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

In the title compound, C(11)H(12)N(2)S(2), the dithio-carbazate group adopts an EE configuration with respect to the C=C and C=N bonds of the propenyl-idene group. The atoms of the propenyl-idene and dithio-carbazate unit are essentially co-planar, with a maximum deviation of 0.058 (1) Å; the phenyl ring forms a dihedral angle of 18.3 (1)° with this fragment. In the crystal, mol-ecules form inversion dimers via pairs of N-H⋯S hydrogen bonds involving the terminal S atom.

Related literature

For the synthesis and a related structure, see: Tarafder et al. (2008 ▶).

Experimental

Crystal data

C11H12N2S2

M = 236.35

Monoclinic,

a = 10.408 (2) Å

b = 5.4950 (9) Å

c = 20.988 (2) Å

β = 100.697 (10)°

V = 1179.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 293 K

0.40 × 0.15 × 0.12 mm

Data collection

Enraf–Nonius DIP1030 image-plate diffractometer

6316 measured reflections

2048 independent reflections

1569 reflections with I > 2.0σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.116

S = 1.04

2048 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.21 e Å−3

Data collection: XPRESS (MacScience, 2002 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810041115/pv2336sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041115/pv2336Isup2.hkl

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

C11H12N2S2	F(000) = 496
Mr = 236.35	Dx = 1.331 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 275 reflections
a = 10.408 (2) Å	θ = 3.6–20.7°
b = 5.4950 (9) Å	µ = 0.42 mm−1
c = 20.988 (2) Å	T = 293 K
β = 100.697 (10)°	Needle, orange
V = 1179.5 (3) Å3	0.40 × 0.15 × 0.12 mm
Z = 4

Enraf–Nonius DIP1030 image-plate diffractometer	1569 reflections with I > 2.0σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
graphite	θmax = 25.3°, θmin = 3.1°
φ–scans with narrow frames	h = −12→12
6316 measured reflections	k = −6→6
2048 independent reflections	l = −25→25

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0721P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2048 reflections	Δρmax = 0.14 e Å−3
138 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (4)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	1.15322 (6)	0.68232 (10)	0.57196 (3)	0.0759 (2)
S2	1.08034 (6)	0.51686 (10)	0.69852 (3)	0.0734 (2)
N1	0.99960 (18)	0.3187 (3)	0.58644 (8)	0.0682 (5)
H1	0.9962	0.2915	0.5458	0.082*
N2	0.92717 (19)	0.1751 (3)	0.62061 (9)	0.0680 (5)
C1	1.1813 (3)	0.7789 (4)	0.72034 (11)	0.0791 (6)
H1A	1.2653	0.7525	0.7089	0.119*
H1B	1.1918	0.8059	0.7662	0.119*
H1C	1.1407	0.9187	0.6976	0.119*
C2	1.0751 (2)	0.4996 (3)	0.61523 (10)	0.0625 (5)
C3	0.8633 (2)	0.0018 (3)	0.58766 (11)	0.0656 (5)
H3	0.8723	−0.0225	0.5449	0.079*
C4	0.7788 (2)	−0.1538 (3)	0.61562 (10)	0.0670 (5)
H4	0.7718	−0.1294	0.6587	0.080*
C5	0.7095 (2)	−0.3328 (3)	0.58259 (10)	0.0653 (5)
H5	0.7240	−0.3613	0.5408	0.078*
C6	0.6139 (2)	−0.4880 (3)	0.60503 (10)	0.0634 (5)
C7	0.5705 (3)	−0.4487 (4)	0.66304 (12)	0.0750 (6)
H7	0.6053	−0.3208	0.6898	0.090*
C8	0.4770 (3)	−0.5962 (5)	0.68147 (14)	0.0898 (7)
H8	0.4487	−0.5659	0.7202	0.108*
C9	0.4250 (3)	−0.7874 (5)	0.64316 (17)	0.0963 (9)
H9	0.3623	−0.8870	0.6560	0.116*
C10	0.4657 (3)	−0.8309 (4)	0.58615 (16)	0.0944 (8)
H10	0.4305	−0.9603	0.5601	0.113*
C11	0.5596 (3)	−0.6831 (4)	0.56675 (13)	0.0799 (7)
H11	0.5866	−0.7146	0.5277	0.096*

	U11	U22	U33	U12	U13	U23
S1	0.0761 (5)	0.0872 (4)	0.0662 (4)	−0.0152 (3)	0.0178 (3)	0.0061 (2)
S2	0.0809 (5)	0.0799 (4)	0.0592 (4)	−0.0143 (3)	0.0122 (3)	0.0035 (2)
N1	0.0743 (13)	0.0726 (10)	0.0600 (10)	−0.0089 (9)	0.0181 (9)	−0.0002 (7)
N2	0.0681 (12)	0.0698 (10)	0.0670 (10)	−0.0066 (8)	0.0150 (9)	0.0030 (8)
C1	0.0811 (17)	0.0813 (13)	0.0730 (14)	−0.0110 (12)	0.0092 (12)	−0.0046 (10)
C2	0.0574 (13)	0.0664 (12)	0.0636 (12)	0.0012 (9)	0.0112 (9)	0.0024 (8)
C3	0.0686 (15)	0.0647 (12)	0.0631 (12)	0.0011 (10)	0.0111 (10)	0.0014 (8)
C4	0.0698 (15)	0.0673 (11)	0.0631 (12)	−0.0028 (10)	0.0104 (10)	0.0010 (9)
C5	0.0682 (14)	0.0658 (12)	0.0611 (11)	0.0013 (10)	0.0099 (10)	−0.0002 (8)
C6	0.0633 (14)	0.0560 (10)	0.0683 (13)	0.0023 (8)	0.0057 (10)	0.0036 (8)
C7	0.0799 (17)	0.0700 (12)	0.0756 (14)	−0.0059 (11)	0.0160 (12)	0.0006 (10)
C8	0.090 (2)	0.0870 (15)	0.0964 (18)	−0.0020 (14)	0.0276 (15)	0.0160 (13)
C9	0.0772 (18)	0.0813 (16)	0.129 (3)	−0.0085 (13)	0.0151 (17)	0.0274 (16)
C10	0.091 (2)	0.0722 (15)	0.114 (2)	−0.0154 (13)	0.0022 (17)	−0.0017 (13)
C11	0.0866 (18)	0.0680 (13)	0.0813 (15)	−0.0038 (12)	0.0061 (13)	−0.0054 (10)

S1—C2	1.664 (2)	C5—C6	1.454 (3)
S2—C2	1.741 (2)	C5—H5	0.9300
S2—C1	1.791 (2)	C6—C7	1.392 (3)
N1—C2	1.339 (3)	C6—C11	1.395 (3)
N1—N2	1.381 (2)	C7—C8	1.376 (3)
N1—H1	0.8600	C7—H7	0.9300
N2—C3	1.287 (3)	C8—C9	1.372 (4)
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—C10	1.363 (4)
C1—H1C	0.9600	C9—H9	0.9300
C3—C4	1.428 (3)	C10—C11	1.388 (4)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.335 (3)	C11—H11	0.9300
C4—H4	0.9300
C2—S2—C1	102.02 (11)	C4—C5—H5	116.6
C2—N1—N2	121.39 (18)	C6—C5—H5	116.6
C2—N1—H1	119.3	C7—C6—C11	117.4 (2)
N2—N1—H1	119.3	C7—C6—C5	123.05 (18)
C3—N2—N1	114.92 (18)	C11—C6—C5	119.5 (2)
S2—C1—H1A	109.5	C8—C7—C6	121.1 (2)
S2—C1—H1B	109.5	C8—C7—H7	119.5
H1A—C1—H1B	109.5	C6—C7—H7	119.5
S2—C1—H1C	109.5	C9—C8—C7	120.6 (3)
H1A—C1—H1C	109.5	C9—C8—H8	119.7
H1B—C1—H1C	109.5	C7—C8—H8	119.7
N1—C2—S1	120.44 (16)	C10—C9—C8	119.7 (3)
N1—C2—S2	113.58 (15)	C10—C9—H9	120.1
S1—C2—S2	125.98 (12)	C8—C9—H9	120.1
N2—C3—C4	121.2 (2)	C9—C10—C11	120.4 (2)
N2—C3—H3	119.4	C9—C10—H10	119.8
C4—C3—H3	119.4	C11—C10—H10	119.8
C5—C4—C3	122.8 (2)	C10—C11—C6	120.8 (3)
C5—C4—H4	118.6	C10—C11—H11	119.6
C3—C4—H4	118.6	C6—C11—H11	119.6
C4—C5—C6	126.9 (2)
C2—N1—N2—C3	−177.27 (18)	C4—C5—C6—C11	−173.6 (2)
N2—N1—C2—S1	−175.70 (15)	C11—C6—C7—C8	−0.5 (3)
N2—N1—C2—S2	4.4 (2)	C5—C6—C7—C8	178.1 (2)
C1—S2—C2—N1	−177.67 (16)	C6—C7—C8—C9	0.6 (4)
C1—S2—C2—S1	2.41 (18)	C7—C8—C9—C10	−0.4 (4)
N1—N2—C3—C4	−176.76 (18)	C8—C9—C10—C11	0.1 (4)
N2—C3—C4—C5	178.9 (2)	C9—C10—C11—C6	0.0 (4)
C3—C4—C5—C6	−174.93 (19)	C7—C6—C11—C10	0.2 (3)
C4—C5—C6—C7	7.9 (3)	C5—C6—C11—C10	−178.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.86	2.67	3.4086 (19)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.86	2.67	3.4086 (19)	145

Symmetry code: (i) .