(Z)-2-(5-Chloro-2-oxoindolin-3-yl­idene)-N-phenyl­hydrazinecarbothio­amide

Qasem Ali, A.; Eltayeb, N.E.; Teoh, S.G.; Salhin, A.; Fun, H.-K.

doi:10.1107/S1600536811044199

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages o3141-o3142

https://doi.org/10.1107/S1600536811044199

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(Z)-2-(5-Chloro-2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide

Amna Qasem Ali,^a,^b Naser Eltaher Eltayeb,^a,^c ‡ Siang Guan Teoh,^a ^* Abdussalam Salhin ^a and Hoong-Kun Fun ^d §

^aSchool of Chemical Sciences, Universiti Sains Malaysia, Minden, Penang, Malaysia, ^bFaculty of Science, Sabha University, Libya, ^cDepartment of Chemistry, International University of Africa, Khartoum, Sudan, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: sgteoh@usm.my

(Received 26 September 2011; accepted 24 October 2011; online 2 November 2011)

In the title compound, C₁₅H₁₁ClN₄OS, the dihedral angle between the nine-membered 5-chloroindolin-2-one ring system and the benzene ring is 10.00 (6)°. Intramolecular cyclic N—H⋯O and C—H⋯S hydrogen-bonding interactions [graph set S(6)] are present in the N—N—C—N chain between the ring systems. In the crystal, molecules form centrosymmetric cyclic dimers through intermolecular N—H⋯O hydrogen bonds [graph-set R₂²(8)] and are extended by C—H⋯Cl interactions into infinite chains which propagate along [100].

Related literature

For related structures, see: Ferrari et al. (2002 ); Pervez et al. (2010 ); Ramzan et al. (2010 ). For various biological activities of Schiff bases, see: Bhandari et al. (2008 ); Bhardwaj et al. (2010 ); Pandeya et al. (1999 ); Sridhar et al. (2002 ); Suryavanshi & Pai (2006 ). For cytotoxic and anticancer activities of isatin and its derivatives, see: Vine et al. (2009 ). For bond-length data, see; Allen et al. (1987 ). For graph-set analysis, see Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₁ClN₄OS
M_r = 330.79
Monoclinic, P 2₁ /c
a = 5.7117 (2) Å
b = 17.9510 (7) Å
c = 14.2455 (5) Å
β = 91.262 (2)°
V = 1460.25 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 100 K
0.53 × 0.16 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.812, T_max = 0.950
15819 measured reflections
4183 independent reflections
3424 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.101
S = 1.04
4183 reflections
211 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.89 (2)	1.98 (2)	2.8560 (17)	171 (2)
N3—H1N3⋯O1	0.86 (2)	2.08 (2)	2.7563 (16)	135.9 (19)
C2—H2A⋯Cl1ⁱⁱ	0.93	2.81	3.6935 (17)	158
C11—H11A⋯S1	0.93	2.61	3.2423 (14)	126
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811044199/zs2150sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811044199/zs2150Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811044199/zs2150Isup3.cml

checkCIF report

Comment top

Isatin (2,3-dioxindole) is an endogenous compound identified in humans, and its effect has been studied in a variety of systems (Vine et al., 2009). Biological properties of isatin and its derivatives include a range of actions in the brain and offer protection against certain types of infections, such as anti-bacterial (Suryavanshi & Pai, 2006) antifungal, anticonvulsant, anti-HIV (Pandeya et al.,1999), anti-depressant and anti-inflammatory activities (Bhandari et al., 2008). In this paper we describe the single-crystal X-ray diffraction study of the title compound, C₁₅H₁₁ClN₄OS.

In this compound (Fig. 1), the dihedral angle between the nine-membered 5-chloroindolin-2-one ring system and benzene ring is 10.00 (6)°. Atoms C8 in the 5-chloroindolin-2-one ring and C10 in the benzene ring are joined by a chain of four atoms (N2/N3/C9/N4) giving a torsion angle 7.47 (19)° while the the torsion angles C8—N2—N3—C9 and C10—N4—C9—N3 are 173.15 (13)° and -178.02 (13)°, respectively. The essentially planar conformation of the molecule is maintained by cyclic intramolecular N3—H···O1 and C11—H···S1 hydrogen-bonding interactions [graph set S(6) (Bernstein et al., 1995)] (Table 1) together with an S(5) N3—H···N2 interaction.

In the crystal the molecules form centrosymmetric cyclic dimers through intermolecular N—H···O hydrogen bonds [graph set R²₂(8)] and are extended by C—H···Cl interactions into infinite chains which propagate along [100] (Fig. 2). Weak C—H···π interactions are also present: C5—H5A···Cg3ⁱⁱⁱ = 3.6321 (18) Å, where Cg3ⁱⁱⁱ is the centroid of the C10—C15 ring [symmetry code: (iii) -x + 1, y + 1/2, -z + 3/2].

Related literature top

For related structures, see: Ferrari et al. (2002); Pervez et al. (2010); Ramzan et al. (2010). For various biological activities of Schiff bases, see: Bhandari et al. (2008); Bhardwaj et al. (2010); Pandeya et al. (1999); Sridhar et al. (2002); Suryavanshi & Pai (2006). For cytotoxic and anticancer activities of isatin and its derivatives, see: Vine et al. (2009). For bond-length data, see; Allen et al. (1987). For graph-set analysis, see Bernstein et al. (1995).

Experimental top

The Schiff base have been synthesized by refluxing the reaction mixture of hot ethanolic solution (30 ml) of 4-phenyl-3-thiosemicarbazide (0.01 mol) and hot ethanolic solution (30 ml) of 5-chloroisatin (0.01 mol) for 2 h. The precipitate formed during reflux was filtered, washed with cold ethanol and recrystallized from hot ethanol: yield 97%; m.p. 521.4-521.9 K). The orange crystals were grown in acetone-DMF (3:1) by slow evaporation at room temperature.

Structure description top

For related structures, see: Ferrari et al. (2002); Pervez et al. (2010); Ramzan et al. (2010). For various biological activities of Schiff bases, see: Bhandari et al. (2008); Bhardwaj et al. (2010); Pandeya et al. (1999); Sridhar et al. (2002); Suryavanshi & Pai (2006). For cytotoxic and anticancer activities of isatin and its derivatives, see: Vine et al. (2009). For bond-length data, see; Allen et al. (1987). For graph-set analysis, see Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound viewed down the a axis. Hydrogen bonds are shown as dashed lines.

(Z)-2-(5-Chloro-2-oxoindolin-3-ylidene)-N- phenylhydrazinecarbothioamide top

Crystal data top

C₁₅H₁₁ClN₄OS	F(000) = 680
M_r = 330.79	D_x = 1.505 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 521.3–521.9 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.7117 (2) Å	Cell parameters from 6388 reflections
b = 17.9510 (7) Å	θ = 2.3–29.8°
c = 14.2455 (5) Å	µ = 0.41 mm⁻¹
β = 91.262 (2)°	T = 100 K
V = 1460.25 (9) Å³	Block, orange
Z = 4	0.53 × 0.16 × 0.13 mm

Data collection top

Bruker APEXII CCD diffractometer	4183 independent reflections
Radiation source: fine-focus sealed tube	3424 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
φ and ω scans	θ_max = 29.9°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
T_min = 0.812, T_max = 0.950	k = −16→25
15819 measured reflections	l = −19→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0482P)² + 0.4941P] where P = (F_o² + 2F_c²)/3
4183 reflections	(Δ/σ)_max = 0.001
211 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₅H₁₁ClN₄OS	V = 1460.25 (9) Å³
M_r = 330.79	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.7117 (2) Å	µ = 0.41 mm⁻¹
b = 17.9510 (7) Å	T = 100 K
c = 14.2455 (5) Å	0.53 × 0.16 × 0.13 mm
β = 91.262 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4183 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3424 reflections with I > 2σ(I)
T_min = 0.812, T_max = 0.950	R_int = 0.044
15819 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.51 e Å⁻³
4183 reflections	Δρ_min = −0.23 e Å⁻³
211 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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
S1	0.08445 (7)	0.29509 (2)	0.51315 (3)	0.02175 (10)
Cl1	0.74643 (8)	0.58625 (3)	1.01336 (3)	0.03431 (13)
O1	0.71079 (18)	0.45044 (6)	0.51237 (8)	0.0202 (2)
N1	0.9178 (2)	0.52737 (7)	0.61568 (10)	0.0192 (3)
N2	0.3993 (2)	0.43359 (7)	0.68077 (9)	0.0169 (2)
N3	0.3263 (2)	0.39602 (7)	0.60374 (9)	0.0176 (2)
N4	0.0298 (2)	0.34863 (7)	0.69041 (9)	0.0162 (2)
C1	0.7024 (2)	0.51529 (8)	0.74926 (11)	0.0175 (3)
C2	0.6515 (3)	0.52627 (8)	0.84293 (11)	0.0202 (3)
H2A	0.5189	0.5055	0.8692	0.024*
C3	0.8066 (3)	0.56950 (9)	0.89592 (11)	0.0213 (3)
C4	1.0055 (3)	0.60157 (9)	0.85810 (12)	0.0226 (3)
H4A	1.1051	0.6301	0.8960	0.027*
C5	1.0559 (3)	0.59112 (9)	0.76381 (12)	0.0218 (3)
H5A	1.1876	0.6125	0.7376	0.026*
C6	0.9031 (2)	0.54775 (8)	0.71060 (11)	0.0177 (3)
C7	0.7407 (2)	0.48082 (8)	0.58967 (11)	0.0176 (3)
C8	0.5894 (2)	0.47276 (8)	0.67398 (10)	0.0164 (3)
C9	0.1396 (2)	0.34679 (8)	0.60775 (10)	0.0163 (3)
C10	−0.1615 (2)	0.30657 (8)	0.72387 (10)	0.0158 (3)
C11	−0.3209 (2)	0.26888 (8)	0.66549 (11)	0.0175 (3)
H11A	−0.3036	0.2690	0.6007	0.021*
C12	−0.5073 (3)	0.23099 (8)	0.70597 (12)	0.0205 (3)
H12A	−0.6127	0.2050	0.6675	0.025*
C13	−0.5381 (3)	0.23133 (9)	0.80179 (12)	0.0227 (3)
H13A	−0.6635	0.2061	0.8277	0.027*
C14	−0.3798 (3)	0.26976 (10)	0.85915 (12)	0.0248 (3)
H14A	−0.4001	0.2707	0.9237	0.030*
C15	−0.1915 (3)	0.30674 (9)	0.82049 (11)	0.0212 (3)
H15A	−0.0849	0.3318	0.8594	0.025*
H1N1	1.030 (4)	0.5395 (14)	0.5766 (17)	0.049 (7)*
H1N3	0.406 (4)	0.3978 (11)	0.5537 (15)	0.029 (5)*
H1N4	0.095 (3)	0.3761 (11)	0.7308 (14)	0.026 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02155 (19)	0.0258 (2)	0.01799 (19)	−0.00283 (14)	0.00246 (14)	−0.00359 (14)
Cl1	0.0431 (3)	0.0386 (3)	0.0214 (2)	−0.01947 (19)	0.00487 (17)	−0.00397 (16)
O1	0.0156 (5)	0.0242 (5)	0.0208 (5)	0.0009 (4)	0.0028 (4)	0.0007 (4)
N1	0.0136 (6)	0.0218 (6)	0.0225 (7)	−0.0018 (5)	0.0038 (5)	0.0018 (5)
N2	0.0141 (5)	0.0175 (6)	0.0192 (6)	0.0004 (4)	0.0003 (5)	0.0011 (5)
N3	0.0148 (6)	0.0202 (6)	0.0178 (6)	−0.0015 (4)	0.0032 (5)	0.0001 (5)
N4	0.0140 (5)	0.0193 (6)	0.0154 (6)	−0.0035 (4)	0.0003 (4)	−0.0013 (5)
C1	0.0140 (6)	0.0153 (6)	0.0233 (8)	−0.0001 (5)	0.0017 (5)	0.0022 (5)
C2	0.0174 (7)	0.0198 (7)	0.0235 (8)	−0.0035 (5)	0.0021 (6)	0.0023 (6)
C3	0.0231 (7)	0.0199 (7)	0.0209 (7)	−0.0022 (6)	0.0007 (6)	0.0009 (6)
C4	0.0200 (7)	0.0200 (7)	0.0277 (8)	−0.0032 (5)	−0.0023 (6)	0.0022 (6)
C5	0.0144 (6)	0.0222 (7)	0.0288 (8)	−0.0025 (5)	0.0025 (6)	0.0016 (6)
C6	0.0136 (6)	0.0166 (6)	0.0231 (7)	0.0017 (5)	0.0033 (5)	0.0026 (5)
C7	0.0126 (6)	0.0182 (7)	0.0221 (7)	0.0028 (5)	0.0027 (5)	0.0046 (5)
C8	0.0127 (6)	0.0179 (7)	0.0188 (7)	0.0010 (5)	0.0018 (5)	0.0026 (5)
C9	0.0132 (6)	0.0174 (6)	0.0183 (7)	0.0014 (5)	−0.0007 (5)	0.0023 (5)
C10	0.0118 (6)	0.0165 (6)	0.0192 (7)	0.0003 (5)	0.0002 (5)	0.0017 (5)
C11	0.0136 (6)	0.0188 (7)	0.0200 (7)	0.0008 (5)	−0.0017 (5)	−0.0002 (5)
C12	0.0136 (6)	0.0180 (7)	0.0298 (8)	−0.0002 (5)	−0.0025 (6)	0.0007 (6)
C13	0.0143 (6)	0.0245 (8)	0.0295 (9)	−0.0013 (5)	0.0026 (6)	0.0059 (6)
C14	0.0187 (7)	0.0364 (9)	0.0192 (8)	−0.0017 (6)	0.0023 (6)	0.0058 (7)
C15	0.0154 (7)	0.0301 (8)	0.0182 (7)	−0.0038 (6)	−0.0011 (5)	0.0005 (6)

Geometric parameters (Å, º) top

S1—C9	1.6606 (15)	C3—C4	1.392 (2)
Cl1—C3	1.7416 (17)	C4—C5	1.393 (2)
O1—C7	1.2374 (18)	C4—H4A	0.9300
N1—C7	1.3573 (19)	C5—C6	1.383 (2)
N1—C6	1.405 (2)	C5—H5A	0.9300
N1—H1N1	0.88 (3)	C7—C8	1.502 (2)
N2—C8	1.2992 (18)	C10—C15	1.391 (2)
N2—N3	1.3462 (18)	C10—C11	1.395 (2)
N3—C9	1.3872 (18)	C11—C12	1.398 (2)
N3—H1N3	0.85 (2)	C11—H11A	0.9300
N4—C9	1.3467 (19)	C12—C13	1.380 (2)
N4—C10	1.4190 (18)	C12—H12A	0.9300
N4—H1N4	0.84 (2)	C13—C14	1.389 (2)
C1—C2	1.386 (2)	C13—H13A	0.9300
C1—C6	1.409 (2)	C14—C15	1.388 (2)
C1—C8	1.456 (2)	C14—H14A	0.9300
C2—C3	1.389 (2)	C15—H15A	0.9300
C2—H2A	0.9300

C7—N1—C6	111.28 (13)	O1—C7—N1	126.99 (14)
C7—N1—H1N1	121.6 (16)	O1—C7—C8	126.77 (13)
C6—N1—H1N1	127.0 (16)	N1—C7—C8	106.23 (13)
C8—N2—N3	117.04 (13)	N2—C8—C1	125.93 (14)
N2—N3—C9	120.67 (13)	N2—C8—C7	127.47 (14)
N2—N3—H1N3	120.1 (14)	C1—C8—C7	106.56 (12)
C9—N3—H1N3	118.8 (14)	N4—C9—N3	113.18 (13)
C9—N4—C10	131.11 (13)	N4—C9—S1	129.76 (11)
C9—N4—H1N4	113.9 (14)	N3—C9—S1	117.06 (11)
C10—N4—H1N4	114.6 (14)	C15—C10—C11	119.87 (13)
C2—C1—C6	120.49 (14)	C15—C10—N4	116.35 (13)
C2—C1—C8	133.22 (13)	C11—C10—N4	123.73 (13)
C6—C1—C8	106.28 (13)	C10—C11—C12	118.89 (14)
C1—C2—C3	117.25 (14)	C10—C11—H11A	120.6
C1—C2—H2A	121.4	C12—C11—H11A	120.6
C3—C2—H2A	121.4	C13—C12—C11	121.37 (14)
C2—C3—C4	122.48 (15)	C13—C12—H12A	119.3
C2—C3—Cl1	118.78 (12)	C11—C12—H12A	119.3
C4—C3—Cl1	118.71 (12)	C12—C13—C14	119.25 (14)
C3—C4—C5	120.36 (15)	C12—C13—H13A	120.4
C3—C4—H4A	119.8	C14—C13—H13A	120.4
C5—C4—H4A	119.8	C15—C14—C13	120.28 (15)
C6—C5—C4	117.56 (14)	C15—C14—H14A	119.9
C6—C5—H5A	121.2	C13—C14—H14A	119.9
C4—C5—H5A	121.2	C14—C15—C10	120.34 (14)
C5—C6—N1	128.57 (14)	C14—C15—H15A	119.8
C5—C6—C1	121.85 (15)	C10—C15—H15A	119.8
N1—C6—C1	109.57 (13)

C8—N2—N3—C9	173.15 (13)	C6—C1—C8—N2	179.26 (14)
C6—C1—C2—C3	−0.6 (2)	C2—C1—C8—C7	−177.07 (15)
C8—C1—C2—C3	177.83 (15)	C6—C1—C8—C7	1.51 (15)
C1—C2—C3—C4	0.5 (2)	O1—C7—C8—N2	−1.1 (2)
C1—C2—C3—Cl1	178.76 (11)	N1—C7—C8—N2	179.62 (14)
C2—C3—C4—C5	0.1 (2)	O1—C7—C8—C1	176.64 (14)
Cl1—C3—C4—C5	−178.24 (12)	N1—C7—C8—C1	−2.68 (15)
C3—C4—C5—C6	−0.4 (2)	C10—N4—C9—N3	−178.02 (13)
C4—C5—C6—N1	−178.16 (14)	C10—N4—C9—S1	1.7 (2)
C4—C5—C6—C1	0.3 (2)	N2—N3—C9—N4	7.47 (19)
C7—N1—C6—C5	176.63 (15)	N2—N3—C9—S1	−172.31 (10)
C7—N1—C6—C1	−1.99 (16)	C9—N4—C10—C15	162.39 (15)
C2—C1—C6—C5	0.2 (2)	C9—N4—C10—C11	−20.3 (2)
C8—C1—C6—C5	−178.57 (13)	C15—C10—C11—C12	−0.8 (2)
C2—C1—C6—N1	178.95 (13)	N4—C10—C11—C12	−178.04 (13)
C8—C1—C6—N1	0.15 (15)	C10—C11—C12—C13	1.1 (2)
C6—N1—C7—O1	−176.46 (14)	C11—C12—C13—C14	−0.4 (2)
C6—N1—C7—C8	2.86 (16)	C12—C13—C14—C15	−0.6 (2)
N3—N2—C8—C1	−177.80 (13)	C13—C14—C15—C10	0.9 (2)
N3—N2—C8—C7	−0.5 (2)	C11—C10—C15—C14	−0.2 (2)
C2—C1—C8—N2	0.7 (3)	N4—C10—C15—C14	177.23 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.89 (2)	1.98 (2)	2.8560 (17)	171 (2)
N3—H1N3···O1	0.86 (2)	2.08 (2)	2.7563 (16)	135.9 (19)
N4—H1N4···N2	0.84 (2)	2.156 (18)	2.6099 (17)	113.8 (16)
C2—H2A···Cl1ⁱⁱ	0.93	2.81	3.6935 (17)	158
C11—H11A···S1	0.93	2.61	3.2423 (14)	126

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁ClN₄OS
M_r	330.79
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.7117 (2), 17.9510 (7), 14.2455 (5)
β (°)	91.262 (2)
V (Å³)	1460.25 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.53 × 0.16 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.812, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	15819, 4183, 3424
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.702

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.101, 1.04
No. of reflections	4183
No. of parameters	211
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.89 (2)	1.98 (2)	2.8560 (17)	171 (2)
N3—H1N3···O1	0.86 (2)	2.08 (2)	2.7563 (16)	135.9 (19)
C2—H2A···Cl1ⁱⁱ	0.93	2.81	3.6935 (17)	158
C11—H11A···S1	0.93	2.61	3.2423 (14)	126

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: E-9395-2011

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the RU research grant (1001/PKIMIA/815067). NEE thanks Universiti Sains Malaysia for a post-doctoral fellowship and the International University of Africa (Sudan) for providing research leave. AQA thanks the Ministry of Higher Education and the University of Sabha (Libya) for a scholarship.

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