2-Amino-5-bromo-pyridinium 3-carb-oxy-4-hy-droxy-benzene-sulfonate.

The asymmetric unit of the title salt, C(5)H(6)BrN(2) (+)·C(7)H(5)O(6)S(-), contains two independent 2-amino-5-bromo-pyridinium cations and two independent 3-carb-oxy-4-hy-droxy-benzene-sulfonate anions. The hy-droxy and carboxyl groups of the anions are involved in intra-molecular O-H⋯O hydrogen bonds, which generate S(6) ring motifs. In the crystal structure, the ions are linked by N-H⋯O and O-H⋯O hydrogen bonds into a two-dimensional network parallel to (110). Adjacent networks are linked via C-H⋯O hydrogen bonds.

Related literature

For applications of pyridinium compounds, see: Akkurt et al. (2005 ▶); Navarro Ranninger et al. (1985 ▶); Krizanovic et al. (1993 ▶); Luque et al. (1997 ▶); Qin et al. (1999 ▶); Yip et al. (1999 ▶); Lah et al. (2002 ▶); Ren et al. (2002 ▶); Rivas et al. (2003 ▶); Luque et al. (1997 ▶); Jin et al. (2000 ▶); Albrecht et al. (2003 ▶). For related structures, see: Hemamalini & Fun (2010 ▶); Quah et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C5H6BrN2 +·C7H5O6S−

M = 391.20

Triclinic,

a = 7.8425 (2) Å

b = 10.8682 (3) Å

c = 16.5457 (5) Å

α = 85.207 (2)°

β = 83.290 (2)°

γ = 86.537 (2)°

V = 1393.87 (7) Å3

Z = 4

Mo Kα radiation

μ = 3.13 mm−1

T = 100 K

0.26 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.498, T max = 0.772

34040 measured reflections

9322 independent reflections

7366 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.181

S = 1.11

9322 reflections

397 parameters

H-atom parameters constrained

Δρmax = 1.65 e Å−3

Δρmin = −0.83 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/S1600536810033908/ci5165sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033908/ci5165Isup2.hkl

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

C5H6BrN2+·C7H5O6S−	Z = 4
Mr = 391.20	F(000) = 784
Triclinic, P1	Dx = 1.864 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8425 (2) Å	Cell parameters from 9916 reflections
b = 10.8682 (3) Å	θ = 3.0–31.4°
c = 16.5457 (5) Å	µ = 3.13 mm−1
α = 85.207 (2)°	T = 100 K
β = 83.290 (2)°	Plate, yellow
γ = 86.537 (2)°	0.26 × 0.14 × 0.09 mm
V = 1393.87 (7) Å3

Bruker SMART APEXII CCD area-detector diffractometer	9322 independent reflections
Radiation source: fine-focus sealed tube	7366 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 31.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.498, Tmax = 0.772	k = −15→16
34040 measured reflections	l = −24→24

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0451P)2 + 14.502P] where P = (Fo2 + 2Fc2)/3
9322 reflections	(Δ/σ)max = 0.001
397 parameters	Δρmax = 1.65 e Å−3
0 restraints	Δρmin = −0.83 e Å−3

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

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
Br1A	0.34842 (7)	1.03576 (5)	0.09171 (3)	0.02290 (13)
N1A	0.3053 (5)	1.0274 (4)	0.3409 (2)	0.0164 (7)
H1NA	0.3775	0.9756	0.3767	0.020*
N2A	0.1288 (6)	1.1186 (4)	0.4427 (3)	0.0220 (9)
H2AB	0.0369	1.1714	0.4514	0.026*
H2NA	0.1650	1.0910	0.4843	0.026*
C1A	0.1717 (6)	1.1047 (5)	0.3644 (3)	0.0179 (9)
C2A	0.0822 (6)	1.1683 (5)	0.3013 (3)	0.0181 (9)
H2AA	−0.0107	1.2229	0.3149	0.022*
C3A	0.1326 (6)	1.1490 (5)	0.2214 (3)	0.0180 (9)
H3AA	0.0732	1.1895	0.1806	0.022*
C4A	0.2754 (6)	1.0674 (5)	0.2008 (3)	0.0161 (8)
C5A	0.3601 (6)	1.0076 (5)	0.2613 (3)	0.0163 (8)
H5AA	0.4544	0.9538	0.2485	0.020*
S1A	0.15205 (14)	0.68598 (11)	0.03315 (6)	0.0126 (2)
O1A	−0.2400 (5)	0.9811 (3)	0.2821 (2)	0.0180 (7)
H1OA	−0.2078	0.9424	0.3229	0.027*
O2A	−0.0584 (5)	0.8634 (4)	0.3883 (2)	0.0227 (8)
O3A	0.1606 (5)	0.7338 (3)	0.3455 (2)	0.0178 (7)
H2OA	0.1921	0.7418	0.3952	0.027*
O4A	0.2922 (4)	0.7619 (3)	−0.0065 (2)	0.0169 (7)
O5A	0.2150 (5)	0.5735 (3)	0.0766 (2)	0.0196 (7)
O6A	0.0315 (5)	0.6618 (4)	−0.0241 (2)	0.0194 (7)
C6A	−0.1432 (6)	0.9151 (4)	0.2271 (3)	0.0134 (8)
C7A	−0.1724 (6)	0.9374 (4)	0.1452 (3)	0.0162 (8)
H7AA	−0.2528	0.9992	0.1304	0.019*
C8A	−0.0827 (6)	0.8683 (4)	0.0861 (3)	0.0150 (8)
H8AA	−0.1028	0.8838	0.0318	0.018*
C9A	0.0377 (6)	0.7754 (4)	0.1079 (3)	0.0134 (8)
C10A	0.0740 (6)	0.7554 (4)	0.1881 (3)	0.0130 (8)
H10A	0.1576	0.6954	0.2018	0.016*
C11A	−0.0146 (6)	0.8250 (4)	0.2484 (3)	0.0129 (8)
C12A	0.0249 (6)	0.8082 (4)	0.3339 (3)	0.0154 (8)
Br1B	0.82103 (7)	0.51159 (5)	0.36511 (3)	0.02183 (12)
N1B	0.7997 (5)	0.5274 (4)	0.1191 (2)	0.0151 (7)
H1NB	0.8554	0.5000	0.0772	0.018*
N2B	0.6286 (6)	0.6276 (4)	0.0271 (2)	0.0185 (8)
H2NB	0.6942	0.6071	−0.0134	0.022*
H3NB	0.5478	0.6641	0.0167	0.022*
C1B	0.6675 (6)	0.6070 (4)	0.1026 (3)	0.0148 (8)
C2B	0.5735 (6)	0.6639 (5)	0.1700 (3)	0.0181 (9)
H2BA	0.4806	0.7187	0.1612	0.022*
C3B	0.6179 (7)	0.6392 (5)	0.2468 (3)	0.0190 (9)
H3BA	0.5569	0.6775	0.2903	0.023*
C4B	0.7588 (6)	0.5541 (5)	0.2600 (3)	0.0157 (8)
C5B	0.8482 (6)	0.5005 (4)	0.1952 (3)	0.0151 (8)
H5BA	0.9418	0.4459	0.2030	0.018*
S1B	0.34815 (15)	0.81374 (11)	0.51288 (7)	0.0149 (2)
O1B	0.7530 (5)	0.5267 (3)	0.7495 (2)	0.0182 (7)
H1OB	0.7144	0.5349	0.7967	0.027*
O2B	0.5619 (5)	0.6350 (4)	0.8632 (2)	0.0196 (7)
O3B	0.3442 (5)	0.7652 (3)	0.8315 (2)	0.0176 (7)
H2OB	0.3280	0.7778	0.8844	0.026*
O4B	0.4611 (5)	0.8372 (4)	0.4372 (2)	0.0239 (8)
O5B	0.2794 (6)	0.9255 (4)	0.5500 (2)	0.0269 (9)
O6B	0.2102 (5)	0.7328 (4)	0.5012 (2)	0.0201 (7)
C6B	0.6577 (6)	0.5938 (4)	0.6973 (3)	0.0133 (8)
C7B	0.6953 (7)	0.5781 (5)	0.6139 (3)	0.0183 (9)
H7BA	0.7826	0.5215	0.5963	0.022*
C8B	0.6037 (6)	0.6462 (5)	0.5575 (3)	0.0186 (9)
H8BA	0.6293	0.6353	0.5021	0.022*
C9B	0.4723 (6)	0.7315 (4)	0.5838 (3)	0.0144 (8)
C10B	0.4318 (6)	0.7471 (4)	0.6658 (3)	0.0131 (8)
H10B	0.3430	0.8031	0.6828	0.016*
C11B	0.5235 (6)	0.6792 (4)	0.7235 (3)	0.0121 (7)
C12B	0.4794 (6)	0.6907 (4)	0.8116 (3)	0.0140 (8)

	U11	U22	U33	U12	U13	U23
Br1A	0.0219 (2)	0.0316 (3)	0.0159 (2)	−0.0003 (2)	−0.00412 (17)	−0.00410 (18)
N1A	0.0165 (18)	0.0151 (19)	0.0166 (17)	0.0003 (15)	−0.0026 (14)	0.0048 (14)
N2A	0.023 (2)	0.025 (2)	0.0170 (19)	0.0012 (17)	0.0003 (16)	0.0000 (16)
C1A	0.018 (2)	0.018 (2)	0.017 (2)	−0.0045 (17)	0.0005 (16)	0.0005 (17)
C2A	0.014 (2)	0.019 (2)	0.021 (2)	0.0019 (17)	−0.0016 (16)	0.0014 (17)
C3A	0.016 (2)	0.018 (2)	0.020 (2)	0.0010 (17)	−0.0052 (17)	0.0013 (17)
C4A	0.015 (2)	0.018 (2)	0.0162 (19)	−0.0050 (17)	−0.0020 (15)	0.0011 (16)
C5A	0.0122 (19)	0.017 (2)	0.019 (2)	0.0010 (16)	−0.0019 (16)	0.0007 (16)
S1A	0.0121 (5)	0.0141 (5)	0.0114 (4)	0.0016 (4)	−0.0007 (3)	−0.0027 (4)
O1A	0.0182 (16)	0.0205 (18)	0.0152 (15)	0.0078 (13)	−0.0030 (12)	−0.0050 (13)
O2A	0.0253 (19)	0.028 (2)	0.0148 (15)	0.0126 (15)	−0.0066 (13)	−0.0063 (14)
O3A	0.0188 (17)	0.0184 (17)	0.0166 (15)	0.0095 (13)	−0.0067 (12)	−0.0042 (12)
O4A	0.0147 (15)	0.0189 (17)	0.0164 (15)	−0.0015 (13)	0.0017 (12)	−0.0024 (12)
O5A	0.0242 (18)	0.0155 (17)	0.0181 (16)	0.0067 (14)	−0.0017 (13)	−0.0009 (12)
O6A	0.0183 (17)	0.0240 (19)	0.0175 (15)	−0.0015 (14)	−0.0032 (13)	−0.0093 (13)
C6A	0.0134 (19)	0.013 (2)	0.0137 (18)	0.0030 (15)	−0.0025 (15)	−0.0029 (15)
C7A	0.019 (2)	0.013 (2)	0.0166 (19)	0.0025 (17)	−0.0040 (16)	−0.0015 (15)
C8A	0.016 (2)	0.016 (2)	0.0127 (18)	0.0030 (16)	−0.0035 (15)	−0.0017 (15)
C9A	0.016 (2)	0.0117 (19)	0.0124 (18)	−0.0016 (15)	0.0025 (15)	−0.0038 (14)
C10A	0.0132 (19)	0.012 (2)	0.0141 (18)	−0.0020 (15)	−0.0015 (15)	−0.0038 (15)
C11A	0.0135 (19)	0.014 (2)	0.0121 (17)	0.0013 (15)	−0.0034 (14)	−0.0021 (14)
C12A	0.018 (2)	0.014 (2)	0.0157 (19)	0.0013 (16)	−0.0043 (16)	−0.0027 (15)
Br1B	0.0238 (3)	0.0286 (3)	0.0131 (2)	−0.0010 (2)	−0.00254 (17)	−0.00132 (17)
N1B	0.0132 (17)	0.019 (2)	0.0130 (16)	−0.0017 (14)	0.0005 (13)	−0.0033 (14)
N2B	0.0172 (19)	0.023 (2)	0.0154 (17)	0.0027 (16)	−0.0034 (14)	−0.0017 (15)
C1B	0.014 (2)	0.015 (2)	0.0155 (19)	−0.0031 (16)	0.0002 (15)	−0.0008 (15)
C2B	0.017 (2)	0.016 (2)	0.022 (2)	0.0019 (17)	−0.0020 (17)	−0.0046 (17)
C3B	0.022 (2)	0.017 (2)	0.017 (2)	−0.0029 (18)	0.0031 (17)	−0.0045 (17)
C4B	0.016 (2)	0.019 (2)	0.0124 (18)	−0.0048 (17)	−0.0014 (15)	−0.0009 (15)
C5B	0.016 (2)	0.012 (2)	0.017 (2)	−0.0002 (16)	−0.0024 (16)	−0.0018 (15)
S1B	0.0165 (5)	0.0162 (5)	0.0123 (4)	0.0028 (4)	−0.0046 (4)	−0.0005 (4)
O1B	0.0190 (17)	0.0208 (18)	0.0139 (14)	0.0071 (13)	−0.0032 (12)	−0.0002 (12)
O2B	0.0237 (18)	0.0205 (18)	0.0136 (15)	0.0073 (14)	−0.0040 (13)	0.0006 (12)
O3B	0.0207 (17)	0.0184 (17)	0.0126 (14)	0.0039 (13)	−0.0008 (12)	0.0001 (12)
O4B	0.0250 (19)	0.029 (2)	0.0166 (16)	0.0023 (16)	−0.0023 (14)	0.0037 (14)
O5B	0.038 (2)	0.0215 (19)	0.0210 (17)	0.0152 (17)	−0.0109 (16)	−0.0052 (14)
O6B	0.0193 (17)	0.0232 (19)	0.0186 (16)	−0.0028 (14)	−0.0076 (13)	0.0011 (13)
C6B	0.0105 (18)	0.015 (2)	0.0144 (18)	0.0015 (15)	−0.0022 (14)	−0.0006 (15)
C7B	0.018 (2)	0.020 (2)	0.016 (2)	0.0066 (18)	−0.0025 (16)	−0.0034 (17)
C8B	0.018 (2)	0.022 (2)	0.015 (2)	0.0070 (18)	−0.0050 (16)	−0.0044 (17)
C9B	0.015 (2)	0.016 (2)	0.0130 (18)	0.0021 (16)	−0.0048 (15)	−0.0020 (15)
C10B	0.0128 (19)	0.013 (2)	0.0142 (18)	0.0003 (15)	−0.0031 (14)	−0.0014 (15)
C11B	0.0129 (19)	0.0116 (19)	0.0121 (17)	0.0011 (15)	−0.0030 (14)	−0.0021 (14)
C12B	0.017 (2)	0.013 (2)	0.0124 (18)	−0.0014 (16)	−0.0020 (15)	0.0005 (14)

Br1A—C4A	1.883 (5)	Br1B—C4B	1.874 (5)
N1A—C1A	1.344 (7)	N1B—C1B	1.348 (6)
N1A—C5A	1.367 (6)	N1B—C5B	1.361 (6)
N1A—H1NA	0.98	N1B—H1NB	0.84
N2A—C1A	1.320 (6)	N2B—C1B	1.318 (6)
N2A—H2AB	0.90	N2B—H2NB	0.83
N2A—H2NA	0.80	N2B—H3NB	0.76
C1A—C2A	1.433 (7)	C1B—C2B	1.427 (6)
C2A—C3A	1.365 (7)	C2B—C3B	1.358 (7)
C2A—H2AA	0.93	C2B—H2BA	0.93
C3A—C4A	1.413 (7)	C3B—C4B	1.422 (7)
C3A—H3AA	0.93	C3B—H3BA	0.93
C4A—C5A	1.364 (7)	C4B—C5B	1.364 (6)
C5A—H5AA	0.93	C5B—H5BA	0.93
S1A—O5A	1.455 (4)	S1B—O5B	1.453 (4)
S1A—O6A	1.464 (4)	S1B—O4B	1.461 (4)
S1A—O4A	1.473 (4)	S1B—O6B	1.475 (4)
S1A—C9A	1.765 (4)	S1B—C9B	1.764 (5)
O1A—C6A	1.343 (5)	O1B—C6B	1.347 (6)
O1A—H1OA	0.82	O1B—H1OB	0.82
O2A—C12A	1.225 (6)	O2B—C12B	1.230 (6)
O3A—C12A	1.319 (6)	O3B—C12B	1.322 (6)
O3A—H2OA	0.90	O3B—H2OB	0.89
C6A—C7A	1.399 (6)	C6B—C7B	1.400 (6)
C6A—C11A	1.417 (6)	C6B—C11B	1.414 (6)
C7A—C8A	1.384 (6)	C7B—C8B	1.384 (7)
C7A—H7AA	0.93	C7B—H7BA	0.93
C8A—C9A	1.395 (7)	C8B—C9B	1.399 (7)
C8A—H8AA	0.93	C8B—H8BA	0.93
C9A—C10A	1.386 (6)	C9B—C10B	1.379 (6)
C10A—C11A	1.397 (6)	C10B—C11B	1.397 (6)
C10A—H10A	0.93	C10B—H10B	0.93
C11A—C12A	1.478 (6)	C11B—C12B	1.472 (6)
C1A—N1A—C5A	123.9 (4)	C1B—N1B—C5B	123.8 (4)
C1A—N1A—H1NA	126.9	C1B—N1B—H1NB	113.6
C5A—N1A—H1NA	109.2	C5B—N1B—H1NB	122.5
C1A—N2A—H2AB	112.1	C1B—N2B—H2NB	123.2
C1A—N2A—H2NA	135.2	C1B—N2B—H3NB	122.4
H2AB—N2A—H2NA	112.7	H2NB—N2B—H3NB	114.2
N2A—C1A—N1A	119.7 (5)	N2B—C1B—N1B	119.9 (4)
N2A—C1A—C2A	123.3 (5)	N2B—C1B—C2B	123.1 (5)
N1A—C1A—C2A	117.1 (4)	N1B—C1B—C2B	117.0 (4)
C3A—C2A—C1A	120.3 (5)	C3B—C2B—C1B	121.0 (5)
C3A—C2A—H2AA	119.9	C3B—C2B—H2BA	119.5
C1A—C2A—H2AA	119.9	C1B—C2B—H2BA	119.5
C2A—C3A—C4A	119.8 (5)	C2B—C3B—C4B	119.2 (4)
C2A—C3A—H3AA	120.1	C2B—C3B—H3BA	120.4
C4A—C3A—H3AA	120.1	C4B—C3B—H3BA	120.4
C5A—C4A—C3A	119.5 (4)	C5B—C4B—C3B	119.4 (4)
C5A—C4A—Br1A	118.9 (4)	C5B—C4B—Br1B	119.3 (4)
C3A—C4A—Br1A	121.5 (4)	C3B—C4B—Br1B	121.3 (3)
C4A—C5A—N1A	119.5 (5)	N1B—C5B—C4B	119.7 (5)
C4A—C5A—H5AA	120.3	N1B—C5B—H5BA	120.2
N1A—C5A—H5AA	120.3	C4B—C5B—H5BA	120.2
O5A—S1A—O6A	112.6 (2)	O5B—S1B—O4B	113.7 (3)
O5A—S1A—O4A	112.6 (2)	O5B—S1B—O6B	111.5 (3)
O6A—S1A—O4A	111.7 (2)	O4B—S1B—O6B	111.1 (2)
O5A—S1A—C9A	106.2 (2)	O5B—S1B—C9B	106.3 (2)
O6A—S1A—C9A	107.2 (2)	O4B—S1B—C9B	107.4 (2)
O4A—S1A—C9A	106.0 (2)	O6B—S1B—C9B	106.3 (2)
C6A—O1A—H1OA	96.5	C6B—O1B—H1OB	111.2
C12A—O3A—H2OA	109.7	C12B—O3B—H2OB	113.5
O1A—C6A—C7A	117.7 (4)	O1B—C6B—C7B	118.0 (4)
O1A—C6A—C11A	123.0 (4)	O1B—C6B—C11B	122.7 (4)
C7A—C6A—C11A	119.3 (4)	C7B—C6B—C11B	119.3 (4)
C8A—C7A—C6A	120.5 (4)	C8B—C7B—C6B	120.5 (4)
C8A—C7A—H7AA	119.7	C8B—C7B—H7BA	119.7
C6A—C7A—H7AA	119.7	C6B—C7B—H7BA	119.7
C7A—C8A—C9A	120.0 (4)	C7B—C8B—C9B	119.9 (4)
C7A—C8A—H8AA	120.0	C7B—C8B—H8BA	120.1
C9A—C8A—H8AA	120.0	C9B—C8B—H8BA	120.1
C10A—C9A—C8A	120.4 (4)	C10B—C9B—C8B	120.5 (4)
C10A—C9A—S1A	119.1 (4)	C10B—C9B—S1B	119.2 (4)
C8A—C9A—S1A	120.5 (3)	C8B—C9B—S1B	120.2 (3)
C9A—C10A—C11A	120.2 (4)	C9B—C10B—C11B	120.3 (4)
C9A—C10A—H10A	119.9	C9B—C10B—H10B	119.9
C11A—C10A—H10A	119.9	C11B—C10B—H10B	119.9
C10A—C11A—C6A	119.5 (4)	C10B—C11B—C6B	119.6 (4)
C10A—C11A—C12A	121.4 (4)	C10B—C11B—C12B	121.5 (4)
C6A—C11A—C12A	119.1 (4)	C6B—C11B—C12B	118.9 (4)
O2A—C12A—O3A	123.4 (4)	O2B—C12B—O3B	122.1 (4)
O2A—C12A—C11A	122.1 (4)	O2B—C12B—C11B	122.6 (4)
O3A—C12A—C11A	114.4 (4)	O3B—C12B—C11B	115.3 (4)
C5A—N1A—C1A—N2A	−179.5 (5)	C5B—N1B—C1B—N2B	−179.8 (4)
C5A—N1A—C1A—C2A	0.6 (7)	C5B—N1B—C1B—C2B	−0.9 (7)
N2A—C1A—C2A—C3A	−179.5 (5)	N2B—C1B—C2B—C3B	179.6 (5)
N1A—C1A—C2A—C3A	0.3 (7)	N1B—C1B—C2B—C3B	0.7 (7)
C1A—C2A—C3A—C4A	−0.9 (7)	C1B—C2B—C3B—C4B	−0.8 (7)
C2A—C3A—C4A—C5A	0.7 (7)	C2B—C3B—C4B—C5B	1.0 (7)
C2A—C3A—C4A—Br1A	179.1 (4)	C2B—C3B—C4B—Br1B	−177.6 (4)
C3A—C4A—C5A—N1A	0.2 (7)	C1B—N1B—C5B—C4B	1.1 (7)
Br1A—C4A—C5A—N1A	−178.3 (3)	C3B—C4B—C5B—N1B	−1.1 (7)
C1A—N1A—C5A—C4A	−0.9 (7)	Br1B—C4B—C5B—N1B	177.5 (3)
O1A—C6A—C7A—C8A	−176.8 (4)	O1B—C6B—C7B—C8B	−178.8 (5)
C11A—C6A—C7A—C8A	3.1 (7)	C11B—C6B—C7B—C8B	0.6 (7)
C6A—C7A—C8A—C9A	0.1 (7)	C6B—C7B—C8B—C9B	0.0 (8)
C7A—C8A—C9A—C10A	−2.9 (7)	C7B—C8B—C9B—C10B	−0.9 (8)
C7A—C8A—C9A—S1A	179.6 (4)	C7B—C8B—C9B—S1B	−177.1 (4)
O5A—S1A—C9A—C10A	22.9 (4)	O5B—S1B—C9B—C10B	27.2 (5)
O6A—S1A—C9A—C10A	143.5 (4)	O4B—S1B—C9B—C10B	149.2 (4)
O4A—S1A—C9A—C10A	−97.1 (4)	O6B—S1B—C9B—C10B	−91.7 (4)
O5A—S1A—C9A—C8A	−159.7 (4)	O5B—S1B—C9B—C8B	−156.5 (4)
O6A—S1A—C9A—C8A	−39.1 (4)	O4B—S1B—C9B—C8B	−34.5 (5)
O4A—S1A—C9A—C8A	80.4 (4)	O6B—S1B—C9B—C8B	84.6 (4)
C8A—C9A—C10A—C11A	2.5 (7)	C8B—C9B—C10B—C11B	1.0 (7)
S1A—C9A—C10A—C11A	179.9 (3)	S1B—C9B—C10B—C11B	177.3 (3)
C9A—C10A—C11A—C6A	0.8 (7)	C9B—C10B—C11B—C6B	−0.4 (7)
C9A—C10A—C11A—C12A	−178.2 (4)	C9B—C10B—C11B—C12B	−177.9 (4)
O1A—C6A—C11A—C10A	176.4 (4)	O1B—C6B—C11B—C10B	178.9 (4)
C7A—C6A—C11A—C10A	−3.5 (7)	C7B—C6B—C11B—C10B	−0.5 (7)
O1A—C6A—C11A—C12A	−4.6 (7)	O1B—C6B—C11B—C12B	−3.5 (7)
C7A—C6A—C11A—C12A	175.5 (4)	C7B—C6B—C11B—C12B	177.1 (4)
C10A—C11A—C12A—O2A	−175.6 (5)	C10B—C11B—C12B—O2B	−177.5 (5)
C6A—C11A—C12A—O2A	5.4 (7)	C6B—C11B—C12B—O2B	5.0 (7)
C10A—C11A—C12A—O3A	7.2 (7)	C10B—C11B—C12B—O3B	2.6 (6)
C6A—C11A—C12A—O3A	−171.8 (4)	C6B—C11B—C12B—O3B	−175.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O4B	0.99	1.86	2.811 (6)	160
N2A—H2AB···O6Bi	0.90	2.23	3.113 (6)	166
N2A—H2NA···O5B	0.80	2.22	2.919 (6)	146
N2A—H2NA···O2Ai	0.80	2.26	2.807 (6)	126
O1A—H1OA···O2A	0.82	1.82	2.596 (5)	158
O3A—H2OA···O4B	0.90	2.60	3.250 (5)	130
O3A—H2OA···O6B	0.90	1.77	2.649 (5)	165
N1B—H1NB···O6Aii	0.84	2.13	2.859 (6)	145
N2B—H2NB···O5Aii	0.83	2.34	3.006 (5)	138
N2B—H3NB···O4A	0.76	2.27	3.024 (6)	175
O1B—H1OB···O2B	0.81	1.89	2.582 (5)	143
O1B—H1OB···O5Aiii	0.81	2.42	3.023 (5)	131
O3B—H2OB···O4Aiv	0.89	1.79	2.661 (5)	166
C5A—H5AA···O1Av	0.93	2.56	3.188 (6)	125
C10A—H10A···O1Biii	0.93	2.56	3.406 (6)	151
C10B—H10B···O1Ai	0.93	2.53	3.364 (6)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O4B	0.99	1.86	2.811 (6)	160
N2A—H2AB⋯O6Bi	0.90	2.23	3.113 (6)	166
N2A—H2NA⋯O5B	0.80	2.22	2.919 (6)	146
N2A—H2NA⋯O2Ai	0.80	2.26	2.807 (6)	126
O1A—H1OA⋯O2A	0.82	1.82	2.596 (5)	158
O3A—H2OA⋯O4B	0.90	2.60	3.250 (5)	130
O3A—H2OA⋯O6B	0.90	1.77	2.649 (5)	165
N1B—H1NB⋯O6Aii	0.84	2.13	2.859 (6)	145
N2B—H2NB⋯O5Aii	0.83	2.34	3.006 (5)	138
N2B—H3NB⋯O4A	0.76	2.27	3.024 (6)	175
O1B—H1OB⋯O2B	0.81	1.89	2.582 (5)	143
O1B—H1OB⋯O5Aiii	0.81	2.42	3.023 (5)	131
O3B—H2OB⋯O4Aiv	0.89	1.79	2.661 (5)	166
C5A—H5AA⋯O1Av	0.93	2.56	3.188 (6)	125
C10A—H10A⋯O1Biii	0.93	2.56	3.406 (6)	151
C10B—H10B⋯O1Ai	0.93	2.53	3.364 (6)	150

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