(Z)-N-Methyl-2-(5-methyl-2-oxoindolin-3-yl­idene)hydrazinecarbothio­amide

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

doi:10.1107/S1600536812005417

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o955-o956

doi:10.1107/S1600536812005417

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(Z)-N-Methyl-2-(5-methyl-2-oxoindolin-3-ylidene)hydrazinecarbothioamide

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 29 January 2012; accepted 7 February 2012; online 3 March 2012)

In the title compound, C₁₁H₁₂N₄OS, an intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the molecules form a helical chain along the a axis through an N—H⋯O hydrogen bond. These chains are extended by an N—H⋯S hydrogen bond and a C—H⋯π interaction into a three-dimensional network.

Related literature

For related structures, see: Ali et al. (2012 ); Qasem Ali et al. (2012 , 2011a ,b ). 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

C₁₁H₁₂N₄OS
M_r = 248.31
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.2826 (2) Å
b = 10.0341 (3) Å
c = 19.1315 (5) Å
V = 1206.05 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 100 K
0.51 × 0.18 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.879, T_max = 0.967
13743 measured reflections
3780 independent reflections
3463 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.097
S = 1.07
3780 reflections
168 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), with 1584 Friedel pairs
Flack parameter: −0.08 (7)

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
N1—H1N1⋯O1ⁱ	0.81 (2)	2.03 (2)	2.8319 (17)	171 (2)
N3—H1N3⋯O1	0.84 (2)	2.079 (19)	2.7525 (17)	136.9 (17)
N4—H1N4⋯S1ⁱⁱ	0.80 (2)	2.85 (2)	3.5538 (13)	148.5 (19)
C3—H3A⋯Cg2ⁱⁱⁱ	0.95	2.62	3.4165 (16)	142
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

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/S1600536812005417/is5066sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005417/is5066Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005417/is5066Isup3.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)-N-methyl-2-(5-nitro-2-oxoindolin-3-ylidene) hydrazinecarbothioamide (Ali et al., 2012). In the present paper we describe the single-crystal X-ray diffraction study of title compound.

In this compound (Fig. 1), the chain N2/N3/C9/S1/N4/C10 connects to the nine-membered 5-methylindolin-2-one ring system at C7. In this chain, C7/N2/N3/C9 and C10/N4/C9/S1 have torsion angles -176.69 (13) and -1.4 (2)°, respectively. The essentially planar conformation of the molecule is maintained by the cyclic intramolecular N3—H1N3···O1 hydrogen-bond (Table 1) [graph set S(6); Bernstein et al., 1995)]. In the crystal, the molecules form a helical chain through an intermolecular N1—H1N1···O1 hydrogen bond and are extended by an N4—H1N4···S1 hydrogen bond and a weak C3—H3A···Cg2 interaction into a three-dimensional network (Table 1, Fig. 2). Cg2 is the centroid of the C1–C6 ring.

Related literature top

For related structures, see: Ali et al. (2012); Qasem Ali et al. (2012, 2011a,b). 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 hot ethanolic solution (30 ml) of 5-methyl-3-thiosemicarbazide (0.01 mol) and hot ethanolic solution (30 ml) of 5-methylisatin (0.01 mol) for 2 h. The precipitate formed during reflux was filtered, washed with cold EtOH and recrystallized from hot EtOH (yield 94%, m.p. 551.7–552.2 K). The yellow crystals were grown in acetone–DMF (3:1) by slow evaporation at room temperature.

Structure description top

For related structures, see: Ali et al. (2012); Qasem Ali et al. (2012, 2011a,b). 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 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)-N-Methyl-2-(5-methyl-2-oxoindolin-3- ylidene)hydrazinecarbothioamide top

Crystal data top

C₁₁H₁₂N₄OS	D_x = 1.368 Mg m⁻³
M_r = 248.31	Melting point = 551.7–552.2 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5511 reflections
a = 6.2826 (2) Å	θ = 2.3–30.7°
b = 10.0341 (3) Å	µ = 0.26 mm⁻¹
c = 19.1315 (5) Å	T = 100 K
V = 1206.05 (6) Å³	Block, orange
Z = 4	0.51 × 0.18 × 0.13 mm
F(000) = 520

Data collection top

Bruker APEXII CCD diffractometer	3780 independent reflections
Radiation source: fine-focus sealed tube	3463 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
φ and ω scans	θ_max = 31.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→9
T_min = 0.879, T_max = 0.967	k = −14→13
13743 measured reflections	l = −26→27

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) = 0.097	w = 1/[σ²(F_o²) + (0.0489P)² + 0.2287P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3780 reflections	Δρ_max = 0.32 e Å⁻³
168 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Absolute structure: Flack (1983), with 1584 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.08 (7)

Crystal data top

C₁₁H₁₂N₄OS	V = 1206.05 (6) Å³
M_r = 248.31	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.2826 (2) Å	µ = 0.26 mm⁻¹
b = 10.0341 (3) Å	T = 100 K
c = 19.1315 (5) Å	0.51 × 0.18 × 0.13 mm

Data collection top

Bruker APEXII CCD diffractometer	3780 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3463 reflections with I > 2σ(I)
T_min = 0.879, T_max = 0.967	R_int = 0.050
13743 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.097	Δρ_max = 0.32 e Å⁻³
S = 1.07	Δρ_min = −0.24 e Å⁻³
3780 reflections	Absolute structure: Flack (1983), with 1584 Friedel pairs
168 parameters	Absolute structure parameter: −0.08 (7)
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
S1	−0.25429 (6)	0.29169 (3)	0.213725 (19)	0.02077 (10)
O1	0.31886 (18)	0.26735 (11)	0.06564 (6)	0.0214 (2)
N1	0.6103 (2)	0.39581 (13)	0.03384 (7)	0.0191 (3)
N2	0.2245 (2)	0.50945 (11)	0.15475 (6)	0.0159 (2)
N3	0.0861 (2)	0.40757 (13)	0.16284 (7)	0.0171 (2)
N4	−0.1126 (2)	0.54025 (13)	0.23530 (7)	0.0181 (2)
C1	0.6888 (2)	0.52394 (15)	0.05069 (8)	0.0170 (3)
C2	0.8718 (2)	0.58576 (17)	0.02731 (8)	0.0206 (3)
H2A	0.9661	0.5427	−0.0042	0.025*
C3	0.9124 (2)	0.71447 (17)	0.05206 (8)	0.0217 (3)
H3A	1.0386	0.7586	0.0374	0.026*
C4	0.7740 (2)	0.78049 (15)	0.09758 (7)	0.0202 (3)
C5	0.5903 (2)	0.71534 (15)	0.12059 (7)	0.0175 (3)
H5A	0.4945	0.7585	0.1516	0.021*
C6	0.5498 (2)	0.58673 (15)	0.09747 (7)	0.0157 (3)
C7	0.3812 (2)	0.49169 (14)	0.11202 (7)	0.0158 (3)
C8	0.4287 (2)	0.37009 (15)	0.06883 (8)	0.0175 (3)
C9	−0.0900 (2)	0.42245 (14)	0.20479 (7)	0.0163 (3)
C10	−0.2903 (2)	0.57322 (17)	0.28065 (9)	0.0246 (3)
H10A	−0.3009	0.6702	0.2853	0.037*
H10B	−0.2675	0.5333	0.3268	0.037*
H10C	−0.4223	0.5383	0.2604	0.037*
C11	0.8227 (3)	0.92103 (18)	0.12193 (9)	0.0288 (4)
H11A	0.9767	0.9361	0.1204	0.043*
H11B	0.7716	0.9327	0.1699	0.043*
H11C	0.7511	0.9851	0.0912	0.043*
H1N1	0.675 (4)	0.345 (2)	0.0091 (12)	0.030 (6)*
H1N3	0.105 (3)	0.337 (2)	0.1401 (10)	0.022 (5)*
H1N4	−0.027 (4)	0.598 (2)	0.2289 (11)	0.028 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01781 (16)	0.01833 (15)	0.02616 (18)	−0.00367 (14)	0.00191 (16)	0.00281 (13)
O1	0.0245 (5)	0.0189 (5)	0.0207 (5)	−0.0035 (4)	−0.0012 (4)	−0.0036 (4)
N1	0.0210 (6)	0.0189 (6)	0.0173 (6)	0.0018 (5)	0.0025 (5)	−0.0022 (5)
N2	0.0162 (6)	0.0145 (5)	0.0171 (5)	−0.0021 (4)	−0.0010 (5)	0.0021 (4)
N3	0.0167 (6)	0.0147 (5)	0.0200 (6)	−0.0019 (5)	0.0022 (5)	−0.0016 (4)
N4	0.0145 (5)	0.0195 (6)	0.0204 (6)	−0.0004 (5)	0.0015 (5)	−0.0009 (5)
C1	0.0175 (6)	0.0185 (6)	0.0149 (6)	0.0012 (5)	−0.0009 (5)	0.0020 (5)
C2	0.0171 (7)	0.0255 (7)	0.0191 (7)	0.0031 (6)	0.0023 (5)	0.0038 (6)
C3	0.0162 (6)	0.0277 (7)	0.0213 (7)	−0.0036 (6)	−0.0010 (5)	0.0069 (6)
C4	0.0211 (7)	0.0220 (6)	0.0174 (6)	−0.0062 (6)	−0.0035 (5)	0.0031 (5)
C5	0.0180 (6)	0.0185 (6)	0.0161 (6)	−0.0013 (6)	−0.0002 (5)	0.0003 (5)
C6	0.0148 (6)	0.0184 (6)	0.0140 (6)	0.0005 (5)	−0.0001 (5)	0.0013 (5)
C7	0.0167 (6)	0.0164 (6)	0.0143 (6)	−0.0005 (5)	−0.0021 (5)	−0.0008 (5)
C8	0.0197 (7)	0.0175 (6)	0.0154 (6)	0.0015 (5)	−0.0018 (5)	−0.0015 (5)
C9	0.0151 (6)	0.0170 (6)	0.0169 (6)	0.0004 (5)	−0.0026 (5)	0.0019 (5)
C10	0.0195 (7)	0.0294 (7)	0.0251 (7)	0.0036 (6)	0.0031 (6)	−0.0041 (6)
C11	0.0322 (8)	0.0273 (8)	0.0271 (8)	−0.0129 (7)	−0.0012 (7)	−0.0017 (7)

Geometric parameters (Å, º) top

S1—C9	1.6781 (15)	C2—H2A	0.9500
O1—C8	1.2419 (18)	C3—C4	1.398 (2)
N1—C8	1.348 (2)	C3—H3A	0.9500
N1—C1	1.414 (2)	C4—C5	1.398 (2)
N1—H1N1	0.81 (2)	C4—C11	1.516 (2)
N2—C7	1.2920 (19)	C5—C6	1.388 (2)
N2—N3	1.3510 (17)	C5—H5A	0.9500
N3—C9	1.3749 (19)	C6—C7	1.452 (2)
N3—H1N3	0.84 (2)	C7—C8	1.503 (2)
N4—C9	1.3259 (19)	C10—H10A	0.9800
N4—C10	1.4520 (19)	C10—H10B	0.9800
N4—H1N4	0.80 (2)	C10—H10C	0.9800
C1—C2	1.381 (2)	C11—H11A	0.9800
C1—C6	1.400 (2)	C11—H11B	0.9800
C2—C3	1.399 (2)	C11—H11C	0.9800

C8—N1—C1	110.85 (13)	C5—C6—C1	120.52 (14)
C8—N1—H1N1	127.0 (16)	C5—C6—C7	133.10 (14)
C1—N1—H1N1	122.0 (16)	C1—C6—C7	106.37 (13)
C7—N2—N3	117.30 (12)	N2—C7—C6	125.90 (13)
N2—N3—C9	120.18 (12)	N2—C7—C8	127.65 (13)
N2—N3—H1N3	119.1 (15)	C6—C7—C8	106.44 (12)
C9—N3—H1N3	120.6 (15)	O1—C8—N1	127.21 (14)
C9—N4—C10	123.25 (13)	O1—C8—C7	126.20 (13)
C9—N4—H1N4	120.3 (16)	N1—C8—C7	106.59 (13)
C10—N4—H1N4	116.4 (16)	N4—C9—N3	116.09 (13)
C2—C1—C6	121.61 (15)	N4—C9—S1	125.91 (11)
C2—C1—N1	128.67 (15)	N3—C9—S1	118.00 (11)
C6—C1—N1	109.72 (13)	N4—C10—H10A	109.5
C1—C2—C3	117.20 (15)	N4—C10—H10B	109.5
C1—C2—H2A	121.4	H10A—C10—H10B	109.5
C3—C2—H2A	121.4	N4—C10—H10C	109.5
C4—C3—C2	122.33 (14)	H10A—C10—H10C	109.5
C4—C3—H3A	118.8	H10B—C10—H10C	109.5
C2—C3—H3A	118.8	C4—C11—H11A	109.5
C3—C4—C5	119.23 (14)	C4—C11—H11B	109.5
C3—C4—C11	120.45 (14)	H11A—C11—H11B	109.5
C5—C4—C11	120.31 (15)	C4—C11—H11C	109.5
C6—C5—C4	119.07 (14)	H11A—C11—H11C	109.5
C6—C5—H5A	120.5	H11B—C11—H11C	109.5
C4—C5—H5A	120.5

C7—N2—N3—C9	−176.69 (13)	N3—N2—C7—C6	−178.16 (13)
C8—N1—C1—C2	178.42 (15)	N3—N2—C7—C8	0.6 (2)
C8—N1—C1—C6	−1.59 (17)	C5—C6—C7—N2	−2.0 (3)
C6—C1—C2—C3	−0.3 (2)	C1—C6—C7—N2	177.54 (14)
N1—C1—C2—C3	179.68 (14)	C5—C6—C7—C8	178.97 (15)
C1—C2—C3—C4	−1.1 (2)	C1—C6—C7—C8	−1.48 (15)
C2—C3—C4—C5	1.3 (2)	C1—N1—C8—O1	179.56 (15)
C2—C3—C4—C11	−178.82 (15)	C1—N1—C8—C7	0.58 (16)
C3—C4—C5—C6	−0.1 (2)	N2—C7—C8—O1	2.6 (2)
C11—C4—C5—C6	−179.99 (14)	C6—C7—C8—O1	−178.43 (14)
C4—C5—C6—C1	−1.2 (2)	N2—C7—C8—N1	−178.43 (14)
C4—C5—C6—C7	178.28 (15)	C6—C7—C8—N1	0.57 (16)
C2—C1—C6—C5	1.5 (2)	C10—N4—C9—N3	179.39 (14)
N1—C1—C6—C5	−178.51 (13)	C10—N4—C9—S1	−1.4 (2)
C2—C1—C6—C7	−178.14 (13)	N2—N3—C9—N4	0.19 (19)
N1—C1—C6—C7	1.87 (16)	N2—N3—C9—S1	−179.14 (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
N1—H1N1···O1ⁱ	0.81 (2)	2.03 (2)	2.8319 (17)	171 (2)
N3—H1N3···O1	0.84 (2)	2.079 (19)	2.7525 (17)	136.9 (17)
N4—H1N4···S1ⁱⁱ	0.80 (2)	2.85 (2)	3.5538 (13)	148.5 (19)
C3—H3A···Cg2ⁱⁱⁱ	0.95	2.62	3.4165 (16)	142

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂N₄OS
M_r	248.31
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	6.2826 (2), 10.0341 (3), 19.1315 (5)
V (Å³)	1206.05 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.51 × 0.18 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.879, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	13743, 3780, 3463
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.724

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.097, 1.07
No. of reflections	3780
No. of parameters	168
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.24
Absolute structure	Flack (1983), with 1584 Friedel pairs
Absolute structure parameter	−0.08 (7)

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
N1—H1N1···O1ⁱ	0.81 (2)	2.03 (2)	2.8319 (17)	171 (2)
N3—H1N3···O1	0.84 (2)	2.079 (19)	2.7525 (17)	136.9 (17)
N4—H1N4···S1ⁱⁱ	0.80 (2)	2.85 (2)	3.5538 (13)	148.5 (19)
C3—H3A···Cg2ⁱⁱⁱ	0.95	2.62	3.4165 (16)	142

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

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

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Volume 68| Part 4| April 2012| Pages o955-o956

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