579 (14) Å
β = 105.150 (14)°
V = 1019 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 296 K
0.21 × 0.20 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.929, T_max = 0.945
5091 measured reflections
3669 independent reflections
1821 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.069
S = 0.99
3669 reflections
271 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), 1624 Friedel pairs
Flack parameter: 0.40 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.93	2.38	3.264 (7)	158
C15—H15B⋯O1ⁱⁱ	0.97	2.45	3.421 (6)	175
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812040883/lh5536sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812040883/lh5536Isup2.hkl

checkCIF report

Comment top

Hydroxamic acid derivatives have received considerable attention in recent years as the result of the discovery of their role in the biochemical toxicology of many drugs and other chemicals (Noh et al., 2009; Zeng et al., 2003). The molecular structure of the title compound is sjown in Fig. 1. The nitro-substituted benzene ring (C16-C24) forms dihedral angles of 66.0 (2) and 59.6 (2)°, with the 4-chloro (C1-C6) and 2-chloro-substituted (C8-C13) benzene rings, respectively. The dihedral angle between the two chloro-substituted benzene rings (C1-6/C8-C13) is 64.2 (2)Å. In the crystal, weak C—H···O hydrogen bonds linke molecules along [010] (Fig .2). The bond legths and angles can be compared to those in N-(2-Chlorophenyl)-1-phenylformamido 3-(2-nitrophenyl)propanoate (Zhang et al., 2012).

Related literature top

For applications of hydroxamic acid derivatives, see: Noh et al. (2009); Zeng et al. (2003). For the synthesis, see: Ayyangark et al. (1986). For a related structure, see: Zhang et al. (2012).

Experimental top

The title compound (I) was prepared according to the method described by Ayyangark et al. (1986). Crystals suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution of (I) in dichloromethane-methanol (1:3 v/v).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. Part of the crystal structure with weak hydrogen bonds shown as dashed lines.

N-(4-chlorobenzoyl)-N-(2-chlorophenyl)-O-[2-(2- nitrophenyl)acetyl]hydroxylamine top

Crystal data top

C₂₁H₁₄Cl₂N₂O₅	F(000) = 456
M_r = 445.24	D_x = 1.450 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 985 reflections
a = 12.366 (14) Å	θ = 2.7–19.2°
b = 6.789 (8) Å	µ = 0.36 mm⁻¹
c = 12.579 (14) Å	T = 296 K
β = 105.150 (14)°	Block, colorless
V = 1019 (2) Å³	0.21 × 0.20 × 0.16 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	3669 independent reflections
Radiation source: fine-focus sealed tube	1821 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.929, T_max = 0.945	k = −8→8
5091 measured reflections	l = −15→14

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0117P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.054	(Δ/σ)_max < 0.001
wR(F²) = 0.069	Δρ_max = 0.17 e Å⁻³
S = 0.99	Δρ_min = −0.16 e Å⁻³
3669 reflections	Absolute structure: Flack (1983), 1624 Friedel pairs
271 parameters	Absolute structure parameter: 0.40 (7)
1 restraint

Crystal data top

C₂₁H₁₄Cl₂N₂O₅	V = 1019 (2) Å³
M_r = 445.24	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 12.366 (14) Å	µ = 0.36 mm⁻¹
b = 6.789 (8) Å	T = 296 K
c = 12.579 (14) Å	0.21 × 0.20 × 0.16 mm
β = 105.150 (14)°

Data collection top

Bruker APEXII CCD diffractometer	3669 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1821 reflections with I > 2σ(I)
T_min = 0.929, T_max = 0.945	R_int = 0.030
5091 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.069	Δρ_max = 0.17 e Å⁻³
S = 0.99	Δρ_min = −0.16 e Å⁻³
3669 reflections	Absolute structure: Flack (1983), 1624 Friedel pairs
271 parameters	Absolute structure parameter: 0.40 (7)
1 restraint

Special details top

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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.0147 (3)	0.5015 (8)	0.8371 (3)	0.0556 (12)
H1	0.0422	0.4007	0.8869	0.067*
C2	−0.0321 (4)	0.6675 (7)	0.8709 (3)	0.0590 (13)
H2	−0.0363	0.6786	0.9434	0.071*
C3	−0.0720 (4)	0.8152 (6)	0.7973 (4)	0.0581 (14)
C4	−0.0663 (4)	0.8041 (7)	0.6904 (4)	0.0642 (15)
H4	−0.0935	0.9061	0.6414	0.077*
C5	−0.0194 (4)	0.6382 (7)	0.6562 (4)	0.0554 (13)
H5	−0.0148	0.6292	0.5838	0.067*
C6	0.0207 (3)	0.4855 (7)	0.7292 (3)	0.0439 (11)
C7	0.0602 (4)	0.3045 (7)	0.6835 (4)	0.0493 (13)
C8	0.2401 (3)	0.3019 (7)	0.8323 (4)	0.0487 (12)
C9	0.2722 (4)	0.2095 (7)	0.9344 (4)	0.0577 (13)
C10	0.3508 (4)	0.2985 (10)	1.0199 (5)	0.0814 (17)
H10	0.3720	0.2376	1.0884	0.098*
C11	0.3970 (4)	0.4729 (11)	1.0044 (5)	0.0906 (19)
H11	0.4484	0.5328	1.0628	0.109*
C12	0.3684 (4)	0.5626 (8)	0.9024 (5)	0.0831 (18)
H12	0.4026	0.6801	0.8915	0.100*
C13	0.2899 (4)	0.4789 (8)	0.8174 (4)	0.0640 (14)
H13	0.2697	0.5411	0.7492	0.077*
C14	0.2324 (3)	0.0798 (8)	0.6138 (4)	0.0493 (13)
C15	0.2469 (3)	−0.1148 (6)	0.5610 (3)	0.0523 (12)
H15A	0.2688	−0.2138	0.6182	0.063*
H15B	0.1754	−0.1543	0.5128	0.063*
C16	0.3330 (4)	−0.1087 (6)	0.4954 (4)	0.0494 (12)
C17	0.2956 (4)	−0.1148 (7)	0.3812 (4)	0.0669 (14)
H17	0.2190	−0.1217	0.3485	0.080*
C18	0.3679 (5)	−0.1107 (8)	0.3152 (4)	0.0791 (16)
H18	0.3406	−0.1116	0.2390	0.095*
C19	0.4823 (5)	−0.1054 (7)	0.3634 (5)	0.0778 (16)
H19	0.5320	−0.1053	0.3191	0.093*
C20	0.5227 (4)	−0.1003 (7)	0.4756 (5)	0.0690 (14)
H20	0.5994	−0.0966	0.5082	0.083*
C21	0.4474 (4)	−0.1006 (6)	0.5391 (4)	0.0511 (12)
Cl1	−0.13093 (10)	1.0228 (2)	0.84135 (10)	0.0924 (4)
Cl2	0.21125 (11)	−0.0100 (2)	0.95615 (10)	0.0868 (4)
N1	0.1548 (3)	0.2169 (6)	0.7465 (3)	0.0501 (9)
N2	0.4985 (4)	−0.0959 (6)	0.6589 (4)	0.0711 (13)
O1	0.0103 (2)	0.2380 (4)	0.5951 (2)	0.0622 (9)
O2	0.1866 (2)	0.0409 (4)	0.7008 (2)	0.0563 (8)
O3	0.4389 (3)	−0.0664 (6)	0.7204 (3)	0.0983 (14)
O4	0.5971 (3)	−0.1181 (7)	0.6925 (3)	0.1191 (16)
O5	0.2537 (2)	0.2392 (5)	0.5864 (2)	0.0613 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.062 (3)	0.066 (3)	0.040 (3)	0.008 (3)	0.015 (2)	0.012 (3)
C2	0.068 (3)	0.077 (4)	0.035 (3)	0.006 (3)	0.017 (3)	0.005 (3)
C3	0.053 (3)	0.053 (3)	0.062 (4)	−0.007 (3)	0.005 (3)	−0.006 (3)
C4	0.068 (4)	0.065 (4)	0.048 (4)	−0.012 (3)	−0.006 (3)	0.005 (3)
C5	0.063 (4)	0.070 (4)	0.035 (3)	−0.020 (3)	0.016 (3)	−0.002 (3)
C6	0.038 (3)	0.058 (3)	0.035 (3)	−0.005 (3)	0.007 (2)	0.007 (3)
C7	0.050 (3)	0.068 (4)	0.036 (3)	−0.006 (3)	0.022 (3)	0.003 (3)
C8	0.029 (3)	0.071 (4)	0.043 (3)	0.003 (3)	0.005 (3)	−0.008 (3)
C9	0.046 (3)	0.065 (3)	0.061 (3)	0.011 (3)	0.010 (3)	0.001 (3)
C10	0.067 (4)	0.103 (5)	0.061 (4)	0.024 (4)	−0.007 (3)	−0.005 (4)
C11	0.076 (4)	0.108 (6)	0.074 (4)	0.011 (5)	−0.006 (3)	−0.012 (5)
C12	0.055 (4)	0.083 (5)	0.104 (5)	−0.008 (4)	0.008 (3)	−0.004 (4)
C13	0.049 (3)	0.082 (4)	0.057 (3)	−0.009 (3)	0.007 (3)	0.012 (3)
C14	0.031 (3)	0.076 (4)	0.042 (3)	−0.004 (3)	0.011 (2)	0.000 (3)
C15	0.042 (3)	0.059 (3)	0.055 (3)	−0.001 (3)	0.010 (2)	−0.006 (3)
C16	0.040 (3)	0.042 (3)	0.068 (4)	0.007 (3)	0.017 (3)	−0.004 (3)
C17	0.067 (4)	0.082 (3)	0.051 (3)	0.009 (3)	0.013 (3)	−0.011 (3)
C18	0.101 (5)	0.082 (4)	0.063 (4)	0.014 (4)	0.036 (4)	−0.003 (3)
C19	0.083 (5)	0.055 (3)	0.114 (5)	0.009 (4)	0.059 (4)	−0.005 (4)
C20	0.050 (3)	0.050 (3)	0.110 (5)	−0.003 (3)	0.025 (3)	−0.012 (4)
C21	0.049 (3)	0.038 (3)	0.069 (4)	−0.001 (3)	0.019 (3)	0.000 (3)
Cl1	0.0909 (10)	0.0798 (10)	0.0966 (10)	0.0165 (10)	0.0068 (8)	−0.0179 (9)
Cl2	0.1014 (10)	0.0849 (11)	0.0788 (9)	0.0064 (10)	0.0320 (7)	0.0200 (9)
N1	0.040 (2)	0.065 (3)	0.044 (2)	0.003 (2)	0.009 (2)	−0.006 (2)
N2	0.060 (4)	0.059 (3)	0.083 (4)	−0.002 (3)	−0.002 (3)	−0.004 (3)
O1	0.057 (2)	0.088 (2)	0.0363 (19)	0.001 (2)	0.0039 (16)	−0.0121 (18)
O2	0.0591 (19)	0.060 (2)	0.0549 (19)	−0.0036 (19)	0.0230 (16)	−0.0048 (18)
O3	0.073 (3)	0.146 (4)	0.067 (3)	0.002 (3)	0.003 (2)	0.003 (3)
O4	0.056 (2)	0.155 (4)	0.124 (3)	0.012 (3)	−0.016 (2)	−0.003 (3)
O5	0.063 (2)	0.062 (2)	0.067 (2)	−0.006 (2)	0.0312 (18)	0.0019 (18)

Geometric parameters (Å, º) top

C1—C6	1.382 (5)	C12—C13	1.366 (5)
C1—C2	1.384 (6)	C12—H12	0.9300
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.366 (6)	C14—O5	1.186 (5)
C2—H2	0.9300	C14—O2	1.384 (5)
C3—C4	1.367 (5)	C14—C15	1.510 (6)
C3—Cl1	1.742 (5)	C15—C16	1.509 (5)
C4—C5	1.386 (5)	C15—H15A	0.9700
C4—H4	0.9300	C15—H15B	0.9700
C5—C6	1.388 (5)	C16—C21	1.379 (5)
C5—H5	0.9300	C16—C17	1.390 (5)
C6—C7	1.492 (6)	C17—C18	1.370 (6)
C7—O1	1.209 (5)	C17—H17	0.9300
C7—N1	1.367 (5)	C18—C19	1.386 (6)
C8—C13	1.385 (5)	C18—H18	0.9300
C8—C9	1.391 (5)	C19—C20	1.369 (6)
C8—N1	1.419 (5)	C19—H19	0.9300
C9—C10	1.386 (6)	C20—C21	1.378 (5)
C9—Cl2	1.724 (5)	C20—H20	0.9300
C10—C11	1.351 (6)	C21—N2	1.474 (6)
C10—H10	0.9300	N1—O2	1.426 (4)
C11—C12	1.381 (6)	N2—O4	1.191 (5)
C11—H11	0.9300	N2—O3	1.216 (4)

C6—C1—C2	120.0 (4)	C12—C13—H13	119.8
C6—C1—H1	120.0	C8—C13—H13	119.8
C2—C1—H1	120.0	O5—C14—O2	124.9 (5)
C3—C2—C1	119.8 (4)	O5—C14—C15	127.6 (4)
C3—C2—H2	120.1	O2—C14—C15	107.5 (4)
C1—C2—H2	120.1	C16—C15—C14	113.5 (4)
C2—C3—C4	121.5 (4)	C16—C15—H15A	108.9
C2—C3—Cl1	119.1 (4)	C14—C15—H15A	108.9
C4—C3—Cl1	119.4 (4)	C16—C15—H15B	108.9
C3—C4—C5	118.9 (4)	C14—C15—H15B	108.9
C3—C4—H4	120.5	H15A—C15—H15B	107.7
C5—C4—H4	120.5	C21—C16—C17	116.3 (4)
C4—C5—C6	120.5 (4)	C21—C16—C15	125.5 (4)
C4—C5—H5	119.7	C17—C16—C15	118.3 (4)
C6—C5—H5	119.7	C18—C17—C16	122.2 (5)
C1—C6—C5	119.3 (5)	C18—C17—H17	118.9
C1—C6—C7	123.4 (5)	C16—C17—H17	118.9
C5—C6—C7	117.2 (4)	C17—C18—C19	119.3 (5)
O1—C7—N1	121.7 (4)	C17—C18—H18	120.4
O1—C7—C6	121.5 (4)	C19—C18—H18	120.4
N1—C7—C6	116.8 (4)	C20—C19—C18	120.5 (5)
C13—C8—C9	119.1 (4)	C20—C19—H19	119.8
C13—C8—N1	121.2 (4)	C18—C19—H19	119.8
C9—C8—N1	119.6 (5)	C19—C20—C21	118.6 (5)
C10—C9—C8	119.5 (5)	C19—C20—H20	120.7
C10—C9—Cl2	120.1 (5)	C21—C20—H20	120.7
C8—C9—Cl2	120.4 (4)	C20—C21—C16	123.2 (5)
C11—C10—C9	120.5 (6)	C20—C21—N2	114.8 (5)
C11—C10—H10	119.7	C16—C21—N2	122.0 (4)
C9—C10—H10	119.7	C7—N1—C8	128.2 (4)
C10—C11—C12	120.3 (6)	C7—N1—O2	114.5 (3)
C10—C11—H11	119.8	C8—N1—O2	114.8 (3)
C12—C11—H11	119.8	O4—N2—O3	122.0 (5)
C13—C12—C11	120.1 (6)	O4—N2—C21	119.0 (5)
C13—C12—H12	120.0	O3—N2—C21	118.9 (4)
C11—C12—H12	120.0	C14—O2—N1	111.9 (3)
C12—C13—C8	120.4 (4)

C6—C1—C2—C3	−0.1 (7)	C14—C15—C16—C17	−107.7 (5)
C1—C2—C3—C4	−0.5 (7)	C21—C16—C17—C18	−0.7 (7)
C1—C2—C3—Cl1	179.9 (3)	C15—C16—C17—C18	−179.7 (4)
C2—C3—C4—C5	0.4 (7)	C16—C17—C18—C19	1.6 (8)
Cl1—C3—C4—C5	−180.0 (3)	C17—C18—C19—C20	−1.3 (8)
C3—C4—C5—C6	0.3 (7)	C18—C19—C20—C21	0.0 (8)
C2—C1—C6—C5	0.7 (6)	C19—C20—C21—C16	1.0 (7)
C2—C1—C6—C7	−174.2 (4)	C19—C20—C21—N2	179.7 (4)
C4—C5—C6—C1	−0.8 (6)	C17—C16—C21—C20	−0.6 (7)
C4—C5—C6—C7	174.4 (4)	C15—C16—C21—C20	178.3 (4)
C1—C6—C7—O1	134.5 (4)	C17—C16—C21—N2	−179.3 (4)
C5—C6—C7—O1	−40.6 (6)	C15—C16—C21—N2	−0.3 (7)
C1—C6—C7—N1	−45.1 (5)	O1—C7—N1—C8	159.2 (4)
C5—C6—C7—N1	139.9 (4)	C6—C7—N1—C8	−21.3 (6)
C13—C8—C9—C10	1.7 (6)	O1—C7—N1—O2	−1.6 (5)
N1—C8—C9—C10	−176.3 (4)	C6—C7—N1—O2	177.9 (3)
C13—C8—C9—Cl2	179.5 (3)	C13—C8—N1—C7	−49.9 (6)
N1—C8—C9—Cl2	1.5 (6)	C9—C8—N1—C7	128.1 (4)
C8—C9—C10—C11	−0.5 (7)	C13—C8—N1—O2	110.9 (4)
Cl2—C9—C10—C11	−178.4 (4)	C9—C8—N1—O2	−71.2 (5)
C9—C10—C11—C12	−1.5 (8)	C20—C21—N2—O4	−9.7 (7)
C10—C11—C12—C13	2.5 (8)	C16—C21—N2—O4	169.1 (5)
C11—C12—C13—C8	−1.3 (7)	C20—C21—N2—O3	169.2 (4)
C9—C8—C13—C12	−0.8 (6)	C16—C21—N2—O3	−12.1 (7)
N1—C8—C13—C12	177.2 (4)	O5—C14—O2—N1	7.0 (6)
O5—C14—C15—C16	23.1 (6)	C15—C14—O2—N1	−171.7 (3)
O2—C14—C15—C16	−158.2 (3)	C7—N1—O2—C14	74.1 (4)
C14—C15—C16—C21	73.3 (6)	C8—N1—O2—C14	−89.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.38	3.264 (7)	158
C15—H15B···O1ⁱⁱ	0.97	2.45	3.421 (6)	175

Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄Cl₂N₂O₅
M_r	445.24
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	12.366 (14), 6.789 (8), 12.579 (14)
β (°)	105.150 (14)
V (Å³)	1019 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.21 × 0.20 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.929, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	5091, 3669, 1821
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.069, 0.99
No. of reflections	3669
No. of parameters	271
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.16
Absolute structure	Flack (1983), 1624 Friedel pairs
Absolute structure parameter	0.40 (7)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.38	3.264 (7)	158
C15—H15B···O1ⁱⁱ	0.97	2.45	3.421 (6)	175

Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x, y−1/2, −z+1.

Acknowledgements

This work was supported by the Natural Science Fund Projects of Gansu Province (0710RJZA124).

References

Ayyangark, N. R., Hrailme, C., Kalkotf, U. R. & Srinivasan, K. V. (1986). Synth. Commun. pp. 938–941. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Noh, E. J., Lim, D. S., Jeong, G. & Lee, J. S. (2009). Biochem. Biophys. Res. Commun. 378, 326–331. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zeng, W., Zeng, G. Y. & Qin, S. Y. (2003). Chin. J. Org. Chem. 23, 1213–1218. CAS Google Scholar
Zhang, H., Qu, D. & Ma, J. (2012). Acta Cryst. E68, o2904. CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 11| November 2012| Page o3067

doi:10.1107/S1600536812040883

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-(4-chloro­benzo­yl)-N-(2-chloro­phen­yl)-O-[2-(2-nitro­phen­yl)acet­yl]hydroxyl­amine

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-(4-chlorobenzoyl)-N-(2-chlorophenyl)-O-[2-(2-nitrophenyl)acetyl]hydroxylamine