Bis-(2-bromo-eth-yl)ammonium bromide.

The title salt, C(4)H(10)Br(2)N(+)·Br(-), crystallizes with four cations and four anions in the asymmetric unit. In the crystal, the bis-(2-bromo-eth-yl)ammonium cations and bromide anions are linked into chains by N-H⋯Br hydrogen bonds describing a binary C(2) (1)(4) motif along [010]. Each of these chains is formed by a unique cation and anion pair. The ammonium cations occur in the less preferred anti conformation, characterized by different NCCBr torsion angles. Adjacent chains are linked by weak C-H⋯Br inter-actions, forming a three-dimensional network. The crystal studied was a pseudo-merohedral twin with twin ratio 0.640 (2):0.360 (2).

Related literature

For structures of related 2-haloethyl­ammonium salts, see: Bojan et al. (2008 ▶); Briggs et al. (2004 ▶); Fischer et al. (1994 ▶); Kane et al. (1992 ▶); Kumar et al. (1998 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶). For the preparation of N-bis­(2-bromo­ethyl­amine) hydro­bromide, see: Pettit et al. (1964) ▶.

Experimental

Crystal data

C4H10Br2N+·Br−

M = 311.86

Monoclinic,

a = 15.8861 (13) Å

b = 7.4891 (6) Å

c = 17.1018 (18) Å

β = 117.450 (5)°

V = 1805.6 (3) Å3

Z = 8

Mo Kα radiation

μ = 13.32 mm−1

T = 173 K

0.59 × 0.08 × 0.02 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: integration [face indexed absorption corrections carried out with XPREP (Bruker, 2005 ▶)] T min = 0.083, T max = 0.552

10233 measured reflections

6819 independent reflections

4058 reflections with I > 2σ(I)

R int = 0.143

Refinement

R[F 2 > 2σ(F 2)] = 0.107

wR(F 2) = 0.285

S = 0.98

6819 reflections

290 parameters

85 restraints

H-atom parameters constrained

Δρmax = 2.13 e Å−3

Δρmin = −2.01 e Å−3

Absolute structure: Flack (1983 ▶), 2573 Friedel pairs

Flack parameter: 0.15 (12)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2 (Bruker, 2005 ▶); data reduction: SAINT-NT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812033417/lr2074sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033417/lr2074Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033417/lr2074Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C4H10Br2N+·Br−	F(000) = 1168
Mr = 311.86	Dx = 2.294 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1740 reflections
a = 15.8861 (13) Å	θ = 2.7–28.0°
b = 7.4891 (6) Å	µ = 13.32 mm−1
c = 17.1018 (18) Å	T = 173 K
β = 117.450 (5)°	Needle, colourless
V = 1805.6 (3) Å3	0.59 × 0.08 × 0.02 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	6819 independent reflections
Radiation source: fine-focus sealed tube	4058 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.143
phi and ω scans	θmax = 27.0°, θmin = 1.3°
Absorption correction: integration [face indexed absorption corrections carried out with XPREP (Bruker, 2005)]	h = −19→20
Tmin = 0.083, Tmax = 0.552	k = −9→9
10233 measured reflections	l = −21→8

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)] = 0.107	H-atom parameters constrained
wR(F2) = 0.285	w = 1/[σ2(Fo2) + (0.1648P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
6819 reflections	Δρmax = 2.13 e Å−3
290 parameters	Δρmin = −2.01 e Å−3
85 restraints	Absolute structure: Flack (1983), 2573 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.15 (12)

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. 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
C1	0.890 (2)	0.595 (5)	0.623 (2)	0.032 (8)
H1C	0.8598	0.4761	0.6060	0.038*
H1D	0.8621	0.6552	0.6580	0.038*
C2	0.868 (2)	0.699 (5)	0.5452 (19)	0.023 (7)
H2C	0.9002	0.8161	0.5628	0.028*
H2D	0.7989	0.7205	0.5133	0.028*
C3	0.842 (3)	0.666 (5)	0.388 (2)	0.032 (8)
H3C	0.7739	0.6447	0.3672	0.038*
H3D	0.8522	0.7949	0.3824	0.038*
C4	0.877 (3)	0.559 (5)	0.334 (2)	0.038 (10)
H4C	0.8756	0.4302	0.3461	0.046*
H4D	0.9425	0.5935	0.3487	0.046*
N1	0.8992 (19)	0.607 (4)	0.4843 (16)	0.024 (6)
H1A	0.8926	0.4855	0.4877	0.029*
H1B	0.9624	0.6305	0.5030	0.029*
Br1	1.0262 (4)	0.5657 (7)	0.6975 (3)	0.0567 (14)
Br2	0.7909 (3)	0.6111 (6)	0.2100 (2)	0.0343 (9)
C5	0.635 (2)	0.016 (4)	0.6613 (18)	0.024 (7)
H5A	0.6675	−0.0672	0.6393	0.028*
H5B	0.5687	−0.0248	0.6399	0.028*
C6	0.636 (2)	0.202 (4)	0.6290 (19)	0.024 (7)
H6A	0.7028	0.2446	0.6549	0.029*
H6B	0.6010	0.2825	0.6493	0.029*
C7	0.649 (3)	0.109 (6)	0.492 (2)	0.041 (9)
H7A	0.7174	0.1302	0.5296	0.049*
H7B	0.6366	−0.0201	0.4924	0.049*
C8	0.623 (2)	0.165 (4)	0.4031 (18)	0.027 (7)
H8A	0.6652	0.1042	0.3834	0.033*
H8B	0.6350	0.2953	0.4036	0.033*
N2	0.5926 (19)	0.211 (4)	0.5289 (15)	0.027 (7)
H2A	0.5321	0.1649	0.5050	0.032*
H2B	0.5880	0.3284	0.5119	0.032*
Br5	0.4962 (3)	0.1204 (6)	0.3201 (2)	0.0408 (9)
Br6	0.7005 (3)	0.0235 (6)	0.7903 (2)	0.0346 (9)
C9	0.273 (2)	0.611 (5)	−0.1351 (19)	0.029 (7)
H9A	0.2123	0.6703	−0.1729	0.034*
H9B	0.2592	0.4882	−0.1235	0.034*
C10	0.321 (2)	0.710 (5)	−0.048 (2)	0.039 (9)
H10A	0.3297	0.8364	−0.0594	0.047*
H10B	0.2788	0.7064	−0.0197	0.047*
C11	0.455 (3)	0.690 (5)	0.106 (2)	0.034 (9)
H11A	0.4765	0.8159	0.1101	0.040*
H11B	0.4065	0.6839	0.1261	0.040*
C12	0.538 (3)	0.574 (6)	0.163 (2)	0.046 (11)
H12A	0.5926	0.5979	0.1510	0.055*
H12B	0.5207	0.4463	0.1507	0.055*
N3	0.4142 (18)	0.629 (4)	0.0114 (15)	0.023 (6)
H3A	0.4564	0.6549	−0.0098	0.028*
H3B	0.4074	0.5064	0.0101	0.028*
Br8	0.5708 (3)	0.6336 (6)	0.2858 (2)	0.0334 (9)
Br9	0.3459 (3)	0.5968 (8)	−0.1998 (3)	0.0546 (13)
C13	0.769 (3)	0.542 (5)	−0.121 (2)	0.037 (9)
H13A	0.7071	0.6012	−0.1541	0.045*
H13B	0.7583	0.4202	−0.1056	0.045*
C14	0.830 (2)	0.647 (5)	−0.037 (2)	0.031 (8)
H14A	0.8405	0.7689	−0.0532	0.037*
H14B	0.7944	0.6584	−0.0024	0.037*
C15	0.966 (3)	0.625 (5)	0.111 (2)	0.035 (8)
H15A	0.9812	0.7533	0.1129	0.042*
H15B	0.9195	0.6104	0.1342	0.042*
C16	1.051 (3)	0.525 (5)	0.165 (2)	0.038 (9)
H16A	1.1015	0.5575	0.1491	0.046*
H16B	1.0382	0.3959	0.1546	0.046*
N4	0.9227 (19)	0.561 (4)	0.0182 (16)	0.026 (6)
H4A	0.9634	0.5856	−0.0051	0.031*
H4B	0.9147	0.4394	0.0172	0.031*
Br11	1.0931 (3)	0.5783 (5)	0.2892 (2)	0.0327 (10)
Br12	0.8319 (3)	0.5275 (7)	−0.1957 (3)	0.0483 (11)
Br3	0.6231 (2)	0.6258 (6)	0.5118 (2)	0.0284 (8)
Br4	0.8830 (2)	0.1738 (4)	0.4877 (2)	0.0282 (9)
Br7	0.3904 (2)	0.1919 (5)	0.0112 (2)	0.0289 (9)
Br10	0.8945 (2)	0.1288 (5)	0.0195 (2)	0.0284 (8)

	U11	U22	U33	U12	U13	U23
C1	0.033 (9)	0.032 (9)	0.032 (9)	0.000 (5)	0.017 (6)	−0.001 (5)
C2	0.024 (8)	0.021 (8)	0.023 (8)	0.003 (5)	0.009 (5)	−0.002 (5)
C3	0.030 (9)	0.033 (10)	0.033 (9)	0.000 (5)	0.015 (6)	0.000 (5)
C4	0.039 (11)	0.038 (11)	0.036 (10)	0.000 (5)	0.017 (6)	0.000 (5)
N1	0.032 (15)	0.014 (13)	0.034 (13)	−0.009 (12)	0.022 (13)	−0.002 (13)
Br1	0.042 (3)	0.070 (4)	0.044 (2)	−0.009 (2)	0.008 (2)	0.005 (2)
Br2	0.0287 (19)	0.041 (2)	0.0319 (18)	0.000 (2)	0.0127 (16)	0.005 (2)
C5	0.025 (8)	0.026 (8)	0.022 (8)	0.000 (5)	0.013 (5)	0.001 (5)
C6	0.024 (8)	0.025 (8)	0.026 (8)	0.001 (5)	0.013 (5)	0.001 (5)
C7	0.042 (10)	0.040 (10)	0.041 (10)	0.001 (5)	0.020 (6)	−0.002 (5)
C8	0.025 (8)	0.029 (9)	0.028 (8)	−0.001 (5)	0.013 (5)	0.000 (5)
N2	0.032 (17)	0.012 (12)	0.019 (12)	−0.006 (12)	−0.003 (12)	−0.003 (11)
Br5	0.034 (2)	0.037 (2)	0.049 (2)	0.004 (2)	0.0167 (18)	−0.005 (2)
Br6	0.032 (2)	0.040 (2)	0.0327 (19)	0.0076 (17)	0.0154 (17)	0.0036 (17)
C9	0.026 (8)	0.027 (8)	0.031 (8)	−0.001 (5)	0.011 (5)	−0.001 (5)
C10	0.012 (17)	0.04 (2)	0.06 (2)	0.003 (16)	0.008 (17)	−0.005 (19)
C11	0.05 (3)	0.017 (15)	0.05 (2)	−0.006 (16)	0.04 (2)	0.001 (16)
C12	0.045 (11)	0.047 (12)	0.045 (11)	0.002 (5)	0.022 (7)	−0.002 (5)
N3	0.023 (7)	0.022 (7)	0.024 (7)	−0.001 (5)	0.011 (5)	−0.002 (5)
Br8	0.0307 (19)	0.037 (2)	0.0353 (18)	−0.0017 (19)	0.0178 (16)	−0.0001 (19)
Br9	0.055 (3)	0.070 (3)	0.039 (2)	−0.010 (3)	0.022 (2)	−0.006 (2)
C13	0.037 (10)	0.037 (10)	0.037 (10)	0.000 (5)	0.016 (6)	0.003 (5)
C14	0.027 (18)	0.022 (18)	0.032 (17)	0.002 (15)	0.003 (15)	−0.011 (15)
C15	0.034 (9)	0.034 (9)	0.035 (9)	0.003 (5)	0.014 (6)	−0.002 (5)
C16	0.036 (10)	0.038 (10)	0.038 (10)	0.004 (5)	0.016 (6)	−0.003 (5)
N4	0.023 (14)	0.032 (16)	0.019 (12)	−0.017 (12)	0.007 (12)	−0.005 (11)
Br11	0.026 (2)	0.041 (2)	0.0324 (19)	−0.0030 (17)	0.0152 (17)	0.0005 (16)
Br12	0.054 (3)	0.054 (3)	0.041 (2)	−0.018 (2)	0.025 (2)	−0.009 (2)
Br3	0.0292 (18)	0.0185 (18)	0.0437 (18)	−0.0031 (16)	0.0221 (15)	−0.0011 (17)
Br4	0.0198 (17)	0.023 (2)	0.047 (2)	0.0011 (13)	0.0193 (16)	0.0033 (15)
Br7	0.0259 (19)	0.0210 (19)	0.046 (2)	−0.0032 (14)	0.0216 (17)	−0.0019 (15)
Br10	0.0318 (19)	0.0171 (17)	0.0480 (19)	−0.0017 (16)	0.0284 (17)	0.0005 (17)

C1—C2	1.44 (5)	C9—C10	1.51 (5)
C1—Br1	1.96 (3)	C9—Br9	1.93 (3)
C1—H1C	0.9900	C9—H9A	0.9900
C1—H1D	0.9900	C9—H9B	0.9900
C2—N1	1.51 (4)	C10—N3	1.49 (4)
C2—H2C	0.9900	C10—H10A	0.9900
C2—H2D	0.9900	C10—H10B	0.9900
C3—C4	1.50 (5)	C11—C12	1.50 (5)
C3—N1	1.53 (4)	C11—N3	1.51 (4)
C3—H3C	0.9900	C11—H11A	0.9900
C3—H3D	0.9900	C11—H11B	0.9900
C4—Br2	1.96 (3)	C12—Br8	1.97 (4)
C4—H4C	0.9900	C12—H12A	0.9900
C4—H4D	0.9900	C12—H12B	0.9900
N1—H1A	0.9200	N3—H3A	0.9200
N1—H1B	0.9200	N3—H3B	0.9200
C5—C6	1.50 (4)	C13—C14	1.53 (5)
C5—Br6	1.96 (3)	C13—Br12	1.94 (4)
C5—H5A	0.9900	C13—H13A	0.9900
C5—H5B	0.9900	C13—H13B	0.9900
C6—N2	1.52 (4)	C14—N4	1.48 (4)
C6—H6A	0.9900	C14—H14A	0.9900
C6—H6B	0.9900	C14—H14B	0.9900
C7—C8	1.44 (5)	C15—C16	1.45 (5)
C7—N2	1.51 (5)	C15—N4	1.49 (4)
C7—H7A	0.9900	C15—H15A	0.9900
C7—H7B	0.9900	C15—H15B	0.9900
C8—Br5	1.89 (3)	C16—Br11	1.95 (3)
C8—H8A	0.9900	C16—H16A	0.9900
C8—H8B	0.9900	C16—H16B	0.9900
N2—H2A	0.9200	N4—H4A	0.9200
N2—H2B	0.9200	N4—H4B	0.9200
C2—C1—Br1	112 (2)	C10—C9—Br9	116 (2)
C2—C1—H1C	109.2	C10—C9—H9A	108.4
Br1—C1—H1C	109.2	Br9—C9—H9A	108.4
C2—C1—H1D	109.2	C10—C9—H9B	108.4
Br1—C1—H1D	109.2	Br9—C9—H9B	108.4
H1C—C1—H1D	107.9	H9A—C9—H9B	107.4
C1—C2—N1	112 (3)	N3—C10—C9	111 (3)
C1—C2—H2C	109.1	N3—C10—H10A	109.4
N1—C2—H2C	109.1	C9—C10—H10A	109.4
C1—C2—H2D	109.1	N3—C10—H10B	109.4
N1—C2—H2D	109.1	C9—C10—H10B	109.4
H2C—C2—H2D	107.8	H10A—C10—H10B	108.0
C4—C3—N1	108 (3)	C12—C11—N3	110 (3)
C4—C3—H3C	110.1	C12—C11—H11A	109.8
N1—C3—H3C	110.1	N3—C11—H11A	109.8
C4—C3—H3D	110.1	C12—C11—H11B	109.8
N1—C3—H3D	110.1	N3—C11—H11B	109.8
H3C—C3—H3D	108.4	H11A—C11—H11B	108.2
C3—C4—Br2	107 (2)	C11—C12—Br8	106 (3)
C3—C4—H4C	110.3	C11—C12—H12A	110.5
Br2—C4—H4C	110.3	Br8—C12—H12A	110.5
C3—C4—H4D	110.3	C11—C12—H12B	110.5
Br2—C4—H4D	110.3	Br8—C12—H12B	110.5
H4C—C4—H4D	108.6	H12A—C12—H12B	108.6
C2—N1—C3	113 (3)	C10—N3—C11	114 (3)
C2—N1—H1A	108.9	C10—N3—H3A	108.7
C3—N1—H1A	108.9	C11—N3—H3A	108.7
C2—N1—H1B	108.9	C10—N3—H3B	108.7
C3—N1—H1B	108.9	C11—N3—H3B	108.7
H1A—N1—H1B	107.8	H3A—N3—H3B	107.6
C6—C5—Br6	107 (2)	C14—C13—Br12	111 (3)
C6—C5—H5A	110.2	C14—C13—H13A	109.4
Br6—C5—H5A	110.2	Br12—C13—H13A	109.4
C6—C5—H5B	110.2	C14—C13—H13B	109.4
Br6—C5—H5B	110.2	Br12—C13—H13B	109.4
H5A—C5—H5B	108.5	H13A—C13—H13B	108.0
C5—C6—N2	112 (3)	N4—C14—C13	113 (3)
C5—C6—H6A	109.2	N4—C14—H14A	109.1
N2—C6—H6A	109.2	C13—C14—H14A	109.1
C5—C6—H6B	109.2	N4—C14—H14B	109.1
N2—C6—H6B	109.2	C13—C14—H14B	109.1
H6A—C6—H6B	107.9	H14A—C14—H14B	107.8
C8—C7—N2	111 (3)	C16—C15—N4	111 (3)
C8—C7—H7A	109.4	C16—C15—H15A	109.5
N2—C7—H7A	109.4	N4—C15—H15A	109.5
C8—C7—H7B	109.4	C16—C15—H15B	109.5
N2—C7—H7B	109.4	N4—C15—H15B	109.5
H7A—C7—H7B	108.0	H15A—C15—H15B	108.1
C7—C8—Br5	115 (2)	C15—C16—Br11	110 (3)
C7—C8—H8A	108.5	C15—C16—H16A	109.6
Br5—C8—H8A	108.5	Br11—C16—H16A	109.6
C7—C8—H8B	108.5	C15—C16—H16B	109.6
Br5—C8—H8B	108.5	Br11—C16—H16B	109.6
H8A—C8—H8B	107.5	H16A—C16—H16B	108.1
C7—N2—C6	113 (3)	C14—N4—C15	112 (3)
C7—N2—H2A	108.9	C14—N4—H4A	109.2
C6—N2—H2A	108.9	C15—N4—H4A	109.2
C7—N2—H2B	108.9	C14—N4—H4B	109.2
C6—N2—H2B	108.9	C15—N4—H4B	109.2
H2A—N2—H2B	107.7	H4A—N4—H4B	107.9
Br1—C1—C2—N1	65 (3)	Br9—C9—C10—N3	−57 (4)
N1—C3—C4—Br2	172 (2)	N3—C11—C12—Br8	−169 (2)
C1—C2—N1—C3	155 (3)	C9—C10—N3—C11	−167 (3)
C4—C3—N1—C2	−177 (3)	C12—C11—N3—C10	168 (3)
Br6—C5—C6—N2	176 (2)	Br12—C13—C14—N4	−62 (3)
N2—C7—C8—Br5	−63 (4)	N4—C15—C16—Br11	−169 (2)
C8—C7—N2—C6	−162 (3)	C13—C14—N4—C15	−160 (3)
C5—C6—N2—C7	−66 (4)	C16—C15—N4—C14	174 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br4	0.92	2.34	3.26 (3)	175
N1—H1B···Br4i	0.92	2.41	3.31 (3)	165
N2—H2B···Br3	0.92	2.30	3.18 (3)	161
N2—H2A···Br3ii	0.92	2.37	3.23 (3)	157
N3—H3B···Br7	0.92	2.37	3.29 (3)	178
N3—H3A···Br7iii	0.92	2.46	3.33 (3)	159
N4—H4B···Br10	0.92	2.35	3.27 (3)	178
N4—H4A···Br10iv	0.92	2.40	3.29 (3)	162
C1—H1D···Br12v	1.00	2.92	3.66 (3)	131
C2—H2C···Br4vi	0.99	2.93	3.73 (4)	138
C2—H2D···Br3	0.99	2.87	3.70 (4)	143
C3—H3C···Br8	0.98	2.87	3.84 (5)	170
C7—H7B···Br3vii	0.99	2.69	3.68 (5)	173
C9—H9A···Br1viii	0.99	2.87	3.65 (3)	137
C10—H10A···Br7vi	0.99	2.90	3.77 (4)	148
C10—H10B···Br10iii	0.99	2.82	3.72 (4)	153
C12—H12A···Br2	1.00	2.83	3.73 (5)	150
C14—H14A···Br10vi	0.99	2.93	3.75 (4)	142
C14—H14B···Br7iii	0.99	2.88	3.74 (4)	145
C15—H15B···Br2	0.99	2.88	3.87 (5)	173
C16—H16A···Br6i	0.99	2.83	3.66 (5)	141

Table 1

Selected torsion angles (°)

Br1—C1—C2—N1	65 (3)
N1—C3—C4—Br2	172 (2)
Br6—C5—C6—N2	176 (2)
N2—C7—C8—Br5	−63 (4)
Br9—C9—C10—N3	−57 (4)
N3—C11—C12—Br8	−169 (2)
Br12—C13—C14—N4	−62 (3)
N4—C15—C16—Br11	−169 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Br4	0.92	2.34	3.26 (3)	175
N1—H1B⋯Br4i	0.92	2.41	3.31 (3)	165
N2—H2B⋯Br3	0.92	2.30	3.18 (3)	161
N2—H2A⋯Br3ii	0.92	2.37	3.23 (3)	157
N3—H3B⋯Br7	0.92	2.37	3.29 (3)	178
N3—H3A⋯Br7iii	0.92	2.46	3.33 (3)	159
N4—H4B⋯Br10	0.92	2.35	3.27 (3)	178
N4—H4A⋯Br10iv	0.92	2.40	3.29 (3)	162
C1—H1D⋯Br12v	1.00	2.92	3.66 (3)	131
C2—H2C⋯Br4vi	0.99	2.93	3.73 (4)	138
C2—H2D⋯Br3	0.99	2.87	3.70 (4)	143
C3—H3C⋯Br8	0.98	2.87	3.84 (5)	170
C7—H7B⋯Br3vii	0.99	2.69	3.68 (5)	173
C9—H9A⋯Br1viii	0.99	2.87	3.65 (3)	137
C10—H10A⋯Br7vi	0.99	2.90	3.77 (4)	148
C10—H10B⋯Br10iii	0.99	2.82	3.72 (4)	153
C12—H12A⋯Br2	1.00	2.83	3.73 (5)	150
C14—H14A⋯Br10vi	0.99	2.93	3.75 (4)	142
C14—H14B⋯Br7iii	0.99	2.88	3.74 (4)	145
C15—H15B⋯Br2	0.99	2.88	3.87 (5)	173
C16—H16A⋯Br6i	0.99	2.83	3.66 (5)	141

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .