N-(2-Chloro­phen­yl)-1-phenyl­formamido 3-(2-nitro­phen­yl)propano­ate

Zhang, H.; Qu, D.; Ma, J.

doi:10.1107/S1600536812037981

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2904

https://doi.org/10.1107/S1600536812037981

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N-(2-Chlorophenyl)-1-phenylformamido 3-(2-nitrophenyl)propanoate

Hongxia Zhang,^a ^* Donghui Qu ^a and Jing Ma ^b

^aGansu Health Center Hospital, Lanzhou 730000, Gansu Province, People's Republic of China, and ^bInstitute of Medicinal Chemistry School of Pharmacy, Lanzhou University, Lanzhou 730000, Gansu Province, People's Republic of China
^*Correspondence e-mail: zhanghongxia0508@126.com

(Received 23 August 2012; accepted 4 September 2012; online 8 September 2012)

In the title molecule, C₂₂H₁₇ClN₂O₅, the nitro-substituted benzene ring makes a dihedral angle of 79.22 (1)° with the benzoyl ring and 53.03 (1)° with the chloro-substituted benzene ring. An intramolecular C—H⋯O hydrogen bond occurs. The crystal structure features weak C—H⋯Cl and C—H⋯O interactions.

Related literature

For applications of hydroxamic acid derivatives, see: Noh et al. (2009 ); Zeng et al. (2003 ). For the preparation, see: Ayyangark et al. (1986 ).

Experimental

Crystal data

C₂₂H₁₇ClN₂O₅
M_r = 424.83
Monoclinic, P 2₁ /n
a = 14.698 (9) Å
b = 8.030 (5) Å
c = 17.495 (11) Å
β = 103.059 (7)°
V = 2011 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.26 × 0.23 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.943, T_max = 0.952
8356 measured reflections
3697 independent reflections
2285 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.114
S = 1.02
3697 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯Cl1ⁱ	0.97	2.68	3.627 (3)	167
C7—H7A⋯O1ⁱⁱ	0.97	2.60	3.520 (3)	158
C8—H8A⋯O2	0.97	2.47	3.092 (3)	121
C18—H18⋯O1ⁱⁱⁱ	0.93	2.62	3.517 (4)	161
C4—H4⋯O1^iv	0.93	2.64	3.468 (4)	149
Symmetry codes: (i) -x+2, -y+2, -z; (ii) -x+1, -y+1, -z; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) x, y+1, z.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812037981/zq2179sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037981/zq2179Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812037981/zq2179Isup3.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. Thus, these compounds continue to attract much attention as potential biological agents (Noh et al., 2009; Zeng et al., 2003).

The title compound, C₂₂H₁₇N₂O₅Cl, was prepared according to the method described by Ayyangark et al. (1986). The molecule contains three branched chains with its centre placed at midpoint of the N2 atom (Fig. 1). The phenyl ring C1—C6 makes dihedral angles of 79.22 (1)° with the phenyl ring C17—C22, and 53.03 (1)° with the phenyl ring C10—C15.

The crystal structure features weak C—H···Cl and C—H···O interactions (Table 1).

Related literature top

For applications of hydroxamic acid derivatives, see: Noh et al. (2009); Zeng et al. (2003). For the preparation, see: Ayyangark et al. (1986).

Experimental top

The title compound was prepared according to the method described by Ayyangark et al. (1986). The colourless crystals were grown from a solution of dichloromethane-methanol (1:3 v/v) by slow evaporation at room temperature.

Structure description top

The crystal structure features weak C—H···Cl and C—H···O interactions (Table 1).

For applications of hydroxamic acid derivatives, see: Noh et al. (2009); Zeng et al. (2003). For the preparation, see: Ayyangark et al. (1986).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atomic numbering and 30% probability displacement ellipsoids (H atoms are shown as small spheres of arbitrary radius).

N-(2-Chlorophenyl)-1-phenylformamido 3-(2-nitrophenyl)propanoate top

Crystal data top

C₂₂H₁₇ClN₂O₅	F(000) = 880
M_r = 424.83	D_x = 1.403 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1690 reflections
a = 14.698 (9) Å	θ = 2.4–22.2°
b = 8.030 (5) Å	µ = 0.23 mm⁻¹
c = 17.495 (11) Å	T = 296 K
β = 103.059 (7)°	Block, colourless
V = 2011 (2) Å³	0.26 × 0.23 × 0.22 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3697 independent reflections
Radiation source: fine-focus sealed tube	2285 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
φ and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→13
T_min = 0.943, T_max = 0.952	k = −9→9
8356 measured reflections	l = −21→19

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.047	w = 1/[σ²(F_o²) + (0.0421P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.114	(Δ/σ)_max = 0.001
S = 1.02	Δρ_max = 0.18 e Å⁻³
3697 reflections	Δρ_min = −0.26 e Å⁻³
271 parameters

Crystal data top

C₂₂H₁₇ClN₂O₅	V = 2011 (2) Å³
M_r = 424.83	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.698 (9) Å	µ = 0.23 mm⁻¹
b = 8.030 (5) Å	T = 296 K
c = 17.495 (11) Å	0.26 × 0.23 × 0.22 mm
β = 103.059 (7)°

Data collection top

Bruker APEXII CCD diffractometer	3697 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2285 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.952	R_int = 0.045
8356 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.02	Δρ_max = 0.18 e Å⁻³
3697 reflections	Δρ_min = −0.26 e Å⁻³
271 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
C1	0.54356 (14)	0.7597 (3)	−0.08505 (13)	0.0364 (5)
C2	0.47799 (16)	0.8218 (3)	−0.14815 (14)	0.0499 (7)
H2	0.4370	0.7502	−0.1809	0.060*
C3	0.47420 (19)	0.9893 (4)	−0.16184 (17)	0.0625 (8)
H3	0.4314	1.0326	−0.2047	0.075*
C4	0.53416 (19)	1.0939 (4)	−0.11187 (18)	0.0626 (8)
H4	0.5323	1.2081	−0.1210	0.075*
C5	0.59688 (16)	1.0288 (3)	−0.04832 (16)	0.0525 (7)
H5	0.6359	1.1014	−0.0145	0.063*
C6	0.60438 (14)	0.8602 (3)	−0.03261 (13)	0.0375 (6)
C7	0.67502 (14)	0.8013 (3)	0.03913 (13)	0.0441 (6)
H7A	0.6520	0.7007	0.0590	0.053*
H7B	0.6820	0.8856	0.0797	0.053*
C8	0.77017 (14)	0.7660 (3)	0.02151 (13)	0.0457 (6)
H8A	0.7677	0.6601	−0.0056	0.055*
H8B	0.7841	0.8517	−0.0132	0.055*
C9	0.84611 (15)	0.7607 (3)	0.09349 (15)	0.0417 (6)
C10	1.07421 (15)	0.7137 (3)	0.15039 (14)	0.0456 (6)
C11	1.05317 (18)	0.5495 (4)	0.15897 (17)	0.0646 (8)
H11	0.9922	0.5189	0.1592	0.077*
C12	1.1218 (2)	0.4293 (4)	0.16719 (17)	0.0701 (9)
H12	1.1067	0.3178	0.1718	0.084*
C13	1.21242 (19)	0.4745 (4)	0.16857 (16)	0.0627 (8)
H13	1.2590	0.3938	0.1756	0.075*
C14	1.23411 (17)	0.6372 (4)	0.15972 (14)	0.0567 (7)
H14	1.2954	0.6674	0.1606	0.068*
C15	1.16538 (16)	0.7572 (3)	0.14945 (13)	0.0467 (6)
C16	0.99784 (16)	0.9673 (3)	0.18933 (15)	0.0428 (6)
C17	0.92056 (15)	1.0900 (3)	0.16295 (14)	0.0414 (6)
C18	0.86650 (17)	1.1325 (3)	0.21517 (15)	0.0527 (7)
H18	0.8794	1.0861	0.2652	0.063*
C19	0.79360 (18)	1.2432 (4)	0.19365 (18)	0.0616 (8)
H19	0.7567	1.2696	0.2287	0.074*
C20	0.7755 (2)	1.3147 (4)	0.12042 (19)	0.0677 (8)
H20	0.7261	1.3891	0.1059	0.081*
C21	0.8295 (2)	1.2771 (4)	0.06901 (18)	0.0666 (8)
H21	0.8176	1.3274	0.0199	0.080*
C22	0.90226 (18)	1.1643 (3)	0.08966 (16)	0.0558 (7)
H22	0.9388	1.1385	0.0543	0.067*
Cl1	1.19330 (5)	0.96079 (10)	0.13393 (4)	0.0716 (3)
N1	0.54447 (14)	0.5788 (3)	−0.07543 (11)	0.0415 (5)
N2	1.00361 (12)	0.8386 (3)	0.13960 (12)	0.0529 (6)
O1	0.46940 (12)	0.5048 (2)	−0.09402 (10)	0.0596 (5)
O2	0.61882 (12)	0.5081 (2)	−0.05065 (10)	0.0556 (5)
O3	0.84162 (11)	0.7242 (2)	0.15847 (10)	0.0573 (5)
O4	0.92840 (9)	0.8124 (2)	0.07409 (9)	0.0457 (4)
O5	1.05461 (11)	0.9793 (2)	0.25171 (10)	0.0536 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0354 (12)	0.0330 (15)	0.0410 (14)	0.0018 (10)	0.0094 (10)	−0.0036 (11)
C2	0.0460 (14)	0.0504 (19)	0.0493 (16)	0.0066 (12)	0.0021 (12)	−0.0035 (13)
C3	0.0597 (17)	0.063 (2)	0.0625 (19)	0.0194 (15)	0.0083 (14)	0.0084 (16)
C4	0.0661 (18)	0.0404 (17)	0.085 (2)	0.0127 (14)	0.0254 (17)	0.0051 (17)
C5	0.0465 (15)	0.0398 (17)	0.071 (2)	−0.0037 (12)	0.0134 (14)	−0.0118 (14)
C6	0.0331 (12)	0.0378 (16)	0.0429 (14)	−0.0005 (10)	0.0113 (11)	−0.0061 (12)
C7	0.0376 (13)	0.0526 (17)	0.0412 (14)	−0.0013 (11)	0.0068 (11)	−0.0110 (12)
C8	0.0360 (12)	0.0627 (18)	0.0366 (14)	−0.0044 (12)	0.0041 (10)	0.0003 (13)
C9	0.0373 (13)	0.0398 (16)	0.0467 (16)	−0.0008 (11)	0.0066 (11)	−0.0053 (13)
C10	0.0365 (13)	0.0526 (18)	0.0450 (15)	0.0034 (12)	0.0037 (11)	−0.0065 (13)
C11	0.0442 (15)	0.057 (2)	0.090 (2)	0.0011 (14)	0.0109 (15)	−0.0104 (17)
C12	0.068 (2)	0.052 (2)	0.087 (2)	0.0074 (16)	0.0099 (17)	−0.0058 (17)
C13	0.0543 (18)	0.074 (2)	0.0562 (18)	0.0248 (16)	0.0042 (13)	−0.0037 (16)
C14	0.0394 (14)	0.087 (2)	0.0448 (16)	0.0105 (15)	0.0123 (12)	−0.0005 (16)
C15	0.0445 (14)	0.0617 (19)	0.0346 (14)	0.0025 (13)	0.0103 (11)	0.0032 (13)
C16	0.0369 (13)	0.0468 (16)	0.0459 (15)	−0.0082 (11)	0.0119 (12)	−0.0032 (13)
C17	0.0410 (13)	0.0376 (15)	0.0448 (15)	−0.0030 (11)	0.0081 (11)	−0.0044 (12)
C18	0.0545 (15)	0.0526 (18)	0.0480 (16)	0.0045 (13)	0.0056 (13)	−0.0054 (14)
C19	0.0560 (16)	0.063 (2)	0.066 (2)	0.0100 (14)	0.0133 (15)	−0.0114 (17)
C20	0.0652 (18)	0.050 (2)	0.078 (2)	0.0126 (14)	−0.0057 (17)	−0.0105 (17)
C21	0.088 (2)	0.0488 (19)	0.0571 (19)	0.0096 (16)	0.0036 (17)	0.0065 (15)
C22	0.0701 (18)	0.0462 (18)	0.0515 (17)	−0.0007 (14)	0.0145 (14)	0.0006 (14)
Cl1	0.0704 (5)	0.0792 (6)	0.0717 (5)	−0.0083 (4)	0.0297 (4)	0.0167 (4)
N1	0.0432 (12)	0.0438 (14)	0.0372 (11)	−0.0062 (11)	0.0083 (9)	−0.0052 (10)
N2	0.0325 (11)	0.0582 (15)	0.0599 (14)	0.0049 (10)	−0.0067 (10)	−0.0175 (12)
O1	0.0559 (11)	0.0587 (13)	0.0631 (12)	−0.0200 (9)	0.0111 (9)	−0.0105 (10)
O2	0.0537 (11)	0.0443 (12)	0.0655 (12)	0.0071 (8)	0.0063 (9)	−0.0012 (9)
O3	0.0567 (10)	0.0718 (14)	0.0408 (11)	−0.0034 (9)	0.0059 (8)	0.0072 (10)
O4	0.0332 (8)	0.0530 (11)	0.0480 (10)	−0.0028 (7)	0.0028 (8)	−0.0075 (8)
O5	0.0436 (9)	0.0657 (13)	0.0483 (11)	−0.0010 (8)	0.0040 (8)	−0.0058 (9)

Geometric parameters (Å, º) top

C1—C2	1.384 (3)	C12—C13	1.376 (4)
C1—C6	1.386 (3)	C12—H12	0.9300
C1—N1	1.462 (3)	C13—C14	1.362 (4)
C2—C3	1.365 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.378 (3)
C3—C4	1.378 (4)	C14—H14	0.9300
C3—H3	0.9300	C15—Cl1	1.722 (3)
C4—C5	1.377 (4)	C16—O5	1.219 (3)
C4—H4	0.9300	C16—N2	1.365 (3)
C5—C6	1.381 (3)	C16—C17	1.496 (3)
C5—H5	0.9300	C17—C18	1.382 (3)
C6—C7	1.513 (3)	C17—C22	1.384 (3)
C7—C8	1.525 (3)	C18—C19	1.377 (4)
C7—H7A	0.9700	C18—H18	0.9300
C7—H7B	0.9700	C19—C20	1.374 (4)
C8—C9	1.483 (3)	C19—H19	0.9300
C8—H8A	0.9700	C20—C21	1.362 (4)
C8—H8B	0.9700	C20—H20	0.9300
C9—O3	1.190 (3)	C21—C22	1.386 (4)
C9—O4	1.391 (3)	C21—H21	0.9300
C10—C11	1.370 (4)	C22—H22	0.9300
C10—C15	1.388 (3)	N1—O2	1.221 (2)
C10—N2	1.425 (3)	N1—O1	1.230 (2)
C11—C12	1.380 (4)	N2—O4	1.417 (2)
C11—H11	0.9300

C2—C1—C6	123.2 (2)	C13—C12—H12	120.0
C2—C1—N1	115.9 (2)	C11—C12—H12	120.0
C6—C1—N1	121.0 (2)	C14—C13—C12	120.1 (3)
C3—C2—C1	119.2 (2)	C14—C13—H13	119.9
C3—C2—H2	120.4	C12—C13—H13	119.9
C1—C2—H2	120.4	C13—C14—C15	120.1 (3)
C2—C3—C4	119.6 (3)	C13—C14—H14	119.9
C2—C3—H3	120.2	C15—C14—H14	119.9
C4—C3—H3	120.2	C14—C15—C10	120.3 (3)
C5—C4—C3	119.8 (3)	C14—C15—Cl1	119.4 (2)
C5—C4—H4	120.1	C10—C15—Cl1	120.4 (2)
C3—C4—H4	120.1	O5—C16—N2	120.1 (2)
C4—C5—C6	122.8 (2)	O5—C16—C17	122.9 (2)
C4—C5—H5	118.6	N2—C16—C17	117.0 (2)
C6—C5—H5	118.6	C18—C17—C22	119.0 (2)
C5—C6—C1	115.4 (2)	C18—C17—C16	118.0 (2)
C5—C6—C7	118.7 (2)	C22—C17—C16	123.0 (2)
C1—C6—C7	125.9 (2)	C19—C18—C17	120.4 (3)
C6—C7—C8	112.28 (19)	C19—C18—H18	119.8
C6—C7—H7A	109.1	C17—C18—H18	119.8
C8—C7—H7A	109.1	C20—C19—C18	120.0 (3)
C6—C7—H7B	109.1	C20—C19—H19	120.0
C8—C7—H7B	109.1	C18—C19—H19	120.0
H7A—C7—H7B	107.9	C21—C20—C19	120.3 (3)
C9—C8—C7	112.48 (19)	C21—C20—H20	119.9
C9—C8—H8A	109.1	C19—C20—H20	119.9
C7—C8—H8A	109.1	C20—C21—C22	120.3 (3)
C9—C8—H8B	109.1	C20—C21—H21	119.9
C7—C8—H8B	109.1	C22—C21—H21	119.9
H8A—C8—H8B	107.8	C17—C22—C21	120.0 (3)
O3—C9—O4	123.0 (2)	C17—C22—H22	120.0
O3—C9—C8	128.7 (2)	C21—C22—H22	120.0
O4—C9—C8	108.3 (2)	O2—N1—O1	123.2 (2)
C11—C10—C15	119.0 (2)	O2—N1—C1	119.14 (19)
C11—C10—N2	121.1 (2)	O1—N1—C1	117.7 (2)
C15—C10—N2	119.8 (2)	C16—N2—O4	118.59 (18)
C10—C11—C12	120.5 (3)	C16—N2—C10	126.6 (2)
C10—C11—H11	119.8	O4—N2—C10	114.47 (18)
C12—C11—H11	119.8	C9—O4—N2	114.17 (17)
C13—C12—C11	120.0 (3)

C6—C1—C2—C3	2.3 (4)	N2—C16—C17—C18	131.7 (2)
N1—C1—C2—C3	−178.7 (2)	O5—C16—C17—C22	129.7 (3)
C1—C2—C3—C4	−1.4 (4)	N2—C16—C17—C22	−49.6 (3)
C2—C3—C4—C5	−0.4 (4)	C22—C17—C18—C19	2.1 (4)
C3—C4—C5—C6	1.4 (4)	C16—C17—C18—C19	−179.1 (2)
C4—C5—C6—C1	−0.5 (3)	C17—C18—C19—C20	−1.3 (4)
C4—C5—C6—C7	−179.5 (2)	C18—C19—C20—C21	−0.2 (4)
C2—C1—C6—C5	−1.4 (3)	C19—C20—C21—C22	1.1 (4)
N1—C1—C6—C5	179.72 (19)	C18—C17—C22—C21	−1.2 (4)
C2—C1—C6—C7	177.5 (2)	C16—C17—C22—C21	−179.9 (2)
N1—C1—C6—C7	−1.4 (3)	C20—C21—C22—C17	−0.4 (4)
C5—C6—C7—C8	−89.7 (3)	C2—C1—N1—O2	145.1 (2)
C1—C6—C7—C8	91.5 (3)	C6—C1—N1—O2	−35.9 (3)
C6—C7—C8—C9	161.9 (2)	C2—C1—N1—O1	−33.9 (3)
C7—C8—C9—O3	27.9 (4)	C6—C1—N1—O1	145.1 (2)
C7—C8—C9—O4	−150.2 (2)	O5—C16—N2—O4	169.69 (19)
C15—C10—C11—C12	0.5 (4)	C17—C16—N2—O4	−11.0 (3)
N2—C10—C11—C12	178.2 (2)	O5—C16—N2—C10	−3.3 (4)
C10—C11—C12—C13	1.5 (4)	C17—C16—N2—C10	176.0 (2)
C11—C12—C13—C14	−1.8 (4)	C11—C10—N2—C16	116.1 (3)
C12—C13—C14—C15	0.1 (4)	C15—C10—N2—C16	−66.3 (3)
C13—C14—C15—C10	1.9 (4)	C11—C10—N2—O4	−57.2 (3)
C13—C14—C15—Cl1	−177.1 (2)	C15—C10—N2—O4	120.5 (2)
C11—C10—C15—C14	−2.2 (4)	O3—C9—O4—N2	−7.8 (3)
N2—C10—C15—C14	−179.9 (2)	C8—C9—O4—N2	170.50 (18)
C11—C10—C15—Cl1	176.8 (2)	C16—N2—O4—C9	−67.4 (3)
N2—C10—C15—Cl1	−0.9 (3)	C10—N2—O4—C9	106.5 (2)
O5—C16—C17—C18	−49.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cl1ⁱ	0.97	2.68	3.627 (3)	167
C7—H7A···O1ⁱⁱ	0.97	2.60	3.520 (3)	158
C8—H8A···O2	0.97	2.47	3.092 (3)	121
C18—H18···O1ⁱⁱⁱ	0.93	2.62	3.517 (4)	161
C4—H4···O1^iv	0.93	2.64	3.468 (4)	149

Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+1, −y+1, −z; (iii) x+1/2, −y+3/2, z+1/2; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇ClN₂O₅
M_r	424.83
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	14.698 (9), 8.030 (5), 17.495 (11)
β (°)	103.059 (7)
V (Å³)	2011 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.26 × 0.23 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.943, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	8356, 3697, 2285
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.114, 1.02
No. of reflections	3697
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.26

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cl1ⁱ	0.97	2.68	3.627 (3)	167.2
C7—H7A···O1ⁱⁱ	0.97	2.60	3.520 (3)	157.8
C8—H8A···O2	0.97	2.47	3.092 (3)	121.4
C18—H18···O1ⁱⁱⁱ	0.93	2.62	3.517 (4)	161.3
C4—H4···O1^iv	0.93	2.64	3.468 (4)	149.1

Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+1, −y+1, −z; (iii) x+1/2, −y+3/2, z+1/2; (iv) x, y+1, z.

Acknowledgements

This work was supported by the Science and Technology plan projects of Lanzhou City (2008–1-74)

References

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