Benzyl 3-[(E,E)-3-phenyl-prop-2-enyl-idene]dithio-carbazate.

The title compound, C(17)H(16)N(2)S(2), a dithio-carbazate derivative, adopts an EE configuration with respect to the C=C and C=N double bonds of the propenyl-idine group. The 3-phenyl-prop-2-enyl-idene and dithio-carbazate fragments lie essentially in the same plane, with a maximum deviation from that plane of 0.074 (2) Å, while the dihedral angle between the 3-phenyl-prop-2-enyl-idene and the benzyl group is 77.78 (7)°. In the crystal structure, mol-ecules are linked by an N-H⋯S hydrogen bond and a weak C-H⋯S inter-action involving the terminal thione S atom, forming dimers that are arranged into sheets parallel to the bc plane. The crystal structure is also stabilized by C-H⋯π inter-actions.

Related literature

For information on values of bond lengths, see Allen et al. (1987 ▶). For related structures of dithio­carbazate derivatives, see, for example: Crouse et al. (2004 ▶); Fun et al. (2008 ▶); Shanmuga Sundara Raj et al. (2000 ▶). For applications and bioactivities of dithio­carbazate derivatives, see, for example: Ali & Tarafder (1977 ▶); Ali et al. (2001 ▶, 2002 ▶, 2008 ▶); Chan et al. (2008 ▶); Chew et al. (2004 ▶); Crouse et al. (2004 ▶); Tarafder et al. (1978 ▶, 1981 ▶, 2001 ▶, 2008 ▶).

Experimental

Crystal data

C17H16N2S2

M = 312.44

Triclinic,

a = 5.4350 (3) Å

b = 11.6333 (7) Å

c = 13.6289 (8) Å

α = 66.869 (4)°

β = 82.723 (4)°

γ = 87.520 (4)°

V = 786.04 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 100.0 (1) K

0.58 × 0.19 × 0.05 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.829, T max = 0.982

16100 measured reflections

3570 independent reflections

2870 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.092

S = 1.07

3570 reflections

194 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013354/sj2494sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013354/sj2494Isup2.hkl

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

C17H16N2S2	Z = 2
Mr = 312.44	F000 = 328
Triclinic, P1	Dx = 1.320 Mg m−3
Hall symbol: -P 1	Melting point: 454 K
a = 5.4350 (3) Å	Mo Kα radiation λ = 0.71073 Å
b = 11.6333 (7) Å	Cell parameters from 3570 reflections
c = 13.6289 (8) Å	θ = 1.9–27.5º
α = 66.869 (4)º	µ = 0.33 mm−1
β = 82.723 (4)º	T = 100.0 (1) K
γ = 87.520 (4)º	Needle, yellow
V = 786.04 (8) Å3	0.58 × 0.19 × 0.05 mm

Bruker SMART APEX2 CCD area-detector diffractometer	3570 independent reflections
Radiation source: fine-focus sealed tube	2870 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.044
Detector resolution: 8.33 pixels mm-1	θmax = 27.5º
T = 100.0(1) K	θmin = 1.9º
ω scans	h = −7→7
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −14→15
Tmin = 0.829, Tmax = 0.982	l = −17→17
16100 measured reflections

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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0368P)2 + 0.3179P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3570 reflections	Δρmax = 0.29 e Å−3
194 parameters	Δρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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 > 2sigma(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	−0.13630 (8)	0.74106 (4)	0.65560 (3)	0.02137 (13)
S2	−0.23454 (8)	0.66804 (4)	0.47403 (4)	0.02329 (13)
N1	0.1010 (3)	0.56987 (15)	0.60587 (12)	0.0209 (3)
N2	0.2180 (3)	0.55500 (14)	0.69440 (11)	0.0212 (3)
C1	−0.2508 (3)	1.02812 (17)	0.63242 (14)	0.0241 (4)
H1A	−0.1133	1.0404	0.5812	0.029*
C2	−0.2838 (3)	1.10363 (18)	0.68983 (15)	0.0270 (4)
H2A	−0.1690	1.1664	0.6771	0.032*
C3	−0.4872 (3)	1.08611 (18)	0.76620 (15)	0.0265 (4)
H3A	−0.5087	1.1364	0.8054	0.032*
C4	−0.6584 (3)	0.99380 (18)	0.78414 (15)	0.0261 (4)
H4A	−0.7964	0.9824	0.8350	0.031*
C5	−0.6253 (3)	0.91803 (17)	0.72668 (15)	0.0230 (4)
H5A	−0.7413	0.8558	0.7393	0.028*
C6	−0.4207 (3)	0.93393 (16)	0.65043 (14)	0.0203 (4)
C7	−0.3781 (3)	0.84724 (17)	0.59218 (14)	0.0222 (4)
H7A	−0.3250	0.8938	0.5164	0.027*
H7B	−0.5287	0.8014	0.5993	0.027*
C8	−0.0802 (3)	0.65301 (16)	0.57678 (14)	0.0199 (4)
C9	0.3953 (3)	0.47537 (16)	0.71089 (14)	0.0205 (4)
H9A	0.4371	0.4369	0.6628	0.025*
C10	0.5303 (3)	0.44442 (16)	0.80163 (14)	0.0207 (4)
H10A	0.4896	0.4829	0.8497	0.025*
C11	0.7138 (3)	0.36108 (16)	0.81818 (14)	0.0209 (4)
H11A	0.7506	0.3277	0.7662	0.025*
C12	0.8636 (3)	0.31572 (16)	0.90742 (14)	0.0202 (4)
C13	0.8492 (3)	0.36609 (17)	0.98578 (15)	0.0254 (4)
H13A	0.7375	0.4298	0.9830	0.030*
C14	0.9991 (4)	0.32206 (18)	1.06702 (15)	0.0285 (4)
H14A	0.9889	0.3570	1.1182	0.034*
C15	1.1645 (4)	0.22635 (19)	1.07320 (15)	0.0298 (4)
H15A	1.2654	0.1972	1.1282	0.036*
C16	1.1791 (3)	0.17447 (19)	0.99739 (15)	0.0306 (5)
H16A	1.2890	0.1096	1.0016	0.037*
C17	1.0301 (3)	0.21890 (18)	0.91488 (15)	0.0257 (4)
H17A	1.0415	0.1836	0.8639	0.031*
H1N1	0.129 (4)	0.519 (2)	0.5733 (18)	0.038 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0237 (2)	0.0250 (2)	0.0198 (2)	0.00424 (18)	−0.00880 (17)	−0.01190 (19)
S2	0.0242 (2)	0.0305 (3)	0.0194 (2)	0.00284 (19)	−0.00832 (17)	−0.0129 (2)
N1	0.0221 (8)	0.0265 (8)	0.0190 (8)	0.0024 (6)	−0.0071 (6)	−0.0128 (7)
N2	0.0218 (8)	0.0265 (8)	0.0165 (7)	−0.0001 (6)	−0.0052 (6)	−0.0090 (6)
C1	0.0193 (9)	0.0296 (10)	0.0230 (9)	0.0001 (8)	0.0002 (7)	−0.0106 (8)
C2	0.0238 (10)	0.0256 (10)	0.0316 (11)	−0.0046 (8)	−0.0010 (8)	−0.0114 (9)
C3	0.0255 (10)	0.0279 (10)	0.0311 (10)	0.0026 (8)	−0.0030 (8)	−0.0172 (9)
C4	0.0193 (9)	0.0321 (11)	0.0279 (10)	−0.0005 (8)	0.0007 (7)	−0.0136 (9)
C5	0.0182 (9)	0.0250 (10)	0.0260 (10)	−0.0033 (7)	−0.0041 (7)	−0.0094 (8)
C6	0.0189 (9)	0.0223 (9)	0.0195 (9)	0.0031 (7)	−0.0076 (7)	−0.0067 (7)
C7	0.0212 (9)	0.0258 (10)	0.0211 (9)	0.0027 (7)	−0.0081 (7)	−0.0095 (8)
C8	0.0197 (9)	0.0225 (9)	0.0174 (9)	−0.0025 (7)	−0.0018 (7)	−0.0076 (7)
C9	0.0199 (9)	0.0229 (9)	0.0212 (9)	−0.0018 (7)	−0.0027 (7)	−0.0109 (8)
C10	0.0230 (9)	0.0233 (9)	0.0185 (9)	−0.0023 (7)	−0.0039 (7)	−0.0102 (7)
C11	0.0226 (9)	0.0217 (9)	0.0207 (9)	−0.0029 (7)	−0.0034 (7)	−0.0103 (7)
C12	0.0179 (9)	0.0206 (9)	0.0209 (9)	−0.0033 (7)	−0.0032 (7)	−0.0063 (7)
C13	0.0279 (10)	0.0239 (10)	0.0245 (10)	0.0001 (8)	−0.0067 (8)	−0.0085 (8)
C14	0.0361 (11)	0.0285 (10)	0.0214 (10)	−0.0048 (8)	−0.0084 (8)	−0.0083 (8)
C15	0.0236 (10)	0.0373 (11)	0.0217 (10)	−0.0033 (8)	−0.0074 (8)	−0.0025 (9)
C16	0.0227 (10)	0.0351 (11)	0.0276 (10)	0.0061 (8)	−0.0033 (8)	−0.0058 (9)
C17	0.0243 (10)	0.0293 (10)	0.0229 (10)	0.0024 (8)	−0.0017 (7)	−0.0100 (8)

S1—C8	1.7466 (17)	C7—H7A	0.9700
S1—C7	1.8187 (17)	C7—H7B	0.9700
S2—C8	1.6696 (18)	C9—C10	1.433 (2)
N1—C8	1.334 (2)	C9—H9A	0.9300
N1—N2	1.382 (2)	C10—C11	1.337 (2)
N1—H1N1	0.87 (2)	C10—H10A	0.9300
N2—C9	1.285 (2)	C11—C12	1.460 (2)
C1—C2	1.381 (3)	C11—H11A	0.9300
C1—C6	1.390 (3)	C12—C17	1.394 (2)
C1—H1A	0.9300	C12—C13	1.399 (3)
C2—C3	1.381 (3)	C13—C14	1.378 (3)
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.379 (3)	C14—C15	1.384 (3)
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.384 (3)	C15—C16	1.380 (3)
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.387 (2)	C16—C17	1.387 (3)
C5—H5A	0.9300	C16—H16A	0.9300
C6—C7	1.504 (2)	C17—H17A	0.9300
C8—S1—C7	102.56 (8)	N1—C8—S1	113.76 (13)
C8—N1—N2	120.49 (15)	S2—C8—S1	124.67 (10)
C8—N1—H1N1	118.0 (15)	N2—C9—C10	121.56 (16)
N2—N1—H1N1	120.9 (15)	N2—C9—H9A	119.2
C9—N2—N1	114.00 (14)	C10—C9—H9A	119.2
C2—C1—C6	120.70 (17)	C11—C10—C9	121.02 (16)
C2—C1—H1A	119.6	C11—C10—H10A	119.5
C6—C1—H1A	119.6	C9—C10—H10A	119.5
C1—C2—C3	120.11 (18)	C10—C11—C12	128.25 (16)
C1—C2—H2A	119.9	C10—C11—H11A	115.9
C3—C2—H2A	119.9	C12—C11—H11A	115.9
C4—C3—C2	119.76 (17)	C17—C12—C13	118.27 (16)
C4—C3—H3A	120.1	C17—C12—C11	118.96 (16)
C2—C3—H3A	120.1	C13—C12—C11	122.77 (16)
C3—C4—C5	120.16 (17)	C14—C13—C12	120.56 (17)
C3—C4—H4A	119.9	C14—C13—H13A	119.7
C5—C4—H4A	119.9	C12—C13—H13A	119.7
C4—C5—C6	120.65 (17)	C13—C14—C15	120.60 (18)
C4—C5—H5A	119.7	C13—C14—H14A	119.7
C6—C5—H5A	119.7	C15—C14—H14A	119.7
C5—C6—C1	118.61 (16)	C16—C15—C14	119.64 (17)
C5—C6—C7	120.57 (17)	C16—C15—H15A	120.2
C1—C6—C7	120.76 (16)	C14—C15—H15A	120.2
C6—C7—S1	105.49 (12)	C15—C16—C17	120.11 (18)
C6—C7—H7A	110.6	C15—C16—H16A	119.9
S1—C7—H7A	110.6	C17—C16—H16A	119.9
C6—C7—H7B	110.6	C16—C17—C12	120.81 (18)
S1—C7—H7B	110.6	C16—C17—H17A	119.6
H7A—C7—H7B	108.8	C12—C17—H17A	119.6
N1—C8—S2	121.57 (13)
C8—N1—N2—C9	−177.45 (16)	C7—S1—C8—S2	−2.52 (14)
C6—C1—C2—C3	0.1 (3)	N1—N2—C9—C10	−177.41 (16)
C1—C2—C3—C4	−0.6 (3)	N2—C9—C10—C11	179.74 (17)
C2—C3—C4—C5	0.7 (3)	C9—C10—C11—C12	−177.74 (17)
C3—C4—C5—C6	−0.1 (3)	C10—C11—C12—C17	173.65 (18)
C4—C5—C6—C1	−0.5 (3)	C10—C11—C12—C13	−6.9 (3)
C4—C5—C6—C7	176.79 (16)	C17—C12—C13—C14	1.0 (3)
C2—C1—C6—C5	0.5 (3)	C11—C12—C13—C14	−178.40 (17)
C2—C1—C6—C7	−176.74 (17)	C12—C13—C14—C15	−0.7 (3)
C5—C6—C7—S1	−102.64 (16)	C13—C14—C15—C16	−0.1 (3)
C1—C6—C7—S1	74.54 (18)	C14—C15—C16—C17	0.6 (3)
C8—S1—C7—C6	−175.27 (12)	C15—C16—C17—C12	−0.2 (3)
N2—N1—C8—S2	−176.88 (13)	C13—C12—C17—C16	−0.6 (3)
N2—N1—C8—S1	3.0 (2)	C11—C12—C17—C16	178.89 (17)
C7—S1—C8—N1	177.58 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···S2i	0.87 (2)	2.53 (2)	3.3714 (19)	165 (2)
C9—H9A···S2i	0.93	2.93	3.7264 (18)	144
C15—H15A···Cg1ii	0.93	2.83	3.649 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯S2i	0.87 (2)	2.53 (2)	3.3714 (19)	165 (2)
C9—H9A⋯S2i	0.93	2.93	3.7264 (18)	144
C15—H15A⋯Cg1ii	0.93	2.83	3.649 (2)	148

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C1–C6 phenyl ring.