4,5-Bis(isopropyl-sulfan-yl)benzene-1,2-dicarbonitrile.

In the title compound, C(14)H(16)N(2)S(2), the C atoms of the aromatic ring, the two cyanide groups and the two S atoms of the isopropyl-sulfanyl groups are almost coplanar [maximum deviation from the mean plane = 0.042 (7) Å]. In the crystal, inversion dimers linked by aromatic π-π stacking occur, with a centroid-centroid separation of 3.7543 (8) Å.

Related literature

For a related structure and background information on phthalocyanines, see: Zhang et al. (2009 ▶). For the synthesis, see: Rey et al. (1998 ▶).

Experimental

Crystal data

C14H16N2S2

M = 276.41

Monoclinic,

a = 10.4929 (7) Å

b = 9.3613 (6) Å

c = 15.4491 (11) Å

β = 96.467 (1)°

V = 1507.87 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 298 K

0.20 × 0.12 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.936, T max = 0.983

7215 measured reflections

2653 independent reflections

2371 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.05

2653 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008755/hb5352sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008755/hb5352Isup2.hkl

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

C14H16N2S2	F(000) = 584
Mr = 276.41	Dx = 1.218 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4590 reflections
a = 10.4929 (7) Å	θ = 2.5–27.4°
b = 9.3613 (6) Å	µ = 0.34 mm−1
c = 15.4491 (11) Å	T = 298 K
β = 96.467 (1)°	Plate, colorless
V = 1507.87 (18) Å3	0.20 × 0.12 × 0.05 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2653 independent reflections
Radiation source: fine-focus sealed tube	2371 reflections with I > 2σ(I)
graphite	Rint = 0.016
Detector resolution: 0 pixels mm-1	θmax = 25.0°, θmin = 2.2°
ω scans	h = −12→9
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −11→11
Tmin = 0.936, Tmax = 0.983	l = −17→18
7215 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0476P)2 + 0.2613P] where P = (Fo2 + 2Fc2)/3
2653 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.19579 (3)	−0.17837 (4)	0.39373 (3)	0.05107 (14)
S2	0.31036 (3)	0.05041 (4)	0.51139 (2)	0.04640 (14)
C1	−0.02406 (13)	0.23666 (15)	0.41156 (9)	0.0420 (3)
C4	0.10593 (12)	−0.02113 (15)	0.39674 (9)	0.0374 (3)
C5	0.16133 (12)	0.08841 (14)	0.45253 (8)	0.0362 (3)
C6	0.09506 (13)	0.21542 (15)	0.45910 (9)	0.0418 (3)
H6	0.1307	0.2873	0.4957	0.050*
C3	−0.01420 (13)	0.00042 (16)	0.35047 (9)	0.0416 (3)
H3	−0.0515	−0.0718	0.3148	0.050*
C2	−0.07884 (13)	0.12884 (16)	0.35707 (9)	0.0408 (3)
C13	0.35421 (14)	0.20982 (16)	0.57640 (9)	0.0448 (3)
H13	0.2780	0.2470	0.6001	0.054*
C7	−0.08952 (15)	0.37074 (18)	0.41839 (11)	0.0538 (4)
C14	0.45028 (15)	0.1574 (2)	0.65105 (10)	0.0583 (4)
H14A	0.4111	0.0850	0.6832	0.088*
H14B	0.4762	0.2360	0.6890	0.088*
H14C	0.5240	0.1184	0.6280	0.088*
N1	−0.14093 (17)	0.47715 (17)	0.42345 (12)	0.0778 (5)
C10	0.10888 (15)	−0.29469 (16)	0.31245 (10)	0.0471 (4)
H10	0.0191	−0.3013	0.3240	0.057*
C8	−0.20085 (14)	0.15434 (18)	0.30676 (10)	0.0507 (4)
N2	−0.29515 (14)	0.1806 (2)	0.26646 (11)	0.0752 (5)
C12	0.4102 (2)	0.3253 (2)	0.52361 (13)	0.0714 (5)
H12A	0.3471	0.3552	0.4773	0.107*
H12B	0.4840	0.2887	0.4995	0.107*
H12C	0.4349	0.4054	0.5605	0.107*
C11	0.1728 (2)	−0.43966 (18)	0.32843 (14)	0.0722 (5)
H11A	0.1680	−0.4681	0.3877	0.108*
H11B	0.2610	−0.4333	0.3179	0.108*
H11C	0.1296	−0.5090	0.2898	0.108*
C9	0.1141 (2)	−0.2436 (2)	0.22038 (12)	0.0700 (5)
H9A	0.0734	−0.1519	0.2130	0.105*
H9B	0.0702	−0.3106	0.1805	0.105*
H9C	0.2019	−0.2358	0.2091	0.105*

	U11	U22	U33	U12	U13	U23
S1	0.0376 (2)	0.0453 (2)	0.0673 (3)	0.00601 (15)	−0.00753 (17)	−0.01699 (17)
S2	0.0365 (2)	0.0456 (2)	0.0536 (2)	0.00658 (15)	−0.01006 (16)	−0.00971 (16)
C1	0.0399 (7)	0.0423 (8)	0.0430 (7)	0.0060 (6)	0.0014 (6)	0.0032 (6)
C4	0.0323 (7)	0.0402 (7)	0.0398 (7)	−0.0001 (5)	0.0044 (5)	−0.0015 (6)
C5	0.0315 (7)	0.0403 (7)	0.0363 (7)	0.0011 (5)	0.0020 (5)	−0.0001 (5)
C6	0.0409 (8)	0.0401 (8)	0.0426 (8)	0.0028 (6)	−0.0031 (6)	−0.0029 (6)
C3	0.0354 (7)	0.0453 (8)	0.0433 (7)	−0.0034 (6)	0.0005 (6)	−0.0035 (6)
C2	0.0320 (7)	0.0489 (8)	0.0406 (7)	0.0008 (6)	0.0005 (6)	0.0062 (6)
C13	0.0383 (7)	0.0513 (9)	0.0434 (8)	0.0002 (6)	−0.0017 (6)	−0.0117 (6)
C7	0.0507 (9)	0.0505 (9)	0.0569 (9)	0.0110 (7)	−0.0083 (7)	0.0004 (7)
C14	0.0425 (8)	0.0797 (12)	0.0499 (9)	0.0037 (8)	−0.0078 (7)	−0.0122 (8)
N1	0.0790 (11)	0.0594 (10)	0.0895 (12)	0.0271 (9)	−0.0150 (9)	−0.0073 (8)
C10	0.0425 (8)	0.0420 (8)	0.0561 (9)	−0.0071 (6)	0.0025 (6)	−0.0093 (7)
C8	0.0384 (8)	0.0609 (10)	0.0513 (9)	0.0004 (7)	−0.0022 (7)	0.0051 (7)
N2	0.0455 (8)	0.1017 (13)	0.0736 (10)	0.0064 (8)	−0.0150 (7)	0.0103 (9)
C12	0.0734 (13)	0.0612 (11)	0.0777 (13)	−0.0156 (9)	0.0006 (10)	0.0011 (9)
C11	0.0770 (13)	0.0440 (10)	0.0921 (14)	0.0008 (9)	−0.0066 (11)	−0.0183 (9)
C9	0.0839 (13)	0.0701 (12)	0.0574 (10)	−0.0124 (10)	0.0142 (9)	−0.0105 (9)

S1—C4	1.7515 (14)	C7—N1	1.140 (2)
S1—C10	1.8265 (15)	C14—H14A	0.9600
S2—C5	1.7545 (13)	C14—H14B	0.9600
S2—C13	1.8284 (15)	C14—H14C	0.9600
C1—C6	1.3909 (19)	C10—C9	1.507 (2)
C1—C2	1.396 (2)	C10—C11	1.521 (2)
C1—C7	1.440 (2)	C10—H10	0.9800
C4—C3	1.3920 (19)	C8—N2	1.135 (2)
C4—C5	1.4211 (19)	C12—H12A	0.9600
C5—C6	1.3868 (19)	C12—H12B	0.9600
C6—H6	0.9300	C12—H12C	0.9600
C3—C2	1.390 (2)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C2—C8	1.441 (2)	C11—H11C	0.9600
C13—C12	1.512 (2)	C9—H9A	0.9600
C13—C14	1.525 (2)	C9—H9B	0.9600
C13—H13	0.9800	C9—H9C	0.9600
C4—S1—C10	106.90 (7)	H14A—C14—H14B	109.5
C5—S2—C13	105.88 (7)	C13—C14—H14C	109.5
C6—C1—C2	119.97 (13)	H14A—C14—H14C	109.5
C6—C1—C7	119.57 (13)	H14B—C14—H14C	109.5
C2—C1—C7	120.46 (13)	C9—C10—C11	111.96 (15)
C3—C4—C5	119.46 (13)	C9—C10—S1	113.04 (11)
C3—C4—S1	124.56 (11)	C11—C10—S1	104.09 (11)
C5—C4—S1	115.97 (10)	C9—C10—H10	109.2
C6—C5—C4	119.26 (12)	C11—C10—H10	109.2
C6—C5—S2	124.12 (10)	S1—C10—H10	109.2
C4—C5—S2	116.61 (10)	N2—C8—C2	176.87 (19)
C5—C6—C1	120.80 (13)	C13—C12—H12A	109.5
C5—C6—H6	119.6	C13—C12—H12B	109.5
C1—C6—H6	119.6	H12A—C12—H12B	109.5
C2—C3—C4	120.59 (13)	C13—C12—H12C	109.5
C2—C3—H3	119.7	H12A—C12—H12C	109.5
C4—C3—H3	119.7	H12B—C12—H12C	109.5
C3—C2—C1	119.90 (12)	C10—C11—H11A	109.5
C3—C2—C8	121.00 (14)	C10—C11—H11B	109.5
C1—C2—C8	119.08 (13)	H11A—C11—H11B	109.5
C12—C13—C14	111.97 (14)	C10—C11—H11C	109.5
C12—C13—S2	112.10 (11)	H11A—C11—H11C	109.5
C14—C13—S2	104.90 (11)	H11B—C11—H11C	109.5
C12—C13—H13	109.3	C10—C9—H9A	109.5
C14—C13—H13	109.3	C10—C9—H9B	109.5
S2—C13—H13	109.3	H9A—C9—H9B	109.5
N1—C7—C1	179.6 (2)	C10—C9—H9C	109.5
C13—C14—H14A	109.5	H9A—C9—H9C	109.5
C13—C14—H14B	109.5	H9B—C9—H9C	109.5