(Z)-2-(2-Oxoindolin-3-yl­idene)-N-phenylhydrazinecarbothio­amide

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

doi:10.1107/S160053681200400X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o962-o963

doi:10.1107/S160053681200400X

Open

access

(Z)-2-(2-Oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide

Amna Qasem Ali,^a,^b Naser Eltaher Eltayeb,^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, Sudan, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: sgteoh@usm.my

(Received 11 January 2012; accepted 30 January 2012; online 7 March 2012)

In the title compound, C₁₅H₁₂N₄OS, the dihedral angle between the nine-membered indolin-2-one ring system and the phenyl ring is 2.72 (7)°. Intramolecular cyclic N—H⋯O and C—H⋯S hydrogen-bonding interactions [graph set S(6)] are present, as are weak N—H⋯N interactions [graph set S(5)]. In the crystal, molecules form centrosymmetric cyclic dimers through pairs of N—H⋯O hydrogen bonds [graph set R₂²(8)] and these are extended by C—H⋯S interactions. The crystal structure also features weak C—H⋯π interactions.

Related literature

For related crystal structures, see: Ali et al. (2012 ); Qasem Ali et al. (2011a ,b ); 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 the cytotoxic and anticancer activities of isatin and its derivatives, see: Vine et al. (2009 ). For graph-set analysis, see Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₂N₄OS
M_r = 296.35
Monoclinic, P 21/c
a = 6.3674 (1) Å
b = 15.4594 (3) Å
c = 14.2199 (3) Å
β = 93.383 (1)°
V = 1397.31 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 100 K
0.47 × 0.13 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.897, T_max = 0.971
15557 measured reflections
4159 independent reflections
2985 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.113
S = 1.02
4159 reflections
202 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring and Cg3 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.88 (2)	2.00 (2)	2.8737 (18)	173.9 (18)
N3—H1N3⋯O1	0.87 (2)	2.07 (2)	2.7646 (18)	136 (2)
N4—H1N4⋯N2	0.88 (2)	2.05 (2)	2.5781 (19)	117.4 (17)
C11—H11A⋯S1ⁱⁱ	0.95	2.83	3.6017 (19)	139
C15—H15A⋯S1	0.95	2.60	3.2735 (19)	128
C2—H2A⋯Cg3ⁱⁱⁱ	0.95	2.80	3.510 (2)	132
C13—H13A⋯Cg2^iv	0.95	2.82	3.5201 (19)	131
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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: 10.1107/S160053681200400X/wn2464sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200400X/wn2464Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681200400X/wn2464Isup3.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. The biological properties of isatin and its derivatives include a range of actions in the brain, offer protection against bacterial (Suryavanshi & Pai, 2006) and fungal infections and possess anticonvulsant, anti-HIV (Pandeya et al., 1999), antidepressant and anti-inflammatory activities (Bhandari et al., 2008). Recently, we reported the crystal structure of (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide (Qasem Ali et al., 2011a). In the present paper we describe the single-crystal X-ray diffraction study of the title compound (Fig. 1).

In the title compound, C₁₅H₁₂N₄OS, the dihedral angle between the nine-membered indolin-2-one ring system and the phenyl ring is 2.72 (7)°. These two ring systems are connected by a chain of four atoms N2—N3—C9—N4; this torsion angle is 4.1 (2)°. The torsion angles C7—N2—N3—C9 and C10—N4—C9—N3 are 173.69 (15)° and 174.00 (16)°, respectively. These values are very close to those in a similar structure (Qasem Ali et al., 2011a).

The essentially planar conformation of the molecule is maintained by cyclic intramolecular N3—H1N3···O1 and C15—H15A···S1 hydrogen-bonding interactions [graph set S(6) (Bernstein et al., 1995)] (Table 1), together with a weak S(5) N4—H1N4···N2 interaction.

In the crystal structure, the molecules form centrosymmetric cyclic dimers through intermolecular N1—H1N1···O1 hydrogen bonds [graph set R²₂(8)] and are extended by C11—H11A···S1 hydrogen bond interactions.

The crystal structure (Fig. 2) is stabilized by weak C—H···π interactions (Table 1) involving the C10–C15 ring (centroid Cg3) and C1–C6 ring (centroid Cg2).

Related literature top

For related crystal structures, see: Ali et al. (2012); Qasem Ali et al. (2011a,b); 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 the cytotoxic and anticancer activities of isatin and its derivatives, see: Vine et al. (2009). For graph-set analysis, see Bernstein et al. (1995).

Experimental top

The Schiff base has been synthesized by refluxing the reaction mixture of a hot ethanolic solution (30 ml) of 4-phenyl-3-thiosemicarbazide (0.01 mol) and a hot ethanolic solution (30 ml) of isatin (0.01 mol) for 2 h. The precipitate formed during reflux was filtered, washed with cold EtOH and recrystallized from hot EtOH. Yield (m.p.): 90% (510.2–511.6 K). The yellow crystals were grown in acetone–dimethylformamide (3:1) by slow evaporation at room temperature.

Structure description top

The crystal structure (Fig. 2) is stabilized by weak C—H···π interactions (Table 1) involving the C10–C15 ring (centroid Cg3) and C1–C6 ring (centroid Cg2).

For related crystal structures, see: Ali et al. (2012); Qasem Ali et al. (2011a,b); 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 the cytotoxic and anticancer activities of isatin and its derivatives, see: Vine et al. (2009). 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. Dashed lines indicate hydrogen bonds.
	Fig. 2. The crystal packing of the title compound, viewed down the a axis. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.

(Z)-2-(2-Oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide top

Crystal data top

C₁₅H₁₂N₄OS	F(000) = 616
M_r = 296.35	D_x = 1.409 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 510.2–511.6 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.3674 (1) Å	Cell parameters from 4743 reflections
b = 15.4594 (3) Å	θ = 3.0–30.1°
c = 14.2199 (3) Å	µ = 0.24 mm⁻¹
β = 93.383 (1)°	T = 100 K
V = 1397.31 (5) Å³	Needle, yellow
Z = 4	0.47 × 0.13 × 0.13 mm

Data collection top

Bruker APEXII CCD diffractometer	4159 independent reflections
Radiation source: fine-focus sealed tube	2985 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 30.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→8
T_min = 0.897, T_max = 0.971	k = −21→18
15557 measured reflections	l = −17→20

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.038P)² + 0.7736P] where P = (F_o² + 2F_c²)/3
4159 reflections	(Δ/σ)_max = 0.001
202 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₅H₁₂N₄OS	V = 1397.31 (5) Å³
M_r = 296.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.3674 (1) Å	µ = 0.24 mm⁻¹
b = 15.4594 (3) Å	T = 100 K
c = 14.2199 (3) Å	0.47 × 0.13 × 0.13 mm
β = 93.383 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4159 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2985 reflections with I > 2σ(I)
T_min = 0.897, T_max = 0.971	R_int = 0.040
15557 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.34 e Å⁻³
4159 reflections	Δρ_min = −0.49 e Å⁻³
202 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	0.15701 (8)	0.72368 (4)	1.06040 (3)	0.03145 (15)
O1	0.73491 (19)	0.55698 (8)	1.00760 (8)	0.0228 (3)
N1	0.9075 (2)	0.50533 (10)	0.87950 (10)	0.0208 (3)
N2	0.4169 (2)	0.61290 (9)	0.85318 (10)	0.0177 (3)
N3	0.3689 (2)	0.63773 (9)	0.94027 (10)	0.0191 (3)
N4	0.0843 (2)	0.70518 (9)	0.87089 (10)	0.0181 (3)
C1	0.8690 (3)	0.50379 (11)	0.78102 (12)	0.0195 (4)
C2	0.9950 (3)	0.47108 (12)	0.71370 (13)	0.0241 (4)
H2A	1.1264	0.4445	0.7306	0.029*
C3	0.9210 (3)	0.47880 (12)	0.61995 (13)	0.0253 (4)
H3A	1.0027	0.4560	0.5719	0.030*
C4	0.7296 (3)	0.51916 (12)	0.59478 (13)	0.0231 (4)
H4A	0.6846	0.5243	0.5301	0.028*
C5	0.6042 (3)	0.55185 (11)	0.66319 (12)	0.0206 (4)
H5A	0.4741	0.5794	0.6462	0.025*
C6	0.6740 (3)	0.54324 (11)	0.75712 (12)	0.0184 (4)
C7	0.5904 (3)	0.57114 (11)	0.84497 (12)	0.0176 (3)
C8	0.7491 (3)	0.54476 (11)	0.92218 (12)	0.0188 (4)
C9	0.1964 (3)	0.68962 (11)	0.95214 (12)	0.0185 (4)
C10	−0.1096 (3)	0.74787 (11)	0.85012 (12)	0.0168 (3)
C11	−0.1753 (3)	0.74938 (11)	0.75467 (12)	0.0190 (4)
H11A	−0.0892	0.7245	0.7095	0.023*
C12	−0.3656 (3)	0.78705 (11)	0.72568 (13)	0.0237 (4)
H12A	−0.4098	0.7878	0.6607	0.028*
C13	−0.4917 (3)	0.82369 (11)	0.79112 (13)	0.0247 (4)
H13A	−0.6228	0.8492	0.7714	0.030*
C14	−0.4248 (3)	0.82279 (11)	0.88559 (13)	0.0229 (4)
H14A	−0.5106	0.8486	0.9303	0.027*
C15	−0.2349 (3)	0.78504 (11)	0.91642 (12)	0.0196 (4)
H15A	−0.1912	0.7846	0.9815	0.024*
H1N1	1.018 (3)	0.4836 (14)	0.9106 (15)	0.037 (6)*
H1N3	0.457 (4)	0.6258 (14)	0.9879 (16)	0.039 (6)*
H1N4	0.144 (3)	0.6806 (14)	0.8234 (15)	0.029 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0267 (2)	0.0507 (3)	0.0168 (2)	0.0076 (2)	0.00014 (18)	−0.0045 (2)
O1	0.0242 (6)	0.0248 (7)	0.0189 (6)	0.0016 (5)	−0.0032 (5)	0.0026 (5)
N1	0.0191 (7)	0.0199 (8)	0.0228 (8)	0.0043 (6)	−0.0032 (6)	0.0020 (6)
N2	0.0189 (7)	0.0153 (7)	0.0187 (7)	−0.0008 (6)	0.0001 (5)	0.0008 (6)
N3	0.0184 (7)	0.0216 (8)	0.0171 (7)	0.0022 (6)	−0.0011 (6)	0.0020 (6)
N4	0.0184 (7)	0.0193 (8)	0.0166 (7)	0.0032 (6)	0.0014 (6)	0.0000 (6)
C1	0.0195 (8)	0.0131 (8)	0.0254 (9)	0.0000 (7)	−0.0025 (7)	0.0014 (7)
C2	0.0211 (9)	0.0197 (9)	0.0315 (10)	0.0045 (7)	0.0006 (8)	0.0030 (8)
C3	0.0265 (9)	0.0231 (9)	0.0268 (9)	0.0049 (8)	0.0064 (8)	0.0016 (8)
C4	0.0248 (9)	0.0220 (9)	0.0225 (9)	0.0017 (7)	0.0004 (7)	0.0018 (7)
C5	0.0187 (8)	0.0181 (9)	0.0248 (9)	0.0010 (7)	−0.0016 (7)	0.0016 (7)
C6	0.0190 (8)	0.0140 (8)	0.0220 (8)	0.0005 (7)	−0.0007 (7)	0.0009 (7)
C7	0.0183 (8)	0.0127 (8)	0.0213 (8)	−0.0015 (6)	−0.0020 (7)	0.0023 (6)
C8	0.0187 (8)	0.0120 (8)	0.0254 (9)	−0.0013 (7)	−0.0021 (7)	0.0031 (7)
C9	0.0173 (8)	0.0186 (8)	0.0195 (8)	−0.0036 (7)	0.0016 (6)	0.0035 (7)
C10	0.0164 (8)	0.0136 (8)	0.0205 (8)	−0.0016 (6)	0.0017 (6)	0.0014 (6)
C11	0.0198 (8)	0.0179 (8)	0.0194 (8)	0.0002 (7)	0.0023 (7)	0.0013 (7)
C12	0.0243 (9)	0.0204 (9)	0.0257 (9)	−0.0013 (7)	−0.0043 (7)	0.0044 (7)
C13	0.0187 (8)	0.0167 (9)	0.0383 (11)	0.0006 (7)	−0.0014 (8)	0.0044 (8)
C14	0.0201 (8)	0.0153 (8)	0.0339 (10)	0.0008 (7)	0.0066 (7)	−0.0026 (8)
C15	0.0214 (8)	0.0165 (8)	0.0211 (8)	−0.0007 (7)	0.0024 (7)	−0.0021 (7)

Geometric parameters (Å, º) top

S1—C9	1.6600 (18)	C4—C5	1.389 (3)
O1—C8	1.238 (2)	C4—H4A	0.9500
N1—C8	1.352 (2)	C5—C6	1.389 (2)
N1—C1	1.408 (2)	C5—H5A	0.9500
N1—H1N1	0.88 (2)	C6—C7	1.452 (2)
N2—C7	1.291 (2)	C7—C8	1.504 (2)
N2—N3	1.349 (2)	C10—C15	1.394 (2)
N3—C9	1.378 (2)	C10—C11	1.397 (2)
N3—H1N3	0.87 (2)	C11—C12	1.385 (2)
N4—C9	1.343 (2)	C11—H11A	0.9500
N4—C10	1.416 (2)	C12—C13	1.386 (3)
N4—H1N4	0.88 (2)	C12—H12A	0.9500
C1—C2	1.381 (3)	C13—C14	1.385 (3)
C1—C6	1.407 (2)	C13—H13A	0.9500
C2—C3	1.393 (3)	C14—C15	1.390 (2)
C2—H2A	0.9500	C14—H14A	0.9500
C3—C4	1.397 (2)	C15—H15A	0.9500
C3—H3A	0.9500

C8—N1—C1	111.31 (14)	N2—C7—C6	125.83 (15)
C8—N1—H1N1	123.0 (14)	N2—C7—C8	127.70 (16)
C1—N1—H1N1	125.7 (14)	C6—C7—C8	106.43 (14)
C7—N2—N3	117.83 (14)	O1—C8—N1	127.51 (15)
N2—N3—C9	120.23 (14)	O1—C8—C7	126.16 (16)
N2—N3—H1N3	118.7 (15)	N1—C8—C7	106.34 (15)
C9—N3—H1N3	120.6 (15)	N4—C9—N3	112.68 (15)
C9—N4—C10	132.49 (16)	N4—C9—S1	129.71 (14)
C9—N4—H1N4	110.5 (13)	N3—C9—S1	117.61 (12)
C10—N4—H1N4	116.9 (13)	C15—C10—C11	119.98 (15)
C2—C1—C6	122.14 (16)	C15—C10—N4	125.29 (15)
C2—C1—N1	128.43 (15)	C11—C10—N4	114.71 (15)
C6—C1—N1	109.42 (15)	C12—C11—C10	120.19 (17)
C1—C2—C3	117.03 (16)	C12—C11—H11A	119.9
C1—C2—H2A	121.5	C10—C11—H11A	119.9
C3—C2—H2A	121.5	C11—C12—C13	120.24 (16)
C2—C3—C4	121.63 (18)	C11—C12—H12A	119.9
C2—C3—H3A	119.2	C13—C12—H12A	119.9
C4—C3—H3A	119.2	C14—C13—C12	119.32 (16)
C5—C4—C3	120.78 (16)	C14—C13—H13A	120.3
C5—C4—H4A	119.6	C12—C13—H13A	120.3
C3—C4—H4A	119.6	C13—C14—C15	121.48 (17)
C6—C5—C4	118.29 (16)	C13—C14—H14A	119.3
C6—C5—H5A	120.9	C15—C14—H14A	119.3
C4—C5—H5A	120.9	C14—C15—C10	118.79 (16)
C5—C6—C1	120.11 (17)	C14—C15—H15A	120.6
C5—C6—C7	133.33 (16)	C10—C15—H15A	120.6
C1—C6—C7	106.50 (14)

C7—N2—N3—C9	173.69 (15)	C1—N1—C8—O1	−179.73 (17)
C8—N1—C1—C2	178.50 (18)	C1—N1—C8—C7	0.46 (18)
C8—N1—C1—C6	−0.7 (2)	N2—C7—C8—O1	2.3 (3)
C6—C1—C2—C3	0.1 (3)	C6—C7—C8—O1	−179.84 (16)
N1—C1—C2—C3	−179.09 (17)	N2—C7—C8—N1	−177.88 (17)
C1—C2—C3—C4	1.1 (3)	C6—C7—C8—N1	−0.03 (18)
C2—C3—C4—C5	−1.1 (3)	C10—N4—C9—N3	174.00 (16)
C3—C4—C5—C6	−0.1 (3)	C10—N4—C9—S1	−6.4 (3)
C4—C5—C6—C1	1.2 (3)	N2—N3—C9—N4	4.1 (2)
C4—C5—C6—C7	177.76 (18)	N2—N3—C9—S1	−175.54 (12)
C2—C1—C6—C5	−1.3 (3)	C9—N4—C10—C15	−0.6 (3)
N1—C1—C6—C5	178.05 (15)	C9—N4—C10—C11	−179.21 (17)
C2—C1—C6—C7	−178.61 (16)	C15—C10—C11—C12	−0.6 (3)
N1—C1—C6—C7	0.69 (19)	N4—C10—C11—C12	178.11 (15)
N3—N2—C7—C6	−176.52 (15)	C10—C11—C12—C13	0.2 (3)
N3—N2—C7—C8	0.9 (3)	C11—C12—C13—C14	0.5 (3)
C5—C6—C7—N2	0.6 (3)	C12—C13—C14—C15	−0.8 (3)
C1—C6—C7—N2	177.50 (16)	C13—C14—C15—C10	0.4 (3)
C5—C6—C7—C8	−177.26 (19)	C11—C10—C15—C14	0.3 (2)
C1—C6—C7—C8	−0.40 (18)	N4—C10—C15—C14	−178.24 (16)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 ring and Cg3 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.88 (2)	2.00 (2)	2.8737 (18)	173.9 (18)
N3—H1N3···O1	0.87 (2)	2.07 (2)	2.7646 (18)	136 (2)
N4—H1N4···N2	0.88 (2)	2.05 (2)	2.5781 (19)	117.4 (17)
C11—H11A···S1ⁱⁱ	0.95	2.83	3.6017 (19)	139
C15—H15A···S1	0.95	2.60	3.2735 (19)	128
C2—H2A···Cg3ⁱⁱⁱ	0.95	2.80	3.510 (2)	132
C13—H13A···Cg2^iv	0.95	2.82	3.5201 (19)	131

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x, −y+3/2, z−1/2; (iii) −x+1, y−1/2, −z+3/2; (iv) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₄OS
M_r	296.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	6.3674 (1), 15.4594 (3), 14.2199 (3)
β (°)	93.383 (1)
V (Å³)	1397.31 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.47 × 0.13 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.897, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	15557, 4159, 2985
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.709

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.113, 1.02
No. of reflections	4159
No. of parameters	202
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.49

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

Cg2 is the centroid of the C1–C6 ring and Cg3 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.88 (2)	2.00 (2)	2.8737 (18)	173.9 (18)
N3—H1N3···O1	0.87 (2)	2.07 (2)	2.7646 (18)	136 (2)
N4—H1N4···N2	0.88 (2)	2.05 (2)	2.5781 (19)	117.4 (17)
C11—H11A···S1ⁱⁱ	0.9500	2.8300	3.6017 (19)	139.00
C15—H15A···S1	0.9500	2.6000	3.2735 (19)	128.00
C2—H2A···Cg3ⁱⁱⁱ	0.9500	2.8000	3.510 (2)	132.00
C13—H13A···Cg2^iv	0.9500	2.8200	3.5201 (19)	131.00

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x, −y+3/2, z−1/2; (iii) −x+1, y−1/2, −z+3/2; (iv) −x, y+1/2, −z+3/2.

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 a Research University grant (No. 1001/PKIMIA/815067). AQA thanks the Ministry of Higher Education and the University of Sabha (Libya) for a scholarship.

References

Ali, A. Q., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2012). Acta Cryst. E68, o285–o286. Web of Science CSD CrossRef IUCr Journals Google Scholar
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
Bhandari, S. V., Bothara, K. G., Raut, M. K., Patil, A. A., Sarkate, A. P. & Mokale, V. J. (2008). Bioorg. Med. Chem. 16, 1822–1831. Web of Science CrossRef PubMed CAS Google Scholar
Bhardwaj, S., Kumar, L., Verma, R. & Sing, U. K. (2010). J. Pharm. Res. 3, 2983–2985. CAS Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ferrari, M. B., Pelizzi, C., Pelosi, G. & Rodriguez-Argüelles, M. C. (2002). Polyhedron, 21, 2593–2599. Web of Science CSD CrossRef CAS Google Scholar
Pandeya, S. N., Sriram, D., Nath, G. & Clercq, E. De. (1999). Indian J. Pharm. Sci. 61, 358–361. Google Scholar
Pervez, H., Yaqub, M., Ramzan, M., Tahir, M. N. & Iqbal, M. S. (2010). Acta Cryst. E66, o1609. Web of Science CSD CrossRef IUCr Journals Google Scholar
Qasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2011a). Acta Cryst. E67, o3141–o3142. Web of Science CSD CrossRef IUCr Journals Google Scholar
Qasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2011b). Acta Cryst. E67, o3476–o3477. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ramzan, M., Pervez, H., Yaqub, M. & Tahir, M. N. (2010). Acta Cryst. E66, o2387. 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
Sridhar, S. K., Pandeya, S. N., Stables, J. P. & Ramesh, A. (2002). Eur. J. Pharm. Sci. 16, 129–132. Web of Science CrossRef PubMed CAS Google Scholar
Suryavanshi, J. P. & Pai, N. R. (2006). Indian J. Chem. Sect. B, 45, 1227–1230. Google Scholar
Vine, K. L., Matesic, L., Locke, J. M., Ranson, M. & Skropeta, D. (2009). Anticancer Agents Med. Chem. 9, 397–414. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o962-o963

doi:10.1107/S160053681200400X

Open

access