2-Chloro-5-nitro-benzaldehyde thio-semicarbazone.

The title Schiff base compound, C(8)H(7)ClN(4)O(2)S, was prepared by the reaction of equimolar quanti-ties of 2-chloro-5-nitro-benzaldehyde with thio-semicarbazide in methanol. The mol-ecule adopts a trans configuration with respect to the azomethine group and the dihedral angle between the benzene ring and the thio-semicarbazide group is 6.8 (3)°. In the crystal, mol-ecules are linked through inter-molecular N-H⋯S hydrogen bonds, forming chains propagating in [010].

Related literature

For the crystal structures of similar Schiff base compounds, see: Ferrari et al. (1999 ▶); Shanmuga Sundara Raj et al. (2000 ▶); Chattopadhyay et al. (1988 ▶). For a similar compound reported by the author, see: Hao (2010 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H7ClN4O2S

M = 258.69

Monoclinic,

a = 11.611 (2) Å

b = 8.439 (2) Å

c = 12.016 (3) Å

β = 113.909 (2)°

V = 1076.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.54 mm−1

T = 298 K

0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.909, T max = 0.914

6657 measured reflections

2344 independent reflections

1573 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.111

S = 1.02

2344 reflections

154 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035701/hb5633sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035701/hb5633Isup2.hkl

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

C8H7ClN4O2S	F(000) = 528
Mr = 258.69	Dx = 1.596 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1613 reflections
a = 11.611 (2) Å	θ = 2.8–24.7°
b = 8.439 (2) Å	µ = 0.54 mm−1
c = 12.016 (3) Å	T = 298 K
β = 113.909 (2)°	Block, yellow
V = 1076.4 (4) Å3	0.18 × 0.17 × 0.17 mm
Z = 4

Bruker SMART CCD diffractometer	2344 independent reflections
Radiation source: fine-focus sealed tube	1573 reflections with I > 2σ(I)
graphite	Rint = 0.038
ω scans	θmax = 27.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.909, Tmax = 0.914	k = −7→10
6657 measured reflections	l = −14→15

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.052P)2 + 0.1148P] where P = (Fo2 + 2Fc2)/3
2344 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.20 e Å−3
4 restraints	Δρmin = −0.17 e Å−3

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
Cl1	0.22502 (8)	−0.41154 (8)	0.48549 (7)	0.0669 (3)
N1	0.11203 (19)	0.1863 (3)	0.67884 (19)	0.0541 (6)
N2	0.33718 (17)	0.0503 (2)	0.40689 (17)	0.0402 (5)
N3	0.39548 (18)	0.0489 (2)	0.32765 (18)	0.0409 (5)
N4	0.4229 (2)	0.3150 (2)	0.3570 (2)	0.0543 (6)
O1	0.13241 (19)	0.3120 (2)	0.64124 (19)	0.0694 (6)
O2	0.0674 (2)	0.1755 (3)	0.7540 (2)	0.0965 (8)
S1	0.50185 (6)	0.18861 (7)	0.19837 (6)	0.0460 (2)
C1	0.2313 (2)	−0.0903 (3)	0.50752 (19)	0.0375 (5)
C2	0.1926 (2)	−0.2336 (3)	0.5392 (2)	0.0424 (6)
C3	0.1273 (2)	−0.2416 (3)	0.6133 (2)	0.0504 (6)
H3A	0.1013	−0.3389	0.6314	0.061*
C4	0.1014 (2)	−0.1031 (3)	0.6600 (2)	0.0506 (6)
H4	0.0584	−0.1054	0.7107	0.061*
C5	0.1405 (2)	0.0385 (3)	0.6300 (2)	0.0422 (6)
C6	0.2036 (2)	0.0480 (3)	0.5549 (2)	0.0406 (5)
H6	0.2275	0.1460	0.5360	0.049*
C7	0.2974 (2)	−0.0829 (3)	0.4273 (2)	0.0407 (5)
H7	0.3105	−0.1747	0.3912	0.049*
C8	0.4371 (2)	0.1867 (2)	0.3007 (2)	0.0382 (5)
H3	0.412 (2)	−0.0446 (19)	0.301 (2)	0.080*
H4B	0.394 (3)	0.312 (3)	0.4146 (19)	0.080*
H4A	0.450 (2)	0.4093 (18)	0.346 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.1005 (6)	0.0371 (4)	0.0800 (5)	−0.0034 (3)	0.0541 (4)	0.0020 (3)
N1	0.0526 (13)	0.0621 (15)	0.0564 (14)	0.0075 (11)	0.0311 (11)	−0.0029 (11)
N2	0.0496 (11)	0.0372 (11)	0.0447 (12)	0.0008 (9)	0.0303 (9)	0.0032 (9)
N3	0.0569 (12)	0.0283 (10)	0.0533 (13)	0.0023 (9)	0.0385 (10)	0.0013 (9)
N4	0.0835 (16)	0.0338 (11)	0.0712 (15)	−0.0090 (11)	0.0578 (13)	−0.0081 (11)
O1	0.0868 (14)	0.0503 (12)	0.0874 (15)	0.0001 (10)	0.0521 (12)	−0.0058 (11)
O2	0.143 (2)	0.0869 (16)	0.1135 (18)	0.0285 (15)	0.1077 (17)	0.0100 (14)
S1	0.0628 (4)	0.0345 (3)	0.0580 (4)	−0.0034 (3)	0.0423 (3)	0.0004 (3)
C1	0.0400 (12)	0.0374 (13)	0.0381 (13)	−0.0023 (10)	0.0190 (11)	0.0026 (10)
C2	0.0497 (14)	0.0366 (12)	0.0432 (14)	−0.0023 (10)	0.0213 (11)	0.0017 (10)
C3	0.0563 (15)	0.0509 (15)	0.0503 (15)	−0.0118 (12)	0.0281 (13)	0.0073 (12)
C4	0.0515 (15)	0.0632 (17)	0.0483 (15)	−0.0046 (13)	0.0317 (12)	0.0042 (13)
C5	0.0416 (13)	0.0480 (14)	0.0413 (14)	0.0005 (11)	0.0214 (11)	−0.0010 (11)
C6	0.0431 (13)	0.0384 (13)	0.0457 (14)	−0.0031 (10)	0.0236 (11)	0.0037 (10)
C7	0.0496 (14)	0.0333 (12)	0.0486 (14)	0.0012 (10)	0.0294 (12)	−0.0009 (11)
C8	0.0435 (13)	0.0310 (12)	0.0460 (14)	−0.0001 (10)	0.0243 (11)	0.0023 (10)

Cl1—C2	1.735 (2)	C1—C6	1.393 (3)
N1—O2	1.214 (3)	C1—C2	1.396 (3)
N1—O1	1.214 (3)	C1—C7	1.456 (3)
N1—C5	1.471 (3)	C2—C3	1.386 (3)
N2—C7	1.277 (3)	C3—C4	1.382 (4)
N2—N3	1.374 (2)	C3—H3A	0.9300
N3—C8	1.348 (3)	C4—C5	1.378 (3)
N3—H3	0.899 (10)	C4—H4	0.9300
N4—C8	1.322 (3)	C5—C6	1.376 (3)
N4—H4B	0.88 (3)	C6—H6	0.9300
N4—H4A	0.886 (10)	C7—H7	0.9300
S1—C8	1.681 (2)
O2—N1—O1	123.3 (2)	C4—C3—H3A	120.5
O2—N1—C5	117.8 (2)	C2—C3—H3A	120.5
O1—N1—C5	118.9 (2)	C5—C4—C3	118.6 (2)
C7—N2—N3	116.36 (19)	C5—C4—H4	120.7
C8—N3—N2	118.95 (18)	C3—C4—H4	120.7
C8—N3—H3	121.7 (18)	C6—C5—C4	122.8 (2)
N2—N3—H3	119.1 (18)	C6—C5—N1	118.5 (2)
C8—N4—H4B	122.8 (17)	C4—C5—N1	118.6 (2)
C8—N4—H4A	122.1 (17)	C5—C6—C1	119.5 (2)
H4B—N4—H4A	115 (2)	C5—C6—H6	120.3
C6—C1—C2	117.5 (2)	C1—C6—H6	120.3
C6—C1—C7	120.4 (2)	N2—C7—C1	119.6 (2)
C2—C1—C7	122.1 (2)	N2—C7—H7	120.2
C3—C2—C1	122.6 (2)	C1—C7—H7	120.2
C3—C2—Cl1	117.04 (19)	N4—C8—N3	116.9 (2)
C1—C2—Cl1	120.40 (18)	N4—C8—S1	123.49 (17)
C4—C3—C2	119.1 (2)	N3—C8—S1	119.59 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···S1i	0.89 (1)	2.53 (1)	3.408 (2)	173 (2)
N3—H3···S1ii	0.90 (1)	2.46 (1)	3.3266 (19)	161 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯S1i	0.89 (1)	2.53 (1)	3.408 (2)	173 (2)
N3—H3⋯S1ii	0.90 (1)	2.46 (1)	3.3266 (19)	161 (2)

Symmetry codes: (i) ; (ii) .