(4-Chlorobenzoyl)(4-chlorophenyl)amino 3-(2-nitrophenyl)propanoate

Ding, Y.; Shao, C.

doi:10.1107/S1600536813007174

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o561

doi:10.1107/S1600536813007174

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(4-Chlorobenzoyl)(4-chlorophenyl)amino 3-(2-nitrophenyl)propanoate

Yi-lan Ding ^a and Chang-jiang Shao ^b ^*

^aLanzhou Maternal and Child Health Care Hospital, Lanzhou 730000, Gansu Province, People's Republic of China, and ^bThe Peoples First Hospital of Lanzhou, Lanzhou 730000, Gansu Province, People's Republic of China
^*Correspondence e-mail: shaochangjiang1020@126.com

(Received 28 February 2013; accepted 15 March 2013; online 23 March 2013)

In the title hydroxamic acid derivate, C₂₂H₁₆Cl₂N₂O₅, the nitro-substituted benzene ring forms dihedral angles of 14.11 (15) and 16.08 (15)°, with the 4-chlorobenzoyl and 4-chlorophenyl benzene rings, respectively. The dihedral angle between the chloro-substituted benzene rings is 2.28 (13)°. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming chains 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 = 6.1710 (3) Å
b = 12.8881 (7) Å
c = 13.3490 (8) Å
α = 89.933 (5)°
β = 76.959 (5)°
γ = 82.114 (4)°
V = 1024.03 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 294 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 = 0.757, T_max = 1.000
7506 measured reflections
4578 independent reflections
3269 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.113
S = 1.02
4578 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1ⁱ	0.93	2.40	3.177 (2)	140
C17—H17B⋯O4ⁱⁱ	0.97	2.55	3.515 (3)	171
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x-1, y, z.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813007174/lh5593sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813007174/lh5593Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813007174/lh5593Isup3.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 (C18-C23) forms dihedral angles of 14.11 (15) and 16.08 (15)°, with the p-chloro (C9-C14) and p-chloro-substituted (C1-C6) benzene rings, respectively. The dihedral angle between the two chloro-substituted benzene rings is 2.28 (13) °. In the crystal, molecules are linked by weak C—H···O hydrogen bonds to form chains along [100]. Closely related structures appear in the literature (Zhang et al., 2012; Ma 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 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: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

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.

(4-Chlorobenzoyl)(4-chlorophenyl)amino 3-(2-nitrophenyl)propanoate top

Crystal data top

C₂₂H₁₆Cl₂N₂O₅	Z = 2
M_r = 459.27	F(000) = 472
Triclinic, P1	D_x = 1.489 Mg m⁻³
a = 6.1710 (3) Å	Mo Kα radiation, λ = 0.7107 Å
b = 12.8881 (7) Å	Cell parameters from 2661 reflections
c = 13.3490 (8) Å	θ = 3.1–28.4°
α = 89.933 (5)°	µ = 0.36 mm⁻¹
β = 76.959 (5)°	T = 294 K
γ = 82.114 (4)°	Block, colourless
V = 1024.03 (10) Å³	0.32 × 0.28 × 0.25 mm

Data collection top

Agilent SuperNova (Dual, Cu at zero) Eos diffractometer	4578 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3269 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.021
Detector resolution: 16.0733 pixels mm^-1	θ_max = 28.5°, θ_min = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −16→16
T_min = 0.757, T_max = 1.000	l = −17→14
7506 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.044	w = 1/[σ²(F_o²) + (0.0388P)² + 0.2287P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.113	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.17 e Å⁻³
4578 reflections	Δρ_min = −0.28 e Å⁻³
280 parameters

Crystal data top

C₂₂H₁₆Cl₂N₂O₅	γ = 82.114 (4)°
M_r = 459.27	V = 1024.03 (10) Å³
Triclinic, P1	Z = 2
a = 6.1710 (3) Å	Mo Kα radiation
b = 12.8881 (7) Å	µ = 0.36 mm⁻¹
c = 13.3490 (8) Å	T = 294 K
α = 89.933 (5)°	0.32 × 0.28 × 0.25 mm
β = 76.959 (5)°

Data collection top

Agilent SuperNova (Dual, Cu at zero) Eos diffractometer	4578 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3269 reflections with I > 2σ(I)
T_min = 0.757, T_max = 1.000	R_int = 0.021
7506 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.02	Δρ_max = 0.17 e Å⁻³
4578 reflections	Δρ_min = −0.28 e Å⁻³
280 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	−0.18649 (10)	0.33888 (6)	0.87407 (5)	0.0768 (2)
Cl2	1.31097 (10)	0.36534 (5)	0.04403 (5)	0.0728 (2)
O1	0.3913 (2)	0.46847 (10)	0.41480 (11)	0.0514 (4)
O2	0.6701 (2)	0.23063 (9)	0.47616 (10)	0.0446 (3)
O3	0.4204 (3)	0.15481 (12)	0.41153 (13)	0.0669 (5)
O4	1.2426 (3)	−0.06198 (14)	0.30600 (14)	0.0745 (5)
O5	1.4243 (3)	−0.09770 (15)	0.14952 (16)	0.0870 (6)
N1	0.5125 (3)	0.32286 (12)	0.48837 (13)	0.0488 (4)
N2	1.2639 (3)	−0.05271 (14)	0.21312 (17)	0.0567 (5)
C1	0.3969 (3)	0.28616 (15)	0.66805 (16)	0.0467 (5)
H1	0.5433	0.2555	0.6661	0.056*
C2	0.2353 (3)	0.28899 (16)	0.75827 (16)	0.0500 (5)
H2	0.2719	0.2603	0.8173	0.060*
C3	0.0195 (3)	0.33459 (15)	0.76041 (15)	0.0451 (5)
C4	−0.0374 (3)	0.37795 (15)	0.67448 (16)	0.0485 (5)
H4	−0.1837	0.4093	0.6772	0.058*
C5	0.1242 (3)	0.37473 (15)	0.58384 (15)	0.0475 (5)
H5	0.0866	0.4035	0.5250	0.057*
C6	0.3422 (3)	0.32880 (13)	0.58035 (14)	0.0402 (4)
C7	0.5349 (3)	0.39283 (14)	0.41068 (14)	0.0408 (4)
C9	0.9520 (3)	0.33060 (15)	0.32673 (15)	0.0455 (5)
H9	0.9773	0.3017	0.3877	0.055*
C10	1.1284 (3)	0.32752 (16)	0.24154 (16)	0.0487 (5)
H10	1.2719	0.2969	0.2450	0.058*
C11	1.0896 (3)	0.37022 (16)	0.15145 (16)	0.0475 (5)
C12	0.8791 (3)	0.41665 (16)	0.14499 (16)	0.0498 (5)
H12	0.8551	0.4451	0.0837	0.060*
C13	0.7042 (3)	0.42046 (15)	0.23050 (15)	0.0441 (4)
H13	0.5621	0.4529	0.2268	0.053*
C14	0.7361 (3)	0.37675 (13)	0.32217 (14)	0.0390 (4)
C15	0.5977 (3)	0.14812 (15)	0.43340 (15)	0.0451 (5)
C16	0.7738 (3)	0.05388 (14)	0.42254 (16)	0.0472 (5)
H16A	0.7454	0.0137	0.4845	0.057*
H16B	0.9199	0.0766	0.4152	0.057*
C17	0.7776 (3)	−0.01623 (15)	0.32980 (16)	0.0479 (5)
H17A	0.8685	−0.0829	0.3345	0.057*
H17B	0.6260	−0.0296	0.3314	0.057*
C18	0.8705 (3)	0.03217 (14)	0.22905 (15)	0.0429 (4)
C19	1.0947 (3)	0.01729 (15)	0.17520 (16)	0.0450 (5)
C20	1.1712 (4)	0.06501 (18)	0.08326 (18)	0.0589 (6)
H20	1.3221	0.0522	0.0498	0.071*
C21	1.0231 (5)	0.13115 (18)	0.04204 (19)	0.0665 (6)
H21	1.0729	0.1647	−0.0188	0.080*
C22	0.8000 (4)	0.14722 (17)	0.09175 (19)	0.0640 (6)
H22	0.6982	0.1915	0.0639	0.077*
C23	0.7258 (4)	0.09832 (16)	0.18248 (18)	0.0542 (5)
H23	0.5735	0.1098	0.2139	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0613 (4)	0.0970 (5)	0.0541 (4)	0.0046 (3)	0.0148 (3)	0.0189 (3)
Cl2	0.0545 (3)	0.0921 (5)	0.0570 (4)	0.0001 (3)	0.0116 (3)	0.0122 (3)
O1	0.0516 (8)	0.0480 (8)	0.0467 (8)	0.0080 (6)	−0.0041 (7)	0.0103 (6)
O2	0.0459 (7)	0.0344 (7)	0.0468 (8)	0.0041 (5)	−0.0020 (6)	0.0021 (6)
O3	0.0497 (9)	0.0645 (10)	0.0839 (12)	0.0104 (7)	−0.0210 (9)	−0.0156 (9)
O4	0.0601 (10)	0.0904 (13)	0.0709 (13)	0.0111 (9)	−0.0239 (9)	0.0071 (10)
O5	0.0570 (10)	0.0872 (13)	0.0979 (15)	0.0279 (9)	−0.0008 (10)	−0.0043 (11)
N1	0.0554 (10)	0.0346 (8)	0.0430 (9)	0.0104 (7)	0.0065 (8)	0.0069 (7)
N2	0.0405 (9)	0.0541 (10)	0.0727 (14)	0.0027 (8)	−0.0128 (9)	−0.0007 (10)
C1	0.0417 (10)	0.0455 (10)	0.0475 (12)	0.0044 (8)	−0.0054 (9)	0.0090 (9)
C2	0.0524 (12)	0.0527 (12)	0.0411 (11)	0.0004 (9)	−0.0074 (9)	0.0115 (9)
C3	0.0450 (11)	0.0441 (10)	0.0399 (11)	−0.0027 (8)	0.0009 (9)	0.0033 (8)
C4	0.0391 (10)	0.0528 (12)	0.0491 (12)	0.0025 (9)	−0.0057 (9)	0.0069 (9)
C5	0.0474 (11)	0.0526 (11)	0.0400 (11)	0.0016 (9)	−0.0097 (9)	0.0079 (9)
C6	0.0452 (10)	0.0339 (9)	0.0366 (10)	−0.0018 (8)	−0.0013 (8)	0.0006 (7)
C7	0.0464 (10)	0.0388 (10)	0.0360 (10)	−0.0029 (8)	−0.0087 (8)	0.0018 (8)
C9	0.0461 (11)	0.0508 (11)	0.0412 (11)	−0.0072 (9)	−0.0134 (9)	0.0090 (9)
C10	0.0385 (10)	0.0549 (12)	0.0514 (12)	−0.0048 (9)	−0.0084 (9)	0.0070 (9)
C11	0.0426 (10)	0.0511 (11)	0.0437 (12)	−0.0063 (9)	0.0003 (9)	0.0011 (9)
C12	0.0523 (12)	0.0556 (12)	0.0385 (11)	−0.0022 (9)	−0.0075 (9)	0.0092 (9)
C13	0.0418 (10)	0.0475 (11)	0.0405 (11)	−0.0008 (8)	−0.0076 (9)	0.0061 (8)
C14	0.0425 (10)	0.0362 (9)	0.0384 (10)	−0.0066 (8)	−0.0088 (8)	0.0014 (7)
C15	0.0465 (11)	0.0416 (10)	0.0408 (11)	0.0017 (8)	−0.0016 (9)	0.0032 (8)
C16	0.0497 (11)	0.0379 (10)	0.0496 (12)	0.0045 (8)	−0.0086 (9)	0.0038 (8)
C17	0.0442 (10)	0.0376 (10)	0.0594 (13)	−0.0014 (8)	−0.0093 (10)	−0.0013 (9)
C18	0.0439 (10)	0.0349 (9)	0.0497 (12)	−0.0014 (8)	−0.0126 (9)	−0.0057 (8)
C19	0.0432 (10)	0.0400 (10)	0.0506 (12)	0.0010 (8)	−0.0120 (9)	−0.0043 (9)
C20	0.0560 (13)	0.0579 (13)	0.0571 (14)	−0.0051 (11)	−0.0024 (11)	−0.0039 (11)
C21	0.0851 (18)	0.0564 (13)	0.0553 (15)	−0.0061 (12)	−0.0128 (13)	0.0077 (11)
C22	0.0783 (17)	0.0532 (13)	0.0615 (16)	0.0066 (11)	−0.0276 (14)	0.0049 (11)
C23	0.0488 (11)	0.0522 (12)	0.0604 (14)	0.0063 (9)	−0.0179 (11)	−0.0040 (10)

Geometric parameters (Å, º) top

Cl1—C3	1.7411 (19)	C10—C11	1.378 (3)
Cl2—C11	1.738 (2)	C10—H10	0.9300
O1—C7	1.216 (2)	C11—C12	1.374 (3)
O2—C15	1.379 (2)	C12—C13	1.378 (3)
O2—N1	1.4131 (18)	C12—H12	0.9300
O3—C15	1.187 (2)	C13—C14	1.389 (3)
O4—N2	1.224 (2)	C13—H13	0.9300
O5—N2	1.225 (2)	C15—C16	1.498 (3)
N1—C7	1.369 (2)	C16—C17	1.528 (3)
N1—C6	1.419 (2)	C16—H16A	0.9700
N2—C19	1.463 (3)	C16—H16B	0.9700
C1—C2	1.376 (3)	C17—C18	1.508 (3)
C1—C6	1.383 (3)	C17—H17A	0.9700
C1—H1	0.9300	C17—H17B	0.9700
C2—C3	1.374 (3)	C18—C19	1.395 (3)
C2—H2	0.9300	C18—C23	1.397 (3)
C3—C4	1.370 (3)	C19—C20	1.387 (3)
C4—C5	1.380 (3)	C20—C21	1.370 (3)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.384 (3)	C21—C22	1.374 (3)
C5—H5	0.9300	C21—H21	0.9300
C7—C14	1.500 (3)	C22—C23	1.379 (3)
C9—C10	1.382 (3)	C22—H22	0.9300
C9—C14	1.397 (3)	C23—H23	0.9300
C9—H9	0.9300

C15—O2—N1	112.51 (14)	C12—C13—C14	121.23 (18)
C7—N1—O2	117.80 (15)	C12—C13—H13	119.4
C7—N1—C6	127.85 (16)	C14—C13—H13	119.4
O2—N1—C6	114.30 (14)	C13—C14—C9	118.39 (17)
O4—N2—O5	123.0 (2)	C13—C14—C7	115.43 (16)
O4—N2—C19	119.16 (18)	C9—C14—C7	125.93 (17)
O5—N2—C19	117.8 (2)	O3—C15—O2	122.88 (18)
C2—C1—C6	120.22 (18)	O3—C15—C16	127.89 (19)
C2—C1—H1	119.9	O2—C15—C16	109.23 (16)
C6—C1—H1	119.9	C15—C16—C17	112.10 (17)
C3—C2—C1	119.43 (19)	C15—C16—H16A	109.2
C3—C2—H2	120.3	C17—C16—H16A	109.2
C1—C2—H2	120.3	C15—C16—H16B	109.2
C4—C3—C2	121.17 (18)	C17—C16—H16B	109.2
C4—C3—Cl1	118.92 (15)	H16A—C16—H16B	107.9
C2—C3—Cl1	119.91 (16)	C18—C17—C16	112.42 (15)
C3—C4—C5	119.45 (18)	C18—C17—H17A	109.1
C3—C4—H4	120.3	C16—C17—H17A	109.1
C5—C4—H4	120.3	C18—C17—H17B	109.1
C4—C5—C6	120.08 (18)	C16—C17—H17B	109.1
C4—C5—H5	120.0	H17A—C17—H17B	107.9
C6—C5—H5	120.0	C19—C18—C23	114.77 (19)
C1—C6—C5	119.65 (18)	C19—C18—C17	125.79 (18)
C1—C6—N1	118.58 (17)	C23—C18—C17	119.44 (18)
C5—C6—N1	121.76 (17)	C20—C19—C18	123.28 (19)
O1—C7—N1	119.37 (17)	C20—C19—N2	115.92 (19)
O1—C7—C14	120.50 (17)	C18—C19—N2	120.79 (18)
N1—C7—C14	120.13 (16)	C21—C20—C19	119.6 (2)
C10—C9—C14	120.58 (18)	C21—C20—H20	120.2
C10—C9—H9	119.7	C19—C20—H20	120.2
C14—C9—H9	119.7	C20—C21—C22	119.1 (2)
C11—C10—C9	119.39 (18)	C20—C21—H21	120.4
C11—C10—H10	120.3	C22—C21—H21	120.4
C9—C10—H10	120.3	C21—C22—C23	120.6 (2)
C12—C11—C10	121.25 (18)	C21—C22—H22	119.7
C12—C11—Cl2	119.40 (16)	C23—C22—H22	119.7
C10—C11—Cl2	119.35 (16)	C22—C23—C18	122.5 (2)
C11—C12—C13	119.15 (19)	C22—C23—H23	118.7
C11—C12—H12	120.4	C18—C23—H23	118.7
C13—C12—H12	120.4

C15—O2—N1—C7	−92.94 (19)	C10—C9—C14—C13	−0.8 (3)
C15—O2—N1—C6	84.64 (19)	C10—C9—C14—C7	−174.88 (17)
C6—C1—C2—C3	−0.1 (3)	O1—C7—C14—C13	−27.1 (3)
C1—C2—C3—C4	−0.5 (3)	N1—C7—C14—C13	153.69 (17)
C1—C2—C3—Cl1	−179.90 (15)	O1—C7—C14—C9	147.14 (19)
C2—C3—C4—C5	0.7 (3)	N1—C7—C14—C9	−32.1 (3)
Cl1—C3—C4—C5	−179.79 (15)	N1—O2—C15—O3	−1.3 (3)
C3—C4—C5—C6	−0.5 (3)	N1—O2—C15—C16	179.71 (14)
C2—C1—C6—C5	0.2 (3)	O3—C15—C16—C17	32.6 (3)
C2—C1—C6—N1	−178.98 (17)	O2—C15—C16—C17	−148.51 (16)
C4—C5—C6—C1	0.1 (3)	C15—C16—C17—C18	71.5 (2)
C4—C5—C6—N1	179.25 (17)	C16—C17—C18—C19	92.1 (2)
C7—N1—C6—C1	−148.3 (2)	C16—C17—C18—C23	−87.9 (2)
O2—N1—C6—C1	34.4 (2)	C23—C18—C19—C20	0.9 (3)
C7—N1—C6—C5	32.5 (3)	C17—C18—C19—C20	−179.16 (19)
O2—N1—C6—C5	−144.76 (17)	C23—C18—C19—N2	−178.00 (17)
O2—N1—C7—O1	173.77 (16)	C17—C18—C19—N2	2.0 (3)
C6—N1—C7—O1	−3.4 (3)	O4—N2—C19—C20	149.1 (2)
O2—N1—C7—C14	−7.0 (3)	O5—N2—C19—C20	−29.2 (3)
C6—N1—C7—C14	175.80 (17)	O4—N2—C19—C18	−31.9 (3)
C14—C9—C10—C11	−0.2 (3)	O5—N2—C19—C18	149.7 (2)
C9—C10—C11—C12	0.6 (3)	C18—C19—C20—C21	0.6 (3)
C9—C10—C11—Cl2	−179.47 (15)	N2—C19—C20—C21	179.52 (19)
C10—C11—C12—C13	0.1 (3)	C19—C20—C21—C22	−1.3 (3)
Cl2—C11—C12—C13	−179.89 (15)	C20—C21—C22—C23	0.6 (3)
C11—C12—C13—C14	−1.1 (3)	C21—C22—C23—C18	1.0 (3)
C12—C13—C14—C9	1.5 (3)	C19—C18—C23—C22	−1.7 (3)
C12—C13—C14—C7	176.16 (17)	C17—C18—C23—C22	178.38 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.93	2.40	3.177 (2)	140
C17—H17B···O4ⁱⁱ	0.97	2.55	3.515 (3)	171

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆Cl₂N₂O₅
M_r	459.27
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	6.1710 (3), 12.8881 (7), 13.3490 (8)
α, β, γ (°)	89.933 (5), 76.959 (5), 82.114 (4)
V (Å³)	1024.03 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
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	0.757, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7506, 4578, 3269
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.113, 1.02
No. of reflections	4578
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.28

Computer programs: CrysAlis PRO (Agilent, 2011), SUPERFLIP (Palatinus & Chapuis, 2007), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.93	2.40	3.177 (2)	140
C17—H17B···O4ⁱⁱ	0.97	2.55	3.515 (3)	171

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

Acknowledgements

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

References

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