(1E,2E)-2-Methyl-3-phenyl-acryl-aldehyde thio-semicarbazone.

In the crystal structure of the title compound, C(11)H(13)N(3)S, mol-ecules form centrosymmetric synthons with an R(2) (2)(8) graph-set motif, linked by pairs of N-H⋯S hydrogen bonds. The synthons are connected through further N-H⋯S hydrogen bonds, extending the packing to form a two-dimensional network lying parallel to (001). In addition, C-H⋯π inter-actions are observed.

Related literature

For related compounds and their biological activity, see: Abid et al. (2008 ▶); Finkielsztein et al. (2008 ▶). For hydrogen bonding in thio­semicarbazones, see: Lima et al. (2002 ▶); Allen et al. (1997 ▶). For the use of resonance-induced hydrogen bonding in supra­molecular chemistry, see: Kearney et al. (1998 ▶). For hydrogen-bond motifs, see Bernstein et al. (1995 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C11H13N3S

M = 219.30

Orthorhombic,

a = 10.9165 (5) Å

b = 7.8150 (3) Å

c = 28.0390 (14) Å

V = 2392.08 (19) Å3

Z = 8

Cu Kα radiation

μ = 2.17 mm−1

T = 293 K

0.51 × 0.06 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.763, T max = 1.000

6973 measured reflections

2241 independent reflections

1644 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.110

S = 1.04

2241 reflections

188 parameters

All H-atom parameters refined

Δρmax = 0.20 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PLATON (Spek, 2009 ▶), PARST95 (Nardelli, 1995 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812022386/ff2068sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022386/ff2068Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022386/ff2068Isup3.cml

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

C11H13N3S	F(000) = 928
Mr = 219.30	Dx = 1.218 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1905 reflections
a = 10.9165 (5) Å	θ = 4.1–70.4°
b = 7.8150 (3) Å	µ = 2.17 mm−1
c = 28.0390 (14) Å	T = 293 K
V = 2392.08 (19) Å3	Plates, white
Z = 8	0.51 × 0.06 × 0.04 mm

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2241 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1644 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 10.2673 pixels mm-1	θmax = 70.5°, θmin = 5.1°
ω scans	h = −9→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −9→8
Tmin = 0.763, Tmax = 1.000	l = −25→34
6973 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	All H-atom parameters refined
S = 1.04	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.029P] where P = (Fo2 + 2Fc2)/3
2241 reflections	(Δ/σ)max < 0.001
188 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction, 2010), Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.33592 (5)	0.16055 (7)	0.01929 (2)	0.0596 (2)
N2	0.37558 (17)	0.4229 (2)	−0.03717 (7)	0.0586 (5)
N1	0.44022 (15)	0.5101 (2)	−0.07187 (6)	0.0561 (4)
C11	0.41598 (18)	0.2686 (2)	−0.02261 (7)	0.0511 (5)
C7	0.4125 (2)	0.9191 (3)	−0.12626 (8)	0.0584 (5)
N3	0.51732 (19)	0.2120 (3)	−0.04238 (9)	0.0692 (6)
C10	0.4010 (2)	0.6596 (3)	−0.08224 (8)	0.0564 (5)
C8	0.46045 (18)	0.7642 (3)	−0.11791 (7)	0.0541 (5)
C6	0.4535 (2)	1.0540 (3)	−0.15896 (7)	0.0573 (5)
C5	0.3674 (3)	1.1629 (3)	−0.17910 (10)	0.0713 (6)
C1	0.5758 (2)	1.0833 (4)	−0.17014 (10)	0.0727 (7)
C9	0.5700 (3)	0.6891 (4)	−0.14221 (11)	0.0764 (7)
C4	0.4017 (3)	1.2909 (4)	−0.21045 (11)	0.0848 (8)
C3	0.5221 (3)	1.3141 (4)	−0.22186 (11)	0.0890 (9)
C2	0.6085 (3)	1.2116 (4)	−0.20136 (11)	0.0883 (9)
H11	0.311 (2)	0.471 (3)	−0.0232 (8)	0.067 (7)*
H12A	0.557 (2)	0.274 (3)	−0.0641 (10)	0.082 (8)*
H7	0.339 (2)	0.944 (3)	−0.1080 (9)	0.069 (7)*
H10	0.332 (2)	0.702 (3)	−0.0649 (8)	0.059 (6)*
H9C	0.641 (3)	0.715 (4)	−0.1228 (13)	0.114 (12)*
H5	0.285 (2)	1.146 (3)	−0.1724 (9)	0.081 (8)*
H9B	0.581 (2)	0.740 (3)	−0.1745 (11)	0.089 (8)*
H9A	0.562 (3)	0.579 (5)	−0.1461 (12)	0.125 (13)*
H1	0.635 (2)	1.014 (3)	−0.1560 (9)	0.076 (8)*
H2	0.690 (3)	1.220 (4)	−0.2086 (11)	0.100 (10)*
H12B	0.546 (3)	0.116 (4)	−0.0339 (9)	0.080 (8)*
H4	0.341 (2)	1.358 (4)	−0.2224 (10)	0.090 (9)*
H3	0.541 (3)	1.403 (4)	−0.2441 (11)	0.098 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.0531 (3)	0.0536 (3)	0.0720 (4)	−0.0009 (2)	−0.0050 (3)	0.0083 (3)
N2	0.0521 (10)	0.0481 (9)	0.0756 (12)	0.0041 (8)	0.0070 (9)	0.0064 (9)
N1	0.0550 (9)	0.0481 (9)	0.0652 (10)	−0.0033 (8)	0.0018 (9)	0.0002 (8)
C11	0.0478 (10)	0.0436 (10)	0.0621 (12)	−0.0031 (8)	−0.0106 (10)	−0.0031 (9)
C7	0.0551 (12)	0.0570 (12)	0.0630 (13)	−0.0016 (10)	0.0047 (11)	0.0018 (10)
N3	0.0636 (12)	0.0543 (11)	0.0898 (15)	0.0106 (10)	0.0142 (11)	0.0096 (11)
C10	0.0531 (11)	0.0504 (11)	0.0656 (13)	0.0009 (10)	0.0041 (10)	0.0010 (10)
C8	0.0543 (11)	0.0526 (11)	0.0553 (11)	−0.0041 (9)	−0.0007 (9)	−0.0026 (10)
C6	0.0696 (13)	0.0494 (11)	0.0528 (11)	−0.0034 (10)	−0.0004 (10)	−0.0014 (9)
C5	0.0783 (16)	0.0580 (13)	0.0776 (16)	0.0026 (13)	−0.0002 (13)	0.0036 (12)
C1	0.0691 (15)	0.0744 (16)	0.0744 (15)	−0.0148 (13)	−0.0067 (13)	0.0121 (13)
C9	0.088 (2)	0.0678 (17)	0.0732 (17)	0.0101 (15)	0.0213 (16)	−0.0001 (14)
C4	0.109 (2)	0.0639 (15)	0.0818 (18)	0.0019 (16)	−0.0199 (18)	0.0136 (14)
C3	0.123 (3)	0.0752 (17)	0.0687 (16)	−0.0288 (18)	−0.0133 (17)	0.0170 (14)
C2	0.088 (2)	0.095 (2)	0.0817 (18)	−0.0314 (17)	0.0004 (17)	0.0151 (16)

S1—C11	1.690 (2)	C6—C5	1.388 (3)
N2—C11	1.347 (3)	C6—C1	1.390 (3)
N2—N1	1.381 (2)	C5—C4	1.384 (4)
N2—H11	0.89 (2)	C5—H5	0.93 (3)
N1—C10	1.278 (3)	C1—C2	1.378 (4)
C11—N3	1.314 (3)	C1—H1	0.93 (3)
C7—C8	1.339 (3)	C9—H9C	0.97 (3)
C7—C6	1.467 (3)	C9—H9B	1.00 (3)
C7—H7	0.97 (2)	C9—H9A	0.87 (4)
N3—H12A	0.89 (3)	C4—C3	1.364 (5)
N3—H12B	0.85 (3)	C4—H4	0.91 (3)
C10—C8	1.446 (3)	C3—C2	1.365 (4)
C10—H10	0.96 (2)	C3—H3	0.96 (3)
C8—C9	1.497 (3)	C2—H2	0.92 (3)
C11—N2—N1	119.17 (18)	C4—C5—C6	121.2 (3)
C11—N2—H11	120.1 (15)	C4—C5—H5	119.7 (17)
N1—N2—H11	120.5 (15)	C6—C5—H5	119.1 (16)
C10—N1—N2	116.09 (17)	C2—C1—C6	120.8 (3)
N3—C11—N2	116.7 (2)	C2—C1—H1	120.9 (16)
N3—C11—S1	124.07 (17)	C6—C1—H1	118.3 (16)
N2—C11—S1	119.25 (16)	C8—C9—H9C	108 (2)
C8—C7—C6	129.7 (2)	C8—C9—H9B	110.5 (16)
C8—C7—H7	114.3 (14)	H9C—C9—H9B	109 (3)
C6—C7—H7	116.0 (14)	C8—C9—H9A	111 (2)
C11—N3—H12A	121.2 (17)	H9C—C9—H9A	111 (3)
C11—N3—H12B	119.2 (18)	H9B—C9—H9A	107 (3)
H12A—N3—H12B	120 (3)	C3—C4—C5	120.4 (3)
N1—C10—C8	121.6 (2)	C3—C4—H4	122.7 (18)
N1—C10—H10	117.6 (13)	C5—C4—H4	116.9 (18)
C8—C10—H10	120.7 (13)	C2—C3—C4	119.3 (3)
C7—C8—C10	117.15 (19)	C2—C3—H3	123.5 (18)
C7—C8—C9	126.0 (2)	C4—C3—H3	117.3 (18)
C10—C8—C9	116.9 (2)	C3—C2—C1	121.1 (3)
C5—C6—C1	117.2 (2)	C3—C2—H2	122.4 (19)
C5—C6—C7	119.2 (2)	C1—C2—H2	116 (2)
C1—C6—C7	123.5 (2)
C11—N2—N1—C10	−176.32 (19)	C8—C7—C6—C5	149.4 (2)
N1—N2—C11—N3	1.0 (3)	C8—C7—C6—C1	−32.5 (4)
N1—N2—C11—N3	1.0 (3)	C1—C6—C5—C4	2.4 (4)
N1—N2—C11—S1	−179.15 (14)	C7—C6—C5—C4	−179.4 (2)
N1—N2—C11—S1	−179.15 (14)	C5—C6—C1—C2	−2.3 (4)
N2—N1—C10—C8	179.95 (18)	C7—C6—C1—C2	179.6 (2)
C6—C7—C8—C10	178.3 (2)	C6—C5—C4—C3	−0.8 (4)
C6—C7—C8—C9	−1.8 (4)	C5—C4—C3—C2	−1.1 (5)
N1—C10—C8—C7	180.0 (2)	C4—C3—C2—C1	1.3 (5)
N1—C10—C8—C9	0.1 (3)	C6—C1—C2—C3	0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H11···S1i	0.89 (2)	2.49 (3)	3.359 (2)	167 (2)
N3—H12B···S1ii	0.85 (3)	2.55 (3)	3.386 (2)	169 (2)
C3—H3···Cg1iii	0.96 (3)	2.89 (3)	3.812 (3)	161 (3)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H11⋯S1i	0.89 (2)	2.49 (3)	3.359 (2)	167 (2)
N3—H12B⋯S1ii	0.85 (3)	2.55 (3)	3.386 (2)	169 (2)
C3—H3⋯Cg1iii	0.96 (3)	2.89 (3)	3.812 (3)	161 (3)

Symmetry codes: (i) ; (ii) ; (iii) .