N-[(E,Z)-1,3-Diphenyl-prop-2-enyl-idene]-N'-(1,3-dithio-lan-2-yl-idene)hydrazine.

Mol-ecules of the title compound, C(18)H(16)N(2)S(2), exist as the (2E, 1'Z)-isomer. The 1,3-dithiol-ane ring has an envelope conformation; the atoms of the C-C bond are disordered over two positions with occupancies of 0.47 (7) and 0.53 (7). The structure exhibits inter-molecular C-H⋯S and C-H⋯π(arene) hydrogen bonds.

Related literature

For related literature, see: Beghidja et al. (2006 ▶); Cremer & Pople (1975 ▶); Gou et al. (2004 ▶); Liu et al. (2001 ▶, 2003 ▶, 2007 ▶, 2008 ▶); Wang et al. (1994 ▶); Xu et al. (2005 ▶); Yang et al. (2007 ▶); Yarishkin et al. (2008 ▶); Zhai et al. (1999 ▶).

Experimental

Crystal data

C18H16N2S2

M = 324.47

Orthorhombic,

a = 30.9008 (9) Å

b = 5.7352 (2) Å

c = 9.1499 (3) Å

V = 1621.57 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 296 (2) K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.909, T max = 0.938

7320 measured reflections

3339 independent reflections

2833 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.117

S = 1.00

3339 reflections

206 parameters

7 restraints

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.34 e Å−3

Absolute structure: Flack (1983 ▶), 1186 Friedel pairs

Flack parameter: −0.03 (9)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018606/om2242sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018606/om2242Isup2.hkl

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

C18H16N2S2	Dx = 1.329 Mg m−3
Mr = 324.47	Melting point: 442 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2883 reflections
a = 30.9008 (9) Å	θ = 2.6–28.1°
b = 5.7352 (2) Å	µ = 0.33 mm−1
c = 9.1499 (3) Å	T = 296 K
V = 1621.57 (9) Å3	Block, yellow
Z = 4	0.30 × 0.30 × 0.20 mm
F(000) = 680

Bruker SMART 1000 CCD diffractometer	3339 independent reflections
Radiation source: fine-focus sealed tube	2833 reflections with I > 2σ(I)
graphite	Rint = 0.055
ω scans	θmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −41→39
Tmin = 0.909, Tmax = 0.938	k = −4→7
7320 measured reflections	l = −12→11

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0727P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.003
3339 reflections	Δρmax = 0.47 e Å−3
206 parameters	Δρmin = −0.34 e Å−3
7 restraints	Absolute structure: Flack (1983), 1186 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (9)

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)
C1	0.00882 (11)	1.1023 (6)	0.9703 (5)	0.0507 (8)
H1	−0.0016	1.0304	0.8863	0.061*
C2	−0.01559 (12)	1.2737 (7)	1.0391 (5)	0.0569 (10)
H2	−0.0428	1.3112	1.0024	0.068*
C3	−0.00045 (12)	1.3879 (6)	1.1592 (4)	0.0526 (9)
H3	−0.0168	1.5053	1.2025	0.063*
C4	0.03941 (11)	1.3275 (7)	1.2162 (5)	0.0547 (9)
H4	0.0500	1.4039	1.2985	0.066*
C5	0.06363 (10)	1.1535 (6)	1.1509 (4)	0.0423 (7)
H5	0.0903	1.1133	1.1908	0.051*
C6	0.04918 (9)	1.0381 (5)	1.0281 (3)	0.0321 (6)
C7	0.07453 (9)	0.8558 (5)	0.9542 (3)	0.0318 (6)
H7	0.0679	0.8263	0.8568	0.038*
C8	0.10609 (9)	0.7288 (5)	1.0139 (3)	0.0302 (6)
H8	0.1126	0.7561	1.1117	0.036*
C9	0.13112 (8)	0.5516 (5)	0.9387 (3)	0.0288 (6)
C10	0.13030 (9)	0.5395 (5)	0.7762 (3)	0.0287 (6)
C11	0.11505 (11)	0.3437 (6)	0.7030 (4)	0.0400 (7)
H11	0.1039	0.2189	0.7559	0.048*
C12	0.11627 (13)	0.3328 (7)	0.5522 (4)	0.0485 (9)
H12	0.1059	0.2011	0.5044	0.058*
C13	0.13278 (10)	0.5157 (6)	0.4720 (4)	0.0457 (8)
H13	0.1341	0.5062	0.3706	0.055*
C14	0.14728 (10)	0.7122 (6)	0.5424 (4)	0.0424 (8)
H14	0.1581	0.8365	0.4883	0.051*
C15	0.14592 (9)	0.7269 (6)	0.6941 (3)	0.0352 (7)
H15	0.1554	0.8615	0.7408	0.042*
C16	0.19817 (8)	0.1107 (5)	1.0334 (3)	0.0267 (6)
C17	0.2416 (6)	−0.261 (2)	1.1233 (8)	0.061 (3)	0.427 (7)
H17C	0.2319	−0.4193	1.1064	0.073*	0.427 (7)
H17D	0.2724	−0.2661	1.1438	0.073*	0.427 (7)
C18	0.2200 (3)	−0.1717 (16)	1.2466 (9)	0.0409 (13)	0.427 (7)
H18C	0.2410	−0.1558	1.3248	0.049*	0.427 (7)
H18D	0.1989	−0.2864	1.2778	0.049*	0.427 (7)
C17'	0.2517 (3)	−0.1970 (15)	1.1350 (5)	0.061 (3)	0.573 (7)
H17A	0.2432	−0.3591	1.1449	0.073*	0.573 (7)
H17B	0.2830	−0.1927	1.1340	0.073*	0.573 (7)
C18'	0.2375 (2)	−0.0777 (12)	1.2611 (6)	0.0409 (13)	0.573 (7)
H18A	0.2612	0.0151	1.2993	0.049*	0.573 (7)
H18B	0.2295	−0.1906	1.3353	0.049*	0.573 (7)
N1	0.15384 (7)	0.4150 (4)	1.0215 (3)	0.0303 (5)
N2	0.17893 (8)	0.2525 (4)	0.9464 (3)	0.0326 (5)
S1	0.23331 (2)	−0.09801 (13)	0.96398 (8)	0.0371 (2)
S2	0.19208 (2)	0.10941 (13)	1.22517 (8)	0.03412 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0449 (17)	0.054 (2)	0.0529 (19)	0.0162 (16)	−0.0127 (17)	−0.0014 (18)
C2	0.0450 (18)	0.064 (3)	0.062 (2)	0.025 (2)	−0.0003 (18)	0.011 (2)
C3	0.0468 (19)	0.048 (2)	0.063 (2)	0.0138 (16)	0.0177 (17)	0.0037 (17)
C4	0.0448 (17)	0.057 (2)	0.062 (2)	0.0032 (17)	0.0105 (19)	−0.014 (2)
C5	0.0282 (14)	0.0498 (19)	0.0489 (19)	0.0002 (14)	0.0035 (13)	−0.0052 (15)
C6	0.0304 (13)	0.0307 (15)	0.0353 (14)	0.0037 (12)	0.0044 (11)	0.0105 (12)
C7	0.0307 (13)	0.0326 (14)	0.0321 (13)	−0.0017 (12)	−0.0014 (12)	0.0042 (13)
C8	0.0300 (12)	0.0319 (15)	0.0287 (13)	0.0000 (12)	0.0000 (10)	0.0062 (11)
C9	0.0245 (12)	0.0292 (14)	0.0326 (14)	−0.0031 (11)	0.0000 (10)	0.0083 (11)
C10	0.0256 (12)	0.0277 (14)	0.0328 (13)	0.0085 (11)	0.0001 (11)	0.0060 (11)
C11	0.0465 (16)	0.0330 (16)	0.0405 (18)	0.0057 (14)	−0.0028 (14)	0.0068 (14)
C12	0.061 (2)	0.0419 (19)	0.0426 (18)	0.0144 (18)	−0.0111 (16)	−0.0071 (15)
C13	0.0507 (18)	0.056 (2)	0.0300 (14)	0.0256 (17)	0.0009 (16)	0.0032 (16)
C14	0.0417 (16)	0.050 (2)	0.0358 (16)	0.0093 (16)	0.0069 (14)	0.0178 (15)
C15	0.0303 (13)	0.0381 (17)	0.0373 (16)	0.0033 (13)	0.0026 (11)	0.0097 (13)
C16	0.0260 (12)	0.0276 (15)	0.0266 (12)	−0.0049 (11)	−0.0006 (10)	0.0055 (11)
C17	0.087 (6)	0.050 (6)	0.046 (2)	0.039 (5)	−0.018 (3)	−0.001 (3)
C18	0.038 (3)	0.039 (4)	0.046 (3)	0.009 (2)	−0.016 (2)	0.008 (3)
C17'	0.087 (6)	0.050 (6)	0.046 (2)	0.039 (5)	−0.018 (3)	−0.001 (3)
C18'	0.038 (3)	0.039 (4)	0.046 (3)	0.009 (2)	−0.016 (2)	0.008 (3)
N1	0.0260 (11)	0.0347 (13)	0.0302 (11)	0.0046 (10)	0.0023 (9)	0.0081 (10)
N2	0.0315 (11)	0.0357 (13)	0.0306 (12)	0.0058 (10)	0.0038 (9)	0.0078 (10)
S1	0.0372 (4)	0.0369 (4)	0.0373 (4)	0.0088 (3)	0.0046 (3)	0.0062 (4)
S2	0.0336 (3)	0.0405 (4)	0.0283 (3)	0.0076 (3)	−0.0037 (3)	0.0034 (3)

C1—C2	1.389 (5)	C13—C14	1.373 (5)
C1—C6	1.404 (4)	C13—H13	0.9300
C1—H1	0.9300	C14—C15	1.391 (4)
C2—C3	1.362 (6)	C14—H14	0.9300
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.381 (5)	C16—N2	1.284 (3)
C3—H3	0.9300	C16—S1	1.736 (3)
C4—C5	1.383 (5)	C16—S2	1.765 (3)
C4—H4	0.9300	C17—C18	1.406 (5)
C5—C6	1.378 (4)	C17—S1	1.750 (5)
C5—H5	0.9300	C17—H17C	0.9700
C6—C7	1.471 (4)	C17—H17D	0.9700
C7—C8	1.334 (4)	C18—S2	1.839 (8)
C7—H7	0.9300	C18—H18C	0.9700
C8—C9	1.451 (4)	C18—H18D	0.9700
C8—H8	0.9300	C17'—C18'	1.410 (5)
C9—N1	1.296 (3)	C17'—S1	1.759 (4)
C9—C10	1.489 (4)	C17'—H17A	0.9700
C10—C11	1.390 (5)	C17'—H17B	0.9700
C10—C15	1.397 (4)	C18'—S2	1.798 (5)
C11—C12	1.382 (5)	C18'—H18A	0.9700
C11—H11	0.9300	C18'—H18B	0.9700
C12—C13	1.378 (5)	N1—N2	1.394 (3)
C12—H12	0.9300
C2—C1—C6	119.8 (4)	C13—C14—C15	120.5 (3)
C2—C1—H1	120.1	C13—C14—H14	119.7
C6—C1—H1	120.1	C15—C14—H14	119.7
C3—C2—C1	121.3 (3)	C14—C15—C10	120.0 (3)
C3—C2—H2	119.4	C14—C15—H15	120.0
C1—C2—H2	119.4	C10—C15—H15	120.0
C2—C3—C4	119.3 (3)	N2—C16—S1	120.0 (2)
C2—C3—H3	120.3	N2—C16—S2	124.7 (2)
C4—C3—H3	120.3	S1—C16—S2	115.30 (15)
C3—C4—C5	120.0 (4)	C18—C17—S1	113.9 (6)
C3—C4—H4	120.0	C18—C17—H17C	108.8
C5—C4—H4	120.0	S1—C17—H17C	108.8
C6—C5—C4	121.5 (3)	C18—C17—H17D	108.8
C6—C5—H5	119.2	S1—C17—H17D	108.8
C4—C5—H5	119.2	H17C—C17—H17D	107.7
C5—C6—C1	118.0 (3)	C17—C18—S2	117.1 (6)
C5—C6—C7	122.9 (3)	C17—C18—H18C	108.0
C1—C6—C7	119.1 (3)	S2—C18—H18C	108.0
C8—C7—C6	126.1 (3)	C17—C18—H18D	108.0
C8—C7—H7	117.0	S2—C18—H18D	108.0
C6—C7—H7	117.0	H18C—C18—H18D	107.3
C7—C8—C9	125.3 (3)	C18'—C17'—S1	118.1 (5)
C7—C8—H8	117.3	C18'—C17'—H17A	107.8
C9—C8—H8	117.3	S1—C17'—H17A	107.8
N1—C9—C8	115.8 (2)	C18'—C17'—H17B	107.8
N1—C9—C10	124.4 (3)	S1—C17'—H17B	107.8
C8—C9—C10	119.8 (2)	H17A—C17'—H17B	107.1
C11—C10—C15	118.6 (3)	C17'—C18'—S2	112.4 (5)
C11—C10—C9	121.7 (3)	C17'—C18'—H18A	109.1
C15—C10—C9	119.7 (3)	S2—C18'—H18A	109.1
C12—C11—C10	120.6 (4)	C17'—C18'—H18B	109.1
C12—C11—H11	119.7	S2—C18'—H18B	109.1
C10—C11—H11	119.7	H18A—C18'—H18B	107.8
C13—C12—C11	120.5 (4)	C9—N1—N2	114.7 (2)
C13—C12—H12	119.8	C16—N2—N1	112.1 (2)
C11—C12—H12	119.8	C16—S1—C17	98.9 (3)
C14—C13—C12	119.7 (3)	C16—S1—C17'	95.7 (3)
C14—C13—H13	120.1	C16—S2—C18'	95.8 (2)
C12—C13—H13	120.1	C16—S2—C18	93.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17'—H17B···Cgi	0.97	2.94	3.842 (9)	156
C18'—H18A···S1ii	0.97	2.69	3.439 (6)	135
C18'—H18B···S1i	0.97	2.86	3.628 (7)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17′—H17B⋯Cgi	0.97	2.94	3.842 (9)	156
C18′—H18A⋯S1ii	0.97	2.69	3.439 (6)	135
C18′—H18B⋯S1i	0.97	2.86	3.628 (7)	137

Symmetry codes: (i) ; (ii) . Cg is the centroid of atoms C10–C15.