N-(2-Chloro-5-nitro-phen-yl)-N'-(3-chloro-propion-yl)thio-urea.

The title compound, C10H9Cl2N3O3S, adopts a trans-cis conformation with respect to the position of chloropropionyl and chloronitrobenzene groups respectively, against the thiono about their C-N bonds. The conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond. In the crystal, there is a short Cl⋯Cl contact with a distance of 3.386 (13) Å.

Related literature

For related structures, see: Othman et al. (2010 ▶); Yamin et al. (2011 ▶); Yamin & Othman (2011 ▶); Yusof et al., (2011 ▶).

Experimental

Crystal data

C10H9Cl2N3O3S

M = 322.16

Monoclinic,

a = 21.764 (6) Å

b = 5.2284 (13) Å

c = 24.134 (6) Å

β = 106.388 (8)°

V = 2634.6 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.66 mm−1

T = 298 K

0.38 × 0.36 × 0.27 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2000 ▶) T min = 0.902, T max = 0.919

12266 measured reflections

2460 independent reflections

2116 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.097

S = 1.05

2460 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813032662/fj2651sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032662/fj2651Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813032662/fj2651Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H9Cl2N3O3S	Z = 8
Mr = 322.16	F(000) = 1312
Monoclinic, C2/c	Dx = 1.624 Mg m−3
a = 21.764 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 5.2284 (13) Å	µ = 0.66 mm−1
c = 24.134 (6) Å	T = 298 K
β = 106.388 (8)°	Block, colorless
V = 2634.6 (12) Å3	0.38 × 0.36 × 0.27 mm

Bruker SMART APEX CCD area-detector diffractometer	2460 independent reflections
Radiation source: fine-focus sealed tube	2116 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 83.66 pixels mm-1	θmax = 25.5°, θmin = 1.8°
ω scans	h = −26→26
Absorption correction: multi-scan (SADABS; Bruker 2000)	k = −6→6
Tmin = 0.902, Tmax = 0.919	l = −29→29
12266 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0496P)2 + 1.9444P] where P = (Fo2 + 2Fc2)/3
2460 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.23 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.

	x	y	z	Uiso*/Ueq
Cl1	0.01680 (3)	0.29301 (14)	−0.16862 (3)	0.0761 (2)
Cl2	0.05486 (3)	1.21922 (11)	−0.00637 (3)	0.05899 (18)
S1	0.23748 (3)	0.45825 (11)	0.07394 (2)	0.05376 (18)
O1	0.09544 (9)	0.7795 (4)	−0.08527 (7)	0.0804 (6)
O2	0.20313 (12)	0.6949 (5)	0.24336 (8)	0.0984 (7)
O3	0.15801 (11)	1.0096 (4)	0.27253 (8)	0.0953 (7)
N1	0.17678 (8)	0.5279 (3)	−0.03529 (7)	0.0463 (4)
H1	0.2031	0.4119	−0.0396	0.056*
N2	0.14400 (8)	0.7943 (3)	0.02607 (7)	0.0493 (4)
H2	0.1213	0.8542	−0.0064	0.059*
N3	0.17078 (11)	0.8880 (5)	0.23452 (9)	0.0698 (6)
C1	0.07531 (12)	0.4940 (5)	−0.18585 (9)	0.0621 (6)
H1A	0.0817	0.4399	−0.2223	0.075*
H1B	0.0599	0.6690	−0.1902	0.075*
C2	0.13788 (11)	0.4820 (5)	−0.13939 (9)	0.0643 (6)
H2A	0.1709	0.5636	−0.1531	0.077*
H2B	0.1499	0.3045	−0.1310	0.077*
C3	0.13382 (11)	0.6119 (5)	−0.08498 (9)	0.0549 (5)
C4	0.18352 (9)	0.6053 (4)	0.02127 (8)	0.0423 (4)
C5	0.13280 (9)	0.9128 (4)	0.07449 (8)	0.0446 (4)
C6	0.15981 (10)	0.8404 (4)	0.13142 (9)	0.0522 (5)
H6	0.1885	0.7046	0.1404	0.063*
C7	0.14349 (11)	0.9724 (4)	0.17438 (9)	0.0542 (5)
C8	0.10111 (12)	1.1733 (5)	0.16383 (11)	0.0633 (6)
H8	0.0910	1.2581	0.1940	0.076*
C9	0.07415 (11)	1.2451 (5)	0.10774 (11)	0.0623 (6)
H9	0.0452	1.3802	0.0994	0.075*
C10	0.08968 (9)	1.1184 (4)	0.06386 (9)	0.0488 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0769 (4)	0.0880 (5)	0.0603 (4)	−0.0004 (3)	0.0144 (3)	0.0036 (3)
Cl2	0.0538 (3)	0.0559 (3)	0.0650 (4)	0.0055 (2)	0.0129 (3)	0.0085 (3)
S1	0.0527 (3)	0.0642 (4)	0.0402 (3)	0.0126 (2)	0.0063 (2)	0.0008 (2)
O1	0.0931 (13)	0.0910 (13)	0.0459 (9)	0.0442 (11)	0.0013 (8)	−0.0009 (9)
O2	0.1354 (19)	0.1033 (17)	0.0538 (11)	0.0309 (15)	0.0222 (11)	0.0075 (11)
O3	0.1274 (18)	0.1121 (16)	0.0543 (11)	0.0061 (13)	0.0387 (11)	−0.0152 (11)
N1	0.0480 (9)	0.0518 (10)	0.0379 (8)	0.0064 (7)	0.0101 (7)	−0.0004 (7)
N2	0.0559 (10)	0.0499 (10)	0.0389 (9)	0.0100 (8)	0.0082 (7)	0.0002 (7)
N3	0.0830 (14)	0.0789 (14)	0.0504 (11)	−0.0075 (12)	0.0233 (10)	−0.0064 (11)
C1	0.0694 (14)	0.0764 (16)	0.0370 (10)	0.0101 (12)	0.0092 (10)	0.0061 (10)
C2	0.0597 (13)	0.0895 (18)	0.0401 (11)	0.0143 (12)	0.0080 (10)	−0.0035 (11)
C3	0.0560 (12)	0.0647 (13)	0.0405 (11)	0.0111 (11)	0.0077 (9)	0.0017 (10)
C4	0.0429 (10)	0.0446 (10)	0.0386 (10)	−0.0046 (8)	0.0104 (8)	−0.0011 (8)
C5	0.0450 (10)	0.0430 (11)	0.0462 (11)	−0.0058 (8)	0.0133 (8)	−0.0055 (9)
C6	0.0551 (12)	0.0519 (12)	0.0499 (12)	−0.0007 (10)	0.0156 (9)	−0.0052 (9)
C7	0.0585 (12)	0.0588 (13)	0.0471 (11)	−0.0104 (10)	0.0177 (10)	−0.0072 (10)
C8	0.0682 (15)	0.0651 (15)	0.0640 (15)	−0.0021 (12)	0.0306 (12)	−0.0160 (12)
C9	0.0588 (13)	0.0592 (14)	0.0733 (16)	0.0069 (11)	0.0257 (12)	−0.0086 (12)
C10	0.0430 (10)	0.0474 (11)	0.0555 (12)	−0.0050 (9)	0.0128 (9)	−0.0013 (9)

Cl1—C1	1.788 (3)	C1—H1A	0.9700
Cl2—C10	1.732 (2)	C1—H1B	0.9700
S1—C4	1.656 (2)	C2—C3	1.503 (3)
O1—C3	1.209 (3)	C2—H2A	0.9700
O2—N3	1.215 (3)	C2—H2B	0.9700
O3—N3	1.211 (3)	C5—C6	1.386 (3)
N1—C3	1.368 (3)	C5—C10	1.402 (3)
N1—C4	1.391 (2)	C6—C7	1.373 (3)
N1—H1	0.8600	C6—H6	0.9300
N2—C4	1.336 (3)	C7—C8	1.373 (3)
N2—C5	1.403 (2)	C8—C9	1.367 (3)
N2—H2	0.8600	C8—H8	0.9300
N3—C7	1.472 (3)	C9—C10	1.370 (3)
C1—C2	1.501 (3)	C9—H9	0.9300
C3—N1—C4	128.54 (18)	N1—C3—C2	115.24 (19)
C3—N1—H1	115.7	N2—C4—N1	114.09 (17)
C4—N1—H1	115.7	N2—C4—S1	127.65 (15)
C4—N2—C5	131.77 (17)	N1—C4—S1	118.27 (15)
C4—N2—H2	114.1	C6—C5—C10	117.74 (19)
C5—N2—H2	114.1	C6—C5—N2	125.45 (19)
O3—N3—O2	123.3 (2)	C10—C5—N2	116.79 (18)
O3—N3—C7	118.3 (2)	C7—C6—C5	118.9 (2)
O2—N3—C7	118.3 (2)	C7—C6—H6	120.5
C2—C1—Cl1	110.94 (17)	C5—C6—H6	120.5
C2—C1—H1A	109.5	C6—C7—C8	123.2 (2)
Cl1—C1—H1A	109.5	C6—C7—N3	118.4 (2)
C2—C1—H1B	109.5	C8—C7—N3	118.4 (2)
Cl1—C1—H1B	109.5	C9—C8—C7	118.1 (2)
H1A—C1—H1B	108.0	C9—C8—H8	120.9
C1—C2—C3	111.67 (19)	C7—C8—H8	120.9
C1—C2—H2A	109.3	C8—C9—C10	120.1 (2)
C3—C2—H2A	109.3	C8—C9—H9	119.9
C1—C2—H2B	109.3	C10—C9—H9	119.9
C3—C2—H2B	109.3	C9—C10—C5	121.8 (2)
H2A—C2—H2B	107.9	C9—C10—Cl2	118.31 (18)
O1—C3—N1	122.5 (2)	C5—C10—Cl2	119.85 (16)
O1—C3—C2	122.22 (19)
Cl1—C1—C2—C3	−70.4 (3)	C5—C6—C7—N3	177.91 (19)
C4—N1—C3—O1	2.2 (4)	O3—N3—C7—C6	177.6 (2)
C4—N1—C3—C2	−178.1 (2)	O2—N3—C7—C6	−4.9 (3)
C1—C2—C3—O1	−25.3 (4)	O3—N3—C7—C8	−4.8 (3)
C1—C2—C3—N1	155.0 (2)	O2—N3—C7—C8	172.7 (2)
C5—N2—C4—N1	175.19 (19)	C6—C7—C8—C9	−0.2 (4)
C5—N2—C4—S1	−4.5 (3)	N3—C7—C8—C9	−177.7 (2)
C3—N1—C4—N2	−3.1 (3)	C7—C8—C9—C10	−0.2 (4)
C3—N1—C4—S1	176.60 (18)	C8—C9—C10—C5	0.4 (3)
C4—N2—C5—C6	−4.7 (3)	C8—C9—C10—Cl2	−179.30 (18)
C4—N2—C5—C10	176.6 (2)	C6—C5—C10—C9	−0.2 (3)
C10—C5—C6—C7	−0.2 (3)	N2—C5—C10—C9	178.68 (19)
N2—C5—C6—C7	−178.95 (19)	C6—C5—C10—Cl2	179.49 (15)
C5—C6—C7—C8	0.4 (3)	N2—C5—C10—Cl2	−1.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.87	2.596 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.87	2.596 (2)	142