#------------------------------------------------------------------------------
#$Date: 2024-12-06 18:18:40 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296349 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/28/1572835.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_1572835
loop_
_publ_author_name
'Izzotti, Anthony R.'
'Gleason, James L.'
_publ_section_title
;
 Driving tert-butyl axial: the surprising cyclopropyl effect.
;
_journal_issue                   44
_journal_name_full               'Chemical science'
_journal_page_first              18592
_journal_page_last               18600
_journal_paper_doi               10.1039/d4sc05470a
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C20 H26 N2, H2 O, 2(C7 H7 O3 S)'
_chemical_formula_sum            'C34 H42 N2 O7 S2'
_chemical_formula_weight         654.81
_chemical_name_systematic
'4,7-dibenzyl-4,7-diazaspiro[2.5]octane-4,7-diium di-4-methylbenzenesulfonate hydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-07-31
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-08-01 deposited with the CCDC.	2024-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.580(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.120(3)
_cell_length_b                   9.381(2)
_cell_length_c                   14.431(3)
_cell_measurement_reflns_used    4842
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.411
_cell_measurement_theta_min      3.488
_cell_volume                     1678.6(7)
_computing_cell_refinement       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1585
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29994
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.411
_diffrn_reflns_theta_min         3.488
_exptl_absorpt_coefficient_mu    1.847
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1706 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.038(12)
_refine_ls_extinction_coef       0.023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         6534
_refine_ls_number_restraints     394
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0666P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                4842
_reflns_number_total             6534
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc05470a3.cif
_cod_data_source_block           AI11106
_cod_depositor_comments
'Adding full bibliography for 1572833--1572835.cif.'
_cod_original_cell_volume        1678.5(7)
_cod_database_code               1572835
_shelx_shelxl_version_number     2019/3
_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_max   0.908
_shelx_estimated_absorpt_t_min   0.380
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
S1A \\sim O0AA \\sim O2AA \\sim O1AA: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.02 within 2A
S1A \\sim O4A \\sim O3A \\sim O2A: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.02 within 2A
Uanis(C11A) \\sim Ueq, Uanis(O1W) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O1W) = Uanis(O2W)
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(O0AA)=Sof(O1AA)=Sof(O2AA)=1-FVAR(1)
 Sof(O2A)=Sof(O3A)=Sof(O4A)=FVAR(1)
 Sof(O2W)=Sof(H2WA)=Sof(H2WB)=1-FVAR(2)
 Sof(O1W)=Sof(H1WA)=Sof(H1WB)=FVAR(2)
4.a Free rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
4.b Ternary CH refined with riding coordinates:
 N1(H1), N4(H4)
4.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B), C5(H5A,H5B), C9(H9A,H9B), C8(H8A,H8B), C7(H7A,H7B),
 C16(H16A,H16B)
4.d Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C6A(H6AA), C7A(H7AA), C6B(H6BA), C7B(H7BA),
 C9A(H9AA), C10A(H10A), C9B(H9BA), C10B(H10B)
4.e Idealised Me refined with riding coordinates:
 C11A(H11A,H11B,H11C), C11B(H11D,H11E,H11F)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4935(3) 0.3270(4) 0.6951(3) 0.0445(8) Uani 1 1 d . . . . .
H1 H 0.537983 0.407996 0.735463 0.053 Uiso 1 1 calc R U . . .
C2 C 0.3837(3) 0.3514(4) 0.6829(3) 0.0434(9) Uani 1 1 d . . . . .
C3 C 0.3037(4) 0.2457(5) 0.6108(3) 0.0461(9) Uani 1 1 d . . . . .
H3A H 0.234075 0.264023 0.606416 0.055 Uiso 1 1 calc R U . . .
H3B H 0.326274 0.150462 0.638852 0.055 Uiso 1 1 calc R U . . .
N4 N 0.2937(3) 0.2546(4) 0.5029(3) 0.0465(8) Uani 1 1 d . . . . .
H4 H 0.268630 0.350595 0.475265 0.056 Uiso 1 1 calc R U . . .
C6 C 0.4855(4) 0.3351(5) 0.5879(3) 0.0512(10) Uani 1 1 d . . . . .
H6A H 0.555417 0.313916 0.593859 0.061 Uiso 1 1 calc R U . . .
H6B H 0.466188 0.431549 0.561119 0.061 Uiso 1 1 calc R U . . .
C5 C 0.4034(4) 0.2334(5) 0.5110(4) 0.0528(10) Uani 1 1 d . . . . .
H5A H 0.427209 0.136355 0.533266 0.063 Uiso 1 1 calc R U . . .
H5B H 0.398033 0.246931 0.442020 0.063 Uiso 1 1 calc R U . . .
C9 C 0.5506(4) 0.1930(5) 0.7559(4) 0.0556(11) Uani 1 1 d . . . . .
H9A H 0.510456 0.109784 0.717133 0.067 Uiso 1 1 calc R U . . .
H9B H 0.621881 0.188173 0.761822 0.067 Uiso 1 1 calc R U . . .
C8 C 0.3509(5) 0.5027(5) 0.6798(4) 0.0616(13) Uani 1 1 d . . . . .
H8A H 0.276224 0.527272 0.632548 0.074 Uiso 1 1 calc R U . . .
H8B H 0.402812 0.575957 0.688028 0.074 Uiso 1 1 calc R U . . .
C7 C 0.3744(4) 0.4112(5) 0.7738(3) 0.0576(12) Uani 1 1 d . . . . .
H7A H 0.440474 0.429266 0.838664 0.069 Uiso 1 1 calc R U . . .
H7B H 0.313878 0.380578 0.783180 0.069 Uiso 1 1 calc R U . . .
C10 C 0.5607(4) 0.1910(5) 0.8636(4) 0.0558(11) Uani 1 1 d . . . . .
C11 C 0.6427(5) 0.2676(6) 0.9448(4) 0.0684(14) Uani 1 1 d . . . . .
H11 H 0.694480 0.313228 0.933100 0.082 Uiso 1 1 calc R U . . .
C12 C 0.6480(6) 0.2766(7) 1.0430(4) 0.0878(19) Uani 1 1 d . . . . .
H12 H 0.703427 0.327019 1.097441 0.105 Uiso 1 1 calc R U . . .
C13 C 0.5697(7) 0.2097(7) 1.0591(5) 0.097(2) Uani 1 1 d . . . . .
H13 H 0.570938 0.219276 1.123803 0.116 Uiso 1 1 calc R U . . .
C14 C 0.4918(7) 0.1309(7) 0.9824(5) 0.0882(18) Uani 1 1 d . . . . .
H14 H 0.441002 0.084065 0.995063 0.106 Uiso 1 1 calc R U . . .
C17 C 0.1025(4) 0.1702(5) 0.4141(3) 0.0551(11) Uani 1 1 d . . . . .
C16 C 0.2127(4) 0.1480(5) 0.4268(4) 0.0580(11) Uani 1 1 d . . . . .
H16A H 0.209826 0.156991 0.358496 0.070 Uiso 1 1 calc R U . . .
H16B H 0.236718 0.052159 0.452535 0.070 Uiso 1 1 calc R U . . .
C15 C 0.4875(5) 0.1200(6) 0.8847(5) 0.0703(14) Uani 1 1 d . . . . .
H15 H 0.434476 0.063889 0.832531 0.084 Uiso 1 1 calc R U . . .
C18 C 0.0345(5) 0.2709(6) 0.3436(4) 0.0695(14) Uani 1 1 d . . . . .
H18 H 0.056456 0.321308 0.301690 0.083 Uiso 1 1 calc R U . . .
C19 C -0.0673(6) 0.2977(8) 0.3347(6) 0.0920(19) Uani 1 1 d . . . . .
H19 H -0.112550 0.366032 0.287686 0.110 Uiso 1 1 calc R U . . .
C20 C -0.0992(6) 0.2217(8) 0.3962(7) 0.097(2) Uani 1 1 d . . . . .
H20 H -0.165845 0.240481 0.391833 0.116 Uiso 1 1 calc R U . . .
O1W O 0.3767(12) 0.9028(10) 0.6438(12) 0.101(4) Uani 0.74(3) 1 d G U P A 1
H1WA H 0.433622 0.854228 0.679452 0.152 Uiso 0.74(3) 1 d G U P A 1
H1WB H 0.333458 0.845164 0.597437 0.152 Uiso 0.74(3) 1 d G U P A 1
O2W O 0.406(3) 0.914(3) 0.611(3) 0.101(4) Uani 0.26(3) 1 d G . P A 2
H2WA H 0.455464 0.859548 0.654099 0.152 Uiso 0.26(3) 1 d G U P A 2
H2WB H 0.366570 0.859632 0.559174 0.152 Uiso 0.26(3) 1 d G U P A 2
S1B S 0.25579(10) 0.63620(12) 0.40614(9) 0.0554(3) Uani 1 1 d . . . . .
S1A S 0.66149(11) 0.67761(14) 0.80595(9) 0.0638(4) Uani 1 1 d . U . . .
C21 C -0.0346(6) 0.1194(8) 0.4634(5) 0.0902(19) Uani 1 1 d . . . . .
H21 H -0.058125 0.066555 0.503049 0.108 Uiso 1 1 calc R U . . .
C22 C 0.0663(5) 0.0940(7) 0.4730(4) 0.0749(16) Uani 1 1 d . . . . .
H22 H 0.110394 0.024487 0.519664 0.090 Uiso 1 1 calc R U . . .
O2A O 0.7314(15) 0.707(2) 0.7637(10) 0.101(5) Uani 0.66(3) 1 d . U P B 1
O3A O 0.5658(14) 0.763(2) 0.7604(11) 0.122(6) Uani 0.66(3) 1 d . U P B 1
O2B O 0.2401(4) 0.7649(4) 0.4509(3) 0.0921(15) Uani 1 1 d . . . . .
O4A O 0.6368(16) 0.5269(13) 0.8026(8) 0.091(4) Uani 0.66(3) 1 d . U P B 1
O3B O 0.3668(3) 0.6048(5) 0.4374(3) 0.0854(13) Uani 1 1 d . . . . .
C5A C 0.7339(4) 0.7214(5) 0.9408(4) 0.0535(11) Uani 1 1 d . . . . .
O4B O 0.2023(3) 0.5156(4) 0.4237(3) 0.0635(9) Uani 1 1 d . . . . .
C6A C 0.8108(4) 0.6282(6) 1.0115(4) 0.0689(14) Uani 1 1 d . . . . .
H6AA H 0.822497 0.540923 0.988064 0.083 Uiso 1 1 calc R U . . .
C5B C 0.1904(4) 0.6629(5) 0.2678(4) 0.0510(10) Uani 1 1 d . . . . .
C7A C 0.8700(5) 0.6650(8) 1.1169(4) 0.0807(17) Uani 1 1 d . . . . .
H7AA H 0.921251 0.601326 1.163336 0.097 Uiso 1 1 calc R U . . .
C6B C 0.1576(4) 0.7967(5) 0.2249(4) 0.0602(12) Uani 1 1 d . . . . .
H6BA H 0.168041 0.874752 0.268483 0.072 Uiso 1 1 calc R U . . .
C8A C 0.8554(5) 0.7933(7) 1.1551(5) 0.0747(15) Uani 1 1 d . . . . .
C7B C 0.1093(5) 0.8144(6) 0.1173(4) 0.0676(14) Uani 1 1 d . . . . .
H7BA H 0.088032 0.905307 0.089300 0.081 Uiso 1 1 calc R U . . .
C9A C 0.7782(5) 0.8828(6) 1.0836(5) 0.0737(15) Uani 1 1 d . . . . .
H9AA H 0.765603 0.969298 1.107326 0.088 Uiso 1 1 calc R U . . .
C8B C 0.0917(4) 0.7022(6) 0.0501(4) 0.0655(13) Uani 1 1 d . . . . .
C10A C 0.7187(5) 0.8496(6) 0.9783(4) 0.0658(13) Uani 1 1 d . . . . .
H10A H 0.667970 0.914008 0.932205 0.079 Uiso 1 1 calc R U . . .
C9B C 0.1263(5) 0.5683(6) 0.0944(4) 0.0651(13) Uani 1 1 d . . . . .
H9BA H 0.116246 0.490638 0.050589 0.078 Uiso 1 1 calc R U . . .
C11A C 0.9232(6) 0.8315(12) 1.2700(5) 0.113(3) Uani 1 1 d . U . . .
H11A H 0.917363 0.931876 1.279127 0.169 Uiso 1 1 calc R U . . .
H11B H 0.997193 0.807617 1.292577 0.169 Uiso 1 1 calc R U . . .
H11C H 0.898231 0.779283 1.311307 0.169 Uiso 1 1 calc R U . . .
C11B C 0.0380(6) 0.7227(8) -0.0681(5) 0.091(2) Uani 1 1 d . . . . .
H11D H -0.028016 0.669200 -0.100789 0.137 Uiso 1 1 calc R U . . .
H11E H 0.085265 0.689900 -0.094093 0.137 Uiso 1 1 calc R U . . .
H11F H 0.022512 0.821979 -0.084446 0.137 Uiso 1 1 calc R U . . .
C10B C 0.1751(4) 0.5481(5) 0.2020(4) 0.0585(12) Uani 1 1 d . . . . .
H10B H 0.197723 0.457541 0.230223 0.070 Uiso 1 1 calc R U . . .
O0AA O 0.589(2) 0.575(3) 0.8021(15) 0.072(6) Uani 0.34(3) 1 d . U P B 2
O1AA O 0.609(2) 0.802(2) 0.7502(18) 0.095(7) Uani 0.34(3) 1 d . U P B 2
O2AA O 0.7404(19) 0.629(4) 0.7762(16) 0.090(7) Uani 0.34(3) 1 d . U P B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1 106.6 . . ?
C2 N1 C6 108.0(3) . . ?
C2 N1 C9 115.3(3) . . ?
C6 N1 H1 106.6 . . ?
C6 N1 C9 113.3(3) . . ?
C9 N1 H1 106.6 . . ?
C3 C2 N1 112.2(3) . . ?
C8 C2 N1 116.1(4) . . ?
C8 C2 C3 119.5(4) . . ?
C8 C2 C7 60.7(3) . . ?
C7 C2 N1 118.6(4) . . ?
C7 C2 C3 120.7(4) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 N4 110.7(3) . . ?
H3A C3 H3B 108.1 . . ?
N4 C3 H3A 109.5 . . ?
N4 C3 H3B 109.5 . . ?
C3 N4 H4 108.1 . . ?
C3 N4 C5 109.2(3) . . ?
C3 N4 C16 112.3(3) . . ?
C5 N4 H4 108.1 . . ?
C5 N4 C16 111.0(3) . . ?
C16 N4 H4 108.1 . . ?
N1 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
N1 C6 C5 112.4(4) . . ?
H6A C6 H6B 107.9 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
N4 C5 H5A 109.2 . . ?
N4 C5 H5B 109.2 . . ?
C6 C5 N4 112.0(4) . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N1 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 N1 111.8(4) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C2 C8 H8A 117.8 . . ?
C2 C8 H8B 117.8 . . ?
C2 C8 C7 59.7(3) . . ?
H8A C8 H8B 114.9 . . ?
C7 C8 H8A 117.8 . . ?
C7 C8 H8B 117.8 . . ?
C2 C7 C8 59.6(3) . . ?
C2 C7 H7A 117.8 . . ?
C2 C7 H7B 117.8 . . ?
C8 C7 H7A 117.8 . . ?
C8 C7 H7B 117.8 . . ?
H7A C7 H7B 114.9 . . ?
C11 C10 C9 119.9(5) . . ?
C15 C10 C9 121.8(5) . . ?
C15 C10 C11 118.2(5) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.7(6) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.2(6) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(6) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(7) . . ?
C15 C14 H14 120.1 . . ?
C18 C17 C16 120.1(5) . . ?
C22 C17 C16 121.5(5) . . ?
C22 C17 C18 118.4(5) . . ?
N4 C16 H16A 109.2 . . ?
N4 C16 H16B 109.2 . . ?
C17 C16 N4 112.1(4) . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C10 C15 C14 121.1(6) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.6(6) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.1(7) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.9(7) . . ?
C21 C20 H20 119.6 . . ?
H1WA O1W H1WB 104.5 . . ?
H2WA O2W H2WB 104.5 . . ?
O2B S1B O3B 114.2(3) . . ?
O2B S1B O4B 111.9(3) . . ?
O2B S1B C5B 106.2(2) . . ?
O3B S1B O4B 111.5(2) . . ?
O3B S1B C5B 106.6(2) . . ?
O4B S1B C5B 105.8(2) . . ?
O2A S1A O3A 113.3(8) . . ?
O2A S1A O4A 112.4(7) . . ?
O2A S1A C5A 106.0(5) . . ?
O3A S1A O4A 111.6(7) . . ?
O3A S1A C5A 107.4(6) . . ?
O4A S1A C5A 105.5(4) . . ?
O0AA S1A C5A 103.5(8) . . ?
O0AA S1A O1AA 111.9(11) . . ?
O0AA S1A O2AA 115.4(12) . . ?
O1AA S1A C5A 107.9(10) . . ?
O1AA S1A O2AA 111.1(14) . . ?
O2AA S1A C5A 106.2(9) . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0(7) . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 121.0(6) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C6A C5A S1A 120.1(4) . . ?
C10A C5A S1A 121.4(4) . . ?
C10A C5A C6A 118.4(5) . . ?
C5A C6A H6AA 120.0 . . ?
C7A C6A C5A 120.0(5) . . ?
C7A C6A H6AA 120.0 . . ?
C6B C5B S1B 121.2(4) . . ?
C6B C5B C10B 119.4(4) . . ?
C10B C5B S1B 119.3(3) . . ?
C6A C7A H7AA 119.0 . . ?
C8A C7A C6A 122.0(6) . . ?
C8A C7A H7AA 119.0 . . ?
C5B C6B H6BA 120.1 . . ?
C7B C6B C5B 119.8(5) . . ?
C7B C6B H6BA 120.1 . . ?
C7A C8A C11A 120.6(7) . . ?
C9A C8A C7A 116.8(5) . . ?
C9A C8A C11A 122.6(6) . . ?
C6B C7B H7BA 119.0 . . ?
C8B C7B C6B 122.0(5) . . ?
C8B C7B H7BA 119.0 . . ?
C8A C9A H9AA 118.7 . . ?
C8A C9A C10A 122.5(5) . . ?
C10A C9A H9AA 118.7 . . ?
C7B C8B C9B 117.7(4) . . ?
C7B C8B C11B 121.6(5) . . ?
C9B C8B C11B 120.7(6) . . ?
C5A C10A H10A 119.8 . . ?
C9A C10A C5A 120.3(5) . . ?
C9A C10A H10A 119.8 . . ?
C8B C9B H9BA 119.3 . . ?
C10B C9B C8B 121.3(5) . . ?
C10B C9B H9BA 119.3 . . ?
C8A C11A H11A 109.5 . . ?
C8A C11A H11B 109.5 . . ?
C8A C11A H11C 109.5 . . ?
H11A C11A H11B 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C8B C11B H11D 109.5 . . ?
C8B C11B H11E 109.5 . . ?
C8B C11B H11F 109.5 . . ?
H11D C11B H11E 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C5B C10B H10B 120.1 . . ?
C9B C10B C5B 119.8(5) . . ?
C9B C10B H10B 120.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1 0.9800 . ?
N1 C2 1.493(5) . ?
N1 C6 1.497(5) . ?
N1 C9 1.524(6) . ?
C2 C3 1.489(6) . ?
C2 C8 1.487(6) . ?
C2 C7 1.488(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 N4 1.497(5) . ?
N4 H4 0.9800 . ?
N4 C5 1.510(6) . ?
N4 C16 1.520(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.502(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.491(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.502(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C10 C11 1.389(7) . ?
C10 C15 1.381(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(10) . ?
C13 H13 0.9300 . ?
C13 C14 1.348(10) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(8) . ?
C17 C16 1.493(7) . ?
C17 C18 1.384(8) . ?
C17 C22 1.381(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C15 H15 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.403(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.371(11) . ?
C20 H20 0.9300 . ?
C20 C21 1.359(10) . ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8501 . ?
O2W H2WA 0.8501 . ?
O2W H2WB 0.8501 . ?
S1B O2B 1.436(4) . ?
S1B O3B 1.439(4) . ?
S1B O4B 1.448(3) . ?
S1B C5B 1.771(5) . ?
S1A O2A 1.413(12) . ?
S1A O3A 1.429(10) . ?
S1A O4A 1.451(9) . ?
S1A C5A 1.760(5) . ?
S1A O0AA 1.392(15) . ?
S1A O1AA 1.41(2) . ?
S1A O2AA 1.446(19) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(9) . ?
C22 H22 0.9300 . ?
C5A C6A 1.388(7) . ?
C5A C10A 1.377(7) . ?
C6A H6AA 0.9300 . ?
C6A C7A 1.384(7) . ?
C5B C6B 1.378(7) . ?
C5B C10B 1.384(7) . ?
C7A H7AA 0.9300 . ?
C7A C8A 1.380(9) . ?
C6B H6BA 0.9300 . ?
C6B C7B 1.374(7) . ?
C8A C9A 1.372(9) . ?
C8A C11A 1.508(8) . ?
C7B H7BA 0.9300 . ?
C7B C8B 1.371(8) . ?
C9A H9AA 0.9300 . ?
C9A C10A 1.375(8) . ?
C8B C9B 1.388(8) . ?
C8B C11B 1.512(7) . ?
C10A H10A 0.9300 . ?
C9B H9BA 0.9300 . ?
C9B C10B 1.377(7) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C10B H10B 0.9300 . ?
