N-(2-Chloro­phen­yl)-1-(4-chloro­phen­yl)formamido 3-(2-nitrophenyl)­propano­ate

Fan, L.-L.; Wang, H.; Ma, J.; Shi, X.-X.

doi:10.1107/S1600536812048726

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3498

doi:10.1107/S1600536812048726

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N-(2-Chlorophenyl)-1-(4-chlorophenyl)formamido 3-(2-nitrophenyl)propanoate

Lin-Lan Fan,^a ^* Hui Wang,^b Jing Ma ^c and Xiu-Xiao Shi ^c

^aDepartment of Laboratory Center for Medical Sciences, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, Gansu Province, People's Republic of China, ^bJiuquan Institute for Food and Drug Control, Jiuquan 735000, Gansu Province, People's Republic of China, and ^cInstitute of Medicinal Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 730000, Gansu Province, People's Republic of China
^*Correspondence e-mail: fanlinlan1020@163.com

(Received 14 November 2012; accepted 27 November 2012; online 30 November 2012)

In the title hydroxamic acid derivative, C₂₂H₁₆Cl₂N₂O₅, the nitro-substituted benzene ring forms dihedral angles of 26.95 (15) and 87.06 (15)°, with the 4-chloro- and 2-chloro-substituted benzene rings, respectively. The dihedral angle between the chloro-substituted benzene rings is 68.19 (13)°. The O atoms of the nitro group were refined as disordered over two sets of sites with equal occupancies. In the crystal, weak C—H⋯O(=C) hydrogen bonds link molecules along [100].

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 related structures, see: Zhang et al. (2012 ); Ma et al. (2012 ).

Experimental

Crystal data

C₂₂H₁₆Cl₂N₂O₅
M_r = 459.27
Triclinic, $[P \overline 1]$
a = 9.1574 (8) Å
b = 10.1976 (6) Å
c = 12.1736 (8) Å
α = 91.847 (5)°
β = 108.327 (8)°
γ = 100.285 (6)°
V = 1057.06 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 293 K
0.32 × 0.28 × 0.25 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.843, T_max = 1.000
7898 measured reflections
4785 independent reflections
3434 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.139
S = 1.04
4785 reflections
298 parameters
24 restraints
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1ⁱ	0.93	2.52	3.354 (4)	150
C13—H13⋯O3ⁱⁱ	0.93	2.48	3.223 (4)	137
Symmetry codes: (i) x+1, y, z; (ii) -x, -y, -z.

Data collection: CrysAlis PRO (Agilent, 2011); 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: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812048726/lh5558sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812048726/lh5558Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812048726/lh5558Isup3.cml

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). We have performed the crystal structure determination of the title hydroxamic acid derivative.

The molecular structure of the title compound is shown in Fig. 1. The nitro-substituted benzene ring (C17-C22) forms dihedral angles of 26.95 (15) and 87.06 (15)°, with the p-chloro (C1-C6) and o-chloro-substituted (C8-C13) benzene rings, respectively. The dihedral angle between the two chloro-substituted benzene rings is 68.19 (13) °. Closely related structures appear in the literature (Zhang et al., 2012; Ma et al., 2012). In the crystal, weak C—H···O(═C) hydrogen bonds links molecules along [100] (Fig. 2).

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 related structures, see: Zhang et al. (2012); Ma et al. (2012).

Experimental top

The title compound (I) was prepared according to the method described by Ayyangark et al. (1986). Crystals of (I) 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: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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 dllipsoids. H atoms are shown as small spheres of arbitrary radius. The disorder is not shown.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines. The disorder is not shown.

N-(2-Chlorophenyl)-1-(4-chlorophenyl)formamido 3-(2-nitrophenyl)propanoate top

Crystal data top

C₂₂H₁₆Cl₂N₂O₅	Z = 2
M_r = 459.27	F(000) = 472
Triclinic, P1	D_x = 1.443 Mg m⁻³
a = 9.1574 (8) Å	Mo Kα radiation, λ = 0.7107 Å
b = 10.1976 (6) Å	Cell parameters from 2906 reflections
c = 12.1736 (8) Å	θ = 3.0–28.5°
α = 91.847 (5)°	µ = 0.34 mm⁻¹
β = 108.327 (8)°	T = 293 K
γ = 100.285 (6)°	Block, colourless
V = 1057.06 (13) Å³	0.32 × 0.28 × 0.25 mm

Data collection top

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer	4785 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3434 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.018
Detector resolution: 16.0733 pixels mm^-1	θ_max = 28.6°, θ_min = 3.0°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→13
T_min = 0.843, T_max = 1.000	l = −12→15
7898 measured reflections

Refinement top

Refinement on F²	24 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.055	w = 1/[σ²(F_o²) + (0.0447P)² + 0.5564P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.139	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.48 e Å⁻³
4785 reflections	Δρ_min = −0.45 e Å⁻³
298 parameters

Crystal data top

C₂₂H₁₆Cl₂N₂O₅	γ = 100.285 (6)°
M_r = 459.27	V = 1057.06 (13) Å³
Triclinic, P1	Z = 2
a = 9.1574 (8) Å	Mo Kα radiation
b = 10.1976 (6) Å	µ = 0.34 mm⁻¹
c = 12.1736 (8) Å	T = 293 K
α = 91.847 (5)°	0.32 × 0.28 × 0.25 mm
β = 108.327 (8)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer	4785 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3434 reflections with I > 2σ(I)
T_min = 0.843, T_max = 1.000	R_int = 0.018
7898 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	24 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.04	Δρ_max = 0.48 e Å⁻³
4785 reflections	Δρ_min = −0.45 e Å⁻³
298 parameters

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	Occ. (<1)
Cl1	0.30250 (8)	0.14141 (7)	0.49104 (6)	0.0635 (2)
Cl2	0.24622 (12)	−0.53403 (8)	0.43213 (9)	0.0942 (3)
O2	0.03359 (18)	0.18128 (15)	0.24969 (15)	0.0496 (4)
O1	−0.1073 (2)	−0.01016 (18)	0.33664 (18)	0.0641 (5)
O3	−0.1782 (3)	0.0981 (2)	0.09403 (19)	0.0827 (7)
N1	0.0768 (2)	0.05360 (18)	0.25036 (18)	0.0455 (5)
C9	0.3548 (3)	0.1106 (2)	0.3701 (2)	0.0473 (5)
C8	0.2407 (3)	0.0716 (2)	0.2637 (2)	0.0436 (5)
C7	0.0030 (3)	−0.0337 (2)	0.3102 (2)	0.0468 (5)
C6	0.0626 (3)	−0.1603 (2)	0.3349 (2)	0.0456 (5)
C3	0.1726 (3)	−0.3910 (2)	0.3938 (3)	0.0583 (7)
C14	−0.0991 (3)	0.1893 (3)	0.1623 (2)	0.0532 (6)
C13	0.2822 (3)	0.0474 (3)	0.1654 (3)	0.0576 (7)
H13	0.2058	0.0246	0.0927	0.069*
C4	0.1748 (3)	−0.3425 (2)	0.2910 (3)	0.0600 (7)
H4	0.2127	−0.3874	0.2414	0.072*
C17	−0.3174 (3)	0.4808 (3)	0.1221 (2)	0.0558 (7)
C1	0.0565 (3)	−0.2147 (3)	0.4362 (2)	0.0565 (6)
H1	0.0148	−0.1728	0.4849	0.068*
C5	0.1203 (3)	−0.2260 (2)	0.2610 (2)	0.0538 (6)
H5	0.1223	−0.1919	0.1915	0.065*
C18	−0.2762 (3)	0.6005 (3)	0.0793 (2)	0.0594 (7)
C15	−0.1275 (3)	0.3281 (2)	0.1738 (2)	0.0545 (6)
H15A	−0.0445	0.3904	0.1583	0.065*
H15B	−0.1223	0.3501	0.2532	0.065*
N2	−0.1934 (4)	0.6103 (4)	−0.0050 (3)	0.0862 (8)
C11	0.5514 (4)	0.0928 (3)	0.2855 (4)	0.0758 (9)
H11	0.6565	0.0978	0.2930	0.091*
C12	0.4391 (4)	0.0577 (3)	0.1778 (3)	0.0731 (9)
H12	0.4689	0.0409	0.1132	0.088*
C10	0.5115 (3)	0.1204 (3)	0.3813 (3)	0.0634 (7)
H10	0.5887	0.1455	0.4533	0.076*
C2	0.1111 (3)	−0.3299 (3)	0.4659 (3)	0.0642 (7)
H2	0.1064	−0.3660	0.5342	0.077*
C16	−0.2842 (3)	0.3464 (3)	0.0924 (3)	0.0670 (8)
H16A	−0.2836	0.3403	0.0129	0.080*
H16B	−0.3667	0.2756	0.0986	0.080*
C20	−0.3816 (4)	0.7203 (4)	0.1959 (3)	0.0823 (10)
H20	−0.4026	0.7998	0.2210	0.099*
C22	−0.3929 (4)	0.4867 (3)	0.2037 (3)	0.0744 (8)
H22	−0.4229	0.4084	0.2350	0.089*
C21	−0.4252 (4)	0.6038 (4)	0.2402 (3)	0.0854 (10)
H21	−0.4768	0.6038	0.2949	0.102*
C19	−0.3082 (4)	0.7198 (3)	0.1157 (3)	0.0744 (9)
H19	−0.2790	0.7987	0.0850	0.089*
O4B	−0.2146 (9)	0.5291 (11)	−0.0774 (8)	0.137 (4)	0.50
O5A	−0.2098 (13)	0.6859 (11)	−0.0663 (10)	0.171 (4)	0.50
O4A	−0.1345 (10)	0.5136 (9)	−0.0205 (7)	0.114 (3)	0.50
O5B	−0.0987 (8)	0.7288 (7)	−0.0029 (5)	0.0943 (17)	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0684 (4)	0.0682 (4)	0.0530 (4)	0.0221 (3)	0.0142 (3)	0.0018 (3)
Cl2	0.1052 (7)	0.0560 (4)	0.1179 (8)	0.0351 (4)	0.0201 (6)	0.0158 (5)
O2	0.0434 (9)	0.0434 (8)	0.0577 (10)	0.0202 (7)	0.0046 (7)	0.0009 (7)
O1	0.0492 (10)	0.0645 (11)	0.0909 (14)	0.0216 (9)	0.0346 (10)	0.0043 (10)
O3	0.0803 (14)	0.0757 (13)	0.0724 (14)	0.0383 (11)	−0.0127 (11)	−0.0204 (11)
N1	0.0394 (10)	0.0423 (10)	0.0578 (12)	0.0189 (8)	0.0140 (9)	0.0052 (9)
C9	0.0416 (12)	0.0391 (11)	0.0630 (15)	0.0134 (9)	0.0159 (11)	0.0125 (11)
C8	0.0388 (12)	0.0397 (11)	0.0571 (14)	0.0161 (9)	0.0171 (10)	0.0110 (10)
C7	0.0368 (12)	0.0475 (12)	0.0557 (14)	0.0117 (10)	0.0133 (10)	−0.0034 (11)
C6	0.0340 (11)	0.0407 (11)	0.0608 (15)	0.0053 (9)	0.0154 (10)	−0.0026 (10)
C3	0.0549 (15)	0.0398 (12)	0.0733 (19)	0.0091 (11)	0.0117 (13)	0.0022 (12)
C14	0.0477 (14)	0.0620 (15)	0.0497 (14)	0.0255 (12)	0.0079 (11)	0.0009 (12)
C13	0.0608 (16)	0.0535 (14)	0.0696 (18)	0.0201 (12)	0.0311 (14)	0.0147 (13)
C4	0.0606 (16)	0.0457 (13)	0.080 (2)	0.0152 (12)	0.0298 (14)	−0.0048 (13)
C17	0.0432 (13)	0.0602 (15)	0.0573 (15)	0.0255 (12)	−0.0009 (11)	0.0024 (12)
C1	0.0568 (15)	0.0526 (14)	0.0655 (17)	0.0093 (12)	0.0289 (13)	0.0018 (12)
C5	0.0560 (15)	0.0455 (13)	0.0635 (16)	0.0116 (11)	0.0243 (12)	0.0003 (11)
C18	0.0480 (14)	0.0698 (17)	0.0559 (16)	0.0250 (13)	0.0032 (12)	0.0071 (13)
C15	0.0506 (14)	0.0529 (14)	0.0571 (15)	0.0240 (11)	0.0064 (11)	0.0015 (12)
N2	0.088 (2)	0.106 (2)	0.071 (2)	0.037 (2)	0.0235 (16)	0.026 (2)
C11	0.0516 (17)	0.0695 (18)	0.122 (3)	0.0229 (14)	0.0430 (19)	0.0298 (19)
C12	0.086 (2)	0.0659 (18)	0.098 (3)	0.0309 (16)	0.063 (2)	0.0240 (17)
C10	0.0421 (14)	0.0575 (15)	0.089 (2)	0.0134 (12)	0.0159 (14)	0.0201 (15)
C2	0.0716 (18)	0.0520 (15)	0.0662 (18)	0.0074 (13)	0.0209 (15)	0.0079 (13)
C16	0.0606 (17)	0.0610 (16)	0.0701 (18)	0.0311 (13)	−0.0015 (14)	0.0003 (14)
C20	0.070 (2)	0.080 (2)	0.089 (2)	0.0403 (18)	0.0030 (18)	−0.0141 (19)
C22	0.0614 (18)	0.084 (2)	0.084 (2)	0.0323 (16)	0.0222 (16)	0.0157 (17)
C21	0.070 (2)	0.111 (3)	0.083 (2)	0.045 (2)	0.0217 (18)	−0.001 (2)
C19	0.0672 (19)	0.0629 (17)	0.082 (2)	0.0270 (15)	0.0005 (16)	0.0067 (16)
O4B	0.106 (6)	0.178 (8)	0.124 (7)	−0.001 (5)	0.055 (5)	−0.074 (6)
O5A	0.222 (9)	0.153 (7)	0.193 (8)	0.065 (7)	0.119 (7)	0.114 (7)
O4A	0.140 (7)	0.131 (5)	0.124 (6)	0.071 (5)	0.087 (5)	0.062 (5)
O5B	0.111 (5)	0.096 (4)	0.082 (4)	0.012 (3)	0.042 (3)	0.027 (3)

Geometric parameters (Å, º) top

Cl1—C9	1.721 (3)	C5—H5	0.9300
Cl2—C3	1.731 (3)	C18—N2	1.451 (4)
O2—N1	1.426 (2)	C18—C19	1.391 (4)
O2—C14	1.357 (3)	C15—H15A	0.9700
O1—C7	1.211 (3)	C15—H15B	0.9700
O3—C14	1.189 (3)	C15—C16	1.513 (3)
N1—C8	1.436 (3)	N2—O4B	1.135 (8)
N1—C7	1.385 (3)	N2—O5A	1.087 (8)
C9—C8	1.377 (3)	N2—O4A	1.241 (8)
C9—C10	1.383 (3)	N2—O5B	1.350 (7)
C8—C13	1.392 (4)	C11—H11	0.9300
C7—C6	1.492 (3)	C11—C12	1.377 (5)
C6—C1	1.381 (4)	C11—C10	1.363 (4)
C6—C5	1.387 (3)	C12—H12	0.9300
C3—C4	1.365 (4)	C10—H10	0.9300
C3—C2	1.370 (4)	C2—H2	0.9300
C14—C15	1.494 (3)	C16—H16A	0.9700
C13—H13	0.9300	C16—H16B	0.9700
C13—C12	1.380 (4)	C20—H20	0.9300
C4—H4	0.9300	C20—C21	1.367 (5)
C4—C5	1.385 (3)	C20—C19	1.348 (5)
C17—C18	1.380 (4)	C22—H22	0.9300
C17—C16	1.512 (3)	C22—C21	1.373 (4)
C17—C22	1.383 (4)	C21—H21	0.9300
C1—H1	0.9300	C19—H19	0.9300
C1—C2	1.372 (4)

C14—O2—N1	114.19 (17)	H15A—C15—H15B	107.7
O2—N1—C8	109.22 (16)	C16—C15—H15A	108.9
C7—N1—O2	112.21 (17)	C16—C15—H15B	108.9
C7—N1—C8	123.88 (18)	O4B—N2—C18	123.7 (6)
C8—C9—Cl1	120.05 (18)	O4B—N2—O5B	119.1 (6)
C8—C9—C10	120.3 (3)	O5A—N2—C18	119.8 (6)
C10—C9—Cl1	119.6 (2)	O5A—N2—O4B	91.5 (9)
C9—C8—N1	121.6 (2)	O5A—N2—O4A	121.4 (7)
C9—C8—C13	120.4 (2)	O5A—N2—O5B	50.8 (6)
C13—C8—N1	118.0 (2)	O4A—N2—C18	116.9 (4)
O1—C7—N1	121.4 (2)	O4A—N2—O5B	112.4 (6)
O1—C7—C6	122.4 (2)	O5B—N2—C18	116.9 (4)
N1—C7—C6	116.12 (19)	C12—C11—H11	119.4
C1—C6—C7	117.4 (2)	C10—C11—H11	119.4
C1—C6—C5	119.0 (2)	C10—C11—C12	121.3 (3)
C5—C6—C7	123.5 (2)	C13—C12—H12	119.9
C4—C3—Cl2	119.1 (2)	C11—C12—C13	120.2 (3)
C4—C3—C2	121.3 (2)	C11—C12—H12	119.9
C2—C3—Cl2	119.6 (2)	C9—C10—H10	120.4
O2—C14—C15	107.5 (2)	C11—C10—C9	119.1 (3)
O3—C14—O2	124.2 (2)	C11—C10—H10	120.4
O3—C14—C15	128.2 (2)	C3—C2—C1	119.2 (3)
C8—C13—H13	120.6	C3—C2—H2	120.4
C12—C13—C8	118.7 (3)	C1—C2—H2	120.4
C12—C13—H13	120.6	C17—C16—C15	110.6 (2)
C3—C4—H4	120.2	C17—C16—H16A	109.5
C3—C4—C5	119.5 (2)	C17—C16—H16B	109.5
C5—C4—H4	120.2	C15—C16—H16A	109.5
C18—C17—C16	127.2 (3)	C15—C16—H16B	109.5
C18—C17—C22	115.7 (3)	H16A—C16—H16B	108.1
C22—C17—C16	117.1 (3)	C21—C20—H20	120.0
C6—C1—H1	119.5	C19—C20—H20	120.0
C2—C1—C6	120.9 (2)	C19—C20—C21	120.0 (3)
C2—C1—H1	119.5	C17—C22—H22	118.8
C6—C5—H5	120.0	C21—C22—C17	122.4 (3)
C4—C5—C6	119.9 (3)	C21—C22—H22	118.8
C4—C5—H5	120.0	C20—C21—C22	119.9 (3)
C17—C18—N2	121.9 (3)	C20—C21—H21	120.0
C17—C18—C19	122.4 (3)	C22—C21—H21	120.0
C19—C18—N2	115.7 (3)	C18—C19—H19	120.2
C14—C15—H15A	108.9	C20—C19—C18	119.6 (3)
C14—C15—H15B	108.9	C20—C19—H19	120.2
C14—C15—C16	113.4 (2)

Cl1—C9—C8—N1	−1.0 (3)	C14—C15—C16—C17	170.5 (3)
Cl1—C9—C8—C13	179.59 (17)	C4—C3—C2—C1	−2.6 (4)
Cl1—C9—C10—C11	178.5 (2)	C17—C18—N2—O4B	36.3 (8)
Cl2—C3—C4—C5	−178.2 (2)	C17—C18—N2—O5A	151.0 (9)
Cl2—C3—C2—C1	178.4 (2)	C17—C18—N2—O4A	−13.5 (7)
O2—N1—C8—C9	78.1 (2)	C17—C18—N2—O5B	−150.8 (4)
O2—N1—C8—C13	−102.5 (2)	C17—C18—C19—C20	0.2 (4)
O2—N1—C7—O1	13.8 (3)	C17—C22—C21—C20	−0.4 (5)
O2—N1—C7—C6	−168.96 (18)	C1—C6—C5—C4	−1.8 (4)
O2—C14—C15—C16	−171.8 (2)	C5—C6—C1—C2	2.1 (4)
O1—C7—C6—C1	−34.9 (3)	C18—C17—C16—C15	89.3 (3)
O1—C7—C6—C5	143.9 (3)	C18—C17—C22—C21	0.0 (4)
O3—C14—C15—C16	5.3 (5)	N2—C18—C19—C20	−178.5 (3)
N1—O2—C14—O3	2.9 (4)	C12—C11—C10—C9	1.1 (4)
N1—O2—C14—C15	−179.87 (19)	C10—C9—C8—N1	176.6 (2)
N1—C8—C13—C12	−176.8 (2)	C10—C9—C8—C13	−2.7 (3)
N1—C7—C6—C1	147.9 (2)	C10—C11—C12—C13	−1.2 (4)
N1—C7—C6—C5	−33.3 (3)	C2—C3—C4—C5	2.9 (4)
C9—C8—C13—C12	2.6 (3)	C16—C17—C18—N2	0.9 (4)
C8—N1—C7—O1	148.4 (2)	C16—C17—C18—C19	−177.7 (2)
C8—N1—C7—C6	−34.3 (3)	C16—C17—C22—C21	178.1 (3)
C8—C9—C10—C11	0.8 (4)	C22—C17—C18—N2	178.7 (3)
C8—C13—C12—C11	−0.7 (4)	C22—C17—C18—C19	0.1 (4)
C7—N1—C8—C9	−57.7 (3)	C22—C17—C16—C15	−88.4 (3)
C7—N1—C8—C13	121.7 (2)	C21—C20—C19—C18	−0.5 (5)
C7—C6—C1—C2	−179.0 (2)	C19—C18—N2—O4B	−145.0 (8)
C7—C6—C5—C4	179.4 (2)	C19—C18—N2—O5A	−30.3 (10)
C6—C1—C2—C3	0.1 (4)	C19—C18—N2—O4A	165.2 (6)
C3—C4—C5—C6	−0.6 (4)	C19—C18—N2—O5B	27.9 (5)
C14—O2—N1—C8	132.4 (2)	C19—C20—C21—C22	0.6 (5)
C14—O2—N1—C7	−86.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱ	0.93	2.52	3.354 (4)	150
C13—H13···O3ⁱⁱ	0.93	2.48	3.223 (4)	137

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆Cl₂N₂O₅
M_r	459.27
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.1574 (8), 10.1976 (6), 12.1736 (8)
α, β, γ (°)	91.847 (5), 108.327 (8), 100.285 (6)
V (Å³)	1057.06 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.32 × 0.28 × 0.25

Data collection
Diffractometer	Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.843, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7898, 4785, 3434
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.674

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.139, 1.04
No. of reflections	4785
No. of parameters	298
No. of restraints	24
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.45

Computer programs: CrysAlis PRO (Agilent, 2011), 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
C11—H11···O1ⁱ	0.93	2.52	3.354 (4)	150
C13—H13···O3ⁱⁱ	0.93	2.48	3.223 (4)	137

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

Acknowledgements

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

References

Agilent (2011). CrysAlis PRO. Aglient Technologies Ltd, Yarnton, England. Google Scholar
Ayyangark, N. R., Hrailme, C., Kalkotf, U. R. & Srinivasan, K. V. (1986). Synth. Commun. pp. 938–941. Google Scholar
Ma, J., Ma, Y. & He, D. (2012). Acta Cryst. E68, o3067. CSD CrossRef 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. (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 12| December 2012| Page o3498

doi:10.1107/S1600536812048726

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

N-(2-Chloro­phen­yl)-1-(4-chloro­phen­yl)formamido 3-(2-nitro­phenyl)­propano­ate

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Experimental

Crystal data

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organic compounds

N-(2-Chlorophenyl)-1-(4-chlorophenyl)formamido 3-(2-nitrophenyl)propanoate