3-Chloro-N-[N-(furan-2-carbon-yl)hydrazinocarbo-thio-yl]benzamide.

In the title compound C13H10ClN3O3S, the benzoyl group maintains its trans conformation against the thiono group about the C-N bond and the intra-molecular hydrogen bond between the benzoyl O atom and thio-amide H atom. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules, forming chains along the b-axis direction. In addition, C-H⋯π inter-actions occur between a phenyl H atom and the furan ring.

Related literature

For bond-lengths data, see: Allen et al. (1987 ▶) and for a description of the Cambridge Structural Database, see: Allen (2002 ▶). For related structures of thio­urea derivatives, see: Yamin & Yusof (2003 ▶); Yusof et al. (2003 ▶); Ali et al. (2004 ▶); Venkatachalam et al. (2004 ▶); Saeed et al. (2011 ▶); Wilson et al. (2010 ▶).

Experimental

Crystal data

C13H10ClN3O3S

M = 323.75

Orthorhombic,

a = 7.286 (4) Å

b = 15.148 (8) Å

c = 25.840 (14) Å

V = 2852 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.43 mm−1

T = 298 K

0.50 × 0.49 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.815, T max = 0.951

15224 measured reflections

2507 independent reflections

1723 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.117

S = 1.02

2507 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 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/S1600536813025440/bg2516sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025440/bg2516Isup2.hkl

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

C13H10ClN3O3S	F(000) = 1328
Mr = 323.75	Dx = 1.508 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1801 reflections
a = 7.286 (4) Å	θ = 1.5–25.0°
b = 15.148 (8) Å	µ = 0.43 mm−1
c = 25.840 (14) Å	T = 298 K
V = 2852 (3) Å3	Block, colourless
Z = 8	0.50 × 0.49 × 0.12 mm

Bruker SMART APEX CCD area-detector diffractometer	2507 independent reflections
Radiation source: fine-focus sealed tube	1723 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
Detector resolution: 83.66 pixels mm-1	θmax = 25.0°, θmin = 1.6°
ω scan	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −18→18
Tmin = 0.815, Tmax = 0.951	l = −30→20
15224 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.P)2 + 1.0899P] where P = (Fo2 + 2Fc2)/3
2507 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.19 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	0.98435 (14)	−0.08651 (5)	−0.18005 (3)	0.0735 (3)
O1	0.7448 (3)	0.04610 (12)	−0.00613 (7)	0.0591 (6)
O2	0.6645 (3)	0.25070 (11)	0.08567 (7)	0.0509 (5)
O3	0.4281 (3)	0.21465 (12)	0.20364 (7)	0.0509 (5)
N1	0.7094 (3)	−0.06226 (13)	0.05323 (8)	0.0436 (6)
H1A	0.7296	−0.1173	0.0592	0.052*
N2	0.6422 (3)	0.07378 (13)	0.08781 (8)	0.0419 (6)
H2A	0.6885	0.0964	0.0602	0.050*
N3	0.5717 (3)	0.12697 (13)	0.12567 (9)	0.0461 (6)
H3A	0.5170	0.1039	0.1519	0.055*
C1	0.8615 (4)	−0.06793 (17)	−0.08220 (11)	0.0436 (7)
H1B	0.8702	−0.0074	−0.0878	0.052*
C2	0.9095 (4)	−0.12615 (18)	−0.12060 (11)	0.0441 (7)
C3	0.8981 (4)	−0.21559 (17)	−0.11338 (12)	0.0474 (7)
H3B	0.9332	−0.2543	−0.1395	0.057*
C4	0.8341 (5)	−0.24695 (18)	−0.06697 (12)	0.0543 (8)
H4A	0.8249	−0.3075	−0.0618	0.065*
C5	0.7834 (4)	−0.19013 (17)	−0.02794 (11)	0.0510 (8)
H5A	0.7379	−0.2123	0.0031	0.061*
C6	0.8002 (4)	−0.09970 (16)	−0.03502 (10)	0.0388 (6)
C7	0.7507 (4)	−0.03252 (17)	0.00457 (10)	0.0418 (7)
C8	0.6385 (4)	−0.01326 (16)	0.09412 (10)	0.0396 (6)
C9	0.5875 (4)	0.21534 (15)	0.12203 (10)	0.0356 (6)
C10	0.5023 (4)	0.26306 (16)	0.16468 (9)	0.0360 (6)
C11	0.4757 (4)	0.34892 (18)	0.17338 (12)	0.0501 (8)
H11A	0.5155	0.3954	0.1527	0.060*
C12	0.3764 (5)	0.3558 (2)	0.21962 (12)	0.0593 (9)
H12A	0.3359	0.4075	0.2353	0.071*
C13	0.3516 (5)	0.2743 (2)	0.23661 (12)	0.0613 (9)
H13A	0.2902	0.2598	0.2670	0.074*
S1	0.55517 (13)	−0.06141 (5)	0.14664 (3)	0.0566 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.1084 (8)	0.0531 (5)	0.0589 (6)	−0.0122 (5)	0.0308 (5)	−0.0102 (4)
O1	0.1014 (18)	0.0309 (11)	0.0451 (12)	0.0079 (10)	0.0097 (11)	0.0008 (9)
O2	0.0729 (15)	0.0372 (10)	0.0427 (11)	−0.0040 (9)	0.0154 (10)	0.0013 (9)
O3	0.0632 (14)	0.0457 (11)	0.0437 (12)	0.0032 (9)	0.0137 (10)	0.0024 (9)
N1	0.0614 (16)	0.0247 (11)	0.0448 (14)	0.0032 (10)	−0.0005 (11)	−0.0022 (10)
N2	0.0572 (15)	0.0303 (11)	0.0381 (13)	0.0018 (10)	0.0081 (11)	−0.0017 (10)
N3	0.0648 (17)	0.0317 (12)	0.0416 (13)	0.0010 (11)	0.0137 (12)	−0.0021 (10)
C1	0.0508 (18)	0.0302 (13)	0.0497 (18)	−0.0015 (12)	−0.0007 (14)	−0.0064 (12)
C2	0.0432 (17)	0.0421 (15)	0.0469 (17)	−0.0036 (13)	0.0029 (13)	−0.0076 (13)
C3	0.0535 (19)	0.0373 (15)	0.0512 (18)	0.0082 (13)	−0.0081 (15)	−0.0126 (13)
C4	0.080 (2)	0.0290 (14)	0.0535 (18)	0.0094 (14)	−0.0144 (16)	−0.0050 (13)
C5	0.076 (2)	0.0367 (16)	0.0406 (17)	0.0027 (14)	−0.0108 (15)	0.0022 (12)
C6	0.0464 (17)	0.0300 (14)	0.0401 (15)	0.0044 (11)	−0.0074 (13)	−0.0023 (11)
C7	0.0494 (17)	0.0344 (15)	0.0417 (17)	0.0026 (12)	−0.0064 (13)	−0.0021 (12)
C8	0.0437 (16)	0.0315 (14)	0.0436 (16)	0.0001 (12)	−0.0046 (13)	−0.0033 (12)
C9	0.0396 (16)	0.0306 (14)	0.0365 (15)	0.0007 (11)	−0.0035 (12)	0.0001 (11)
C10	0.0396 (16)	0.0354 (13)	0.0329 (14)	−0.0010 (12)	−0.0013 (12)	0.0003 (11)
C11	0.065 (2)	0.0369 (15)	0.0489 (18)	0.0036 (14)	0.0038 (15)	−0.0045 (13)
C12	0.072 (2)	0.0511 (19)	0.055 (2)	0.0136 (16)	0.0045 (17)	−0.0165 (16)
C13	0.062 (2)	0.076 (2)	0.0457 (18)	0.0112 (18)	0.0154 (16)	−0.0076 (16)
S1	0.0856 (6)	0.0331 (4)	0.0513 (5)	−0.0044 (4)	0.0144 (4)	0.0026 (3)

Cl1—C2	1.737 (3)	C2—C3	1.370 (4)
O1—C7	1.223 (3)	C3—C4	1.372 (4)
O2—C9	1.219 (3)	C3—H3B	0.9300
O3—C10	1.358 (3)	C4—C5	1.376 (4)
O3—C13	1.362 (3)	C4—H4A	0.9300
N1—C7	1.369 (3)	C5—C6	1.388 (4)
N1—C8	1.391 (3)	C5—H5A	0.9300
N1—H1A	0.8600	C6—C7	1.488 (4)
N2—C8	1.329 (3)	C8—S1	1.656 (3)
N2—N3	1.368 (3)	C9—C10	1.457 (3)
N2—H2A	0.8600	C10—C11	1.334 (4)
N3—C9	1.347 (3)	C11—C12	1.401 (4)
N3—H3A	0.8600	C11—H11A	0.9300
C1—C2	1.373 (4)	C12—C13	1.322 (4)
C1—C6	1.385 (4)	C12—H12A	0.9300
C1—H1B	0.9300	C13—H13A	0.9300
C10—O3—C13	105.6 (2)	C1—C6—C5	119.2 (2)
C7—N1—C8	127.1 (2)	C1—C6—C7	116.5 (2)
C7—N1—H1A	116.4	C5—C6—C7	124.3 (3)
C8—N1—H1A	116.4	O1—C7—N1	121.4 (2)
C8—N2—N3	119.3 (2)	O1—C7—C6	121.3 (3)
C8—N2—H2A	120.4	N1—C7—C6	117.4 (2)
N3—N2—H2A	120.4	N2—C8—N1	115.4 (2)
C9—N3—N2	120.2 (2)	N2—C8—S1	123.0 (2)
C9—N3—H3A	119.9	N1—C8—S1	121.59 (18)
N2—N3—H3A	119.9	O2—C9—N3	122.0 (2)
C2—C1—C6	119.7 (2)	O2—C9—C10	124.2 (2)
C2—C1—H1B	120.2	N3—C9—C10	113.8 (2)
C6—C1—H1B	120.2	C11—C10—O3	110.1 (2)
C3—C2—C1	121.4 (3)	C11—C10—C9	132.3 (2)
C3—C2—Cl1	118.8 (2)	O3—C10—C9	117.5 (2)
C1—C2—Cl1	119.8 (2)	C10—C11—C12	106.9 (3)
C2—C3—C4	118.8 (3)	C10—C11—H11A	126.5
C2—C3—H3B	120.6	C12—C11—H11A	126.5
C4—C3—H3B	120.6	C13—C12—C11	106.6 (3)
C3—C4—C5	121.0 (3)	C13—C12—H12A	126.7
C3—C4—H4A	119.5	C11—C12—H12A	126.7
C5—C4—H4A	119.5	C12—C13—O3	110.9 (3)
C4—C5—C6	119.8 (3)	C12—C13—H13A	124.6
C4—C5—H5A	120.1	O3—C13—H13A	124.6
C6—C5—H5A	120.1
C8—N2—N3—C9	174.6 (2)	N3—N2—C8—N1	178.7 (2)
C6—C1—C2—C3	0.0 (4)	N3—N2—C8—S1	−1.2 (4)
C6—C1—C2—Cl1	179.4 (2)	C7—N1—C8—N2	−12.8 (4)
C1—C2—C3—C4	1.2 (4)	C7—N1—C8—S1	167.1 (2)
Cl1—C2—C3—C4	−178.2 (2)	N2—N3—C9—O2	−0.3 (4)
C2—C3—C4—C5	−0.6 (5)	N2—N3—C9—C10	178.8 (2)
C3—C4—C5—C6	−1.3 (5)	C13—O3—C10—C11	0.9 (3)
C2—C1—C6—C5	−1.8 (4)	C13—O3—C10—C9	−177.3 (2)
C2—C1—C6—C7	−179.9 (3)	O2—C9—C10—C11	5.0 (5)
C4—C5—C6—C1	2.5 (4)	N3—C9—C10—C11	−174.1 (3)
C4—C5—C6—C7	−179.6 (3)	O2—C9—C10—O3	−177.3 (2)
C8—N1—C7—O1	7.6 (5)	N3—C9—C10—O3	3.6 (3)
C8—N1—C7—C6	−171.5 (2)	O3—C10—C11—C12	−1.2 (3)
C1—C6—C7—O1	8.0 (4)	C9—C10—C11—C12	176.6 (3)
C5—C6—C7—O1	−170.0 (3)	C10—C11—C12—C13	1.1 (4)
C1—C6—C7—N1	−172.9 (2)	C11—C12—C13—O3	−0.5 (4)
C5—C6—C7—N1	9.1 (4)	C10—O3—C13—C12	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.92	2.574 (3)	132
N1—H1A···O2i	0.86	2.25	3.094 (3)	167
C5—H5A···O2i	0.93	2.32	3.093 (4)	140
C13—H13A···Cgii	0.93	2.83	3.516 (4)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.92	2.574 (3)	132
N1—H1A⋯O2i	0.86	2.25	3.094 (3)	167
C5—H5A⋯O2i	0.93	2.32	3.093 (4)	140
C13—H13A⋯Cg ii	0.93	2.83	3.516 (4)	132

Symmetry codes: (i) ; (ii) .