Crystal structure of 4-amino-1-(4-methyl-benz-yl)pyridinium bromide.

The title mol-ecular salt, C13H15N2 (+)·Br(-), crystallized with two independent ion pairs (A and B) in the asymmetric unit. In the cations, the planes of the pyridine and benzene rings are inclined to one another by 79.32 (8) and 82.30 (10)° in ion pairs A and B, respectively. In the crystal, the anions and cations are connected by N-H⋯Br hydrogen bonds, forming a centrosymmetric tetra-mer-like unit enclosing an R 8 (4)(16) ring motif. These units are linked via C-H⋯Br hydrogen bonds, forming a three-dimensional network.

Related literature

For the solid-phase synthesis of 1,3,5-tris­ubstituted pyridinium salts, see: Lago et al. (1998 ▶). For a review on quaternary pyridinium salts, see: Madaan & Tyagi (2008 ▶). For anti­microbial properties of quarternary amine derivatives, see: Thorsteinsson et al. (2003 ▶). For the pharmacological activity of 4-amino­pyridine compounds, see: Hansebout & Blight (1996 ▶); Kumar & Rao (2005 ▶). For the anti­microbial activity of 4-am­ino­pyridine compounds, see: Ilangovan et al. (2012 ▶); Sundararaman et al. (2013 ▶). For the crystal structures of related compounds, see: Seethalakshmi et al. (2006 ▶); Sundar et al. (2006a ▶,b ▶,c ▶).

Experimental

Crystal data

C13H15N2 +·Br−

M = 279.18

Orthorhombic,

a = 10.5646 (6) Å

b = 18.7980 (11) Å

c = 26.9782 (16) Å

V = 5357.7 (5) Å3

Z = 16

Mo Kα radiation

μ = 3.05 mm−1

T = 294 K

0.13 × 0.11 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.66, T max = 0.79

59314 measured reflections

6400 independent reflections

4055 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.110

S = 1.01

6400 reflections

307 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814025343/su5023sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814025343/su5023Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814025343/su5023Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814025343/su5023fig1.tif

The mol­ecular structure of the two independent cations and anions of the title mol­ecular salt, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814025343/su5023fig2.tif

A view of the mol­ecular overlay of the two independent cations (cation A blue, cation B red).

Click here for additional data file.

. DOI: 10.1107/S1600536814025343/su5023fig3.tif

A view of the tetra­mer-like unit enclosing an (16) ring motif in the crystal structure of the title salt. The N–H⋯Br hydrogen bonds are shown as dashed lines (see Table 1 for details).

Click here for additional data file.

a . DOI: 10.1107/S1600536814025343/su5023fig4.tif

Crystal packing of the title compound, viewed along the a axis, showing the N–H⋯Br and C-H⋯Br hydrogen bonds as dashed lines (see Table 1 for details; H atoms not involved in these inter­actions have been omitted for clarity).

CCDC reference: 1034948

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H15N2+·Br−	Dx = 1.384 Mg m−3
Mr = 279.18	Melting point: 495 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 10.5646 (6) Å	Cell parameters from 5959 reflections
b = 18.7980 (11) Å	θ = 2.3–24.2°
c = 26.9782 (16) Å	µ = 3.05 mm−1
V = 5357.7 (5) Å3	T = 294 K
Z = 16	Block, yellow
F(000) = 2272	0.13 × 0.11 × 0.09 mm

Bruker SMART CCD area-detector diffractometer	6400 independent reflections
Radiation source: fine focus sealed tube	4055 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
ω scans	θmax = 28.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→13
Tmin = 0.66, Tmax = 0.79	k = −24→24
59314 measured reflections	l = −35→35

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)] = 0.039	Hydrogen site location: mixed
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0541P)2 + 1.4559P] where P = (Fo2 + 2Fc2)/3
6400 reflections	(Δ/σ)max = 0.003
307 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	0.20297 (3)	0.08005 (2)	0.52655 (2)	0.06129 (12)
Br2	0.49073 (3)	0.11126 (2)	0.33059 (2)	0.07094 (13)
N1	0.8934 (2)	0.23701 (13)	0.47182 (8)	0.0526 (6)
N2	0.6590 (3)	0.07346 (18)	0.43327 (13)	0.0690 (8)
N3	−0.0725 (2)	0.02494 (12)	0.31892 (8)	0.0527 (6)
N4	0.2390 (3)	0.07293 (16)	0.40281 (12)	0.0643 (7)
C1	0.8056 (3)	0.24614 (16)	0.43621 (11)	0.0545 (7)
H1	0.7986	0.2902	0.4208	0.065*
C2	0.7276 (3)	0.19293 (15)	0.42224 (10)	0.0512 (7)
H2	0.6685	0.2005	0.3972	0.061*
C3	0.7354 (3)	0.12630 (15)	0.44526 (11)	0.0512 (7)
C4	0.8294 (3)	0.11806 (17)	0.48171 (11)	0.0579 (7)
H4	0.8399	0.0744	0.4974	0.069*
C5	0.9042 (3)	0.17331 (16)	0.49393 (11)	0.0571 (7)
H5	0.9652	0.1672	0.5184	0.069*
C6	0.9791 (3)	0.29613 (17)	0.48495 (13)	0.0663 (9)
H6A	1.0192	0.2859	0.5165	0.080*
H6B	0.9301	0.3394	0.4887	0.080*
C7	1.0797 (3)	0.30778 (15)	0.44639 (11)	0.0564 (7)
C8	1.0930 (3)	0.37270 (18)	0.42366 (14)	0.0748 (10)
H8	1.0377	0.4095	0.4314	0.090*
C9	1.1883 (4)	0.3837 (2)	0.38927 (15)	0.0849 (11)
H9	1.1959	0.4282	0.3744	0.102*
C10	1.2714 (3)	0.3313 (2)	0.37666 (13)	0.0753 (10)
C11	1.2567 (3)	0.26595 (19)	0.39924 (14)	0.0767 (10)
H11	1.3122	0.2292	0.3914	0.092*
C12	1.1617 (3)	0.25412 (17)	0.43303 (13)	0.0684 (9)
H12	1.1527	0.2092	0.4471	0.082*
C13	1.3778 (5)	0.3440 (3)	0.34078 (15)	0.1151 (16)
H13A	1.4552	0.3511	0.3588	0.173*
H13B	1.3598	0.3855	0.3213	0.173*
H13C	1.3866	0.3035	0.3194	0.173*
C14	−0.0710 (3)	0.01177 (16)	0.36826 (10)	0.0579 (7)
H14	−0.1418	−0.0089	0.3828	0.069*
C15	0.0289 (3)	0.02757 (16)	0.39685 (10)	0.0580 (7)
H15	0.0259	0.0183	0.4307	0.070*
C16	0.1381 (3)	0.05795 (14)	0.37614 (10)	0.0503 (7)
C17	0.1351 (3)	0.07113 (16)	0.32494 (10)	0.0579 (7)
H17	0.2052	0.0911	0.3093	0.070*
C18	0.0305 (3)	0.05486 (16)	0.29817 (11)	0.0576 (7)
H18	0.0298	0.0647	0.2644	0.069*
C19	−0.1864 (3)	0.00951 (18)	0.28897 (12)	0.0677 (9)
H19A	−0.1702	0.0227	0.2548	0.081*
H19B	−0.2560	0.0385	0.3009	0.081*
C20	−0.2245 (3)	−0.06752 (17)	0.29092 (11)	0.0585 (8)
C21	−0.3357 (3)	−0.08812 (19)	0.31320 (13)	0.0685 (9)
H21	−0.3878	−0.0542	0.3279	0.082*
C22	−0.3705 (4)	−0.1588 (2)	0.31388 (13)	0.0787 (10)
H22	−0.4461	−0.1716	0.3291	0.094*
C23	−0.2974 (4)	−0.2105 (2)	0.29295 (15)	0.0845 (11)
C24	−0.1864 (4)	−0.1896 (2)	0.27187 (18)	0.1021 (14)
H24	−0.1337	−0.2239	0.2580	0.122*
C25	−0.1498 (4)	−0.1197 (2)	0.27045 (16)	0.0883 (12)
H25	−0.0736	−0.1074	0.2555	0.106*
C26	−0.3374 (5)	−0.2880 (2)	0.29280 (19)	0.1277 (19)
H26A	−0.4078	−0.2944	0.3149	0.192*
H26B	−0.2680	−0.3171	0.3036	0.192*
H26C	−0.3618	−0.3017	0.2599	0.192*
H1N2	0.613 (3)	0.0776 (16)	0.4100 (12)	0.057 (10)*
H1N4	0.305 (3)	0.0899 (17)	0.3877 (13)	0.074 (11)*
H2N4	0.230 (3)	0.0685 (15)	0.4322 (13)	0.055 (9)*
H2N2	0.674 (3)	0.0357 (18)	0.4451 (12)	0.059 (10)*

	U11	U22	U33	U12	U13	U23
Br1	0.0765 (2)	0.05288 (19)	0.05445 (19)	−0.00899 (15)	−0.00301 (14)	0.00835 (13)
Br2	0.0549 (2)	0.1048 (3)	0.05311 (19)	0.00089 (17)	−0.00372 (14)	−0.01363 (17)
N1	0.0399 (12)	0.0587 (15)	0.0591 (14)	0.0007 (11)	−0.0039 (10)	−0.0095 (11)
N2	0.0686 (19)	0.0570 (19)	0.081 (2)	−0.0046 (15)	−0.0201 (17)	0.0050 (16)
N3	0.0518 (13)	0.0577 (14)	0.0486 (13)	0.0059 (11)	0.0006 (11)	0.0076 (11)
N4	0.073 (2)	0.0718 (19)	0.0485 (16)	−0.0098 (15)	0.0005 (15)	−0.0026 (14)
C1	0.0522 (16)	0.0535 (17)	0.0578 (17)	0.0041 (14)	−0.0007 (13)	−0.0003 (13)
C2	0.0463 (15)	0.0568 (17)	0.0506 (15)	0.0048 (13)	−0.0067 (12)	−0.0039 (13)
C3	0.0441 (15)	0.0553 (18)	0.0542 (16)	0.0020 (13)	−0.0001 (12)	−0.0051 (13)
C4	0.0562 (17)	0.0577 (19)	0.0596 (18)	0.0088 (14)	−0.0068 (14)	0.0011 (14)
C5	0.0481 (16)	0.066 (2)	0.0575 (17)	0.0103 (15)	−0.0097 (13)	−0.0048 (15)
C6	0.0542 (18)	0.066 (2)	0.078 (2)	−0.0051 (15)	−0.0061 (15)	−0.0222 (17)
C7	0.0517 (17)	0.0467 (17)	0.0709 (19)	−0.0067 (13)	−0.0070 (14)	−0.0114 (14)
C8	0.072 (2)	0.0532 (19)	0.099 (3)	0.0015 (17)	−0.014 (2)	−0.0066 (18)
C9	0.102 (3)	0.062 (2)	0.090 (3)	−0.025 (2)	−0.012 (2)	0.011 (2)
C10	0.083 (2)	0.072 (2)	0.071 (2)	−0.026 (2)	0.0015 (18)	−0.0113 (18)
C11	0.071 (2)	0.063 (2)	0.096 (3)	−0.0114 (18)	0.0198 (19)	−0.0146 (19)
C12	0.070 (2)	0.0451 (17)	0.090 (2)	−0.0081 (15)	0.0087 (18)	−0.0014 (16)
C13	0.126 (4)	0.122 (4)	0.097 (3)	−0.054 (3)	0.029 (3)	−0.012 (3)
C14	0.0540 (17)	0.0681 (19)	0.0515 (16)	0.0025 (15)	0.0119 (14)	0.0086 (14)
C15	0.070 (2)	0.0645 (19)	0.0397 (14)	0.0002 (15)	0.0102 (14)	0.0036 (13)
C16	0.0550 (17)	0.0477 (16)	0.0481 (16)	0.0051 (13)	0.0061 (13)	−0.0061 (12)
C17	0.0582 (18)	0.067 (2)	0.0490 (16)	−0.0052 (15)	0.0103 (14)	0.0033 (14)
C18	0.0652 (19)	0.0655 (19)	0.0422 (15)	0.0035 (15)	0.0077 (13)	0.0094 (13)
C19	0.0534 (17)	0.083 (2)	0.0666 (19)	0.0043 (16)	−0.0105 (15)	0.0140 (17)
C20	0.0488 (17)	0.072 (2)	0.0544 (17)	0.0084 (14)	−0.0113 (13)	−0.0025 (14)
C21	0.067 (2)	0.074 (2)	0.065 (2)	0.0093 (17)	0.0011 (16)	−0.0046 (17)
C22	0.085 (2)	0.080 (3)	0.071 (2)	−0.011 (2)	−0.0082 (19)	0.0051 (19)
C23	0.098 (3)	0.072 (2)	0.084 (3)	0.006 (2)	−0.045 (2)	−0.005 (2)
C24	0.087 (3)	0.085 (3)	0.134 (4)	0.029 (2)	−0.019 (3)	−0.043 (3)
C25	0.059 (2)	0.103 (3)	0.102 (3)	0.010 (2)	0.001 (2)	−0.028 (2)
C26	0.166 (5)	0.074 (3)	0.143 (4)	−0.007 (3)	−0.074 (4)	−0.017 (3)

N1—C5	1.343 (4)	C11—C12	1.374 (4)
N1—C1	1.346 (3)	C11—H11	0.9300
N1—C6	1.477 (4)	C12—H12	0.9300
N2—C3	1.320 (4)	C13—H13A	0.9600
N2—H1N2	0.80 (3)	C13—H13B	0.9600
N2—H2N2	0.79 (3)	C13—H13C	0.9600
N3—C18	1.347 (4)	C14—C15	1.341 (4)
N3—C14	1.354 (3)	C14—H14	0.9300
N3—C19	1.478 (4)	C15—C16	1.403 (4)
N4—C16	1.316 (4)	C15—H15	0.9300
N4—H1N4	0.87 (3)	C16—C17	1.404 (4)
N4—H2N4	0.80 (3)	C17—C18	1.355 (4)
C1—C2	1.350 (4)	C17—H17	0.9300
C1—H1	0.9300	C18—H18	0.9300
C2—C3	1.400 (4)	C19—C20	1.504 (4)
C2—H2	0.9300	C19—H19A	0.9700
C3—C4	1.406 (4)	C19—H19B	0.9700
C4—C5	1.346 (4)	C20—C21	1.375 (5)
C4—H4	0.9300	C20—C25	1.375 (5)
C5—H5	0.9300	C21—C22	1.378 (5)
C6—C7	1.503 (4)	C21—H21	0.9300
C6—H6A	0.9700	C22—C23	1.363 (5)
C6—H6B	0.9700	C22—H22	0.9300
C7—C8	1.373 (4)	C23—C24	1.361 (6)
C7—C12	1.378 (4)	C23—C26	1.519 (6)
C8—C9	1.385 (5)	C24—C25	1.370 (6)
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.363 (5)	C25—H25	0.9300
C9—H9	0.9300	C26—H26A	0.9600
C10—C11	1.380 (5)	C26—H26B	0.9600
C10—C13	1.503 (5)	C26—H26C	0.9600
C5—N1—C1	119.3 (2)	C10—C13—H13A	109.5
C5—N1—C6	120.8 (2)	C10—C13—H13B	109.5
C1—N1—C6	119.8 (3)	H13A—C13—H13B	109.5
C3—N2—H1N2	119 (2)	C10—C13—H13C	109.5
C3—N2—H2N2	117 (2)	H13A—C13—H13C	109.5
H1N2—N2—H2N2	122 (3)	H13B—C13—H13C	109.5
C18—N3—C14	118.4 (2)	C15—C14—N3	122.3 (3)
C18—N3—C19	120.8 (2)	C15—C14—H14	118.9
C14—N3—C19	120.7 (2)	N3—C14—H14	118.9
C16—N4—H1N4	118 (2)	C14—C15—C16	120.6 (3)
C16—N4—H2N4	115 (2)	C14—C15—H15	119.7
H1N4—N4—H2N4	127 (3)	C16—C15—H15	119.7
N1—C1—C2	121.7 (3)	N4—C16—C15	122.4 (3)
N1—C1—H1	119.2	N4—C16—C17	121.2 (3)
C2—C1—H1	119.2	C15—C16—C17	116.4 (3)
C1—C2—C3	120.2 (3)	C18—C17—C16	120.2 (3)
C1—C2—H2	119.9	C18—C17—H17	119.9
C3—C2—H2	119.9	C16—C17—H17	119.9
N2—C3—C2	121.9 (3)	N3—C18—C17	122.1 (3)
N2—C3—C4	121.4 (3)	N3—C18—H18	118.9
C2—C3—C4	116.8 (3)	C17—C18—H18	118.9
C5—C4—C3	120.1 (3)	N3—C19—C20	112.8 (2)
C5—C4—H4	120.0	N3—C19—H19A	109.0
C3—C4—H4	120.0	C20—C19—H19A	109.0
N1—C5—C4	122.0 (3)	N3—C19—H19B	109.0
N1—C5—H5	119.0	C20—C19—H19B	109.0
C4—C5—H5	119.0	H19A—C19—H19B	107.8
N1—C6—C7	112.2 (2)	C21—C20—C25	117.7 (3)
N1—C6—H6A	109.2	C21—C20—C19	121.0 (3)
C7—C6—H6A	109.2	C25—C20—C19	121.3 (3)
N1—C6—H6B	109.2	C20—C21—C22	120.3 (3)
C7—C6—H6B	109.2	C20—C21—H21	119.8
H6A—C6—H6B	107.9	C22—C21—H21	119.8
C8—C7—C12	118.0 (3)	C23—C22—C21	122.0 (4)
C8—C7—C6	120.7 (3)	C23—C22—H22	119.0
C12—C7—C6	121.3 (3)	C21—C22—H22	119.0
C7—C8—C9	120.5 (3)	C24—C23—C22	117.1 (4)
C7—C8—H8	119.8	C24—C23—C26	121.1 (4)
C9—C8—H8	119.8	C22—C23—C26	121.8 (4)
C10—C9—C8	121.8 (3)	C23—C24—C25	122.1 (4)
C10—C9—H9	119.1	C23—C24—H24	119.0
C8—C9—H9	119.1	C25—C24—H24	119.0
C9—C10—C11	117.5 (3)	C24—C25—C20	120.7 (4)
C9—C10—C13	121.8 (4)	C24—C25—H25	119.6
C11—C10—C13	120.7 (4)	C20—C25—H25	119.6
C12—C11—C10	121.3 (3)	C23—C26—H26A	109.5
C12—C11—H11	119.4	C23—C26—H26B	109.5
C10—C11—H11	119.4	H26A—C26—H26B	109.5
C11—C12—C7	121.0 (3)	C23—C26—H26C	109.5
C11—C12—H12	119.5	H26A—C26—H26C	109.5
C7—C12—H12	119.5	H26B—C26—H26C	109.5
C5—N1—C1—C2	0.3 (4)	C18—N3—C14—C15	0.1 (4)
C6—N1—C1—C2	178.3 (3)	C19—N3—C14—C15	−177.5 (3)
N1—C1—C2—C3	0.8 (4)	N3—C14—C15—C16	−0.9 (5)
C1—C2—C3—N2	178.6 (3)	C14—C15—C16—N4	−178.7 (3)
C1—C2—C3—C4	−1.8 (4)	C14—C15—C16—C17	0.7 (4)
N2—C3—C4—C5	−178.6 (3)	N4—C16—C17—C18	179.6 (3)
C2—C3—C4—C5	1.8 (4)	C15—C16—C17—C18	0.2 (4)
C1—N1—C5—C4	−0.3 (4)	C14—N3—C18—C17	0.9 (4)
C6—N1—C5—C4	−178.2 (3)	C19—N3—C18—C17	178.4 (3)
C3—C4—C5—N1	−0.8 (5)	C16—C17—C18—N3	−1.0 (5)
C5—N1—C6—C7	103.4 (3)	C18—N3—C19—C20	123.3 (3)
C1—N1—C6—C7	−74.6 (3)	C14—N3—C19—C20	−59.2 (4)
N1—C6—C7—C8	122.9 (3)	N3—C19—C20—C21	113.3 (3)
N1—C6—C7—C12	−57.6 (4)	N3—C19—C20—C25	−66.9 (4)
C12—C7—C8—C9	−1.5 (5)	C25—C20—C21—C22	−1.1 (5)
C6—C7—C8—C9	178.0 (3)	C19—C20—C21—C22	178.8 (3)
C7—C8—C9—C10	0.2 (6)	C20—C21—C22—C23	0.1 (5)
C8—C9—C10—C11	0.4 (6)	C21—C22—C23—C24	1.2 (5)
C8—C9—C10—C13	−177.7 (4)	C21—C22—C23—C26	−178.6 (3)
C9—C10—C11—C12	0.2 (5)	C22—C23—C24—C25	−1.5 (6)
C13—C10—C11—C12	178.4 (4)	C26—C23—C24—C25	178.3 (4)
C10—C11—C12—C7	−1.6 (5)	C23—C24—C25—C20	0.5 (7)
C8—C7—C12—C11	2.2 (5)	C21—C20—C25—C24	0.8 (6)
C6—C7—C12—C11	−177.3 (3)	C19—C20—C25—C24	−179.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···Br2	0.80 (3)	2.58 (3)	3.367 (4)	169 (3)
N4—H1N4···Br2	0.87 (3)	2.52 (4)	3.375 (3)	166 (3)
N4—H2N4···Br1	0.80 (3)	2.57 (3)	3.363 (3)	169 (3)
N2—H2N2···Br1i	0.79 (3)	2.65 (3)	3.410 (4)	161 (3)
C6—H6B···Br1ii	0.97	2.87	3.745 (3)	151
C14—H14···Br1iii	0.93	2.86	3.602 (3)	138
C18—H18···Br2iv	0.93	2.74	3.656 (3)	169

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N2H1N2Br2	0.80(3)	2.58(3)	3.367(4)	169(3)
N4H1N4Br2	0.87(3)	2.52(4)	3.375(3)	166(3)
N4H2N4Br1	0.80(3)	2.57(3)	3.363(3)	169(3)
N2H2N2Br1i	0.79(3)	2.65(3)	3.410(4)	161(3)
C6H6BBr1ii	0.97	2.87	3.745(3)	151
C14H14Br1iii	0.93	2.86	3.602(3)	138
C18H18Br2iv	0.93	2.74	3.656(3)	169

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .