2-Methyl-5-[(3-methyl-4-nitro­benz­yl)sulfan­yl]-1,3,4-thia­diazole

Fun, H.-K.; Chantrapromma, S.; Chandrakantha, B.; Isloor, A.M.; Shetty, P.

doi:10.1107/S1600536810052505

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Pages o205-o206

https://doi.org/10.1107/S1600536810052505

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2-Methyl-5-[(3-methyl-4-nitrobenzyl)sulfanyl]-1,3,4-thiadiazole

Hoong-Kun Fun,^a ^*‡ Suchada Chantrapromma,^b § B. Chandrakantha,^c Arun M. Isloor ^d and Prakash Shetty ^e

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^cDepartment of Chemistry, Manipal Institute of Technology, Manipal 576 104, India, ^dOrganic Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and ^eDepartment of Printing, Manipal Institute of Technology, Manipal 576 104, India
^*Correspondence e-mail: hkfun@usm.my

(Received 10 December 2010; accepted 14 December 2010; online 24 December 2010)

The molecule of the title thiadiazole derivative, C₁₁H₁₁N₃O₂S₂, has a butterfly-like structure and the whole molecule is disordered with a site-occupancy ratio of 0.629 (4):0.371 (4). The molecule is disordered in such a way that the 3-methyl-4-nitrophenyl units of the major and minor components are approximately related by 180° rotation around the C—N bond axis. The dihedral angle between the 1,3,4-thiadiazole and benzene rings is 70.8 (4)° in the major component and 74.9 (6)° in the minor component. In the crystal, molecules are arranged into screw chains along the c axis. These chains are stacked along the b axis. Weak intermolecular C—H⋯O and C—H⋯π interactions and a short C⋯O contact [3.005 (7) Å] are present.

Related literature

For bond-length data, see: Allen et al. (1987 ). For related structures, see: Fun et al. (2011 ); Wang et al. (2010 ). For background to and applications of thiadiazole derivatives, see: Bernard et al. (1985 ); Chandrakantha et al. (2010 ); Isloor et al. (2010 ); Kalluraya et al. (2004 ); Oruç et al. (2004 ); Salimon et al. (2010 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₁H₁₁N₃O₂S₂
M_r = 281.37
Orthorhombic, P n a 2₁
a = 13.8210 (14) Å
b = 4.5720 (5) Å
c = 19.7929 (19) Å
V = 1250.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 100 K
0.46 × 0.30 × 0.10 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.831, T_max = 0.959
10019 measured reflections
3754 independent reflections
3250 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.091
S = 1.10
3754 reflections
330 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.42 e Å⁻³
Absolute structure: Flack (1983 ), 1234 Friedel pairs
Flack parameter: 0.04 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the S2/C9/N1/N2/C8, C1–C6 and C1A–C6A rings, respectively

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O2ⁱ	0.96	2.58	3.534 (11)	171
C7—H7B⋯Cg2ⁱⁱ	0.97	2.65	3.417 (6)	134
C7—H7B⋯Cg3ⁱⁱ	0.97	2.65	3.489 (6)	145
C7A—H7D⋯Cg2ⁱⁱ	0.97	2.63	3.269 (10)	124
C7A—H7D⋯Cg3ⁱⁱ	0.97	2.50	3.258 (10)	135
C10A—H10F⋯Cg1ⁱⁱⁱ	0.96	2.98	3.683 (18)	132
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) x, y-1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810052505/is2643sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810052505/is2643Isup2.hkl

checkCIF report

Comment top

Many classes of thiadiazole compounds have been intensely investigated with a number of them having found to be biologically and pharmacologically active. The 1,3,4-thiadiazole derivatives exhibit a wide spectrum of pharmacological and biological properties such as antituberculosis, anti-inflammatory, antifungal and antibacterial activities (Bernard et al., 1985; Chandrakantha et al., 2010; Isloor et al., 2010; Kalluraya et al., 2004; Oruç et al., 2004; Salimon et al., 2010). The title 1,3,4-thiadiazole derivative, (I), was synthesized in order to study its biological activity. Herein we report the crystal structure of (I).

The whole molecule of (I), C₁₁H₁₁N₃O₂S₂, is disordered over two sites with the major component and minor A components having refined site-occupancy ratio of 0.629 (3)/0.371 (3) and has a butterfly-like structure with a torsion angle C8–S1–C7–C6 = -79.8 (5)° in major component [-79.6 (9)° in minor A component]. The molecule is disordered in such a way that the 3-methyl-4-nitrophenyl unit in the major and minor components is related by 180° rotation. The dihedral angle between the 1,3,4-thiadiazole and benzene rings is 70.8 (4)° in the major component [74.9 (6)° in the minor A component]. In both components the nitro group is slightly twisted with respect to the attached benzene ring with the torsion angles O2–N3–C3–C2 = 8.4 (4)° and O3–N3–C3–C2 = -172.5 (3)° in the major component [the corresponding values are -12.1 (7) and 168.7 (5)° in the minor A component]. The bond distances are of normal values (Allen et al., 1987) and are comparable with the related structures (Fun et al., 2011; Wang et al., 2010).

In the crystal packing (Fig. 2), the molecules are arranged into screw chains along the c axis. These chains are stacked along the b axis. The crystal is stabilized by C—H···O and C—H···π weak interactions (Table 1). A short C···O contact [3.005 (7) Å; symmetry code: 1/2 + x, -1/2 - y, z] is observed.

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2011); Wang et al. (2010). For background to and applications of thiadiazole derivatives, see: Bernard et al. (1985); Chandrakantha et al. (2010); Isloor et al. (2010); Kalluraya et al. (2004); Oruç et al. (2004); Salimon et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was synthesized by adding 3-methyl-4-nitrobenzylbromide (3.47 g, 0.0151 mol) dropwise to a stirred solution of 5-methyl-1,3,4-thiadiazole-2-thiol (2.00 g, 0.0151 mol) and anhydrous potassium carbonate (4.16 g, 0.03 mol) in dry acetonitrile (50 ml) at room temperature and the reaction mixture was stirred at room temperature for 5 h. After the completion of reaction, the reaction mixture was filtered and the filtrate was concentrated. The crude product was recrystallized with hot ethanol to afford the title compound as yellow solid (2.20 g, 52% yield). Yellow plate-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from ethanol by the slow evaporation of the solvent at room temperature after several days (M.p. 443–445 K).

Structure description top

For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2011); Wang et al. (2010). For background to and applications of thiadiazole derivatives, see: Bernard et al. (1985); Chandrakantha et al. (2010); Isloor et al. (2010); Kalluraya et al. (2004); Oruç et al. (2004); Salimon et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Open bond show the minor A component.
	Fig. 2. The crystal packing of the title compound viewd along the b axis, showing screw chains running along the c axis.

2-Methyl-5-[(3-methyl-4-nitrobenzyl)sulfanyl]-1,3,4-thiadiazole top

Crystal data top

C₁₁H₁₁N₃O₂S₂	D_x = 1.494 Mg m⁻³
M_r = 281.37	Melting point = 443–445 K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3.12 reflections
a = 13.8210 (14) Å	θ = 30.0–2899°
b = 4.5720 (5) Å	µ = 0.42 mm⁻¹
c = 19.7929 (19) Å	T = 100 K
V = 1250.7 (2) Å³	Plate, yellow
Z = 4	0.46 × 0.30 × 0.10 mm
F(000) = 584

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	3754 independent reflections
Radiation source: sealed tube	3250 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 33.7°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→21
T_min = 0.831, T_max = 0.959	k = −7→6
10019 measured reflections	l = −30→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0501P)²] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
3754 reflections	Δρ_max = 0.45 e Å⁻³
330 parameters	Δρ_min = −0.42 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1234 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (6)

Crystal data top

C₁₁H₁₁N₃O₂S₂	V = 1250.7 (2) Å³
M_r = 281.37	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 13.8210 (14) Å	µ = 0.42 mm⁻¹
b = 4.5720 (5) Å	T = 100 K
c = 19.7929 (19) Å	0.46 × 0.30 × 0.10 mm

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	3754 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3250 reflections with I > 2σ(I)
T_min = 0.831, T_max = 0.959	R_int = 0.026
10019 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.091	Δρ_max = 0.45 e Å⁻³
S = 1.10	Δρ_min = −0.42 e Å⁻³
3754 reflections	Absolute structure: Flack (1983), 1234 Friedel pairs
330 parameters	Absolute structure parameter: 0.04 (6)
1 restraint

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.03130 (17)	0.3490 (8)	0.96362 (19)	0.0300 (3)	0.629 (4)
S2	0.1578 (2)	−0.0159 (8)	0.8790 (3)	0.0328 (6)	0.629 (4)
O2	−0.0136 (2)	−0.4228 (6)	1.29413 (14)	0.0518 (8)	0.629 (4)
O3	−0.1559 (3)	−0.4789 (7)	1.25002 (19)	0.0478 (9)	0.629 (4)
N1	0.2757 (4)	−0.0884 (15)	0.9791 (3)	0.0420 (11)	0.629 (4)
N2	0.2002 (4)	0.0921 (19)	1.0023 (4)	0.0346 (12)	0.629 (4)
N3	−0.0749 (2)	−0.3679 (6)	1.25069 (13)	0.0349 (6)	0.629 (4)
C1	0.0766 (3)	0.1353 (6)	1.14831 (15)	0.0289 (5)	0.629 (4)
H1A	0.1410	0.1947	1.1471	0.035*	0.629 (4)
C2	0.0461 (3)	−0.0654 (6)	1.19695 (14)	0.0289 (5)	0.629 (4)
H2A	0.0897	−0.1386	1.2285	0.035*	0.629 (4)
C3	−0.0489 (4)	−0.1543 (6)	1.19794 (14)	0.0262 (5)	0.629 (4)
C4	−0.1181 (3)	−0.0516 (6)	1.15221 (16)	0.0278 (5)	0.629 (4)
C5	−0.0843 (3)	0.1537 (7)	1.10453 (16)	0.0266 (6)	0.629 (4)
H5A	−0.1281	0.2301	1.0735	0.032*	0.629 (4)
C6	0.0110 (3)	0.2467 (7)	1.10173 (18)	0.0244 (5)	0.629 (4)
C7	0.0414 (3)	0.4654 (12)	1.0497 (3)	0.0319 (9)	0.629 (4)
H7A	0.1082	0.5185	1.0583	0.038*	0.629 (4)
H7B	0.0026	0.6404	1.0556	0.038*	0.629 (4)
C8	0.1361 (6)	0.136 (2)	0.9548 (6)	0.0258 (13)	0.629 (4)
C9	0.2662 (7)	−0.157 (3)	0.9161 (5)	0.0336 (14)	0.629 (4)
C10	0.3367 (8)	−0.341 (2)	0.8795 (5)	0.050 (2)	0.629 (4)
H10A	0.3740	−0.4522	0.9113	0.075*	0.629 (4)
H10B	0.3791	−0.2182	0.8535	0.075*	0.629 (4)
H10C	0.3029	−0.4718	0.8498	0.075*	0.629 (4)
S1A	0.0080 (3)	0.3638 (14)	0.9625 (4)	0.0331 (7)	0.371 (4)
S2A	0.1561 (5)	−0.0237 (15)	0.8860 (6)	0.0398 (14)	0.371 (4)
O2A	−0.0852 (4)	−0.5184 (9)	1.2745 (3)	0.0507 (12)	0.371 (4)
O3A	−0.2234 (4)	−0.4513 (11)	1.2302 (3)	0.0600 (14)	0.371 (4)
N1A	0.2532 (5)	−0.046 (2)	0.9912 (4)	0.0311 (14)	0.371 (4)
N2A	0.1738 (7)	0.115 (3)	1.0101 (6)	0.0321 (15)	0.371 (4)
N3A	−0.1378 (4)	−0.3973 (13)	1.2341 (3)	0.0327 (11)	0.371 (4)
C1A	0.0286 (4)	0.1374 (9)	1.1504 (2)	0.0254 (8)	0.371 (4)
H1B	0.0910	0.2118	1.1541	0.031*	0.371 (4)
C2A	−0.0029 (4)	−0.0698 (9)	1.1981 (2)	0.0196 (7)	0.371 (4)
C3A	−0.0968 (4)	−0.1718 (9)	1.1884 (2)	0.0232 (8)	0.371 (4)
C4A	−0.1560 (4)	−0.0847 (11)	1.1368 (3)	0.0292 (10)	0.371 (4)
H4B	−0.2178	−0.1628	1.1322	0.035*	0.371 (4)
C5A	−0.1220 (5)	0.1226 (12)	1.0913 (3)	0.0320 (11)	0.371 (4)
H5B	−0.1613	0.1869	1.0562	0.038*	0.371 (4)
C6A	−0.0289 (5)	0.2336 (11)	1.0987 (3)	0.0238 (10)	0.371 (4)
C7A	0.0060 (7)	0.479 (2)	1.0507 (5)	0.0379 (19)	0.371 (4)
H7C	0.0705	0.5389	1.0640	0.045*	0.371 (4)
H7D	−0.0365	0.6463	1.0553	0.045*	0.371 (4)
C8A	0.1157 (10)	0.166 (4)	0.9600 (8)	0.0220 (18)	0.371 (4)
C9A	0.2489 (11)	−0.138 (4)	0.9296 (7)	0.0294 (19)	0.371 (4)
C10A	0.3250 (10)	−0.317 (4)	0.8965 (8)	0.043 (3)	0.371 (4)
H10D	0.3736	−0.3676	0.9291	0.065*	0.371 (4)
H10E	0.3539	−0.2066	0.8606	0.065*	0.371 (4)
H10F	0.2966	−0.4921	0.8786	0.065*	0.371 (4)
C11	−0.2234 (2)	−0.1340 (8)	1.14972 (19)	0.0438 (7)	0.629 (4)
H11A	−0.2292	−0.3416	1.1436	0.066*	0.629 (4)
H11B	−0.2540	−0.0349	1.1127	0.066*	0.629 (4)
H11C	−0.2541	−0.0783	1.1913	0.066*	0.629 (4)
C11A	0.0647 (3)	−0.1528 (12)	1.2541 (2)	0.0357 (11)	0.371 (4)
H11D	0.1235	−0.0425	1.2500	0.053*	0.371 (4)
H11E	0.0790	−0.3579	1.2513	0.053*	0.371 (4)
H11F	0.0348	−0.1111	1.2968	0.053*	0.371 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0368 (8)	0.0311 (6)	0.0220 (4)	0.0045 (6)	−0.0004 (8)	0.0056 (4)
S2	0.0371 (10)	0.0316 (9)	0.0298 (14)	0.0018 (7)	−0.0078 (6)	0.0015 (6)
O2	0.0612 (16)	0.0623 (16)	0.0319 (13)	0.0179 (13)	0.0060 (11)	0.0219 (12)
O3	0.067 (2)	0.0426 (16)	0.0343 (17)	−0.0141 (14)	0.0107 (15)	0.0050 (11)
N1	0.032 (2)	0.051 (2)	0.043 (3)	0.0138 (15)	0.0031 (15)	0.0084 (18)
N2	0.027 (2)	0.050 (3)	0.027 (2)	−0.003 (2)	−0.0033 (17)	0.0076 (17)
N3	0.0559 (17)	0.0290 (12)	0.0197 (10)	0.0099 (10)	0.0105 (10)	0.0022 (9)
C1	0.0360 (15)	0.0260 (12)	0.0248 (12)	−0.0017 (11)	−0.0003 (11)	−0.0036 (9)
C2	0.0373 (16)	0.0297 (12)	0.0197 (11)	0.0073 (11)	−0.0029 (10)	−0.0019 (9)
C3	0.0370 (17)	0.0252 (12)	0.0163 (11)	0.0075 (13)	0.0031 (11)	0.0012 (9)
C4	0.0294 (14)	0.0300 (12)	0.0241 (13)	0.0047 (11)	0.0033 (11)	−0.0032 (11)
C5	0.0340 (18)	0.0252 (12)	0.0206 (12)	0.0064 (13)	−0.0037 (12)	−0.0014 (10)
C6	0.0324 (14)	0.0178 (10)	0.0230 (11)	−0.0012 (12)	0.0007 (13)	−0.0038 (9)
C7	0.052 (2)	0.0167 (14)	0.0273 (16)	0.0025 (17)	0.005 (2)	−0.0016 (11)
C8	0.030 (3)	0.019 (2)	0.029 (3)	−0.0045 (17)	0.0014 (19)	0.0020 (18)
C9	0.027 (3)	0.0321 (19)	0.041 (4)	−0.0015 (19)	0.0047 (19)	0.011 (2)
C10	0.044 (3)	0.038 (2)	0.068 (6)	0.0098 (17)	0.011 (3)	0.008 (3)
S1A	0.050 (2)	0.0273 (7)	0.0214 (7)	0.0055 (15)	0.0021 (18)	0.0007 (6)
S2A	0.054 (2)	0.042 (2)	0.0236 (17)	−0.0138 (14)	−0.0082 (9)	−0.0056 (12)
O2A	0.063 (3)	0.037 (2)	0.052 (3)	0.0047 (17)	0.016 (2)	0.019 (2)
O3A	0.042 (2)	0.085 (3)	0.053 (3)	−0.029 (2)	0.008 (2)	0.006 (2)
N1A	0.028 (4)	0.038 (3)	0.027 (3)	0.007 (3)	−0.006 (2)	−0.002 (2)
N2A	0.035 (4)	0.036 (3)	0.025 (3)	−0.005 (4)	−0.004 (3)	0.001 (2)
N3A	0.032 (2)	0.035 (3)	0.031 (3)	−0.0079 (18)	0.0141 (19)	−0.0017 (19)
C1A	0.031 (2)	0.0239 (18)	0.0215 (19)	−0.0072 (17)	0.0047 (17)	−0.0059 (14)
C2A	0.0142 (18)	0.0248 (19)	0.0199 (17)	0.0023 (16)	0.0023 (14)	−0.0001 (13)
C3A	0.0221 (19)	0.0241 (18)	0.023 (2)	0.0049 (16)	0.0023 (16)	−0.0002 (15)
C4A	0.022 (2)	0.031 (2)	0.034 (3)	0.0036 (17)	−0.0040 (18)	−0.0013 (18)
C5A	0.039 (3)	0.025 (2)	0.032 (3)	0.010 (2)	−0.005 (2)	0.0006 (18)
C6A	0.034 (3)	0.0163 (17)	0.021 (2)	−0.003 (2)	0.005 (2)	−0.0015 (14)
C7A	0.070 (5)	0.020 (2)	0.024 (2)	0.014 (4)	0.015 (4)	−0.0003 (17)
C8A	0.039 (6)	0.015 (3)	0.012 (2)	−0.004 (3)	0.002 (4)	0.000 (2)
C9A	0.030 (5)	0.028 (4)	0.030 (5)	−0.008 (4)	0.003 (3)	0.010 (3)
C10A	0.030 (4)	0.046 (6)	0.053 (6)	−0.010 (4)	0.000 (4)	0.009 (4)
C11	0.0323 (13)	0.062 (2)	0.0372 (16)	−0.0044 (12)	0.0038 (11)	0.0024 (14)
C11A	0.0303 (18)	0.052 (3)	0.025 (2)	0.0046 (17)	−0.0020 (16)	0.0000 (18)

Geometric parameters (Å, º) top

S1—C8	1.756 (7)	S2A—C8A	1.791 (17)
S1—C7	1.791 (8)	O2A—N3A	1.213 (9)
S2—C8	1.678 (12)	O3A—N3A	1.211 (7)
S2—C9	1.790 (12)	N1A—C9A	1.291 (16)
O2—N3	1.233 (4)	N1A—N2A	1.376 (11)
O3—N3	1.229 (5)	N2A—C8A	1.30 (2)
N1—C9	1.293 (11)	N3A—C3A	1.485 (7)
N1—N2	1.407 (7)	C1A—C6A	1.368 (8)
N2—C8	1.306 (14)	C1A—C2A	1.407 (6)
N3—C3	1.474 (4)	C1A—H1B	0.9300
C1—C6	1.390 (5)	C2A—C3A	1.391 (7)
C1—C2	1.396 (4)	C2A—C11A	1.498 (7)
C1—H1A	0.9300	C3A—C4A	1.369 (7)
C2—C3	1.374 (6)	C4A—C5A	1.389 (8)
C2—H2A	0.9300	C4A—H4B	0.9300
C3—C4	1.397 (5)	C5A—C6A	1.391 (8)
C4—C5	1.410 (4)	C5A—H5B	0.9300
C4—C11	1.504 (5)	C6A—C7A	1.546 (11)
C5—C6	1.385 (4)	C7A—H7C	0.9700
C5—H5A	0.9300	C7A—H7D	0.9700
C6—C7	1.495 (7)	C9A—C10A	1.48 (2)
C7—H7A	0.9700	C10A—H10D	0.9600
C7—H7B	0.9700	C10A—H10E	0.9600
C9—C10	1.476 (13)	C10A—H10F	0.9600
C10—H10A	0.9600	C11—H11A	0.9600
C10—H10B	0.9600	C11—H11B	0.9600
C10—H10C	0.9600	C11—H11C	0.9600
S1A—C8A	1.742 (12)	C11A—H11D	0.9600
S1A—C7A	1.822 (13)	C11A—H11E	0.9600
S2A—C9A	1.63 (2)	C11A—H11F	0.9600

C8—S1—C7	101.3 (5)	O2A—N3A—C3A	119.3 (5)
C8—S2—C9	86.1 (5)	C6A—C1A—C2A	122.5 (5)
C9—N1—N2	112.4 (7)	C6A—C1A—H1B	118.7
C8—N2—N1	111.0 (6)	C2A—C1A—H1B	118.7
O3—N3—O2	123.3 (3)	C3A—C2A—C1A	115.0 (4)
O3—N3—C3	119.2 (3)	C3A—C2A—C11A	126.8 (4)
O2—N3—C3	117.5 (3)	C1A—C2A—C11A	118.2 (5)
C6—C1—C2	120.1 (3)	C4A—C3A—C2A	124.3 (4)
C6—C1—H1A	120.0	C4A—C3A—N3A	115.4 (5)
C2—C1—H1A	120.0	C2A—C3A—N3A	120.3 (5)
C3—C2—C1	119.6 (3)	C3A—C4A—C5A	118.7 (5)
C3—C2—H2A	120.2	C3A—C4A—H4B	120.7
C1—C2—H2A	120.2	C5A—C4A—H4B	120.7
C2—C3—C4	123.0 (3)	C4A—C5A—C6A	119.6 (5)
C2—C3—N3	116.0 (3)	C4A—C5A—H5B	120.2
C4—C3—N3	121.0 (4)	C6A—C5A—H5B	120.2
C3—C4—C5	115.5 (3)	C1A—C6A—C5A	119.9 (5)
C3—C4—C11	126.8 (3)	C1A—C6A—C7A	120.8 (7)
C5—C4—C11	117.7 (3)	C5A—C6A—C7A	119.2 (7)
C6—C5—C4	123.1 (3)	C6A—C7A—S1A	112.6 (7)
C6—C5—H5A	118.5	C6A—C7A—H7C	109.1
C4—C5—H5A	118.5	S1A—C7A—H7C	109.1
C5—C6—C1	118.8 (3)	C6A—C7A—H7D	109.1
C5—C6—C7	120.0 (3)	S1A—C7A—H7D	109.1
C1—C6—C7	121.2 (3)	H7C—C7A—H7D	107.8
C6—C7—S1	115.7 (4)	N2A—C8A—S1A	126.9 (11)
C6—C7—H7A	108.3	N2A—C8A—S2A	110.2 (9)
S1—C7—H7A	108.3	S1A—C8A—S2A	122.8 (10)
C6—C7—H7B	108.3	N1A—C9A—C10A	124.2 (16)
S1—C7—H7B	108.3	N1A—C9A—S2A	115.5 (11)
H7A—C7—H7B	107.4	C10A—C9A—S2A	120.1 (12)
N2—C8—S2	117.3 (5)	C9A—C10A—H10D	109.5
N2—C8—S1	124.9 (8)	C9A—C10A—H10E	109.5
S2—C8—S1	117.7 (7)	H10D—C10A—H10E	109.5
N1—C9—C10	123.1 (10)	C9A—C10A—H10F	109.5
N1—C9—S2	113.1 (6)	H10D—C10A—H10F	109.5
C10—C9—S2	123.8 (9)	H10E—C10A—H10F	109.5
C8A—S1A—C7A	101.0 (7)	C2A—C11A—H11D	109.5
C9A—S2A—C8A	88.2 (8)	C2A—C11A—H11E	109.5
C9A—N1A—N2A	113.3 (10)	H11D—C11A—H11E	109.5
C8A—N2A—N1A	112.5 (10)	C2A—C11A—H11F	109.5
O3A—N3A—O2A	122.3 (6)	H11D—C11A—H11F	109.5
O3A—N3A—C3A	118.4 (6)	H11E—C11A—H11F	109.5

C9—N1—N2—C8	2.8 (11)	C9A—N1A—N2A—C8A	−6.5 (18)
C6—C1—C2—C3	0.7 (4)	C6A—C1A—C2A—C3A	0.6 (6)
C1—C2—C3—C4	−0.3 (4)	C6A—C1A—C2A—C11A	−178.0 (4)
C1—C2—C3—N3	179.7 (2)	C1A—C2A—C3A—C4A	0.5 (6)
O3—N3—C3—C2	−172.5 (3)	C11A—C2A—C3A—C4A	178.9 (4)
O2—N3—C3—C2	8.4 (4)	C1A—C2A—C3A—N3A	178.3 (4)
O3—N3—C3—C4	7.4 (4)	C11A—C2A—C3A—N3A	−3.3 (7)
O2—N3—C3—C4	−171.6 (3)	O3A—N3A—C3A—C4A	−12.1 (7)
C2—C3—C4—C5	−0.5 (4)	O2A—N3A—C3A—C4A	168.7 (5)
N3—C3—C4—C5	179.6 (2)	O3A—N3A—C3A—C2A	169.9 (5)
C2—C3—C4—C11	−179.5 (3)	O2A—N3A—C3A—C2A	−9.3 (7)
N3—C3—C4—C11	0.6 (4)	C2A—C3A—C4A—C5A	−1.2 (7)
C3—C4—C5—C6	0.9 (4)	N3A—C3A—C4A—C5A	−179.1 (5)
C11—C4—C5—C6	−180.0 (3)	C3A—C4A—C5A—C6A	0.8 (8)
C4—C5—C6—C1	−0.6 (5)	C2A—C1A—C6A—C5A	−1.0 (7)
C4—C5—C6—C7	−179.9 (3)	C2A—C1A—C6A—C7A	175.3 (5)
C2—C1—C6—C5	−0.3 (4)	C4A—C5A—C6A—C1A	0.2 (8)
C2—C1—C6—C7	179.1 (3)	C4A—C5A—C6A—C7A	−176.1 (6)
C5—C6—C7—S1	−63.8 (4)	C1A—C6A—C7A—S1A	121.8 (6)
C1—C6—C7—S1	116.9 (4)	C5A—C6A—C7A—S1A	−61.9 (7)
C8—S1—C7—C6	−79.8 (5)	C8A—S1A—C7A—C6A	−79.6 (9)
N1—N2—C8—S2	−1.9 (12)	N1A—N2A—C8A—S1A	−179.7 (12)
N1—N2—C8—S1	−179.9 (7)	N1A—N2A—C8A—S2A	5.2 (17)
C9—S2—C8—N2	0.4 (9)	C7A—S1A—C8A—N2A	2.0 (18)
C9—S2—C8—S1	178.6 (7)	C7A—S1A—C8A—S2A	176.5 (10)
C7—S1—C8—N2	−0.7 (11)	C9A—S2A—C8A—N2A	−2.4 (14)
C7—S1—C8—S2	−178.7 (6)	C9A—S2A—C8A—S1A	−177.7 (12)
N2—N1—C9—C10	179.0 (9)	N2A—N1A—C9A—C10A	179.9 (13)
N2—N1—C9—S2	−2.5 (10)	N2A—N1A—C9A—S2A	4.6 (16)
C8—S2—C9—N1	1.3 (8)	C8A—S2A—C9A—N1A	−1.3 (13)
C8—S2—C9—C10	179.7 (10)	C8A—S2A—C9A—C10A	−176.8 (14)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the S2/C9/N1/N2/C8, C1–C6 and C1A–C6A rings, respectively

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O2ⁱ	0.96	2.58	3.534 (11)	171
C7—H7B···Cg2ⁱⁱ	0.97	2.65	3.417 (6)	134
C7—H7B···Cg3ⁱⁱ	0.97	2.65	3.489 (6)	145
C7A—H7D···Cg2ⁱⁱ	0.97	2.63	3.269 (10)	124
C7A—H7D···Cg3ⁱⁱ	0.97	2.50	3.258 (10)	135
C10A—H10F···Cg1ⁱⁱⁱ	0.96	2.98	3.683 (18)	132

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁N₃O₂S₂
M_r	281.37
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	13.8210 (14), 4.5720 (5), 19.7929 (19)
V (Å³)	1250.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.46 × 0.30 × 0.10

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.831, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	10019, 3754, 3250
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.780

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.091, 1.10
No. of reflections	3754
No. of parameters	330
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.42
Absolute structure	Flack (1983), 1234 Friedel pairs
Absolute structure parameter	0.04 (6)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the S2/C9/N1/N2/C8, C1–C6 and C1A–C6A rings, respectively

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O2ⁱ	0.96	2.58	3.534 (11)	171
C7—H7B···Cg2ⁱⁱ	0.97	2.65	3.417 (6)	134
C7—H7B···Cg3ⁱⁱ	0.97	2.65	3.489 (6)	145
C7A—H7D···Cg2ⁱⁱ	0.97	2.63	3.269 (10)	124
C7A—H7D···Cg3ⁱⁱ	0.97	2.50	3.258 (10)	135
C10A—H10F···Cg1ⁱⁱⁱ	0.96	2.98	3.683 (18)	132

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

AMI is thankful to the Director of the National Institute of Technology for providing research facilities and also thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India, for the Young Scientist award. SC thanks the Prince of Songkla University for generous support through the Crystal Materials Research Unit. The authors also thank Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bernard, A. M., Cocco, M. T., Maccioni, A. & Plumitallo, A. (1985). Farmaco, 40, 259–271. CAS Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chandrakantha, B., Shetty, P., Nambiyar, V., Isloor, N. & Isloor, A. M. (2010). Eur. J. Med. Chem. 45, 1206–1210. Web of Science CrossRef CAS PubMed Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Chantrapromma, S., Chandrakantha, B., Isloor, A. M. & Shetty, P. (2011). Acta Cryst. E67, o163. Web of Science CrossRef IUCr Journals Google Scholar
Isloor, A. M., Kalluraya, B. & Pai, K. S. (2010). Eur. J. Med. Chem. 45, 825–830. Web of Science CrossRef PubMed CAS Google Scholar
Kalluraya, B., Jagadeesha, R. L. & Isloor, A. M. (2004). Indian J. Het. Chem. 13, 245–248. CAS Google Scholar
Oruç, E. E., Rollas, S., Kandemirli, F., Shvets, N. & Dimoglo, A. S. (2004). J. Med. Chem. 47, 6760–6767. Web of Science PubMed Google Scholar
Salimon, J., Salih, N., Hameed, A., Ibraheem, H. & Yousif, E. (2010). J. Appl. Sci. Res. 6, 866–870. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, H., Gao, Y. & Wang, W. (2010). Acta Cryst. E66, o3085. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 1| January 2011| Pages o205-o206

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