# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 2328851'
loop_
_audit_author_name
_audit_author_address
'Chen Kang'
;Nanchang University
China
;
_audit_update_record             
;
2024-01-27 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_audit_creation_date             2024-01-07
_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         '0.27(C10 H9 Br N2 O2 S)'
_chemical_formula_sum            'C H Br0.07 Cl N O S0.07'
_chemical_formula_weight         85.94
_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'
Cl Cl 0.1484 0.1585 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.976(3)
_cell_length_b                   12.668(4)
_cell_length_c                   12.714(4)
_cell_angle_alpha                101.928(6)
_cell_angle_beta                 102.068(6)
_cell_angle_gamma                105.796(6)
_cell_volume                     1160.5(7)
_cell_formula_units_Z            15
_cell_measurement_reflns_used    2037
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.26
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.867
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2825
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1487 before and 0.0468 after correction.
The Ratio of minimum to maximum transmission is 0.3789.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             636
_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  0.0432
_diffrn_reflns_av_unetI/netI     0.1244
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7022
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.855
_diffrn_reflns_theta_min         2.740
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2603
_reflns_number_total             5121
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         1.132
_refine_diff_density_min         -0.987
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1530
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      0.994
_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)+(0.0705P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1674
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C)
;
_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
Br1 Br 0.94271(12) 0.06778(6) 0.87231(6) 0.0650(3) Uani 1 1 d . . . . .
O1 O 1.1862(6) 0.3492(4) 0.5322(4) 0.0600(13) Uani 1 1 d . . . . .
S1 S 1.0575(2) 0.24254(14) 0.51936(13) 0.0426(4) Uani 1 1 d . . . . .
N1 N 1.0642(7) 0.2297(4) 0.6482(4) 0.0373(12) Uani 1 1 d . . . . .
C1 C 0.8382(8) 0.2460(5) 0.4682(5) 0.0374(15) Uani 1 1 d . . . . .
N2 N 1.0765(7) 0.3225(4) 0.7313(4) 0.0385(12) Uani 1 1 d . . . . .
C2 C 0.8077(11) 0.3484(6) 0.4818(6) 0.0559(19) Uani 1 1 d . . . . .
H2 H 0.903750 0.416602 0.514814 0.067 Uiso 1 1 calc R . . . .
O2 O 1.0737(6) 0.1394(4) 0.4604(4) 0.0555(12) Uani 1 1 d . . . . .
C3 C 0.6347(14) 0.3493(8) 0.4463(7) 0.071(2) Uani 1 1 d . . . . .
H3 H 0.612325 0.418468 0.456544 0.086 Uiso 1 1 calc R . . . .
C4 C 0.4941(12) 0.2494(11) 0.3959(6) 0.076(3) Uani 1 1 d . . . . .
H4 H 0.376370 0.250502 0.371690 0.091 Uiso 1 1 calc R . . . .
C5 C 0.5265(11) 0.1484(9) 0.3813(6) 0.075(3) Uani 1 1 d . . . . .
H5 H 0.430722 0.080476 0.345636 0.090 Uiso 1 1 calc R . . . .
C6 C 0.7007(10) 0.1452(6) 0.4190(6) 0.0548(19) Uani 1 1 d . . . . .
H6 H 0.722819 0.075945 0.410740 0.066 Uiso 1 1 calc R . . . .
C7 C 1.0167(8) 0.1318(5) 0.6786(5) 0.0370(15) Uani 1 1 d . . . . .
H7 H 0.995895 0.058203 0.635311 0.044 Uiso 1 1 calc R . . . .
C8 C 1.0059(8) 0.1629(5) 0.7845(5) 0.0378(15) Uani 1 1 d . . . . .
C9 C 1.0428(8) 0.2818(5) 0.8152(5) 0.0342(14) Uani 1 1 d . . . . .
C10 C 1.0493(10) 0.3569(5) 0.9244(5) 0.0540(19) Uani 1 1 d . . . . .
H10A H 1.094925 0.435528 0.925155 0.081 Uiso 1 1 calc GR . . . .
H10B H 1.127913 0.343197 0.984565 0.081 Uiso 1 1 calc GR . . . .
H10C H 0.929378 0.340314 0.933717 0.081 Uiso 1 1 calc GR . . . .
S2 S 0.4852(2) 0.20639(13) 0.08902(13) 0.0367(4) Uani 1 1 d . . . . .
Br2 Br 0.53468(11) 0.17607(7) -0.34381(6) 0.0650(3) Uani 1 1 d . . . . .
N3 N 0.4679(7) 0.2272(4) -0.0380(4) 0.0374(12) Uani 1 1 d . . . . .
O3 O 0.3980(6) 0.2753(4) 0.1427(3) 0.0499(12) Uani 1 1 d . . . . .
N4 N 0.4945(7) 0.3347(4) -0.0454(4) 0.0426(13) Uani 1 1 d . . . . .
O4 O 0.4206(6) 0.0862(4) 0.0679(4) 0.0528(12) Uani 1 1 d . . . . .
C11 C 0.7183(7) 0.2605(5) 0.1530(5) 0.0301(13) Uani 1 1 d . . . . .
C12 C 0.8020(9) 0.3760(5) 0.2023(5) 0.0390(16) Uani 1 1 d . . . . .
H12 H 0.734138 0.425119 0.205372 0.047 Uiso 1 1 calc R . . . .
C13 C 0.9878(9) 0.4178(5) 0.2469(5) 0.0428(16) Uani 1 1 d . . . . .
H13 H 1.045682 0.495782 0.279743 0.051 Uiso 1 1 calc R . . . .
C14 C 1.0878(9) 0.3463(5) 0.2435(5) 0.0438(16) Uani 1 1 d . . . . .
H14 H 1.213061 0.375180 0.274596 0.053 Uiso 1 1 calc R . . . .
C15 C 1.0032(9) 0.2317(5) 0.1942(6) 0.0475(18) Uani 1 1 d . . . . .
H15 H 1.071507 0.182729 0.192267 0.057 Uiso 1 1 calc R . . . .
C16 C 0.8205(9) 0.1886(5) 0.1482(5) 0.0418(16) Uani 1 1 d . . . . .
H16 H 0.764354 0.110742 0.113471 0.050 Uiso 1 1 calc R . . . .
C17 C 0.4853(8) 0.1567(5) -0.1301(5) 0.0371(15) Uani 1 1 d . . . . .
H17 H 0.477868 0.080459 -0.141776 0.045 Uiso 1 1 calc R . . . .
C18 C 0.5148(8) 0.2210(5) -0.1986(5) 0.0407(15) Uani 1 1 d . . . . .
C19 C 0.5176(8) 0.3307(5) -0.1465(5) 0.0355(15) Uani 1 1 d . . . . .
C20 C 0.5483(10) 0.4333(6) -0.1874(6) 0.060(2) Uani 1 1 d . . . . .
H20A H 0.526988 0.492724 -0.137030 0.091 Uiso 1 1 calc GR . . . .
H20B H 0.466504 0.414987 -0.260659 0.091 Uiso 1 1 calc GR . . . .
H20C H 0.671247 0.458798 -0.191029 0.091 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
Br1 C8 1.848(6) . ?
O1 S1 1.410(4) . ?
S1 N1 1.670(5) . ?
S1 C1 1.749(7) . ?
S1 O2 1.420(4) . ?
N1 N2 1.374(6) . ?
N1 C7 1.354(7) . ?
C1 C2 1.367(9) . ?
C1 C6 1.359(8) . ?
N2 C9 1.322(7) . ?
C2 C3 1.363(11) . ?
C3 C4 1.365(12) . ?
C4 C5 1.357(12) . ?
C5 C6 1.387(10) . ?
C7 C8 1.351(8) . ?
C8 C9 1.405(8) . ?
C9 C10 1.494(8) . ?
S2 N3 1.673(5) . ?
S2 O3 1.412(4) . ?
S2 O4 1.415(4) . ?
S2 C11 1.741(6) . ?
Br2 C18 1.869(6) . ?
N3 N4 1.346(6) . ?
N3 C17 1.375(7) . ?
N4 C19 1.329(7) . ?
C11 C12 1.375(7) . ?
C11 C16 1.379(8) . ?
C12 C13 1.377(8) . ?
C13 C14 1.359(8) . ?
C14 C15 1.367(8) . ?
C15 C16 1.357(9) . ?
C17 C18 1.323(8) . ?
C18 C19 1.403(8) . ?
C19 C20 1.476(8) . ?

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 106.7(3) . . ?
O1 S1 C1 109.7(3) . . ?
O1 S1 O2 120.9(3) . . ?
N1 S1 C1 103.3(3) . . ?
O2 S1 N1 104.7(3) . . ?
O2 S1 C1 109.9(3) . . ?
N2 N1 S1 119.3(4) . . ?
C7 N1 S1 127.4(4) . . ?
C7 N1 N2 111.4(5) . . ?
C2 C1 S1 119.9(5) . . ?
C6 C1 S1 118.4(5) . . ?
C6 C1 C2 121.6(7) . . ?
C9 N2 N1 105.5(5) . . ?
C3 C2 C1 119.2(7) . . ?
C2 C3 C4 120.5(8) . . ?
C5 C4 C3 119.8(8) . . ?
C4 C5 C6 120.8(8) . . ?
C1 C6 C5 118.1(8) . . ?
C8 C7 N1 105.9(5) . . ?
C7 C8 Br1 127.1(4) . . ?
C7 C8 C9 107.5(5) . . ?
C9 C8 Br1 125.4(5) . . ?
N2 C9 C8 109.6(5) . . ?
N2 C9 C10 122.4(5) . . ?
C8 C9 C10 128.1(6) . . ?
N3 S2 C11 103.1(3) . . ?
O3 S2 N3 106.1(3) . . ?
O3 S2 O4 120.8(3) . . ?
O3 S2 C11 110.0(3) . . ?
O4 S2 N3 104.5(3) . . ?
O4 S2 C11 110.6(3) . . ?
N4 N3 S2 117.7(4) . . ?
N4 N3 C17 112.5(4) . . ?
C17 N3 S2 126.6(4) . . ?
C19 N4 N3 104.5(5) . . ?
C12 C11 S2 120.0(4) . . ?
C12 C11 C16 120.0(6) . . ?
C16 C11 S2 119.9(4) . . ?
C11 C12 C13 119.1(5) . . ?
C14 C13 C12 120.8(6) . . ?
C13 C14 C15 119.7(6) . . ?
C16 C15 C14 120.6(6) . . ?
C15 C16 C11 119.8(5) . . ?
C18 C17 N3 105.0(5) . . ?
C17 C18 Br2 127.7(5) . . ?
C17 C18 C19 108.1(6) . . ?
C19 C18 Br2 124.2(5) . . ?
N4 C19 C18 109.8(5) . . ?
N4 C19 C20 121.0(6) . . ?
C18 C19 C20 129.1(6) . . ?

_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_t_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2328852'
loop_
_audit_author_name
_audit_author_address
'Chen Kang'
;Nanchang University
China
;
_audit_update_record             
;
2024-01-27 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_audit_creation_date             2024-01-07
_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         '0.15(C12 H12 N2 O4 S)'
_chemical_formula_sum            'C H Cl0 N O S0.08'
_chemical_formula_weight         45.49
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3939(16)
_cell_length_b                   7.7731(17)
_cell_length_c                   13.160(3)
_cell_angle_alpha                84.179(4)
_cell_angle_beta                 73.900(3)
_cell_angle_gamma                63.163(3)
_cell_volume                     648.2(2)
_cell_formula_units_Z            13
_cell_measurement_reflns_used    2377
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.94
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5742
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0726 before and 0.0295 after correction.
The Ratio of minimum to maximum transmission is 0.7701.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             302
_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  0.0220
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3956
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.684
_diffrn_reflns_theta_min         2.938
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2361
_reflns_number_total             2865
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.200
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.61(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2865
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.060
_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)+(0.0529P)²+0.1768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1127
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 0.07359(6) 0.78766(6) 0.81580(3) 0.04118(18) Uani 1 1 d . . . . .
C1 C 0.1914(3) 0.5953(2) 0.89284(12) 0.0361(4) Uani 1 1 d . . . . .
O1 O -0.0160(2) 0.7345(2) 0.74962(11) 0.0530(4) Uani 1 1 d . . . . .
N1 N 0.2821(2) 0.8056(2) 0.72941(11) 0.0381(3) Uani 1 1 d . . . . .
O2 O -0.0412(2) 0.96108(19) 0.87701(11) 0.0602(4) Uani 1 1 d . . . . .
N2 N 0.3964(3) 0.8755(2) 0.76205(12) 0.0497(4) Uani 1 1 d . . . . .
C2 C 0.2991(3) 0.4117(3) 0.84747(15) 0.0488(4) Uani 1 1 d . . . . .
H2 H 0.305547 0.390916 0.777930 0.059 Uiso 1 1 calc R . . . .
C3 C 0.3967(4) 0.2603(3) 0.90771(18) 0.0613(6) Uani 1 1 d . . . . .
H3 H 0.471214 0.135713 0.878518 0.074 Uiso 1 1 calc R . . . .
O3 O 0.6448(3) 0.6548(2) 0.41672(11) 0.0654(4) Uani 1 1 d . . . . .
C4 C 0.3847(4) 0.2920(3) 1.01054(18) 0.0596(5) Uani 1 1 d . . . . .
H4 H 0.451733 0.189118 1.050589 0.071 Uiso 1 1 calc R . . . .
O4 O 0.8402(2) 0.75912(19) 0.47096(10) 0.0487(3) Uani 1 1 d . . . . .
C5 C 0.2752(4) 0.4734(3) 1.05414(15) 0.0576(5) Uani 1 1 d . . . . .
H5 H 0.265982 0.492791 1.124335 0.069 Uiso 1 1 calc R . . . .
C6 C 0.1775(3) 0.6291(3) 0.99598(14) 0.0465(4) Uani 1 1 d . . . . .
H6 H 0.104388 0.753342 1.025604 0.056 Uiso 1 1 calc R . . . .
C7 C 0.5506(3) 0.8549(3) 0.67825(14) 0.0469(4) Uani 1 1 d . . . . .
H7 H 0.655429 0.891081 0.676215 0.056 Uiso 1 1 calc R . . . .
C8 C 0.5390(3) 0.7713(2) 0.59149(13) 0.0375(4) Uani 1 1 d . . . . .
C9 C 0.3659(3) 0.7405(2) 0.62783(13) 0.0398(4) Uani 1 1 d . . . . .
H9 H 0.314856 0.685273 0.590151 0.048 Uiso 1 1 calc R . . . .
C10 C 0.6768(3) 0.7219(2) 0.48417(14) 0.0421(4) Uani 1 1 d . . . . .
C11 C 0.9853(3) 0.7138(3) 0.36649(15) 0.0536(5) Uani 1 1 d . . . . .
H11A H 0.912556 0.784580 0.313501 0.064 Uiso 1 1 calc R . . . .
H11B H 1.046041 0.576990 0.350158 0.064 Uiso 1 1 calc R . . . .
C12 C 1.1521(4) 0.7699(4) 0.3669(2) 0.0707(7) Uani 1 1 d . . . . .
H12A H 1.247440 0.746848 0.297707 0.106 Uiso 1 1 calc GR . . . .
H12B H 1.227211 0.694684 0.417276 0.106 Uiso 1 1 calc GR . . . .
H12C H 1.089621 0.904275 0.386051 0.106 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 C1 1.7405(17) . ?
S1 O1 1.4170(13) . ?
S1 N1 1.6967(15) . ?
S1 O2 1.4123(14) . ?
C1 C2 1.382(2) . ?
C1 C6 1.376(2) . ?
N1 N2 1.363(2) . ?
N1 C9 1.350(2) . ?
N2 C7 1.310(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(3) . ?
O3 C10 1.199(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.359(3) . ?
O4 C10 1.328(2) . ?
O4 C11 1.450(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.410(2) . ?
C8 C9 1.356(2) . ?
C8 C10 1.462(2) . ?
C9 H9 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.483(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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 C1 110.53(8) . . ?
O1 S1 N1 103.13(8) . . ?
N1 S1 C1 102.88(7) . . ?
O2 S1 C1 110.55(9) . . ?
O2 S1 O1 121.21(9) . . ?
O2 S1 N1 106.56(8) . . ?
C2 C1 S1 118.48(13) . . ?
C6 C1 S1 119.70(14) . . ?
C6 C1 C2 121.81(17) . . ?
N2 N1 S1 120.76(12) . . ?
C9 N1 S1 126.53(12) . . ?
C9 N1 N2 112.45(14) . . ?
C7 N2 N1 103.96(14) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.40(17) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.26(19) . . ?
C5 C4 H4 119.9 . . ?
C10 O4 C11 115.68(14) . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.08(18) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.05(18) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
N2 C7 H7 124.0 . . ?
N2 C7 C8 112.09(16) . . ?
C8 C7 H7 124.0 . . ?
C7 C8 C10 130.52(16) . . ?
C9 C8 C7 104.98(15) . . ?
C9 C8 C10 124.50(15) . . ?
N1 C9 C8 106.51(15) . . ?
N1 C9 H9 126.7 . . ?
C8 C9 H9 126.7 . . ?
O3 C10 O4 124.46(17) . . ?
O3 C10 C8 123.39(17) . . ?
O4 C10 C8 112.14(15) . . ?
O4 C11 H11A 110.2 . . ?
O4 C11 H11B 110.2 . . ?
O4 C11 C12 107.50(18) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.2 . . ?
C12 C11 H11B 110.2 . . ?
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 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
