2-(4-Bromo­phen­yl)-2-oxoethyl 2-methyl­benzoate

Fun, H.-K.; Ooi, C.W.; Garudachari, B.; Isloor, A.M.; Satyanarayan, M.N.

doi:10.1107/S1600536811044564

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3119

doi:10.1107/S1600536811044564

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2-(4-Bromophenyl)-2-oxoethyl 2-methylbenzoate

Hoong-Kun Fun,^a ^*‡ Chin Wei Ooi,^a B. Garudachari,^b Arun M. Isloor ^b and M. N. Satyanarayan ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bOrganic Electronics Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and ^cDepartment of Physics, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 24 October 2011; accepted 25 October 2011; online 29 October 2011)

In the title compound, C₁₆H₁₃BrO₃, the dihedral angle formed between the bromo- and methyl-substituted benzene rings is 66.66 (8)°. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the ac plane. The crystal packing is further consolidated by C—H⋯π interactions.

Related literature

For background and applications of phenacyl benzoates, see: Rather & Reid (1919 ); Sheehan & Umezaw (1973 ); Ruzicka et al. (2002 ); Litera et al. (2006 ); Huang et al. (1996 ); Gandhi et al. (1995 ). For a related structure, see: Fun et al. (2011 ). For the synthesis, see: Judefind & Reid (1920 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₃BrO₃
M_r = 333.17
Monoclinic, P 2₁ /c
a = 5.4519 (1) Å
b = 31.2382 (5) Å
c = 9.7206 (1) Å
β = 120.410 (1)°
V = 1427.74 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.88 mm⁻¹
T = 100 K
0.51 × 0.36 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.323, T_max = 0.811
20164 measured reflections
5211 independent reflections
4181 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.094
S = 1.04
5211 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O2ⁱ	0.99	2.32	3.224 (2)	151
C8—H8B⋯O2ⁱⁱ	0.99	2.52	3.447 (3)	156
C15—H15A⋯Cg1ⁱⁱⁱ	0.95	2.74	3.5472 (19)	143
C16—H16B⋯Cg1^iv	0.98	2.98	3.4909 (19)	114
C2—H2A⋯Cg2^v	0.95	2.91	3.5915 (19)	130
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) $[x-1, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iv) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811044564/is2797sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044564/is2797Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811044564/is2797Isup3.cml

checkCIF report

Comment top

Phenacyl benzoate derivatives are very important in identification of organic acids (Rather & Reid, 1919), since they undergo photolysis in neutral and mild conditions (Sheehan & Umezaw, 1973; Ruzicka et al., 2002; Litera et al., 2006). They find applications in the field of synthetic chemistry for the synthesis of oxazoles, imidazoles (Huang et al., 1996) and benzoxazepine (Gandhi et al., 1995). We hereby report the crystal structure of 2-(4-bromophenyl)-2-oxoethyl 2-methylbenzoate which has potential commercial importance.

In the title compound (Fig. 1), the dihedral angle formed between the bromo-substituted (C1–C6) and the methyl-substituted (C10–C15) benzene rings is 66.66 (8)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structure (Fun et al., 2011).

In the crystal packing (Fig. 2), the molecules are linked by intermolecular C8—H8A···O2 and C8—H8B···O2 hydrogen bonds (Table 1), forming a two-dimensional network parallel to the ac plane. The crystal packing is further consolidated by C—H···π interactions, involving the centroids of the bromo-substituted (C1–C6; Cg1; Table 1) and methyl-substituted benzene rings (C10–C15; Cg2; Table 1).

Related literature top

For background and applications of phenacyl benzoates, see: Rather & Reid (1919); Sheehan & Umezaw (1973); Ruzicka et al. (2002); Litera et al. (2006); Huang et al. (1996); Gandhi et al. (1995). For a related structure, see: Fun et al. (2011). For the synthesis, see: Judefind & Reid (1920). For bond-length data, see: Allen et al. (1987).

Experimental top

The mixture of 2-methylbenzoic acid (1.0 g, 0.0073 mol), potassium carbonate (1.10 g, 0.0080 mol) and 2-bromo-1-(4-bromophenyl)ethanone (2.02 g, 0.0073 mol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. On cooling, colourless needle-shaped crystals of 2-(4-bromophenyl)-2-oxoethyl 2-methylbenzoate began to separate out. It was collected by filtration and recrystallized from ethanol. Yield: 2.35 g, 96.3%. M.p.: 330–331 K (Judefind & Reid, 1920).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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, showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds.

2-(4-Bromophenyl)-2-oxoethyl 2-methylbenzoate top

Crystal data top

C₁₆H₁₃BrO₃	F(000) = 672
M_r = 333.17	D_x = 1.550 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7724 reflections
a = 5.4519 (1) Å	θ = 2.6–32.6°
b = 31.2382 (5) Å	µ = 2.88 mm⁻¹
c = 9.7206 (1) Å	T = 100 K
β = 120.410 (1)°	Plate, colourless
V = 1427.74 (4) Å³	0.51 × 0.36 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5211 independent reflections
Radiation source: fine-focus sealed tube	4181 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 32.7°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.323, T_max = 0.811	k = −35→47
20164 measured reflections	l = −14→14

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0391P)² + 0.9854P] where P = (F_o² + 2F_c²)/3
5211 reflections	(Δ/σ)_max = 0.003
182 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₆H₁₃BrO₃	V = 1427.74 (4) Å³
M_r = 333.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.4519 (1) Å	µ = 2.88 mm⁻¹
b = 31.2382 (5) Å	T = 100 K
c = 9.7206 (1) Å	0.51 × 0.36 × 0.08 mm
β = 120.410 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5211 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4181 reflections with I > 2σ(I)
T_min = 0.323, T_max = 0.811	R_int = 0.032
20164 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.04	Δρ_max = 0.85 e Å⁻³
5211 reflections	Δρ_min = −0.43 e Å⁻³
182 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Br1	0.17278 (4)	0.970131 (6)	0.70447 (3)	0.03247 (7)
O1	0.2143 (2)	0.70425 (4)	0.82251 (14)	0.0169 (2)
O2	0.4582 (2)	0.75657 (4)	0.70793 (14)	0.0185 (2)
O3	−0.1113 (3)	0.70407 (4)	0.56018 (15)	0.0219 (3)
C1	0.1466 (3)	0.84316 (5)	0.81729 (19)	0.0167 (3)
H1A	0.0726	0.8273	0.8715	0.020*
C2	0.1160 (3)	0.88749 (6)	0.8057 (2)	0.0194 (3)
H2A	0.0232	0.9020	0.8526	0.023*
C3	0.2231 (3)	0.91002 (6)	0.7248 (2)	0.0197 (3)
C4	0.3636 (4)	0.88967 (6)	0.6568 (2)	0.0202 (3)
H4A	0.4370	0.9057	0.6024	0.024*
C5	0.3940 (3)	0.84555 (6)	0.6701 (2)	0.0177 (3)
H5A	0.4897	0.8312	0.6246	0.021*
C6	0.2854 (3)	0.82191 (5)	0.74968 (18)	0.0145 (3)
C7	0.3187 (3)	0.77446 (5)	0.75677 (18)	0.0147 (3)
C8	0.1688 (4)	0.74932 (5)	0.8257 (2)	0.0170 (3)
H8A	0.2405	0.7585	0.9371	0.020*
H8B	−0.0376	0.7554	0.7635	0.020*
C9	0.0627 (3)	0.68539 (5)	0.67839 (19)	0.0156 (3)
C10	0.1268 (3)	0.63882 (5)	0.68481 (19)	0.0154 (3)
C11	0.4045 (3)	0.62214 (6)	0.7696 (2)	0.0178 (3)
C12	0.4349 (4)	0.57773 (6)	0.7654 (2)	0.0234 (3)
H12A	0.6203	0.5657	0.8198	0.028*
C13	0.2030 (4)	0.55090 (6)	0.6846 (2)	0.0259 (4)
H13A	0.2306	0.5208	0.6866	0.031*
C14	−0.0708 (4)	0.56778 (6)	0.6002 (2)	0.0239 (3)
H14A	−0.2306	0.5495	0.5440	0.029*
C15	−0.1062 (3)	0.61174 (6)	0.5995 (2)	0.0191 (3)
H15A	−0.2917	0.6236	0.5400	0.023*
C16	0.6654 (3)	0.64980 (6)	0.8579 (2)	0.0223 (3)
H16A	0.8327	0.6338	0.8739	0.033*
H16B	0.6905	0.6579	0.9616	0.033*
H16C	0.6428	0.6757	0.7954	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03491 (11)	0.01766 (9)	0.04329 (13)	0.00216 (7)	0.01866 (9)	0.00472 (8)
O1	0.0187 (5)	0.0162 (5)	0.0144 (5)	0.0007 (4)	0.0074 (4)	−0.0001 (4)
O2	0.0168 (5)	0.0230 (6)	0.0175 (6)	0.0007 (4)	0.0101 (4)	−0.0028 (4)
O3	0.0182 (5)	0.0211 (6)	0.0189 (6)	0.0023 (4)	0.0038 (5)	0.0018 (5)
C1	0.0155 (7)	0.0202 (7)	0.0153 (7)	−0.0010 (6)	0.0085 (6)	−0.0001 (6)
C2	0.0162 (7)	0.0205 (8)	0.0207 (8)	0.0020 (6)	0.0086 (6)	−0.0017 (6)
C3	0.0161 (7)	0.0180 (7)	0.0214 (8)	−0.0003 (6)	0.0068 (6)	0.0011 (6)
C4	0.0191 (7)	0.0228 (8)	0.0190 (8)	−0.0032 (6)	0.0099 (6)	0.0020 (6)
C5	0.0149 (7)	0.0244 (8)	0.0157 (7)	−0.0013 (6)	0.0090 (6)	−0.0012 (6)
C6	0.0106 (6)	0.0193 (7)	0.0117 (6)	−0.0006 (5)	0.0044 (5)	−0.0008 (5)
C7	0.0111 (6)	0.0203 (7)	0.0094 (6)	−0.0006 (5)	0.0028 (5)	−0.0020 (5)
C8	0.0210 (7)	0.0163 (7)	0.0168 (7)	−0.0002 (6)	0.0118 (6)	−0.0016 (6)
C9	0.0135 (6)	0.0182 (7)	0.0151 (7)	−0.0016 (5)	0.0073 (5)	−0.0007 (5)
C10	0.0163 (7)	0.0168 (7)	0.0139 (7)	0.0002 (5)	0.0081 (6)	0.0007 (5)
C11	0.0173 (7)	0.0226 (8)	0.0154 (7)	0.0020 (6)	0.0096 (6)	0.0026 (6)
C12	0.0226 (8)	0.0229 (8)	0.0282 (9)	0.0072 (6)	0.0155 (7)	0.0058 (7)
C13	0.0307 (9)	0.0178 (8)	0.0343 (10)	0.0040 (7)	0.0203 (8)	0.0044 (7)
C14	0.0258 (8)	0.0201 (8)	0.0280 (9)	−0.0044 (7)	0.0152 (7)	−0.0018 (7)
C15	0.0168 (7)	0.0211 (8)	0.0185 (8)	−0.0005 (6)	0.0082 (6)	0.0000 (6)
C16	0.0140 (7)	0.0303 (9)	0.0204 (8)	0.0018 (6)	0.0072 (6)	−0.0009 (7)

Geometric parameters (Å, º) top

Br1—C3	1.8935 (18)	C8—H8A	0.9900
O1—C9	1.3493 (19)	C8—H8B	0.9900
O1—C8	1.433 (2)	C9—C10	1.490 (2)
O2—C7	1.2170 (19)	C10—C15	1.397 (2)
O3—C9	1.207 (2)	C10—C11	1.407 (2)
C1—C2	1.392 (2)	C11—C12	1.400 (2)
C1—C6	1.396 (2)	C11—C16	1.507 (2)
C1—H1A	0.9500	C12—C13	1.383 (3)
C2—C3	1.386 (2)	C12—H12A	0.9500
C2—H2A	0.9500	C13—C14	1.393 (3)
C3—C4	1.393 (2)	C13—H13A	0.9500
C4—C5	1.386 (2)	C14—C15	1.386 (2)
C4—H4A	0.9500	C14—H14A	0.9500
C5—C6	1.399 (2)	C15—H15A	0.9500
C5—H5A	0.9500	C16—H16A	0.9800
C6—C7	1.491 (2)	C16—H16B	0.9800
C7—C8	1.512 (2)	C16—H16C	0.9800

C9—O1—C8	115.46 (13)	O3—C9—O1	123.39 (15)
C2—C1—C6	120.43 (15)	O3—C9—C10	124.51 (15)
C2—C1—H1A	119.8	O1—C9—C10	112.05 (13)
C6—C1—H1A	119.8	C15—C10—C11	120.62 (15)
C3—C2—C1	118.88 (15)	C15—C10—C9	116.27 (14)
C3—C2—H2A	120.6	C11—C10—C9	123.10 (14)
C1—C2—H2A	120.6	C12—C11—C10	117.24 (15)
C2—C3—C4	121.92 (16)	C12—C11—C16	119.55 (15)
C2—C3—Br1	118.84 (13)	C10—C11—C16	123.17 (15)
C4—C3—Br1	119.24 (13)	C13—C12—C11	121.96 (16)
C5—C4—C3	118.51 (15)	C13—C12—H12A	119.0
C5—C4—H4A	120.7	C11—C12—H12A	119.0
C3—C4—H4A	120.7	C12—C13—C14	120.28 (17)
C4—C5—C6	120.84 (15)	C12—C13—H13A	119.9
C4—C5—H5A	119.6	C14—C13—H13A	119.9
C6—C5—H5A	119.6	C15—C14—C13	118.89 (17)
C1—C6—C5	119.42 (15)	C15—C14—H14A	120.6
C1—C6—C7	122.24 (14)	C13—C14—H14A	120.6
C5—C6—C7	118.33 (14)	C14—C15—C10	120.96 (16)
O2—C7—C6	121.60 (15)	C14—C15—H15A	119.5
O2—C7—C8	121.25 (15)	C10—C15—H15A	119.5
C6—C7—C8	117.14 (13)	C11—C16—H16A	109.5
O1—C8—C7	111.25 (13)	C11—C16—H16B	109.5
O1—C8—H8A	109.4	H16A—C16—H16B	109.5
C7—C8—H8A	109.4	C11—C16—H16C	109.5
O1—C8—H8B	109.4	H16A—C16—H16C	109.5
C7—C8—H8B	109.4	H16B—C16—H16C	109.5
H8A—C8—H8B	108.0

C6—C1—C2—C3	0.6 (2)	C8—O1—C9—O3	−3.7 (2)
C1—C2—C3—C4	−0.9 (3)	C8—O1—C9—C10	178.78 (12)
C1—C2—C3—Br1	178.42 (12)	O3—C9—C10—C15	−40.3 (2)
C2—C3—C4—C5	0.5 (3)	O1—C9—C10—C15	137.23 (15)
Br1—C3—C4—C5	−178.80 (12)	O3—C9—C10—C11	139.03 (17)
C3—C4—C5—C6	0.2 (2)	O1—C9—C10—C11	−43.5 (2)
C2—C1—C6—C5	0.0 (2)	C15—C10—C11—C12	−0.6 (2)
C2—C1—C6—C7	−178.94 (14)	C9—C10—C11—C12	−179.87 (15)
C4—C5—C6—C1	−0.4 (2)	C15—C10—C11—C16	177.21 (16)
C4—C5—C6—C7	178.59 (15)	C9—C10—C11—C16	−2.1 (2)
C1—C6—C7—O2	−174.45 (15)	C10—C11—C12—C13	−1.3 (3)
C5—C6—C7—O2	6.6 (2)	C16—C11—C12—C13	−179.19 (17)
C1—C6—C7—C8	6.2 (2)	C11—C12—C13—C14	1.8 (3)
C5—C6—C7—C8	−172.78 (14)	C12—C13—C14—C15	−0.3 (3)
C9—O1—C8—C7	−75.92 (17)	C13—C14—C15—C10	−1.6 (3)
O2—C7—C8—O1	−0.4 (2)	C11—C10—C15—C14	2.0 (3)
C6—C7—C8—O1	178.89 (12)	C9—C10—C15—C14	−178.63 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2ⁱ	0.99	2.32	3.224 (2)	151
C8—H8B···O2ⁱⁱ	0.99	2.52	3.447 (3)	156
C15—H15A···Cg1ⁱⁱⁱ	0.95	2.74	3.5472 (19)	143
C16—H16B···Cg1^iv	0.98	2.98	3.4909 (19)	114
C2—H2A···Cg2^v	0.95	2.91	3.5915 (19)	130

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃BrO₃
M_r	333.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.4519 (1), 31.2382 (5), 9.7206 (1)
β (°)	120.410 (1)
V (Å³)	1427.74 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.88
Crystal size (mm)	0.51 × 0.36 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.323, 0.811
No. of measured, independent and observed [I > 2σ(I)] reflections	20164, 5211, 4181
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.759

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.094, 1.04
No. of reflections	5211
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.43

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2ⁱ	0.99	2.32	3.224 (2)	151
C8—H8B···O2ⁱⁱ	0.99	2.52	3.447 (3)	156
C15—H15A···Cg1ⁱⁱⁱ	0.95	2.74	3.5472 (19)	143
C16—H16B···Cg1^iv	0.98	2.98	3.4909 (19)	114
C2—H2A···Cg2^v	0.95	2.91	3.5915 (19)	130

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). CWO also thanks the Malaysian Government and USM for the award of the post of research assistant under the Research University Grant (1001/PFIZIK/811151). AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India for the Young scientist award. SMN thanks the Department of Information Technology, New Delhi, India, for financial support.

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