2,3-Dibromo-3-(4-chloro­phen­yl)-1-(2-hy­droxy­phen­yl)propan-1-one

Fun, H.-K.; Loh, W.-S.; Sarojini, B.K.; Khaleel, V.M.; Narayana, B.

doi:10.1107/S1600536811036798

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Pages o2651-o2652

https://doi.org/10.1107/S1600536811036798

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2,3-Dibromo-3-(4-chlorophenyl)-1-(2-hydroxyphenyl)propan-1-one

Hoong-Kun Fun,^a ^*‡ Wan-Sin Loh,^a § B. K. Sarojini,^b V. Musthafa Khaleel ^b and B. Narayana ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, P. A. College of Engineering, Mangalore 574 153, India, and ^cDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 2 September 2011; accepted 10 September 2011; online 17 September 2011)

In the title molecule, C₁₅H₁₁Br₂ClO₂, an S(6) ring motif is formed via an intramolecular O—H⋯O hydrogen bond. The dihedral angle formed between the chloro- and hydroxy-substituted benzene rings is 34.10 (15)°. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into chains along the c axis.

Related literature

For applications of chalcone compounds, see: Liu et al. (2003 ); Nielson et al. (1998 ); Rajas et al. (2002 ); Dinkova-Kostova et al. (1998 ); Goto et al. (1991 ); Uchida et al. (1998); Tam et al. (1989 ); Indira et al. (2002 ); Sarojini et al. (2006 ). For related structures, see: Butcher, Yathirajan, Anilkumar et al. (2006 ); Butcher, Yathirajan, Sarojini et al. (2006 ); Harrison et al. (2005 ); Yathirajan, Mayekar et al. (2007 ); Yathirajan, Vijesh et al. (2007 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₁Br₂ClO₂
M_r = 418.51
Monoclinic, C 2/c
a = 29.075 (3) Å
b = 9.2358 (10) Å
c = 11.4374 (12) Å
β = 103.290 (2)°
V = 2989.0 (6) Å³
Z = 8
Mo Kα radiation
μ = 5.60 mm⁻¹
T = 297 K
0.39 × 0.36 × 0.22 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.218, T_max = 0.379
16663 measured reflections
5375 independent reflections
3337 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.122
S = 1.04
5375 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.80	1.87	2.591 (3)	150
C11—H11A⋯O2ⁱ	0.93	2.53	3.416 (4)	160
Symmetry code: (i) $[x, -y+2, z-{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536811036798/lh5331sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036798/lh5331Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811036798/lh5331Isup3.cml

checkCIF report

Comment top

For a structurally simple group of compounds, chalcones display an impressive array of biological activities, among which antimalarial (Liu et al., 2003), antiprotozoal (Nielson et al., 1998), nitric oxide inhibition (Rajas et al., 2002) and anticancer activities (Dinkova-Kostova et al., 1998) have been reported in the literature. Among several organic compounds reported for non-linear optical (NLO) properties, chalcone derivatives are notable materials for their excellent blue light transmittance and good crystallizability. They provide a necessary configuration to show NLO properties, with two planar rings connected through a conjugated double bond (Goto et al., 1991; Uchida et al., 1998; Tam et al., 1989; Indira et al., 2002; Sarojini et al., 2006). The substitution of a bromo group on either of the phenyl rings can influence the non-centrosymmetric crystal packing. The bromo group can obviously improve the molecular first-order hyperpolarizabilities and can effectively reduce dipole-dipole interactions between the molecules. Chalcone derivatives usually have a lower melting temperature, which can be a drawback when we use these crystals in optical instruments. Chalcone dibromides usually have higher melting points and are thermally stable. Only a few structures of these compounds have been reported (Butcher, Yathirajan, Anilkumar et al., 2006; Butcher, Yathirajan, Sarojini et al.,2006; Harrison et al., 2005; Yathirajan, Mayekar et al., 2007; Yathirajan, Vijesh et al., 2007). In continuation to our studies on crystal structures of chalcones, we report the synthesis and crystal structure of the title compound.

In the title compound (Fig. 1), an S(6) ring motif (Bernstein et al., 1995) is formed via the intramolecular O1—H1O1···O2 hydrogen bond (Table 1). The dihedral angle formed between the chloro-substituted benzene ring (C1–C6) and hydroxy-substituted benzene ring (C10–C15) is 34.10 (15)°.

In the crystal packing (Fig. 2), intermolecular C11—H11A···O2ⁱ hydrogen bonds (Table 1) link the molecules into chains along the c axis.

Related literature top

For applications of chalcone compounds, see: Liu et al. (2003); Nielson et al. (1998); Rajas et al. (2002); Dinkova-Kostova et al. (1998); Goto et al. (1991); Uchida et al. (1998); Tam et al. (1989); Indira et al. (2002); Sarojini et al. (2006). For related structures, see: Butcher, Yathirajan, Anilkumar et al. (2006); Butcher, Yathirajan, Sarojini et al. (2006); Harrison et al. (2005); Yathirajan, Mayekar et al. (2007); Yathirajan, Vijesh et al. (2007). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

(2E)-1-(2-Hydroxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one (0.01 mol) was treated with bromine in acetic acid (30%) until the orange colour of the solution persisted. After stirring for half an hour, the contents were poured onto crushed ice. The resulting solid mass was collected by filtration. The compound was dried and recrystallized from ethanol. Crystals suitable for structure determination were obtained from acetone by slow evaporation (m. p. = 395–397 K). Composition: Found (Calculated) for C₁₅H₁₁Br₂ClO₂, C: 43.19 (43.05); H: 2.68 (2.65).

Structure description top

In the crystal packing (Fig. 2), intermolecular C11—H11A···O2ⁱ hydrogen bonds (Table 1) link the molecules into chains along the c axis.

For applications of chalcone compounds, see: Liu et al. (2003); Nielson et al. (1998); Rajas et al. (2002); Dinkova-Kostova et al. (1998); Goto et al. (1991); Uchida et al. (1998); Tam et al. (1989); Indira et al. (2002); Sarojini et al. (2006). For related structures, see: Butcher, Yathirajan, Anilkumar et al. (2006); Butcher, Yathirajan, Sarojini et al. (2006); Harrison et al. (2005); Yathirajan, Mayekar et al. (2007); Yathirajan, Vijesh et al. (2007). For hydrogen-bond motifs, see: Bernstein et al. (1995).

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 30% probability displacement ellipsoids. The dashed line shows an intramolecular hydrogen bond.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. Weak C—H···O hydrogen bonds are shown as dashed lines.

2,3-Dibromo-3-(4-chlorophenyl)-1-(2-hydroxyphenyl)propan-1-one top

Crystal data top

C₁₅H₁₁Br₂ClO₂	F(000) = 1632
M_r = 418.51	D_x = 1.860 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4431 reflections
a = 29.075 (3) Å	θ = 2.9–29.1°
b = 9.2358 (10) Å	µ = 5.60 mm⁻¹
c = 11.4374 (12) Å	T = 297 K
β = 103.290 (2)°	Block, yellow
V = 2989.0 (6) Å³	0.39 × 0.36 × 0.22 mm
Z = 8

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	5375 independent reflections
Radiation source: fine-focus sealed tube	3337 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 32.6°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −43→39
T_min = 0.218, T_max = 0.379	k = −13→13
16663 measured reflections	l = −13→17

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0657P)²] where P = (F_o² + 2F_c²)/3
5375 reflections	(Δ/σ)_max = 0.001
181 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₅H₁₁Br₂ClO₂	V = 2989.0 (6) Å³
M_r = 418.51	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 29.075 (3) Å	µ = 5.60 mm⁻¹
b = 9.2358 (10) Å	T = 297 K
c = 11.4374 (12) Å	0.39 × 0.36 × 0.22 mm
β = 103.290 (2)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	5375 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3337 reflections with I > 2σ(I)
T_min = 0.218, T_max = 0.379	R_int = 0.034
16663 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.04	Δρ_max = 0.61 e Å⁻³
5375 reflections	Δρ_min = −0.47 e Å⁻³
181 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
Cl1	0.04064 (3)	0.29705 (9)	0.14615 (9)	0.0677 (2)
Br1	0.191164 (10)	0.81997 (3)	0.36623 (3)	0.05335 (11)
Br2	0.046011 (11)	0.98145 (4)	0.41259 (3)	0.06342 (12)
O1	0.19186 (10)	1.3218 (2)	0.57890 (18)	0.0611 (6)
H1O1	0.1812	1.2476	0.5965	0.092*
O2	0.15388 (9)	1.0666 (2)	0.55101 (17)	0.0574 (5)
C1	0.06311 (12)	0.7159 (3)	0.2247 (3)	0.0545 (7)
H1A	0.0577	0.8040	0.1845	0.065*
C2	0.04955 (11)	0.5874 (3)	0.1622 (3)	0.0553 (7)
H2A	0.0355	0.5891	0.0805	0.066*
C3	0.05732 (10)	0.4580 (3)	0.2236 (3)	0.0480 (6)
C4	0.07828 (10)	0.4529 (3)	0.3435 (3)	0.0480 (6)
H4A	0.0835	0.3645	0.3832	0.058*
C5	0.09170 (10)	0.5816 (3)	0.4055 (3)	0.0469 (6)
H5A	0.1056	0.5791	0.4873	0.056*
C6	0.08443 (9)	0.7138 (3)	0.3460 (2)	0.0422 (5)
C7	0.10038 (10)	0.8494 (3)	0.4158 (3)	0.0444 (6)
H7A	0.1148	0.8237	0.4993	0.053*
C8	0.13502 (9)	0.9403 (3)	0.3658 (2)	0.0417 (5)
H8A	0.1204	0.9719	0.2839	0.050*
C9	0.15471 (10)	1.0703 (3)	0.4438 (2)	0.0421 (5)
C10	0.17415 (9)	1.1927 (2)	0.3898 (2)	0.0376 (5)
C11	0.17591 (11)	1.1946 (3)	0.2682 (2)	0.0481 (6)
H11A	0.1641	1.1165	0.2191	0.058*
C12	0.19496 (12)	1.3112 (3)	0.2210 (3)	0.0550 (7)
H12A	0.1959	1.3116	0.1403	0.066*
C13	0.21269 (11)	1.4279 (3)	0.2937 (3)	0.0545 (7)
H13A	0.2253	1.5066	0.2611	0.065*
C14	0.21187 (10)	1.4284 (3)	0.4115 (3)	0.0516 (7)
H14A	0.2242	1.5071	0.4593	0.062*
C15	0.19263 (10)	1.3118 (3)	0.4619 (2)	0.0428 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0831 (6)	0.0495 (4)	0.0769 (5)	−0.0197 (4)	0.0312 (4)	−0.0233 (4)
Br1	0.05194 (17)	0.04197 (15)	0.0691 (2)	0.00312 (11)	0.02003 (14)	−0.00637 (12)
Br2	0.05503 (19)	0.05123 (18)	0.0874 (3)	0.00816 (13)	0.02336 (16)	−0.00960 (15)
O1	0.0985 (17)	0.0433 (10)	0.0428 (11)	−0.0141 (10)	0.0186 (11)	−0.0098 (8)
O2	0.0898 (16)	0.0454 (10)	0.0388 (10)	−0.0148 (10)	0.0190 (10)	−0.0032 (8)
C1	0.0681 (18)	0.0395 (13)	0.0523 (17)	−0.0053 (13)	0.0062 (14)	0.0032 (12)
C2	0.0684 (18)	0.0489 (15)	0.0468 (16)	−0.0067 (13)	0.0092 (13)	−0.0065 (12)
C3	0.0495 (14)	0.0417 (13)	0.0570 (17)	−0.0074 (11)	0.0206 (12)	−0.0129 (12)
C4	0.0531 (15)	0.0315 (11)	0.0615 (18)	−0.0039 (10)	0.0174 (13)	0.0012 (11)
C5	0.0507 (14)	0.0390 (12)	0.0507 (15)	−0.0021 (11)	0.0111 (11)	0.0028 (11)
C6	0.0475 (13)	0.0345 (11)	0.0454 (14)	−0.0047 (10)	0.0121 (11)	−0.0022 (10)
C7	0.0536 (14)	0.0328 (11)	0.0476 (14)	−0.0016 (10)	0.0132 (11)	0.0000 (10)
C8	0.0507 (13)	0.0330 (11)	0.0418 (13)	−0.0013 (10)	0.0118 (11)	−0.0011 (9)
C9	0.0561 (14)	0.0320 (10)	0.0365 (13)	−0.0020 (10)	0.0076 (11)	−0.0007 (9)
C10	0.0464 (12)	0.0305 (10)	0.0354 (12)	−0.0008 (9)	0.0083 (10)	−0.0001 (9)
C11	0.0611 (16)	0.0437 (13)	0.0388 (14)	−0.0058 (12)	0.0100 (12)	−0.0031 (10)
C12	0.0691 (18)	0.0549 (16)	0.0433 (15)	−0.0072 (14)	0.0178 (13)	0.0084 (12)
C13	0.0631 (17)	0.0412 (13)	0.0581 (18)	−0.0073 (12)	0.0119 (14)	0.0105 (12)
C14	0.0586 (16)	0.0306 (11)	0.0623 (18)	−0.0067 (11)	0.0077 (13)	−0.0024 (11)
C15	0.0513 (14)	0.0319 (11)	0.0432 (14)	0.0005 (10)	0.0065 (11)	−0.0002 (9)

Geometric parameters (Å, º) top

Cl1—C3	1.741 (3)	C6—C7	1.501 (3)
Br1—C8	1.974 (3)	C7—C8	1.520 (4)
Br2—C7	1.990 (3)	C7—H7A	0.9800
O1—C15	1.347 (3)	C8—C9	1.527 (3)
O1—H1O1	0.7971	C8—H8A	0.9800
O2—C9	1.232 (3)	C9—C10	1.463 (3)
C1—C6	1.383 (4)	C10—C11	1.403 (4)
C1—C2	1.395 (4)	C10—C15	1.406 (3)
C1—H1A	0.9300	C11—C12	1.376 (4)
C2—C3	1.378 (4)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.386 (4)
C3—C4	1.367 (4)	C12—H12A	0.9300
C4—C5	1.393 (4)	C13—C14	1.353 (4)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.390 (4)	C14—C15	1.398 (4)
C5—H5A	0.9300	C14—H14A	0.9300

C15—O1—H1O1	106.8	C7—C8—Br1	107.91 (17)
C6—C1—C2	120.7 (3)	C9—C8—Br1	104.04 (17)
C6—C1—H1A	119.6	C7—C8—H8A	110.2
C2—C1—H1A	119.6	C9—C8—H8A	110.2
C3—C2—C1	118.9 (3)	Br1—C8—H8A	110.2
C3—C2—H2A	120.6	O2—C9—C10	122.7 (2)
C1—C2—H2A	120.6	O2—C9—C8	118.0 (2)
C4—C3—C2	121.6 (2)	C10—C9—C8	119.3 (2)
C4—C3—Cl1	119.2 (2)	C11—C10—C15	118.4 (2)
C2—C3—Cl1	119.2 (2)	C11—C10—C9	122.3 (2)
C3—C4—C5	119.3 (3)	C15—C10—C9	119.3 (2)
C3—C4—H4A	120.3	C12—C11—C10	120.6 (3)
C5—C4—H4A	120.3	C12—C11—H11A	119.7
C6—C5—C4	120.4 (3)	C10—C11—H11A	119.7
C6—C5—H5A	119.8	C11—C12—C13	120.0 (3)
C4—C5—H5A	119.8	C11—C12—H12A	120.0
C1—C6—C5	119.1 (2)	C13—C12—H12A	120.0
C1—C6—C7	122.3 (2)	C14—C13—C12	120.7 (3)
C5—C6—C7	118.6 (2)	C14—C13—H13A	119.6
C6—C7—C8	114.2 (2)	C12—C13—H13A	119.6
C6—C7—Br2	110.76 (19)	C13—C14—C15	120.5 (3)
C8—C7—Br2	104.30 (16)	C13—C14—H14A	119.7
C6—C7—H7A	109.1	C15—C14—H14A	119.7
C8—C7—H7A	109.1	O1—C15—C14	117.2 (2)
Br2—C7—H7A	109.1	O1—C15—C10	123.0 (2)
C7—C8—C9	113.9 (2)	C14—C15—C10	119.7 (3)

C6—C1—C2—C3	0.7 (5)	Br1—C8—C9—O2	−94.9 (3)
C1—C2—C3—C4	−0.6 (5)	C7—C8—C9—C10	−158.4 (2)
C1—C2—C3—Cl1	−179.8 (3)	Br1—C8—C9—C10	84.4 (2)
C2—C3—C4—C5	0.7 (4)	O2—C9—C10—C11	178.6 (3)
Cl1—C3—C4—C5	179.9 (2)	C8—C9—C10—C11	−0.7 (4)
C3—C4—C5—C6	−0.8 (4)	O2—C9—C10—C15	−0.2 (4)
C2—C1—C6—C5	−0.8 (5)	C8—C9—C10—C15	−179.5 (2)
C2—C1—C6—C7	178.8 (3)	C15—C10—C11—C12	−0.5 (4)
C4—C5—C6—C1	0.9 (4)	C9—C10—C11—C12	−179.3 (3)
C4—C5—C6—C7	−178.7 (3)	C10—C11—C12—C13	0.1 (5)
C1—C6—C7—C8	−56.8 (4)	C11—C12—C13—C14	0.5 (5)
C5—C6—C7—C8	122.8 (3)	C12—C13—C14—C15	−0.7 (5)
C1—C6—C7—Br2	60.6 (3)	C13—C14—C15—O1	−178.2 (3)
C5—C6—C7—Br2	−119.8 (2)	C13—C14—C15—C10	0.3 (4)
C6—C7—C8—C9	−174.5 (2)	C11—C10—C15—O1	178.7 (3)
Br2—C7—C8—C9	64.5 (2)	C9—C10—C15—O1	−2.5 (4)
C6—C7—C8—Br1	−59.5 (3)	C11—C10—C15—C14	0.3 (4)
Br2—C7—C8—Br1	179.45 (11)	C9—C10—C15—C14	179.2 (3)
C7—C8—C9—O2	22.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.80	1.87	2.591 (3)	150
C11—H11A···O2ⁱ	0.93	2.53	3.416 (4)	160

Symmetry code: (i) x, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁Br₂ClO₂
M_r	418.51
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	297
a, b, c (Å)	29.075 (3), 9.2358 (10), 11.4374 (12)
β (°)	103.290 (2)
V (Å³)	2989.0 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.60
Crystal size (mm)	0.39 × 0.36 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.218, 0.379
No. of measured, independent and observed [I > 2σ(I)] reflections	16663, 5375, 3337
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.757

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.122, 1.04
No. of reflections	5375
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.47

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
O1—H1O1···O2	0.80	1.87	2.591 (3)	150
C11—H11A···O2ⁱ	0.93	2.53	3.416 (4)	160.3

Symmetry code: (i) x, −y+2, z−1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7581-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of a research fellowship. VMK thanks P. A. College of Engineering for research facilities.

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