2-Amino-5-bromo-pyridinium 2-carb-oxy-benzoate.

The asymmetric unit of the title compound, C(5)H(6)BrN(2) (+)·C(8)H(5)O(4) (-), consists of two crystallographically independent 2-amino-5-bromo-pyridinium cations (A and B) and two 2-carb-oxy-benzoate anions (A and B). Each 2-amino-5-bromo-pyridinium cation is approximately planar, with a maximum deviation of 0.047 (1) Å in cation A and 0.027 (1) Å in cation B. The 2-amino-5-bromo-pyridinium unit in cation A is inclined at dihedral angles of 4.9 (3) and 2.2 (3)° with the phenyl rings of the A and B 2-carb-oxy-benzoate anions, respectively. The corresponding angles for cation B are 3.0 (3) and 5.6 (3)°. The mol-ecular structure is stabilized by an intra-molecular O-H⋯O hydrogen bond,which generates an S(7) ring motif. The cations and anions are linked via inter-molecular N-H⋯O and C-H⋯O hydrogen bonds, generating R(2) (2)(8) ring motifs. In the crystal packing, mol-ecules are linked into wave-like chains along [001] via adjacent ring motifs. Short inter-molecular distances between the phenyl and pyridine rings [3.613 (4) and 3.641 (4) Å] indicate the existence of π-π inter-actions. The crystal structure is a non-merohedral twin with a contribution of 0.271 (3) of the minor component.

Related literature

For applications of phthalic acid, see: Dale et al. (2004 ▶); Ballabh et al. (2005 ▶). For related structures, see: Schuckmann et al. (1978 ▶); Küppers (1978 ▶); Jessen & Küppers (1991 ▶); Quah et al. (2008 ▶, 2010a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C5H6BrN2 +·C8H5O4 −

M = 339.15

Triclinic,

a = 9.0192 (4) Å

b = 10.2689 (5) Å

c = 14.4092 (6) Å

α = 82.269 (2)°

β = 83.969 (2)°

γ = 87.845 (2)°

V = 1314.72 (10) Å3

Z = 4

Mo Kα radiation

μ = 3.14 mm−1

T = 100 K

0.24 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.526, T max = 0.740

7631 measured reflections

7631 independent reflections

5583 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.194

S = 1.09

7631 reflections

364 parameters

H-atom parameters constrained

Δρmax = 1.14 e Å−3

Δρmin = −1.25 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030977/bt5311sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030977/bt5311Isup2.hkl

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

C5H6BrN2+·C8H5O4−	Z = 4
Mr = 339.15	F(000) = 680
Triclinic, P1	Dx = 1.713 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0192 (4) Å	Cell parameters from 9951 reflections
b = 10.2689 (5) Å	θ = 2.3–27.7°
c = 14.4092 (6) Å	µ = 3.14 mm−1
α = 82.269 (2)°	T = 100 K
β = 83.969 (2)°	Block, colourless
γ = 87.845 (2)°	0.24 × 0.20 × 0.10 mm
V = 1314.72 (10) Å3

Bruker SMART APEXII CCD area-detector diffractometer	7631 independent reflections
Radiation source: fine-focus sealed tube	5583 reflections with I > 2σ(I)
graphite	Rint = 0.000
φ and ω scans	θmax = 30.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.526, Tmax = 0.740	k = −14→14
7631 measured reflections	l = −6→20

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0079P)2 + 15.1445P] where P = (Fo2 + 2Fc2)/3
7631 reflections	(Δ/σ)max < 0.001
364 parameters	Δρmax = 1.14 e Å−3
0 restraints	Δρmin = −1.25 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
Br1A	0.79304 (8)	0.52547 (8)	0.47978 (5)	0.03121 (19)
N1A	0.6074 (6)	0.6549 (5)	0.7230 (4)	0.0196 (10)
H1N1	0.6339	0.6324	0.7790	0.023*
N2A	0.3893 (6)	0.7645 (6)	0.7726 (4)	0.0236 (11)
H2NA	0.2872	0.7862	0.7731	0.02 (2)*
H3NA	0.4231	0.7281	0.8335	0.03 (2)*
C1A	0.7009 (7)	0.6012 (7)	0.6581 (4)	0.0223 (13)
H1AA	0.7894	0.5596	0.6749	0.027*
C2A	0.6649 (7)	0.6083 (7)	0.5678 (4)	0.0223 (13)
C3A	0.5324 (7)	0.6715 (7)	0.5428 (4)	0.0243 (13)
H3AA	0.5077	0.6766	0.4813	0.029*
C4A	0.4383 (8)	0.7262 (7)	0.6095 (4)	0.0244 (13)
H4AA	0.3505	0.7696	0.5932	0.029*
C5A	0.4765 (7)	0.7158 (6)	0.7033 (4)	0.0206 (12)
H2O3	1.0538	0.7571	0.5815	0.031*
Br1B	0.69848 (8)	0.98559 (8)	0.01879 (5)	0.03200 (19)
N1B	0.8885 (6)	0.8524 (6)	0.2596 (4)	0.0221 (11)
H2N1	0.8515	0.8432	0.3223	0.027*
N2B	1.0992 (7)	0.7300 (6)	0.2998 (4)	0.0261 (12)
H3N2	1.2048	0.7046	0.2816	0.031*
H4N2	1.0882	0.7577	0.3502	0.031*
C1B	0.7963 (7)	0.9101 (7)	0.1972 (4)	0.0222 (13)
H1BA	0.7119	0.9571	0.2180	0.027*
C2B	0.8265 (7)	0.8995 (7)	0.1045 (4)	0.0229 (13)
C3B	0.9539 (8)	0.8290 (7)	0.0737 (5)	0.0257 (14)
H3BA	0.9755	0.8216	0.0101	0.031*
C4B	1.0461 (8)	0.7713 (7)	0.1368 (4)	0.0245 (13)
H4BA	1.1305	0.7237	0.1168	0.029*
C5B	1.0122 (7)	0.7843 (7)	0.2339 (4)	0.0222 (13)
O1B	0.7873 (6)	0.9253 (6)	0.4244 (3)	0.0348 (13)
O2B	0.9788 (5)	0.8164 (5)	0.4822 (3)	0.0255 (10)
O3B	1.0802 (6)	0.7552 (5)	0.6291 (3)	0.0301 (11)
O4B	1.0764 (6)	0.8386 (5)	0.7617 (3)	0.0291 (11)
C10B	0.8034 (7)	0.9257 (6)	0.5868 (4)	0.0195 (12)
C6B	0.7961 (8)	0.9415 (7)	0.7535 (4)	0.0232 (13)
H6BA	0.8386	0.9233	0.8101	0.028*
C7B	0.6601 (8)	1.0105 (7)	0.7525 (5)	0.0252 (13)
H7BA	0.6122	1.0362	0.8077	0.030*
C8B	0.5967 (8)	1.0405 (7)	0.6684 (5)	0.0253 (13)
H8BA	0.5074	1.0884	0.6663	0.030*
C9B	0.6676 (7)	0.9984 (7)	0.5881 (4)	0.0216 (12)
H9BA	0.6239	1.0188	0.5321	0.026*
C11B	0.8708 (7)	0.8986 (6)	0.6729 (4)	0.0202 (12)
C12B	0.8597 (7)	0.8867 (6)	0.4919 (4)	0.0200 (12)
C13B	1.0179 (7)	0.8290 (7)	0.6895 (5)	0.0233 (13)
O1A	0.4113 (6)	0.6654 (5)	1.2511 (3)	0.0313 (11)
O2A	0.3986 (6)	0.7420 (5)	1.1025 (3)	0.0284 (11)
H1OA	0.4630	0.7831	1.0627	0.043*
O3A	0.5145 (5)	0.6946 (5)	0.9528 (3)	0.0271 (10)
O4A	0.7025 (6)	0.5820 (6)	0.8916 (3)	0.0344 (13)
C6A	0.8161 (7)	0.5016 (7)	1.0550 (4)	0.0222 (13)
H6AB	0.8572	0.4762	0.9981	0.027*
C7A	0.8877 (7)	0.4632 (7)	1.1348 (5)	0.0247 (13)
H7AB	0.9766	0.4145	1.1309	0.030*
C8A	0.8256 (8)	0.4979 (7)	1.2215 (4)	0.0245 (13)
H8AB	0.8736	0.4741	1.2755	0.029*
C9A	0.6919 (7)	0.5682 (6)	1.2255 (4)	0.0219 (12)
H9AB	0.6506	0.5902	1.2834	0.026*
C10A	0.6164 (7)	0.6075 (6)	1.1468 (4)	0.0197 (12)
C11A	0.6819 (7)	0.5788 (6)	1.0570 (4)	0.0190 (12)
C12A	0.4671 (8)	0.6747 (7)	1.1692 (5)	0.0240 (13)
C13A	0.6295 (7)	0.6207 (7)	0.9607 (4)	0.0215 (12)

	U11	U22	U33	U12	U13	U23
Br1A	0.0271 (4)	0.0455 (4)	0.0232 (3)	−0.0034 (3)	0.0011 (3)	−0.0148 (3)
N1A	0.022 (3)	0.024 (3)	0.013 (2)	−0.003 (2)	−0.0037 (19)	−0.0040 (19)
N2A	0.022 (3)	0.030 (3)	0.020 (3)	−0.001 (2)	−0.002 (2)	−0.006 (2)
C1A	0.020 (3)	0.026 (3)	0.021 (3)	−0.005 (2)	−0.002 (2)	−0.004 (2)
C2A	0.024 (3)	0.030 (3)	0.014 (3)	−0.008 (3)	0.003 (2)	−0.008 (2)
C3A	0.026 (3)	0.033 (4)	0.017 (3)	−0.007 (3)	−0.006 (2)	−0.008 (3)
C4A	0.023 (3)	0.030 (4)	0.020 (3)	−0.005 (3)	−0.007 (2)	0.000 (2)
C5A	0.022 (3)	0.022 (3)	0.019 (3)	−0.005 (2)	−0.003 (2)	−0.004 (2)
Br1B	0.0262 (4)	0.0485 (5)	0.0208 (3)	−0.0002 (3)	−0.0066 (3)	0.0002 (3)
N1B	0.023 (3)	0.028 (3)	0.016 (2)	0.000 (2)	0.001 (2)	−0.006 (2)
N2B	0.028 (3)	0.031 (3)	0.019 (3)	0.004 (2)	0.000 (2)	−0.004 (2)
C1B	0.021 (3)	0.024 (3)	0.022 (3)	−0.005 (2)	−0.002 (2)	−0.004 (2)
C2B	0.022 (3)	0.028 (3)	0.020 (3)	−0.005 (3)	−0.004 (2)	−0.004 (2)
C3B	0.028 (3)	0.030 (4)	0.019 (3)	−0.006 (3)	0.003 (2)	−0.009 (3)
C4B	0.026 (3)	0.029 (3)	0.018 (3)	0.000 (3)	0.003 (2)	−0.008 (2)
C5B	0.024 (3)	0.023 (3)	0.019 (3)	−0.005 (2)	0.001 (2)	−0.002 (2)
O1B	0.036 (3)	0.051 (3)	0.018 (2)	0.014 (3)	−0.007 (2)	−0.007 (2)
O2B	0.022 (2)	0.033 (3)	0.021 (2)	0.0008 (19)	0.0014 (18)	−0.0059 (19)
O3B	0.034 (3)	0.037 (3)	0.020 (2)	0.012 (2)	−0.008 (2)	−0.007 (2)
O4B	0.029 (3)	0.033 (3)	0.028 (2)	0.003 (2)	−0.014 (2)	−0.004 (2)
C10B	0.022 (3)	0.021 (3)	0.016 (3)	−0.003 (2)	−0.003 (2)	−0.001 (2)
C6B	0.033 (3)	0.024 (3)	0.014 (3)	0.000 (3)	−0.005 (2)	−0.004 (2)
C7B	0.030 (3)	0.027 (3)	0.019 (3)	−0.003 (3)	0.001 (3)	−0.008 (2)
C8B	0.023 (3)	0.030 (4)	0.024 (3)	0.004 (3)	−0.001 (2)	−0.007 (3)
C9B	0.023 (3)	0.027 (3)	0.015 (3)	−0.002 (2)	−0.001 (2)	−0.002 (2)
C11B	0.022 (3)	0.021 (3)	0.018 (3)	−0.002 (2)	−0.001 (2)	−0.004 (2)
C12B	0.020 (3)	0.023 (3)	0.016 (3)	−0.002 (2)	−0.001 (2)	0.000 (2)
C13B	0.020 (3)	0.024 (3)	0.026 (3)	0.004 (2)	−0.008 (2)	−0.004 (2)
O1A	0.035 (3)	0.033 (3)	0.021 (2)	0.008 (2)	0.008 (2)	0.002 (2)
O2A	0.030 (3)	0.035 (3)	0.018 (2)	0.009 (2)	0.0023 (18)	−0.0023 (19)
O3A	0.027 (2)	0.036 (3)	0.019 (2)	0.010 (2)	−0.0050 (18)	−0.0047 (19)
O4A	0.033 (3)	0.057 (4)	0.013 (2)	0.015 (3)	−0.0048 (19)	−0.005 (2)
C6A	0.021 (3)	0.029 (3)	0.016 (3)	0.000 (3)	0.003 (2)	−0.006 (2)
C7A	0.021 (3)	0.028 (3)	0.022 (3)	0.002 (3)	0.001 (2)	0.002 (3)
C8A	0.026 (3)	0.030 (3)	0.018 (3)	−0.003 (3)	−0.005 (2)	0.000 (2)
C9A	0.028 (3)	0.023 (3)	0.014 (3)	−0.002 (3)	0.001 (2)	−0.004 (2)
C10A	0.023 (3)	0.020 (3)	0.016 (3)	0.000 (2)	0.002 (2)	−0.005 (2)
C11A	0.021 (3)	0.022 (3)	0.014 (3)	−0.002 (2)	0.002 (2)	−0.004 (2)
C12A	0.028 (3)	0.020 (3)	0.024 (3)	0.002 (3)	0.001 (3)	−0.004 (2)
C13A	0.022 (3)	0.028 (3)	0.015 (3)	−0.004 (2)	−0.002 (2)	−0.002 (2)

Br1A—C2A	1.891 (6)	O3B—H2O3	0.7471
N1A—C1A	1.352 (8)	O4B—C13B	1.231 (8)
N1A—C5A	1.354 (8)	C10B—C9B	1.410 (9)
N1A—H1N1	0.8651	C10B—C11B	1.428 (8)
N2A—C5A	1.343 (8)	C10B—C12B	1.508 (9)
N2A—H2NA	0.9388	C6B—C7B	1.394 (10)
N2A—H3NA	0.9814	C6B—C11B	1.396 (9)
C1A—C2A	1.366 (9)	C6B—H6BA	0.9300
C1A—H1AA	0.9300	C7B—C8B	1.385 (9)
C2A—C3A	1.396 (10)	C7B—H7BA	0.9300
C3A—C4A	1.378 (9)	C8B—C9B	1.375 (9)
C3A—H3AA	0.9300	C8B—H8BA	0.9300
C4A—C5A	1.418 (9)	C9B—H9BA	0.9300
C4A—H4AA	0.9300	C11B—C13B	1.510 (9)
Br1B—C2B	1.889 (7)	O1A—C12A	1.226 (8)
N1B—C5B	1.340 (8)	O2A—C12A	1.302 (8)
N1B—C1B	1.352 (8)	O2A—H1OA	0.8532
N1B—H2N1	0.9235	O3A—C13A	1.267 (8)
N2B—C5B	1.345 (8)	O4A—C13A	1.239 (8)
N2B—H3N2	0.9952	C6A—C7A	1.381 (9)
N2B—H4N2	0.8108	C6A—C11A	1.421 (9)
C1B—C2B	1.353 (9)	C6A—H6AB	0.9300
C1B—H1BA	0.9300	C7A—C8A	1.399 (9)
C2B—C3B	1.400 (10)	C7A—H7AB	0.9300
C3B—C4B	1.359 (10)	C8A—C9A	1.382 (9)
C3B—H3BA	0.9300	C8A—H8AB	0.9300
C4B—C5B	1.423 (9)	C9A—C10A	1.389 (9)
C4B—H4BA	0.9300	C9A—H9AB	0.9300
O1B—C12B	1.241 (8)	C10A—C11A	1.428 (8)
O2B—C12B	1.277 (8)	C10A—C12A	1.514 (9)
O3B—C13B	1.300 (8)	C11A—C13A	1.515 (8)
C1A—N1A—C5A	123.1 (5)	C7B—C6B—C11B	122.4 (6)
C1A—N1A—H1N1	111.1	C7B—C6B—H6BA	118.8
C5A—N1A—H1N1	124.9	C11B—C6B—H6BA	118.8
C5A—N2A—H2NA	126.7	C8B—C7B—C6B	119.4 (6)
C5A—N2A—H3NA	109.3	C8B—C7B—H7BA	120.3
H2NA—N2A—H3NA	115.7	C6B—C7B—H7BA	120.3
N1A—C1A—C2A	119.7 (6)	C9B—C8B—C7B	119.2 (6)
N1A—C1A—H1AA	120.2	C9B—C8B—H8BA	120.4
C2A—C1A—H1AA	120.2	C7B—C8B—H8BA	120.4
C1A—C2A—C3A	119.9 (6)	C8B—C9B—C10B	123.0 (6)
C1A—C2A—Br1A	118.9 (5)	C8B—C9B—H9BA	118.5
C3A—C2A—Br1A	121.1 (5)	C10B—C9B—H9BA	118.5
C4A—C3A—C2A	119.8 (6)	C6B—C11B—C10B	118.3 (6)
C4A—C3A—H3AA	120.1	C6B—C11B—C13B	113.6 (6)
C2A—C3A—H3AA	120.1	C10B—C11B—C13B	128.2 (6)
C3A—C4A—C5A	119.4 (6)	O1B—C12B—O2B	121.6 (6)
C3A—C4A—H4AA	120.3	O1B—C12B—C10B	118.0 (6)
C5A—C4A—H4AA	120.3	O2B—C12B—C10B	120.4 (6)
N2A—C5A—N1A	119.0 (6)	O4B—C13B—O3B	120.1 (6)
N2A—C5A—C4A	122.9 (6)	O4B—C13B—C11B	120.0 (6)
N1A—C5A—C4A	118.1 (6)	O3B—C13B—C11B	119.9 (6)
C5B—N1B—C1B	122.7 (6)	C12A—O2A—H1OA	108.9
C5B—N1B—H2N1	118.9	C7A—C6A—C11A	122.3 (6)
C1B—N1B—H2N1	116.7	C7A—C6A—H6AB	118.9
C5B—N2B—H3N2	120.3	C11A—C6A—H6AB	118.9
C5B—N2B—H4N2	117.1	C6A—C7A—C8A	119.7 (6)
H3N2—N2B—H4N2	112.4	C6A—C7A—H7AB	120.2
N1B—C1B—C2B	120.1 (6)	C8A—C7A—H7AB	120.2
N1B—C1B—H1BA	120.0	C9A—C8A—C7A	119.0 (6)
C2B—C1B—H1BA	120.0	C9A—C8A—H8AB	120.5
C1B—C2B—C3B	119.6 (6)	C7A—C8A—H8AB	120.5
C1B—C2B—Br1B	119.0 (5)	C8A—C9A—C10A	122.8 (6)
C3B—C2B—Br1B	121.4 (5)	C8A—C9A—H9AB	118.6
C4B—C3B—C2B	120.0 (6)	C10A—C9A—H9AB	118.6
C4B—C3B—H3BA	120.0	C9A—C10A—C11A	119.0 (6)
C2B—C3B—H3BA	120.0	C9A—C10A—C12A	113.5 (5)
C3B—C4B—C5B	119.3 (6)	C11A—C10A—C12A	127.5 (6)
C3B—C4B—H4BA	120.3	C6A—C11A—C10A	117.1 (6)
C5B—C4B—H4BA	120.3	C6A—C11A—C13A	113.9 (5)
N1B—C5B—N2B	119.5 (6)	C10A—C11A—C13A	129.0 (6)
N1B—C5B—C4B	118.2 (6)	O1A—C12A—O2A	120.2 (6)
N2B—C5B—C4B	122.2 (6)	O1A—C12A—C10A	119.2 (6)
C13B—O3B—H2O3	121.4	O2A—C12A—C10A	120.6 (6)
C9B—C10B—C11B	117.6 (6)	O4A—C13A—O3A	122.0 (6)
C9B—C10B—C12B	114.3 (5)	O4A—C13A—C11A	118.2 (6)
C11B—C10B—C12B	128.1 (6)	O3A—C13A—C11A	119.8 (5)
C5A—N1A—C1A—C2A	0.5 (10)	C9B—C10B—C11B—C13B	−177.0 (6)
N1A—C1A—C2A—C3A	0.3 (10)	C12B—C10B—C11B—C13B	2.7 (11)
N1A—C1A—C2A—Br1A	−177.1 (5)	C9B—C10B—C12B—O1B	2.9 (9)
C1A—C2A—C3A—C4A	−0.1 (10)	C11B—C10B—C12B—O1B	−176.8 (6)
Br1A—C2A—C3A—C4A	177.3 (5)	C9B—C10B—C12B—O2B	−177.4 (6)
C2A—C3A—C4A—C5A	−0.9 (10)	C11B—C10B—C12B—O2B	2.9 (10)
C1A—N1A—C5A—N2A	178.9 (6)	C6B—C11B—C13B—O4B	−15.4 (9)
C1A—N1A—C5A—C4A	−1.6 (9)	C10B—C11B—C13B—O4B	163.8 (7)
C3A—C4A—C5A—N2A	−178.8 (6)	C6B—C11B—C13B—O3B	162.2 (6)
C3A—C4A—C5A—N1A	1.7 (10)	C10B—C11B—C13B—O3B	−18.6 (10)
C5B—N1B—C1B—C2B	0.5 (10)	C11A—C6A—C7A—C8A	1.5 (10)
N1B—C1B—C2B—C3B	−0.2 (10)	C6A—C7A—C8A—C9A	1.2 (10)
N1B—C1B—C2B—Br1B	−178.2 (5)	C7A—C8A—C9A—C10A	−0.7 (10)
C1B—C2B—C3B—C4B	0.2 (10)	C8A—C9A—C10A—C11A	−2.5 (10)
Br1B—C2B—C3B—C4B	178.1 (5)	C8A—C9A—C10A—C12A	175.9 (6)
C2B—C3B—C4B—C5B	−0.5 (10)	C7A—C6A—C11A—C10A	−4.6 (10)
C1B—N1B—C5B—N2B	179.7 (6)	C7A—C6A—C11A—C13A	174.7 (6)
C1B—N1B—C5B—C4B	−0.7 (10)	C9A—C10A—C11A—C6A	5.0 (9)
C3B—C4B—C5B—N1B	0.7 (10)	C12A—C10A—C11A—C6A	−173.1 (6)
C3B—C4B—C5B—N2B	−179.7 (7)	C9A—C10A—C11A—C13A	−174.2 (6)
C11B—C6B—C7B—C8B	−1.2 (11)	C12A—C10A—C11A—C13A	7.7 (11)
C6B—C7B—C8B—C9B	1.7 (10)	C9A—C10A—C12A—O1A	−14.9 (9)
C7B—C8B—C9B—C10B	−0.2 (11)	C11A—C10A—C12A—O1A	163.3 (7)
C11B—C10B—C9B—C8B	−1.7 (10)	C9A—C10A—C12A—O2A	164.9 (6)
C12B—C10B—C9B—C8B	178.5 (6)	C11A—C10A—C12A—O2A	−16.9 (10)
C7B—C6B—C11B—C10B	−0.7 (10)	C6A—C11A—C13A—O4A	2.3 (9)
C7B—C6B—C11B—C13B	178.5 (6)	C10A—C11A—C13A—O4A	−178.5 (7)
C9B—C10B—C11B—C6B	2.1 (9)	C6A—C11A—C13A—O3A	−177.0 (6)
C12B—C10B—C11B—C6B	−178.2 (6)	C10A—C11A—C13A—O3A	2.2 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1N1···O4A	0.86	1.80	2.664 (7)	176
N2A—H2NA···O4Bi	0.94	1.97	2.910 (8)	175
N2A—H3NA···O3A	0.98	1.97	2.930 (7)	167
O3B—H2O3···O2B	0.75	1.68	2.391 (6)	159
N1B—H2N1···O1B	0.92	1.82	2.647 (7)	147
N2B—H3N2···O1Aii	1.00	1.91	2.903 (8)	176
N2B—H4N2···O2B	0.81	2.20	2.971 (7)	160
C4A—H4AA···O3Bi	0.93	2.44	3.219 (9)	141
C4B—H4BA···O2Aii	0.93	2.42	3.175 (9)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1N1⋯O4A	0.86	1.80	2.664 (7)	176
N2A—H2NA⋯O4Bi	0.94	1.97	2.910 (8)	175
N2A—H3NA⋯O3A	0.98	1.97	2.930 (7)	167
O3B—H2O3⋯O2B	0.75	1.68	2.391 (6)	159
N1B—H2N1⋯O1B	0.92	1.82	2.647 (7)	147
N2B—H3N2⋯O1Aii	1.00	1.91	2.903 (8)	176
N2B—H4N2⋯O2B	0.81	2.20	2.971 (7)	160
C4A—H4AA⋯O3Bi	0.93	2.44	3.219 (9)	141
C4B—H4BA⋯O2Aii	0.93	2.42	3.175 (9)	139

Symmetry codes: (i) ; (ii) .