(E)-1-(3-Bromo­phen­yl)-3-(4-ethoxy­phen­yl)prop-2-en-1-one

Fun, H.-K.; Chantrapromma, S.; Patil, P.S.; Dharmaprakash, S.M.

doi:10.1107/S1600536808018850

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Pages o1356-o1357

doi:10.1107/S1600536808018850

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(E)-1-(3-Bromophenyl)-3-(4-ethoxyphenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^* Suchada Chantrapromma,^b ‡ P. S. Patil ^c and S. M. Dharmaprakash ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 19 June 2008; accepted 22 June 2008; online 28 June 2008)

The title compound, C₁₇H₁₅BrO₂, adopts an E configuration. The dihedral angle between the two benzene rings is 10.09 (11)°. The enone plane makes dihedral angles of 12.05 (11) and 9.87 (11)°, respectively, with the bromophenyl and ethoxyphenyl rings. The ethoxy group is nearly coplanar with the attached benzene ring. In the crystal structure, the molecules are linked by C—H⋯O hydrogen bonds, forming a zigzag ribbon-like structure along the b-axis direction.

Related literature

For bond-length data, see: Allen et al. (1987 ). For related structures, see: Patil, Fun et al. (2007 ); Patil, Ng et al. (2007 ); Sathiya Moorthi et al. (2005a ,b ). For background to chalcones, see: Chopra et al. (2007 ); DiCesare et al. (2000 ); Gu et al. (2008a ,b ); Jiang et al. (1994 ); Lokaj et al. (2001 ); Low et al. (2002 ); Nel et al. (1998 ); Patil & Dharmaprakash (2007 ); Patil et al. (2006 ); Schmalle et al. (1990 ); Wang et al. (2004 ).

Experimental

Crystal data

C₁₇H₁₅BrO₂
M_r = 331.19
Monoclinic, P 2₁
a = 4.0516 (1) Å
b = 9.6501 (2) Å
c = 17.9120 (4) Å
β = 92.396 (1)°
V = 699.72 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.94 mm⁻¹
T = 100.0 (1) K
0.53 × 0.31 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.305, T_max = 0.641 (expected range = 0.289–0.607)
14837 measured reflections
5989 independent reflections
4682 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.093
S = 1.04
5989 reflections
182 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.65 e Å⁻³
Absolute structure: Flack (1983 ), 2764 Friedel pairs
Flack parameter: 0.021 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1	0.93	2.36	2.746 (3)	105
C16—H16B⋯O1ⁱ	0.97	2.49	3.400 (3)	157
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+2]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018850/ci2619sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018850/ci2619Isup2.hkl

checkCIF report

Comment top

Extensive research in recent years suggests organic materials to be the ideal candidates for tailoring the material properties. As an interesting type of organic materials, chalcone and its derivatives have received much attention from physicists, chemists and material scientists who have been extensively investigating their optical, physical and chemical properties for fundamental understanding and technological applications (Chopra et al., 2007; Lokaj et al., 2001; Low et al., 2002; Sathiya Moorthi et al., 2005a,b; Schmalle et al., 1990; Wang et al., 2004). Earlier studies have indicated that chalcone and its derivatives are potential candidates for optical limiting applications (Gu et al., 2008a,b). Owing to their electronic structures, chalcones also find unique applications in fluorescent probes for the sensing of metal ions (DiCesare et al., 2000; Jiang et al., 1994), and in biological use (Nel et al., 1998). The chalcone derivatives with typical D-π-A mode have been reported to crystallize in a noncentrosymmetric crystal structure and possess second harmonic generation properties (Patil et al., 2006; Patil & Dharmaprakash, 2007; Patil et al., 2007b). In our previous investigation, the crystal structure of 1-(4-chlorophenyl)-3-(4-ethoxyphenyl)prop-2-en-1-one has been reported (Patil et al., 2007a). To further understand the structure-property relationship, the title chalcone derivative was synthesized with ethoxy as an electron-donor group. The title compound crystallized in the non-centrosymmetric monoclinic P2₁ space group and therefore it should exhibit second-order nonlinear optical properties.

The title molecule (Fig.1) is nearly planar and exists in an E configuration with respect to the C8═C9 double bond [1.341 (3) Å]; the C7–C8–C9–C10 torsion angle is -177.6 (2)°. The dihedral angle between rings A and B is 10.09 (11)°. The enone unit (C7–C9/O1) is essentially planar, with a maximum deviation of 0.040 (2) Å for atom C8. The mean plane through the enone unit makes dihedral angles of 12.05 (11)° and 9.87 (11)° with the planes of rings A and B, respectively. The planar ethoxy group [C13—O2—C16—C17 = 176.3 (2)°] is almost coplanar with the ring B [C16—O2—C13—C12 of -2.1 (3)°]. The deviations of atoms O2, C16 and C17 from ring B are 0.007 (2), 0.052 (3) and -0.056 (3) Å, respectively. A weak C9–H9A···O1 interaction generates an S(5) ring motif. The bond distances and angles have normal values (Allen et al., 1987) and are comparable with those observed in related structures (Patil et al., 2007a,b).

In the crystal structure, the molecules are linked by C—H···O hydrogen bonds (Table 1) to form a zigzag ribbon-like structure along the b direction (Fig.2 and Fig.3).

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Patil et al. (2007a,b). Sathiya Moorthi et al. (2005a,b). For background to chalcones, see: Chopra et al. (2007); DiCesare et al. (2000); Gu et al. (2008a,b); Jiang et al. (1994); Lokaj et al. (2001); Low et al. (2002); Nel et al. (1998); Patil & Dharmaprakash (2007); Patil et al. (2006); Schmalle et al. (1990); Wang et al. (2004).

Experimental top

The title compound was synthesized by the condensation of 4-ethoxybenzaldehyde (0.01mol, 1.39 ml) with 3-bromoacetophenone (0.01 mol, 1.99 g)) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 20%). After stirring for 3 h, the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 4 h. The resulting crude solid was filtered and dried. Single crystals were obtained by recrystallization from acetone.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. The dashed line represent a C—H···O interaction.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.
	Fig. 3. The crystal packing of the title compound, showing zigzag ribbon-like structure running along the b axis. Hydrogen bonds are shown as dashed lines.

1-(3-Bromophenyl)-3-(4-ethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₇H₁₅BrO₂	F(000) = 336
M_r = 331.19	D_x = 1.572 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5989 reflections
a = 4.0516 (1) Å	θ = 1.1–35.0°
b = 9.6501 (2) Å	µ = 2.94 mm⁻¹
c = 17.9120 (4) Å	T = 100 K
β = 92.396 (1)°	Block, colourless
V = 699.72 (3) Å³	0.53 × 0.31 × 0.17 mm
Z = 2

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5989 independent reflections
Radiation source: fine-focus sealed tube	4682 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 8.33 pixels mm^-1	θ_max = 35.0°, θ_min = 1.1°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
T_min = 0.305, T_max = 0.642	l = −28→23
14837 measured reflections

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)] = 0.034	H-atom parameters constrained
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.0372P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.002
5989 reflections	Δρ_max = 0.69 e Å⁻³
182 parameters	Δρ_min = −0.65 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2764 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.021 (8)

Crystal data top

C₁₇H₁₅BrO₂	V = 699.72 (3) Å³
M_r = 331.19	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 4.0516 (1) Å	µ = 2.94 mm⁻¹
b = 9.6501 (2) Å	T = 100 K
c = 17.9120 (4) Å	0.53 × 0.31 × 0.17 mm
β = 92.396 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5989 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4682 reflections with I > 2σ(I)
T_min = 0.305, T_max = 0.642	R_int = 0.033
14837 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.093	Δρ_max = 0.69 e Å⁻³
S = 1.04	Δρ_min = −0.65 e Å⁻³
5989 reflections	Absolute structure: Flack (1983), 2764 Friedel pairs
182 parameters	Absolute structure parameter: 0.021 (8)
1 restraint

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Br1	0.44099 (5)	0.22151 (3)	0.509606 (11)	0.02359 (7)
O1	0.6257 (5)	0.16393 (19)	0.80200 (10)	0.0229 (4)
O2	0.0554 (4)	0.29630 (17)	1.23694 (9)	0.0191 (3)
C1	0.4078 (6)	0.2599 (2)	0.66571 (13)	0.0179 (4)
H1A	0.5320	0.1789	0.6686	0.021*
C2	0.3124 (6)	0.3148 (2)	0.59698 (13)	0.0174 (4)
C3	0.1291 (6)	0.4369 (2)	0.59085 (14)	0.0194 (4)
H3A	0.0668	0.4731	0.5443	0.023*
C4	0.0418 (6)	0.5031 (2)	0.65597 (14)	0.0194 (4)
H4A	−0.0799	0.5848	0.6528	0.023*
C5	0.1332 (6)	0.4494 (2)	0.72574 (14)	0.0173 (4)
H5A	0.0725	0.4948	0.7689	0.021*
C6	0.3170 (6)	0.3266 (2)	0.73090 (13)	0.0155 (4)
C7	0.4277 (6)	0.2592 (2)	0.80334 (13)	0.0163 (4)
C8	0.2936 (6)	0.3067 (2)	0.87445 (13)	0.0170 (4)
H8A	0.1488	0.3814	0.8756	0.020*
C9	0.3862 (5)	0.2391 (3)	0.93731 (12)	0.0162 (4)
H9A	0.5380	0.1681	0.9313	0.019*
C10	0.2857 (6)	0.2599 (2)	1.01363 (13)	0.0161 (4)
C11	0.0989 (6)	0.3739 (2)	1.03642 (13)	0.0165 (4)
H11A	0.0263	0.4389	1.0011	0.020*
C12	0.0207 (6)	0.3914 (2)	1.11050 (13)	0.0171 (4)
H12A	−0.0990	0.4684	1.1249	0.020*
C13	0.1238 (6)	0.2920 (2)	1.16333 (13)	0.0156 (4)
C14	0.3094 (6)	0.1789 (2)	1.14161 (13)	0.0169 (4)
H14A	0.3792	0.1131	1.1768	0.020*
C15	0.3906 (6)	0.1639 (2)	1.06790 (13)	0.0166 (4)
H15A	0.5173	0.0884	1.0542	0.020*
C16	−0.1265 (6)	0.4130 (3)	1.26362 (14)	0.0194 (5)
H16A	−0.3355	0.4225	1.2356	0.023*
H16B	−0.0010	0.4978	1.2584	0.023*
C17	−0.1832 (9)	0.3845 (3)	1.34460 (16)	0.0323 (7)
H17C	−0.3014	0.4605	1.3654	0.048*
H17A	0.0256	0.3736	1.3713	0.048*
H17B	−0.3101	0.3010	1.3488	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02512 (11)	0.03165 (12)	0.01422 (9)	−0.00028 (13)	0.00341 (7)	−0.00396 (12)
O1	0.0289 (10)	0.0226 (8)	0.0170 (8)	0.0094 (7)	0.0001 (7)	0.0002 (7)
O2	0.0236 (9)	0.0196 (8)	0.0144 (8)	0.0049 (7)	0.0052 (6)	0.0037 (6)
C1	0.0184 (10)	0.0188 (10)	0.0165 (10)	−0.0003 (7)	0.0022 (8)	0.0009 (7)
C2	0.0153 (10)	0.0197 (10)	0.0173 (11)	−0.0035 (8)	0.0026 (8)	−0.0029 (8)
C3	0.0210 (11)	0.0199 (10)	0.0175 (11)	−0.0043 (9)	0.0006 (8)	0.0042 (9)
C4	0.0200 (12)	0.0149 (10)	0.0231 (12)	−0.0007 (9)	−0.0016 (9)	0.0017 (9)
C5	0.0201 (11)	0.0150 (10)	0.0166 (11)	−0.0017 (8)	0.0004 (8)	−0.0012 (8)
C6	0.0186 (10)	0.0132 (9)	0.0147 (10)	−0.0024 (8)	0.0011 (8)	−0.0004 (7)
C7	0.0179 (10)	0.0145 (9)	0.0164 (10)	−0.0011 (7)	0.0004 (8)	−0.0020 (7)
C8	0.0190 (11)	0.0168 (10)	0.0151 (10)	0.0003 (8)	0.0006 (8)	−0.0025 (8)
C9	0.0176 (9)	0.0141 (12)	0.0168 (9)	−0.0005 (8)	0.0007 (7)	−0.0023 (8)
C10	0.0172 (10)	0.0142 (9)	0.0170 (10)	−0.0027 (7)	0.0009 (8)	−0.0001 (7)
C11	0.0179 (10)	0.0150 (9)	0.0165 (10)	−0.0013 (8)	−0.0008 (8)	0.0028 (8)
C12	0.0189 (11)	0.0147 (9)	0.0176 (11)	−0.0013 (8)	0.0013 (8)	0.0003 (8)
C13	0.0144 (10)	0.0161 (10)	0.0166 (10)	−0.0015 (8)	0.0036 (8)	0.0004 (8)
C14	0.0184 (11)	0.0136 (8)	0.0186 (11)	0.0009 (7)	0.0005 (8)	0.0043 (7)
C15	0.0161 (10)	0.0150 (9)	0.0188 (11)	0.0007 (8)	0.0011 (8)	0.0004 (8)
C16	0.0232 (12)	0.0161 (10)	0.0194 (11)	−0.0015 (8)	0.0060 (9)	−0.0003 (8)
C17	0.0467 (19)	0.0282 (13)	0.0230 (14)	0.0146 (13)	0.0146 (12)	0.0044 (11)

Geometric parameters (Å, º) top

Br1—C2	1.897 (2)	C9—C10	1.457 (3)
O1—C7	1.221 (3)	C9—H9A	0.93
O2—C13	1.359 (3)	C10—C15	1.397 (3)
O2—C16	1.439 (3)	C10—C11	1.405 (3)
C1—C2	1.381 (3)	C11—C12	1.387 (3)
C1—C6	1.396 (3)	C11—H11A	0.93
C1—H1A	0.93	C12—C13	1.399 (3)
C2—C3	1.394 (3)	C12—H12A	0.93
C3—C4	1.389 (3)	C13—C14	1.390 (3)
C3—H3A	0.93	C14—C15	1.381 (3)
C4—C5	1.389 (4)	C14—H14A	0.93
C4—H4A	0.93	C15—H15A	0.93
C5—C6	1.401 (3)	C16—C17	1.504 (4)
C5—H5A	0.93	C16—H16A	0.97
C6—C7	1.503 (3)	C16—H16B	0.97
C7—C8	1.478 (3)	C17—H17C	0.96
C8—C9	1.341 (3)	C17—H17A	0.96
C8—H8A	0.93	C17—H17B	0.96

C13—O2—C16	118.31 (18)	C15—C10—C9	118.2 (2)
C2—C1—C6	119.7 (2)	C11—C10—C9	123.8 (2)
C2—C1—H1A	120.2	C12—C11—C10	121.4 (2)
C6—C1—H1A	120.2	C12—C11—H11A	119.3
C1—C2—C3	121.5 (2)	C10—C11—H11A	119.3
C1—C2—Br1	118.50 (18)	C11—C12—C13	119.3 (2)
C3—C2—Br1	119.98 (18)	C11—C12—H12A	120.3
C4—C3—C2	118.4 (2)	C13—C12—H12A	120.3
C4—C3—H3A	120.8	O2—C13—C14	115.5 (2)
C2—C3—H3A	120.8	O2—C13—C12	124.6 (2)
C3—C4—C5	121.1 (2)	C14—C13—C12	119.9 (2)
C3—C4—H4A	119.5	C15—C14—C13	120.2 (2)
C5—C4—H4A	119.5	C15—C14—H14A	119.9
C4—C5—C6	119.7 (2)	C13—C14—H14A	119.9
C4—C5—H5A	120.1	C14—C15—C10	121.2 (2)
C6—C5—H5A	120.1	C14—C15—H15A	119.4
C1—C6—C5	119.5 (2)	C10—C15—H15A	119.4
C1—C6—C7	116.3 (2)	O2—C16—C17	106.1 (2)
C5—C6—C7	124.2 (2)	O2—C16—H16A	110.5
O1—C7—C8	121.0 (2)	C17—C16—H16A	110.5
O1—C7—C6	118.8 (2)	O2—C16—H16B	110.5
C8—C7—C6	120.19 (19)	C17—C16—H16B	110.5
C9—C8—C7	118.2 (2)	H16A—C16—H16B	108.7
C9—C8—H8A	120.9	C16—C17—H17C	109.5
C7—C8—H8A	120.9	C16—C17—H17A	109.5
C8—C9—C10	129.9 (2)	H17C—C17—H17A	109.5
C8—C9—H9A	115.0	C16—C17—H17B	109.5
C10—C9—H9A	115.0	H17C—C17—H17B	109.5
C15—C10—C11	118.0 (2)	H17A—C17—H17B	109.5

C6—C1—C2—C3	0.7 (4)	C7—C8—C9—C10	−177.6 (2)
C6—C1—C2—Br1	179.90 (17)	C8—C9—C10—C15	172.5 (3)
C1—C2—C3—C4	−0.2 (4)	C8—C9—C10—C11	−9.9 (4)
Br1—C2—C3—C4	−179.42 (18)	C15—C10—C11—C12	0.2 (3)
C2—C3—C4—C5	−0.2 (4)	C9—C10—C11—C12	−177.5 (2)
C3—C4—C5—C6	0.1 (4)	C10—C11—C12—C13	−1.4 (4)
C2—C1—C6—C5	−0.7 (3)	C16—O2—C13—C14	178.0 (2)
C2—C1—C6—C7	179.4 (2)	C16—O2—C13—C12	−2.1 (3)
C4—C5—C6—C1	0.3 (3)	C11—C12—C13—O2	−178.4 (2)
C4—C5—C6—C7	−179.8 (2)	C11—C12—C13—C14	1.5 (3)
C1—C6—C7—O1	10.3 (3)	O2—C13—C14—C15	179.5 (2)
C5—C6—C7—O1	−169.6 (2)	C12—C13—C14—C15	−0.4 (3)
C1—C6—C7—C8	−168.7 (2)	C13—C14—C15—C10	−0.8 (4)
C5—C6—C7—C8	11.4 (3)	C11—C10—C15—C14	1.0 (3)
O1—C7—C8—C9	−2.3 (3)	C9—C10—C15—C14	178.7 (2)
C6—C7—C8—C9	176.7 (2)	C13—O2—C16—C17	176.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.93	2.36	2.746 (3)	105
C16—H16B···O1ⁱ	0.97	2.49	3.400 (3)	157

Symmetry code: (i) −x+1, y+1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅BrO₂
M_r	331.19
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	4.0516 (1), 9.6501 (2), 17.9120 (4)
β (°)	92.396 (1)
V (Å³)	699.72 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.94
Crystal size (mm)	0.53 × 0.31 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.305, 0.642
No. of measured, independent and observed [I > 2σ(I)] reflections	14837, 5989, 4682
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.093, 1.04
No. of reflections	5989
No. of parameters	182
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.65
Absolute structure	Flack (1983), 2764 Friedel pairs
Absolute structure parameter	0.021 (8)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.93	2.36	2.746 (3)	105
C16—H16B···O1ⁱ	0.97	2.49	3.400 (3)	157

Symmetry code: (i) −x+1, y+1/2, −z+2.

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

This work is supported by the Department of Science and Technology (DST), Government of India, under grant No. SR/S2/LOP-17/2006. SC thanks Prince of Songkla University for generous support. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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