#------------------------------------------------------------------------------
#$Date: 2020-06-05 14:30:01 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252920 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157491.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_7157491
loop_
_publ_author_name
'Tota, Arianna'
'Carlucci, Claudia'
'Pisano, Luisa'
'Cutolo, Giuliano'
'Clarkson, Guy J.'
'Romanazzi, Giuseppe'
'Degennaro, Leonardo'
'Bull, James A.'
'Rollin, Patrick'
'Luisi, Renzo'
_publ_section_title
;
 Synthesis of glycosyl sulfoximines by a highly chemo- and stereoselective
 NH- and O-transfer to thioglycosides.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3893
_journal_page_last               3897
_journal_paper_doi               10.1039/d0ob00647e
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         '2(C20 H31 N O10 S), C5 H12'
_chemical_formula_sum            'C45 H74 N2 O20 S2'
_chemical_formula_weight         1027.18
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-24 deposited with the CCDC.	2020-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.74142(5)
_cell_length_b                   9.74142(5)
_cell_length_c                   55.7588(4)
_cell_measurement_reflns_used    25529
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.6410
_cell_measurement_theta_min      3.1180
_cell_volume                     5291.25(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6093
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  34.00   1.00    1.00    --  -41.82  77.00 -90.00  108
  2  ω    -66.00  33.00   1.00    1.00    --  -41.82  37.00-180.00   99
  3  ω    103.00 178.00   1.00    4.00    --  107.00  77.00 120.00   75
  4  ω    103.00 178.00   1.00    4.00    --  107.00  77.00  60.00   75
  5  ω     81.00 178.00   1.00    4.00    --  107.00  45.00-150.00   97
  6  ω    103.00 178.00   1.00    4.00    --  107.00  77.00   0.00   75
  7  ω     81.00 178.00   1.00    4.00    --  107.00  45.00-120.00   97
  8  ω     81.00 178.00   1.00    4.00    --  107.00  45.00 -30.00   97
  9  ω     35.00 136.00   1.00    4.00    --  107.00 -61.00 -90.00  101
 10  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00-120.00  100
 11  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00  30.00  100
 12  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00 150.00  100
 13  ω     81.00 178.00   1.00    4.00    --  107.00  45.00  90.00   97
 14  ω     24.00 107.00   1.00    4.00    --  107.00 -94.00-150.00   83
 15  ω     34.00 112.00   1.00    4.00    --  107.00-125.00 120.00   78
 16  ω     78.00 178.00   1.00    4.00    --  107.00  61.00 -90.00  100
 17  ω     78.00 178.00   1.00    4.00    --  107.00  61.00 150.00  100
 18  ω     34.00 112.00   1.00    4.00    --  107.00-125.00-180.00   78
 19  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00  90.00  100
 20  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00 -30.00  100
 21  ω     61.00 131.00   1.00    1.00    --   41.82 178.00 150.00   70
 22  ω     78.00 178.00   1.00    4.00    --  107.00  61.00 120.00  100
 23  ω     78.00 178.00   1.00    4.00    --  107.00  61.00   0.00  100
 24  ω     24.00 107.00   1.00    4.00    --  107.00 -94.00 -90.00   83
 25  ω     78.00 162.00   1.00    4.00    --  107.00  61.00 -60.00   84
 26  ω     78.00 178.00   1.00    4.00    --  107.00  61.00  30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0031424000
_diffrn_orient_matrix_UB_12      0.1543298000
_diffrn_orient_matrix_UB_13      -0.0059787000
_diffrn_orient_matrix_UB_21      -0.0220009000
_diffrn_orient_matrix_UB_22      -0.0343954000
_diffrn_orient_matrix_UB_23      -0.0266963000
_diffrn_orient_matrix_UB_31      -0.1565826000
_diffrn_orient_matrix_UB_32      0.0017829000
_diffrn_orient_matrix_UB_33      0.0038777000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       68
_diffrn_reflns_limit_l_min       -69
_diffrn_reflns_number            78929
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.704
_diffrn_reflns_theta_min         3.170
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.547
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             2200
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1983 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Flack x: 0.007(5) Shelx 2018
Hooft y: -0.002(5)  Olex2
the molecule contains known chiral centres that are not affected by the synthetic steps
;
_refine_ls_abs_structure_Flack   0.007(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5339
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0464
_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)+(0.0544P)²+5.3337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1193
_reflns_Friedel_coverage         0.648
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                5274
_reflns_number_total             5339
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00647e2.cif
_cod_data_source_block           rl3
_cod_depositor_comments          'Adding full bibliography for 7157491.cif.'
_cod_original_cell_volume        5291.24(7)
_cod_database_code               7157491
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H20 N2 O2'
_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   0.886
_shelx_estimated_absorpt_t_min   0.654
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
The determination of the oxygen and nitrogen of the sulfoximine was decided by taking into account the thermal 
ellipsoids of the two atoms, bond lengths (S=O shorter than S=N as confirmed from related structures in the CCDC) 
and the hydrogen was located in a difference map confirming the identity of the nitrogen (see below). 
The hydrogen (H7) on the nitrogen was located in a difference map and its position allowed to refine freely but 
given thermal ellipsoids 1.2 times the equivalent isotropic displacement parameter of N7

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C100, C101, C102
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
3. Others
 Fixed Sof: H10G(0.5) H10F(0.5)
4.a Ternary CH refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C13(H13A,
 H13B), C101(H10D,H10E), C102(H10G,H10F)
4.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C100(H10A,H10B,H10C)
;
_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 31.292
_oxdiff_exptl_absorpt_empirical_full_min 0.497
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'
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
C1 C 0.6864(3) 0.6252(4) 0.42141(6) 0.0271(7) Uani 1 1 d . . . . .
H1A H 0.623365 0.642407 0.407807 0.033 Uiso 1 1 calc R . . . .
H1B H 0.750277 0.703853 0.422635 0.033 Uiso 1 1 calc R . . . .
C2 C 0.6034(4) 0.6124(4) 0.44468(6) 0.0358(8) Uani 1 1 d . . . . .
H2A H 0.555292 0.699952 0.447925 0.043 Uiso 1 1 calc R . . . .
H2B H 0.533430 0.539477 0.442864 0.043 Uiso 1 1 calc R . . . .
C3 C 0.6977(5) 0.5778(5) 0.46576(7) 0.0476(11) Uani 1 1 d . . . . .
H3A H 0.763420 0.653885 0.468332 0.057 Uiso 1 1 calc R . . . .
H3B H 0.642248 0.567165 0.480524 0.057 Uiso 1 1 calc R . . . .
C4 C 0.7758(5) 0.4463(5) 0.46090(7) 0.0449(10) Uani 1 1 d . . . . .
H4A H 0.710065 0.369403 0.459200 0.054 Uiso 1 1 calc R . . . .
H4B H 0.836687 0.425885 0.474658 0.054 Uiso 1 1 calc R . . . .
C5 C 0.8619(4) 0.4585(4) 0.43800(6) 0.0306(7) Uani 1 1 d . . . . .
H5A H 0.909919 0.370746 0.434867 0.037 Uiso 1 1 calc R . . . .
H5B H 0.931878 0.531324 0.439995 0.037 Uiso 1 1 calc R . . . .
C6 C 0.7676(3) 0.4935(3) 0.41684(5) 0.0224(6) Uani 1 1 d . . . . .
H6 H 0.701824 0.416086 0.414286 0.027 Uiso 1 1 calc R . . . .
N7 N 0.9304(3) 0.3682(3) 0.38658(5) 0.0269(6) Uani 1 1 d . . . . .
H7 H 0.999(5) 0.367(4) 0.3773(8) 0.032 Uiso 1 1 d R . . . .
O7 O 0.9629(2) 0.6290(2) 0.39288(4) 0.0285(5) Uani 1 1 d . . . . .
S7 S 0.87340(7) 0.51133(7) 0.39066(2) 0.01909(17) Uani 1 1 d . . . . .
C8 C 0.7499(3) 0.5608(3) 0.36739(5) 0.0187(6) Uani 1 1 d . . . . .
H8 H 0.725895 0.660279 0.368826 0.022 Uiso 1 1 calc R . . . .
O8 O 0.6343(2) 0.4787(2) 0.37160(4) 0.0194(4) Uani 1 1 d . . . . .
C9 C 0.8074(3) 0.5296(3) 0.34256(5) 0.0190(6) Uani 1 1 d . . . . .
H9 H 0.850765 0.436605 0.342570 0.023 Uiso 1 1 calc R . . . .
O9 O 0.9085(2) 0.6316(2) 0.33631(4) 0.0230(5) Uani 1 1 d . . . . .
C10 C 0.6960(3) 0.5356(3) 0.32333(5) 0.0205(6) Uani 1 1 d . . . . .
H10 H 0.674648 0.633687 0.319558 0.025 Uiso 1 1 calc R . . . .
O10 O 0.7571(2) 0.4715(3) 0.30265(4) 0.0263(5) Uani 1 1 d . . . . .
C11 C 0.5649(3) 0.4623(3) 0.33082(5) 0.0202(6) Uani 1 1 d . . . . .
H11 H 0.579369 0.360644 0.331024 0.024 Uiso 1 1 calc R . . . .
O11 O 0.4558(2) 0.4980(2) 0.31441(4) 0.0265(5) Uani 1 1 d . . . . .
C12 C 0.5231(3) 0.5132(3) 0.35566(5) 0.0192(6) Uani 1 1 d . . . . .
H12 H 0.508601 0.614822 0.355395 0.023 Uiso 1 1 calc R . . . .
C13 C 0.3970(3) 0.4422(3) 0.36500(6) 0.0223(6) Uani 1 1 d . . . . .
H13A H 0.318839 0.461313 0.354162 0.027 Uiso 1 1 calc R . . . .
H13B H 0.412739 0.341764 0.365086 0.027 Uiso 1 1 calc R . . . .
O14 O 0.3627(2) 0.4869(2) 0.38896(4) 0.0241(5) Uani 1 1 d . . . . .
C15 C 0.3061(3) 0.6121(3) 0.39096(6) 0.0255(7) Uani 1 1 d . . . . .
O15 O 0.2894(3) 0.6878(3) 0.37421(5) 0.0399(7) Uani 1 1 d . . . . .
C16 C 0.2682(4) 0.6447(4) 0.41630(6) 0.0322(8) Uani 1 1 d . . . . .
H16A H 0.168414 0.655950 0.417503 0.048 Uiso 1 1 calc GR . . . .
H16B H 0.313518 0.729974 0.421224 0.048 Uiso 1 1 calc GR . . . .
H16C H 0.297651 0.569603 0.426797 0.048 Uiso 1 1 calc GR . . . .
C17 C 0.4260(4) 0.4074(4) 0.29669(6) 0.0304(8) Uani 1 1 d . . . . .
O17 O 0.4852(3) 0.3008(3) 0.29412(5) 0.0435(7) Uani 1 1 d . . . . .
C18 C 0.3125(5) 0.4602(6) 0.28137(7) 0.0498(12) Uani 1 1 d . . . . .
H18A H 0.224328 0.443243 0.289306 0.075 Uiso 1 1 calc GR . . . .
H18B H 0.314036 0.413120 0.265845 0.075 Uiso 1 1 calc GR . . . .
H18C H 0.324363 0.559102 0.278885 0.075 Uiso 1 1 calc GR . . . .
C19 C 0.7359(4) 0.5286(4) 0.28093(6) 0.0366(8) Uani 1 1 d . . . . .
O19 O 0.6584(4) 0.6233(4) 0.27754(5) 0.0575(9) Uani 1 1 d . . . . .
C20 C 0.8223(6) 0.4576(5) 0.26249(7) 0.0542(12) Uani 1 1 d . . . . .
H20A H 0.919535 0.467689 0.266668 0.081 Uiso 1 1 calc GR . . . .
H20B H 0.805572 0.498755 0.246721 0.081 Uiso 1 1 calc GR . . . .
H20C H 0.798443 0.359916 0.262013 0.081 Uiso 1 1 calc GR . . . .
C21 C 1.0379(3) 0.5888(3) 0.33164(6) 0.0245(7) Uani 1 1 d . . . . .
O21 O 1.0741(3) 0.4710(3) 0.33351(6) 0.0428(7) Uani 1 1 d . . . . .
C22 C 1.1251(4) 0.7072(4) 0.32407(6) 0.0323(8) Uani 1 1 d . . . . .
H22A H 1.096079 0.738739 0.308172 0.048 Uiso 1 1 calc GR . . . .
H22B H 1.221419 0.678354 0.323434 0.048 Uiso 1 1 calc GR . . . .
H22C H 1.115100 0.782268 0.335647 0.048 Uiso 1 1 calc GR . . . .
C100 C 1.1724(10) 0.4279(11) 0.47598(15) 0.130(3) Uani 1 1 d . U . . .
H10A H 1.101748 0.373207 0.484071 0.196 Uiso 1 1 calc GR . . . .
H10B H 1.197409 0.383669 0.460810 0.196 Uiso 1 1 calc GR . . . .
H10C H 1.136717 0.520115 0.472771 0.196 Uiso 1 1 calc GR . . . .
C101 C 1.2912(12) 0.4375(12) 0.49103(17) 0.137(3) Uani 1 1 d . U . . .
H10D H 1.370288 0.470857 0.481520 0.165 Uiso 1 1 calc R . . . .
H10E H 1.273909 0.504062 0.504101 0.165 Uiso 1 1 calc R . . . .
C102 C 1.3194(14) 0.3194(14) 0.500000 0.158(4) Uani 1 2 d S TU P . .
H10G H 1.302073 0.250818 0.487246 0.190 Uiso 0.5 1 calc R . . . .
H10F H 1.250810 0.302057 0.512752 0.190 Uiso 0.5 1 calc R . . . .
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
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
C6 C1 H1A 109.6 . . ?
C6 C1 H1B 109.6 . . ?
C6 C1 C2 110.2(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 C1 110.6(3) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 C2 110.5(3) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C3 C4 C5 111.0(4) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
C4 C5 C6 109.3(3) . . ?
H5A C5 H5B 108.3 . . ?
C6 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
C1 C6 C5 111.6(3) . . ?
C1 C6 H6 109.0 . . ?
C1 C6 S7 110.6(2) . . ?
C5 C6 H6 109.0 . . ?
C5 C6 S7 107.6(2) . . ?
S7 C6 H6 109.0 . . ?
S7 N7 H7 113(3) . . ?
C6 S7 C8 102.94(14) . . ?
N7 S7 C6 104.08(16) . . ?
N7 S7 C8 112.06(15) . . ?
O7 S7 C6 110.69(15) . . ?
O7 S7 N7 121.34(16) . . ?
O7 S7 C8 104.37(14) . . ?
S7 C8 H8 110.6 . . ?
O8 C8 S7 105.01(19) . . ?
O8 C8 H8 110.6 . . ?
O8 C8 C9 109.5(2) . . ?
C9 C8 S7 110.5(2) . . ?
C9 C8 H8 110.6 . . ?
C8 O8 C12 111.6(2) . . ?
C8 C9 H9 109.6 . . ?
C8 C9 C10 111.7(2) . . ?
O9 C9 C8 109.5(2) . . ?
O9 C9 H9 109.6 . . ?
O9 C9 C10 106.8(2) . . ?
C10 C9 H9 109.6 . . ?
C21 O9 C9 118.1(2) . . ?
C9 C10 H10 109.4 . . ?
O10 C10 C9 104.6(2) . . ?
O10 C10 H10 109.4 . . ?
O10 C10 C11 111.3(3) . . ?
C11 C10 C9 112.7(2) . . ?
C11 C10 H10 109.4 . . ?
C19 O10 C10 118.5(3) . . ?
C10 C11 H11 110.4 . . ?
C10 C11 C12 108.7(2) . . ?
O11 C11 C10 109.3(2) . . ?
O11 C11 H11 110.4 . . ?
O11 C11 C12 107.5(2) . . ?
C12 C11 H11 110.4 . . ?
C17 O11 C11 117.5(3) . . ?
O8 C12 C11 106.4(2) . . ?
O8 C12 H12 110.2 . . ?
O8 C12 C13 107.0(2) . . ?
C11 C12 H12 110.2 . . ?
C13 C12 C11 112.5(3) . . ?
C13 C12 H12 110.2 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
O14 C13 C12 111.7(2) . . ?
O14 C13 H13A 109.3 . . ?
O14 C13 H13B 109.3 . . ?
C15 O14 C13 116.5(3) . . ?
O14 C15 C16 111.9(3) . . ?
O15 C15 O14 123.3(3) . . ?
O15 C15 C16 124.8(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O11 C17 C18 110.6(3) . . ?
O17 C17 O11 123.3(3) . . ?
O17 C17 C18 126.1(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O10 C19 C20 109.9(3) . . ?
O19 C19 O10 123.5(4) . . ?
O19 C19 C20 126.6(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O9 C21 C22 110.3(3) . . ?
O21 C21 O9 123.3(3) . . ?
O21 C21 C22 126.4(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H10A C100 H10B 109.5 . . ?
H10A C100 H10C 109.5 . . ?
H10B C100 H10C 109.5 . . ?
C101 C100 H10A 109.5 . . ?
C101 C100 H10B 109.5 . . ?
C101 C100 H10C 109.5 . . ?
C100 C101 H10D 109.7 . . ?
C100 C101 H10E 109.7 . . ?
H10D C101 H10E 108.2 . . ?
C102 C101 C100 110.0(13) . . ?
C102 C101 H10D 109.7 . . ?
C102 C101 H10E 109.7 . . ?
C101 C102 C101 122(2) . 7_646 ?
C101 C102 H10G 106.8 7_646 . ?
C101 C102 H10G 106.8 . . ?
C101 C102 H10F 106.8 7_646 . ?
C101 C102 H10F 106.8 . . ?
H10G C102 H10F 106.6 . . ?
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
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.534(5) . ?
C1 C6 1.528(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.529(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.514(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.532(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.534(4) . ?
C6 H6 1.0000 . ?
C6 S7 1.795(3) . ?
N7 H7 0.85(4) . ?
N7 S7 1.518(3) . ?
O7 S7 1.445(2) . ?
S7 C8 1.834(3) . ?
C8 H8 1.0000 . ?
C8 O8 1.402(4) . ?
C8 C9 1.524(4) . ?
O8 C12 1.441(3) . ?
C9 H9 1.0000 . ?
C9 O9 1.442(4) . ?
C9 C10 1.527(4) . ?
O9 C21 1.353(4) . ?
C10 H10 1.0000 . ?
C10 O10 1.440(4) . ?
C10 C11 1.522(4) . ?
O10 C19 1.348(4) . ?
C11 H11 1.0000 . ?
C11 O11 1.445(4) . ?
C11 C12 1.526(4) . ?
O11 C17 1.357(4) . ?
C12 H12 1.0000 . ?
C12 C13 1.503(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 O14 1.444(4) . ?
O14 C15 1.343(4) . ?
C15 O15 1.201(4) . ?
C15 C16 1.495(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O17 1.196(5) . ?
C17 C18 1.489(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O19 1.207(5) . ?
C19 C20 1.498(6) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 O21 1.205(4) . ?
C21 C22 1.494(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C100 H10A 0.9800 . ?
C100 H10B 0.9800 . ?
C100 H10C 0.9800 . ?
C100 C101 1.433(13) . ?
C101 H10D 0.9900 . ?
C101 H10E 0.9900 . ?
C101 C102 1.284(13) . ?
C102 H10G 0.9900 . ?
C102 H10F 0.9900 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N7 H7 O15 0.85(4) 2.70(4) 3.302(4) 129(3) 5_645 yes
N7 H7 O21 0.85(4) 2.74(4) 3.423(4) 139(4) . yes
