# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rl3
_database_code_depnum_ccdc_archive 'CCDC 1979887'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2020-01-24 deposited with the CCDC.	2020-05-04 downloaded from the CCDC.
;
_audit_creation_date             2019-06-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C20 H31 N O10 S), C5 H12'
_chemical_formula_sum            'C45 H74 N2 O20 S2'
_chemical_formula_weight         1027.18
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2'
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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
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'

_cell_length_a                   9.74142(5)
_cell_length_b                   9.74142(5)
_cell_length_c                   55.7588(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5291.24(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25529
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.6410
_cell_measurement_theta_min      3.1180
_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.654
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_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_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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_coef       .
_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_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.053
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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

_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
