Bis(4-carbamoylpiperidinium) biphenyl-4,4'-disulfonate.

In the title isonipecotamide salt 2C(6)H(13)N(2)O(+)·C(12)H(8)O(6)S(2) (2-), the asymmetric unit comprises one biphenyl-4,4'-disulfonate dianion which lies across a crystallographic inversion centre and another in a general position [dihedral angle between the two phenyl rings is 37.1 (1)°], together with three isonipecotamide cations. Two of these cations give a cyclic homomeric amide-amide dimer inter-action [graph set R(2) (2)(8)], the other giving a similar dimeric inter-action but across an inversion centre, both dimers then forming lateral cyclic R(4) (2)(8) pyrimidinium-amide N-H⋯O inter-actions. These units are linked both laterally and longitudinally to the sulfonate groups of the dianions through piperidinium N-H⋯O hydrogen bonds, giving a three-dimensional framework structure.

Related literature

For structural data on bipyridine-4,4′-disulfonate salts and related compounds, see: Swift & Ward (1998 ▶); Swift et al. (1998 ▶); Holman & Ward (2000 ▶); Liao et al. (2001 ▶); Smith et al. (2010 ▶). For isonipecotamide salt structures, see: Smith & Wermuth (2010a ▶,b ▶,c ▶). For graph-set motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

2C6H13N2O+·C12H8O6S2 −

M = 570.69

Triclinic,

a = 8.2530 (4) Å

b = 16.0418 (8) Å

c = 16.7408 (11) Å

α = 112.255 (5)°

β = 97.166 (5)°

γ = 101.714 (4)°

V = 1958.2 (2) Å3

Z = 3

Mo Kα radiation

μ = 0.26 mm−1

T = 200 K

0.40 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Gemini-S Ultra CCD-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.911, T max = 0.980

23474 measured reflections

7679 independent reflections

6364 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.09

7679 reflections

562 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.51 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within WinGX (Farrugia, 1999 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045526/fl2328sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045526/fl2328Isup2.hkl

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

2C6H13N2O+·C12H8O6S2−	Z = 3
Mr = 570.69	F(000) = 906
Triclinic, P1	Dx = 1.452 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2530 (4) Å	Cell parameters from 8867 reflections
b = 16.0418 (8) Å	θ = 3.2–28.8°
c = 16.7408 (11) Å	µ = 0.26 mm−1
α = 112.255 (5)°	T = 200 K
β = 97.166 (5)°	Plate, colourless
γ = 101.714 (4)°	0.40 × 0.40 × 0.20 mm
V = 1958.2 (2) Å3

Oxford Diffraction Gemini-S Ultra CCD-detector diffractometer	7679 independent reflections
Radiation source: Enhance (Mo) X-ray source	6364 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 26.0°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −10→10
Tmin = 0.911, Tmax = 0.980	k = −19→19
23474 measured reflections	l = −20→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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0573P)2 + 0.215P] where P = (Fo2 + 2Fc2)/3
7679 reflections	(Δ/σ)max = 0.002
562 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

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
S4A	0.82703 (5)	0.13767 (3)	0.09291 (3)	0.0190 (1)
S41A	1.06493 (5)	0.86976 (3)	0.25435 (3)	0.0176 (1)
O41A	0.66717 (15)	0.10391 (8)	0.02904 (8)	0.0316 (4)
O42A	0.96363 (15)	0.10371 (8)	0.05433 (9)	0.0298 (4)
O43A	0.81159 (17)	0.12200 (8)	0.17254 (8)	0.0320 (4)
O44A	1.20766 (16)	0.92224 (8)	0.32924 (8)	0.0325 (4)
O45A	1.09354 (15)	0.87918 (8)	0.17312 (8)	0.0262 (4)
O46A	0.90432 (15)	0.88868 (8)	0.27438 (8)	0.0274 (4)
C1A	0.9569 (2)	0.45553 (11)	0.17383 (11)	0.0232 (5)
C2A	1.0003 (3)	0.39525 (13)	0.09888 (13)	0.0360 (6)
C3A	0.9652 (3)	0.29980 (13)	0.07588 (13)	0.0328 (6)
C4A	0.88737 (19)	0.26213 (11)	0.12834 (10)	0.0187 (5)
C5A	0.8481 (2)	0.32059 (11)	0.20427 (11)	0.0253 (5)
C6A	0.8821 (2)	0.41650 (12)	0.22664 (11)	0.0264 (5)
C11A	0.9856 (2)	0.55740 (11)	0.19442 (11)	0.0228 (5)
C21A	0.9620 (3)	0.58684 (12)	0.12643 (12)	0.0317 (6)
C31A	0.9889 (2)	0.68127 (12)	0.14384 (11)	0.0278 (5)
C41A	1.03869 (19)	0.74839 (10)	0.23078 (10)	0.0179 (4)
C51A	1.0628 (2)	0.72092 (11)	0.29954 (11)	0.0222 (5)
C61A	1.0355 (2)	0.62611 (12)	0.28137 (11)	0.0254 (5)
S4B	0.68682 (5)	0.13983 (3)	0.41642 (3)	0.0197 (1)
O41B	0.76007 (16)	0.12258 (8)	0.49054 (8)	0.0296 (4)
O42B	0.50633 (15)	0.13283 (9)	0.41138 (9)	0.0337 (4)
O43B	0.7264 (2)	0.08532 (9)	0.33419 (9)	0.0468 (5)
C1B	0.9546 (2)	0.44969 (10)	0.48803 (10)	0.0204 (5)
C2B	0.8136 (2)	0.42503 (12)	0.52040 (12)	0.0295 (6)
C3B	0.7291 (2)	0.33169 (12)	0.49779 (12)	0.0297 (6)
C4B	0.7862 (2)	0.26027 (11)	0.44236 (10)	0.0189 (5)
C5B	0.9239 (3)	0.28263 (13)	0.40861 (15)	0.0405 (7)
C6B	1.0080 (3)	0.37604 (13)	0.43145 (15)	0.0445 (7)
O41C	0.57028 (18)	0.62179 (8)	0.78553 (9)	0.0366 (4)
N1C	0.81523 (19)	0.94193 (10)	0.83011 (10)	0.0240 (4)
N41C	0.5061 (3)	0.58553 (13)	0.64025 (13)	0.0569 (8)
C2C	0.8147 (2)	0.88438 (12)	0.73590 (11)	0.0253 (5)
C3C	0.7609 (2)	0.77985 (11)	0.71370 (11)	0.0241 (5)
C4C	0.5934 (2)	0.75021 (11)	0.74070 (11)	0.0222 (5)
C5C	0.6059 (2)	0.81317 (11)	0.83729 (11)	0.0250 (5)
C6C	0.6456 (2)	0.91528 (12)	0.85156 (12)	0.0268 (5)
C41C	0.5546 (2)	0.64687 (12)	0.72451 (12)	0.0261 (5)
O41D	0.4858 (2)	−0.39280 (9)	0.08881 (9)	0.0455 (5)
N1D	0.68074 (18)	−0.06252 (10)	0.16379 (9)	0.0194 (4)
N41D	0.4860 (3)	−0.41732 (12)	−0.05238 (12)	0.0491 (7)
C2D	0.5026 (2)	−0.10376 (11)	0.16829 (11)	0.0217 (5)
C3D	0.4735 (2)	−0.20812 (11)	0.14410 (11)	0.0236 (5)
C4D	0.5034 (2)	−0.25961 (11)	0.05190 (11)	0.0215 (5)
C5D	0.6816 (2)	−0.21258 (11)	0.04612 (11)	0.0225 (5)
C6D	0.7099 (2)	−0.10792 (11)	0.07259 (11)	0.0221 (5)
C41D	0.4893 (2)	−0.36272 (12)	0.03098 (12)	0.0284 (5)
O41E	0.40936 (19)	0.39100 (9)	0.59760 (9)	0.0419 (5)
N1E	0.30389 (18)	0.06166 (10)	0.51160 (10)	0.0218 (4)
N41E	0.4681 (3)	0.41519 (13)	0.74075 (12)	0.0486 (7)
C2E	0.1532 (2)	0.10154 (11)	0.50968 (12)	0.0253 (5)
C3E	0.2165 (2)	0.20717 (11)	0.53852 (12)	0.0260 (5)
C4E	0.3342 (2)	0.25597 (11)	0.63063 (11)	0.0235 (5)
C5E	0.4817 (2)	0.21023 (11)	0.63280 (11)	0.0217 (5)
C6E	0.4159 (2)	0.10470 (11)	0.60222 (11)	0.0226 (5)
C41E	0.4060 (2)	0.36065 (12)	0.65494 (12)	0.0279 (6)
H2A	1.05390	0.41990	0.06390	0.0430*
H3A	0.99360	0.26100	0.02550	0.0390*
H5A	0.79910	0.29580	0.24040	0.0300*
H6A	0.85450	0.45500	0.27750	0.0320*
H21A	0.92760	0.54240	0.06810	0.0380*
H31A	0.97360	0.69930	0.09740	0.0330*
H51A	1.09720	0.76570	0.35780	0.0270*
H61A	1.05070	0.60830	0.32800	0.0300*
H2B	0.77440	0.47210	0.55830	0.0350*
H3B	0.63440	0.31750	0.52000	0.0360*
H5B	0.96150	0.23510	0.37020	0.0490*
H6B	1.10180	0.38960	0.40840	0.0530*
H4C	0.50110	0.75830	0.70390	0.0270*
H11C	0.896 (3)	0.9334 (14)	0.8666 (14)	0.035 (5)*
H12C	0.841 (3)	1.0017 (15)	0.8368 (13)	0.040 (6)*
H21C	0.73720	0.89820	0.69720	0.0300*
H22C	0.92740	0.90080	0.72550	0.0300*
H31C	0.74690	0.74480	0.65050	0.0290*
H32C	0.85010	0.76410	0.74390	0.0290*
H41C	0.493 (3)	0.6046 (19)	0.6029 (18)	0.065 (9)*
H42C	0.476 (3)	0.5247 (18)	0.6280 (15)	0.052 (7)*
H51C	0.69450	0.80460	0.87490	0.0300*
H52C	0.49940	0.79590	0.85360	0.0300*
H61C	0.64880	0.95470	0.91260	0.0320*
H62C	0.55820	0.92410	0.81360	0.0320*
H4D	0.41820	−0.25600	0.00790	0.0260*
H11D	0.700 (2)	−0.0010 (14)	0.1780 (12)	0.027 (5)*
H12D	0.758 (3)	−0.0705 (13)	0.2020 (13)	0.030 (5)*
H21D	0.42150	−0.09430	0.12760	0.0260*
H22D	0.48600	−0.07260	0.22760	0.0260*
H31D	0.35810	−0.23460	0.14580	0.0280*
H32D	0.54980	−0.21690	0.18740	0.0280*
H41D	0.484 (3)	−0.4805 (18)	−0.0685 (16)	0.055 (7)*
H42D	0.494 (3)	−0.3950 (17)	−0.0905 (16)	0.057 (7)*
H51D	0.76660	−0.22230	0.08460	0.0270*
H52D	0.69560	−0.24200	−0.01400	0.0270*
H61D	0.82510	−0.08030	0.07130	0.0270*
H62D	0.63250	−0.09770	0.03090	0.0270*
H4E	0.26970	0.24880	0.67400	0.0280*
H11E	0.364 (2)	0.0718 (12)	0.4732 (12)	0.020 (5)*
H12E	0.266 (2)	−0.0024 (15)	0.4951 (12)	0.032 (5)*
H21E	0.08570	0.08870	0.54930	0.0300*
H22E	0.08230	0.07240	0.45030	0.0300*
H31E	0.27690	0.21920	0.49610	0.0310*
H32E	0.12000	0.23310	0.53880	0.0310*
H41E	0.460 (3)	0.3938 (18)	0.7821 (18)	0.068 (8)*
H42E	0.508 (3)	0.4760 (17)	0.7557 (15)	0.051 (7)*
H51E	0.55330	0.22300	0.59470	0.0260*
H52E	0.55040	0.23760	0.69260	0.0260*
H61E	0.51080	0.07760	0.60160	0.0270*
H62E	0.35260	0.09170	0.64320	0.0270*

	U11	U22	U33	U12	U13	U23
S4A	0.0211 (2)	0.0127 (2)	0.0207 (2)	0.0049 (2)	0.0017 (2)	0.0052 (2)
S41A	0.0192 (2)	0.0124 (2)	0.0199 (2)	0.0052 (2)	0.0027 (2)	0.0055 (2)
O41A	0.0267 (7)	0.0239 (7)	0.0320 (7)	0.0073 (5)	−0.0051 (5)	0.0021 (5)
O42A	0.0309 (7)	0.0219 (6)	0.0413 (8)	0.0150 (5)	0.0121 (6)	0.0128 (6)
O43A	0.0493 (8)	0.0170 (6)	0.0270 (7)	0.0023 (6)	0.0056 (6)	0.0106 (5)
O44A	0.0327 (7)	0.0181 (6)	0.0346 (7)	0.0023 (5)	−0.0101 (6)	0.0060 (5)
O45A	0.0357 (7)	0.0166 (6)	0.0290 (7)	0.0065 (5)	0.0112 (5)	0.0116 (5)
O46A	0.0286 (7)	0.0271 (7)	0.0342 (7)	0.0173 (5)	0.0124 (5)	0.0142 (6)
C1A	0.0283 (9)	0.0170 (8)	0.0249 (9)	0.0079 (7)	0.0060 (7)	0.0084 (7)
C2A	0.0603 (13)	0.0238 (9)	0.0373 (11)	0.0163 (9)	0.0300 (10)	0.0185 (8)
C3A	0.0530 (12)	0.0220 (9)	0.0325 (10)	0.0184 (9)	0.0247 (9)	0.0121 (8)
C4A	0.0190 (8)	0.0145 (8)	0.0214 (8)	0.0051 (6)	0.0017 (6)	0.0067 (6)
C5A	0.0319 (10)	0.0191 (8)	0.0242 (9)	0.0031 (7)	0.0094 (7)	0.0091 (7)
C6A	0.0367 (10)	0.0190 (9)	0.0219 (9)	0.0080 (7)	0.0104 (8)	0.0055 (7)
C11A	0.0282 (9)	0.0169 (8)	0.0253 (9)	0.0089 (7)	0.0082 (7)	0.0087 (7)
C21A	0.0575 (13)	0.0173 (9)	0.0186 (9)	0.0126 (8)	0.0079 (8)	0.0046 (7)
C31A	0.0461 (11)	0.0207 (9)	0.0201 (8)	0.0135 (8)	0.0092 (8)	0.0095 (7)
C41A	0.0169 (8)	0.0132 (7)	0.0230 (8)	0.0055 (6)	0.0049 (6)	0.0061 (6)
C51A	0.0260 (9)	0.0174 (8)	0.0191 (8)	0.0038 (7)	0.0014 (7)	0.0053 (7)
C61A	0.0333 (10)	0.0206 (9)	0.0232 (9)	0.0070 (7)	0.0034 (7)	0.0112 (7)
S4B	0.0249 (2)	0.0130 (2)	0.0166 (2)	0.0002 (2)	0.0045 (2)	0.0037 (2)
O41B	0.0354 (7)	0.0175 (6)	0.0318 (7)	0.0035 (5)	−0.0030 (6)	0.0109 (5)
O42B	0.0215 (6)	0.0284 (7)	0.0480 (8)	−0.0020 (5)	−0.0003 (6)	0.0193 (6)
O43B	0.0765 (11)	0.0197 (7)	0.0295 (7)	−0.0044 (7)	0.0292 (7)	−0.0018 (6)
C1B	0.0217 (8)	0.0163 (9)	0.0213 (8)	0.0044 (7)	0.0034 (7)	0.0067 (7)
C2B	0.0372 (10)	0.0176 (9)	0.0342 (10)	0.0094 (8)	0.0197 (8)	0.0066 (8)
C3B	0.0333 (10)	0.0204 (9)	0.0365 (10)	0.0053 (8)	0.0201 (8)	0.0103 (8)
C4B	0.0221 (8)	0.0150 (8)	0.0171 (8)	0.0021 (6)	0.0017 (6)	0.0063 (6)
C5B	0.0443 (12)	0.0163 (9)	0.0570 (13)	0.0063 (8)	0.0335 (10)	0.0054 (9)
C6B	0.0456 (12)	0.0184 (9)	0.0676 (15)	0.0040 (9)	0.0410 (11)	0.0097 (9)
O41C	0.0556 (9)	0.0188 (6)	0.0341 (7)	0.0073 (6)	0.0081 (6)	0.0116 (6)
N1C	0.0262 (8)	0.0150 (7)	0.0277 (8)	0.0031 (6)	−0.0010 (6)	0.0091 (6)
N41C	0.1053 (19)	0.0143 (9)	0.0331 (10)	0.0013 (10)	−0.0090 (11)	0.0059 (8)
C2C	0.0263 (9)	0.0234 (9)	0.0280 (9)	0.0057 (7)	0.0068 (7)	0.0128 (8)
C3C	0.0273 (9)	0.0194 (9)	0.0237 (9)	0.0074 (7)	0.0065 (7)	0.0061 (7)
C4C	0.0227 (8)	0.0159 (8)	0.0252 (9)	0.0049 (7)	0.0009 (7)	0.0070 (7)
C5C	0.0276 (9)	0.0192 (9)	0.0283 (9)	0.0070 (7)	0.0106 (7)	0.0084 (7)
C6C	0.0306 (10)	0.0185 (9)	0.0292 (9)	0.0096 (7)	0.0082 (8)	0.0057 (7)
C41C	0.0246 (9)	0.0184 (9)	0.0303 (10)	0.0041 (7)	0.0039 (7)	0.0065 (7)
O41D	0.0883 (12)	0.0197 (7)	0.0329 (8)	0.0176 (7)	0.0187 (8)	0.0127 (6)
N1D	0.0213 (7)	0.0128 (7)	0.0204 (7)	0.0038 (6)	0.0017 (6)	0.0044 (6)
N41D	0.1010 (17)	0.0167 (9)	0.0259 (9)	0.0179 (9)	0.0114 (10)	0.0050 (7)
C2D	0.0216 (8)	0.0179 (8)	0.0238 (8)	0.0066 (7)	0.0063 (7)	0.0058 (7)
C3D	0.0235 (9)	0.0179 (8)	0.0289 (9)	0.0046 (7)	0.0080 (7)	0.0091 (7)
C4D	0.0242 (9)	0.0144 (8)	0.0223 (8)	0.0052 (6)	0.0012 (7)	0.0050 (7)
C5D	0.0266 (9)	0.0206 (8)	0.0201 (8)	0.0108 (7)	0.0061 (7)	0.0058 (7)
C6D	0.0236 (9)	0.0201 (8)	0.0224 (8)	0.0055 (7)	0.0070 (7)	0.0082 (7)
C41D	0.0361 (10)	0.0162 (8)	0.0278 (9)	0.0058 (7)	0.0028 (8)	0.0059 (7)
O41E	0.0664 (10)	0.0169 (6)	0.0357 (8)	0.0029 (6)	0.0097 (7)	0.0087 (6)
N1E	0.0237 (8)	0.0137 (7)	0.0252 (8)	0.0040 (6)	0.0054 (6)	0.0058 (6)
N41E	0.0875 (16)	0.0170 (9)	0.0299 (10)	0.0026 (9)	0.0118 (10)	0.0040 (8)
C2E	0.0216 (9)	0.0196 (9)	0.0308 (9)	0.0053 (7)	0.0022 (7)	0.0077 (7)
C3E	0.0242 (9)	0.0191 (9)	0.0329 (10)	0.0081 (7)	0.0030 (7)	0.0088 (7)
C4E	0.0258 (9)	0.0156 (8)	0.0279 (9)	0.0062 (7)	0.0098 (7)	0.0063 (7)
C5E	0.0196 (8)	0.0208 (9)	0.0214 (8)	0.0033 (7)	0.0044 (7)	0.0064 (7)
C6E	0.0241 (9)	0.0210 (8)	0.0243 (9)	0.0091 (7)	0.0053 (7)	0.0098 (7)
C41E	0.0336 (10)	0.0170 (9)	0.0301 (10)	0.0067 (7)	0.0100 (8)	0.0059 (7)

S4A—O41A	1.4479 (13)	C51A—H51A	0.9300
S4A—O42A	1.4661 (14)	C61A—H61A	0.9300
S4A—O43A	1.4628 (14)	C1B—C2B	1.392 (2)
S4A—C4A	1.7921 (19)	C1B—C6B	1.398 (3)
S41A—O44A	1.4483 (13)	C1B—C1Bi	1.507 (2)
S41A—O45A	1.4660 (13)	C2B—C3B	1.397 (3)
S41A—O46A	1.4693 (13)	C3B—C4B	1.385 (3)
S41A—C41A	1.7941 (18)	C4B—C5B	1.374 (3)
S4B—O42B	1.4602 (14)	C5B—C6B	1.397 (3)
S4B—O43B	1.4432 (15)	C2B—H2B	0.9300
S4B—C4B	1.7962 (19)	C3B—H3B	0.9300
S4B—O41B	1.4569 (14)	C5B—H5B	0.9300
O41C—C41C	1.234 (2)	C6B—H6B	0.9300
O41D—C41D	1.235 (2)	C2C—C3C	1.527 (3)
O41E—C41E	1.231 (2)	C3C—C4C	1.547 (2)
N1C—C2C	1.495 (2)	C4C—C5C	1.525 (2)
N1C—C6C	1.507 (2)	C4C—C41C	1.532 (3)
N41C—C41C	1.329 (3)	C5C—C6C	1.521 (3)
N1C—H12C	0.90 (3)	C2C—H22C	0.9700
N1C—H11C	0.91 (2)	C2C—H21C	0.9700
N41C—H42C	0.89 (3)	C3C—H32C	0.9700
N41C—H41C	0.80 (3)	C3C—H31C	0.9700
N1D—C2D	1.508 (2)	C4C—H4C	0.9800
N1D—C6D	1.497 (2)	C5C—H52C	0.9700
N41D—C41D	1.331 (3)	C5C—H51C	0.9700
N1D—H11D	0.90 (2)	C6C—H62C	0.9700
N1D—H12D	0.91 (2)	C6C—H61C	0.9700
N41D—H41D	0.94 (3)	C2D—C3D	1.524 (3)
N41D—H42D	0.85 (3)	C3D—C4D	1.529 (2)
N1E—C2E	1.512 (2)	C4D—C5D	1.543 (2)
N1E—C6E	1.493 (2)	C4D—C41D	1.531 (3)
N41E—C41E	1.332 (3)	C5D—C6D	1.524 (3)
N1E—H11E	0.901 (19)	C2D—H22D	0.9700
N1E—H12E	0.93 (2)	C2D—H21D	0.9700
N41E—H42E	0.89 (3)	C3D—H31D	0.9700
N41E—H41E	0.89 (3)	C3D—H32D	0.9700
C1A—C11A	1.497 (3)	C4D—H4D	0.9800
C1A—C6A	1.398 (3)	C5D—H52D	0.9700
C1A—C2A	1.404 (3)	C5D—H51D	0.9700
C2A—C3A	1.386 (3)	C6D—H62D	0.9700
C3A—C4A	1.391 (3)	C6D—H61D	0.9700
C4A—C5A	1.387 (2)	C2E—C3E	1.528 (3)
C5A—C6A	1.396 (3)	C3E—C4E	1.529 (2)
C11A—C21A	1.395 (3)	C4E—C41E	1.535 (3)
C11A—C61A	1.398 (2)	C4E—C5E	1.547 (2)
C21A—C31A	1.394 (3)	C5E—C6E	1.524 (3)
C31A—C41A	1.390 (2)	C2E—H21E	0.9700
C41A—C51A	1.386 (2)	C2E—H22E	0.9700
C51A—C61A	1.396 (3)	C3E—H31E	0.9700
C2A—H2A	0.9300	C3E—H32E	0.9700
C3A—H3A	0.9300	C4E—H4E	0.9800
C5A—H5A	0.9300	C5E—H51E	0.9700
C6A—H6A	0.9300	C5E—H52E	0.9700
C21A—H21A	0.9300	C6E—H61E	0.9700
C31A—H31A	0.9300	C6E—H62E	0.9700
O41A—S4A—O42A	113.10 (8)	N1C—C2C—C3C	111.39 (15)
O41A—S4A—O43A	113.03 (8)	C2C—C3C—C4C	112.68 (14)
O41A—S4A—C4A	105.39 (8)	C3C—C4C—C41C	110.21 (14)
O42A—S4A—O43A	112.15 (8)	C3C—C4C—C5C	109.64 (14)
O42A—S4A—C4A	106.45 (8)	C5C—C4C—C41C	111.56 (15)
O43A—S4A—C4A	106.00 (8)	C4C—C5C—C6C	110.43 (15)
O44A—S41A—O45A	113.64 (8)	N1C—C6C—C5C	108.74 (14)
O44A—S41A—O46A	112.80 (8)	O41C—C41C—C4C	122.36 (16)
O44A—S41A—C41A	106.64 (8)	N41C—C41C—C4C	115.82 (17)
O45A—S41A—O46A	111.65 (8)	O41C—C41C—N41C	121.8 (2)
O45A—S41A—C41A	105.75 (8)	N1C—C2C—H21C	109.00
O46A—S41A—C41A	105.63 (8)	H21C—C2C—H22C	108.00
O41B—S4B—C4B	105.82 (8)	C3C—C2C—H21C	109.00
O42B—S4B—O43B	114.33 (9)	C3C—C2C—H22C	109.00
O42B—S4B—C4B	105.54 (9)	N1C—C2C—H22C	109.00
O43B—S4B—C4B	106.30 (8)	C2C—C3C—H31C	109.00
O41B—S4B—O42B	111.02 (8)	H31C—C3C—H32C	108.00
O41B—S4B—O43B	113.05 (9)	C4C—C3C—H31C	109.00
C2C—N1C—C6C	111.72 (14)	C2C—C3C—H32C	109.00
C6C—N1C—H12C	110.7 (16)	C4C—C3C—H32C	109.00
C2C—N1C—H12C	105.9 (13)	C41C—C4C—H4C	108.00
H11C—N1C—H12C	110 (2)	C3C—C4C—H4C	108.00
C2C—N1C—H11C	109.3 (14)	C5C—C4C—H4C	108.00
C6C—N1C—H11C	108.7 (15)	C4C—C5C—H51C	110.00
C41C—N41C—H42C	118.7 (15)	C6C—C5C—H51C	110.00
H41C—N41C—H42C	122 (3)	C6C—C5C—H52C	110.00
C41C—N41C—H41C	119 (2)	H51C—C5C—H52C	108.00
C2D—N1D—C6D	111.19 (13)	C4C—C5C—H52C	110.00
H11D—N1D—H12D	108.3 (18)	H61C—C6C—H62C	108.00
C6D—N1D—H12D	108.2 (14)	C5C—C6C—H62C	110.00
C2D—N1D—H11D	110.7 (11)	C5C—C6C—H61C	110.00
C6D—N1D—H11D	107.7 (12)	N1C—C6C—H62C	110.00
C2D—N1D—H12D	110.6 (15)	N1C—C6C—H61C	110.00
C41D—N41D—H41D	120.1 (15)	N1D—C2D—C3D	109.63 (14)
C41D—N41D—H42D	120.8 (18)	C2D—C3D—C4D	111.47 (15)
H41D—N41D—H42D	119 (2)	C3D—C4D—C41D	111.38 (15)
C2E—N1E—C6E	111.37 (14)	C3D—C4D—C5D	109.69 (14)
C2E—N1E—H12E	109.5 (11)	C5D—C4D—C41D	109.04 (14)
C6E—N1E—H11E	109.5 (11)	C4D—C5D—C6D	112.15 (14)
H11E—N1E—H12E	109.0 (17)	N1D—C6D—C5D	109.64 (14)
C6E—N1E—H12E	107.9 (12)	O41D—C41D—C4D	121.79 (16)
C2E—N1E—H11E	109.5 (12)	O41D—C41D—N41D	122.00 (19)
C41E—N41E—H42E	116.8 (15)	N41D—C41D—C4D	116.18 (17)
H41E—N41E—H42E	120 (2)	N1D—C2D—H22D	110.00
C41E—N41E—H41E	122.5 (19)	N1D—C2D—H21D	110.00
C2A—C1A—C6A	117.65 (18)	C3D—C2D—H22D	110.00
C6A—C1A—C11A	121.55 (15)	H21D—C2D—H22D	108.00
C2A—C1A—C11A	120.78 (17)	C3D—C2D—H21D	110.00
C1A—C2A—C3A	121.5 (2)	H31D—C3D—H32D	108.00
C2A—C3A—C4A	119.86 (19)	C2D—C3D—H31D	109.00
S4A—C4A—C5A	120.85 (14)	C2D—C3D—H32D	109.00
C3A—C4A—C5A	119.74 (18)	C4D—C3D—H32D	109.00
S4A—C4A—C3A	119.29 (13)	C4D—C3D—H31D	109.00
C4A—C5A—C6A	120.16 (16)	C41D—C4D—H4D	109.00
C1A—C6A—C5A	121.03 (16)	C3D—C4D—H4D	109.00
C1A—C11A—C61A	121.88 (16)	C5D—C4D—H4D	109.00
C21A—C11A—C61A	117.61 (17)	C6D—C5D—H51D	109.00
C1A—C11A—C21A	120.51 (16)	C4D—C5D—H51D	109.00
C11A—C21A—C31A	121.60 (17)	C4D—C5D—H52D	109.00
C21A—C31A—C41A	119.81 (17)	H51D—C5D—H52D	108.00
C31A—C41A—C51A	119.70 (16)	C6D—C5D—H52D	109.00
S41A—C41A—C31A	120.26 (13)	N1D—C6D—H62D	110.00
S41A—C41A—C51A	120.01 (12)	N1D—C6D—H61D	110.00
C41A—C51A—C61A	120.03 (15)	C5D—C6D—H62D	110.00
C11A—C61A—C51A	121.24 (17)	H61D—C6D—H62D	108.00
C3A—C2A—H2A	119.00	C5D—C6D—H61D	110.00
C1A—C2A—H2A	119.00	N1E—C2E—C3E	109.19 (14)
C4A—C3A—H3A	120.00	C2E—C3E—C4E	111.85 (15)
C2A—C3A—H3A	120.00	C3E—C4E—C41E	110.66 (15)
C6A—C5A—H5A	120.00	C5E—C4E—C41E	109.62 (14)
C4A—C5A—H5A	120.00	C3E—C4E—C5E	109.63 (14)
C5A—C6A—H6A	119.00	C4E—C5E—C6E	111.42 (14)
C1A—C6A—H6A	120.00	N1E—C6E—C5E	110.18 (15)
C31A—C21A—H21A	119.00	O41E—C41E—C4E	121.27 (16)
C11A—C21A—H21A	119.00	N41E—C41E—C4E	116.03 (17)
C41A—C31A—H31A	120.00	O41E—C41E—N41E	122.7 (2)
C21A—C31A—H31A	120.00	N1E—C2E—H21E	110.00
C41A—C51A—H51A	120.00	N1E—C2E—H22E	110.00
C61A—C51A—H51A	120.00	C3E—C2E—H21E	110.00
C51A—C61A—H61A	119.00	C3E—C2E—H22E	110.00
C11A—C61A—H61A	119.00	H21E—C2E—H22E	108.00
C2B—C1B—C6B	116.53 (17)	C2E—C3E—H31E	109.00
C1Bi—C1B—C6B	121.34 (16)	C2E—C3E—H32E	109.00
C1Bi—C1B—C2B	122.13 (15)	C4E—C3E—H31E	109.00
C1B—C2B—C3B	122.04 (17)	C4E—C3E—H32E	109.00
C2B—C3B—C4B	120.08 (16)	H31E—C3E—H32E	108.00
S4B—C4B—C5B	119.76 (15)	C3E—C4E—H4E	109.00
C3B—C4B—C5B	119.07 (18)	C5E—C4E—H4E	109.00
S4B—C4B—C3B	121.16 (14)	C41E—C4E—H4E	109.00
C4B—C5B—C6B	120.6 (2)	C4E—C5E—H51E	109.00
C1B—C6B—C5B	121.6 (2)	C4E—C5E—H52E	109.00
C3B—C2B—H2B	119.00	C6E—C5E—H51E	109.00
C1B—C2B—H2B	119.00	C6E—C5E—H52E	109.00
C4B—C3B—H3B	120.00	H51E—C5E—H52E	108.00
C2B—C3B—H3B	120.00	N1E—C6E—H61E	110.00
C6B—C5B—H5B	120.00	N1E—C6E—H62E	110.00
C4B—C5B—H5B	120.00	C5E—C6E—H61E	110.00
C1B—C6B—H6B	119.00	C5E—C6E—H62E	110.00
C5B—C6B—H6B	119.00	H61E—C6E—H62E	108.00
O41A—S4A—C4A—C3A	−81.03 (17)	S41A—C41A—C51A—C61A	177.33 (13)
O41A—S4A—C4A—C5A	94.97 (15)	C41A—C51A—C61A—C11A	0.7 (3)
O42A—S4A—C4A—C3A	39.33 (17)	C2B—C1B—C6B—C5B	0.1 (3)
O42A—S4A—C4A—C5A	−144.66 (14)	C2B—C1B—C1Bi—C6Bi	0.3 (3)
O43A—S4A—C4A—C3A	158.91 (16)	C6B—C1B—C1Bi—C6Bi	−180.00 (19)
O43A—S4A—C4A—C5A	−25.09 (16)	C6B—C1B—C1Bi—C2Bi	−0.3 (3)
O44A—S41A—C41A—C31A	−143.79 (14)	C1Bi—C1B—C2B—C3B	179.69 (16)
O44A—S41A—C41A—C51A	38.29 (16)	C2B—C1B—C1Bi—C2Bi	180.00 (17)
O45A—S41A—C41A—C31A	−22.51 (16)	C1Bi—C1B—C6B—C5B	−179.65 (19)
O45A—S41A—C41A—C51A	159.56 (14)	C6B—C1B—C2B—C3B	0.0 (3)
O46A—S41A—C41A—C31A	95.98 (15)	C1B—C2B—C3B—C4B	0.8 (3)
O46A—S41A—C41A—C51A	−81.95 (15)	C2B—C3B—C4B—S4B	176.90 (14)
O43B—S4B—C4B—C5B	−24.14 (18)	C2B—C3B—C4B—C5B	−1.5 (3)
O42B—S4B—C4B—C3B	35.67 (16)	C3B—C4B—C5B—C6B	1.6 (3)
O41B—S4B—C4B—C3B	−82.09 (15)	S4B—C4B—C5B—C6B	−176.87 (17)
O41B—S4B—C4B—C5B	96.31 (16)	C4B—C5B—C6B—C1B	−0.9 (3)
O42B—S4B—C4B—C5B	−145.93 (16)	N1C—C2C—C3C—C4C	50.99 (19)
O43B—S4B—C4B—C3B	157.47 (15)	C2C—C3C—C4C—C41C	−174.92 (14)
C6C—N1C—C2C—C3C	−55.64 (19)	C2C—C3C—C4C—C5C	−51.75 (19)
C2C—N1C—C6C—C5C	60.94 (19)	C3C—C4C—C41C—N41C	−71.7 (2)
C6D—N1D—C2D—C3D	60.39 (18)	C3C—C4C—C41C—O41C	107.02 (19)
C2D—N1D—C6D—C5D	−59.47 (18)	C5C—C4C—C41C—N41C	166.30 (18)
C2E—N1E—C6E—C5E	−59.72 (18)	C41C—C4C—C5C—C6C	179.63 (14)
C6E—N1E—C2E—C3E	59.69 (19)	C3C—C4C—C5C—C6C	57.26 (18)
C2A—C1A—C11A—C61A	−143.92 (19)	C5C—C4C—C41C—O41C	−15.0 (2)
C11A—C1A—C6A—C5A	176.71 (16)	C4C—C5C—C6C—N1C	−61.90 (18)
C6A—C1A—C2A—C3A	2.2 (3)	N1D—C2D—C3D—C4D	−57.77 (17)
C2A—C1A—C6A—C5A	−1.5 (3)	C2D—C3D—C4D—C41D	175.04 (14)
C6A—C1A—C11A—C21A	−141.7 (2)	C2D—C3D—C4D—C5D	54.23 (19)
C6A—C1A—C11A—C61A	37.9 (2)	C3D—C4D—C41D—O41D	−12.3 (2)
C11A—C1A—C2A—C3A	−176.04 (19)	C3D—C4D—C41D—N41D	169.59 (18)
C2A—C1A—C11A—C21A	36.5 (3)	C5D—C4D—C41D—N41D	−69.2 (2)
C1A—C2A—C3A—C4A	−0.9 (3)	C5D—C4D—C41D—O41D	108.90 (19)
C2A—C3A—C4A—S4A	174.89 (17)	C3D—C4D—C5D—C6D	−53.70 (19)
C2A—C3A—C4A—C5A	−1.2 (3)	C41D—C4D—C5D—C6D	−175.91 (14)
C3A—C4A—C5A—C6A	1.8 (3)	C4D—C5D—C6D—N1D	56.29 (18)
S4A—C4A—C5A—C6A	−174.16 (13)	N1E—C2E—C3E—C4E	−57.49 (18)
C4A—C5A—C6A—C1A	−0.5 (3)	C2E—C3E—C4E—C5E	54.81 (19)
C1A—C11A—C21A—C31A	−179.60 (18)	C2E—C3E—C4E—C41E	175.84 (14)
C21A—C11A—C61A—C51A	−0.8 (3)	C41E—C4E—C5E—C6E	−175.66 (14)
C1A—C11A—C61A—C51A	179.60 (16)	C3E—C4E—C41E—O41E	−20.9 (2)
C61A—C11A—C21A—C31A	0.8 (3)	C3E—C4E—C41E—N41E	161.03 (18)
C11A—C21A—C31A—C41A	−0.7 (3)	C5E—C4E—C41E—O41E	100.16 (19)
C21A—C31A—C41A—C51A	0.6 (3)	C5E—C4E—C41E—N41E	−77.9 (2)
C21A—C31A—C41A—S41A	−177.32 (16)	C3E—C4E—C5E—C6E	−54.01 (19)
C31A—C41A—C51A—C61A	−0.6 (3)	C4E—C5E—C6E—N1E	56.66 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1C—H11C···O42Ai	0.91 (2)	1.99 (2)	2.889 (2)	169 (2)
N1C—H12C···O45Aii	0.90 (3)	1.95 (3)	2.838 (2)	168.1 (18)
N1D—H11D···O43A	0.90 (2)	2.04 (2)	2.878 (2)	154.6 (16)
N1D—H11D···O43B	0.90 (2)	2.407 (18)	2.855 (2)	111.0 (15)
N1D—H12D···O46Aiii	0.91 (2)	1.98 (2)	2.877 (2)	170 (2)
N1E—H11E···O42B	0.901 (19)	2.003 (19)	2.878 (2)	163.5 (18)
N1E—H12E···O44Aiv	0.93 (2)	2.508 (18)	2.908 (2)	106.2 (15)
N41C—H42C···O41E	0.89 (3)	1.95 (3)	2.836 (3)	178 (2)
N41D—H41D···O41Dv	0.94 (3)	2.00 (3)	2.936 (3)	171 (2)
N41D—H42D···O41Cvi	0.85 (3)	2.34 (3)	3.134 (2)	158 (2)
N41E—H41E···O41Dvii	0.89 (3)	2.16 (3)	2.996 (2)	158 (3)
N41E—H42E···O41C	0.89 (3)	2.13 (3)	3.014 (3)	172 (2)
C5B—H5B···O43B	0.93	2.57	2.939 (3)	104
C2C—H21C···O42Bviii	0.97	2.36	3.276 (2)	156
C2D—H21D···O41Aix	0.97	2.57	3.423 (2)	147
C31A—H31A···O45A	0.93	2.58	2.944 (2)	104
C51A—H51A···O41Bi	0.93	2.45	3.367 (2)	169
C6C—H61C···O41Ax	0.97	2.41	3.295 (2)	152
C6E—H61E···O44Ai	0.97	2.46	3.345 (2)	151
C6D—H62D···O41Aix	0.97	2.52	3.380 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1C—H11C⋯O42Ai	0.91 (2)	1.99 (2)	2.889 (2)	169 (2)
N1C—H12C⋯O45Aii	0.90 (3)	1.95 (3)	2.838 (2)	168.1 (18)
N1D—H11D⋯O43A	0.90 (2)	2.04 (2)	2.878 (2)	154.6 (16)
N1D—H11D⋯O43B	0.90 (2)	2.407 (18)	2.855 (2)	111.0 (15)
N1D—H12D⋯O46Aiii	0.91 (2)	1.98 (2)	2.877 (2)	170 (2)
N1E—H11E⋯O42B	0.901 (19)	2.003 (19)	2.878 (2)	163.5 (18)
N1E—H12E⋯O44Aiv	0.93 (2)	2.508 (18)	2.908 (2)	106.2 (15)
N41C—H42C⋯O41E	0.89 (3)	1.95 (3)	2.836 (3)	178 (2)
N41D—H41D⋯O41Dv	0.94 (3)	2.00 (3)	2.936 (3)	171 (2)
N41D—H42D⋯O41Cvi	0.85 (3)	2.34 (3)	3.134 (2)	158 (2)
N41E—H41E⋯O41Dvii	0.89 (3)	2.16 (3)	2.996 (2)	158 (3)
N41E—H42E⋯O41C	0.89 (3)	2.13 (3)	3.014 (3)	172 (2)

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