3-Benzyl-5-butyl-1,3,5-thia­diazinane-2-thione

Arfan, M.; Tahir, M.N.; Shah, M.I.A.; Iqbal, M.S.

doi:10.1107/S1600536809003882

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o468

doi:10.1107/S1600536809003882

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3-Benzyl-5-butyl-1,3,5-thiadiazinane-2-thione

Mohammad Arfan,^a M. Nawaz Tahir,^b ^* Muhammad Ishaq Ali Shah ^a and Mohammad S. Iqbal ^c

^aInstitute of Chemical Sciences, University of Peshawar, Peshawar 25120, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cDepartment of Chemistry, Government College University, Lahore, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 30 January 2009; accepted 2 February 2009; online 6 February 2009)

In the title compound, C₁₄H₂₀N₂S₂, the 1,3,5-thiadiazinane-2-thione ring adopts an envelope conformation. The S=C bond length is 1.6776 (15) Å, whereas the S—C bond lengths are 1.7470 (15) and 1.8479 (17) Å. The intramolecular C—H⋯S hydrogen bond between the thione and the benzyl units along with the C—H⋯π interaction between the butyl group and the centroid of the benzene ring may be effective in stabilizing the molecule.

Related literature

For the synthesis of the 1,3,5-thiadiazinane-2-thione nucleus, see: Aboul-fadi et al. (2002 ); Ertan et al. (1991 , 1996 ). For its biological activity, see: Coro et al. (2005 ). For a related structure, see: Perez et al. (2001 ). For bond-length data, see: Allen (2002 );

Experimental

Crystal data

C₁₄H₂₀N₂S₂
M_r = 280.44
Triclinic, $[P \overline 1]$
a = 7.6559 (2) Å
b = 9.9586 (3) Å
c = 11.1531 (4) Å
α = 66.917 (2)°
β = 70.649 (1)°
γ = 76.076 (2)°
V = 732.03 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 (2) K
0.26 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.922, T_max = 0.942
15790 measured reflections
3759 independent reflections
2990 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.100
S = 1.03
3759 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯S1	0.97	2.60	3.0978 (16)	112
C12—H12B⋯CgA	0.97	2.96	3.7937 (19)	145
CgA is the centroid of the C1–C6 ring.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007); 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, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2003).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003882/at2719sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003882/at2719Isup2.hkl

checkCIF report

Comment top

1,3,5-Thiadiazinane-2-thione nucleus is an important pharmacophoric nucleus and large number of its analogs have been synthesized through different synthetic approaches, including amines and carbon disulfide in aqueous KOH, via diathiocarbamate salt intermediate (Ertan et al., 1991), from isothiocyanates and amines (Ertan et al., 1996), and resin supported solid phase organic synthesis (Aboul-fadi et al., 2002). Diverse bioactivities including antibacterial, antifungal, antimycobactarial, antitubercular, antiprotozoal, leishmanicidal, nematocidal and antiviral are reported for this nucleus in the literature (Coro et al., 2005).

The crystal structure of 5-(2-carboxyethyl)-3-(fur-2-ylmethyl)-tetrahydro- 2H-1,3,5-thiadiazine-2-thione (Perez et al., 2001) contains the same heterocyclic ring as the title compound (I), (Fig 1). The heterocyclic ring is in envelop form with the group (N1/C8/S2/C10/C9) in plane and the N2 displaced by -0.6778 (17) Å from it. The dihedral angle between the benzene ring A(C1—C6) and this group is 81.22 (5)°. The CCDC search (Allen et al., 2002) showed that there are very few crystal structures having 1,3,5-thiadiazinane-2-thione nucleus, so some important bond lengths and bond angles are given in Table 1.

There are no indications of intermolecular contacts, however some weak intramolecular H-bonding is given in Table 2 [CgA is a centroid of the phenyl ring C1–C6].

Related literature top

For the synthesis of the 1,3,5-thiadiazinane-2-thione nucleus, see: Aboul-fadi et al. (2002); Ertan et al. (1991, 1996). For its biological activity, see: Coro et al. (2005). For a related structure, see: Perez et al. (2001). For bond-length data, see: Allen (2002);

Experimental top

The 1,3,5-thiadizinane thione was synthesized following the synthetic procedure reported by Ertan et al., 1991. Carbon disulfide (20 mmol) was added portion-wise to a magnetically stirred solution of benzylamine (2.18 ml, 20 mmol) and potassium hydroxide (20 mmol) in 30 ml of water. The contents were stirred for 4 h at room temperature. Formaldehyde (37%, 40 mmol) was added to the reaction mixture and stirred for further 1 h. The reaction content was filtered and the filtrate was added drop-wise to a suspension of n-butylamine (1.97 ml, 20 mmol) to the phosphate buffer (pH 7.8) and stirred for 1 h at ambient temperature. The filterate of the reaction mixture was exhaustively extracted with dichloromethane. The aqueous reaction content was acidified with 15% HCl. The precipitated product was filtered off under suction and thoroughly washed with water. The air dried product was re-crystallized from ethanol. A colourless crystalline product [yield: 76%, m.p.: 381–383 K] was obtained.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinG (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

Fig. 1. ORTEP drawing of the title compound, with the atom numbering scheme. The thermal ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii. The intramolecular H-bonding is shown by dotted lines.

3-Benzyl-5-butyl-1,3,5-thiadiazinane-2-thione top

Crystal data top

C₁₄H₂₀N₂S₂	Z = 2
M_r = 280.44	F(000) = 300
Triclinic, P1	D_x = 1.272 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6559 (2) Å	Cell parameters from 2990 reflections
b = 9.9586 (3) Å	θ = 2.1–28.7°
c = 11.1531 (4) Å	µ = 0.35 mm⁻¹
α = 66.917 (2)°	T = 296 K
β = 70.649 (1)°	Prismatic, colourless
γ = 76.076 (2)°	0.26 × 0.20 × 0.18 mm
V = 732.03 (4) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	3759 independent reflections
Radiation source: fine-focus sealed tube	2990 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.7°, θ_min = 2.1°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→13
T_min = 0.922, T_max = 0.942	l = −15→14
15790 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0507P)² + 0.1133P] where P = (F_o² + 2F_c²)/3
3759 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₄H₂₀N₂S₂	γ = 76.076 (2)°
M_r = 280.44	V = 732.03 (4) Å³
Triclinic, P1	Z = 2
a = 7.6559 (2) Å	Mo Kα radiation
b = 9.9586 (3) Å	µ = 0.35 mm⁻¹
c = 11.1531 (4) Å	T = 296 K
α = 66.917 (2)°	0.26 × 0.20 × 0.18 mm
β = 70.649 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3759 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2990 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.942	R_int = 0.025
15790 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.03	Δρ_max = 0.22 e Å⁻³
3759 reflections	Δρ_min = −0.20 e Å⁻³
163 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.37143 (5)	0.10537 (5)	0.24801 (4)	0.0559 (1)
S2	0.72763 (5)	0.05293 (4)	0.29926 (4)	0.0542 (1)
N1	0.44875 (14)	0.24375 (12)	0.38422 (10)	0.0392 (3)
N2	0.76229 (15)	0.27317 (13)	0.37678 (11)	0.0446 (3)
C1	0.25768 (16)	0.48352 (15)	0.31596 (13)	0.0404 (4)
C2	0.20907 (19)	0.59310 (17)	0.37238 (15)	0.0501 (5)
C3	0.2155 (3)	0.73893 (19)	0.2912 (2)	0.0663 (6)
C4	0.2704 (3)	0.7760 (2)	0.1528 (2)	0.0733 (7)
C5	0.3168 (3)	0.6681 (2)	0.09567 (17)	0.0680 (6)
C6	0.3104 (2)	0.52245 (18)	0.17638 (15)	0.0525 (5)
C7	0.25828 (17)	0.32402 (15)	0.40427 (14)	0.0447 (4)
C8	0.50163 (17)	0.14720 (14)	0.32035 (13)	0.0408 (3)
C9	0.8377 (2)	0.12518 (17)	0.38223 (16)	0.0541 (5)
C10	0.56811 (17)	0.27834 (16)	0.44744 (13)	0.0431 (4)
C11	0.80744 (19)	0.38248 (16)	0.24024 (13)	0.0449 (4)
C12	0.7732 (2)	0.53983 (16)	0.23571 (14)	0.0488 (4)
C13	0.8309 (2)	0.64508 (17)	0.09273 (15)	0.0560 (5)
C14	0.8034 (3)	0.8041 (2)	0.0821 (2)	0.0821 (7)
H2	0.17173	0.56829	0.46589	0.0601*
H3	0.18275	0.81193	0.32993	0.0796*
H4	0.27603	0.87410	0.09782	0.0878*
H5	0.35270	0.69350	0.00210	0.0817*
H6	0.34143	0.45000	0.13712	0.0630*
H7A	0.20828	0.31702	0.49831	0.0537*
H7B	0.17844	0.27896	0.38314	0.0537*
H9A	0.82125	0.06214	0.47607	0.0649*
H9B	0.97069	0.12161	0.33891	0.0649*
H10A	0.52272	0.37597	0.45308	0.0516*
H10B	0.55480	0.20912	0.53898	0.0516*
H11A	0.73375	0.37322	0.18858	0.0538*
H11B	0.93788	0.36004	0.19640	0.0538*
H12A	0.84292	0.54959	0.28969	0.0586*
H12B	0.64162	0.56520	0.27472	0.0586*
H13A	0.96161	0.61717	0.05363	0.0672*
H13B	0.75950	0.63540	0.03977	0.0672*
H14A	0.84286	0.86437	−0.01109	0.1232*
H14B	0.87606	0.81541	0.13228	0.1232*
H14C	0.67380	0.83370	0.11828	0.1232*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0586 (2)	0.0591 (2)	0.0578 (2)	−0.0195 (2)	−0.0143 (2)	−0.0221 (2)
S2	0.0483 (2)	0.0444 (2)	0.0635 (3)	0.0008 (1)	−0.0102 (2)	−0.0197 (2)
N1	0.0350 (5)	0.0416 (6)	0.0381 (6)	−0.0065 (4)	−0.0072 (4)	−0.0118 (5)
N2	0.0389 (5)	0.0526 (7)	0.0390 (6)	−0.0087 (5)	−0.0112 (4)	−0.0100 (5)
C1	0.0315 (5)	0.0469 (7)	0.0422 (7)	−0.0041 (5)	−0.0099 (5)	−0.0150 (6)
C2	0.0469 (7)	0.0558 (9)	0.0505 (8)	−0.0020 (6)	−0.0139 (6)	−0.0230 (7)
C3	0.0691 (10)	0.0496 (9)	0.0874 (13)	0.0017 (7)	−0.0303 (9)	−0.0284 (9)
C4	0.0758 (11)	0.0464 (9)	0.0843 (14)	−0.0061 (8)	−0.0335 (10)	0.0005 (9)
C5	0.0694 (10)	0.0707 (11)	0.0470 (9)	−0.0072 (8)	−0.0176 (8)	−0.0018 (8)
C6	0.0538 (8)	0.0582 (9)	0.0446 (8)	−0.0032 (6)	−0.0131 (6)	−0.0189 (7)
C7	0.0341 (6)	0.0493 (8)	0.0443 (7)	−0.0075 (5)	−0.0021 (5)	−0.0148 (6)
C8	0.0415 (6)	0.0372 (6)	0.0365 (6)	−0.0109 (5)	−0.0062 (5)	−0.0052 (5)
C9	0.0422 (7)	0.0555 (9)	0.0545 (8)	−0.0025 (6)	−0.0164 (6)	−0.0076 (7)
C10	0.0434 (6)	0.0513 (8)	0.0331 (6)	−0.0106 (5)	−0.0087 (5)	−0.0115 (6)
C11	0.0448 (6)	0.0506 (8)	0.0380 (7)	−0.0121 (5)	−0.0067 (5)	−0.0139 (6)
C12	0.0507 (7)	0.0533 (8)	0.0435 (8)	−0.0120 (6)	−0.0096 (6)	−0.0169 (6)
C13	0.0636 (9)	0.0532 (9)	0.0485 (8)	−0.0137 (7)	−0.0140 (7)	−0.0116 (7)
C14	0.0893 (13)	0.0532 (10)	0.0946 (15)	−0.0123 (9)	−0.0219 (11)	−0.0158 (10)

Geometric parameters (Å, º) top

S1—C8	1.6776 (15)	C3—H3	0.9300
S2—C8	1.7470 (15)	C4—H4	0.9300
S2—C9	1.8479 (17)	C5—H5	0.9300
N1—C7	1.4760 (19)	C6—H6	0.9300
N1—C8	1.3246 (18)	C7—H7A	0.9700
N1—C10	1.4899 (18)	C7—H7B	0.9700
N2—C9	1.433 (2)	C9—H9A	0.9700
N2—C10	1.4326 (19)	C9—H9B	0.9700
N2—C11	1.4683 (18)	C10—H10A	0.9700
C1—C2	1.383 (2)	C10—H10B	0.9700
C1—C6	1.387 (2)	C11—H11A	0.9700
C1—C7	1.505 (2)	C11—H11B	0.9700
C2—C3	1.380 (3)	C12—H12A	0.9700
C3—C4	1.376 (3)	C12—H12B	0.9700
C4—C5	1.375 (3)	C13—H13A	0.9700
C5—C6	1.378 (3)	C13—H13B	0.9700
C11—C12	1.509 (2)	C14—H14A	0.9600
C12—C13	1.511 (2)	C14—H14B	0.9600
C13—C14	1.508 (3)	C14—H14C	0.9600
C2—H2	0.9300

S1···H6	3.1400	H9A···S1ⁱⁱⁱ	2.9300
S1···H7B	2.6000	H9B···S1^vi	2.8800
S1···H9Bⁱ	2.8800	H9B···H11B	2.2900
S1···H5ⁱⁱ	3.1600	H10A···C1	2.7100
S1···H9Aⁱⁱⁱ	2.9300	H10A···C2	2.9400
S1···H10Bⁱⁱⁱ	3.1600	H10A···C12	2.7500
S2···H11A	2.9400	H10A···H7A	2.4600
N1···H11A	2.6800	H10A···H12B	2.2400
C6···C8	3.593 (2)	H10B···H9A	2.2800
C8···C11	3.374 (2)	H10B···S1ⁱⁱⁱ	3.1600
C8···C6	3.593 (2)	H11A···S2	2.9400
C11···C8	3.374 (2)	H11A···N1	2.6800
C1···H12B	3.0800	H11A···C8	2.8300
C1···H10A	2.7100	H11A···H13B	2.5000
C2···H10A	2.9400	H11B···H9B	2.2900
C4···H14Bⁱ	3.0200	H11B···H13A	2.4400
C5···H13Aⁱ	3.0900	H11B···H13A^vii	2.5700
C8···H11A	2.8300	H12A···H14B	2.5600
C10···H12B	2.8200	H12A···H2^v	2.4800
C12···H10A	2.7500	H12B···C1	3.0800
C14···H4^iv	3.0800	H12B···C10	2.8200
H2···H7A	2.3400	H12B···H10A	2.2400
H2···H12A^v	2.4800	H12B···H14C	2.5700
H4···C14^iv	3.0800	H13A···C5^vi	3.0900
H4···H14A^iv	2.4500	H13A···H11B	2.4400
H5···S1ⁱⁱ	3.1600	H13A···H11B^vii	2.5700
H6···S1	3.1400	H13B···H11A	2.5000
H7A···H2	2.3400	H14A···H4^iv	2.4500
H7A···H10A	2.4600	H14B···C4^vi	3.0200
H7B···S1	2.6000	H14B···H12A	2.5600
H9A···H10B	2.2800	H14C···H12B	2.5700

C8—S2—C9	103.11 (7)	N1—C7—H7B	109.00
C7—N1—C8	122.01 (12)	C1—C7—H7A	109.00
C7—N1—C10	113.20 (11)	C1—C7—H7B	109.00
C8—N1—C10	124.74 (12)	H7A—C7—H7B	108.00
C9—N2—C10	109.50 (12)	S2—C9—H9A	109.00
C9—N2—C11	113.75 (12)	S2—C9—H9B	109.00
C10—N2—C11	115.24 (12)	N2—C9—H9A	109.00
C2—C1—C6	119.00 (14)	N2—C9—H9B	109.00
C2—C1—C7	120.70 (12)	H9A—C9—H9B	108.00
C6—C1—C7	120.29 (14)	N1—C10—H10A	109.00
C1—C2—C3	120.62 (15)	N1—C10—H10B	109.00
C2—C3—C4	119.82 (18)	N2—C10—H10A	109.00
C3—C4—C5	120.03 (18)	N2—C10—H10B	109.00
C4—C5—C6	120.31 (16)	H10A—C10—H10B	108.00
C1—C6—C5	120.21 (16)	N2—C11—H11A	109.00
N1—C7—C1	111.22 (11)	N2—C11—H11B	109.00
S1—C8—S2	112.92 (8)	C12—C11—H11A	109.00
S1—C8—N1	126.10 (11)	C12—C11—H11B	109.00
S2—C8—N1	120.94 (11)	H11A—C11—H11B	108.00
S2—C9—N2	113.13 (11)	C11—C12—H12A	109.00
N1—C10—N2	114.50 (11)	C11—C12—H12B	109.00
N2—C11—C12	114.63 (12)	C13—C12—H12A	109.00
C11—C12—C13	111.58 (12)	C13—C12—H12B	109.00
C12—C13—C14	113.99 (14)	H12A—C12—H12B	108.00
C1—C2—H2	120.00	C12—C13—H13A	109.00
C3—C2—H2	120.00	C12—C13—H13B	109.00
C2—C3—H3	120.00	C14—C13—H13A	109.00
C4—C3—H3	120.00	C14—C13—H13B	109.00
C3—C4—H4	120.00	H13A—C13—H13B	108.00
C5—C4—H4	120.00	C13—C14—H14A	109.00
C4—C5—H5	120.00	C13—C14—H14B	109.00
C6—C5—H5	120.00	C13—C14—H14C	109.00
C1—C6—H6	120.00	H14A—C14—H14B	109.00
C5—C6—H6	120.00	H14A—C14—H14C	109.00
N1—C7—H7A	109.00	H14B—C14—H14C	109.00

C9—S2—C8—S1	178.01 (8)	C9—N2—C11—C12	−165.23 (13)
C9—S2—C8—N1	−0.05 (12)	C10—N2—C11—C12	67.14 (17)
C8—S2—C9—N2	−29.53 (12)	C6—C1—C2—C3	−1.0 (2)
C8—N1—C7—C1	−108.21 (14)	C7—C1—C2—C3	177.50 (17)
C10—N1—C7—C1	74.18 (14)	C2—C1—C6—C5	1.0 (2)
C7—N1—C8—S1	2.68 (19)	C7—C1—C6—C5	−177.45 (17)
C7—N1—C8—S2	−179.54 (10)	C2—C1—C7—N1	−114.76 (15)
C10—N1—C8—S1	−180.00 (10)	C6—C1—C7—N1	63.68 (17)
C10—N1—C8—S2	−2.21 (18)	C1—C2—C3—C4	0.1 (3)
C7—N1—C10—N2	−147.79 (12)	C2—C3—C4—C5	0.7 (4)
C8—N1—C10—N2	34.68 (18)	C3—C4—C5—C6	−0.6 (4)
C10—N2—C9—S2	62.06 (13)	C4—C5—C6—C1	−0.2 (3)
C11—N2—C9—S2	−68.49 (15)	N2—C11—C12—C13	177.42 (13)
C9—N2—C10—N1	−65.65 (15)	C11—C12—C13—C14	−178.86 (16)
C11—N2—C10—N1	64.09 (17)

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+2, −z; (v) −x+1, −y+1, −z+1; (vi) x+1, y, z; (vii) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···S1	0.97	2.60	3.0978 (16)	112
C12—H12B···CgA	0.97	2.96	3.7937 (19)	145

Experimental details

Crystal data
Chemical formula	C₁₄H₂₀N₂S₂
M_r	280.44
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.6559 (2), 9.9586 (3), 11.1531 (4)
α, β, γ (°)	66.917 (2), 70.649 (1), 76.076 (2)
V (Å³)	732.03 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.26 × 0.20 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.922, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	15790, 3759, 2990
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.100, 1.03
No. of reflections	3759
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.20

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinG (Farrugia, 1999) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

S1—C8	1.6776 (15)	N1—C10	1.4899 (18)
S2—C8	1.7470 (15)	N2—C9	1.433 (2)
S2—C9	1.8479 (17)	N2—C10	1.4326 (19)
N1—C7	1.4760 (19)	N2—C11	1.4683 (18)
N1—C8	1.3246 (18)

C8—S2—C9	103.11 (7)	N1—C7—C1	111.22 (11)
C7—N1—C8	122.01 (12)	S1—C8—S2	112.92 (8)
C7—N1—C10	113.20 (11)	S1—C8—N1	126.10 (11)
C8—N1—C10	124.74 (12)	S2—C8—N1	120.94 (11)
C9—N2—C10	109.50 (12)	S2—C9—N2	113.13 (11)
C9—N2—C11	113.75 (12)	N1—C10—N2	114.50 (11)
C10—N2—C11	115.24 (12)	N2—C11—C12	114.63 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···S1	0.97	2.60	3.0978 (16)	112
C12—H12B···CgA	0.97	2.96	3.7937 (19)	145

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore.

References

Aboul-fadi, T., Hussein, M. A., El-Shorbagi, A. N. & Khalil, A. R. (2002). Arch. Pharm. Med. Chem. 9, 438–442. Google Scholar
Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Coro, J., Perez, R., Rodriguez, H., Suarez, M., Vega, C., Rolon, M., Montero, D., Nogal, J. J. & Gomez-Barrio, A. (2005). Bioorg. Med. Chem. 13, 3413–3421. Web of Science CrossRef PubMed CAS Google Scholar
Ertan, M., Ayyildiz, H. G. & Yulug, N. (1991). Arzneim. Forsch. Drug Res. 41, 1182–1185. CAS Google Scholar
Ertan, M., Tayman, A. B. & Yulung, N. (1996). Arch. Pharmacol. 323, 605–609. CrossRef Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Perez, R., Suarez, M., Ochoa, E., Rodriguez, H., Martin, N., Seoane, C., Novoa, H., Blaton, N., Peeters, O. M. & De Ranter, C. (2001). Tetrahedron, 57, 7361–7367. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar