3-[(N-Methyl-anilino)meth-yl]-5-(thio-phen-2-yl)-1,3,4-oxadiazole-2(3H)-thione.

In the title compound, C(14)H(13)N(3)OS(2), the thio-phene ring is disordered over two orientations by ca 180° about the C-C bond axis linking the ring to the rest of the mol-ecule, 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 thio-phene ring and the terminal phenyl ring, respectively. In the crystal, no significant inter-molecular hydrogen bonds are observed. The crystal packing is stabilized by π-π inter-actions [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 = 303.39

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.156

S = 0.97

2676 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812014419/is5107sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812014419/is5107Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H13N3OS2	F(000) = 632
Mr = 303.39	Dx = 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

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

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(Fo2) + (0.0811P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.001
2676 reflections	Δρmax = 0.16 e Å−3
220 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)