#------------------------------------------------------------------------------
#$Date: 2022-09-13 04:48:08 +0300 (Tue, 13 Sep 2022) $
#$Revision: 277787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022665.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022665
loop_
_publ_author_name
'Kayukova, Lyudmila A.'
'Vologzhanina, Anna V.'
'Yergaliyeva, Elmira M.'
'Baitursynova, Gulnur P.'
'Shulgau, Zarina T.'
'Sergazy, Shynggys'
_publ_section_title
;
 Crystal structure and antidiabetic activity of 2-aminospiropyrazolinium
 tosylates and the product of O-tosylation of
 β-(benzimidazol-1-yl)propioamidoxime
;
_journal_coeditor_code           ZO3026
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229622008464
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C13 H19 N4 +, C7 H7 O3 S -'
_chemical_formula_moiety         'C13 H19 N4 +, C7 H7 O3 S -'
_chemical_formula_sum            'C20 H26 N4 O3 S'
_chemical_formula_weight         402.51
_chemical_name_common
;
2-Amino-8-phenyl-1,5,8-triazaspiro[4.5]dec-1-en-5-ium tosylate
;
_chemical_name_systematic
;
2-Amino-8-phenyl-1,5,8-triazaspiro[4.5]dec-1-en-5-ium 4-methylbenzenesulfonate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                100.3150(10)
_cell_angle_beta                 96.5330(10)
_cell_angle_gamma                95.678(2)
_cell_formula_units_Z            4
_cell_length_a                   8.4423(3)
_cell_length_b                   12.0126(4)
_cell_length_c                   20.3063(6)
_cell_measurement_reflns_used    5975
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.42
_cell_volume                     1997.85(11)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            32048
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.544
_diffrn_reflns_theta_min         1.840
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.506
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         12050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0470P)²+0.5831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1281
_reflns_number_gt                8283
_reflns_number_total             12050
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zo3026sup1.cif
_cod_data_source_block           9
_cod_database_code               2022665
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.994
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_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_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1A 0.22897(5) 0.27108(3) 0.62635(2) 0.01242(9) Uani d 1 . .
O O1A 0.33527(16) 0.36856(11) 0.61689(6) 0.0205(3) Uani d 1 . .
O O2A 0.25158(16) 0.16556(11) 0.58232(6) 0.0187(3) Uani d 1 . .
O O3A 0.06131(15) 0.29161(11) 0.62272(6) 0.0182(3) Uani d 1 . .
C C14A 0.2841(2) 0.25202(14) 0.71034(8) 0.0143(3) Uani d 1 . .
C C15A 0.2317(3) 0.32296(18) 0.76325(10) 0.0295(5) Uani d 1 . .
H H15A 0.1674 0.3807 0.7545 0.035 Uiso calc 1 . .
C C16A 0.2742(4) 0.3086(2) 0.82885(10) 0.0399(6) Uani d 1 . .
H H16A 0.2383 0.3570 0.8650 0.048 Uiso calc 1 . .
C C17A 0.3684(3) 0.22468(19) 0.84311(10) 0.0303(5) Uani d 1 . .
C C18A 0.4160(3) 0.15363(17) 0.78939(10) 0.0227(4) Uani d 1 . .
H H18A 0.4785 0.0950 0.7981 0.027 Uiso calc 1 . .
C C19A 0.3748(2) 0.16586(15) 0.72286(9) 0.0176(4) Uani d 1 . .
H H19A 0.4082 0.1160 0.6866 0.021 Uiso calc 1 . .
C C20A 0.4125(4) 0.2097(2) 0.91504(11) 0.0496(8) Uani d 1 . .
H H20A 0.4412 0.2847 0.9446 0.074 Uiso calc 1 . .
H H20B 0.5041 0.1658 0.9174 0.074 Uiso calc 1 . .
H H20C 0.3206 0.1689 0.9297 0.074 Uiso calc 1 . .
S S1B 0.76188(5) 0.20010(4) 0.37318(2) 0.01294(9) Uani d 1 . .
O O1B 0.90086(17) 0.27540(12) 0.41026(6) 0.0246(3) Uani d 1 . .
O O2B 0.78796(18) 0.08137(11) 0.36021(6) 0.0214(3) Uani d 1 . .
O O3B 0.61544(16) 0.21880(11) 0.40376(7) 0.0207(3) Uani d 1 . .
C C14B 0.7299(2) 0.23792(15) 0.29212(8) 0.0149(3) Uani d 1 . .
C C15B 0.7849(2) 0.17221(15) 0.23751(9) 0.0190(4) Uani d 1 . .
H H15B 0.8329 0.1056 0.2430 0.023 Uiso calc 1 . .
C C16B 0.7689(3) 0.20502(17) 0.17479(9) 0.0224(4) Uani d 1 . .
H H16B 0.8069 0.1603 0.1377 0.027 Uiso calc 1 . .
C C17B 0.6987(2) 0.30145(17) 0.16550(9) 0.0225(4) Uani d 1 . .
C C18B 0.6424(3) 0.36536(17) 0.22052(10) 0.0249(4) Uani d 1 . .
H H18B 0.5928 0.4312 0.2147 0.030 Uiso calc 1 . .
C C19B 0.6574(2) 0.33474(16) 0.28367(9) 0.0208(4) Uani d 1 . .
H H19B 0.6187 0.3793 0.3206 0.025 Uiso calc 1 . .
C C20B 0.6873(3) 0.3396(2) 0.09798(10) 0.0330(5) Uani d 1 . .
H H20D 0.7812 0.3942 0.0974 0.049 Uiso calc 1 . .
H H20E 0.5893 0.3759 0.0912 0.049 Uiso calc 1 . .
H H20F 0.6842 0.2732 0.0617 0.049 Uiso calc 1 . .
N N1A 0.21592(18) 0.52737(12) 0.37860(7) 0.0127(3) Uani d 1 . .
N N2A 0.33798(18) 0.45039(12) 0.38983(7) 0.0145(3) Uani d 1 . .
N N3A 0.41482(19) 0.35688(12) 0.47664(7) 0.0159(3) Uani d 1 . .
H H3AA 0.4855 0.3235 0.4539 0.019 Uiso calc 1 . .
H H3AB 0.4029 0.3437 0.5172 0.019 Uiso calc 1 . .
N N4A 0.1726(2) 0.51015(13) 0.23363(7) 0.0182(3) Uani d 1 . .
C C1A 0.3258(2) 0.42746(14) 0.44972(8) 0.0138(3) Uani d 1 . .
C C2A 0.2018(2) 0.48318(15) 0.48668(9) 0.0154(3) Uani d 1 . .
H H2AA 0.2439 0.5147 0.5346 0.018 Uiso calc 1 . .
H H2AB 0.1033 0.4297 0.4841 0.018 Uiso calc 1 . .
C C3A 0.1721(2) 0.57666(15) 0.44743(8) 0.0162(3) Uani d 1 . .
H H3AC 0.2415 0.6485 0.4683 0.019 Uiso calc 1 . .
H H3AD 0.0583 0.5910 0.4443 0.019 Uiso calc 1 . .
C C4A 0.0711(2) 0.46040(15) 0.33313(9) 0.0159(3) Uani d 1 . .
H H4AA -0.0148 0.5101 0.3289 0.019 Uiso calc 1 . .
H H4AB 0.0298 0.3961 0.3534 0.019 Uiso calc 1 . .
C C5A 0.1141(2) 0.41488(15) 0.26387(9) 0.0183(4) Uani d 1 . .
H H5AA 0.1983 0.3637 0.2678 0.022 Uiso calc 1 . .
H H5AB 0.0184 0.3704 0.2348 0.022 Uiso calc 1 . .
C C6A 0.3183(2) 0.57318(15) 0.27534(9) 0.0173(4) Uani d 1 . .
H H6AA 0.3590 0.6365 0.2542 0.021 Uiso calc 1 . .
H H6AB 0.4025 0.5218 0.2781 0.021 Uiso calc 1 . .
C C7A 0.2836(2) 0.62043(14) 0.34553(8) 0.0147(3) Uani d 1 . .
H H7AA 0.3839 0.6604 0.3733 0.018 Uiso calc 1 . .
H H7AB 0.2059 0.6766 0.3430 0.018 Uiso calc 1 . .
C C8A 0.1846(3) 0.48537(17) 0.16327(9) 0.0240(4) Uani d 1 . .
C C9A 0.2072(4) 0.5767(2) 0.13014(11) 0.0434(7) Uani d 1 . .
H H9A 0.2170 0.6526 0.1549 0.052 Uiso calc 1 . .
C C10A 0.2156(5) 0.5574(3) 0.06155(13) 0.0663(11) Uani d 1 . .
H H10A 0.2302 0.6202 0.0394 0.080 Uiso calc 1 . .
C C11A 0.2030(5) 0.4474(3) 0.02493(12) 0.0644(10) Uani d 1 . .
H H11A 0.2097 0.4346 -0.0222 0.077 Uiso calc 1 . .
C C12A 0.1806(4) 0.3565(2) 0.05725(12) 0.0472(7) Uani d 1 . .
H H12A 0.1717 0.2808 0.0323 0.057 Uiso calc 1 . .
C C13A 0.1710(3) 0.37502(19) 0.12624(10) 0.0316(5) Uani d 1 . .
H H13A 0.1551 0.3120 0.1481 0.038 Uiso calc 1 . .
N N1B 0.80637(18) -0.00380(12) 0.63126(7) 0.0144(3) Uani d 1 . .
N N2B 0.65824(18) 0.04813(12) 0.61763(7) 0.0148(3) Uani d 1 . .
N N3B 0.55495(19) 0.13834(12) 0.53314(7) 0.0160(3) Uani d 1 . .
H H3BA 0.4700 0.1519 0.5533 0.019 Uiso calc 1 . .
H H3BB 0.5657 0.1608 0.4948 0.019 Uiso calc 1 . .
N N4B 0.81343(19) -0.01232(13) 0.77410(7) 0.0177(3) Uani d 1 . .
C C1B 0.6674(2) 0.08371(14) 0.56074(8) 0.0140(3) Uani d 1 . .
C C2B 0.8150(2) 0.06218(15) 0.52832(9) 0.0166(3) Uani d 1 . .
H H2BA 0.8920 0.1323 0.5354 0.020 Uiso calc 1 . .
H H2BB 0.7883 0.0311 0.4793 0.020 Uiso calc 1 . .
C C3B 0.8799(2) -0.02526(17) 0.56597(9) 0.0193(4) Uani d 1 . .
H H3BC 0.9987 -0.0129 0.5748 0.023 Uiso calc 1 . .
H H3BD 0.8450 -0.1038 0.5404 0.023 Uiso calc 1 . .
C C4B 0.9214(2) 0.07556(15) 0.68588(9) 0.0162(3) Uani d 1 . .
H H4BA 0.9455 0.1493 0.6716 0.019 Uiso calc 1 . .
H H4BB 1.0234 0.0423 0.6926 0.019 Uiso calc 1 . .
C C5B 0.8518(2) 0.09573(15) 0.75176(9) 0.0175(4) Uani d 1 . .
H H5BA 0.9301 0.1473 0.7867 0.021 Uiso calc 1 . .
H H5BB 0.7531 0.1331 0.7458 0.021 Uiso calc 1 . .
C C6B 0.7008(2) -0.09183(15) 0.72248(9) 0.0171(4) Uani d 1 . .
H H6BA 0.5973 -0.0602 0.7164 0.021 Uiso calc 1 . .
H H6BB 0.6803 -0.1651 0.7377 0.021 Uiso calc 1 . .
C C7B 0.7668(2) -0.11262(15) 0.65576(9) 0.0178(4) Uani d 1 . .
H H7BA 0.8650 -0.1507 0.6610 0.021 Uiso calc 1 . .
H H7BB 0.6867 -0.1643 0.6216 0.021 Uiso calc 1 . .
C C8B 0.7837(2) -0.00414(16) 0.84190(9) 0.0190(4) Uani d 1 . .
C C9B 0.6624(3) -0.07563(17) 0.86021(10) 0.0229(4) Uani d 1 . .
H H9B 0.5940 -0.1295 0.8263 0.028 Uiso calc 1 . .
C C10B 0.6412(3) -0.06842(19) 0.92796(10) 0.0296(5) Uani d 1 . .
H H10B 0.5592 -0.1185 0.9396 0.036 Uiso calc 1 . .
C C11B 0.7363(3) 0.0094(2) 0.97812(10) 0.0344(5) Uani d 1 . .
H H11B 0.7201 0.0142 1.0240 0.041 Uiso calc 1 . .
C C12B 0.8566(4) 0.0810(2) 0.96025(11) 0.0461(7) Uani d 1 . .
H H12B 0.9233 0.1356 0.9944 0.055 Uiso calc 1 . .
C C13B 0.8809(3) 0.0739(2) 0.89359(10) 0.0362(6) Uani d 1 . .
H H13B 0.9651 0.1230 0.8827 0.043 Uiso calc 1 . .
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_3
_geom_angle
_geom_angle_publ_flag
O1A S1A C14A . . 106.64(8) ?
O2A S1A O1A . . 112.46(8) ?
O2A S1A C14A . . 106.20(8) ?
O3A S1A O1A . . 112.85(8) ?
O3A S1A O2A . . 112.69(8) ?
O3A S1A C14A . . 105.32(8) ?
C15A C14A S1A . . 118.94(15) ?
C19A C14A S1A . . 120.59(14) ?
C19A C14A C15A . . 120.45(17) ?
C14A C15A H15A . . 120.4 ?
C16A C15A C14A . . 119.2(2) ?
C16A C15A H15A . . 120.4 ?
C15A C16A H16A . . 119.2 ?
C15A C16A C17A . . 121.6(2) ?
C17A C16A H16A . . 119.2 ?
C16A C17A C20A . . 120.8(2) ?
C18A C17A C16A . . 117.95(19) ?
C18A C17A C20A . . 121.2(2) ?
C17A C18A H18A . . 119.1 ?
C17A C18A C19A . . 121.72(19) ?
C19A C18A H18A . . 119.1 ?
C14A C19A C18A . . 118.99(18) ?
C14A C19A H19A . . 120.5 ?
C18A C19A H19A . . 120.5 ?
C17A C20A H20A . . 109.5 ?
C17A C20A H20B . . 109.5 ?
C17A C20A H20C . . 109.5 ?
H20A C20A H20B . . 109.5 ?
H20A C20A H20C . . 109.5 ?
H20B C20A H20C . . 109.5 ?
O1B S1B O3B . . 112.20(8) ?
O1B S1B C14B . . 106.29(8) ?
O2B S1B O1B . . 113.37(9) ?
O2B S1B O3B . . 112.74(8) ?
O2B S1B C14B . . 105.47(8) ?
O3B S1B C14B . . 106.04(8) ?
C15B C14B S1B . . 119.11(14) ?
C15B C14B C19B . . 120.08(16) ?
C19B C14B S1B . . 120.75(14) ?
C14B C15B H15B . . 120.2 ?
C14B C15B C16B . . 119.50(18) ?
C16B C15B H15B . . 120.2 ?
C15B C16B H16B . . 119.3 ?
C17B C16B C15B . . 121.32(19) ?
C17B C16B H16B . . 119.3 ?
C16B C17B C18B . . 118.38(17) ?
C16B C17B C20B . . 121.21(19) ?
C18B C17B C20B . . 120.4(2) ?
C17B C18B H18B . . 119.3 ?
C19B C18B C17B . . 121.45(19) ?
C19B C18B H18B . . 119.3 ?
C14B C19B H19B . . 120.4 ?
C18B C19B C14B . . 119.26(18) ?
C18B C19B H19B . . 120.4 ?
C17B C20B H20D . . 109.5 ?
C17B C20B H20E . . 109.5 ?
C17B C20B H20F . . 109.5 ?
H20D C20B H20E . . 109.5 ?
H20D C20B H20F . . 109.5 ?
H20E C20B H20F . . 109.5 ?
N2A N1A C3A . . 106.90(12) ?
N2A N1A C4A . . 109.30(13) ?
N2A N1A C7A . . 109.84(13) ?
C4A N1A C3A . . 110.90(13) ?
C7A N1A C3A . . 110.76(13) ?
C7A N1A C4A . . 109.11(13) ?
C1A N2A N1A . . 105.54(14) ?
H3AA N3A H3AB . . 120.0 ?
C1A N3A H3AA . . 120.0 ?
C1A N3A H3AB . . 120.0 ?
C5A N4A C6A . . 109.75(14) ?
C8A N4A C5A . . 116.75(15) ?
C8A N4A C6A . . 114.11(15) ?
N2A C1A N3A . . 122.85(17) ?
N2A C1A C2A . . 116.04(16) ?
N3A C1A C2A . . 121.09(15) ?
C1A C2A H2AA . . 111.6 ?
C1A C2A H2AB . . 111.6 ?
C1A C2A C3A . . 100.69(14) ?
H2AA C2A H2AB . . 109.4 ?
C3A C2A H2AA . . 111.6 ?
C3A C2A H2AB . . 111.6 ?
N1A C3A H3AC . . 111.3 ?
N1A C3A H3AD . . 111.3 ?
C2A C3A N1A . . 102.33(14) ?
C2A C3A H3AC . . 111.3 ?
C2A C3A H3AD . . 111.3 ?
H3AC C3A H3AD . . 109.2 ?
N1A C4A H4AA . . 109.5 ?
N1A C4A H4AB . . 109.5 ?
N1A C4A C5A . . 110.69(14) ?
H4AA C4A H4AB . . 108.1 ?
C5A C4A H4AA . . 109.5 ?
C5A C4A H4AB . . 109.5 ?
N4A C5A C4A . . 109.40(14) ?
N4A C5A H5AA . . 109.8 ?
N4A C5A H5AB . . 109.8 ?
C4A C5A H5AA . . 109.8 ?
C4A C5A H5AB . . 109.8 ?
H5AA C5A H5AB . . 108.2 ?
N4A C6A H6AA . . 109.5 ?
N4A C6A H6AB . . 109.5 ?
N4A C6A C7A . . 110.58(15) ?
H6AA C6A H6AB . . 108.1 ?
C7A C6A H6AA . . 109.5 ?
C7A C6A H6AB . . 109.5 ?
N1A C7A C6A . . 111.26(13) ?
N1A C7A H7AA . . 109.4 ?
N1A C7A H7AB . . 109.4 ?
C6A C7A H7AA . . 109.4 ?
C6A C7A H7AB . . 109.4 ?
H7AA C7A H7AB . . 108.0 ?
C9A C8A N4A . . 118.02(18) ?
C13A C8A N4A . . 123.05(18) ?
C13A C8A C9A . . 118.92(19) ?
C8A C9A H9A . . 119.8 ?
C10A C9A C8A . . 120.4(2) ?
C10A C9A H9A . . 119.8 ?
C9A C10A H10A . . 119.8 ?
C9A C10A C11A . . 120.5(3) ?
C11A C10A H10A . . 119.8 ?
C10A C11A H11A . . 120.2 ?
C12A C11A C10A . . 119.5(2) ?
C12A C11A H11A . . 120.2 ?
C11A C12A H12A . . 119.8 ?
C11A C12A C13A . . 120.4(2) ?
C13A C12A H12A . . 119.8 ?
C8A C13A C12A . . 120.2(2) ?
C8A C13A H13A . . 119.9 ?
C12A C13A H13A . . 119.9 ?
N2B N1B C3B . . 107.54(13) ?
N2B N1B C4B . . 109.94(13) ?
N2B N1B C7B . . 109.48(13) ?
C4B N1B C3B . . 110.48(14) ?
C7B N1B C3B . . 111.39(14) ?
C7B N1B C4B . . 108.02(13) ?
C1B N2B N1B . . 105.85(14) ?
H3BA N3B H3BB . . 120.0 ?
C1B N3B H3BA . . 120.0 ?
C1B N3B H3BB . . 120.0 ?
C6B N4B C5B . . 110.79(14) ?
C8B N4B C5B . . 116.43(14) ?
C8B N4B C6B . . 116.90(14) ?
N2B C1B N3B . . 122.89(17) ?
N2B C1B C2B . . 116.08(16) ?
N3B C1B C2B . . 121.01(15) ?
C1B C2B H2BA . . 111.5 ?
C1B C2B H2BB . . 111.5 ?
C1B C2B C3B . . 101.15(14) ?
H2BA C2B H2BB . . 109.4 ?
C3B C2B H2BA . . 111.5 ?
C3B C2B H2BB . . 111.5 ?
N1B C3B H3BC . . 111.2 ?
N1B C3B H3BD . . 111.2 ?
C2B C3B N1B . . 102.81(14) ?
C2B C3B H3BC . . 111.2 ?
C2B C3B H3BD . . 111.2 ?
H3BC C3B H3BD . . 109.1 ?
N1B C4B H4BA . . 109.4 ?
N1B C4B H4BB . . 109.4 ?
N1B C4B C5B . . 111.23(14) ?
H4BA C4B H4BB . . 108.0 ?
C5B C4B H4BA . . 109.4 ?
C5B C4B H4BB . . 109.4 ?
N4B C5B C4B . . 110.74(15) ?
N4B C5B H5BA . . 109.5 ?
N4B C5B H5BB . . 109.5 ?
C4B C5B H5BA . . 109.5 ?
C4B C5B H5BB . . 109.5 ?
H5BA C5B H5BB . . 108.1 ?
N4B C6B H6BA . . 109.4 ?
N4B C6B H6BB . . 109.4 ?
N4B C6B C7B . . 111.11(15) ?
H6BA C6B H6BB . . 108.0 ?
C7B C6B H6BA . . 109.4 ?
C7B C6B H6BB . . 109.4 ?
N1B C7B C6B . . 111.94(14) ?
N1B C7B H7BA . . 109.2 ?
N1B C7B H7BB . . 109.2 ?
C6B C7B H7BA . . 109.2 ?
C6B C7B H7BB . . 109.2 ?
H7BA C7B H7BB . . 107.9 ?
C9B C8B N4B . . 122.07(16) ?
C9B C8B C13B . . 117.59(17) ?
C13B C8B N4B . . 120.29(17) ?
C8B C9B H9B . . 119.8 ?
C10B C9B C8B . . 120.44(18) ?
C10B C9B H9B . . 119.8 ?
C9B C10B H10B . . 119.3 ?
C11B C10B C9B . . 121.40(19) ?
C11B C10B H10B . . 119.3 ?
C10B C11B H11B . . 120.8 ?
C10B C11B C12B . . 118.45(19) ?
C12B C11B H11B . . 120.8 ?
C11B C12B H12B . . 119.5 ?
C13B C12B C11B . . 120.9(2) ?
C13B C12B H12B . . 119.5 ?
C8B C13B H13B . . 119.4 ?
C12B C13B C8B . . 121.2(2) ?
C12B C13B H13B . . 119.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1A O1A . 1.4578(13) ?
S1A O2A . 1.4572(13) ?
S1A O3A . 1.4565(14) ?
S1A C14A . 1.7771(17) ?
C14A C15A . 1.390(3) ?
C14A C19A . 1.389(3) ?
C15A H15A . 0.9500 ?
C15A C16A . 1.385(3) ?
C16A H16A . 0.9500 ?
C16A C17A . 1.394(3) ?
C17A C18A . 1.383(3) ?
C17A C20A . 1.513(3) ?
C18A H18A . 0.9500 ?
C18A C19A . 1.394(2) ?
C19A H19A . 0.9500 ?
C20A H20A . 0.9800 ?
C20A H20B . 0.9800 ?
C20A H20C . 0.9800 ?
S1B O1B . 1.4515(13) ?
S1B O2B . 1.4466(13) ?
S1B O3B . 1.4643(14) ?
S1B C14B . 1.7831(17) ?
C14B C15B . 1.394(3) ?
C14B C19B . 1.395(3) ?
C15B H15B . 0.9500 ?
C15B C16B . 1.395(3) ?
C16B H16B . 0.9500 ?
C16B C17B . 1.385(3) ?
C17B C18B . 1.396(3) ?
C17B C20B . 1.517(3) ?
C18B H18B . 0.9500 ?
C18B C19B . 1.392(3) ?
C19B H19B . 0.9500 ?
C20B H20D . 0.9800 ?
C20B H20E . 0.9800 ?
C20B H20F . 0.9800 ?
N1A N2A . 1.476(2) ?
N1A C3A . 1.518(2) ?
N1A C4A . 1.509(2) ?
N1A C7A . 1.502(2) ?
N2A C1A . 1.307(2) ?
N3A H3AA . 0.8800 ?
N3A H3AB . 0.8800 ?
N3A C1A . 1.335(2) ?
N4A C5A . 1.463(2) ?
N4A C6A . 1.467(2) ?
N4A C8A . 1.424(2) ?
C1A C2A . 1.498(2) ?
C2A H2AA . 0.9900 ?
C2A H2AB . 0.9900 ?
C2A C3A . 1.513(2) ?
C3A H3AC . 0.9900 ?
C3A H3AD . 0.9900 ?
C4A H4AA . 0.9900 ?
C4A H4AB . 0.9900 ?
C4A C5A . 1.513(2) ?
C5A H5AA . 0.9900 ?
C5A H5AB . 0.9900 ?
C6A H6AA . 0.9900 ?
C6A H6AB . 0.9900 ?
C6A C7A . 1.509(2) ?
C7A H7AA . 0.9900 ?
C7A H7AB . 0.9900 ?
C8A C9A . 1.394(3) ?
C8A C13A . 1.389(3) ?
C9A H9A . 0.9500 ?
C9A C10A . 1.382(3) ?
C10A H10A . 0.9500 ?
C10A C11A . 1.383(4) ?
C11A H11A . 0.9500 ?
C11A C12A . 1.380(4) ?
C12A H12A . 0.9500 ?
C12A C13A . 1.391(3) ?
C13A H13A . 0.9500 ?
N1B N2B . 1.472(2) ?
N1B C3B . 1.519(2) ?
N1B C4B . 1.508(2) ?
N1B C7B . 1.501(2) ?
N2B C1B . 1.309(2) ?
N3B H3BA . 0.8800 ?
N3B H3BB . 0.8800 ?
N3B C1B . 1.334(2) ?
N4B C5B . 1.469(2) ?
N4B C6B . 1.466(2) ?
N4B C8B . 1.416(2) ?
C1B C2B . 1.498(3) ?
C2B H2BA . 0.9900 ?
C2B H2BB . 0.9900 ?
C2B C3B . 1.515(3) ?
C3B H3BC . 0.9900 ?
C3B H3BD . 0.9900 ?
C4B H4BA . 0.9900 ?
C4B H4BB . 0.9900 ?
C4B C5B . 1.512(2) ?
C5B H5BA . 0.9900 ?
C5B H5BB . 0.9900 ?
C6B H6BA . 0.9900 ?
C6B H6BB . 0.9900 ?
C6B C7B . 1.512(2) ?
C7B H7BA . 0.9900 ?
C7B H7BB . 0.9900 ?
C8B C9B . 1.396(3) ?
C8B C13B . 1.398(3) ?
C9B H9B . 0.9500 ?
C9B C10B . 1.396(3) ?
C10B H10B . 0.9500 ?
C10B C11B . 1.371(3) ?
C11B H11B . 0.9500 ?
C11B C12B . 1.388(3) ?
C12B H12B . 0.9500 ?
C12B C13B . 1.381(3) ?
C13B H13B . 0.9500 ?

_cod_database_fobs_code 2022665
