(E)-1-(3,4-Dimeth­oxy­phen­yl)-3-[4-(methyl­sulfan­yl)phen­yl]prop-2-en-1-one

Fun, H.-K.; Asik, S.I.J.; Lobo, P.L.; Prasad, D.J.; Bojapoojary

doi:10.1107/S160053681103323X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2403

doi:10.1107/S160053681103323X

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(E)-1-(3,4-Dimethoxyphenyl)-3-[4-(methylsulfanyl)phenyl]prop-2-en-1-one

Hoong-Kun Fun,^a ^*‡ Safra Izuani Jama Asik,^a Prajwal L. Lobo,^b D. Jagadeesh Prasad ^b and Bojapoojary ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Mangalore University, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 11 August 2011; accepted 16 August 2011; online 27 August 2011)

In the title compound, C₁₈H₁₈O₃S, the C=C double bond exists in an E configuration and the dihedral angle between the two benzene rings is 11.74 (8)°. In the crystal, molecules are linked into a three-dimensional network by C—H⋯O hydrogen bonds. The crystal structure is also stabilized by weak C—H⋯π interactions.

Related literature

For the biological activity of chalcone derivatives, see: Rajendra Prasad et al. (2008 ); Won et al. (2005); Sivakumar et al. (2007 ); Churkin et al. (1982 ). For related structures, see: Narayana et al. (2007 ); Fun et al. (2011 ).

Experimental

Crystal data

C₁₈H₁₈O₃S
M_r = 314.38
Tetragonal, $[P \overline 42_1 c ]$
a = 19.0863 (7) Å
c = 8.9633 (4) Å
V = 3265.2 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.60 × 0.27 × 0.21 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.886, T_max = 0.957
65941 measured reflections
4760 independent reflections
3944 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.100
S = 1.03
4760 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), 2109 Friedel pairs
Flack parameter: −0.01 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯O1ⁱ	0.96	2.33	3.235 (2)	157
C17—H17A⋯O3ⁱⁱ	0.96	2.47	3.344 (2)	151
C4—H4A⋯Cg1ⁱⁱⁱ	0.93	2.79	3.5776 (17)	143
Symmetry codes: (i) $[y-{\script{1\over 2}}, x+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) y-1, -x+1, -z-1; (iii) -x-1, -y+1, 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/S160053681103323X/wn2447sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681103323X/wn2447Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681103323X/wn2447Isup3.cml

checkCIF report

Comment top

Chalcones are condensation products of simple or substituted aromatic aldehydes with simple or substituted acetophenones in the presence of alkali. Chalcones constitute an important group of natural products and some of them possess a wide range of biological activities such as antimicrobial (Rajendra Prasad et al., 2008), anticancer (Won et al., 2005), antitubercular (Sivakumar et al., 2007) and antiviral (Churkin et al., 1982) properties. The crystal structures of (2E)-1-(2-thienyl)-3-(2,3,5-trichlorophenyl)prop-2-ene-1-one (Narayana et al., 2007) and (E)-3-(4-chlorophenyl)-1- (2,3,4-trichlorophenyl)prop-2-en-1-one (Fun et al., 2011) have been reported.

As shown in Fig. 1, the C8═C9 double bond exists in an E configuration with an O1—C7—C8—C9 torsion angle of -1.3 (2)°. The dihedral angle between the two benzene (C1–C6 and C10–C15) rings is 11.74 (8)°. The torsion angles C18—S1—C13—C14, C17—O3—C3—C4 and C16—O2—C2—C1 are 4.19 (8), -5.0 (2) and 7.8 (2)°, respectively, showing that the methylthio and methoxy substituents are essentially coplanar with the attached benzene rings.

In the crystal structure (Fig. 2), the molecules are linked into a three-dimensional network by C16—H16B···O1 and C17—H17A···O3 hydrogen bonds. The crystal structure is also stabilized by a weak C—H···π interaction (Table 1), with a distance of 3.5776 (17) Å.

Related literature top

For the biological activity of chalcone derivatives, see: Rajendra Prasad et al. (2008); Won et al. (2005); Sivakumar et al. (2007); Churkin et al. (1982). For related structures, see: Narayana et al. (2007); Fun et al. (2011).

Experimental top

4-Methylthiobenzaldehyde (0.1mol) and 3,4-dimethoxyacetophenone (0.1mol) in the presence of NaOH in ethanol were stirred at room temperature for 2 h. The resulting product was filtered, washed, dried and recrystallised from ethanol.

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 structure of the title compound, showing 50% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal packing, viewed along the c-axis, showing the molecules linked into a three-dimensional network. Hydrogen atoms not involved in hydrogen bonding (dashed lines) are omitted for clarity.

(E)-1-(3,4-Dimethoxyphenyl)-3-[4-(methylsulfanyl)phenyl]prop-2-en-1-one top

Crystal data top

C₁₈H₁₈O₃S	D_x = 1.279 Mg m⁻³
M_r = 314.38	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42₁c	Cell parameters from 9341 reflections
Hall symbol: P -4 2n	θ = 2.4–26.5°
a = 19.0863 (7) Å	µ = 0.21 mm⁻¹
c = 8.9633 (4) Å	T = 296 K
V = 3265.2 (2) Å³	Block, colourless
Z = 8	0.60 × 0.27 × 0.21 mm
F(000) = 1328

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	4760 independent reflections
Radiation source: fine-focus sealed tube	3944 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −26→26
T_min = 0.886, T_max = 0.957	k = −26→26
65941 measured reflections	l = −12→12

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0476P)² + 0.3471P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4760 reflections	Δρ_max = 0.13 e Å⁻³
202 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2109 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (7)

Crystal data top

C₁₈H₁₈O₃S	Z = 8
M_r = 314.38	Mo Kα radiation
Tetragonal, P42₁c	µ = 0.21 mm⁻¹
a = 19.0863 (7) Å	T = 296 K
c = 8.9633 (4) Å	0.60 × 0.27 × 0.21 mm
V = 3265.2 (2) Å³

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	4760 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3944 reflections with I > 2σ(I)
T_min = 0.886, T_max = 0.957	R_int = 0.028
65941 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.100	Δρ_max = 0.13 e Å⁻³
S = 1.03	Δρ_min = −0.18 e Å⁻³
4760 reflections	Absolute structure: Flack (1983), 2109 Friedel pairs
202 parameters	Absolute structure parameter: −0.01 (7)
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	−0.04907 (3)	0.61987 (3)	0.96772 (6)	0.08374 (17)
O1	0.20901 (6)	0.80886 (8)	0.25811 (15)	0.0801 (4)
O2	0.18232 (6)	0.88384 (6)	−0.28422 (13)	0.0638 (3)
O3	0.04997 (6)	0.89660 (7)	−0.32673 (13)	0.0682 (3)
C1	0.16475 (7)	0.84377 (7)	−0.02843 (18)	0.0498 (3)
H1A	0.2126	0.8392	−0.0120	0.060*
C2	0.14116 (7)	0.86658 (7)	−0.16444 (16)	0.0496 (3)
C3	0.06866 (8)	0.87441 (8)	−0.18887 (17)	0.0533 (3)
C4	0.02241 (8)	0.85920 (9)	−0.07543 (19)	0.0613 (4)
H4A	−0.0255	0.8649	−0.0906	0.074*
C5	0.04682 (8)	0.83541 (8)	0.06130 (17)	0.0558 (3)
H5A	0.0151	0.8249	0.1368	0.067*
C6	0.11757 (7)	0.82725 (7)	0.08653 (16)	0.0482 (3)
C7	0.14607 (8)	0.80464 (8)	0.23353 (18)	0.0535 (3)
C8	0.09822 (8)	0.77645 (8)	0.34700 (17)	0.0554 (3)
H8A	0.0505	0.7747	0.3263	0.067*
C9	0.12086 (8)	0.75347 (8)	0.47766 (17)	0.0550 (3)
H9A	0.1687	0.7578	0.4951	0.066*
C10	0.07975 (8)	0.72221 (8)	0.59750 (16)	0.0513 (3)
C11	0.00713 (9)	0.71448 (11)	0.59020 (18)	0.0697 (5)
H11A	−0.0166	0.7301	0.5058	0.084*
C12	−0.03014 (9)	0.68459 (12)	0.7040 (2)	0.0727 (5)
H12A	−0.0786	0.6807	0.6963	0.087*
C13	0.00383 (9)	0.65988 (9)	0.83166 (17)	0.0570 (3)
C14	0.07588 (8)	0.66729 (8)	0.84138 (17)	0.0574 (3)
H14A	0.0996	0.6513	0.9254	0.069*
C15	0.11254 (8)	0.69847 (8)	0.72617 (17)	0.0551 (3)
H15A	0.1608	0.7037	0.7352	0.066*
C16	0.25489 (9)	0.86904 (11)	−0.2721 (3)	0.0832 (6)
H16A	0.2770	0.8761	−0.3671	0.125*
H16B	0.2612	0.8213	−0.2413	0.125*
H16C	0.2756	0.8997	−0.1996	0.125*
C17	−0.02357 (10)	0.89919 (13)	−0.3594 (2)	0.0833 (6)
H17A	−0.0302	0.9087	−0.4636	0.125*
H17B	−0.0451	0.9356	−0.3015	0.125*
H17C	−0.0447	0.8550	−0.3348	0.125*
C18	0.01027 (13)	0.59980 (14)	1.1152 (2)	0.0967 (7)
H18A	−0.0149	0.5788	1.1964	0.145*
H18B	0.0324	0.6421	1.1490	0.145*
H18C	0.0453	0.5677	1.0797	0.145*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0711 (3)	0.1198 (4)	0.0603 (2)	−0.0176 (3)	0.0045 (2)	0.0147 (3)
O1	0.0511 (6)	0.1106 (10)	0.0786 (8)	0.0013 (6)	−0.0057 (6)	0.0289 (8)
O2	0.0579 (6)	0.0706 (7)	0.0629 (6)	0.0057 (5)	0.0190 (5)	0.0133 (6)
O3	0.0606 (6)	0.0881 (8)	0.0560 (6)	0.0054 (6)	0.0033 (5)	0.0256 (6)
C1	0.0445 (6)	0.0461 (7)	0.0588 (7)	0.0023 (5)	0.0042 (6)	0.0027 (6)
C2	0.0507 (7)	0.0441 (6)	0.0540 (7)	0.0009 (5)	0.0118 (6)	0.0046 (6)
C3	0.0545 (7)	0.0541 (7)	0.0512 (7)	0.0038 (6)	0.0042 (6)	0.0101 (6)
C4	0.0445 (7)	0.0786 (10)	0.0608 (9)	0.0041 (7)	0.0025 (6)	0.0185 (8)
C5	0.0479 (7)	0.0671 (9)	0.0523 (8)	0.0016 (6)	0.0072 (6)	0.0145 (7)
C6	0.0486 (7)	0.0442 (6)	0.0519 (7)	0.0023 (5)	0.0040 (6)	0.0042 (5)
C7	0.0513 (7)	0.0519 (7)	0.0573 (8)	0.0048 (6)	−0.0002 (6)	0.0067 (6)
C8	0.0526 (7)	0.0619 (8)	0.0518 (8)	0.0014 (6)	−0.0029 (6)	0.0063 (6)
C9	0.0527 (7)	0.0604 (8)	0.0519 (7)	0.0007 (6)	−0.0046 (6)	0.0019 (6)
C10	0.0525 (7)	0.0559 (8)	0.0456 (7)	0.0004 (6)	−0.0051 (6)	0.0001 (6)
C11	0.0569 (9)	0.1012 (13)	0.0509 (8)	−0.0060 (9)	−0.0156 (7)	0.0129 (9)
C12	0.0497 (8)	0.1083 (14)	0.0602 (10)	−0.0101 (9)	−0.0099 (7)	0.0117 (10)
C13	0.0588 (8)	0.0664 (9)	0.0456 (7)	−0.0050 (7)	−0.0008 (6)	−0.0015 (6)
C14	0.0574 (8)	0.0661 (9)	0.0486 (7)	0.0021 (7)	−0.0092 (6)	0.0064 (7)
C15	0.0486 (7)	0.0635 (8)	0.0532 (7)	0.0004 (6)	−0.0072 (6)	0.0053 (6)
C16	0.0605 (9)	0.0824 (12)	0.1066 (15)	0.0140 (9)	0.0337 (10)	0.0321 (12)
C17	0.0682 (11)	0.1129 (16)	0.0687 (11)	0.0062 (10)	−0.0067 (9)	0.0341 (11)
C18	0.0957 (16)	0.1238 (19)	0.0706 (12)	−0.0081 (14)	0.0019 (11)	0.0352 (13)

Geometric parameters (Å, º) top

S1—C13	1.7579 (16)	C9—H9A	0.9300
S1—C18	1.783 (2)	C10—C15	1.388 (2)
O1—C7	1.2239 (19)	C10—C11	1.396 (2)
O2—C2	1.3705 (16)	C11—C12	1.368 (2)
O2—C16	1.418 (2)	C11—H11A	0.9300
O3—C3	1.3541 (18)	C12—C13	1.397 (2)
O3—C17	1.435 (2)	C12—H12A	0.9300
C1—C2	1.371 (2)	C13—C14	1.385 (2)
C1—C6	1.4042 (19)	C14—C15	1.382 (2)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.409 (2)	C15—H15A	0.9300
C3—C4	1.378 (2)	C16—H16A	0.9600
C4—C5	1.387 (2)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600
C5—C6	1.378 (2)	C17—H17A	0.9600
C5—H5A	0.9300	C17—H17B	0.9600
C6—C7	1.489 (2)	C17—H17C	0.9600
C7—C8	1.469 (2)	C18—H18A	0.9600
C8—C9	1.323 (2)	C18—H18B	0.9600
C8—H8A	0.9300	C18—H18C	0.9600
C9—C10	1.458 (2)

C13—S1—C18	104.06 (9)	C12—C11—C10	121.70 (15)
C2—O2—C16	116.87 (13)	C12—C11—H11A	119.1
C3—O3—C17	117.05 (13)	C10—C11—H11A	119.1
C2—C1—C6	120.90 (13)	C11—C12—C13	120.67 (15)
C2—C1—H1A	119.6	C11—C12—H12A	119.7
C6—C1—H1A	119.6	C13—C12—H12A	119.7
O2—C2—C1	125.80 (13)	C14—C13—C12	118.54 (15)
O2—C2—C3	114.56 (13)	C14—C13—S1	124.81 (12)
C1—C2—C3	119.63 (12)	C12—C13—S1	116.64 (12)
O3—C3—C4	124.80 (13)	C15—C14—C13	119.97 (14)
O3—C3—C2	115.71 (13)	C15—C14—H14A	120.0
C4—C3—C2	119.49 (13)	C13—C14—H14A	120.0
C3—C4—C5	120.39 (14)	C14—C15—C10	122.21 (14)
C3—C4—H4A	119.8	C14—C15—H15A	118.9
C5—C4—H4A	119.8	C10—C15—H15A	118.9
C6—C5—C4	120.73 (14)	O2—C16—H16A	109.5
C6—C5—H5A	119.6	O2—C16—H16B	109.5
C4—C5—H5A	119.6	H16A—C16—H16B	109.5
C5—C6—C1	118.85 (13)	O2—C16—H16C	109.5
C5—C6—C7	122.40 (13)	H16A—C16—H16C	109.5
C1—C6—C7	118.69 (12)	H16B—C16—H16C	109.5
O1—C7—C8	120.64 (15)	O3—C17—H17A	109.5
O1—C7—C6	119.91 (14)	O3—C17—H17B	109.5
C8—C7—C6	119.44 (13)	H17A—C17—H17B	109.5
C9—C8—C7	122.08 (14)	O3—C17—H17C	109.5
C9—C8—H8A	119.0	H17A—C17—H17C	109.5
C7—C8—H8A	119.0	H17B—C17—H17C	109.5
C8—C9—C10	127.74 (14)	S1—C18—H18A	109.5
C8—C9—H9A	116.1	S1—C18—H18B	109.5
C10—C9—H9A	116.1	H18A—C18—H18B	109.5
C15—C10—C11	116.89 (14)	S1—C18—H18C	109.5
C15—C10—C9	120.21 (13)	H18A—C18—H18C	109.5
C11—C10—C9	122.91 (14)	H18B—C18—H18C	109.5

C16—O2—C2—C1	7.8 (2)	C5—C6—C7—C8	12.6 (2)
C16—O2—C2—C3	−172.66 (15)	C1—C6—C7—C8	−170.27 (13)
C6—C1—C2—O2	−179.74 (13)	O1—C7—C8—C9	−1.3 (3)
C6—C1—C2—C3	0.8 (2)	C6—C7—C8—C9	177.77 (14)
C17—O3—C3—C4	−4.9 (2)	C7—C8—C9—C10	−177.71 (15)
C17—O3—C3—C2	174.67 (17)	C8—C9—C10—C15	177.66 (16)
O2—C2—C3—O3	1.0 (2)	C8—C9—C10—C11	−2.3 (3)
C1—C2—C3—O3	−179.45 (14)	C15—C10—C11—C12	−0.3 (3)
O2—C2—C3—C4	−179.36 (15)	C9—C10—C11—C12	179.63 (18)
C1—C2—C3—C4	0.2 (2)	C10—C11—C12—C13	−0.8 (3)
O3—C3—C4—C5	178.71 (16)	C11—C12—C13—C14	1.0 (3)
C2—C3—C4—C5	−0.9 (3)	C11—C12—C13—S1	−177.93 (16)
C3—C4—C5—C6	0.6 (3)	C18—S1—C13—C14	4.20 (19)
C4—C5—C6—C1	0.3 (2)	C18—S1—C13—C12	−176.97 (16)
C4—C5—C6—C7	177.46 (15)	C12—C13—C14—C15	−0.1 (2)
C2—C1—C6—C5	−1.0 (2)	S1—C13—C14—C15	178.71 (13)
C2—C1—C6—C7	−178.28 (13)	C13—C14—C15—C10	−1.0 (2)
C5—C6—C7—O1	−168.32 (16)	C11—C10—C15—C14	1.2 (2)
C1—C6—C7—O1	8.8 (2)	C9—C10—C15—C14	−178.74 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O1ⁱ	0.96	2.33	3.235 (2)	157
C17—H17A···O3ⁱⁱ	0.96	2.47	3.344 (2)	151
C4—H4A···Cg1ⁱⁱⁱ	0.93	2.79	3.5776 (17)	143

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₃S
M_r	314.38
Crystal system, space group	Tetragonal, P42₁c
Temperature (K)	296
a, c (Å)	19.0863 (7), 8.9633 (4)
V (Å³)	3265.2 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.60 × 0.27 × 0.21

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.886, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	65941, 4760, 3944
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.100, 1.03
No. of reflections	4760
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.18
Absolute structure	Flack (1983), 2109 Friedel pairs
Absolute structure parameter	−0.01 (7)

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 the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O1ⁱ	0.96	2.33	3.235 (2)	157
C17—H17A···O3ⁱⁱ	0.96	2.47	3.344 (2)	151
C4—H4A···Cg1ⁱⁱⁱ	0.93	2.79	3.5776 (17)	143

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and SIJA thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grants (Nos.1001/PFIZIK/811160 and 1001/PFIZIK/ 811151).

References

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