Ethyl 3-[2-(p-tolyl­carbamothio­yl)hydrazinyl­idene]butano­ate

Zhang, Y.-L.; Hou, X.-F.; Zhang, F.-J.; Yang, F.-L.

doi:10.1107/S160053681004290X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2971

https://doi.org/10.1107/S160053681004290X

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Ethyl 3-[2-(p-tolylcarbamothioyl)hydrazinylidene]butanoate

Yan-Ling Zhang,^a Xu-Feng Hou,^a Fu-Juan Zhang ^a and Feng-Ling Yang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Xuchang University, Henan 461000, People's Republic of China
^*Correspondence e-mail: zhangyanling315@126.com

(Received 20 October 2010; accepted 21 October 2010; online 30 October 2010)

The title compound, C₁₄H₁₉N₃O₂S, was obtained from a condensation reaction of N-(p-tolyl)hydrazinecarbothioamide and ethyl acetoacetate. The molecule assumes an E configuration; the thiosemicarbazide and ester groups are located on the opposite sides of the C=N bond. The almost planar thiosemicarbazide unit (r.m.s. deviation = 0.0130 Å) is tilted at a dihedral angle of 49.54 (12)° with respect to the benzene ring. Intermolecular N—H⋯N and N—H⋯S hydrogen bonding stabilizes the crystal structure. The ethoxy group of the ester unit is disordered over two positions, with a site-occupancy ratio of 0.680 (10):0.320 (10).

Related literature

For biological applications of thiosemicarbazones, see: Okabe et al. (1993 ); Hu et al. (2006 ). For related structures, see: Zhang et al. (2005 ); Shan & Zhang (2006 ).

Experimental

Crystal data

C₁₄H₁₉N₃O₂S
M_r = 293.38
Orthorhombic, I b c a
a = 14.1747 (3) Å
b = 25.1439 (4) Å
c = 17.4381 (2) Å
V = 6215.08 (17) Å³
Z = 16
Cu Kα radiation
μ = 1.90 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.703, T_max = 0.726
6852 measured reflections
2775 independent reflections
2380 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.175
S = 1.07
2775 reflections
199 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N3ⁱ	0.81 (3)	2.54 (3)	3.300 (3)	155 (2)
N2—H2B⋯S1ⁱⁱ	0.86	2.85	3.5572 (18)	141
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y, -z+1]$ ; (ii) $[x, -y+1, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; 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: https://doi.org/10.1107/S160053681004290X/xu5056sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004290X/xu5056Isup2.hkl

checkCIF report

Comment top

Thiosemicarbazones have attracted much attention as they show potential application in the biological field (Okabe et al., 1993; Hu et al., 2006). There are a few single-crystal reports about them (Zhang et al., 2005; Shan et al., 2006). Detailed information on their molecular and crystal structures is necessary to understand their anticancer activity. The molecular structure of (I) is shown in Fig 1. The molecule of (I) exhibits an E configuration. The thiosemicarbazide and Ethyl acetoacetate unit are located on opposite sides of the N3=C9 bond. The thiosemicarbazide unit has a planar configuration and is tilted with respect to the p-methylphenyl mean plane, forming a dihedral angle of 49.54 (12)°.In the crystal structure of the title compound, there are N(1)—H(1 N)···N(3)#1, N(1)—H(1 N)···N(1)#1 and N(2)—H(2B)···S(1)#2 hydrogen-bond interactions in molecules (Fig. 2).

Related literature top

For biological applications of thiosemicarbazones, see: Okabe et al. (1993); Hu et al. (2006). For related structures, see: Zhang et al. (2005); Shan & Zhang (2006).

Experimental top

N-(p-Tolyl)thiosemicarbazide (1.8 g,10 mmol) and ethyl acetoacetate (1.3 g, 10 mmol) was dissolved in 95% ethanol (15 ml) and the solution was refluxed for 2 h. Fine colorless crystals appeared on cooling. They were filtered and washed by 95% ethanol to give 2.13 g of the title compound in 71.7% yield. Single crystals suitable for X-ray measurements were obtained from mother liquid by slow evaporation at room temperature.

Structure description top

For biological applications of thiosemicarbazones, see: Okabe et al. (1993); Hu et al. (2006). For related structures, see: Zhang et al. (2005); Shan & Zhang (2006).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); 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, with displacement ellipsoids drawn at 30% probability level.
	Fig. 2. The packing diagram of the title compound. Intermolecular hydrogen bonds are shown as dashed line.

Ethyl 3-[2-(p-tolylcarbamothioyl)hydrazinylidene]butanoate top

Crystal data top

C₁₄H₁₉N₃O₂S	F(000) = 2496
M_r = 293.38	D_x = 1.254 Mg m⁻³
Orthorhombic, Ibca	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -I 2b 2c	Cell parameters from 4042 reflections
a = 14.1747 (3) Å	θ = 3.1–72.2°
b = 25.1439 (4) Å	µ = 1.90 mm⁻¹
c = 17.4381 (2) Å	T = 293 K
V = 6215.08 (17) Å³	Prismatic, colorless
Z = 16	0.20 × 0.18 × 0.18 mm

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2775 independent reflections
Radiation source: fine-focus sealed tube	2380 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 67.0°, θ_min = 3.5°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −16→13
T_min = 0.703, T_max = 0.726	k = −30→29
6852 measured reflections	l = −20→10

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.111P)² + 3.488P] where P = (F_o² + 2F_c²)/3
2775 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₄H₁₉N₃O₂S	V = 6215.08 (17) Å³
M_r = 293.38	Z = 16
Orthorhombic, Ibca	Cu Kα radiation
a = 14.1747 (3) Å	µ = 1.90 mm⁻¹
b = 25.1439 (4) Å	T = 293 K
c = 17.4381 (2) Å	0.20 × 0.18 × 0.18 mm

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2775 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2380 reflections with I > 2σ(I)
T_min = 0.703, T_max = 0.726	R_int = 0.018
6852 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.33 e Å⁻³
2775 reflections	Δρ_min = −0.37 e Å⁻³
199 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	Occ. (<1)
S1	0.89584 (5)	0.56086 (3)	0.67758 (3)	0.0567 (3)
N1	0.84677 (12)	0.51980 (8)	0.54081 (10)	0.0426 (4)
N2	0.78883 (13)	0.47864 (8)	0.64691 (10)	0.0468 (5)
H2B	0.7853	0.4742	0.6957	0.056*
N3	0.74049 (14)	0.44509 (7)	0.59763 (10)	0.0456 (5)
C1	0.88957 (13)	0.55867 (8)	0.49298 (12)	0.0405 (5)
C2	0.93995 (16)	0.54086 (9)	0.42997 (11)	0.0449 (5)
H2A	0.9461	0.5046	0.4210	0.054*
C3	0.98110 (17)	0.57697 (10)	0.38031 (13)	0.0521 (6)
H3A	1.0146	0.5646	0.3381	0.063*
C4	0.97320 (18)	0.63105 (10)	0.39238 (14)	0.0569 (6)
C5	0.9206 (2)	0.64823 (10)	0.45486 (15)	0.0595 (6)
H5A	0.9137	0.6845	0.4636	0.071*
C6	0.87831 (18)	0.61255 (10)	0.50432 (14)	0.0513 (5)
H6A	0.8423	0.6249	0.5452	0.062*
C7	1.0220 (3)	0.66988 (14)	0.33947 (19)	0.0859 (10)
H7A	1.0114	0.7055	0.3573	0.129*
H7B	0.9970	0.6662	0.2886	0.129*
H7C	1.0885	0.6627	0.3389	0.129*
C8	0.84189 (14)	0.51858 (9)	0.61720 (11)	0.0420 (5)
C9	0.68544 (16)	0.41050 (9)	0.62652 (13)	0.0479 (5)
C10	0.6300 (2)	0.37820 (11)	0.56998 (17)	0.0627 (7)
H10A	0.6424	0.3924	0.5193	0.075*
H10B	0.5636	0.3838	0.5805	0.075*
C11	0.6470 (3)	0.31894 (13)	0.56713 (19)	0.0735 (8)
C12	0.6676 (2)	0.40351 (14)	0.71046 (17)	0.0765 (9)
H12A	0.7242	0.3913	0.7350	0.115*
H12B	0.6183	0.3778	0.7178	0.115*
H12C	0.6489	0.4369	0.7324	0.115*
O1	0.6285 (3)	0.29160 (13)	0.5138 (2)	0.1299 (13)
C13	0.7213 (7)	0.2436 (2)	0.6246 (4)	0.113 (3)	0.680 (10)
H13A	0.7212	0.2299	0.5726	0.135*	0.680 (10)
H13B	0.7831	0.2372	0.6466	0.135*	0.680 (10)
C14	0.6501 (10)	0.2163 (3)	0.6696 (5)	0.143 (4)	0.680 (10)
H14A	0.6632	0.1789	0.6701	0.214*	0.680 (10)
H14B	0.5891	0.2224	0.6473	0.214*	0.680 (10)
H14C	0.6509	0.2297	0.7211	0.214*	0.680 (10)
O2	0.7016 (4)	0.30089 (13)	0.6237 (2)	0.0891 (18)	0.680 (10)
C13'	0.6327 (18)	0.2371 (11)	0.6442 (15)	0.138 (8)*	0.320 (10)
H13C	0.6033	0.2200	0.6005	0.165*	0.320 (10)
H13D	0.5973	0.2272	0.6896	0.165*	0.320 (10)
C14'	0.7322 (16)	0.2172 (10)	0.6520 (14)	0.137 (7)*	0.320 (10)
H14D	0.7318	0.1792	0.6561	0.206*	0.320 (10)
H14E	0.7603	0.2322	0.6972	0.206*	0.320 (10)
H14F	0.7680	0.2276	0.6078	0.206*	0.320 (10)
O2'	0.6275 (10)	0.2960 (5)	0.6341 (7)	0.115 (4)*	0.320 (10)
H1N	0.8246 (18)	0.4946 (12)	0.5181 (15)	0.046 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0723 (5)	0.0606 (4)	0.0371 (4)	−0.0171 (3)	−0.0054 (2)	−0.0039 (2)
N1	0.0470 (9)	0.0466 (10)	0.0342 (9)	−0.0067 (8)	−0.0016 (7)	−0.0005 (7)
N2	0.0538 (10)	0.0543 (11)	0.0322 (8)	−0.0077 (8)	0.0016 (7)	0.0029 (7)
N3	0.0515 (10)	0.0467 (10)	0.0386 (9)	−0.0045 (8)	−0.0002 (8)	0.0017 (7)
C1	0.0393 (10)	0.0482 (11)	0.0341 (10)	−0.0022 (8)	−0.0036 (7)	0.0046 (8)
C2	0.0517 (11)	0.0466 (11)	0.0365 (10)	−0.0001 (9)	0.0001 (9)	0.0009 (8)
C3	0.0532 (12)	0.0639 (14)	0.0392 (11)	−0.0003 (11)	0.0042 (9)	0.0060 (10)
C4	0.0628 (14)	0.0594 (14)	0.0486 (12)	−0.0090 (12)	−0.0029 (11)	0.0148 (10)
C5	0.0755 (15)	0.0432 (12)	0.0599 (14)	0.0016 (11)	−0.0050 (12)	0.0069 (10)
C6	0.0582 (12)	0.0512 (12)	0.0447 (11)	0.0072 (10)	0.0020 (10)	0.0012 (10)
C7	0.105 (3)	0.080 (2)	0.0724 (18)	−0.0259 (19)	0.0066 (18)	0.0257 (16)
C8	0.0431 (10)	0.0485 (11)	0.0343 (10)	0.0003 (8)	−0.0005 (8)	0.0004 (8)
C9	0.0478 (11)	0.0475 (11)	0.0483 (12)	−0.0010 (9)	0.0000 (9)	0.0068 (9)
C10	0.0680 (15)	0.0528 (14)	0.0674 (16)	−0.0119 (12)	−0.0098 (13)	0.0079 (12)
C11	0.087 (2)	0.0642 (17)	0.0695 (17)	−0.0118 (15)	−0.0066 (15)	−0.0055 (14)
C12	0.0829 (19)	0.090 (2)	0.0560 (15)	−0.0268 (17)	0.0156 (14)	0.0096 (14)
O1	0.172 (3)	0.098 (2)	0.120 (2)	0.027 (2)	−0.048 (2)	−0.0389 (19)
C13	0.166 (7)	0.061 (3)	0.111 (5)	0.016 (4)	0.012 (5)	0.013 (3)
C14	0.250 (13)	0.073 (4)	0.106 (5)	−0.010 (6)	0.047 (7)	0.013 (4)
O2	0.130 (4)	0.0540 (18)	0.083 (2)	0.0084 (19)	−0.021 (2)	0.0044 (15)

Geometric parameters (Å, º) top

S1—C8	1.680 (2)	C10—C11	1.510 (4)
N1—C8	1.334 (3)	C10—H10A	0.9700
N1—C1	1.421 (3)	C10—H10B	0.9700
N1—H1N	0.81 (3)	C11—O1	1.186 (4)
N2—C8	1.357 (3)	C11—O2'	1.332 (12)
N2—N3	1.386 (3)	C11—O2	1.333 (5)
N2—H2B	0.8600	C12—H12A	0.9600
N3—C9	1.272 (3)	C12—H12B	0.9600
C1—C6	1.378 (3)	C12—H12C	0.9600
C1—C2	1.385 (3)	C13—C14	1.450 (13)
C2—C3	1.384 (3)	C13—O2	1.468 (7)
C2—H2A	0.9300	C13—H13A	0.9700
C3—C4	1.381 (4)	C13—H13B	0.9700
C3—H3A	0.9300	C14—H14A	0.9600
C4—C5	1.389 (4)	C14—H14B	0.9600
C4—C7	1.511 (3)	C14—H14C	0.9600
C5—C6	1.381 (4)	C13'—O2'	1.49 (3)
C5—H5A	0.9300	C13'—C14'	1.50 (4)
C6—H6A	0.9300	C13'—H13C	0.9700
C7—H7A	0.9600	C13'—H13D	0.9700
C7—H7B	0.9600	C14'—H14D	0.9600
C7—H7C	0.9600	C14'—H14E	0.9600
C9—C12	1.496 (3)	C14'—H14F	0.9600
C9—C10	1.500 (4)

C8—N1—C1	128.61 (19)	C11—C10—H10B	107.8
C8—N1—H1N	116.7 (18)	H10A—C10—H10B	107.1
C1—N1—H1N	114.7 (18)	O1—C11—O2'	113.0 (6)
C8—N2—N3	119.19 (16)	O1—C11—O2	120.8 (4)
C8—N2—H2B	120.4	O2'—C11—O2	47.5 (6)
N3—N2—H2B	120.4	O1—C11—C10	124.2 (3)
C9—N3—N2	118.29 (19)	O2'—C11—C10	111.4 (6)
C6—C1—C2	119.4 (2)	O2—C11—C10	113.8 (3)
C6—C1—N1	122.8 (2)	C9—C12—H12A	109.5
C2—C1—N1	117.6 (2)	C9—C12—H12B	109.5
C3—C2—C1	120.1 (2)	H12A—C12—H12B	109.5
C3—C2—H2A	119.9	C9—C12—H12C	109.5
C1—C2—H2A	119.9	H12A—C12—H12C	109.5
C4—C3—C2	121.1 (2)	H12B—C12—H12C	109.5
C4—C3—H3A	119.4	C14—C13—O2	109.7 (8)
C2—C3—H3A	119.4	C14—C13—H13A	109.7
C3—C4—C5	118.0 (2)	O2—C13—H13A	109.7
C3—C4—C7	120.4 (3)	C14—C13—H13B	109.7
C5—C4—C7	121.6 (3)	O2—C13—H13B	109.7
C6—C5—C4	121.4 (2)	H13A—C13—H13B	108.2
C6—C5—H5A	119.3	C13—C14—H14A	109.5
C4—C5—H5A	119.3	C13—C14—H14B	109.5
C1—C6—C5	119.9 (2)	H14A—C14—H14B	109.5
C1—C6—H6A	120.0	C13—C14—H14C	109.5
C5—C6—H6A	120.0	H14A—C14—H14C	109.5
C4—C7—H7A	109.5	H14B—C14—H14C	109.5
C4—C7—H7B	109.5	C11—O2—C13	116.9 (5)
H7A—C7—H7B	109.5	O2'—C13'—C14'	113 (2)
C4—C7—H7C	109.5	O2'—C13'—H13C	109.0
H7A—C7—H7C	109.5	C14'—C13'—H13C	109.0
H7B—C7—H7C	109.5	O2'—C13'—H13D	109.0
N1—C8—N2	115.26 (19)	C14'—C13'—H13D	109.0
N1—C8—S1	125.98 (17)	H13C—C13'—H13D	107.8
N2—C8—S1	118.75 (15)	C13'—C14'—H14D	109.5
N3—C9—C12	124.8 (2)	C13'—C14'—H14E	109.5
N3—C9—C10	115.5 (2)	H14D—C14'—H14E	109.5
C12—C9—C10	119.4 (2)	C13'—C14'—H14F	109.5
C9—C10—C11	118.2 (2)	H14D—C14'—H14F	109.5
C9—C10—H10A	107.8	H14E—C14'—H14F	109.5
C11—C10—H10A	107.8	C11—O2'—C13'	121.6 (14)
C9—C10—H10B	107.8

C8—N2—N3—C9	−174.7 (2)	N3—N2—C8—S1	176.99 (15)
C8—N1—C1—C6	−44.9 (3)	N2—N3—C9—C12	0.8 (4)
C8—N1—C1—C2	138.9 (2)	N2—N3—C9—C10	175.7 (2)
C6—C1—C2—C3	2.1 (3)	N3—C9—C10—C11	116.9 (3)
N1—C1—C2—C3	178.3 (2)	C12—C9—C10—C11	−67.9 (4)
C1—C2—C3—C4	0.2 (3)	C9—C10—C11—O1	−158.9 (4)
C2—C3—C4—C5	−1.6 (4)	C9—C10—C11—O2'	60.4 (7)
C2—C3—C4—C7	177.4 (2)	C9—C10—C11—O2	8.7 (5)
C3—C4—C5—C6	0.9 (4)	O1—C11—O2—C13	−11.8 (7)
C7—C4—C5—C6	−178.2 (3)	O2'—C11—O2—C13	82.2 (9)
C2—C1—C6—C5	−2.8 (3)	C10—C11—O2—C13	−180.0 (5)
N1—C1—C6—C5	−178.9 (2)	C14—C13—O2—C11	−90.3 (9)
C4—C5—C6—C1	1.3 (4)	O1—C11—O2'—C13'	30.6 (18)
C1—N1—C8—N2	174.30 (19)	O2—C11—O2'—C13'	−80.9 (16)
C1—N1—C8—S1	−6.5 (3)	C10—C11—O2'—C13'	175.9 (14)
N3—N2—C8—N1	−3.8 (3)	C14'—C13'—O2'—C11	77 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N3ⁱ	0.81 (3)	2.54 (3)	3.300 (3)	155 (2)
N2—H2B···S1ⁱⁱ	0.86	2.85	3.5572 (18)	141

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₉N₃O₂S
M_r	293.38
Crystal system, space group	Orthorhombic, Ibca
Temperature (K)	293
a, b, c (Å)	14.1747 (3), 25.1439 (4), 17.4381 (2)
V (Å³)	6215.08 (17)
Z	16
Radiation type	Cu Kα
µ (mm⁻¹)	1.90
Crystal size (mm)	0.20 × 0.18 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.703, 0.726
No. of measured, independent and observed [I > 2σ(I)] reflections	6852, 2775, 2380
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.175, 1.07
No. of reflections	2775
No. of parameters	199
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.37

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N3ⁱ	0.81 (3)	2.54 (3)	3.300 (3)	155 (2)
N2—H2B···S1ⁱⁱ	0.86	2.85	3.5572 (18)	141

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

Acknowledgements

The authors thank the Natural Science Foundation of the Education Department of Henan Province, China (2010B150029) and the Science and Technique Foundation of Henan Province, China (0624290013, 082300420110) for supporting this work.

References

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