# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_aaaa
_database_code_depnum_ccdc_archive 'CCDC 2034600'
loop_
_audit_author_name
_audit_author_address
'Dong-Liang Mo'
;Guangxi Normal University
China
;
_audit_update_record             
;
2020-09-29 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2020-05-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 N O3 S'
_chemical_formula_sum            'C24 H21 N O3 S'
_chemical_formula_weight         403.48
_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                   18.9549(16)
_cell_length_b                   8.4866(7)
_cell_length_c                   24.972(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.8970(10)
_cell_angle_gamma                90
_cell_volume                     4011.9(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6387
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23934
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.591
_diffrn_reflns_theta_min         1.633
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                3164
_reflns_number_total             4169
_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 v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.047
_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)+(0.0635P)²+1.7936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1217
_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:
 C7(H7), C13(H13), C21(H21), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_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 0.08054(3) 0.94754(5) 0.14478(2) 0.04875(16) Uani 1 1 d . . . . .
N1 N 0.11574(8) 0.77038(16) 0.14241(5) 0.0419(3) Uani 1 1 d . . . . .
O2 O 0.18462(7) 0.45633(16) 0.16977(5) 0.0573(4) Uani 1 1 d . . . . .
C3 C 0.07592(9) 0.5603(2) 0.08256(7) 0.0420(4) Uani 1 1 d . . . . .
O4 O 0.11446(9) 1.04326(15) 0.10660(6) 0.0650(4) Uani 1 1 d . . . . .
O5 O 0.08296(9) 0.99339(16) 0.19992(5) 0.0617(4) Uani 1 1 d . . . . .
C6 C 0.11683(9) 0.6950(2) 0.09066(6) 0.0403(4) Uani 1 1 d . . . . .
C7 C 0.11370(9) 0.66757(19) 0.19037(6) 0.0397(4) Uani 1 1 d . . . . .
H7 H 0.0985 0.7282 0.2211 0.048 Uiso 1 1 calc R . . . .
C8 C 0.18604(10) 0.5212(2) 0.25866(7) 0.0476(4) Uani 1 1 d . . . . .
C9 C 0.07857(11) 0.4822(3) 0.03396(8) 0.0543(5) Uani 1 1 d . . . . .
H9 H 0.0534 0.3889 0.0285 0.065 Uiso 1 1 calc R . . . .
C10 C -0.00834(11) 0.92837(19) 0.12208(7) 0.0469(4) Uani 1 1 d . . . . .
C11 C 0.14376(11) 0.3888(2) 0.25136(7) 0.0499(4) Uani 1 1 d . . . . .
C12 C -0.02503(12) 0.9205(3) 0.06723(8) 0.0596(5) Uani 1 1 d . . . . .
H12 H 0.0103 0.9285 0.0429 0.071 Uiso 1 1 calc R . . . .
C13 C 0.06693(10) 0.5176(2) 0.18208(7) 0.0432(4) Uani 1 1 d . . . . .
H13 H 0.0320 0.5127 0.2097 0.052 Uiso 1 1 calc R . . . .
C14 C -0.13021(12) 0.8996(3) 0.13954(8) 0.0606(5) Uani 1 1 d . . . . .
H14 H -0.1656 0.8932 0.1639 0.073 Uiso 1 1 calc R . . . .
C15 C 0.11812(11) 0.5410(3) -0.00657(8) 0.0610(6) Uani 1 1 d . . . . .
H15 H 0.1186 0.4889 -0.0393 0.073 Uiso 1 1 calc R . . . .
C16 C 0.21407(12) 0.5614(3) 0.30865(8) 0.0601(5) Uani 1 1 d . . . . .
H16 H 0.2428 0.6496 0.3136 0.072 Uiso 1 1 calc R . . . .
C17 C -0.06112(12) 0.9173(2) 0.15815(8) 0.0538(5) Uani 1 1 d . . . . .
H17 H -0.0500 0.9218 0.1948 0.065 Uiso 1 1 calc R . . . .
C18 C 0.15778(10) 0.7531(2) 0.05071(7) 0.0511(5) Uani 1 1 d . . . . .
H18 H 0.1856 0.8422 0.0568 0.061 Uiso 1 1 calc R . . . .
C19 C 0.19787(13) 0.4650(3) 0.35172(8) 0.0645(6) Uani 1 1 d . . . . .
H19 H 0.2166 0.4885 0.3859 0.077 Uiso 1 1 calc R . . . .
C20 C -0.09453(12) 0.9008(3) 0.04939(8) 0.0629(6) Uani 1 1 d . . . . .
H20 H -0.1056 0.8939 0.0128 0.076 Uiso 1 1 calc R . . . .
C21 C 0.18750(10) 0.5941(2) 0.20344(7) 0.0496(4) Uani 1 1 d . . . . .
H21 H 0.2275 0.6645 0.1981 0.060 Uiso 1 1 calc R . . . .
C22 C -0.14810(11) 0.8910(2) 0.08487(8) 0.0592(5) Uani 1 1 d . . . . .
C23 C 0.12298(11) 0.3877(2) 0.19209(7) 0.0517(5) Uani 1 1 d . . . . .
H23 H 0.1096 0.2841 0.1775 0.062 Uiso 1 1 calc R . . . .
C24 C 0.02945(10) 0.5099(2) 0.12613(7) 0.0485(4) Uani 1 1 d . . . . .
H24A H 0.0136 0.4028 0.1192 0.058 Uiso 1 1 calc R . . . .
H24B H -0.0120 0.5771 0.1255 0.058 Uiso 1 1 calc R . . . .
C25 C 0.15682(11) 0.6769(3) 0.00166(7) 0.0594(5) Uani 1 1 d . . . . .
H25 H 0.1825 0.7178 -0.0259 0.071 Uiso 1 1 calc R . . . .
C26 C 0.12636(13) 0.2961(2) 0.29394(8) 0.0630(6) Uani 1 1 d . . . . .
H26 H 0.0967 0.2095 0.2892 0.076 Uiso 1 1 calc R . . . .
C27 C 0.15491(13) 0.3370(3) 0.34432(8) 0.0659(6) Uani 1 1 d . . . . .
H27 H 0.1445 0.2757 0.3738 0.079 Uiso 1 1 calc R . . . .
C28 C -0.22365(13) 0.8706(4) 0.06453(11) 0.0867(8) Uani 1 1 d . . . . .
H28A H -0.2390 0.7655 0.0721 0.130 Uiso 1 1 calc GR . . . .
H28B H -0.2272 0.8881 0.0265 0.130 Uiso 1 1 calc GR . . . .
H28C H -0.2529 0.9450 0.0820 0.130 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 N1 1.6471(14) . ?
S1 O4 1.4297(14) . ?
S1 O5 1.4294(13) . ?
S1 C10 1.758(2) . ?
N1 C6 1.443(2) . ?
N1 C7 1.4839(19) . ?
O2 C21 1.439(2) . ?
O2 C23 1.442(2) . ?
C3 C6 1.390(2) . ?
C3 C9 1.386(2) . ?
C3 C24 1.496(2) . ?
C6 C18 1.385(2) . ?
C7 C13 1.559(2) . ?
C7 C21 1.551(3) . ?
C8 C11 1.387(3) . ?
C8 C16 1.375(3) . ?
C8 C21 1.513(2) . ?
C9 C15 1.383(3) . ?
C10 C12 1.392(3) . ?
C10 C17 1.383(3) . ?
C11 C23 1.512(2) . ?
C11 C26 1.376(3) . ?
C12 C20 1.379(3) . ?
C13 C23 1.542(3) . ?
C13 C24 1.536(2) . ?
C14 C17 1.376(3) . ?
C14 C22 1.392(3) . ?
C15 C25 1.377(3) . ?
C16 C19 1.398(3) . ?
C18 C25 1.384(3) . ?
C19 C27 1.365(3) . ?
C20 C22 1.383(3) . ?
C22 C28 1.505(3) . ?
C26 C27 1.388(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
N1 S1 C10 106.70(8) . . ?
O4 S1 N1 107.34(8) . . ?
O4 S1 C10 107.07(9) . . ?
O5 S1 N1 106.84(8) . . ?
O5 S1 O4 119.60(9) . . ?
O5 S1 C10 108.63(9) . . ?
C6 N1 S1 117.46(11) . . ?
C6 N1 C7 117.65(13) . . ?
C7 N1 S1 118.73(11) . . ?
C21 O2 C23 96.30(13) . . ?
C6 C3 C24 118.27(15) . . ?
C9 C3 C6 118.42(17) . . ?
C9 C3 C24 123.28(17) . . ?
C3 C6 N1 117.50(14) . . ?
C18 C6 N1 121.38(16) . . ?
C18 C6 C3 121.12(16) . . ?
N1 C7 C13 114.25(13) . . ?
N1 C7 C21 110.26(13) . . ?
C21 C7 C13 101.55(13) . . ?
C11 C8 C21 104.39(15) . . ?
C16 C8 C11 120.98(18) . . ?
C16 C8 C21 134.60(18) . . ?
C15 C9 C3 120.87(19) . . ?
C12 C10 S1 119.23(15) . . ?
C17 C10 S1 120.63(15) . . ?
C17 C10 C12 120.12(19) . . ?
C8 C11 C23 104.69(15) . . ?
C26 C11 C8 121.40(18) . . ?
C26 C11 C23 133.81(19) . . ?
C20 C12 C10 119.30(19) . . ?
C23 C13 C7 100.34(14) . . ?
C24 C13 C7 112.90(14) . . ?
C24 C13 C23 113.59(15) . . ?
C17 C14 C22 121.2(2) . . ?
C25 C15 C9 119.85(18) . . ?
C8 C16 C19 117.6(2) . . ?
C14 C17 C10 119.68(18) . . ?
C25 C18 C6 119.21(18) . . ?
C27 C19 C16 121.0(2) . . ?
C12 C20 C22 121.37(19) . . ?
O2 C21 C7 101.33(14) . . ?
O2 C21 C8 101.45(15) . . ?
C8 C21 C7 107.36(14) . . ?
C14 C22 C28 121.2(2) . . ?
C20 C22 C14 118.3(2) . . ?
C20 C22 C28 120.5(2) . . ?
O2 C23 C11 101.53(15) . . ?
O2 C23 C13 102.34(14) . . ?
C11 C23 C13 107.32(14) . . ?
C3 C24 C13 112.77(14) . . ?
C15 C25 C18 120.42(18) . . ?
C11 C26 C27 117.4(2) . . ?
C19 C27 C26 121.6(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_aaaa_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2034601'
loop_
_audit_author_name
_audit_author_address
'Dong-Liang Mo'
;Guangxi Normal University
China
;
_audit_update_record             
;
2020-09-29 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2020-09-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.15(C25 H20 N O3 S)'
_chemical_formula_sum            'C3.85 H3.23 N0.15 O0.46 S0.15'
_chemical_formula_weight         63.92
_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                   19.956(3)
_cell_length_b                   8.6435(12)
_cell_length_c                   24.548(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.934(2)
_cell_angle_gamma                90
_cell_volume                     4224.3(10)
_cell_formula_units_Z            52
_cell_measurement_reflns_used    5342
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.10
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            27754
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.705
_diffrn_reflns_theta_min         1.663
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                3420
_reflns_number_total             4950
_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 v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4950
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      0.906
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1938
_refine_ls_wR_factor_ref         0.2374
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C0AA(H0AA), C1AA(H1AA), C7AA(H7AA), C1CA(H1CA), C2CA(H2CA)
2.b Aromatic/amide H refined with riding coordinates:
 C8AA(H8AA), C5AA(H5AA), C3CA(H3CA), C9AA(H9AA), C0BA(H0BA), C1BA(H1BA),
 C2BA(H2BA), C3BA(H3BA), C4BA(H4BA), C6BA(H6BA), C7BA(H7BA), C8BA(H8BA)
2.c Idealised Me refined as rotating group:
 C0CA(H0CA,H0CB,H0CC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
S0A S 0.41732(3) 0.07188(7) 0.35400(2) 0.0449(2) Uani 1 1 d . . . . .
C8AA C 0.41471(15) 0.5304(3) 0.46817(11) 0.0548(7) Uani 1 1 d . . . . .
H8AA H 0.4383 0.6219 0.4750 0.066 Uiso 1 1 calc R . . . .
N N 0.38562(10) 0.2460(2) 0.35670(8) 0.0418(5) Uani 1 1 d . . . . .
C2AA C 0.50236(13) 0.0860(3) 0.37735(10) 0.0417(5) Uani 1 1 d . . . . .
C3AA C 0.41966(12) 0.4546(3) 0.41824(10) 0.0419(5) Uani 1 1 d . . . . .
C0AA C 0.38296(12) 0.3469(3) 0.30791(10) 0.0406(5) Uani 1 1 d . . . . .
H0AA H 0.3991 0.2914 0.2766 0.049 Uiso 1 1 calc R . . . .
C4AA C 0.34386(12) 0.6228(3) 0.24935(10) 0.0438(6) Uani 1 1 d . . . . .
C5AA C 0.55190(15) 0.0927(3) 0.34027(11) 0.0526(7) Uani 1 1 d . . . . .
H5AA H 0.5405 0.0896 0.3029 0.063 Uiso 1 1 calc R . . . .
C6AA C 0.30905(13) 0.4849(3) 0.23953(10) 0.0470(6) Uani 1 1 d . . . . .
C C 0.38237(12) 0.3193(3) 0.40898(9) 0.0403(5) Uani 1 1 d . . . . .
C3CA C 0.34014(15) 0.3383(4) 0.49769(11) 0.0597(7) Uani 1 1 d . . . . .
H3CA H 0.3144 0.2984 0.5246 0.072 Uiso 1 1 calc R . . . .
C9AA C 0.34235(13) 0.2621(3) 0.44826(10) 0.0494(6) Uani 1 1 d . . . . .
H9AA H 0.3171 0.1730 0.4415 0.059 Uiso 1 1 calc R . . . .
C0BA C 0.28335(15) 0.4435(4) 0.18799(12) 0.0573(7) Uani 1 1 d . . . . .
H0BA H 0.2602 0.3511 0.1818 0.069 Uiso 1 1 calc R . . . .
C1BA C 0.61823(16) 0.1041(3) 0.35986(12) 0.0589(7) Uani 1 1 d . . . . .
H1BA H 0.6513 0.1093 0.3350 0.071 Uiso 1 1 calc R . . . .
C2BA C 0.29371(16) 0.5472(4) 0.14515(11) 0.0601(8) Uani 1 1 d . . . . .
H2BA H 0.2766 0.5242 0.1099 0.072 Uiso 1 1 calc R . . . .
C1AA C 0.42263(12) 0.5017(3) 0.31796(10) 0.0406(5) Uani 1 1 d . . . . .
H1AA H 0.4536 0.5155 0.2890 0.049 Uiso 1 1 calc R . . . .
C3BA C 0.35568(14) 0.7230(3) 0.20725(11) 0.0551(7) Uani 1 1 d . . . . .
H3BA H 0.3803 0.8134 0.2134 0.066 Uiso 1 1 calc R . . . .
C7AA C 0.46274(12) 0.5069(3) 0.37394(11) 0.0459(6) Uani 1 1 d . . . . .
H7AA H 0.4991 0.4312 0.3725 0.055 Uiso 1 1 calc R . . . .
C4BA C 0.51992(15) 0.0898(3) 0.43309(11) 0.0520(6) Uani 1 1 d . . . . .
H4BA H 0.4868 0.0847 0.4579 0.062 Uiso 1 1 calc R . . . .
C5BA C 0.63748(15) 0.1083(3) 0.41510(12) 0.0538(7) Uani 1 1 d . . . . .
C6BA C 0.32898(16) 0.6824(4) 0.15496(11) 0.0616(8) Uani 1 1 d . . . . .
H6BA H 0.3353 0.7489 0.1260 0.074 Uiso 1 1 calc R . . . .
C7BA C 0.37586(16) 0.4725(4) 0.50717(11) 0.0613(8) Uani 1 1 d . . . . .
H7BA H 0.3736 0.5243 0.5402 0.074 Uiso 1 1 calc R . . . .
C8BA C 0.58641(15) 0.1012(3) 0.45163(11) 0.0563(7) Uani 1 1 d . . . . .
H8BA H 0.5977 0.1042 0.4890 0.068 Uiso 1 1 calc R . . . .
C0CA C 0.49562(16) 0.6632(3) 0.38401(15) 0.0683(9) Uani 1 1 d . . . . .
H0CA H 0.4619 0.7385 0.3910 0.102 Uiso 1 1 calc GR . . . .
H0CB H 0.5182 0.6934 0.3524 0.102 Uiso 1 1 calc GR . . . .
H0CC H 0.5275 0.6566 0.4150 0.102 Uiso 1 1 calc GR . . . .
C1CA C 0.31112(13) 0.4065(3) 0.29483(11) 0.0481(6) Uani 1 1 d . . . . .
H1CA H 0.2757 0.3296 0.2989 0.058 Uiso 1 1 calc R . . . .
C2CA C 0.36483(13) 0.6202(3) 0.30972(10) 0.0453(6) Uani 1 1 d . . . . .
H2CA H 0.3741 0.7219 0.3262 0.054 Uiso 1 1 calc R . . . .
O O 0.30908(9) 0.5377(2) 0.33084(7) 0.0511(5) Uani 1 1 d . . . . .
O1 O 0.41368(11) 0.0280(2) 0.29779(8) 0.0594(5) Uani 1 1 d . . . . .
O2 O 0.38518(11) -0.0210(2) 0.39287(8) 0.0584(5) Uani 1 1 d . . . . .
C1 C 0.7101(2) 0.1206(5) 0.43639(16) 0.0805(10) Uiso 1 1 d . . . . .


_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
S0A N 1.636(2) . ?
S0A C2AA 1.758(3) . ?
S0A O1 1.4281(19) . ?
S0A O2 1.432(2) . ?
C8AA C3AA 1.399(3) . ?
C8AA C7BA 1.367(4) . ?
N C0AA 1.479(3) . ?
N C 1.437(3) . ?
C2AA C5AA 1.390(4) . ?
C2AA C4BA 1.389(3) . ?
C3AA C 1.397(3) . ?
C3AA C7AA 1.501(4) . ?
C0AA C1AA 1.566(3) . ?
C0AA C1CA 1.536(3) . ?
C4AA C6AA 1.393(4) . ?
C4AA C3BA 1.381(3) . ?
C4AA C2CA 1.512(3) . ?
C5AA C1BA 1.380(4) . ?
C6AA C0BA 1.379(4) . ?
C6AA C1CA 1.515(3) . ?
C C9AA 1.385(3) . ?
C3CA C9AA 1.384(4) . ?
C3CA C7BA 1.374(5) . ?
C0BA C2BA 1.408(4) . ?
C1BA C5BA 1.384(4) . ?
C2BA C6BA 1.377(5) . ?
C1AA C7AA 1.543(3) . ?
C1AA C2CA 1.546(3) . ?
C3BA C6BA 1.400(4) . ?
C7AA C0CA 1.514(4) . ?
C4BA C8BA 1.376(4) . ?
C5BA C8BA 1.404(4) . ?
C5BA C1 1.510(5) . ?
C1CA O 1.440(3) . ?
C2CA O 1.447(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
N S0A C2AA 106.89(11) . . ?
O1 S0A N 106.82(11) . . ?
O1 S0A C2AA 108.51(13) . . ?
O2 S0A N 107.25(11) . . ?
O2 S0A C2AA 106.75(12) . . ?
O2 S0A O1 119.97(13) . . ?
C7BA C8AA C3AA 121.3(3) . . ?
C0AA N S0A 120.13(15) . . ?
C N S0A 118.90(15) . . ?
C N C0AA 117.51(18) . . ?
C5AA C2AA S0A 120.2(2) . . ?
C5AA C2AA C4BA 120.1(2) . . ?
C4BA C2AA S0A 119.7(2) . . ?
C8AA C3AA C7AA 124.9(2) . . ?
C C3AA C8AA 117.8(2) . . ?
C C3AA C7AA 117.4(2) . . ?
N C0AA C1AA 112.74(19) . . ?
N C0AA C1CA 110.35(19) . . ?
C1CA C0AA C1AA 101.59(19) . . ?
C6AA C4AA C3BA 121.1(2) . . ?
C6AA C4AA C2CA 105.0(2) . . ?
C3BA C4AA C2CA 133.9(3) . . ?
C1BA C5AA C2AA 118.9(2) . . ?
C4AA C6AA C0BA 122.0(2) . . ?
C4AA C6AA C1CA 104.2(2) . . ?
C0BA C6AA C1CA 133.8(3) . . ?
C3AA C N 117.3(2) . . ?
C3AA C C9AA 120.8(2) . . ?
C9AA C N 121.9(2) . . ?
C7BA C3CA C9AA 120.2(3) . . ?
C3CA C9AA C 119.7(3) . . ?
C6AA C0BA C2BA 117.1(3) . . ?
C5AA C1BA C5BA 122.6(3) . . ?
C6BA C2BA C0BA 120.6(3) . . ?
C7AA C1AA C0AA 113.02(19) . . ?
C2CA C1AA C0AA 100.44(19) . . ?
C2CA C1AA C7AA 115.7(2) . . ?
C4AA C3BA C6BA 117.1(3) . . ?
C3AA C7AA C1AA 110.4(2) . . ?
C3AA C7AA C0CA 114.4(2) . . ?
C0CA C7AA C1AA 111.3(2) . . ?
C8BA C4BA C2AA 120.0(3) . . ?
C1BA C5BA C1 122.4(3) . . ?
C8BA C5BA C1BA 117.4(3) . . ?
C8BA C5BA C1 120.2(3) . . ?
C2BA C6BA C3BA 122.0(3) . . ?
C8AA C7BA C3CA 120.2(3) . . ?
C4BA C8BA C5BA 121.2(3) . . ?
C6AA C1CA C0AA 107.7(2) . . ?
O C1CA C0AA 101.59(19) . . ?
O C1CA C6AA 101.4(2) . . ?
C4AA C2CA C1AA 107.0(2) . . ?
O C2CA C4AA 101.0(2) . . ?
O C2CA C1AA 102.21(19) . . ?
C2CA O C1CA 96.53(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
