(2Z)-N-(2-Chloro­benz­yl)-2-(2-oxo-2,3-dihydro-1H-indol-3-yl­idene)hydrazinecarbothio­amide

Pervez, H.; Khan, N.; Iqbal, M.S.; Yaqub, M.; Tahir, M.N.

doi:10.1107/S1600536812035076

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2731

doi:10.1107/S1600536812035076

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(2Z)-N-(2-Chlorobenzyl)-2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)hydrazinecarbothioamide

Humayun Pervez,^a Nazia Khan,^a Mohammad S. Iqbal,^b Muhammad Yaqub ^a and M. Nawaz Tahir ^c ^*

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, ^bDepartment of Chemistry, Forman Christian College, Lahore 54600, Pakistan, and ^cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 31 July 2012; accepted 8 August 2012; online 23 August 2012)

In the title compound, C₁₆H₁₃ClN₄OS, the isatin ring system is oriented at dihedral angles of 10.60 (7) and 72.60 (3)° with respect to the thiosemicarbazide and 2-chlorobenzyl groups, respectively. The near planarity of the isatin and thiosemicarbazide groups [r.m.s. deviations of 0.0420 and 0.0163 Å, respectively] is reinforced by intramolecular N—H⋯O and N—H⋯N hydrogen bonds, which generate S(6) and S(5) rings, respectively. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R₂²(8) loops. Aromatic π–π stacking interactions between the centroids of heterocyclic five-membered and benzene rings [distance = 3.6866 (11) Å] are also observed.

Related literature

For biochemical background to isatins, see: Pervez et al. (2012 ). For a related structure, see: Ramzan et al. (2010 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₃ClN₄OS
M_r = 344.81
Monoclinic, P 2₁ /c
a = 13.7017 (10) Å
b = 14.1585 (10) Å
c = 8.2698 (5) Å
β = 93.151 (3)°
V = 1601.88 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 296 K
0.32 × 0.23 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.888, T_max = 0.929
14957 measured reflections
3935 independent reflections
2541 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.105
S = 1.02
3935 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.86	2.05	2.7416 (19)	137
N4—H4A⋯N2	0.86	2.28	2.663 (2)	107
N1—H1⋯O1ⁱ	0.86	2.09	2.903 (2)	157
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812035076/hb6928sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812035076/hb6928Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812035076/hb6928Isup3.cml

checkCIF report

Comment top

As a part of our ongoing work on the synthesis of isatin-thiosemicarbazones having certain pharmaceutical applications (Pervez et al., 2012), we report herein the synthesis and crystal structure of the title compound (Fig. 1). The crystal structure of 1-(2-oxoindolin-3-ylidene)-4-[2-(trifluoromethoxy)phenyl]thiosemicarbazide (Ramzan et al. 2010) has been published which is related to the title compound.

In the title compound, the group A (C1—C8/N1/O1) of isatin moiety, group B (N2/N3/C9/S1/N4) of thiosemicarbazide and group C (C10—C16/CL1) of 2-chlorobenzyl are planar with r.m.s. deviations of 0.0230 Å, 0.0420 Å and 0.0163 Å, respectively. The dihedral angle between A/B, A/C and B/C are 10.60 (7)°, 72.60 (3)° and 72.89 (3)°, respectively. In the title compound, S(5) and S(6) ring motifs (Bernstein et al., 1995) are formed due to intramolecular H-bondings of N—H···N and N—H···O types, respectively (Table 1, Fig. 1). The molecules are stabilized in the form of dimers due to H-bonding of N—H···O type (Table 1, Fig. 2) with R₂²(8) ring motif. There exists π–π interaction between Cg1···Cg2ⁱ [i = x, 1/2 - y, -1/2 + z] at a distance of 3.6866 (11) Å, where Cg1 and Cg2 are the centroids of heterocyclic five membered ring (C1/C6/N1/C7/C8) and the benzene ring (C1—C6), respectively. Similarly, π–π interaction exists between Cg2···Cg1ⁱⁱ [ii = x, 1/2 - y, 1/2 + z] at a distance of 3.6866 (11) Å.

Related literature top

For biochemical background to isatins, see: Pervez et al. (2012). For a related structure, see: Ramzan et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

To a hot solution of isatin (0.74 g, 5 mmol) in 50% aqueous ethanol (15 ml) was added 4-(2-chlorobenzyl)thiosemicarbazide (1.08 g, 5 mmol) dissolved in ethanol (10 ml) under stirring. The reaction mixture was then refluxed for 2 h. The orange crystalline solid formed during heating was collected by suction filtration. Thorough washing with hot aqueous ethanol afforded the title compound in pure form (1.55 g, 90%), m.p. 525 K. The orange prisms of title compound were grown from chloroform solution by slow evaporation of the solvent.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level. The dotted lines represent the intramolecular hydrogen bonds.

Fig. 2. The partial packing diagram, which shows that molecules form dimers with R₂²(8) ring motifs.

(2Z)-N-(2-Chlorobenzyl)-2-(2-oxo-2,3-dihydro-1H-indol- 3-ylidene)hydrazinecarbothioamide top

Crystal data top

C₁₆H₁₃ClN₄OS	F(000) = 712
M_r = 344.81	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2075 reflections
a = 13.7017 (10) Å	θ = 1.5–28.4°
b = 14.1585 (10) Å	µ = 0.38 mm⁻¹
c = 8.2698 (5) Å	T = 296 K
β = 93.151 (3)°	Prism, orange
V = 1601.88 (19) Å³	0.32 × 0.23 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3935 independent reflections
Radiation source: fine-focus sealed tube	2541 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 7.50 pixels mm^-1	θ_max = 28.4°, θ_min = 1.5°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→18
T_min = 0.888, T_max = 0.929	l = −8→11
14957 measured reflections

Refinement top

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0415P)² + 0.3273P] where P = (F_o² + 2F_c²)/3
3935 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₆H₁₃ClN₄OS	V = 1601.88 (19) Å³
M_r = 344.81	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.7017 (10) Å	µ = 0.38 mm⁻¹
b = 14.1585 (10) Å	T = 296 K
c = 8.2698 (5) Å	0.32 × 0.23 × 0.20 mm
β = 93.151 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3935 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2541 reflections with I > 2σ(I)
T_min = 0.888, T_max = 0.929	R_int = 0.033
14957 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.02	Δρ_max = 0.21 e Å⁻³
3935 reflections	Δρ_min = −0.29 e Å⁻³
208 parameters

Special details top

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 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.34601 (5)	−0.04349 (4)	0.12764 (8)	0.0798 (3)
S1	0.30114 (4)	0.37338 (4)	−0.01319 (6)	0.0502 (2)
O1	0.07991 (10)	0.44729 (9)	0.35390 (16)	0.0505 (5)
N1	−0.05032 (11)	0.37716 (11)	0.47406 (17)	0.0434 (5)
N2	0.11200 (10)	0.24682 (10)	0.24169 (15)	0.0336 (4)
N3	0.17023 (10)	0.31195 (10)	0.17804 (16)	0.0363 (5)
N4	0.26056 (11)	0.19523 (11)	0.06682 (17)	0.0402 (5)
C1	−0.02814 (12)	0.22197 (12)	0.40963 (19)	0.0352 (5)
C2	−0.04817 (15)	0.12656 (14)	0.4110 (2)	0.0488 (7)
C3	−0.12841 (17)	0.09610 (16)	0.4929 (3)	0.0615 (8)
C4	−0.18653 (16)	0.16013 (18)	0.5692 (3)	0.0628 (8)
C5	−0.16717 (15)	0.25630 (16)	0.5693 (2)	0.0517 (7)
C6	−0.08666 (13)	0.28509 (13)	0.48984 (19)	0.0382 (6)
C7	0.02986 (13)	0.37795 (13)	0.3854 (2)	0.0380 (6)
C8	0.04609 (12)	0.27811 (12)	0.33533 (18)	0.0329 (5)
C9	0.24367 (12)	0.28702 (12)	0.07912 (19)	0.0351 (5)
C10	0.34135 (14)	0.15508 (15)	−0.0198 (2)	0.0469 (7)
C11	0.42635 (14)	0.12971 (14)	0.0949 (2)	0.0424 (6)
C12	0.43573 (15)	0.04174 (14)	0.1681 (2)	0.0493 (7)
C13	0.51332 (19)	0.01890 (19)	0.2740 (3)	0.0655 (9)
C14	0.5822 (2)	0.0854 (2)	0.3117 (3)	0.0775 (10)
C15	0.57512 (18)	0.1745 (2)	0.2452 (3)	0.0716 (10)
C16	0.49822 (16)	0.19569 (16)	0.1363 (3)	0.0563 (8)
H1	−0.07566	0.42658	0.51532	0.0520*
H2	−0.00915	0.08379	0.35873	0.0585*
H3	−0.14309	0.03203	0.49624	0.0737*
H3A	0.16137	0.37063	0.19967	0.0436*
H4	−0.24022	0.13810	0.62202	0.0754*
H4A	0.22182	0.15693	0.11237	0.0482*
H5	−0.20661	0.29916	0.62051	0.0620*
H10A	0.36248	0.20052	−0.09843	0.0563*
H10B	0.31882	0.09901	−0.07802	0.0563*
H13	0.51841	−0.04121	0.31903	0.0786*
H14	0.63470	0.07069	0.38322	0.0930*
H15	0.62188	0.22004	0.27339	0.0861*
H16	0.49455	0.25549	0.08983	0.0676*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0945 (5)	0.0626 (4)	0.0842 (4)	−0.0105 (3)	0.0230 (4)	0.0024 (3)
S1	0.0545 (3)	0.0484 (3)	0.0491 (3)	−0.0073 (3)	0.0144 (2)	0.0011 (2)
O1	0.0604 (9)	0.0332 (7)	0.0602 (8)	−0.0045 (7)	0.0230 (7)	−0.0027 (6)
N1	0.0451 (10)	0.0386 (9)	0.0477 (9)	0.0048 (7)	0.0148 (7)	−0.0051 (7)
N2	0.0338 (8)	0.0342 (8)	0.0326 (7)	0.0000 (7)	−0.0002 (6)	−0.0001 (6)
N3	0.0378 (9)	0.0321 (8)	0.0396 (8)	0.0006 (7)	0.0073 (7)	−0.0032 (6)
N4	0.0364 (9)	0.0423 (9)	0.0424 (8)	0.0042 (7)	0.0080 (7)	0.0018 (7)
C1	0.0363 (10)	0.0384 (10)	0.0304 (8)	−0.0040 (8)	−0.0014 (7)	−0.0002 (7)
C2	0.0574 (13)	0.0422 (11)	0.0466 (11)	−0.0061 (10)	0.0023 (9)	−0.0018 (9)
C3	0.0712 (16)	0.0534 (13)	0.0598 (13)	−0.0266 (12)	0.0038 (12)	0.0019 (11)
C4	0.0571 (14)	0.0799 (17)	0.0526 (12)	−0.0262 (13)	0.0135 (11)	0.0042 (12)
C5	0.0434 (12)	0.0663 (14)	0.0460 (11)	−0.0069 (11)	0.0091 (9)	−0.0059 (10)
C6	0.0381 (11)	0.0440 (10)	0.0323 (9)	−0.0036 (9)	0.0007 (8)	−0.0011 (8)
C7	0.0415 (11)	0.0363 (10)	0.0366 (9)	0.0018 (9)	0.0057 (8)	−0.0005 (7)
C8	0.0350 (10)	0.0340 (9)	0.0295 (8)	0.0011 (8)	−0.0010 (7)	−0.0008 (7)
C9	0.0343 (10)	0.0420 (10)	0.0287 (8)	0.0015 (8)	−0.0015 (7)	−0.0040 (7)
C10	0.0504 (12)	0.0531 (12)	0.0376 (10)	0.0165 (10)	0.0065 (9)	−0.0019 (9)
C11	0.0421 (12)	0.0499 (11)	0.0364 (9)	0.0132 (10)	0.0121 (8)	−0.0004 (8)
C12	0.0519 (13)	0.0535 (12)	0.0439 (11)	0.0106 (10)	0.0159 (10)	−0.0010 (9)
C13	0.0745 (17)	0.0705 (16)	0.0519 (13)	0.0304 (15)	0.0065 (12)	0.0110 (11)
C14	0.0614 (17)	0.103 (2)	0.0668 (16)	0.0278 (17)	−0.0094 (13)	−0.0021 (15)
C15	0.0481 (14)	0.090 (2)	0.0766 (16)	0.0000 (14)	0.0015 (12)	−0.0178 (15)
C16	0.0509 (14)	0.0575 (14)	0.0615 (13)	0.0094 (12)	0.0111 (11)	0.0021 (10)

Geometric parameters (Å, º) top

Cl1—C12	1.742 (2)	C5—C6	1.376 (3)
S1—C9	1.6625 (18)	C7—C8	1.493 (2)
O1—C7	1.234 (2)	C10—C11	1.505 (3)
N1—C6	1.404 (2)	C11—C16	1.387 (3)
N1—C7	1.354 (2)	C11—C12	1.388 (3)
N2—N3	1.345 (2)	C12—C13	1.378 (3)
N2—C8	1.299 (2)	C13—C14	1.357 (4)
N3—C9	1.377 (2)	C14—C15	1.378 (4)
N4—C9	1.325 (2)	C15—C16	1.381 (3)
N4—C10	1.466 (2)	C2—H2	0.9300
N1—H1	0.8600	C3—H3	0.9300
N3—H3A	0.8600	C4—H4	0.9300
N4—H4A	0.8600	C5—H5	0.9300
C1—C8	1.453 (2)	C10—H10A	0.9700
C1—C2	1.379 (3)	C10—H10B	0.9700
C1—C6	1.393 (2)	C13—H13	0.9300
C2—C3	1.391 (3)	C14—H14	0.9300
C3—C4	1.382 (3)	C15—H15	0.9300
C4—C5	1.387 (3)	C16—H16	0.9300

C6—N1—C7	111.13 (15)	C10—C11—C16	120.63 (18)
N3—N2—C8	116.49 (14)	C10—C11—C12	122.63 (18)
N2—N3—C9	121.67 (14)	C11—C12—C13	122.5 (2)
C9—N4—C10	123.90 (15)	Cl1—C12—C11	119.38 (15)
C7—N1—H1	124.00	Cl1—C12—C13	118.11 (17)
C6—N1—H1	124.00	C12—C13—C14	119.1 (2)
C9—N3—H3A	119.00	C13—C14—C15	120.7 (2)
N2—N3—H3A	119.00	C14—C15—C16	119.6 (2)
C9—N4—H4A	118.00	C11—C16—C15	121.4 (2)
C10—N4—H4A	118.00	C1—C2—H2	121.00
C2—C1—C6	120.31 (16)	C3—C2—H2	121.00
C2—C1—C8	133.12 (16)	C2—C3—H3	120.00
C6—C1—C8	106.56 (15)	C4—C3—H3	120.00
C1—C2—C3	118.08 (18)	C3—C4—H4	119.00
C2—C3—C4	120.6 (2)	C5—C4—H4	119.00
C3—C4—C5	122.0 (2)	C4—C5—H5	122.00
C4—C5—C6	116.66 (19)	C6—C5—H5	122.00
N1—C6—C1	109.58 (15)	N4—C10—H10A	109.00
N1—C6—C5	128.09 (17)	N4—C10—H10B	109.00
C1—C6—C5	122.33 (18)	C11—C10—H10A	109.00
O1—C7—N1	126.73 (17)	C11—C10—H10B	109.00
O1—C7—C8	127.01 (16)	H10A—C10—H10B	108.00
N1—C7—C8	106.26 (15)	C12—C13—H13	120.00
N2—C8—C7	127.38 (15)	C14—C13—H13	120.00
N2—C8—C1	126.22 (16)	C13—C14—H14	120.00
C1—C8—C7	106.39 (14)	C15—C14—H14	120.00
S1—C9—N3	117.66 (13)	C14—C15—H15	120.00
S1—C9—N4	126.66 (13)	C16—C15—H15	120.00
N3—C9—N4	115.68 (15)	C11—C16—H16	119.00
N4—C10—C11	111.33 (14)	C15—C16—H16	119.00
C12—C11—C16	116.71 (18)

C7—N1—C6—C1	0.42 (19)	C1—C2—C3—C4	0.6 (3)
C7—N1—C6—C5	−179.26 (17)	C2—C3—C4—C5	−0.8 (4)
C6—N1—C7—O1	−177.87 (17)	C3—C4—C5—C6	−0.2 (3)
C6—N1—C7—C8	1.46 (18)	C4—C5—C6—N1	−178.93 (18)
C8—N2—N3—C9	178.97 (14)	C4—C5—C6—C1	1.4 (3)
N3—N2—C8—C1	176.21 (14)	O1—C7—C8—N2	−4.5 (3)
N3—N2—C8—C7	−2.4 (2)	O1—C7—C8—C1	176.61 (17)
N2—N3—C9—S1	171.76 (11)	N1—C7—C8—N2	176.14 (16)
N2—N3—C9—N4	−7.8 (2)	N1—C7—C8—C1	−2.73 (18)
C10—N4—C9—S1	6.5 (2)	N4—C10—C11—C12	89.5 (2)
C10—N4—C9—N3	−174.00 (14)	N4—C10—C11—C16	−88.4 (2)
C9—N4—C10—C11	98.6 (2)	C10—C11—C12—Cl1	−0.3 (2)
C6—C1—C2—C3	0.6 (3)	C10—C11—C12—C13	−179.54 (19)
C8—C1—C2—C3	−178.34 (19)	C16—C11—C12—Cl1	177.75 (15)
C2—C1—C6—N1	178.63 (15)	C16—C11—C12—C13	−1.5 (3)
C2—C1—C6—C5	−1.7 (3)	C10—C11—C16—C15	178.0 (2)
C8—C1—C6—N1	−2.16 (18)	C12—C11—C16—C15	−0.1 (3)
C8—C1—C6—C5	177.54 (16)	Cl1—C12—C13—C14	−177.65 (19)
C2—C1—C8—N2	3.1 (3)	C11—C12—C13—C14	1.7 (3)
C2—C1—C8—C7	−177.98 (18)	C12—C13—C14—C15	−0.1 (4)
C6—C1—C8—N2	−175.93 (15)	C13—C14—C15—C16	−1.4 (4)
C6—C1—C8—C7	2.96 (17)	C14—C15—C16—C11	1.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.86	2.05	2.7416 (19)	137
N4—H4A···N2	0.86	2.28	2.663 (2)	107
N1—H1···O1ⁱ	0.86	2.09	2.903 (2)	157

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClN₄OS
M_r	344.81
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.7017 (10), 14.1585 (10), 8.2698 (5)
β (°)	93.151 (3)
V (Å³)	1601.88 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.32 × 0.23 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.888, 0.929
No. of measured, independent and observed [I > 2σ(I)] reflections	14957, 3935, 2541
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.105, 1.02
No. of reflections	3935
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.29

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.86	2.05	2.7416 (19)	137
N4—H4A···N2	0.86	2.28	2.663 (2)	107
N1—H1···O1ⁱ	0.86	2.09	2.903 (2)	157

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

HP, MSI and NK thank the Higher Education Commission (HEC), Pakistan, for financial assistance under the National Research Program for Universities (project No. 20–873/R&D/07/452).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Pervez, H., Ramzan, M., Yaqub, M., Nasim, F. H. & Khan, K. M. (2012). Med. Chem. 8, 505–514. Web of Science CrossRef CAS PubMed Google Scholar
Ramzan, M., Pervez, H., Tahir, M. N., Yaqub, M. & Iqbal, M. S. (2010). Acta Cryst. E66, o2447. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 9| September 2012| Page o2731

doi:10.1107/S1600536812035076

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2Z)-N-(2-Chloro­benz­yl)-2-(2-oxo-2,3-di­hydro-1H-indol-3-yl­­idene)hydrazinecarbo­thio­amide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(2Z)-N-(2-Chlorobenzyl)-2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)hydrazinecarbothioamide