1-(Naphthalen-1-yl)-3-[(thio­phen-2-yl)carbon­yl]thio­urea

Singh, D.P.; Pratap, S.; Gupta, S.K.; Butcher, R.J.

doi:10.1107/S1600536812035350

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Pages o2882-o2883

https://doi.org/10.1107/S1600536812035350

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1-(Naphthalen-1-yl)-3-[(thiophen-2-yl)carbonyl]thiourea

Durga P. Singh,^a Seema Pratap,^a Sushil K. Gupta ^b and Ray J. Butcher ^c ^*

^aDepartment of Chemistry, M. M. V., Banaras Hindu University, Varanasi 221 005, India, ^bSchool of Studies in Chemistry, Jiwaji University, Gwalior 474 011, India, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: rbutcher99@yahoo.com

(Received 29 June 2012; accepted 9 August 2012; online 8 September 2012)

In the title compound, C₁₆H₁₂N₂OS₂, the dihedral angles between the mean planes of the central thiourea core and the thiophene ring and the naphthalene ring system are 1.8 (2) and 6.45 (18)°, respectively. The molecule adopts a trans–cis conformation with respect to the position of thiophenoyl and naphthyl groups relative to the S atom across the thiourea C—N bonds. Both the thiophene ring and the sulfanylidene S atom are disordered over two sets of sites with occupancies of 0.862 (3):0.138 (3) and 0.977 (3):0.023 (3), respectively. An intramolecular N—H⋯O hydrogen bond is observed. The crystal packing features two N—H⋯S hydrogen bonds.

Related literature

For heterocyclic thiourea derivatives, metal complexes and their applications, see: D'hooghe et al. (2005 ); Aly et al. (2007 ); Estévez-Hernández et al. (2007 ); Saeed et al. (2008a ,b ,c ). For related structures, see: Singh et al. (2012 ); Koch (2001 ); Pérez et al. (2008 ). For the synthesis, see: Otazo-Sánchez et al. (2001 ).

Experimental

Crystal data

C₁₆H₁₂N₂OS₂
M_r = 312.40
Monoclinic, P 2₁ /c
a = 14.929 (2) Å
b = 5.9086 (8) Å
c = 17.071 (3) Å
β = 104.030 (14)°
V = 1460.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 173 K
0.35 × 0.25 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.712, T_max = 1.000
4822 measured reflections
2625 independent reflections
1626 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.165
S = 1.09
2625 reflections
210 parameters
10 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.88	1.86	2.615 (3)	143
N2—H2A⋯S2B	0.88	2.57	3.026 (14)	113
N2—H2A⋯S1Aⁱ	0.88	2.56	3.41 (4)	164
N2—H2A⋯S1Bⁱ	0.88	2.80	3.557 (3)	145
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812035350/bq2371sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812035350/bq2371Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812035350/bq2371Isup3.cml

checkCIF report

Comment top

Aroylythiourea and its derivatives are an important class of organic compounds due to their ability to form a variety of heterocyclic compounds (D'hooghe et al., 2005) and metal complexes that can be used as ionophores in potentiometric and amperometric sensors (Aly et al., 2007; Estévez-Hernández et al., 2007) and as epoxy resin curing agents and accelerators (Saeed et al., 2008a, 2008b, 2008c). The title compound, N-(naphthalen-1-yl)-3-oxo-3-(thiophen-2-yl)propanethioamide is an important precursor with O and S as potential donor sites, and can be used to form heterocycles and metal complexes. We have reported recently the synthesis and crystal structure of methyl 2-(thiophene-2-carboxamido)benzoate (Singh et al., 2012). We herein report the synthesis and crystal structure of the biologically active title compound.

In the title compound (Fig.1) the bond lengths and angles are within the ranges observed for similar compounds (Koch, 2001; Pérez et al., 2008). The C11—S1B [1.661 (3) Å] and C12—O1 [1.230 (3) Å] bonds show typical double-bond character. However, the C—N bond lengths, C12—N2 [1.376 (4) Å], C11—N1 [1.326 (4) Å], C11—N2 [1.397 (4) Å] and C1—N1 [1.419 (4) Å] are all shorter than the normal C—N single-bond length of about 1.48 Å and indicate some degree of delocalization. The central thiourea fragment (N1/C11/N2/C12/O1) makes a dihedral angle of 2.03 (41)° with the major part of the 2-thiophenoyl group (S2/C13/C14/C15/C16) and 6.51 (16)° with the naphthalene ring (C1/C2/C3/C4/C5/C6/C7/C8/C9/C10), respectively. Thus, the conformation is almost planar and adopts a trans-cis configuration with respect to the position of the thiophenoyl and naphthyl groups relative to the S atom across the thiourea C—N bonds. This geometry is stabilized by both an N1—H1···O1 intramolecular hydrogen bond and two intermolecular N—H···S hydrogen bonds (Fig.2). In addition, both the thiophene ring and the thio S are disordered over two positions with occupancies of 0.862 (3)/0.138 (3) and 0.977 (3)/0.023 (3), respectively.

Related literature top

For heterocyclic derivatives, metal complexes and their applications, see: D'hooghe et al. (2005); Aly et al. (2007); Estévez-Hernández et al. (2007); Saeed et al. (2008a,b,c). For related structures, see: Singh et al. (2012); Koch (2001); Pérez et al. (2008). For the synthesis, see: Otazo-Sánchez et al. (2001).

Experimental top

The title compound was synthesized according to a previous report (Otazo-Sánchez et al., 2001), by converting furoyl choride into furoyl isothiocyanate and then condensing with α-naphthylamine. The resulting solid product was crystallized from ethanol yielding X-ray quality single crystals (M.P.: 459 K). Anal. Calc. for C₁₆H₁₂N₂OS₂ (%): C, 61.51; H, 3.87; N, 8.97. Found: C, 61.20; H, 3.80; N, 9.10.

Structure description top

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); 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. Molecular structure of the title compound (major component only) showing the atom labeling scheme and 30% probability displacement ellipsoids. Dashed lines indicate an intramolecular N—H···O hydrogen bond.
	Fig. 2. Crystal packing for the title compound viewed along b axis. Dashed lines indicate intramolecular N—H···O and intermolecular N—H···S hydrogen bonds.

1-(Naphthalen-1-yl)-3-[(thiophen-2-yl)carbonyl]thiourea top

Crystal data top

C₁₆H₁₂N₂OS₂	F(000) = 648
M_r = 312.40	D_x = 1.420 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.929 (2) Å	Cell parameters from 1174 reflections
b = 5.9086 (8) Å	θ = 3.3–27.3°
c = 17.071 (3) Å	µ = 0.36 mm⁻¹
β = 104.030 (14)°	T = 173 K
V = 1460.9 (4) Å³	Prism, colorless
Z = 4	0.35 × 0.25 × 0.15 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2625 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1626 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
Detector resolution: 16.0938 pixels mm^-1	θ_max = 25.5°, θ_min = 3.7°
ω scans	h = −18→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −6→7
T_min = 0.712, T_max = 1.000	l = −17→20
4822 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.165	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.058P)² + 0.3695P] where P = (F_o² + 2F_c²)/3
2625 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.33 e Å⁻³
10 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₆H₁₂N₂OS₂	V = 1460.9 (4) Å³
M_r = 312.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.929 (2) Å	µ = 0.36 mm⁻¹
b = 5.9086 (8) Å	T = 173 K
c = 17.071 (3) Å	0.35 × 0.25 × 0.15 mm
β = 104.030 (14)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2625 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	1626 reflections with I > 2σ(I)
T_min = 0.712, T_max = 1.000	R_int = 0.052
4822 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	10 restraints
wR(F²) = 0.165	H-atom parameters constrained
S = 1.09	Δρ_max = 0.33 e Å⁻³
2625 reflections	Δρ_min = −0.31 e Å⁻³
210 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)
S1A	0.962 (3)	0.732 (11)	0.421 (4)	0.0764 (5)	0.023 (3)
S1B	0.98334 (7)	0.6323 (3)	0.38685 (9)	0.0764 (5)	0.977 (3)
S2A	0.66455 (8)	−0.0348 (2)	0.46547 (8)	0.0582 (4)	0.862 (3)
C13A	0.7707 (3)	0.0902 (7)	0.4715 (3)	0.0404 (11)	0.862 (3)
C14A	0.8378 (4)	−0.0413 (13)	0.5210 (5)	0.0655 (19)	0.862 (3)
H14A	0.9018	−0.0083	0.5310	0.079*	0.862 (3)
C15A	0.8041 (4)	−0.2228 (11)	0.5543 (4)	0.0655 (15)	0.862 (3)
H15A	0.8419	−0.3270	0.5900	0.079*	0.862 (3)
C16A	0.7114 (4)	−0.2380 (12)	0.5309 (6)	0.0695 (14)	0.862 (3)
H16A	0.6765	−0.3515	0.5496	0.083*	0.862 (3)
S2B	0.8612 (8)	−0.036 (2)	0.5239 (9)	0.0582 (4)	0.138 (3)
C13B	0.7593 (17)	0.051 (5)	0.4590 (19)	0.0404 (11)	0.138 (3)
C14B	0.6895 (17)	−0.046 (5)	0.488 (2)	0.0655 (19)	0.138 (3)
H14B	0.6294	0.0174	0.4803	0.079*	0.138 (3)
C15B	0.716 (2)	−0.242 (7)	0.530 (4)	0.0655 (15)	0.138 (3)
H15B	0.6767	−0.3658	0.5338	0.079*	0.138 (3)
C16B	0.807 (2)	−0.233 (7)	0.566 (3)	0.0695 (14)	0.138 (3)
H16B	0.8373	−0.3273	0.6097	0.083*	0.138 (3)
O1	0.69721 (14)	0.3590 (3)	0.37691 (14)	0.0546 (6)
N1	0.79871 (16)	0.6726 (4)	0.33310 (16)	0.0440 (7)
H1A	0.7462	0.6094	0.3360	0.053*
N2	0.85320 (16)	0.3884 (4)	0.42315 (16)	0.0452 (7)
H2A	0.9009	0.3300	0.4579	0.054*
C1	0.7879 (2)	0.8627 (5)	0.28085 (19)	0.0432 (8)
C2	0.8584 (2)	1.0074 (5)	0.2753 (2)	0.0541 (9)
H2	0.9196	0.9774	0.3054	0.065*
C3	0.8401 (3)	1.1985 (5)	0.2255 (2)	0.0585 (10)
H3	0.8894	1.2973	0.2223	0.070*
C4	0.7537 (3)	1.2454 (5)	0.1817 (2)	0.0570 (9)
H4	0.7429	1.3778	0.1492	0.068*
C5	0.6798 (2)	1.0997 (5)	0.1838 (2)	0.0468 (8)
C6	0.5901 (3)	1.1427 (6)	0.1368 (2)	0.0594 (10)
H6	0.5788	1.2741	0.1038	0.071*
C7	0.5189 (3)	0.9981 (6)	0.1379 (2)	0.0659 (11)
H7	0.4587	1.0297	0.1060	0.079*
C8	0.5347 (2)	0.8048 (6)	0.1857 (2)	0.0574 (10)
H8	0.4851	0.7044	0.1859	0.069*
C9	0.6200 (2)	0.7578 (5)	0.2319 (2)	0.0494 (9)
H9	0.6291	0.6249	0.2642	0.059*
C10	0.6962 (2)	0.9031 (5)	0.23326 (19)	0.0416 (8)
C11	0.8727 (2)	0.5719 (5)	0.37841 (19)	0.0434 (8)
C12	0.7696 (2)	0.2864 (5)	0.4203 (2)	0.0433 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.0282 (5)	0.1166 (10)	0.0801 (9)	−0.0049 (6)	0.0048 (5)	0.0291 (8)
S1B	0.0282 (5)	0.1166 (10)	0.0801 (9)	−0.0049 (6)	0.0048 (5)	0.0291 (8)
S2A	0.0543 (7)	0.0566 (6)	0.0598 (9)	−0.0107 (6)	0.0061 (5)	0.0071 (6)
C13A	0.0405 (19)	0.035 (2)	0.041 (2)	−0.0003 (16)	0.0015 (16)	−0.0068 (18)
C14A	0.057 (4)	0.064 (3)	0.077 (4)	0.000 (3)	0.020 (4)	−0.010 (2)
C15A	0.091 (4)	0.048 (2)	0.051 (3)	0.023 (3)	0.004 (3)	0.006 (2)
C16A	0.090 (4)	0.053 (3)	0.063 (3)	−0.015 (3)	0.015 (3)	0.002 (2)
S2B	0.0543 (7)	0.0566 (6)	0.0598 (9)	−0.0107 (6)	0.0061 (5)	0.0071 (6)
C13B	0.0405 (19)	0.035 (2)	0.041 (2)	−0.0003 (16)	0.0015 (16)	−0.0068 (18)
C14B	0.057 (4)	0.064 (3)	0.077 (4)	0.000 (3)	0.020 (4)	−0.010 (2)
C15B	0.091 (4)	0.048 (2)	0.051 (3)	0.023 (3)	0.004 (3)	0.006 (2)
C16B	0.090 (4)	0.053 (3)	0.063 (3)	−0.015 (3)	0.015 (3)	0.002 (2)
O1	0.0340 (12)	0.0537 (13)	0.0694 (16)	−0.0034 (10)	−0.0006 (11)	0.0150 (12)
N1	0.0286 (13)	0.0453 (14)	0.0541 (17)	−0.0030 (11)	0.0021 (12)	0.0007 (13)
N2	0.0302 (13)	0.0547 (15)	0.0472 (16)	0.0030 (12)	0.0026 (11)	0.0113 (13)
C1	0.0381 (17)	0.0383 (15)	0.0503 (19)	−0.0019 (14)	0.0050 (14)	−0.0047 (14)
C2	0.0455 (19)	0.0503 (18)	0.067 (2)	−0.0095 (16)	0.0136 (17)	−0.0035 (17)
C3	0.063 (2)	0.0504 (18)	0.068 (2)	−0.0188 (18)	0.0281 (19)	−0.0075 (18)
C4	0.072 (2)	0.0452 (17)	0.059 (2)	−0.0030 (19)	0.0254 (19)	0.0032 (16)
C5	0.0516 (19)	0.0406 (16)	0.050 (2)	0.0058 (16)	0.0165 (16)	−0.0023 (15)
C6	0.062 (2)	0.057 (2)	0.059 (2)	0.0175 (19)	0.0146 (19)	0.0156 (18)
C7	0.051 (2)	0.075 (2)	0.067 (3)	0.018 (2)	0.0062 (19)	0.017 (2)
C8	0.0409 (19)	0.064 (2)	0.065 (2)	0.0007 (17)	0.0078 (17)	0.0111 (19)
C9	0.0421 (18)	0.0506 (17)	0.052 (2)	−0.0010 (16)	0.0044 (15)	0.0080 (16)
C10	0.0387 (17)	0.0380 (15)	0.0477 (19)	0.0024 (14)	0.0092 (14)	−0.0061 (14)
C11	0.0342 (16)	0.0593 (18)	0.0356 (17)	−0.0004 (15)	0.0065 (13)	0.0002 (15)
C12	0.0322 (16)	0.0423 (16)	0.0513 (19)	0.0028 (14)	0.0023 (14)	−0.0017 (15)

Geometric parameters (Å, º) top

S1A—C11	1.65 (5)	N1—H1A	0.8800
S1B—C11	1.661 (3)	N2—C12	1.376 (4)
S2A—C16A	1.674 (6)	N2—C11	1.397 (4)
S2A—C13A	1.729 (4)	N2—H2A	0.8800
C13A—C14A	1.383 (7)	C1—C2	1.377 (4)
C13A—C12	1.449 (5)	C1—C10	1.432 (4)
C14A—C15A	1.365 (8)	C2—C3	1.401 (5)
C14A—H14A	0.9500	C2—H2	0.9500
C15A—C16A	1.347 (6)	C3—C4	1.353 (5)
C15A—H15A	0.9500	C3—H3	0.9500
C16A—H16A	0.9500	C4—C5	1.408 (5)
S2B—C16B	1.67 (2)	C4—H4	0.9500
S2B—C13B	1.728 (19)	C5—C6	1.407 (4)
C13B—C14B	1.39 (2)	C5—C10	1.422 (4)
C13B—C12	1.56 (3)	C6—C7	1.367 (5)
C14B—C15B	1.37 (2)	C6—H6	0.9500
C14B—H14B	0.9500	C7—C8	1.390 (5)
C15B—C16B	1.350 (18)	C7—H7	0.9500
C15B—H15B	0.9500	C8—C9	1.354 (4)
C16B—H16B	0.9500	C8—H8	0.9500
O1—C12	1.230 (3)	C9—C10	1.421 (4)
N1—C11	1.326 (4)	C9—H9	0.9500
N1—C1	1.419 (4)

C16A—S2A—C13A	92.2 (2)	C3—C2—H2	119.9
C14A—C13A—C12	136.0 (5)	C4—C3—C2	121.3 (3)
C14A—C13A—S2A	108.3 (4)	C4—C3—H3	119.3
C12—C13A—S2A	115.4 (3)	C2—C3—H3	119.3
C15A—C14A—C13A	114.2 (5)	C3—C4—C5	120.6 (3)
C15A—C14A—H14A	122.9	C3—C4—H4	119.7
C13A—C14A—H14A	122.9	C5—C4—H4	119.7
C16A—C15A—C14A	112.6 (5)	C4—C5—C6	121.3 (3)
C16A—C15A—H15A	123.7	C4—C5—C10	119.4 (3)
C14A—C15A—H15A	123.7	C6—C5—C10	119.3 (3)
C15A—C16A—S2A	112.5 (5)	C7—C6—C5	121.0 (3)
C15A—C16A—H16A	123.7	C7—C6—H6	119.5
S2A—C16A—H16A	123.7	C5—C6—H6	119.5
C16B—S2B—C13B	92.5 (12)	C6—C7—C8	119.9 (3)
C14B—C13B—C12	133 (2)	C6—C7—H7	120.0
C14B—C13B—S2B	105.6 (15)	C8—C7—H7	120.0
C12—C13B—S2B	112.0 (16)	C9—C8—C7	120.8 (3)
C15B—C14B—C13B	113 (2)	C9—C8—H8	119.6
C15B—C14B—H14B	123.6	C7—C8—H8	119.6
C13B—C14B—H14B	123.6	C8—C9—C10	121.4 (3)
C16B—C15B—C14B	110 (2)	C8—C9—H9	119.3
C16B—C15B—H15B	125.2	C10—C9—H9	119.3
C14B—C15B—H15B	125.2	C9—C10—C5	117.5 (3)
C15B—C16B—S2B	112 (2)	C9—C10—C1	124.0 (3)
C15B—C16B—H16B	124.2	C5—C10—C1	118.5 (3)
S2B—C16B—H16B	124.2	N1—C11—N2	114.4 (3)
C11—N1—C1	132.4 (3)	N1—C11—S1A	118 (2)
C11—N1—H1A	113.8	N2—C11—S1A	117.1 (18)
C1—N1—H1A	113.8	N1—C11—S1B	128.6 (3)
C12—N2—C11	128.9 (2)	N2—C11—S1B	117.0 (2)
C12—N2—H2A	115.5	S1A—C11—S1B	33 (3)
C11—N2—H2A	115.5	O1—C12—N2	121.7 (3)
C2—C1—N1	124.2 (3)	O1—C12—C13A	121.5 (3)
C2—C1—C10	119.9 (3)	N2—C12—C13A	116.8 (3)
N1—C1—C10	115.9 (3)	O1—C12—C13B	113.8 (9)
C1—C2—C3	120.2 (3)	N2—C12—C13B	123.8 (9)
C1—C2—H2	119.9	C13A—C12—C13B	11.9 (13)

C16A—S2A—C13A—C14A	3.3 (6)	C4—C5—C10—C9	−178.4 (3)
C16A—S2A—C13A—C12	178.1 (5)	C6—C5—C10—C9	0.4 (5)
C12—C13A—C14A—C15A	−176.1 (6)	C4—C5—C10—C1	1.4 (4)
S2A—C13A—C14A—C15A	−2.9 (8)	C6—C5—C10—C1	−179.8 (3)
C13A—C14A—C15A—C16A	0.8 (11)	C2—C1—C10—C9	176.9 (3)
C14A—C15A—C16A—S2A	1.9 (11)	N1—C1—C10—C9	−4.5 (5)
C13A—S2A—C16A—C15A	−3.0 (8)	C2—C1—C10—C5	−2.8 (5)
C16B—S2B—C13B—C14B	13 (4)	N1—C1—C10—C5	175.8 (3)
C16B—S2B—C13B—C12	164 (3)	C1—N1—C11—N2	178.7 (3)
C12—C13B—C14B—C15B	−169 (4)	C1—N1—C11—S1A	35 (3)
S2B—C13B—C14B—C15B	−27 (5)	C1—N1—C11—S1B	−2.6 (5)
C13B—C14B—C15B—C16B	30 (6)	C12—N2—C11—N1	7.1 (5)
C14B—C15B—C16B—S2B	−19 (7)	C12—N2—C11—S1A	151 (3)
C13B—S2B—C16B—C15B	3 (5)	C12—N2—C11—S1B	−171.6 (3)
C11—N1—C1—C2	−9.6 (5)	C11—N2—C12—O1	−3.4 (5)
C11—N1—C1—C10	171.8 (3)	C11—N2—C12—C13A	177.1 (3)
N1—C1—C2—C3	−176.2 (3)	C11—N2—C12—C13B	165.9 (17)
C10—C1—C2—C3	2.3 (5)	C14A—C13A—C12—O1	174.0 (6)
C1—C2—C3—C4	−0.2 (5)	S2A—C13A—C12—O1	1.2 (5)
C2—C3—C4—C5	−1.3 (5)	C14A—C13A—C12—N2	−6.5 (8)
C3—C4—C5—C6	−178.1 (3)	S2A—C13A—C12—N2	−179.4 (3)
C3—C4—C5—C10	0.7 (5)	C14A—C13A—C12—C13B	122 (7)
C4—C5—C6—C7	178.6 (4)	S2A—C13A—C12—C13B	−51 (6)
C10—C5—C6—C7	−0.2 (5)	C14B—C13B—C12—O1	−36 (4)
C5—C6—C7—C8	−0.3 (6)	S2B—C13B—C12—O1	−176.6 (15)
C6—C7—C8—C9	0.4 (6)	C14B—C13B—C12—N2	154 (3)
C7—C8—C9—C10	−0.2 (5)	S2B—C13B—C12—N2	13 (3)
C8—C9—C10—C5	−0.3 (5)	C14B—C13B—C12—C13A	96 (9)
C8—C9—C10—C1	180.0 (3)	S2B—C13B—C12—C13A	−44 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.88	1.86	2.615 (3)	143
N2—H2A···S2B	0.88	2.57	3.026 (14)	113
N2—H2A···S1Aⁱ	0.88	2.56	3.41 (4)	164
N2—H2A···S1Bⁱ	0.88	2.80	3.557 (3)	145

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₂OS₂
M_r	312.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	14.929 (2), 5.9086 (8), 17.071 (3)
β (°)	104.030 (14)
V (Å³)	1460.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.35 × 0.25 × 0.15

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.712, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4822, 2625, 1626
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.165, 1.09
No. of reflections	2625
No. of parameters	210
No. of restraints	10
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.31

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.88	1.86	2.615 (3)	142.7
N2—H2A···S2B	0.88	2.57	3.026 (14)	112.9
N2—H2A···S1Aⁱ	0.88	2.56	3.41 (4)	163.7
N2—H2A···S1Bⁱ	0.88	2.80	3.557 (3)	145.2

Symmetry code: (i) −x+2, −y+1, −z+1.

Acknowledgements

DPS and SP are grateful to Banaras Hindu University, Varanasi, for financial support. RJB acknowledges the NSF–MRI program (grant No. CHE0619278) for funds to purchase the X-ray diffractometer. SKG wishes to acknowledge the USIEF for the award of a Fulbright–Nehru Senior Research Fellowship.

References

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