Polymorphism of 4-bromobenzophenone

A combination of single-crystal and powder X-ray diffractometry was used to study the structure of two polymorphs of 4-bromobenzophenone over the temperature range from 100 to 300 K. One of the polymorphs of the title compound was known previously and its structure has been determined at room temperature [Ebbinghaus et al. (1997). Z. Kristallogr. 212, 339–340]. Two crystal growth methods were employed, one of which (a modification of the Bridgman–Stockbarger technique) resulted in single crystals of a previously unknown structure. The basic physical properties of the stable polymorph are: growth method, from 2-propanol solutions or gradient sublimation; space group, monoclinic P2₁/c; melting point, T_m = 355.2 K; X-ray density (at 100 K), D_x = 1.646 g cm⁻³. The same properties of the metastable polymorph (triclinic ) are: growth method, modified Bridgman–Stockbarger method; X-ray density (at 100 K), D_x = 1.645 g cm⁻³; T_m = 354 K. Thermograms suggest that the melting of the metastable form is accompanied by at least a partial crystallization presumably into the monoclinic form; the transformation is therefore monotropic. Analysis of short distances in both polymorphs shows that numerous weak hydrogen bonds of the C—H...π type ensure additional stabilization within the respective planes normal to the longest dimension of the molecules. The strong temperature dependence of the lattice constants and of the weak bond distances in the monoclinic form suggest that the weak bond interactions might be responsible for both the large thermal expansion within plane bc and the considerable thermal expansion anisotropy.

Computing details

For all compounds, data collection: Oxford Diffraction CrysAlis; cell refinement: Oxford Diffraction CrysAlis; data reduction: Oxford Diffraction CrysAlis; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

(4m250) (4-bromophenyl)(phenyl)methanone

Crystal data

C13H9BrO	F(000) = 520
Mr = 261.11	Dx = 1.599 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.124 (2) Å	Cell parameters from 700 reflections
b = 14.646 (3) Å	θ = 10–11°
c = 6.1585 (12) Å	µ = 3.76 mm^−1
β = 97.38 (3)°	T = 150 K
V = 1084.5 (4) Å^3	Plate, colourless
Z = 4	0.4 × 0.2 × 0.04 mm

Data collection

Oxford Diffraction diffractometer	3514 independent reflections
Radiation source: fine-focus sealed tube	1560 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.116
ο scans	θmax = 32.2°, θmin = 3.3°
Absorption correction: empirical (using intensity measurements) ?	h = −16→17
Tmin = 0.235, Tmax = 0.734	k = −20→21
8971 measured reflections	l = −9→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.069	H-atom parameters constrained
wR(F^2) = 0.228	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
3514 reflections	Δρmax = 0.41 e Å^−3
137 parameters	Δρmin = −0.56 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.96358 (4)	0.36488 (4)	1.14487 (9)	0.1031 (3)
O1	0.5249 (3)	0.3859 (3)	0.3404 (5)	0.0857 (9)
C1	0.5197 (4)	0.3810 (2)	0.5368 (6)	0.0654 (8)
C1A	0.6245 (3)	0.3793 (2)	0.6925 (6)	0.0617 (8)
C2A	0.6320 (4)	0.3405 (2)	0.9001 (7)	0.0670 (8)
H2A	0.5671	0.3171	0.9516	0.080*
C3A	0.7336 (4)	0.3358 (3)	1.0327 (7)	0.0721 (9)
H3A	0.7383	0.3088	1.1738	0.087*
C4A	0.8266 (4)	0.3703 (2)	0.9589 (7)	0.0702 (9)
C5A	0.8215 (4)	0.4092 (3)	0.7518 (7)	0.0747 (9)
H5A	0.8866	0.4327	0.7012	0.090*
C6A	0.7207 (3)	0.4130 (2)	0.6218 (6)	0.0700 (9)
H6A	0.7168	0.4394	0.4801	0.084*
C1B	0.4077 (3)	0.3761 (2)	0.6160 (6)	0.0643 (8)
C2B	0.3218 (3)	0.3368 (3)	0.4774 (7)	0.0717 (9)
H2B	0.3359	0.3108	0.3424	0.086*
C3B	0.2157 (4)	0.3357 (3)	0.5356 (9)	0.0851 (12)
H3B	0.1569	0.3079	0.4417	0.102*
C4B	0.1949 (4)	0.3751 (3)	0.7316 (9)	0.0834 (12)
H4B	0.1216	0.3756	0.7709	0.100*
C5B	0.2808 (4)	0.4133 (3)	0.8677 (8)	0.0807 (11)
H5B	0.2667	0.4399	1.0021	0.097*
C6B	0.3865 (3)	0.4136 (2)	0.8131 (6)	0.0677 (8)
H6B	0.4454	0.4396	0.9100	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0741 (4)	0.1374 (6)	0.0941 (5)	0.0036 (2)	−0.0030 (3)	0.0131 (3)
O1	0.085 (2)	0.116 (2)	0.0567 (16)	−0.0012 (15)	0.0104 (15)	−0.0019 (14)
C1	0.079 (2)	0.0623 (16)	0.0550 (18)	0.0015 (15)	0.0100 (16)	0.0008 (14)
C1A	0.0686 (19)	0.0597 (16)	0.0575 (18)	0.0008 (13)	0.0105 (15)	0.0004 (13)
C2A	0.077 (2)	0.0621 (17)	0.063 (2)	0.0011 (15)	0.0157 (17)	−0.0009 (14)
C3A	0.084 (2)	0.0718 (19)	0.060 (2)	0.0005 (17)	0.0091 (18)	−0.0009 (16)
C4A	0.071 (2)	0.076 (2)	0.063 (2)	0.0000 (15)	0.0080 (17)	−0.0025 (16)
C5A	0.072 (2)	0.078 (2)	0.076 (2)	0.0011 (17)	0.0174 (18)	0.0047 (18)
C6A	0.079 (2)	0.0705 (19)	0.063 (2)	0.0008 (16)	0.0179 (17)	0.0058 (16)
C1B	0.075 (2)	0.0588 (16)	0.0582 (18)	0.0027 (14)	0.0058 (16)	−0.0017 (13)
C2B	0.076 (2)	0.0711 (19)	0.067 (2)	0.0012 (17)	0.0031 (18)	−0.0012 (16)
C3B	0.075 (3)	0.084 (2)	0.093 (3)	−0.0016 (19)	−0.003 (2)	0.007 (2)
C4B	0.072 (2)	0.090 (3)	0.091 (3)	0.0101 (19)	0.021 (2)	0.010 (2)
C5B	0.091 (3)	0.073 (2)	0.079 (3)	0.0121 (19)	0.016 (2)	0.0017 (18)
C6B	0.078 (2)	0.0644 (17)	0.0607 (19)	0.0025 (15)	0.0087 (16)	−0.0028 (15)

Geometric parameters (Å, º)

Br1—C4A	1.894 (5)	C6A—H6A	0.9500
O1—C1	1.222 (5)	C1B—C2B	1.383 (6)
C1—C1A	1.491 (6)	C1B—C6B	1.386 (5)
C1—C1B	1.503 (6)	C2B—C3B	1.379 (6)
C1A—C6A	1.387 (5)	C2B—H2B	0.9500
C1A—C2A	1.391 (5)	C3B—C4B	1.390 (7)
C2A—C3A	1.389 (6)	C3B—H3B	0.9500
C2A—H2A	0.9500	C4B—C5B	1.370 (7)
C3A—C4A	1.366 (6)	C4B—H4B	0.9500
C3A—H3A	0.9500	C5B—C6B	1.365 (6)
C4A—C5A	1.391 (6)	C5B—H5B	0.9500
C5A—C6A	1.373 (6)	C6B—H6B	0.9500
C5A—H5A	0.9500
O1—C1—C1A	119.3 (4)	C1A—C6A—H6A	119.2
O1—C1—C1B	119.2 (4)	C2B—C1B—C6B	119.7 (4)
C1A—C1—C1B	121.4 (3)	C2B—C1B—C1	117.4 (3)
C6A—C1A—C2A	118.4 (4)	C6B—C1B—C1	122.8 (3)
C6A—C1A—C1	118.3 (3)	C3B—C2B—C1B	119.9 (4)
C2A—C1A—C1	123.2 (3)	C3B—C2B—H2B	120.1
C3A—C2A—C1A	120.6 (4)	C1B—C2B—H2B	120.1
C3A—C2A—H2A	119.7	C2B—C3B—C4B	120.0 (4)
C1A—C2A—H2A	119.7	C2B—C3B—H3B	120.0
C4A—C3A—C2A	119.6 (4)	C4B—C3B—H3B	120.0
C4A—C3A—H3A	120.2	C5B—C4B—C3B	119.4 (4)
C2A—C3A—H3A	120.2	C5B—C4B—H4B	120.3
C3A—C4A—C5A	121.0 (4)	C3B—C4B—H4B	120.3
C3A—C4A—Br1	118.7 (3)	C6B—C5B—C4B	121.0 (4)
C5A—C4A—Br1	120.3 (3)	C6B—C5B—H5B	119.5
C6A—C5A—C4A	118.9 (4)	C4B—C5B—H5B	119.5
C6A—C5A—H5A	120.5	C5B—C6B—C1B	120.0 (4)
C4A—C5A—H5A	120.5	C5B—C6B—H6B	120.0
C5A—C6A—C1A	121.5 (4)	C1B—C6B—H6B	120.0
C5A—C6A—H6A	119.2

(4bmlt) (4-bromophenyl)(phenyl)methanone

Crystal data

C13H9BrO	F(000) = 520
Mr = 261.11	Dx = 1.646 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.092 (2) Å	Cell parameters from 700 reflections
b = 14.343 (3) Å	θ = 10–11°
c = 6.1243 (12) Å	µ = 3.87 mm^−1
β = 97.26 (3)°	T = 100 K
V = 1053.7 (4) Å^3	Plate, colourless
Z = 4	0.4 × 0.2 × 0.04 mm

Data collection

XCalibur-3 (Oxford Diffraction Ltd.) diffractometer	3444 independent reflections
Radiation source: fine-focus sealed tube	2253 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.121
ο scans	θmax = 32.1°, θmin = 2.8°
Absorption correction: empirical (using intensity measurements) ?	h = −17→17
Tmin = 0.235, Tmax = 0.734	k = −21→20
12546 measured reflections	l = −9→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.294	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.184P)^2 + 0.7463P] where P = (Fo^2 + 2Fc^2)/3
3444 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.98 e Å^−3
0 restraints	Δρmin = −0.91 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.46547 (5)	0.63531 (5)	1.14501 (10)	0.0610 (3)
O1	0.0247 (3)	0.6129 (3)	0.3383 (6)	0.0538 (8)
C1	0.0201 (5)	0.6177 (4)	0.5344 (8)	0.0487 (10)
C1A	0.1249 (5)	0.6205 (4)	0.6928 (9)	0.0479 (9)
C2A	0.1317 (5)	0.6596 (4)	0.9010 (9)	0.0499 (10)
H2A	0.0663	0.6829	0.9531	0.060*
C3A	0.2342 (5)	0.6649 (4)	1.0351 (9)	0.0515 (10)
H3A	0.2388	0.6923	1.1771	0.062*
C4A	0.3296 (4)	0.6295 (4)	0.9583 (9)	0.0484 (10)
C5A	0.3248 (5)	0.5909 (4)	0.7506 (9)	0.0529 (11)
H5A	0.3905	0.5677	0.6995	0.063*
C6A	0.2226 (4)	0.5861 (3)	0.6165 (9)	0.0490 (9)
H6A	0.2187	0.5597	0.4735	0.059*
C1B	−0.0920 (5)	0.6235 (3)	0.6145 (9)	0.0486 (10)
C2B	−0.1132 (5)	0.5862 (4)	0.8171 (9)	0.0503 (10)
H2B	−0.0541	0.5604	0.9157	0.060*
C3B	−0.2215 (5)	0.5871 (4)	0.8728 (9)	0.0547 (11)
H3B	−0.2358	0.5610	1.0090	0.066*
C4B	−0.3077 (5)	0.6252 (4)	0.7345 (10)	0.0543 (11)
H4B	−0.3814	0.6246	0.7733	0.065*
C5B	−0.2858 (5)	0.6654 (4)	0.5338 (10)	0.0553 (11)
H5B	−0.3447	0.6933	0.4385	0.066*
C6B	−0.1785 (5)	0.6641 (4)	0.4754 (9)	0.0531 (11)
H6B	−0.1641	0.6910	0.3401	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0525 (4)	0.0737 (5)	0.0558 (4)	−0.0014 (2)	0.0029 (2)	−0.0046 (2)
O1	0.052 (2)	0.066 (2)	0.0431 (18)	0.0008 (16)	0.0066 (15)	−0.0014 (15)
C1	0.054 (3)	0.049 (2)	0.042 (2)	−0.0014 (18)	0.0025 (18)	0.0007 (17)
C1A	0.051 (2)	0.048 (2)	0.044 (2)	0.0013 (17)	0.0070 (18)	0.0009 (17)
C2A	0.055 (3)	0.047 (2)	0.050 (2)	0.0018 (18)	0.0118 (19)	0.0007 (18)
C3A	0.056 (3)	0.053 (2)	0.045 (2)	−0.002 (2)	0.0077 (19)	−0.0031 (19)
C4A	0.044 (2)	0.055 (3)	0.045 (2)	0.0008 (17)	0.0005 (18)	0.0015 (17)
C5A	0.056 (3)	0.052 (3)	0.052 (2)	0.003 (2)	0.013 (2)	−0.002 (2)
C6A	0.051 (2)	0.047 (2)	0.049 (2)	0.0009 (17)	0.0077 (18)	−0.0011 (18)
C1B	0.049 (2)	0.047 (2)	0.049 (2)	−0.0002 (17)	0.0050 (19)	−0.0001 (17)
C2B	0.054 (2)	0.048 (2)	0.049 (2)	0.0005 (18)	0.0082 (19)	0.0027 (18)
C3B	0.063 (3)	0.049 (2)	0.054 (3)	−0.005 (2)	0.012 (2)	−0.004 (2)
C4B	0.052 (3)	0.059 (3)	0.053 (3)	−0.007 (2)	0.010 (2)	−0.001 (2)
C5B	0.055 (3)	0.053 (3)	0.056 (3)	0.001 (2)	0.001 (2)	−0.004 (2)
C6B	0.056 (3)	0.051 (2)	0.053 (3)	−0.006 (2)	0.011 (2)	−0.002 (2)

Geometric parameters (Å, º)

Br1—C4A	1.881 (5)	C6A—H6A	0.9500
O1—C1	1.212 (6)	C1B—C6B	1.390 (8)
C1—C1A	1.496 (8)	C1B—C2B	1.405 (7)
C1—C1B	1.501 (8)	C2B—C3B	1.394 (8)
C1A—C2A	1.386 (7)	C2B—H2B	0.9500
C1A—C6A	1.412 (7)	C3B—C4B	1.371 (9)
C2A—C3A	1.399 (8)	C3B—H3B	0.9500
C2A—H2A	0.9500	C4B—C5B	1.412 (8)
C3A—C4A	1.395 (8)	C4B—H4B	0.9500
C3A—H3A	0.9500	C5B—C6B	1.390 (8)
C4A—C5A	1.382 (7)	C5B—H5B	0.9500
C5A—C6A	1.397 (8)	C6B—H6B	0.9500
C5A—H5A	0.9500
O1—C1—C1A	120.2 (5)	C1A—C6A—H6A	119.9
O1—C1—C1B	119.0 (5)	C6B—C1B—C2B	119.6 (5)
C1A—C1—C1B	120.9 (5)	C6B—C1B—C1	117.6 (5)
C2A—C1A—C6A	119.4 (5)	C2B—C1B—C1	122.7 (5)
C2A—C1A—C1	123.6 (5)	C3B—C2B—C1B	119.6 (5)
C6A—C1A—C1	116.8 (5)	C3B—C2B—H2B	120.2
C1A—C2A—C3A	120.4 (5)	C1B—C2B—H2B	120.2
C1A—C2A—H2A	119.8	C4B—C3B—C2B	121.2 (5)
C3A—C2A—H2A	119.8	C4B—C3B—H3B	119.4
C4A—C3A—C2A	119.4 (5)	C2B—C3B—H3B	119.4
C4A—C3A—H3A	120.3	C3B—C4B—C5B	119.2 (6)
C2A—C3A—H3A	120.3	C3B—C4B—H4B	120.4
C5A—C4A—C3A	121.1 (5)	C5B—C4B—H4B	120.4
C5A—C4A—Br1	120.6 (4)	C6B—C5B—C4B	120.2 (5)
C3A—C4A—Br1	118.4 (4)	C6B—C5B—H5B	119.9
C4A—C5A—C6A	119.5 (5)	C4B—C5B—H5B	119.9
C4A—C5A—H5A	120.3	C5B—C6B—C1B	120.2 (5)
C6A—C5A—H5A	120.3	C5B—C6B—H6B	119.9
C5A—C6A—C1A	120.2 (5)	C1B—C6B—H6B	119.9
C5A—C6A—H6A	119.9

(4btlt) (4-bromophenyl)(phenyl)methanone

Crystal data

C13H9BrO	Z = 2
Mr = 261.11	F(000) = 260
Triclinic, P1	Dx = 1.647 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.1056 (10) Å	Cell parameters from 700 reflections
b = 7.2931 (16) Å	θ = 10–11°
c = 12.0999 (17) Å	µ = 3.87 mm^−1
α = 98.197 (15)°	T = 100 K
β = 98.735 (13)°	Plate, colourless
γ = 91.111 (15)°	0.3 × 0.2 × 0.04 mm
V = 526.64 (16) Å^3

Data collection

Xcalibur-3 (Oxford Diffraction Ltd.) diffractometer	3710 independent reflections
Radiation source: fine-focus sealed tube	2748 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
ο scans	θmax = 34.0°, θmin = 3.1°
Absorption correction: empirical (using intensity measurements) ?	h = −9→9
Tmin = 0.110, Tmax = 0.576	k = −11→11
5351 measured reflections	l = −18→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.204	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.090P)^2 + 3.010P] where P = (Fo^2 + 2Fc^2)/3
3710 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 1.47 e Å^−3
0 restraints	Δρmin = −0.86 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.35586 (9)	0.73983 (8)	−0.44840 (4)	0.02974 (18)
O1	1.1749 (6)	0.7283 (6)	−0.0012 (3)	0.0308 (8)
C1	0.9770 (7)	0.7387 (6)	0.0040 (4)	0.0205 (8)
C1A	0.8161 (7)	0.7338 (6)	−0.1033 (4)	0.0177 (7)
C2A	0.6074 (7)	0.8090 (6)	−0.1068 (4)	0.0195 (8)
H2A	0.5580	0.8578	−0.0382	0.023*
C3A	0.4710 (7)	0.8133 (6)	−0.2089 (4)	0.0215 (8)
H3A	0.3293	0.8654	−0.2106	0.026*
C4A	0.5440 (8)	0.7409 (6)	−0.3082 (4)	0.0211 (8)
C5A	0.7518 (8)	0.6650 (6)	−0.3083 (4)	0.0226 (8)
H5A	0.7992	0.6166	−0.3775	0.027*
C6A	0.8879 (8)	0.6613 (6)	−0.2064 (4)	0.0207 (8)
H6A	1.0299	0.6100	−0.2054	0.025*
C1B	0.8983 (7)	0.7566 (6)	0.1154 (4)	0.0181 (7)
C2B	0.6942 (7)	0.6830 (6)	0.1329 (4)	0.0207 (8)
H2B	0.5922	0.6243	0.0701	0.025*
C3B	0.6402 (8)	0.6947 (7)	0.2399 (4)	0.0235 (8)
H3B	0.5022	0.6427	0.2502	0.028*
C4B	0.7858 (9)	0.7819 (7)	0.3335 (4)	0.0270 (9)
H4B	0.7491	0.7875	0.4074	0.032*
C5B	0.9860 (9)	0.8608 (7)	0.3170 (4)	0.0251 (9)
H5B	1.0831	0.9259	0.3798	0.030*
C6B	1.0445 (8)	0.8451 (6)	0.2101 (4)	0.0216 (8)
H6B	1.1843	0.8945	0.2005	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0314 (3)	0.0334 (3)	0.0219 (2)	0.00693 (18)	−0.00187 (17)	0.00122 (18)
O1	0.0158 (15)	0.049 (2)	0.0259 (17)	0.0006 (14)	0.0044 (13)	−0.0016 (16)
C1	0.0179 (18)	0.0222 (19)	0.0205 (19)	−0.0001 (14)	0.0047 (15)	−0.0010 (15)
C1A	0.0142 (16)	0.0190 (17)	0.0196 (18)	0.0017 (13)	0.0036 (14)	0.0008 (14)
C2A	0.0162 (17)	0.0220 (18)	0.0194 (18)	0.0017 (14)	0.0026 (14)	0.0004 (15)
C3A	0.0161 (18)	0.0218 (18)	0.028 (2)	0.0021 (14)	0.0040 (15)	0.0079 (17)
C4A	0.0211 (19)	0.0195 (18)	0.0205 (19)	0.0006 (14)	−0.0038 (15)	0.0029 (15)
C5A	0.025 (2)	0.0231 (19)	0.0204 (19)	0.0026 (16)	0.0070 (16)	0.0018 (16)
C6A	0.0211 (19)	0.0205 (18)	0.0203 (19)	0.0025 (14)	0.0051 (15)	0.0007 (15)
C1B	0.0160 (17)	0.0189 (17)	0.0196 (18)	−0.0001 (13)	0.0033 (14)	0.0030 (14)
C2B	0.0159 (17)	0.0206 (18)	0.025 (2)	−0.0002 (14)	0.0041 (15)	0.0000 (16)
C3B	0.022 (2)	0.0228 (19)	0.028 (2)	0.0034 (15)	0.0085 (17)	0.0068 (17)
C4B	0.031 (2)	0.030 (2)	0.023 (2)	0.0054 (18)	0.0084 (18)	0.0102 (18)
C5B	0.028 (2)	0.024 (2)	0.023 (2)	0.0001 (17)	0.0000 (17)	0.0057 (17)
C6B	0.0203 (19)	0.0216 (18)	0.0222 (19)	0.0004 (15)	0.0025 (15)	0.0015 (16)

Geometric parameters (Å, º)

Br1—C4A	1.898 (4)	C6A—H6A	0.9500
O1—C1	1.223 (6)	C1B—C2B	1.405 (6)
C1—C1B	1.487 (6)	C1B—C6B	1.407 (6)
C1—C1A	1.500 (6)	C2B—C3B	1.375 (7)
C1A—C2A	1.394 (6)	C2B—H2B	0.9500
C1A—C6A	1.420 (6)	C3B—C4B	1.394 (8)
C2A—C3A	1.386 (6)	C3B—H3B	0.9500
C2A—H2A	0.9500	C4B—C5B	1.395 (7)
C3A—C4A	1.383 (7)	C4B—H4B	0.9500
C3A—H3A	0.9500	C5B—C6B	1.384 (7)
C4A—C5A	1.394 (7)	C5B—H5B	0.9500
C5A—C6A	1.382 (7)	C6B—H6B	0.9500
C5A—H5A	0.9500
O1—C1—C1B	120.2 (4)	C1A—C6A—H6A	119.9
O1—C1—C1A	119.0 (4)	C2B—C1B—C6B	118.2 (4)
C1B—C1—C1A	120.8 (4)	C2B—C1B—C1	124.4 (4)
C2A—C1A—C6A	118.9 (4)	C6B—C1B—C1	117.3 (4)
C2A—C1A—C1	123.0 (4)	C3B—C2B—C1B	120.8 (4)
C6A—C1A—C1	117.9 (4)	C3B—C2B—H2B	119.6
C3A—C2A—C1A	120.9 (4)	C1B—C2B—H2B	119.6
C3A—C2A—H2A	119.5	C2B—C3B—C4B	120.7 (5)
C1A—C2A—H2A	119.5	C2B—C3B—H3B	119.6
C4A—C3A—C2A	119.1 (4)	C4B—C3B—H3B	119.6
C4A—C3A—H3A	120.5	C3B—C4B—C5B	119.1 (5)
C2A—C3A—H3A	120.5	C3B—C4B—H4B	120.5
C3A—C4A—C5A	121.7 (4)	C5B—C4B—H4B	120.5
C3A—C4A—Br1	119.6 (3)	C6B—C5B—C4B	120.5 (5)
C5A—C4A—Br1	118.7 (4)	C6B—C5B—H5B	119.7
C6A—C5A—C4A	119.1 (4)	C4B—C5B—H5B	119.7
C6A—C5A—H5A	120.5	C5B—C6B—C1B	120.5 (4)
C4A—C5A—H5A	120.5	C5B—C6B—H6B	119.7
C5A—C6A—C1A	120.2 (4)	C1B—C6B—H6B	119.7
C5A—C6A—H6A	119.9