(2E)-2-Benzyl­idene-5,6-dimethoxy­indan-1-one

Ali, M.A.; Ismail, R.; Tan, S.C.; Yeap, C.S.; Fun, H.-K.

doi:10.1107/S1600536810035695

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2531-o2532

doi:10.1107/S1600536810035695

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(2E)-2-Benzylidene-5,6-dimethoxyindan-1-one

Mohamed Ashraf Ali,^a Rusli Ismail,^a Soo Choon Tan,^a Chin Sing Yeap ^b ‡ and Hoong-Kun Fun ^b ^*§

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 3 September 2010; accepted 6 September 2010; online 11 September 2010)

The molecular structure of the title compound, C₁₈H₁₆O₃, is roughly planar; the maximum deviation of the indanone ring system is 0.027 (1) Å and it makes a dihedral angle of 2.69 (3)° with the phenyl ring. The torsion angles between the two methoxy groups and the indanone ring are −14.67 (11) and −1.11 (12)°. In the crystal, molecules are connected into a ribbon along the a axis via weak intermolecular C—H⋯O hydrogen bonds. Weak intermolecular C—H⋯π and π–π [centroid–centroid distance = 3.7086 (6) Å] interactions are also observed.

Related literature

For general background to and the biological activity of chalcone derivatives, see: Boumendjel et al. (2009 ); D'Archivio et al. (2008 ); Dicarlo et al. (1999 ); Echeverria et al. (2009 ); Heidenreich et al. (2008 ); Katsori & Hadjipavlou-Latina (2009 ); Miranda et al. (1999 ); Nowakowska (2007 ); Shah et al. (2008 ); Syed et al. (2008 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₈H₁₆O₃
M_r = 280.31
Monoclinic, P 2₁ /c
a = 6.0209 (6) Å
b = 14.8550 (14) Å
c = 15.2292 (15) Å
β = 90.603 (2)°
V = 1362.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.44 × 0.29 × 0.16 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.960, T_max = 0.985
31475 measured reflections
6003 independent reflections
4902 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.130
S = 1.09
6003 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O3ⁱ	0.96	2.53	3.4107 (11)	152
C18—H18B⋯O2ⁱⁱ	0.96	2.58	3.5320 (11)	173
C16—H16A⋯Cg1ⁱⁱⁱ	0.93	2.99	3.7224 (9)	137
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x+1, y, z; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

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/S1600536810035695/is2598sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035695/is2598Isup2.hkl

checkCIF report

Comment top

Chalcones have been reported to possess antiinflammatory, antimicrobial, antioxidant and anticancer properties (Echeverria et al., 2009; Nowakowska, 2007; Miranda et al., 1999; Shah et al., 2008; Boumendjel et al., 2009; Katsori & Hadjipavlou-Latina, 2009). Chalcones are one of the major classes of natural products with widespread distribution in spices, tea, beer, fruits and vegetables. They have been recently subjects of great interest for their pharmacological activities (Dicarlo et al., 1999). Prostate cancer is one of the most commonly diagnosed cancers in men and the second leading cause of cancer deaths in the European Union and United States of America (Heidenreich et al., 2008). Many antitumor drugs have been developed for prostate cancer patients, but their intolerable systemic toxicity often limits their clinical use. Chemoprevention is one of the most promising approaches in prostate cancer research, in which natural or synthetic agents are used to prevent this malignant disease (Heidenreich et al., 2008; Syed et al., 2008; D'Archivio et al., 2008).

The molecular structure of the title compound is essentially coplanar (Fig. 1). The maximum deviation of the indanone group is 0.027 (1) Å and it makes dihedral angle of 2.69 (3)° with the phenyl ring [C11–C16]. The torsion angles of the two methoxy groups are [C17–O2–C4–C5] 165.99 (7) and [C18–O3–C5–C4] 179.19 (7)°.

In the crystal structure, intermolecular C17—H17A···O3 hydrogen bonds (Table 1) link the molecules into dimers (Fig. 2). These dimers are interconnected into ribbons propagating along the [100] direction via intermolecular C18—H18B···O2 hydrogen bonds (Fig. 2, Table 1). Weak intermolecular C—H···π (Table 1) and π–π interactions are also observed. [Cg1···Cg2^iv of 3.7086 (6) Å; (iv) 1 - x, 1 - y, -z. Cg1 and Cg2 are the centroids of C2–C7 and C11–C16 benzene ring.]

Related literature top

For general background to and the biological activity of chalcone derivatives, see: Boumendjel et al. (2009); D'Archivio et al. (2008); Dicarlo et al. (1999); Echeverria et al. (2009); Heidenreich et al. (2008); Katsori & Hadjipavlou-Latina (2009); Miranda et al. (1999); Nowakowska (2007); Shah et al. (2008); Syed et al. (2008). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 5,6-dimethoxyindan-1-one (0.001 mmol) and benzaldehyde (0.001 mmol) were dissolved in methanol (10 ml) and 30% sodium hydroxide solution (5 ml) was added and stirred for 5 h. After completion of the reaction as evident from TLC, the mixture was poured into crushed ice then neutralized with concentrated HCl. The precipitated solid was filtered, washed with water and recrystallized from ethanol to reveal the title compound as light yellow crystals.

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 with atom labels and 50% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of title compound, showing chains along the [100] direction. Intermolecular hydrogen bonds are shown as dashed lines.

(2E)-2-Benzylidene-5,6-dimethoxyindan-1-one top

Crystal data top

C₁₈H₁₆O₃	F(000) = 592
M_r = 280.31	D_x = 1.367 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7296 reflections
a = 6.0209 (6) Å	θ = 2.7–34.9°
b = 14.8550 (14) Å	µ = 0.09 mm⁻¹
c = 15.2292 (15) Å	T = 100 K
β = 90.603 (2)°	Yellow, colourless
V = 1362.0 (2) Å³	0.44 × 0.29 × 0.16 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	6003 independent reflections
Radiation source: fine-focus sealed tube	4902 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ϕ and ω scans	θ_max = 35.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.960, T_max = 0.985	k = −23→23
31475 measured reflections	l = −23→24

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0698P)² + 0.2363P] where P = (F_o² + 2F_c²)/3
6003 reflections	(Δ/σ)_max = 0.001
192 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

C₁₈H₁₆O₃	V = 1362.0 (2) Å³
M_r = 280.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.0209 (6) Å	µ = 0.09 mm⁻¹
b = 14.8550 (14) Å	T = 100 K
c = 15.2292 (15) Å	0.44 × 0.29 × 0.16 mm
β = 90.603 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	6003 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4902 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.985	R_int = 0.048
31475 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.09	Δρ_max = 0.60 e Å⁻³
6003 reflections	Δρ_min = −0.58 e Å⁻³
192 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
O1	0.07043 (10)	0.71482 (4)	0.09037 (4)	0.01685 (13)
O2	0.07512 (10)	0.55593 (4)	0.41523 (4)	0.01527 (12)
O3	0.42675 (10)	0.46101 (4)	0.40716 (4)	0.01623 (13)
C1	0.22764 (13)	0.66575 (5)	0.11035 (5)	0.01189 (13)
C2	0.26214 (13)	0.61731 (5)	0.19344 (5)	0.01122 (13)
C3	0.12486 (13)	0.61613 (5)	0.26768 (5)	0.01208 (13)
H3A	−0.0055	0.6497	0.2689	0.014*
C4	0.18842 (13)	0.56395 (5)	0.33862 (5)	0.01188 (13)
C5	0.38768 (13)	0.51154 (5)	0.33496 (5)	0.01213 (13)
C6	0.52425 (13)	0.51522 (5)	0.26166 (5)	0.01263 (14)
H6A	0.6561	0.4827	0.2602	0.015*
C7	0.45911 (12)	0.56873 (5)	0.19043 (5)	0.01121 (13)
C8	0.57760 (13)	0.58179 (5)	0.10412 (5)	0.01231 (13)
H8A	0.5966	0.5249	0.0738	0.015*
H8B	0.7219	0.6095	0.1131	0.015*
C9	0.42250 (13)	0.64368 (5)	0.05349 (5)	0.01186 (13)
C10	0.43407 (13)	0.67809 (5)	−0.02828 (5)	0.01274 (14)
H10A	0.3154	0.7150	−0.0441	0.015*
C11	0.60191 (13)	0.66724 (5)	−0.09638 (5)	0.01229 (13)
C12	0.79718 (14)	0.61621 (6)	−0.08618 (5)	0.01469 (14)
H12A	0.8259	0.5868	−0.0334	0.018*
C13	0.94801 (14)	0.60945 (6)	−0.15463 (6)	0.01690 (15)
H13A	1.0760	0.5751	−0.1472	0.020*
C14	0.90917 (15)	0.65353 (6)	−0.23413 (6)	0.01682 (15)
H14A	1.0106	0.6487	−0.2795	0.020*
C15	0.71743 (15)	0.70489 (6)	−0.24506 (6)	0.01576 (15)
H15A	0.6910	0.7349	−0.2977	0.019*
C16	0.56526 (14)	0.71135 (5)	−0.17716 (5)	0.01416 (14)
H16A	0.4370	0.7454	−0.1853	0.017*
C17	−0.09525 (14)	0.62140 (6)	0.43137 (6)	0.01619 (15)
H17A	−0.1545	0.6122	0.4890	0.024*
H17B	−0.2118	0.6149	0.3883	0.024*
H17C	−0.0333	0.6808	0.4276	0.024*
C18	0.62128 (14)	0.40534 (6)	0.40883 (6)	0.01640 (15)
H18A	0.6235	0.3701	0.4617	0.025*
H18B	0.7514	0.4426	0.4071	0.025*
H18C	0.6192	0.3660	0.3588	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0151 (3)	0.0202 (3)	0.0153 (3)	0.0057 (2)	0.0018 (2)	0.0026 (2)
O2	0.0144 (3)	0.0191 (3)	0.0123 (3)	0.0035 (2)	0.0052 (2)	0.0029 (2)
O3	0.0157 (3)	0.0197 (3)	0.0133 (3)	0.0048 (2)	0.0024 (2)	0.0056 (2)
C1	0.0121 (3)	0.0125 (3)	0.0111 (3)	0.0000 (2)	0.0014 (2)	−0.0003 (2)
C2	0.0117 (3)	0.0116 (3)	0.0104 (3)	−0.0001 (2)	0.0013 (2)	0.0003 (2)
C3	0.0116 (3)	0.0128 (3)	0.0119 (3)	0.0004 (2)	0.0017 (2)	0.0001 (2)
C4	0.0109 (3)	0.0137 (3)	0.0111 (3)	−0.0003 (2)	0.0024 (2)	0.0000 (2)
C5	0.0122 (3)	0.0126 (3)	0.0116 (3)	0.0001 (2)	0.0005 (2)	0.0014 (2)
C6	0.0116 (3)	0.0143 (3)	0.0120 (3)	0.0013 (2)	0.0012 (2)	0.0009 (2)
C7	0.0112 (3)	0.0114 (3)	0.0110 (3)	−0.0005 (2)	0.0013 (2)	−0.0001 (2)
C8	0.0118 (3)	0.0140 (3)	0.0111 (3)	0.0013 (2)	0.0021 (2)	0.0007 (2)
C9	0.0118 (3)	0.0124 (3)	0.0115 (3)	0.0005 (2)	0.0019 (2)	0.0000 (2)
C10	0.0134 (3)	0.0130 (3)	0.0118 (3)	0.0010 (2)	0.0015 (2)	0.0003 (2)
C11	0.0136 (3)	0.0120 (3)	0.0113 (3)	−0.0004 (2)	0.0015 (2)	0.0002 (2)
C12	0.0143 (3)	0.0165 (3)	0.0133 (3)	0.0018 (3)	0.0019 (3)	0.0014 (3)
C13	0.0148 (3)	0.0193 (4)	0.0167 (4)	0.0021 (3)	0.0038 (3)	−0.0005 (3)
C14	0.0175 (4)	0.0185 (4)	0.0146 (3)	−0.0029 (3)	0.0057 (3)	−0.0015 (3)
C15	0.0186 (4)	0.0164 (3)	0.0123 (3)	−0.0030 (3)	0.0024 (3)	0.0015 (3)
C16	0.0154 (3)	0.0145 (3)	0.0126 (3)	0.0003 (2)	0.0012 (3)	0.0013 (2)
C17	0.0141 (3)	0.0189 (4)	0.0156 (3)	0.0024 (3)	0.0043 (3)	−0.0007 (3)
C18	0.0153 (3)	0.0169 (3)	0.0171 (4)	0.0032 (3)	−0.0010 (3)	0.0032 (3)

Geometric parameters (Å, º) top

O1—C1	1.2303 (10)	C10—C11	1.4645 (11)
O2—C4	1.3628 (10)	C10—H10A	0.9300
O2—C17	1.4366 (10)	C11—C12	1.4061 (11)
O3—C5	1.3499 (10)	C11—C16	1.4092 (11)
O3—C18	1.4338 (10)	C12—C13	1.3933 (12)
C1—C2	1.4687 (11)	C12—H12A	0.9300
C1—C9	1.5017 (11)	C13—C14	1.3941 (12)
C2—C7	1.3894 (11)	C13—H13A	0.9300
C2—C3	1.4076 (11)	C14—C15	1.3923 (13)
C3—C4	1.3805 (11)	C14—H14A	0.9300
C3—H3A	0.9300	C15—C16	1.3920 (12)
C4—C5	1.4318 (11)	C15—H15A	0.9300
C5—C6	1.3945 (11)	C16—H16A	0.9300
C6—C7	1.3977 (11)	C17—H17A	0.9600
C6—H6A	0.9300	C17—H17B	0.9600
C7—C8	1.5146 (11)	C17—H17C	0.9600
C8—C9	1.5154 (11)	C18—H18A	0.9600
C8—H8A	0.9700	C18—H18B	0.9600
C8—H8B	0.9700	C18—H18C	0.9600
C9—C10	1.3487 (11)

C4—O2—C17	116.88 (6)	C9—C10—H10A	114.5
C5—O3—C18	118.07 (7)	C11—C10—H10A	114.5
O1—C1—C2	127.21 (7)	C12—C11—C16	118.04 (7)
O1—C1—C9	126.20 (7)	C12—C11—C10	124.30 (7)
C2—C1—C9	106.59 (6)	C16—C11—C10	117.65 (7)
C7—C2—C3	121.92 (7)	C13—C12—C11	120.47 (8)
C7—C2—C1	109.82 (7)	C13—C12—H12A	119.8
C3—C2—C1	128.26 (7)	C11—C12—H12A	119.8
C4—C3—C2	118.38 (7)	C12—C13—C14	120.74 (8)
C4—C3—H3A	120.8	C12—C13—H13A	119.6
C2—C3—H3A	120.8	C14—C13—H13A	119.6
O2—C4—C3	125.58 (7)	C15—C14—C13	119.50 (8)
O2—C4—C5	114.40 (7)	C15—C14—H14A	120.2
C3—C4—C5	120.02 (7)	C13—C14—H14A	120.2
O3—C5—C6	125.08 (7)	C16—C15—C14	120.02 (8)
O3—C5—C4	114.17 (7)	C16—C15—H15A	120.0
C6—C5—C4	120.75 (7)	C14—C15—H15A	120.0
C5—C6—C7	118.72 (7)	C15—C16—C11	121.21 (8)
C5—C6—H6A	120.6	C15—C16—H16A	119.4
C7—C6—H6A	120.6	C11—C16—H16A	119.4
C2—C7—C6	120.16 (7)	O2—C17—H17A	109.5
C2—C7—C8	111.85 (7)	O2—C17—H17B	109.5
C6—C7—C8	127.99 (7)	H17A—C17—H17B	109.5
C7—C8—C9	103.06 (6)	O2—C17—H17C	109.5
C7—C8—H8A	111.2	H17A—C17—H17C	109.5
C9—C8—H8A	111.2	H17B—C17—H17C	109.5
C7—C8—H8B	111.2	O3—C18—H18A	109.5
C9—C8—H8B	111.2	O3—C18—H18B	109.5
H8A—C8—H8B	109.1	H18A—C18—H18B	109.5
C10—C9—C1	119.86 (7)	O3—C18—H18C	109.5
C10—C9—C8	131.47 (7)	H18A—C18—H18C	109.5
C1—C9—C8	108.67 (6)	H18B—C18—H18C	109.5
C9—C10—C11	130.91 (7)

O1—C1—C2—C7	179.73 (8)	C5—C6—C7—C2	0.24 (11)
C9—C1—C2—C7	−0.12 (8)	C5—C6—C7—C8	−178.92 (7)
O1—C1—C2—C3	0.09 (13)	C2—C7—C8—C9	−1.30 (8)
C9—C1—C2—C3	−179.76 (7)	C6—C7—C8—C9	177.91 (8)
C7—C2—C3—C4	−0.86 (11)	O1—C1—C9—C10	−0.86 (13)
C1—C2—C3—C4	178.74 (7)	C2—C1—C9—C10	179.00 (7)
C17—O2—C4—C3	−14.67 (11)	O1—C1—C9—C8	179.44 (8)
C17—O2—C4—C5	165.99 (7)	C2—C1—C9—C8	−0.71 (8)
C2—C3—C4—O2	179.62 (7)	C7—C8—C9—C10	−178.48 (8)
C2—C3—C4—C5	−1.07 (11)	C7—C8—C9—C1	1.18 (8)
C18—O3—C5—C6	−1.11 (12)	C1—C9—C10—C11	−179.66 (8)
C18—O3—C5—C4	179.19 (7)	C8—C9—C10—C11	−0.03 (15)
O2—C4—C5—O3	1.72 (10)	C9—C10—C11—C12	−1.40 (14)
C3—C4—C5—O3	−177.66 (7)	C9—C10—C11—C16	178.97 (8)
O2—C4—C5—C6	−178.00 (7)	C16—C11—C12—C13	−0.44 (12)
C3—C4—C5—C6	2.62 (12)	C10—C11—C12—C13	179.93 (8)
O3—C5—C6—C7	178.15 (7)	C11—C12—C13—C14	0.46 (13)
C4—C5—C6—C7	−2.16 (12)	C12—C13—C14—C15	0.04 (13)
C3—C2—C7—C6	1.31 (11)	C13—C14—C15—C16	−0.54 (13)
C1—C2—C7—C6	−178.36 (7)	C14—C15—C16—C11	0.55 (12)
C3—C2—C7—C8	−179.41 (7)	C12—C11—C16—C15	−0.06 (12)
C1—C2—C7—C8	0.92 (9)	C10—C11—C16—C15	179.60 (7)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O3ⁱ	0.96	2.53	3.4107 (11)	152
C18—H18B···O2ⁱⁱ	0.96	2.58	3.5320 (11)	173
C16—H16A···Cg1ⁱⁱⁱ	0.93	2.99	3.7224 (9)	137

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆O₃
M_r	280.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	6.0209 (6), 14.8550 (14), 15.2292 (15)
β (°)	90.603 (2)
V (Å³)	1362.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.44 × 0.29 × 0.16

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.960, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	31475, 6003, 4902
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.808

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.130, 1.09
No. of reflections	6003
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.58

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O3ⁱ	0.96	2.53	3.4107 (11)	152
C18—H18B···O2ⁱⁱ	0.96	2.58	3.5320 (11)	173
C16—H16A···Cg1ⁱⁱⁱ	0.93	2.99	3.7224 (9)	137

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

Footnotes

‡Thomson Reuters ResearcherID: A-5523-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors wish to express their thanks to Universiti Sains Malysia (USM) for providing research facilities. HKF thanks USM for the Research University Grant No. 1001/PFIZIK/811160 and CSY thanks USM for the award of a USM Fellowship.

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Volume 66| Part 10| October 2010| Pages o2531-o2532

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