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

The asymmetric unit of the title salt, C(6)H(9)N(2) (+)·C(7)H(5)O(6)S(-), contains two crystallographically independent 2-amino-5-methylpyridinium cations and two sulfosalicylate anions. In the crystal structure, the sulfonate group of each 3-carb-oxy-4-hy-droxy-benzene-sulfonate anion inter-acts with the corresponding 2-amino-5-methyl-pyridinium cation via a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. The ionic units are linked by N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds. Furthermore, the crystal structure is stabilized by π-π inter-actions between the benzene and pyridine rings [centroid-centroid distances = 3.5579 (8) and 3.8309 (8) Å]. There are also intra-molecular O-H⋯O hydrogen bonds in the anions, which generate S(6) ring motifs.

Related literature

For details of weak inter­actions, see: Moghimi et al. (2002 ▶); Aghabozorg et al. (2005 ▶). For applications of sulfosalicylic acid, see: Smith et al. (2004 ▶); Raj et al. (2003 ▶); Muthiah et al. (2003 ▶); Wang & Wei (2007 ▶). For related structures, see: Nahringbauer & Kvick (1977 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C6H9N2 +·C7H5O6S−

M = 326.32

Triclinic,

a = 7.8635 (1) Å

b = 10.8827 (1) Å

c = 16.3907 (2) Å

α = 84.612 (1)°

β = 81.802 (1)°

γ = 86.290 (1)°

V = 1380.31 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.27 × 0.16 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.931, T max = 0.960

28351 measured reflections

7325 independent reflections

6209 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.04

7325 reflections

439 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.42 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/S1600536810029636/is2580sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029636/is2580Isup2.hkl

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

C6H9N2+·C7H5O6S−	Z = 4
Mr = 326.32	F(000) = 680
Triclinic, P1	Dx = 1.570 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8635 (1) Å	Cell parameters from 9890 reflections
b = 10.8827 (1) Å	θ = 2.4–30.2°
c = 16.3907 (2) Å	µ = 0.27 mm−1
α = 84.612 (1)°	T = 100 K
β = 81.802 (1)°	Block, colourless
γ = 86.290 (1)°	0.27 × 0.16 × 0.15 mm
V = 1380.31 (3) Å3

Bruker APEXII CCD area-detector diffractometer	7325 independent reflections
Radiation source: fine-focus sealed tube	6209 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 29.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.931, Tmax = 0.960	k = −14→14
28351 measured reflections	l = −22→22

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0439P)2 + 0.7462P] where P = (Fo2 + 2Fc2)/3
7325 reflections	(Δ/σ)max = 0.001
439 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.42 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
N1A	0.70541 (15)	0.97702 (11)	0.37753 (7)	0.0143 (2)
N2A	0.87358 (16)	0.87759 (12)	0.47109 (8)	0.0187 (2)
C1A	0.65985 (18)	1.00244 (13)	0.30014 (8)	0.0157 (3)
H1AA	0.5659	1.0567	0.2928	0.019*
C2A	0.83866 (17)	0.89880 (12)	0.39405 (8)	0.0148 (3)
C3A	0.93427 (18)	0.84175 (13)	0.32623 (9)	0.0184 (3)
H3AA	1.0272	0.7871	0.3347	0.022*
C4A	0.88974 (19)	0.86717 (13)	0.24861 (9)	0.0196 (3)
H4AA	0.9532	0.8292	0.2047	0.024*
C5A	0.74866 (18)	0.95025 (13)	0.23365 (9)	0.0177 (3)
C6A	0.6994 (2)	0.97934 (16)	0.14844 (9)	0.0254 (3)
H6AA	0.6016	1.0371	0.1508	0.038*
H6AB	0.6711	0.9048	0.1276	0.038*
H6AC	0.7941	1.0148	0.1124	0.038*
N1B	0.80370 (15)	0.51730 (11)	0.82703 (7)	0.0164 (2)
N2B	0.62446 (18)	0.60847 (12)	0.93174 (8)	0.0203 (3)
C1B	0.85961 (18)	0.50127 (13)	0.74565 (8)	0.0171 (3)
H1BA	0.9540	0.4474	0.7322	0.021*
C2B	0.66881 (18)	0.59477 (12)	0.85203 (9)	0.0163 (3)
C3B	0.58139 (18)	0.65888 (13)	0.78921 (9)	0.0185 (3)
H3BA	0.4866	0.7120	0.8036	0.022*
C4B	0.63620 (19)	0.64269 (13)	0.70806 (9)	0.0195 (3)
H4BA	0.5779	0.6852	0.6676	0.023*
C5B	0.78034 (18)	0.56232 (13)	0.68388 (9)	0.0179 (3)
C6B	0.8423 (2)	0.54427 (16)	0.59433 (9)	0.0256 (3)
H6BA	0.9511	0.4983	0.5899	0.038*
H6BB	0.8552	0.6234	0.5635	0.038*
H6BC	0.7600	0.4996	0.5725	0.038*
S1A	0.65009 (4)	0.18717 (3)	0.536127 (19)	0.01282 (8)
O1A	0.79222 (12)	0.26353 (9)	0.49587 (6)	0.0174 (2)
O2A	0.71260 (13)	0.07391 (9)	0.57916 (6)	0.0191 (2)
O3A	0.53262 (13)	0.16622 (9)	0.47817 (6)	0.0181 (2)
O4A	0.25189 (13)	0.48004 (9)	0.79013 (6)	0.0177 (2)
O5A	0.64439 (13)	0.22501 (9)	0.85364 (6)	0.0190 (2)
O6A	0.42614 (14)	0.35554 (10)	0.89784 (6)	0.0220 (2)
C7A	0.56636 (17)	0.25282 (12)	0.69411 (8)	0.0127 (2)
H7AA	0.6474	0.1912	0.7079	0.015*
C8A	0.53508 (17)	0.27527 (12)	0.61292 (8)	0.0128 (2)
C9A	0.41623 (17)	0.36980 (12)	0.59126 (8)	0.0146 (2)
H9AA	0.3982	0.3861	0.5364	0.018*
C10A	0.32577 (18)	0.43881 (12)	0.65118 (8)	0.0153 (3)
H10A	0.2478	0.5021	0.6364	0.018*
C11A	0.35090 (17)	0.41392 (12)	0.73440 (8)	0.0133 (2)
C12A	0.47654 (17)	0.32248 (12)	0.75539 (8)	0.0127 (2)
C13A	0.51185 (17)	0.30248 (12)	0.84203 (8)	0.0144 (2)
S1B	0.85292 (4)	0.31409 (3)	0.00943 (2)	0.01532 (8)
O1B	0.79350 (15)	0.43064 (10)	0.04277 (6)	0.0251 (2)
O2B	0.70905 (13)	0.23442 (10)	0.00786 (6)	0.0218 (2)
O3B	0.95916 (14)	0.32797 (10)	−0.07089 (6)	0.0210 (2)
O4B	1.26682 (13)	0.03415 (9)	0.24475 (6)	0.0184 (2)
O5B	1.06979 (13)	0.13883 (9)	0.36187 (6)	0.0189 (2)
O6B	0.84902 (13)	0.26692 (9)	0.33138 (6)	0.0166 (2)
C7B	0.93897 (17)	0.25027 (12)	0.16353 (8)	0.0133 (2)
H7BA	0.8489	0.3052	0.1816	0.016*
C8B	0.98051 (17)	0.23526 (12)	0.08005 (8)	0.0144 (2)
C9B	1.11603 (19)	0.15321 (14)	0.05255 (9)	0.0199 (3)
H9BA	1.1431	0.1435	−0.0037	0.024*
C10B	1.21005 (19)	0.08647 (14)	0.10831 (9)	0.0197 (3)
H10B	1.3000	0.0319	0.0895	0.024*
C11B	1.17031 (17)	0.10077 (12)	0.19298 (8)	0.0146 (3)
C12B	1.03250 (17)	0.18283 (12)	0.22094 (8)	0.0129 (2)
C13B	0.98732 (17)	0.19430 (12)	0.31039 (8)	0.0135 (2)
H1OA	0.281 (3)	0.455 (2)	0.8388 (14)	0.043 (6)*
H2OA	0.656 (3)	0.225 (2)	0.9052 (14)	0.042 (6)*
H1OB	1.228 (3)	0.051 (2)	0.2945 (16)	0.053 (7)*
H2OB	0.833 (3)	0.264 (2)	0.3844 (15)	0.047 (6)*
H1NA	0.640 (2)	1.0158 (17)	0.4175 (12)	0.025 (5)*
H2NA	0.814 (2)	0.9185 (17)	0.5103 (12)	0.023 (5)*
H3NA	0.970 (3)	0.8352 (17)	0.4780 (11)	0.022 (5)*
H1NB	0.858 (3)	0.474 (2)	0.8631 (13)	0.036 (6)*
H2NB	0.683 (3)	0.565 (2)	0.9689 (14)	0.040 (6)*
H3NB	0.531 (3)	0.6531 (18)	0.9467 (12)	0.029 (5)*

	U11	U22	U33	U12	U13	U23
N1A	0.0140 (5)	0.0164 (5)	0.0126 (5)	0.0000 (4)	−0.0004 (4)	−0.0044 (4)
N2A	0.0164 (6)	0.0243 (6)	0.0155 (6)	0.0031 (5)	−0.0034 (5)	−0.0036 (5)
C1A	0.0158 (6)	0.0167 (6)	0.0152 (6)	−0.0020 (5)	−0.0031 (5)	−0.0015 (5)
C2A	0.0140 (6)	0.0143 (6)	0.0164 (6)	−0.0022 (5)	−0.0014 (5)	−0.0022 (5)
C3A	0.0165 (6)	0.0170 (6)	0.0213 (7)	0.0016 (5)	0.0001 (5)	−0.0050 (5)
C4A	0.0206 (7)	0.0199 (7)	0.0180 (7)	−0.0031 (5)	0.0035 (5)	−0.0078 (5)
C5A	0.0196 (7)	0.0196 (6)	0.0147 (6)	−0.0064 (5)	−0.0012 (5)	−0.0034 (5)
C6A	0.0289 (8)	0.0334 (8)	0.0148 (7)	−0.0055 (7)	−0.0023 (6)	−0.0044 (6)
N1B	0.0175 (6)	0.0181 (6)	0.0130 (5)	0.0004 (4)	−0.0030 (4)	0.0015 (4)
N2B	0.0216 (6)	0.0233 (6)	0.0149 (6)	0.0020 (5)	−0.0006 (5)	−0.0007 (5)
C1B	0.0164 (6)	0.0193 (6)	0.0155 (6)	−0.0016 (5)	−0.0005 (5)	−0.0023 (5)
C2B	0.0168 (6)	0.0153 (6)	0.0166 (6)	−0.0031 (5)	−0.0013 (5)	−0.0002 (5)
C3B	0.0161 (6)	0.0178 (6)	0.0213 (7)	0.0003 (5)	−0.0038 (5)	0.0006 (5)
C4B	0.0209 (7)	0.0190 (7)	0.0198 (7)	−0.0038 (5)	−0.0085 (6)	0.0033 (5)
C5B	0.0182 (7)	0.0213 (7)	0.0149 (6)	−0.0065 (5)	−0.0027 (5)	0.0001 (5)
C6B	0.0286 (8)	0.0335 (8)	0.0152 (7)	−0.0066 (7)	−0.0035 (6)	−0.0012 (6)
S1A	0.01335 (15)	0.01459 (15)	0.01021 (14)	0.00201 (11)	−0.00056 (11)	−0.00296 (11)
O1A	0.0158 (5)	0.0214 (5)	0.0144 (5)	−0.0015 (4)	0.0018 (4)	−0.0034 (4)
O2A	0.0237 (5)	0.0166 (5)	0.0157 (5)	0.0069 (4)	−0.0010 (4)	−0.0019 (4)
O3A	0.0169 (5)	0.0235 (5)	0.0151 (5)	0.0014 (4)	−0.0035 (4)	−0.0078 (4)
O4A	0.0200 (5)	0.0201 (5)	0.0125 (5)	0.0077 (4)	−0.0026 (4)	−0.0053 (4)
O5A	0.0229 (5)	0.0211 (5)	0.0143 (5)	0.0066 (4)	−0.0085 (4)	−0.0050 (4)
O6A	0.0271 (6)	0.0263 (5)	0.0125 (5)	0.0095 (4)	−0.0047 (4)	−0.0065 (4)
C7A	0.0124 (6)	0.0130 (6)	0.0131 (6)	0.0009 (5)	−0.0025 (5)	−0.0019 (4)
C8A	0.0132 (6)	0.0134 (6)	0.0114 (6)	0.0001 (5)	−0.0005 (5)	−0.0027 (4)
C9A	0.0162 (6)	0.0165 (6)	0.0111 (6)	0.0010 (5)	−0.0031 (5)	−0.0001 (5)
C10A	0.0161 (6)	0.0156 (6)	0.0141 (6)	0.0038 (5)	−0.0039 (5)	−0.0009 (5)
C11A	0.0136 (6)	0.0131 (6)	0.0133 (6)	0.0012 (5)	−0.0011 (5)	−0.0038 (5)
C12A	0.0142 (6)	0.0125 (6)	0.0118 (6)	−0.0002 (5)	−0.0030 (5)	−0.0017 (4)
C13A	0.0170 (6)	0.0132 (6)	0.0135 (6)	0.0006 (5)	−0.0043 (5)	−0.0024 (5)
S1B	0.01759 (16)	0.01824 (16)	0.01035 (15)	0.00332 (12)	−0.00421 (12)	−0.00176 (11)
O1B	0.0344 (6)	0.0232 (5)	0.0183 (5)	0.0122 (5)	−0.0093 (5)	−0.0059 (4)
O2B	0.0212 (5)	0.0286 (6)	0.0165 (5)	−0.0029 (4)	−0.0080 (4)	0.0019 (4)
O3B	0.0228 (5)	0.0264 (5)	0.0124 (5)	0.0021 (4)	−0.0017 (4)	0.0015 (4)
O4B	0.0186 (5)	0.0211 (5)	0.0150 (5)	0.0075 (4)	−0.0045 (4)	−0.0012 (4)
O5B	0.0220 (5)	0.0216 (5)	0.0127 (4)	0.0058 (4)	−0.0041 (4)	−0.0004 (4)
O6B	0.0187 (5)	0.0192 (5)	0.0107 (4)	0.0049 (4)	−0.0003 (4)	−0.0012 (4)
C7B	0.0128 (6)	0.0137 (6)	0.0136 (6)	0.0003 (5)	−0.0022 (5)	−0.0023 (5)
C8B	0.0153 (6)	0.0161 (6)	0.0122 (6)	0.0020 (5)	−0.0042 (5)	−0.0024 (5)
C9B	0.0221 (7)	0.0252 (7)	0.0125 (6)	0.0056 (6)	−0.0032 (5)	−0.0059 (5)
C10B	0.0193 (7)	0.0236 (7)	0.0155 (6)	0.0085 (6)	−0.0015 (5)	−0.0059 (5)
C11B	0.0141 (6)	0.0153 (6)	0.0145 (6)	0.0018 (5)	−0.0034 (5)	−0.0016 (5)
C12B	0.0135 (6)	0.0132 (6)	0.0125 (6)	−0.0003 (5)	−0.0023 (5)	−0.0021 (5)
C13B	0.0155 (6)	0.0123 (6)	0.0125 (6)	−0.0010 (5)	−0.0015 (5)	−0.0011 (4)

N1A—C2A	1.3483 (18)	S1A—O1A	1.4771 (10)
N1A—C1A	1.3655 (17)	S1A—C8A	1.7639 (13)
N1A—H1NA	0.89 (2)	O4A—C11A	1.3440 (16)
N2A—C2A	1.3264 (18)	O4A—H1OA	0.88 (2)
N2A—H2NA	0.88 (2)	O5A—C13A	1.3213 (16)
N2A—H3NA	0.88 (2)	O5A—H2OA	0.86 (2)
C1A—C5A	1.359 (2)	O6A—C13A	1.2238 (17)
C1A—H1AA	0.9300	C7A—C8A	1.3840 (18)
C2A—C3A	1.4203 (19)	C7A—C12A	1.3977 (18)
C3A—C4A	1.366 (2)	C7A—H7AA	0.9300
C3A—H3AA	0.9300	C8A—C9A	1.3998 (18)
C4A—C5A	1.419 (2)	C9A—C10A	1.3801 (19)
C4A—H4AA	0.9300	C9A—H9AA	0.9300
C5A—C6A	1.502 (2)	C10A—C11A	1.4047 (18)
C6A—H6AA	0.9600	C10A—H10A	0.9300
C6A—H6AB	0.9600	C11A—C12A	1.4107 (18)
C6A—H6AC	0.9600	C12A—C13A	1.4791 (18)
N1B—C2B	1.3524 (18)	S1B—O1B	1.4513 (11)
N1B—C1B	1.3673 (18)	S1B—O3B	1.4558 (10)
N1B—H1NB	0.87 (2)	S1B—O2B	1.4737 (11)
N2B—C2B	1.3231 (18)	S1B—C8B	1.7651 (13)
N2B—H2NB	0.90 (2)	O4B—C11B	1.3485 (16)
N2B—H3NB	0.87 (2)	O4B—H1OB	0.86 (3)
C1B—C5B	1.3621 (19)	O5B—C13B	1.2275 (16)
C1B—H1BA	0.9300	O6B—C13B	1.3262 (16)
C2B—C3B	1.4229 (19)	O6B—H2OB	0.86 (2)
C3B—C4B	1.363 (2)	C7B—C8B	1.3833 (18)
C3B—H3BA	0.9300	C7B—C12B	1.4009 (18)
C4B—C5B	1.420 (2)	C7B—H7BA	0.9300
C4B—H4BA	0.9300	C8B—C9B	1.3969 (19)
C5B—C6B	1.506 (2)	C9B—C10B	1.3813 (19)
C6B—H6BA	0.9600	C9B—H9BA	0.9300
C6B—H6BB	0.9600	C10B—C11B	1.3994 (19)
C6B—H6BC	0.9600	C10B—H10B	0.9300
S1A—O2A	1.4545 (10)	C11B—C12B	1.4113 (18)
S1A—O3A	1.4580 (10)	C12B—C13B	1.4736 (18)
C2A—N1A—C1A	123.30 (12)	O3A—S1A—O1A	111.39 (6)
C2A—N1A—H1NA	121.4 (12)	O2A—S1A—C8A	106.31 (6)
C1A—N1A—H1NA	115.3 (12)	O3A—S1A—C8A	107.62 (6)
C2A—N2A—H2NA	119.6 (12)	O1A—S1A—C8A	105.57 (6)
C2A—N2A—H3NA	116.7 (12)	C11A—O4A—H1OA	107.3 (15)
H2NA—N2A—H3NA	122.3 (17)	C13A—O5A—H2OA	105.9 (15)
C5A—C1A—N1A	121.50 (13)	C8A—C7A—C12A	120.22 (12)
C5A—C1A—H1AA	119.2	C8A—C7A—H7AA	119.9
N1A—C1A—H1AA	119.2	C12A—C7A—H7AA	119.9
N2A—C2A—N1A	119.77 (13)	C7A—C8A—C9A	120.24 (12)
N2A—C2A—C3A	123.29 (13)	C7A—C8A—S1A	119.75 (10)
N1A—C2A—C3A	116.94 (12)	C9A—C8A—S1A	119.99 (10)
C4A—C3A—C2A	120.04 (13)	C10A—C9A—C8A	120.17 (12)
C4A—C3A—H3AA	120.0	C10A—C9A—H9AA	119.9
C2A—C3A—H3AA	120.0	C8A—C9A—H9AA	119.9
C3A—C4A—C5A	121.37 (13)	C9A—C10A—C11A	120.30 (12)
C3A—C4A—H4AA	119.3	C9A—C10A—H10A	119.8
C5A—C4A—H4AA	119.3	C11A—C10A—H10A	119.8
C1A—C5A—C4A	116.84 (13)	O4A—C11A—C10A	117.21 (12)
C1A—C5A—C6A	121.41 (14)	O4A—C11A—C12A	123.50 (12)
C4A—C5A—C6A	121.74 (13)	C10A—C11A—C12A	119.29 (12)
C5A—C6A—H6AA	109.5	C7A—C12A—C11A	119.64 (12)
C5A—C6A—H6AB	109.5	C7A—C12A—C13A	121.04 (12)
H6AA—C6A—H6AB	109.5	C11A—C12A—C13A	119.32 (12)
C5A—C6A—H6AC	109.5	O6A—C13A—O5A	123.14 (12)
H6AA—C6A—H6AC	109.5	O6A—C13A—C12A	122.18 (12)
H6AB—C6A—H6AC	109.5	O5A—C13A—C12A	114.67 (12)
C2B—N1B—C1B	123.07 (12)	O1B—S1B—O3B	113.74 (7)
C2B—N1B—H1NB	120.3 (14)	O1B—S1B—O2B	111.56 (7)
C1B—N1B—H1NB	116.6 (14)	O3B—S1B—O2B	111.44 (6)
C2B—N2B—H2NB	119.5 (14)	O1B—S1B—C8B	106.35 (6)
C2B—N2B—H3NB	118.2 (13)	O3B—S1B—C8B	107.66 (6)
H2NB—N2B—H3NB	121.9 (19)	O2B—S1B—C8B	105.54 (6)
C5B—C1B—N1B	121.57 (13)	C11B—O4B—H1OB	108.1 (17)
C5B—C1B—H1BA	119.2	C13B—O6B—H2OB	106.8 (15)
N1B—C1B—H1BA	119.2	C8B—C7B—C12B	120.05 (12)
N2B—C2B—N1B	119.93 (13)	C8B—C7B—H7BA	120.0
N2B—C2B—C3B	123.15 (13)	C12B—C7B—H7BA	120.0
N1B—C2B—C3B	116.91 (13)	C7B—C8B—C9B	120.24 (12)
C4B—C3B—C2B	120.18 (13)	C7B—C8B—S1B	119.28 (10)
C4B—C3B—H3BA	119.9	C9B—C8B—S1B	120.38 (10)
C2B—C3B—H3BA	119.9	C10B—C9B—C8B	120.42 (13)
C3B—C4B—C5B	121.44 (13)	C10B—C9B—H9BA	119.8
C3B—C4B—H4BA	119.3	C8B—C9B—H9BA	119.8
C5B—C4B—H4BA	119.3	C9B—C10B—C11B	120.15 (13)
C1B—C5B—C4B	116.81 (13)	C9B—C10B—H10B	119.9
C1B—C5B—C6B	121.38 (14)	C11B—C10B—H10B	119.9
C4B—C5B—C6B	121.80 (13)	O4B—C11B—C10B	117.80 (12)
C5B—C6B—H6BA	109.5	O4B—C11B—C12B	122.69 (12)
C5B—C6B—H6BB	109.5	C10B—C11B—C12B	119.50 (12)
H6BA—C6B—H6BB	109.5	C7B—C12B—C11B	119.63 (12)
C5B—C6B—H6BC	109.5	C7B—C12B—C13B	121.07 (12)
H6BA—C6B—H6BC	109.5	C11B—C12B—C13B	119.29 (12)
H6BB—C6B—H6BC	109.5	O5B—C13B—O6B	122.40 (12)
O2A—S1A—O3A	113.38 (6)	O5B—C13B—C12B	122.43 (12)
O2A—S1A—O1A	112.01 (6)	O6B—C13B—C12B	115.15 (11)
C2A—N1A—C1A—C5A	−0.6 (2)	C8A—C7A—C12A—C11A	1.5 (2)
C1A—N1A—C2A—N2A	−179.12 (13)	C8A—C7A—C12A—C13A	−178.13 (12)
C1A—N1A—C2A—C3A	0.21 (19)	O4A—C11A—C12A—C7A	176.05 (12)
N2A—C2A—C3A—C4A	179.36 (13)	C10A—C11A—C12A—C7A	−3.99 (19)
N1A—C2A—C3A—C4A	0.0 (2)	O4A—C11A—C12A—C13A	−4.4 (2)
C2A—C3A—C4A—C5A	0.0 (2)	C10A—C11A—C12A—C13A	175.62 (12)
N1A—C1A—C5A—C4A	0.6 (2)	C7A—C12A—C13A—O6A	−174.32 (13)
N1A—C1A—C5A—C6A	−179.37 (13)	C11A—C12A—C13A—O6A	6.1 (2)
C3A—C4A—C5A—C1A	−0.4 (2)	C7A—C12A—C13A—O5A	6.87 (19)
C3A—C4A—C5A—C6A	179.63 (14)	C11A—C12A—C13A—O5A	−172.73 (12)
C2B—N1B—C1B—C5B	−0.8 (2)	C12B—C7B—C8B—C9B	−0.2 (2)
C1B—N1B—C2B—N2B	−178.11 (13)	C12B—C7B—C8B—S1B	176.22 (10)
C1B—N1B—C2B—C3B	1.5 (2)	O1B—S1B—C8B—C7B	33.14 (13)
N2B—C2B—C3B—C4B	178.47 (14)	O3B—S1B—C8B—C7B	155.40 (11)
N1B—C2B—C3B—C4B	−1.2 (2)	O2B—S1B—C8B—C7B	−85.48 (12)
C2B—C3B—C4B—C5B	0.0 (2)	O1B—S1B—C8B—C9B	−150.46 (12)
N1B—C1B—C5B—C4B	−0.4 (2)	O3B—S1B—C8B—C9B	−28.20 (14)
N1B—C1B—C5B—C6B	−179.94 (13)	O2B—S1B—C8B—C9B	90.92 (13)
C3B—C4B—C5B—C1B	0.8 (2)	C7B—C8B—C9B—C10B	−0.1 (2)
C3B—C4B—C5B—C6B	−179.74 (14)	S1B—C8B—C9B—C10B	−176.49 (12)
C12A—C7A—C8A—C9A	1.5 (2)	C8B—C9B—C10B—C11B	−0.1 (2)
C12A—C7A—C8A—S1A	179.70 (10)	C9B—C10B—C11B—O4B	−179.52 (13)
O2A—S1A—C8A—C7A	21.40 (13)	C9B—C10B—C11B—C12B	0.6 (2)
O3A—S1A—C8A—C7A	143.18 (11)	C8B—C7B—C12B—C11B	0.7 (2)
O1A—S1A—C8A—C7A	−97.74 (11)	C8B—C7B—C12B—C13B	−178.08 (12)
O2A—S1A—C8A—C9A	−160.40 (11)	O4B—C11B—C12B—C7B	179.22 (12)
O3A—S1A—C8A—C9A	−38.61 (12)	C10B—C11B—C12B—C7B	−1.0 (2)
O1A—S1A—C8A—C9A	80.46 (12)	O4B—C11B—C12B—C13B	−1.9 (2)
C7A—C8A—C9A—C10A	−1.9 (2)	C10B—C11B—C12B—C13B	177.88 (13)
S1A—C8A—C9A—C10A	179.89 (11)	C7B—C12B—C13B—O5B	−178.04 (13)
C8A—C9A—C10A—C11A	−0.7 (2)	C11B—C12B—C13B—O5B	3.1 (2)
C9A—C10A—C11A—O4A	−176.43 (12)	C7B—C12B—C13B—O6B	3.28 (18)
C9A—C10A—C11A—C12A	3.6 (2)	C11B—C12B—C13B—O6B	−175.54 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O4A—H1OA···O6A	0.88 (2)	1.84 (2)	2.6135 (14)	147 (2)
O4A—H1OA···O1Bi	0.88 (2)	2.39 (2)	2.9581 (14)	123.2 (18)
O5A—H2OA···O2Bii	0.86 (2)	1.80 (2)	2.6609 (14)	172 (2)
O4B—H1OB···O5B	0.86 (3)	1.83 (2)	2.5918 (14)	147 (2)
O4B—H1OB···O2Aiii	0.86 (3)	2.45 (2)	3.0349 (14)	125.4 (18)
O6B—H2OB···O1A	0.86 (2)	1.81 (2)	2.6664 (14)	178 (2)
N1A—H1NA···O3Aiv	0.894 (19)	2.066 (19)	2.9057 (15)	156.0 (17)
N2A—H2NA···O2Aiv	0.878 (19)	2.167 (19)	3.0043 (16)	159.1 (17)
N2A—H2NA···O5Bv	0.878 (19)	2.417 (19)	2.8235 (16)	108.7 (13)
N2A—H3NA···O1Av	0.88 (2)	2.17 (2)	3.0472 (16)	175.6 (15)
N1B—H1NB···O3Bii	0.87 (2)	2.02 (2)	2.8547 (16)	161 (2)
N2B—H2NB···O1Bii	0.90 (2)	2.04 (2)	2.9188 (17)	166 (2)
N2B—H2NB···O6Avi	0.90 (2)	2.45 (2)	2.8254 (16)	105.9 (17)
N2B—H3NB···O2Bi	0.87 (2)	2.26 (2)	3.1270 (17)	177.1 (18)
C7A—H7AA···O4Biii	0.93	2.58	3.4257 (16)	152
C7B—H7BA···O4Ai	0.93	2.48	3.3116 (16)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4A—H1OA⋯O6A	0.88 (2)	1.84 (2)	2.6135 (14)	147 (2)
O4A—H1OA⋯O1Bi	0.88 (2)	2.39 (2)	2.9581 (14)	123.2 (18)
O5A—H2OA⋯O2Bii	0.86 (2)	1.80 (2)	2.6609 (14)	172 (2)
O4B—H1OB⋯O5B	0.86 (3)	1.83 (2)	2.5918 (14)	147 (2)
O4B—H1OB⋯O2Aiii	0.86 (3)	2.45 (2)	3.0349 (14)	125.4 (18)
O6B—H2OB⋯O1A	0.86 (2)	1.81 (2)	2.6664 (14)	178 (2)
N1A—H1NA⋯O3Aiv	0.894 (19)	2.066 (19)	2.9057 (15)	156.0 (17)
N2A—H2NA⋯O2Aiv	0.878 (19)	2.167 (19)	3.0043 (16)	159.1 (17)
N2A—H2NA⋯O5Bv	0.878 (19)	2.417 (19)	2.8235 (16)	108.7 (13)
N2A—H3NA⋯O1Av	0.88 (2)	2.17 (2)	3.0472 (16)	175.6 (15)
N1B—H1NB⋯O3Bii	0.87 (2)	2.02 (2)	2.8547 (16)	161 (2)
N2B—H2NB⋯O1Bii	0.90 (2)	2.04 (2)	2.9188 (17)	166 (2)
N2B—H2NB⋯O6Avi	0.90 (2)	2.45 (2)	2.8254 (16)	105.9 (17)
N2B—H3NB⋯O2Bi	0.87 (2)	2.26 (2)	3.1270 (17)	177.1 (18)
C7A—H7AA⋯O4Biii	0.93	2.58	3.4257 (16)	152
C7B—H7BA⋯O4Ai	0.93	2.48	3.3116 (16)	148

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