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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3160–o3161.
Published online 2010 November 13. doi:  10.1107/S1600536810045526
PMCID: PMC3011572

Bis(4-carbamoylpiperidinium) biphenyl-4,4′-disulfonate

Abstract

In the title isonipecotamide salt 2C6H13N2O+·C12H8O6S2 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 inter­action [graph set R 2 2(8)], the other giving a similar dimeric inter­action but across an inversion centre, both dimers then forming lateral cyclic R 4 2(8) pyrimidinium–amide N—H(...)O inter­actions. 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 [triangle]); Swift et al. (1998 [triangle]); Holman & Ward (2000 [triangle]); Liao et al. (2001 [triangle]); Smith et al. (2010 [triangle]). For isonipecotamide salt structures, see: Smith & Wermuth (2010a [triangle],b [triangle],c [triangle]). For graph-set motifs, see: Etter et al. (1990 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3160-scheme1.jpg

Experimental

Crystal data

  • 2C6H13N2O+·C12H8O6S2
  • M r = 570.69
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3160-efi3.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]) within WinGX (Farrugia, 1999 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The authors acknowledge financial support from the Australian Research Council, the Faculty of Science and Technology, Queensland University of Technology and the School of Biomolecular and Physical Sciences, Griffith University.

supplementary crystallographic information

Comment

The structures of the Lewis base salts of biphenyl-4,4'-disulfonic acid (BPDS) are not prevalent in the CSD, e.g. with β-alanine (Liao et al., 2001) and with 2-(2,4-dinitrobenzyl)pyridine (Smith et al., 2010), but the bis(guanidinium) salt is notable as a co-host structure for cooperative guest recognition in clathrate formation, with numerous aromatic monocyclic and polycyclic hydrocarbons (Swift & Ward, 1998; Swift et al., 1998; Holman & Ward, 2000). The amide 4-carbamoylpiperidine (isonipecotamide, INIPA) is a compound for which there were no structures in the crystallographic literature. We therefore initiated a project aimed at synthesizing a series of salts of INIPA with a number of carboxylic acids, mainly aromatic, with a view of producing crystalline materials suitable for X-ray structural analysis. This amide has proved to be a particularly useful synthon for this purpose, giving the structures of largely anhydrous 1:1 salts with picric acid, 3,5-dinitrosalicylic acid (two polymorphs) (Smith & Wermuth, 2010a) as well as with the three isomeric mononitrobenzoic acids and 3,5-dinitrobenzoic acid (Smith & Wermuth, 2010b). All of these are 1:1 anhydrous salts while the acetate (Smith & Wermuth, 2010c) is a monohydrate.

Our reaction of 4-carbamoylpiperidine with biphenyl-4,4'-disulfonic acid in aqueous ethanol gave good anhydrous crystals of the title compound, (I) and the structure is reported here. With compound (I) (Fig. 1), the asymmetric unit comprises one BPDS dianion (B) which lies across a crystallographic inversion centre and another dianion (A in a general position, together with three INIPA anions (C, D, E). Two of these anions (C and E) give a cyclic dimeric amide–amide interaction [graph set R22(8) (Etter et al., 1990)], the other giving a similar but monomeric interaction across an inversion centre. The two dimers also give a lateral cyclic R24(8) amide-amide interaction (Table 1), these units being 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 (Fig 2). One of the amide H-atoms (H41C) has no possible H-bond association.

With all three isonipecotamide cations the amide group is rotated ca 100° out of the plane of the benzene ring [comparative torsion angles C3/C5–C4–C41–O41: 107.02 (19)° (C), 108.90 (19)° (D), 100.16 (19)° (E]. In the planar BPDS B dianions there are short intramolecular H2B···H6Bi/H6B···H2Bi contacts (2.07 Å) [for symmetry code (i) see Table 1] similar to those observed in the structure of the 2-(2,4-dinitrobenzyl)pyridinium salt of BPDS (Smith et al., 2010), in which the dianion is also centrosymmetric. The two phenyl rings of the A dianions are non-coplanar [torsion angle C2A–C1A–C11A–C21A, 143.92 (19)°].

Experimental

The title compound was synthesized by heating together under reflux for 10 minutes, 2 mmol of 4-carbamoylpiperidine (isonipecotamide) and 1 mmol of biphenyl-4,4'-disulfonic acid in 50 ml of 50% ethanol–water. After concentration to ca 30 ml, partial room temperature evaporation of the hot-filtered solution gave large colourless plates of (I) from which a specimen was cleaved for the X-ray analysis.

Refinement

Hydrogen atoms involved in hydrogen-bonding interactions were located by difference methods and their positional and isotropic displacement parameters were refined. The H-atoms were included in the refinement at calculated positions [C–H = 0.93 Å (aromatic) or 0.97 Å (aliphatic)] and with Uiso(H) = 1.2Ueq(C), while using a riding-model approximation.

Figures

Fig. 1.
Molecular configuration and atom naming scheme for the three INIPA cations (C, D, E) and the two BPDS dianions (A and B) in the asymmetric unit of (I). The dianion B lies across an inversion centre [for symmetry code (i), see Table 1] and displacement ...
Fig. 2.
The three-dimensional hydrogen-bonded framework structure of (I) viewed down the a cell direction showing the cyclic R22(8) and R24(8) amide–amide hydrogen-bonding interactions and their extension through the BPDS dianions. Non-associative H atoms ...

Crystal data

2C6H13N2O+·C12H8O6S2Z = 3
Mr = 570.69F(000) = 906
Triclinic, P1Dx = 1.452 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2530 (4) ÅCell parameters from 8867 reflections
b = 16.0418 (8) Åθ = 3.2–28.8°
c = 16.7408 (11) ŵ = 0.26 mm1
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

Data collection

Oxford Diffraction Gemini-S Ultra CCD-detector diffractometer7679 independent reflections
Radiation source: Enhance (Mo) X-ray source6364 reflections with I > 2σ(I)
graphiteRint = 0.031
ω scansθmax = 26.0°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)h = −10→10
Tmin = 0.911, Tmax = 0.980k = −19→19
23474 measured reflectionsl = −20→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.09w = 1/[σ2(Fo2) + (0.0573P)2 + 0.215P] where P = (Fo2 + 2Fc2)/3
7679 reflections(Δ/σ)max = 0.002
562 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = −0.51 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S4A0.82703 (5)0.13767 (3)0.09291 (3)0.0190 (1)
S41A1.06493 (5)0.86976 (3)0.25435 (3)0.0176 (1)
O41A0.66717 (15)0.10391 (8)0.02904 (8)0.0316 (4)
O42A0.96363 (15)0.10371 (8)0.05433 (9)0.0298 (4)
O43A0.81159 (17)0.12200 (8)0.17254 (8)0.0320 (4)
O44A1.20766 (16)0.92224 (8)0.32924 (8)0.0325 (4)
O45A1.09354 (15)0.87918 (8)0.17312 (8)0.0262 (4)
O46A0.90432 (15)0.88868 (8)0.27438 (8)0.0274 (4)
C1A0.9569 (2)0.45553 (11)0.17383 (11)0.0232 (5)
C2A1.0003 (3)0.39525 (13)0.09888 (13)0.0360 (6)
C3A0.9652 (3)0.29980 (13)0.07588 (13)0.0328 (6)
C4A0.88737 (19)0.26213 (11)0.12834 (10)0.0187 (5)
C5A0.8481 (2)0.32059 (11)0.20427 (11)0.0253 (5)
C6A0.8821 (2)0.41650 (12)0.22664 (11)0.0264 (5)
C11A0.9856 (2)0.55740 (11)0.19442 (11)0.0228 (5)
C21A0.9620 (3)0.58684 (12)0.12643 (12)0.0317 (6)
C31A0.9889 (2)0.68127 (12)0.14384 (11)0.0278 (5)
C41A1.03869 (19)0.74839 (10)0.23078 (10)0.0179 (4)
C51A1.0628 (2)0.72092 (11)0.29954 (11)0.0222 (5)
C61A1.0355 (2)0.62611 (12)0.28137 (11)0.0254 (5)
S4B0.68682 (5)0.13983 (3)0.41642 (3)0.0197 (1)
O41B0.76007 (16)0.12258 (8)0.49054 (8)0.0296 (4)
O42B0.50633 (15)0.13283 (9)0.41138 (9)0.0337 (4)
O43B0.7264 (2)0.08532 (9)0.33419 (9)0.0468 (5)
C1B0.9546 (2)0.44969 (10)0.48803 (10)0.0204 (5)
C2B0.8136 (2)0.42503 (12)0.52040 (12)0.0295 (6)
C3B0.7291 (2)0.33169 (12)0.49779 (12)0.0297 (6)
C4B0.7862 (2)0.26027 (11)0.44236 (10)0.0189 (5)
C5B0.9239 (3)0.28263 (13)0.40861 (15)0.0405 (7)
C6B1.0080 (3)0.37604 (13)0.43145 (15)0.0445 (7)
O41C0.57028 (18)0.62179 (8)0.78553 (9)0.0366 (4)
N1C0.81523 (19)0.94193 (10)0.83011 (10)0.0240 (4)
N41C0.5061 (3)0.58553 (13)0.64025 (13)0.0569 (8)
C2C0.8147 (2)0.88438 (12)0.73590 (11)0.0253 (5)
C3C0.7609 (2)0.77985 (11)0.71370 (11)0.0241 (5)
C4C0.5934 (2)0.75021 (11)0.74070 (11)0.0222 (5)
C5C0.6059 (2)0.81317 (11)0.83729 (11)0.0250 (5)
C6C0.6456 (2)0.91528 (12)0.85156 (12)0.0268 (5)
C41C0.5546 (2)0.64687 (12)0.72451 (12)0.0261 (5)
O41D0.4858 (2)−0.39280 (9)0.08881 (9)0.0455 (5)
N1D0.68074 (18)−0.06252 (10)0.16379 (9)0.0194 (4)
N41D0.4860 (3)−0.41732 (12)−0.05238 (12)0.0491 (7)
C2D0.5026 (2)−0.10376 (11)0.16829 (11)0.0217 (5)
C3D0.4735 (2)−0.20812 (11)0.14410 (11)0.0236 (5)
C4D0.5034 (2)−0.25961 (11)0.05190 (11)0.0215 (5)
C5D0.6816 (2)−0.21258 (11)0.04612 (11)0.0225 (5)
C6D0.7099 (2)−0.10792 (11)0.07259 (11)0.0221 (5)
C41D0.4893 (2)−0.36272 (12)0.03098 (12)0.0284 (5)
O41E0.40936 (19)0.39100 (9)0.59760 (9)0.0419 (5)
N1E0.30389 (18)0.06166 (10)0.51160 (10)0.0218 (4)
N41E0.4681 (3)0.41519 (13)0.74075 (12)0.0486 (7)
C2E0.1532 (2)0.10154 (11)0.50968 (12)0.0253 (5)
C3E0.2165 (2)0.20717 (11)0.53852 (12)0.0260 (5)
C4E0.3342 (2)0.25597 (11)0.63063 (11)0.0235 (5)
C5E0.4817 (2)0.21023 (11)0.63280 (11)0.0217 (5)
C6E0.4159 (2)0.10470 (11)0.60222 (11)0.0226 (5)
C41E0.4060 (2)0.36065 (12)0.65494 (12)0.0279 (6)
H2A1.053900.419900.063900.0430*
H3A0.993600.261000.025500.0390*
H5A0.799100.295800.240400.0300*
H6A0.854500.455000.277500.0320*
H21A0.927600.542400.068100.0380*
H31A0.973600.699300.097400.0330*
H51A1.097200.765700.357800.0270*
H61A1.050700.608300.328000.0300*
H2B0.774400.472100.558300.0350*
H3B0.634400.317500.520000.0360*
H5B0.961500.235100.370200.0490*
H6B1.101800.389600.408400.0530*
H4C0.501100.758300.703900.0270*
H11C0.896 (3)0.9334 (14)0.8666 (14)0.035 (5)*
H12C0.841 (3)1.0017 (15)0.8368 (13)0.040 (6)*
H21C0.737200.898200.697200.0300*
H22C0.927400.900800.725500.0300*
H31C0.746900.744800.650500.0290*
H32C0.850100.764100.743900.0290*
H41C0.493 (3)0.6046 (19)0.6029 (18)0.065 (9)*
H42C0.476 (3)0.5247 (18)0.6280 (15)0.052 (7)*
H51C0.694500.804600.874900.0300*
H52C0.499400.795900.853600.0300*
H61C0.648800.954700.912600.0320*
H62C0.558200.924100.813600.0320*
H4D0.41820−0.256000.007900.0260*
H11D0.700 (2)−0.0010 (14)0.1780 (12)0.027 (5)*
H12D0.758 (3)−0.0705 (13)0.2020 (13)0.030 (5)*
H21D0.42150−0.094300.127600.0260*
H22D0.48600−0.072600.227600.0260*
H31D0.35810−0.234600.145800.0280*
H32D0.54980−0.216900.187400.0280*
H41D0.484 (3)−0.4805 (18)−0.0685 (16)0.055 (7)*
H42D0.494 (3)−0.3950 (17)−0.0905 (16)0.057 (7)*
H51D0.76660−0.222300.084600.0270*
H52D0.69560−0.24200−0.014000.0270*
H61D0.82510−0.080300.071300.0270*
H62D0.63250−0.097700.030900.0270*
H4E0.269700.248800.674000.0280*
H11E0.364 (2)0.0718 (12)0.4732 (12)0.020 (5)*
H12E0.266 (2)−0.0024 (15)0.4951 (12)0.032 (5)*
H21E0.085700.088700.549300.0300*
H22E0.082300.072400.450300.0300*
H31E0.276900.219200.496100.0310*
H32E0.120000.233100.538800.0310*
H41E0.460 (3)0.3938 (18)0.7821 (18)0.068 (8)*
H42E0.508 (3)0.4760 (17)0.7557 (15)0.051 (7)*
H51E0.553300.223000.594700.0260*
H52E0.550400.237600.692600.0260*
H61E0.510800.077600.601600.0270*
H62E0.352600.091700.643200.0270*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S4A0.0211 (2)0.0127 (2)0.0207 (2)0.0049 (2)0.0017 (2)0.0052 (2)
S41A0.0192 (2)0.0124 (2)0.0199 (2)0.0052 (2)0.0027 (2)0.0055 (2)
O41A0.0267 (7)0.0239 (7)0.0320 (7)0.0073 (5)−0.0051 (5)0.0021 (5)
O42A0.0309 (7)0.0219 (6)0.0413 (8)0.0150 (5)0.0121 (6)0.0128 (6)
O43A0.0493 (8)0.0170 (6)0.0270 (7)0.0023 (6)0.0056 (6)0.0106 (5)
O44A0.0327 (7)0.0181 (6)0.0346 (7)0.0023 (5)−0.0101 (6)0.0060 (5)
O45A0.0357 (7)0.0166 (6)0.0290 (7)0.0065 (5)0.0112 (5)0.0116 (5)
O46A0.0286 (7)0.0271 (7)0.0342 (7)0.0173 (5)0.0124 (5)0.0142 (6)
C1A0.0283 (9)0.0170 (8)0.0249 (9)0.0079 (7)0.0060 (7)0.0084 (7)
C2A0.0603 (13)0.0238 (9)0.0373 (11)0.0163 (9)0.0300 (10)0.0185 (8)
C3A0.0530 (12)0.0220 (9)0.0325 (10)0.0184 (9)0.0247 (9)0.0121 (8)
C4A0.0190 (8)0.0145 (8)0.0214 (8)0.0051 (6)0.0017 (6)0.0067 (6)
C5A0.0319 (10)0.0191 (8)0.0242 (9)0.0031 (7)0.0094 (7)0.0091 (7)
C6A0.0367 (10)0.0190 (9)0.0219 (9)0.0080 (7)0.0104 (8)0.0055 (7)
C11A0.0282 (9)0.0169 (8)0.0253 (9)0.0089 (7)0.0082 (7)0.0087 (7)
C21A0.0575 (13)0.0173 (9)0.0186 (9)0.0126 (8)0.0079 (8)0.0046 (7)
C31A0.0461 (11)0.0207 (9)0.0201 (8)0.0135 (8)0.0092 (8)0.0095 (7)
C41A0.0169 (8)0.0132 (7)0.0230 (8)0.0055 (6)0.0049 (6)0.0061 (6)
C51A0.0260 (9)0.0174 (8)0.0191 (8)0.0038 (7)0.0014 (7)0.0053 (7)
C61A0.0333 (10)0.0206 (9)0.0232 (9)0.0070 (7)0.0034 (7)0.0112 (7)
S4B0.0249 (2)0.0130 (2)0.0166 (2)0.0002 (2)0.0045 (2)0.0037 (2)
O41B0.0354 (7)0.0175 (6)0.0318 (7)0.0035 (5)−0.0030 (6)0.0109 (5)
O42B0.0215 (6)0.0284 (7)0.0480 (8)−0.0020 (5)−0.0003 (6)0.0193 (6)
O43B0.0765 (11)0.0197 (7)0.0295 (7)−0.0044 (7)0.0292 (7)−0.0018 (6)
C1B0.0217 (8)0.0163 (9)0.0213 (8)0.0044 (7)0.0034 (7)0.0067 (7)
C2B0.0372 (10)0.0176 (9)0.0342 (10)0.0094 (8)0.0197 (8)0.0066 (8)
C3B0.0333 (10)0.0204 (9)0.0365 (10)0.0053 (8)0.0201 (8)0.0103 (8)
C4B0.0221 (8)0.0150 (8)0.0171 (8)0.0021 (6)0.0017 (6)0.0063 (6)
C5B0.0443 (12)0.0163 (9)0.0570 (13)0.0063 (8)0.0335 (10)0.0054 (9)
C6B0.0456 (12)0.0184 (9)0.0676 (15)0.0040 (9)0.0410 (11)0.0097 (9)
O41C0.0556 (9)0.0188 (6)0.0341 (7)0.0073 (6)0.0081 (6)0.0116 (6)
N1C0.0262 (8)0.0150 (7)0.0277 (8)0.0031 (6)−0.0010 (6)0.0091 (6)
N41C0.1053 (19)0.0143 (9)0.0331 (10)0.0013 (10)−0.0090 (11)0.0059 (8)
C2C0.0263 (9)0.0234 (9)0.0280 (9)0.0057 (7)0.0068 (7)0.0128 (8)
C3C0.0273 (9)0.0194 (9)0.0237 (9)0.0074 (7)0.0065 (7)0.0061 (7)
C4C0.0227 (8)0.0159 (8)0.0252 (9)0.0049 (7)0.0009 (7)0.0070 (7)
C5C0.0276 (9)0.0192 (9)0.0283 (9)0.0070 (7)0.0106 (7)0.0084 (7)
C6C0.0306 (10)0.0185 (9)0.0292 (9)0.0096 (7)0.0082 (8)0.0057 (7)
C41C0.0246 (9)0.0184 (9)0.0303 (10)0.0041 (7)0.0039 (7)0.0065 (7)
O41D0.0883 (12)0.0197 (7)0.0329 (8)0.0176 (7)0.0187 (8)0.0127 (6)
N1D0.0213 (7)0.0128 (7)0.0204 (7)0.0038 (6)0.0017 (6)0.0044 (6)
N41D0.1010 (17)0.0167 (9)0.0259 (9)0.0179 (9)0.0114 (10)0.0050 (7)
C2D0.0216 (8)0.0179 (8)0.0238 (8)0.0066 (7)0.0063 (7)0.0058 (7)
C3D0.0235 (9)0.0179 (8)0.0289 (9)0.0046 (7)0.0080 (7)0.0091 (7)
C4D0.0242 (9)0.0144 (8)0.0223 (8)0.0052 (6)0.0012 (7)0.0050 (7)
C5D0.0266 (9)0.0206 (8)0.0201 (8)0.0108 (7)0.0061 (7)0.0058 (7)
C6D0.0236 (9)0.0201 (8)0.0224 (8)0.0055 (7)0.0070 (7)0.0082 (7)
C41D0.0361 (10)0.0162 (8)0.0278 (9)0.0058 (7)0.0028 (8)0.0059 (7)
O41E0.0664 (10)0.0169 (6)0.0357 (8)0.0029 (6)0.0097 (7)0.0087 (6)
N1E0.0237 (8)0.0137 (7)0.0252 (8)0.0040 (6)0.0054 (6)0.0058 (6)
N41E0.0875 (16)0.0170 (9)0.0299 (10)0.0026 (9)0.0118 (10)0.0040 (8)
C2E0.0216 (9)0.0196 (9)0.0308 (9)0.0053 (7)0.0022 (7)0.0077 (7)
C3E0.0242 (9)0.0191 (9)0.0329 (10)0.0081 (7)0.0030 (7)0.0088 (7)
C4E0.0258 (9)0.0156 (8)0.0279 (9)0.0062 (7)0.0098 (7)0.0063 (7)
C5E0.0196 (8)0.0208 (9)0.0214 (8)0.0033 (7)0.0044 (7)0.0064 (7)
C6E0.0241 (9)0.0210 (8)0.0243 (9)0.0091 (7)0.0053 (7)0.0098 (7)
C41E0.0336 (10)0.0170 (9)0.0301 (10)0.0067 (7)0.0100 (8)0.0059 (7)

Geometric parameters (Å, °)

S4A—O41A1.4479 (13)C51A—H51A0.9300
S4A—O42A1.4661 (14)C61A—H61A0.9300
S4A—O43A1.4628 (14)C1B—C2B1.392 (2)
S4A—C4A1.7921 (19)C1B—C6B1.398 (3)
S41A—O44A1.4483 (13)C1B—C1Bi1.507 (2)
S41A—O45A1.4660 (13)C2B—C3B1.397 (3)
S41A—O46A1.4693 (13)C3B—C4B1.385 (3)
S41A—C41A1.7941 (18)C4B—C5B1.374 (3)
S4B—O42B1.4602 (14)C5B—C6B1.397 (3)
S4B—O43B1.4432 (15)C2B—H2B0.9300
S4B—C4B1.7962 (19)C3B—H3B0.9300
S4B—O41B1.4569 (14)C5B—H5B0.9300
O41C—C41C1.234 (2)C6B—H6B0.9300
O41D—C41D1.235 (2)C2C—C3C1.527 (3)
O41E—C41E1.231 (2)C3C—C4C1.547 (2)
N1C—C2C1.495 (2)C4C—C5C1.525 (2)
N1C—C6C1.507 (2)C4C—C41C1.532 (3)
N41C—C41C1.329 (3)C5C—C6C1.521 (3)
N1C—H12C0.90 (3)C2C—H22C0.9700
N1C—H11C0.91 (2)C2C—H21C0.9700
N41C—H42C0.89 (3)C3C—H32C0.9700
N41C—H41C0.80 (3)C3C—H31C0.9700
N1D—C2D1.508 (2)C4C—H4C0.9800
N1D—C6D1.497 (2)C5C—H52C0.9700
N41D—C41D1.331 (3)C5C—H51C0.9700
N1D—H11D0.90 (2)C6C—H62C0.9700
N1D—H12D0.91 (2)C6C—H61C0.9700
N41D—H41D0.94 (3)C2D—C3D1.524 (3)
N41D—H42D0.85 (3)C3D—C4D1.529 (2)
N1E—C2E1.512 (2)C4D—C5D1.543 (2)
N1E—C6E1.493 (2)C4D—C41D1.531 (3)
N41E—C41E1.332 (3)C5D—C6D1.524 (3)
N1E—H11E0.901 (19)C2D—H22D0.9700
N1E—H12E0.93 (2)C2D—H21D0.9700
N41E—H42E0.89 (3)C3D—H31D0.9700
N41E—H41E0.89 (3)C3D—H32D0.9700
C1A—C11A1.497 (3)C4D—H4D0.9800
C1A—C6A1.398 (3)C5D—H52D0.9700
C1A—C2A1.404 (3)C5D—H51D0.9700
C2A—C3A1.386 (3)C6D—H62D0.9700
C3A—C4A1.391 (3)C6D—H61D0.9700
C4A—C5A1.387 (2)C2E—C3E1.528 (3)
C5A—C6A1.396 (3)C3E—C4E1.529 (2)
C11A—C21A1.395 (3)C4E—C41E1.535 (3)
C11A—C61A1.398 (2)C4E—C5E1.547 (2)
C21A—C31A1.394 (3)C5E—C6E1.524 (3)
C31A—C41A1.390 (2)C2E—H21E0.9700
C41A—C51A1.386 (2)C2E—H22E0.9700
C51A—C61A1.396 (3)C3E—H31E0.9700
C2A—H2A0.9300C3E—H32E0.9700
C3A—H3A0.9300C4E—H4E0.9800
C5A—H5A0.9300C5E—H51E0.9700
C6A—H6A0.9300C5E—H52E0.9700
C21A—H21A0.9300C6E—H61E0.9700
C31A—H31A0.9300C6E—H62E0.9700
O41A—S4A—O42A113.10 (8)N1C—C2C—C3C111.39 (15)
O41A—S4A—O43A113.03 (8)C2C—C3C—C4C112.68 (14)
O41A—S4A—C4A105.39 (8)C3C—C4C—C41C110.21 (14)
O42A—S4A—O43A112.15 (8)C3C—C4C—C5C109.64 (14)
O42A—S4A—C4A106.45 (8)C5C—C4C—C41C111.56 (15)
O43A—S4A—C4A106.00 (8)C4C—C5C—C6C110.43 (15)
O44A—S41A—O45A113.64 (8)N1C—C6C—C5C108.74 (14)
O44A—S41A—O46A112.80 (8)O41C—C41C—C4C122.36 (16)
O44A—S41A—C41A106.64 (8)N41C—C41C—C4C115.82 (17)
O45A—S41A—O46A111.65 (8)O41C—C41C—N41C121.8 (2)
O45A—S41A—C41A105.75 (8)N1C—C2C—H21C109.00
O46A—S41A—C41A105.63 (8)H21C—C2C—H22C108.00
O41B—S4B—C4B105.82 (8)C3C—C2C—H21C109.00
O42B—S4B—O43B114.33 (9)C3C—C2C—H22C109.00
O42B—S4B—C4B105.54 (9)N1C—C2C—H22C109.00
O43B—S4B—C4B106.30 (8)C2C—C3C—H31C109.00
O41B—S4B—O42B111.02 (8)H31C—C3C—H32C108.00
O41B—S4B—O43B113.05 (9)C4C—C3C—H31C109.00
C2C—N1C—C6C111.72 (14)C2C—C3C—H32C109.00
C6C—N1C—H12C110.7 (16)C4C—C3C—H32C109.00
C2C—N1C—H12C105.9 (13)C41C—C4C—H4C108.00
H11C—N1C—H12C110 (2)C3C—C4C—H4C108.00
C2C—N1C—H11C109.3 (14)C5C—C4C—H4C108.00
C6C—N1C—H11C108.7 (15)C4C—C5C—H51C110.00
C41C—N41C—H42C118.7 (15)C6C—C5C—H51C110.00
H41C—N41C—H42C122 (3)C6C—C5C—H52C110.00
C41C—N41C—H41C119 (2)H51C—C5C—H52C108.00
C2D—N1D—C6D111.19 (13)C4C—C5C—H52C110.00
H11D—N1D—H12D108.3 (18)H61C—C6C—H62C108.00
C6D—N1D—H12D108.2 (14)C5C—C6C—H62C110.00
C2D—N1D—H11D110.7 (11)C5C—C6C—H61C110.00
C6D—N1D—H11D107.7 (12)N1C—C6C—H62C110.00
C2D—N1D—H12D110.6 (15)N1C—C6C—H61C110.00
C41D—N41D—H41D120.1 (15)N1D—C2D—C3D109.63 (14)
C41D—N41D—H42D120.8 (18)C2D—C3D—C4D111.47 (15)
H41D—N41D—H42D119 (2)C3D—C4D—C41D111.38 (15)
C2E—N1E—C6E111.37 (14)C3D—C4D—C5D109.69 (14)
C2E—N1E—H12E109.5 (11)C5D—C4D—C41D109.04 (14)
C6E—N1E—H11E109.5 (11)C4D—C5D—C6D112.15 (14)
H11E—N1E—H12E109.0 (17)N1D—C6D—C5D109.64 (14)
C6E—N1E—H12E107.9 (12)O41D—C41D—C4D121.79 (16)
C2E—N1E—H11E109.5 (12)O41D—C41D—N41D122.00 (19)
C41E—N41E—H42E116.8 (15)N41D—C41D—C4D116.18 (17)
H41E—N41E—H42E120 (2)N1D—C2D—H22D110.00
C41E—N41E—H41E122.5 (19)N1D—C2D—H21D110.00
C2A—C1A—C6A117.65 (18)C3D—C2D—H22D110.00
C6A—C1A—C11A121.55 (15)H21D—C2D—H22D108.00
C2A—C1A—C11A120.78 (17)C3D—C2D—H21D110.00
C1A—C2A—C3A121.5 (2)H31D—C3D—H32D108.00
C2A—C3A—C4A119.86 (19)C2D—C3D—H31D109.00
S4A—C4A—C5A120.85 (14)C2D—C3D—H32D109.00
C3A—C4A—C5A119.74 (18)C4D—C3D—H32D109.00
S4A—C4A—C3A119.29 (13)C4D—C3D—H31D109.00
C4A—C5A—C6A120.16 (16)C41D—C4D—H4D109.00
C1A—C6A—C5A121.03 (16)C3D—C4D—H4D109.00
C1A—C11A—C61A121.88 (16)C5D—C4D—H4D109.00
C21A—C11A—C61A117.61 (17)C6D—C5D—H51D109.00
C1A—C11A—C21A120.51 (16)C4D—C5D—H51D109.00
C11A—C21A—C31A121.60 (17)C4D—C5D—H52D109.00
C21A—C31A—C41A119.81 (17)H51D—C5D—H52D108.00
C31A—C41A—C51A119.70 (16)C6D—C5D—H52D109.00
S41A—C41A—C31A120.26 (13)N1D—C6D—H62D110.00
S41A—C41A—C51A120.01 (12)N1D—C6D—H61D110.00
C41A—C51A—C61A120.03 (15)C5D—C6D—H62D110.00
C11A—C61A—C51A121.24 (17)H61D—C6D—H62D108.00
C3A—C2A—H2A119.00C5D—C6D—H61D110.00
C1A—C2A—H2A119.00N1E—C2E—C3E109.19 (14)
C4A—C3A—H3A120.00C2E—C3E—C4E111.85 (15)
C2A—C3A—H3A120.00C3E—C4E—C41E110.66 (15)
C6A—C5A—H5A120.00C5E—C4E—C41E109.62 (14)
C4A—C5A—H5A120.00C3E—C4E—C5E109.63 (14)
C5A—C6A—H6A119.00C4E—C5E—C6E111.42 (14)
C1A—C6A—H6A120.00N1E—C6E—C5E110.18 (15)
C31A—C21A—H21A119.00O41E—C41E—C4E121.27 (16)
C11A—C21A—H21A119.00N41E—C41E—C4E116.03 (17)
C41A—C31A—H31A120.00O41E—C41E—N41E122.7 (2)
C21A—C31A—H31A120.00N1E—C2E—H21E110.00
C41A—C51A—H51A120.00N1E—C2E—H22E110.00
C61A—C51A—H51A120.00C3E—C2E—H21E110.00
C51A—C61A—H61A119.00C3E—C2E—H22E110.00
C11A—C61A—H61A119.00H21E—C2E—H22E108.00
C2B—C1B—C6B116.53 (17)C2E—C3E—H31E109.00
C1Bi—C1B—C6B121.34 (16)C2E—C3E—H32E109.00
C1Bi—C1B—C2B122.13 (15)C4E—C3E—H31E109.00
C1B—C2B—C3B122.04 (17)C4E—C3E—H32E109.00
C2B—C3B—C4B120.08 (16)H31E—C3E—H32E108.00
S4B—C4B—C5B119.76 (15)C3E—C4E—H4E109.00
C3B—C4B—C5B119.07 (18)C5E—C4E—H4E109.00
S4B—C4B—C3B121.16 (14)C41E—C4E—H4E109.00
C4B—C5B—C6B120.6 (2)C4E—C5E—H51E109.00
C1B—C6B—C5B121.6 (2)C4E—C5E—H52E109.00
C3B—C2B—H2B119.00C6E—C5E—H51E109.00
C1B—C2B—H2B119.00C6E—C5E—H52E109.00
C4B—C3B—H3B120.00H51E—C5E—H52E108.00
C2B—C3B—H3B120.00N1E—C6E—H61E110.00
C6B—C5B—H5B120.00N1E—C6E—H62E110.00
C4B—C5B—H5B120.00C5E—C6E—H61E110.00
C1B—C6B—H6B119.00C5E—C6E—H62E110.00
C5B—C6B—H6B119.00H61E—C6E—H62E108.00
O41A—S4A—C4A—C3A−81.03 (17)S41A—C41A—C51A—C61A177.33 (13)
O41A—S4A—C4A—C5A94.97 (15)C41A—C51A—C61A—C11A0.7 (3)
O42A—S4A—C4A—C3A39.33 (17)C2B—C1B—C6B—C5B0.1 (3)
O42A—S4A—C4A—C5A−144.66 (14)C2B—C1B—C1Bi—C6Bi0.3 (3)
O43A—S4A—C4A—C3A158.91 (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—C3B179.69 (16)
O44A—S41A—C41A—C51A38.29 (16)C2B—C1B—C1Bi—C2Bi180.00 (17)
O45A—S41A—C41A—C31A−22.51 (16)C1Bi—C1B—C6B—C5B−179.65 (19)
O45A—S41A—C41A—C51A159.56 (14)C6B—C1B—C2B—C3B0.0 (3)
O46A—S41A—C41A—C31A95.98 (15)C1B—C2B—C3B—C4B0.8 (3)
O46A—S41A—C41A—C51A−81.95 (15)C2B—C3B—C4B—S4B176.90 (14)
O43B—S4B—C4B—C5B−24.14 (18)C2B—C3B—C4B—C5B−1.5 (3)
O42B—S4B—C4B—C3B35.67 (16)C3B—C4B—C5B—C6B1.6 (3)
O41B—S4B—C4B—C3B−82.09 (15)S4B—C4B—C5B—C6B−176.87 (17)
O41B—S4B—C4B—C5B96.31 (16)C4B—C5B—C6B—C1B−0.9 (3)
O42B—S4B—C4B—C5B−145.93 (16)N1C—C2C—C3C—C4C50.99 (19)
O43B—S4B—C4B—C3B157.47 (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—C5C60.94 (19)C3C—C4C—C41C—N41C−71.7 (2)
C6D—N1D—C2D—C3D60.39 (18)C3C—C4C—C41C—O41C107.02 (19)
C2D—N1D—C6D—C5D−59.47 (18)C5C—C4C—C41C—N41C166.30 (18)
C2E—N1E—C6E—C5E−59.72 (18)C41C—C4C—C5C—C6C179.63 (14)
C6E—N1E—C2E—C3E59.69 (19)C3C—C4C—C5C—C6C57.26 (18)
C2A—C1A—C11A—C61A−143.92 (19)C5C—C4C—C41C—O41C−15.0 (2)
C11A—C1A—C6A—C5A176.71 (16)C4C—C5C—C6C—N1C−61.90 (18)
C6A—C1A—C2A—C3A2.2 (3)N1D—C2D—C3D—C4D−57.77 (17)
C2A—C1A—C6A—C5A−1.5 (3)C2D—C3D—C4D—C41D175.04 (14)
C6A—C1A—C11A—C21A−141.7 (2)C2D—C3D—C4D—C5D54.23 (19)
C6A—C1A—C11A—C61A37.9 (2)C3D—C4D—C41D—O41D−12.3 (2)
C11A—C1A—C2A—C3A−176.04 (19)C3D—C4D—C41D—N41D169.59 (18)
C2A—C1A—C11A—C21A36.5 (3)C5D—C4D—C41D—N41D−69.2 (2)
C1A—C2A—C3A—C4A−0.9 (3)C5D—C4D—C41D—O41D108.90 (19)
C2A—C3A—C4A—S4A174.89 (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—C6A1.8 (3)C4D—C5D—C6D—N1D56.29 (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—C5E54.81 (19)
C1A—C11A—C21A—C31A−179.60 (18)C2E—C3E—C4E—C41E175.84 (14)
C21A—C11A—C61A—C51A−0.8 (3)C41E—C4E—C5E—C6E−175.66 (14)
C1A—C11A—C61A—C51A179.60 (16)C3E—C4E—C41E—O41E−20.9 (2)
C61A—C11A—C21A—C31A0.8 (3)C3E—C4E—C41E—N41E161.03 (18)
C11A—C21A—C31A—C41A−0.7 (3)C5E—C4E—C41E—O41E100.16 (19)
C21A—C31A—C41A—C51A0.6 (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—N1E56.66 (18)

Symmetry codes: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1C—H11C···O42Ai0.91 (2)1.99 (2)2.889 (2)169 (2)
N1C—H12C···O45Aii0.90 (3)1.95 (3)2.838 (2)168.1 (18)
N1D—H11D···O43A0.90 (2)2.04 (2)2.878 (2)154.6 (16)
N1D—H11D···O43B0.90 (2)2.407 (18)2.855 (2)111.0 (15)
N1D—H12D···O46Aiii0.91 (2)1.98 (2)2.877 (2)170 (2)
N1E—H11E···O42B0.901 (19)2.003 (19)2.878 (2)163.5 (18)
N1E—H12E···O44Aiv0.93 (2)2.508 (18)2.908 (2)106.2 (15)
N41C—H42C···O41E0.89 (3)1.95 (3)2.836 (3)178 (2)
N41D—H41D···O41Dv0.94 (3)2.00 (3)2.936 (3)171 (2)
N41D—H42D···O41Cvi0.85 (3)2.34 (3)3.134 (2)158 (2)
N41E—H41E···O41Dvii0.89 (3)2.16 (3)2.996 (2)158 (3)
N41E—H42E···O41C0.89 (3)2.13 (3)3.014 (3)172 (2)
C5B—H5B···O43B0.932.572.939 (3)104
C2C—H21C···O42Bviii0.972.363.276 (2)156
C2D—H21D···O41Aix0.972.573.423 (2)147
C31A—H31A···O45A0.932.582.944 (2)104
C51A—H51A···O41Bi0.932.453.367 (2)169
C6C—H61C···O41Ax0.972.413.295 (2)152
C6E—H61E···O44Ai0.972.463.345 (2)151
C6D—H62D···O41Aix0.972.523.380 (2)148

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, −y+2, −z+1; (iii) x, y−1, z; (iv) x−1, y−1, z; (v) −x+1, −y−1, −z; (vi) x, y−1, z−1; (vii) −x+1, −y, −z+1; (viii) −x+1, −y+1, −z+1; (ix) −x+1, −y, −z; (x) x, y+1, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2328).

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