# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_191118shc
_database_code_depnum_ccdc_archive 'CCDC 2088169'
loop_
_audit_author_name
_audit_author_address
'Xiang Wu'
;Hefei University of Technology
China
;
_audit_update_record             
;
2021-06-05 deposited with the CCDC.	2021-08-24 downloaded from the CCDC.
;
_audit_creation_date             2019-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N O2 S'
_chemical_formula_sum            'C19 H21 N O2 S'
_chemical_formula_weight         327.43
_chemical_absolute_configuration rmad
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2924 0.4247 '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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.1578(3)
_cell_length_b                   8.9611(4)
_cell_length_c                   9.5418(5)
_cell_angle_alpha                92.623(2)
_cell_angle_beta                 103.7520(10)
_cell_angle_gamma                95.143(2)
_cell_volume                     425.62(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8444
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.99
_cell_measurement_theta_min      5.79
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    1.140
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1435 before and 0.0823 after correction. The Ratio of minimum to maximum transmission is 0.6811. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             174
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7143
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.965
_diffrn_reflns_theta_min         5.790
_diffrn_ambient_temperature      170.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_full    0.928
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                3044
_reflns_number_total             3092
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.384
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1410 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.048(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.071
_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)+(0.0184P)²+0.1349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0922
_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:
 C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_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
S1 S 0.68490(10) 0.72831(7) 0.60625(7) 0.0248(2) Uani 1 1 d . . . . .
O1 O 0.9494(4) 0.6853(3) 0.6148(3) 0.0326(6) Uani 1 1 d . . . . .
O2 O 0.6453(5) 0.8554(3) 0.6918(3) 0.0352(6) Uani 1 1 d . . . . .
N1 N 0.5109(6) 0.5849(3) 0.6487(3) 0.0250(6) Uani 1 1 d . . . . .
H1 H 0.359(10) 0.597(5) 0.654(4) 0.030(11) Uiso 1 1 d . . . . .
C1 C 0.5278(6) 0.4322(3) 0.5905(3) 0.0237(7) Uani 1 1 d . . . . .
H1A H 0.666994 0.435993 0.533116 0.028 Uiso 1 1 calc R . . . .
C2 C 0.5988(7) 0.3231(4) 0.7090(4) 0.0276(7) Uani 1 1 d . . . . .
C3 C 0.4122(7) 0.2052(4) 0.6840(4) 0.0308(8) Uani 1 1 d . . . . .
H3 H 0.417862 0.121239 0.741510 0.037 Uiso 1 1 calc R . . . .
C4 C 0.1973(7) 0.2229(4) 0.5558(4) 0.0287(7) Uani 1 1 d . . . . .
C5 C -0.0384(8) 0.1350(4) 0.4909(4) 0.0354(8) Uani 1 1 d . . . . .
H5 H -0.086813 0.044651 0.531067 0.042 Uiso 1 1 calc R . . . .
C6 C -0.2037(8) 0.1801(4) 0.3664(4) 0.0371(8) Uani 1 1 d . . . . .
H6 H -0.366089 0.120104 0.321456 0.045 Uiso 1 1 calc R . . . .
C7 C -0.1346(7) 0.3122(4) 0.3066(4) 0.0344(8) Uani 1 1 d . . . . .
H7 H -0.248929 0.341188 0.220868 0.041 Uiso 1 1 calc R . . . .
C8 C 0.1027(7) 0.4022(4) 0.3723(4) 0.0299(7) Uani 1 1 d . . . . .
H8 H 0.150707 0.492762 0.332277 0.036 Uiso 1 1 calc R . . . .
C9 C 0.2661(6) 0.3571(3) 0.4967(3) 0.0254(7) Uani 1 1 d . . . . .
C10 C 0.8512(7) 0.3561(4) 0.8251(4) 0.0330(8) Uani 1 1 d . . . . .
H10A H 0.827760 0.439433 0.891278 0.040 Uiso 1 1 calc R . . . .
H10B H 0.997934 0.391209 0.780146 0.040 Uiso 1 1 calc R . . . .
C11 C 0.9369(8) 0.2240(4) 0.9143(4) 0.0381(9) Uani 1 1 d . . . . .
H11A H 0.949432 0.137450 0.848886 0.046 Uiso 1 1 calc R . . . .
H11B H 0.799561 0.193884 0.967438 0.046 Uiso 1 1 calc R . . . .
C12 C 1.2079(9) 0.2650(5) 1.0220(4) 0.0454(10) Uani 1 1 d . . . . .
H12A H 1.343896 0.295080 0.969609 0.068 Uiso 1 1 calc GR . . . .
H12B H 1.259563 0.177828 1.076524 0.068 Uiso 1 1 calc GR . . . .
H12C H 1.193957 0.348424 1.089056 0.068 Uiso 1 1 calc GR . . . .
C13 C 0.5445(7) 0.7582(4) 0.4225(4) 0.0276(7) Uani 1 1 d . . . . .
C14 C 0.6417(8) 0.6900(4) 0.3147(4) 0.0367(8) Uani 1 1 d . . . . .
H14 H 0.788240 0.631151 0.338766 0.044 Uiso 1 1 calc R . . . .
C15 C 0.5219(9) 0.7090(5) 0.1715(4) 0.0438(10) Uani 1 1 d . . . . .
H15 H 0.585709 0.660855 0.097402 0.053 Uiso 1 1 calc R . . . .
C16 C 0.3110(9) 0.7966(4) 0.1338(4) 0.0422(10) Uani 1 1 d . . . . .
C17 C 0.2201(8) 0.8637(4) 0.2432(4) 0.0404(9) Uani 1 1 d . . . . .
H17 H 0.075438 0.923955 0.219093 0.048 Uiso 1 1 calc R . . . .
C18 C 0.3341(7) 0.8457(4) 0.3876(4) 0.0324(8) Uani 1 1 d . . . . .
H18 H 0.268510 0.892908 0.461444 0.039 Uiso 1 1 calc R . . . .
C19 C 0.1857(13) 0.8147(6) -0.0236(5) 0.0699(16) Uani 1 1 d . . . . .
H19A H 0.031900 0.873251 -0.031356 0.105 Uiso 1 1 calc GR . . . .
H19B H 0.125228 0.715466 -0.074243 0.105 Uiso 1 1 calc GR . . . .
H19C H 0.318538 0.867037 -0.067339 0.105 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 O1 1.435(2) . ?
S1 O2 1.428(2) . ?
S1 N1 1.623(3) . ?
S1 C13 1.773(3) . ?
N1 H1 0.81(5) . ?
N1 C1 1.471(4) . ?
C1 H1A 1.0000 . ?
C1 C2 1.529(4) . ?
C1 C9 1.511(4) . ?
C2 C3 1.335(5) . ?
C2 C10 1.492(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.468(5) . ?
C4 C5 1.381(5) . ?
C4 C9 1.404(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.398(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.525(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.528(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.388(5) . ?
C13 C18 1.381(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(6) . ?
C16 C17 1.378(6) . ?
C16 C19 1.510(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(5) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
O1 S1 N1 106.75(15) . . ?
O1 S1 C13 106.94(16) . . ?
O2 S1 O1 120.74(15) . . ?
O2 S1 N1 106.54(15) . . ?
O2 S1 C13 107.51(15) . . ?
N1 S1 C13 107.78(15) . . ?
S1 N1 H1 116(3) . . ?
C1 N1 S1 120.7(2) . . ?
C1 N1 H1 112(3) . . ?
N1 C1 H1A 109.1 . . ?
N1 C1 C2 112.6(3) . . ?
N1 C1 C9 114.1(3) . . ?
C2 C1 H1A 109.1 . . ?
C9 C1 H1A 109.1 . . ?
C9 C1 C2 102.7(3) . . ?
C3 C2 C1 109.6(3) . . ?
C3 C2 C10 130.6(3) . . ?
C10 C2 C1 119.8(3) . . ?
C2 C3 H3 124.5 . . ?
C2 C3 C4 110.9(3) . . ?
C4 C3 H3 124.5 . . ?
C5 C4 C3 132.2(3) . . ?
C5 C4 C9 120.0(3) . . ?
C9 C4 C3 107.7(3) . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.3(3) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.7(3) . . ?
C9 C8 H8 120.6 . . ?
C4 C9 C1 109.0(3) . . ?
C8 C9 C1 130.1(3) . . ?
C8 C9 C4 120.9(3) . . ?
C2 C10 H10A 108.5 . . ?
C2 C10 H10B 108.5 . . ?
C2 C10 C11 115.0(3) . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C10 C11 C12 111.2(3) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 S1 119.7(3) . . ?
C18 C13 S1 119.8(3) . . ?
C18 C13 C14 120.5(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.5(4) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C19 120.0(4) . . ?
C17 C16 C15 118.1(3) . . ?
C17 C16 C19 121.9(4) . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.7(4) . . ?
C18 C17 H17 119.2 . . ?
C13 C18 C17 119.1(4) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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_200110dd_0m
_database_code_depnum_ccdc_archive 'CCDC 2088170'
loop_
_audit_author_name
_audit_author_address
'Xiang Wu'
;Hefei University of Technology
China
;
_audit_update_record             
;
2021-06-05 deposited with the CCDC.	2021-08-24 downloaded from the CCDC.
;
_audit_creation_date             2020-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H23 N O4 S'
_chemical_formula_sum            'C24 H23 N O4 S'
_chemical_formula_weight         421.49
_chemical_absolute_configuration rmad
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2924 0.4247 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.1788(3)
_cell_length_b                   7.7926(3)
_cell_length_c                   16.7712(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.581(2)
_cell_angle_gamma                90
_cell_volume                     1039.01(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2480
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      54.84
_cell_measurement_theta_min      7.60
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.901
_exptl_absorpt_coefficient_mu    1.064
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1494 before and 0.0614 after correction. The Ratio of minimum to maximum transmission is 0.6570. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.006
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13886
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.960
_diffrn_reflns_theta_min         4.720
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3679
_reflns_number_total             3912
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.286
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1543 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.037(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3912
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.048
_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)+(0.0475P)²+0.1318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0926
_refine_special_details          ?
_olex2_refinement_description    
;
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.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3)
2.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15), C19(H19),
 C20(H20), C22(H22), C23(H23)
2.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
;
_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
S1 S -0.08686(8) -0.26208(9) -0.10543(4) 0.03242(19) Uani 1 1 d . . . . .
O1 O -0.2009(3) -0.6016(3) -0.32658(12) 0.0461(6) Uani 1 1 d . . . . .
O2 O -0.8569(3) -0.7424(4) -0.48767(12) 0.0592(7) Uani 1 1 d . . . . .
O3 O -0.2379(3) -0.1682(3) -0.14075(14) 0.0434(5) Uani 1 1 d . . . . .
O4 O 0.0105(3) -0.2168(3) -0.02515(11) 0.0435(6) Uani 1 1 d . . . . .
N1 N -0.1356(3) -0.4610(3) -0.10013(14) 0.0352(6) Uani 1 1 d . . . . .
H1 H -0.045960 -0.522408 -0.093221 0.042 Uiso 1 1 d R . . . .
C1 C -0.2714(3) -0.5433(4) -0.15906(16) 0.0305(6) Uani 1 1 d . . . . .
H1A H -0.310310 -0.461820 -0.205707 0.037 Uiso 1 1 calc R . . . .
C2 C -0.2285(3) -0.7149(4) -0.19511(17) 0.0356(7) Uani 1 1 d . . . . .
H2 H -0.168784 -0.789594 -0.148905 0.043 Uiso 1 1 calc R . . . .
C3 C -0.4034(4) -0.7940(4) -0.23208(16) 0.0340(6) Uani 1 1 d . . . . .
H3 H -0.396282 -0.922083 -0.230366 0.041 Uiso 1 1 calc R . . . .
C4 C -0.5051(3) -0.7305(4) -0.17305(15) 0.0308(6) Uani 1 1 d . . . . .
C5 C -0.6545(4) -0.7931(4) -0.15774(17) 0.0381(7) Uani 1 1 d . . . . .
H5 H -0.713823 -0.883549 -0.190047 0.046 Uiso 1 1 calc R . . . .
C6 C -0.7150(4) -0.7215(4) -0.09469(18) 0.0422(8) Uani 1 1 d . . . . .
H6 H -0.816998 -0.763289 -0.084091 0.051 Uiso 1 1 calc R . . . .
C7 C -0.6296(4) -0.5903(5) -0.04694(19) 0.0412(7) Uani 1 1 d . . . . .
H7 H -0.671502 -0.545125 -0.003034 0.049 Uiso 1 1 calc R . . . .
C8 C -0.4817(4) -0.5237(4) -0.06296(17) 0.0374(7) Uani 1 1 d . . . . .
H8 H -0.422766 -0.432922 -0.030709 0.045 Uiso 1 1 calc R . . . .
C9 C -0.4234(3) -0.5933(4) -0.12687(16) 0.0303(6) Uani 1 1 d . . . . .
C10 C -0.1210(4) -0.7012(5) -0.25686(19) 0.0456(8) Uani 1 1 d . . . . .
H10A H -0.011976 -0.647855 -0.230374 0.055 Uiso 1 1 calc R . . . .
H10B H -0.098111 -0.817779 -0.275071 0.055 Uiso 1 1 calc R . . . .
C11 C -0.3648(4) -0.6458(4) -0.36186(19) 0.0384(7) Uani 1 1 d . . . . .
C12 C -0.4273(4) -0.5907(4) -0.44276(18) 0.0448(8) Uani 1 1 d . . . . .
H12 H -0.356031 -0.530094 -0.470279 0.054 Uiso 1 1 calc R . . . .
C13 C -0.5900(5) -0.6236(5) -0.48229(19) 0.0476(8) Uani 1 1 d . . . . .
H13 H -0.631452 -0.586228 -0.537249 0.057 Uiso 1 1 calc R . . . .
C14 C -0.6953(4) -0.7119(4) -0.44215(17) 0.0431(8) Uani 1 1 d . . . . .
C15 C -0.6352(4) -0.7651(5) -0.36220(16) 0.0380(6) Uani 1 1 d . . . . .
H15 H -0.707843 -0.824525 -0.334998 0.046 Uiso 1 1 calc R . . . .
C16 C -0.4689(4) -0.7327(4) -0.32063(15) 0.0336(6) Uani 1 1 d . . . . .
C17 C -0.9742(5) -0.8164(7) -0.4469(2) 0.0774(16) Uani 1 1 d . . . . .
H17A H -1.084011 -0.827315 -0.485478 0.116 Uiso 1 1 calc GR . . . .
H17B H -0.984774 -0.742740 -0.400984 0.116 Uiso 1 1 calc GR . . . .
H17C H -0.934425 -0.930203 -0.426019 0.116 Uiso 1 1 calc GR . . . .
C18 C 0.0465(3) -0.2437(4) -0.17396(15) 0.0321(6) Uani 1 1 d . . . . .
C19 C 0.2191(3) -0.2357(4) -0.14375(17) 0.0353(6) Uani 1 1 d . . . . .
H19 H 0.265825 -0.231949 -0.086294 0.042 Uiso 1 1 calc R . . . .
C20 C 0.3230(3) -0.2332(4) -0.19829(18) 0.0389(7) Uani 1 1 d . . . . .
H20 H 0.441402 -0.226300 -0.177667 0.047 Uiso 1 1 calc R . . . .
C21 C 0.2575(4) -0.2405(4) -0.28226(17) 0.0395(7) Uani 1 1 d . . . . .
C22 C 0.0841(4) -0.2464(6) -0.31096(17) 0.0483(8) Uani 1 1 d . . . . .
H22 H 0.037405 -0.250825 -0.368409 0.058 Uiso 1 1 calc R . . . .
C23 C -0.0228(4) -0.2461(5) -0.25787(16) 0.0438(7) Uani 1 1 d . . . . .
H23 H -0.141327 -0.247570 -0.278555 0.053 Uiso 1 1 calc R . . . .
C24 C 0.3741(5) -0.2456(6) -0.3404(2) 0.0554(9) Uani 1 1 d . . . . .
H24A H 0.483988 -0.198492 -0.312888 0.083 Uiso 1 1 calc GR . . . .
H24B H 0.325982 -0.177148 -0.389265 0.083 Uiso 1 1 calc GR . . . .
H24C H 0.387829 -0.364645 -0.356571 0.083 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 O3 1.438(2) . ?
S1 O4 1.438(2) . ?
S1 N1 1.608(3) . ?
S1 C18 1.766(3) . ?
O1 C10 1.428(4) . ?
O1 C11 1.376(4) . ?
O2 C14 1.383(4) . ?
O2 C17 1.425(5) . ?
N1 H1 0.8600 . ?
N1 C1 1.451(3) . ?
C1 H1A 1.0000 . ?
C1 C2 1.541(4) . ?
C1 C9 1.518(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.548(4) . ?
C2 C10 1.511(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.518(4) . ?
C3 C16 1.532(4) . ?
C4 C5 1.394(4) . ?
C4 C9 1.395(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.399(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.400(4) . ?
C11 C16 1.392(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.364(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(5) . ?
C14 C15 1.379(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.399(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.385(4) . ?
C18 C23 1.388(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(4) . ?
C21 C22 1.387(4) . ?
C21 C24 1.516(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(4) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
O3 S1 N1 108.26(13) . . ?
O3 S1 C18 107.02(13) . . ?
O4 S1 O3 119.60(14) . . ?
O4 S1 N1 105.93(13) . . ?
O4 S1 C18 107.38(12) . . ?
N1 S1 C18 108.23(14) . . ?
C11 O1 C10 115.3(3) . . ?
C14 O2 C17 117.9(2) . . ?
S1 N1 H1 109.2 . . ?
C1 N1 S1 123.25(19) . . ?
C1 N1 H1 109.7 . . ?
N1 C1 H1A 107.7 . . ?
N1 C1 C2 116.2(2) . . ?
N1 C1 C9 115.5(2) . . ?
C2 C1 H1A 107.7 . . ?
C9 C1 H1A 107.7 . . ?
C9 C1 C2 101.4(2) . . ?
C1 C2 H2 108.4 . . ?
C1 C2 C3 103.2(2) . . ?
C3 C2 H2 108.4 . . ?
C10 C2 C1 115.5(3) . . ?
C10 C2 H2 108.4 . . ?
C10 C2 C3 112.7(2) . . ?
C2 C3 H3 110.1 . . ?
C4 C3 C2 101.9(2) . . ?
C4 C3 H3 110.1 . . ?
C4 C3 C16 114.2(2) . . ?
C16 C3 C2 110.1(2) . . ?
C16 C3 H3 110.1 . . ?
C5 C4 C3 130.1(3) . . ?
C5 C4 C9 119.5(3) . . ?
C9 C4 C3 110.3(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.3(3) . . ?
C9 C8 H8 120.8 . . ?
C4 C9 C1 109.0(2) . . ?
C8 C9 C1 129.5(3) . . ?
C8 C9 C4 121.6(3) . . ?
O1 C10 C2 111.8(2) . . ?
O1 C10 H10A 109.3 . . ?
O1 C10 H10B 109.3 . . ?
C2 C10 H10A 109.3 . . ?
C2 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
O1 C11 C12 115.9(3) . . ?
O1 C11 C16 123.8(3) . . ?
C16 C11 C12 120.2(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
O2 C14 C13 115.9(3) . . ?
C15 C14 O2 124.1(3) . . ?
C15 C14 C13 119.9(3) . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.9(3) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C3 121.2(3) . . ?
C11 C16 C15 118.5(3) . . ?
C15 C16 C3 120.3(3) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 S1 119.9(2) . . ?
C19 C18 C23 120.6(2) . . ?
C23 C18 S1 119.4(2) . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.3(2) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.2(3) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C22 118.3(3) . . ?
C20 C21 C24 120.2(3) . . ?
C22 C21 C24 121.5(3) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 C21 121.6(3) . . ?
C23 C22 H22 119.2 . . ?
C18 C23 H23 120.6 . . ?
C22 C23 C18 118.8(3) . . ?
C22 C23 H23 120.6 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
