5-(3-Chloro­phen­ylsulfan­yl)-1-methyl-3-trifluoro­methyl-1H-pyrazole-4-carbaldehyde O-[(2-chloro-1,3-thia­zol-5-yl)meth­yl]oxime

Dai, H.; Li, S.; Luo, K.-P.; Fang, J.-X.; Shi, Y.-J.

doi:10.1107/S160053681105358X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o155

doi:10.1107/S160053681105358X

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5-(3-Chlorophenylsulfanyl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde O-[(2-chloro-1,3-thiazol-5-yl)methyl]oxime

Hong Dai,^a,^b Shuang Li,^a Kun-Peng Luo,^a Jian-Xin Fang ^b ^* and Yu-Jun Shi ^a

^aCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, People's Republic of China, and ^bState Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China
^*Correspondence e-mail: daihong_2001@yahoo.com.cn

(Received 17 October 2011; accepted 12 December 2011; online 17 December 2011)

In the title compound, C₁₆H₁₁Cl₂F₃N₄OS₂, the benzene ring and the thiazole ring make dihedral angles of 83.2 (3) and 78.3 (3)°, respectively, with the pyrazole ring. The crystal packing shows S⋯N contacts of 3.309 (2) Å.

Related literature

For the bioactivity of pyrazole oxime derivatives, see: Takao et al. (1994 ); Watanabe et al. (2001 ). For the biological activity of thiazole derivatives, see: Fahmy & Bekhit (2002 ); Sidoova et al. (1999 ); Zhang et al. (2000 ).

Experimental

Crystal data

C₁₆H₁₁Cl₂F₃N₄OS₂
M_r = 467.31
Monoclinic, P 2₁ /n
a = 12.328 (3) Å
b = 12.787 (3) Å
c = 13.139 (3) Å
β = 110.16 (3)°
V = 1944.3 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 113 K
0.20 × 0.16 × 0.10 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ) T_min = 0.891, T_max = 0.943
9881 measured reflections
3309 independent reflections
2725 reflections with I > 2σ(I)
R_int = 0.116

Refinement

R[F² > 2σ(F²)] = 0.088
wR(F²) = 0.273
S = 1.10
3309 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.94 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; 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 global, I. DOI: 10.1107/S160053681105358X/aa2035sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681105358X/aa2035Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681105358X/aa2035Isup3.cml

checkCIF report

Comment top

Recently, pyrazole oximes are reported to possess diverse biological activities, such as fungicidal, insecticidal, and acaricidal activities (Takao et al., 1994; Watanabe et al., 2001). On the other hand, many thiazole derivatives have been found to show insecticidal, herbicidal, and anticancer activities (Sidoova et al., 1999; Zhang et al., 2000; Fahmy & Bekhit, 2002). In search of novel pyrazole oxime derivatives with good bioactivities, we have sought to synthesize new pyrazole oxime ethers containing thiazole units. We report here the crystal structure of the target compound, (I). It contains three planes, the pyrazole ring (C2/C3/C4/N1/N2), the substituted phenyl ring (C6/C7/C8/C9/C10/C11) and the thiazole ring (C15/C14/S2/C16/N4) (Fig. 1). The dihedral angles between the the phenyl ring and the pyrazole ring and between the thiazole ring and the pyrazole ring are 83.2 (3)° and 78.3 (3)°, respectively. The crystal structure of (I) is stabilized by S···N contacts.

Related literature top

For the bioactivity of pyrazole oxime derivatives, see: Takao et al. (1994); Watanabe et al. (2001). For the biological activity of thiazole derivatives, see: Fahmy & Bekhit (2002); Sidoova et al. (1999); Zhang et al. (2000).

Experimental top

To a violently stirred solution of 1-methyl-3-trifluoromethyl-5- (3-chlorophenylthio)-1H-pyrazole-4-carbaldehyde oxime (3 mmol) and potassium carbonate (9 mmol) in 20 ml of anhydrous N,N-dimethylformamide, was added dropwise a solution of 2-chloro-5-chloromethylthiazole (3.6 mmol) in 10 ml of anhydrous N,N-dimethylformamide. Then, to the above mixture was added a catalytic amount of caesium chloride at room temperature. The resulting solution was heated to 373 K for 6 h. After cooling to room temperature, the mixture was poured into water (200 ml) and extracted with ethyl acetate (3 × 50 ml). The organic layer was washed with 10% sodium carbonate solution (3 × 30 ml) and dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was separated by column chromatography on silica gel using a mixture of petroleum ether/ethyl acetate to obtain colourless crystals.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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. View of the title compound (I), with displacement ellipsoids drawn at the 30% probability level.

5-(3-Chlorophenylsulfanyl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4- carbaldehyde O-[(2-chloro-1,3-thiazol-5-yl)methyl]oxime top

Crystal data top

C₁₆H₁₁Cl₂F₃N₄OS₂	F(000) = 944
M_r = 467.31	D_x = 1.597 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5433 reflections
a = 12.328 (3) Å	θ = 1.6–27.2°
b = 12.787 (3) Å	µ = 0.59 mm⁻¹
c = 13.139 (3) Å	T = 113 K
β = 110.16 (3)°	Prism, colourless
V = 1944.3 (9) Å³	0.20 × 0.16 × 0.10 mm
Z = 4

Data collection top

Rigaku Saturn diffractometer	3309 independent reflections
Radiation source: rotating anode	2725 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.116
ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	h = −11→14
T_min = 0.891, T_max = 0.943	k = −15→14
9881 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.273	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
3309 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.81 e Å⁻³
0 restraints	Δρ_min = −0.94 e Å⁻³

Crystal data top

C₁₆H₁₁Cl₂F₃N₄OS₂	V = 1944.3 (9) Å³
M_r = 467.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.328 (3) Å	µ = 0.59 mm⁻¹
b = 12.787 (3) Å	T = 113 K
c = 13.139 (3) Å	0.20 × 0.16 × 0.10 mm
β = 110.16 (3)°

Data collection top

Rigaku Saturn diffractometer	3309 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	2725 reflections with I > 2σ(I)
T_min = 0.891, T_max = 0.943	R_int = 0.116
9881 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.088	0 restraints
wR(F²) = 0.273	H-atom parameters constrained
S = 1.10	Δρ_max = 0.81 e Å⁻³
3309 reflections	Δρ_min = −0.94 e Å⁻³
254 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Cl1	0.01343 (10)	0.94499 (10)	0.66778 (11)	0.0519 (5)
Cl2	0.57227 (10)	0.80206 (10)	0.00569 (10)	0.0483 (4)
S1	0.36532 (9)	1.11017 (8)	0.55348 (9)	0.0348 (4)
S2	0.38132 (9)	0.80301 (8)	0.09658 (8)	0.0334 (4)
F1	0.2428 (2)	0.69627 (18)	0.3650 (2)	0.0403 (7)
F2	0.3861 (2)	0.62954 (18)	0.49260 (18)	0.0396 (7)
F3	0.4134 (2)	0.70073 (18)	0.3550 (2)	0.0388 (7)
O1	0.1746 (3)	0.9511 (2)	0.1630 (2)	0.0351 (7)
N1	0.4428 (3)	0.9119 (3)	0.6202 (2)	0.0280 (7)
N2	0.4393 (3)	0.8114 (2)	0.5871 (3)	0.0293 (8)
N3	0.2447 (3)	0.8956 (2)	0.2545 (3)	0.0312 (8)
N4	0.3842 (3)	0.9182 (3)	−0.0643 (3)	0.0402 (9)
C1	0.3548 (3)	0.7100 (3)	0.4235 (3)	0.0305 (9)
C2	0.3752 (3)	0.8122 (3)	0.4828 (3)	0.0283 (9)
C3	0.3354 (3)	0.9140 (3)	0.4454 (3)	0.0279 (8)
C4	0.3791 (3)	0.9760 (3)	0.5370 (3)	0.0285 (8)
C5	0.5030 (4)	0.9391 (3)	0.7338 (3)	0.0381 (10)
H5A	0.4487	0.9410	0.7714	0.057*
H5B	0.5386	1.0065	0.7379	0.057*
H5C	0.5613	0.8876	0.7666	0.057*
C6	0.2689 (3)	1.1125 (3)	0.6278 (3)	0.0310 (9)
C7	0.2734 (4)	1.2006 (3)	0.6906 (3)	0.0348 (10)
H7	0.3280	1.2526	0.6967	0.042*
C8	0.1934 (4)	1.2099 (3)	0.7451 (4)	0.0405 (11)
H8	0.1950	1.2690	0.7869	0.049*
C9	0.1125 (4)	1.1326 (3)	0.7376 (3)	0.0397 (10)
H9	0.0596	1.1389	0.7734	0.048*
C10	0.1127 (4)	1.0458 (3)	0.6753 (3)	0.0345 (9)
C11	0.1877 (3)	1.0346 (3)	0.6185 (3)	0.0328 (9)
H11	0.1839	0.9763	0.5750	0.039*
C12	0.2648 (3)	0.9524 (3)	0.3388 (3)	0.0308 (9)
H12	0.2339	1.0195	0.3321	0.037*
C13	0.1586 (4)	0.8867 (3)	0.0688 (3)	0.0351 (10)
H13A	0.0938	0.9134	0.0089	0.042*
H13B	0.1397	0.8161	0.0841	0.042*
C14	0.2639 (3)	0.8834 (3)	0.0357 (3)	0.0302 (9)
C15	0.2824 (4)	0.9380 (3)	−0.0462 (3)	0.0360 (10)
H15	0.2288	0.9862	−0.0877	0.043*
C16	0.4424 (4)	0.8484 (3)	0.0046 (3)	0.0355 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0347 (7)	0.0614 (8)	0.0707 (9)	−0.0063 (5)	0.0322 (6)	−0.0026 (5)
Cl2	0.0299 (7)	0.0728 (9)	0.0460 (7)	0.0030 (5)	0.0179 (5)	−0.0001 (5)
S1	0.0347 (7)	0.0345 (6)	0.0437 (7)	−0.0039 (4)	0.0244 (5)	−0.0030 (4)
S2	0.0270 (7)	0.0436 (7)	0.0312 (7)	0.0031 (4)	0.0119 (5)	0.0028 (4)
F1	0.0242 (13)	0.0447 (14)	0.0503 (15)	−0.0077 (9)	0.0109 (11)	−0.0058 (10)
F2	0.0461 (16)	0.0323 (12)	0.0411 (14)	0.0024 (10)	0.0161 (12)	0.0052 (9)
F3	0.0392 (15)	0.0408 (13)	0.0442 (14)	−0.0027 (10)	0.0244 (12)	−0.0076 (10)
O1	0.0342 (16)	0.0420 (15)	0.0284 (14)	0.0115 (11)	0.0100 (12)	0.0036 (11)
N1	0.0197 (16)	0.0392 (17)	0.0297 (17)	−0.0036 (13)	0.0143 (13)	−0.0025 (13)
N2	0.0219 (17)	0.0339 (17)	0.0336 (18)	−0.0021 (12)	0.0115 (14)	−0.0001 (13)
N3	0.0263 (18)	0.0370 (18)	0.0319 (17)	0.0058 (13)	0.0120 (14)	0.0054 (13)
N4	0.036 (2)	0.054 (2)	0.0329 (19)	−0.0050 (17)	0.0147 (16)	0.0029 (17)
C1	0.022 (2)	0.040 (2)	0.033 (2)	0.0003 (15)	0.0145 (16)	0.0024 (16)
C2	0.0200 (19)	0.037 (2)	0.032 (2)	−0.0028 (14)	0.0142 (16)	−0.0006 (15)
C3	0.0203 (19)	0.0370 (19)	0.032 (2)	−0.0006 (14)	0.0160 (16)	0.0011 (15)
C4	0.0191 (18)	0.040 (2)	0.034 (2)	−0.0026 (15)	0.0190 (16)	−0.0001 (15)
C5	0.031 (2)	0.048 (2)	0.035 (2)	−0.0055 (17)	0.0110 (18)	−0.0068 (18)
C6	0.026 (2)	0.040 (2)	0.0281 (19)	0.0018 (15)	0.0111 (16)	0.0017 (15)
C7	0.036 (2)	0.035 (2)	0.036 (2)	0.0047 (15)	0.016 (2)	0.0016 (15)
C8	0.042 (3)	0.047 (2)	0.036 (2)	0.0157 (19)	0.019 (2)	−0.0039 (18)
C9	0.033 (2)	0.056 (3)	0.035 (2)	0.0158 (19)	0.0181 (19)	0.0011 (19)
C10	0.024 (2)	0.046 (2)	0.036 (2)	0.0040 (16)	0.0134 (17)	0.0046 (17)
C11	0.026 (2)	0.041 (2)	0.033 (2)	0.0066 (16)	0.0125 (17)	0.0007 (16)
C12	0.025 (2)	0.036 (2)	0.035 (2)	0.0039 (15)	0.0158 (17)	0.0010 (15)
C13	0.029 (2)	0.047 (2)	0.029 (2)	0.0040 (16)	0.0098 (17)	0.0009 (16)
C14	0.0233 (19)	0.038 (2)	0.0286 (19)	0.0009 (15)	0.0077 (16)	−0.0017 (15)
C15	0.033 (2)	0.040 (2)	0.034 (2)	0.0066 (16)	0.0105 (18)	0.0056 (16)
C16	0.030 (2)	0.047 (2)	0.031 (2)	−0.0041 (17)	0.0120 (17)	−0.0030 (17)

Geometric parameters (Å, º) top

Cl1—C10	1.756 (4)	C3—C12	1.456 (5)
Cl2—C16	1.703 (4)	C5—H5A	0.9600
S1—C4	1.744 (4)	C5—H5B	0.9600
S1—C6	1.780 (4)	C5—H5C	0.9600
S2—C16	1.729 (4)	C6—C7	1.386 (6)
S2—C14	1.730 (4)	C6—C11	1.387 (6)
F1—C1	1.341 (5)	C7—C8	1.409 (6)
F2—C1	1.338 (5)	C7—H7	0.9300
F3—C1	1.339 (5)	C8—C9	1.383 (7)
O1—N3	1.407 (4)	C8—H8	0.9300
O1—C13	1.442 (5)	C9—C10	1.380 (6)
N1—N2	1.352 (5)	C9—H9	0.9300
N1—C4	1.376 (5)	C10—C11	1.382 (6)
N1—C5	1.461 (5)	C11—H11	0.9300
N2—C2	1.325 (5)	C12—H12	0.9300
N3—C12	1.275 (5)	C13—C14	1.505 (6)
N4—C16	1.298 (6)	C13—H13A	0.9700
N4—C15	1.379 (6)	C13—H13B	0.9700
C1—C2	1.497 (5)	C14—C15	1.366 (6)
C2—C3	1.418 (5)	C15—H15	0.9300
C3—C4	1.386 (5)

C4—S1—C6	101.37 (18)	C6—C7—C8	118.7 (4)
C16—S2—C14	88.5 (2)	C6—C7—H7	120.7
N3—O1—C13	107.9 (3)	C8—C7—H7	120.7
N2—N1—C4	111.4 (3)	C9—C8—C7	121.1 (4)
N2—N1—C5	120.2 (3)	C9—C8—H8	119.4
C4—N1—C5	128.3 (3)	C7—C8—H8	119.4
C2—N2—N1	105.5 (3)	C10—C9—C8	117.9 (4)
C12—N3—O1	109.5 (3)	C10—C9—H9	121.0
C16—N4—C15	108.8 (4)	C8—C9—H9	121.0
F2—C1—F3	107.0 (3)	C9—C10—C11	122.8 (4)
F2—C1—F1	106.7 (3)	C9—C10—Cl1	118.7 (3)
F3—C1—F1	106.9 (3)	C11—C10—Cl1	118.5 (3)
F2—C1—C2	111.1 (3)	C10—C11—C6	118.4 (4)
F3—C1—C2	113.3 (3)	C10—C11—H11	120.8
F1—C1—C2	111.6 (3)	C6—C11—H11	120.8
N2—C2—C3	112.2 (3)	N3—C12—C3	121.1 (4)
N2—C2—C1	117.7 (3)	N3—C12—H12	119.5
C3—C2—C1	130.1 (4)	C3—C12—H12	119.5
C4—C3—C2	103.9 (3)	O1—C13—C14	112.8 (3)
C4—C3—C12	124.5 (4)	O1—C13—H13A	109.0
C2—C3—C12	131.6 (3)	C14—C13—H13A	109.0
N1—C4—C3	107.0 (3)	O1—C13—H13B	109.0
N1—C4—S1	122.7 (3)	C14—C13—H13B	109.0
C3—C4—S1	130.2 (3)	H13A—C13—H13B	107.8
N1—C5—H5A	109.5	C15—C14—C13	127.5 (4)
N1—C5—H5B	109.5	C15—C14—S2	109.1 (3)
H5A—C5—H5B	109.5	C13—C14—S2	123.4 (3)
N1—C5—H5C	109.5	C14—C15—N4	116.8 (4)
H5A—C5—H5C	109.5	C14—C15—H15	121.6
H5B—C5—H5C	109.5	N4—C15—H15	121.6
C7—C6—C11	121.0 (4)	N4—C16—Cl2	122.5 (3)
C7—C6—S1	116.3 (3)	N4—C16—S2	116.7 (3)
C11—C6—S1	122.5 (3)	Cl2—C16—S2	120.8 (3)

C4—N1—N2—C2	1.0 (4)	C4—S1—C6—C11	−28.8 (4)
C5—N1—N2—C2	177.4 (3)	C11—C6—C7—C8	0.0 (6)
C13—O1—N3—C12	177.1 (3)	S1—C6—C7—C8	175.6 (3)
N1—N2—C2—C3	0.1 (4)	C6—C7—C8—C9	0.7 (6)
N1—N2—C2—C1	−179.5 (3)	C7—C8—C9—C10	0.2 (6)
F2—C1—C2—N2	13.1 (5)	C8—C9—C10—C11	−1.8 (6)
F3—C1—C2—N2	−107.4 (4)	C8—C9—C10—Cl1	178.2 (3)
F1—C1—C2—N2	131.9 (4)	C9—C10—C11—C6	2.4 (6)
F2—C1—C2—C3	−166.4 (4)	Cl1—C10—C11—C6	−177.6 (3)
F3—C1—C2—C3	73.2 (5)	C7—C6—C11—C10	−1.4 (6)
F1—C1—C2—C3	−47.5 (5)	S1—C6—C11—C10	−176.8 (3)
N2—C2—C3—C4	−1.1 (4)	O1—N3—C12—C3	179.8 (3)
C1—C2—C3—C4	178.4 (4)	C4—C3—C12—N3	167.3 (4)
N2—C2—C3—C12	179.3 (4)	C2—C3—C12—N3	−13.1 (7)
C1—C2—C3—C12	−1.3 (7)	N3—O1—C13—C14	−75.3 (4)
N2—N1—C4—C3	−1.7 (4)	O1—C13—C14—C15	−100.8 (5)
C5—N1—C4—C3	−177.7 (4)	O1—C13—C14—S2	81.4 (4)
N2—N1—C4—S1	179.5 (3)	C16—S2—C14—C15	−1.1 (3)
C5—N1—C4—S1	3.5 (5)	C16—S2—C14—C13	177.0 (4)
C2—C3—C4—N1	1.6 (4)	C13—C14—C15—N4	−177.1 (4)
C12—C3—C4—N1	−178.7 (3)	S2—C14—C15—N4	0.9 (5)
C2—C3—C4—S1	−179.7 (3)	C16—N4—C15—C14	−0.1 (5)
C12—C3—C4—S1	0.0 (6)	C15—N4—C16—Cl2	178.8 (3)
C6—S1—C4—N1	−74.0 (3)	C15—N4—C16—S2	−0.9 (5)
C6—S1—C4—C3	107.5 (4)	C14—S2—C16—N4	1.2 (3)
C4—S1—C6—C7	155.6 (3)	C14—S2—C16—Cl2	−178.5 (3)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁Cl₂F₃N₄OS₂
M_r	467.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	12.328 (3), 12.787 (3), 13.139 (3)
β (°)	110.16 (3)
V (Å³)	1944.3 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.20 × 0.16 × 0.10

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2008)
T_min, T_max	0.891, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	9881, 3309, 2725
R_int	0.116
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.088, 0.273, 1.10
No. of reflections	3309
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.94

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (NNSFC) (grant No. 20772068), the Science and Technology Projects Fund of Nantong City (grant Nos. K2010016, AS2010005), the Science Foundation of Nantong University (grant Nos. 09Z010, 09 C001) and the Scientific Research Foundation for Talent Introduction of Nantong University.

References

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