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

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

doi:10.1107/S1600536812007386

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o964-o965

doi:10.1107/S1600536812007386

Open

access

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

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, Khartoum, Sudan, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: sgteoh@usm.my

(Received 18 January 2012; accepted 18 February 2012; online 7 March 2012)

In the title compound, C₁₀H₉ClN₄OS, an intramolecular N—H⋯O hydrogen-bonding interaction and an N—H⋯N interaction generate ring motifs [graph sets S(6) and S(5), respectively]. In the crystal, molecules form a chain through N—H⋯O hydrogen bonds, and these are extended by N—H⋯S hydrogen-bonding interactions into an infinite three-dimensional network. The crystal structure also exhibits weak C—H⋯π interactions.

Related literature

For related structures, see: Qasem Ali et al. (2012 , 2011a ,b ); Ali et al. (2012 ). 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 graph-set analysis, see Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₀H₉ClN₄OS
M_r = 268.72
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.2558 (1) Å
b = 10.1449 (1) Å
c = 18.5682 (2) Å
V = 1178.42 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 100 K
0.34 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.853, T_max = 0.961
16807 measured reflections
4886 independent reflections
4072 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.078
S = 1.05
4886 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ), 2074 Friedel pairs
Flack parameter: 0.01 (5)

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H1N4⋯N2	0.88 (2)	2.27 (2)	2.6416 (18)	105.6 (15)
N4—H1N4⋯S1ⁱ	0.88 (2)	2.70 (2)	3.4972 (13)	152.2 (16)
N3—H1N3⋯O1	0.86 (2)	2.086 (19)	2.7526 (16)	134.3 (17)
N1—H1N1⋯O1ⁱⁱ	0.81 (2)	2.01 (2)	2.8161 (16)	175 (2)
C3—H3A⋯Cg2ⁱⁱⁱ	0.95	2.59	3.38	141
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ .

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: 10.1107/S1600536812007386/zs2177sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007386/zs2177Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007386/zs2177Isup3.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. 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), anti-depressant and anti-inflammatory activities (Bhandari et al., 2008). Recently, we reported the crystal structure of (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)-N-methylhydrazinecarbothioamide (Qasem Ali et al., 2012). In the present paper we describe the single-crystal X-ray diffraction study of title compound, C₁₀H₉ClN₄OS (Fig. 1).

In this compound, the chain N2/N3/C9/S1/N4/C10 is connected to the nine-membered 5-chloroindolin-2-one ring system at C7. In this chain C7—N2—N3—C9 and C10—N4—C9—S1 torsion angles are -177.77 (13)° and 2.7 (2)°, respectively. The essentially planar conformation of the molecule is maintained by the cyclic intramolecular N3—H1N3···O1 hydrogen-bonding interaction together with the N4—H1N4···N2 interaction [graph sets S(6) and S(5), respectively (Bernstein et al., 1995)] (Table 1).

In the crystal the molecules form chain substructures through intermolecular N1—H1N1···O1 hydrogen bonds and these are extended by N4—H1N4···S1 hydrogen-bonding interactions into an infinite a three-dimensional network (Table 1, Fig. 2). Weak C—H···π interactions are also present [C3—H···Cg2ⁱⁱⁱ = 3.38 Å], where Cg2 is the centroid of the C1—C6 ring. For symmetry code (iii), see Table 1.

Related literature top

For related structures, see: Qasem Ali et al. (2012, 2011a,b); Ali et al. (2012). 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 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 5-methyl-3-thiosemicarbazide (0.01 mol) and a hot ethanolic solution (30 ml) of 5-chloroisatin (0.01 mol) for 2 hr. The precipitate formed during reflux was filtered, washed with cold ethanol and recrystallized from hot ethanol. Yield (m.p.): 85% (568.4–569.0 K). The yellow crystals were grown in ethylacetate–DMF (3:1) by slow evaporation at room temperature.

Structure description top

For related structures, see: Qasem Ali et al. (2012, 2011a,b); Ali et al. (2012). 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 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 and the atom-numbering scheme of the title compound, with 50% probability displacement ellipsoids.
	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- methylhydrazinecarbothioamide top

Crystal data top

C₁₀H₉ClN₄OS	D_x = 1.515 Mg m⁻³
M_r = 268.72	Melting point = 568.4–569.0 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5715 reflections
a = 6.2558 (1) Å	θ = 3.0–34.1°
b = 10.1449 (1) Å	µ = 0.49 mm⁻¹
c = 18.5682 (2) Å	T = 100 K
V = 1178.42 (3) Å³	Needle, yellow
Z = 4	0.34 × 0.10 × 0.08 mm
F(000) = 552

Data collection top

Bruker APEXII CCD diffractometer	4886 independent reflections
Radiation source: fine-focus sealed tube	4072 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
φ and ω scans	θ_max = 34.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→9
T_min = 0.853, T_max = 0.961	k = −16→16
16807 measured reflections	l = −29→29

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0318P)² + 0.1624P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4886 reflections	Δρ_max = 0.41 e Å⁻³
167 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2074 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (5)

Crystal data top

C₁₀H₉ClN₄OS	V = 1178.42 (3) Å³
M_r = 268.72	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.2558 (1) Å	µ = 0.49 mm⁻¹
b = 10.1449 (1) Å	T = 100 K
c = 18.5682 (2) Å	0.34 × 0.10 × 0.08 mm

Data collection top

Bruker APEXII CCD diffractometer	4886 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4072 reflections with I > 2σ(I)
T_min = 0.853, T_max = 0.961	R_int = 0.037
16807 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.078	Δρ_max = 0.41 e Å⁻³
S = 1.05	Δρ_min = −0.32 e Å⁻³
4886 reflections	Absolute structure: Flack (1983), 2074 Friedel pairs
167 parameters	Absolute structure parameter: 0.01 (5)
0 restraints

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
Cl1	−0.30754 (7)	0.94253 (3)	0.877263 (19)	0.02071 (9)
S1	0.74171 (6)	0.27814 (3)	0.785567 (19)	0.01723 (8)
O1	0.15801 (18)	0.26544 (10)	0.93453 (5)	0.0176 (2)
N1	−0.1313 (2)	0.39745 (12)	0.96526 (6)	0.0154 (3)
N2	0.2697 (2)	0.50267 (11)	0.84352 (6)	0.0131 (2)
N3	0.4038 (2)	0.39983 (12)	0.83590 (6)	0.0144 (2)
N4	0.6135 (2)	0.52656 (12)	0.76196 (7)	0.0147 (2)
C1	−0.2019 (3)	0.52525 (13)	0.94808 (7)	0.0138 (3)
C2	−0.3841 (3)	0.58915 (15)	0.97154 (7)	0.0160 (3)
H2A	−0.4830	0.5474	1.0029	0.019*
C3	−0.4167 (2)	0.71814 (15)	0.94706 (7)	0.0163 (3)
H3A	−0.5411	0.7650	0.9613	0.020*
C4	−0.2680 (3)	0.77827 (13)	0.90194 (7)	0.0148 (3)
C5	−0.0871 (2)	0.71336 (14)	0.87730 (7)	0.0139 (3)
H5A	0.0114	0.7551	0.8458	0.017*
C6	−0.0562 (2)	0.58458 (14)	0.90075 (7)	0.0124 (3)
C7	0.1086 (2)	0.48782 (13)	0.88630 (7)	0.0127 (3)
C8	0.0532 (3)	0.36840 (14)	0.93058 (7)	0.0139 (3)
C9	0.5824 (2)	0.41081 (13)	0.79306 (7)	0.0127 (3)
C10	0.7903 (3)	0.55324 (15)	0.71346 (8)	0.0201 (3)
H10A	0.8041	0.6486	0.7065	0.030*
H10B	0.7634	0.5107	0.6670	0.030*
H10C	0.9228	0.5184	0.7342	0.030*
H1N4	0.516 (4)	0.588 (2)	0.7671 (10)	0.033 (6)*
H1N3	0.383 (3)	0.328 (2)	0.8590 (10)	0.032 (6)*
H1N1	−0.189 (4)	0.3462 (19)	0.9928 (11)	0.035 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0223 (2)	0.01646 (14)	0.02338 (15)	0.00725 (15)	−0.00058 (16)	0.00258 (13)
S1	0.01584 (18)	0.01392 (14)	0.02193 (15)	0.00320 (15)	0.00197 (16)	−0.00174 (13)
O1	0.0214 (6)	0.0140 (4)	0.0174 (4)	0.0042 (5)	−0.0002 (4)	0.0032 (4)
N1	0.0183 (7)	0.0138 (5)	0.0141 (5)	−0.0012 (5)	0.0033 (5)	0.0017 (4)
N2	0.0134 (6)	0.0118 (4)	0.0140 (5)	0.0016 (5)	−0.0007 (5)	−0.0013 (4)
N3	0.0150 (7)	0.0122 (5)	0.0161 (5)	0.0026 (5)	0.0026 (5)	0.0008 (4)
N4	0.0129 (6)	0.0138 (5)	0.0175 (5)	0.0005 (5)	0.0018 (5)	0.0017 (4)
C1	0.0155 (7)	0.0135 (5)	0.0123 (5)	−0.0014 (5)	−0.0011 (6)	−0.0011 (4)
C2	0.0145 (7)	0.0189 (6)	0.0148 (6)	−0.0014 (6)	0.0018 (6)	−0.0014 (5)
C3	0.0130 (7)	0.0201 (6)	0.0159 (6)	0.0021 (6)	−0.0002 (6)	−0.0040 (5)
C4	0.0157 (7)	0.0142 (5)	0.0146 (5)	0.0022 (6)	−0.0034 (6)	−0.0002 (5)
C5	0.0144 (7)	0.0146 (5)	0.0128 (5)	0.0000 (6)	0.0003 (6)	0.0013 (5)
C6	0.0119 (7)	0.0145 (6)	0.0108 (5)	−0.0006 (5)	−0.0009 (5)	−0.0003 (4)
C7	0.0142 (7)	0.0109 (5)	0.0129 (6)	0.0000 (5)	−0.0013 (5)	0.0010 (4)
C8	0.0168 (7)	0.0135 (6)	0.0113 (5)	−0.0019 (6)	−0.0007 (6)	0.0010 (4)
C9	0.0115 (7)	0.0129 (5)	0.0136 (6)	0.0000 (5)	−0.0023 (5)	−0.0026 (5)
C10	0.0162 (8)	0.0229 (7)	0.0211 (6)	−0.0025 (6)	0.0021 (6)	0.0042 (6)

Geometric parameters (Å, º) top

Cl1—C4	1.7458 (14)	C1—C6	1.402 (2)
S1—C9	1.6806 (14)	C2—C3	1.400 (2)
O1—C8	1.2354 (18)	C2—H2A	0.9500
N1—C8	1.355 (2)	C3—C4	1.392 (2)
N1—C1	1.4062 (18)	C3—H3A	0.9500
N1—H1N1	0.81 (2)	C4—C5	1.387 (2)
N2—C7	1.292 (2)	C5—C6	1.3906 (19)
N2—N3	1.3463 (17)	C5—H5A	0.9500
N3—C9	1.376 (2)	C6—C7	1.449 (2)
N3—H1N3	0.86 (2)	C7—C8	1.5044 (19)
N4—C9	1.3229 (18)	C10—H10A	0.9800
N4—C10	1.4520 (19)	C10—H10B	0.9800
N4—H1N4	0.88 (2)	C10—H10C	0.9800
C1—C2	1.382 (2)

C8—N1—C1	111.11 (12)	C4—C5—C6	117.14 (13)
C8—N1—H1N1	122.4 (16)	C4—C5—H5A	121.4
C1—N1—H1N1	126.4 (16)	C6—C5—H5A	121.4
C7—N2—N3	117.41 (11)	C5—C6—C1	120.62 (14)
N2—N3—C9	120.27 (12)	C5—C6—C7	132.66 (13)
N2—N3—H1N3	121.0 (14)	C1—C6—C7	106.73 (12)
C9—N3—H1N3	118.7 (14)	N2—C7—C6	126.15 (12)
C9—N4—C10	123.25 (13)	N2—C7—C8	127.55 (13)
C9—N4—H1N4	119.0 (14)	C6—C7—C8	106.30 (12)
C10—N4—H1N4	117.5 (14)	O1—C8—N1	127.44 (13)
C2—C1—C6	122.18 (13)	O1—C8—C7	126.25 (14)
C2—C1—N1	128.31 (14)	N1—C8—C7	106.31 (12)
C6—C1—N1	109.52 (13)	N4—C9—N3	116.33 (13)
C1—C2—C3	117.14 (14)	N4—C9—S1	125.98 (12)
C1—C2—H2A	121.4	N3—C9—S1	117.69 (10)
C3—C2—H2A	121.4	N4—C10—H10A	109.5
C4—C3—C2	120.50 (14)	N4—C10—H10B	109.5
C4—C3—H3A	119.7	H10A—C10—H10B	109.5
C2—C3—H3A	119.7	N4—C10—H10C	109.5
C5—C4—C3	122.37 (13)	H10A—C10—H10C	109.5
C5—C4—Cl1	118.82 (11)	H10B—C10—H10C	109.5
C3—C4—Cl1	118.79 (12)

C7—N2—N3—C9	−177.77 (13)	N3—N2—C7—C6	−178.53 (13)
C8—N1—C1—C2	178.80 (14)	N3—N2—C7—C8	1.2 (2)
C8—N1—C1—C6	−0.92 (16)	C5—C6—C7—N2	−2.2 (3)
C6—C1—C2—C3	−1.2 (2)	C1—C6—C7—N2	177.97 (14)
N1—C1—C2—C3	179.15 (13)	C5—C6—C7—C8	177.99 (15)
C1—C2—C3—C4	−1.0 (2)	C1—C6—C7—C8	−1.83 (15)
C2—C3—C4—C5	2.3 (2)	C1—N1—C8—O1	179.09 (15)
C2—C3—C4—Cl1	−176.16 (11)	C1—N1—C8—C7	−0.27 (16)
C3—C4—C5—C6	−1.3 (2)	N2—C7—C8—O1	2.1 (3)
Cl1—C4—C5—C6	177.14 (11)	C6—C7—C8—O1	−178.07 (14)
C4—C5—C6—C1	−0.9 (2)	N2—C7—C8—N1	−178.50 (14)
C4—C5—C6—C7	179.33 (14)	C6—C7—C8—N1	1.30 (15)
C2—C1—C6—C5	2.1 (2)	C10—N4—C9—N3	−178.06 (13)
N1—C1—C6—C5	−178.12 (13)	C10—N4—C9—S1	2.7 (2)
C2—C1—C6—C7	−178.02 (13)	N2—N3—C9—N4	1.08 (19)
N1—C1—C6—C7	1.72 (15)	N2—N3—C9—S1	−179.58 (10)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···N2	0.88 (2)	2.27 (2)	2.6416 (18)	105.6 (15)
N4—H1N4···S1ⁱ	0.88 (2)	2.70 (2)	3.4972 (13)	152.2 (16)
N3—H1N3···O1	0.86 (2)	2.086 (19)	2.7526 (16)	134.3 (17)
N1—H1N1···O1ⁱⁱ	0.81 (2)	2.01 (2)	2.8161 (16)	175 (2)
C3—H3A···Cg2ⁱⁱⁱ	0.95	2.59	3.38	141

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

Experimental details

Crystal data
Chemical formula	C₁₀H₉ClN₄OS
M_r	268.72
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	6.2558 (1), 10.1449 (1), 18.5682 (2)
V (Å³)	1178.42 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.49
Crystal size (mm)	0.34 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.853, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	16807, 4886, 4072
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.795

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.078, 1.05
No. of reflections	4886
No. of parameters	167
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.32
Absolute structure	Flack (1983), 2074 Friedel pairs
Absolute structure parameter	0.01 (5)

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.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···N2	0.88 (2)	2.27 (2)	2.6416 (18)	105.6 (15)
N4—H1N4···S1ⁱ	0.88 (2)	2.70 (2)	3.4972 (13)	152.2 (16)
N3—H1N3···O1	0.86 (2)	2.086 (19)	2.7526 (16)	134.3 (17)
N1—H1N1···O1ⁱⁱ	0.81 (2)	2.01 (2)	2.8161 (16)	175 (2)
C3—H3A···Cg2ⁱⁱⁱ	0.95	2.59	3.38	141

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1/2, −y+1/2, −z+2; (iii) x−1/2, −y+3/2, −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 (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
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Pandeya, S. N., Sriram, D., Nath, G. & Clercq, E. De. (1999). Indian J. Pharm. Sci. 61, 358–361. 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
Qasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2012). Acta Cryst. E68, o953–o954. 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). Ind. 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 o964-o965

doi:10.1107/S1600536812007386

Open

access