2-Bromo-1,3-diphenyl­propan-1,3-dione

Arifin, Z.; Ng, S.W.

doi:10.1107/S1600536808038646

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2439

doi:10.1107/S1600536808038646

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2-Bromo-1,3-diphenylpropan-1,3-dione

Zainudin Arifin ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 11 November 2008; accepted 19 November 2008; online 26 November 2008)

The title compound, C₁₅H₁₁BrO₂, exists as a diketone in which the two benzoyl groups are nearly perpendicular to each other [dihedral angles = 79.9 (1) and 87.4 (1)° in the two independent molecules].

Related literature

The compound is claimed to exist in the enol form as it condenses with 2-aminothiazole and 2-mercaptoimidazoline; see: Robert & Panouse (1979 ). The parent dibenzoylmethane molecule exists in two modications, as 1,3-diphenyl-1-hydroxypropen-1-one; see: Kaitner & Meštrović (1993 ); Ozturk et al. (1997 ).

Experimental

Crystal data

C₁₅H₁₁BrO₂
M_r = 303.15
Orthorhombic, P c a 2₁
a = 28.0680 (6) Å
b = 5.6508 (1) Å
c = 15.3741 (3) Å
V = 2438.43 (8) Å³
Z = 8
Mo Kα radiation
μ = 3.36 mm⁻¹
T = 100 (2) K
0.27 × 0.20 × 0.06 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.464, T_max = 0.824
21610 measured reflections
5562 independent reflections
4774 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.086
S = 0.99
5562 reflections
325 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.52 e Å⁻³
Absolute structure: Flack (1983 ), 2644 Fridel pairs
Flack parameter: −0.002 (9)

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038646/pk2135sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038646/pk2135Isup2.hkl

checkCIF report

Related literature top

The compound is claimed to exist in the enol form as it condenses with 2-aminothiazole and 2-mercaptoimidazoline; see: Robert & Panouse (1979). The parent dibenzoylmethane molecule exists in two modications, as 1,3-diphenyl-1-hydroxypropen-1-one; see: Kaitner & Meštrović (1993); Ozturk et al. (1997).

Experimental top

The commerically available compound was recrystallized from toluene.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

Fig. 1. Thermal ellipsoid (Barbour, 2001) plot of the two independent molecules of C₁₅H₁₁BrO₂ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

2-Bromo-1,3-diphenylpropan-1,3-dione top

Crystal data top

C₁₅H₁₁BrO₂	F(000) = 1216
M_r = 303.15	D_x = 1.652 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4583 reflections
a = 28.0680 (6) Å	θ = 2.6–25.4°
b = 5.6508 (1) Å	µ = 3.36 mm⁻¹
c = 15.3741 (3) Å	T = 100 K
V = 2438.43 (8) Å³	Plate, colorless
Z = 8	0.27 × 0.20 × 0.06 mm

Data collection top

Bruker SMART APEX diffractometer	5562 independent reflections
Radiation source: fine-focus sealed tube	4774 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −36→35
T_min = 0.464, T_max = 0.824	k = −7→7
21610 measured reflections	l = −19→19

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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0511P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
5562 reflections	Δρ_max = 0.76 e Å⁻³
325 parameters	Δρ_min = −0.52 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2644 Fridel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.002 (9)

Crystal data top

C₁₅H₁₁BrO₂	V = 2438.43 (8) Å³
M_r = 303.15	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 28.0680 (6) Å	µ = 3.36 mm⁻¹
b = 5.6508 (1) Å	T = 100 K
c = 15.3741 (3) Å	0.27 × 0.20 × 0.06 mm

Data collection top

Bruker SMART APEX diffractometer	5562 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4774 reflections with I > 2σ(I)
T_min = 0.464, T_max = 0.824	R_int = 0.060
21610 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.087	Δρ_max = 0.76 e Å⁻³
S = 0.99	Δρ_min = −0.52 e Å⁻³
5562 reflections	Absolute structure: Flack (1983), 2644 Fridel pairs
325 parameters	Absolute structure parameter: −0.002 (9)
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.264659 (13)	0.21340 (7)	0.50000 (3)	0.01660 (9)
Br2	0.355868 (14)	1.36089 (7)	0.23689 (3)	0.01981 (10)
O1	0.18018 (11)	−0.0909 (5)	0.52553 (18)	0.0212 (7)
O2	0.17207 (11)	0.1525 (5)	0.33248 (18)	0.0181 (6)
O3	0.44667 (12)	1.6039 (6)	0.1914 (2)	0.0312 (8)
O4	0.44450 (11)	1.4517 (5)	0.39763 (19)	0.0216 (7)
C1	0.11351 (15)	0.1585 (6)	0.5074 (3)	0.0147 (8)
C2	0.09476 (15)	0.3667 (8)	0.4735 (3)	0.0183 (9)
H2	0.1153	0.4846	0.4505	0.022*
C3	0.04576 (15)	0.4012 (8)	0.4733 (3)	0.0188 (9)
H3	0.0330	0.5411	0.4482	0.023*
C4	0.01566 (16)	0.2367 (7)	0.5086 (3)	0.0233 (10)
H4	−0.0178	0.2623	0.5080	0.028*
C5	0.03430 (16)	0.0314 (8)	0.5455 (3)	0.0208 (9)
H5	0.0136	−0.0818	0.5711	0.025*
C6	0.08317 (16)	−0.0077 (8)	0.5446 (3)	0.0194 (9)
H6	0.0959	−0.1481	0.5695	0.023*
C7	0.16522 (15)	0.1006 (7)	0.5035 (3)	0.0171 (8)
C8	0.19934 (14)	0.2929 (7)	0.4686 (3)	0.0145 (8)
H8	0.1906	0.4505	0.4936	0.017*
C9	0.19594 (15)	0.3008 (7)	0.3688 (3)	0.0150 (8)
C10	0.22242 (14)	0.4836 (7)	0.3189 (2)	0.0138 (8)
C11	0.22560 (13)	0.4551 (7)	0.2283 (3)	0.0165 (8)
H11	0.2121	0.3196	0.2013	0.020*
C12	0.24831 (16)	0.6234 (8)	0.1785 (3)	0.0168 (9)
H12	0.2501	0.6042	0.1172	0.020*
C13	0.26858 (15)	0.8212 (8)	0.2174 (3)	0.0188 (9)
H13	0.2841	0.9373	0.1829	0.023*
C14	0.26596 (15)	0.8482 (7)	0.3067 (3)	0.0176 (9)
H14	0.2800	0.9830	0.3334	0.021*
C15	0.24308 (15)	0.6804 (7)	0.3579 (3)	0.0153 (8)
H15	0.2416	0.7000	0.4192	0.018*
C16	0.39938 (16)	1.1076 (8)	0.4260 (3)	0.0168 (9)
C17	0.37847 (15)	0.9021 (8)	0.3946 (3)	0.0174 (9)
H17	0.3785	0.8690	0.3341	0.021*
C18	0.35758 (18)	0.7456 (8)	0.4527 (3)	0.0198 (10)
H18	0.3440	0.6026	0.4318	0.024*
C19	0.3564 (2)	0.7951 (9)	0.5399 (3)	0.0252 (11)
H19	0.3413	0.6878	0.5786	0.030*
C20	0.37725 (19)	1.0017 (9)	0.5725 (3)	0.0272 (11)
H20	0.3769	1.0341	0.6331	0.033*
C21	0.39847 (16)	1.1585 (7)	0.5150 (3)	0.0214 (10)
H21	0.4124	1.3006	0.5361	0.026*
C22	0.42297 (14)	1.2851 (8)	0.3686 (3)	0.0159 (8)
C23	0.42002 (14)	1.2619 (8)	0.2686 (3)	0.0159 (9)
H23	0.4256	1.0942	0.2505	0.019*
C24	0.45729 (14)	1.4232 (7)	0.2285 (3)	0.0187 (8)
C25	0.50847 (14)	1.3574 (7)	0.2417 (3)	0.0163 (8)
C26	0.52174 (17)	1.1460 (7)	0.2826 (3)	0.0175 (9)
H26	0.4980	1.0340	0.2985	0.021*
C27	0.56937 (15)	1.0990 (7)	0.3001 (3)	0.0170 (9)
H27	0.5783	0.9553	0.3276	0.020*
C28	0.60386 (16)	1.2646 (8)	0.2768 (3)	0.0193 (9)
H28	0.6364	1.2366	0.2901	0.023*
C29	0.59053 (14)	1.4708 (7)	0.2339 (3)	0.0190 (8)
H29	0.6141	1.5809	0.2159	0.023*
C30	0.54305 (15)	1.5154 (8)	0.2177 (2)	0.0179 (9)
H30	0.5342	1.6581	0.1893	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01624 (19)	0.01938 (19)	0.01417 (16)	0.00186 (15)	−0.00319 (19)	−0.00273 (19)
Br2	0.01400 (19)	0.0249 (2)	0.02058 (18)	0.00115 (17)	−0.0026 (2)	−0.00051 (18)
O1	0.0241 (17)	0.0178 (16)	0.0216 (15)	0.0040 (13)	0.0017 (12)	0.0053 (11)
O2	0.0206 (17)	0.0167 (16)	0.0169 (14)	−0.0018 (12)	−0.0004 (12)	−0.0016 (12)
O3	0.0200 (18)	0.026 (2)	0.047 (2)	0.0031 (14)	−0.0006 (16)	0.0203 (16)
O4	0.0191 (17)	0.0190 (16)	0.0269 (16)	−0.0045 (13)	0.0007 (13)	−0.0065 (13)
C1	0.018 (2)	0.015 (2)	0.0107 (18)	0.0009 (14)	−0.0032 (17)	0.0021 (18)
C2	0.023 (2)	0.016 (2)	0.0162 (19)	−0.0028 (17)	0.0000 (17)	−0.0040 (15)
C3	0.020 (2)	0.016 (2)	0.021 (2)	0.0056 (16)	−0.0044 (17)	0.0010 (16)
C4	0.017 (2)	0.027 (3)	0.025 (2)	0.0053 (16)	0.001 (2)	−0.002 (2)
C5	0.020 (2)	0.027 (3)	0.015 (2)	−0.0058 (19)	0.0001 (17)	0.0050 (18)
C6	0.023 (2)	0.017 (2)	0.018 (2)	−0.0011 (17)	0.0024 (18)	0.0005 (17)
C7	0.024 (2)	0.018 (2)	0.0094 (16)	0.0007 (16)	0.0012 (18)	0.0010 (19)
C8	0.015 (2)	0.015 (2)	0.0140 (16)	0.0032 (16)	0.0006 (15)	−0.0054 (16)
C9	0.016 (2)	0.013 (2)	0.0155 (18)	0.0025 (17)	−0.0016 (16)	−0.0046 (15)
C10	0.011 (2)	0.014 (2)	0.0168 (19)	−0.0004 (15)	−0.0006 (15)	0.0013 (16)
C11	0.0124 (18)	0.018 (2)	0.019 (2)	−0.0006 (15)	−0.0032 (19)	0.0013 (18)
C12	0.022 (2)	0.021 (2)	0.0079 (17)	0.0013 (17)	−0.0003 (16)	−0.0039 (17)
C13	0.020 (2)	0.016 (2)	0.021 (2)	−0.0026 (16)	0.0036 (17)	−0.0006 (16)
C14	0.018 (2)	0.015 (2)	0.021 (2)	−0.0008 (17)	−0.0016 (17)	−0.0037 (16)
C15	0.016 (2)	0.016 (2)	0.0138 (18)	0.0020 (16)	−0.0038 (16)	−0.0024 (16)
C16	0.018 (2)	0.017 (2)	0.0153 (19)	0.0037 (17)	−0.0010 (17)	0.0029 (17)
C17	0.016 (2)	0.021 (2)	0.0158 (19)	0.0024 (17)	−0.0009 (17)	0.0000 (17)
C18	0.014 (2)	0.017 (2)	0.028 (3)	−0.0018 (18)	0.000 (2)	0.0058 (18)
C19	0.024 (3)	0.026 (3)	0.026 (2)	0.006 (2)	0.007 (2)	0.006 (2)
C20	0.038 (3)	0.029 (3)	0.014 (2)	0.002 (2)	−0.0012 (19)	0.0036 (18)
C21	0.026 (2)	0.017 (2)	0.021 (2)	0.0014 (17)	−0.0040 (18)	−0.0013 (17)
C22	0.010 (2)	0.019 (2)	0.0186 (19)	0.0059 (17)	−0.0013 (16)	−0.0006 (17)
C23	0.008 (2)	0.021 (2)	0.0192 (19)	0.0036 (16)	−0.0002 (16)	0.0040 (16)
C24	0.020 (2)	0.020 (2)	0.016 (2)	0.0006 (16)	0.000 (2)	0.0043 (18)
C25	0.018 (2)	0.0157 (19)	0.0155 (18)	0.0032 (17)	0.004 (2)	−0.0018 (17)
C26	0.024 (2)	0.012 (2)	0.017 (2)	−0.0009 (17)	0.0009 (18)	−0.0021 (16)
C27	0.022 (2)	0.013 (2)	0.0164 (19)	0.0042 (16)	0.0014 (17)	−0.0012 (15)
C28	0.016 (2)	0.023 (2)	0.019 (2)	0.0013 (17)	0.0012 (17)	−0.0073 (18)
C29	0.021 (2)	0.018 (2)	0.0180 (17)	−0.0010 (16)	0.003 (2)	0.0013 (19)
C30	0.018 (2)	0.017 (2)	0.020 (2)	0.0005 (16)	0.0001 (16)	0.0003 (16)

Geometric parameters (Å, º) top

Br1—C8	1.948 (4)	C14—C15	1.389 (6)
Br2—C23	1.947 (4)	C14—H14	0.9500
O1—C7	1.209 (5)	C15—H15	0.9500
O2—C9	1.209 (5)	C16—C17	1.388 (6)
O3—C24	1.207 (5)	C16—C21	1.398 (6)
O4—C22	1.204 (5)	C16—C22	1.491 (6)
C1—C2	1.390 (6)	C17—C18	1.387 (6)
C1—C6	1.391 (6)	C17—H17	0.9500
C1—C7	1.489 (6)	C18—C19	1.369 (6)
C2—C3	1.389 (6)	C18—H18	0.9500
C2—H2	0.9500	C19—C20	1.399 (7)
C3—C4	1.369 (6)	C19—H19	0.9500
C3—H3	0.9500	C20—C21	1.386 (6)
C4—C5	1.393 (6)	C20—H20	0.9500
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.389 (6)	C22—C23	1.545 (6)
C5—H5	0.9500	C23—C24	1.518 (6)
C6—H6	0.9500	C23—H23	1.0000
C7—C8	1.544 (6)	C24—C25	1.498 (6)
C8—C9	1.538 (5)	C25—C30	1.370 (6)
C8—H8	1.0000	C25—C26	1.400 (6)
C9—C10	1.487 (6)	C26—C27	1.389 (6)
C10—C15	1.391 (6)	C26—H26	0.9500
C10—C11	1.405 (6)	C27—C28	1.393 (6)
C11—C12	1.377 (6)	C27—H27	0.9500
C11—H11	0.9500	C28—C29	1.390 (6)
C12—C13	1.390 (6)	C28—H28	0.9500
C12—H12	0.9500	C29—C30	1.379 (6)
C13—C14	1.384 (6)	C29—H29	0.9500
C13—H13	0.9500	C30—H30	0.9500

C2—C1—C6	119.6 (4)	C17—C16—C21	120.3 (4)
C2—C1—C7	122.7 (4)	C17—C16—C22	123.0 (4)
C6—C1—C7	117.7 (3)	C21—C16—C22	116.7 (4)
C3—C2—C1	119.7 (4)	C18—C17—C16	119.3 (4)
C3—C2—H2	120.2	C18—C17—H17	120.4
C1—C2—H2	120.2	C16—C17—H17	120.4
C4—C3—C2	121.0 (4)	C19—C18—C17	120.7 (5)
C4—C3—H3	119.5	C19—C18—H18	119.7
C2—C3—H3	119.5	C17—C18—H18	119.7
C3—C4—C5	119.7 (4)	C18—C19—C20	120.7 (5)
C3—C4—H4	120.2	C18—C19—H19	119.6
C5—C4—H4	120.2	C20—C19—H19	119.6
C6—C5—C4	120.0 (4)	C21—C20—C19	119.0 (4)
C6—C5—H5	120.0	C21—C20—H20	120.5
C4—C5—H5	120.0	C19—C20—H20	120.5
C5—C6—C1	120.0 (4)	C20—C21—C16	120.0 (4)
C5—C6—H6	120.0	C20—C21—H21	120.0
C1—C6—H6	120.0	C16—C21—H21	120.0
O1—C7—C1	121.6 (4)	O4—C22—C16	121.9 (4)
O1—C7—C8	120.8 (4)	O4—C22—C23	117.5 (4)
C1—C7—C8	117.6 (3)	C16—C22—C23	120.5 (4)
C9—C8—C7	109.2 (3)	C24—C23—C22	108.4 (3)
C9—C8—Br1	108.2 (3)	C24—C23—Br2	111.3 (3)
C7—C8—Br1	109.6 (3)	C22—C23—Br2	105.9 (3)
C9—C8—H8	110.0	C24—C23—H23	110.4
C7—C8—H8	110.0	C22—C23—H23	110.4
Br1—C8—H8	110.0	Br2—C23—H23	110.4
O2—C9—C10	121.3 (4)	O3—C24—C25	120.7 (4)
O2—C9—C8	118.4 (4)	O3—C24—C23	122.0 (4)
C10—C9—C8	120.3 (3)	C25—C24—C23	117.2 (3)
C15—C10—C11	119.5 (4)	C30—C25—C26	119.3 (4)
C15—C10—C9	122.8 (4)	C30—C25—C24	118.8 (4)
C11—C10—C9	117.7 (3)	C26—C25—C24	121.8 (4)
C12—C11—C10	120.1 (4)	C27—C26—C25	120.4 (4)
C12—C11—H11	120.0	C27—C26—H26	119.8
C10—C11—H11	120.0	C25—C26—H26	119.8
C11—C12—C13	120.4 (4)	C26—C27—C28	119.4 (4)
C11—C12—H12	119.8	C26—C27—H27	120.3
C13—C12—H12	119.8	C28—C27—H27	120.3
C14—C13—C12	119.6 (4)	C29—C28—C27	119.9 (4)
C14—C13—H13	120.2	C29—C28—H28	120.1
C12—C13—H13	120.2	C27—C28—H28	120.1
C13—C14—C15	120.8 (4)	C30—C29—C28	119.9 (4)
C13—C14—H14	119.6	C30—C29—H29	120.0
C15—C14—H14	119.6	C28—C29—H29	120.0
C14—C15—C10	119.6 (4)	C25—C30—C29	121.1 (4)
C14—C15—H15	120.2	C25—C30—H30	119.4
C10—C15—H15	120.2	C29—C30—H30	119.4

C6—C1—C2—C3	−3.2 (6)	C21—C16—C17—C18	−1.4 (7)
C7—C1—C2—C3	175.0 (4)	C22—C16—C17—C18	179.5 (4)
C1—C2—C3—C4	2.2 (6)	C16—C17—C18—C19	1.7 (8)
C2—C3—C4—C5	0.1 (7)	C17—C18—C19—C20	−1.5 (9)
C3—C4—C5—C6	−1.3 (7)	C18—C19—C20—C21	1.1 (8)
C4—C5—C6—C1	0.3 (6)	C19—C20—C21—C16	−0.8 (7)
C2—C1—C6—C5	1.9 (6)	C17—C16—C21—C20	1.0 (7)
C7—C1—C6—C5	−176.4 (4)	C22—C16—C21—C20	−179.9 (4)
C2—C1—C7—O1	−172.5 (4)	C17—C16—C22—O4	−173.4 (4)
C6—C1—C7—O1	5.7 (6)	C21—C16—C22—O4	7.5 (6)
C2—C1—C7—C8	6.3 (6)	C17—C16—C22—C23	7.3 (6)
C6—C1—C7—C8	−175.4 (4)	C21—C16—C22—C23	−171.9 (4)
O1—C7—C8—C9	101.3 (5)	O4—C22—C23—C24	15.6 (5)
C1—C7—C8—C9	−77.6 (5)	C16—C22—C23—C24	−165.0 (4)
O1—C7—C8—Br1	−17.1 (5)	O4—C22—C23—Br2	−103.9 (4)
C1—C7—C8—Br1	164.1 (3)	C16—C22—C23—Br2	75.4 (4)
C7—C8—C9—O2	−6.1 (5)	C22—C23—C24—O3	−107.7 (5)
Br1—C8—C9—O2	113.1 (4)	Br2—C23—C24—O3	8.4 (6)
C7—C8—C9—C10	175.3 (3)	C22—C23—C24—C25	68.5 (5)
Br1—C8—C9—C10	−65.5 (4)	Br2—C23—C24—C25	−175.4 (3)
O2—C9—C10—C15	168.2 (4)	O3—C24—C25—C30	5.6 (7)
C8—C9—C10—C15	−13.3 (6)	C23—C24—C25—C30	−170.6 (4)
O2—C9—C10—C11	−10.7 (6)	O3—C24—C25—C26	−178.3 (4)
C8—C9—C10—C11	167.9 (4)	C23—C24—C25—C26	5.5 (6)
C15—C10—C11—C12	−1.2 (6)	C30—C25—C26—C27	1.2 (6)
C9—C10—C11—C12	177.8 (4)	C24—C25—C26—C27	−174.9 (4)
C10—C11—C12—C13	0.6 (7)	C25—C26—C27—C28	0.2 (6)
C11—C12—C13—C14	0.2 (7)	C26—C27—C28—C29	−2.1 (6)
C12—C13—C14—C15	−0.3 (7)	C27—C28—C29—C30	2.6 (7)
C13—C14—C15—C10	−0.3 (6)	C26—C25—C30—C29	−0.7 (7)
C11—C10—C15—C14	1.0 (6)	C24—C25—C30—C29	175.5 (4)
C9—C10—C15—C14	−177.9 (4)	C28—C29—C30—C25	−1.2 (7)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁BrO₂
M_r	303.15
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	100
a, b, c (Å)	28.0680 (6), 5.6508 (1), 15.3741 (3)
V (Å³)	2438.43 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.36
Crystal size (mm)	0.27 × 0.20 × 0.06

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.464, 0.824
No. of measured, independent and observed [I > 2σ(I)] reflections	21610, 5562, 4774
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.087, 0.99
No. of reflections	5562
No. of parameters	325
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.52
Absolute structure	Flack (1983), 2644 Fridel pairs
Absolute structure parameter	−0.002 (9)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Acknowledgements

We thank the University of Malaya for supporting this study.

References

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