(E)-2-[4-(Trifluoro­meth­yl)benzyl­idene]-2,3-dihydro-1H-inden-1-one

Wei, A.C.; Ali, M.A.; Choon, T.S.; Razak, I.A.; Arshad, S.

doi:10.1107/S1600536812003157

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o545-o546

doi:10.1107/S1600536812003157

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(E)-2-[4-(Trifluoromethyl)benzylidene]-2,3-dihydro-1H-inden-1-one

Ang Chee Wei,^a Mohamed Ashraf Ali,^a Tan Soo Choon,^a Ibrahim Abdul Razak ^b ^*‡ and Suhana Arshad ^b

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, and ^bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 17 January 2012; accepted 25 January 2012; online 31 January 2012)

In the title molecule, C₁₇H₁₁F₃O, the indan ring system and the trifluoromethyl-substituted benzene ring are approximately individually planar and form a dihedral angle of 1.81 (5)° with each other. In the crystal, molecules are linked by pairs of weak bifurcated (C—H)₂⋯O hydrogen bonds to form centrosymmetric dimers, generating R₂¹(6) and R₂²(10) ring motifs. These dimers are connected by further weak C—H⋯O hydrogen bonds into one-dimensional chains along the b axis. Weak C—H⋯π interactions are also present.

Related literature

For the biological activity of chalcone compounds, see: Gurubasavaraja Swamy & Agasimundin (2008 ); Shibata (1994 ); Charris et al. (2007 ); Sharma et al. (2009 ). For related structures, see: Ali et al. (2011a ,b ,c ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₇H₁₁F₃O
M_r = 288.26
Monoclinic, P 2₁ /c
a = 15.6546 (13) Å
b = 6.2050 (6) Å
c = 14.6546 (13) Å
β = 113.774 (2)°
V = 1302.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100 K
0.40 × 0.18 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.954, T_max = 0.988
10643 measured reflections
3804 independent reflections
3033 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.129
S = 1.06
3804 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O1ⁱ	0.99	2.45	3.2713 (17)	140
C10—H10A⋯O1ⁱⁱ	0.95	2.54	3.3566 (17)	144
C12—H12A⋯O1ⁱⁱ	0.95	2.45	3.2765 (17)	146
C15—H15A⋯Cg1ⁱⁱⁱ	0.95	2.78	3.5163 (14)	135
C3—H3A⋯Cg2ⁱⁱⁱ	0.95	2.81	3.5035 (15)	130
Symmetry codes: (i) x, y+1, z; (ii) -x, -y, -z+1; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536812003157/lh5408sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003157/lh5408Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812003157/lh5408Isup3.cml

checkCIF report

Comment top

Chalcones are an important group of natural products and many of these compounds possess various biological activities including antibacterial (Gurubasavaraja Swamy & Agasimundin, 2008), antitumor (Shibata, 1994), antimalarial (Charris et al., 2007) and antitubercular (Sharma et al., 2009). Indanones have been studied extensively as they are very useful intermediates for the synthesis of heterocyclic compounds. As part of our ongoing search to discover novel indanone related compounds (Ali et al., 2011a,b) our group has synthesized the title compound as described below.

In the molecular structure (Fig 1), the 2,3-dihydro-1H-indene ring system (C1–C9) and the benzene ring (C11–C16) are approximately planar with a dihedral angle of 1.81 (5)° between them. The bond lengths and angles are within normal ranges and comparable to the related structure (Ali et al., 2011c).

The crystal packing is shown in Fig. 2. The molecules are linked by intermolecular C1—H1B···O1ⁱ, C10—H10A···O1ⁱⁱ and C12—H12A···O1ⁱⁱ interactions (Table 1) to form dimers, generating R¹₂(6) and R²₂(10) ring motifs (Bernstein et al., 1995). Furthermore, these sets of ring motifs are connected into one-dimensional chains along the b-axis. In addition, the crystal structure is further stabilized by weak intermolecular C15—H15A···Cg1ⁱⁱⁱ and C3—H3A···Cg2ⁱⁱⁱ (Table 1) interactions (Cg1 and Cg2 are the centroids of C2–C7 and C11–C16 rings, respectively).

Related literature top

For the biological activity of chalcone compounds, see: Gurubasavaraja Swamy & Agasimundin (2008); Shibata (1994); Charris et al. (2007); Sharma et al. (2009). For related structures, see: Ali et al. (2011a,b,c). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 2,3-dihydro-1H-indene-1-one (0.001 mol) and 4-(trifluoromethyl)benzaldehyde (0.001 mol) were dissolved in ethanolic sodium hydroxide solution (15 ml) and the mixture was 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 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, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

(E)-2-[4-(Trifluoromethyl)benzylidene]-2,3-dihydro-1H-inden-1-one top

Crystal data top

C₁₇H₁₁F₃O	F(000) = 592
M_r = 288.26	D_x = 1.470 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3626 reflections
a = 15.6546 (13) Å	θ = 2.8–30.1°
b = 6.2050 (6) Å	µ = 0.12 mm⁻¹
c = 14.6546 (13) Å	T = 100 K
β = 113.774 (2)°	Plate, colourless
V = 1302.7 (2) Å³	0.40 × 0.18 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3804 independent reflections
Radiation source: fine-focus sealed tube	3033 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→22
T_min = 0.954, T_max = 0.988	k = −8→8
10643 measured reflections	l = −20→20

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0567P)² + 0.6847P] where P = (F_o² + 2F_c²)/3
3804 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₇H₁₁F₃O	V = 1302.7 (2) Å³
M_r = 288.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.6546 (13) Å	µ = 0.12 mm⁻¹
b = 6.2050 (6) Å	T = 100 K
c = 14.6546 (13) Å	0.40 × 0.18 × 0.10 mm
β = 113.774 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3804 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3033 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.988	R_int = 0.023
10643 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.06	Δρ_max = 0.55 e Å⁻³
3804 reflections	Δρ_min = −0.32 e Å⁻³
190 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
F1	−0.41885 (6)	0.88298 (16)	0.17877 (8)	0.0335 (2)
F2	−0.47050 (6)	0.62598 (19)	0.23994 (8)	0.0392 (3)
F3	−0.45949 (7)	0.5856 (2)	0.09945 (8)	0.0450 (3)
O1	0.11757 (7)	0.05902 (17)	0.48959 (8)	0.0225 (2)
C1	0.07259 (8)	0.5913 (2)	0.37708 (10)	0.0170 (3)
H1A	0.0478	0.6137	0.3041	0.020*
H1B	0.0544	0.7149	0.4081	0.020*
C2	0.17752 (8)	0.5624 (2)	0.42083 (9)	0.0158 (2)
C3	0.24539 (9)	0.7074 (2)	0.42066 (10)	0.0192 (3)
H3A	0.2285	0.8445	0.3897	0.023*
C4	0.33894 (9)	0.6456 (3)	0.46729 (10)	0.0221 (3)
H4A	0.3861	0.7427	0.4680	0.026*
C5	0.36474 (9)	0.4440 (3)	0.51297 (10)	0.0215 (3)
H5A	0.4289	0.4062	0.5440	0.026*
C6	0.29734 (9)	0.2987 (2)	0.51332 (9)	0.0187 (3)
H6A	0.3141	0.1614	0.5441	0.022*
C7	0.20371 (8)	0.3623 (2)	0.46647 (9)	0.0154 (2)
C8	0.12026 (8)	0.2400 (2)	0.45815 (9)	0.0166 (3)
C9	0.03802 (8)	0.3802 (2)	0.40223 (9)	0.0163 (2)
C10	−0.04785 (8)	0.3083 (2)	0.38672 (9)	0.0167 (2)
H10A	−0.0496	0.1677	0.4116	0.020*
C11	−0.13924 (8)	0.4128 (2)	0.33745 (9)	0.0164 (2)
C12	−0.21766 (8)	0.2952 (2)	0.33344 (9)	0.0159 (2)
H12A	−0.2091	0.1570	0.3637	0.019*
C13	−0.30716 (8)	0.3780 (2)	0.28612 (9)	0.0173 (3)
H13A	−0.3595	0.2959	0.2829	0.021*
C14	−0.31963 (8)	0.5819 (2)	0.24335 (9)	0.0166 (3)
C15	−0.24327 (9)	0.7038 (2)	0.24696 (9)	0.0175 (3)
H15A	−0.2523	0.8430	0.2176	0.021*
C16	−0.15373 (9)	0.6189 (2)	0.29410 (10)	0.0182 (3)
H16A	−0.1016	0.7016	0.2970	0.022*
C17	−0.41652 (9)	0.6688 (3)	0.19105 (10)	0.0219 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0274 (4)	0.0258 (5)	0.0519 (6)	0.0129 (4)	0.0208 (4)	0.0134 (5)
F2	0.0209 (4)	0.0532 (7)	0.0507 (6)	0.0122 (4)	0.0218 (4)	0.0260 (5)
F3	0.0284 (5)	0.0563 (8)	0.0316 (5)	0.0171 (5)	−0.0074 (4)	−0.0106 (5)
O1	0.0210 (4)	0.0179 (5)	0.0275 (5)	−0.0019 (4)	0.0086 (4)	0.0045 (4)
C1	0.0148 (5)	0.0169 (6)	0.0181 (5)	−0.0023 (5)	0.0055 (4)	0.0026 (5)
C2	0.0156 (5)	0.0179 (6)	0.0143 (5)	−0.0030 (5)	0.0065 (4)	−0.0011 (5)
C3	0.0192 (6)	0.0195 (7)	0.0196 (6)	−0.0044 (5)	0.0086 (5)	−0.0004 (5)
C4	0.0177 (6)	0.0274 (8)	0.0227 (6)	−0.0077 (5)	0.0097 (5)	−0.0034 (6)
C5	0.0143 (5)	0.0296 (8)	0.0197 (6)	−0.0025 (5)	0.0061 (5)	−0.0029 (6)
C6	0.0161 (5)	0.0218 (7)	0.0175 (5)	−0.0004 (5)	0.0059 (4)	−0.0018 (5)
C7	0.0140 (5)	0.0178 (6)	0.0145 (5)	−0.0026 (5)	0.0059 (4)	−0.0015 (5)
C8	0.0145 (5)	0.0179 (6)	0.0162 (5)	−0.0016 (5)	0.0050 (4)	−0.0003 (5)
C9	0.0162 (5)	0.0154 (6)	0.0165 (5)	−0.0003 (5)	0.0059 (4)	−0.0002 (5)
C10	0.0159 (5)	0.0157 (6)	0.0176 (5)	0.0001 (5)	0.0059 (4)	−0.0002 (5)
C11	0.0141 (5)	0.0178 (6)	0.0155 (5)	−0.0006 (5)	0.0042 (4)	0.0008 (5)
C12	0.0146 (5)	0.0157 (6)	0.0164 (5)	−0.0010 (5)	0.0053 (4)	0.0008 (5)
C13	0.0141 (5)	0.0194 (6)	0.0186 (6)	−0.0013 (5)	0.0069 (4)	0.0002 (5)
C14	0.0149 (5)	0.0191 (6)	0.0161 (5)	0.0032 (5)	0.0065 (4)	0.0002 (5)
C15	0.0185 (6)	0.0163 (6)	0.0176 (5)	0.0019 (5)	0.0071 (4)	0.0021 (5)
C16	0.0163 (5)	0.0180 (6)	0.0190 (6)	−0.0020 (5)	0.0057 (4)	0.0023 (5)
C17	0.0174 (6)	0.0252 (7)	0.0236 (6)	0.0059 (5)	0.0088 (5)	0.0054 (6)

Geometric parameters (Å, º) top

F1—C17	1.3395 (18)	C6—H6A	0.9500
F2—C17	1.3365 (16)	C7—C8	1.4727 (17)
F3—C17	1.3391 (18)	C8—C9	1.4951 (18)
O1—C8	1.2211 (17)	C9—C10	1.3460 (17)
C1—C2	1.5141 (17)	C10—C11	1.4683 (17)
C1—C9	1.5180 (19)	C10—H10A	0.9500
C1—H1A	0.9900	C11—C16	1.4049 (19)
C1—H1B	0.9900	C11—C12	1.4090 (17)
C2—C7	1.3912 (19)	C12—C13	1.3871 (17)
C2—C3	1.3932 (18)	C12—H12A	0.9500
C3—C4	1.3971 (19)	C13—C14	1.3907 (19)
C3—H3A	0.9500	C13—H13A	0.9500
C4—C5	1.399 (2)	C14—C15	1.3974 (18)
C4—H4A	0.9500	C14—C17	1.4972 (17)
C5—C6	1.3895 (19)	C15—C16	1.3926 (18)
C5—H5A	0.9500	C15—H15A	0.9500
C6—C7	1.4016 (17)	C16—H16A	0.9500

C2—C1—C9	103.13 (11)	C8—C9—C1	108.82 (10)
C2—C1—H1A	111.1	C9—C10—C11	130.19 (13)
C9—C1—H1A	111.1	C9—C10—H10A	114.9
C2—C1—H1B	111.1	C11—C10—H10A	114.9
C9—C1—H1B	111.1	C16—C11—C12	118.25 (11)
H1A—C1—H1B	109.1	C16—C11—C10	124.90 (11)
C7—C2—C3	120.00 (12)	C12—C11—C10	116.85 (12)
C7—C2—C1	111.62 (11)	C13—C12—C11	121.11 (12)
C3—C2—C1	128.37 (12)	C13—C12—H12A	119.4
C2—C3—C4	118.14 (13)	C11—C12—H12A	119.4
C2—C3—H3A	120.9	C12—C13—C14	119.48 (12)
C4—C3—H3A	120.9	C12—C13—H13A	120.3
C3—C4—C5	121.53 (13)	C14—C13—H13A	120.3
C3—C4—H4A	119.2	C13—C14—C15	120.86 (12)
C5—C4—H4A	119.2	C13—C14—C17	119.19 (12)
C6—C5—C4	120.58 (12)	C15—C14—C17	119.94 (12)
C6—C5—H5A	119.7	C16—C15—C14	119.25 (13)
C4—C5—H5A	119.7	C16—C15—H15A	120.4
C5—C6—C7	117.46 (13)	C14—C15—H15A	120.4
C5—C6—H6A	121.3	C15—C16—C11	121.03 (12)
C7—C6—H6A	121.3	C15—C16—H16A	119.5
C2—C7—C6	122.29 (12)	C11—C16—H16A	119.5
C2—C7—C8	109.90 (11)	F2—C17—F3	106.87 (13)
C6—C7—C8	127.81 (13)	F2—C17—F1	106.30 (12)
O1—C8—C7	127.37 (12)	F3—C17—F1	105.80 (12)
O1—C8—C9	126.09 (12)	F2—C17—C14	112.52 (11)
C7—C8—C9	106.53 (11)	F3—C17—C14	111.72 (12)
C10—C9—C8	118.70 (12)	F1—C17—C14	113.15 (12)
C10—C9—C1	132.43 (12)

C9—C1—C2—C7	−0.08 (14)	C2—C1—C9—C8	0.30 (13)
C9—C1—C2—C3	−179.37 (13)	C8—C9—C10—C11	178.11 (12)
C7—C2—C3—C4	−0.10 (19)	C1—C9—C10—C11	1.1 (2)
C1—C2—C3—C4	179.14 (13)	C9—C10—C11—C16	0.8 (2)
C2—C3—C4—C5	0.2 (2)	C9—C10—C11—C12	−179.53 (13)
C3—C4—C5—C6	−0.1 (2)	C16—C11—C12—C13	1.41 (19)
C4—C5—C6—C7	0.02 (19)	C10—C11—C12—C13	−178.26 (12)
C3—C2—C7—C6	0.01 (19)	C11—C12—C13—C14	−1.11 (19)
C1—C2—C7—C6	−179.36 (12)	C12—C13—C14—C15	0.38 (19)
C3—C2—C7—C8	179.18 (11)	C12—C13—C14—C17	179.09 (12)
C1—C2—C7—C8	−0.18 (15)	C13—C14—C15—C16	0.01 (19)
C5—C6—C7—C2	0.03 (19)	C17—C14—C15—C16	−178.69 (12)
C5—C6—C7—C8	−178.99 (12)	C14—C15—C16—C11	0.3 (2)
C2—C7—C8—O1	179.80 (13)	C12—C11—C16—C15	−1.01 (19)
C6—C7—C8—O1	−1.1 (2)	C10—C11—C16—C15	178.63 (12)
C2—C7—C8—C9	0.36 (14)	C13—C14—C17—F2	41.38 (18)
C6—C7—C8—C9	179.48 (12)	C15—C14—C17—F2	−139.90 (14)
O1—C8—C9—C10	2.5 (2)	C13—C14—C17—F3	−78.84 (16)
C7—C8—C9—C10	−178.09 (11)	C15—C14—C17—F3	99.88 (16)
O1—C8—C9—C1	−179.86 (13)	C13—C14—C17—F1	161.88 (12)
C7—C8—C9—C1	−0.41 (14)	C15—C14—C17—F1	−19.40 (18)
C2—C1—C9—C10	177.55 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C2–C7 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1ⁱ	0.99	2.45	3.2713 (17)	140
C10—H10A···O1ⁱⁱ	0.95	2.54	3.3566 (17)	144
C12—H12A···O1ⁱⁱ	0.95	2.45	3.2765 (17)	146
C15—H15A···Cg1ⁱⁱⁱ	0.95	2.78	3.5163 (14)	135
C3—H3A···Cg2ⁱⁱⁱ	0.95	2.81	3.5035 (15)	130

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₁F₃O
M_r	288.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	15.6546 (13), 6.2050 (6), 14.6546 (13)
β (°)	113.774 (2)
V (Å³)	1302.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.40 × 0.18 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.954, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	10643, 3804, 3033
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.129, 1.06
No. of reflections	3804
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.32

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 C2–C7 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1ⁱ	0.9900	2.4500	3.2713 (17)	140.00
C10—H10A···O1ⁱⁱ	0.9500	2.5400	3.3566 (17)	144.00
C12—H12A···O1ⁱⁱ	0.9500	2.4500	3.2765 (17)	146.00
C15—H15A···Cg1ⁱⁱⁱ	0.9500	2.7800	3.5163 (14)	135.00
C3—H3A···Cg2ⁱⁱⁱ	0.9500	2.8100	3.5035 (15)	130.00

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

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for Research University grants Nos. 1001/PFIZIK/811151 and 1001/PSK/8620012. The authors are also grateful to Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti Sains Malaysia.

References

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Volume 68| Part 2| February 2012| Pages o545-o546

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