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

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

doi:10.1107/S1600536812001183

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o953-o954

doi:10.1107/S1600536812001183

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(Z)-N-Methyl-2-(5-nitro-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, Sudan, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: sgteoh@usm.my

(Received 6 January 2012; accepted 10 January 2012; online 3 March 2012)

In the title compound, C₁₀H₉N₅O₃S, an intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked via N—H⋯S hydrogen bonds into a zigzag chain along the b axis. C—H⋯O interactions are observed between the chains.

Related literature

For related structures, see: 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 activity of isatin and its derivatives, see: Vine et al. (2009 ). For graph-set analysis, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₀H₉N₅O₃S
M_r = 279.28
Monoclinic, P 2₁ /c
a = 4.6316 (4) Å
b = 9.3157 (8) Å
c = 26.458 (2) Å
β = 94.485 (2)°
V = 1138.09 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 100 K
0.36 × 0.12 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.900, T_max = 0.979
10734 measured reflections
2710 independent reflections
2177 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.102
S = 1.10
2710 reflections
185 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 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—H1N3⋯O1	0.84 (3)	2.02 (3)	2.697 (2)	137 (3)
N1—H1N1⋯S1ⁱ	0.81 (3)	2.52 (3)	3.320 (2)	171 (3)
C2—H2A⋯O1ⁱⁱ	0.95	2.39	3.317 (3)	165
C10—H10A⋯O2ⁱⁱⁱ	0.98	2.56	3.079 (3)	113
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z+1.

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/S1600536812001183/is5048sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001183/is5048Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812001183/is5048Isup3.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 antifungal 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-phenylhydrazinecarbothioamide (Qasem Ali et al., 2011a). In the present paper we describe the single-crystal X-ray diffraction study of title compound, Fig. 1.

In this compound (Fig. 1), the chain N2/N3//C9/S1/N4/C10 connected to the nine-membered 5-nitroindolin-2-one ring system in C7. In this chain, C7—N2—N3—C9 and C10—N4—C9—S1 have torsion angles 177.82 (19) and -0.9 (3)°, respectively. The essentially planar conformation of the molecule is maintained by an intramolecular N3—H1N3···O1 hydrogen bond (Table 1) with a graph-set S(6) (Bernstein et al., 1995) In the crystal, molecules are linked via an intermolecular N1—H1N1···S1ⁱ hydrogen bond into an infinite one-dimensional chain along the b axis (Table 1 and Fig. 2). C2—H2A···O1ⁱⁱ and C10—H10A···O2ⁱⁱⁱ hydrogen bonds (Table 1) are also observed between the chains.

Related literature top

For related structures, see: 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 activity of isatin and its derivatives, see: Vine et al. (2009). 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 5-methyl-3-thiosemicarbazide (0.01 mol) and hot ethanolic solution (30 ml) of 5-nitroisatin (0.01 mol) for 2 hrs. The precipitate formed during reflux was filtered, washed with cold EtOH and recrystallized from hot EtOH (yield 80%, m.p. 579.8–580.3 K). The orange crystals were grown in an acetone-DMF (3:1) solution by slow evaporation at room temperature.

Structure description top

For related structures, see: 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 activity 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-nitro-2-oxoindolin-3- ylidene)hydrazinecarbothioamide top

Crystal data top

C₁₀H₉N₅O₃S	F(000) = 576
M_r = 279.28	D_x = 1.630 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 579.8–580.3 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 4.6316 (4) Å	Cell parameters from 3870 reflections
b = 9.3157 (8) Å	θ = 2.7–30.1°
c = 26.458 (2) Å	µ = 0.30 mm⁻¹
β = 94.485 (2)°	T = 100 K
V = 1138.09 (17) Å³	Needle, orange
Z = 4	0.36 × 0.12 × 0.07 mm

Data collection top

Bruker APEXII CCD diffractometer	2710 independent reflections
Radiation source: fine-focus sealed tube	2177 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
φ and ω scans	θ_max = 28.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
T_min = 0.900, T_max = 0.979	k = −11→12
10734 measured reflections	l = −34→34

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0189P)² + 1.8143P] where P = (F_o² + 2F_c²)/3
2710 reflections	(Δ/σ)_max = 0.001
185 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₀H₉N₅O₃S	V = 1138.09 (17) Å³
M_r = 279.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.6316 (4) Å	µ = 0.30 mm⁻¹
b = 9.3157 (8) Å	T = 100 K
c = 26.458 (2) Å	0.36 × 0.12 × 0.07 mm
β = 94.485 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2710 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2177 reflections with I > 2σ(I)
T_min = 0.900, T_max = 0.979	R_int = 0.045
10734 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.40 e Å⁻³
2710 reflections	Δρ_min = −0.29 e Å⁻³
185 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	1.21633 (12)	0.51362 (6)	0.32848 (2)	0.01849 (15)
O1	0.5410 (3)	0.21885 (18)	0.25632 (6)	0.0199 (4)
O2	−0.1914 (4)	−0.2525 (2)	0.47157 (8)	0.0409 (5)
O3	0.1838 (4)	−0.1372 (2)	0.50290 (7)	0.0304 (4)
N1	0.2084 (4)	0.0484 (2)	0.27784 (8)	0.0187 (4)
N2	0.6885 (4)	0.2193 (2)	0.36918 (7)	0.0159 (4)
N3	0.8430 (4)	0.3086 (2)	0.34179 (7)	0.0166 (4)
N4	1.0960 (4)	0.3840 (2)	0.41442 (7)	0.0189 (4)
N5	0.0142 (5)	−0.1717 (2)	0.46698 (8)	0.0242 (5)
C1	0.1322 (5)	−0.0181 (2)	0.32196 (8)	0.0167 (5)
C2	−0.0740 (5)	−0.1225 (3)	0.32723 (9)	0.0198 (5)
H2A	−0.1871	−0.1592	0.2986	0.024*
C3	−0.1108 (5)	−0.1721 (3)	0.37559 (9)	0.0212 (5)
H3A	−0.2502	−0.2444	0.3807	0.025*
C4	0.0580 (5)	−0.1154 (3)	0.41667 (9)	0.0198 (5)
C5	0.2677 (5)	−0.0110 (3)	0.41212 (9)	0.0185 (5)
H5A	0.3813	0.0249	0.4408	0.022*
C6	0.3033 (5)	0.0383 (2)	0.36375 (8)	0.0166 (5)
C7	0.4952 (5)	0.1430 (2)	0.34383 (8)	0.0155 (4)
C8	0.4257 (5)	0.1451 (2)	0.28722 (8)	0.0166 (5)
C9	1.0477 (5)	0.3984 (2)	0.36484 (8)	0.0164 (5)
C10	1.3117 (5)	0.4679 (3)	0.44437 (9)	0.0257 (6)
H10A	1.2463	0.4842	0.4782	0.039*
H10B	1.3383	0.5604	0.4277	0.039*
H10C	1.4959	0.4157	0.4473	0.039*
H1N3	0.803 (6)	0.317 (3)	0.3104 (11)	0.020 (7)*
H1N4	1.013 (6)	0.318 (3)	0.4291 (10)	0.021 (7)*
H1N1	0.123 (6)	0.039 (3)	0.2501 (11)	0.024 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0212 (3)	0.0194 (3)	0.0137 (3)	0.0002 (2)	−0.0055 (2)	0.0021 (2)
O1	0.0248 (8)	0.0222 (9)	0.0117 (8)	0.0021 (7)	−0.0052 (7)	−0.0004 (7)
O2	0.0460 (12)	0.0433 (12)	0.0332 (11)	−0.0198 (10)	0.0027 (9)	0.0087 (10)
O3	0.0335 (10)	0.0384 (11)	0.0183 (9)	−0.0006 (8)	−0.0046 (8)	0.0046 (8)
N1	0.0225 (10)	0.0215 (10)	0.0107 (10)	0.0014 (8)	−0.0081 (8)	−0.0037 (8)
N2	0.0173 (9)	0.0160 (9)	0.0135 (9)	0.0022 (7)	−0.0039 (7)	−0.0008 (8)
N3	0.0211 (10)	0.0193 (10)	0.0082 (9)	0.0007 (8)	−0.0062 (7)	0.0012 (8)
N4	0.0221 (10)	0.0222 (11)	0.0111 (10)	−0.0047 (8)	−0.0055 (8)	−0.0006 (8)
N5	0.0274 (11)	0.0227 (11)	0.0224 (11)	0.0017 (9)	0.0013 (9)	0.0036 (9)
C1	0.0173 (10)	0.0165 (11)	0.0153 (11)	0.0060 (9)	−0.0047 (8)	−0.0041 (9)
C2	0.0190 (11)	0.0189 (12)	0.0203 (12)	0.0019 (9)	−0.0066 (9)	−0.0068 (10)
C3	0.0216 (11)	0.0155 (11)	0.0258 (13)	0.0013 (9)	−0.0015 (10)	−0.0016 (10)
C4	0.0226 (11)	0.0186 (12)	0.0177 (12)	0.0045 (9)	−0.0012 (9)	0.0010 (9)
C5	0.0183 (10)	0.0188 (12)	0.0176 (11)	0.0039 (9)	−0.0037 (9)	−0.0020 (9)
C6	0.0165 (10)	0.0170 (11)	0.0155 (11)	0.0037 (8)	−0.0041 (9)	−0.0034 (9)
C7	0.0175 (10)	0.0170 (11)	0.0111 (11)	0.0053 (8)	−0.0043 (8)	−0.0016 (9)
C8	0.0190 (11)	0.0182 (11)	0.0113 (11)	0.0049 (9)	−0.0063 (8)	−0.0032 (9)
C9	0.0174 (10)	0.0156 (11)	0.0152 (11)	0.0047 (9)	−0.0048 (9)	−0.0036 (9)
C10	0.0283 (13)	0.0315 (14)	0.0157 (12)	−0.0081 (11)	−0.0086 (10)	−0.0036 (11)

Geometric parameters (Å, º) top

S1—C9	1.675 (2)	C1—C2	1.378 (3)
O1—C8	1.222 (3)	C1—C6	1.410 (3)
O2—N5	1.227 (3)	C2—C3	1.383 (3)
O3—N5	1.227 (3)	C2—H2A	0.9500
N1—C8	1.359 (3)	C3—C4	1.392 (3)
N1—C1	1.391 (3)	C3—H3A	0.9500
N1—H1N1	0.81 (3)	C4—C5	1.387 (3)
N2—C7	1.289 (3)	C5—C6	1.382 (3)
N2—N3	1.346 (3)	C5—H5A	0.9500
N3—C9	1.371 (3)	C6—C7	1.446 (3)
N3—H1N3	0.84 (3)	C7—C8	1.507 (3)
N4—C9	1.320 (3)	C10—H10A	0.9800
N4—C10	1.454 (3)	C10—H10B	0.9800
N4—H1N4	0.84 (3)	C10—H10C	0.9800
N5—C4	1.460 (3)

C8—N1—C1	112.00 (19)	C5—C4—N5	118.6 (2)
C8—N1—H1N1	123 (2)	C3—C4—N5	117.8 (2)
C1—N1—H1N1	125 (2)	C6—C5—C4	116.7 (2)
C7—N2—N3	115.95 (19)	C6—C5—H5A	121.7
N2—N3—C9	121.06 (19)	C4—C5—H5A	121.7
N2—N3—H1N3	120.3 (18)	C5—C6—C1	120.1 (2)
C9—N3—H1N3	118.3 (18)	C5—C6—C7	133.1 (2)
C9—N4—C10	122.9 (2)	C1—C6—C7	106.81 (19)
C9—N4—H1N4	119.1 (19)	N2—C7—C6	127.1 (2)
C10—N4—H1N4	117.7 (19)	N2—C7—C8	126.5 (2)
O2—N5—O3	122.6 (2)	C6—C7—C8	106.34 (19)
O2—N5—C4	118.3 (2)	O1—C8—N1	127.4 (2)
O3—N5—C4	119.1 (2)	O1—C8—C7	127.0 (2)
C2—C1—N1	128.5 (2)	N1—C8—C7	105.67 (19)
C2—C1—C6	122.4 (2)	N4—C9—N3	116.0 (2)
N1—C1—C6	109.2 (2)	N4—C9—S1	125.82 (18)
C1—C2—C3	117.8 (2)	N3—C9—S1	118.22 (17)
C1—C2—H2A	121.1	N4—C10—H10A	109.5
C3—C2—H2A	121.1	N4—C10—H10B	109.5
C2—C3—C4	119.5 (2)	H10A—C10—H10B	109.5
C2—C3—H3A	120.2	N4—C10—H10C	109.5
C4—C3—H3A	120.2	H10A—C10—H10C	109.5
C5—C4—C3	123.6 (2)	H10B—C10—H10C	109.5

C7—N2—N3—C9	177.82 (19)	C2—C1—C6—C7	179.3 (2)
C8—N1—C1—C2	−178.9 (2)	N1—C1—C6—C7	−0.7 (2)
C8—N1—C1—C6	1.1 (3)	N3—N2—C7—C6	179.3 (2)
N1—C1—C2—C3	−179.9 (2)	N3—N2—C7—C8	−0.4 (3)
C6—C1—C2—C3	0.0 (3)	C5—C6—C7—N2	−0.5 (4)
C1—C2—C3—C4	0.3 (3)	C1—C6—C7—N2	−179.7 (2)
C2—C3—C4—C5	−0.7 (4)	C5—C6—C7—C8	179.3 (2)
C2—C3—C4—N5	−179.4 (2)	C1—C6—C7—C8	0.1 (2)
O2—N5—C4—C5	172.4 (2)	C1—N1—C8—O1	179.1 (2)
O3—N5—C4—C5	−7.9 (3)	C1—N1—C8—C7	−1.0 (2)
O2—N5—C4—C3	−8.9 (3)	N2—C7—C8—O1	0.2 (4)
O3—N5—C4—C3	170.8 (2)	C6—C7—C8—O1	−179.6 (2)
C3—C4—C5—C6	0.8 (3)	N2—C7—C8—N1	−179.7 (2)
N5—C4—C5—C6	179.5 (2)	C6—C7—C8—N1	0.5 (2)
C4—C5—C6—C1	−0.5 (3)	C10—N4—C9—N3	178.2 (2)
C4—C5—C6—C7	−179.5 (2)	C10—N4—C9—S1	−0.9 (3)
C2—C1—C6—C5	0.1 (3)	N2—N3—C9—N4	4.5 (3)
N1—C1—C6—C5	180.0 (2)	N2—N3—C9—S1	−176.25 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O1	0.84 (3)	2.02 (3)	2.697 (2)	137 (3)
N1—H1N1···S1ⁱ	0.81 (3)	2.52 (3)	3.320 (2)	171 (3)
C2—H2A···O1ⁱⁱ	0.95	2.39	3.317 (3)	165
C10—H10A···O2ⁱⁱⁱ	0.98	2.56	3.079 (3)	113

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

Experimental details

Crystal data
Chemical formula	C₁₀H₉N₅O₃S
M_r	279.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	4.6316 (4), 9.3157 (8), 26.458 (2)
β (°)	94.485 (2)
V (Å³)	1138.09 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.36 × 0.12 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.900, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	10734, 2710, 2177
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.102, 1.10
No. of reflections	2710
No. of parameters	185
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.29

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
N3—H1N3···O1	0.84 (3)	2.02 (3)	2.697 (2)	137 (3)
N1—H1N1···S1ⁱ	0.81 (3)	2.52 (3)	3.320 (2)	171 (3)
C2—H2A···O1ⁱⁱ	0.9500	2.3900	3.317 (3)	165.00
C10—H10A···O2ⁱⁱⁱ	0.9800	2.5600	3.079 (3)	113.00

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

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). AQA thanks the Ministry of Higher Education and the University of Sabha (Libya) for a scholarship.

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