2-[2-(4-Methyl-benzo-yl)-3,3-bis-(methyl-sulfan-yl)prop-2-enyl-idene]malononitrile.

The title compound, C(16)H(14)N(2)OS(2), is an example of a push-pull butadiene in which the electron-releasing and electron-withdrawing attachments on either end of the butadiene chain enhance the conjugation in the system. The mol-ecules are linked by inter-molecular C-H⋯N inter-actions.

Related literature

For related literature, see: Anabha & Asokan (2006 ▶); Dahne (1978 ▶); Dastidar et al. (1993 ▶); Freier et al. (1999 ▶); Homrig­hausen & Krause Bauer (2004 ▶); Michalik et al. (2002 ▶).

Experimental

Crystal data

C16H14N2OS2

M = 314.41

Monoclinic,

a = 16.6050 (13) Å

b = 10.760 (2) Å

c = 9.905 (2) Å

β = 110.09 (2)°

V = 1662.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 295 (2) K

0.25 × 0.25 × 0.20 mm

Data collection

MacScience DIPLabo 32001 diffractometer

Absorption correction: none

4433 measured reflections

2717 independent reflections

2583 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.156

S = 1.11

2717 reflections

194 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), with 1210 Friedel pairs

Flack parameter: 0.11 (12)

Data collection: XPRESS (MacScience, 2002 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶) and ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808004054/pv2055sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004054/pv2055Isup2.hkl

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

C16H14N2OS2	F000 = 656
Mr = 314.41	Dx = 1.257 Mg m−3
Monoclinic, C2	Mo Kα radiation λ = 0.71070 Å
Hall symbol: C 2y	Cell parameters from 4224 reflections
a = 16.6050 (13) Å	θ = 3.5–25.5º
b = 10.760 (2) Å	µ = 0.32 mm−1
c = 9.905 (2) Å	T = 295 (2) K
β = 110.09 (2)º	Block, pale yellow
V = 1662.0 (5) Å3	0.25 × 0.25 × 0.20 mm
Z = 4

MacScience DIPLabo 32001 diffractometer	2717 independent reflections
Radiation source: fine-focus sealed tube	2583 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
Detector resolution: 10.0 pixels mm-1	θmax = 25.5º
T = 295(2) K	θmin = 3.5º
ω scans	h = −20→20
Absorption correction: none	k = −11→11
4433 measured reflections	l = −11→11

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.1066P)2 + 0.5386P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.156	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.30 e Å−3
2717 reflections	Δρmin = −0.28 e Å−3
194 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.015 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Flack parameter: 0.11 (12)

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	0.33194 (6)	0.02065 (9)	0.76965 (9)	0.0543 (3)
S2	0.16024 (7)	−0.08895 (12)	0.75086 (11)	0.0689 (4)
C5	0.1681 (2)	−0.0204 (3)	1.1171 (4)	0.0458 (8)
C13	0.3562 (2)	0.0395 (4)	1.0845 (3)	0.0471 (7)
H13	0.3801	0.0925	1.0344	0.057*
C9	0.2833 (2)	−0.0289 (3)	0.9991 (3)	0.0430 (7)
C8	0.2276 (2)	−0.0956 (4)	1.0693 (3)	0.0471 (8)
C14	0.3959 (2)	0.0379 (4)	1.2301 (3)	0.0508 (8)
C10	0.2604 (2)	−0.0317 (3)	0.8523 (4)	0.0468 (7)
O1	0.2346 (2)	−0.2092 (3)	1.0871 (3)	0.0680 (8)
C4	0.1194 (3)	−0.0773 (4)	1.1895 (5)	0.0622 (10)
H4	0.1228	−0.1628	1.2041	0.075*
C6	0.1602 (3)	0.1060 (4)	1.0927 (5)	0.0592 (10)
H6	0.1916	0.1447	1.0428	0.071*
C16	0.4673 (2)	0.1193 (4)	1.2927 (4)	0.0553 (9)
C15	0.3732 (3)	−0.0373 (4)	1.3306 (4)	0.0588 (10)
C3	0.0660 (3)	−0.0065 (5)	1.2394 (5)	0.0716 (12)
H3	0.0341	−0.0452	1.2882	0.086*
C2	0.0592 (3)	0.1204 (6)	1.2184 (5)	0.0729 (13)
N1	0.3560 (3)	−0.0944 (5)	1.4132 (4)	0.0905 (14)
N2	0.5237 (3)	0.1858 (5)	1.3400 (5)	0.0795 (12)
C11	0.2658 (3)	0.1102 (5)	0.6206 (5)	0.0724 (12)
H11A	0.2391	0.0562	0.5405	0.109*
H11B	0.3003	0.1705	0.5942	0.109*
H11C	0.2223	0.1521	0.6470	0.109*
C12	0.1815 (4)	−0.1799 (6)	0.6150 (5)	0.0828 (15)
H12A	0.1970	−0.1258	0.5508	0.124*
H12B	0.1311	−0.2261	0.5620	0.124*
H12C	0.2278	−0.2364	0.6595	0.124*
C7	0.1061 (3)	0.1753 (5)	1.1419 (6)	0.0738 (13)
H7	0.1008	0.2602	1.1236	0.089*
C1	0.0013 (5)	0.2004 (8)	1.2746 (9)	0.105 (2)
H1A	−0.0539	0.1616	1.2510	0.157*
H1B	−0.0052	0.2812	1.2311	0.157*
H1C	0.0267	0.2085	1.3771	0.157*

	U11	U22	U33	U12	U13	U23
S1	0.0555 (5)	0.0664 (6)	0.0453 (5)	−0.0047 (4)	0.0227 (4)	−0.0002 (4)
S2	0.0532 (5)	0.0949 (9)	0.0551 (5)	−0.0188 (5)	0.0141 (4)	−0.0181 (5)
C5	0.0452 (17)	0.046 (2)	0.0481 (17)	−0.0059 (12)	0.0189 (14)	−0.0031 (13)
C13	0.0479 (16)	0.054 (2)	0.0413 (16)	−0.0045 (14)	0.0172 (13)	−0.0025 (13)
C9	0.0473 (17)	0.0434 (18)	0.0393 (15)	−0.0042 (12)	0.0162 (13)	−0.0027 (11)
C8	0.0526 (18)	0.049 (2)	0.0410 (16)	−0.0073 (14)	0.0176 (14)	−0.0026 (13)
C14	0.0494 (17)	0.063 (2)	0.0405 (15)	0.0010 (16)	0.0163 (13)	−0.0063 (15)
C10	0.0491 (18)	0.0487 (19)	0.0456 (17)	−0.0060 (13)	0.0202 (14)	−0.0053 (13)
O1	0.090 (2)	0.0475 (19)	0.081 (2)	−0.0027 (14)	0.0481 (17)	−0.0039 (13)
C4	0.062 (2)	0.062 (3)	0.072 (2)	0.0035 (18)	0.036 (2)	0.0115 (19)
C6	0.053 (2)	0.052 (3)	0.077 (3)	−0.0072 (15)	0.0284 (19)	−0.0051 (17)
C16	0.0472 (19)	0.071 (2)	0.0447 (18)	−0.0072 (17)	0.0118 (15)	−0.0098 (16)
C15	0.062 (2)	0.065 (3)	0.0454 (18)	−0.0017 (17)	0.0130 (16)	−0.0001 (17)
C3	0.069 (3)	0.076 (4)	0.085 (3)	0.0031 (19)	0.047 (2)	0.010 (2)
C2	0.052 (2)	0.090 (4)	0.079 (3)	−0.002 (2)	0.026 (2)	−0.024 (2)
N1	0.104 (3)	0.112 (4)	0.052 (2)	−0.021 (3)	0.023 (2)	0.015 (2)
N2	0.062 (2)	0.105 (4)	0.065 (2)	−0.020 (2)	0.0144 (19)	−0.016 (2)
C11	0.083 (3)	0.077 (3)	0.056 (2)	−0.003 (2)	0.024 (2)	0.016 (2)
C12	0.089 (3)	0.096 (4)	0.060 (3)	−0.033 (3)	0.022 (2)	−0.026 (2)
C7	0.071 (3)	0.052 (3)	0.107 (4)	−0.0002 (18)	0.041 (3)	−0.010 (2)
C1	0.090 (4)	0.104 (5)	0.140 (6)	−0.002 (3)	0.065 (4)	−0.036 (4)

S1—C10	1.751 (3)	C6—H6	0.9300
S1—C11	1.790 (5)	C16—N2	1.142 (6)
S2—C10	1.734 (3)	C15—N1	1.135 (6)
S2—C12	1.795 (5)	C3—C2	1.381 (8)
C5—C6	1.379 (6)	C3—H3	0.9300
C5—C4	1.393 (5)	C2—C7	1.390 (7)
C5—C8	1.475 (5)	C2—C1	1.531 (7)
C13—C14	1.364 (5)	C11—H11A	0.9600
C13—C9	1.421 (5)	C11—H11B	0.9600
C13—H13	0.9300	C11—H11C	0.9600
C9—C10	1.372 (5)	C12—H12A	0.9600
C9—C8	1.515 (4)	C12—H12B	0.9600
C8—O1	1.235 (5)	C12—H12C	0.9600
C14—C15	1.430 (6)	C7—H7	0.9300
C14—C16	1.433 (5)	C1—H1A	0.9600
C4—C3	1.383 (6)	C1—H1B	0.9600
C4—H4	0.9300	C1—H1C	0.9600
C6—C7	1.380 (6)
C10—S1—C11	103.7 (2)	C2—C3—C4	121.4 (4)
C10—S2—C12	103.4 (2)	C2—C3—H3	119.3
C6—C5—C4	119.2 (4)	C4—C3—H3	119.3
C6—C5—C8	121.2 (3)	C3—C2—C7	118.0 (4)
C4—C5—C8	119.6 (3)	C3—C2—C1	122.0 (5)
C14—C13—C9	128.7 (3)	C7—C2—C1	119.9 (6)
C14—C13—H13	115.6	S1—C11—H11A	109.5
C9—C13—H13	115.6	S1—C11—H11B	109.5
C10—C9—C13	120.8 (3)	H11A—C11—H11B	109.5
C10—C9—C8	119.1 (3)	S1—C11—H11C	109.5
C13—C9—C8	120.1 (3)	H11A—C11—H11C	109.5
O1—C8—C5	122.6 (3)	H11B—C11—H11C	109.5
O1—C8—C9	119.4 (3)	S2—C12—H12A	109.5
C5—C8—C9	118.0 (3)	S2—C12—H12B	109.5
C13—C14—C15	126.6 (3)	H12A—C12—H12B	109.5
C13—C14—C16	118.5 (3)	S2—C12—H12C	109.5
C15—C14—C16	115.0 (3)	H12A—C12—H12C	109.5
C9—C10—S2	118.9 (3)	H12B—C12—H12C	109.5
C9—C10—S1	120.2 (3)	C6—C7—C2	121.2 (5)
S2—C10—S1	120.88 (19)	C6—C7—H7	119.4
C3—C4—C5	119.9 (4)	C2—C7—H7	119.4
C3—C4—H4	120.1	C2—C1—H1A	109.5
C5—C4—H4	120.1	C2—C1—H1B	109.5
C5—C6—C7	120.3 (4)	H1A—C1—H1B	109.5
C5—C6—H6	119.9	C2—C1—H1C	109.5
C7—C6—H6	119.9	H1A—C1—H1C	109.5
N2—C16—C14	178.5 (5)	H1B—C1—H1C	109.5
N1—C15—C14	178.0 (5)
C14—C13—C9—C10	−169.0 (4)	C8—C9—C10—S1	−169.0 (3)
C14—C13—C9—C8	13.6 (6)	C12—S2—C10—C9	−138.8 (3)
C6—C5—C8—O1	−178.5 (4)	C12—S2—C10—S1	40.6 (3)
C4—C5—C8—O1	2.1 (6)	C11—S1—C10—C9	−136.9 (3)
C6—C5—C8—C9	3.1 (5)	C11—S1—C10—S2	43.7 (3)
C4—C5—C8—C9	−176.3 (3)	C6—C5—C4—C3	−1.9 (6)
C10—C9—C8—O1	80.2 (5)	C8—C5—C4—C3	177.5 (4)
C13—C9—C8—O1	−102.4 (4)	C4—C5—C6—C7	1.3 (7)
C10—C9—C8—C5	−101.3 (4)	C8—C5—C6—C7	−178.1 (4)
C13—C9—C8—C5	76.1 (4)	C5—C4—C3—C2	0.5 (7)
C9—C13—C14—C15	1.7 (6)	C4—C3—C2—C7	1.6 (8)
C9—C13—C14—C16	−177.8 (4)	C4—C3—C2—C1	−179.2 (5)
C13—C9—C10—S2	−167.0 (3)	C5—C6—C7—C2	0.9 (8)
C8—C9—C10—S2	10.4 (5)	C3—C2—C7—C6	−2.3 (8)
C13—C9—C10—S1	13.6 (5)	C1—C2—C7—C6	178.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···N2i	0.96	2.49	3.3871	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12B⋯N2i	0.96	2.49	3.3871	155

Symmetry code: (i) .