4,4'-[(1,3,4-Thia-diazole-2,5-di-yl)bis-(thio-methyl-ene)]dibenzonitrile.

The title mol-ecule, C(18)H(12)N(4)S(3), consists of three essentially planar fragments, viz. two methyl-substituted benzonitrile rings and a substituted thia-diazole ring. The dihedral angles between the substituted benzonitrile rings and the central thia-diazole ring are 28.29 (10) and 78.83 (6)°, and the dihedral angle between the two benzonitrile rings is 72.89 (7)°.

Related literature

For related literature, see: Tarafder et al., (2000 ▶); El-Shekeil et al. (1988 ▶); Jinxia et al. (2003 ▶).

Experimental

Crystal data

C18H12N4S3

M = 380.50

Monoclinic,

a = 7.6974 (15) Å

b = 8.4375 (17) Å

c = 27.272 (6) Å

β = 92.53 (3)°

V = 1769.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 293 (2) K

0.45 × 0.40 × 0.30 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.814, T max = 0.903

15327 measured reflections

4028 independent reflections

2754 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.115

S = 1.05

4028 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022848/fl2207sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022848/fl2207Isup2.hkl

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

C18H12N4S3	F(000) = 784
Mr = 380.50	Dx = 1.428 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12716 reflections
a = 7.6974 (15) Å	θ = 3.3–27.3°
b = 8.4375 (17) Å	µ = 0.43 mm−1
c = 27.272 (6) Å	T = 293 K
β = 92.53 (3)°	Prism, colorless
V = 1769.5 (6) Å3	0.45 × 0.40 × 0.30 mm
Z = 4

Rigaku Mercury2 diffractometer	4028 independent reflections
Radiation source: fine-focus sealed tube	2754 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
CCD_Profile_fitting scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.814, Tmax = 0.903	l = −35→35
15327 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0435P)2 + 0.4638P] where P = (Fo2 + 2Fc2)/3
4028 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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
C1	0.6555 (3)	0.3789 (3)	0.34124 (8)	0.0469 (5)
C2	0.9214 (3)	0.3764 (3)	0.38800 (8)	0.0476 (6)
C3	0.4395 (3)	0.2503 (3)	0.27094 (10)	0.0619 (7)
H3A	0.5357	0.2535	0.2491	0.074*
H3B	0.4455	0.1514	0.2891	0.074*
C4	0.2700 (3)	0.2614 (3)	0.24188 (9)	0.0494 (6)
C5	0.1254 (3)	0.1815 (3)	0.25715 (10)	0.0681 (8)
H5	0.1344	0.1193	0.2853	0.082*
C6	−0.0313 (3)	0.1926 (3)	0.23136 (10)	0.0675 (8)
H6	−0.1277	0.1379	0.2419	0.081*
C7	−0.0448 (3)	0.2853 (3)	0.18983 (8)	0.0463 (5)
C8	0.0971 (3)	0.3662 (3)	0.17434 (8)	0.0504 (6)
H8	0.0873	0.4293	0.1464	0.060*
C9	0.2533 (3)	0.3540 (3)	0.20014 (9)	0.0521 (6)
H9	0.3494	0.4087	0.1894	0.062*
C10	−0.2123 (3)	0.3038 (3)	0.16434 (9)	0.0576 (7)
C11	1.2030 (3)	0.2210 (3)	0.42467 (10)	0.0602 (7)
H11A	1.1265	0.1432	0.4386	0.072*
H11B	1.2195	0.1920	0.3908	0.072*
C12	1.3756 (3)	0.2188 (3)	0.45268 (8)	0.0489 (6)
C13	1.4027 (3)	0.2929 (3)	0.49739 (9)	0.0571 (6)
H13	1.3126	0.3500	0.5106	0.068*
C14	1.5604 (3)	0.2838 (3)	0.52286 (9)	0.0568 (6)
H14	1.5767	0.3346	0.5530	0.068*
C15	1.6945 (3)	0.1987 (3)	0.50351 (9)	0.0486 (6)
C16	1.6682 (3)	0.1221 (3)	0.45909 (9)	0.0563 (6)
H16	1.7575	0.0631	0.4462	0.068*
C17	1.5102 (3)	0.1328 (3)	0.43390 (9)	0.0553 (6)
H17	1.4936	0.0815	0.4039	0.066*
C18	1.8610 (3)	0.1876 (3)	0.52986 (9)	0.0558 (6)
N1	0.7442 (3)	0.2519 (3)	0.33425 (8)	0.0576 (5)
N2	0.9002 (3)	0.2507 (2)	0.36166 (8)	0.0573 (5)
N3	−0.3451 (3)	0.3216 (4)	0.14549 (9)	0.0848 (8)
N4	1.9930 (3)	0.1766 (3)	0.54989 (9)	0.0740 (7)
S1	0.75230 (9)	0.51067 (8)	0.38233 (2)	0.0594 (2)
S2	0.45247 (8)	0.41683 (8)	0.31298 (2)	0.0595 (2)
S3	1.10283 (9)	0.41341 (8)	0.42665 (3)	0.0642 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0514 (13)	0.0435 (13)	0.0451 (13)	−0.0003 (11)	−0.0051 (10)	−0.0021 (10)
C2	0.0521 (14)	0.0403 (13)	0.0499 (13)	−0.0007 (11)	−0.0046 (10)	0.0007 (10)
C3	0.0557 (15)	0.0595 (16)	0.0689 (17)	0.0079 (13)	−0.0167 (12)	−0.0152 (13)
C4	0.0475 (13)	0.0459 (14)	0.0540 (14)	0.0037 (11)	−0.0076 (11)	−0.0056 (11)
C5	0.0654 (17)	0.0724 (19)	0.0653 (17)	−0.0093 (15)	−0.0122 (14)	0.0269 (14)
C6	0.0509 (15)	0.081 (2)	0.0694 (18)	−0.0132 (14)	−0.0042 (13)	0.0272 (15)
C7	0.0423 (13)	0.0497 (14)	0.0463 (13)	0.0028 (11)	−0.0039 (10)	−0.0007 (10)
C8	0.0535 (14)	0.0511 (14)	0.0464 (13)	−0.0022 (12)	−0.0002 (11)	0.0072 (11)
C9	0.0470 (14)	0.0515 (15)	0.0577 (15)	−0.0082 (12)	0.0031 (11)	−0.0010 (12)
C10	0.0511 (16)	0.0691 (18)	0.0523 (15)	0.0021 (14)	0.0005 (12)	0.0068 (13)
C11	0.0546 (15)	0.0506 (15)	0.0741 (17)	−0.0006 (12)	−0.0122 (13)	−0.0093 (13)
C12	0.0502 (14)	0.0396 (13)	0.0561 (15)	−0.0038 (11)	−0.0052 (11)	0.0033 (11)
C13	0.0517 (14)	0.0607 (16)	0.0584 (15)	0.0103 (13)	−0.0014 (12)	−0.0096 (13)
C14	0.0565 (15)	0.0585 (16)	0.0547 (15)	0.0084 (13)	−0.0059 (12)	−0.0061 (12)
C15	0.0464 (13)	0.0427 (13)	0.0564 (15)	−0.0002 (11)	−0.0037 (11)	0.0103 (11)
C16	0.0526 (15)	0.0525 (15)	0.0640 (16)	0.0085 (12)	0.0038 (12)	0.0001 (13)
C17	0.0603 (16)	0.0527 (15)	0.0526 (15)	0.0027 (13)	−0.0019 (12)	−0.0080 (12)
C18	0.0553 (16)	0.0512 (15)	0.0607 (16)	0.0061 (13)	0.0001 (12)	0.0081 (12)
N1	0.0526 (12)	0.0538 (13)	0.0648 (13)	0.0076 (10)	−0.0160 (10)	−0.0139 (10)
N2	0.0525 (12)	0.0532 (13)	0.0647 (13)	0.0061 (10)	−0.0147 (10)	−0.0131 (10)
N3	0.0503 (14)	0.126 (2)	0.0771 (17)	0.0071 (15)	−0.0094 (12)	0.0204 (16)
N4	0.0572 (14)	0.0870 (18)	0.0765 (16)	0.0146 (13)	−0.0119 (12)	0.0068 (13)
S1	0.0657 (4)	0.0441 (4)	0.0664 (4)	0.0074 (3)	−0.0187 (3)	−0.0101 (3)
S2	0.0572 (4)	0.0556 (4)	0.0640 (4)	0.0118 (3)	−0.0159 (3)	−0.0095 (3)
S3	0.0646 (4)	0.0468 (4)	0.0786 (5)	0.0012 (3)	−0.0278 (3)	−0.0094 (3)

C1—N1	1.289 (3)	C9—H9	0.9300
C1—S1	1.725 (2)	C10—N3	1.134 (3)
C1—S2	1.742 (2)	C11—C12	1.503 (3)
C2—N2	1.287 (3)	C11—S3	1.799 (3)
C2—S1	1.727 (2)	C11—H11A	0.9700
C2—S3	1.740 (2)	C11—H11B	0.9700
C3—C4	1.499 (3)	C12—C13	1.378 (3)
C3—S2	1.814 (2)	C12—C17	1.382 (3)
C3—H3A	0.9700	C13—C14	1.374 (3)
C3—H3B	0.9700	C13—H13	0.9300
C4—C5	1.381 (3)	C14—C15	1.381 (3)
C4—C9	1.382 (3)	C14—H14	0.9300
C5—C6	1.372 (3)	C15—C16	1.380 (3)
C5—H5	0.9300	C15—C18	1.445 (3)
C6—C7	1.376 (3)	C16—C17	1.373 (3)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.371 (3)	C17—H17	0.9300
C7—C10	1.446 (3)	C18—N4	1.136 (3)
C8—C9	1.370 (3)	N1—N2	1.386 (3)
C8—H8	0.9300
N1—C1—S1	114.56 (17)	C12—C11—S3	111.49 (17)
N1—C1—S2	123.94 (18)	C12—C11—H11A	109.3
S1—C1—S2	121.49 (14)	S3—C11—H11A	109.3
N2—C2—S1	114.47 (17)	C12—C11—H11B	109.3
N2—C2—S3	124.36 (18)	S3—C11—H11B	109.3
S1—C2—S3	121.18 (14)	H11A—C11—H11B	108.0
C4—C3—S2	107.93 (16)	C13—C12—C17	118.7 (2)
C4—C3—H3A	110.1	C13—C12—C11	122.7 (2)
S2—C3—H3A	110.1	C17—C12—C11	118.6 (2)
C4—C3—H3B	110.1	C14—C13—C12	121.2 (2)
S2—C3—H3B	110.1	C14—C13—H13	119.4
H3A—C3—H3B	108.4	C12—C13—H13	119.4
C5—C4—C9	118.5 (2)	C13—C14—C15	119.6 (2)
C5—C4—C3	120.3 (2)	C13—C14—H14	120.2
C9—C4—C3	121.2 (2)	C15—C14—H14	120.2
C6—C5—C4	120.9 (2)	C16—C15—C14	119.7 (2)
C6—C5—H5	119.6	C16—C15—C18	119.9 (2)
C4—C5—H5	119.6	C14—C15—C18	120.4 (2)
C5—C6—C7	119.6 (2)	C17—C16—C15	120.0 (2)
C5—C6—H6	120.2	C17—C16—H16	120.0
C7—C6—H6	120.2	C15—C16—H16	120.0
C8—C7—C6	120.3 (2)	C16—C17—C12	120.7 (2)
C8—C7—C10	120.2 (2)	C16—C17—H17	119.6
C6—C7—C10	119.4 (2)	C12—C17—H17	119.6
C9—C8—C7	119.8 (2)	N4—C18—C15	178.6 (3)
C9—C8—H8	120.1	C1—N1—N2	112.22 (19)
C7—C8—H8	120.1	C2—N2—N1	112.35 (19)
C8—C9—C4	120.9 (2)	C1—S1—C2	86.40 (12)
C8—C9—H9	119.5	C1—S2—C3	99.23 (11)
C4—C9—H9	119.5	C2—S3—C11	98.82 (11)
N3—C10—C7	177.8 (3)