Bending the bonds: unveiling halogen interactions in the elastic polymorph of 2,5-bis­(3-bromo­phenyl)­furan

This paper investigates the structural properties of 2,5-bis­(3-bromo­phenyl)­furan polymorphs, focusing on the halogen interactions and their influence on crystal mechanical properties. In this study, three different polymorphic modifications were obtained which crystallize in the orthorhombic system. Two of the polymorphs possess halogen interactions but only one exhibits elastic properties. Through X-ray diffraction, crystallographic analysis and computational modelling, intricate bromine-based halogen interactions and their impact on the packing arrangement and stability were revealed. The correlation between these interactions and crystal properties, including molecular arrangement and intermolecular forces, is explored. Understanding these relationships is vital for materials design and supramolecular chemistry, enabling the rational synthesis of tailored materials.

Computing details

(alpha)

Crystal data

C16H10Br2O	Dx = 1.863 Mg m^−3
Mr = 378.06	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 13880 reflections
a = 8.226 (3) Å	θ = 2.9–29.1°
b = 13.408 (4) Å	µ = 6.00 mm^−1
c = 12.222 (4) Å	T = 100 K
V = 1348.0 (8) Å^3	Rhombohedral, clear colourless
Z = 4	0.44 × 0.19 × 0.09 mm
F(000) = 736

Data collection

Xcalibur, Atlas diffractometer	3505 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	3224 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 10.6249 pixels mm^-1	θmax = 29.5°, θmin = 2.9°
ω scans	h = −11→11
Absorption correction: multi-scan CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −18→17
Tmin = 0.469, Tmax = 1.000	l = −15→16
27898 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.022	w = 1/[σ^2(Fo^2) + (0.0181P)^2 + 0.3092P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.041	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.54 e Å^−3
3505 reflections	Δρmin = −0.34 e Å^−3
172 parameters	Absolute structure: Flack x determined using 1401 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraint	Absolute structure parameter: −0.014 (4)
Primary atom site location: dual

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br2	0.20026 (3)	0.89190 (2)	0.71508 (3)	0.01983 (8)
Br1	0.44383 (3)	0.33814 (2)	0.56968 (3)	0.02011 (8)
O1	0.6098 (2)	0.70586 (15)	0.43522 (17)	0.0140 (4)
C7	0.5619 (3)	0.3957 (2)	0.4504 (3)	0.0161 (7)
C16	0.4526 (3)	0.8525 (2)	0.5620 (3)	0.0148 (6)
H16	0.428198	0.785858	0.575078	0.018*
C14	0.4056 (4)	1.0273 (2)	0.6014 (3)	0.0182 (7)
H14	0.349651	1.076403	0.639725	0.022*
C2	0.7845 (4)	0.7104 (2)	0.2956 (3)	0.0169 (7)
H2	0.851840	0.690905	0.238309	0.020*
C9	0.7261 (4)	0.3782 (3)	0.2921 (3)	0.0230 (7)
H9	0.775868	0.338167	0.239741	0.028*
C8	0.6361 (4)	0.3339 (2)	0.3753 (3)	0.0199 (7)
H8	0.626297	0.264918	0.380111	0.024*
C5	0.6674 (4)	0.5423 (2)	0.3631 (3)	0.0147 (6)
C6	0.5737 (3)	0.4987 (2)	0.4461 (2)	0.0147 (6)
H6	0.520488	0.538184	0.497348	0.018*
C15	0.3713 (4)	0.9270 (2)	0.6175 (3)	0.0173 (7)
C3	0.7600 (4)	0.8093 (3)	0.3334 (3)	0.0174 (7)
H3	0.807739	0.866887	0.305574	0.021*
C11	0.5729 (4)	0.8787 (2)	0.4855 (3)	0.0153 (6)
C1	0.6915 (3)	0.6496 (2)	0.3584 (3)	0.0146 (6)
C10	0.7428 (4)	0.4803 (2)	0.2858 (3)	0.0192 (7)
H10	0.804447	0.508240	0.229895	0.023*
C13	0.5261 (4)	1.0523 (3)	0.5262 (3)	0.0198 (7)
H13	0.550814	1.119108	0.513922	0.024*
C12	0.6090 (4)	0.9797 (2)	0.4700 (3)	0.0181 (7)
H12	0.690107	0.997915	0.420857	0.022*
C4	0.6528 (3)	0.8037 (2)	0.4184 (3)	0.0151 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br2	0.02329 (14)	0.01841 (15)	0.01781 (15)	0.00139 (12)	0.00313 (15)	−0.00050 (16)
Br1	0.02431 (14)	0.01562 (14)	0.02040 (16)	0.00138 (12)	0.00569 (15)	0.00363 (16)
O1	0.0148 (10)	0.0134 (11)	0.0137 (12)	−0.0002 (9)	0.0005 (8)	−0.0003 (9)
C7	0.0152 (15)	0.0193 (17)	0.0137 (17)	−0.0004 (12)	0.0000 (12)	0.0024 (13)
C16	0.0151 (12)	0.0141 (14)	0.0152 (16)	−0.0002 (11)	−0.0052 (13)	0.0005 (15)
C14	0.0194 (14)	0.0164 (16)	0.0187 (18)	0.0030 (13)	−0.0040 (12)	−0.0025 (13)
C2	0.0166 (15)	0.0212 (17)	0.0130 (17)	0.0010 (12)	−0.0008 (12)	0.0015 (14)
C9	0.0274 (18)	0.0234 (18)	0.0182 (19)	0.0059 (15)	0.0045 (14)	−0.0041 (16)
C8	0.0245 (16)	0.0148 (16)	0.0204 (19)	0.0021 (13)	0.0004 (14)	0.0005 (14)
C5	0.0139 (14)	0.0174 (16)	0.0128 (16)	0.0006 (12)	−0.0031 (12)	−0.0012 (13)
C6	0.0149 (14)	0.0158 (16)	0.0134 (17)	0.0036 (12)	−0.0009 (11)	0.0009 (13)
C15	0.0164 (15)	0.0199 (17)	0.0155 (16)	−0.0018 (13)	−0.0032 (12)	0.0020 (14)
C3	0.0176 (15)	0.0180 (16)	0.0168 (18)	−0.0033 (13)	−0.0027 (12)	0.0034 (13)
C11	0.0142 (14)	0.0162 (16)	0.0156 (17)	0.0004 (12)	−0.0054 (12)	0.0003 (13)
C1	0.0121 (13)	0.0183 (16)	0.0135 (16)	0.0020 (12)	−0.0034 (12)	−0.0002 (13)
C10	0.0224 (16)	0.0192 (17)	0.0159 (17)	0.0023 (14)	0.0042 (13)	0.0023 (14)
C13	0.0222 (16)	0.0125 (16)	0.0246 (18)	−0.0032 (13)	−0.0069 (13)	−0.0001 (13)
C12	0.0169 (15)	0.0175 (17)	0.0200 (18)	−0.0016 (13)	−0.0020 (12)	0.0012 (13)
C4	0.0150 (14)	0.0139 (15)	0.0163 (17)	−0.0013 (12)	−0.0055 (12)	0.0020 (13)

Geometric parameters (Å, º)

Br2—C15	1.904 (3)	C9—C8	1.391 (5)
Br1—C7	1.914 (3)	C9—C10	1.378 (5)
O1—C1	1.379 (4)	C8—H8	0.9300
O1—C4	1.374 (4)	C5—C6	1.402 (4)
C7—C8	1.379 (5)	C5—C1	1.453 (5)
C7—C6	1.385 (4)	C5—C10	1.403 (4)
C16—H16	0.9300	C6—H6	0.9300
C16—C15	1.380 (5)	C3—H3	0.9300
C16—C11	1.406 (5)	C3—C4	1.365 (5)
C14—H14	0.9300	C11—C12	1.399 (5)
C14—C15	1.387 (5)	C11—C4	1.456 (5)
C14—C13	1.393 (5)	C10—H10	0.9300
C2—H2	0.9300	C13—H13	0.9300
C2—C3	1.419 (5)	C13—C12	1.373 (5)
C2—C1	1.357 (4)	C12—H12	0.9300
C9—H9	0.9300
C4—O1—C1	107.1 (2)	C16—C15—Br2	119.1 (2)
C8—C7—Br1	119.3 (2)	C16—C15—C14	122.2 (3)
C8—C7—C6	122.9 (3)	C14—C15—Br2	118.6 (2)
C6—C7—Br1	117.8 (2)	C2—C3—H3	126.6
C15—C16—H16	120.4	C4—C3—C2	106.7 (3)
C15—C16—C11	119.1 (3)	C4—C3—H3	126.6
C11—C16—H16	120.4	C16—C11—C4	121.3 (3)
C15—C14—H14	120.9	C12—C11—C16	118.8 (3)
C15—C14—C13	118.1 (3)	C12—C11—C4	119.8 (3)
C13—C14—H14	120.9	O1—C1—C5	116.6 (3)
C3—C2—H2	126.3	C2—C1—O1	109.4 (3)
C1—C2—H2	126.3	C2—C1—C5	134.0 (3)
C1—C2—C3	107.3 (3)	C9—C10—C5	120.5 (3)
C8—C9—H9	119.4	C9—C10—H10	119.7
C10—C9—H9	119.4	C5—C10—H10	119.7
C10—C9—C8	121.2 (3)	C14—C13—H13	119.6
C7—C8—C9	117.7 (3)	C12—C13—C14	120.8 (3)
C7—C8—H8	121.1	C12—C13—H13	119.6
C9—C8—H8	121.1	C11—C12—H12	119.6
C6—C5—C1	121.1 (3)	C13—C12—C11	120.9 (3)
C6—C5—C10	118.8 (3)	C13—C12—H12	119.6
C10—C5—C1	120.0 (3)	O1—C4—C11	117.3 (3)
C7—C6—C5	118.8 (3)	C3—C4—O1	109.5 (3)
C7—C6—H6	120.6	C3—C4—C11	133.1 (3)
C5—C6—H6	120.6
Br1—C7—C8—C9	−177.6 (2)	C11—C16—C15—Br2	176.6 (2)
Br1—C7—C6—C5	176.3 (2)	C11—C16—C15—C14	−0.8 (5)
C16—C11—C12—C13	−1.5 (5)	C1—O1—C4—C3	−0.4 (3)
C16—C11—C4—O1	−2.1 (4)	C1—O1—C4—C11	176.0 (3)
C16—C11—C4—C3	173.2 (3)	C1—C2—C3—C4	0.2 (3)
C14—C13—C12—C11	0.9 (5)	C1—C5—C6—C7	−176.5 (3)
C2—C3—C4—O1	0.1 (3)	C1—C5—C10—C9	177.4 (3)
C2—C3—C4—C11	−175.5 (3)	C10—C9—C8—C7	1.0 (5)
C8—C7—C6—C5	−1.1 (5)	C10—C5—C6—C7	1.5 (4)
C8—C9—C10—C5	−0.7 (5)	C10—C5—C1—O1	178.2 (3)
C6—C7—C8—C9	−0.1 (5)	C10—C5—C1—C2	−4.7 (5)
C6—C5—C1—O1	−3.8 (4)	C13—C14—C15—Br2	−177.2 (2)
C6—C5—C1—C2	173.3 (3)	C13—C14—C15—C16	0.2 (5)
C6—C5—C10—C9	−0.6 (5)	C12—C11—C4—O1	−178.4 (3)
C15—C16—C11—C12	1.5 (5)	C12—C11—C4—C3	−3.1 (5)
C15—C16—C11—C4	−174.9 (3)	C4—O1—C1—C2	0.5 (3)
C15—C14—C13—C12	−0.2 (5)	C4—O1—C1—C5	178.3 (3)
C3—C2—C1—O1	−0.5 (3)	C4—C11—C12—C13	174.9 (3)
C3—C2—C1—C5	−177.7 (3)

(beta)

Crystal data

C16H10Br2O	Dx = 1.868 Mg m^−3
Mr = 378.06	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 20762 reflections
a = 6.217 (3) Å	θ = 2.9–29.2°
b = 30.110 (8) Å	µ = 6.02 mm^−1
c = 7.180 (3) Å	T = 100 K
V = 1344.1 (9) Å^3	Plate, clear yellow
Z = 4	0.42 × 0.22 × 0.06 mm
F(000) = 736

Data collection

Xcalibur, Atlas diffractometer	1831 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	1505 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
Detector resolution: 10.6249 pixels mm^-1	θmax = 29.5°, θmin = 2.7°
ω scans	h = −8→8
Absorption correction: multi-scan CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −40→41
Tmin = 0.404, Tmax = 1.000	l = −9→9
53049 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0362P)^2 + 3.533P] where P = (Fo^2 + 2Fc^2)/3
S = 1.19	(Δ/σ)max < 0.001
1831 reflections	Δρmax = 0.73 e Å^−3
88 parameters	Δρmin = −0.37 e Å^−3
0 restraints

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.18812 (5)	0.46091 (2)	0.58355 (5)	0.02249 (13)
O1	0.3973 (5)	0.250000	0.4914 (4)	0.0167 (6)
C6	0.5599 (5)	0.41415 (10)	0.4581 (4)	0.0185 (6)
H6	0.621712	0.442743	0.441875	0.022*
C7	0.3532 (5)	0.40937 (10)	0.5292 (4)	0.0179 (6)
C8	0.2595 (5)	0.36816 (10)	0.5580 (4)	0.0174 (6)
H8	0.120765	0.365798	0.612619	0.021*
C3	0.3735 (5)	0.33005 (10)	0.5048 (4)	0.0163 (6)
C4	0.5817 (5)	0.33448 (10)	0.4317 (4)	0.0175 (6)
H4	0.660187	0.308788	0.395891	0.021*
C5	0.6734 (5)	0.37619 (11)	0.4114 (4)	0.0190 (6)
H5	0.815955	0.378738	0.364941	0.023*
C1	0.2729 (5)	0.28667 (10)	0.5270 (4)	0.0174 (6)
C2	0.0717 (5)	0.27360 (10)	0.5815 (4)	0.0185 (6)
H2	−0.045290	0.292425	0.613173	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02405 (19)	0.01690 (18)	0.0265 (2)	0.00374 (11)	0.00224 (13)	0.00014 (12)
O1	0.0159 (14)	0.0169 (14)	0.0173 (15)	0.000	0.0017 (12)	0.000
C6	0.0181 (14)	0.0206 (14)	0.0169 (14)	−0.0034 (12)	−0.0028 (12)	0.0015 (11)
C7	0.0214 (15)	0.0183 (14)	0.0140 (13)	0.0045 (12)	−0.0017 (11)	−0.0014 (11)
C8	0.0187 (14)	0.0211 (15)	0.0125 (14)	0.0005 (12)	−0.0024 (11)	0.0012 (11)
C3	0.0181 (14)	0.0197 (14)	0.0111 (13)	0.0014 (11)	−0.0029 (11)	0.0010 (11)
C4	0.0179 (15)	0.0214 (14)	0.0131 (13)	0.0011 (12)	−0.0019 (12)	−0.0010 (11)
C5	0.0171 (14)	0.0253 (16)	0.0147 (14)	−0.0009 (12)	0.0006 (11)	0.0007 (11)
C1	0.0201 (14)	0.0189 (15)	0.0133 (13)	0.0028 (12)	−0.0023 (11)	−0.0005 (11)
C2	0.0191 (15)	0.0206 (15)	0.0158 (14)	0.0023 (12)	0.0001 (12)	−0.0010 (11)

Geometric parameters (Å, º)

Br1—C7	1.901 (3)	C3—C4	1.403 (4)
O1—C1^i	1.372 (3)	C3—C1	1.457 (4)
O1—C1	1.372 (3)	C4—H4	0.9500
C6—H6	0.9500	C4—C5	1.387 (4)
C6—C7	1.390 (5)	C5—H5	0.9500
C6—C5	1.384 (4)	C1—C2	1.368 (5)
C7—C8	1.386 (4)	C2—C2^i	1.421 (6)
C8—H8	0.9500	C2—H2	0.9500
C8—C3	1.402 (4)
C1^i—O1—C1	107.2 (3)	C3—C4—H4	119.8
C7—C6—H6	120.8	C5—C4—C3	120.3 (3)
C5—C6—H6	120.8	C5—C4—H4	119.8
C5—C6—C7	118.3 (3)	C6—C5—C4	120.8 (3)
C6—C7—Br1	119.3 (2)	C6—C5—H5	119.6
C8—C7—Br1	118.2 (2)	C4—C5—H5	119.6
C8—C7—C6	122.4 (3)	O1—C1—C3	117.3 (3)
C7—C8—H8	120.7	C2—C1—O1	109.7 (3)
C7—C8—C3	118.6 (3)	C2—C1—C3	133.0 (3)
C3—C8—H8	120.7	C1—C2—C2^i	106.72 (18)
C8—C3—C4	119.4 (3)	C1—C2—H2	126.6
C8—C3—C1	119.2 (3)	C2^i—C2—H2	126.6
C4—C3—C1	121.5 (3)
Br1—C7—C8—C3	175.1 (2)	C3—C4—C5—C6	−1.7 (5)
O1—C1—C2—C2^i	0.6 (3)	C3—C1—C2—C2^i	−178.1 (3)
C6—C7—C8—C3	−3.2 (4)	C4—C3—C1—O1	6.4 (4)
C7—C6—C5—C4	1.3 (5)	C4—C3—C1—C2	−174.9 (3)
C7—C8—C3—C4	2.7 (4)	C5—C6—C7—Br1	−177.0 (2)
C7—C8—C3—C1	−177.4 (3)	C5—C6—C7—C8	1.2 (5)
C8—C3—C4—C5	−0.3 (4)	C1^i—O1—C1—C3	178.02 (18)
C8—C3—C1—O1	−173.5 (3)	C1^i—O1—C1—C2	−0.9 (4)
C8—C3—C1—C2	5.2 (5)	C1—C3—C4—C5	179.8 (3)

Symmetry code: (i) x, −y+1/2, z.

2,5-bis(3-bromophenyl)furan (gamma)

Crystal data

C16H10Br2O	Dx = 1.876 Mg m^−3
Mr = 378.06	Melting point: 392 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54184 Å
a = 3.9774 (1) Å	Cell parameters from 9023 reflections
b = 10.7746 (2) Å	θ = 2.9–75.1°
c = 31.2387 (5) Å	µ = 7.57 mm^−1
V = 1338.73 (5) Å^3	T = 100 K
Z = 4	Plate, clear yellowish colourless
F(000) = 736	0.7 × 0.06 × 0.02 mm

Data collection

XtaLAB Synergy R, DW system, HyPix-Arc 150 diffractometer	2726 independent reflections
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source	2648 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.034
Detector resolution: 10.0000 pixels mm^-1	θmax = 75.7°, θmin = 2.8°
ω scans	h = −4→4
Absorption correction: multi-scan CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −12→13
Tmin = 0.645, Tmax = 1.000	l = −39→38
11796 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.031	w = 1/[σ^2(Fo^2) + (0.0463P)^2 + 1.5992P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.082	(Δ/σ)max = 0.002
S = 1.10	Δρmax = 0.58 e Å^−3
2726 reflections	Δρmin = −0.90 e Å^−3
173 parameters	Absolute structure: Refined as an inversion twin.
0 restraints	Absolute structure parameter: 0.18 (4)
Primary atom site location: dual

Special details

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. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.40547 (14)	0.58305 (5)	0.35180 (2)	0.02617 (16)
Br2	0.52513 (14)	0.64283 (6)	0.75686 (2)	0.03021 (17)
O1	0.6268 (9)	0.4849 (3)	0.55605 (10)	0.0186 (7)
C16	0.8179 (13)	0.4008 (4)	0.63847 (15)	0.0183 (10)
H16	0.876490	0.352628	0.614924	0.022*
C1	0.4972 (14)	0.5443 (4)	0.52079 (15)	0.0201 (10)
C6	0.7530 (14)	0.3774 (4)	0.47546 (17)	0.0218 (11)
H6	0.823399	0.336113	0.500033	0.026*
C8	0.7272 (14)	0.3884 (4)	0.39844 (17)	0.0226 (11)
H8	0.778277	0.355654	0.371669	0.027*
C10	0.4683 (13)	0.5495 (4)	0.44161 (14)	0.0194 (10)
H10	0.344385	0.622503	0.443186	0.023*
C12	0.5552 (13)	0.5847 (4)	0.66895 (14)	0.0198 (9)
H12	0.437843	0.658707	0.665650	0.024*
C5	0.5739 (13)	0.4893 (4)	0.47912 (15)	0.0181 (10)
C4	0.5327 (13)	0.5553 (4)	0.59124 (14)	0.0177 (10)
C9	0.5506 (14)	0.4989 (4)	0.40220 (15)	0.0194 (10)
C11	0.6393 (13)	0.5125 (4)	0.63304 (15)	0.0177 (9)
C2	0.3272 (13)	0.6460 (5)	0.53263 (16)	0.0209 (10)
H2	0.214905	0.700540	0.514518	0.025*
C14	0.8240 (14)	0.4347 (5)	0.71538 (16)	0.0237 (11)
H14	0.885656	0.409213	0.742719	0.028*
C13	0.6489 (14)	0.5444 (5)	0.70916 (16)	0.0216 (10)
C15	0.9052 (15)	0.3637 (5)	0.67959 (17)	0.0256 (11)
H15	1.020878	0.289491	0.683314	0.031*
C7	0.8258 (14)	0.3279 (5)	0.43559 (17)	0.0254 (12)
H7	0.942106	0.253227	0.433701	0.031*
C3	0.3500 (13)	0.6554 (5)	0.57795 (16)	0.0210 (10)
H3	0.258637	0.717305	0.595115	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0252 (3)	0.0325 (3)	0.0208 (2)	−0.0013 (2)	−0.0021 (2)	0.0012 (2)
Br2	0.0264 (3)	0.0390 (3)	0.0252 (3)	0.0018 (2)	−0.0012 (2)	−0.0102 (2)
O1	0.0197 (18)	0.0156 (15)	0.0205 (16)	0.0019 (13)	0.0018 (14)	0.0003 (12)
C16	0.015 (2)	0.016 (2)	0.024 (2)	0.0002 (18)	−0.0032 (19)	−0.0020 (18)
C1	0.020 (3)	0.020 (2)	0.021 (2)	−0.005 (2)	−0.002 (2)	0.0070 (17)
C6	0.020 (3)	0.018 (2)	0.028 (3)	−0.0001 (19)	0.000 (2)	0.0035 (19)
C8	0.021 (3)	0.021 (2)	0.026 (2)	−0.0039 (19)	0.002 (2)	−0.0045 (19)
C10	0.017 (3)	0.019 (2)	0.022 (2)	−0.0041 (19)	0.000 (2)	−0.0008 (17)
C12	0.016 (3)	0.019 (2)	0.024 (2)	0.001 (2)	−0.0003 (19)	0.0009 (19)
C5	0.013 (3)	0.017 (2)	0.025 (2)	−0.0033 (18)	−0.0017 (19)	0.0005 (17)
C4	0.016 (3)	0.016 (2)	0.020 (2)	−0.0008 (18)	0.002 (2)	−0.0035 (16)
C9	0.017 (3)	0.019 (2)	0.022 (2)	−0.0044 (19)	−0.0009 (19)	0.0009 (18)
C11	0.013 (2)	0.016 (2)	0.023 (2)	−0.0015 (18)	−0.0020 (19)	0.0016 (17)
C2	0.019 (3)	0.022 (2)	0.021 (2)	−0.001 (2)	0.0000 (19)	0.004 (2)
C14	0.023 (3)	0.026 (3)	0.022 (2)	−0.002 (2)	−0.005 (2)	0.0018 (19)
C13	0.017 (3)	0.024 (2)	0.024 (2)	−0.0029 (19)	0.000 (2)	−0.0030 (19)
C15	0.024 (3)	0.022 (2)	0.031 (3)	0.001 (2)	−0.003 (2)	0.001 (2)
C7	0.020 (3)	0.021 (3)	0.035 (3)	0.001 (2)	0.004 (2)	−0.002 (2)
C3	0.016 (3)	0.021 (2)	0.026 (2)	0.001 (2)	0.001 (2)	−0.001 (2)

Geometric parameters (Å, º)

Br1—C9	1.906 (5)	C10—C5	1.404 (6)
Br2—C13	1.894 (5)	C10—C9	1.386 (6)
O1—C1	1.374 (5)	C12—H12	0.9300
O1—C4	1.387 (5)	C12—C11	1.405 (6)
C16—H16	0.9300	C12—C13	1.380 (7)
C16—C11	1.408 (6)	C4—C11	1.448 (6)
C16—C15	1.389 (7)	C4—C3	1.365 (7)
C1—C5	1.462 (6)	C2—H2	0.9300
C1—C2	1.340 (7)	C2—C3	1.422 (7)
C6—H6	0.9300	C14—H14	0.9300
C6—C5	1.405 (7)	C14—C13	1.386 (7)
C6—C7	1.385 (8)	C14—C15	1.393 (7)
C8—H8	0.9300	C15—H15	0.9300
C8—C9	1.387 (7)	C7—H7	0.9300
C8—C7	1.388 (8)	C3—H3	0.9300
C10—H10	0.9300
C1—O1—C4	106.2 (4)	C8—C9—Br1	119.5 (4)
C11—C16—H16	120.5	C10—C9—Br1	118.4 (4)
C15—C16—H16	120.5	C10—C9—C8	122.2 (5)
C15—C16—C11	118.9 (4)	C16—C11—C4	121.9 (4)
O1—C1—C5	116.5 (4)	C12—C11—C16	119.8 (4)
C2—C1—O1	110.4 (4)	C12—C11—C4	118.3 (4)
C2—C1—C5	133.0 (5)	C1—C2—H2	126.3
C5—C6—H6	119.7	C1—C2—C3	107.5 (5)
C7—C6—H6	119.7	C3—C2—H2	126.3
C7—C6—C5	120.6 (5)	C13—C14—H14	120.9
C9—C8—H8	120.8	C13—C14—C15	118.2 (5)
C9—C8—C7	118.4 (5)	C15—C14—H14	120.9
C7—C8—H8	120.8	C12—C13—Br2	118.1 (4)
C5—C10—H10	120.3	C12—C13—C14	122.1 (5)
C9—C10—H10	120.3	C14—C13—Br2	119.8 (4)
C9—C10—C5	119.3 (5)	C16—C15—C14	121.8 (5)
C11—C12—H12	120.4	C16—C15—H15	119.1
C13—C12—H12	120.4	C14—C15—H15	119.1
C13—C12—C11	119.2 (5)	C6—C7—C8	120.8 (5)
C6—C5—C1	121.7 (4)	C6—C7—H7	119.6
C10—C5—C1	119.6 (4)	C8—C7—H7	119.6
C10—C5—C6	118.7 (4)	C4—C3—C2	106.3 (4)
O1—C4—C11	117.5 (4)	C4—C3—H3	126.9
C3—C4—O1	109.5 (4)	C2—C3—H3	126.9
C3—C4—C11	133.0 (4)
O1—C1—C5—C6	3.8 (7)	C11—C12—C13—Br2	−179.0 (4)
O1—C1—C5—C10	−175.9 (4)	C11—C12—C13—C14	0.0 (8)
O1—C1—C2—C3	0.9 (6)	C11—C4—C3—C2	−179.6 (5)
O1—C4—C11—C16	−3.0 (7)	C2—C1—C5—C6	−178.1 (6)
O1—C4—C11—C12	178.1 (4)	C2—C1—C5—C10	2.2 (9)
O1—C4—C3—C2	0.5 (6)	C13—C12—C11—C16	−0.2 (8)
C1—O1—C4—C11	−179.9 (4)	C13—C12—C11—C4	178.8 (5)
C1—O1—C4—C3	0.0 (5)	C13—C14—C15—C16	0.6 (8)
C1—C2—C3—C4	−0.9 (6)	C15—C16—C11—C12	0.5 (8)
C5—C1—C2—C3	−177.3 (6)	C15—C16—C11—C4	−178.4 (5)
C5—C6—C7—C8	0.8 (8)	C15—C14—C13—Br2	178.8 (4)
C5—C10—C9—Br1	−179.7 (4)	C15—C14—C13—C12	−0.2 (8)
C5—C10—C9—C8	1.8 (8)	C7—C6—C5—C1	−179.3 (5)
C4—O1—C1—C5	177.9 (4)	C7—C6—C5—C10	0.4 (7)
C4—O1—C1—C2	−0.6 (5)	C7—C8—C9—Br1	−179.0 (4)
C9—C8—C7—C6	−0.7 (8)	C7—C8—C9—C10	−0.6 (8)
C9—C10—C5—C1	178.0 (5)	C3—C4—C11—C16	177.1 (5)
C9—C10—C5—C6	−1.7 (7)	C3—C4—C11—C12	−1.8 (9)
C11—C16—C15—C14	−0.7 (8)