# 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_mw330_a
_database_code_depnum_ccdc_archive 'CCDC 2024596'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2020-08-20 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;
_audit_creation_date             2019-10-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H24 N2 O1.03 S'
_chemical_formula_sum            'C36 H24 N2 O1.03 S'
_chemical_formula_weight         533.07
_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'
N N 0.0061 0.0033 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.117(6)
_cell_length_b                   5.3771(12)
_cell_length_c                   20.697(5)
_cell_angle_alpha                90
_cell_angle_beta                 128.911(5)
_cell_angle_gamma                90
_cell_volume                     2521.4(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6120
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      27.525
_cell_measurement_theta_min      2.530
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0744 before and 0.0632 after correction. The Ratio of minimum to maximum transmission is 0.8683. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1113
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.331
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            32420
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.364
_diffrn_reflns_theta_min         1.798
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2392
_reflns_number_total             3137
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.316
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.078
_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)+(0.0406P)²+3.9258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1136
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C17(H17), C18(H18)
;
_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 0.500000 -0.22098(11) 0.250000 0.01888(17) Uani 1 2 d S T P . .
O1 O 0.45410(12) -0.3300(5) 0.25944(16) 0.0231(9) Uani 0.514(5) 1 d . . . . .
N1 N 0.64656(7) 0.4344(3) 0.54872(9) 0.0167(3) Uani 1 1 d . . . . .
C1 C 0.69960(8) 0.5467(3) 0.57581(11) 0.0165(4) Uani 1 1 d . . . . .
C2 C 0.73727(8) 0.4809(3) 0.55910(12) 0.0213(4) Uani 1 1 d . . . . .
H2 H 0.728315 0.349063 0.523812 0.026 Uiso 1 1 calc R . . . .
C3 C 0.78858(9) 0.6172(4) 0.59646(12) 0.0231(4) Uani 1 1 d . . . . .
H3 H 0.814607 0.575373 0.586466 0.028 Uiso 1 1 calc R . . . .
C4 C 0.80192(9) 0.8172(3) 0.64908(12) 0.0229(4) Uani 1 1 d . . . . .
H4 H 0.836086 0.909252 0.672328 0.027 Uiso 1 1 calc R . . . .
C5 C 0.76491(8) 0.8790(3) 0.66677(11) 0.0206(4) Uani 1 1 d . . . . .
H5 H 0.774017 1.011343 0.701974 0.025 Uiso 1 1 calc R . . . .
C6 C 0.71356(8) 0.7401(3) 0.63111(11) 0.0175(4) Uani 1 1 d . . . . .
C7 C 0.66821(8) 0.7437(3) 0.63978(11) 0.0166(4) Uani 1 1 d . . . . .
C8 C 0.65843(9) 0.8949(3) 0.68493(11) 0.0202(4) Uani 1 1 d . . . . .
H8 H 0.685068 1.019902 0.719129 0.024 Uiso 1 1 calc R . . . .
C9 C 0.60882(9) 0.8563(3) 0.67810(12) 0.0222(4) Uani 1 1 d . . . . .
H9 H 0.601681 0.957092 0.707455 0.027 Uiso 1 1 calc R . . . .
C10 C 0.56907(9) 0.6667(3) 0.62739(12) 0.0209(4) Uani 1 1 d . . . . .
H10 H 0.536015 0.642401 0.624075 0.025 Uiso 1 1 calc R . . . .
C11 C 0.57774(8) 0.5137(3) 0.58186(11) 0.0187(4) Uani 1 1 d . . . . .
H11 H 0.550995 0.388609 0.547986 0.022 Uiso 1 1 calc R . . . .
C12 C 0.62768(8) 0.5539(3) 0.58863(11) 0.0163(4) Uani 1 1 d . . . . .
C13 C 0.61085(8) 0.2827(3) 0.47693(11) 0.0153(4) Uani 1 1 d . . . . .
C14 C 0.57948(8) 0.0828(3) 0.47484(11) 0.0164(4) Uani 1 1 d . . . . .
H14 H 0.582083 0.046335 0.520963 0.020 Uiso 1 1 calc R . . . .
C15 C 0.54440(8) -0.0614(3) 0.40378(11) 0.0160(4) Uani 1 1 d . . . . .
H15 H 0.523251 -0.194350 0.402134 0.019 Uiso 1 1 calc R . . . .
C16 C 0.54075(8) -0.0080(3) 0.33504(11) 0.0156(4) Uani 1 1 d . . . . .
C17 C 0.57195(8) 0.1909(3) 0.33680(11) 0.0162(4) Uani 1 1 d . . . . .
H17 H 0.569645 0.225552 0.290812 0.019 Uiso 1 1 calc R . . . .
C18 C 0.60642(8) 0.3372(3) 0.40715(11) 0.0161(4) Uani 1 1 d . . . . .
H18 H 0.626751 0.472371 0.408075 0.019 Uiso 1 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
S1 O1 1.580(3) 2_655 ?
S1 O1 1.580(3) . ?
S1 C16 1.7872(18) 2_655 ?
S1 C16 1.7872(18) . ?
N1 C1 1.406(2) . ?
N1 C12 1.403(2) . ?
N1 C13 1.419(2) . ?
C1 C2 1.387(3) . ?
C1 C6 1.404(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.401(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.397(3) . ?
C6 C7 1.440(3) . ?
C7 C8 1.396(2) . ?
C7 C12 1.409(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.398(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(3) . ?
C13 C14 1.393(2) . ?
C13 C18 1.398(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(2) . ?
C16 C17 1.389(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(2) . ?
C18 H18 0.9300 . ?

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
O1 S1 O1 136.45(19) 2_655 . ?
O1 S1 C16 105.64(11) . 2_655 ?
O1 S1 C16 101.88(11) . . ?
O1 S1 C16 101.88(11) 2_655 2_655 ?
O1 S1 C16 105.64(11) 2_655 . ?
C16 S1 C16 100.29(11) 2_655 . ?
C1 N1 C13 124.30(15) . . ?
C12 N1 C1 107.88(14) . . ?
C12 N1 C13 125.41(15) . . ?
C2 C1 N1 129.33(16) . . ?
C2 C1 C6 121.50(17) . . ?
C6 C1 N1 109.04(15) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 118.08(18) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.05(18) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.67(18) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.11(18) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 107.03(16) . . ?
C5 C6 C1 119.49(17) . . ?
C5 C6 C7 133.46(17) . . ?
C8 C7 C6 132.82(17) . . ?
C8 C7 C12 119.87(17) . . ?
C12 C7 C6 107.29(15) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.06(17) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.52(17) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.58(18) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 121.1 . . ?
C12 C11 C10 117.73(17) . . ?
C12 C11 H11 121.1 . . ?
N1 C12 C7 108.74(16) . . ?
C11 C12 N1 130.00(16) . . ?
C11 C12 C7 121.23(16) . . ?
C14 C13 N1 120.74(16) . . ?
C14 C13 C18 119.75(16) . . ?
C18 C13 N1 119.50(16) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.78(17) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.16(16) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 S1 116.91(13) . . ?
C15 C16 C17 120.32(16) . . ?
C17 C16 S1 122.55(14) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.74(17) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.24(16) . . ?
C17 C18 H18 119.9 . . ?

_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_mw372_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2024597'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2020-08-20 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;
_audit_creation_date             2019-10-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H24 N2 O2 S'
_chemical_formula_sum            'C36 H24 N2 O2 S'
_chemical_formula_weight         548.63
_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'
N N 0.0061 0.0033 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.655(5)
_cell_length_b                   5.5039(11)
_cell_length_c                   20.506(4)
_cell_angle_alpha                90
_cell_angle_beta                 128.655(5)
_cell_angle_gamma                90
_cell_volume                     2525.6(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3280
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      26.506
_cell_measurement_theta_min      2.856
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1915 before and 0.0499 after correction. The Ratio of minimum to maximum transmission is 0.8550. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9461
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.534
_diffrn_reflns_theta_min         1.820
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1834
_reflns_number_total             2616
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2616
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.052
_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)+(0.0413P)²+1.3158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1030
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C17(H17), C18(H18)
;
_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 0.500000 -0.18239(14) 0.250000 0.0158(2) Uani 1 2 d S T P . .
O1 O 0.46025(6) -0.3146(3) 0.25685(8) 0.0214(4) Uani 1 1 d . . . . .
N1 N 0.64881(7) 0.4374(3) 0.55212(9) 0.0177(4) Uani 1 1 d . . . . .
C1 C 0.70171(9) 0.5501(4) 0.57907(11) 0.0184(5) Uani 1 1 d . . . . .
C2 C 0.74026(9) 0.4887(4) 0.56293(12) 0.0244(5) Uani 1 1 d . . . . .
H2 H 0.731854 0.356372 0.527303 0.029 Uiso 1 1 calc R . . . .
C3 C 0.79123(10) 0.6252(4) 0.60006(12) 0.0257(5) Uani 1 1 d . . . . .
H3 H 0.818478 0.585399 0.589965 0.031 Uiso 1 1 calc R . . . .
C4 C 0.80396(10) 0.8203(4) 0.65206(12) 0.0250(5) Uani 1 1 d . . . . .
H4 H 0.839171 0.913353 0.675992 0.030 Uiso 1 1 calc R . . . .
C5 C 0.76599(9) 0.8789(4) 0.66894(11) 0.0228(5) Uani 1 1 d . . . . .
H5 H 0.774615 1.011944 0.704427 0.027 Uiso 1 1 calc R . . . .
C6 C 0.71486(9) 0.7413(4) 0.63350(11) 0.0182(5) Uani 1 1 d . . . . .
C7 C 0.66844(9) 0.7422(4) 0.64134(11) 0.0168(5) Uani 1 1 d . . . . .
C8 C 0.65765(9) 0.8912(4) 0.68567(11) 0.0219(5) Uani 1 1 d . . . . .
H8 H 0.684358 1.018996 0.719907 0.026 Uiso 1 1 calc R . . . .
C9 C 0.60743(10) 0.8484(4) 0.67857(11) 0.0233(5) Uani 1 1 d . . . . .
H9 H 0.599248 0.948159 0.708150 0.028 Uiso 1 1 calc R . . . .
C10 C 0.56854(9) 0.6615(4) 0.62882(11) 0.0229(5) Uani 1 1 d . . . . .
H10 H 0.534268 0.635422 0.625332 0.027 Uiso 1 1 calc R . . . .
C11 C 0.57820(9) 0.5118(4) 0.58412(11) 0.0204(5) Uani 1 1 d . . . . .
H11 H 0.551247 0.384368 0.550029 0.024 Uiso 1 1 calc R . . . .
C12 C 0.62859(9) 0.5551(4) 0.59103(11) 0.0171(5) Uani 1 1 d . . . . .
C13 C 0.61336(8) 0.2880(4) 0.48051(11) 0.0154(5) Uani 1 1 d . . . . .
C14 C 0.58205(9) 0.0931(4) 0.47825(11) 0.0164(5) Uani 1 1 d . . . . .
H14 H 0.585388 0.053991 0.526131 0.020 Uiso 1 1 calc R . . . .
C15 C 0.54591(9) -0.0451(4) 0.40670(11) 0.0164(5) Uani 1 1 d . . . . .
H15 H 0.523591 -0.176762 0.404670 0.020 Uiso 1 1 calc R . . . .
C16 C 0.54250(9) 0.0099(4) 0.33782(11) 0.0151(5) Uani 1 1 d . . . . .
C17 C 0.57374(9) 0.2029(4) 0.33962(11) 0.0163(5) Uani 1 1 d . . . . .
H17 H 0.571297 0.238397 0.292223 0.020 Uiso 1 1 calc R . . . .
C18 C 0.60859(9) 0.3445(4) 0.41022(11) 0.0177(5) Uani 1 1 d . . . . .
H18 H 0.629361 0.480596 0.411092 0.021 Uiso 1 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
S1 O1 1.4305(14) 2_655 ?
S1 O1 1.4306(14) . ?
S1 C16 1.7623(19) 2_655 ?
S1 C16 1.7624(19) . ?
N1 C1 1.393(3) . ?
N1 C12 1.403(2) . ?
N1 C13 1.415(2) . ?
C1 C2 1.379(3) . ?
C1 C6 1.403(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.370(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C6 C7 1.436(3) . ?
C7 C8 1.395(3) . ?
C7 C12 1.399(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.373(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(3) . ?
C13 C14 1.380(3) . ?
C13 C18 1.395(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(3) . ?
C16 C17 1.375(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.377(3) . ?
C18 H18 0.9500 . ?

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
O1 S1 O1 118.84(12) 2_655 . ?
O1 S1 C16 106.83(8) . . ?
O1 S1 C16 108.75(8) 2_655 . ?
O1 S1 C16 108.75(8) . 2_655 ?
O1 S1 C16 106.83(8) 2_655 2_655 ?
C16 S1 C16 106.19(13) 2_655 . ?
C1 N1 C12 107.61(16) . . ?
C1 N1 C13 124.64(16) . . ?
C12 N1 C13 125.07(17) . . ?
N1 C1 C6 109.53(18) . . ?
C2 C1 N1 129.21(19) . . ?
C2 C1 C6 121.2(2) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.7(2) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 106.53(18) . . ?
C5 C6 C1 119.86(19) . . ?
C5 C6 C7 133.59(19) . . ?
C8 C7 C6 132.3(2) . . ?
C8 C7 C12 120.14(19) . . ?
C12 C7 C6 107.53(17) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.3(2) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.9(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 121.3 . . ?
C12 C11 C10 117.3(2) . . ?
C12 C11 H11 121.3 . . ?
C7 C12 N1 108.79(17) . . ?
C11 C12 N1 129.71(19) . . ?
C11 C12 C7 121.48(18) . . ?
C14 C13 N1 121.13(17) . . ?
C14 C13 C18 119.75(17) . . ?
C18 C13 N1 119.08(19) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.30(18) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.4(2) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 S1 118.27(16) . . ?
C17 C16 S1 120.94(14) . . ?
C17 C16 C15 120.72(18) . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.87(18) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 119.9(2) . . ?
C17 C18 H18 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
