(E)-3-(Anthracen-9-yl)-1-(4-bromo­phen­yl)prop-2-en-1-one

Suwunwong, T.; Chantrapromma, S.; Karalai, C.; Pakdeevanich, P.; Fun, H.-K.

doi:10.1107/S1600536809003122

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages o420-o421

doi:10.1107/S1600536809003122

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(E)-3-(Anthracen-9-yl)-1-(4-bromophenyl)prop-2-en-1-one †

Thitipone Suwunwong,^a Suchada Chantrapromma,^b ^* Chatchanok Karalai,^b Paradorn Pakdeevanich ^c and Hoong-Kun Fun ^d ‡

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^cDepartment of Physics, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 31 December 2008; accepted 26 January 2009; online 31 January 2009)

In the title molecule, C₂₃H₁₅BrO, the prop-2-en-1-one unit is planar and it makes dihedral angles of 20.9 (1) and 45.8 (1)°, respectively, with the 4-bromophenyl ring and the anthracene ring system. The interplanar angle between the 4-bromophenyl ring and the anthracene ring system is 35.52 (7)°. In the crystal structure, molecules are linked into dimers by C—H⋯Br hydrogen bonds, and the dimers are linked into a zigzag network parallel to the bc plane by weak C—H⋯O hydrogen bonds and C—H⋯π interactions involving the central benzene ring of the anthracene ring system.

Related literature

For bond-length data, see: Allen et al. (1987 ). For related structures, see: Ng et al. (2006 ); Patil et al. (2006 ); Patil, Chantrapromma et al. (2007 ); Suwunwong et al. (2009 ). For background and applications of chalcones, see: Jung et al. (2008 ); Patil, Chantrapromma et al. (2007); Patil, Dharmaprakash et al. (2007 ); Patil & Dharmaprakash (2008 ); Prasad et al. (2008 ).

Experimental

Crystal data

C₂₃H₁₅BrO
M_r = 387.25
Monoclinic, P 2₁ /c
a = 5.3792 (1) Å
b = 19.1030 (4) Å
c = 16.3005 (4) Å
β = 95.944 (1)°
V = 1666.02 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.47 mm⁻¹
T = 100.0 (1) K
0.57 × 0.27 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.331, T_max = 0.714
29994 measured reflections
4866 independent reflections
3803 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.076
S = 1.02
4866 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1ⁱ	0.93	2.42	3.308 (2)	159
C13—H13A⋯O1ⁱⁱ	0.93	2.57	3.288 (2)	135
C21—H21A⋯Br1ⁱⁱⁱ	0.93	2.93	3.4722 (19)	119
C9—H9A⋯Cg1^iv	0.93	2.83	3.4479 (18)	125
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y+1, -z+2; (iii) -x, -y+1, -z+1; (iv) x+1, y, z.

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/S1600536809003122/ci2756sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003122/ci2756Isup2.hkl

checkCIF report

Comment top

Chalcones are compounds which have a wide range of applications covering from non-linear optical (Patil & Dharmaprakash, 2008) and electro-active fluorescent materials (Jung et al., 2008) to materials with various biological activities (Prasad et al., 2008). Our previous work (Patil Dharmaprakash et al., 2007) has reported that 1-(4-bromophenyl)-3-(2,4,5-trimethoxyphenyl)-propenone shows efficient second-order nonlinear optical properties. The various interesting properties of chalcone derivatives lead us to synthesize the title chalcone derivative in order to study its photoluminescence and antimicrobial activities.

The molecule of the title chalcone derivative (Fig. 1) exists in an E configuration with respect to the C8═C9 double bond [1.333 (2) Å]. The anthracene ring system is planar, with atom C21 deviating a maximum of 0.147 (2) Å. The molecule is twisted as indicated by the interplanar angle between 4-bromophenyl ring and anthracene ring system of 35.52 (7)°, and torsion angles C5–C6–C7–C8 of 22.9 (1)° and C8–C9–C10–C23 of -50.2 (3)°. The pro-2-en-1-one unit (C7-C9/O1) is planar as evidenced by the torsion angle O1–C7–C8–C9 of 0.1 (3)°. The O1/C6-C9 plane makes dihedral angles of 20.9 (1)° and 45.8 (1)°, respectively, with the 4-bromophenyl ring and anthracene ring system. The bond distances show normal values (Allen et al., 1987) and are comparable with those observed in related structures (Ng et al., 2006; Patil et al., 2006; Patil, Chantrapromma et al., 2007; Suwunwong et al., 2009).

In the crystal packing (Fig. 2), the molecules are linked into dimers by weak C—H···Br interactions (Table 1) and the dimers are further linked into a zigzag network parallel to the bc plane by weak C—H···O and C—H···π interactions (Table 1).

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Ng et al. (2006); Patil et al. (2006); Patil, Chantrapromma et al. (2007); Suwunwong et al. (2009). For background and applications of chalcones, see: Jung et al. (2008); Patil, Chantrapromma et al. (2007); Patil, Dharmaprakash et al. (2007); Patil & Dharmaprakash (2008); Prasad et al. (2008).

Experimental top

The title compound was synthesized by the condensation of anthracene-9-carbaldehyde (0.01 mol) with 4-bromoacetophenone (0.01 mol) in ethanol (40 ml) in the presence of NaOH (10 ml, 10%). After stirring for 2 h, a yellow solid appeared and was then collected by filtration, washed with distilled water, dried and purified by repeated recrystallization from acetone. Yellow plate-shaped single crystals of the title compound suitable for X-ray structure determination were obtained by slow evaporation of an acetone solution at room temperature after several days.

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 60% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Part of the crystal packing of the title compound, viewed along the a axis, showing hydrogen-bonded (dashed lines) dimers.

(E)-3-(Anthracen-9-yl)-1-(4-bromophenyl)prop-2-en-1-one top

Crystal data top

C₂₃H₁₅BrO	F(000) = 784
M_r = 387.25	D_x = 1.544 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4866 reflections
a = 5.3792 (1) Å	θ = 2.1–30.0°
b = 19.1030 (4) Å	µ = 2.47 mm⁻¹
c = 16.3005 (4) Å	T = 100 K
β = 95.944 (1)°	Plate, yellow
V = 1666.02 (6) Å³	0.57 × 0.27 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4866 independent reflections
Radiation source: fine-focus sealed tube	3803 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 2.1°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −26→26
T_min = 0.331, T_max = 0.714	l = −22→22
29994 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0322P)² + 1.1607P] where P = (F_o² + 2F_c²)/3
4866 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₂₃H₁₅BrO	V = 1666.02 (6) Å³
M_r = 387.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.3792 (1) Å	µ = 2.47 mm⁻¹
b = 19.1030 (4) Å	T = 100 K
c = 16.3005 (4) Å	0.57 × 0.27 × 0.15 mm
β = 95.944 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4866 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3803 reflections with I > 2σ(I)
T_min = 0.331, T_max = 0.714	R_int = 0.036
29994 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.02	Δρ_max = 0.53 e Å⁻³
4866 reflections	Δρ_min = −0.54 e Å⁻³
226 parameters

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	0.32584 (4)	0.344013 (10)	0.411244 (11)	0.02530 (7)
O1	0.9073 (2)	0.51056 (7)	0.74450 (8)	0.0213 (3)
C1	0.7274 (4)	0.41439 (9)	0.62533 (11)	0.0201 (4)
H1A	0.8800	0.4043	0.6552	0.024*
C2	0.6526 (4)	0.37631 (10)	0.55484 (12)	0.0219 (4)
H2A	0.7530	0.3408	0.5374	0.026*
C3	0.4261 (4)	0.39203 (9)	0.51095 (10)	0.0180 (4)
C4	0.2711 (4)	0.44314 (10)	0.53719 (11)	0.0206 (4)
H4A	0.1176	0.4523	0.5075	0.025*
C5	0.3464 (3)	0.48075 (10)	0.60836 (10)	0.0184 (4)
H5A	0.2419	0.5149	0.6267	0.022*
C6	0.5781 (3)	0.46766 (9)	0.65244 (10)	0.0152 (3)
C7	0.6813 (3)	0.51052 (9)	0.72478 (10)	0.0159 (3)
C8	0.5083 (3)	0.55087 (9)	0.77158 (10)	0.0159 (3)
H8A	0.3374	0.5499	0.7555	0.019*
C9	0.5978 (3)	0.58858 (9)	0.83690 (10)	0.0161 (3)
H9A	0.7707	0.5920	0.8471	0.019*
C10	0.4492 (3)	0.62533 (9)	0.89440 (10)	0.0158 (3)
C11	0.5151 (3)	0.61533 (9)	0.98020 (10)	0.0157 (3)
C12	0.7151 (4)	0.57046 (10)	1.01164 (11)	0.0195 (4)
H12A	0.8015	0.5452	0.9749	0.023*
C13	0.7822 (4)	0.56385 (10)	1.09428 (11)	0.0219 (4)
H13A	0.9149	0.5349	1.1132	0.026*
C14	0.6506 (4)	0.60082 (10)	1.15145 (11)	0.0220 (4)
H14A	0.7002	0.5970	1.2076	0.026*
C15	0.4527 (4)	0.64183 (10)	1.12478 (11)	0.0224 (4)
H15A	0.3652	0.6648	1.1631	0.027*
C16	0.3767 (3)	0.65030 (9)	1.03860 (10)	0.0169 (3)
C17	0.1715 (4)	0.69108 (9)	1.01020 (10)	0.0187 (4)
H17A	0.0769	0.7118	1.0482	0.022*
C18	0.1036 (3)	0.70178 (9)	0.92633 (10)	0.0167 (3)
C19	−0.1040 (4)	0.74534 (9)	0.89840 (11)	0.0196 (4)
H19A	−0.2054	0.7629	0.9365	0.023*
C20	−0.1560 (4)	0.76158 (9)	0.81740 (11)	0.0211 (4)
H20A	−0.2925	0.7898	0.8002	0.025*
C21	−0.0008 (4)	0.73530 (9)	0.75909 (11)	0.0205 (4)
H21A	−0.0309	0.7487	0.7041	0.025*
C22	0.1913 (3)	0.69077 (9)	0.78224 (10)	0.0184 (4)
H22A	0.2862	0.6730	0.7424	0.022*
C23	0.2504 (3)	0.67066 (9)	0.86689 (10)	0.0153 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03907 (13)	0.02093 (10)	0.01575 (9)	−0.00663 (8)	0.00217 (7)	−0.00386 (7)
O1	0.0137 (7)	0.0297 (7)	0.0203 (6)	0.0009 (5)	0.0009 (5)	−0.0031 (5)
C1	0.0181 (10)	0.0199 (9)	0.0219 (9)	0.0037 (7)	0.0000 (7)	−0.0002 (7)
C2	0.0238 (10)	0.0180 (9)	0.0239 (9)	0.0060 (7)	0.0029 (7)	−0.0027 (7)
C3	0.0238 (10)	0.0159 (8)	0.0146 (8)	−0.0052 (7)	0.0032 (6)	−0.0018 (6)
C4	0.0170 (10)	0.0258 (9)	0.0182 (8)	−0.0003 (7)	−0.0010 (7)	−0.0016 (7)
C5	0.0158 (9)	0.0228 (9)	0.0168 (8)	0.0022 (7)	0.0020 (6)	−0.0031 (7)
C6	0.0155 (9)	0.0169 (8)	0.0134 (7)	−0.0013 (6)	0.0024 (6)	0.0007 (6)
C7	0.0156 (9)	0.0176 (8)	0.0148 (7)	−0.0011 (7)	0.0027 (6)	0.0005 (6)
C8	0.0119 (9)	0.0206 (8)	0.0155 (7)	−0.0010 (7)	0.0022 (6)	−0.0008 (6)
C9	0.0133 (9)	0.0179 (8)	0.0175 (8)	−0.0016 (7)	0.0032 (6)	0.0007 (6)
C10	0.0157 (9)	0.0163 (8)	0.0155 (8)	−0.0035 (7)	0.0024 (6)	−0.0019 (6)
C11	0.0163 (9)	0.0155 (8)	0.0154 (8)	−0.0034 (7)	0.0018 (6)	−0.0006 (6)
C12	0.0195 (10)	0.0211 (9)	0.0184 (8)	−0.0005 (7)	0.0034 (7)	−0.0008 (7)
C13	0.0209 (10)	0.0240 (9)	0.0202 (8)	−0.0003 (8)	−0.0003 (7)	0.0026 (7)
C14	0.0292 (11)	0.0223 (9)	0.0140 (8)	−0.0036 (8)	−0.0004 (7)	0.0005 (7)
C15	0.0307 (11)	0.0227 (9)	0.0141 (8)	−0.0017 (8)	0.0042 (7)	−0.0017 (7)
C16	0.0210 (9)	0.0144 (8)	0.0156 (8)	−0.0040 (7)	0.0036 (6)	−0.0015 (6)
C17	0.0225 (10)	0.0168 (8)	0.0175 (8)	−0.0003 (7)	0.0054 (7)	−0.0032 (6)
C18	0.0182 (9)	0.0142 (8)	0.0178 (8)	−0.0032 (7)	0.0021 (6)	−0.0015 (6)
C19	0.0193 (10)	0.0156 (8)	0.0244 (9)	−0.0002 (7)	0.0050 (7)	−0.0024 (7)
C20	0.0200 (10)	0.0160 (8)	0.0266 (9)	−0.0010 (7)	−0.0018 (7)	0.0006 (7)
C21	0.0216 (10)	0.0209 (9)	0.0182 (8)	−0.0033 (7)	−0.0016 (7)	0.0014 (7)
C22	0.0192 (10)	0.0191 (9)	0.0168 (8)	−0.0029 (7)	0.0020 (6)	−0.0020 (7)
C23	0.0155 (9)	0.0154 (8)	0.0150 (7)	−0.0048 (6)	0.0013 (6)	−0.0018 (6)

Geometric parameters (Å, º) top

Br1—C3	1.8954 (17)	C12—C13	1.364 (2)
O1—C7	1.225 (2)	C12—H12A	0.93
C1—C2	1.384 (3)	C13—C14	1.416 (3)
C1—C6	1.396 (2)	C13—H13A	0.93
C1—H1A	0.93	C14—C15	1.356 (3)
C2—C3	1.380 (3)	C14—H14A	0.93
C2—H2A	0.93	C15—C16	1.431 (2)
C3—C4	1.380 (3)	C15—H15A	0.93
C4—C5	1.389 (2)	C16—C17	1.391 (3)
C4—H4A	0.93	C17—C18	1.393 (2)
C5—C6	1.395 (2)	C17—H17A	0.93
C5—H5A	0.93	C18—C19	1.429 (3)
C6—C7	1.495 (2)	C18—C23	1.440 (2)
C7—C8	1.480 (2)	C19—C20	1.357 (3)
C8—C9	1.333 (2)	C19—H19A	0.93
C8—H8A	0.93	C20—C21	1.420 (3)
C9—C10	1.472 (2)	C20—H20A	0.93
C9—H9A	0.93	C21—C22	1.361 (3)
C10—C23	1.413 (3)	C21—H21A	0.93
C10—C11	1.420 (2)	C22—C23	1.436 (2)
C11—C12	1.428 (3)	C22—H22A	0.93
C11—C16	1.433 (2)

C2—C1—C6	121.23 (17)	C11—C12—H12A	119.3
C2—C1—H1A	119.4	C12—C13—C14	120.32 (18)
C6—C1—H1A	119.4	C12—C13—H13A	119.8
C3—C2—C1	118.75 (17)	C14—C13—H13A	119.8
C3—C2—H2A	120.6	C15—C14—C13	120.41 (17)
C1—C2—H2A	120.6	C15—C14—H14A	119.8
C4—C3—C2	121.49 (16)	C13—C14—H14A	119.8
C4—C3—Br1	118.73 (14)	C14—C15—C16	121.00 (17)
C2—C3—Br1	119.78 (14)	C14—C15—H15A	119.5
C3—C4—C5	119.44 (17)	C16—C15—H15A	119.5
C3—C4—H4A	120.3	C17—C16—C15	121.78 (16)
C5—C4—H4A	120.3	C17—C16—C11	119.28 (16)
C4—C5—C6	120.34 (17)	C15—C16—C11	118.94 (17)
C4—C5—H5A	119.8	C16—C17—C18	121.81 (16)
C6—C5—H5A	119.8	C16—C17—H17A	119.1
C5—C6—C1	118.69 (16)	C18—C17—H17A	119.1
C5—C6—C7	123.18 (16)	C17—C18—C19	120.98 (16)
C1—C6—C7	118.04 (16)	C17—C18—C23	119.57 (16)
O1—C7—C8	121.62 (16)	C19—C18—C23	119.41 (15)
O1—C7—C6	119.02 (15)	C20—C19—C18	121.24 (17)
C8—C7—C6	119.35 (15)	C20—C19—H19A	119.4
C9—C8—C7	119.93 (16)	C18—C19—H19A	119.4
C9—C8—H8A	120.0	C19—C20—C21	119.62 (18)
C7—C8—H8A	120.0	C19—C20—H20A	120.2
C8—C9—C10	126.25 (17)	C21—C20—H20A	120.2
C8—C9—H9A	116.9	C22—C21—C20	121.16 (16)
C10—C9—H9A	116.9	C22—C21—H21A	119.4
C23—C10—C11	119.94 (15)	C20—C21—H21A	119.4
C23—C10—C9	122.24 (15)	C21—C22—C23	121.31 (17)
C11—C10—C9	117.80 (16)	C21—C22—H22A	119.3
C10—C11—C12	122.43 (16)	C23—C22—H22A	119.3
C10—C11—C16	119.84 (16)	C10—C23—C22	123.65 (16)
C12—C11—C16	117.72 (15)	C10—C23—C18	119.29 (15)
C13—C12—C11	121.49 (17)	C22—C23—C18	116.99 (16)
C13—C12—H12A	119.3

C6—C1—C2—C3	0.3 (3)	C13—C14—C15—C16	−1.8 (3)
C1—C2—C3—C4	−1.9 (3)	C14—C15—C16—C17	178.78 (18)
C1—C2—C3—Br1	176.90 (14)	C14—C15—C16—C11	−0.8 (3)
C2—C3—C4—C5	1.4 (3)	C10—C11—C16—C17	3.0 (3)
Br1—C3—C4—C5	−177.43 (14)	C12—C11—C16—C17	−176.19 (16)
C3—C4—C5—C6	0.8 (3)	C10—C11—C16—C15	−177.41 (16)
C4—C5—C6—C1	−2.4 (3)	C12—C11—C16—C15	3.4 (2)
C4—C5—C6—C7	174.05 (17)	C15—C16—C17—C18	177.22 (17)
C2—C1—C6—C5	1.9 (3)	C11—C16—C17—C18	−3.2 (3)
C2—C1—C6—C7	−174.75 (17)	C16—C17—C18—C19	−178.36 (17)
C5—C6—C7—O1	−158.07 (17)	C16—C17—C18—C23	−0.7 (3)
C1—C6—C7—O1	18.4 (2)	C17—C18—C19—C20	173.37 (17)
C5—C6—C7—C8	22.9 (2)	C23—C18—C19—C20	−4.3 (3)
C1—C6—C7—C8	−160.59 (16)	C18—C19—C20—C21	−0.4 (3)
O1—C7—C8—C9	0.1 (3)	C19—C20—C21—C22	3.8 (3)
C6—C7—C8—C9	179.10 (16)	C20—C21—C22—C23	−2.3 (3)
C7—C8—C9—C10	−173.26 (16)	C11—C10—C23—C22	171.79 (16)
C8—C9—C10—C23	−50.2 (3)	C9—C10—C23—C22	−6.7 (3)
C8—C9—C10—C11	131.30 (19)	C11—C10—C23—C18	−5.1 (3)
C23—C10—C11—C12	−179.68 (17)	C9—C10—C23—C18	176.46 (16)
C9—C10—C11—C12	−1.1 (3)	C21—C22—C23—C10	−179.25 (18)
C23—C10—C11—C16	1.1 (3)	C21—C22—C23—C18	−2.3 (3)
C9—C10—C11—C16	179.69 (16)	C17—C18—C23—C10	4.9 (3)
C10—C11—C12—C13	177.21 (17)	C19—C18—C23—C10	−177.42 (16)
C16—C11—C12—C13	−3.6 (3)	C17—C18—C23—C22	−172.15 (16)
C11—C12—C13—C14	1.1 (3)	C19—C18—C23—C22	5.5 (2)
C12—C13—C14—C15	1.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1ⁱ	0.93	2.42	3.308 (2)	159
C13—H13A···O1ⁱⁱ	0.93	2.57	3.288 (2)	135
C21—H21A···Br1ⁱⁱⁱ	0.93	2.93	3.4722 (19)	119
C9—H9A···Cg1^iv	0.93	2.83	3.4479 (18)	125

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₅BrO
M_r	387.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.3792 (1), 19.1030 (4), 16.3005 (4)
β (°)	95.944 (1)
V (Å³)	1666.02 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.47
Crystal size (mm)	0.57 × 0.27 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.331, 0.714
No. of measured, independent and observed [I > 2σ(I)] reflections	29994, 4866, 3803
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.076, 1.02
No. of reflections	4866
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.54

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
C8—H8A···O1ⁱ	0.93	2.42	3.308 (2)	159
C13—H13A···O1ⁱⁱ	0.93	2.57	3.288 (2)	135
C21—H21A···Br1ⁱⁱⁱ	0.93	2.93	3.4722 (19)	119
C9—H9A···Cg1^iv	0.93	2.83	3.4479 (18)	125

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

Footnotes

†This paper is dedicated to the late Her Royal Highness Princess Galyani Vadhana Krom Luang Naradhiwas Rajanagarindra for her patronage of Science in Thailand.

‡Additional correspondence author, e-mail: hkfun@usm.my.

Acknowledgements

Financial support from the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Commision on Higher Education, Ministry of Education, Thailand, is gratefully acknowledged. The authors also thank the Thailand Research Fund (TRF) and the Prince of Songkla University for financial support, and the Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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