3-[(N-Methyl­anilino)meth­yl]-5-(thio­phen-2-yl)-1,3,4-oxadiazole-2(3H)-thione

El-Emam, A.A.; Al-Omar, M.A.; Ghabbour, H.A.; Fun, H.-K.; Chia, T.S.

doi:10.1107/S1600536812014419

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1345-o1346

doi:10.1107/S1600536812014419

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3-[(N-Methylanilino)methyl]-5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione

Ali A. El-Emam,^a Mohamed A. Al-Omar,^a Hazem A. Ghabbour,^a Hoong-Kun Fun ^b ^*‡ and Tze Shyang Chia ^b

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 28 March 2012; accepted 3 April 2012; online 13 April 2012)

In the title compound, C₁₄H₁₃N₃OS₂, the thiophene ring is disordered over two orientations by ca 180° about the C—C bond axis linking the ring to the rest of the molecule, with a site-occupancy ratio of 0.651 (5):0.349 (5). The central 1,3,4-oxadiazole-2(3H)-thione ring forms dihedral angles of 9.2 (5), 4.6 (11) and 47.70 (7)° with the major and minor parts of the disordered thiophene ring and the terminal phenyl ring, respectively. In the crystal, no significant intermolecular hydrogen bonds are observed. The crystal packing is stabilized by π–π interactions [centroid–centroid distance = 3.589 (2) Å].

Related literature

For the biological activity of 1,3,4-oxadiazole derivatives, see: Navarrete-Vázquez et al. (2007 ); Kadi et al. (2007 ); Padmavathi et al. (2009 ); El-Emam et al. (2004 ); Al-Deeb et al. (2006 ). For the synthesis of the title compound, see: Al-Omar (2010 ). For related 1,3,4-oxadiazole structures, see: Fun et al. (2011 ); El-Emam et al. (2012 ).

Experimental

Crystal data

C₁₄H₁₃N₃OS₂
M_r = 303.39
Monoclinic, P 2₁ /n
a = 11.9682 (8) Å
b = 7.4526 (5) Å
c = 17.0749 (14) Å
β = 108.072 (6)°
V = 1447.85 (18) Å³
Z = 4
Cu Kα radiation
μ = 3.32 mm⁻¹
T = 296 K
0.92 × 0.16 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.150, T_max = 0.754
10021 measured reflections
2676 independent reflections
1516 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.156
S = 0.97
2676 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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: 10.1107/S1600536812014419/is5107sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014419/is5107Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812014419/is5107Isup3.cml

checkCIF report

Comment top

Considerable attention has been devoted to 1,3,4-oxadiazole derivatives which have long been known for their diverse chemotherapeutic properties as antiviral agents against the HIV-1 viruses (El-Emam et al., 2004), antibacterial agents (Navarrete-Vázquez et al., 2007; Padmavathi et al., 2009) and anti-inflammatory agents (Kadi et al., 2007; Al-Deeb et al., 2006). The title compound (I) was synthesized among a series of 2-thienyl-1,3,4-oxadiazoles and related derivatives as potential antimicrobial agents (Al-Omar, 2010).

The molecular structure of the title compound is shown in Fig. 1. The thiophene ring is disordered by ca. 180° rotation about the C2—C3 bond axis with a site-occupancy ratio of 0.651 (5):0.349 (5). The central 1,3,4-oxadiazole-2(3H)-thione ring (N1/N2/C1/O1/C2/S2; maximum deviation = 0.0157 (12) Å at atom S2) forms dihedral angles of 9.23 (51), 4.6 (11) and 47.70 (7)° with the major and minor parts of the disordered thiophene ring [S1/C3–C6: maximum deviation = 0.024 (11) Å at atom C4 and S1A/C3/C4A–C6A: maximum deviation = 0.04 (3) Å at atom C6A] and the terminal phenyl ring (C9–C14), respectively.

In the crystal packing, no significant intermolecular hydrogen bondings are observed. The crystal packing is stabilized by a π–π interaction with Cg2···Cg4 distance = 3.589 (2) Å (symmetry code: 3/2-x, -1/2+y, 3/2-z), where Cg2 and Cg4 are the centroids of O1/C1/C2/N1/N2 and C9–C14 rings, respectively.

Related literature top

For the biological activity of 1,3,4-oxadiazole derivatives, see: Navarrete-Vázquez et al. (2007); Kadi et al. (2007); Padmavathi et al. (2009); El-Emam et al. (2004); Al-Deeb et al. (2006). For the synthesis of the title compound, see: Al-Omar (2010). For related 1,3,4-oxadiazole structures, see: Fun et al. (2011); El-Emam et al. (2012).

Experimental top

N-Methylaniline (214 mg, 2 mmol) and 37% formaldehyde solution (0.5 ml) were added to a solution of 5-(thiophen-2-yl)-1,3,4-oxadiazole-2-thiol (369 mg, 2 mmol) in ethanol (8 ml). The mixture was stirred at room temperature for 2 h and allowed to stand overnight. The precipitated crude product was filtered, washed with cold ethanol, dried, and crystallized from ethanol to yield 558 mg (92%) of the title compound (I) as colorless needle crystals. M.p.: 112–114 °C. ¹H NMR (CDCl₃, 500.13 MHz): δ 3.28 (s, 3H, CH₃), 5.64 (d, 2H, NCH₂N), 6.83–7.36 (m, 6H, Ar—H & Thiophene-H), 7.55 (d, 1H, Thiophene-H, J = 5.0 Hz), 7.70 (d, 1H, Thiophene-H, J = 5.0 Hz). ¹³C NMR (CDCl₃, 125.76 MHz): δ 39.54 (CH₃), 66.80 (CH₂), 113.72, 119.12, 123.65, 128.30, 129.36, 130.36, 131.07, 146.69 (Ar—C & Thiophene-C), 155.89 (Oxadiazole C-5), 176.32 (C=S).

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 with atom labels and 30% probability displacement ellipsoids. Atoms of the minor occupancy component are labelled with the suffix A.

3-[(N-Methylanilino)methyl]-5-(thiophen-2-yl)-1,3,4-oxadiazole- 2(3H)-thione top

Crystal data top

C₁₄H₁₃N₃OS₂	F(000) = 632
M_r = 303.39	D_x = 1.392 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 587 reflections
a = 11.9682 (8) Å	θ = 4.0–45.3°
b = 7.4526 (5) Å	µ = 3.32 mm⁻¹
c = 17.0749 (14) Å	T = 296 K
β = 108.072 (6)°	Needle, colorless
V = 1447.85 (18) Å³	0.92 × 0.16 × 0.09 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2676 independent reflections
Radiation source: fine-focus sealed tube	1516 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ϕ and ω scans	θ_max = 69.5°, θ_min = 4.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
T_min = 0.150, T_max = 0.754	k = −8→7
10021 measured reflections	l = −20→18

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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.156	w = 1/[σ²(F_o²) + (0.0811P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.001
2676 reflections	Δρ_max = 0.16 e Å⁻³
220 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0019 (4)

Crystal data top

C₁₄H₁₃N₃OS₂	V = 1447.85 (18) Å³
M_r = 303.39	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 11.9682 (8) Å	µ = 3.32 mm⁻¹
b = 7.4526 (5) Å	T = 296 K
c = 17.0749 (14) Å	0.92 × 0.16 × 0.09 mm
β = 108.072 (6)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2676 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1516 reflections with I > 2σ(I)
T_min = 0.150, T_max = 0.754	R_int = 0.066
10021 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 0.97	Δρ_max = 0.16 e Å⁻³
2676 reflections	Δρ_min = −0.20 e Å⁻³
220 parameters

Special details top

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)
S2	0.86759 (10)	0.22270 (15)	1.02672 (6)	0.0941 (4)
O1	0.6522 (2)	0.3191 (3)	0.93576 (13)	0.0697 (6)
N1	0.6491 (2)	0.2726 (3)	0.80711 (15)	0.0627 (7)
N2	0.7564 (2)	0.2228 (3)	0.86200 (15)	0.0628 (6)
N3	0.8999 (2)	0.2802 (4)	0.79288 (16)	0.0707 (7)
C1	0.7617 (3)	0.2516 (4)	0.94048 (19)	0.0672 (8)
C2	0.5908 (3)	0.3288 (4)	0.85393 (19)	0.0620 (8)
C3	0.4743 (3)	0.4013 (4)	0.8291 (2)	0.0651 (8)
C4	0.413 (2)	0.451 (3)	0.8829 (15)	0.093 (8)	0.651 (5)
H4A	0.4370	0.4340	0.9396	0.111*	0.651 (5)
C5	0.2989 (18)	0.542 (3)	0.8296 (11)	0.083 (5)	0.651 (5)
H5A	0.2436	0.5951	0.8503	0.100*	0.651 (5)
C6	0.2904 (15)	0.533 (2)	0.7508 (13)	0.092 (5)	0.651 (5)
H6A	0.2254	0.5768	0.7096	0.110*	0.651 (5)
S1	0.4025 (5)	0.4400 (7)	0.7304 (4)	0.0799 (9)	0.651 (5)
S1A	0.4022 (12)	0.4715 (16)	0.8908 (8)	0.0785 (19)	0.349 (5)
C6A	0.293 (3)	0.522 (6)	0.825 (3)	0.125 (17)	0.349 (5)
H6AA	0.2263	0.5592	0.8375	0.150*	0.349 (5)
C5A	0.292 (3)	0.512 (4)	0.745 (2)	0.112 (13)	0.349 (5)
H5AA	0.2322	0.5508	0.6995	0.135*	0.349 (5)
C4A	0.416 (3)	0.420 (5)	0.745 (2)	0.090 (13)	0.349 (5)
H4AA	0.4405	0.3878	0.7008	0.108*	0.349 (5)
C7	0.8480 (3)	0.1488 (4)	0.83120 (19)	0.0694 (8)
H7A	0.9088	0.0953	0.8767	0.083*
H7B	0.8143	0.0545	0.7918	0.083*
C8	0.9964 (3)	0.3838 (6)	0.8467 (2)	0.0919 (12)
H8A	0.9945	0.5035	0.8255	0.138*
H8B	1.0697	0.3280	0.8492	0.138*
H8C	0.9887	0.3883	0.9010	0.138*
C9	0.8762 (3)	0.2882 (4)	0.70804 (19)	0.0638 (8)
C10	0.9562 (3)	0.3627 (4)	0.6735 (2)	0.0806 (10)
H10A	1.0280	0.4050	0.7073	0.097*
C11	0.9293 (5)	0.3740 (6)	0.5890 (3)	0.1074 (15)
H11A	0.9838	0.4249	0.5669	0.129*
C12	0.8256 (6)	0.3131 (7)	0.5371 (3)	0.1167 (17)
H12A	0.8090	0.3218	0.4803	0.140*
C13	0.7459 (4)	0.2383 (5)	0.5709 (3)	0.0997 (14)
H13A	0.6744	0.1965	0.5363	0.120*
C14	0.7697 (3)	0.2240 (4)	0.6550 (2)	0.0766 (9)
H14A	0.7150	0.1717	0.6764	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S2	0.0998 (8)	0.1138 (8)	0.0625 (6)	0.0053 (5)	0.0162 (5)	−0.0036 (5)
O1	0.0771 (16)	0.0794 (14)	0.0594 (13)	−0.0076 (10)	0.0311 (12)	−0.0051 (9)
N1	0.0636 (17)	0.0670 (14)	0.0627 (15)	−0.0058 (12)	0.0270 (14)	−0.0015 (11)
N2	0.0631 (18)	0.0750 (15)	0.0545 (14)	−0.0025 (12)	0.0245 (14)	−0.0021 (11)
N3	0.0626 (17)	0.0918 (18)	0.0619 (16)	−0.0176 (12)	0.0255 (14)	−0.0119 (13)
C1	0.071 (2)	0.0719 (19)	0.0627 (19)	−0.0063 (14)	0.0268 (18)	−0.0024 (13)
C2	0.068 (2)	0.0644 (18)	0.0607 (18)	−0.0118 (14)	0.0297 (17)	−0.0054 (13)
C3	0.063 (2)	0.0739 (19)	0.065 (2)	−0.0117 (14)	0.030 (2)	−0.0079 (15)
C4	0.076 (11)	0.096 (9)	0.093 (13)	−0.001 (6)	0.010 (8)	−0.011 (6)
C5	0.092 (12)	0.080 (6)	0.099 (9)	−0.013 (5)	0.059 (9)	−0.012 (5)
C6	0.067 (9)	0.082 (6)	0.105 (11)	0.002 (5)	−0.002 (7)	0.002 (6)
S1	0.071 (2)	0.1025 (17)	0.0634 (11)	−0.0140 (14)	0.0171 (11)	−0.0039 (14)
S1A	0.082 (4)	0.087 (3)	0.082 (3)	−0.006 (3)	0.049 (3)	−0.006 (3)
C6A	0.044 (17)	0.13 (3)	0.20 (3)	0.002 (14)	0.03 (2)	−0.03 (2)
C5A	0.077 (18)	0.18 (3)	0.09 (2)	−0.040 (14)	0.050 (15)	0.024 (17)
C4A	0.044 (12)	0.130 (18)	0.11 (3)	0.011 (9)	0.041 (15)	0.031 (12)
C7	0.070 (2)	0.0747 (19)	0.067 (2)	0.0020 (15)	0.0258 (17)	0.0004 (15)
C8	0.077 (3)	0.115 (3)	0.080 (2)	−0.026 (2)	0.020 (2)	−0.016 (2)
C9	0.065 (2)	0.0672 (17)	0.0646 (19)	0.0082 (14)	0.0283 (17)	−0.0042 (13)
C10	0.088 (3)	0.078 (2)	0.090 (3)	0.0077 (17)	0.048 (2)	0.0057 (17)
C11	0.147 (4)	0.096 (3)	0.109 (4)	0.034 (3)	0.082 (3)	0.026 (3)
C12	0.175 (5)	0.110 (4)	0.072 (3)	0.050 (3)	0.049 (3)	0.013 (2)
C13	0.117 (4)	0.099 (3)	0.072 (2)	0.027 (2)	0.014 (3)	−0.010 (2)
C14	0.080 (2)	0.080 (2)	0.070 (2)	0.0079 (17)	0.024 (2)	−0.0098 (16)

Geometric parameters (Å, º) top

S2—C1	1.632 (3)	C6A—C5A	1.35 (6)
O1—C2	1.364 (3)	C6A—H6AA	0.9300
O1—C1	1.382 (4)	C5A—C4A	1.63 (5)
N1—C2	1.283 (4)	C5A—H5AA	0.9300
N1—N2	1.385 (3)	C4A—H4AA	0.9300
N2—C1	1.339 (4)	C7—H7A	0.9700
N2—C7	1.464 (4)	C7—H7B	0.9700
N3—C9	1.388 (4)	C8—H8A	0.9600
N3—C7	1.423 (4)	C8—H8B	0.9600
N3—C8	1.455 (4)	C8—H8C	0.9600
C2—C3	1.432 (4)	C9—C10	1.386 (4)
C3—C4	1.388 (19)	C9—C14	1.400 (5)
C3—C4A	1.39 (3)	C10—C11	1.379 (5)
C3—S1A	1.641 (12)	C10—H10A	0.9300
C3—S1	1.663 (6)	C11—C12	1.360 (6)
C4—C5	1.55 (3)	C11—H11A	0.9300
C4—H4A	0.9300	C12—C13	1.377 (6)
C5—C6	1.32 (3)	C12—H12A	0.9300
C5—H5A	0.9300	C13—C14	1.378 (5)
C6—S1	1.641 (19)	C13—H13A	0.9300
C6—H6A	0.9300	C14—H14A	0.9300
S1A—C6A	1.49 (5)

C2—O1—C1	106.2 (2)	C6A—C5A—C4A	107 (3)
C2—N1—N2	103.6 (2)	C6A—C5A—H5AA	126.3
C1—N2—N1	112.3 (3)	C4A—C5A—H5AA	126.3
C1—N2—C7	127.7 (3)	C3—C4A—C5A	102 (2)
N1—N2—C7	119.9 (2)	C3—C4A—H4AA	128.9
C9—N3—C7	122.2 (3)	C5A—C4A—H4AA	128.9
C9—N3—C8	120.1 (3)	N3—C7—N2	112.9 (3)
C7—N3—C8	116.7 (3)	N3—C7—H7A	109.0
N2—C1—O1	104.5 (3)	N2—C7—H7A	109.0
N2—C1—S2	131.6 (3)	N3—C7—H7B	109.0
O1—C1—S2	123.9 (2)	N2—C7—H7B	109.0
N1—C2—O1	113.4 (3)	H7A—C7—H7B	107.8
N1—C2—C3	127.3 (3)	N3—C8—H8A	109.5
O1—C2—C3	119.3 (3)	N3—C8—H8B	109.5
C4—C3—C4A	116.9 (19)	H8A—C8—H8B	109.5
C4—C3—C2	124.6 (12)	N3—C8—H8C	109.5
C4A—C3—C2	118.5 (15)	H8A—C8—H8C	109.5
C4A—C3—S1A	115.5 (15)	H8B—C8—H8C	109.5
C2—C3—S1A	126.0 (6)	C10—C9—N3	121.1 (3)
C4—C3—S1	114.3 (12)	C10—C9—C14	118.1 (3)
C2—C3—S1	121.0 (3)	N3—C9—C14	120.7 (3)
S1A—C3—S1	112.7 (6)	C11—C10—C9	120.1 (4)
C3—C4—C5	106.2 (16)	C11—C10—H10A	119.9
C3—C4—H4A	126.9	C9—C10—H10A	119.9
C5—C4—H4A	126.9	C12—C11—C10	122.1 (4)
C6—C5—C4	110.7 (15)	C12—C11—H11A	119.0
C6—C5—H5A	124.7	C10—C11—H11A	119.0
C4—C5—H5A	124.7	C11—C12—C13	118.2 (4)
C5—C6—S1	115.3 (13)	C11—C12—H12A	120.9
C5—C6—H6A	122.4	C13—C12—H12A	120.9
S1—C6—H6A	122.4	C12—C13—C14	121.4 (5)
C6—S1—C3	93.3 (8)	C12—C13—H13A	119.3
C6A—S1A—C3	96.2 (18)	C14—C13—H13A	119.3
C5A—C6A—S1A	118 (3)	C13—C14—C9	120.1 (4)
C5A—C6A—H6AA	120.8	C13—C14—H14A	120.0
S1A—C6A—H6AA	120.8	C9—C14—H14A	120.0

C2—N1—N2—C1	−0.7 (3)	C2—C3—S1—C6	−175.1 (6)
C2—N1—N2—C7	179.4 (2)	S1A—C3—S1—C6	−0.3 (8)
N1—N2—C1—O1	1.3 (3)	C4A—C3—S1A—C6A	3 (3)
C7—N2—C1—O1	−178.9 (3)	C2—C3—S1A—C6A	−179.0 (19)
N1—N2—C1—S2	−177.7 (2)	S1—C3—S1A—C6A	6 (2)
C7—N2—C1—S2	2.1 (5)	C3—S1A—C6A—C5A	−6 (4)
C2—O1—C1—N2	−1.3 (3)	S1A—C6A—C5A—C4A	7 (5)
C2—O1—C1—S2	177.8 (2)	C4—C3—C4A—C5A	4 (3)
N2—N1—C2—O1	−0.2 (3)	C2—C3—C4A—C5A	−177.8 (14)
N2—N1—C2—C3	178.2 (3)	S1A—C3—C4A—C5A	1 (3)
C1—O1—C2—N1	1.0 (3)	S1—C3—C4A—C5A	−52 (19)
C1—O1—C2—C3	−177.6 (3)	C6A—C5A—C4A—C3	−4 (4)
N1—C2—C3—C4	176.5 (11)	C9—N3—C7—N2	−106.3 (3)
O1—C2—C3—C4	−5.2 (11)	C8—N3—C7—N2	85.5 (4)
N1—C2—C3—C4A	−2.0 (17)	C1—N2—C7—N3	−107.6 (3)
O1—C2—C3—C4A	176.4 (17)	N1—N2—C7—N3	72.2 (3)
N1—C2—C3—S1A	179.8 (5)	C7—N3—C9—C10	−154.3 (3)
O1—C2—C3—S1A	−1.9 (6)	C8—N3—C9—C10	13.5 (4)
N1—C2—C3—S1	−6.1 (5)	C7—N3—C9—C14	26.8 (4)
O1—C2—C3—S1	172.2 (3)	C8—N3—C9—C14	−165.3 (3)
C4A—C3—C4—C5	−8 (2)	N3—C9—C10—C11	−178.1 (3)
C2—C3—C4—C5	173.5 (10)	C14—C9—C10—C11	0.8 (5)
S1A—C3—C4—C5	55 (29)	C9—C10—C11—C12	−0.3 (6)
S1—C3—C4—C5	−4.1 (17)	C10—C11—C12—C13	0.1 (6)
C3—C4—C5—C6	4 (2)	C11—C12—C13—C14	−0.3 (6)
C4—C5—C6—S1	−3 (2)	C12—C13—C14—C9	0.8 (5)
C5—C6—S1—C3	0.2 (15)	C10—C9—C14—C13	−1.0 (5)
C4—C3—S1—C6	2.6 (12)	N3—C9—C14—C13	177.9 (3)
C4A—C3—S1—C6	129 (20)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃N₃OS₂
M_r	303.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	11.9682 (8), 7.4526 (5), 17.0749 (14)
β (°)	108.072 (6)
V (Å³)	1447.85 (18)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.32
Crystal size (mm)	0.92 × 0.16 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.150, 0.754
No. of measured, independent and observed [I > 2σ(I)] reflections	10021, 2676, 1516
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.156, 0.97
No. of reflections	2676
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.20

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

AAEE, MAAO and HAG thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, for financial support. HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship.

References

Al-Deeb, O. A., Al-Omar, M. A., El-Brollosy, N. R., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2006). Arzneim. Forsch. Drug. Res. 56, 40–47. CAS Google Scholar
Al-Omar, M. A. (2010). Molecules, 15, 502–514. Web of Science CAS PubMed Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107–5113. Web of Science CrossRef PubMed CAS Google Scholar
El-Emam, A. A., Kadi, A. A., El-Brollosy, N. R., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o795. CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Arshad, S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3372. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235–242. Web of Science CrossRef PubMed CAS Google Scholar
Navarrete-Vázquez, G., Molina-Salinas, G. M., Duarte-Fajardo, Z. V., Vargas-Villarreal, J., Estrada-Soto, S. & Gonzàlez-Salazar, F. (2007). Bioorg. Med. Chem. 15, 5502–5508. Web of Science PubMed Google Scholar
Padmavathi, V., Reddy, G. S., Padmaja, A., Kondaiah, P. & Shazia, A. (2009). Eur. J. Med. Chem. 44, 2106–2112. Web of Science CrossRef PubMed 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