2-Carboxy-quinolinium-2,4,6-trinitro-benzene-sulfonate-quinolinium-2-carboxyl-ate (1/1/1).

The structure of the title adduct compound, C(10)H(8)NO(2) (+)·C(6)H(2)N(3)O(9)S(-)·C(10)H(7)NO(2), from the reaction of 2,4,6-trinitro-benzene-sulfonic acid (picrylsulfonic acid) with quinoline-2-carboxylic acid (quinaldic acid) in 2-propanol-water, has been determined at 130 (2) K. The cation and the adduct species form a twisted cyclic hydrogen-bonded R(2) (2)(10) pseudo-dimer which is extended into a one-dimensional chain structure through short head-to-tail carboxylic acid O-H⋯O(carbox-yl) associations [O⋯O = 2.4711 (19) Å]. The picrylsulfonate anions are attached peripherally by single N-H⋯O(sulfonate) hydrogen bonds [N⋯O = 2.8643 (19) Å].

Related literature

For other related picrylsulfonate and quinaldic acid structures, see: Russell & Ward (1997 ▶); Smith et al. (2004 ▶); Smith, Wermuth & Healy (2006 ▶); Smith, Wermuth & White (2006 ▶); Smith, Wermuth, Healy & White (2007 ▶); Smith, Wermuth & White (2007 ▶); Dobrzyńska & Jerzykiewicz (2004 ▶).

For graph-set nomenclature, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C10H8NO2 +·C6H2N3O9S−·C10H7NO2

M = 639.51

Triclinic,

a = 7.8872 (6) Å

b = 12.4753 (10) Å

c = 14.6617 (12) Å

α = 66.227 (1)°

β = 74.997 (2)°

γ = 82.191 (2)°

V = 1274.42 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 130 (2) K

0.40 × 0.30 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.93, T max = 0.98

6761 measured reflections

4446 independent reflections

3779 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 1.00

4446 reflections

419 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062757/sf2012sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062757/sf2012Isup2.hkl

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

C10H8NO2+·C6H2N3O9S–·C10H7NO2	Z = 2
Mr = 639.51	F000 = 656
Triclinic, P1	Dx = 1.667 Mg m−3
Hall symbol: -P 1	Melting point = 495–496 K
a = 7.8872 (6) Å	Mo Kα radiation λ = 0.71073 Å
b = 12.4753 (10) Å	Cell parameters from 3558 reflections
c = 14.6617 (12) Å	θ = 2.7–27.5º
α = 66.227 (1)º	µ = 0.21 mm−1
β = 74.997 (2)º	T = 130 (2) K
γ = 82.191 (2)º	Plate, colourless
V = 1274.42 (18) Å3	0.40 × 0.30 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	4446 independent reflections
Radiation source: sealed tube	3779 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
T = 130(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Bruker, 1999)	h = −9→9
Tmin = 0.93, Tmax = 0.98	k = −14→14
6761 measured reflections	l = −10→17

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0504P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.090	(Δ/σ)max = 0.001
S = 1.00	Δρmax = 0.26 e Å−3
4446 reflections	Δρmin = −0.36 e Å−3
419 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0035 (9)
Secondary atom site location: difference Fourier map

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O21A	0.58977 (15)	0.59940 (10)	0.39221 (10)	0.0254 (4)
O21B	1.00107 (15)	0.64175 (10)	0.34714 (10)	0.0241 (4)
O22A	0.38775 (15)	0.50663 (10)	0.36987 (9)	0.0228 (4)
O22B	1.16069 (15)	0.60475 (11)	0.46423 (10)	0.0259 (4)
N1A	0.84672 (18)	0.51549 (12)	0.27485 (11)	0.0189 (4)
N1B	0.74154 (18)	0.73921 (12)	0.45119 (11)	0.0185 (5)
C2A	0.6823 (2)	0.48449 (14)	0.29343 (13)	0.0195 (5)
C2B	0.8899 (2)	0.70550 (14)	0.48319 (13)	0.0180 (5)
C3A	0.6451 (2)	0.41203 (14)	0.24976 (14)	0.0223 (5)
C3B	0.9103 (2)	0.72614 (14)	0.56645 (13)	0.0213 (5)
C4A	0.7771 (2)	0.37568 (15)	0.18609 (14)	0.0236 (6)
C4B	0.7771 (2)	0.78111 (15)	0.61378 (14)	0.0232 (5)
C5A	1.0908 (2)	0.38090 (16)	0.09579 (14)	0.0274 (6)
C5B	0.4742 (2)	0.86973 (15)	0.62801 (14)	0.0246 (6)
C6A	1.2556 (2)	0.41723 (16)	0.07874 (14)	0.0284 (6)
C6B	0.3237 (2)	0.89788 (15)	0.59302 (15)	0.0267 (6)
C7A	1.2868 (2)	0.48655 (16)	0.12761 (14)	0.0265 (6)
C7B	0.3095 (2)	0.87352 (15)	0.50922 (14)	0.0248 (6)
C8A	1.1553 (2)	0.51932 (15)	0.19338 (13)	0.0224 (5)
C8B	0.4452 (2)	0.82010 (14)	0.46165 (14)	0.0217 (5)
C9A	0.9842 (2)	0.48298 (14)	0.21127 (13)	0.0200 (5)
C9B	0.6008 (2)	0.79115 (14)	0.49680 (13)	0.0176 (5)
C10A	0.9496 (2)	0.41196 (14)	0.16341 (14)	0.0217 (6)
C10B	0.6178 (2)	0.81513 (14)	0.58089 (13)	0.0202 (5)
C21A	0.5445 (2)	0.53589 (14)	0.35874 (13)	0.0198 (5)
C21B	1.0288 (2)	0.64568 (14)	0.42510 (14)	0.0206 (5)
S1	0.67941 (6)	0.96877 (4)	0.18966 (3)	0.0221 (1)
O11	0.79371 (16)	1.05360 (11)	0.18376 (10)	0.0275 (4)
O12	0.49579 (16)	0.99398 (11)	0.22231 (9)	0.0270 (4)
O13	0.73845 (16)	0.84886 (11)	0.23828 (9)	0.0288 (4)
O21	0.48489 (16)	0.78413 (11)	0.16864 (10)	0.0287 (4)
O22	0.69059 (17)	0.69083 (10)	0.09636 (10)	0.0296 (4)
O41	0.89200 (16)	0.91344 (11)	−0.26263 (10)	0.0280 (4)
O42	0.90947 (17)	1.10219 (11)	−0.31897 (9)	0.0328 (4)
O61	0.92941 (16)	1.23709 (11)	−0.02903 (10)	0.0295 (4)
O62	0.64569 (16)	1.23611 (11)	0.02533 (10)	0.0295 (4)
N2	0.61840 (19)	0.78074 (13)	0.10551 (11)	0.0222 (5)
N4	0.87752 (18)	1.00599 (13)	−0.25023 (11)	0.0224 (5)
N6	0.78729 (19)	1.19400 (12)	−0.00650 (11)	0.0219 (5)
C1	0.7125 (2)	0.98489 (15)	0.05707 (13)	0.0182 (5)
C2	0.6957 (2)	0.89262 (14)	0.02920 (13)	0.0183 (5)
C3	0.7470 (2)	0.89921 (14)	−0.07008 (13)	0.0189 (5)
C4	0.8198 (2)	1.00040 (15)	−0.14463 (13)	0.0187 (5)
C5	0.8392 (2)	1.09627 (15)	−0.12484 (13)	0.0194 (5)
C6	0.7815 (2)	1.08587 (14)	−0.02403 (13)	0.0189 (5)
H1A	0.863 (3)	0.5625 (18)	0.3025 (16)	0.036 (6)*
H1B	0.737 (3)	0.7269 (19)	0.3989 (18)	0.047 (7)*
H3A	0.52850	0.38810	0.26420	0.0270*
H3B	1.01600	0.70210	0.59000	0.0260*
H4A	0.75210	0.32560	0.15700	0.0280*
H4B	0.79170	0.79670	0.66950	0.0280*
H5A	1.07080	0.33450	0.06200	0.0330*
H5B	0.48240	0.88690	0.68420	0.0300*
H6A	1.34990	0.39550	0.03350	0.0340*
H6B	0.22730	0.93430	0.62530	0.0320*
H7A	1.40250	0.51120	0.11450	0.0320*
H7B	0.20370	0.89460	0.48550	0.0300*
H8A	1.17860	0.56560	0.22640	0.0270*
H8B	0.43400	0.80300	0.40590	0.0260*
H22A	0.298 (3)	0.5460 (19)	0.4062 (18)	0.057 (7)*
H3	0.73240	0.83520	−0.08650	0.0230*
H5	0.88950	1.16590	−0.17750	0.0230*

	U11	U22	U33	U12	U13	U23
O21A	0.0235 (7)	0.0263 (7)	0.0307 (8)	−0.0017 (5)	−0.0044 (6)	−0.0160 (6)
O21B	0.0219 (7)	0.0299 (7)	0.0259 (7)	−0.0004 (5)	−0.0044 (6)	−0.0169 (6)
O22A	0.0186 (7)	0.0258 (7)	0.0267 (7)	−0.0008 (5)	−0.0045 (6)	−0.0131 (6)
O22B	0.0215 (7)	0.0315 (7)	0.0275 (7)	0.0055 (5)	−0.0079 (6)	−0.0148 (6)
N1A	0.0204 (8)	0.0189 (7)	0.0192 (8)	−0.0005 (6)	−0.0049 (6)	−0.0090 (7)
N1B	0.0215 (8)	0.0199 (8)	0.0162 (8)	−0.0008 (6)	−0.0036 (6)	−0.0094 (7)
C2A	0.0225 (9)	0.0155 (8)	0.0176 (9)	0.0001 (7)	−0.0066 (8)	−0.0025 (7)
C2B	0.0198 (9)	0.0145 (8)	0.0174 (9)	−0.0026 (7)	−0.0043 (7)	−0.0031 (7)
C3A	0.0227 (9)	0.0185 (9)	0.0246 (10)	−0.0028 (7)	−0.0050 (8)	−0.0068 (8)
C3B	0.0228 (9)	0.0216 (9)	0.0190 (9)	−0.0024 (7)	−0.0062 (8)	−0.0060 (8)
C4A	0.0301 (10)	0.0191 (9)	0.0246 (10)	−0.0015 (8)	−0.0070 (8)	−0.0106 (8)
C4B	0.0306 (10)	0.0237 (9)	0.0180 (9)	−0.0064 (8)	−0.0054 (8)	−0.0092 (8)
C5A	0.0334 (11)	0.0268 (10)	0.0238 (10)	0.0017 (8)	−0.0044 (9)	−0.0136 (9)
C5B	0.0326 (11)	0.0208 (9)	0.0202 (10)	−0.0043 (8)	0.0018 (8)	−0.0113 (8)
C6A	0.0278 (10)	0.0302 (10)	0.0237 (10)	0.0040 (8)	−0.0005 (8)	−0.0116 (9)
C6B	0.0261 (10)	0.0208 (9)	0.0275 (11)	−0.0007 (8)	0.0048 (8)	−0.0103 (8)
C7A	0.0217 (10)	0.0296 (10)	0.0244 (10)	0.0000 (8)	−0.0031 (8)	−0.0080 (9)
C7B	0.0218 (10)	0.0218 (9)	0.0279 (11)	−0.0018 (7)	−0.0016 (8)	−0.0086 (8)
C8A	0.0224 (9)	0.0240 (9)	0.0210 (10)	−0.0007 (8)	−0.0061 (8)	−0.0081 (8)
C8B	0.0234 (9)	0.0210 (9)	0.0206 (10)	−0.0035 (7)	−0.0032 (8)	−0.0081 (8)
C9A	0.0239 (9)	0.0179 (9)	0.0155 (9)	0.0030 (7)	−0.0049 (7)	−0.0046 (7)
C9B	0.0203 (9)	0.0147 (8)	0.0165 (9)	−0.0021 (7)	−0.0003 (7)	−0.0065 (7)
C10A	0.0255 (10)	0.0178 (9)	0.0208 (10)	0.0020 (7)	−0.0065 (8)	−0.0065 (8)
C10B	0.0260 (10)	0.0156 (8)	0.0171 (9)	−0.0050 (7)	−0.0004 (8)	−0.0057 (7)
C21A	0.0225 (9)	0.0160 (8)	0.0190 (9)	−0.0001 (7)	−0.0054 (8)	−0.0046 (8)
C21B	0.0197 (9)	0.0190 (9)	0.0221 (10)	−0.0035 (7)	−0.0031 (8)	−0.0069 (8)
S1	0.0203 (2)	0.0327 (3)	0.0160 (2)	0.0025 (2)	−0.0048 (2)	−0.0128 (2)
O11	0.0244 (7)	0.0413 (8)	0.0250 (7)	−0.0010 (6)	−0.0066 (6)	−0.0205 (6)
O12	0.0215 (7)	0.0408 (8)	0.0223 (7)	0.0018 (6)	−0.0029 (5)	−0.0179 (6)
O13	0.0304 (7)	0.0362 (8)	0.0181 (7)	0.0055 (6)	−0.0078 (6)	−0.0094 (6)
O21	0.0224 (7)	0.0347 (7)	0.0228 (7)	−0.0028 (6)	−0.0002 (6)	−0.0072 (6)
O22	0.0380 (8)	0.0202 (7)	0.0280 (7)	0.0022 (6)	−0.0056 (6)	−0.0087 (6)
O41	0.0296 (7)	0.0351 (8)	0.0272 (7)	−0.0040 (6)	−0.0021 (6)	−0.0217 (6)
O42	0.0425 (8)	0.0357 (8)	0.0172 (7)	−0.0152 (6)	−0.0019 (6)	−0.0057 (6)
O61	0.0277 (7)	0.0296 (7)	0.0372 (8)	−0.0040 (6)	−0.0095 (6)	−0.0166 (6)
O62	0.0289 (7)	0.0296 (7)	0.0350 (8)	0.0063 (6)	−0.0075 (6)	−0.0196 (6)
N2	0.0228 (8)	0.0248 (8)	0.0200 (8)	0.0008 (6)	−0.0081 (7)	−0.0082 (7)
N4	0.0209 (8)	0.0300 (9)	0.0175 (8)	−0.0058 (7)	−0.0023 (6)	−0.0101 (7)
N6	0.0229 (9)	0.0238 (8)	0.0225 (8)	0.0009 (7)	−0.0072 (7)	−0.0116 (7)
C1	0.0151 (8)	0.0244 (9)	0.0168 (9)	0.0037 (7)	−0.0057 (7)	−0.0096 (8)
C2	0.0172 (9)	0.0182 (8)	0.0185 (9)	0.0016 (7)	−0.0056 (7)	−0.0059 (7)
C3	0.0183 (9)	0.0202 (9)	0.0213 (9)	0.0030 (7)	−0.0067 (7)	−0.0110 (8)
C4	0.0169 (9)	0.0249 (9)	0.0160 (9)	0.0012 (7)	−0.0040 (7)	−0.0100 (8)
C5	0.0171 (9)	0.0208 (9)	0.0203 (10)	0.0006 (7)	−0.0053 (7)	−0.0075 (8)
C6	0.0174 (9)	0.0214 (9)	0.0228 (10)	0.0037 (7)	−0.0078 (8)	−0.0129 (8)

S1—C1	1.8232 (18)	C5A—C10A	1.412 (3)
S1—O13	1.4442 (15)	C5A—C6A	1.363 (2)
S1—O11	1.4440 (15)	C5B—C6B	1.361 (2)
S1—O12	1.4367 (14)	C5B—C10B	1.410 (3)
O21A—C21A	1.215 (2)	C6A—C7A	1.404 (3)
O21B—C21B	1.239 (2)	C6B—C7B	1.413 (3)
O22A—C21A	1.288 (2)	C7A—C8A	1.363 (3)
O22B—C21B	1.265 (2)	C7B—C8B	1.368 (3)
O22A—H22A	0.97 (2)	C8A—C9A	1.408 (2)
O21—N2	1.218 (2)	C8B—C9B	1.400 (2)
O22—N2	1.228 (2)	C9A—C10A	1.421 (3)
O41—N4	1.226 (2)	C9B—C10B	1.422 (2)
O42—N4	1.223 (2)	C3A—H3A	0.9500
O61—N6	1.218 (2)	C3B—H3B	0.9500
O62—N6	1.229 (2)	C4A—H4A	0.9500
N1A—C2A	1.332 (2)	C4B—H4B	0.9500
N1A—C9A	1.368 (2)	C5A—H5A	0.9500
N1B—C9B	1.367 (2)	C5B—H5B	0.9500
N1B—C2B	1.326 (2)	C6A—H6A	0.9500
N1A—H1A	0.87 (2)	C6B—H6B	0.9500
N1B—H1B	0.85 (2)	C7A—H7A	0.9500
N2—C2	1.480 (2)	C7B—H7B	0.9500
N4—C4	1.472 (2)	C8A—H8A	0.9500
N6—C6	1.480 (2)	C8B—H8B	0.9500
C2A—C3A	1.396 (3)	C1—C2	1.399 (3)
C2A—C21A	1.509 (3)	C1—C6	1.393 (3)
C2B—C21B	1.513 (3)	C2—C3	1.377 (2)
C2B—C3B	1.396 (2)	C3—C4	1.370 (3)
C3A—C4A	1.368 (3)	C4—C5	1.375 (3)
C3B—C4B	1.366 (3)	C5—C6	1.386 (2)
C4A—C10A	1.407 (2)	C3—H3	0.9500
C4B—C10B	1.413 (2)	C5—H5	0.9500
O12—S1—O13	115.62 (8)	C5B—C10B—C9B	118.43 (15)
O12—S1—C1	105.96 (8)	C4B—C10B—C5B	123.52 (16)
O13—S1—C1	102.31 (8)	O21A—C21A—C2A	118.93 (15)
O11—S1—C1	103.56 (8)	O22A—C21A—C2A	113.06 (15)
O11—S1—O12	114.08 (9)	O21A—C21A—O22A	127.99 (17)
O11—S1—O13	113.42 (8)	O21B—C21B—C2B	117.66 (15)
C21A—O22A—H22A	113.0 (15)	O22B—C21B—C2B	114.26 (16)
C2A—N1A—C9A	123.24 (16)	O21B—C21B—O22B	128.07 (17)
C2B—N1B—C9B	124.03 (15)	C2A—C3A—H3A	120.00
C9A—N1A—H1A	120.2 (16)	C4A—C3A—H3A	120.00
C2A—N1A—H1A	116.5 (16)	C2B—C3B—H3B	120.00
C9B—N1B—H1B	119.9 (17)	C4B—C3B—H3B	120.00
C2B—N1B—H1B	116.0 (17)	C10A—C4A—H4A	120.00
O21—N2—C2	118.58 (16)	C3A—C4A—H4A	120.00
O22—N2—C2	116.42 (14)	C10B—C4B—H4B	120.00
O21—N2—O22	124.89 (16)	C3B—C4B—H4B	120.00
O41—N4—C4	117.43 (15)	C6A—C5A—H5A	120.00
O41—N4—O42	124.80 (15)	C10A—C5A—H5A	120.00
O42—N4—C4	117.77 (16)	C6B—C5B—H5B	120.00
O61—N6—C6	118.03 (15)	C10B—C5B—H5B	120.00
O62—N6—C6	116.65 (15)	C5A—C6A—H6A	120.00
O61—N6—O62	125.23 (16)	C7A—C6A—H6A	120.00
C3A—C2A—C21A	123.84 (15)	C5B—C6B—H6B	120.00
N1A—C2A—C21A	116.27 (16)	C7B—C6B—H6B	120.00
N1A—C2A—C3A	119.84 (16)	C6A—C7A—H7A	119.00
N1B—C2B—C3B	119.65 (16)	C8A—C7A—H7A	119.00
C3B—C2B—C21B	123.91 (15)	C6B—C7B—H7B	119.00
N1B—C2B—C21B	116.44 (15)	C8B—C7B—H7B	119.00
C2A—C3A—C4A	119.76 (16)	C7A—C8A—H8A	121.00
C2B—C3B—C4B	119.51 (16)	C9A—C8A—H8A	121.00
C3A—C4A—C10A	120.41 (17)	C7B—C8B—H8B	121.00
C3B—C4B—C10B	120.86 (17)	C9B—C8B—H8B	121.00
C6A—C5A—C10A	120.34 (18)	S1—C1—C2	123.06 (14)
C6B—C5B—C10B	120.03 (17)	S1—C1—C6	121.54 (14)
C5A—C6A—C7A	120.44 (17)	C2—C1—C6	114.77 (16)
C5B—C6B—C7B	120.70 (17)	N2—C2—C1	121.68 (15)
C6A—C7A—C8A	121.67 (16)	N2—C2—C3	115.28 (16)
C6B—C7B—C8B	121.20 (16)	C1—C2—C3	123.04 (16)
C7A—C8A—C9A	118.51 (17)	C2—C3—C4	118.32 (17)
C7B—C8B—C9B	118.57 (17)	N4—C4—C3	118.03 (17)
C8A—C9A—C10A	120.87 (16)	N4—C4—C5	119.17 (16)
N1A—C9A—C8A	120.92 (16)	C3—C4—C5	122.80 (16)
N1A—C9A—C10A	118.21 (15)	C4—C5—C6	116.46 (16)
N1B—C9B—C8B	121.07 (16)	N6—C6—C1	120.05 (15)
N1B—C9B—C10B	117.84 (15)	N6—C6—C5	115.32 (15)
C8B—C9B—C10B	121.08 (16)	C1—C6—C5	124.54 (17)
C4A—C10A—C5A	123.37 (17)	C2—C3—H3	121.00
C5A—C10A—C9A	118.16 (16)	C4—C3—H3	121.00
C4A—C10A—C9A	118.47 (16)	C4—C5—H5	122.00
C4B—C10B—C9B	118.05 (16)	C6—C5—H5	122.00
O13—S1—C1—C6	−138.21 (15)	C3A—C4A—C10A—C9A	2.5 (3)
O12—S1—C1—C2	−89.31 (16)	C3B—C4B—C10B—C5B	178.54 (18)
O11—S1—C1—C2	150.32 (15)	C3B—C4B—C10B—C9B	−0.4 (3)
O11—S1—C1—C6	−20.10 (17)	C6A—C5A—C10A—C4A	−178.72 (18)
O12—S1—C1—C6	100.27 (15)	C6A—C5A—C10A—C9A	0.9 (3)
O13—S1—C1—C2	32.21 (16)	C10A—C5A—C6A—C7A	−0.4 (3)
C9A—N1A—C2A—C21A	−175.27 (16)	C6B—C5B—C10B—C9B	0.2 (3)
C9A—N1A—C2A—C3A	2.3 (3)	C10B—C5B—C6B—C7B	−0.3 (3)
C2A—N1A—C9A—C10A	−0.5 (3)	C6B—C5B—C10B—C4B	−178.74 (18)
C2A—N1A—C9A—C8A	179.27 (17)	C5A—C6A—C7A—C8A	0.3 (3)
C9B—N1B—C2B—C3B	−2.1 (3)	C5B—C6B—C7B—C8B	0.7 (3)
C2B—N1B—C9B—C10B	2.9 (3)	C6A—C7A—C8A—C9A	−0.6 (3)
C9B—N1B—C2B—C21B	177.93 (16)	C6B—C7B—C8B—C9B	−0.9 (3)
C2B—N1B—C9B—C8B	−177.26 (17)	C7A—C8A—C9A—C10A	1.1 (3)
O21—N2—C2—C3	−134.74 (17)	C7A—C8A—C9A—N1A	−178.59 (17)
O21—N2—C2—C1	44.5 (2)	C7B—C8B—C9B—N1B	−179.04 (17)
O22—N2—C2—C1	−139.19 (17)	C7B—C8B—C9B—C10B	0.8 (3)
O22—N2—C2—C3	41.6 (2)	N1A—C9A—C10A—C4A	−1.9 (3)
O41—N4—C4—C3	−15.1 (2)	C8A—C9A—C10A—C5A	−1.3 (3)
O42—N4—C4—C5	−13.6 (2)	N1A—C9A—C10A—C5A	178.43 (16)
O41—N4—C4—C5	165.55 (16)	C8A—C9A—C10A—C4A	178.37 (17)
O42—N4—C4—C3	165.79 (16)	N1B—C9B—C10B—C4B	−1.6 (3)
O61—N6—C6—C1	122.44 (18)	N1B—C9B—C10B—C5B	179.39 (16)
O62—N6—C6—C1	−61.0 (2)	C8B—C9B—C10B—C4B	178.57 (17)
O62—N6—C6—C5	115.70 (17)	C8B—C9B—C10B—C5B	−0.4 (3)
O61—N6—C6—C5	−60.9 (2)	S1—C1—C2—N2	11.3 (2)
N1A—C2A—C3A—C4A	−1.6 (3)	S1—C1—C2—C3	−169.48 (14)
C21A—C2A—C3A—C4A	175.71 (17)	C6—C1—C2—N2	−177.64 (15)
C3A—C2A—C21A—O22A	−0.4 (2)	C6—C1—C2—C3	1.5 (3)
N1A—C2A—C21A—O21A	−1.6 (2)	S1—C1—C6—N6	−15.7 (2)
N1A—C2A—C21A—O22A	177.05 (15)	S1—C1—C6—C5	167.94 (14)
C3A—C2A—C21A—O21A	−178.99 (17)	C2—C1—C6—N6	173.10 (15)
N1B—C2B—C3B—C4B	−0.2 (3)	C2—C1—C6—C5	−3.2 (3)
C21B—C2B—C3B—C4B	179.87 (17)	N2—C2—C3—C4	−179.94 (15)
N1B—C2B—C21B—O21B	6.2 (2)	C1—C2—C3—C4	0.8 (3)
C3B—C2B—C21B—O22B	6.6 (3)	C2—C3—C4—N4	178.82 (15)
C3B—C2B—C21B—O21B	−173.77 (17)	C2—C3—C4—C5	−1.8 (3)
N1B—C2B—C21B—O22B	−173.36 (16)	N4—C4—C5—C6	179.65 (15)
C2A—C3A—C4A—C10A	−0.8 (3)	C3—C4—C5—C6	0.3 (3)
C2B—C3B—C4B—C10B	1.3 (3)	C4—C5—C6—N6	−174.09 (15)
C3A—C4A—C10A—C5A	−177.87 (18)	C4—C5—C6—C1	2.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O21A	0.87 (2)	2.31 (2)	2.690 (2)	106.3 (18)
N1A—H1A···O21B	0.87 (2)	1.94 (2)	2.761 (2)	155 (2)
N1B—H1B···O13	0.85 (2)	2.23 (2)	2.8643 (19)	132 (2)
N1B—H1B···O21A	0.85 (2)	2.14 (3)	2.746 (2)	128 (2)
N1B—H1B···O21B	0.85 (2)	2.30 (3)	2.683 (2)	108 (2)
O22A—H22A···O22Bi	0.97 (2)	1.50 (2)	2.4711 (19)	179 (3)
C4B—H4B···O41ii	0.95	2.37	3.240 (2)	152
C5B—H5B···O12iii	0.95	2.44	3.339 (2)	158
C8A—H8A···O21B	0.95	2.39	3.122 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯O21A	0.87 (2)	2.31 (2)	2.690 (2)	106.3 (18)
N1A—H1A⋯O21B	0.87 (2)	1.94 (2)	2.761 (2)	155 (2)
N1B—H1B⋯O13	0.85 (2)	2.23 (2)	2.8643 (19)	132 (2)
N1B—H1B⋯O21A	0.85 (2)	2.14 (3)	2.746 (2)	128 (2)
N1B—H1B⋯O21B	0.85 (2)	2.30 (3)	2.683 (2)	108 (2)
O22A—H22A⋯O22Bi	0.97 (2)	1.50 (2)	2.4711 (19)	179 (3)
C4B—H4B⋯O41ii	0.95	2.37	3.240 (2)	152
C5B—H5B⋯O12iii	0.95	2.44	3.339 (2)	158
C8A—H8A⋯O21B	0.95	2.39	3.122 (2)	134

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