4-(Phenyl-sulfan-yl)benzene-1,2-dicarbonitrile.

In the title compound, C(14)H(8)N(2)S, the dicyano-substituted aromatic ring and the phenyl ring attached to the central S atom adopt an angular V-shaped configuration. The dihedral angle between the rings is 103.6°.

Related literature

The title compound is a precusor in the synthesis of phthalocyanine derivatives. For applications of phthalocyanines, see: Ao et al. (1995 ▶); Rey et al. (1998 ▶); Zhang et al. (2009 ▶); Beltrán et al. (2004 ▶); LukCentyanets (1999 ▶); Shirk & Pong (2000 ▶).

Experimental

Crystal data

C14H8N2S

M = 236.28

Monoclinic,

a = 7.8515 (7) Å

b = 9.7739 (9) Å

c = 15.6248 (14) Å

β = 91.544 (2)°

V = 1198.61 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 273 K

0.31 × 0.25 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.928, T max = 0.950

5758 measured reflections

2102 independent reflections

1818 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.04

2102 reflections

154 parameters

17 restraints

H-atom parameters not refined

Δρmax = 0.33 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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 global, I. DOI: 10.1107/S1600536810043011/pb2042sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043011/pb2042Isup2.hkl

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

C14H8N2S	F(000) = 488
Mr = 236.28	Dx = 1.309 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2102 reflections
a = 7.8515 (7) Å	θ = 2.2–25.0°
b = 9.7739 (9) Å	µ = 0.25 mm−1
c = 15.6248 (14) Å	T = 273 K
β = 91.544 (2)°	Block, colorless
V = 1198.61 (19) Å3	0.31 × 0.25 × 0.21 mm
Z = 4

Bruker APEXII CCD diffractometer	2102 independent reflections
Radiation source: fine-focus sealed tube	1818 reflections with I > 2σ(I)
graphite	Rint = 0.015
phi and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→9
Tmin = 0.928, Tmax = 0.950	k = −11→11
5758 measured reflections	l = −14→18

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters not refined
S = 1.04	w = 1/[σ2(Fo2) + (0.043P)2 + 0.3751P] where P = (Fo2 + 2Fc2)/3
2102 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.33 e Å−3
17 restraints	Δρmin = −0.38 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
S1	1.02062 (6)	−0.13035 (5)	0.20832 (4)	0.0706 (2)
N1	1.1713 (2)	0.44401 (17)	−0.06030 (11)	0.0689 (5)
N2	1.5357 (2)	0.1851 (2)	−0.00461 (12)	0.0759 (5)
C1	1.10678 (19)	0.23614 (16)	0.03502 (9)	0.0428 (4)
C2	1.23816 (19)	0.14420 (16)	0.05715 (10)	0.0437 (4)
C3	1.2075 (2)	0.03475 (17)	0.11030 (11)	0.0496 (4)
H3	1.2954	−0.0253	0.1252	0.060*
C4	1.0448 (2)	0.01386 (16)	0.14187 (11)	0.0466 (4)
C5	0.9148 (2)	0.10349 (18)	0.11842 (11)	0.0508 (4)
H5	0.8056	0.0890	0.1383	0.061*
C6	0.9453 (2)	0.21380 (17)	0.06595 (11)	0.0504 (4)
H6	0.8571	0.2735	0.0512	0.061*
C7	1.1412 (2)	0.35200 (18)	−0.01832 (11)	0.0498 (4)
C8	1.4050 (2)	0.16575 (18)	0.02351 (12)	0.0539 (4)
C9	0.8157 (2)	−0.10711 (17)	0.25164 (11)	0.0493 (4)
C10	0.7880 (3)	−0.0083 (2)	0.31328 (12)	0.0629 (5)
H10	0.8762	0.0491	0.3316	0.075*
C11	0.6272 (3)	0.0044 (2)	0.34748 (13)	0.0723 (6)
H11	0.6075	0.0708	0.3887	0.087*
C12	0.4977 (3)	−0.0807 (2)	0.32069 (14)	0.0724 (6)
H12	0.3900	−0.0715	0.3434	0.087*
C13	0.5263 (3)	−0.1780 (2)	0.26123 (15)	0.0736 (6)
H13	0.4380	−0.2358	0.2437	0.088*
C14	0.6849 (2)	−0.1927 (2)	0.22626 (12)	0.0601 (5)
H14	0.7032	−0.2604	0.1857	0.072*

	U11	U22	U33	U12	U13	U23
S1	0.0552 (3)	0.0589 (3)	0.0988 (4)	0.0124 (2)	0.0230 (3)	0.0307 (3)
N1	0.0704 (11)	0.0639 (10)	0.0736 (11)	0.0084 (8)	0.0214 (8)	0.0192 (9)
N2	0.0501 (10)	0.0816 (12)	0.0971 (13)	0.0050 (8)	0.0241 (9)	0.0081 (10)
C1	0.0433 (8)	0.0425 (8)	0.0428 (8)	0.0005 (7)	0.0046 (6)	−0.0009 (7)
C2	0.0387 (8)	0.0459 (9)	0.0470 (9)	0.0015 (7)	0.0079 (6)	−0.0033 (7)
C3	0.0418 (9)	0.0483 (9)	0.0590 (10)	0.0091 (7)	0.0062 (7)	0.0042 (8)
C4	0.0442 (9)	0.0439 (9)	0.0520 (9)	0.0004 (7)	0.0064 (7)	0.0012 (7)
C5	0.0373 (8)	0.0530 (10)	0.0623 (10)	0.0005 (7)	0.0082 (7)	0.0071 (8)
C6	0.0397 (8)	0.0517 (9)	0.0600 (10)	0.0069 (7)	0.0039 (7)	0.0072 (8)
C7	0.0458 (9)	0.0522 (10)	0.0519 (9)	0.0062 (8)	0.0100 (7)	0.0016 (8)
C8	0.0449 (9)	0.0535 (10)	0.0638 (11)	0.0065 (8)	0.0098 (8)	0.0049 (8)
C9	0.0517 (9)	0.0456 (9)	0.0510 (9)	0.0027 (7)	0.0070 (7)	0.0115 (7)
C10	0.0732 (12)	0.0524 (10)	0.0626 (11)	−0.0007 (9)	−0.0059 (9)	0.0000 (9)
C11	0.0989 (16)	0.0647 (12)	0.0539 (11)	0.0253 (12)	0.0141 (11)	−0.0029 (9)
C12	0.0647 (12)	0.0775 (14)	0.0762 (14)	0.0134 (11)	0.0239 (10)	0.0126 (11)
C13	0.0578 (11)	0.0763 (14)	0.0875 (15)	−0.0109 (10)	0.0137 (10)	−0.0022 (12)
C14	0.0647 (11)	0.0573 (11)	0.0588 (11)	−0.0039 (9)	0.0129 (9)	−0.0059 (9)

S1—C4	1.7638 (16)	C5—H5	0.9300
S1—C9	1.7770 (17)	C6—H6	0.9300
N1—C7	1.142 (2)	C9—C14	1.375 (3)
N2—C8	1.143 (2)	C9—C10	1.385 (3)
C1—C6	1.386 (2)	C10—C11	1.389 (3)
C1—C2	1.404 (2)	C10—H10	0.9300
C1—C7	1.436 (2)	C11—C12	1.370 (3)
C2—C3	1.379 (2)	C11—H11	0.9300
C2—C8	1.440 (2)	C12—C13	1.353 (3)
C3—C4	1.397 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.381 (3)
C4—C5	1.387 (2)	C13—H13	0.9300
C5—C6	1.379 (2)	C14—H14	0.9300
C4—S1—C9	103.59 (7)	N2—C8—C2	178.3 (2)
C6—C1—C2	119.07 (14)	C14—C9—C10	119.68 (17)
C6—C1—C7	120.97 (14)	C14—C9—S1	119.29 (14)
C2—C1—C7	119.95 (14)	C10—C9—S1	120.97 (14)
C3—C2—C1	120.38 (14)	C9—C10—C11	119.38 (18)
C3—C2—C8	120.55 (14)	C9—C10—H10	120.3
C1—C2—C8	119.07 (14)	C11—C10—H10	120.3
C2—C3—C4	120.13 (14)	C12—C11—C10	120.21 (18)
C2—C3—H3	119.9	C12—C11—H11	119.9
C4—C3—H3	119.9	C10—C11—H11	119.9
C5—C4—C3	119.22 (15)	C13—C12—C11	120.05 (19)
C5—C4—S1	124.76 (12)	C13—C12—H12	120.0
C3—C4—S1	116.01 (12)	C11—C12—H12	120.0
C6—C5—C4	120.80 (15)	C12—C13—C14	120.9 (2)
C6—C5—H5	119.6	C12—C13—H13	119.6
C4—C5—H5	119.6	C14—C13—H13	119.6
C5—C6—C1	120.39 (15)	C9—C14—C13	119.80 (18)
C5—C6—H6	119.8	C9—C14—H14	120.1
C1—C6—H6	119.8	C13—C14—H14	120.1
N1—C7—C1	178.87 (19)