5-Chloro-2-hy-droxy-benzaldehyde thio-semicarbazone.

In the title compound, C(8)H(8)ClN(3)OS, the whole mol-ecule assumes a planar structure, with an r.m.s. deviation of 0.108 (2) Å, and an intra-molecular O-H⋯N hydrogen bond generates and S(6) and ring motif. In the crystal structure, each of two pairs of inter-molecular N-H⋯S hydrogen bonds connects two mol-ecules, forming inversion dimers with R(2) (2)(8) motifs.

Related literature

For the biological activities and pharmaceutical properties of thio­semicarbazones and their derivatives, see: Casas et al. (2000 ▶); Ferrari et al. (2000 ▶); Maccioni et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H8ClN3OS

M = 229.69

Monoclinic,

a = 5.8303 (4) Å

b = 23.6579 (17) Å

c = 7.5893 (5) Å

β = 104.164 (6)°

V = 1014.99 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.55 mm−1

T = 296 K

0.52 × 0.33 × 0.08 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.763, T max = 0.957

4469 measured reflections

1895 independent reflections

1524 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.120

S = 1.04

1895 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.37 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043448/is2621sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043448/is2621Isup2.hkl

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

C8H8ClN3OS	F(000) = 472
Mr = 229.69	Dx = 1.503 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8344 reflections
a = 5.8303 (4) Å	θ = 1.7–26.2°
b = 23.6579 (17) Å	µ = 0.55 mm−1
c = 7.5893 (5) Å	T = 296 K
β = 104.164 (6)°	Prism, colourless
V = 1014.99 (12) Å3	0.52 × 0.33 × 0.08 mm
Z = 4

Stoe IPDS II diffractometer	1895 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1524 reflections with I > 2σ(I)
plane graphite	Rint = 0.051
Detector resolution: 6.67 pixels mm-1	θmax = 25.6°, θmin = 1.7°
ω scans	h = −5→7
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −28→26
Tmin = 0.763, Tmax = 0.957	l = −9→9
4469 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0681P)2 + 0.120P] where P = (Fo2 + 2Fc2)/3
1895 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.36123 (17)	0.20555 (4)	−0.30970 (10)	0.0868 (3)
S1	0.15507 (9)	0.01021 (3)	0.79551 (8)	0.0559 (2)
O1	0.8537 (3)	0.13549 (11)	0.4272 (3)	0.0750 (8)
N1	0.4525 (3)	0.08332 (9)	0.4467 (3)	0.0489 (6)
N2	0.3002 (3)	0.05468 (10)	0.5260 (3)	0.0523 (6)
N3	0.5874 (3)	0.04298 (10)	0.7883 (3)	0.0524 (7)
C1	0.4996 (4)	0.13306 (11)	0.1830 (3)	0.0493 (8)
C2	0.7333 (4)	0.15067 (12)	0.2573 (4)	0.0573 (8)
C3	0.8480 (5)	0.18395 (14)	0.1559 (4)	0.0687 (10)
C4	0.7368 (6)	0.20095 (13)	−0.0164 (4)	0.0702 (10)
C5	0.5049 (5)	0.18372 (12)	−0.0912 (4)	0.0604 (9)
C6	0.3886 (5)	0.15099 (11)	0.0062 (3)	0.0542 (8)
C7	0.3665 (4)	0.09979 (11)	0.2818 (3)	0.0507 (8)
C8	0.3636 (4)	0.03756 (11)	0.6999 (3)	0.0454 (7)
H1	0.76270	0.12040	0.48000	0.1120*
H2	0.15960	0.04740	0.46260	0.0630*
H3	1.00350	0.19500	0.20550	0.0830*
H3A	0.68790	0.05710	0.73440	0.0630*
H3B	0.63280	0.03240	0.89980	0.0630*
H4	0.81520	0.22370	−0.08260	0.0840*
H6	0.23310	0.14030	−0.04510	0.0650*
H7	0.21210	0.08970	0.22430	0.0610*

	U11	U22	U33	U12	U13	U23
Cl1	0.1118 (7)	0.0820 (6)	0.0700 (4)	0.0054 (5)	0.0287 (4)	0.0188 (4)
S1	0.0349 (3)	0.0795 (5)	0.0526 (3)	−0.0048 (3)	0.0096 (2)	0.0063 (3)
O1	0.0458 (10)	0.0951 (17)	0.0791 (12)	−0.0077 (10)	0.0058 (9)	0.0132 (11)
N1	0.0379 (9)	0.0554 (12)	0.0544 (10)	−0.0011 (8)	0.0131 (8)	0.0019 (9)
N2	0.0336 (9)	0.0683 (14)	0.0529 (10)	−0.0059 (9)	0.0065 (8)	0.0074 (9)
N3	0.0334 (9)	0.0742 (15)	0.0485 (10)	−0.0031 (9)	0.0079 (7)	0.0017 (9)
C1	0.0447 (12)	0.0466 (14)	0.0597 (13)	0.0017 (10)	0.0189 (10)	−0.0007 (10)
C2	0.0453 (12)	0.0558 (16)	0.0729 (15)	0.0009 (11)	0.0186 (11)	0.0020 (12)
C3	0.0489 (14)	0.0623 (18)	0.100 (2)	−0.0044 (12)	0.0281 (14)	0.0079 (15)
C4	0.0725 (17)	0.0577 (18)	0.0926 (19)	0.0020 (14)	0.0438 (15)	0.0108 (15)
C5	0.0729 (17)	0.0490 (15)	0.0653 (14)	0.0056 (13)	0.0283 (12)	0.0030 (11)
C6	0.0540 (13)	0.0505 (15)	0.0595 (12)	0.0029 (11)	0.0168 (10)	−0.0014 (11)
C7	0.0403 (12)	0.0544 (15)	0.0570 (12)	0.0002 (10)	0.0111 (10)	0.0015 (11)
C8	0.0344 (10)	0.0510 (14)	0.0505 (11)	0.0009 (9)	0.0096 (9)	−0.0029 (10)

Cl1—C5	1.743 (3)	C1—C2	1.404 (4)
S1—C8	1.690 (2)	C1—C6	1.405 (3)
O1—C2	1.357 (4)	C1—C7	1.438 (3)
O1—H1	0.8200	C2—C3	1.383 (4)
N1—N2	1.368 (3)	C3—C4	1.370 (4)
N1—C7	1.289 (3)	C4—C5	1.393 (5)
N2—C8	1.343 (3)	C5—C6	1.361 (4)
N3—C8	1.319 (3)	C3—H3	0.9300
N2—H2	0.8600	C4—H4	0.9300
N3—H3A	0.8600	C6—H6	0.9300
N3—H3B	0.8600	C7—H7	0.9300
Cl1···C5i	3.606 (3)	C7···C8vi	3.598 (4)
S1···N3ii	3.387 (2)	C7···N3vi	3.440 (4)
S1···N2iii	3.491 (2)	C7···C3ii	3.550 (4)
S1···N3iv	3.390 (2)	C8···C7vi	3.598 (4)
S1···H3Aii	2.8700	C8···C6vii	3.530 (3)
S1···H2iii	2.7000	C8···N1vi	3.339 (3)
S1···H3Biv	2.5500	C3···H7v	3.0300
S1···H7iii	3.1700	C3···H4viii	2.9900
O1···N1	2.681 (3)	C7···H3ii	3.0500
O1···N2v	3.168 (3)	C7···H1	2.4800
O1···H2v	2.7100	H1···N1	1.9700
N1···O1	2.681 (3)	H1···C7	2.4800
N1···N3	2.693 (3)	H1···H3A	2.5600
N1···C8vi	3.339 (3)	H2···O1ii	2.7100
N2···O1ii	3.168 (3)	H2···H7	2.1500
N2···S1iii	3.491 (2)	H2···S1iii	2.7000
N3···C6vii	3.398 (3)	H3···C7v	3.0500
N3···S1iv	3.390 (2)	H3A···S1v	2.8700
N3···S1v	3.387 (2)	H3A···N1	2.3600
N3···N1	2.693 (3)	H3A···H1	2.5600
N3···C7vi	3.440 (4)	H3B···S1iv	2.5500
N1···H1	1.9700	H4···C3i	2.9900
N1···H3A	2.3600	H6···H7	2.4000
C3···C7v	3.550 (4)	H7···C3ii	3.0300
C5···Cl1viii	3.606 (3)	H7···H2	2.1500
C6···N3ix	3.398 (3)	H7···H6	2.4000
C6···C8ix	3.530 (3)	H7···S1iii	3.1700
C2—O1—H1	109.00	Cl1—C5—C4	119.6 (2)
N2—N1—C7	115.9 (2)	Cl1—C5—C6	119.9 (2)
N1—N2—C8	122.0 (2)	C4—C5—C6	120.5 (3)
C8—N2—H2	119.00	C1—C6—C5	121.1 (3)
N1—N2—H2	119.00	N1—C7—C1	122.7 (2)
H3A—N3—H3B	120.00	N2—C8—N3	118.1 (2)
C8—N3—H3A	120.00	S1—C8—N2	118.92 (18)
C8—N3—H3B	120.00	S1—C8—N3	123.01 (18)
C2—C1—C6	118.0 (2)	C2—C3—H3	119.00
C6—C1—C7	118.8 (2)	C4—C3—H3	119.00
C2—C1—C7	123.2 (2)	C3—C4—H4	120.00
O1—C2—C1	121.9 (2)	C5—C4—H4	120.00
C1—C2—C3	120.0 (3)	C1—C6—H6	119.00
O1—C2—C3	118.1 (2)	C5—C6—H6	119.00
C2—C3—C4	121.2 (3)	N1—C7—H7	119.00
C3—C4—C5	119.2 (3)	C1—C7—H7	119.00
C7—N1—N2—C8	−176.7 (2)	C6—C1—C2—C3	−0.9 (4)
N2—N1—C7—C1	176.5 (2)	C7—C1—C2—O1	2.5 (4)
N1—N2—C8—S1	171.99 (18)	O1—C2—C3—C4	−179.8 (3)
N1—N2—C8—N3	−8.0 (4)	C1—C2—C3—C4	0.9 (5)
C7—C1—C2—C3	−178.2 (3)	C2—C3—C4—C5	−0.8 (5)
C2—C1—C6—C5	1.0 (4)	C3—C4—C5—Cl1	179.5 (2)
C7—C1—C6—C5	178.3 (3)	C3—C4—C5—C6	0.8 (5)
C2—C1—C7—N1	−0.3 (4)	Cl1—C5—C6—C1	−179.6 (2)
C6—C1—C7—N1	−177.6 (2)	C4—C5—C6—C1	−0.9 (4)
C6—C1—C2—O1	179.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.97	2.681 (3)	144
N2—H2···S1iii	0.86	2.70	3.491 (2)	153
N3—H3A···S1v	0.86	2.87	3.387 (2)	120
N3—H3A···N1	0.86	2.36	2.693 (3)	103
N3—H3B···S1iv	0.86	2.55	3.390 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1i	0.86	2.70	3.491 (2)	153
N3—H3A⋯S1ii	0.86	2.87	3.387 (2)	120
N3—H3A⋯N1	0.86	2.36	2.693 (3)	103
N3—H3B⋯S1iii	0.86	2.55	3.390 (2)	167

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