#------------------------------------------------------------------------------
#$Date: 2022-03-03 11:41:52 +0200 (Thu, 03 Mar 2022) $
#$Revision: 273219 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/46/8104610.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_8104610
loop_
_publ_author_name
'Chen, Hai-Lin'
'Huang, Xiu-Xiang'
'Yao, Dong-Mei'
'Wang, Yan-Ping'
'Lu, Xiao-Bing'
_publ_section_title
;
 Synthesis and crystal structure of
 5-(8-((3-carboxyazetidin-1-ium-1-yl)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate
 monohydrate, C20H19NO10S
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1371
_journal_page_last               1373
_journal_paper_doi               10.1515/ncrs-2021-0346
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C20 H17 N O9 S, H2 O'
_chemical_formula_sum            'C20 H19 N O10 S'
_chemical_formula_weight         465.42
_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   mixed
_cell_angle_alpha                102.413(2)
_cell_angle_beta                 103.199(2)
_cell_angle_gamma                97.753(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3470(2)
_cell_length_b                   9.6701(2)
_cell_length_c                   12.9523(3)
_cell_measurement_reflns_used    7183
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      75.3590
_cell_measurement_theta_min      3.6020
_cell_volume                     975.26(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.64a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     12.00  78.00   0.50    0.05    --   39.20  37.00  60.00  132
  2  ω     85.00 120.00   0.50    0.05    --   39.20  37.00  60.00   70
  3  ω     84.00 109.00   0.50    0.17    --  111.82  45.00 120.00   50
  4  ω    113.00 170.00   0.50    0.17    --  111.82  45.00 120.00  114
  5  ω    131.00 175.00   0.50    0.17    --  111.82  61.00  90.00   88
  6  ω     75.00 174.00   0.50    0.17    --  111.82  30.00  30.00  198
  7  ω     33.00  90.00   0.50    0.17    --  111.82   0.00 -90.00  114
  8  ω     94.00 168.00   0.50    0.17    --  111.82   0.00 -90.00  148
  9  ω    -38.00  20.00   0.50    0.17    --  -62.00  30.00-150.00  116
 10  ω    -25.00  11.00   0.50    0.17    --  -62.00  15.00   0.00   72
 11  ω    -28.00  20.00   0.50    0.17    --  -62.00  15.00 120.00   96
 12  ω    -37.00  17.00   0.50    0.17    --  -62.00  30.00 150.00  108
 13  ω     76.00 109.00   0.50    0.05    --   39.20-158.00 134.00   66
 14  ω     86.00 122.00   0.50    0.17    --  111.82-158.00 134.00   72
 15  ω     69.00 104.00   0.50    0.17    --  111.82-111.00  60.00   70
 16  ω     38.00  66.00   0.50    0.17    --  111.82-111.00 -60.00   56
 17  ω     78.00 109.00   0.50    0.17    --  111.82-118.00 -72.00   62
 18  ω     71.00 102.00   0.50    0.17    --  111.82-111.00 -60.00   62
 19  ω     70.00 107.00   0.50    0.17    --  111.82-111.00-150.00   74
 20  ω     35.00  61.00   0.50    0.17    --  111.82-111.00-150.00   52
 21  ω     13.00  89.00   0.50    0.05    --   39.20-118.00 -72.00  152
 22  ω     63.00  89.00   0.50    0.17    --  111.82 -94.00  90.00   52
 23  ω     79.00 106.00   0.50    0.17    --  111.82-111.00 150.00   54
 24  ω     37.00 101.00   0.50    0.17    --  111.82 -94.00 150.00  128
 25  ω     34.00  60.00   0.50    0.17    --  111.82 -94.00  90.00   52
 26  ω     35.00  89.00   0.50    0.17    --  111.82 -94.00-120.00  108
 27  ω     74.00 102.00   0.50    0.17    --  111.82 -77.00 -60.00   56
 28  ω     64.00 102.00   0.50    0.17    --  111.82 -77.00 -90.00   76
 29  ω     46.00  77.00   0.50    0.17    --  111.82 -77.00-180.00   62
 30  ω     38.00  63.00   0.50    0.17    --  111.82 -61.00 -60.00   50
 31  ω     39.00  65.00   0.50    0.17    --  111.82 -77.00 -60.00   52
 32  ω     38.00  63.00   0.50    0.17    --  111.82 -61.00 -90.00   50
 33  ω     59.00 102.00   0.50    0.17    --  111.82 -77.00  30.00   86
 34  ω     39.00  65.00   0.50    0.17    --  111.82 -61.00  90.00   52
 35  ω     42.00  68.00   0.50    0.17    --  111.82 -61.00 120.00   52
 36  ω     38.00  66.00   0.50    0.17    --  111.82 -61.00  30.00   56
 37  ω     39.00  65.00   0.50    0.17    --  111.82 -61.00   0.00   52
 38  ω     -8.00  19.00   0.50    0.05    --   39.20 -19.00-120.00   54
 39  ω    -42.00  23.00   0.50    0.05    --   39.20 -19.00 -30.00  130
 40  ω     84.00 134.00   0.50    0.17    --  111.82 111.00  60.00  100
 41  ω     82.00 108.00   0.50    0.17    --  111.82 158.00 167.00   52
 42  ω     55.00 110.00   0.50    0.05    --   39.20 158.00 167.00  110
 43  ω    125.00 160.00   0.50    0.17    --  111.82 118.00  13.00   70
 44  ω     97.00 153.00   0.50    0.17    --  111.82 111.00 -30.00  112
 45  ω     87.00 112.00   0.50    0.17    --  111.82 111.00-150.00   50
 46  ω    -95.00 -68.00   0.50    0.05    --  -39.20 -77.00 120.00   54
 47  ω   -111.00 -70.00   0.50    0.05    --  -39.20-158.00 134.00   82
 48  ω   -122.00 -97.00   0.50    0.17    --  -62.00-158.00 134.00   50
 49  ω   -138.00-113.00   0.50    0.17    --  -62.00-118.00 -72.00   50
 50  ω    -44.00  -4.00   0.50    0.05    --  -39.20 -77.00 120.00   80
 51  ω    -88.00 -63.00   0.50    0.17    --  -62.00 118.00  13.00   50
 52  ω    -59.00 -33.00   0.50    0.05    --  -39.20 118.00  13.00   52
 53  ω    -95.00 -70.00   0.50    0.05    --  -39.20 158.00 167.00   50
 54  ω   -110.00 -85.00   0.50    0.17    --  -62.00 158.00 167.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0132876000
_diffrn_orient_matrix_UB_12      0.0335826000
_diffrn_orient_matrix_UB_13      -0.1090893000
_diffrn_orient_matrix_UB_21      0.0812483000
_diffrn_orient_matrix_UB_22      0.1577688000
_diffrn_orient_matrix_UB_23      0.0614490000
_diffrn_orient_matrix_UB_31      0.1748078000
_diffrn_orient_matrix_UB_32      -0.0403202000
_diffrn_orient_matrix_UB_33      0.0168671000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10313
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.765
_diffrn_reflns_theta_min         3.625
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.64a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3921
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0549P)²+0.6407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3522
_reflns_number_total             3921
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0346_suppl.cif
_cod_data_source_block           nchl-chl8.24-ding-100k
_cod_database_code               8104610
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 N1-C16 \\sim N1A-C16
 with sigma of 0.02
 N1-C19 \\sim N1A-C19
 with sigma of 0.02
 N1-C17 \\sim N1A-C17
 with sigma of 0.02
 O9-C20 \\sim O9A-C20A
 with sigma of 0.02
 O9-C18 \\sim O9A-C18
 with sigma of 0.04
 O8-C20 \\sim O8A-C20A
 with sigma of 0.02
 C18-C20 \\sim C18-C20A
 with sigma of 0.02
 O8-C18 \\sim O8A-C18
 with sigma of 0.04
 O9-O8 \\sim O9A-O8A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(N1A)
Uanis(O8) = Uanis(O8A)
Uanis(O9) = Uanis(O9A)
Uanis(C20) = Uanis(C20A)
4. Others
 Sof(H16C)=Sof(H16D)=Sof(H17C)=Sof(H17D)=Sof(H19C)=Sof(H19D)=Sof(N1A)=
 Sof(H1AA)=1-FVAR(1)
 Sof(H16A)=Sof(H16B)=Sof(H17A)=Sof(H17B)=Sof(H19A)=Sof(H19B)=Sof(N1)=Sof(H1A)=
 FVAR(1)
 Sof(H18A)=Sof(O8A)=Sof(H8A)=Sof(O9A)=Sof(C20A)=1-FVAR(2)
 Sof(H18)=Sof(O8)=Sof(O9)=Sof(H9A)=Sof(C20)=FVAR(2)
5.a Free rotating group:
 O10(H10A,H10B)
5.b Ternary CH refined with riding coordinates:
 C18(H18), C18(H18A), N1(H1A), N1A(H1AA)
5.c Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C16(H16C,H16D), C17(H17A,H17B), C17(H17C,H17D), C19(H19A,
 H19B), C19(H19C,H19D)
5.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C9(H9), C11(H11), C14(H14), C15(H15)
5.e Tetrahedral OH refined with riding coordinates:
 O8A(H8A)
5.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O9(H9A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.701
_oxdiff_exptl_absorpt_empirical_full_min 0.637
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
S1 S 0.32952(6) 1.02505(6) 0.27507(4) 0.02944(15) Uani 1 1 d . . . . .
O1 O 0.8547(2) 0.31935(17) 0.70992(13) 0.0349(4) Uani 1 1 d . . . . .
H1 H 0.812691 0.230914 0.686191 0.052 Uiso 1 1 calc R U . . .
O2 O 0.7064(2) 0.53247(16) 0.27267(12) 0.0345(4) Uani 1 1 d . . . . .
O3 O 0.91535(18) 0.74483(15) 0.59367(11) 0.0276(3) Uani 1 1 d . . . . .
O4 O 0.54484(19) 1.10244(18) 0.13564(13) 0.0350(4) Uani 1 1 d . . . . .
H4 H 0.606955 1.120779 0.095664 0.052 Uiso 1 1 calc R U . . .
O5 O 0.36072(19) 1.18161(17) 0.31074(14) 0.0354(4) Uani 1 1 d . . . . .
O6 O 0.27614(19) 0.95781(17) 0.35597(13) 0.0336(3) Uani 1 1 d . . . . .
O7 O 0.21524(19) 0.96833(18) 0.16621(13) 0.0353(4) Uani 1 1 d . . . . .
C1 C 0.8307(3) 0.3832(2) 0.62611(17) 0.0298(4) Uani 1 1 d . . . . .
C2 C 0.7558(3) 0.3033(2) 0.51718(18) 0.0303(4) Uani 1 1 d . . . . .
H2 H 0.720157 0.201624 0.501020 0.036 Uiso 1 1 calc R U . . .
C3 C 0.7340(3) 0.3724(2) 0.43402(18) 0.0296(4) Uani 1 1 d . . . . .
H3 H 0.683211 0.318161 0.360512 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7866(2) 0.5232(2) 0.45705(17) 0.0267(4) Uani 1 1 d . . . . .
C5 C 0.8598(2) 0.5986(2) 0.56547(17) 0.0266(4) Uani 1 1 d . . . . .
C6 C 0.8830(2) 0.5328(2) 0.65227(17) 0.0281(4) Uani 1 1 d . . . . .
C7 C 0.7621(3) 0.5994(2) 0.37095(17) 0.0279(4) Uani 1 1 d . . . . .
C8 C 0.8017(2) 0.7557(2) 0.40900(17) 0.0274(4) Uani 1 1 d . . . . .
C9 C 0.8767(3) 0.8169(2) 0.51582(17) 0.0280(4) Uani 1 1 d . . . . .
H9 H 0.904785 0.919306 0.538307 0.034 Uiso 1 1 calc R U . . .
C10 C 0.7430(3) 0.8490(2) 0.33547(17) 0.0273(4) Uani 1 1 d . . . . .
C11 C 0.5911(3) 0.8909(2) 0.33709(17) 0.0283(4) Uani 1 1 d . . . . .
H11 H 0.530742 0.861269 0.385058 0.034 Uiso 1 1 calc R U . . .
C12 C 0.5252(3) 0.9753(2) 0.27009(17) 0.0281(4) Uani 1 1 d . . . . .
C13 C 0.6136(3) 1.0209(2) 0.19941(17) 0.0288(4) Uani 1 1 d . . . . .
C14 C 0.7673(3) 0.9801(2) 0.19900(17) 0.0296(4) Uani 1 1 d . . . . .
H14 H 0.829442 1.011125 0.152384 0.036 Uiso 1 1 calc R U . . .
C15 C 0.8308(3) 0.8950(2) 0.26545(18) 0.0291(4) Uani 1 1 d . . . . .
H15 H 0.935378 0.867537 0.263397 0.035 Uiso 1 1 calc R U . . .
C16 C 0.9590(3) 0.6194(3) 0.76862(18) 0.0328(5) Uani 1 1 d D . . . .
H16A H 1.044340 0.702711 0.771243 0.039 Uiso 0.805(4) 1 calc R U P A 1
H16B H 1.014112 0.558952 0.813030 0.039 Uiso 0.805(4) 1 calc R U P A 1
H16C H 1.071882 0.596747 0.791700 0.039 Uiso 0.195(4) 1 calc R U P A 2
H16D H 0.976312 0.722136 0.767019 0.039 Uiso 0.195(4) 1 calc R U P A 2
C17 C 0.8602(3) 0.7436(2) 0.93544(18) 0.0337(5) Uani 1 1 d D . . . .
H17A H 0.868785 0.849548 0.952386 0.040 Uiso 0.805(4) 1 calc R U P A 1
H17B H 0.958451 0.717166 0.980506 0.040 Uiso 0.805(4) 1 calc R U P A 1
H17C H 0.945466 0.769669 1.007065 0.040 Uiso 0.195(4) 1 calc R U P A 2
H17D H 0.851131 0.828605 0.904998 0.040 Uiso 0.195(4) 1 calc R U P A 2
C18 C 0.6900(3) 0.6598(3) 0.93670(19) 0.0366(5) Uani 1 1 d D . . . .
H18 H 0.599331 0.717743 0.934275 0.044 Uiso 0.833(2) 1 calc R U P B 1
H18A H 0.612944 0.724971 0.914152 0.044 Uiso 0.167(2) 1 calc R U P B 2
C19 C 0.6853(3) 0.5632(3) 0.82590(19) 0.0351(5) Uani 1 1 d D . . . .
H19A H 0.718724 0.469796 0.830475 0.042 Uiso 0.805(4) 1 calc R U P A 1
H19B H 0.577189 0.548190 0.770036 0.042 Uiso 0.805(4) 1 calc R U P A 1
H19C H 0.623800 0.594047 0.762558 0.042 Uiso 0.195(4) 1 calc R U P A 2
H19D H 0.645980 0.459292 0.818317 0.042 Uiso 0.195(4) 1 calc R U P A 2
O8 O 0.7990(3) 0.4901(2) 1.03187(17) 0.0393(5) Uani 0.833(2) 1 d D . P B 1
O9 O 0.6237(2) 0.6199(2) 1.09650(15) 0.0320(4) Uani 0.833(2) 1 d D . P B 1
H9A H 0.665273 0.600332 1.155863 0.048 Uiso 0.833(2) 1 calc R U P B 1
N1 N 0.8202(3) 0.6712(2) 0.81336(18) 0.0294(5) Uani 0.805(4) 1 d D . P A 1
H1A H 0.768690 0.735728 0.770122 0.035 Uiso 0.805(4) 1 calc R U P A 1
C20 C 0.7088(3) 0.5797(3) 1.0269(2) 0.0292(5) Uani 0.833(2) 1 d D . P B 1
O8A O 0.7696(12) 0.5924(11) 1.0976(9) 0.0393(5) Uani 0.167(2) 1 d D . P B 2
H8A H 0.733365 0.553297 1.141914 0.059 Uiso 0.167(2) 1 calc R U P B 2
O9A O 0.5176(11) 0.6564(10) 1.0654(7) 0.0320(4) Uani 0.167(2) 1 d D . P B 2
N1A N 0.8817(10) 0.6091(9) 0.8531(7) 0.0294(5) Uani 0.195(4) 1 d D . P A 2
H1AA H 0.934801 0.544207 0.895186 0.035 Uiso 0.195(4) 1 calc R U P A 2
C20A C 0.6481(14) 0.6395(15) 1.0394(10) 0.0292(5) Uani 0.167(2) 1 d D . P B 2
O10 O 0.7320(2) 1.19437(18) 0.01927(13) 0.0365(4) Uani 1 1 d G . . . .
H10A H 0.734750 1.144244 -0.044482 0.055 Uiso 1 1 d G U . . .
H10B H 0.724942 1.280205 0.010318 0.055 Uiso 1 1 d G U . . .
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
O5 S1 O6 111.90(10) . .
O5 S1 C12 106.89(10) . .
O6 S1 C12 104.83(9) . .
O7 S1 O5 112.81(9) . .
O7 S1 O6 112.10(10) . .
O7 S1 C12 107.74(10) . .
C1 O1 H1 109.5 . .
C9 O3 C5 118.15(16) . .
C13 O4 H4 109.5 . .
O1 C1 C2 121.7(2) . .
O1 C1 C6 117.05(19) . .
C6 C1 C2 121.24(19) . .
C1 C2 H2 120.0 . .
C3 C2 C1 119.9(2) . .
C3 C2 H2 120.0 . .
C2 C3 H3 119.7 . .
C2 C3 C4 120.5(2) . .
C4 C3 H3 119.7 . .
C3 C4 C7 121.64(19) . .
C5 C4 C3 117.98(18) . .
C5 C4 C7 120.36(19) . .
O3 C5 C4 121.14(18) . .
O3 C5 C6 115.56(18) . .
C4 C5 C6 123.29(19) . .
C1 C6 C5 117.04(19) . .
C1 C6 C16 121.58(19) . .
C5 C6 C16 121.37(19) . .
O2 C7 C4 121.05(19) . .
O2 C7 C8 123.80(19) . .
C8 C7 C4 115.11(18) . .
C7 C8 C10 121.44(18) . .
C9 C8 C7 118.87(18) . .
C9 C8 C10 119.27(19) . .
O3 C9 H9 117.3 . .
C8 C9 O3 125.37(19) . .
C8 C9 H9 117.3 . .
C11 C10 C8 117.42(18) . .
C11 C10 C15 118.48(18) . .
C15 C10 C8 124.10(18) . .
C10 C11 H11 119.3 . .
C10 C11 C12 121.43(19) . .
C12 C11 H11 119.3 . .
C11 C12 S1 119.51(16) . .
C11 C12 C13 119.95(19) . .
C13 C12 S1 120.54(15) . .
O4 C13 C12 117.99(19) . .
O4 C13 C14 123.55(19) . .
C14 C13 C12 118.46(18) . .
C13 C14 H14 119.5 . .
C15 C14 C13 120.99(19) . .
C15 C14 H14 119.5 . .
C10 C15 H15 119.7 . .
C14 C15 C10 120.69(19) . .
C14 C15 H15 119.7 . .
C6 C16 H16A 110.1 . .
C6 C16 H16B 110.1 . .
C6 C16 H16C 106.7 . .
C6 C16 H16D 106.7 . .
C6 C16 N1 107.90(17) . .
H16A C16 H16B 108.4 . .
H16C C16 H16D 106.6 . .
N1 C16 H16A 110.1 . .
N1 C16 H16B 110.1 . .
N1A C16 C6 122.6(4) . .
N1A C16 H16C 106.7 . .
N1A C16 H16D 106.7 . .
H17A C17 H17B 111.1 . .
H17C C17 H17D 111.0 . .
C18 C17 H17A 113.9 . .
C18 C17 H17B 113.9 . .
C18 C17 H17C 113.7 . .
C18 C17 H17D 113.7 . .
C18 C17 N1A 89.4(3) . .
N1 C17 H17A 113.9 . .
N1 C17 H17B 113.9 . .
N1 C17 C18 88.54(17) . .
N1A C17 H17C 113.7 . .
N1A C17 H17D 113.7 . .
C17 C18 H18 114.1 . .
C17 C18 H18A 101.3 . .
C19 C18 C17 87.43(17) . .
C19 C18 H18 114.1 . .
C19 C18 H18A 101.3 . .
C19 C18 C20 112.4(2) . .
C20 C18 C17 111.89(19) . .
C20 C18 H18 114.1 . .
C20A C18 C17 123.3(5) . .
C20A C18 H18A 101.3 . .
C20A C18 C19 136.5(6) . .
C18 C19 H19A 113.6 . .
C18 C19 H19B 113.6 . .
C18 C19 H19C 113.8 . .
C18 C19 H19D 113.8 . .
C18 C19 N1A 89.3(3) . .
H19A C19 H19B 110.8 . .
H19C C19 H19D 111.0 . .
N1 C19 C18 90.43(18) . .
N1 C19 H19A 113.6 . .
N1 C19 H19B 113.6 . .
N1A C19 H19C 113.8 . .
N1A C19 H19D 113.8 . .
C20 O9 H9A 109.5 . .
C16 N1 C17 118.18(18) . .
C16 N1 H1A 109.6 . .
C17 N1 H1A 109.6 . .
C19 N1 C16 119.09(19) . .
C19 N1 C17 89.29(17) . .
C19 N1 H1A 109.6 . .
O8 C20 C18 121.9(2) . .
O8 C20 O9 125.2(2) . .
O9 C20 C18 112.9(2) . .
C20A O8A H8A 109.5 . .
C16 N1A C17 122.8(6) . .
C16 N1A C19 120.1(6) . .
C16 N1A H1AA 108.8 . .
C17 N1A C19 85.3(4) . .
C17 N1A H1AA 108.8 . .
C19 N1A H1AA 108.8 . .
O8A C20A C18 109.5(9) . .
O9A C20A C18 126.7(10) . .
O9A C20A O8A 123.7(11) . .
H10A O10 H10B 104.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O5 1.4530(17) .
S1 O6 1.4654(15) .
S1 O7 1.4529(17) .
S1 C12 1.775(2) .
O1 H1 0.8400 .
O1 C1 1.350(2) .
O2 C7 1.245(3) .
O3 C5 1.368(2) .
O3 C9 1.349(2) .
O4 H4 0.8400 .
O4 C13 1.349(2) .
C1 C2 1.406(3) .
C1 C6 1.396(3) .
C2 H2 0.9500 .
C2 C3 1.376(3) .
C3 H3 0.9500 .
C3 C4 1.410(3) .
C4 C5 1.387(3) .
C4 C7 1.455(3) .
C5 C6 1.396(3) .
C6 C16 1.501(3) .
C7 C8 1.451(3) .
C8 C9 1.345(3) .
C8 C10 1.496(3) .
C9 H9 0.9500 .
C10 C11 1.385(3) .
C10 C15 1.395(3) .
C11 H11 0.9500 .
C11 C12 1.389(3) .
C12 C13 1.404(3) .
C13 C14 1.394(3) .
C14 H14 0.9500 .
C14 C15 1.383(3) .
C15 H15 0.9500 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C16 H16C 0.9900 .
C16 H16D 0.9900 .
C16 N1 1.506(3) .
C16 N1A 1.405(8) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C17 H17C 0.9900 .
C17 H17D 0.9900 .
C17 C18 1.543(3) .
C17 N1 1.524(3) .
C17 N1A 1.554(9) .
C18 H18 1.0000 .
C18 H18A 1.0000 .
C18 C19 1.524(3) .
C18 C20 1.525(3) .
C18 C20A 1.495(12) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C19 H19C 0.9900 .
C19 H19D 0.9900 .
C19 N1 1.492(3) .
C19 N1A 1.575(8) .
O8 C20 1.224(3) .
O9 H9A 0.8400 .
O9 C20 1.298(3) .
N1 H1A 1.0000 .
O8A H8A 0.8400 .
O8A C20A 1.315(13) .
O9A C20A 1.232(13) .
N1A H1AA 1.0000 .
O10 H10A 0.8699 .
O10 H10B 0.8702 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
S1 C12 C13 O4 -0.3(3) . . . .
S1 C12 C13 C14 179.51(16) . . . .
O1 C1 C2 C3 -179.81(19) . . . .
O1 C1 C6 C5 179.38(18) . . . .
O1 C1 C6 C16 -1.3(3) . . . .
O2 C7 C8 C9 -173.5(2) . . . .
O2 C7 C8 C10 13.9(3) . . . .
O3 C5 C6 C1 -178.77(17) . . . .
O3 C5 C6 C16 2.0(3) . . . .
O4 C13 C14 C15 -179.3(2) . . . .
O5 S1 C12 C11 118.32(18) . . . .
O5 S1 C12 C13 -61.5(2) . . . .
O6 S1 C12 C11 -0.6(2) . . . .
O6 S1 C12 C13 179.60(17) . . . .
O7 S1 C12 C11 -120.18(18) . . . .
O7 S1 C12 C13 60.0(2) . . . .
C1 C2 C3 C4 0.1(3) . . . .
C1 C6 C16 N1 -93.0(2) . . . .
C1 C6 C16 N1A -51.9(5) . . . .
C2 C1 C6 C5 -0.9(3) . . . .
C2 C1 C6 C16 178.36(19) . . . .
C2 C3 C4 C5 -0.2(3) . . . .
C2 C3 C4 C7 -178.76(19) . . . .
C3 C4 C5 O3 179.30(17) . . . .
C3 C4 C5 C6 -0.3(3) . . . .
C3 C4 C7 O2 -6.0(3) . . . .
C3 C4 C7 C8 171.98(18) . . . .
C4 C5 C6 C1 0.8(3) . . . .
C4 C5 C6 C16 -178.47(19) . . . .
C4 C7 C8 C9 8.5(3) . . . .
C4 C7 C8 C10 -164.03(18) . . . .
C5 O3 C9 C8 -7.0(3) . . . .
C5 C4 C7 O2 175.45(19) . . . .
C5 C4 C7 C8 -6.5(3) . . . .
C5 C6 C16 N1 86.2(2) . . . .
C5 C6 C16 N1A 127.3(5) . . . .
C6 C1 C2 C3 0.5(3) . . . .
C6 C16 N1 C17 171.29(18) . . . .
C6 C16 N1 C19 64.9(2) . . . .
C6 C16 N1A C17 -132.0(5) . . . .
C6 C16 N1A C19 -26.9(8) . . . .
C7 C4 C5 O3 -2.1(3) . . . .
C7 C4 C5 C6 178.32(19) . . . .
C7 C8 C9 O3 -2.1(3) . . . .
C7 C8 C10 C11 92.0(2) . . . .
C7 C8 C10 C15 -87.6(3) . . . .
C8 C10 C11 C12 -178.80(19) . . . .
C8 C10 C15 C14 179.3(2) . . . .
C9 O3 C5 C4 9.0(3) . . . .
C9 O3 C5 C6 -171.44(17) . . . .
C9 C8 C10 C11 -80.6(3) . . . .
C9 C8 C10 C15 99.9(3) . . . .
C10 C8 C9 O3 170.68(18) . . . .
C10 C11 C12 S1 179.69(16) . . . .
C10 C11 C12 C13 -0.5(3) . . . .
C11 C10 C15 C14 -0.2(3) . . . .
C11 C12 C13 O4 179.86(19) . . . .
C11 C12 C13 C14 -0.3(3) . . . .
C12 C13 C14 C15 0.8(3) . . . .
C13 C14 C15 C10 -0.6(3) . . . .
C15 C10 C11 C12 0.8(3) . . . .
C17 C18 C19 N1 -15.67(17) . . . .
C17 C18 C19 N1A 21.9(4) . . . .
C17 C18 C20 O8 -58.0(3) . . . .
C17 C18 C20 O9 120.4(2) . . . .
C17 C18 C20A O8A -49.7(13) . . . .
C17 C18 C20A O9A 133.7(11) . . . .
C18 C17 N1 C16 -138.7(2) . . . .
C18 C17 N1 C19 -15.66(17) . . . .
C18 C17 N1A C16 144.6(6) . . . .
C18 C17 N1A C19 21.5(3) . . . .
C18 C19 N1 C16 138.1(2) . . . .
C18 C19 N1 C17 15.86(17) . . . .
C18 C19 N1A C16 -147.3(6) . . . .
C18 C19 N1A C17 -21.8(3) . . . .
C19 C18 C20 O8 38.6(3) . . . .
C19 C18 C20 O9 -143.1(2) . . . .
C19 C18 C20A O8A 78.3(11) . . . .
C19 C18 C20A O9A -98.3(14) . . . .
N1 C17 C18 C19 15.34(17) . . . .
N1 C17 C18 C20 128.5(2) . . . .
C20 C18 C19 N1 -128.3(2) . . . .
N1A C17 C18 C19 -22.3(4) . . . .
N1A C17 C18 C20A 124.9(7) . . . .
C20A C18 C19 N1A -116.8(8) . . . .
