5-(4-Methyl­phen­yl)-3-phenyl­cyclo­hex-2-en-1-one

Mohamed, S.K.; Akkurt, M.; Abdelhamid, A.A.; Singh, K.; Allah, O.A.A.A.

doi:10.1107/S1600536812027031

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2157

https://doi.org/10.1107/S1600536812027031

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5-(4-Methylphenyl)-3-phenylcyclohex-2-en-1-one

Shaaban K. Mohamed,^a Mehmet Akkurt,^b ^* Antar A Abdelhamid,^a Kuldip Singh ^c and Omyma A. A. Abd Allah ^d

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Chemistry, University of Leicester, Leicester, England, and ^dDepartment of Chemistry, Faculty of Science, Sohag University, Sohag, Egypt
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 13 June 2012; accepted 14 June 2012; online 20 June 2012)

In the title compound, C₁₉H₁₈O, the cyclohexene ring has an envelope conformation with the methine C atom on the flap. The phenyl and methylphenyl rings form a dihedral angle of 85.93 (11)°. The crystal packing is consolidated by van der Waals forces and weak C—H⋯π interactions.

Related literature

For the biological activity of α,β-unsaturated carbonyl compounds, see: Podraze (1991 ); Suksamrarn et al. (2003 ); Modzelewska et al. (2006 ); Shettigar et al. (2006 ); Ferrer et al. (2009 ); Asiri (2003 ); Forestier et al. (1989 ); Kumar et al. (2003 ). For the synthesis of cyclohexenones, see: Diao & Stahl (2011 ); González et al. (2009 ); Zhang et al. (2008 ). For geometric analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₉H₁₈O
M_r = 262.33
Monoclinic, P 2₁ /c
a = 17.085 (4) Å
b = 5.6807 (11) Å
c = 15.689 (3) Å
β = 113.152 (4)°
V = 1400.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 150 K
0.42 × 0.24 × 0.12 mm

Data collection

Bruker APEX 2000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.979, T_max = 0.991
9636 measured reflections
2473 independent reflections
1497 reflections with I > 2σ(I)
R_int = 0.106

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.114
S = 0.90
2473 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C13–C18 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cgⁱ	0.95	2.77	3.601 (3)	147
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (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: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812027031/xu5565sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027031/xu5565Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812027031/xu5565Isup3.cml

checkCIF report

Comment top

α,β-Unsaturated carbonyl compounds have shown various biological activities such as antioxidant (Suksamrarn et al., 2003), antitumor (Kumar et al., 2003), anticancer (Modzelewska et al., 2006) and antimalarial (Ferrer et al., 2009). In addition, chalcones also were widely used in cosmetic compositions (Forestier et al., 1989; Podraze, 1991) and applications of dyes (Asiri, 2003). Apart from being biologically important compounds, chalcone derivatives show non-linear optical (NLO) properties with excellent blue light transmittance and good crystallizability (Shettigar et al., 2006). In this context, herein we report the synthesis and crystal structure of the title compound (I).

As seen in Fig. 1, the title compound is not planar. The C1–C6 cyclohexene ring in (I) has a nearly envelope conformation [puckering parameters (Cremer & Pople, 1975) Q_T = 0.511 (3) Å, θ = 53.4 (3) ° and φ = 247.6 (4) °]. The C7–C12 phenyl ring makes a dihedral angle of 85.93 (11)° with the methyl-substituted C13 C18 benzene ring.

The crystal packing of (I) is stabilized by van der Waals forces and weak C—H···π interactions (Table 1, Fig. 2).

Related literature top

For the biological activity of α,β-unsaturated carbonyl compounds, see: Podraze (1991); Suksamrarn et al. (2003); Modzelewska et al. (2006); Shettigar et al. (2006); Ferrer et al. (2009); Asiri (2003); Forestier et al. (1989); Kumar et al. (2003). For the synthesis of cyclohexenones, see: Diao & Stahl (2011); González et al. (2009); Zhang et al. (2008). For geometric analysis, see: Cremer & Pople (1975).

Experimental top

To a solution of 222 mg (1 mmol) (2E)-3-(4-methylphenyl)-1-phenylprop-2-en-1-one in 40 ml e thanol, 100 mg of acetyl acetone was added in presence of 60 mg MeONa. The reaction mixture was refluxed for 7 h then cooled to room temperature (Diao & Stahl, 2011; González et al., 2009; Zhang et al., 2008). The excess solvent was removed under vacuum to afford the solid product which was filltered off and recrystallized from ethanol. The obtained crystals were in good quality (m.p. 343 K) for X-ray diffraction without further crystallization.

Structure description top

The crystal packing of (I) is stabilized by van der Waals forces and weak C—H···π interactions (Table 1, Fig. 2).

For the biological activity of α,β-unsaturated carbonyl compounds, see: Podraze (1991); Suksamrarn et al. (2003); Modzelewska et al. (2006); Shettigar et al. (2006); Ferrer et al. (2009); Asiri (2003); Forestier et al. (1989); Kumar et al. (2003). For the synthesis of cyclohexenones, see: Diao & Stahl (2011); González et al. (2009); Zhang et al. (2008). For geometric analysis, see: Cremer & Pople (1975).

Computing details top

Data collection: SMART (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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. View of the molecular packing of the title compound along the b axis.

5-(4-Methylphenyl)-3-phenylcyclohex-2-en-1-one top

Crystal data top

C₁₉H₁₈O	F(000) = 560
M_r = 262.33	D_x = 1.245 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 879 reflections
a = 17.085 (4) Å	θ = 2.6–28.4°
b = 5.6807 (11) Å	µ = 0.08 mm⁻¹
c = 15.689 (3) Å	T = 150 K
β = 113.152 (4)°	Plate, colourless
V = 1400.1 (5) Å³	0.42 × 0.24 × 0.12 mm
Z = 4

Data collection top

Bruker APEX 2000 CCD area-detector diffractometer	2473 independent reflections
Radiation source: fine-focus sealed tube	1497 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.106
phi and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −20→20
T_min = 0.979, T_max = 0.991	k = −6→6
9636 measured reflections	l = −18→18

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) = 0.114	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.040P)²] where P = (F_o² + 2F_c²)/3
2473 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₉H₁₈O	V = 1400.1 (5) Å³
M_r = 262.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.085 (4) Å	µ = 0.08 mm⁻¹
b = 5.6807 (11) Å	T = 150 K
c = 15.689 (3) Å	0.42 × 0.24 × 0.12 mm
β = 113.152 (4)°

Data collection top

Bruker APEX 2000 CCD area-detector diffractometer	2473 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1497 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.991	R_int = 0.106
9636 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 0.90	Δρ_max = 0.22 e Å⁻³
2473 reflections	Δρ_min = −0.19 e Å⁻³
182 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O1	0.26608 (10)	0.8925 (3)	1.12374 (11)	0.0414 (6)
C1	0.23739 (15)	0.7390 (4)	1.06451 (16)	0.0310 (8)
C2	0.14596 (15)	0.7212 (4)	1.00905 (15)	0.0297 (8)
C3	0.11153 (14)	0.5617 (4)	0.94080 (15)	0.0240 (8)
C4	0.16904 (13)	0.3960 (4)	0.91730 (15)	0.0279 (8)
C5	0.25840 (14)	0.4974 (4)	0.94353 (15)	0.0278 (8)
C6	0.29405 (14)	0.5614 (4)	1.04625 (15)	0.0329 (8)
C7	0.01837 (14)	0.5429 (4)	0.88700 (15)	0.0253 (8)
C8	−0.01655 (14)	0.3458 (4)	0.83212 (15)	0.0303 (8)
C9	−0.10293 (15)	0.3268 (4)	0.78170 (16)	0.0337 (9)
C10	−0.15772 (14)	0.5021 (4)	0.78364 (16)	0.0312 (8)
C11	−0.12489 (15)	0.6993 (4)	0.83717 (16)	0.0315 (9)
C12	−0.03831 (14)	0.7195 (4)	0.88790 (15)	0.0299 (8)
C13	0.31421 (13)	0.3378 (4)	0.91407 (15)	0.0258 (8)
C14	0.34825 (14)	0.1297 (4)	0.96021 (16)	0.0297 (8)
C15	0.39595 (14)	−0.0172 (4)	0.92875 (16)	0.0326 (8)
C16	0.41086 (14)	0.0364 (4)	0.85029 (16)	0.0298 (8)
C17	0.37680 (14)	0.2433 (4)	0.80440 (17)	0.0315 (8)
C18	0.32954 (14)	0.3917 (4)	0.83590 (16)	0.0299 (8)
C19	0.46239 (15)	−0.1244 (5)	0.81565 (18)	0.0438 (10)
H2	0.10900	0.82740	1.02180	0.0360*
H4A	0.14380	0.36270	0.84990	0.0330*
H4B	0.17310	0.24530	0.95050	0.0330*
H5	0.25190	0.64790	0.90840	0.0330*
H6A	0.29790	0.41820	1.08370	0.0390*
H6B	0.35200	0.62730	1.06470	0.0390*
H8	0.01990	0.22230	0.82950	0.0360*
H9	−0.12500	0.19050	0.74500	0.0400*
H10	−0.21720	0.48770	0.74870	0.0370*
H11	−0.16200	0.82180	0.83910	0.0380*
H12	−0.01680	0.85660	0.92430	0.0360*
H14	0.33870	0.08750	1.01390	0.0360*
H15	0.41900	−0.15800	0.96180	0.0390*
H17	0.38590	0.28460	0.75030	0.0380*
H18	0.30720	0.53340	0.80320	0.0360*
H19A	0.42480	−0.19810	0.75740	0.0660*
H19B	0.48940	−0.24660	0.86200	0.0660*
H19C	0.50630	−0.03270	0.80500	0.0660*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0401 (11)	0.0482 (12)	0.0358 (10)	−0.0067 (9)	0.0149 (9)	−0.0171 (9)
C1	0.0361 (15)	0.0347 (15)	0.0259 (14)	−0.0045 (12)	0.0162 (12)	−0.0028 (12)
C2	0.0302 (14)	0.0327 (15)	0.0303 (14)	0.0009 (11)	0.0162 (12)	−0.0025 (12)
C3	0.0284 (14)	0.0235 (14)	0.0236 (12)	0.0014 (11)	0.0139 (11)	0.0030 (11)
C4	0.0288 (14)	0.0281 (14)	0.0275 (13)	0.0007 (11)	0.0119 (11)	−0.0002 (11)
C5	0.0288 (13)	0.0285 (14)	0.0260 (14)	0.0006 (11)	0.0107 (11)	−0.0017 (11)
C6	0.0318 (14)	0.0377 (16)	0.0287 (14)	0.0005 (12)	0.0113 (12)	−0.0038 (12)
C7	0.0275 (13)	0.0268 (14)	0.0242 (13)	0.0022 (11)	0.0129 (11)	0.0037 (11)
C8	0.0296 (14)	0.0297 (15)	0.0310 (14)	0.0024 (11)	0.0114 (11)	−0.0023 (12)
C9	0.0326 (15)	0.0304 (15)	0.0365 (15)	−0.0035 (12)	0.0119 (12)	−0.0050 (12)
C10	0.0238 (13)	0.0362 (16)	0.0303 (14)	0.0009 (11)	0.0071 (11)	0.0056 (12)
C11	0.0319 (15)	0.0313 (15)	0.0336 (15)	0.0065 (12)	0.0153 (12)	0.0033 (12)
C12	0.0324 (15)	0.0275 (14)	0.0305 (14)	−0.0014 (11)	0.0132 (12)	−0.0029 (11)
C13	0.0214 (13)	0.0275 (14)	0.0266 (13)	−0.0026 (11)	0.0073 (11)	−0.0027 (11)
C14	0.0293 (14)	0.0347 (15)	0.0274 (13)	−0.0023 (12)	0.0135 (11)	0.0008 (12)
C15	0.0276 (14)	0.0294 (15)	0.0384 (15)	0.0008 (11)	0.0105 (12)	0.0015 (12)
C16	0.0230 (13)	0.0312 (15)	0.0351 (14)	−0.0040 (11)	0.0113 (11)	−0.0062 (12)
C17	0.0282 (14)	0.0359 (15)	0.0338 (15)	−0.0041 (12)	0.0159 (12)	−0.0028 (12)
C18	0.0314 (14)	0.0285 (15)	0.0283 (13)	−0.0031 (11)	0.0103 (11)	−0.0012 (11)
C19	0.0377 (16)	0.0459 (17)	0.0542 (17)	0.0025 (13)	0.0250 (14)	−0.0032 (14)

Geometric parameters (Å, º) top

O1—C1	1.227 (3)	C16—C19	1.510 (4)
C1—C2	1.462 (4)	C17—C18	1.386 (3)
C1—C6	1.502 (4)	C2—H2	0.9500
C2—C3	1.348 (3)	C4—H4A	0.9900
C3—C4	1.507 (3)	C4—H4B	0.9900
C3—C7	1.484 (3)	C5—H5	1.0000
C4—C5	1.529 (3)	C6—H6A	0.9900
C5—C6	1.526 (3)	C6—H6B	0.9900
C5—C13	1.514 (3)	C8—H8	0.9500
C7—C8	1.395 (3)	C9—H9	0.9500
C7—C12	1.398 (3)	C10—H10	0.9500
C8—C9	1.378 (4)	C11—H11	0.9500
C9—C10	1.375 (4)	C12—H12	0.9500
C10—C11	1.380 (3)	C14—H14	0.9500
C11—C12	1.382 (4)	C15—H15	0.9500
C13—C14	1.389 (3)	C17—H17	0.9500
C13—C18	1.385 (3)	C18—H18	0.9500
C14—C15	1.386 (3)	C19—H19A	0.9800
C15—C16	1.385 (3)	C19—H19B	0.9800
C16—C17	1.382 (3)	C19—H19C	0.9800

O1—C1—C2	121.0 (2)	C5—C4—H4B	109.00
O1—C1—C6	121.8 (2)	H4A—C4—H4B	108.00
C2—C1—C6	117.3 (2)	C4—C5—H5	107.00
C1—C2—C3	123.3 (2)	C6—C5—H5	107.00
C2—C3—C4	119.4 (2)	C13—C5—H5	107.00
C2—C3—C7	122.4 (2)	C1—C6—H6A	110.00
C4—C3—C7	118.20 (19)	C1—C6—H6B	110.00
C3—C4—C5	112.14 (19)	C5—C6—H6A	110.00
C4—C5—C6	108.40 (19)	C5—C6—H6B	110.00
C4—C5—C13	111.98 (19)	H6A—C6—H6B	108.00
C6—C5—C13	115.3 (2)	C7—C8—H8	119.00
C1—C6—C5	110.00 (19)	C9—C8—H8	119.00
C3—C7—C8	120.8 (2)	C8—C9—H9	119.00
C3—C7—C12	122.3 (2)	C10—C9—H9	119.00
C8—C7—C12	116.9 (2)	C9—C10—H10	121.00
C7—C8—C9	121.3 (2)	C11—C10—H10	121.00
C8—C9—C10	121.0 (2)	C10—C11—H11	120.00
C9—C10—C11	118.9 (2)	C12—C11—H11	120.00
C10—C11—C12	120.3 (2)	C7—C12—H12	119.00
C7—C12—C11	121.6 (2)	C11—C12—H12	119.00
C5—C13—C14	122.4 (2)	C13—C14—H14	120.00
C5—C13—C18	119.9 (2)	C15—C14—H14	120.00
C14—C13—C18	117.6 (2)	C14—C15—H15	119.00
C13—C14—C15	120.8 (2)	C16—C15—H15	119.00
C14—C15—C16	121.6 (2)	C16—C17—H17	119.00
C15—C16—C17	117.6 (2)	C18—C17—H17	119.00
C15—C16—C19	121.6 (2)	C13—C18—H18	119.00
C17—C16—C19	120.8 (2)	C17—C18—H18	119.00
C16—C17—C18	121.1 (2)	C16—C19—H19A	109.00
C13—C18—C17	121.4 (2)	C16—C19—H19B	109.00
C1—C2—H2	118.00	C16—C19—H19C	109.00
C3—C2—H2	118.00	H19A—C19—H19B	110.00
C3—C4—H4A	109.00	H19A—C19—H19C	109.00
C3—C4—H4B	109.00	H19B—C19—H19C	110.00
C5—C4—H4A	109.00

O1—C1—C2—C3	177.4 (2)	C6—C5—C13—C18	−132.9 (2)
C6—C1—C2—C3	−3.0 (3)	C3—C7—C8—C9	−179.8 (2)
O1—C1—C6—C5	−146.2 (2)	C12—C7—C8—C9	−0.3 (3)
C2—C1—C6—C5	34.2 (3)	C3—C7—C12—C11	179.8 (2)
C1—C2—C3—C4	−1.8 (3)	C8—C7—C12—C11	0.3 (3)
C1—C2—C3—C7	178.4 (2)	C7—C8—C9—C10	0.1 (4)
C2—C3—C4—C5	−25.3 (3)	C8—C9—C10—C11	0.0 (4)
C7—C3—C4—C5	154.5 (2)	C9—C10—C11—C12	0.0 (4)
C2—C3—C7—C8	−165.5 (2)	C10—C11—C12—C7	−0.2 (4)
C2—C3—C7—C12	15.0 (4)	C5—C13—C14—C15	177.1 (2)
C4—C3—C7—C8	14.8 (3)	C18—C13—C14—C15	0.2 (4)
C4—C3—C7—C12	−164.7 (2)	C5—C13—C18—C17	−176.7 (2)
C3—C4—C5—C6	55.5 (2)	C14—C13—C18—C17	0.3 (4)
C3—C4—C5—C13	−176.21 (18)	C13—C14—C15—C16	−0.5 (4)
C4—C5—C6—C1	−59.4 (2)	C14—C15—C16—C17	0.4 (4)
C13—C5—C6—C1	174.2 (2)	C14—C15—C16—C19	−179.6 (2)
C4—C5—C13—C14	−74.3 (3)	C15—C16—C17—C18	0.1 (4)
C4—C5—C13—C18	102.5 (2)	C19—C16—C17—C18	−179.9 (2)
C6—C5—C13—C14	50.3 (3)	C16—C17—C18—C13	−0.4 (4)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C13–C18 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cgⁱ	0.95	2.77	3.601 (3)	147

Symmetry code: (i) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈O
M_r	262.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	17.085 (4), 5.6807 (11), 15.689 (3)
β (°)	113.152 (4)
V (Å³)	1400.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.42 × 0.24 × 0.12

Data collection
Diffractometer	Bruker APEX 2000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.979, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	9636, 2473, 1497
R_int	0.106
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.114, 0.90
No. of reflections	2473
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.19

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C13–C18 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cgⁱ	0.95	2.77	3.601 (3)	147

Symmetry code: (i) −x, y+1/2, −z+3/2.

Acknowledgements

The authors are grateful to the Higher Education Ministry of Egypt for financial support and also thank Manchester Metropolitan University, Erciyes University and the University of Leicester for supporting this study.

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