1-Benzoyl-3,5-diphenyl-4,5-dihydro-1H-pyrazole

Zheng, C.-Z.; Wang, L.; Liu, J.

doi:10.1107/S1600536811003631

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o556

doi:10.1107/S1600536811003631

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1-Benzoyl-3,5-diphenyl-4,5-dihydro-1H-pyrazole

Chang-Zheng Zheng,^a Liang Wang ^a ^* and Juan Liu ^a

^aCollege of Environment and Chemical Engineering, Xi'an Polytechnic University, 710048 Xi'an, Shaanxi, People's Republic of China
^*Correspondence e-mail: wllily315668256@yahoo.com.cn

(Received 26 December 2010; accepted 28 January 2011; online 5 February 2011)

In the title compound, C₂₂H₁₈N₂O, the pyrazole ring is almost planar (r.m.s. deviation = 0.0098 Å) and its mean plane makes dihedral angles of 62.2 (2), 87.2 (2) and 8.0 (2)° with the phenyl and benzoyl rings, respectively. The crystal packing is stabilized by π–π stacking interactions [centroid–centroid distance = 3.658 (2) Å] and weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the coordination properties of aroylhydrazones, see: Egli et al. (2006 ); Ge (2006 ); Chopra et al. (2006 ). For related structures, see: Seebacher et al. (2003 ); Ge (2006); Jian & Wang (2006 ); Fun et al. (2010 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₂H₁₈N₂O
M_r = 326.38
Orthorhombic, P c a 2₁
a = 20.276 (6) Å
b = 5.7859 (17) Å
c = 14.786 (4) Å
V = 1734.5 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.18 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2006) T_min = 0.986, T_max = 0.991
8497 measured reflections
1601 independent reflections
1100 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.081
S = 1.09
1601 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O1ⁱ	0.93	2.72	3.399 (5)	131
C22—H22⋯O1ⁱ	0.93	3.00	3.540 (4)	119
C10—H10⋯O1ⁱⁱ	0.93	2.87	3.793 (5)	174
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+1, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z.

Data collection: SMART (Bruker, 1996 ); cell refinement: SAINT (Bruker, 1996); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003631/zq2084sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003631/zq2084Isup2.hkl

checkCIF report

Comment top

The chemistry of aroylhydrazones continues to attract much attention due to their coordination ability to metal ions (Egli et al., 2006; Ge, 2006) and their biological activity (Egli et al., 2006; Chopra et al., 2006). As an extension of work on the structural characterization of aroylhydrazone derivatives, the title compound,C₂₂H₁₈N₂O, was successfully synthesized and its crystal structure is reported here.

In the title complex, C₂₂H₁₈N₂O, all bond lengths and angles are normal (Allen et al., 1987). The pyrazole ring is planar (rms deviation = 0.0098 Å) and its mean plane makes dihedral angles of 62.2 (1), 87.2 (1) and 8.0 (2)° with the benzene rings C2-C7, C9-C14 and C17-C22, respectively (Fig. 1). The crystal packing is stabilized by π-π stacking interactions between the pyrazole ring and one benzene ring with a centroid-centroid separation of 3.658 (2) Å and by weak intermolecular C—H···O hydrogen bonds (Fig.2; Table 1).

Related literature top

For the coordination properties of aroylhydrazones, see: Egli et al. (2006); Ge (2006); Chopra et al. (2006). For related structures, see: Seebacher et al. (2003); Ge (2006); Jian & Wang (2006); Fun et al. (2010). For bond-length data, see: Allen et al. (1987).

Experimental top

A methanol solution (10 ml) of N'-(E)-(benzylidene acetophenone phenmethyl acylhydrazone) (0.25 mmol,0.082 g) was mixed with a DMF solution (5 ml). The mixture was stirred at 298 K for 2 h. and then filtered. A colorless precipitate was produced after about 20 days. A DMF amount (5 ml) was used to dissolve the precipitate at 330 K. Colorless block-shaped crystals of the title complex were obtained after one month (yield 30%).

Computing details top

Data collection: SMART (Bruker, 1996); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT (Bruker, 1996); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. The crystal packing of the title compound.

1-Benzoyl-3,5-diphenyl-4,5-dihydro-1H-pyrazole top

Crystal data top

C₂₂H₁₈N₂O	F(000) = 688
M_r = 326.38	D_x = 1.250 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1072 reflections
a = 20.276 (6) Å	θ = 2.4–17.6°
b = 5.7859 (17) Å	µ = 0.08 mm⁻¹
c = 14.786 (4) Å	T = 298 K
V = 1734.5 (9) Å³	Block, colorless
Z = 4	0.18 × 0.16 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1601 independent reflections
Radiation source: fine-focus sealed tube	1100 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2006)	h = −24→23
T_min = 0.986, T_max = 0.991	k = −6→6
8497 measured reflections	l = −17→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0335P)²] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
1601 reflections	Δρ_max = 0.13 e Å⁻³
227 parameters	Δρ_min = −0.10 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0113 (15)

Crystal data top

C₂₂H₁₈N₂O	V = 1734.5 (9) Å³
M_r = 326.38	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 20.276 (6) Å	µ = 0.08 mm⁻¹
b = 5.7859 (17) Å	T = 298 K
c = 14.786 (4) Å	0.18 × 0.16 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1601 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2006)	1100 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.991	R_int = 0.050
8497 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 1.09	Δρ_max = 0.13 e Å⁻³
1601 reflections	Δρ_min = −0.10 e Å⁻³
227 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
O1	0.27196 (11)	0.5466 (4)	0.77340 (17)	0.0769 (7)
N1	0.28823 (12)	0.8795 (5)	0.84788 (17)	0.0617 (7)
N2	0.33000 (12)	1.0610 (4)	0.87296 (18)	0.0587 (7)
C1	0.30374 (16)	0.7269 (6)	0.7810 (2)	0.0607 (8)
C2	0.35797 (16)	0.7877 (6)	0.7181 (2)	0.0602 (8)
C3	0.36177 (18)	0.9982 (7)	0.6747 (3)	0.0742 (10)
H3	0.3325	1.1160	0.6895	0.089*
C4	0.4093 (2)	1.0336 (9)	0.6092 (3)	0.0904 (12)
H4	0.4105	1.1731	0.5780	0.109*
C5	0.4545 (2)	0.8659 (11)	0.5897 (3)	0.1057 (16)
H5	0.4870	0.8929	0.5465	0.127*
C6	0.4521 (2)	0.6593 (10)	0.6336 (3)	0.1046 (16)
H6	0.4833	0.5458	0.6209	0.125*
C7	0.40374 (18)	0.6183 (7)	0.6965 (3)	0.0840 (11)
H7	0.4016	0.4752	0.7250	0.101*
C8	0.23482 (15)	0.8362 (6)	0.9137 (2)	0.0630 (9)
H8	0.2392	0.6799	0.9386	0.076*
C9	0.16756 (15)	0.8651 (6)	0.8719 (2)	0.0566 (8)
C10	0.15150 (17)	1.0621 (6)	0.8242 (3)	0.0719 (10)
H10	0.1833	1.1755	0.8150	0.086*
C11	0.0887 (2)	1.0930 (7)	0.7897 (3)	0.0838 (11)
H11	0.0788	1.2254	0.7568	0.101*
C12	0.04134 (19)	0.9293 (9)	0.8040 (3)	0.0874 (12)
H12	−0.0014	0.9531	0.7830	0.105*
C13	0.05668 (19)	0.7314 (8)	0.8490 (3)	0.0860 (12)
H13	0.0248	0.6176	0.8568	0.103*
C14	0.11969 (17)	0.6987 (6)	0.8833 (3)	0.0726 (10)
H14	0.1297	0.5632	0.9142	0.087*
C15	0.25078 (16)	1.0154 (6)	0.9873 (2)	0.0690 (9)
H15A	0.2141	1.1206	0.9964	0.083*
H15B	0.2612	0.9407	1.0443	0.083*
C16	0.30982 (15)	1.1402 (5)	0.9498 (2)	0.0572 (8)
C17	0.34201 (15)	1.3367 (6)	0.9937 (2)	0.0578 (8)
C18	0.39084 (15)	1.4622 (6)	0.9502 (3)	0.0655 (9)
H18	0.4046	1.4170	0.8929	0.079*
C19	0.41933 (17)	1.6525 (6)	0.9903 (3)	0.0745 (10)
H19	0.4518	1.7353	0.9598	0.089*
C20	0.39988 (19)	1.7206 (7)	1.0755 (3)	0.0785 (11)
H20	0.4191	1.8490	1.1027	0.094*
C21	0.3520 (2)	1.5976 (7)	1.1199 (3)	0.0802 (11)
H21	0.3391	1.6421	1.1777	0.096*
C22	0.32291 (17)	1.4088 (6)	1.0798 (2)	0.0718 (10)
H22	0.2901	1.3283	1.1104	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0671 (16)	0.0745 (15)	0.0890 (18)	−0.0040 (13)	−0.0021 (13)	−0.0112 (14)
N1	0.0474 (15)	0.0756 (18)	0.0622 (18)	0.0008 (14)	0.0018 (13)	−0.0107 (15)
N2	0.0485 (14)	0.0682 (18)	0.0594 (17)	0.0074 (14)	−0.0021 (13)	−0.0077 (15)
C1	0.049 (2)	0.070 (2)	0.062 (2)	0.0125 (18)	−0.0095 (17)	−0.008 (2)
C2	0.056 (2)	0.074 (2)	0.051 (2)	0.0028 (18)	−0.0054 (16)	−0.0150 (19)
C3	0.066 (2)	0.094 (3)	0.063 (2)	−0.002 (2)	−0.0115 (19)	−0.007 (2)
C4	0.094 (3)	0.116 (3)	0.062 (2)	−0.027 (3)	−0.002 (2)	−0.010 (2)
C5	0.090 (3)	0.149 (4)	0.077 (3)	−0.039 (4)	0.024 (3)	−0.051 (3)
C6	0.084 (3)	0.121 (4)	0.109 (4)	−0.002 (3)	0.027 (3)	−0.055 (3)
C7	0.073 (3)	0.095 (3)	0.083 (3)	0.004 (2)	0.012 (2)	−0.024 (2)
C8	0.052 (2)	0.073 (2)	0.064 (2)	0.0006 (17)	0.0000 (16)	0.0051 (18)
C9	0.0491 (17)	0.064 (2)	0.057 (2)	−0.0009 (16)	0.0016 (15)	−0.0036 (18)
C10	0.062 (2)	0.075 (2)	0.079 (2)	−0.0017 (19)	−0.0084 (18)	0.001 (2)
C11	0.078 (3)	0.091 (3)	0.083 (3)	0.015 (2)	−0.020 (2)	−0.002 (2)
C12	0.053 (2)	0.123 (3)	0.086 (3)	0.012 (3)	−0.007 (2)	−0.015 (3)
C13	0.057 (2)	0.116 (4)	0.085 (3)	−0.022 (2)	0.006 (2)	−0.013 (3)
C14	0.063 (2)	0.078 (3)	0.077 (2)	−0.007 (2)	0.0091 (19)	−0.002 (2)
C15	0.0513 (18)	0.100 (2)	0.056 (2)	−0.0009 (19)	0.0007 (16)	−0.003 (2)
C16	0.0480 (18)	0.075 (2)	0.0483 (19)	0.0102 (16)	−0.0053 (15)	−0.0023 (18)
C17	0.0468 (18)	0.078 (2)	0.0482 (19)	0.0109 (17)	−0.0077 (16)	−0.0046 (17)
C18	0.052 (2)	0.089 (2)	0.0554 (19)	0.0029 (18)	−0.0022 (18)	−0.008 (2)
C19	0.063 (2)	0.091 (3)	0.070 (3)	−0.0057 (19)	−0.0032 (19)	−0.007 (2)
C20	0.071 (3)	0.090 (3)	0.075 (3)	0.008 (2)	−0.018 (2)	−0.020 (2)
C21	0.077 (3)	0.103 (3)	0.060 (2)	0.004 (2)	−0.005 (2)	−0.019 (2)
C22	0.068 (2)	0.098 (3)	0.049 (2)	0.0001 (19)	−0.0013 (17)	−0.006 (2)

Geometric parameters (Å, º) top

O1—C1	1.231 (4)	C10—H10	0.9300
N1—C1	1.362 (4)	C11—C12	1.365 (5)
N1—N2	1.399 (3)	C11—H11	0.9300
N1—C8	1.478 (4)	C12—C13	1.360 (5)
N2—C16	1.292 (4)	C12—H12	0.9300
C1—C2	1.482 (4)	C13—C14	1.387 (5)
C2—C3	1.379 (5)	C13—H13	0.9300
C2—C7	1.387 (4)	C14—H14	0.9300
C3—C4	1.381 (5)	C15—C16	1.504 (5)
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.366 (6)	C15—H15B	0.9700
C4—H4	0.9300	C16—C17	1.463 (4)
C5—C6	1.361 (6)	C17—C18	1.386 (4)
C5—H5	0.9300	C17—C22	1.394 (4)
C6—C7	1.373 (6)	C18—C19	1.378 (5)
C6—H6	0.9300	C18—H18	0.9300
C7—H7	0.9300	C19—C20	1.378 (5)
C8—C9	1.507 (4)	C19—H19	0.9300
C8—C15	1.537 (4)	C20—C21	1.371 (5)
C8—H8	0.9800	C20—H20	0.9300
C9—C14	1.377 (4)	C21—C22	1.377 (5)
C9—C10	1.380 (4)	C21—H21	0.9300
C10—C11	1.383 (5)	C22—H22	0.9300

C1—N1—N2	122.6 (3)	C12—C11—H11	120.0
C1—N1—C8	122.5 (3)	C10—C11—H11	120.0
N2—N1—C8	113.3 (3)	C13—C12—C11	119.9 (4)
C16—N2—N1	107.9 (3)	C13—C12—H12	120.0
O1—C1—N1	119.6 (3)	C11—C12—H12	120.0
O1—C1—C2	122.1 (3)	C12—C13—C14	120.3 (4)
N1—C1—C2	118.2 (3)	C12—C13—H13	119.9
C3—C2—C7	118.7 (3)	C14—C13—H13	119.9
C3—C2—C1	122.9 (3)	C9—C14—C13	120.6 (4)
C7—C2—C1	118.2 (3)	C9—C14—H14	119.7
C2—C3—C4	119.7 (4)	C13—C14—H14	119.7
C2—C3—H3	120.1	C16—C15—C8	103.3 (3)
C4—C3—H3	120.1	C16—C15—H15A	111.1
C5—C4—C3	120.7 (4)	C8—C15—H15A	111.1
C5—C4—H4	119.6	C16—C15—H15B	111.1
C3—C4—H4	119.6	C8—C15—H15B	111.1
C6—C5—C4	120.0 (4)	H15A—C15—H15B	109.1
C6—C5—H5	120.0	N2—C16—C17	121.6 (3)
C4—C5—H5	120.0	N2—C16—C15	114.0 (3)
C5—C6—C7	120.0 (4)	C17—C16—C15	124.4 (3)
C5—C6—H6	120.0	C18—C17—C22	117.7 (3)
C7—C6—H6	120.0	C18—C17—C16	121.4 (3)
C6—C7—C2	120.8 (4)	C22—C17—C16	120.9 (3)
C6—C7—H7	119.6	C19—C18—C17	121.3 (3)
C2—C7—H7	119.6	C19—C18—H18	119.4
N1—C8—C9	112.0 (2)	C17—C18—H18	119.4
N1—C8—C15	101.4 (3)	C18—C19—C20	120.1 (4)
C9—C8—C15	114.0 (3)	C18—C19—H19	119.9
N1—C8—H8	109.7	C20—C19—H19	119.9
C9—C8—H8	109.7	C21—C20—C19	119.5 (4)
C15—C8—H8	109.7	C21—C20—H20	120.2
C14—C9—C10	118.2 (3)	C19—C20—H20	120.2
C14—C9—C8	120.7 (3)	C20—C21—C22	120.6 (4)
C10—C9—C8	121.0 (3)	C20—C21—H21	119.7
C9—C10—C11	120.8 (4)	C22—C21—H21	119.7
C9—C10—H10	119.6	C21—C22—C17	120.8 (4)
C11—C10—H10	119.6	C21—C22—H22	119.6
C12—C11—C10	120.1 (4)	C17—C22—H22	119.6

C1—N1—N2—C16	−165.4 (3)	C14—C9—C10—C11	0.9 (5)
C8—N1—N2—C16	0.8 (3)	C8—C9—C10—C11	−176.8 (3)
N2—N1—C1—O1	166.0 (3)	C9—C10—C11—C12	1.1 (6)
C8—N1—C1—O1	1.0 (4)	C10—C11—C12—C13	−2.7 (6)
N2—N1—C1—C2	−15.4 (4)	C11—C12—C13—C14	2.3 (6)
C8—N1—C1—C2	179.6 (3)	C10—C9—C14—C13	−1.3 (5)
O1—C1—C2—C3	128.9 (3)	C8—C9—C14—C13	176.4 (3)
N1—C1—C2—C3	−49.7 (4)	C12—C13—C14—C9	−0.3 (6)
O1—C1—C2—C7	−45.7 (4)	N1—C8—C15—C16	2.1 (3)
N1—C1—C2—C7	135.7 (3)	C9—C8—C15—C16	−118.4 (3)
C7—C2—C3—C4	2.0 (5)	N1—N2—C16—C17	−178.2 (2)
C1—C2—C3—C4	−172.5 (3)	N1—N2—C16—C15	0.8 (3)
C2—C3—C4—C5	−3.0 (5)	C8—C15—C16—N2	−1.9 (4)
C3—C4—C5—C6	1.5 (6)	C8—C15—C16—C17	177.0 (3)
C4—C5—C6—C7	0.8 (7)	N2—C16—C17—C18	7.1 (4)
C5—C6—C7—C2	−1.8 (6)	C15—C16—C17—C18	−171.7 (3)
C3—C2—C7—C6	0.3 (5)	N2—C16—C17—C22	−175.0 (3)
C1—C2—C7—C6	175.2 (3)	C15—C16—C17—C22	6.2 (4)
C1—N1—C8—C9	−73.8 (4)	C22—C17—C18—C19	−0.4 (5)
N2—N1—C8—C9	120.0 (3)	C16—C17—C18—C19	177.5 (3)
C1—N1—C8—C15	164.3 (3)	C17—C18—C19—C20	0.6 (5)
N2—N1—C8—C15	−1.9 (3)	C18—C19—C20—C21	0.0 (5)
N1—C8—C9—C14	131.1 (3)	C19—C20—C21—C22	−0.7 (5)
C15—C8—C9—C14	−114.5 (3)	C20—C21—C22—C17	0.9 (5)
N1—C8—C9—C10	−51.3 (4)	C18—C17—C22—C21	−0.3 (5)
C15—C8—C9—C10	63.1 (4)	C16—C17—C22—C21	−178.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O1ⁱ	0.93	2.72	3.399 (5)	131
C22—H22···O1ⁱ	0.93	3.00	3.540 (4)	119
C10—H10···O1ⁱⁱ	0.93	2.87	3.793 (5)	174

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₈N₂O
M_r	326.38
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	298
a, b, c (Å)	20.276 (6), 5.7859 (17), 14.786 (4)
V (Å³)	1734.5 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.18 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2006)
T_min, T_max	0.986, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	8497, 1601, 1100
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.081, 1.09
No. of reflections	1601
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.10

Computer programs: SMART (Bruker, 1996), SAINT (Bruker, 1996), 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
C21—H21···O1ⁱ	0.93	2.72	3.399 (5)	131
C22—H22···O1ⁱ	0.93	3.00	3.540 (4)	119
C10—H10···O1ⁱⁱ	0.93	2.87	3.793 (5)	174

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

Acknowledgements

The authors thank the National Natural Science Foundation of Shaanxi Province, China (2009JM2012) for financial support.

References

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