#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/83/2228317.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228317
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
'Young, David J.'
_publ_section_title
;
 Bis(4-carbamoylpiperidinium) biphenyl-4,4'-disulfonate
;
_journal_coeditor_code           FL2328
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3160
_journal_page_last               o3161
_journal_paper_doi               10.1107/S1600536810045526
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '2C6 H13 N2 O +, C12 H8 O6 S2 -'
_chemical_formula_moiety         '2(C6 H13 N2 O +), C12 H8 O6 S2 -'
_chemical_formula_sum            'C24 H34 N4 O8 S2'
_chemical_formula_weight         570.69
_chemical_name_common            'isponipecotamide biphenyl-4,4'-disulfonate'
_chemical_name_systematic
;
bis(4-carbamoylpiperidinium) biphenyl-4,4'-disulfonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                112.255(5)
_cell_angle_beta                 97.166(5)
_cell_angle_gamma                101.714(4)
_cell_formula_units_Z            3
_cell_length_a                   8.2530(4)
_cell_length_b                   16.0418(8)
_cell_length_c                   16.7408(11)
_cell_measurement_reflns_used    8867
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.82
_cell_measurement_theta_min      3.15
_cell_volume                     1958.2(2)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S Ultra CCD-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23474
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(CrysAlis Pro; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             906
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.511
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     562
_refine_ls_number_reflns         7679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0573P)²+0.2150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                6364
_reflns_number_total             7679
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2328.cif
_cod_data_source_block           I
_cod_database_code               2228317
_cod_database_fobs_code          2228317
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S4A 0.82703(5) 0.13767(3) 0.09291(3) 0.01900(10) Uani . . 1.000
S S41A 1.06493(5) 0.86976(3) 0.25435(3) 0.01760(10) Uani . . 1.000
O O41A 0.66717(15) 0.10391(8) 0.02904(8) 0.0316(4) Uani . . 1.000
O O42A 0.96363(15) 0.10371(8) 0.05433(9) 0.0298(4) Uani . . 1.000
O O43A 0.81159(17) 0.12200(8) 0.17254(8) 0.0320(4) Uani . . 1.000
O O44A 1.20766(16) 0.92224(8) 0.32924(8) 0.0325(4) Uani . . 1.000
O O45A 1.09354(15) 0.87918(8) 0.17312(8) 0.0262(4) Uani . . 1.000
O O46A 0.90432(15) 0.88868(8) 0.27438(8) 0.0274(4) Uani . . 1.000
C C1A 0.9569(2) 0.45553(11) 0.17383(11) 0.0232(5) Uani . . 1.000
C C2A 1.0003(3) 0.39525(13) 0.09888(13) 0.0360(6) Uani . . 1.000
C C3A 0.9652(3) 0.29980(13) 0.07588(13) 0.0328(6) Uani . . 1.000
C C4A 0.88737(19) 0.26213(11) 0.12834(10) 0.0187(5) Uani . . 1.000
C C5A 0.8481(2) 0.32059(11) 0.20427(11) 0.0253(5) Uani . . 1.000
C C6A 0.8821(2) 0.41650(12) 0.22664(11) 0.0264(5) Uani . . 1.000
C C11A 0.9856(2) 0.55740(11) 0.19442(11) 0.0228(5) Uani . . 1.000
C C21A 0.9620(3) 0.58684(12) 0.12643(12) 0.0317(6) Uani . . 1.000
C C31A 0.9889(2) 0.68127(12) 0.14384(11) 0.0278(5) Uani . . 1.000
C C41A 1.03869(19) 0.74839(10) 0.23078(10) 0.0179(4) Uani . . 1.000
C C51A 1.0628(2) 0.72092(11) 0.29954(11) 0.0222(5) Uani . . 1.000
C C61A 1.0355(2) 0.62611(12) 0.28137(11) 0.0254(5) Uani . . 1.000
S S4B 0.68682(5) 0.13983(3) 0.41642(3) 0.01970(10) Uani . . 1.000
O O41B 0.76007(16) 0.12258(8) 0.49054(8) 0.0296(4) Uani . . 1.000
O O42B 0.50633(15) 0.13283(9) 0.41138(9) 0.0337(4) Uani . . 1.000
O O43B 0.7264(2) 0.08532(9) 0.33419(9) 0.0468(5) Uani . . 1.000
C C1B 0.9546(2) 0.44969(10) 0.48803(10) 0.0204(5) Uani . . 1.000
C C2B 0.8136(2) 0.42503(12) 0.52040(12) 0.0295(6) Uani . . 1.000
C C3B 0.7291(2) 0.33169(12) 0.49779(12) 0.0297(6) Uani . . 1.000
C C4B 0.7862(2) 0.26027(11) 0.44236(10) 0.0189(5) Uani . . 1.000
C C5B 0.9239(3) 0.28263(13) 0.40861(15) 0.0405(7) Uani . . 1.000
C C6B 1.0080(3) 0.37604(13) 0.43145(15) 0.0445(7) Uani . . 1.000
O O41C 0.57028(18) 0.62179(8) 0.78553(9) 0.0366(4) Uani . . 1.000
N N1C 0.81523(19) 0.94193(10) 0.83011(10) 0.0240(4) Uani . . 1.000
N N41C 0.5061(3) 0.58553(13) 0.64025(13) 0.0569(8) Uani . . 1.000
C C2C 0.8147(2) 0.88438(12) 0.73590(11) 0.0253(5) Uani . . 1.000
C C3C 0.7609(2) 0.77985(11) 0.71370(11) 0.0241(5) Uani . . 1.000
C C4C 0.5934(2) 0.75021(11) 0.74070(11) 0.0222(5) Uani . . 1.000
C C5C 0.6059(2) 0.81317(11) 0.83729(11) 0.0250(5) Uani . . 1.000
C C6C 0.6456(2) 0.91528(12) 0.85156(12) 0.0268(5) Uani . . 1.000
C C41C 0.5546(2) 0.64687(12) 0.72451(12) 0.0261(5) Uani . . 1.000
O O41D 0.4858(2) -0.39280(9) 0.08881(9) 0.0455(5) Uani . . 1.000
N N1D 0.68074(18) -0.06252(10) 0.16379(9) 0.0194(4) Uani . . 1.000
N N41D 0.4860(3) -0.41732(12) -0.05238(12) 0.0491(7) Uani . . 1.000
C C2D 0.5026(2) -0.10376(11) 0.16829(11) 0.0217(5) Uani . . 1.000
C C3D 0.4735(2) -0.20812(11) 0.14410(11) 0.0236(5) Uani . . 1.000
C C4D 0.5034(2) -0.25961(11) 0.05190(11) 0.0215(5) Uani . . 1.000
C C5D 0.6816(2) -0.21258(11) 0.04612(11) 0.0225(5) Uani . . 1.000
C C6D 0.7099(2) -0.10792(11) 0.07259(11) 0.0221(5) Uani . . 1.000
C C41D 0.4893(2) -0.36272(12) 0.03098(12) 0.0284(5) Uani . . 1.000
O O41E 0.40936(19) 0.39100(9) 0.59760(9) 0.0419(5) Uani . . 1.000
N N1E 0.30389(18) 0.06166(10) 0.51160(10) 0.0218(4) Uani . . 1.000
N N41E 0.4681(3) 0.41519(13) 0.74075(12) 0.0486(7) Uani . . 1.000
C C2E 0.1532(2) 0.10154(11) 0.50968(12) 0.0253(5) Uani . . 1.000
C C3E 0.2165(2) 0.20717(11) 0.53852(12) 0.0260(5) Uani . . 1.000
C C4E 0.3342(2) 0.25597(11) 0.63063(11) 0.0235(5) Uani . . 1.000
C C5E 0.4817(2) 0.21023(11) 0.63280(11) 0.0217(5) Uani . . 1.000
C C6E 0.4159(2) 0.10470(11) 0.60222(11) 0.0226(5) Uani . . 1.000
C C41E 0.4060(2) 0.36065(12) 0.65494(12) 0.0279(6) Uani . . 1.000
H H2A 1.05390 0.41990 0.06390 0.0430 Uiso calc R 1.000
H H3A 0.99360 0.26100 0.02550 0.0390 Uiso calc R 1.000
H H5A 0.79910 0.29580 0.24040 0.0300 Uiso calc R 1.000
H H6A 0.85450 0.45500 0.27750 0.0320 Uiso calc R 1.000
H H21A 0.92760 0.54240 0.06810 0.0380 Uiso calc R 1.000
H H31A 0.97360 0.69930 0.09740 0.0330 Uiso calc R 1.000
H H51A 1.09720 0.76570 0.35780 0.0270 Uiso calc R 1.000
H H61A 1.05070 0.60830 0.32800 0.0300 Uiso calc R 1.000
H H2B 0.77440 0.47210 0.55830 0.0350 Uiso calc R 1.000
H H3B 0.63440 0.31750 0.52000 0.0360 Uiso calc R 1.000
H H5B 0.96150 0.23510 0.37020 0.0490 Uiso calc R 1.000
H H6B 1.10180 0.38960 0.40840 0.0530 Uiso calc R 1.000
H H4C 0.50110 0.75830 0.70390 0.0270 Uiso calc R 1.000
H H11C 0.896(3) 0.9334(14) 0.8666(14) 0.035(5) Uiso . . 1.000
H H12C 0.841(3) 1.0017(15) 0.8368(13) 0.040(6) Uiso . . 1.000
H H21C 0.73720 0.89820 0.69720 0.0300 Uiso calc R 1.000
H H22C 0.92740 0.90080 0.72550 0.0300 Uiso calc R 1.000
H H31C 0.74690 0.74480 0.65050 0.0290 Uiso calc R 1.000
H H32C 0.85010 0.76410 0.74390 0.0290 Uiso calc R 1.000
H H41C 0.493(3) 0.6046(19) 0.6029(18) 0.065(9) Uiso . . 1.000
H H42C 0.476(3) 0.5247(18) 0.6280(15) 0.052(7) Uiso . . 1.000
H H51C 0.69450 0.80460 0.87490 0.0300 Uiso calc R 1.000
H H52C 0.49940 0.79590 0.85360 0.0300 Uiso calc R 1.000
H H61C 0.64880 0.95470 0.91260 0.0320 Uiso calc R 1.000
H H62C 0.55820 0.92410 0.81360 0.0320 Uiso calc R 1.000
H H4D 0.41820 -0.25600 0.00790 0.0260 Uiso calc R 1.000
H H11D 0.700(2) -0.0010(14) 0.1780(12) 0.027(5) Uiso . . 1.000
H H12D 0.758(3) -0.0705(13) 0.2020(13) 0.030(5) Uiso . . 1.000
H H21D 0.42150 -0.09430 0.12760 0.0260 Uiso calc R 1.000
H H22D 0.48600 -0.07260 0.22760 0.0260 Uiso calc R 1.000
H H31D 0.35810 -0.23460 0.14580 0.0280 Uiso calc R 1.000
H H32D 0.54980 -0.21690 0.18740 0.0280 Uiso calc R 1.000
H H41D 0.484(3) -0.4805(18) -0.0685(16) 0.055(7) Uiso . . 1.000
H H42D 0.494(3) -0.3950(17) -0.0905(16) 0.057(7) Uiso . . 1.000
H H51D 0.76660 -0.22230 0.08460 0.0270 Uiso calc R 1.000
H H52D 0.69560 -0.24200 -0.01400 0.0270 Uiso calc R 1.000
H H61D 0.82510 -0.08030 0.07130 0.0270 Uiso calc R 1.000
H H62D 0.63250 -0.09770 0.03090 0.0270 Uiso calc R 1.000
H H4E 0.26970 0.24880 0.67400 0.0280 Uiso calc R 1.000
H H11E 0.364(2) 0.0718(12) 0.4732(12) 0.020(5) Uiso . . 1.000
H H12E 0.266(2) -0.0024(15) 0.4951(12) 0.032(5) Uiso . . 1.000
H H21E 0.08570 0.08870 0.54930 0.0300 Uiso calc R 1.000
H H22E 0.08230 0.07240 0.45030 0.0300 Uiso calc R 1.000
H H31E 0.27690 0.21920 0.49610 0.0310 Uiso calc R 1.000
H H32E 0.12000 0.23310 0.53880 0.0310 Uiso calc R 1.000
H H41E 0.460(3) 0.3938(18) 0.7821(18) 0.068(8) Uiso . . 1.000
H H42E 0.508(3) 0.4760(17) 0.7557(15) 0.051(7) Uiso . . 1.000
H H51E 0.55330 0.22300 0.59470 0.0260 Uiso calc R 1.000
H H52E 0.55040 0.23760 0.69260 0.0260 Uiso calc R 1.000
H H61E 0.51080 0.07760 0.60160 0.0270 Uiso calc R 1.000
H H62E 0.35260 0.09170 0.64320 0.0270 Uiso calc R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O41A S4A O42A . . . 113.10(8) no
O41A S4A O43A . . . 113.03(8) no
O41A S4A C4A . . . 105.39(8) no
O42A S4A O43A . . . 112.15(8) no
O42A S4A C4A . . . 106.45(8) no
O43A S4A C4A . . . 106.00(8) no
O44A S41A O45A . . . 113.64(8) no
O44A S41A O46A . . . 112.80(8) no
O44A S41A C41A . . . 106.64(8) no
O45A S41A O46A . . . 111.65(8) no
O45A S41A C41A . . . 105.75(8) no
O46A S41A C41A . . . 105.63(8) no
O41B S4B C4B . . . 105.82(8) no
O42B S4B O43B . . . 114.33(9) no
O42B S4B C4B . . . 105.54(9) no
O43B S4B C4B . . . 106.30(8) no
O41B S4B O42B . . . 111.02(8) no
O41B S4B O43B . . . 113.05(9) no
C2C N1C C6C . . . 111.72(14) no
C6C N1C H12C . . . 110.7(16) no
C2C N1C H12C . . . 105.9(13) no
H11C N1C H12C . . . 110(2) no
C2C N1C H11C . . . 109.3(14) no
C6C N1C H11C . . . 108.7(15) no
C41C N41C H42C . . . 118.7(15) no
H41C N41C H42C . . . 122(3) no
C41C N41C H41C . . . 119(2) no
C2D N1D C6D . . . 111.19(13) no
H11D N1D H12D . . . 108.3(18) no
C6D N1D H12D . . . 108.2(14) no
C2D N1D H11D . . . 110.7(11) no
C6D N1D H11D . . . 107.7(12) no
C2D N1D H12D . . . 110.6(15) no
C41D N41D H41D . . . 120.1(15) no
C41D N41D H42D . . . 120.8(18) no
H41D N41D H42D . . . 119(2) no
C2E N1E C6E . . . 111.37(14) no
C2E N1E H12E . . . 109.5(11) no
C6E N1E H11E . . . 109.5(11) no
H11E N1E H12E . . . 109.0(17) no
C6E N1E H12E . . . 107.9(12) no
C2E N1E H11E . . . 109.5(12) no
C41E N41E H42E . . . 116.8(15) no
H41E N41E H42E . . . 120(2) no
C41E N41E H41E . . . 122.5(19) no
C2A C1A C6A . . . 117.65(18) no
C6A C1A C11A . . . 121.55(15) no
C2A C1A C11A . . . 120.78(17) no
C1A C2A C3A . . . 121.5(2) no
C2A C3A C4A . . . 119.86(19) no
S4A C4A C5A . . . 120.85(14) no
C3A C4A C5A . . . 119.74(18) no
S4A C4A C3A . . . 119.29(13) no
C4A C5A C6A . . . 120.16(16) no
C1A C6A C5A . . . 121.03(16) no
C1A C11A C61A . . . 121.88(16) no
C21A C11A C61A . . . 117.61(17) no
C1A C11A C21A . . . 120.51(16) no
C11A C21A C31A . . . 121.60(17) no
C21A C31A C41A . . . 119.81(17) no
C31A C41A C51A . . . 119.70(16) no
S41A C41A C31A . . . 120.26(13) no
S41A C41A C51A . . . 120.01(12) no
C41A C51A C61A . . . 120.03(15) no
C11A C61A C51A . . . 121.24(17) no
C3A C2A H2A . . . 119.00 no
C1A C2A H2A . . . 119.00 no
C4A C3A H3A . . . 120.00 no
C2A C3A H3A . . . 120.00 no
C6A C5A H5A . . . 120.00 no
C4A C5A H5A . . . 120.00 no
C5A C6A H6A . . . 119.00 no
C1A C6A H6A . . . 120.00 no
C31A C21A H21A . . . 119.00 no
C11A C21A H21A . . . 119.00 no
C41A C31A H31A . . . 120.00 no
C21A C31A H31A . . . 120.00 no
C41A C51A H51A . . . 120.00 no
C61A C51A H51A . . . 120.00 no
C51A C61A H61A . . . 119.00 no
C11A C61A H61A . . . 119.00 no
C2B C1B C6B . . . 116.53(17) no
C1B C1B C6B 2_766 . . 121.34(16) no
C1B C1B C2B 2_766 . . 122.13(15) no
C1B C2B C3B . . . 122.04(17) no
C2B C3B C4B . . . 120.08(16) no
S4B C4B C5B . . . 119.76(15) no
C3B C4B C5B . . . 119.07(18) no
S4B C4B C3B . . . 121.16(14) no
C4B C5B C6B . . . 120.6(2) no
C1B C6B C5B . . . 121.6(2) no
C3B C2B H2B . . . 119.00 no
C1B C2B H2B . . . 119.00 no
C4B C3B H3B . . . 120.00 no
C2B C3B H3B . . . 120.00 no
C6B C5B H5B . . . 120.00 no
C4B C5B H5B . . . 120.00 no
C1B C6B H6B . . . 119.00 no
C5B C6B H6B . . . 119.00 no
N1C C2C C3C . . . 111.39(15) no
C2C C3C C4C . . . 112.68(14) no
C3C C4C C41C . . . 110.21(14) no
C3C C4C C5C . . . 109.64(14) no
C5C C4C C41C . . . 111.56(15) no
C4C C5C C6C . . . 110.43(15) no
N1C C6C C5C . . . 108.74(14) no
O41C C41C C4C . . . 122.36(16) no
N41C C41C C4C . . . 115.82(17) no
O41C C41C N41C . . . 121.8(2) no
N1C C2C H21C . . . 109.00 no
H21C C2C H22C . . . 108.00 no
C3C C2C H21C . . . 109.00 no
C3C C2C H22C . . . 109.00 no
N1C C2C H22C . . . 109.00 no
C2C C3C H31C . . . 109.00 no
H31C C3C H32C . . . 108.00 no
C4C C3C H31C . . . 109.00 no
C2C C3C H32C . . . 109.00 no
C4C C3C H32C . . . 109.00 no
C41C C4C H4C . . . 108.00 no
C3C C4C H4C . . . 108.00 no
C5C C4C H4C . . . 108.00 no
C4C C5C H51C . . . 110.00 no
C6C C5C H51C . . . 110.00 no
C6C C5C H52C . . . 110.00 no
H51C C5C H52C . . . 108.00 no
C4C C5C H52C . . . 110.00 no
H61C C6C H62C . . . 108.00 no
C5C C6C H62C . . . 110.00 no
C5C C6C H61C . . . 110.00 no
N1C C6C H62C . . . 110.00 no
N1C C6C H61C . . . 110.00 no
N1D C2D C3D . . . 109.63(14) no
C2D C3D C4D . . . 111.47(15) no
C3D C4D C41D . . . 111.38(15) no
C3D C4D C5D . . . 109.69(14) no
C5D C4D C41D . . . 109.04(14) no
C4D C5D C6D . . . 112.15(14) no
N1D C6D C5D . . . 109.64(14) no
O41D C41D C4D . . . 121.79(16) no
O41D C41D N41D . . . 122.00(19) no
N41D C41D C4D . . . 116.18(17) no
N1D C2D H22D . . . 110.00 no
N1D C2D H21D . . . 110.00 no
C3D C2D H22D . . . 110.00 no
H21D C2D H22D . . . 108.00 no
C3D C2D H21D . . . 110.00 no
H31D C3D H32D . . . 108.00 no
C2D C3D H31D . . . 109.00 no
C2D C3D H32D . . . 109.00 no
C4D C3D H32D . . . 109.00 no
C4D C3D H31D . . . 109.00 no
C41D C4D H4D . . . 109.00 no
C3D C4D H4D . . . 109.00 no
C5D C4D H4D . . . 109.00 no
C6D C5D H51D . . . 109.00 no
C4D C5D H51D . . . 109.00 no
C4D C5D H52D . . . 109.00 no
H51D C5D H52D . . . 108.00 no
C6D C5D H52D . . . 109.00 no
N1D C6D H62D . . . 110.00 no
N1D C6D H61D . . . 110.00 no
C5D C6D H62D . . . 110.00 no
H61D C6D H62D . . . 108.00 no
C5D C6D H61D . . . 110.00 no
N1E C2E C3E . . . 109.19(14) no
C2E C3E C4E . . . 111.85(15) no
C3E C4E C41E . . . 110.66(15) no
C5E C4E C41E . . . 109.62(14) no
C3E C4E C5E . . . 109.63(14) no
C4E C5E C6E . . . 111.42(14) no
N1E C6E C5E . . . 110.18(15) no
O41E C41E C4E . . . 121.27(16) no
N41E C41E C4E . . . 116.03(17) no
O41E C41E N41E . . . 122.7(2) no
N1E C2E H21E . . . 110.00 no
N1E C2E H22E . . . 110.00 no
C3E C2E H21E . . . 110.00 no
C3E C2E H22E . . . 110.00 no
H21E C2E H22E . . . 108.00 no
C2E C3E H31E . . . 109.00 no
C2E C3E H32E . . . 109.00 no
C4E C3E H31E . . . 109.00 no
C4E C3E H32E . . . 109.00 no
H31E C3E H32E . . . 108.00 no
C3E C4E H4E . . . 109.00 no
C5E C4E H4E . . . 109.00 no
C41E C4E H4E . . . 109.00 no
C4E C5E H51E . . . 109.00 no
C4E C5E H52E . . . 109.00 no
C6E C5E H51E . . . 109.00 no
C6E C5E H52E . . . 109.00 no
H51E C5E H52E . . . 108.00 no
N1E C6E H61E . . . 110.00 no
N1E C6E H62E . . . 110.00 no
C5E C6E H61E . . . 110.00 no
C5E C6E H62E . . . 110.00 no
H61E C6E H62E . . . 108.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S4A O41A . . 1.4479(13) no
S4A O42A . . 1.4661(14) no
S4A O43A . . 1.4628(14) no
S4A C4A . . 1.7921(19) no
S41A O44A . . 1.4483(13) no
S41A O45A . . 1.4660(13) no
S41A O46A . . 1.4693(13) no
S41A C41A . . 1.7941(18) no
S4B O42B . . 1.4602(14) no
S4B O43B . . 1.4432(15) no
S4B C4B . . 1.7962(19) no
S4B O41B . . 1.4569(14) no
O41C C41C . . 1.234(2) no
O41D C41D . . 1.235(2) no
O41E C41E . . 1.231(2) no
N1C C2C . . 1.495(2) no
N1C C6C . . 1.507(2) no
N41C C41C . . 1.329(3) no
N1C H12C . . 0.90(3) no
N1C H11C . . 0.91(2) no
N41C H42C . . 0.89(3) no
N41C H41C . . 0.80(3) no
N1D C2D . . 1.508(2) no
N1D C6D . . 1.497(2) no
N41D C41D . . 1.331(3) no
N1D H11D . . 0.90(2) no
N1D H12D . . 0.91(2) no
N41D H41D . . 0.94(3) no
N41D H42D . . 0.85(3) no
N1E C2E . . 1.512(2) no
N1E C6E . . 1.493(2) no
N41E C41E . . 1.332(3) no
N1E H11E . . 0.901(19) no
N1E H12E . . 0.93(2) no
N41E H42E . . 0.89(3) no
N41E H41E . . 0.89(3) no
C1A C11A . . 1.497(3) no
C1A C6A . . 1.398(3) no
C1A C2A . . 1.404(3) no
C2A C3A . . 1.386(3) no
C3A C4A . . 1.391(3) no
C4A C5A . . 1.387(2) no
C5A C6A . . 1.396(3) no
C11A C21A . . 1.395(3) no
C11A C61A . . 1.398(2) no
C21A C31A . . 1.394(3) no
C31A C41A . . 1.390(2) no
C41A C51A . . 1.386(2) no
C51A C61A . . 1.396(3) no
C2A H2A . . 0.9300 no
C3A H3A . . 0.9300 no
C5A H5A . . 0.9300 no
C6A H6A . . 0.9300 no
C21A H21A . . 0.9300 no
C31A H31A . . 0.9300 no
C51A H51A . . 0.9300 no
C61A H61A . . 0.9300 no
C1B C2B . . 1.392(2) no
C1B C6B . . 1.398(3) no
C1B C1B . 2_766 1.507(2) no
C2B C3B . . 1.397(3) no
C3B C4B . . 1.385(3) no
C4B C5B . . 1.374(3) no
C5B C6B . . 1.397(3) no
C2B H2B . . 0.9300 no
C3B H3B . . 0.9300 no
C5B H5B . . 0.9300 no
C6B H6B . . 0.9300 no
C2C C3C . . 1.527(3) no
C3C C4C . . 1.547(2) no
C4C C5C . . 1.525(2) no
C4C C41C . . 1.532(3) no
C5C C6C . . 1.521(3) no
C2C H22C . . 0.9700 no
C2C H21C . . 0.9700 no
C3C H32C . . 0.9700 no
C3C H31C . . 0.9700 no
C4C H4C . . 0.9800 no
C5C H52C . . 0.9700 no
C5C H51C . . 0.9700 no
C6C H62C . . 0.9700 no
C6C H61C . . 0.9700 no
C2D C3D . . 1.524(3) no
C3D C4D . . 1.529(2) no
C4D C5D . . 1.543(2) no
C4D C41D . . 1.531(3) no
C5D C6D . . 1.524(3) no
C2D H22D . . 0.9700 no
C2D H21D . . 0.9700 no
C3D H31D . . 0.9700 no
C3D H32D . . 0.9700 no
C4D H4D . . 0.9800 no
C5D H52D . . 0.9700 no
C5D H51D . . 0.9700 no
C6D H62D . . 0.9700 no
C6D H61D . . 0.9700 no
C2E C3E . . 1.528(3) no
C3E C4E . . 1.529(2) no
C4E C41E . . 1.535(3) no
C4E C5E . . 1.547(2) no
C5E C6E . . 1.524(3) no
C2E H21E . . 0.9700 no
C2E H22E . . 0.9700 no
C3E H31E . . 0.9700 no
C3E H32E . . 0.9700 no
C4E H4E . . 0.9800 no
C5E H51E . . 0.9700 no
C5E H52E . . 0.9700 no
C6E H61E . . 0.9700 no
C6E H62E . . 0.9700 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1C H11C O42A 2_766 0.91(2) 1.99(2) 2.889(2) 169(2) yes
N1C H12C O45A 2_776 0.90(3) 1.95(3) 2.838(2) 168.1(18) yes
N1D H11D O43A . 0.90(2) 2.04(2) 2.878(2) 154.6(16) yes
N1D H11D O43B . 0.90(2) 2.407(18) 2.855(2) 111.0(15) yes
N1D H12D O46A 1_545 0.91(2) 1.98(2) 2.877(2) 170(2) yes
N1E H11E O42B . 0.901(19) 2.003(19) 2.878(2) 163.5(18) yes
N1E H12E O44A 1_445 0.93(2) 2.508(18) 2.908(2) 106.2(15) yes
N41C H42C O41E . 0.89(3) 1.95(3) 2.836(3) 178(2) yes
N41D H41D O41D 2_645 0.94(3) 2.00(3) 2.936(3) 171(2) yes
N41D H42D O41C 1_544 0.85(3) 2.34(3) 3.134(2) 158(2) yes
N41E H41E O41D 2_656 0.89(3) 2.16(3) 2.996(2) 158(3) yes
N41E H42E O41C . 0.89(3) 2.13(3) 3.014(3) 172(2) yes
C5B H5B O43B . 0.93 2.57 2.939(3) 104 no
C2C H21C O42B 2_666 0.97 2.36 3.276(2) 156 no
C2D H21D O41A 2_655 0.97 2.57 3.423(2) 147 no
C31A H31A O45A . 0.93 2.58 2.944(2) 104 no
C51A H51A O41B 2_766 0.93 2.45 3.367(2) 169 no
C6C H61C O41A 1_566 0.97 2.41 3.295(2) 152 no
C6E H61E O44A 2_766 0.97 2.46 3.345(2) 151 no
C6D H62D O41A 2_655 0.97 2.52 3.380(2) 148 no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O41A S4A C4A C3A . . . . -81.03(17) no
O41A S4A C4A C5A . . . . 94.97(15) no
O42A S4A C4A C3A . . . . 39.33(17) no
O42A S4A C4A C5A . . . . -144.66(14) no
O43A S4A C4A C3A . . . . 158.91(16) no
O43A S4A C4A C5A . . . . -25.09(16) no
O44A S41A C41A C31A . . . . -143.79(14) no
O44A S41A C41A C51A . . . . 38.29(16) no
O45A S41A C41A C31A . . . . -22.51(16) no
O45A S41A C41A C51A . . . . 159.56(14) no
O46A S41A C41A C31A . . . . 95.98(15) no
O46A S41A C41A C51A . . . . -81.95(15) no
O43B S4B C4B C5B . . . . -24.14(18) no
O42B S4B C4B C3B . . . . 35.67(16) no
O41B S4B C4B C3B . . . . -82.09(15) no
O41B S4B C4B C5B . . . . 96.31(16) no
O42B S4B C4B C5B . . . . -145.93(16) no
O43B S4B C4B C3B . . . . 157.47(15) no
C6C N1C C2C C3C . . . . -55.64(19) no
C2C N1C C6C C5C . . . . 60.94(19) no
C6D N1D C2D C3D . . . . 60.39(18) no
C2D N1D C6D C5D . . . . -59.47(18) no
C2E N1E C6E C5E . . . . -59.72(18) no
C6E N1E C2E C3E . . . . 59.69(19) no
C2A C1A C11A C61A . . . . -143.92(19) no
C11A C1A C6A C5A . . . . 176.71(16) no
C6A C1A C2A C3A . . . . 2.2(3) no
C2A C1A C6A C5A . . . . -1.5(3) no
C6A C1A C11A C21A . . . . -141.7(2) no
C6A C1A C11A C61A . . . . 37.9(2) no
C11A C1A C2A C3A . . . . -176.04(19) no
C2A C1A C11A C21A . . . . 36.5(3) no
C1A C2A C3A C4A . . . . -0.9(3) no
C2A C3A C4A S4A . . . . 174.89(17) no
C2A C3A C4A C5A . . . . -1.2(3) no
C3A C4A C5A C6A . . . . 1.8(3) no
S4A C4A C5A C6A . . . . -174.16(13) no
C4A C5A C6A C1A . . . . -0.5(3) no
C1A C11A C21A C31A . . . . -179.60(18) no
C21A C11A C61A C51A . . . . -0.8(3) no
C1A C11A C61A C51A . . . . 179.60(16) no
C61A C11A C21A C31A . . . . 0.8(3) no
C11A C21A C31A C41A . . . . -0.7(3) no
C21A C31A C41A C51A . . . . 0.6(3) no
C21A C31A C41A S41A . . . . -177.32(16) no
C31A C41A C51A C61A . . . . -0.6(3) no
S41A C41A C51A C61A . . . . 177.33(13) no
C41A C51A C61A C11A . . . . 0.7(3) no
C2B C1B C6B C5B . . . . 0.1(3) no
C2B C1B C1B C6B . . 2_766 2_766 0.3(3) no
C6B C1B C1B C6B . . 2_766 2_766 -180.00(19) no
C6B C1B C1B C2B . . 2_766 2_766 -0.3(3) no
C1B C1B C2B C3B 2_766 . . . 179.69(16) no
C2B C1B C1B C2B . . 2_766 2_766 180.00(17) no
C1B C1B C6B C5B 2_766 . . . -179.65(19) no
C6B C1B C2B C3B . . . . 0.0(3) no
C1B C2B C3B C4B . . . . 0.8(3) no
C2B C3B C4B S4B . . . . 176.90(14) no
C2B C3B C4B C5B . . . . -1.5(3) no
C3B C4B C5B C6B . . . . 1.6(3) no
S4B C4B C5B C6B . . . . -176.87(17) no
C4B C5B C6B C1B . . . . -0.9(3) no
N1C C2C C3C C4C . . . . 50.99(19) no
C2C C3C C4C C41C . . . . -174.92(14) no
C2C C3C C4C C5C . . . . -51.75(19) no
C3C C4C C41C N41C . . . . -71.7(2) no
C3C C4C C41C O41C . . . . 107.02(19) no
C5C C4C C41C N41C . . . . 166.30(18) no
C41C C4C C5C C6C . . . . 179.63(14) no
C3C C4C C5C C6C . . . . 57.26(18) no
C5C C4C C41C O41C . . . . -15.0(2) no
C4C C5C C6C N1C . . . . -61.90(18) no
N1D C2D C3D C4D . . . . -57.77(17) no
C2D C3D C4D C41D . . . . 175.04(14) no
C2D C3D C4D C5D . . . . 54.23(19) no
C3D C4D C41D O41D . . . . -12.3(2) no
C3D C4D C41D N41D . . . . 169.59(18) no
C5D C4D C41D N41D . . . . -69.2(2) no
C5D C4D C41D O41D . . . . 108.90(19) no
C3D C4D C5D C6D . . . . -53.70(19) no
C41D C4D C5D C6D . . . . -175.91(14) no
C4D C5D C6D N1D . . . . 56.29(18) no
N1E C2E C3E C4E . . . . -57.49(18) no
C2E C3E C4E C5E . . . . 54.81(19) no
C2E C3E C4E C41E . . . . 175.84(14) no
C41E C4E C5E C6E . . . . -175.66(14) no
C3E C4E C41E O41E . . . . -20.9(2) no
C3E C4E C41E N41E . . . . 161.03(18) no
C5E C4E C41E O41E . . . . 100.16(19) no
C5E C4E C41E N41E . . . . -77.9(2) no
C3E C4E C5E C6E . . . . -54.01(19) no
C4E C5E C6E N1E . . . . 56.66(18) no
