(E)-1-[1-(4-Chloro-phen-yl)ethyl-idene]thio-semicarbazide.

In the crystal structure of the title compound, C(9)H(10)ClN(3)S, the mol-ecules form chains parallel to [001] through N-H⋯S hydrogen bonds. In addition, weak inter-molecular N-H⋯Cl hydrogen bonds connect the chains, forming a two-dimensional network parallel to (001).

Related literature

For related compounds and their biological activity, see: Odenike et al. (2008 ▶); Rebolledo et al. (2008 ▶). For a related structure, see: Wang et al. (2007 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C9H10ClN3S

M = 227.71

Monoclinic,

a = 9.2760 (2) Å

b = 13.9990 (3) Å

c = 8.3970 (2) Å

β = 97.448 (2)°

V = 1081.19 (4) Å3

Z = 4

Cu Kα radiation

μ = 4.64 mm−1

T = 293 K

0.53 × 0.10 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.256, T max = 1.000

6043 measured reflections

2024 independent reflections

1807 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.104

S = 1.06

2024 reflections

167 parameters

All H-atom parameters refined

Δρmax = 0.31 e Å−3

Δρmin = −0.30 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: SIR2008 (Burla et al., 2007 ▶); 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/S1600536812029133/kp2427sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029133/kp2427Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029133/kp2427Isup3.cml

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

C9H10ClN3S	F(000) = 472
Mr = 227.71	Dx = 1.399 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
a = 9.2760 (2) Å	Cell parameters from 4083 reflections
b = 13.9990 (3) Å	θ = 4.8–70.4°
c = 8.3970 (2) Å	µ = 4.64 mm−1
β = 97.448 (2)°	T = 293 K
V = 1081.19 (4) Å3	Needle, white
Z = 4	0.53 × 0.10 × 0.10 mm

Oxford Diffraction Xcalibur (Ruby, Gemini) diffractometer	2024 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1807 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 10.2673 pixels mm-1	θmax = 70.6°, θmin = 4.8°
ω scans	h = −9→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −16→16
Tmin = 0.256, Tmax = 1.000	l = −10→9
6043 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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F2) = 0.104	All H-atom parameters refined
S = 1.06	w = 1/[σ2(Fo2) + (0.0575P)2 + 0.2508P] where P = (Fo2 + 2Fc2)/3
2024 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) 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	0.83335 (6)	0.21962 (3)	0.00603 (5)	0.05163 (19)
Cl1	0.57019 (7)	0.94286 (4)	−0.18264 (9)	0.0821 (2)
N2	0.81521 (19)	0.39415 (10)	−0.11515 (19)	0.0491 (4)
N1	0.77525 (18)	0.48923 (10)	−0.10634 (18)	0.0476 (4)
C9	0.8022 (2)	0.33823 (12)	0.0125 (2)	0.0432 (4)
N3	0.7653 (2)	0.38062 (13)	0.1416 (2)	0.0605 (5)
C7	0.8045 (2)	0.54568 (12)	−0.2186 (2)	0.0438 (4)
C5	0.8203 (2)	0.72184 (13)	−0.2668 (3)	0.0515 (5)
C4	0.7665 (2)	0.81370 (14)	−0.2571 (3)	0.0565 (5)
C6	0.74834 (19)	0.64447 (12)	−0.2095 (2)	0.0424 (4)
C3	0.6403 (2)	0.82766 (12)	−0.1920 (2)	0.0520 (5)
C1	0.6206 (2)	0.66152 (13)	−0.1440 (3)	0.0529 (5)
C2	0.5654 (2)	0.75293 (15)	−0.1350 (3)	0.0587 (5)
C8	0.8862 (3)	0.51830 (16)	−0.3537 (3)	0.0637 (6)
H5	0.908 (3)	0.7122 (16)	−0.314 (3)	0.065 (7)*
H4	0.812 (3)	0.8684 (18)	−0.300 (3)	0.068 (7)*
H1	0.572 (2)	0.6117 (16)	−0.111 (3)	0.053 (6)*
H2	0.482 (3)	0.7642 (18)	−0.088 (3)	0.069 (7)*
H9	0.825 (3)	0.3660 (17)	−0.208 (3)	0.068 (7)*
H10B	0.764 (2)	0.3508 (19)	0.228 (3)	0.064 (7)*
H10A	0.748 (3)	0.4403 (19)	0.138 (3)	0.061 (6)*
H24	0.958 (3)	0.477 (2)	−0.323 (3)	0.085 (8)*
H25	0.913 (4)	0.570 (3)	−0.406 (4)	0.105 (10)*
H23	0.820 (4)	0.488 (3)	−0.430 (4)	0.115 (12)*

	U11	U22	U33	U12	U13	U23
S1	0.0813 (4)	0.0306 (3)	0.0452 (3)	0.00960 (19)	0.0166 (2)	0.00294 (15)
Cl1	0.0895 (5)	0.0360 (3)	0.1238 (6)	0.0149 (2)	0.0247 (4)	0.0101 (3)
N2	0.0750 (11)	0.0292 (7)	0.0452 (8)	0.0056 (7)	0.0163 (7)	0.0029 (6)
N1	0.0665 (10)	0.0281 (7)	0.0493 (8)	0.0045 (6)	0.0121 (7)	0.0020 (6)
C9	0.0566 (10)	0.0317 (8)	0.0422 (8)	0.0027 (7)	0.0100 (7)	0.0003 (6)
N3	0.1046 (15)	0.0321 (9)	0.0482 (9)	0.0092 (8)	0.0234 (9)	0.0027 (7)
C7	0.0549 (10)	0.0308 (8)	0.0459 (9)	−0.0027 (7)	0.0078 (7)	0.0015 (7)
C5	0.0563 (11)	0.0365 (9)	0.0636 (12)	−0.0035 (8)	0.0149 (9)	0.0039 (8)
C4	0.0660 (12)	0.0306 (9)	0.0740 (13)	−0.0058 (8)	0.0130 (10)	0.0066 (9)
C6	0.0532 (10)	0.0304 (8)	0.0434 (8)	−0.0021 (7)	0.0051 (7)	0.0026 (6)
C3	0.0620 (12)	0.0308 (9)	0.0622 (11)	0.0036 (8)	0.0041 (9)	0.0034 (8)
C1	0.0624 (12)	0.0332 (9)	0.0659 (12)	−0.0032 (8)	0.0188 (10)	0.0078 (8)
C2	0.0622 (13)	0.0427 (11)	0.0743 (13)	0.0036 (9)	0.0203 (11)	0.0046 (9)
C8	0.0942 (18)	0.0367 (11)	0.0664 (13)	0.0043 (11)	0.0346 (13)	0.0046 (10)

S1—C9	1.6875 (17)	C5—C6	1.390 (3)
Cl1—C3	1.7443 (18)	C5—H5	0.96 (2)
N2—C9	1.345 (2)	C4—C3	1.369 (3)
N2—N1	1.386 (2)	C4—H4	0.97 (2)
N2—H9	0.89 (3)	C6—C1	1.390 (3)
N1—C7	1.286 (2)	C3—C2	1.375 (3)
C9—N3	1.319 (2)	C1—C2	1.384 (3)
N3—H10B	0.84 (3)	C1—H1	0.89 (2)
N3—H10A	0.85 (3)	C2—H2	0.93 (3)
C7—C6	1.483 (2)	C8—H24	0.90 (3)
C7—C8	1.493 (3)	C8—H25	0.90 (4)
C5—C4	1.386 (3)	C8—H23	0.93 (4)
C9—N2—N1	117.64 (15)	C5—C6—C1	118.38 (17)
C9—N2—H9	118.2 (16)	C5—C6—C7	121.38 (17)
N1—N2—H9	122.1 (16)	C1—C6—C7	120.23 (16)
C7—N1—N2	117.88 (15)	C4—C3—C2	121.79 (18)
N3—C9—N2	116.91 (16)	C4—C3—Cl1	119.54 (15)
N3—C9—S1	122.19 (14)	C2—C3—Cl1	118.67 (17)
N2—C9—S1	120.89 (13)	C2—C1—C6	121.34 (18)
C9—N3—H10B	121.6 (17)	C2—C1—H1	120.2 (14)
C9—N3—H10A	118.9 (16)	C6—C1—H1	118.5 (14)
H10B—N3—H10A	119 (2)	C3—C2—C1	118.5 (2)
N1—C7—C6	115.22 (16)	C3—C2—H2	120.4 (16)
N1—C7—C8	125.12 (17)	C1—C2—H2	121.0 (16)
C6—C7—C8	119.66 (16)	C7—C8—H24	112.5 (18)
C4—C5—C6	120.66 (19)	C7—C8—H25	111 (2)
C4—C5—H5	119.0 (14)	H24—C8—H25	115 (3)
C6—C5—H5	120.3 (14)	C7—C8—H23	107 (2)
C3—C4—C5	119.27 (18)	H24—C8—H23	107 (3)
C3—C4—H4	118.2 (15)	H25—C8—H23	103 (3)
C5—C4—H4	122.5 (15)
C9—N2—N1—C7	171.36 (17)	N1—C7—C6—C1	−30.9 (2)
N1—N2—C9—N3	−6.1 (3)	C8—C7—C6—C1	148.1 (2)
N1—N2—C9—S1	174.28 (14)	C5—C4—C3—C2	0.3 (3)
N2—N1—C7—C6	175.21 (15)	C5—C4—C3—Cl1	−178.89 (17)
N2—N1—C7—C8	−3.8 (3)	C5—C6—C1—C2	−0.2 (3)
C6—C5—C4—C3	−0.8 (3)	C7—C6—C1—C2	−179.58 (19)
C4—C5—C6—C1	0.7 (3)	C4—C3—C2—C1	0.2 (3)
C4—C5—C6—C7	−179.92 (18)	Cl1—C3—C2—C1	179.40 (17)
N1—C7—C6—C5	149.71 (19)	C6—C1—C2—C3	−0.3 (3)
C8—C7—C6—C5	−31.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H9···S1i	0.89 (3)	2.69 (3)	3.581 (2)	175 (2)
N3—H10B···S1ii	0.84 (3)	2.54 (3)	3.351 (2)	163 (2)
N3—H10A···Cl1iii	0.85 (3)	2.88 (2)	3.500 (2)	131 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H9⋯S1i	0.89 (3)	2.69 (3)	3.581 (2)	175 (2)
N3—H10B⋯S1ii	0.84 (3)	2.54 (3)	3.351 (2)	163 (2)
N3—H10A⋯Cl1iii	0.85 (3)	2.88 (2)	3.500 (2)	131 (2)

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