2-(4-Bromo­phen­yl)-2-oxoethyl anthracene-9-carboxyl­ate

Fun, H.-K.; Asik, S.I.J.; Garudachari, B.; Isloor, A.M.; Satyanarayan, M.N.

doi:10.1107/S1600536812022684

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1876

doi:10.1107/S1600536812022684

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2-(4-Bromophenyl)-2-oxoethyl anthracene-9-carboxylate

Hoong-Kun Fun,^a ^*‡ Safra Izuani Jama Asik,^a B. Garudachari,^b Arun M. Isloor ^b and M. N Satyanarayan ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bOrganic Electronics Division, Department of Chemistry, National Institute of Technology–Karnataka, Surathkal, Mangalore 575 025, India, and ^cDepartment of Physics, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 9 May 2012; accepted 18 May 2012; online 26 May 2012)

In the title compound, C₂₃H₁₅BrO₃, the anthracene ring system is essentially planar [maximum deviation = 0.29 (2) Å] and makes a dihedral angle of 5.74 (8)° with the mean plane of the bromo-substituted benzene ring. An intramolecular C—H⋯O hydrogen bond generates an S(9) ring motif. In the crystal, molecules are linked by C—H⋯O interactions, forming a two-dimensional network parallel to the ac plane. π–π stacking interactions are observed between benzene rings [centroid–centroid distances = 3.5949 (14) and 3.5960 (13) Å].

Related literature

For background to the applications of anthracene, see: Bae et al. (2010 ); Reddy et al. (2011 ); Rather & Reid (1919 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₃H₁₅BrO₃
M_r = 419.26
Monoclinic, P 2₁ /c
a = 10.1906 (8) Å
b = 15.0591 (12) Å
c = 13.7938 (8) Å
β = 122.376 (4)°
V = 1787.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.32 mm⁻¹
T = 100 K
0.29 × 0.19 × 0.18 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.550, T_max = 0.677
23513 measured reflections
6409 independent reflections
4600 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.141
S = 1.01
6409 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 1.67 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O3	0.93	2.50	3.401 (3)	164
C20—H20A⋯O1ⁱ	0.93	2.47	3.394 (3)	176
C22—H22A⋯O3ⁱⁱ	0.93	2.31	3.199 (3)	159
Symmetry codes: (i) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536812022684/rz2758sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022684/rz2758Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022684/rz2758Isup3.cml

checkCIF report

Comment top

Anthracene is a solid polycyclic aromatic hydrocarbon consisting of three fused benzene rings. It is used in the production of the dyes and organic semiconductor (Bae et al., 2010) as high energy photons, electrons and alpha particle detectors and also used in blue light emitter in OLEDs (Reddy et al., 2011) and identification of organic acids (Rather & Reid, 1919). Keeping this in view, the title compound (I) was synthesized to study its crystal structure.

In the title compound of (I), (Fig. 1), the anthracene (C1–C14) is essentially planar with maximum deviation of 0.029 (2) Å at atom C7 and makes a dihedral angle of 5.74 (8)° with the mean plane of bromo-substituted benzene (C18–C23) ring. The intramolecular C12—H12A···O3 interaction generates a S(9) ring motif (Bernstein et al., 1995).

In the crystal structure of (Fig, 2), the molecules are linked by C20—H20A···O1 and C22—H22A···O3 interactions to form a two-dimensional network parallel to ac plane. π–π stacking interactions are observed between benzene rings with Cg2···Cg3 and Cg2···Cg4 distances of 3.5949 (14) and 3.5960 (13) Å, respectively. [Cg2 , Cg3 and Cg4 are the centroids of (C1/C6–C8/C13–C14), (C8–C13) and (C18–C23) rings, respectively.]

Related literature top

For background to the applications of anthracene, see: Bae et al. (2010); Reddy et al. (2011); Rather & Reid (1919). For hydrogen-bond motifs, see: Bernstein et al. (1995). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of anthracene-9-carboxylic acid (1.0 g, 0.0044 mol), potassium carbonate (0.589 g, 0.0043 mol) and 2-bromo-1-(4-bromophenyl)ethanone (0.746 g, 0.0053 mol) in dimethylformamide (10 ml) was stirred at room temperature for 1 h. On cooling, colourless needle-shaped crystals of 2-(4-bromophenyl)-2-oxoethyl anthracene-9-carboxylate separated. They were collected by filtration and recrystallized from ethanol. Yield: 1.60 g, 85.1 %, M.p. 421–423 K.

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. An intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing viewed along the b-axis, showing the molecules linked into a two-dimensional network parallel to ac plane. Hydrogen atoms not involved in hydrogen bonding (dashed lines) are omitted for clarity.

2-(4-Bromophenyl)-2-oxoethyl anthracene-9-carboxylate top

Crystal data top

C₂₃H₁₅BrO₃	F(000) = 848
M_r = 419.26	D_x = 1.558 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5144 reflections
a = 10.1906 (8) Å	θ = 2.5–31.7°
b = 15.0591 (12) Å	µ = 2.32 mm⁻¹
c = 13.7938 (8) Å	T = 100 K
β = 122.376 (4)°	Block, colourless
V = 1787.8 (2) Å³	0.29 × 0.19 × 0.18 mm
Z = 4

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	6409 independent reflections
Radiation source: fine-focus sealed tube	4600 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 32.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
T_min = 0.550, T_max = 0.677	k = −22→22
23513 measured reflections	l = −20→17

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0886P)² + 0.0927P] where P = (F_o² + 2F_c²)/3
6409 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 1.67 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₂₃H₁₅BrO₃	V = 1787.8 (2) Å³
M_r = 419.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.1906 (8) Å	µ = 2.32 mm⁻¹
b = 15.0591 (12) Å	T = 100 K
c = 13.7938 (8) Å	0.29 × 0.19 × 0.18 mm
β = 122.376 (4)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	6409 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4600 reflections with I > 2σ(I)
T_min = 0.550, T_max = 0.677	R_int = 0.042
23513 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.01	Δρ_max = 1.67 e Å⁻³
6409 reflections	Δρ_min = −0.48 e Å⁻³
244 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 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
Br1	0.87070 (3)	0.870236 (16)	0.94495 (2)	0.03087 (9)
O1	0.1433 (2)	0.62950 (10)	0.30661 (16)	0.0325 (4)
O2	0.29082 (18)	0.51653 (10)	0.41883 (13)	0.0240 (3)
O3	0.50031 (19)	0.63375 (10)	0.44349 (14)	0.0261 (3)
C1	−0.0111 (2)	0.44108 (13)	0.19350 (18)	0.0216 (4)
C2	−0.0870 (3)	0.45257 (15)	0.2544 (2)	0.0260 (4)
H2A	−0.0463	0.4923	0.3154	0.031*
C3	−0.2193 (3)	0.40581 (17)	0.2243 (2)	0.0323 (5)
H3A	−0.2672	0.4139	0.2651	0.039*
C4	−0.2831 (3)	0.34522 (17)	0.1312 (3)	0.0371 (6)
H4A	−0.3731	0.3140	0.1109	0.045*
C5	−0.2135 (3)	0.33265 (15)	0.0721 (2)	0.0335 (5)
H5A	−0.2562	0.2920	0.0120	0.040*
C6	−0.0757 (3)	0.38009 (14)	0.0990 (2)	0.0257 (4)
C7	−0.0046 (3)	0.36890 (14)	0.0382 (2)	0.0271 (4)
H7A	−0.0492	0.3308	−0.0246	0.033*
C8	0.1329 (2)	0.41350 (15)	0.06852 (18)	0.0253 (4)
C9	0.2078 (3)	0.40118 (17)	0.0066 (2)	0.0308 (5)
H9A	0.1644	0.3627	−0.0558	0.037*
C10	0.3417 (3)	0.44494 (18)	0.0377 (2)	0.0338 (5)
H10A	0.3901	0.4352	−0.0025	0.041*
C11	0.4079 (3)	0.50561 (17)	0.1314 (2)	0.0307 (5)
H11A	0.4992	0.5353	0.1519	0.037*
C12	0.3393 (2)	0.52057 (15)	0.19129 (19)	0.0248 (4)
H12A	0.3829	0.5612	0.2514	0.030*
C13	0.1998 (2)	0.47415 (14)	0.16253 (17)	0.0218 (4)
C14	0.1252 (2)	0.48732 (13)	0.22245 (17)	0.0200 (4)
C15	0.1862 (2)	0.55352 (14)	0.31773 (18)	0.0212 (4)
C16	0.3542 (3)	0.57382 (15)	0.51649 (18)	0.0240 (4)
H16A	0.3999	0.5385	0.5860	0.029*
H16B	0.2719	0.6096	0.5119	0.029*
C17	0.4772 (2)	0.63405 (12)	0.52133 (18)	0.0195 (4)
C18	0.5685 (2)	0.69144 (13)	0.62398 (17)	0.0183 (3)
C19	0.7085 (2)	0.72715 (14)	0.64551 (17)	0.0225 (4)
H19A	0.7410	0.7148	0.5955	0.027*
C20	0.7993 (3)	0.78068 (14)	0.74042 (18)	0.0244 (4)
H20A	0.8934	0.8035	0.7557	0.029*
C21	0.7457 (2)	0.79908 (13)	0.81176 (18)	0.0215 (4)
C22	0.6081 (2)	0.76560 (14)	0.79325 (18)	0.0227 (4)
H22A	0.5750	0.7796	0.8425	0.027*
C23	0.5203 (2)	0.71067 (14)	0.69956 (18)	0.0212 (4)
H23A	0.4285	0.6863	0.6867	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03828 (15)	0.03103 (13)	0.02549 (13)	−0.00894 (9)	0.01853 (11)	−0.00714 (8)
O1	0.0254 (8)	0.0250 (8)	0.0331 (9)	0.0049 (6)	0.0064 (7)	−0.0067 (6)
O2	0.0261 (8)	0.0231 (7)	0.0187 (7)	−0.0025 (6)	0.0094 (6)	−0.0007 (5)
O3	0.0233 (7)	0.0367 (9)	0.0196 (7)	−0.0046 (6)	0.0124 (6)	−0.0027 (6)
C1	0.0187 (9)	0.0187 (8)	0.0222 (10)	0.0003 (7)	0.0075 (8)	0.0013 (7)
C2	0.0236 (10)	0.0257 (10)	0.0273 (11)	−0.0005 (8)	0.0127 (9)	0.0023 (8)
C3	0.0282 (11)	0.0326 (12)	0.0380 (13)	−0.0033 (9)	0.0191 (11)	0.0031 (10)
C4	0.0275 (12)	0.0303 (11)	0.0485 (16)	−0.0099 (10)	0.0169 (12)	0.0008 (11)
C5	0.0266 (11)	0.0206 (10)	0.0389 (13)	−0.0058 (9)	0.0079 (10)	−0.0069 (9)
C6	0.0231 (10)	0.0191 (9)	0.0257 (10)	0.0033 (7)	0.0070 (9)	−0.0008 (7)
C7	0.0271 (11)	0.0216 (10)	0.0224 (10)	0.0016 (8)	0.0065 (9)	−0.0025 (8)
C8	0.0263 (11)	0.0223 (10)	0.0219 (10)	0.0089 (8)	0.0092 (9)	0.0002 (7)
C9	0.0365 (12)	0.0318 (11)	0.0199 (10)	0.0119 (10)	0.0123 (10)	0.0031 (9)
C10	0.0403 (13)	0.0424 (13)	0.0274 (11)	0.0161 (11)	0.0240 (11)	0.0090 (10)
C11	0.0256 (11)	0.0398 (12)	0.0286 (11)	0.0049 (9)	0.0157 (10)	0.0083 (10)
C12	0.0207 (9)	0.0302 (10)	0.0204 (10)	0.0029 (8)	0.0091 (8)	0.0006 (8)
C13	0.0185 (9)	0.0240 (9)	0.0195 (9)	0.0048 (7)	0.0079 (8)	0.0015 (7)
C14	0.0181 (9)	0.0200 (8)	0.0182 (9)	0.0022 (7)	0.0073 (7)	0.0000 (7)
C15	0.0191 (9)	0.0241 (9)	0.0220 (9)	−0.0012 (7)	0.0121 (8)	−0.0009 (7)
C16	0.0270 (10)	0.0276 (10)	0.0186 (9)	−0.0070 (8)	0.0131 (8)	−0.0035 (8)
C17	0.0180 (9)	0.0203 (9)	0.0203 (9)	0.0014 (7)	0.0104 (8)	0.0014 (7)
C18	0.0172 (8)	0.0199 (8)	0.0190 (9)	0.0009 (7)	0.0104 (7)	0.0027 (7)
C19	0.0222 (9)	0.0300 (10)	0.0196 (9)	−0.0043 (8)	0.0140 (8)	−0.0002 (8)
C20	0.0244 (10)	0.0290 (10)	0.0243 (10)	−0.0051 (8)	0.0160 (9)	−0.0003 (8)
C21	0.0265 (10)	0.0197 (9)	0.0184 (9)	−0.0007 (7)	0.0119 (8)	0.0003 (7)
C22	0.0253 (10)	0.0240 (9)	0.0226 (10)	0.0027 (8)	0.0154 (9)	0.0013 (8)
C23	0.0206 (9)	0.0252 (9)	0.0221 (9)	0.0012 (7)	0.0143 (8)	0.0031 (8)

Geometric parameters (Å, º) top

Br1—C21	1.908 (2)	C10—C11	1.424 (4)
O1—C15	1.205 (2)	C10—H10A	0.9300
O2—C15	1.342 (3)	C11—C12	1.356 (3)
O2—C16	1.430 (3)	C11—H11A	0.9300
O3—C17	1.216 (2)	C12—C13	1.436 (3)
C1—C14	1.406 (3)	C12—H12A	0.9300
C1—C2	1.425 (3)	C13—C14	1.405 (3)
C1—C6	1.434 (3)	C14—C15	1.494 (3)
C2—C3	1.373 (3)	C16—C17	1.520 (3)
C2—H2A	0.9300	C16—H16A	0.9700
C3—C4	1.418 (4)	C16—H16B	0.9700
C3—H3A	0.9300	C17—C18	1.485 (3)
C4—C5	1.350 (4)	C18—C19	1.400 (3)
C4—H4A	0.9300	C18—C23	1.400 (3)
C5—C6	1.436 (3)	C19—C20	1.387 (3)
C5—H5A	0.9300	C19—H19A	0.9300
C6—C7	1.382 (3)	C20—C21	1.385 (3)
C7—C8	1.401 (3)	C20—H20A	0.9300
C7—H7A	0.9300	C21—C22	1.380 (3)
C8—C13	1.426 (3)	C22—C23	1.384 (3)
C8—C9	1.430 (3)	C22—H22A	0.9300
C9—C10	1.361 (4)	C23—H23A	0.9300
C9—H9A	0.9300

C15—O2—C16	115.81 (17)	C14—C13—C8	118.66 (19)
C14—C1—C2	122.51 (19)	C14—C13—C12	122.43 (19)
C14—C1—C6	118.6 (2)	C8—C13—C12	118.9 (2)
C2—C1—C6	118.9 (2)	C13—C14—C1	121.74 (19)
C3—C2—C1	121.0 (2)	C13—C14—C15	120.68 (18)
C3—C2—H2A	119.5	C1—C14—C15	117.56 (18)
C1—C2—H2A	119.5	O1—C15—O2	124.0 (2)
C2—C3—C4	120.3 (2)	O1—C15—C14	124.7 (2)
C2—C3—H3A	119.9	O2—C15—C14	111.23 (17)
C4—C3—H3A	119.9	O2—C16—C17	110.32 (16)
C5—C4—C3	120.2 (2)	O2—C16—H16A	109.6
C5—C4—H4A	119.9	C17—C16—H16A	109.6
C3—C4—H4A	119.9	O2—C16—H16B	109.6
C4—C5—C6	122.1 (2)	C17—C16—H16B	109.6
C4—C5—H5A	119.0	H16A—C16—H16B	108.1
C6—C5—H5A	119.0	O3—C17—C18	121.71 (18)
C7—C6—C1	119.7 (2)	O3—C17—C16	120.27 (18)
C7—C6—C5	122.7 (2)	C18—C17—C16	118.01 (17)
C1—C6—C5	117.6 (2)	C19—C18—C23	119.11 (19)
C6—C7—C8	121.7 (2)	C19—C18—C17	118.19 (17)
C6—C7—H7A	119.1	C23—C18—C17	122.70 (18)
C8—C7—H7A	119.1	C20—C19—C18	120.87 (19)
C7—C8—C13	119.6 (2)	C20—C19—H19A	119.6
C7—C8—C9	121.9 (2)	C18—C19—H19A	119.6
C13—C8—C9	118.6 (2)	C21—C20—C19	117.97 (19)
C10—C9—C8	121.0 (2)	C21—C20—H20A	121.0
C10—C9—H9A	119.5	C19—C20—H20A	121.0
C8—C9—H9A	119.5	C22—C21—C20	122.95 (19)
C9—C10—C11	120.3 (2)	C22—C21—Br1	118.15 (15)
C9—C10—H10A	119.9	C20—C21—Br1	118.86 (16)
C11—C10—H10A	119.9	C21—C22—C23	118.40 (18)
C12—C11—C10	120.8 (2)	C21—C22—H22A	120.8
C12—C11—H11A	119.6	C23—C22—H22A	120.8
C10—C11—H11A	119.6	C22—C23—C18	120.67 (19)
C11—C12—C13	120.5 (2)	C22—C23—H23A	119.7
C11—C12—H12A	119.7	C18—C23—H23A	119.7
C13—C12—H12A	119.7

C14—C1—C2—C3	−179.5 (2)	C12—C13—C14—C15	2.1 (3)
C6—C1—C2—C3	0.5 (3)	C2—C1—C14—C13	179.01 (19)
C1—C2—C3—C4	−0.2 (4)	C6—C1—C14—C13	−1.0 (3)
C2—C3—C4—C5	0.5 (4)	C2—C1—C14—C15	−2.7 (3)
C3—C4—C5—C6	−0.9 (4)	C6—C1—C14—C15	177.28 (18)
C14—C1—C6—C7	−0.8 (3)	C16—O2—C15—O1	−1.3 (3)
C2—C1—C6—C7	179.3 (2)	C16—O2—C15—C14	−178.65 (16)
C14—C1—C6—C5	179.10 (19)	C13—C14—C15—O1	93.4 (3)
C2—C1—C6—C5	−0.9 (3)	C1—C14—C15—O1	−84.9 (3)
C4—C5—C6—C7	−179.0 (2)	C13—C14—C15—O2	−89.2 (2)
C4—C5—C6—C1	1.1 (4)	C1—C14—C15—O2	92.5 (2)
C1—C6—C7—C8	2.2 (3)	C15—O2—C16—C17	−78.0 (2)
C5—C6—C7—C8	−177.7 (2)	O2—C16—C17—O3	5.7 (3)
C6—C7—C8—C13	−1.9 (3)	O2—C16—C17—C18	−173.42 (17)
C6—C7—C8—C9	179.2 (2)	O3—C17—C18—C19	−17.1 (3)
C7—C8—C9—C10	−179.8 (2)	C16—C17—C18—C19	162.00 (19)
C13—C8—C9—C10	1.2 (3)	O3—C17—C18—C23	163.1 (2)
C8—C9—C10—C11	−1.4 (4)	C16—C17—C18—C23	−17.7 (3)
C9—C10—C11—C12	0.2 (4)	C23—C18—C19—C20	0.2 (3)
C10—C11—C12—C13	1.2 (3)	C17—C18—C19—C20	−179.53 (19)
C7—C8—C13—C14	0.1 (3)	C18—C19—C20—C21	−1.3 (3)
C9—C8—C13—C14	179.09 (19)	C19—C20—C21—C22	0.9 (3)
C7—C8—C13—C12	−178.89 (19)	C19—C20—C21—Br1	178.53 (16)
C9—C8—C13—C12	0.1 (3)	C20—C21—C22—C23	0.5 (3)
C11—C12—C13—C14	179.8 (2)	Br1—C21—C22—C23	−177.15 (15)
C11—C12—C13—C8	−1.3 (3)	C21—C22—C23—C18	−1.6 (3)
C8—C13—C14—C1	1.3 (3)	C19—C18—C23—C22	1.2 (3)
C12—C13—C14—C1	−179.75 (19)	C17—C18—C23—C22	−179.03 (18)
C8—C13—C14—C15	−176.91 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O3	0.93	2.50	3.401 (3)	164
C20—H20A···O1ⁱ	0.93	2.47	3.394 (3)	176
C22—H22A···O3ⁱⁱ	0.93	2.31	3.199 (3)	159

Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₅BrO₃
M_r	419.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.1906 (8), 15.0591 (12), 13.7938 (8)
β (°)	122.376 (4)
V (Å³)	1787.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.32
Crystal size (mm)	0.29 × 0.19 × 0.18

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.550, 0.677
No. of measured, independent and observed [I > 2σ(I)] reflections	23513, 6409, 4600
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.757

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.141, 1.01
No. of reflections	6409
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.67, −0.48

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O3	0.93	2.50	3.401 (3)	164
C20—H20A···O1ⁱ	0.93	2.47	3.394 (3)	176
C22—H22A···O3ⁱⁱ	0.93	2.31	3.199 (3)	159

Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) x, −y+3/2, z+1/2.

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). AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award. SMN thanks Department of Information Technology, New Delhi, India, for financial support.

References

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