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

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

doi:10.1107/S1600536808021776

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages o1540-o1541

doi:10.1107/S1600536808021776

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

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

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

(Received 22 June 2008; accepted 13 July 2008; online 19 July 2008)

The title compound, C₁₇H₁₅BrO₂, consists of two substituted benzene rings connected by a prop-2-en-1-one group. The molecule is nearly planar and adopts an E configuration. The dihedral angle between the two benzene rings is 8.51 (19)°. The enone plane makes dihedral angles of 11.06 (19) and 7.69 (19)°, respectively, with the bromophenyl and ethoxyphenyl rings. The molecules are linked by C—H⋯O hydrogen bonds to form a zigzag ribbon-like structure along the b direction. The crystal structure is stabilized by weak intra- and intermolecular C—H⋯O interactions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For similar structures, see: Fun et al. (2008 ); Patil, Fun et al. (2007 ); Patil, Ng et al. (2007 ). For background on chalcones, see: Chopra et al. (2007 ); Fichou et al. (1988 ); Goto et al. (1991 ); Gu, Ji, Patil & Dharmaprakash (2008 ); Gu, Ji, Patil, Dharmaprakash & Wang (2008 ); Sathiya Moorthi, Chinnakali, Nanjundan, Radhika et al. (2005 ); Sathiya Moorthi, Chinnakali, Nanjundan, Selvam et al. (2005 ); Schmalle et al. (1990 ); Uchida et al. (1998 ); Wang et al. (2004 ); Zhao et al. (2000 ).

Experimental

Crystal data

C₁₇H₁₅BrO₂
M_r = 331.19
Monoclinic, P 2₁
a = 3.9855 (1) Å
b = 10.0681 (3) Å
c = 17.5270 (4) Å
β = 92.227 (2)°
V = 702.77 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.92 mm⁻¹
T = 100.0 (1) K
0.47 × 0.17 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.340, T_max = 0.781
7696 measured reflections
2620 independent reflections
2339 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.095
S = 1.08
2620 reflections
182 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −0.53 e Å⁻³
Absolute structure: Flack (1983 ), 656 Friedel pairs
Flack parameter: 0.013 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O2ⁱ	0.93	2.57	3.257 (5)	131
C9—H9A⋯O1	0.93	2.48	2.814 (5)	102
C16—H16B⋯O1ⁱⁱ	0.97	2.49	3.446 (5)	170
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+2]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+2]$ .

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/S1600536808021776/fl2206sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021776/fl2206Isup2.hkl

checkCIF report

Comment top

Chalcone and its derivatives have received much attention due to their interesting biological (Nel et al., 1998) and non-linear optical properties (Chopra et al., 2007; Sathiya Moorthi, Chinnakali, Nanjundan, Radhika et al., 2005; Sathiya Moorthi, Chinnakali, Nanjundan, Selvam et al., 2005; Schmalle et al., 1990; Wang et al., 2004; Gu, Ji, Patil & Dharmaprakash, 2008; Gu, Ji, Patil, Dharmaprakash & Wang, 2008). Understanding the origin and magnitude of nonlinearity in such exotic molecules is very important from both a fundamental point of view and for its wide range of applications. Some chalcone derivatives exhibiting second harmonic generation (SHG) also possess other attributes such as transparency in the relevant wavelengths, ability to withstand laser irradiation, and chemical stability (Fichou et al., 1988; Goto et al., 1991; Uchida et al., 1998; Zhao et al., 2000). We previously reported the crystal structure of a related chalcone derivative, 1-(3-bromophenyl)-3-(4-ethoxyphenyl) prop-2-en-1-one, (II) (Fun et al., 2008). In our continuing systematic study, we report here the structure of the title compound, (I) which also crystallized in a non-centrosymmetric space group and, as with (II), it should exhibit second-order nonlinear optical properties.

The molecular structure of (I) (Fig. 1) consists of two planar six-membered rings C1–C6 (ring A) and C10–C15 (ring B), with maximum deviations of 0.009 (4) and -0.010 (4) Å for atoms C6 (ring A) and C12(ring B), respectively. The molecule exists in an E configuration with respect to the C8=C9 double bond [1.336 (6) Å]: the torsion angle C7–C8–C9–C10 = -179.4 (4)°. The molecule is nearly planar with a dihedral angle between rings A and B of 8.51 (19)° [10.09 (11)° in (II) by Fun et al., 2008]. The mean plane C through enone unit (C7–C9/O1) makes dihedral angles of 11.06 (19)° and 7.69 (19)° with the planes of rings A and B, respectively [the corresponding values are 12.05 (11)° and 9.87 (11)° in (II)]. The ethoxy group itself is slightly twisted as indicated by the torsion angle C13—O2—C16—C17 = 173.4 (4)° but co-planar with the attached benzene ring B with the torsion angle C16/O2/C13/C12 = -1.2 (6)°. A weak C9–H9A···O1 intramolecular interaction (Fig. 1) generates an S(5) ring motif (Bernstein et al., 1995). The overall conformation of (I) is flatter than that observed for (II) which can be attributed to the different positions of the Br substituent on ring A (para in (I) and meta in (II). The bond distances and angles in (I) have normal values and are comparable with a number of closely related structures (Fun et al., 2008; Patil, Fun et al., 2007; Patil, Ng et al., 2007).

In the crystal packing, the molecules are arranged in an anti-parallel manner and linked by weak C—H···O interactions (Table 1) into a zigzag ribbon-like structure along the b direction (Fig. 2 and Fig. 3). Similar packing characteristics were observed in (II) (Fun et al., 2008). In (I) the same weak C—H···O (C16—H16B···O1) interaction is involved in the ribbon-linkage but there is also an additional weak C—H···O interaction which links the molecules (Table 1). This is also due to the different positions of the meta and para Br substitutions in (I) and (II) which made (I) more favourable for the C—H···O contacts.

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For similar structures, see: Fun et al. (2008); Patil, Fun et al. (2007); Patil, Ng et al. (2007). For background on chalcones, see: Chopra et al. (2007); Fichou et al. (1988); Goto et al. (1991); Gu, Ji, Patil & Dharmaprakash (2008); Gu, Ji, Patil, Dharmaprakash & Wang (2008); Nel et al. (1998); Sathiya Moorthi, Chinnakali, Nanjundan, Radhika et al. (2005); Sathiya Moorthi, Chinnakali, Nanjundan, Selvam et al. (2005); Schmalle et al. (1990); Uchida et al. (1998); Wang et al. (2004); Zhao et al. (2000).

Experimental top

The title compound was synthesized by the condensation of 4-ethoxybenzaldehyde (0.01 mol, 1.39 ml) with 4-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 (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme. The dashed line represents the intra-molcular C—H···O interaction.
	Fig. 2. Crystal packing for (I) viewed along the a axis showing an antiparallel arrangement of the molecules. Hydrogen bonds are shown as dashed lines.
	Fig. 3. Crystal packing for (I) showing the zigzag ribbon-like structure running along the b axis. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₇H₁₅BrO₂	F(000) = 336
M_r = 331.19	D_x = 1.565 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2620 reflections
a = 3.9855 (1) Å	θ = 1.2–29.0°
b = 10.0681 (3) Å	µ = 2.92 mm⁻¹
c = 17.5270 (4) Å	T = 100 K
β = 92.227 (2)°	Block, colorless
V = 702.77 (3) Å³	0.47 × 0.17 × 0.09 mm
Z = 2

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2620 independent reflections
Radiation source: fine-focus sealed tube	2339 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 8.33 pixels mm^-1	θ_max = 29.0°, θ_min = 1.2°
ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→8
T_min = 0.340, T_max = 0.781	l = −23→23
7696 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)] = 0.033	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0562P)²] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2620 reflections	Δρ_max = 0.98 e Å⁻³
182 parameters	Δρ_min = −0.53 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 640 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.013 (13)

Crystal data top

C₁₇H₁₅BrO₂	V = 702.77 (3) Å³
M_r = 331.19	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 3.9855 (1) Å	µ = 2.92 mm⁻¹
b = 10.0681 (3) Å	T = 100 K
c = 17.5270 (4) Å	0.47 × 0.17 × 0.09 mm
β = 92.227 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2620 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2339 reflections with I > 2σ(I)
T_min = 0.340, T_max = 0.781	R_int = 0.033
7696 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.095	Δρ_max = 0.98 e Å⁻³
S = 1.08	Δρ_min = −0.53 e Å⁻³
2620 reflections	Absolute structure: Flack (1983), 640 Friedel pairs
182 parameters	Absolute structure parameter: 0.013 (13)
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	0.43528 (8)	0.23538 (6)	0.502628 (18)	0.02637 (12)
O1	−0.1514 (7)	0.6546 (3)	0.77360 (17)	0.0282 (7)
O2	0.5201 (7)	0.5258 (3)	1.22900 (16)	0.0234 (6)
C1	0.0563 (11)	0.5256 (4)	0.6436 (3)	0.0234 (9)
H1A	−0.0604	0.6052	0.6379	0.028*
C2	0.1400 (10)	0.4543 (4)	0.5789 (2)	0.0210 (8)
H2A	0.0835	0.4859	0.5302	0.025*
C3	0.3114 (9)	0.3340 (4)	0.5890 (2)	0.0195 (8)
C4	0.3966 (9)	0.2855 (4)	0.6611 (2)	0.0229 (8)
H4A	0.5097	0.2051	0.6669	0.027*
C5	0.3112 (10)	0.3583 (4)	0.7242 (2)	0.0216 (8)
H5A	0.3659	0.3258	0.7728	0.026*
C6	0.1443 (10)	0.4796 (4)	0.7165 (2)	0.0197 (8)
C7	0.0421 (11)	0.5603 (4)	0.7834 (2)	0.0241 (9)
C8	0.1824 (10)	0.5255 (5)	0.8602 (2)	0.0249 (9)
H8A	0.3356	0.4561	0.8655	0.030*
C9	0.0927 (10)	0.5921 (4)	0.9221 (2)	0.0236 (9)
H9A	−0.0626	0.6601	0.9142	0.028*
C10	0.2115 (10)	0.5700 (4)	1.0008 (2)	0.0219 (8)
C11	0.4006 (10)	0.4600 (4)	1.0240 (3)	0.0235 (9)
H11A	0.4597	0.3979	0.9876	0.028*
C12	0.5036 (10)	0.4399 (4)	1.0993 (2)	0.0241 (9)
H12A	0.6252	0.3643	1.1133	0.029*
C13	0.4243 (10)	0.5332 (4)	1.1541 (2)	0.0220 (8)
C14	0.2317 (10)	0.6439 (4)	1.1322 (2)	0.0228 (9)
H14A	0.1741	0.7059	1.1687	0.027*
C15	0.1258 (10)	0.6625 (4)	1.0569 (2)	0.0223 (8)
H15A	−0.0028	0.7365	1.0433	0.027*
C16	0.7128 (11)	0.4120 (4)	1.2541 (3)	0.0247 (9)
H16A	0.9075	0.4014	1.2231	0.030*
H16B	0.5773	0.3322	1.2495	0.030*
C17	0.8217 (13)	0.4350 (5)	1.3364 (3)	0.0328 (12)
H17A	0.9605	0.3625	1.3541	0.049*
H17B	0.6272	0.4407	1.3669	0.049*
H17C	0.9465	0.5163	1.3406	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02618 (18)	0.0284 (2)	0.02459 (17)	−0.0013 (3)	0.00238 (12)	−0.0061 (2)
O1	0.0305 (16)	0.0211 (17)	0.0332 (16)	0.0038 (13)	0.0033 (13)	−0.0008 (13)
O2	0.0222 (14)	0.0203 (15)	0.0275 (14)	0.0029 (12)	−0.0015 (12)	−0.0018 (12)
C1	0.026 (2)	0.014 (2)	0.030 (2)	−0.0016 (19)	0.0027 (18)	0.0004 (18)
C2	0.0227 (19)	0.019 (2)	0.0218 (18)	−0.0029 (17)	0.0000 (15)	0.0045 (15)
C3	0.0184 (17)	0.017 (2)	0.0229 (18)	−0.0049 (15)	0.0036 (14)	−0.0029 (15)
C4	0.0199 (17)	0.0192 (18)	0.029 (2)	0.0005 (17)	−0.0002 (15)	0.0007 (17)
C5	0.0247 (19)	0.017 (2)	0.0226 (19)	−0.0001 (16)	−0.0030 (16)	0.0040 (16)
C6	0.021 (2)	0.0155 (18)	0.0222 (18)	−0.0033 (15)	0.0012 (16)	−0.0020 (17)
C7	0.026 (2)	0.020 (2)	0.027 (2)	−0.0048 (17)	0.0057 (17)	0.0006 (17)
C8	0.0225 (19)	0.020 (2)	0.032 (2)	0.0018 (17)	0.0013 (17)	0.0015 (18)
C9	0.0233 (19)	0.018 (2)	0.029 (2)	−0.0030 (17)	0.0013 (16)	−0.0010 (17)
C10	0.0191 (18)	0.018 (2)	0.029 (2)	−0.0054 (16)	0.0046 (15)	−0.0038 (16)
C11	0.023 (2)	0.016 (2)	0.032 (2)	−0.0033 (16)	0.0084 (16)	−0.0057 (16)
C12	0.0209 (19)	0.0152 (19)	0.036 (2)	0.0016 (17)	0.0035 (17)	−0.0028 (18)
C13	0.0178 (18)	0.0172 (19)	0.031 (2)	−0.0035 (16)	0.0026 (16)	−0.0046 (17)
C14	0.0220 (19)	0.0169 (19)	0.030 (2)	−0.0018 (16)	0.0029 (16)	−0.0068 (17)
C15	0.0201 (18)	0.017 (2)	0.030 (2)	−0.0004 (15)	0.0011 (16)	−0.0030 (16)
C16	0.024 (2)	0.013 (2)	0.037 (2)	−0.0003 (16)	−0.0013 (18)	0.0026 (18)
C17	0.032 (3)	0.025 (2)	0.042 (3)	−0.002 (2)	−0.003 (2)	0.008 (2)

Geometric parameters (Å, º) top

Br1—C3	1.892 (4)	C9—C10	1.456 (6)
O1—C7	1.231 (5)	C9—H9A	0.9300
O2—C13	1.354 (5)	C10—C11	1.392 (6)
O2—C16	1.438 (5)	C10—C15	1.406 (6)
C1—C6	1.391 (6)	C11—C12	1.383 (6)
C1—C2	1.393 (6)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.389 (6)
C2—C3	1.399 (6)	C12—H12A	0.9300
C2—H2A	0.9300	C13—C14	1.399 (6)
C3—C4	1.385 (6)	C14—C15	1.383 (6)
C4—C5	1.381 (6)	C14—H14A	0.9300
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.395 (6)	C16—C17	1.508 (6)
C5—H5A	0.9300	C16—H16A	0.9700
C6—C7	1.496 (6)	C16—H16B	0.9700
C7—C8	1.480 (6)	C17—H17A	0.9600
C8—C9	1.336 (6)	C17—H17B	0.9600
C8—H8A	0.9300	C17—H17C	0.9600

C13—O2—C16	117.9 (3)	C11—C10—C9	123.4 (4)
C6—C1—C2	121.1 (4)	C15—C10—C9	118.8 (4)
C6—C1—H1A	119.5	C12—C11—C10	122.2 (4)
C2—C1—H1A	119.5	C12—C11—H11A	118.9
C1—C2—C3	118.3 (4)	C10—C11—H11A	118.9
C1—C2—H2A	120.8	C11—C12—C13	119.6 (4)
C3—C2—H2A	120.8	C11—C12—H12A	120.2
C4—C3—C2	121.5 (4)	C13—C12—H12A	120.2
C4—C3—Br1	118.9 (3)	O2—C13—C12	124.7 (4)
C2—C3—Br1	119.6 (3)	O2—C13—C14	116.2 (4)
C5—C4—C3	119.0 (4)	C12—C13—C14	119.1 (4)
C5—C4—H4A	120.5	C15—C14—C13	121.0 (4)
C3—C4—H4A	120.5	C15—C14—H14A	119.5
C4—C5—C6	121.2 (4)	C13—C14—H14A	119.5
C4—C5—H5A	119.4	C14—C15—C10	120.3 (4)
C6—C5—H5A	119.4	C14—C15—H15A	119.8
C1—C6—C5	118.9 (4)	C10—C15—H15A	119.8
C1—C6—C7	118.2 (4)	O2—C16—C17	107.5 (4)
C5—C6—C7	122.8 (4)	O2—C16—H16A	110.2
O1—C7—C8	121.5 (4)	C17—C16—H16A	110.2
O1—C7—C6	119.8 (4)	O2—C16—H16B	110.2
C8—C7—C6	118.7 (4)	C17—C16—H16B	110.2
C9—C8—C7	121.1 (4)	H16A—C16—H16B	108.5
C9—C8—H8A	119.4	C16—C17—H17A	109.5
C7—C8—H8A	119.4	C16—C17—H17B	109.5
C8—C9—C10	127.2 (4)	H17A—C17—H17B	109.5
C8—C9—H9A	116.4	C16—C17—H17C	109.5
C10—C9—H9A	116.4	H17A—C17—H17C	109.5
C11—C10—C15	117.8 (4)	H17B—C17—H17C	109.5

C6—C1—C2—C3	0.9 (6)	C7—C8—C9—C10	−179.4 (4)
C1—C2—C3—C4	0.2 (6)	C8—C9—C10—C11	−10.6 (7)
C1—C2—C3—Br1	−179.1 (3)	C8—C9—C10—C15	170.8 (4)
C2—C3—C4—C5	−0.3 (6)	C15—C10—C11—C12	0.1 (6)
Br1—C3—C4—C5	179.0 (3)	C9—C10—C11—C12	−178.5 (4)
C3—C4—C5—C6	−0.6 (6)	C10—C11—C12—C13	−1.5 (6)
C2—C1—C6—C5	−1.8 (6)	C16—O2—C13—C12	−1.2 (6)
C2—C1—C6—C7	−179.2 (4)	C16—O2—C13—C14	178.8 (3)
C4—C5—C6—C1	1.6 (6)	C11—C12—C13—O2	−178.0 (4)
C4—C5—C6—C7	178.9 (4)	C11—C12—C13—C14	2.1 (6)
C1—C6—C7—O1	9.3 (6)	O2—C13—C14—C15	178.8 (4)
C5—C6—C7—O1	−168.0 (4)	C12—C13—C14—C15	−1.2 (6)
C1—C6—C7—C8	−169.7 (4)	C13—C14—C15—C10	−0.2 (6)
C5—C6—C7—C8	13.0 (6)	C11—C10—C15—C14	0.8 (6)
O1—C7—C8—C9	2.8 (7)	C9—C10—C15—C14	179.4 (4)
C6—C7—C8—C9	−178.3 (4)	C13—O2—C16—C17	173.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O2ⁱ	0.93	2.57	3.257 (5)	131
C9—H9A···O1	0.93	2.48	2.814 (5)	102
C16—H16B···O1ⁱⁱ	0.97	2.49	3.446 (5)	170

Symmetry codes: (i) −x+1, y−1/2, −z+2; (ii) −x, 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)	3.9855 (1), 10.0681 (3), 17.5270 (4)
β (°)	92.227 (2)
V (Å³)	702.77 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.92
Crystal size (mm)	0.47 × 0.17 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.340, 0.781
No. of measured, independent and observed [I > 2σ(I)] reflections	7696, 2620, 2339
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.095, 1.08
No. of reflections	2620
No. of parameters	182
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.98, −0.53
Absolute structure	Flack (1983), 640 Friedel pairs
Absolute structure parameter	0.013 (13)

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
C4—H4A···O2ⁱ	0.93	2.5727	3.257 (5)	131
C9—H9A···O1	0.93	2.4766	2.814 (5)	102
C16—H16B···O1ⁱⁱ	0.97	2.4878	3.446 (5)	170

Symmetry codes: (i) −x+1, y−1/2, −z+2; (ii) −x, 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 the Prince of Songkla University for generous support. The authors also thank the Universiti Sains Malaysia for the Research University Golden Goose Grant No. 1001/PFIZIK/811012.

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