# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_22019647_0m
_database_code_depnum_ccdc_archive 'CCDC 1989296'
loop_
_audit_author_name
_audit_author_address
'Zaiyong Zhang'
;School of Pharmacy, China Pharmaceutical University
China
;
_audit_update_record             
;
2020-03-10 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;
_audit_creation_date             2019-06-03
_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 H20 N2 O3 S'
_chemical_formula_sum            'C20 H20 N2 O3 S'
_chemical_formula_weight         368.44
_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'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.8840(5)
_cell_length_b                   19.9039(11)
_cell_length_c                   20.2479(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3580.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4069
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.965
_cell_measurement_theta_min      2.280
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1322 before and 0.0740 after correction. The Ratio of minimum to maximum transmission is 0.8240. 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    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24907
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.418
_diffrn_reflns_theta_min         2.280
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_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                2286
_reflns_number_total             3649
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3649
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.075
_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)+(0.0434P)²+2.4722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1329
_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:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C19(H19), C14(H14), C16(H16), C6(H6), C17(H17), C18(H18), C4(H4),
 C7(H7), C3(H3)
2.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.58105(8) 0.33455(4) 0.50210(4) 0.0298(2) Uani 1 1 d . . . . .
O002 O 0.8249(2) 0.51658(9) 0.47713(9) 0.0273(5) Uani 1 1 d . . . . .
O2 O 0.4594(2) 0.38168(9) 0.50346(10) 0.0319(5) Uani 1 1 d . . . . .
O1 O 0.6069(2) 0.29389(10) 0.55938(10) 0.0384(6) Uani 1 1 d . . . . .
N1 N 0.7389(2) 0.41292(11) 0.43090(11) 0.0237(5) Uani 1 1 d . . . . .
N2 N 0.7446(3) 0.37065(11) 0.48673(11) 0.0256(5) Uani 1 1 d . . . . .
C20 C 0.8496(3) 0.39868(13) 0.38294(14) 0.0236(6) Uani 1 1 d . . . . .
C15 C 0.8610(3) 0.44268(14) 0.32910(14) 0.0259(7) Uani 1 1 d . . . . .
C12 C 0.7044(3) 0.48324(13) 0.44385(14) 0.0253(7) Uani 1 1 d . . . . .
H12 H 0.610660 0.486423 0.471006 0.030 Uiso 1 1 calc R . . . .
C13 C 0.6814(3) 0.51864(13) 0.37952(14) 0.0276(7) Uani 1 1 d . . . . .
H13 H 0.610538 0.554242 0.376346 0.033 Uiso 1 1 calc R . . . .
C19 C 0.9417(3) 0.34244(14) 0.38650(14) 0.0272(7) Uani 1 1 d . . . . .
H19 H 0.932299 0.312066 0.422449 0.033 Uiso 1 1 calc R . . . .
C14 C 0.7598(3) 0.50031(14) 0.32709(14) 0.0287(7) Uani 1 1 d . . . . .
H14 H 0.750094 0.525193 0.287276 0.034 Uiso 1 1 calc R . . . .
C16 C 0.9681(3) 0.42993(14) 0.28071(15) 0.0309(7) Uani 1 1 d . . . . .
H16 H 0.976961 0.459697 0.244240 0.037 Uiso 1 1 calc R . . . .
C8 C 0.8425(3) 0.39074(15) 0.54239(15) 0.0320(7) Uani 1 1 d . . . . .
H8A H 0.944690 0.400113 0.525192 0.038 Uiso 1 1 calc R . . . .
H8B H 0.850474 0.352663 0.573651 0.038 Uiso 1 1 calc R . . . .
C5 C 0.5585(3) 0.28416(13) 0.43197(15) 0.0295(7) Uani 1 1 d . . . . .
C6 C 0.4540(3) 0.30105(14) 0.38451(15) 0.0329(7) Uani 1 1 d . . . . .
H6 H 0.393428 0.339990 0.389884 0.039 Uiso 1 1 calc R . . . .
C17 C 1.0622(3) 0.37467(15) 0.28465(15) 0.0344(7) Uani 1 1 d . . . . .
H17 H 1.135977 0.366905 0.251561 0.041 Uiso 1 1 calc R . . . .
C18 C 1.0476(3) 0.33069(14) 0.33751(15) 0.0324(7) Uani 1 1 d . . . . .
H18 H 1.110663 0.292239 0.340135 0.039 Uiso 1 1 calc R . . . .
C11 C 0.8112(3) 0.51874(15) 0.54771(14) 0.0322(7) Uani 1 1 d . . . . .
H11A H 0.725661 0.548362 0.559364 0.039 Uiso 1 1 calc R . . . .
H11B H 0.903618 0.539063 0.566296 0.039 Uiso 1 1 calc R . . . .
C4 C 0.6471(3) 0.22685(15) 0.42468(17) 0.0380(8) Uani 1 1 d . . . . .
H4 H 0.718324 0.214647 0.457553 0.046 Uiso 1 1 calc R . . . .
C9 C 0.7872(3) 0.45162(15) 0.57928(15) 0.0326(7) Uani 1 1 d . . . . .
C2 C 0.5251(4) 0.20432(15) 0.32005(17) 0.0399(8) Uani 1 1 d . . . . .
C7 C 0.4375(4) 0.26112(15) 0.32890(16) 0.0371(8) Uani 1 1 d . . . . .
H7 H 0.365017 0.272905 0.296406 0.045 Uiso 1 1 calc R . . . .
C3 C 0.6289(4) 0.18803(15) 0.36834(19) 0.0439(9) Uani 1 1 d . . . . .
H3 H 0.689549 0.149121 0.362774 0.053 Uiso 1 1 calc R . . . .
C10 C 0.7225(4) 0.4463(2) 0.63756(16) 0.0541(10) Uani 1 1 d . . . . .
H10A H 0.690259 0.485495 0.660296 0.065 Uiso 1 1 calc R . . . .
H10B H 0.708195 0.403287 0.656879 0.065 Uiso 1 1 calc R . . . .
C1 C 0.5073(4) 0.16148(17) 0.25888(19) 0.0562(10) Uani 1 1 d . . . . .
H1A H 0.407445 0.168960 0.239715 0.084 Uiso 1 1 calc GR . . . .
H1B H 0.518310 0.113994 0.270716 0.084 Uiso 1 1 calc GR . . . .
H1C H 0.584751 0.173731 0.226572 0.084 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 1.4317(19) . ?
S1 O1 1.433(2) . ?
S1 N2 1.651(2) . ?
S1 C5 1.750(3) . ?
O002 C12 1.428(3) . ?
O002 C11 1.435(3) . ?
N1 N2 1.410(3) . ?
N1 C20 1.411(3) . ?
N1 C12 1.456(3) . ?
N2 C8 1.479(4) . ?
C20 C15 1.402(4) . ?
C20 C19 1.389(4) . ?
C15 C14 1.458(4) . ?
C15 C16 1.389(4) . ?
C12 H12 1.0000 . ?
C12 C13 1.495(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.321(4) . ?
C19 H19 0.9500 . ?
C19 C18 1.387(4) . ?
C14 H14 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.384(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.506(4) . ?
C5 C6 1.378(4) . ?
C5 C4 1.394(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(4) . ?
C18 H18 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C9 1.496(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.387(5) . ?
C9 C10 1.317(4) . ?
C2 C7 1.384(4) . ?
C2 C3 1.383(5) . ?
C2 C1 1.512(5) . ?
C7 H7 0.9500 . ?
C3 H3 0.9500 . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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 O1 118.42(13) . . ?
O2 S1 N2 112.52(11) . . ?
O2 S1 C5 107.74(13) . . ?
O1 S1 N2 104.90(12) . . ?
O1 S1 C5 110.58(14) . . ?
N2 S1 C5 101.38(13) . . ?
C12 O002 C11 114.9(2) . . ?
N2 N1 C20 114.0(2) . . ?
N2 N1 C12 115.9(2) . . ?
C20 N1 C12 117.6(2) . . ?
N1 N2 S1 112.30(17) . . ?
N1 N2 C8 118.1(2) . . ?
C8 N2 S1 119.46(18) . . ?
C15 C20 N1 117.4(2) . . ?
C19 C20 N1 122.5(2) . . ?
C19 C20 C15 120.1(3) . . ?
C20 C15 C14 117.9(3) . . ?
C16 C15 C20 118.9(3) . . ?
C16 C15 C14 123.1(3) . . ?
O002 C12 N1 111.9(2) . . ?
O002 C12 H12 109.6 . . ?
O002 C12 C13 107.1(2) . . ?
N1 C12 H12 109.6 . . ?
N1 C12 C13 109.0(2) . . ?
C13 C12 H12 109.6 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 C20 119.9(3) . . ?
C18 C19 H19 120.0 . . ?
C15 C14 H14 119.3 . . ?
C13 C14 C15 121.3(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
N2 C8 H8A 108.8 . . ?
N2 C8 H8B 108.8 . . ?
N2 C8 C9 113.8(2) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C6 C5 S1 120.2(2) . . ?
C6 C5 C4 120.4(3) . . ?
C4 C5 S1 119.4(2) . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.9(3) . . ?
C7 C6 H6 120.1 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.3(3) . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
O002 C11 H11A 108.7 . . ?
O002 C11 H11B 108.7 . . ?
O002 C11 C9 114.3(2) . . ?
H11A C11 H11B 107.6 . . ?
C9 C11 H11A 108.7 . . ?
C9 C11 H11B 108.7 . . ?
C5 C4 H4 120.7 . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 H4 120.7 . . ?
C11 C9 C8 117.4(2) . . ?
C10 C9 C8 121.5(3) . . ?
C10 C9 C11 121.1(3) . . ?
C7 C2 C1 120.5(3) . . ?
C3 C2 C7 118.4(3) . . ?
C3 C2 C1 121.1(3) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 C6 120.9(3) . . ?
C2 C7 H7 119.5 . . ?
C4 C3 H3 119.0 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3 119.0 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?


_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_22019576_0m
_database_code_depnum_ccdc_archive 'CCDC 1989297'
loop_
_audit_author_name
_audit_author_address
'Zaiyong Zhang'
;School of Pharmacy, China Pharmaceutical University
China
;
_audit_update_record             
;
2020-03-10 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;
_audit_creation_date             2019-05-22
_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 H20 N2 O3 S'
_chemical_formula_sum            'C20 H20 N2 O3 S'
_chemical_formula_weight         368.44
_chemical_absolute_configuration rm
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.0044(7)
_cell_length_b                   10.0276(15)
_cell_length_c                   30.040(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1808.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1853
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.385
_cell_measurement_theta_min      2.442
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1061 before and 0.0759 after correction. The Ratio of minimum to maximum transmission is 0.5852. 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    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_av_unetI/netI     0.1089
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            10149
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.320
_diffrn_reflns_theta_min         2.442
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_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         0.690
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2166
_reflns_number_total             3254
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 643 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0591P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1399
_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:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C3(H3), C7(H7), C6(H6), C11(H11), C9(H9), C14(H14), C13(H13),
 C12(H12)
2.d X=CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.5228(2) 0.75583(17) 0.41851(5) 0.0260(4) Uani 1 1 d . . . . .
O2 O 0.6858(6) 0.7555(5) 0.38371(12) 0.0295(9) Uani 1 1 d . . . . .
O3 O 0.3357(7) 0.3380(4) 0.38125(13) 0.0293(10) Uani 1 1 d . . . . .
O1 O 0.5902(6) 0.7651(4) 0.46409(12) 0.0304(10) Uani 1 1 d . . . . .
N2 N 0.3293(8) 0.5741(5) 0.37153(15) 0.0231(12) Uani 1 1 d . . . . .
N1 N 0.3889(7) 0.6115(5) 0.41508(16) 0.0251(12) Uani 1 1 d . . . . .
C16 C 0.4260(9) 0.4500(6) 0.35794(18) 0.0243(14) Uani 1 1 d . . . . .
H16 H 0.590922 0.453255 0.362498 0.029 Uiso 1 1 calc R . . . .
C18 C 0.2029(10) 0.4254(7) 0.4522(2) 0.0305(16) Uani 1 1 d . . . . .
C4 C 0.3399(11) 0.9482(6) 0.3672(2) 0.0289(16) Uani 1 1 d . . . . .
H4 H 0.453816 0.928359 0.346316 0.035 Uiso 1 1 calc R . . . .
C5 C 0.3308(9) 0.8825(6) 0.40734(19) 0.0241(15) Uani 1 1 d . . . . .
C19 C 0.2348(10) 0.5733(7) 0.4512(2) 0.0325(17) Uani 1 1 d . . . . .
H19A H 0.089286 0.617554 0.446658 0.039 Uiso 1 1 calc R . . . .
H19B H 0.295765 0.603490 0.480144 0.039 Uiso 1 1 calc R . . . .
C8 C 0.1160(10) 0.6058(6) 0.3566(2) 0.0288(15) Uani 1 1 d . . . . .
H8 H 0.025137 0.664214 0.373681 0.035 Uiso 1 1 calc R . . . .
C3 C 0.1804(10) 1.0439(6) 0.3577(2) 0.0323(16) Uani 1 1 d . . . . .
H3 H 0.187770 1.091084 0.330338 0.039 Uiso 1 1 calc R . . . .
C7 C 0.0074(11) 1.0049(6) 0.4280(2) 0.0342(16) Uani 1 1 d . . . . .
H7 H -0.106051 1.024961 0.449042 0.041 Uiso 1 1 calc R . . . .
C17 C 0.3675(10) 0.3379(7) 0.42862(18) 0.0306(16) Uani 1 1 d . . . . .
H17A H 0.520156 0.369033 0.435434 0.037 Uiso 1 1 calc R . . . .
H17B H 0.352825 0.245517 0.439894 0.037 Uiso 1 1 calc R . . . .
C2 C 0.0105(10) 1.0721(6) 0.3874(2) 0.0321(15) Uani 1 1 d . . . . .
C6 C 0.1657(10) 0.9095(6) 0.4385(2) 0.0312(16) Uani 1 1 d . . . . .
H6 H 0.161654 0.863819 0.466195 0.037 Uiso 1 1 calc R . . . .
C15 C 0.3762(10) 0.4241(6) 0.3094(2) 0.0277(15) Uani 1 1 d . . . . .
C11 C 0.1167(11) 0.4331(7) 0.2485(2) 0.0404(19) Uani 1 1 d . . . . .
H11 H -0.019394 0.463845 0.236086 0.049 Uiso 1 1 calc R . . . .
C10 C 0.1742(11) 0.4686(6) 0.2921(2) 0.0312(16) Uani 1 1 d . . . . .
C9 C 0.0384(11) 0.5553(7) 0.3188(2) 0.0342(16) Uani 1 1 d . . . . .
H9 H -0.108298 0.576586 0.309331 0.041 Uiso 1 1 calc R . . . .
C14 C 0.5188(12) 0.3475(6) 0.2835(2) 0.0366(16) Uani 1 1 d . . . . .
H14 H 0.658160 0.319186 0.295045 0.044 Uiso 1 1 calc R . . . .
C13 C 0.4568(12) 0.3128(7) 0.2408(2) 0.0423(19) Uani 1 1 d . . . . .
H13 H 0.553974 0.260065 0.223081 0.051 Uiso 1 1 calc R . . . .
C12 C 0.2564(13) 0.3536(8) 0.2235(2) 0.045(2) Uani 1 1 d . . . . .
H12 H 0.213927 0.327140 0.194372 0.054 Uiso 1 1 calc R . . . .
C20 C 0.0353(13) 0.3732(7) 0.4742(2) 0.0461(19) Uani 1 1 d . . . . .
H20A H -0.066311 0.429333 0.489541 0.055 Uiso 1 1 calc R . . . .
H20B H 0.015522 0.279182 0.474688 0.055 Uiso 1 1 calc R . . . .
C1 C -0.1634(11) 1.1738(7) 0.3755(3) 0.048(2) Uani 1 1 d . . . . .
H1A H -0.093060 1.261508 0.372239 0.071 Uiso 1 1 calc GR . . . .
H1B H -0.275919 1.177704 0.399064 0.071 Uiso 1 1 calc GR . . . .
H1C H -0.234463 1.148648 0.347341 0.071 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 1.432(4) . ?
S1 O1 1.431(4) . ?
S1 N1 1.659(5) . ?
S1 C5 1.747(6) . ?
O3 C16 1.431(7) . ?
O3 C17 1.436(7) . ?
N2 N1 1.407(6) . ?
N2 C16 1.433(7) . ?
N2 C8 1.394(7) . ?
N1 C19 1.477(7) . ?
C16 H16 1.0000 . ?
C16 C15 1.511(8) . ?
C18 C19 1.495(9) . ?
C18 C17 1.499(8) . ?
C18 C20 1.313(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(8) . ?
C4 C3 1.385(8) . ?
C5 C6 1.390(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C8 H8 0.9500 . ?
C8 C9 1.329(8) . ?
C3 H3 0.9500 . ?
C3 C2 1.384(8) . ?
C7 H7 0.9500 . ?
C7 C2 1.395(8) . ?
C7 C6 1.385(9) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C2 C1 1.503(9) . ?
C6 H6 0.9500 . ?
C15 C10 1.393(9) . ?
C15 C14 1.389(8) . ?
C11 H11 0.9500 . ?
C11 C10 1.399(8) . ?
C11 C12 1.379(9) . ?
C10 C9 1.437(9) . ?
C9 H9 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.380(8) . ?
C13 H13 0.9500 . ?
C13 C12 1.372(10) . ?
C12 H12 0.9500 . ?
C20 H20A 0.9500 . ?
C20 H20B 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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 N1 106.5(3) . . ?
O2 S1 C5 108.2(3) . . ?
O1 S1 O2 120.4(2) . . ?
O1 S1 N1 104.7(3) . . ?
O1 S1 C5 108.9(3) . . ?
N1 S1 C5 107.6(3) . . ?
C17 O3 C16 115.8(4) . . ?
N1 N2 C16 113.2(4) . . ?
C8 N2 N1 118.1(5) . . ?
C8 N2 C16 118.6(5) . . ?
N2 N1 S1 114.4(4) . . ?
N2 N1 C19 117.1(5) . . ?
C19 N1 S1 118.9(4) . . ?
O3 C16 H16 109.5 . . ?
O3 C16 C15 105.2(5) . . ?
N2 C16 O3 112.9(4) . . ?
N2 C16 H16 109.5 . . ?
N2 C16 C15 110.1(5) . . ?
C15 C16 H16 109.5 . . ?
C19 C18 C17 119.1(5) . . ?
C20 C18 C19 120.3(6) . . ?
C20 C18 C17 120.6(6) . . ?
C5 C4 H4 120.5 . . ?
C5 C4 C3 119.1(6) . . ?
C3 C4 H4 120.5 . . ?
C4 C5 S1 119.4(5) . . ?
C4 C5 C6 121.7(6) . . ?
C6 C5 S1 118.9(5) . . ?
N1 C19 C18 110.6(5) . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
N2 C8 H8 119.7 . . ?
C9 C8 N2 120.6(6) . . ?
C9 C8 H8 119.7 . . ?
C4 C3 H3 119.4 . . ?
C2 C3 C4 121.2(6) . . ?
C2 C3 H3 119.4 . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C2 121.5(6) . . ?
O3 C17 C18 112.3(5) . . ?
O3 C17 H17A 109.1 . . ?
O3 C17 H17B 109.1 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
C3 C2 C7 118.4(6) . . ?
C3 C2 C1 119.8(6) . . ?
C7 C2 C1 121.8(6) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 C5 118.1(6) . . ?
C7 C6 H6 120.9 . . ?
C10 C15 C16 118.5(6) . . ?
C14 C15 C16 120.9(6) . . ?
C14 C15 C10 120.3(6) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C12 C11 C10 120.4(7) . . ?
C15 C10 C11 118.8(6) . . ?
C15 C10 C9 118.6(6) . . ?
C11 C10 C9 122.4(6) . . ?
C8 C9 C10 120.7(6) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C15 C14 H14 120.2 . . ?
C13 C14 C15 119.6(6) . . ?
C13 C14 H14 120.2 . . ?
C14 C13 H13 119.6 . . ?
C12 C13 C14 120.8(7) . . ?
C12 C13 H13 119.6 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(6) . . ?
C13 C12 H12 120.0 . . ?
C18 C20 H20A 120.0 . . ?
C18 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
