2,5-Bis(bromo­meth­yl)biphen­yl

Kuś, P.; Zemanek, A.; Jones, P.G.

doi:10.1107/S1600536809018066

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1327

doi:10.1107/S1600536809018066

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2,5-Bis(bromomethyl)biphenyl

Piotr Kuś,^a Aleksander Zemanek ^a and Peter G. Jones ^b ^*

^aDepartment of Chemistry, University of Silesia, 9 Szkolna Street, 40-006 Katowice, Poland, and ^bInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Postfach 3329, 38023 Braunschweig, Germany
^*Correspondence e-mail: p.jones@tu-bs.de

(Received 12 May 2009; accepted 13 May 2009; online 20 May 2009)

In the title compound, C₁₄H₁₂Br₂, the Br atoms lie on opposite sides of their ring plane. The biphenyl interplanar angle is 53.52 (8)°. The packing is characterized by several H⋯Br contacts to each Br atom, but at long distances of 3.07–3.43 Å.

Related literature

For the structures of bromomethyl-substituted aromatic ring systems, see: Jones & Kuś (2005 , 2007 ); Jones et al. (2007 ). For the synthesis, see: Czuchajowski & Zemanek (1990 ); For a related structure with a similar conformation, see: Obrey et al. (2002 ). For the phenomenon of tertiary contacts, see: Du Mont et al. (2008 );

Experimental

Crystal data

C₁₄H₁₂Br₂
M_r = 340.06
Monoclinic, C 2/c
a = 33.084 (4) Å
b = 4.3354 (6) Å
c = 18.017 (2) Å
β = 103.702 (4)°
V = 2510.7 (5) Å³
Z = 8
Mo Kα radiation
μ = 6.43 mm⁻¹
T = 133 K
0.25 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.316, T_max = 0.566 (expected range = 0.294–0.526)
18269 measured reflections
3120 independent reflections
2518 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.085
S = 1.05
3120 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 1.00 e Å⁻³
Δρ_min = −1.00 e Å⁻³

Table 1
H⋯Br contacts (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯Br1ⁱ	0.99	3.23	3.773 (3)	116
C12—H12⋯Br1ⁱⁱ	0.95	3.07	3.782 (3)	133
C13—H13⋯Br1ⁱⁱ	0.95	3.37	3.931 (3)	120
C13—H13⋯Br1ⁱⁱⁱ	0.95	3.24	3.634 (3)	107
C14—H14⋯Br1^iv	0.95	3.37	3.971 (3)	123
C14—H14⋯Br1^v	0.95	3.43	4.326 (3)	157
C4—H4⋯Br2^vi	0.95	3.37	4.260 (3)	156
C4—H4⋯Br2^vii	0.95	3.26	3.845 (3)	122
C6—H6⋯Br2^viii	0.95	3.20	4.124 (3)	166
C8—H8B⋯Br2^ix	0.99	3.29	3.746 (3)	110
C8—H8A⋯Br2^ix	0.99	3.43	3.746 (3)	101
C15—H15⋯Br2^x	0.95	3.27	3.913 (3)	127
C16—H16⋯Br2^viii	0.95	3.41	3.918 (3)	116
C16—H16⋯Br2^x	0.95	3.24	3.898 (3)	128
Symmetry codes: (i) x, y+1, z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x, -y+1, z+{\script{1\over 2}}]$ ; (v) $[x, -y+2, z+{\script{1\over 2}}]$ ; (vi) -x, -y, -z; (vii) -x, -y+1, -z; (viii) $[-x, y, -z+{\script{1\over 2}}]$ ; (ix) x, y-1, z; (x) $[-x, y+1, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018066/bt2951sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809018066/bt2951Isup2.hkl

checkCIF report

Comment top

We are interested in the structures of bromomethyl-substituted aromatic ring systems, compounds that are often used as synthestic intermediates; e.g. various bromomethylbenzenes (Jones & Kuś, 2007), 2,2"- and 2',5'- bis(bromomethyl)-p-terphenyl (Jones & Kuś, 2005; Jones et al., 2007). The packing patterns are often characterized by secondary interactions such as C—H···Br, Br···Br and C—H···π.

As a part of the synthesis of phenyl derivatives of [2.2]paracyclophane (Czuchajowski & Zemanek 1990), 2,5-di(bromomethyl)biphenyl (1) was obtained by bromination of 2,5-dimethylbiphenyl. Here we present its structure (Fig. 1).

Bond lengths and angles may be regarded as normal (e.g. the single bond between the rings is 1.486 (4) Å; ring angles at the substituted atoms C1, C2, C5 are all about 1° less than the ideal 120°). The interplanar angle is 53.52 (8)°. The bromomethyl groups adopt an anti-conformation whereby Br1 and Br2 lie out of their ring plane by 1.680 (4) and -1.736 (4) Å; associated torsion angles are C3—C2—C7—Br1 - 77.2 (3) and C4—C5—C8—Br2 - 87.9 (3)°. A similar conformation was observed in 2,6-di(bromomethyl)biphenyl (Obrey et al., 2002), whereas 2',5'-di(bromomethyl)-p-terphenyl adopts a syn-conformation (Jones et al. 2007).

The packing (Fig. 2) appears at first sight to be characterized by an almost total lack of secondary contacts. The shortest H···Br contact is H12···Br1 3.07 Å (operator 0.5 - x,-1/2 + y,0.5 - z) and there are no other H···Br < 3.19 Å; there are no Br···Br contacts < 4.2 Å and no H···π contacts < 2.95 Å (and these with very narrow angles). Both bromine atoms however are situated in a pocket surrounded by several H atoms; Br1 by six H at distances of 3.07–3.43, Br2 by eight H from 3.20–3.43 Å. This corresponds to the phenomenon of tertiary contacts as postulated by Du Mont et al. (2008).

Related literature top

For the structures of bromomethyl-substituted aromatic ring systems, see: Jones & Kuś (2005, 2007); Jones et al. (2007). For the synthesis, see: Czuchajowski & Zemanek (1990); For a related structure with a similar conformation, see: Obrey et al. (2002). For the phenomenon of tertiary contacts, see: Du Mont et al. (2008);

Experimental top

The title compound was obtained from 2,5-dimethylbiphenyl according to the method of Czuchajowski & Zemanek (1990). The analytical and spectroscopic data are consistent with the literature. Single crystals were grown by slow evaporation of a hexane solution. NMR data for (1): ¹H NMR (CDCl₃, 400 MHz): δ 7.52 (d, 1H), 7.50–7.39 (m, 6H), 7.29 (d, 1H), 4.50 (s, 2H), 4.44(s, 2H); ¹³C NMR (100 MHz): δ 142.54, 139.57, 138.07, 135.46, 131.53, 131.03, 128.94, 128.61, 128.44, 127.77, 32.75, 31.58.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The title compound in the crystal. Displacement ellipsoids represent 50% probability levels.
	Fig. 2. Packing diagram of the title compound viewed parallel to the short b axis.

2,5-Bis(bromomethyl)biphenyl top

Crystal data top

C₁₄H₁₂Br₂	F(000) = 1328
M_r = 340.06	D_x = 1.799 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 33.084 (4) Å	Cell parameters from 6730 reflections
b = 4.3354 (6) Å	θ = 2.3–28.8°
c = 18.017 (2) Å	µ = 6.43 mm⁻¹
β = 103.702 (4)°	T = 133 K
V = 2510.7 (5) Å³	Prism, colourless
Z = 8	0.25 × 0.10 × 0.10 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3120 independent reflections
Radiation source: fine-focus sealed tube	2518 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 8.192 pixels mm^-1	θ_max = 28.3°, θ_min = 1.3°
ϕ and ω scans	h = −44→44
Absorption correction: multi-scan (SADABS; Bruker, 1998)	k = −5→5
T_min = 0.316, T_max = 0.566	l = −24→24
18269 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0515P)² + 1.9201P] where P = (F_o² + 2F_c²)/3
3120 reflections	(Δ/σ)_max = 0.001
145 parameters	Δρ_max = 1.00 e Å⁻³
0 restraints	Δρ_min = −1.00 e Å⁻³

Crystal data top

C₁₄H₁₂Br₂	V = 2510.7 (5) Å³
M_r = 340.06	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 33.084 (4) Å	µ = 6.43 mm⁻¹
b = 4.3354 (6) Å	T = 133 K
c = 18.017 (2) Å	0.25 × 0.10 × 0.10 mm
β = 103.702 (4)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3120 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2518 reflections with I > 2σ(I)
T_min = 0.316, T_max = 0.566	R_int = 0.040
18269 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.05	Δρ_max = 1.00 e Å⁻³
3120 reflections	Δρ_min = −1.00 e Å⁻³
145 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
Br1	0.219743 (8)	0.60712 (7)	0.152339 (16)	0.02600 (10)
Br2	−0.025878 (8)	0.25836 (8)	0.108852 (19)	0.03229 (11)
C1	0.11964 (8)	0.5306 (6)	0.22477 (14)	0.0176 (5)
C2	0.13425 (8)	0.6193 (6)	0.16080 (15)	0.0179 (5)
C3	0.11266 (8)	0.5205 (7)	0.08827 (15)	0.0209 (5)
H3	0.1219	0.5856	0.0447	0.025*
C4	0.07831 (9)	0.3310 (7)	0.07839 (17)	0.0244 (6)
H4	0.0647	0.2621	0.0287	0.029*
C5	0.06355 (8)	0.2407 (6)	0.14127 (17)	0.0222 (6)
C6	0.08387 (8)	0.3445 (7)	0.21324 (16)	0.0209 (6)
H6	0.0733	0.2883	0.2560	0.025*
C7	0.17006 (8)	0.8325 (7)	0.16619 (16)	0.0211 (6)
H7A	0.1765	0.9347	0.2168	0.025*
H7B	0.1625	0.9942	0.1265	0.025*
C8	0.02710 (8)	0.0280 (7)	0.13151 (19)	0.0304 (7)
H8A	0.0294	−0.0937	0.1788	0.037*
H8B	0.0273	−0.1176	0.0893	0.037*
C11	0.14006 (8)	0.6257 (7)	0.30405 (14)	0.0187 (5)
C12	0.18247 (9)	0.5758 (7)	0.33539 (16)	0.0247 (6)
H12	0.1989	0.4783	0.3056	0.030*
C13	0.20058 (9)	0.6669 (8)	0.40922 (17)	0.0300 (7)
H13	0.2293	0.6288	0.4300	0.036*
C14	0.17707 (10)	0.8145 (8)	0.45354 (17)	0.0306 (7)
H14	0.1898	0.8822	0.5038	0.037*
C15	0.13489 (9)	0.8614 (8)	0.42342 (16)	0.0279 (7)
H15	0.1186	0.9615	0.4532	0.033*
C16	0.11642 (9)	0.7626 (7)	0.34998 (16)	0.0225 (6)
H16	0.0873	0.7883	0.3306	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01373 (14)	0.03068 (18)	0.03439 (16)	−0.00368 (11)	0.00730 (10)	−0.00446 (13)
Br2	0.01203 (15)	0.0309 (2)	0.0514 (2)	−0.00186 (11)	0.00244 (12)	0.00305 (14)
C1	0.0114 (11)	0.0171 (13)	0.0231 (12)	0.0036 (10)	0.0018 (9)	0.0018 (11)
C2	0.0130 (11)	0.0162 (13)	0.0236 (12)	0.0016 (10)	0.0027 (9)	0.0000 (11)
C3	0.0177 (12)	0.0208 (14)	0.0234 (12)	0.0028 (11)	0.0036 (10)	0.0026 (11)
C4	0.0165 (13)	0.0260 (15)	0.0273 (14)	0.0032 (11)	−0.0013 (10)	−0.0023 (12)
C5	0.0120 (12)	0.0158 (14)	0.0371 (15)	0.0029 (10)	0.0025 (11)	−0.0001 (12)
C6	0.0135 (12)	0.0208 (14)	0.0278 (13)	0.0025 (10)	0.0033 (10)	0.0051 (11)
C7	0.0174 (13)	0.0201 (14)	0.0264 (13)	0.0016 (11)	0.0064 (10)	0.0013 (11)
C8	0.0137 (13)	0.0213 (15)	0.0528 (19)	0.0011 (12)	0.0009 (12)	0.0013 (14)
C11	0.0139 (12)	0.0221 (14)	0.0194 (12)	0.0007 (10)	0.0027 (9)	0.0045 (11)
C12	0.0162 (13)	0.0326 (17)	0.0252 (13)	0.0037 (12)	0.0049 (10)	−0.0003 (12)
C13	0.0156 (13)	0.045 (2)	0.0266 (14)	0.0033 (13)	−0.0003 (11)	0.0033 (14)
C14	0.0276 (16)	0.0415 (19)	0.0209 (13)	−0.0006 (14)	0.0018 (11)	0.0002 (13)
C15	0.0260 (15)	0.0366 (18)	0.0233 (13)	0.0043 (13)	0.0104 (11)	0.0026 (13)
C16	0.0174 (13)	0.0252 (16)	0.0254 (13)	0.0055 (11)	0.0059 (10)	0.0057 (12)

Geometric parameters (Å, º) top

Br1—C7	1.978 (3)	C14—C15	1.387 (4)
Br2—C8	1.974 (3)	C15—C16	1.387 (4)
C1—C2	1.405 (4)	C3—H3	0.9500
C1—C6	1.407 (4)	C4—H4	0.9500
C1—C11	1.486 (4)	C6—H6	0.9500
C2—C3	1.400 (4)	C7—H7A	0.9900
C2—C7	1.487 (4)	C7—H7B	0.9900
C3—C4	1.379 (4)	C8—H8A	0.9900
C4—C5	1.392 (4)	C8—H8B	0.9900
C5—C6	1.387 (4)	C12—H12	0.9500
C5—C8	1.495 (4)	C13—H13	0.9500
C11—C16	1.398 (4)	C14—H14	0.9500
C11—C12	1.400 (4)	C15—H15	0.9500
C12—C13	1.381 (4)	C16—H16	0.9500
C13—C14	1.395 (4)

C2—C1—C6	118.5 (2)	C3—C4—H4	120.0
C2—C1—C11	123.1 (2)	C5—C4—H4	120.0
C6—C1—C11	118.4 (2)	C5—C6—H6	119.0
C3—C2—C1	118.9 (2)	C1—C6—H6	119.0
C3—C2—C7	118.3 (2)	C2—C7—H7A	109.4
C1—C2—C7	122.7 (2)	Br1—C7—H7A	109.4
C4—C3—C2	121.7 (3)	C2—C7—H7B	109.4
C3—C4—C5	120.0 (3)	Br1—C7—H7B	109.4
C6—C5—C4	119.0 (3)	H7A—C7—H7B	108.0
C6—C5—C8	120.6 (3)	C5—C8—H8A	109.4
C4—C5—C8	120.4 (3)	Br2—C8—H8A	109.4
C5—C6—C1	121.9 (3)	C5—C8—H8B	109.4
C2—C7—Br1	111.0 (2)	Br2—C8—H8B	109.4
C5—C8—Br2	111.4 (2)	H8A—C8—H8B	108.0
C16—C11—C12	118.3 (3)	C13—C12—H12	119.7
C16—C11—C1	119.7 (2)	C11—C12—H12	119.7
C12—C11—C1	121.9 (2)	C12—C13—H13	119.7
C13—C12—C11	120.6 (3)	C14—C13—H13	119.7
C12—C13—C14	120.6 (3)	C15—C14—H14	120.4
C15—C14—C13	119.3 (3)	C13—C14—H14	120.4
C14—C15—C16	120.2 (3)	C14—C15—H15	119.9
C15—C16—C11	120.9 (3)	C16—C15—H15	119.9
C4—C3—H3	119.1	C15—C16—H16	119.5
C2—C3—H3	119.1	C11—C16—H16	119.5

C6—C1—C2—C3	0.2 (4)	C6—C5—C8—Br2	93.8 (3)
C11—C1—C2—C3	−179.4 (3)	C4—C5—C8—Br2	−87.9 (3)
C6—C1—C2—C7	175.8 (3)	C2—C1—C11—C16	128.0 (3)
C11—C1—C2—C7	−3.8 (4)	C6—C1—C11—C16	−51.6 (4)
C1—C2—C3—C4	−2.1 (4)	C2—C1—C11—C12	−53.6 (4)
C7—C2—C3—C4	−177.8 (3)	C6—C1—C11—C12	126.8 (3)
C2—C3—C4—C5	1.9 (4)	C16—C11—C12—C13	−1.6 (4)
C3—C4—C5—C6	0.1 (4)	C1—C11—C12—C13	179.9 (3)
C3—C4—C5—C8	−178.2 (3)	C11—C12—C13—C14	−1.0 (5)
C4—C5—C6—C1	−1.9 (4)	C12—C13—C14—C15	1.8 (5)
C8—C5—C6—C1	176.3 (3)	C13—C14—C15—C16	−0.1 (5)
C2—C1—C6—C5	1.8 (4)	C14—C15—C16—C11	−2.5 (5)
C11—C1—C6—C5	−178.6 (3)	C12—C11—C16—C15	3.3 (4)
C3—C2—C7—Br1	−77.2 (3)	C1—C11—C16—C15	−178.2 (3)
C1—C2—C7—Br1	107.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···Br1ⁱ	0.99	3.23	3.773 (3)	116
C12—H12···Br1ⁱⁱ	0.95	3.07	3.782 (3)	133
C13—H13···Br1ⁱⁱ	0.95	3.37	3.931 (3)	120
C13—H13···Br1ⁱⁱⁱ	0.95	3.24	3.634 (3)	107
C14—H14···Br1^iv	0.95	3.37	3.971 (3)	123
C14—H14···Br1^v	0.95	3.43	4.326 (3)	157
C4—H4···Br2^vi	0.95	3.37	4.260 (3)	156
C4—H4···Br2^vii	0.95	3.26	3.845 (3)	122
C6—H6···Br2^viii	0.95	3.20	4.124 (3)	166
C8—H8B···Br2^ix	0.99	3.29	3.746 (3)	110
C8—H8A···Br2^ix	0.99	3.43	3.746 (3)	101
C15—H15···Br2^x	0.95	3.27	3.913 (3)	127
C16—H16···Br2^viii	0.95	3.41	3.918 (3)	116
C16—H16···Br2^x	0.95	3.24	3.898 (3)	128

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂Br₂
M_r	340.06
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	133
a, b, c (Å)	33.084 (4), 4.3354 (6), 18.017 (2)
β (°)	103.702 (4)
V (Å³)	2510.7 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	6.43
Crystal size (mm)	0.25 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.316, 0.566
No. of measured, independent and observed [I > 2σ(I)] reflections	18269, 3120, 2518
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.085, 1.05
No. of reflections	3120
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.00, −1.00

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Siemens, 1994).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···Br1ⁱ	0.99	3.23	3.773 (3)	116.1
C12—H12···Br1ⁱⁱ	0.95	3.07	3.782 (3)	132.8
C13—H13···Br1ⁱⁱ	0.95	3.37	3.931 (3)	120.1
C13—H13···Br1ⁱⁱⁱ	0.95	3.24	3.634 (3)	106.7
C14—H14···Br1^iv	0.95	3.37	3.971 (3)	122.8
C14—H14···Br1^v	0.95	3.43	4.326 (3)	157.3
C4—H4···Br2^vi	0.95	3.37	4.260 (3)	156.3
C4—H4···Br2^vii	0.95	3.26	3.845 (3)	122.0
C6—H6···Br2^viii	0.95	3.20	4.124 (3)	165.8
C8—H8B···Br2^ix	0.99	3.29	3.746 (3)	109.9
C8—H8A···Br2^ix	0.99	3.43	3.746 (3)	101.2
C15—H15···Br2^x	0.95	3.27	3.913 (3)	126.8
C16—H16···Br2^viii	0.95	3.41	3.918 (3)	115.6
C16—H16···Br2^x	0.95	3.24	3.898 (3)	127.7

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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