(2E)-N-Methyl-2-[(2E)-3-phenyl-prop-2-en-1-yl-idene]hydrazinecarbothio-amide.

The title compound, C(11)H(13)N(3)S, is close to being planar, with a dihedral angle of 9.64 (3)° between the benzene ring and the thio-semicarbazone mean plane, maintained by the presence of π-conjugation in the chain linking the the two systems. In the crystal, N-H⋯S hydrogen bonds form centrosymmetric dimers through a cyclic association [graph-set R(2) (2)(8)].

Related literature

For the biological activity and pharmaceutical properties of thio­semicarbazones and their derivatives, see: Casas et al. (2000 ▶); Ferrari et al. (2000 ▶); Murali Krishna et al. (2008 ▶); Murali Krishna & Hussain Reddy (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related compounds, see: Chumakov et al. (2006 ▶).

Experimental

Crystal data

C11H13N3S

M = 219.31

Monoclinic,

a = 5.5265 (11) Å

b = 9.4670 (19) Å

c = 22.534 (5) Å

β = 91.206 (3)°

V = 1178.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 291 K

0.45 × 0.26 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer

8363 measured reflections

2201 independent reflections

1564 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.174

S = 1.06

2201 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PARST (Nardelli, 1995 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037397/zs2229sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037397/zs2229Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037397/zs2229Isup3.cml

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

C11H13N3S	F(000) = 464
Mr = 219.31	Dx = 1.236 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 290 reflections
a = 5.5265 (11) Å	θ = 1.5–26.8°
b = 9.4670 (19) Å	µ = 0.25 mm−1
c = 22.534 (5) Å	T = 291 K
β = 91.206 (3)°	Needle, pale yellow
V = 1178.7 (4) Å3	0.45 × 0.26 × 0.24 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1564 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 25.5°, θmin = 1.8°
ψ and ω scans	h = −6→6
8363 measured reflections	k = −11→11
2201 independent reflections	l = −27→27

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0883P)2 + 0.2979P] where P = (Fo2 + 2Fc2)/3
2201 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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	−0.18251 (17)	0.19579 (9)	1.02989 (4)	0.0887 (4)
N1	0.2855 (4)	0.1898 (2)	0.90259 (9)	0.0638 (6)
N2	0.1638 (4)	0.1576 (3)	0.95336 (10)	0.0675 (6)
H2	0.2067	0.086	0.9746	0.081*
N3	−0.0653 (4)	0.3521 (3)	0.93696 (10)	0.0709 (7)
H3	0.0296	0.3671	0.9079	0.085*
C1	1.1293 (5)	−0.0205 (3)	0.76071 (12)	0.0668 (7)
H1	1.1667	−0.0888	0.7891	0.08*
C2	1.2696 (5)	−0.0095 (4)	0.71108 (13)	0.0764 (8)
H2A	1.4009	−0.0698	0.7066	0.092*
C3	1.2180 (5)	0.0884 (3)	0.66856 (14)	0.0753 (8)
H3A	1.3135	0.0957	0.6352	0.09*
C4	1.0231 (6)	0.1766 (3)	0.67547 (14)	0.0760 (8)
H4	0.9867	0.2435	0.6464	0.091*
C5	0.8811 (5)	0.1673 (3)	0.72468 (13)	0.0685 (7)
H5	0.7493	0.2275	0.7283	0.082*
C6	0.9323 (4)	0.0688 (3)	0.76925 (11)	0.0571 (6)
C7	0.7899 (4)	0.0553 (3)	0.82258 (11)	0.0616 (7)
H7	0.8363	−0.0157	0.849	0.074*
C8	0.6004 (5)	0.1334 (3)	0.83780 (12)	0.0626 (7)
H8	0.5532	0.2071	0.8128	0.075*
C9	0.4655 (5)	0.1101 (3)	0.89050 (11)	0.0627 (7)
H9	0.5088	0.0368	0.9161	0.075*
C10	−0.0242 (5)	0.2395 (3)	0.96975 (12)	0.0621 (7)
C11	−0.2592 (6)	0.4535 (4)	0.94608 (16)	0.0907 (10)
H11A	−0.4034	0.422	0.9256	0.136*
H11B	−0.2123	0.544	0.9309	0.136*
H11C	−0.2896	0.4613	0.9877	0.136*

	U11	U22	U33	U12	U13	U23
S1	0.1036 (7)	0.0873 (6)	0.0769 (6)	−0.0033 (5)	0.0421 (5)	−0.0020 (4)
N1	0.0603 (13)	0.0759 (15)	0.0558 (13)	−0.0073 (11)	0.0119 (10)	−0.0001 (11)
N2	0.0673 (14)	0.0775 (15)	0.0582 (13)	0.0019 (12)	0.0148 (11)	0.0093 (11)
N3	0.0657 (14)	0.0768 (15)	0.0705 (14)	−0.0019 (12)	0.0103 (11)	0.0037 (12)
C1	0.0565 (15)	0.0770 (18)	0.0668 (17)	0.0015 (13)	−0.0017 (13)	−0.0026 (14)
C2	0.0565 (16)	0.095 (2)	0.077 (2)	0.0084 (15)	0.0084 (14)	−0.0134 (17)
C3	0.0700 (18)	0.085 (2)	0.0713 (18)	−0.0077 (16)	0.0201 (14)	−0.0150 (16)
C4	0.084 (2)	0.0718 (19)	0.0728 (19)	−0.0015 (16)	0.0184 (15)	0.0046 (14)
C5	0.0659 (16)	0.0680 (17)	0.0722 (18)	0.0046 (13)	0.0148 (13)	0.0011 (14)
C6	0.0461 (13)	0.0651 (15)	0.0601 (15)	−0.0095 (12)	0.0042 (11)	−0.0082 (12)
C7	0.0517 (14)	0.0700 (16)	0.0628 (15)	−0.0083 (12)	−0.0008 (12)	0.0007 (13)
C8	0.0555 (15)	0.0743 (17)	0.0581 (15)	−0.0084 (13)	0.0056 (12)	−0.0023 (13)
C9	0.0577 (15)	0.0745 (18)	0.0560 (15)	−0.0083 (14)	0.0034 (12)	−0.0030 (13)
C10	0.0608 (15)	0.0658 (16)	0.0601 (16)	−0.0071 (13)	0.0094 (12)	−0.0074 (13)
C11	0.076 (2)	0.081 (2)	0.115 (3)	0.0053 (16)	0.0029 (18)	0.0001 (19)

S1—C10	1.680 (3)	C3—H3A	0.93
N1—C9	1.282 (3)	C4—C5	1.375 (4)
N1—N2	1.373 (3)	C4—H4	0.93
N2—C10	1.354 (3)	C5—C6	1.395 (4)
N2—H2	0.86	C5—H5	0.93
N3—C10	1.314 (4)	C6—C7	1.456 (3)
N3—C11	1.456 (4)	C7—C8	1.333 (4)
N3—H3	0.86	C7—H7	0.93
C1—C2	1.378 (4)	C8—C9	1.432 (4)
C1—C6	1.394 (4)	C8—H8	0.93
C1—H1	0.93	C9—H9	0.93
C2—C3	1.359 (4)	C11—H11A	0.96
C2—H2A	0.93	C11—H11B	0.96
C3—C4	1.374 (4)	C11—H11C	0.96
C9—N1—N2	116.3 (2)	C1—C6—C5	116.9 (2)
C10—N2—N1	119.5 (2)	C1—C6—C7	119.8 (2)
C10—N2—H2	120.2	C5—C6—C7	123.2 (2)
N1—N2—H2	120.2	C8—C7—C6	127.2 (3)
C10—N3—C11	125.0 (3)	C8—C7—H7	116.4
C10—N3—H3	117.5	C6—C7—H7	116.4
C11—N3—H3	117.5	C7—C8—C9	123.6 (3)
C2—C1—C6	121.4 (3)	C7—C8—H8	118.2
C2—C1—H1	119.3	C9—C8—H8	118.2
C6—C1—H1	119.3	N1—C9—C8	120.3 (3)
C3—C2—C1	120.7 (3)	N1—C9—H9	119.8
C3—C2—H2A	119.7	C8—C9—H9	119.8
C1—C2—H2A	119.7	N3—C10—N2	115.8 (2)
C2—C3—C4	119.2 (3)	N3—C10—S1	124.5 (2)
C2—C3—H3A	120.4	N2—C10—S1	119.7 (2)
C4—C3—H3A	120.4	N3—C11—H11A	109.5
C5—C4—C3	121.0 (3)	N3—C11—H11B	109.5
C5—C4—H4	119.5	H11A—C11—H11B	109.5
C3—C4—H4	119.5	N3—C11—H11C	109.5
C4—C5—C6	120.9 (3)	H11A—C11—H11C	109.5
C4—C5—H5	119.6	H11B—C11—H11C	109.5
C6—C5—H5	119.6
C9—N1—N2—C10	178.3 (2)	C1—C6—C7—C8	178.7 (2)
C6—C1—C2—C3	−0.6 (4)	C5—C6—C7—C8	−1.9 (4)
C1—C2—C3—C4	−0.2 (4)	C6—C7—C8—C9	178.0 (2)
C2—C3—C4—C5	0.3 (5)	N2—N1—C9—C8	178.6 (2)
C3—C4—C5—C6	0.5 (5)	C7—C8—C9—N1	179.7 (2)
C2—C1—C6—C5	1.4 (4)	C11—N3—C10—N2	179.2 (3)
C2—C1—C6—C7	−179.2 (2)	C11—N3—C10—S1	−2.5 (4)
C4—C5—C6—C1	−1.3 (4)	N1—N2—C10—N3	−4.7 (4)
C4—C5—C6—C7	179.3 (3)	N1—N2—C10—S1	176.89 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1i	0.86	2.67	3.368 (3)	139
N3—H3···N1	0.86	2.20	2.604 (6)	109
C11—H11C···S1	0.96	2.75	3.108 (6)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1i	0.86	2.67	3.368 (3)	139

Symmetry code: (i) .