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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 12| December 2010| Pages o3160-o3161
https://doi.org/10.1107/S1600536810045526

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

Graham Smith,a* Urs D. Wermutha and David J. Youngb

aFaculty of Science and Technology, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia, and bFaculty of Science, Universiti Brunei Darussalam, Jalan Tungku Link BE 1410, Negara Brunei Darussalam
*Correspondence e-mail: g.smith@qut.edu.au

(Received 4 November 2010; accepted 6 November 2010; online 13 November 2010)

In the title isonipecotamide salt 2C6H13N2O+·C12H8O6S22−, 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 R22(8)], the other giving a similar dimeric inter­action but across an inversion centre, both dimers then forming lateral cyclic R42(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[Swift, J. A. & Ward, M. D. (1998). Chem. Mater. 10, 1501-1504.]); Swift et al. (1998[Swift, J. A., Reynolds, A. M. & Ward, M. D. (1998). Chem. Mater. 10, 4159-4168.]); Holman & Ward (2000[Holman, K. T. & Ward, M. D. (2000). Angew. Chem. Int. Ed. 39, 1653-1655.]); Liao et al. (2001[Liao, C.-Z., Feng, X.-L., Yao, J.-H. & Cai, J.-W. (2001). Acta Cryst. C57, 1215-1216.]); Smith et al. (2010[Smith, G., Wermuth, U. D. & Young, D. J. (2010). Acta Cryst. E66, o1184-o1185.]). For isonipecotamide salt structures, see: Smith & Wermuth (2010a[Smith, G. & Wermuth, U. D. (2010a). Acta Cryst. C66. Submitted. [FG3206]],b[Smith, G. & Wermuth, U. D. (2010b). Acta Cryst. C66. Accepted. [SU3056]],c[Smith, G. & Wermuth, U. D. (2010c). Acta Cryst. E66, o3162.]). For graph-set motifs, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data

  • 2C6H13N2O+·C12H8O6S2−

  • Mr = 570.69

  • Triclinic, [P \overline 1]

  • 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[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd., Yarnton, Oxfordshire, England.]) Tmin = 0.911, Tmax = 0.980

  • 23474 measured reflections

  • 7679 independent reflections

  • 6364 reflections with I > 2σ(I)

  • Rint = 0.031
Refinement

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 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

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) -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.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd., Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) within WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045526/fl2328Isup2.hkl

checkCIF report


Comment top

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)°].

Related literature top

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 top

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 top

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.

Structure description top

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)°].

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).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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 (Spek, 2009).

Figures top
[Figure 1] 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 ellipsoids are drawn at the 50% probability level.
[Figure 2] 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 are omitted. For symmetry codes, see Table 1.
bis(4-carbamoylpiperidinium) biphenyl-4,4'-disulfonate top
Crystal data top
2C6H13N2O+·C12H8O6S2−Z = 3
Mr = 570.69F(000) = 906
Triclinic, P1Dx = 1.452 Mg m−3
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 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
Data collection top
Oxford Diffraction Gemini-S Ultra CCD-detector
diffractometer		7679 independent reflections
Radiation source: Enhance (Mo) X-ray source6364 reflections with I > 2σ(I)
Graphite monochromatorRint = 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 top
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 = 1.09 w = 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 Å−3
0 restraintsΔρmin = −0.51 e Å−3
Crystal data top
2C6H13N2O+·C12H8O6S2−γ = 101.714 (4)°
Mr = 570.69V = 1958.2 (2) Å3
Triclinic, P1Z = 3
a = 8.2530 (4) ÅMo Kα radiation
b = 16.0418 (8) ŵ = 0.26 mm−1
c = 16.7408 (11) ÅT = 200 K
α = 112.255 (5)°0.40 × 0.40 × 0.20 mm
β = 97.166 (5)°
Data collection top
Oxford Diffraction Gemini-S Ultra CCD-detector
diffractometer		7679 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		6364 reflections with I > 2σ(I)
Tmin = 0.911, Tmax = 0.980Rint = 0.031
23474 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.40 e Å−3
7679 reflectionsΔρmin = −0.51 e Å−3
562 parameters
Special details top

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) top
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) top
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, º) top
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 code: (i) −x+2, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
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.

Experimental details

Crystal data
Chemical formula2C6H13N2O+·C12H8O6S2−
Mr570.69
Crystal system, space groupTriclinic, P1
Temperature (K)200
a, b, c (Å)8.2530 (4), 16.0418 (8), 16.7408 (11)
α, β, γ (°)112.255 (5), 97.166 (5), 101.714 (4)
V (Å3)1958.2 (2)
Z3
Radiation typeMo Kα
µ (mm−1)0.26
Crystal size (mm)0.40 × 0.40 × 0.20
Data collection
DiffractometerOxford Diffraction Gemini-S Ultra CCD-detector
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.911, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections		23474, 7679, 6364
Rint0.031
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.098, 1.09
No. of reflections7679
No. of parameters562
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.40, −0.51

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
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)
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.
 

Acknowledgements

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.

References

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Pages o3160-o3161
https://doi.org/10.1107/S1600536810045526
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