N-(4-Methyl­phen­yl)-N-{[(2-nitro­phen­yl)acet­yl]­oxy}benzamide

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

doi:10.1107/S1600536812039360

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2974

https://doi.org/10.1107/S1600536812039360

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N-(4-Methylphenyl)-N-{[(2-nitrophenyl)acetyl]oxy}benzamide

Dong-Hui Qu,^a ^* Hong-Xia Zhang ^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: qudonghui1020@126.com

(Received 12 September 2012; accepted 15 September 2012; online 22 September 2012)

In the title molecule, C₂₂H₁₈N₂O₅, the nitro-substituted benzene ring makes dihedral angles of 71.56 (1)° with the benzoyl ring and 16.28 (1)° with the methyl-substituted benzene ring. The crystal structure features C—H⋯O interactions, which generate chains.

Related literature

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

Experimental

Crystal data

C₂₂H₁₈N₂O₅
M_r = 390.38
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.246 (3) Å
b = 11.911 (4) Å
c = 17.923 (6) Å
V = 1974.0 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.25 × 0.23 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.977, T_max = 0.980
8939 measured reflections
3605 independent reflections
2280 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.111
S = 1.01
3605 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.93	2.55	3.456 (4)	165
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536812039360/zq2182sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039360/zq2182Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812039360/zq2182Isup3.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, C₂₂H₁₈N₂O₅, 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 nitro-substituted benzene ring makes a dihedral angle of 71.56 (1)° with the benzoyl ring and 16.28 (1)° with the methyl-substituted benzene ring. The crystal structure features weak intra- and inter-molecular C—H···O interactions (Table 1).

Related literature top

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

Experimental top

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

Structure description top

For biological applications of hydroxamic acid derivatives, see: Noh et al. (2009); Zeng et al. (2003). For the preparation of the title compound, 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 50% probability displacement ellipsoids (H atoms are shown as small spheres of arbitrary radius).

N-(4-Methylphenyl)-N-{[(2-nitrophenyl)acetyl]oxy}benzamide top

Crystal data top

C₂₂H₁₈N₂O₅	F(000) = 816
M_r = 390.38	D_x = 1.314 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2167 reflections
a = 9.246 (3) Å	θ = 2.5–20.3°
b = 11.911 (4) Å	µ = 0.09 mm⁻¹
c = 17.923 (6) Å	T = 296 K
V = 1974.0 (11) Å³	Block, yellow
Z = 4	0.25 × 0.23 × 0.22 mm

Data collection top

Bruker APEXII CCD diffractometer	3605 independent reflections
Radiation source: fine-focus sealed tube	2280 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
T_min = 0.977, T_max = 0.980	k = −14→14
8939 measured reflections	l = −18→21

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0508P)² + 0.0436P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.040	(Δ/σ)_max = 0.001
wR(F²) = 0.111	Δρ_max = 0.11 e Å⁻³
S = 1.01	Δρ_min = −0.12 e Å⁻³
3605 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008)
264 parameters	Extinction coefficient: 0.0097 (13)
0 restraints

Crystal data top

C₂₂H₁₈N₂O₅	V = 1974.0 (11) Å³
M_r = 390.38	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.246 (3) Å	µ = 0.09 mm⁻¹
b = 11.911 (4) Å	T = 296 K
c = 17.923 (6) Å	0.25 × 0.23 × 0.22 mm

Data collection top

Bruker APEXII CCD diffractometer	3605 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2280 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.980	R_int = 0.033
8939 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.01	Δρ_max = 0.11 e Å⁻³
3605 reflections	Δρ_min = −0.12 e Å⁻³
264 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	0.3532 (3)	0.1353 (2)	−0.07101 (14)	0.0662 (7)
C2	0.2883 (3)	0.1027 (3)	−0.13739 (17)	0.0852 (9)
H2	0.2795	0.0271	−0.1496	0.102*
C3	0.2368 (3)	0.1853 (4)	−0.18535 (16)	0.0961 (11)
H3	0.1933	0.1658	−0.2303	0.115*
C4	0.2508 (4)	0.2945 (3)	−0.16565 (19)	0.0956 (10)
H4	0.2173	0.3502	−0.1977	0.115*
C5	0.3124 (3)	0.3237 (3)	−0.10045 (17)	0.0817 (8)
H5	0.3186	0.3995	−0.0886	0.098*
C6	0.3665 (3)	0.2469 (2)	−0.05063 (13)	0.0637 (7)
C7	0.4263 (3)	0.2894 (2)	0.02163 (14)	0.0747 (8)
H7A	0.5196	0.2548	0.0306	0.090*
H7B	0.4409	0.3698	0.0181	0.090*
C8	0.3285 (3)	0.2649 (2)	0.08568 (14)	0.0648 (7)
C9	0.1744 (3)	0.3805 (2)	0.21269 (15)	0.0675 (7)
C10	0.0711 (3)	0.3651 (2)	0.27535 (14)	0.0613 (7)
C11	−0.0023 (3)	0.4586 (2)	0.30155 (17)	0.0779 (8)
H11	0.0173	0.5291	0.2817	0.094*
C12	−0.1047 (4)	0.4469 (3)	0.35739 (19)	0.0914 (10)
H12	−0.1526	0.5098	0.3757	0.110*
C13	−0.1356 (4)	0.3429 (3)	0.38569 (17)	0.0914 (9)
H13	−0.2047	0.3353	0.4230	0.110*
C14	−0.0659 (3)	0.2509 (3)	0.35956 (16)	0.0808 (8)
H14	−0.0882	0.1804	0.3786	0.097*
C15	0.0376 (3)	0.2615 (2)	0.30509 (15)	0.0687 (7)
H15	0.0858	0.1980	0.2880	0.082*
C16	0.3668 (3)	0.2615 (2)	0.27241 (13)	0.0587 (6)
C17	0.4158 (3)	0.1531 (2)	0.26885 (16)	0.0714 (7)
H17	0.3964	0.1095	0.2270	0.086*
C18	0.4936 (3)	0.1090 (2)	0.32708 (16)	0.0750 (8)
H18	0.5281	0.0358	0.3236	0.090*
C19	0.5220 (3)	0.1707 (2)	0.39074 (14)	0.0668 (7)
C20	0.4722 (3)	0.2792 (2)	0.39293 (15)	0.0727 (8)
H20	0.4898	0.3226	0.4351	0.087*
C21	0.3968 (3)	0.3255 (2)	0.33402 (15)	0.0680 (7)
H21	0.3663	0.3998	0.3361	0.082*
C22	0.6051 (4)	0.1213 (3)	0.45524 (15)	0.0997 (11)
H22A	0.5407	0.0785	0.4862	0.150*
H22B	0.6475	0.1808	0.4841	0.150*
H22C	0.6802	0.0733	0.4365	0.150*
N1	0.4064 (4)	0.0451 (2)	−0.02206 (17)	0.0970 (8)
N2	0.2881 (2)	0.3064 (2)	0.21067 (12)	0.0713 (6)
O1	0.2230 (3)	0.20874 (17)	0.08620 (10)	0.0923 (7)
O2	0.37898 (19)	0.32093 (15)	0.14693 (9)	0.0750 (5)
O3	0.1555 (2)	0.44895 (17)	0.16349 (12)	0.0973 (7)
O4	0.3608 (4)	−0.0472 (2)	−0.03322 (16)	0.1591 (12)
O5	0.4911 (4)	0.0655 (2)	0.02581 (17)	0.1589 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0596 (16)	0.0736 (17)	0.0655 (17)	0.0017 (14)	0.0069 (14)	0.0037 (14)
C2	0.072 (2)	0.104 (2)	0.080 (2)	−0.0155 (18)	0.0139 (17)	−0.0225 (19)
C3	0.0593 (19)	0.175 (4)	0.0541 (18)	0.000 (2)	0.0040 (15)	−0.003 (2)
C4	0.080 (2)	0.123 (3)	0.084 (2)	0.017 (2)	0.0039 (19)	0.026 (2)
C5	0.085 (2)	0.0853 (19)	0.0753 (19)	0.0026 (17)	0.0079 (17)	0.0145 (17)
C6	0.0573 (16)	0.0715 (17)	0.0622 (15)	−0.0049 (14)	0.0097 (13)	0.0099 (14)
C7	0.078 (2)	0.0780 (17)	0.0681 (17)	−0.0196 (15)	0.0065 (16)	0.0010 (14)
C8	0.0636 (18)	0.0685 (16)	0.0624 (15)	−0.0117 (15)	−0.0025 (14)	0.0002 (13)
C9	0.0651 (19)	0.0595 (16)	0.0780 (18)	−0.0091 (15)	−0.0111 (15)	0.0001 (14)
C10	0.0515 (15)	0.0589 (15)	0.0735 (17)	0.0002 (13)	−0.0114 (13)	−0.0039 (13)
C11	0.0778 (19)	0.0615 (16)	0.095 (2)	0.0096 (17)	−0.0190 (19)	−0.0074 (15)
C12	0.080 (2)	0.098 (2)	0.096 (2)	0.028 (2)	−0.015 (2)	−0.037 (2)
C13	0.072 (2)	0.117 (3)	0.085 (2)	0.006 (2)	0.0023 (18)	−0.013 (2)
C14	0.0641 (19)	0.089 (2)	0.090 (2)	−0.0034 (17)	0.0018 (17)	0.0038 (18)
C15	0.0571 (18)	0.0627 (17)	0.0864 (18)	0.0001 (13)	−0.0021 (15)	−0.0073 (14)
C16	0.0491 (14)	0.0635 (15)	0.0636 (15)	−0.0052 (12)	0.0035 (13)	−0.0056 (13)
C17	0.0775 (19)	0.0649 (17)	0.0717 (17)	−0.0025 (15)	0.0056 (15)	−0.0173 (14)
C18	0.0778 (19)	0.0603 (16)	0.0869 (19)	0.0090 (16)	0.0150 (17)	0.0030 (15)
C19	0.0643 (17)	0.0671 (17)	0.0690 (17)	0.0077 (14)	0.0126 (15)	0.0068 (14)
C20	0.0708 (19)	0.0748 (18)	0.0725 (17)	0.0015 (15)	−0.0061 (16)	−0.0120 (14)
C21	0.0658 (17)	0.0614 (15)	0.0768 (18)	0.0042 (15)	−0.0112 (14)	−0.0112 (13)
C22	0.107 (3)	0.114 (2)	0.0781 (19)	0.025 (2)	0.0122 (19)	0.0285 (18)
N1	0.119 (2)	0.0711 (18)	0.101 (2)	0.0019 (18)	0.0082 (18)	0.0082 (16)
N2	0.0609 (14)	0.0913 (16)	0.0618 (13)	0.0061 (13)	−0.0007 (12)	−0.0030 (11)
O1	0.0954 (14)	0.1119 (16)	0.0698 (12)	−0.0502 (14)	0.0065 (11)	−0.0052 (11)
O2	0.0661 (12)	0.0943 (13)	0.0647 (11)	−0.0177 (11)	0.0017 (10)	−0.0068 (10)
O3	0.0899 (15)	0.0888 (13)	0.1131 (16)	−0.0055 (13)	−0.0006 (13)	0.0337 (13)
O4	0.238 (4)	0.0828 (17)	0.157 (2)	−0.020 (2)	−0.017 (3)	0.0193 (16)
O5	0.192 (3)	0.116 (2)	0.169 (3)	0.001 (2)	−0.093 (3)	0.0317 (19)

Geometric parameters (Å, º) top

C1—C6	1.384 (4)	C12—H12	0.9300
C1—C2	1.387 (3)	C13—C14	1.354 (4)
C1—N1	1.472 (4)	C13—H13	0.9300
C2—C3	1.390 (4)	C14—C15	1.373 (4)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.354 (5)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.369 (4)
C4—C5	1.346 (4)	C16—C21	1.370 (3)
C4—H4	0.9300	C16—N2	1.429 (3)
C5—C6	1.373 (4)	C17—C18	1.372 (4)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.496 (3)	C18—C19	1.383 (4)
C7—C8	1.490 (3)	C18—H18	0.9300
C7—H7A	0.9700	C19—C20	1.372 (3)
C7—H7B	0.9700	C19—C22	1.508 (4)
C8—O1	1.183 (3)	C20—C21	1.380 (3)
C8—O2	1.367 (3)	C20—H20	0.9300
C9—O3	1.214 (3)	C21—H21	0.9300
C9—N2	1.372 (3)	C22—H22A	0.9600
C9—C10	1.486 (4)	C22—H22B	0.9600
C10—C15	1.379 (3)	C22—H22C	0.9600
C10—C11	1.386 (3)	N1—O5	1.187 (3)
C11—C12	1.385 (4)	N1—O4	1.194 (3)
C11—H11	0.9300	N2—O2	1.429 (3)
C12—C13	1.369 (4)

C6—C1—C2	122.2 (3)	C14—C13—H13	119.9
C6—C1—N1	120.9 (3)	C12—C13—H13	119.9
C2—C1—N1	116.9 (3)	C13—C14—C15	120.2 (3)
C1—C2—C3	118.7 (3)	C13—C14—H14	119.9
C1—C2—H2	120.6	C15—C14—H14	119.9
C3—C2—H2	120.6	C14—C15—C10	120.9 (3)
C4—C3—C2	119.0 (3)	C14—C15—H15	119.6
C4—C3—H3	120.5	C10—C15—H15	119.6
C2—C3—H3	120.5	C17—C16—C21	119.7 (2)
C5—C4—C3	121.0 (3)	C17—C16—N2	119.1 (2)
C5—C4—H4	119.5	C21—C16—N2	121.2 (2)
C3—C4—H4	119.5	C16—C17—C18	119.9 (2)
C4—C5—C6	123.1 (3)	C16—C17—H17	120.0
C4—C5—H5	118.4	C18—C17—H17	120.0
C6—C5—H5	118.4	C17—C18—C19	121.6 (2)
C5—C6—C1	115.8 (3)	C17—C18—H18	119.2
C5—C6—C7	118.2 (3)	C19—C18—H18	119.2
C1—C6—C7	125.9 (2)	C20—C19—C18	117.4 (2)
C8—C7—C6	112.1 (2)	C20—C19—C22	121.1 (3)
C8—C7—H7A	109.2	C18—C19—C22	121.5 (2)
C6—C7—H7A	109.2	C19—C20—C21	121.6 (3)
C8—C7—H7B	109.2	C19—C20—H20	119.2
C6—C7—H7B	109.2	C21—C20—H20	119.2
H7A—C7—H7B	107.9	C16—C21—C20	119.8 (2)
O1—C8—O2	123.5 (2)	C16—C21—H21	120.1
O1—C8—C7	128.1 (2)	C20—C21—H21	120.1
O2—C8—C7	108.4 (2)	C19—C22—H22A	109.5
O3—C9—N2	121.5 (3)	C19—C22—H22B	109.5
O3—C9—C10	122.6 (3)	H22A—C22—H22B	109.5
N2—C9—C10	115.7 (2)	C19—C22—H22C	109.5
C15—C10—C11	118.6 (3)	H22A—C22—H22C	109.5
C15—C10—C9	123.1 (2)	H22B—C22—H22C	109.5
C11—C10—C9	118.1 (2)	O5—N1—O4	122.9 (3)
C12—C11—C10	119.9 (3)	O5—N1—C1	120.1 (3)
C12—C11—H11	120.1	O4—N1—C1	117.0 (3)
C10—C11—H11	120.1	C9—N2—O2	113.2 (2)
C13—C12—C11	120.1 (3)	C9—N2—C16	127.6 (2)
C13—C12—H12	119.9	O2—N2—C16	111.39 (19)
C11—C12—H12	119.9	C8—O2—N2	112.48 (19)
C14—C13—C12	120.3 (3)

C6—C1—C2—C3	0.8 (4)	C21—C16—C17—C18	0.5 (4)
N1—C1—C2—C3	−179.9 (3)	N2—C16—C17—C18	179.0 (2)
C1—C2—C3—C4	−0.3 (4)	C16—C17—C18—C19	1.3 (4)
C2—C3—C4—C5	−0.6 (5)	C17—C18—C19—C20	−1.5 (4)
C3—C4—C5—C6	1.0 (5)	C17—C18—C19—C22	178.9 (3)
C4—C5—C6—C1	−0.5 (4)	C18—C19—C20—C21	0.0 (4)
C4—C5—C6—C7	−177.2 (3)	C22—C19—C20—C21	179.6 (3)
C2—C1—C6—C5	−0.4 (4)	C17—C16—C21—C20	−2.0 (4)
N1—C1—C6—C5	−179.7 (3)	N2—C16—C21—C20	179.6 (2)
C2—C1—C6—C7	176.0 (2)	C19—C20—C21—C16	1.8 (4)
N1—C1—C6—C7	−3.3 (4)	C6—C1—N1—O5	−18.3 (5)
C5—C6—C7—C8	106.5 (3)	C2—C1—N1—O5	162.4 (3)
C1—C6—C7—C8	−69.8 (4)	C6—C1—N1—O4	161.9 (3)
C6—C7—C8—O1	8.2 (4)	C2—C1—N1—O4	−17.4 (4)
C6—C7—C8—O2	−170.7 (2)	O3—C9—N2—O2	1.1 (3)
O3—C9—C10—C15	141.9 (3)	C10—C9—N2—O2	176.52 (19)
N2—C9—C10—C15	−33.4 (3)	O3—C9—N2—C16	147.4 (3)
O3—C9—C10—C11	−33.6 (4)	C10—C9—N2—C16	−37.2 (3)
N2—C9—C10—C11	151.1 (2)	C17—C16—N2—C9	144.5 (3)
C15—C10—C11—C12	1.2 (4)	C21—C16—N2—C9	−37.0 (4)
C9—C10—C11—C12	176.8 (2)	C17—C16—N2—O2	−68.7 (3)
C10—C11—C12—C13	−1.3 (4)	C21—C16—N2—O2	109.7 (3)
C11—C12—C13—C14	0.3 (5)	O1—C8—O2—N2	−1.6 (4)
C12—C13—C14—C15	0.8 (4)	C7—C8—O2—N2	177.4 (2)
C13—C14—C15—C10	−0.9 (4)	C9—N2—O2—C8	−84.8 (2)
C11—C10—C15—C14	−0.1 (4)	C16—N2—O2—C8	123.4 (2)
C9—C10—C15—C14	−175.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O5	0.97	2.27	2.734 (4)	108
C12—H12···O1ⁱ	0.93	2.55	3.456 (4)	165

Symmetry code: (i) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₈N₂O₅
M_r	390.38
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	9.246 (3), 11.911 (4), 17.923 (6)
V (Å³)	1974.0 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.23 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.977, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	8939, 3605, 2280
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.111, 1.01
No. of reflections	3605
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.12

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
C7—H7A···O5	0.97	2.27	2.734 (4)	108
C12—H12···O1ⁱ	0.93	2.55	3.456 (4)	165

Symmetry code: (i) −x, y+1/2, −z+1/2.

Acknowledgements

This work was supported by the Science and Technology Plan Projects of Lanzhou City (grant No. 2008-1-74)

References

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