(2E)-1-(2-Bromo­phen­yl)-3-(4-meth­oxy­phen­yl)prop-2-en-1-one

Jasinski, J.P.; Butcher, R.J.; Veena, K.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S160053681002218X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1661

doi:10.1107/S160053681002218X

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(2E)-1-(2-Bromophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one

Jerry P. Jasinski,^a ^* Ray J. Butcher,^b K. Veena,^c B. Narayana ^c and H. S. Yathirajan ^d

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA, ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, 574 199, India, and ^dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 3 June 2010; accepted 9 June 2010; online 16 June 2010)

In the title compound, C₁₆H₁₃BrO₂, two benzene rings form a dihedral angle of 44.3 (9)°. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into chains propagating in [010]. The crystal packing also exhibits short Br⋯Br contacts of 3.4787 (8) Å. A comparison of the DFT-optimized gas-phase molecular geometry with that in the crystal structure revealed only small differences.

Related literature

For the radical quenching properties of included phenol groups, see: Dhar (1981 ). For related structures, see: Arai et al. (1994 ); Li et al. (1992 ); Patil et al. (2007 ); Shettigar et al. (2006 ). For standard bond lengths, see Allen et al. (1987 ). For density functional theory, see: Schmidt & Polik (2007 ); Hehre et al. (1986 ).

Experimental

Crystal data

C₁₆H₁₃BrO₂
M_r = 317.17
Monoclinic, P 2₁
a = 12.7300 (8) Å
b = 4.0061 (3) Å
c = 13.0035 (6) Å
β = 100.671 (5)°
V = 651.68 (7) Å³
Z = 2
Cu Kα radiation
μ = 4.25 mm⁻¹
T = 110 K
0.48 × 0.41 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini Cu) detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.423, T_max = 1.000
2117 measured reflections
1641 independent reflections
1621 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.091
S = 1.07
1641 reflections
173 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.65 e Å⁻³
Absolute structure: Flack (1983 ), 133 Friedel pairs
Flack parameter: 0.00 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1ⁱ	0.95	2.59	3.541 (5)	174
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S160053681002218X/cv2728sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681002218X/cv2728Isup2.hkl

checkCIF report

Comment top

Chalcones, or 1,3-diaryl-2-propen-1-ones, belong to the flavonoid family. Chemically they consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α,β-unsaturated carbonyl system. A vast number of naturally occurring chalcones are polyhydroxylated in the aryl rings. The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using the compounds or chalcone rich plant extracts as drugs or food preservatives (Dhar, 1981). The crystal structures of some closely related chalcones, viz., 1-(4-bromophenyl)-3-(3-methoxy-phenyl)prop-2-en-1-one (Patil et al., 2007); 4-bromo-4'-methoxy-chalcone (Li et al., 1992), 4-bromo-4'-methoxychalcone (Arai et al., 1994) and 1-(4-bromophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (Shettigar et al., 2006) have been reported. Hence in continuation with the synthesis and crystal structure determination and also owing to the importance of these flavonoid analogs, this new bromo chalcone, (I), C₁₆H₁₃BrO₂, is synthesized and its crystal structure is reported.

The title compound, (I), C₁₆H₁₃BrO₂, is a chalcone with 4-methoxyphenyl and 2-bromophenyl rings bonded at opposite rings of a propene group (Fig. 1). The dihedral angle between mean planes of the para-methoxy and ortho-bromo substituted benzene rings is 44.3 (9)°. The angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 4-meyhoxyphenyl and 2-bromophenyl rings are 6.3 (1)° and 44.6(36°, respectively. Bond distances and angles are in normal ranges (Allen et al., 1987). While no classical hydrogen bonds are present, a weak intermolecular C12—H12A···O1 interaction (Table 1) is observed which contributes to the stability of crystal packing.

A density functional theory (DFT) geometry optimization molecular orbital calculation (Schmidt & Polik, 2007) was performed on (I) with the B3LYP 6–31-G(d) basis set (Hehre et al., 1986). The dihedral angle between mean planes of the para-methoxy and ortho-bromo substituted benzene rings becomes 45.98°, an increase of 1.59°. The angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 4-meyhoxyphenyl and 2-bromophenyl rings become 3.65° and 42.40°, changes of -2.65° and +0.74°, respectively. These observations suggest that the weak intermolecular C12—H12A···O1 interaction produces a small effect on crystal stability.

Related literature top

For the radical quenching properties of included phenol groups, see: Dhar (1981). For related structures, see: Arai et al. (1994); Li et al. (1992); Patil et al. (2007); Shettigar et al. (2006). For standard bond lengths, see Allen et al. (1987). For density functional theory, see: Schmidt & Polik (2007); Hehre et al. (1986).

Experimental top

A 50% KOH solution was added to a mixture of 2-bromo acetophenone (0.01 mol, 1.99 g) and 4-methoxy benzaldehyde (0.01 mol, 1.36 g) in 25 ml of ethanol (Fig. 2). The mixture was stirred for an hour at room temperature and the precipitate was collected by filtration and purified by recrystallization from ethanol. The single-crystal was grown from ethyl acetate by slow evaporation method and yield of the compound was 50% (m.p.336–338 K). Analytical data, composition (%): found (calculated): C: 60.52 (60.59%); H: 4.10 (4.13%).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); 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).

Figures top

	Fig. 1. Molecular structure of (I) showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Scheme for the synthesis of (I).

(2E)-1-(2-Bromophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₃BrO₂	F(000) = 320
M_r = 317.17	D_x = 1.616 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 1981 reflections
a = 12.7300 (8) Å	θ = 4.5–74.1°
b = 4.0061 (3) Å	µ = 4.25 mm⁻¹
c = 13.0035 (6) Å	T = 110 K
β = 100.671 (5)°	Chunk, colourless
V = 651.68 (7) Å³	0.48 × 0.41 × 0.28 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini Cu) detector	1641 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1621 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 10.5081 pixels mm^-1	θ_max = 74.1°, θ_min = 4.5°
ω scans	h = −9→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −2→4
T_min = 0.423, T_max = 1.000	l = −15→16
2117 measured reflections

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)] = 0.034	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0718P)² + 0.5775P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
1641 reflections	Δρ_max = 0.71 e Å⁻³
173 parameters	Δρ_min = −0.65 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 133 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (3)

Crystal data top

C₁₆H₁₃BrO₂	V = 651.68 (7) Å³
M_r = 317.17	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 12.7300 (8) Å	µ = 4.25 mm⁻¹
b = 4.0061 (3) Å	T = 110 K
c = 13.0035 (6) Å	0.48 × 0.41 × 0.28 mm
β = 100.671 (5)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini Cu) detector	1641 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	1621 reflections with I > 2σ(I)
T_min = 0.423, T_max = 1.000	R_int = 0.018
2117 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.091	Δρ_max = 0.71 e Å⁻³
S = 1.07	Δρ_min = −0.65 e Å⁻³
1641 reflections	Absolute structure: Flack (1983), 133 Friedel pairs
173 parameters	Absolute structure parameter: 0.00 (3)
1 restraint

Special details top

Experimental. IR data (KBr) ν cm^-1: 2998 cm^-1, 2937 cm^-1, 2839 cm^-1 (C—H al.str), 3058 cm^-1 (C—H ar. str) 1646 cm^-1 (C=O), 1580 cm^-1 (C=C); 1245 cm^-1 (C—O—C).

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
Br	0.38764 (3)	0.18817 (18)	0.46303 (2)	0.01538 (15)
O1	0.2178 (2)	0.2427 (10)	0.1406 (2)	0.0211 (8)
O2	0.8860 (2)	0.2977 (9)	0.1659 (2)	0.0209 (7)
C1	0.2190 (3)	0.4727 (13)	0.3077 (3)	0.0149 (9)
C2	0.2577 (3)	0.4233 (12)	0.4142 (3)	0.0119 (8)
C3	0.2022 (3)	0.5312 (12)	0.4896 (3)	0.0166 (9)
H3A	0.2299	0.4917	0.5616	0.020*
C4	0.1060 (3)	0.6971 (19)	0.4599 (3)	0.0223 (8)
H4A	0.0679	0.7740	0.5116	0.027*
C5	0.0651 (3)	0.7513 (12)	0.3545 (3)	0.0211 (11)
H5A	−0.0008	0.8660	0.3342	0.025*
C6	0.1203 (3)	0.6385 (14)	0.2797 (3)	0.0187 (10)
H6A	0.0913	0.6732	0.2078	0.022*
C7	0.2730 (3)	0.3590 (12)	0.2195 (3)	0.0173 (9)
C8	0.3891 (3)	0.4058 (13)	0.2303 (3)	0.0160 (9)
H8A	0.4255	0.5526	0.2824	0.019*
C9	0.4441 (3)	0.2431 (12)	0.1673 (3)	0.0161 (10)
H9A	0.4037	0.1037	0.1154	0.019*
C10	0.5595 (3)	0.2564 (10)	0.1697 (3)	0.0145 (11)
C11	0.5999 (3)	0.1064 (11)	0.0878 (3)	0.0164 (10)
H11A	0.5519	−0.0064	0.0344	0.020*
C12	0.7083 (3)	0.1171 (11)	0.0822 (3)	0.0155 (10)
H12A	0.7334	0.0191	0.0248	0.019*
C13	0.7787 (3)	0.2733 (11)	0.1619 (3)	0.0156 (10)
C14	0.7411 (4)	0.4183 (13)	0.2470 (3)	0.0186 (9)
H14A	0.7897	0.5209	0.3022	0.022*
C15	0.6327 (3)	0.4102 (13)	0.2495 (3)	0.0175 (9)
H15A	0.6075	0.5107	0.3065	0.021*
C16	0.9272 (3)	0.1512 (18)	0.0810 (3)	0.0223 (11)
H16A	0.9121	−0.0888	0.0783	0.033*
H16B	1.0046	0.1870	0.0916	0.033*
H16C	0.8930	0.2553	0.0151	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.0159 (2)	0.0153 (2)	0.0148 (2)	−0.0005 (2)	0.00224 (13)	0.00195 (19)
O1	0.0204 (13)	0.028 (2)	0.0151 (11)	−0.0044 (15)	0.0031 (10)	−0.0034 (14)
O2	0.0169 (14)	0.027 (2)	0.0207 (14)	−0.0012 (13)	0.0070 (12)	−0.0027 (13)
C1	0.0154 (18)	0.016 (2)	0.0154 (17)	−0.0033 (18)	0.0081 (15)	−0.0001 (17)
C2	0.0083 (16)	0.008 (2)	0.0179 (17)	0.0027 (16)	−0.0026 (13)	0.0032 (17)
C3	0.021 (2)	0.014 (2)	0.0160 (18)	−0.0060 (18)	0.0067 (15)	−0.0023 (16)
C4	0.0242 (18)	0.018 (2)	0.0292 (19)	−0.004 (3)	0.0173 (15)	−0.006 (3)
C5	0.0136 (17)	0.016 (3)	0.034 (2)	0.0014 (18)	0.0047 (16)	0.0002 (19)
C6	0.0165 (17)	0.016 (3)	0.0228 (17)	−0.003 (2)	0.0023 (14)	0.0024 (19)
C7	0.023 (2)	0.015 (2)	0.0152 (18)	−0.0028 (19)	0.0061 (16)	0.0040 (17)
C8	0.0176 (19)	0.015 (3)	0.0155 (17)	−0.0006 (18)	0.0036 (14)	0.0011 (17)
C9	0.0189 (17)	0.016 (3)	0.0131 (15)	−0.0011 (18)	0.0025 (13)	0.0027 (18)
C10	0.0197 (18)	0.014 (3)	0.0113 (15)	0.0016 (17)	0.0058 (14)	0.0018 (15)
C11	0.0208 (19)	0.015 (3)	0.0135 (16)	0.0001 (17)	0.0037 (14)	0.0000 (15)
C12	0.0200 (18)	0.015 (3)	0.0124 (15)	0.0016 (17)	0.0062 (14)	−0.0020 (15)
C13	0.0179 (18)	0.014 (3)	0.0159 (17)	0.0019 (16)	0.0068 (14)	0.0034 (16)
C14	0.024 (2)	0.019 (2)	0.0122 (16)	−0.001 (2)	0.0024 (15)	−0.0014 (18)
C15	0.022 (2)	0.020 (3)	0.0116 (16)	0.002 (2)	0.0071 (15)	0.0001 (18)
C16	0.0181 (17)	0.025 (3)	0.0261 (18)	0.000 (2)	0.0101 (14)	−0.004 (2)

Geometric parameters (Å, º) top

Br—C2	1.907 (4)	C8—H8A	0.9500
O1—C7	1.224 (5)	C9—C10	1.464 (5)
O2—C13	1.361 (5)	C9—H9A	0.9500
O2—C16	1.433 (5)	C10—C11	1.401 (6)
C1—C2	1.396 (5)	C10—C15	1.403 (6)
C1—C6	1.408 (6)	C11—C12	1.396 (6)
C1—C7	1.512 (5)	C11—H11A	0.9500
C2—C3	1.380 (6)	C12—C13	1.387 (6)
C3—C4	1.384 (7)	C12—H12A	0.9500
C3—H3A	0.9500	C13—C14	1.410 (6)
C4—C5	1.390 (6)	C14—C15	1.387 (6)
C4—H4A	0.9500	C14—H14A	0.9500
C5—C6	1.379 (6)	C15—H15A	0.9500
C5—H5A	0.9500	C16—H16A	0.9800
C6—H6A	0.9500	C16—H16B	0.9800
C7—C8	1.471 (6)	C16—H16C	0.9800
C8—C9	1.341 (6)

C13—O2—C16	116.7 (3)	C8—C9—H9A	116.4
C2—C1—C6	117.3 (4)	C10—C9—H9A	116.4
C2—C1—C7	125.7 (4)	C11—C10—C15	117.6 (4)
C6—C1—C7	117.1 (4)	C11—C10—C9	118.5 (4)
C3—C2—C1	121.9 (4)	C15—C10—C9	123.9 (4)
C3—C2—Br	116.4 (3)	C12—C11—C10	122.2 (4)
C1—C2—Br	121.7 (3)	C12—C11—H11A	118.9
C2—C3—C4	119.7 (4)	C10—C11—H11A	118.9
C2—C3—H3A	120.2	C13—C12—C11	118.9 (4)
C4—C3—H3A	120.2	C13—C12—H12A	120.6
C3—C4—C5	120.1 (4)	C11—C12—H12A	120.6
C3—C4—H4A	120.0	O2—C13—C12	124.5 (4)
C5—C4—H4A	120.0	O2—C13—C14	115.1 (4)
C6—C5—C4	119.9 (4)	C12—C13—C14	120.4 (4)
C6—C5—H5A	120.1	C15—C14—C13	119.5 (4)
C4—C5—H5A	120.1	C15—C14—H14A	120.2
C5—C6—C1	121.3 (4)	C13—C14—H14A	120.2
C5—C6—H6A	119.4	C14—C15—C10	121.3 (4)
C1—C6—H6A	119.4	C14—C15—H15A	119.3
O1—C7—C8	122.6 (4)	C10—C15—H15A	119.3
O1—C7—C1	118.7 (4)	O2—C16—H16A	109.5
C8—C7—C1	118.6 (4)	O2—C16—H16B	109.5
C9—C8—C7	120.5 (4)	H16A—C16—H16B	109.5
C9—C8—H8A	119.7	O2—C16—H16C	109.5
C7—C8—H8A	119.7	H16A—C16—H16C	109.5
C8—C9—C10	127.2 (4)	H16B—C16—H16C	109.5

C6—C1—C2—C3	0.1 (7)	C1—C7—C8—C9	164.4 (4)
C7—C1—C2—C3	−179.0 (4)	C7—C8—C9—C10	−178.4 (4)
C6—C1—C2—Br	177.7 (4)	C8—C9—C10—C11	−170.9 (4)
C7—C1—C2—Br	−1.3 (7)	C8—C9—C10—C15	9.4 (7)
C1—C2—C3—C4	−0.8 (7)	C15—C10—C11—C12	−2.4 (6)
Br—C2—C3—C4	−178.6 (4)	C9—C10—C11—C12	177.9 (4)
C2—C3—C4—C5	0.7 (8)	C10—C11—C12—C13	1.9 (6)
C3—C4—C5—C6	0.2 (9)	C16—O2—C13—C12	0.2 (7)
C4—C5—C6—C1	−1.1 (8)	C16—O2—C13—C14	179.6 (5)
C2—C1—C6—C5	0.9 (7)	C11—C12—C13—O2	179.4 (4)
C7—C1—C6—C5	180.0 (4)	C11—C12—C13—C14	0.0 (6)
C2—C1—C7—O1	139.4 (5)	O2—C13—C14—C15	179.2 (4)
C6—C1—C7—O1	−39.6 (7)	C12—C13—C14—C15	−1.4 (7)
C2—C1—C7—C8	−43.2 (7)	C13—C14—C15—C10	0.8 (7)
C6—C1—C7—C8	137.8 (5)	C11—C10—C15—C14	1.0 (7)
O1—C7—C8—C9	−18.2 (7)	C9—C10—C15—C14	−179.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.95	2.59	3.541 (5)	174

Symmetry code: (i) −x+1, y−1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃BrO₂
M_r	317.17
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	110
a, b, c (Å)	12.7300 (8), 4.0061 (3), 13.0035 (6)
β (°)	100.671 (5)
V (Å³)	651.68 (7)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	4.25
Crystal size (mm)	0.48 × 0.41 × 0.28

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini Cu) detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.423, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	2117, 1641, 1621
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.091, 1.07
No. of reflections	1641
No. of parameters	173
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.65
Absolute structure	Flack (1983), 133 Friedel pairs
Absolute structure parameter	0.00 (3)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.95	2.59	3.541 (5)	174.3

Symmetry code: (i) −x+1, y−1/2, −z.

Acknowledgements

KV thanks the UGC for the sanction of a Junior Research Fellowship and for a SAP Chemical grant. HSY thanks the UOM for sabbatical leave. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

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