# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1897779'
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
_audit_creation_date             2019-02-16
_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         'C22 H20 O3 S'
_chemical_formula_sum            'C22 H20 O3 S'
_chemical_formula_weight         364.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.855(3)
_cell_length_b                   5.7928(7)
_cell_length_c                   16.427(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.359(13)
_cell_angle_gamma                90
_cell_volume                     1821.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1469
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4250
_cell_measurement_theta_min      4.2590
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7635
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.201
_diffrn_reflns_theta_min         3.530
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2750
_reflns_number_total             4207
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0029(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+0.1879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1139
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C10(H10), C11(H11), C5(H5), C12(H12), C22(H22), C1(H1),
 C19(H19), C3(H3), C13(H13), C17(H17), C2(H2), C4(H4)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
S1 S 0.30361(3) 0.89300(9) 0.08956(3) 0.04093(17) Uani 1 1 d . . . . .
O2 O 0.28407(8) 0.6599(2) 0.10130(9) 0.0538(4) Uani 1 1 d . . . . .
C6 C 0.04551(10) 1.1018(4) 0.11005(12) 0.0417(5) Uani 1 1 d . . . . .
C14 C 0.22852(10) 1.0725(4) 0.07155(12) 0.0410(5) Uani 1 1 d . . . . .
H14A H 0.243910 1.230925 0.083029 0.049 Uiso 1 1 calc R . . . .
H14B H 0.203721 1.062911 0.012234 0.049 Uiso 1 1 calc R . . . .
C15 C 0.36161(10) 0.9900(3) 0.18389(12) 0.0373(4) Uani 1 1 d . . . . .
O3 O 0.33472(8) 0.9421(3) 0.02181(8) 0.0571(4) Uani 1 1 d . . . . .
C8 C 0.17710(10) 1.0163(3) 0.12381(11) 0.0382(5) Uani 1 1 d . . . . .
H8 H 0.162399 0.854875 0.114129 0.046 Uiso 1 1 calc R . . . .
O1 O 0.11846(8) 1.3552(3) 0.06082(12) 0.0750(6) Uani 1 1 d . . . . .
C16 C 0.37091(10) 0.8620(4) 0.25670(12) 0.0426(5) Uani 1 1 d . . . . .
H16 H 0.348833 0.720028 0.255677 0.051 Uiso 1 1 calc R . . . .
C20 C 0.39523(11) 1.1984(4) 0.18490(13) 0.0459(5) Uani 1 1 d . . . . .
H20 H 0.389504 1.282928 0.135390 0.055 Uiso 1 1 calc R . . . .
C9 C 0.20743(10) 1.0547(3) 0.21789(12) 0.0376(5) Uani 1 1 d . . . . .
C10 C 0.20546(10) 0.8805(4) 0.27519(13) 0.0446(5) Uani 1 1 d . . . . .
H10 H 0.183893 0.740991 0.255978 0.054 Uiso 1 1 calc R . . . .
C7 C 0.11311(11) 1.1724(4) 0.09397(13) 0.0456(5) Uani 1 1 d . . . . .
C11 C 0.23515(11) 0.9123(4) 0.36033(13) 0.0512(6) Uani 1 1 d . . . . .
H11 H 0.233780 0.793925 0.398100 0.061 Uiso 1 1 calc R . . . .
C5 C 0.03496(11) 0.8939(4) 0.14590(14) 0.0520(6) Uani 1 1 d . . . . .
H5 H 0.071128 0.786984 0.160263 0.062 Uiso 1 1 calc R . . . .
C12 C 0.26667(12) 1.1176(4) 0.38951(13) 0.0539(6) Uani 1 1 d . . . . .
H12 H 0.287033 1.138095 0.446919 0.065 Uiso 1 1 calc R . . . .
C22 C 0.23847(11) 1.2626(4) 0.24845(13) 0.0462(5) Uani 1 1 d . . . . .
H22 H 0.239356 1.382689 0.211169 0.055 Uiso 1 1 calc R . . . .
C1 C -0.00982(11) 1.2555(4) 0.08769(14) 0.0535(6) Uani 1 1 d . . . . .
H1 H -0.003842 1.395542 0.062799 0.064 Uiso 1 1 calc R . . . .
C19 C 0.43735(11) 1.2806(4) 0.25979(14) 0.0503(6) Uani 1 1 d . . . . .
H19 H 0.460297 1.420882 0.260531 0.060 Uiso 1 1 calc R . . . .
C3 C -0.08234(12) 0.9991(5) 0.13870(15) 0.0629(7) Uani 1 1 d . . . . .
H3 H -0.125154 0.965525 0.148970 0.075 Uiso 1 1 calc R . . . .
C13 C 0.26811(12) 1.2930(4) 0.33377(14) 0.0528(6) Uani 1 1 d . . . . .
H13 H 0.289134 1.432928 0.353601 0.063 Uiso 1 1 calc R . . . .
C17 C 0.41318(11) 0.9466(4) 0.33082(13) 0.0507(6) Uani 1 1 d . . . . .
H17 H 0.419799 0.859880 0.379956 0.061 Uiso 1 1 calc R . . . .
C18 C 0.44601(11) 1.1574(4) 0.33396(14) 0.0539(6) Uani 1 1 d . . . . .
C2 C -0.07302(12) 1.2045(5) 0.10166(16) 0.0656(7) Uani 1 1 d . . . . .
H2 H -0.109716 1.309160 0.086048 0.079 Uiso 1 1 calc R . . . .
C4 C -0.02858(12) 0.8431(5) 0.16062(15) 0.0590(6) Uani 1 1 d . . . . .
H4 H -0.035013 0.703362 0.185381 0.071 Uiso 1 1 calc R . . . .
C21 C 0.48931(16) 1.2563(6) 0.41624(16) 0.0933(10) Uani 1 1 d . . . . .
H21A H 0.506850 1.405086 0.406191 0.140 Uiso 1 1 calc GR . . . .
H21B H 0.527749 1.154901 0.439907 0.140 Uiso 1 1 calc GR . . . .
H21C H 0.460867 1.271900 0.454946 0.140 Uiso 1 1 calc GR . . . .


_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
S1 O2 1.4319(15) . ?
S1 C14 1.777(2) . ?
S1 C15 1.760(2) . ?
S1 O3 1.4370(14) . ?
C6 C7 1.492(3) . ?
C6 C5 1.381(3) . ?
C6 C1 1.386(3) . ?
C14 C8 1.533(3) . ?
C15 C16 1.378(3) . ?
C15 C20 1.378(3) . ?
C8 C9 1.519(3) . ?
C8 C7 1.530(3) . ?
O1 C7 1.208(3) . ?
C16 C17 1.373(3) . ?
C20 C19 1.377(3) . ?
C9 C10 1.387(3) . ?
C9 C22 1.385(3) . ?
C10 C11 1.379(3) . ?
C11 C12 1.370(3) . ?
C5 C4 1.378(3) . ?
C12 C13 1.373(3) . ?
C22 C13 1.380(3) . ?
C1 C2 1.366(3) . ?
C19 C18 1.383(3) . ?
C3 C2 1.371(4) . ?
C3 C4 1.372(3) . ?
C17 C18 1.379(3) . ?
C18 C21 1.510(3) . ?

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
O2 S1 C14 109.20(10) . . ?
O2 S1 C15 108.66(9) . . ?
O2 S1 O3 118.57(10) . . ?
C15 S1 C14 106.51(9) . . ?
O3 S1 C14 105.61(9) . . ?
O3 S1 C15 107.66(9) . . ?
C5 C6 C7 124.04(19) . . ?
C5 C6 C1 118.3(2) . . ?
C1 C6 C7 117.7(2) . . ?
C8 C14 S1 115.88(14) . . ?
C16 C15 S1 119.90(16) . . ?
C16 C15 C20 120.55(19) . . ?
C20 C15 S1 119.49(15) . . ?
C9 C8 C14 113.28(16) . . ?
C9 C8 C7 108.13(15) . . ?
C7 C8 C14 108.35(16) . . ?
C17 C16 C15 119.2(2) . . ?
C19 C20 C15 119.45(19) . . ?
C10 C9 C8 120.59(18) . . ?
C22 C9 C8 120.97(17) . . ?
C22 C9 C10 118.44(18) . . ?
C11 C10 C9 120.7(2) . . ?
C6 C7 C8 119.39(18) . . ?
O1 C7 C6 120.70(19) . . ?
O1 C7 C8 119.84(19) . . ?
C12 C11 C10 120.3(2) . . ?
C4 C5 C6 120.7(2) . . ?
C11 C12 C13 119.8(2) . . ?
C13 C22 C9 120.5(2) . . ?
C2 C1 C6 121.0(2) . . ?
C20 C19 C18 120.9(2) . . ?
C2 C3 C4 120.1(2) . . ?
C12 C13 C22 120.3(2) . . ?
C16 C17 C18 121.4(2) . . ?
C19 C18 C21 120.1(2) . . ?
C17 C18 C19 118.5(2) . . ?
C17 C18 C21 121.4(2) . . ?
C1 C2 C3 120.0(2) . . ?
C3 C4 C5 119.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1897875'
_audit_update_record             
;
2019-02-18 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
_audit_creation_date             2019-02-16
_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         'C20 H22 O3 S'
_chemical_formula_sum            'C20 H22 O3 S'
_chemical_formula_weight         342.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2575(7)
_cell_length_b                   9.6845(7)
_cell_length_c                   10.1145(8)
_cell_angle_alpha                79.903(6)
_cell_angle_beta                 84.497(7)
_cell_angle_gamma                80.659(6)
_cell_volume                     878.80(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1969
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3240
_cell_measurement_theta_min      4.0000
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.830
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6448
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.194
_diffrn_reflns_theta_min         3.811
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.830
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2892
_reflns_number_total             3958
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.196
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3958
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.017
_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)+(0.0508P)²+0.2515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1308
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C9(H9A,H9B), C8(H8A,H8B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C20(H20), C15(H15), C4(H4), C19(H19), C2(H2), C3(H3), C16(H16)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_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
S1 S 0.61101(6) 0.15550(6) 0.35433(5) 0.05277(18) Uani 1 1 d . . . . .
O1 O 0.93555(15) 0.21344(15) 0.52498(15) 0.0581(4) Uani 1 1 d . . . . .
O2 O 0.47434(14) 0.18419(16) 0.43203(16) 0.0638(4) Uani 1 1 d . . . . .
O3 O 0.6116(2) 0.0886(2) 0.23834(17) 0.0832(5) Uani 1 1 d . . . . .
C13 C 0.7389(2) 0.0466(2) 0.4624(2) 0.0472(5) Uani 1 1 d . . . . .
H13A H 0.719335 -0.050333 0.474119 0.057 Uiso 1 1 calc R . . . .
H13B H 0.836735 0.048759 0.418810 0.057 Uiso 1 1 calc R . . . .
C10 C 0.73699(18) 0.08865(18) 0.60056(18) 0.0397(4) Uani 1 1 d . . . . .
H10 H 0.635159 0.117576 0.632729 0.048 Uiso 1 1 calc R . . . .
C11 C 0.82359(19) 0.20920(18) 0.59816(18) 0.0403(4) Uani 1 1 d . . . . .
C9 C 0.8058(2) -0.04065(19) 0.6997(2) 0.0498(5) Uani 1 1 d . . . . .
H9A H 0.734566 -0.105650 0.724063 0.060 Uiso 1 1 calc R . . . .
H9B H 0.889800 -0.089393 0.652838 0.060 Uiso 1 1 calc R . . . .
C12 C 0.77659(19) 0.32030(18) 0.68489(19) 0.0438(4) Uani 1 1 d . . . . .
C5 C 0.6923(2) 0.3045(2) 0.8081(2) 0.0516(5) Uani 1 1 d . . . . .
C14 C 0.6786(2) 0.3175(2) 0.30372(19) 0.0489(5) Uani 1 1 d . . . . .
C8 C 0.8552(2) -0.0082(2) 0.8282(2) 0.0575(5) Uani 1 1 d . . . . .
H8A H 0.912492 -0.093397 0.873039 0.069 Uiso 1 1 calc R . . . .
H8B H 0.919780 0.063157 0.803925 0.069 Uiso 1 1 calc R . . . .
C1 C 0.8276(2) 0.4490(2) 0.6354(2) 0.0586(6) Uani 1 1 d . . . . .
H1 H 0.883608 0.458491 0.553805 0.070 Uiso 1 1 calc R . . . .
C20 C 0.6092(2) 0.4359(2) 0.3534(2) 0.0617(6) Uani 1 1 d . . . . .
H20 H 0.525892 0.430512 0.412212 0.074 Uiso 1 1 calc R . . . .
C6 C 0.6269(2) 0.1736(2) 0.8740(2) 0.0630(6) Uani 1 1 d . . . . .
H6A H 0.569927 0.147475 0.809112 0.076 Uiso 1 1 calc R . . . .
H6B H 0.559414 0.198485 0.948460 0.076 Uiso 1 1 calc R . . . .
C15 C 0.8008(3) 0.3259(3) 0.2152(2) 0.0700(7) Uani 1 1 d . . . . .
H15 H 0.847840 0.246440 0.180180 0.084 Uiso 1 1 calc R . . . .
C4 C 0.6678(3) 0.4210(3) 0.8766(3) 0.0739(7) Uani 1 1 d . . . . .
H4 H 0.615557 0.413027 0.960185 0.089 Uiso 1 1 calc R . . . .
C17 C 0.7848(3) 0.5740(3) 0.2298(3) 0.0744(8) Uani 1 1 d . . . . .
C7 C 0.7351(3) 0.0433(3) 0.9270(2) 0.0740(7) Uani 1 1 d . . . . .
H7A H 0.780396 0.064595 1.002144 0.089 Uiso 1 1 calc R . . . .
H7B H 0.679761 -0.033789 0.961649 0.089 Uiso 1 1 calc R . . . .
C19 C 0.6629(3) 0.5629(3) 0.3163(3) 0.0740(7) Uani 1 1 d . . . . .
H19 H 0.615228 0.642481 0.350808 0.089 Uiso 1 1 calc R . . . .
C2 C 0.7972(3) 0.5614(2) 0.7040(3) 0.0793(8) Uani 1 1 d . . . . .
H2 H 0.830111 0.646980 0.668514 0.095 Uiso 1 1 calc R . . . .
C3 C 0.7184(3) 0.5465(3) 0.8245(4) 0.0893(9) Uani 1 1 d . . . . .
H3 H 0.698465 0.621940 0.872311 0.107 Uiso 1 1 calc R . . . .
C16 C 0.8522(3) 0.4543(4) 0.1795(3) 0.0822(8) Uani 1 1 d . . . . .
H16 H 0.934593 0.460255 0.119741 0.099 Uiso 1 1 calc R . . . .
C18 C 0.8438(4) 0.7136(3) 0.1916(4) 0.1216(14) Uani 1 1 d . . . . .
H18A H 0.764132 0.788804 0.170330 0.182 Uiso 1 1 calc GR . . . .
H18B H 0.912527 0.709422 0.114511 0.182 Uiso 1 1 calc GR . . . .
H18C H 0.892039 0.731038 0.265560 0.182 Uiso 1 1 calc GR . . . .


_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
S1 O2 1.4378(15) . ?
S1 O3 1.4355(17) . ?
S1 C13 1.774(2) . ?
S1 C14 1.758(2) . ?
O1 C11 1.216(2) . ?
C13 C10 1.520(3) . ?
C10 C11 1.515(2) . ?
C10 C9 1.550(2) . ?
C11 C12 1.491(3) . ?
C9 C8 1.517(3) . ?
C12 C5 1.404(3) . ?
C12 C1 1.398(3) . ?
C5 C6 1.514(3) . ?
C5 C4 1.402(3) . ?
C14 C20 1.372(3) . ?
C14 C15 1.377(3) . ?
C8 C7 1.506(3) . ?
C1 C2 1.370(3) . ?
C20 C19 1.379(3) . ?
C6 C7 1.529(3) . ?
C15 C16 1.380(4) . ?
C4 C3 1.374(4) . ?
C17 C19 1.367(4) . ?
C17 C16 1.380(4) . ?
C17 C18 1.514(3) . ?
C2 C3 1.356(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
O2 S1 C13 108.22(9) . . ?
O2 S1 C14 107.29(9) . . ?
O3 S1 O2 118.33(10) . . ?
O3 S1 C13 107.32(10) . . ?
O3 S1 C14 108.78(10) . . ?
C14 S1 C13 106.30(9) . . ?
C10 C13 S1 114.88(13) . . ?
C13 C10 C9 109.18(15) . . ?
C11 C10 C13 112.14(14) . . ?
C11 C10 C9 108.15(15) . . ?
O1 C11 C10 118.78(16) . . ?
O1 C11 C12 119.51(16) . . ?
C12 C11 C10 121.70(15) . . ?
C8 C9 C10 116.08(16) . . ?
C5 C12 C11 126.20(17) . . ?
C1 C12 C11 114.03(18) . . ?
C1 C12 C5 119.75(18) . . ?
C12 C5 C6 126.22(17) . . ?
C4 C5 C12 116.5(2) . . ?
C4 C5 C6 117.2(2) . . ?
C20 C14 S1 119.55(15) . . ?
C20 C14 C15 120.0(2) . . ?
C15 C14 S1 120.45(18) . . ?
C7 C8 C9 115.98(19) . . ?
C2 C1 C12 121.6(2) . . ?
C14 C20 C19 120.0(2) . . ?
C5 C6 C7 116.55(19) . . ?
C14 C15 C16 118.8(2) . . ?
C3 C4 C5 122.2(3) . . ?
C19 C17 C16 117.9(2) . . ?
C19 C17 C18 120.7(3) . . ?
C16 C17 C18 121.4(3) . . ?
C8 C7 C6 116.69(18) . . ?
C17 C19 C20 121.2(3) . . ?
C3 C2 C1 119.2(3) . . ?
C2 C3 C4 120.7(2) . . ?
C17 C16 C15 121.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
