(2Z)-3-(2,4-Di­chloro­phen­yl)-3-hy­droxy-N-phenyl­prop-2-ene­thio­amide

Kour, D.; Singh, K.; Aitawade, M.M.; Deshmukh, M.B.; Anbhule, P.V.; Gupta, V.K.; Kant, R.

doi:10.1107/S1600536813017339

organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Pages o1173-o1174

https://doi.org/10.1107/S1600536813017339

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(2Z)-3-(2,4-Dichlorophenyl)-3-hydroxy-N-phenylprop-2-enethioamide

Dalbir Kour,^a Kuldeep Singh,^a Mayur M. Aitawade,^b Madhukar B. Deshmukh,^c Prashant V. Anbhule,^c Vivek K. Gupta ^a and Rajni Kant ^a ^*

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, ^bDepartment of Agrochemicals & Pest Management, Shivaji University, Kolhapur, India, and ^cDepartment of Chemistry, Shivaji University, Kolhapur, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 17 June 2013; accepted 24 June 2013; online 29 June 2013)

In the title molecule, C₁₅H₁₁Cl₂NOS, the dihedral angle between the phenyl and benzene rings is 72.24 (1)°. In the crystal, pairs of N—H⋯S hydrogen bonds form dimers with twofold rotational symmetry. The dimers are connected by weak C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to (001). An intramolecular O—H⋯S hydrogen bond is also observed.

Related literature

For the biological activity and applications of thioamides, see: Zahid et al. (2009 ); Jagodzinski (2003 ); Lebana et al. (2008 ). For the synthesis of thioamides, see: Bauer & Kuhlein (1985 ); Cava & Levinson (1985 ). For the synthesis of the title compound, see: Rudrof et al. (1979 ). For related structures, see: Xu et al. (2005 ); Cowley et al. (2002 ); Jiang (2009 ); Patil et al. (2011 ); Deshmukh et al. (2009 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₁Cl₂NOS
M_r = 324.21
Orthorhombic, P c c n
a = 28.9562 (6) Å
b = 13.2610 (3) Å
c = 7.5284 (2) Å
V = 2890.82 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.1 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.835, T_max = 1.000
63107 measured reflections
2836 independent reflections
2275 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.091
S = 1.11
2836 reflections
185 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1ⁱ	0.86	2.61	3.4397 (18)	162
C3′—H3′⋯O1ⁱⁱ	0.93	2.59	3.496 (3)	164
O1—H11⋯S1	0.89 (3)	2.10 (3)	2.9315 (18)	157 (2)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813017339/lh5625sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813017339/lh5625Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813017339/lh5625Isup3.cml

checkCIF report

Comment top

Thioamides exhibit a wide range of applications, not only as synthetic intermediates in the synthesis of a variety of hetero-cyclic compounds (Zahid et al., 2009), but also numerous biological activities have been associated with them (Jagodzinski, 2003). Moreover, thioamides are important ligands in the field of coordination chemistry (Lebana et al., 2008). Several synthetic reports on thioamides have been published involving the uses of Lawesson's regent (Cava & Levinson, 1985) and phosphorus pentasulfide (Bauer & Kuhlein, 1985). Our ongoing research involves the development of newer synthetic methodologies for heterocyclic compounds (Patil et al., 2011; Deshmukh et al., 2009). The crystal structure of the title compound is described herein.

The molecular structure of the title compound (I) is shown in Fig. 1. The bond lengths (Allen, et al., 1987) and angles observed in (I) show normal values and are comparable with related structures (Xu, et al., 2005; Jiang, 2009). The dihedral angle between the phenyl and benzene rings [C1'-C6' and C4-C9] is 72.24 (1)°. The two chlorine atoms Cl1 and Cl2 which were not included in the calculation of the least-squares plane of the C1'-C6' ring, deviate from the plane by 0.1336 (1) and 0.0310 (1) Å. The C1—S1 bond length of 1.695 (2) Å is comparable with the value [1.688 (2) Å] in a related structure (Cowley et al., 2002). In the crystal, pairs of N—H···S hydrogen bonds form dimers with twofold rotational symmetry. The dimers are connected by weak C—H···O hydrogen bonds to form a two-dimensional network parallel to (001). An intramolecular O—H···S hydrogen bond is also observed. The hydrogen bonds are shown in Fig. 2.

Related literature top

For the biological activity and applications of thioamides, see: Zahid et al. (2009); Jagodzinski (2003); Lebana et al. (2008). For the synthesis of thioamides, see: Bauer & Kuhlein (1985); Cava & Levinson (1985). For the synthesis of the title compound, see: Rudrof et al. (1979). For related structures, see: Xu et al. (2005); Cowley et al. (2002); Jiang (2009); Patil et al. (2011); Deshmukh et al. (2009). For standard bond-length data, see: Allen et al. (1987).

Experimental top

(2Z)-3-(2,4-dichlorophenyl)-3-hydroxy-N-phenylprop-2-enethioamide was synthesized by a previously reported procedure (Rudrof et al., 1979). The product dissolved in EtOH, on slow evaporation of the solvent formed crystals of the title compound. Yield: 85%. IR (KBr): 3442, 3207, 1607, 1364, 1224 cm-1. 1H NMR (300 MHz, CDCl3): dH = 5.97 (s, 1H, CH), 7.19–7.53 (m, 8H, Ar—H),8.29 (bs, 1H, NH), 14.75 (s, 1H, OH). 13 C NMR (CDCl3): dc = 136.3, 133.7, 132.6, 131.2, 137.0, 130.9, 129.4, 128.8, 127.5, 127.1, 126.8, 125.2, 123.1. (m/z) = 324.

Structure description top

For the biological activity and applications of thioamides, see: Zahid et al. (2009); Jagodzinski (2003); Lebana et al. (2008). For the synthesis of thioamides, see: Bauer & Kuhlein (1985); Cava & Levinson (1985). For the synthesis of the title compound, see: Rudrof et al. (1979). For related structures, see: Xu et al. (2005); Cowley et al. (2002); Jiang (2009); Patil et al. (2011); Deshmukh et al. (2009). For standard bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dotted lines.

(2Z)-3-(2,4-Dichlorophenyl)-3-hydroxy-N-phenylprop-2-enethioamide top

Crystal data top

C₁₅H₁₁Cl₂NOS	F(000) = 1328
M_r = 324.21	D_x = 1.490 Mg m⁻³
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 24816 reflections
a = 28.9562 (6) Å	θ = 3.4–29.1°
b = 13.2610 (3) Å	µ = 0.59 mm⁻¹
c = 7.5284 (2) Å	T = 293 K
V = 2890.82 (12) Å³	Block, orange
Z = 8	0.3 × 0.2 × 0.1 mm

Data collection top

Agilent Xcalibur Sapphire3 diffractometer	2836 independent reflections
Radiation source: fine-focus sealed tube	2275 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.4°
ω scan	h = −35→35
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −16→16
T_min = 0.835, T_max = 1.000	l = −9→9
63107 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0293P)² + 2.0935P] where P = (F_o² + 2F_c²)/3
2836 reflections	(Δ/σ)_max = 0.001
185 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₅H₁₁Cl₂NOS	V = 2890.82 (12) Å³
M_r = 324.21	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 28.9562 (6) Å	µ = 0.59 mm⁻¹
b = 13.2610 (3) Å	T = 293 K
c = 7.5284 (2) Å	0.3 × 0.2 × 0.1 mm

Data collection top

Agilent Xcalibur Sapphire3 diffractometer	2836 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2275 reflections with I > 2σ(I)
T_min = 0.835, T_max = 1.000	R_int = 0.067
63107 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.22 e Å⁻³
2836 reflections	Δρ_min = −0.18 e Å⁻³
185 parameters

Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
S1	0.31822 (2)	0.16889 (5)	0.20313 (10)	0.04414 (18)
O1	0.41937 (6)	0.17165 (12)	0.2188 (3)	0.0476 (5)
N1	0.29969 (6)	0.36160 (14)	0.2171 (3)	0.0391 (5)
H1	0.2719	0.3391	0.2114	0.047*
Cl1	0.44813 (2)	0.49703 (5)	0.15039 (11)	0.0581 (2)
Cl2	0.61091 (2)	0.40683 (7)	0.43216 (13)	0.0718 (3)
C1	0.33303 (8)	0.29196 (17)	0.2249 (3)	0.0338 (5)
C1'	0.46507 (7)	0.31015 (16)	0.2953 (3)	0.0320 (5)
C2	0.37934 (7)	0.32640 (17)	0.2576 (3)	0.0333 (5)
H2	0.3828	0.3945	0.2840	0.040*
C2'	0.48099 (8)	0.40787 (17)	0.2622 (3)	0.0360 (5)
C3	0.41830 (7)	0.27056 (16)	0.2540 (3)	0.0315 (5)
C3'	0.52538 (8)	0.43770 (19)	0.3058 (3)	0.0430 (6)
H3'	0.5351	0.5033	0.2834	0.052*
C4	0.30453 (7)	0.46842 (17)	0.2172 (3)	0.0343 (5)
C4'	0.55494 (8)	0.3693 (2)	0.3827 (3)	0.0440 (6)
C5	0.28010 (8)	0.5236 (2)	0.3398 (4)	0.0463 (6)
H5	0.2619	0.4912	0.4241	0.056*
C5'	0.54086 (8)	0.2721 (2)	0.4168 (4)	0.0478 (7)
H5'	0.5610	0.2261	0.4685	0.057*
C6	0.28268 (10)	0.6273 (2)	0.3371 (4)	0.0565 (8)
H6	0.2661	0.6647	0.4200	0.068*
C6'	0.49660 (8)	0.2442 (2)	0.3733 (3)	0.0404 (6)
H6'	0.4873	0.1784	0.3969	0.048*
C7	0.30932 (10)	0.6760 (2)	0.2137 (4)	0.0534 (7)
H7	0.3111	0.7460	0.2134	0.064*
C8	0.33346 (9)	0.6208 (2)	0.0902 (4)	0.0476 (7)
H8	0.3515	0.6537	0.0062	0.057*
C9	0.33111 (8)	0.51666 (18)	0.0900 (3)	0.0401 (6)
H9	0.3472	0.4795	0.0055	0.048*
H11	0.3902 (11)	0.152 (2)	0.210 (4)	0.070 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0340 (3)	0.0307 (3)	0.0677 (4)	−0.0066 (3)	0.0007 (3)	0.0007 (3)
O1	0.0327 (10)	0.0286 (9)	0.0816 (13)	0.0008 (7)	0.0009 (9)	−0.0031 (9)
N1	0.0216 (10)	0.0322 (10)	0.0636 (14)	−0.0034 (8)	−0.0027 (9)	0.0025 (10)
Cl1	0.0339 (3)	0.0381 (3)	0.1022 (6)	−0.0011 (3)	−0.0061 (4)	0.0241 (4)
Cl2	0.0333 (4)	0.0834 (6)	0.0989 (6)	−0.0046 (4)	−0.0186 (4)	−0.0110 (5)
C1	0.0319 (13)	0.0313 (12)	0.0382 (13)	−0.0035 (10)	0.0017 (10)	0.0014 (10)
C1'	0.0279 (11)	0.0327 (12)	0.0354 (12)	0.0031 (9)	0.0028 (9)	0.0003 (10)
C2	0.0292 (12)	0.0258 (11)	0.0451 (13)	−0.0016 (9)	0.0008 (10)	0.0000 (10)
C2'	0.0298 (12)	0.0331 (12)	0.0452 (13)	0.0025 (10)	0.0006 (10)	0.0015 (11)
C3	0.0303 (12)	0.0268 (12)	0.0375 (12)	0.0001 (9)	0.0028 (10)	0.0023 (10)
C3'	0.0322 (13)	0.0378 (13)	0.0591 (16)	−0.0023 (11)	−0.0001 (12)	−0.0034 (12)
C4	0.0236 (11)	0.0310 (12)	0.0484 (14)	0.0020 (9)	−0.0073 (10)	0.0016 (11)
C4'	0.0270 (13)	0.0569 (16)	0.0480 (15)	−0.0003 (11)	−0.0039 (11)	−0.0075 (13)
C5	0.0357 (14)	0.0479 (15)	0.0552 (16)	0.0073 (11)	0.0058 (12)	0.0036 (13)
C5'	0.0363 (14)	0.0518 (17)	0.0552 (16)	0.0091 (12)	−0.0079 (12)	0.0076 (13)
C6	0.0555 (18)	0.0457 (16)	0.069 (2)	0.0163 (14)	−0.0018 (15)	−0.0087 (15)
C6'	0.0343 (13)	0.0391 (13)	0.0477 (14)	0.0028 (11)	0.0003 (11)	0.0094 (12)
C7	0.0519 (17)	0.0324 (14)	0.076 (2)	0.0054 (12)	−0.0157 (15)	0.0011 (14)
C8	0.0381 (14)	0.0434 (15)	0.0613 (17)	−0.0052 (11)	−0.0074 (13)	0.0148 (13)
C9	0.0301 (13)	0.0420 (14)	0.0481 (14)	0.0000 (10)	−0.0002 (11)	0.0021 (12)

Geometric parameters (Å, º) top

S1—C1	1.695 (2)	C3'—H3'	0.9300
O1—C3	1.339 (3)	C4—C5	1.374 (3)
O1—H11	0.89 (3)	C4—C9	1.385 (3)
N1—C1	1.337 (3)	C4'—C5'	1.376 (4)
N1—C4	1.423 (3)	C5—C6	1.377 (4)
N1—H1	0.8600	C5—H5	0.9300
Cl1—C2'	1.735 (2)	C5'—C6'	1.374 (3)
Cl2—C4'	1.736 (2)	C5'—H5'	0.9300
C1—C2	1.438 (3)	C6—C7	1.369 (4)
C1'—C6'	1.394 (3)	C6—H6	0.9300
C1'—C2'	1.398 (3)	C6'—H6'	0.9300
C1'—C3	1.485 (3)	C7—C8	1.374 (4)
C2—C3	1.350 (3)	C7—H7	0.9300
C2—H2	0.9300	C8—C9	1.382 (3)
C2'—C3'	1.384 (3)	C8—H8	0.9300
C3'—C4'	1.375 (3)	C9—H9	0.9300

C3—O1—H11	106 (2)	C3'—C4'—C5'	120.8 (2)
C1—N1—C4	128.05 (19)	C3'—C4'—Cl2	118.8 (2)
C1—N1—H1	116.0	C5'—C4'—Cl2	120.3 (2)
C4—N1—H1	116.0	C4—C5—C6	119.6 (3)
N1—C1—C2	117.5 (2)	C4—C5—H5	120.2
N1—C1—S1	118.57 (17)	C6—C5—H5	120.2
C2—C1—S1	123.93 (17)	C6'—C5'—C4'	119.0 (2)
C6'—C1'—C2'	116.2 (2)	C6'—C5'—H5'	120.5
C6'—C1'—C3	117.6 (2)	C4'—C5'—H5'	120.5
C2'—C1'—C3	126.2 (2)	C7—C6—C5	120.7 (3)
C3—C2—C1	127.0 (2)	C7—C6—H6	119.6
C3—C2—H2	116.5	C5—C6—H6	119.6
C1—C2—H2	116.5	C5'—C6'—C1'	122.8 (2)
C3'—C2'—C1'	121.9 (2)	C5'—C6'—H6'	118.6
C3'—C2'—Cl1	115.43 (18)	C1'—C6'—H6'	118.6
C1'—C2'—Cl1	122.49 (18)	C6—C7—C8	119.7 (3)
O1—C3—C2	124.1 (2)	C6—C7—H7	120.2
O1—C3—C1'	111.51 (18)	C8—C7—H7	120.2
C2—C3—C1'	124.3 (2)	C7—C8—C9	120.5 (3)
C4'—C3'—C2'	119.3 (2)	C7—C8—H8	119.7
C4'—C3'—H3'	120.3	C9—C8—H8	119.7
C2'—C3'—H3'	120.3	C8—C9—C4	119.2 (2)
C5—C4—C9	120.3 (2)	C8—C9—H9	120.4
C5—C4—N1	118.7 (2)	C4—C9—H9	120.4
C9—C4—N1	120.9 (2)

C4—N1—C1—C2	7.8 (4)	C1—N1—C4—C9	56.9 (4)
C4—N1—C1—S1	−174.3 (2)	C2'—C3'—C4'—C5'	−0.1 (4)
N1—C1—C2—C3	−173.3 (2)	C2'—C3'—C4'—Cl2	178.55 (19)
S1—C1—C2—C3	8.9 (4)	C9—C4—C5—C6	−0.9 (4)
C6'—C1'—C2'—C3'	−0.6 (3)	N1—C4—C5—C6	−177.1 (2)
C3—C1'—C2'—C3'	180.0 (2)	C3'—C4'—C5'—C6'	−0.2 (4)
C6'—C1'—C2'—Cl1	174.85 (18)	Cl2—C4'—C5'—C6'	−178.9 (2)
C3—C1'—C2'—Cl1	−4.6 (3)	C4—C5—C6—C7	0.0 (4)
C1—C2—C3—O1	−0.2 (4)	C4'—C5'—C6'—C1'	0.1 (4)
C1—C2—C3—C1'	−177.8 (2)	C2'—C1'—C6'—C5'	0.3 (4)
C6'—C1'—C3—O1	−29.6 (3)	C3—C1'—C6'—C5'	179.7 (2)
C2'—C1'—C3—O1	149.8 (2)	C5—C6—C7—C8	0.5 (4)
C6'—C1'—C3—C2	148.2 (2)	C6—C7—C8—C9	−0.1 (4)
C2'—C1'—C3—C2	−32.4 (4)	C7—C8—C9—C4	−0.8 (4)
C1'—C2'—C3'—C4'	0.5 (4)	C5—C4—C9—C8	1.3 (4)
Cl1—C2'—C3'—C4'	−175.2 (2)	N1—C4—C9—C8	177.4 (2)
C1—N1—C4—C5	−126.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.86	2.61	3.4397 (18)	162
C3′—H3′···O1ⁱⁱ	0.93	2.59	3.496 (3)	164
O1—H11···S1	0.89 (3)	2.10 (3)	2.9315 (18)	157 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁Cl₂NOS
M_r	324.21
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	293
a, b, c (Å)	28.9562 (6), 13.2610 (3), 7.5284 (2)
V (Å³)	2890.82 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.3 × 0.2 × 0.1

Data collection
Diffractometer	Agilent Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.835, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	63107, 2836, 2275
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.091, 1.11
No. of reflections	2836
No. of parameters	185
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.86	2.61	3.4397 (18)	162
C3'—H3'···O1ⁱⁱ	0.93	2.59	3.496 (3)	164
O1—H11···S1	0.89 (3)	2.10 (3)	2.9315 (18)	157 (2)

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

Acknowledgements

RK is thankful to the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/ CMP-47/2003.

References

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