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

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

doi:10.1107/S1600536807018648

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

P. S. Patil, S. Chantrapromma, H.-K. Fun, S. M. Dharmaprakash and H. B. R. Babu

The title compound, C₁₆H₁₃BrO₂, crystallizes with two independent molecules (A and B) in the asymmetric unit. The dihedral angle between the two benzene rings is 45.94 (8)° in molecule A and 46.82 (7)° in molecule B. The crystal packing is stabilized by weak C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807018648/ci2364sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807018648/ci2364Isup2.hkl Contains datablock I

CCDC reference: 647615

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.034
wR factor = 0.075
Data-to-parameter ratio = 27.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.85
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          5
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1A   ..  O2B     ..       3.23 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.847
            Tmax scaled      0.372 Tmin scaled      0.231

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Chalcone derivatives have been synthesized by us to study their nonlinear optical properties, since they are prominent materials with excellent blue-light transmittance and good crystallizability (Patil, Teh et al., 2006; Patil, Dharmaprakash et al., 2006; Shettigar et al., 2006; Patil, Ng et al., 2007; Patil, Rosli et al., 2007; Patil, Chantrapromma et al., 2007). The single-crystal X-ray structural study of the title compound, (I), was undertaken in order to establish the structure and conformation of the various groups. Crystallization of compound (I) in a centrosymmetric space group precludes second-order nonlinear optical properties.

There are two independent molecules, A and B, in the asymmetric unit of (I) (Fig. 1). Bond lengths and angles in (I) are in normal ranges (Allen et al., 1987) and comparable with those in related structures (Patil, Teh et al., 2006; Patil, Dharmaprakash et al., 2006; Shettigar et al., 2006; Patil, Ng et al., 2007; Patil, Chantrapromma et al., 2007). The dihedral angle between the two benzene rings is 45.94 (8)° in molecule A and 46.82 (7)°

in molecule B. In molecule A, the least-squares plane through the

O1/C6/C7/C8 group makes dihedral angles of 28.83 (9) and 21.34 (9)° with the C1–C6 and C10–C15 benzene rings, repectively; the corresponding values are 27.56 (9) and 23.85 (9)°, respectively, in molecule B.

A view of the molecular packing in the crystal structure is shown in Fig. 2. The crystal packing is stabilized by weak C—H···π interactions (Table 1; Cg1, Cg2, Cg3 and Cg4 denote the centroids of the rings C1A–C6A, C10A–C15A, C1B–C6B and C10B–C15B, respectively).

Related literature top

For bond length data, see: Allen et al. (1987). For related literature, see: Patil, Chantrapromma et al. (2007); Patil, Dharmaprakash et al. (2006); Patil, Ng et al. (2007); Patil, Rosli et al. (2007); Patil, Teh et al. (2006); Shettigar et al. (2006).

Experimental top

3-Methoxybenzaldehyde (0.01 mol) and 4-bromoacetophenone (0.01 mol) were stirred in methanol (60 ml) at room temperature. 10% NaOH aqueous solution (5 g) was added and the mixture was stirred for 4 h. The resulting precipitate was filtered off, washed with water and dried. The resulting crude product was recrystallized from acetone. Colourless block-shaped single crystals of (I) suitable for X-ray analysis were grown by slow evaporation of an acetone solution at room temperature.

Structure description top

in molecule B. In molecule A, the least-squares plane through the

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures top

	Fig. 1. The asymmetric unit of (I), showing the atomic numbering scheme and with 80% probability displacement ellipsoids.
	Fig. 2. The crystal packing of (I), viewed down the a axis.

1-(4-bromophenyl)-3-(3-methoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₃BrO₂	Z = 4
M_r = 317.17	F(000) = 640
Triclinic, P1	D_x = 1.587 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8459 (1) Å	Cell parameters from 9572 reflections
b = 7.3649 (2) Å	θ = 0.7–32.5°
c = 31.1430 (8) Å	µ = 3.09 mm⁻¹
α = 83.866 (1)°	T = 100 K
β = 87.023 (1)°	Block, colourless
γ = 85.297 (1)°	0.57 × 0.40 × 0.32 mm
V = 1327.42 (5) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	9572 independent reflections
Radiation source: fine-focus sealed tube	7816 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 8.33 pixels mm^-1	θ_max = 32.5°, θ_min = 0.7°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
T_min = 0.273, T_max = 0.439	l = −47→47
35306 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0228P)² + 1.5366P] where P = (F_o² + 2F_c²)/3
9572 reflections	(Δ/σ)_max = 0.002
345 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.81 e Å⁻³

Crystal data top

C₁₆H₁₃BrO₂	γ = 85.297 (1)°
M_r = 317.17	V = 1327.42 (5) Å³
Triclinic, P1	Z = 4
a = 5.8459 (1) Å	Mo Kα radiation
b = 7.3649 (2) Å	µ = 3.09 mm⁻¹
c = 31.1430 (8) Å	T = 100 K
α = 83.866 (1)°	0.57 × 0.40 × 0.32 mm
β = 87.023 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	9572 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	7816 reflections with I > 2σ(I)
T_min = 0.273, T_max = 0.439	R_int = 0.030
35306 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.04	Δρ_max = 0.55 e Å⁻³
9572 reflections	Δρ_min = −0.81 e Å⁻³
345 parameters

Special details top

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
Br1A	0.84725 (3)	0.07145 (3)	−0.205507 (6)	0.02172 (5)
O1A	0.2884 (2)	0.21055 (19)	−0.01168 (4)	0.0204 (3)
O2A	0.6853 (3)	0.3419 (2)	0.20030 (4)	0.0254 (3)
C1A	0.8077 (3)	0.0967 (2)	−0.07324 (6)	0.0165 (3)
H1AA	0.9060	0.0692	−0.0505	0.020*
C2A	0.8833 (3)	0.0624 (2)	−0.11480 (6)	0.0170 (3)
H2AA	1.0306	0.0092	−0.1200	0.020*
C3A	0.7361 (3)	0.1088 (2)	−0.14859 (5)	0.0163 (3)
C4A	0.5133 (3)	0.1835 (2)	−0.14150 (6)	0.0178 (3)
H4AA	0.4166	0.2133	−0.1644	0.021*
C5A	0.4373 (3)	0.2129 (2)	−0.09972 (6)	0.0166 (3)
H5AA	0.2872	0.2600	−0.0945	0.020*
C6A	0.5841 (3)	0.1723 (2)	−0.06541 (5)	0.0147 (3)
C7A	0.4952 (3)	0.2110 (2)	−0.02116 (5)	0.0154 (3)
C8A	0.6620 (3)	0.2555 (2)	0.00939 (6)	0.0175 (3)
H8AA	0.8125	0.2735	−0.0003	0.021*
C9A	0.5984 (3)	0.2703 (2)	0.05092 (6)	0.0158 (3)
H9AA	0.4490	0.2440	0.0595	0.019*
C10A	0.7409 (3)	0.3237 (2)	0.08403 (5)	0.0148 (3)
C11A	0.6590 (3)	0.3073 (2)	0.12715 (6)	0.0161 (3)
H11A	0.5181	0.2593	0.1343	0.019*
C12A	0.7854 (3)	0.3620 (2)	0.15958 (6)	0.0181 (3)
C13A	0.9971 (3)	0.4331 (3)	0.14927 (6)	0.0192 (3)
H13A	1.0830	0.4694	0.1707	0.023*
C14A	1.0781 (3)	0.4489 (2)	0.10627 (6)	0.0185 (3)
H14A	1.2192	0.4968	0.0993	0.022*
C15A	0.9548 (3)	0.3956 (2)	0.07379 (6)	0.0167 (3)
H15A	1.0128	0.4071	0.0453	0.020*
C16A	0.8057 (4)	0.4059 (3)	0.23368 (7)	0.0296 (4)
H16A	0.7184	0.3889	0.2606	0.044*
H16B	0.8272	0.5337	0.2267	0.044*
H16C	0.9527	0.3382	0.2363	0.044*
Br1B	0.23024 (3)	0.57967 (3)	0.299714 (6)	0.02259 (5)
O1B	0.7133 (2)	0.28906 (19)	0.49324 (4)	0.0207 (3)
O2B	0.1579 (2)	−0.0121 (2)	0.70895 (4)	0.0231 (3)
C1B	0.2181 (3)	0.4494 (2)	0.43231 (6)	0.0168 (3)
H1BA	0.1101	0.4569	0.4552	0.020*
C2B	0.1585 (3)	0.5166 (2)	0.39075 (6)	0.0167 (3)
H2BA	0.0125	0.5722	0.3857	0.020*
C3B	0.3193 (3)	0.4997 (2)	0.35684 (6)	0.0161 (3)
C4B	0.5420 (3)	0.4240 (2)	0.36360 (6)	0.0170 (3)
H4BA	0.6489	0.4155	0.3406	0.020*
C5B	0.6012 (3)	0.3613 (2)	0.40554 (6)	0.0160 (3)
H5BA	0.7502	0.3126	0.4107	0.019*
C6B	0.4393 (3)	0.3708 (2)	0.43998 (5)	0.0144 (3)
C7B	0.5106 (3)	0.2960 (2)	0.48421 (6)	0.0162 (3)
C8B	0.3309 (3)	0.2270 (2)	0.51541 (6)	0.0176 (3)
H8BA	0.1864	0.2125	0.5057	0.021*
C9B	0.3712 (3)	0.1849 (2)	0.55731 (5)	0.0157 (3)
H9BA	0.5138	0.2091	0.5663	0.019*
C10B	0.2108 (3)	0.1040 (2)	0.59027 (5)	0.0150 (3)
C11B	0.2677 (3)	0.0902 (2)	0.63390 (5)	0.0156 (3)
H11B	0.4023	0.1355	0.6414	0.019*
C12B	0.1220 (3)	0.0086 (2)	0.66576 (6)	0.0167 (3)
C13B	−0.0778 (3)	−0.0626 (2)	0.65429 (6)	0.0185 (3)
H13B	−0.1724	−0.1211	0.6754	0.022*
C14B	−0.1347 (3)	−0.0459 (2)	0.61143 (6)	0.0174 (3)
H14B	−0.2696	−0.0911	0.6040	0.021*
C15B	0.0068 (3)	0.0375 (2)	0.57933 (6)	0.0164 (3)
H15B	−0.0341	0.0491	0.5506	0.020*
C16B	0.3534 (4)	0.0636 (4)	0.72329 (7)	0.0320 (5)
H16D	0.4902	0.0109	0.7096	0.048*
H16E	0.3604	0.0372	0.7541	0.048*
H16F	0.3415	0.1939	0.7159	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1A	0.02332 (9)	0.02702 (10)	0.01429 (8)	0.00146 (7)	0.00084 (6)	−0.00305 (6)
O1A	0.0156 (6)	0.0263 (7)	0.0194 (6)	−0.0016 (5)	0.0007 (5)	−0.0042 (5)
O2A	0.0286 (7)	0.0341 (8)	0.0140 (6)	−0.0040 (6)	0.0008 (5)	−0.0050 (5)
C1A	0.0157 (7)	0.0178 (8)	0.0155 (7)	0.0001 (6)	−0.0015 (6)	−0.0004 (6)
C2A	0.0155 (7)	0.0174 (8)	0.0177 (8)	0.0007 (6)	−0.0012 (6)	−0.0012 (6)
C3A	0.0186 (8)	0.0163 (8)	0.0139 (7)	−0.0014 (6)	0.0005 (6)	−0.0022 (6)
C4A	0.0175 (8)	0.0187 (8)	0.0175 (8)	0.0008 (6)	−0.0041 (6)	−0.0025 (6)
C5A	0.0139 (7)	0.0171 (8)	0.0191 (8)	−0.0009 (6)	−0.0014 (6)	−0.0025 (6)
C6A	0.0159 (7)	0.0122 (7)	0.0160 (7)	−0.0028 (6)	0.0006 (6)	−0.0013 (6)
C7A	0.0167 (7)	0.0142 (7)	0.0154 (7)	−0.0012 (6)	−0.0005 (6)	−0.0015 (6)
C8A	0.0163 (7)	0.0187 (8)	0.0177 (8)	−0.0025 (6)	−0.0006 (6)	−0.0024 (6)
C9A	0.0151 (7)	0.0143 (7)	0.0181 (7)	−0.0010 (6)	−0.0012 (6)	−0.0021 (6)
C10A	0.0159 (7)	0.0134 (7)	0.0151 (7)	0.0004 (6)	−0.0009 (6)	−0.0020 (6)
C11A	0.0159 (7)	0.0147 (7)	0.0174 (7)	−0.0007 (6)	0.0004 (6)	−0.0015 (6)
C12A	0.0207 (8)	0.0171 (8)	0.0160 (7)	0.0014 (6)	−0.0013 (6)	−0.0020 (6)
C13A	0.0208 (8)	0.0183 (8)	0.0188 (8)	−0.0005 (6)	−0.0056 (6)	−0.0025 (6)
C14A	0.0156 (7)	0.0169 (8)	0.0230 (8)	−0.0016 (6)	−0.0014 (6)	−0.0012 (6)
C15A	0.0167 (7)	0.0160 (8)	0.0170 (7)	−0.0009 (6)	−0.0002 (6)	−0.0009 (6)
C16A	0.0408 (12)	0.0316 (11)	0.0176 (9)	−0.0019 (9)	−0.0043 (8)	−0.0074 (8)
Br1B	0.02450 (9)	0.02607 (10)	0.01655 (8)	−0.00148 (7)	−0.00473 (6)	0.00236 (7)
O1B	0.0165 (6)	0.0268 (7)	0.0189 (6)	−0.0023 (5)	−0.0033 (5)	−0.0008 (5)
O2B	0.0220 (6)	0.0318 (8)	0.0157 (6)	−0.0066 (5)	−0.0009 (5)	0.0001 (5)
C1B	0.0162 (7)	0.0173 (8)	0.0173 (7)	−0.0011 (6)	0.0005 (6)	−0.0045 (6)
C2B	0.0143 (7)	0.0153 (8)	0.0207 (8)	0.0002 (6)	−0.0025 (6)	−0.0028 (6)
C3B	0.0187 (8)	0.0140 (7)	0.0157 (7)	−0.0025 (6)	−0.0021 (6)	−0.0004 (6)
C4B	0.0170 (7)	0.0173 (8)	0.0164 (7)	−0.0013 (6)	0.0014 (6)	−0.0015 (6)
C5B	0.0144 (7)	0.0157 (8)	0.0177 (7)	−0.0012 (6)	−0.0010 (6)	−0.0012 (6)
C6B	0.0152 (7)	0.0134 (7)	0.0153 (7)	−0.0026 (6)	−0.0011 (5)	−0.0029 (5)
C7B	0.0185 (8)	0.0149 (7)	0.0157 (7)	−0.0020 (6)	−0.0008 (6)	−0.0029 (6)
C8B	0.0170 (7)	0.0188 (8)	0.0173 (8)	−0.0041 (6)	−0.0009 (6)	−0.0009 (6)
C9B	0.0161 (7)	0.0144 (7)	0.0167 (7)	−0.0008 (6)	−0.0004 (6)	−0.0025 (6)
C10B	0.0152 (7)	0.0136 (7)	0.0161 (7)	0.0004 (6)	−0.0009 (6)	−0.0023 (6)
C11B	0.0150 (7)	0.0159 (8)	0.0162 (7)	−0.0013 (6)	−0.0004 (6)	−0.0024 (6)
C12B	0.0169 (7)	0.0164 (8)	0.0164 (7)	−0.0002 (6)	−0.0002 (6)	−0.0014 (6)
C13B	0.0173 (8)	0.0165 (8)	0.0213 (8)	−0.0027 (6)	0.0029 (6)	−0.0014 (6)
C14B	0.0152 (7)	0.0147 (8)	0.0227 (8)	−0.0015 (6)	−0.0013 (6)	−0.0035 (6)
C15B	0.0160 (7)	0.0149 (8)	0.0187 (8)	0.0001 (6)	−0.0021 (6)	−0.0030 (6)
C16B	0.0212 (9)	0.0568 (15)	0.0201 (9)	−0.0081 (9)	−0.0009 (7)	−0.0101 (9)

Geometric parameters (Å, º) top

Br1A—C3A	1.8960 (17)	Br1B—C3B	1.8987 (17)
O1A—C7A	1.230 (2)	O1B—C7B	1.228 (2)
O2A—C12A	1.367 (2)	O2B—C12B	1.363 (2)
O2A—C16A	1.426 (2)	O2B—C16B	1.424 (3)
C1A—C2A	1.388 (2)	C1B—C2B	1.387 (2)
C1A—C6A	1.398 (2)	C1B—C6B	1.394 (2)
C1A—H1AA	0.93	C1B—H1BA	0.93
C2A—C3A	1.390 (2)	C2B—C3B	1.385 (2)
C2A—H2AA	0.93	C2B—H2BA	0.93
C3A—C4A	1.388 (2)	C3B—C4B	1.391 (2)
C4A—C5A	1.386 (2)	C4B—C5B	1.389 (2)
C4A—H4AA	0.93	C4B—H4BA	0.93
C5A—C6A	1.397 (2)	C5B—C6B	1.397 (2)
C5A—H5AA	0.93	C5B—H5BA	0.93
C6A—C7A	1.495 (2)	C6B—C7B	1.494 (2)
C7A—C8A	1.476 (2)	C7B—C8B	1.477 (2)
C8A—C9A	1.340 (2)	C8B—C9B	1.337 (2)
C8A—H8AA	0.93	C8B—H8BA	0.93
C9A—C10A	1.464 (2)	C9B—C10B	1.466 (2)
C9A—H9AA	0.93	C9B—H9BA	0.93
C10A—C11A	1.398 (2)	C10B—C15B	1.397 (2)
C10A—C15A	1.406 (2)	C10B—C11B	1.407 (2)
C11A—C12A	1.394 (2)	C11B—C12B	1.393 (2)
C11A—H11A	0.93	C11B—H11B	0.93
C12A—C13A	1.392 (3)	C12B—C13B	1.397 (3)
C13A—C14A	1.393 (3)	C13B—C14B	1.383 (3)
C13A—H13A	0.93	C13B—H13B	0.93
C14A—C15A	1.380 (3)	C14B—C15B	1.388 (2)
C14A—H14A	0.93	C14B—H14B	0.93
C15A—H15A	0.93	C15B—H15B	0.93
C16A—H16A	0.96	C16B—H16D	0.96
C16A—H16B	0.96	C16B—H16E	0.96
C16A—H16C	0.96	C16B—H16F	0.96

C12A—O2A—C16A	116.41 (16)	C12B—O2B—C16B	117.92 (15)
C2A—C1A—C6A	120.24 (16)	C2B—C1B—C6B	120.29 (16)
C2A—C1A—H1AA	119.9	C2B—C1B—H1BA	119.9
C6A—C1A—H1AA	119.9	C6B—C1B—H1BA	119.9
C1A—C2A—C3A	119.15 (16)	C3B—C2B—C1B	119.19 (16)
C1A—C2A—H2AA	120.4	C3B—C2B—H2BA	120.4
C3A—C2A—H2AA	120.4	C1B—C2B—H2BA	120.4
C4A—C3A—C2A	121.51 (16)	C2B—C3B—C4B	121.72 (16)
C4A—C3A—Br1A	119.93 (13)	C2B—C3B—Br1B	118.76 (13)
C2A—C3A—Br1A	118.55 (13)	C4B—C3B—Br1B	119.52 (13)
C5A—C4A—C3A	118.90 (16)	C5B—C4B—C3B	118.48 (16)
C5A—C4A—H4AA	120.5	C5B—C4B—H4BA	120.8
C3A—C4A—H4AA	120.5	C3B—C4B—H4BA	120.8
C4A—C5A—C6A	120.66 (16)	C4B—C5B—C6B	120.73 (16)
C4A—C5A—H5AA	119.7	C4B—C5B—H5BA	119.6
C6A—C5A—H5AA	119.7	C6B—C5B—H5BA	119.6
C5A—C6A—C1A	119.50 (16)	C1B—C6B—C5B	119.52 (16)
C5A—C6A—C7A	118.48 (15)	C1B—C6B—C7B	122.08 (15)
C1A—C6A—C7A	122.03 (15)	C5B—C6B—C7B	118.40 (15)
O1A—C7A—C8A	122.18 (16)	O1B—C7B—C8B	122.20 (16)
O1A—C7A—C6A	120.01 (15)	O1B—C7B—C6B	120.13 (16)
C8A—C7A—C6A	117.78 (15)	C8B—C7B—C6B	117.64 (15)
C9A—C8A—C7A	120.57 (16)	C9B—C8B—C7B	121.50 (16)
C9A—C8A—H8AA	119.7	C9B—C8B—H8BA	119.3
C7A—C8A—H8AA	119.7	C7B—C8B—H8BA	119.3
C8A—C9A—C10A	126.44 (16)	C8B—C9B—C10B	125.81 (16)
C8A—C9A—H9AA	116.8	C8B—C9B—H9BA	117.1
C10A—C9A—H9AA	116.8	C10B—C9B—H9BA	117.1
C11A—C10A—C15A	118.87 (16)	C15B—C10B—C11B	119.60 (16)
C11A—C10A—C9A	118.94 (15)	C15B—C10B—C9B	121.75 (15)
C15A—C10A—C9A	122.17 (15)	C11B—C10B—C9B	118.64 (15)
C12A—C11A—C10A	120.94 (16)	C12B—C11B—C10B	119.85 (16)
C12A—C11A—H11A	119.5	C12B—C11B—H11B	120.1
C10A—C11A—H11A	119.5	C10B—C11B—H11B	120.1
O2A—C12A—C13A	124.65 (17)	O2B—C12B—C11B	125.29 (16)
O2A—C12A—C11A	115.38 (16)	O2B—C12B—C13B	114.70 (15)
C13A—C12A—C11A	119.96 (16)	C11B—C12B—C13B	120.01 (16)
C12A—C13A—C14A	118.87 (17)	C14B—C13B—C12B	119.83 (16)
C12A—C13A—H13A	120.6	C14B—C13B—H13B	120.1
C14A—C13A—H13A	120.6	C12B—C13B—H13B	120.1
C15A—C14A—C13A	121.84 (17)	C13B—C14B—C15B	120.89 (16)
C15A—C14A—H14A	119.1	C13B—C14B—H14B	119.6
C13A—C14A—H14A	119.1	C15B—C14B—H14B	119.6
C14A—C15A—C10A	119.52 (16)	C14B—C15B—C10B	119.78 (16)
C14A—C15A—H15A	120.2	C14B—C15B—H15B	120.1
C10A—C15A—H15A	120.2	C10B—C15B—H15B	120.1
O2A—C16A—H16A	109.5	O2B—C16B—H16D	109.5
O2A—C16A—H16B	109.5	O2B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
O2A—C16A—H16C	109.5	O2B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5

C6A—C1A—C2A—C3A	1.7 (3)	C6B—C1B—C2B—C3B	1.9 (3)
C1A—C2A—C3A—C4A	−1.9 (3)	C1B—C2B—C3B—C4B	−2.7 (3)
C1A—C2A—C3A—Br1A	177.12 (13)	C1B—C2B—C3B—Br1B	176.50 (13)
C2A—C3A—C4A—C5A	0.3 (3)	C2B—C3B—C4B—C5B	1.1 (3)
Br1A—C3A—C4A—C5A	−178.73 (13)	Br1B—C3B—C4B—C5B	−178.07 (13)
C3A—C4A—C5A—C6A	1.6 (3)	C3B—C4B—C5B—C6B	1.3 (3)
C4A—C5A—C6A—C1A	−1.8 (3)	C2B—C1B—C6B—C5B	0.5 (3)
C4A—C5A—C6A—C7A	178.50 (16)	C2B—C1B—C6B—C7B	−179.74 (16)
C2A—C1A—C6A—C5A	0.1 (3)	C4B—C5B—C6B—C1B	−2.1 (3)
C2A—C1A—C6A—C7A	179.84 (16)	C4B—C5B—C6B—C7B	178.13 (16)
C5A—C6A—C7A—O1A	27.0 (2)	C1B—C6B—C7B—O1B	−153.84 (18)
C1A—C6A—C7A—O1A	−152.69 (17)	C5B—C6B—C7B—O1B	25.9 (2)
C5A—C6A—C7A—C8A	−150.78 (16)	C1B—C6B—C7B—C8B	28.0 (2)
C1A—C6A—C7A—C8A	29.5 (2)	C5B—C6B—C7B—C8B	−152.18 (16)
O1A—C7A—C8A—C9A	10.1 (3)	O1B—C7B—C8B—C9B	12.6 (3)
C6A—C7A—C8A—C9A	−172.12 (16)	C6B—C7B—C8B—C9B	−169.30 (16)
C7A—C8A—C9A—C10A	−176.23 (16)	C7B—C8B—C9B—C10B	−175.57 (16)
C8A—C9A—C10A—C11A	−171.02 (17)	C8B—C9B—C10B—C15B	9.6 (3)
C8A—C9A—C10A—C15A	10.7 (3)	C8B—C9B—C10B—C11B	−171.76 (17)
C15A—C10A—C11A—C12A	0.4 (3)	C15B—C10B—C11B—C12B	0.8 (3)
C9A—C10A—C11A—C12A	−177.94 (16)	C9B—C10B—C11B—C12B	−177.94 (16)
C16A—O2A—C12A—C13A	2.5 (3)	C16B—O2B—C12B—C11B	3.4 (3)
C16A—O2A—C12A—C11A	−176.78 (17)	C16B—O2B—C12B—C13B	−177.54 (18)
C10A—C11A—C12A—O2A	178.96 (16)	C10B—C11B—C12B—O2B	−179.75 (17)
C10A—C11A—C12A—C13A	−0.4 (3)	C10B—C11B—C12B—C13B	1.3 (3)
O2A—C12A—C13A—C14A	−178.98 (17)	O2B—C12B—C13B—C14B	178.57 (16)
C11A—C12A—C13A—C14A	0.3 (3)	C11B—C12B—C13B—C14B	−2.4 (3)
C12A—C13A—C14A—C15A	−0.2 (3)	C12B—C13B—C14B—C15B	1.4 (3)
C13A—C14A—C15A—C10A	0.2 (3)	C13B—C14B—C15B—C10B	0.7 (3)
C11A—C10A—C15A—C14A	−0.3 (3)	C11B—C10B—C15B—C14B	−1.7 (3)
C9A—C10A—C15A—C14A	177.95 (16)	C9B—C10B—C15B—C14B	176.94 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2A—H2AA···Cg2ⁱ	0.93	2.86	3.4495 (17)	123
C5A—H5AA···Cg2ⁱⁱ	0.93	2.77	3.3798 (17)	124
C2B—H2BA···Cg4ⁱⁱⁱ	0.93	2.97	3.5305 (16)	120
C5B—H5BA···Cg4^iv	0.93	2.88	3.4596 (17)	122
C14A—H14A···Cg1^v	0.93	2.86	3.5094 (17)	128
C14B—H14B···Cg3^vi	0.93	2.69	3.3678 (17)	131

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃BrO₂
M_r	317.17
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.8459 (1), 7.3649 (2), 31.1430 (8)
α, β, γ (°)	83.866 (1), 87.023 (1), 85.297 (1)
V (Å³)	1327.42 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.09
Crystal size (mm)	0.57 × 0.40 × 0.32

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.273, 0.439
No. of measured, independent and observed [I > 2σ(I)] reflections	35306, 9572, 7816
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.075, 1.04
No. of reflections	9572
No. of parameters	345
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.81

Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).