1-(4-Chloro-benzyl-idene)-4-ethyl-thio-semicarbazide.

In the title compound, C(10)H(12)ClN(3)S, the dihedral angle between the benzene ring and the thio-urea unit is 2.35 (19)°. In the crystal, inversion dimers linked by pairs of N-H⋯S hydrogen bonds generate R(2) (2)(8) loops.

Related literature

For related structures, see: Li & Jian (2010 ▶); Li & Meng (2010 ▶).

Experimental

Crystal data

C10H12ClN3S

M = 241.75

Monoclinic,

a = 4.6769 (10) Å

b = 26.727 (6) Å

c = 9.791 (3) Å

β = 102.59 (3)°

V = 1194.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.47 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

11437 measured reflections

2723 independent reflections

1388 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.272

S = 1.09

2723 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.34 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/S1600536810047446/hb5737sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047446/hb5737Isup2.hkl

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

C10H12ClN3S	F(000) = 504
Mr = 241.75	Dx = 1.344 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2723 reflections
a = 4.6769 (10) Å	θ = 3.1–27.5°
b = 26.727 (6) Å	µ = 0.47 mm−1
c = 9.791 (3) Å	T = 293 K
β = 102.59 (3)°	Bar, colorless
V = 1194.4 (5) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	1388 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.066
graphite	θmax = 27.5°, θmin = 3.1°
phi and ω scans	h = −6→5
11437 measured reflections	k = −34→34
2723 independent reflections	l = −12→12

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.272	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.1156P)2 + 1.1747P] where P = (Fo2 + 2Fc2)/3
2723 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.33 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	1.2104 (3)	−0.01352 (5)	0.72223 (14)	0.0738 (5)
Cl1	−0.3450 (4)	0.27875 (6)	0.46099 (18)	0.1022 (6)
N2	0.7928 (8)	0.04912 (15)	0.6097 (4)	0.0637 (10)
H2A	0.7695	0.0311	0.5354	0.076*
N3	0.6207 (8)	0.09071 (14)	0.6128 (4)	0.0616 (10)
C5	0.2251 (9)	0.14199 (17)	0.4970 (5)	0.0576 (11)
C4	0.4166 (10)	0.09865 (18)	0.5041 (5)	0.0622 (11)
H4A	0.3907	0.0765	0.4291	0.075*
N1	1.0195 (10)	0.06662 (17)	0.8346 (4)	0.0789 (13)
H1A	0.8985	0.0912	0.8260	0.095*
C10	0.0157 (10)	0.15053 (19)	0.3771 (5)	0.0664 (12)
H10A	−0.0066	0.1281	0.3028	0.080*
C6	0.2528 (11)	0.1751 (2)	0.6072 (5)	0.0723 (13)
H6A	0.3933	0.1695	0.6889	0.087*
C9	−0.1627 (11)	0.1925 (2)	0.3665 (5)	0.0709 (13)
H9A	−0.3045	0.1983	0.2853	0.085*
C3	0.9998 (10)	0.03689 (17)	0.7250 (5)	0.0602 (11)
C8	−0.1287 (11)	0.22552 (19)	0.4764 (5)	0.0679 (12)
C7	0.0731 (14)	0.2164 (2)	0.5967 (6)	0.0836 (16)
H7A	0.0898	0.2382	0.6721	0.100*
C2	1.2242 (16)	0.0617 (2)	0.9669 (6)	0.096 (2)
H2B	1.1446	0.0383	1.0247	0.116*
H2C	1.4045	0.0475	0.9506	0.116*
C1	1.290 (2)	0.1061 (3)	1.0404 (9)	0.130 (3)
H1B	1.4287	0.0997	1.1264	0.196*
H1C	1.1142	0.1199	1.0606	0.196*
H1D	1.3723	0.1294	0.9851	0.196*

	U11	U22	U33	U12	U13	U23
S1	0.0781 (9)	0.0700 (8)	0.0700 (8)	0.0180 (6)	0.0089 (6)	0.0022 (6)
Cl1	0.1142 (13)	0.0852 (11)	0.1023 (12)	0.0396 (9)	0.0129 (9)	0.0139 (8)
N2	0.060 (2)	0.069 (2)	0.061 (2)	0.0125 (19)	0.0087 (17)	−0.0022 (18)
N3	0.060 (2)	0.062 (2)	0.063 (2)	0.0073 (19)	0.0145 (18)	0.0012 (17)
C5	0.054 (2)	0.062 (3)	0.055 (2)	−0.002 (2)	0.0104 (19)	0.0026 (19)
C4	0.057 (3)	0.069 (3)	0.059 (3)	0.008 (2)	0.010 (2)	−0.001 (2)
N1	0.087 (3)	0.079 (3)	0.063 (3)	0.025 (2)	0.000 (2)	−0.008 (2)
C10	0.063 (3)	0.070 (3)	0.062 (3)	0.002 (2)	0.006 (2)	−0.001 (2)
C6	0.072 (3)	0.077 (3)	0.060 (3)	0.014 (3)	−0.003 (2)	−0.004 (2)
C9	0.066 (3)	0.077 (3)	0.064 (3)	0.009 (3)	0.001 (2)	0.013 (2)
C3	0.057 (2)	0.063 (3)	0.062 (3)	0.006 (2)	0.013 (2)	0.005 (2)
C8	0.068 (3)	0.067 (3)	0.067 (3)	0.011 (2)	0.011 (2)	0.012 (2)
C7	0.098 (4)	0.079 (4)	0.068 (3)	0.025 (3)	0.005 (3)	−0.011 (3)
C2	0.111 (5)	0.085 (4)	0.077 (4)	0.012 (4)	−0.014 (3)	−0.005 (3)
C1	0.153 (7)	0.094 (5)	0.112 (6)	−0.002 (5)	−0.039 (5)	−0.022 (4)

S1—C3	1.673 (5)	C10—H10A	0.9300
Cl1—C8	1.733 (5)	C6—C7	1.379 (7)
N2—C3	1.357 (6)	C6—H6A	0.9300
N2—N3	1.377 (5)	C9—C8	1.373 (7)
N2—H2A	0.8600	C9—H9A	0.9300
N3—C4	1.283 (6)	C8—C7	1.361 (7)
C5—C10	1.374 (6)	C7—H7A	0.9300
C5—C6	1.379 (7)	C2—C1	1.386 (9)
C5—C4	1.457 (6)	C2—H2B	0.9700
C4—H4A	0.9300	C2—H2C	0.9700
N1—C3	1.322 (6)	C1—H1B	0.9600
N1—C2	1.439 (7)	C1—H1C	0.9600
N1—H1A	0.8600	C1—H1D	0.9600
C10—C9	1.389 (7)
C3—N2—N3	119.4 (4)	N1—C3—N2	116.2 (4)
C3—N2—H2A	120.3	N1—C3—S1	124.1 (4)
N3—N2—H2A	120.3	N2—C3—S1	119.7 (4)
C4—N3—N2	116.6 (4)	C7—C8—C9	120.3 (5)
C10—C5—C6	119.3 (4)	C7—C8—Cl1	120.2 (4)
C10—C5—C4	119.3 (4)	C9—C8—Cl1	119.5 (4)
C6—C5—C4	121.4 (4)	C8—C7—C6	120.2 (5)
N3—C4—C5	120.6 (4)	C8—C7—H7A	119.9
N3—C4—H4A	119.7	C6—C7—H7A	119.9
C5—C4—H4A	119.7	C1—C2—N1	114.7 (6)
C3—N1—C2	126.2 (5)	C1—C2—H2B	108.6
C3—N1—H1A	116.9	N1—C2—H2B	108.6
C2—N1—H1A	116.9	C1—C2—H2C	108.6
C5—C10—C9	120.2 (5)	N1—C2—H2C	108.6
C5—C10—H10A	119.9	H2B—C2—H2C	107.6
C9—C10—H10A	119.9	C2—C1—H1B	109.5
C5—C6—C7	120.3 (5)	C2—C1—H1C	109.5
C5—C6—H6A	119.9	H1B—C1—H1C	109.5
C7—C6—H6A	119.9	C2—C1—H1D	109.5
C8—C9—C10	119.7 (4)	H1B—C1—H1D	109.5
C8—C9—H9A	120.2	H1C—C1—H1D	109.5
C10—C9—H9A	120.2

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1i	0.86	2.59	3.383 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯S1i	0.86	2.59	3.383 (4)	154

Symmetry code: (i) .