N-(3-Chloro-4-eth­oxy­benzo­yl)-N′-(2-meth­oxy­phen­yl)thio­urea

Hu, J.-H.; Luo, Z.-Y.; Ding, C.-F.; Song, X.-L.

doi:10.1107/S1600536810054644

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o376

doi:10.1107/S1600536810054644

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N-(3-Chloro-4-ethoxybenzoyl)-N′-(2-methoxyphenyl)thiourea

Jing-Han Hu,^a ^* Zhong-Yi Luo,^a Chen-Fei Ding ^a and Xiao-Li Song ^a

^aCollege of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: hujinghan62@163.com

(Received 16 December 2010; accepted 29 December 2010; online 12 January 2011)

In the title compound, C₁₇H₁₇ClN₂O₃S, the central carbonylthiourea unit is nearly planar [maximum atomic deviation = 0.019 (3) Å] and makes dihedral angles of 2.47 (7) and 17.76 (6)° with the terminal benzene rings. An intramolecular N—H⋯O hydrogen bond occurs. Weak intermolecular C—H⋯S and C—H⋯Cl hydrogen bonding is observed in the crystal structure.

Related literature

For applications of thiourea derivatives, see: Antholine & Taketa (1982 ); Schroeder (1955 ). For related structures, see: Yusof & Yamin (2004a ,b ); Ali et al. (2004 ). For related acylthiourea derivatives, see: Zhang et al. (2003 , 2006 ).

Experimental

Crystal data

C₁₇H₁₇ClN₂O₃S
M_r = 364.84
Triclinic, $[P \overline 1]$
a = 7.8238 (8) Å
b = 8.4791 (11) Å
c = 14.9867 (13) Å
α = 76.365 (7)°
β = 89.384 (5)°
γ = 62.647 (4)°
V = 852.65 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 296 K
0.38 × 0.35 × 0.27 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.874, T_max = 0.908
4903 measured reflections
3314 independent reflections
2679 reflections with I > 2σ(I)
R_int = 0.012

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.216
S = 1.06
3314 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.85 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.86	1.88	2.613 (3)	143
C6—H6⋯S1ⁱ	0.93	2.86	3.468 (2)	124
C14—H14⋯Cl1ⁱⁱ	0.93	2.81	3.680 (3)	156
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x, y+1, z-1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054644/xu5125sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054644/xu5125Isup2.hkl

checkCIF report

Comment top

Thiourea derivatives have been studied for their potential use in agriculture, medicine and analytical chemistry (Schroeder, 1955; Antholine & Taketa, 1982). As part of our ongoing work on acylthiourea derivatives (Zhang et al., 2003; Zhang et al., 2006), we present here the structure of the title thiourea derivative, (I).

Benzoylthiourea derivatives can be synthesized from the reaction between benzoylisothiocyanate and amine compounds. In the title compound, (I), the molecular structure and dimensions are similar to those in other benzoylthiourea derivatives, such as N-(2-chlorophenyl)-N'-(4-methoxybenzoyl)thiourea (Yusof & Yamin, 2004a), N-(4-methoxybenzoyl-N'-(o-tolyl)thiourea (Yusof & Yamin, 2004b) and N-(p-methoxybenzoyl)-N'-(o-methoxyphenyl)thiourea (Ali et al., 2004). The molecule maintains its trans-cis configuration with respect to the position of the 3-chloro-4-ethoxybenzoyl and 2-methoxyphenyl groups relative to the S atom across the thiourea C—N bonds.

The central carbonyl thiourea moiety (S1/O2/N1/N2/C9/C10), the 2-methoxyphenyl group (C11–C16/O3/C23) and the 3-chloro-4-ethoxybenzoyl (C1–C6/C8/O1) group are individually planar. The C10—S1, C10—N1 and C10—N2 bond lengths are1.665 (2), 1.392 (2) and 1.333 (3) Å, respectively, comparable with those in N-(2-chlorophenyl)-N'- (4-methoxybenzoyl)-thiourea [C═S = 1.662 (2) Å, C8—N1 = 1.386 (3) Å and C8—N2 = 1.331 (3) Å; Yusof & Yamin, 2004a] and other benzoylthiourea derivatives. There is one intramolecular hydrogen bonds, via N2—H2···O2; as a result, one pseudo-six-membered rings, is formed (Fig. 1).

Related literature top

For applications of thiourea derivatives, see: Antholine & Taketa (1982); Schroeder (1955). For related structures, see: Yusof & Yamin (2004a,b); Ali et al. (2004). For related acylthiourea derivatives, see: Zhang et al. (2003, 2006).

Experimental top

Potassium thiocyanate (7.5 mmol), 3-chloro-4-ethoxybenzoyl chloride (5 mmol), PEG-400 (3% with respect to ammonium thiocyanate) and dichloromethane (20 ml) were placed in a dried flask and stirred at room temperature for 1 h, then 2-methoxyaniline (5 mmol) was added. The mixture was stirred for 0.5 h at room temperature and a precipitate was formed. This was filtered off, washed with water and dried. yellow single crystals of (I) were obtained from an ethanol–dimethylformamide (1:1) solution.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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, shown with 50% probability displacement ellipsoids.

N-(3-Chloro-4-ethoxybenzoyl)-N'-(2-methoxyphenyl)thiourea top

Crystal data top

C₁₇H₁₇ClN₂O₃S	Z = 2
M_r = 364.84	F(000) = 380
Triclinic, P1	D_x = 1.421 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8238 (8) Å	Cell parameters from 2087 reflections
b = 8.4791 (11) Å	θ = 2.8–29.3°
c = 14.9867 (13) Å	µ = 0.36 mm⁻¹
α = 76.365 (7)°	T = 296 K
β = 89.384 (5)°	Block, yellow
γ = 62.647 (4)°	0.38 × 0.35 × 0.27 mm
V = 852.65 (16) Å³

Data collection top

Bruker APEXII CCD diffractometer	3314 independent reflections
Radiation source: fine-focus sealed tube	2679 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.874, T_max = 0.908	k = −10→9
4903 measured reflections	l = −18→17

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.216	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.1281P)² + 0.5121P] where P = (F_o² + 2F_c²)/3
3314 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.85 e Å⁻³

Crystal data top

C₁₇H₁₇ClN₂O₃S	γ = 62.647 (4)°
M_r = 364.84	V = 852.65 (16) Å³
Triclinic, P1	Z = 2
a = 7.8238 (8) Å	Mo Kα radiation
b = 8.4791 (11) Å	µ = 0.36 mm⁻¹
c = 14.9867 (13) Å	T = 296 K
α = 76.365 (7)°	0.38 × 0.35 × 0.27 mm
β = 89.384 (5)°

Data collection top

Bruker APEXII CCD diffractometer	3314 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2679 reflections with I > 2σ(I)
T_min = 0.874, T_max = 0.908	R_int = 0.012
4903 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.216	H-atom parameters constrained
S = 1.06	Δρ_max = 0.33 e Å⁻³
3314 reflections	Δρ_min = −0.85 e Å⁻³
219 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	0.7479 (5)	0.3322 (4)	0.6563 (2)	0.0500 (7)
C2	0.9023 (5)	0.1588 (4)	0.6605 (2)	0.0484 (7)
C3	1.0005 (5)	0.1342 (4)	0.5825 (2)	0.0535 (7)
H3	1.1037	0.0201	0.5832	0.064*
C4	0.9454 (5)	0.2778 (4)	0.5048 (2)	0.0507 (7)
H4	1.0123	0.2591	0.4534	0.061*
C5	0.7916 (4)	0.4512 (4)	0.50087 (19)	0.0455 (7)
C6	0.6918 (4)	0.4750 (4)	0.5784 (2)	0.0467 (7)
H6	0.5868	0.5883	0.5772	0.056*
C7	1.0853 (5)	−0.1587 (4)	0.7415 (2)	0.0600 (8)
H7A	1.2106	−0.1668	0.7289	0.072*
H7B	1.0421	−0.1991	0.6950	0.072*
C8	1.0993 (6)	−0.2751 (5)	0.8357 (3)	0.0758 (11)
H8A	1.1418	−0.2333	0.8809	0.114*
H8B	1.1905	−0.4008	0.8396	0.114*
H8C	0.9745	−0.2659	0.8472	0.114*
C9	0.7458 (4)	0.5941 (4)	0.4133 (2)	0.0488 (7)
C10	0.5447 (4)	0.9307 (4)	0.34023 (19)	0.0435 (6)
C11	0.5829 (4)	1.0267 (4)	0.17305 (19)	0.0438 (6)
C12	0.7042 (4)	0.9479 (4)	0.1091 (2)	0.0465 (7)
C13	0.6871 (5)	1.0502 (4)	0.0204 (2)	0.0557 (8)
H13	0.7675	0.9962	−0.0217	0.067*
C14	0.5509 (5)	1.2321 (5)	−0.0058 (2)	0.0607 (8)
H14	0.5390	1.3018	−0.0657	0.073*
C15	0.4325 (5)	1.3110 (4)	0.0562 (2)	0.0624 (9)
H15	0.3413	1.4346	0.0379	0.075*
C16	0.4464 (5)	1.2103 (4)	0.1452 (2)	0.0552 (8)
H16	0.3641	1.2656	0.1863	0.066*
C23	0.9845 (6)	0.6837 (5)	0.0906 (3)	0.0777 (12)
H23A	0.9323	0.6801	0.0339	0.117*
H23B	1.0716	0.5608	0.1254	0.117*
H23C	1.0533	0.7541	0.0770	0.117*
Cl1	0.6221 (2)	0.36762 (17)	0.75042 (8)	0.0918 (4)
N1	0.6147 (4)	0.7725 (3)	0.41304 (16)	0.0461 (6)
H1	0.5705	0.7877	0.4648	0.055*
N2	0.6167 (4)	0.9049 (3)	0.26084 (16)	0.0480 (6)
H2	0.6994	0.7928	0.2638	0.058*
O1	0.9466 (4)	0.0284 (3)	0.74006 (15)	0.0597 (6)
O2	0.8217 (4)	0.5561 (3)	0.34440 (15)	0.0700 (7)
O3	0.8333 (4)	0.7658 (3)	0.14238 (16)	0.0636 (7)
S1	0.38700 (13)	1.12797 (11)	0.36170 (5)	0.0603 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0574 (17)	0.0502 (16)	0.0453 (16)	−0.0268 (14)	0.0093 (13)	−0.0143 (13)
C2	0.0594 (18)	0.0439 (15)	0.0419 (15)	−0.0256 (14)	−0.0015 (12)	−0.0080 (12)
C3	0.0589 (18)	0.0428 (15)	0.0447 (16)	−0.0135 (13)	0.0026 (13)	−0.0086 (13)
C4	0.0574 (17)	0.0429 (15)	0.0420 (15)	−0.0150 (13)	0.0073 (12)	−0.0120 (12)
C5	0.0512 (16)	0.0412 (14)	0.0407 (15)	−0.0183 (13)	0.0019 (12)	−0.0115 (12)
C6	0.0514 (16)	0.0394 (14)	0.0470 (16)	−0.0188 (13)	0.0064 (12)	−0.0128 (12)
C7	0.067 (2)	0.0490 (17)	0.0524 (18)	−0.0226 (16)	−0.0052 (15)	−0.0028 (14)
C8	0.087 (3)	0.062 (2)	0.067 (2)	−0.037 (2)	−0.006 (2)	0.0087 (18)
C9	0.0557 (17)	0.0391 (14)	0.0419 (15)	−0.0151 (13)	0.0026 (12)	−0.0086 (12)
C10	0.0443 (15)	0.0400 (14)	0.0414 (14)	−0.0151 (12)	0.0039 (11)	−0.0124 (11)
C11	0.0467 (15)	0.0392 (14)	0.0383 (14)	−0.0154 (12)	0.0033 (11)	−0.0080 (11)
C12	0.0498 (16)	0.0395 (14)	0.0442 (15)	−0.0168 (12)	0.0060 (12)	−0.0091 (12)
C13	0.0631 (19)	0.0518 (17)	0.0456 (16)	−0.0220 (15)	0.0154 (14)	−0.0119 (13)
C14	0.068 (2)	0.0560 (19)	0.0449 (17)	−0.0253 (16)	0.0057 (14)	0.0015 (14)
C15	0.0605 (19)	0.0432 (16)	0.0551 (18)	−0.0080 (14)	0.0061 (15)	0.0023 (14)
C16	0.0524 (17)	0.0445 (16)	0.0475 (16)	−0.0079 (13)	0.0095 (13)	−0.0066 (13)
C23	0.069 (2)	0.053 (2)	0.090 (3)	−0.0121 (17)	0.032 (2)	−0.0168 (19)
Cl1	0.1143 (9)	0.0876 (8)	0.0697 (7)	−0.0445 (7)	0.0403 (6)	−0.0216 (5)
N1	0.0549 (14)	0.0374 (12)	0.0348 (11)	−0.0131 (10)	0.0070 (10)	−0.0083 (9)
N2	0.0556 (14)	0.0361 (12)	0.0380 (12)	−0.0101 (10)	0.0073 (10)	−0.0092 (10)
O1	0.0798 (16)	0.0468 (12)	0.0420 (11)	−0.0253 (11)	0.0027 (10)	−0.0027 (9)
O2	0.0962 (18)	0.0416 (11)	0.0400 (12)	−0.0062 (12)	0.0159 (11)	−0.0103 (9)
O3	0.0711 (15)	0.0417 (11)	0.0552 (13)	−0.0089 (10)	0.0227 (11)	−0.0106 (10)
S1	0.0673 (6)	0.0436 (5)	0.0466 (5)	−0.0055 (4)	0.0105 (4)	−0.0144 (3)

Geometric parameters (Å, º) top

C1—C6	1.371 (4)	C10—N2	1.333 (4)
C1—C2	1.397 (4)	C10—N1	1.392 (4)
C1—Cl1	1.716 (3)	C10—S1	1.665 (3)
C2—O1	1.341 (4)	C11—C16	1.384 (4)
C2—C3	1.396 (4)	C11—C12	1.402 (4)
C3—C4	1.373 (4)	C11—N2	1.408 (4)
C3—H3	0.9300	C12—O3	1.367 (3)
C4—C5	1.395 (4)	C12—C13	1.375 (4)
C4—H4	0.9300	C13—C14	1.372 (5)
C5—C6	1.395 (4)	C13—H13	0.9300
C5—C9	1.477 (4)	C14—C15	1.369 (5)
C6—H6	0.9300	C14—H14	0.9300
C7—O1	1.448 (4)	C15—C16	1.379 (4)
C7—C8	1.492 (5)	C15—H15	0.9300
C7—H7A	0.9700	C16—H16	0.9300
C7—H7B	0.9700	C23—O3	1.402 (4)
C8—H8A	0.9600	C23—H23A	0.9600
C8—H8B	0.9600	C23—H23B	0.9600
C8—H8C	0.9600	C23—H23C	0.9600
C9—O2	1.221 (4)	N1—H1	0.8600
C9—N1	1.383 (4)	N2—H2	0.8600

C6—C1—C2	121.7 (3)	N2—C10—S1	127.6 (2)
C6—C1—Cl1	118.8 (2)	N1—C10—S1	117.5 (2)
C2—C1—Cl1	119.4 (2)	C16—C11—C12	118.5 (3)
O1—C2—C3	124.8 (3)	C16—C11—N2	127.1 (3)
O1—C2—C1	117.2 (3)	C12—C11—N2	114.4 (2)
C3—C2—C1	118.0 (3)	O3—C12—C13	124.7 (3)
C4—C3—C2	120.2 (3)	O3—C12—C11	114.4 (2)
C4—C3—H3	119.9	C13—C12—C11	120.9 (3)
C2—C3—H3	119.9	C14—C13—C12	119.7 (3)
C3—C4—C5	121.7 (3)	C14—C13—H13	120.2
C3—C4—H4	119.1	C12—C13—H13	120.2
C5—C4—H4	119.1	C15—C14—C13	120.0 (3)
C6—C5—C4	118.0 (3)	C15—C14—H14	120.0
C6—C5—C9	125.4 (3)	C13—C14—H14	120.0
C4—C5—C9	116.6 (3)	C14—C15—C16	121.1 (3)
C1—C6—C5	120.3 (3)	C14—C15—H15	119.4
C1—C6—H6	119.9	C16—C15—H15	119.4
C5—C6—H6	119.9	C15—C16—C11	119.8 (3)
O1—C7—C8	106.8 (3)	C15—C16—H16	120.1
O1—C7—H7A	110.4	C11—C16—H16	120.1
C8—C7—H7A	110.4	O3—C23—H23A	109.5
O1—C7—H7B	110.4	O3—C23—H23B	109.5
C8—C7—H7B	110.4	H23A—C23—H23B	109.5
H7A—C7—H7B	108.6	O3—C23—H23C	109.5
C7—C8—H8A	109.5	H23A—C23—H23C	109.5
C7—C8—H8B	109.5	H23B—C23—H23C	109.5
H8A—C8—H8B	109.5	C9—N1—C10	128.7 (2)
C7—C8—H8C	109.5	C9—N1—H1	115.6
H8A—C8—H8C	109.5	C10—N1—H1	115.6
H8B—C8—H8C	109.5	C10—N2—C11	132.1 (2)
O2—C9—N1	121.6 (3)	C10—N2—H2	114.0
O2—C9—C5	121.3 (3)	C11—N2—H2	114.0
N1—C9—C5	117.1 (3)	C2—O1—C7	118.0 (2)
N2—C10—N1	114.8 (2)	C12—O3—C23	118.7 (3)

C6—C1—C2—O1	179.6 (3)	O3—C12—C13—C14	179.5 (3)
Cl1—C1—C2—O1	−1.3 (4)	C11—C12—C13—C14	0.6 (5)
C6—C1—C2—C3	0.4 (5)	C12—C13—C14—C15	−0.1 (6)
Cl1—C1—C2—C3	179.5 (2)	C13—C14—C15—C16	−0.5 (6)
O1—C2—C3—C4	−178.9 (3)	C14—C15—C16—C11	0.6 (6)
C1—C2—C3—C4	0.2 (5)	C12—C11—C16—C15	−0.1 (5)
C2—C3—C4—C5	0.1 (5)	N2—C11—C16—C15	179.8 (3)
C3—C4—C5—C6	−0.9 (5)	O2—C9—N1—C10	1.6 (5)
C3—C4—C5—C9	−179.8 (3)	C5—C9—N1—C10	−178.8 (3)
C2—C1—C6—C5	−1.3 (5)	N2—C10—N1—C9	−0.9 (5)
Cl1—C1—C6—C5	179.6 (2)	S1—C10—N1—C9	−179.7 (3)
C4—C5—C6—C1	1.5 (5)	N1—C10—N2—C11	179.6 (3)
C9—C5—C6—C1	−179.8 (3)	S1—C10—N2—C11	−1.8 (5)
C6—C5—C9—O2	−169.5 (3)	C16—C11—N2—C10	−6.2 (5)
C4—C5—C9—O2	9.2 (5)	C12—C11—N2—C10	173.6 (3)
C6—C5—C9—N1	11.0 (5)	C3—C2—O1—C7	−10.3 (5)
C4—C5—C9—N1	−170.3 (3)	C1—C2—O1—C7	170.6 (3)
C16—C11—C12—O3	−179.5 (3)	C8—C7—O1—C2	−177.0 (3)
N2—C11—C12—O3	0.7 (4)	C13—C12—O3—C23	13.3 (5)
C16—C11—C12—C13	−0.5 (5)	C11—C12—O3—C23	−167.8 (3)
N2—C11—C12—C13	179.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	1.88	2.613 (3)	143
C6—H6···S1ⁱ	0.93	2.86	3.468 (2)	124
C14—H14···Cl1ⁱⁱ	0.93	2.81	3.680 (3)	156

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇ClN₂O₃S
M_r	364.84
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.8238 (8), 8.4791 (11), 14.9867 (13)
α, β, γ (°)	76.365 (7), 89.384 (5), 62.647 (4)
V (Å³)	852.65 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.38 × 0.35 × 0.27

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.874, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	4903, 3314, 2679
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.216, 1.06
No. of reflections	3314
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.85

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	1.88	2.613 (3)	143
C6—H6···S1ⁱ	0.93	2.86	3.468 (2)	124
C14—H14···Cl1ⁱⁱ	0.93	2.81	3.680 (3)	156

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

Acknowledgements

We acknowledge the support of the Colleges and Universities Graduate Advisor Research Project in Gansu Province, China (No. 0804–11)

References

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