(E)-1-(4-Chloro-benzyl-idene)thio-semi-carbazide.

In the crystal of the title compound, C(8)H(8)ClN(3)S, mol-ecules are connected by N-H⋯S hydrogen bonds into strips parallel to the (112) planes and running along [10]. One of the amino H atoms is not involved in a classical hydrogen bond. In addition, there is a rather short inter-molecular Cl⋯S distance of 3.3814 (5) Å.

Related literature

For background to Schiff bases, see: Mobinikhaledi et al. (2010 ▶); Hamaker et al. (2010 ▶); Mirkhani et al. (2010 ▶); Thangadurai et al. (2002 ▶). Ji & Lu (2010a ▶,b ▶); Lü et al. (2008 ▶). For a related structure, see: Zhang & Li (2008 ▶). For bioactivity, see: Chohan et al. (2004 ▶).

Experimental

Crystal data

C8H8ClN3S

M = 213.68

Triclinic,

a = 5.7611 (5) Å

b = 7.8329 (7) Å

c = 11.2016 (10) Å

α = 83.852 (7)°

β = 75.373 (7)°

γ = 76.353 (7)°

V = 474.69 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.58 mm−1

T = 173 K

0.38 × 0.35 × 0.27 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2009; ▶ Blessing, 1995 ▶) T min = 0.811, T max = 0.860

8657 measured reflections

2179 independent reflections

2054 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.079

S = 1.10

2179 reflections

131 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.27 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004120/bg2386sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004120/bg2386Isup2.hkl

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

C8H8ClN3S	Z = 2
Mr = 213.68	F(000) = 220
Triclinic, P1	Dx = 1.495 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7611 (5) Å	Cell parameters from 7492 reflections
b = 7.8329 (7) Å	θ = 3.4–27.8°
c = 11.2016 (10) Å	µ = 0.58 mm−1
α = 83.852 (7)°	T = 173 K
β = 75.373 (7)°	Block, colourless
γ = 76.353 (7)°	0.38 × 0.35 × 0.27 mm
V = 474.69 (7) Å3

Stoe IPDS II two-circle diffractometer	2179 independent reflections
Radiation source: fine-focus sealed tube	2054 reflections with I > 2σ(I)
graphite	Rint = 0.055
ω scans	θmax = 27.7°, θmin = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −7→7
Tmin = 0.811, Tmax = 0.860	k = −10→10
8657 measured reflections	l = −14→14

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079	w = 1/[σ2(Fo2) + (0.0425P)2 + 0.1107P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
2179 reflections	Δρmax = 0.39 e Å−3
131 parameters	Δρmin = −0.27 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.061 (7)

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
Cl1	0.16691 (5)	0.24404 (4)	0.64870 (3)	0.02702 (12)
S1	1.79101 (5)	0.26359 (4)	−0.06509 (3)	0.02625 (12)
N1	1.18834 (19)	0.23473 (14)	0.18778 (10)	0.0215 (2)
N2	1.35359 (19)	0.28547 (14)	0.08531 (10)	0.0220 (2)
H2	1.322 (3)	0.392 (3)	0.0550 (17)	0.033 (4)*
N3	1.6366 (2)	0.03361 (14)	0.11273 (11)	0.0256 (2)
H3A	1.787 (3)	−0.030 (3)	0.0942 (17)	0.037 (5)*
H3B	1.529 (4)	0.002 (2)	0.1674 (19)	0.037 (5)*
C1	0.9739 (2)	0.33723 (16)	0.20735 (11)	0.0206 (2)
H1	0.9408	0.4333	0.1503	0.025*
C2	1.5844 (2)	0.18669 (15)	0.05230 (11)	0.0200 (2)
C11	0.7791 (2)	0.30948 (15)	0.31550 (11)	0.0194 (2)
C12	0.8261 (2)	0.19449 (17)	0.41513 (12)	0.0258 (3)
H12	0.9887	0.1297	0.4129	0.031*
C13	0.6388 (2)	0.17389 (17)	0.51702 (12)	0.0275 (3)
H13	0.6721	0.0962	0.5847	0.033*
C14	0.4012 (2)	0.26838 (16)	0.51905 (11)	0.0209 (2)
C15	0.3492 (2)	0.38356 (16)	0.42174 (11)	0.0221 (2)
H15	0.1859	0.4470	0.4241	0.027*
C16	0.5394 (2)	0.40491 (16)	0.32075 (11)	0.0216 (2)
H16	0.5060	0.4855	0.2544	0.026*

	U11	U22	U33	U12	U13	U23
Cl1	0.02137 (17)	0.02970 (19)	0.02380 (18)	−0.00376 (12)	0.00323 (12)	0.00098 (12)
S1	0.01985 (17)	0.02394 (18)	0.02535 (18)	0.00043 (12)	0.00505 (12)	0.00406 (12)
N1	0.0187 (5)	0.0228 (5)	0.0206 (5)	−0.0050 (4)	0.0009 (4)	−0.0024 (4)
N2	0.0171 (5)	0.0214 (5)	0.0217 (5)	−0.0008 (4)	0.0018 (4)	0.0005 (4)
N3	0.0193 (5)	0.0236 (5)	0.0260 (5)	0.0001 (4)	0.0024 (4)	0.0035 (4)
C1	0.0185 (5)	0.0218 (5)	0.0206 (5)	−0.0041 (4)	−0.0026 (4)	−0.0023 (4)
C2	0.0192 (5)	0.0212 (5)	0.0177 (5)	−0.0023 (4)	−0.0021 (4)	−0.0023 (4)
C11	0.0165 (5)	0.0190 (5)	0.0215 (6)	−0.0035 (4)	−0.0016 (4)	−0.0040 (4)
C12	0.0167 (5)	0.0248 (6)	0.0298 (6)	0.0024 (4)	−0.0023 (5)	0.0017 (5)
C13	0.0223 (6)	0.0259 (6)	0.0278 (6)	0.0011 (5)	−0.0031 (5)	0.0064 (5)
C14	0.0173 (5)	0.0216 (5)	0.0209 (5)	−0.0031 (4)	0.0003 (4)	−0.0032 (4)
C15	0.0148 (5)	0.0260 (6)	0.0233 (6)	−0.0005 (4)	−0.0034 (4)	−0.0027 (5)
C16	0.0183 (5)	0.0248 (6)	0.0201 (5)	−0.0016 (4)	−0.0047 (4)	−0.0010 (4)

Cl1—C14	1.7435 (12)	C11—C16	1.3967 (16)
S1—C2	1.6992 (12)	C11—C12	1.3972 (18)
N1—C1	1.2853 (16)	C12—C13	1.3835 (18)
N1—N2	1.3824 (14)	C12—H12	0.9500
N2—C2	1.3530 (15)	C13—C14	1.3898 (17)
N2—H2	0.863 (19)	C13—H13	0.9500
N3—C2	1.3211 (16)	C14—C15	1.3851 (17)
N3—H3A	0.877 (19)	C15—C16	1.3886 (17)
N3—H3B	0.82 (2)	C15—H15	0.9500
C1—C11	1.4648 (16)	C16—H16	0.9500
C1—H1	0.9500
C1—N1—N2	114.01 (10)	C13—C12—C11	120.82 (11)
C2—N2—N1	120.12 (10)	C13—C12—H12	119.6
C2—N2—H2	119.3 (12)	C11—C12—H12	119.6
N1—N2—H2	118.7 (12)	C12—C13—C14	119.15 (12)
C2—N3—H3A	118.9 (13)	C12—C13—H13	120.4
C2—N3—H3B	119.0 (13)	C14—C13—H13	120.4
H3A—N3—H3B	122.1 (18)	C15—C14—C13	121.30 (11)
N1—C1—C11	121.62 (11)	C15—C14—Cl1	119.81 (9)
N1—C1—H1	119.2	C13—C14—Cl1	118.88 (10)
C11—C1—H1	119.2	C14—C15—C16	119.00 (11)
N3—C2—N2	117.92 (11)	C14—C15—H15	120.5
N3—C2—S1	123.29 (9)	C16—C15—H15	120.5
N2—C2—S1	118.78 (9)	C15—C16—C11	120.85 (11)
C16—C11—C12	118.86 (11)	C15—C16—H16	119.6
C16—C11—C1	118.86 (11)	C11—C16—H16	119.6
C12—C11—C1	122.26 (10)
C1—N1—N2—C2	−178.33 (11)	C11—C12—C13—C14	0.5 (2)
N2—N1—C1—C11	−176.64 (10)	C12—C13—C14—C15	−0.6 (2)
N1—N2—C2—N3	6.86 (18)	C12—C13—C14—Cl1	−179.11 (10)
N1—N2—C2—S1	−173.83 (8)	C13—C14—C15—C16	−0.29 (19)
N1—C1—C11—C16	−168.81 (11)	Cl1—C14—C15—C16	178.22 (9)
N1—C1—C11—C12	13.02 (19)	C14—C15—C16—C11	1.31 (18)
C16—C11—C12—C13	0.53 (19)	C12—C11—C16—C15	−1.43 (18)
C1—C11—C12—C13	178.70 (12)	C1—C11—C16—C15	−179.66 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1i	0.863 (19)	2.628 (19)	3.4288 (12)	154.7 (16)
N3—H3A···S1ii	0.877 (19)	2.65 (2)	3.5119 (12)	170.1 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1i	0.863 (19)	2.628 (19)	3.4288 (12)	154.7 (16)
N3—H3A⋯S1ii	0.877 (19)	2.65 (2)	3.5119 (12)	170.1 (17)

Symmetry codes: (i) ; (ii) .