(2E)-1-(2-Hy­droxy-5-methyl­phen­yl)-3-(4-meth­oxy­phen­yl)prop-2-en-1-one

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

doi:10.1107/S1600536811015054

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1248-o1249

doi:10.1107/S1600536811015054

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(2E)-1-(2-Hydroxy-5-methylphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^*‡ Suhana Arshad,^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 Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India.
^*Correspondence e-mail: hkfun@usm.my

(Received 15 April 2011; accepted 21 April 2011; online 29 April 2011)

In the title compound, C₁₇H₁₆O₃, the dihedral angle between the aromatic rings is 4.59 (7)° and an intramolecular O—H⋯O hydrogen bond generates an S(6) ring. In the crystal, adjacent molecules are linked by C—H⋯O hydrogen bonds, leading to the formation of [001] supramolecular chains. Weak C—H⋯π interactions consolidate the packing.

Related literature

For a related structure and background references to chalcones, see: Fun et al. (2010 ). For related structures, see: Chantrapromma et al. (2009 , 2010 ); Fun et al. (2009 ); Horkaew et al. (2010 ); Lu et al. (2009 ); Suwunwong et al. (2009 ); Wang et al. (2009 , 2010 ); Jasinski et al. (2011 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₁₆O₃
M_r = 268.30
Monoclinic, P 2₁ /c
a = 12.6990 (18) Å
b = 8.8022 (13) Å
c = 13.172 (2) Å
β = 105.565 (2)°
V = 1418.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.46 × 0.32 × 0.18 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.962, T_max = 0.984
11493 measured reflections
4090 independent reflections
2608 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.131
S = 1.02
4090 reflections
187 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.95 (2)	1.65 (2)	2.5112 (18)	149.4 (19)
C11—H11A⋯O3ⁱ	0.93	2.60	3.4317 (17)	149
C16—H16C⋯Cg1ⁱⁱ	0.96	2.81	3.5800 (18)	138
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y, -z.

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/S1600536811015054/hb5847sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015054/hb5847Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811015054/hb5847Isup3.cml

checkCIF report

Comment top

In continuation of our studies on the crystal structures of chalcones (Fun et al., 2010), we now report the synthesis and crystal structure of the title compound, (I). The structures of some related chalcones viz: (Z)-3-(9-anthryl)-1-(4-methoxyphenyl)prop-2-en-1-one (Chantrapromma et al., 2009), (Z)-3-(9-anthryl)- 1-(2-thienyl)prop-2-en-1-one (Fun et al., 2009), (E)-3- (anthracen-9-yl)-1-(4-bromophenyl)prop-2-en-1-one (Suwunwong et al., 2009), (Z)-3-(9-anthryl)-1-(4-bromophenyl)-2-(4-nitro-1H- imidazol-1-yl)prop-2-en-1-one (Lu et al., 2009),(Z)-3- (9-anthryl)-2-(4-nitro-1H-imidazol-1-yl)-1-p-tolylprop- 2-en-1-one (Wang et al., 2009), (E)-3-(9-anthryl)-1- (4-fluorophenyl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one (Wang et al., 2010), (E)-3-(anthracen-9-yl)-1-(furan-2-yl) prop-2-en-1-one (Horkaew et al., 2010), and an orthorhombic polymorph of (Z)-3-(9-anthryl)-1-(2-thienyl)prop-2-en-1-one (Chantrapromma et al., 2010) and 2(E)-3-(4-hydroxyphenyl)-1-(4-chlorophenyl) prop-2-en-1-one (Jasinski et al.,2011) have been reported.

The molecular structure is shown in Fig. 1. An intramolecular O1—H1O1···O2 hydrogen bond (Table 1) stabilizes the molecular structure and forms an S(6) ring motif (Bernstein et al., 1995). The dihedral angle between the phenyl (C1–C6) ring and the methoxy-substituted phenyl (C10–C15) ring is 4.59 (7)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structures (Fun et al., 2010).

In the crystal packing (Fig. 2), the molecules are linked into infinite one-dimensional chain along the c-axis by intermolecular C11—H11A···O3 hydrogen bonds (Table 1). There are also C—H···π interactions (Table 1) which involves C16 and phenyl ring (Cg1 = C1–C6).

Related literature top

For a related structure and background references to chalcones, see: Fun et al. (2010). For related structures, see: Chantrapromma et al. (2009, 2010); Fun et al. (2009); Horkaew et al. (2010); Lu et al. (2009); Suwunwong et al. (2009); Wang et al. (2009, 2010); Jasinski et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987).

Experimental top

2-Hydroxy-5-methylacetophenone (1.50 g, 0.01 mol) was mixed with 4-methoxybenzaldehyde (1.36 g, 0.01 mol) and dissolved in ethanol (40 ml). To this solution, 5 ml of KOH (50%) was added at 278 K. The reaction mixture stirred for 6 h and poured on to crushed ice. The pH of this mixture was adjusted to 3–4 with 2 M HCl aqueous solution. The resulting crude yellow solid was filtered, washed successively with dilute HCl solution and distilled water and finally recrystallized from ethanol (95%) to give the pure chalcone. Orange blocks of (I) were grown by the slow evaporation of the solution of the compound in ethyl alcohol (m. p.: 361 K). Composition: Found (Calculated) for C₁₇H₁₆O₃, C: 76.10 (76.16); H: 6.01 (6.05).

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. The dashed line indicates the intramolecular bond.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis.

(2E)-1-(2-Hydroxy-5-methylphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₇H₁₆O₃	F(000) = 568
M_r = 268.30	D_x = 1.256 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2769 reflections
a = 12.6990 (18) Å	θ = 2.8–28.6°
b = 8.8022 (13) Å	µ = 0.09 mm⁻¹
c = 13.172 (2) Å	T = 296 K
β = 105.565 (2)°	Block, orange
V = 1418.3 (4) Å³	0.46 × 0.32 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	4090 independent reflections
Radiation source: fine-focus sealed tube	2608 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 29.9°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
T_min = 0.962, T_max = 0.984	k = −10→12
11493 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0547P)² + 0.1652P] where P = (F_o² + 2F_c²)/3
4090 reflections	(Δ/σ)_max < 0.001
187 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₇H₁₆O₃	V = 1418.3 (4) Å³
M_r = 268.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.6990 (18) Å	µ = 0.09 mm⁻¹
b = 8.8022 (13) Å	T = 296 K
c = 13.172 (2) Å	0.46 × 0.32 × 0.18 mm
β = 105.565 (2)°

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	4090 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2608 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.984	R_int = 0.024
11493 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.16 e Å⁻³
4090 reflections	Δρ_min = −0.16 e Å⁻³
187 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
O1	0.13821 (11)	0.18686 (15)	0.32930 (8)	0.0794 (4)
O2	0.26594 (9)	0.35672 (14)	0.26545 (7)	0.0758 (3)
O3	0.51456 (8)	0.87081 (13)	−0.15126 (7)	0.0666 (3)
C1	0.03317 (10)	0.26022 (14)	0.04622 (10)	0.0486 (3)
H1A	0.0518	0.3125	−0.0078	0.058*
C2	−0.06268 (11)	0.17724 (16)	0.02260 (12)	0.0553 (3)
C3	−0.08898 (13)	0.10217 (19)	0.10552 (15)	0.0704 (4)
H3A	−0.1538	0.0472	0.0921	0.084*
C4	−0.02277 (15)	0.10664 (19)	0.20568 (15)	0.0728 (4)
H4A	−0.0427	0.0543	0.2590	0.087*
C5	0.07432 (12)	0.18853 (16)	0.22906 (11)	0.0581 (4)
C6	0.10376 (10)	0.26897 (14)	0.14840 (10)	0.0468 (3)
C7	0.20644 (11)	0.35632 (16)	0.17338 (10)	0.0502 (3)
C8	0.23943 (10)	0.44232 (15)	0.09183 (10)	0.0488 (3)
H8A	0.1929	0.4469	0.0240	0.059*
C9	0.33518 (10)	0.51410 (15)	0.11356 (10)	0.0478 (3)
H9A	0.3790	0.5037	0.1822	0.057*
C10	0.38013 (9)	0.60674 (14)	0.04375 (9)	0.0442 (3)
C11	0.48166 (10)	0.67433 (16)	0.08326 (10)	0.0501 (3)
H11A	0.5188	0.6589	0.1536	0.060*
C12	0.52938 (10)	0.76377 (16)	0.02169 (10)	0.0504 (3)
H12A	0.5973	0.8081	0.0504	0.060*
C13	0.47519 (10)	0.78657 (15)	−0.08275 (9)	0.0477 (3)
C14	0.37276 (11)	0.72165 (17)	−0.12373 (10)	0.0581 (4)
H14A	0.3355	0.7385	−0.1939	0.070*
C15	0.32612 (10)	0.63348 (16)	−0.06231 (10)	0.0542 (3)
H15A	0.2577	0.5907	−0.0912	0.065*
C16	−0.13460 (12)	0.16543 (19)	−0.08791 (14)	0.0704 (4)
H16A	−0.1021	0.2204	−0.1347	0.106*
H16B	−0.2051	0.2077	−0.0911	0.106*
H16C	−0.1427	0.0606	−0.1086	0.106*
C17	0.61893 (12)	0.93974 (19)	−0.11419 (12)	0.0645 (4)
H17A	0.6362	0.9942	−0.1708	0.097*
H17B	0.6731	0.8627	−0.0886	0.097*
H17C	0.6181	1.0090	−0.0581	0.097*
H1O1	0.2008 (17)	0.245 (2)	0.3290 (16)	0.107 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1019 (9)	0.0879 (9)	0.0533 (6)	−0.0055 (7)	0.0295 (6)	0.0145 (6)
O2	0.0760 (7)	0.1013 (9)	0.0451 (5)	−0.0174 (6)	0.0078 (5)	0.0079 (5)
O3	0.0642 (6)	0.0840 (8)	0.0509 (5)	−0.0187 (5)	0.0142 (5)	0.0088 (5)
C1	0.0523 (7)	0.0438 (7)	0.0542 (7)	0.0022 (6)	0.0222 (6)	−0.0008 (6)
C2	0.0514 (7)	0.0456 (8)	0.0729 (9)	0.0012 (6)	0.0239 (6)	−0.0062 (6)
C3	0.0651 (9)	0.0595 (10)	0.0961 (13)	−0.0098 (7)	0.0380 (9)	−0.0011 (9)
C4	0.0863 (11)	0.0626 (10)	0.0845 (11)	−0.0079 (9)	0.0488 (10)	0.0088 (8)
C5	0.0756 (9)	0.0509 (8)	0.0567 (8)	0.0042 (7)	0.0331 (7)	0.0038 (6)
C6	0.0552 (7)	0.0413 (7)	0.0496 (7)	0.0036 (6)	0.0241 (6)	−0.0015 (5)
C7	0.0570 (7)	0.0503 (8)	0.0454 (6)	0.0025 (6)	0.0172 (6)	−0.0010 (5)
C8	0.0537 (7)	0.0499 (7)	0.0428 (6)	−0.0015 (6)	0.0130 (5)	−0.0013 (5)
C9	0.0503 (6)	0.0489 (7)	0.0435 (6)	0.0024 (6)	0.0114 (5)	−0.0028 (5)
C10	0.0445 (6)	0.0453 (7)	0.0427 (6)	0.0028 (5)	0.0113 (5)	−0.0040 (5)
C11	0.0458 (6)	0.0617 (9)	0.0395 (6)	0.0009 (6)	0.0058 (5)	0.0004 (6)
C12	0.0400 (6)	0.0621 (9)	0.0462 (6)	−0.0029 (6)	0.0065 (5)	−0.0027 (6)
C13	0.0483 (6)	0.0521 (8)	0.0434 (6)	−0.0004 (6)	0.0135 (5)	−0.0012 (5)
C14	0.0554 (7)	0.0723 (10)	0.0401 (6)	−0.0100 (7)	0.0016 (6)	0.0034 (6)
C15	0.0465 (7)	0.0632 (9)	0.0481 (7)	−0.0098 (6)	0.0042 (5)	−0.0018 (6)
C16	0.0544 (8)	0.0657 (10)	0.0876 (11)	−0.0045 (7)	0.0131 (8)	−0.0117 (8)
C17	0.0614 (8)	0.0662 (10)	0.0707 (9)	−0.0104 (7)	0.0257 (7)	−0.0025 (7)

Geometric parameters (Å, º) top

O1—C5	1.3517 (18)	C9—C10	1.4554 (17)
O1—H1O1	0.94 (2)	C9—H9A	0.9300
O2—C7	1.2449 (15)	C10—C11	1.3881 (17)
O3—C13	1.3624 (15)	C10—C15	1.4011 (17)
O3—C17	1.4198 (17)	C11—C12	1.3814 (18)
C1—C2	1.3815 (18)	C11—H11A	0.9300
C1—C6	1.4048 (18)	C12—C13	1.3778 (17)
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.392 (2)	C13—C14	1.3903 (18)
C2—C16	1.500 (2)	C14—C15	1.3656 (19)
C3—C4	1.361 (2)	C14—H14A	0.9300
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.390 (2)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.4082 (18)	C16—H16C	0.9600
C6—C7	1.4729 (18)	C17—H17A	0.9600
C7—C8	1.4641 (18)	C17—H17B	0.9600
C8—C9	1.3315 (17)	C17—H17C	0.9600
C8—H8A	0.9300

C5—O1—H1O1	106.0 (13)	C11—C10—C9	119.05 (11)
C13—O3—C17	118.65 (11)	C15—C10—C9	123.64 (11)
C2—C1—C6	122.82 (12)	C12—C11—C10	122.26 (11)
C2—C1—H1A	118.6	C12—C11—H11A	118.9
C6—C1—H1A	118.6	C10—C11—H11A	118.9
C1—C2—C3	117.18 (14)	C13—C12—C11	119.26 (11)
C1—C2—C16	121.70 (13)	C13—C12—H12A	120.4
C3—C2—C16	121.11 (14)	C11—C12—H12A	120.4
C4—C3—C2	122.06 (15)	O3—C13—C12	124.53 (11)
C4—C3—H3A	119.0	O3—C13—C14	115.97 (11)
C2—C3—H3A	119.0	C12—C13—C14	119.50 (12)
C3—C4—C5	120.69 (14)	C15—C14—C13	120.86 (12)
C3—C4—H4A	119.7	C15—C14—H14A	119.6
C5—C4—H4A	119.7	C13—C14—H14A	119.6
O1—C5—C4	118.37 (13)	C14—C15—C10	120.80 (12)
O1—C5—C6	122.08 (14)	C14—C15—H15A	119.6
C4—C5—C6	119.54 (14)	C10—C15—H15A	119.6
C1—C6—C5	117.70 (12)	C2—C16—H16A	109.5
C1—C6—C7	122.80 (11)	C2—C16—H16B	109.5
C5—C6—C7	119.49 (12)	H16A—C16—H16B	109.5
O2—C7—C8	119.66 (12)	C2—C16—H16C	109.5
O2—C7—C6	119.25 (12)	H16A—C16—H16C	109.5
C8—C7—C6	121.09 (11)	H16B—C16—H16C	109.5
C9—C8—C7	120.81 (12)	O3—C17—H17A	109.5
C9—C8—H8A	119.6	O3—C17—H17B	109.5
C7—C8—H8A	119.6	H17A—C17—H17B	109.5
C8—C9—C10	128.35 (12)	O3—C17—H17C	109.5
C8—C9—H9A	115.8	H17A—C17—H17C	109.5
C10—C9—H9A	115.8	H17B—C17—H17C	109.5
C11—C10—C15	117.30 (12)

C6—C1—C2—C3	1.0 (2)	O2—C7—C8—C9	3.8 (2)
C6—C1—C2—C16	−177.83 (13)	C6—C7—C8—C9	−176.22 (12)
C1—C2—C3—C4	−1.3 (2)	C7—C8—C9—C10	−178.59 (12)
C16—C2—C3—C4	177.45 (14)	C8—C9—C10—C11	178.78 (13)
C2—C3—C4—C5	0.5 (3)	C8—C9—C10—C15	−0.7 (2)
C3—C4—C5—O1	−178.70 (15)	C15—C10—C11—C12	−0.5 (2)
C3—C4—C5—C6	0.7 (2)	C9—C10—C11—C12	−179.97 (12)
C2—C1—C6—C5	0.22 (19)	C10—C11—C12—C13	−0.4 (2)
C2—C1—C6—C7	179.43 (12)	C17—O3—C13—C12	0.6 (2)
O1—C5—C6—C1	178.32 (12)	C17—O3—C13—C14	−179.83 (13)
C4—C5—C6—C1	−1.1 (2)	C11—C12—C13—O3	−179.21 (13)
O1—C5—C6—C7	−0.9 (2)	C11—C12—C13—C14	1.2 (2)
C4—C5—C6—C7	179.72 (13)	O3—C13—C14—C15	179.21 (13)
C1—C6—C7—O2	−178.73 (13)	C12—C13—C14—C15	−1.2 (2)
C5—C6—C7—O2	0.47 (19)	C13—C14—C15—C10	0.3 (2)
C1—C6—C7—C8	1.27 (19)	C11—C10—C15—C14	0.5 (2)
C5—C6—C7—C8	−179.54 (12)	C9—C10—C15—C14	179.98 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.95 (2)	1.65 (2)	2.5112 (18)	149.4 (19)
C11—H11A···O3ⁱ	0.93	2.60	3.4317 (17)	149
C16—H16C···Cg1ⁱⁱ	0.96	2.81	3.5800 (18)	138

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆O₃
M_r	268.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.6990 (18), 8.8022 (13), 13.172 (2)
β (°)	105.565 (2)
V (Å³)	1418.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.46 × 0.32 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.962, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	11493, 4090, 2608
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.702

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.131, 1.02
No. of reflections	4090
No. of parameters	187
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.16

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	0.95 (2)	1.65 (2)	2.5112 (18)	149.4 (19)
C11—H11A···O3ⁱ	0.93	2.60	3.4317 (17)	149.4
C16—H16C···Cg1ⁱⁱ	0.96	2.81	3.5800 (18)	138

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). SA thanks the Malaysian Government and USM for the award of a research scholarship. VMK also thanks P. A. College of Engineering for research facilities.

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