O,O′-Dimethyl (cyclo­hexyl­amido)­thio­phosphate

Sabbaghi, F.; Pourayoubi, M.; Nečas, M.

doi:10.1107/S160053681203766X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2891

https://doi.org/10.1107/S160053681203766X

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O,O′-Dimethyl (cyclohexylamido)thiophosphate

Fahimeh Sabbaghi,^a ^* Mehrdad Pourayoubi ^b and Marek Nečas ^c

^aDepartment of Chemistry, Zanjan Branch, Islamic Azad University, Zanjan, Iran, ^bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran, and ^cDepartment of Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, Brno CZ-61137, Czech Republic
^*Correspondence e-mail: fahimeh_sabbaghi@yahoo.com

(Received 5 August 2012; accepted 1 September 2012; online 8 September 2012)

The P atom in the title compound, C₈H₁₈NO₂PS, is bonded in a distorted tetrahedral PSO₂N environment with bond angles in the range of 99.23 (5)–115.17 (4)°. The cyclohexane ring is disordered over two sets of sites with refined occupancies of 0.528 (5) and 0.472 (5). The ring in both disorder components adopts a chair conformation with the N—H group oriented equatorially. In the crystal, pairs of P=S⋯H—N hydrogen bonds form inversion dimers.

Related literature

For related structures, see: Chivers et al. (2003 ); Balazs et al. (1999 ); García-Hernández et al. (2006 ). For compounds with a P(S)(N)(O)₂ skeleton, see: García-Hernández et al. (2006). For the distorted tetrahedral configuration of phosphoramidates and their chalco-derivatives, see: Rudd et al. (1996 ).

Experimental

Crystal data

C₈H₁₈NO₂PS
M_r = 223.26
Triclinic, $[P \overline 1]$
a = 6.5214 (4) Å
b = 9.2078 (6) Å
c = 10.5763 (7) Å
α = 67.447 (6)°
β = 80.212 (5)°
γ = 78.863 (5)°
V = 572.24 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 120 K
0.50 × 0.50 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.942, T_max = 1.000
3413 measured reflections
2017 independent reflections
1731 reflections with I > 2σ(I)
R_int = 0.011

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.069
S = 1.07
2017 reflections
170 parameters
163 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯S1ⁱ	0.791 (16)	2.695 (17)	3.4633 (13)	164.3 (14)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681203766X/lh5513sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681203766X/lh5513Isup2.hkl

checkCIF report

Comment top

The structure determination of the title compound (Fig. 1) was performed as a part of a project on the synthesis of a new phosphorus(V)-nitrogen compound belonging to the family of phosphoramidothioate with potential applications as S-donor ligands, similar to those observed for reported compounds with a P═S bond (Chivers et al., 2003; Balazs et al., 1999; García-Hernández et al., 2006).

The P═S (1.9351 (5) Å), P—O (1.5823 (10) and 1.5853 (9) Å) and P—N (1.6153 (12) Å) bond lengths are within the expected values for compounds with a P(S)(N)(O)₂ skeleton (García-Hernández et al., 2006).

The P atom has a distorted tetrahedral configuration (Fig. 1) as it has been noted for phosphoramidates and their chalco-derivatives (Rudd et al., 1996). The bond angles at the P atom vary in the range 99.23 (5) [O1—P1—O2] to 115.17 (4)° [O1—P1—S1]. The C—O—P bond angles are 120.01 (9) [C1—O1—P1] and 119.12 (9)° [C2—O2—P1]. In the crystal, inversion dimers are formed by pairs of P═S···H—N hydrogen bonds, Table 1 and Fig. 2.

Related literature top

For related structures, see: Chivers et al. (2003); Balazs et al. (1999); García-Hernández et al. (2006). For compounds with a P(S)(N)(O)₂ skeleton, see: García-Hernández et al. (2006). For the distorted tetrahedral configuration of phosphoramidates and their chalco-derivatives, see: Rudd et al. (1996).

Experimental top

To a solution of [CH₃O]₂P(S)Cl (1.7 mmol) in dry CH₃CN (30 ml), a solution of cyclohexylamine (3.4 mmol) in the same solvent (5 ml) was added at ice bath temperature. After 4 h stirring, the solvent was removed and the product was washed with distilled water and recrystallized from methanol at room temperature. The single crystals, suitable for X-ray analysis were obtained from this solution after a few days at room temperature.

Structure description top

For related structures, see: Chivers et al. (2003); Balazs et al. (1999); García-Hernández et al. (2006). For compounds with a P(S)(N)(O)₂ skeleton, see: García-Hernández et al. (2006). For the distorted tetrahedral configuration of phosphoramidates and their chalco-derivatives, see: Rudd et al. (1996).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Figures top

	Fig. 1. The molecular structure of the title compound with ellipsoids shown at the 50% probability level and H atoms are drawn as small spheres of arbitrary radii. The minor component of disordered part has been omitted for clarity and only one orientation is shown for the disordered cyclohexyl group.
	Fig. 2. Pair of P═S···H—N hydrogen bonds (shown as dotted lines) in the hydrogen-bonded dimer. The H atoms not involved in hydrogen bonding have been omitted for clarity.

O,O'-Dimethyl (cyclohexylamido)thiophosphate top

Crystal data top

C₈H₁₈NO₂PS	Z = 2
M_r = 223.26	F(000) = 240
Triclinic, P1	D_x = 1.296 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5214 (4) Å	Cell parameters from 2495 reflections
b = 9.2078 (6) Å	θ = 3.2–27.7°
c = 10.5763 (7) Å	µ = 0.40 mm⁻¹
α = 67.447 (6)°	T = 120 K
β = 80.212 (5)°	Prism, colourless
γ = 78.863 (5)°	0.50 × 0.50 × 0.30 mm
V = 572.24 (6) Å³

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	2017 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1731 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
Detector resolution: 8.4353 pixels mm^-1	θ_max = 25.0°, θ_min = 3.2°
ω scan	h = −6→7
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −10→10
T_min = 0.942, T_max = 1.000	l = −11→12
3413 measured reflections

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0424P)²] where P = (F_o² + 2F_c²)/3
2017 reflections	(Δ/σ)_max < 0.001
170 parameters	Δρ_max = 0.21 e Å⁻³
163 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₈H₁₈NO₂PS	γ = 78.863 (5)°
M_r = 223.26	V = 572.24 (6) Å³
Triclinic, P1	Z = 2
a = 6.5214 (4) Å	Mo Kα radiation
b = 9.2078 (6) Å	µ = 0.40 mm⁻¹
c = 10.5763 (7) Å	T = 120 K
α = 67.447 (6)°	0.50 × 0.50 × 0.30 mm
β = 80.212 (5)°

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	2017 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1731 reflections with I > 2σ(I)
T_min = 0.942, T_max = 1.000	R_int = 0.011
3413 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	163 restraints
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.21 e Å⁻³
2017 reflections	Δρ_min = −0.33 e Å⁻³
170 parameters

Special details top

Experimental. IR (KBr, cm^-1): 3298, 2924, 2852, 1441, 1296, 1237, 1189, 1096, 1043, 926, 800, 644.

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	0.70121 (6)	−0.24913 (4)	0.59384 (4)	0.02256 (13)
P1	0.79402 (5)	−0.18144 (4)	0.39881 (4)	0.01557 (12)
O1	0.71651 (15)	−0.27186 (11)	0.31916 (10)	0.0220 (3)
O2	1.03994 (14)	−0.21705 (11)	0.36207 (10)	0.0185 (2)
N1	0.7238 (2)	0.00511 (14)	0.31544 (13)	0.0186 (3)
C1	0.7583 (3)	−0.44339 (18)	0.36569 (19)	0.0353 (4)
H1B	0.6703	−0.4816	0.3219	0.053*
H1C	0.7260	−0.4884	0.4659	0.053*
H1D	0.9068	−0.4763	0.3407	0.053*
C2	1.1800 (2)	−0.15705 (18)	0.41653 (17)	0.0270 (4)
H2A	1.3260	−0.1927	0.3884	0.041*
H2B	1.1550	−0.1971	0.5173	0.041*
H2C	1.1541	−0.0407	0.3809	0.041*
C3A	0.7713 (2)	0.08687 (16)	0.16597 (15)	0.0193 (3)
H3A	0.8465	0.0061	0.1261	0.023*	0.528 (5)
C4A	0.5781 (5)	0.1703 (6)	0.0909 (3)	0.0248 (9)	0.528 (5)
H4A1	0.4971	0.2458	0.1332	0.030*	0.528 (5)
H4A2	0.4873	0.0906	0.1020	0.030*	0.528 (5)
C5A	0.6336 (6)	0.2606 (7)	−0.0631 (4)	0.0305 (12)	0.528 (5)
H5A1	0.7026	0.1841	−0.1076	0.037*	0.528 (5)
H5A2	0.5031	0.3161	−0.1064	0.037*	0.528 (5)
C6A	0.7785 (8)	0.3804 (5)	−0.0864 (4)	0.0309 (11)	0.528 (5)
H6A1	0.7043	0.4631	−0.0501	0.037*	0.528 (5)
H6A2	0.8168	0.4328	−0.1865	0.037*	0.528 (5)
C7A	0.9772 (7)	0.3018 (4)	−0.0158 (4)	0.0251 (9)	0.528 (5)
H7A1	1.0658	0.3835	−0.0290	0.030*	0.528 (5)
H7A2	1.0585	0.2260	−0.0578	0.030*	0.528 (5)
C8A	0.9216 (7)	0.2137 (5)	0.1383 (4)	0.0235 (9)	0.528 (5)
H8A1	0.8522	0.2914	0.1814	0.028*	0.528 (5)
H8A2	1.0524	0.1596	0.1818	0.028*	0.528 (5)
H3B	0.8963	0.0240	0.1326	0.023*	0.472 (5)
C4B	0.5791 (6)	0.0888 (6)	0.0963 (4)	0.0202 (9)	0.472 (5)
H4B1	0.5555	−0.0214	0.1169	0.024*	0.472 (5)
H4B2	0.4515	0.1442	0.1329	0.024*	0.472 (5)
C5B	0.6199 (7)	0.1738 (6)	−0.0588 (4)	0.0237 (10)	0.472 (5)
H5B1	0.7365	0.1106	−0.0964	0.028*	0.472 (5)
H5B2	0.4929	0.1831	−0.1025	0.028*	0.472 (5)
C6B	0.6762 (10)	0.3388 (6)	−0.0932 (5)	0.0257 (12)	0.472 (5)
H6B1	0.7101	0.3888	−0.1940	0.031*	0.472 (5)
H6B2	0.5536	0.4057	−0.0646	0.031*	0.472 (5)
C7B	0.8621 (10)	0.3311 (6)	−0.0215 (5)	0.0299 (11)	0.472 (5)
H7B1	0.8908	0.4402	−0.0426	0.036*	0.472 (5)
H7B2	0.9880	0.2730	−0.0569	0.036*	0.472 (5)
C8B	0.8214 (9)	0.2479 (5)	0.1350 (4)	0.0250 (10)	0.472 (5)
H8B1	0.9475	0.2403	0.1789	0.030*	0.472 (5)
H8B2	0.7026	0.3100	0.1722	0.030*	0.472 (5)
H1N	0.634 (2)	0.0509 (18)	0.3521 (16)	0.021 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0223 (2)	0.0192 (2)	0.0187 (2)	0.00165 (15)	0.00233 (15)	−0.00272 (16)
P1	0.0129 (2)	0.0147 (2)	0.0178 (2)	0.00016 (14)	−0.00189 (15)	−0.00541 (16)
O1	0.0211 (5)	0.0169 (5)	0.0302 (6)	0.0007 (4)	−0.0100 (5)	−0.0095 (5)
O2	0.0130 (5)	0.0207 (5)	0.0226 (6)	−0.0006 (4)	−0.0017 (4)	−0.0097 (4)
N1	0.0186 (6)	0.0164 (7)	0.0174 (7)	0.0025 (5)	0.0009 (5)	−0.0060 (5)
C1	0.0376 (10)	0.0200 (9)	0.0541 (12)	0.0017 (7)	−0.0183 (9)	−0.0170 (8)
C2	0.0171 (8)	0.0286 (9)	0.0380 (10)	−0.0048 (6)	−0.0065 (7)	−0.0126 (8)
C3A	0.0214 (8)	0.0181 (8)	0.0163 (8)	0.0006 (6)	−0.0008 (6)	−0.0059 (6)
C4A	0.0235 (16)	0.030 (2)	0.0192 (16)	−0.0038 (17)	−0.0037 (12)	−0.0069 (17)
C5A	0.026 (2)	0.044 (4)	0.0176 (19)	−0.005 (3)	−0.0063 (15)	−0.005 (2)
C6A	0.031 (3)	0.026 (2)	0.023 (2)	−0.0014 (19)	0.0021 (18)	0.0004 (16)
C7A	0.027 (2)	0.0221 (18)	0.0242 (18)	−0.0088 (17)	0.0028 (18)	−0.0068 (14)
C8A	0.026 (2)	0.021 (2)	0.0226 (17)	−0.0055 (17)	−0.0026 (18)	−0.0059 (14)
C3B	0.0214 (8)	0.0181 (8)	0.0163 (8)	0.0006 (6)	−0.0008 (6)	−0.0059 (6)
C4B	0.0229 (17)	0.017 (2)	0.0189 (18)	−0.0018 (18)	−0.0045 (13)	−0.0045 (17)
C5B	0.031 (2)	0.021 (2)	0.0209 (18)	−0.0037 (18)	−0.0053 (14)	−0.0081 (18)
C6B	0.038 (3)	0.017 (3)	0.018 (2)	−0.005 (2)	−0.003 (2)	−0.0017 (19)
C7B	0.037 (3)	0.024 (2)	0.028 (2)	−0.015 (2)	−0.004 (2)	−0.0028 (18)
C8B	0.031 (3)	0.021 (2)	0.0230 (19)	−0.007 (2)	−0.006 (2)	−0.0051 (16)

Geometric parameters (Å, º) top

S1—P1	1.9351 (5)	C6A—C7A	1.521 (5)
P1—O1	1.5823 (10)	C6A—H6A1	0.9900
P1—O2	1.5853 (9)	C6A—H6A2	0.9900
P1—N1	1.6153 (12)	C7A—C8A	1.531 (5)
O1—C1	1.4471 (18)	C7A—H7A1	0.9900
O2—C2	1.4456 (17)	C7A—H7A2	0.9900
N1—C3A	1.4739 (18)	C8A—H8A1	0.9900
N1—H1N	0.791 (16)	C8A—H8A2	0.9900
C1—H1B	0.9800	C4B—C5B	1.523 (5)
C1—H1C	0.9800	C4B—H4B1	0.9900
C1—H1D	0.9800	C4B—H4B2	0.9900
C2—H2A	0.9800	C5B—C6B	1.523 (5)
C2—H2B	0.9800	C5B—H5B1	0.9900
C2—H2C	0.9800	C5B—H5B2	0.9900
C3A—C4A	1.519 (4)	C6B—C7B	1.513 (6)
C3A—C8A	1.578 (4)	C6B—H6B1	0.9900
C3A—H3A	1.0000	C6B—H6B2	0.9900
C4A—C5A	1.533 (5)	C7B—C8B	1.534 (6)
C4A—H4A1	0.9900	C7B—H7B1	0.9900
C4A—H4A2	0.9900	C7B—H7B2	0.9900
C5A—C6A	1.512 (6)	C8B—H8B1	0.9900
C5A—H5A1	0.9900	C8B—H8B2	0.9900
C5A—H5A2	0.9900

O1—P1—O2	99.23 (5)	C5A—C6A—H6A1	109.4
O1—P1—N1	105.48 (6)	C7A—C6A—H6A1	109.4
O2—P1—N1	107.01 (6)	C5A—C6A—H6A2	109.4
O1—P1—S1	115.17 (4)	C7A—C6A—H6A2	109.4
O2—P1—S1	114.80 (4)	H6A1—C6A—H6A2	108.0
N1—P1—S1	113.73 (5)	C6A—C7A—C8A	110.4 (3)
C1—O1—P1	120.01 (9)	C6A—C7A—H7A1	109.6
C2—O2—P1	119.12 (9)	C8A—C7A—H7A1	109.6
C3A—N1—P1	124.89 (10)	C6A—C7A—H7A2	109.6
C3A—N1—H1N	115.6 (11)	C8A—C7A—H7A2	109.6
P1—N1—H1N	117.5 (11)	H7A1—C7A—H7A2	108.1
O1—C1—H1B	109.5	C7A—C8A—C3A	112.0 (3)
O1—C1—H1C	109.5	C7A—C8A—H8A1	109.2
H1B—C1—H1C	109.5	C3A—C8A—H8A1	109.2
O1—C1—H1D	109.5	C7A—C8A—H8A2	109.2
H1B—C1—H1D	109.5	C3A—C8A—H8A2	109.2
H1C—C1—H1D	109.5	H8A1—C8A—H8A2	107.9
O2—C2—H2A	109.5	C5B—C4B—H4B1	109.8
O2—C2—H2B	109.5	C5B—C4B—H4B2	109.8
H2A—C2—H2B	109.5	H4B1—C4B—H4B2	108.3
O2—C2—H2C	109.5	C6B—C5B—C4B	111.1 (3)
H2A—C2—H2C	109.5	C6B—C5B—H5B1	109.4
H2B—C2—H2C	109.5	C4B—C5B—H5B1	109.4
N1—C3A—C4A	113.92 (16)	C6B—C5B—H5B2	109.4
N1—C3A—C8A	109.76 (17)	C4B—C5B—H5B2	109.4
C4A—C3A—C8A	108.4 (2)	H5B1—C5B—H5B2	108.0
N1—C3A—H3A	108.2	C7B—C6B—C5B	111.3 (4)
C4A—C3A—H3A	108.2	C7B—C6B—H6B1	109.4
C8A—C3A—H3A	108.2	C5B—C6B—H6B1	109.4
C3A—C4A—C5A	112.6 (3)	C7B—C6B—H6B2	109.4
C3A—C4A—H4A1	109.1	C5B—C6B—H6B2	109.4
C5A—C4A—H4A1	109.1	H6B1—C6B—H6B2	108.0
C3A—C4A—H4A2	109.1	C6B—C7B—C8B	111.5 (4)
C5A—C4A—H4A2	109.1	C6B—C7B—H7B1	109.3
H4A1—C4A—H4A2	107.8	C8B—C7B—H7B1	109.3
C6A—C5A—C4A	111.4 (3)	C6B—C7B—H7B2	109.3
C6A—C5A—H5A1	109.3	C8B—C7B—H7B2	109.3
C4A—C5A—H5A1	109.3	H7B1—C7B—H7B2	108.0
C6A—C5A—H5A2	109.3	C7B—C8B—H8B1	109.8
C4A—C5A—H5A2	109.3	C7B—C8B—H8B2	109.8
H5A1—C5A—H5A2	108.0	H8B1—C8B—H8B2	108.3
C5A—C6A—C7A	111.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1ⁱ	0.791 (16)	2.695 (17)	3.4633 (13)	164.3 (14)

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₈H₁₈NO₂PS
M_r	223.26
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	6.5214 (4), 9.2078 (6), 10.5763 (7)
α, β, γ (°)	67.447 (6), 80.212 (5), 78.863 (5)
V (Å³)	572.24 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.50 × 0.50 × 0.30

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire2
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.942, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3413, 2017, 1731
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.069, 1.07
No. of reflections	2017
No. of parameters	170
No. of restraints	163
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.33

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1ⁱ	0.791 (16)	2.695 (17)	3.4633 (13)	164.3 (14)

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

Support of this investigation by the Zanjan Branch, Islamic Azad University, is gratefully acknowledged.

References

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