1-Benzyl-idene-4-ethyl-thio-semicarbazide.

The title compound, C(10)H(13)N(3)S, was prepared by the reaction of 4-ethyl-thio-semicarbazide and benzaldehyde. The dihedral angle between the benzene ring and the thio-urea unit is 8.96 (7)° and an intra-molecular N-H⋯N hydrogen bond generates an S(5) ring. In the crystal, inversion dimers linked by pairs of N-H⋯S hydrogen bonds generate R(2) (2)(8) loops.

Related literature

For background to the coordination chemistry of Schiff bases, see: Habermehl et al. (2006 ▶). For a related structure, see: Li & Jian (2010 ▶).

Experimental

Crystal data

C10H13N3S

M = 207.30

Monoclinic,

a = 8.4899 (17) Å

b = 13.467 (3) Å

c = 10.015 (2) Å

β = 96.04 (3)°

V = 1138.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

10048 measured reflections

2596 independent reflections

2118 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.152

S = 1.09

2596 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.40 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038444/hb5654sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038444/hb5654Isup2.hkl

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

C10H13N3S	F(000) = 440
Mr = 207.30	Dx = 1.209 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2596 reflections
a = 8.4899 (17) Å	θ = 3.0–27.5°
b = 13.467 (3) Å	µ = 0.25 mm−1
c = 10.015 (2) Å	T = 293 K
β = 96.04 (3)°	Block, colorless
V = 1138.7 (4) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	2118 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 27.5°, θmin = 3.0°
phi and ω scans	h = −10→9
10048 measured reflections	k = −17→17
2596 independent reflections	l = −13→13

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0834P)2 + 0.1728P] where P = (Fo2 + 2Fc2)/3
2596 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.40 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	0.28967 (7)	0.39580 (4)	−0.07292 (4)	0.0744 (2)
N1	0.25491 (17)	0.29999 (11)	0.15603 (14)	0.0596 (4)
H1A	0.2916	0.2862	0.2372	0.072*
N2	0.46620 (17)	0.40411 (10)	0.15771 (13)	0.0537 (3)
H2A	0.5279	0.4416	0.1171	0.064*
N3	0.50010 (15)	0.38467 (9)	0.29257 (13)	0.0479 (3)
C4	0.61893 (18)	0.43036 (12)	0.35133 (16)	0.0504 (4)
H4A	0.6768	0.4724	0.3014	0.061*
C3	0.3357 (2)	0.36416 (12)	0.08914 (15)	0.0516 (4)
C5	0.66728 (17)	0.41886 (11)	0.49435 (16)	0.0473 (3)
C6	0.5847 (2)	0.35906 (13)	0.57650 (17)	0.0566 (4)
H6A	0.4966	0.3235	0.5399	0.068*
C10	0.7983 (2)	0.47106 (14)	0.55174 (19)	0.0624 (4)
H10A	0.8542	0.5117	0.4983	0.075*
C7	0.6330 (3)	0.35251 (16)	0.71139 (19)	0.0721 (5)
H7A	0.5773	0.3125	0.7658	0.087*
C9	0.8465 (2)	0.46324 (17)	0.6869 (2)	0.0765 (6)
H9A	0.9356	0.4977	0.7238	0.092*
C8	0.7637 (3)	0.40488 (16)	0.7670 (2)	0.0775 (6)
H8A	0.7953	0.4005	0.8586	0.093*
C1	−0.0363 (3)	0.3091 (2)	0.1253 (3)	0.1024 (9)
H1B	−0.1290	0.2740	0.0876	0.154*
H1C	−0.0324	0.3729	0.0832	0.154*
H1D	−0.0405	0.3176	0.2200	0.154*
C2	0.1083 (3)	0.25096 (16)	0.1020 (2)	0.0777 (6)
H2B	0.1027	0.1862	0.1435	0.093*
H2C	0.1102	0.2410	0.0063	0.093*

	U11	U22	U33	U12	U13	U23
S1	0.0973 (4)	0.0820 (4)	0.0422 (3)	−0.0240 (3)	−0.0006 (2)	0.00516 (19)
N1	0.0682 (9)	0.0602 (8)	0.0491 (7)	−0.0158 (7)	0.0001 (6)	0.0046 (6)
N2	0.0586 (8)	0.0584 (8)	0.0443 (7)	−0.0070 (6)	0.0066 (6)	0.0044 (5)
N3	0.0514 (7)	0.0472 (7)	0.0451 (7)	0.0009 (5)	0.0046 (5)	0.0014 (5)
C4	0.0470 (8)	0.0513 (8)	0.0534 (8)	−0.0022 (6)	0.0070 (6)	0.0066 (7)
C3	0.0598 (9)	0.0503 (8)	0.0450 (8)	−0.0013 (7)	0.0070 (6)	−0.0036 (6)
C5	0.0444 (7)	0.0436 (7)	0.0533 (8)	0.0039 (6)	0.0026 (6)	0.0001 (6)
C6	0.0599 (9)	0.0524 (8)	0.0572 (9)	−0.0016 (7)	0.0049 (7)	0.0063 (7)
C10	0.0529 (9)	0.0616 (10)	0.0714 (11)	−0.0050 (8)	0.0000 (8)	−0.0015 (8)
C7	0.0932 (14)	0.0654 (11)	0.0584 (10)	0.0106 (10)	0.0110 (9)	0.0107 (9)
C9	0.0693 (12)	0.0740 (12)	0.0806 (13)	0.0041 (10)	−0.0182 (10)	−0.0179 (10)
C8	0.0976 (15)	0.0781 (13)	0.0528 (10)	0.0246 (11)	−0.0108 (10)	−0.0087 (9)
C1	0.0765 (14)	0.0977 (18)	0.126 (2)	−0.0322 (14)	−0.0217 (14)	0.0169 (15)
C2	0.0950 (15)	0.0722 (12)	0.0629 (11)	−0.0365 (11)	−0.0059 (10)	0.0025 (9)

S1—C3	1.6838 (16)	C10—C9	1.376 (3)
N1—C3	1.328 (2)	C10—H10A	0.9300
N1—C2	1.462 (2)	C7—C8	1.382 (3)
N1—H1A	0.8600	C7—H7A	0.9300
N2—C3	1.352 (2)	C9—C8	1.370 (3)
N2—N3	1.3761 (18)	C9—H9A	0.9300
N2—H2A	0.8600	C8—H8A	0.9300
N3—C4	1.272 (2)	C1—C2	1.495 (4)
C4—C5	1.456 (2)	C1—H1B	0.9600
C4—H4A	0.9300	C1—H1C	0.9600
C5—C10	1.389 (2)	C1—H1D	0.9600
C5—C6	1.392 (2)	C2—H2B	0.9700
C6—C7	1.373 (2)	C2—H2C	0.9700
C6—H6A	0.9300
C3—N1—C2	124.92 (15)	C6—C7—C8	120.6 (2)
C3—N1—H1A	117.5	C6—C7—H7A	119.7
C2—N1—H1A	117.5	C8—C7—H7A	119.7
C3—N2—N3	119.89 (13)	C8—C9—C10	120.19 (19)
C3—N2—H2A	120.1	C8—C9—H9A	119.9
N3—N2—H2A	120.1	C10—C9—H9A	119.9
C4—N3—N2	115.84 (13)	C9—C8—C7	119.75 (19)
N3—C4—C5	122.10 (14)	C9—C8—H8A	120.1
N3—C4—H4A	118.9	C7—C8—H8A	120.1
C5—C4—H4A	118.9	C2—C1—H1B	109.5
N1—C3—N2	116.22 (14)	C2—C1—H1C	109.5
N1—C3—S1	124.84 (13)	H1B—C1—H1C	109.5
N2—C3—S1	118.92 (13)	C2—C1—H1D	109.5
C10—C5—C6	118.67 (15)	H1B—C1—H1D	109.5
C10—C5—C4	118.95 (15)	H1C—C1—H1D	109.5
C6—C5—C4	122.37 (14)	N1—C2—C1	112.78 (18)
C7—C6—C5	120.11 (17)	N1—C2—H2B	109.0
C7—C6—H6A	119.9	C1—C2—H2B	109.0
C5—C6—H6A	119.9	N1—C2—H2C	109.0
C9—C10—C5	120.71 (18)	C1—C2—H2C	109.0
C9—C10—H10A	119.6	H2B—C2—H2C	107.8
C5—C10—H10A	119.6

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3	0.86	2.23	2.628 (2)	108
N2—H2A···S1i	0.86	2.74	3.5565 (16)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N3	0.86	2.23	2.628 (2)	108
N2—H2A⋯S1i	0.86	2.74	3.5565 (16)	158

Symmetry code: (i) .