# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_cxy0280
_audit_block_doi                 10.5517/ccdc.csd.cc22jzcz
_database_code_depnum_ccdc_archive 'CCDC 1922941'
loop_
_audit_author_name
_audit_author_address
'Zhiyuan Chen'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2019-06-14 deposited with the CCDC.	2019-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 N O3 S'
_chemical_formula_weight         379.46

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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                   19.5977(12)
_cell_length_b                   8.1238(4)
_cell_length_c                   23.2996(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.182(5)
_cell_angle_gamma                90
_cell_volume                     3709.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4603
_cell_measurement_theta_min      4.1470
_cell_measurement_theta_max      28.6690

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.197
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76479
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   sadabs
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9887
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.498
_diffrn_reflns_theta_max         25.593
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             3319
_reflns_number_gt                2988
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+5.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3319
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.20851(10) 0.8006(2) 0.13778(8) 0.0361(5) Uani 1 1 d . . . . .
C2 C 0.15492(10) 0.8036(2) 0.09735(8) 0.0356(4) Uani 1 1 d . . . . .
C3 C 0.16733(10) 0.8791(3) 0.04480(8) 0.0385(5) Uani 1 1 d . . . . .
H3A H 0.1323 0.8836 0.0178 0.046 Uiso 1 1 calc R U . . .
C4 C 0.23015(10) 0.9479(3) 0.03121(8) 0.0381(5) Uani 1 1 d . . . . .
C5 C 0.28269(11) 0.9402(3) 0.07111(9) 0.0454(5) Uani 1 1 d . . . . .
H5A H 0.3253 0.9838 0.0624 0.054 Uiso 1 1 calc R U . . .
C6 C 0.27156(11) 0.8680(3) 0.12361(9) 0.0447(5) Uani 1 1 d . . . . .
H6A H 0.3070 0.8640 0.1503 0.054 Uiso 1 1 calc R U . . .
C7 C 0.23882(11) 1.0265(3) -0.02579(9) 0.0429(5) Uani 1 1 d . . . . .
C8 C 0.31676(14) 1.1655(3) -0.08583(11) 0.0591(7) Uani 1 1 d . . . . .
H8A H 0.3630 1.2043 -0.0856 0.089 Uiso 1 1 calc R U . . .
H8B H 0.3108 1.0875 -0.1164 0.089 Uiso 1 1 calc R U . . .
H8C H 0.2863 1.2567 -0.0915 0.089 Uiso 1 1 calc R U . . .
C9 C 0.04337(12) 0.6800(3) 0.05685(9) 0.0529(6) Uani 1 1 d . . . . .
H9A H 0.0675 0.6560 0.0210 0.064 Uiso 1 1 calc R U . . .
C10 C 0.08930(11) 0.7125(3) 0.11035(9) 0.0394(5) Uani 1 1 d . . . . .
H10A H 0.1018 0.6052 0.1265 0.047 Uiso 1 1 calc R U . . .
C11 C 0.03689(10) 0.7971(3) 0.15357(8) 0.0365(5) Uani 1 1 d . . . . .
H11A H 0.0290 0.7202 0.1852 0.044 Uiso 1 1 calc R U . . .
C12 C -0.02976(11) 0.8039(3) 0.11662(10) 0.0505(6) Uani 1 1 d . . . . .
H12A H -0.0649 0.8810 0.1297 0.061 Uiso 1 1 calc R U . . .
C13 C -0.05147(13) 0.6266(4) 0.11091(10) 0.0609(7) Uani 1 1 d . . . . .
H13A H -0.0884 0.5777 0.1291 0.073 Uiso 1 1 calc R U . . .
C14 C -0.00873(14) 0.5531(4) 0.07549(10) 0.0625(7) Uani 1 1 d . . . . .
H14A H -0.0103 0.4435 0.0641 0.075 Uiso 1 1 calc R U . . .
C15 C -0.00145(12) 0.8344(4) 0.05638(10) 0.0586(7) Uani 1 1 d . . . . .
H15A H -0.0364 0.8315 0.0268 0.070 Uiso 1 1 calc R U . . .
H15B H 0.0248 0.9353 0.0537 0.070 Uiso 1 1 calc R U . . .
C16 C 0.06086(10) 0.9580(2) 0.17918(8) 0.0349(4) Uani 1 1 d . . . . .
C17 C 0.11344(10) 0.9624(2) 0.22030(8) 0.0328(4) Uani 1 1 d . . . . .
C18 C 0.13527(11) 1.1083(3) 0.24528(10) 0.0431(5) Uani 1 1 d . . . . .
H18A H 0.1707 1.1073 0.2719 0.052 Uiso 1 1 calc R U . . .
C19 C 0.10441(13) 1.2547(3) 0.23061(11) 0.0524(6) Uani 1 1 d . . . . .
H19A H 0.1185 1.3528 0.2475 0.063 Uiso 1 1 calc R U . . .
C20 C 0.05296(13) 1.2544(3) 0.19108(11) 0.0539(6) Uani 1 1 d . . . . .
H20A H 0.0320 1.3531 0.1811 0.065 Uiso 1 1 calc R U . . .
C21 C 0.03138(11) 1.1092(3) 0.16550(10) 0.0463(5) Uani 1 1 d . . . . .
H21A H -0.0037 1.1128 0.1385 0.056 Uiso 1 1 calc R U . . .
C22 C 0.20813(12) 0.8202(3) 0.29886(9) 0.0484(5) Uani 1 1 d . . . . .
H22A H 0.2417 0.9003 0.2881 0.073 Uiso 1 1 calc R U . . .
H22B H 0.1808 0.8632 0.3295 0.073 Uiso 1 1 calc R U . . .
H22C H 0.2305 0.7214 0.3115 0.073 Uiso 1 1 calc R U . . .
N1 N 0.20259(10) 0.7203(2) 0.19122(7) 0.0451(5) Uani 1 1 d . . . . .
O1 O 0.19573(9) 1.0359(3) -0.06235(7) 0.0631(5) Uani 1 1 d . . . . .
O2 O 0.30192(8) 1.0874(2) -0.03196(7) 0.0543(4) Uani 1 1 d . . . . .
O3 O 0.10711(8) 0.65490(18) 0.25965(6) 0.0475(4) Uani 1 1 d . . . . .
S1 S 0.15542(3) 0.77528(6) 0.23918(2) 0.03342(16) Uani 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
C1 C6 1.392(3) . ?
C1 C2 1.409(3) . ?
C1 N1 1.410(3) . ?
C2 C3 1.391(3) . ?
C2 C10 1.515(3) . ?
C3 C4 1.389(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.386(3) . ?
C4 C7 1.484(3) . ?
C5 C6 1.375(3) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 O1 1.200(3) . ?
C7 O2 1.340(3) . ?
C8 O2 1.437(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.516(3) . ?
C9 C15 1.531(4) . ?
C9 C10 1.558(3) . ?
C9 H9A 0.9800 . ?
C10 C11 1.596(3) . ?
C10 H10A 0.9800 . ?
C11 C16 1.511(3) . ?
C11 C12 1.563(3) . ?
C11 H11A 0.9800 . ?
C12 C13 1.508(4) . ?
C12 C15 1.531(3) . ?
C12 H12A 0.9800 . ?
C13 C14 1.321(4) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C21 1.394(3) . ?
C16 C17 1.405(3) . ?
C17 C18 1.388(3) . ?
C17 S1 1.7827(19) . ?
C18 C19 1.377(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.364(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.387(3) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C22 S1 1.768(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 S1 1.5194(18) . ?
O3 S1 1.4434(15) . ?

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
C6 C1 C2 119.65(18) . . ?
C6 C1 N1 117.82(19) . . ?
C2 C1 N1 122.36(19) . . ?
C3 C2 C1 117.65(18) . . ?
C3 C2 C10 122.83(18) . . ?
C1 C2 C10 119.27(18) . . ?
C4 C3 C2 122.36(19) . . ?
C4 C3 H3A 118.8 . . ?
C2 C3 H3A 118.8 . . ?
C5 C4 C3 119.07(19) . . ?
C5 C4 C7 122.17(19) . . ?
C3 C4 C7 118.76(19) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C5 C6 C1 121.5(2) . . ?
C5 C6 H6A 119.3 . . ?
C1 C6 H6A 119.3 . . ?
O1 C7 O2 123.2(2) . . ?
O1 C7 C4 125.5(2) . . ?
O2 C7 C4 111.30(19) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C15 99.9(2) . . ?
C14 C9 C10 105.89(18) . . ?
C15 C9 C10 101.37(19) . . ?
C14 C9 H9A 115.8 . . ?
C15 C9 H9A 115.8 . . ?
C10 C9 H9A 115.8 . . ?
C2 C10 C9 114.29(17) . . ?
C2 C10 C11 117.62(16) . . ?
C9 C10 C11 101.91(17) . . ?
C2 C10 H10A 107.5 . . ?
C9 C10 H10A 107.5 . . ?
C11 C10 H10A 107.5 . . ?
C16 C11 C12 116.42(18) . . ?
C16 C11 C10 114.96(16) . . ?
C12 C11 C10 101.90(16) . . ?
C16 C11 H11A 107.7 . . ?
C12 C11 H11A 107.7 . . ?
C10 C11 H11A 107.7 . . ?
C13 C12 C15 100.1(2) . . ?
C13 C12 C11 104.5(2) . . ?
C15 C12 C11 101.89(17) . . ?
C13 C12 H12A 116.0 . . ?
C15 C12 H12A 116.0 . . ?
C11 C12 H12A 116.0 . . ?
C14 C13 C12 107.9(2) . . ?
C14 C13 H13A 126.0 . . ?
C12 C13 H13A 126.0 . . ?
C13 C14 C9 107.5(2) . . ?
C13 C14 H14A 126.3 . . ?
C9 C14 H14A 126.3 . . ?
C9 C15 C12 94.06(19) . . ?
C9 C15 H15A 112.9 . . ?
C12 C15 H15A 112.9 . . ?
C9 C15 H15B 112.9 . . ?
C12 C15 H15B 112.9 . . ?
H15A C15 H15B 110.3 . . ?
C21 C16 C17 115.87(19) . . ?
C21 C16 C11 122.95(19) . . ?
C17 C16 C11 121.14(17) . . ?
C18 C17 C16 122.11(18) . . ?
C18 C17 S1 118.92(16) . . ?
C16 C17 S1 118.93(14) . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18A 120.0 . . ?
C17 C18 H18A 120.0 . . ?
C20 C19 C18 119.3(2) . . ?
C20 C19 H19A 120.4 . . ?
C18 C19 H19A 120.4 . . ?
C19 C20 C21 121.0(2) . . ?
C19 C20 H20A 119.5 . . ?
C21 C20 H20A 119.5 . . ?
C20 C21 C16 121.7(2) . . ?
C20 C21 H21A 119.2 . . ?
C16 C21 H21A 119.1 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 N1 S1 124.43(14) . . ?
C7 O2 C8 116.48(19) . . ?
O3 S1 N1 116.44(10) . . ?
O3 S1 C22 105.20(10) . . ?
N1 S1 C22 106.49(11) . . ?
O3 S1 C17 110.88(9) . . ?
N1 S1 C17 110.51(9) . . ?
C22 S1 C17 106.64(10) . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.038



####################################################################### 
# 
# 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_CXY20181116c
_database_code_depnum_ccdc_archive 'CCDC 1937567'
loop_
_audit_author_name
_audit_author_address
'Zhiyuan Chen'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 Br3 Cl2 N O3 S'
_chemical_formula_weight         703.10

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1990(7)
_cell_length_b                   11.3055(13)
_cell_length_c                   14.2419(11)
_cell_angle_alpha                100.441(8)
_cell_angle_beta                 100.282(7)
_cell_angle_gamma                91.136(8)
_cell_volume                     1275.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2797
_cell_measurement_theta_min      3.6890
_cell_measurement_theta_max      28.8410

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_F_000             692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    5.062
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.02602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6186
_diffrn_reflns_av_unetI/netI     0.1999
_diffrn_reflns_av_R_equivalents  0.0997
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.330
_diffrn_reflns_theta_max         25.098
_diffrn_reflns_theta_full        25.098
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             4471
_reflns_number_gt                2341
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+20.7579P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0047(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4471
_refine_ls_number_parameters     299
_refine_ls_number_restraints     307
_refine_ls_R_factor_all          0.2451
_refine_ls_R_factor_gt           0.1666
_refine_ls_wR_factor_ref         0.3351
_refine_ls_wR_factor_gt          0.2851
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.6387(16) 0.5129(14) 0.6370(10) 0.034(3) Uani 1 1 d . U . . .
C2 C 0.6788(16) 0.6327(13) 0.6539(10) 0.031(3) Uani 1 1 d . U . . .
C3 C 0.5568(18) 0.7198(15) 0.6615(12) 0.043(4) Uani 1 1 d . U . . .
H3A H 0.5870 0.8015 0.6712 0.051 Uiso 1 1 calc R U . . .
C4 C 0.3954(19) 0.6827(17) 0.6543(12) 0.049(4) Uani 1 1 d . U . . .
H4A H 0.3152 0.7385 0.6635 0.059 Uiso 1 1 calc R U . . .
C5 C 0.3534(18) 0.5638(18) 0.6337(12) 0.050(4) Uani 1 1 d . U . . .
H5A H 0.2420 0.5383 0.6230 0.060 Uiso 1 1 calc R U . . .
C6 C 0.4711(17) 0.4788(16) 0.6282(11) 0.041(3) Uani 1 1 d . U . . .
H6A H 0.4386 0.3975 0.6184 0.049 Uiso 1 1 calc R U . . .
C7 C 0.8596(17) 0.4922(14) 0.8161(11) 0.036(3) Uani 1 1 d . U . . .
C8 C 0.9111(18) 0.6134(15) 0.8323(12) 0.041(3) Uani 1 1 d . U . . .
C9 C 0.903(2) 0.6906(15) 0.9192(13) 0.050(3) Uani 1 1 d . U . . .
C10 C 0.834(2) 0.6427(17) 0.9900(12) 0.050(3) Uani 1 1 d . U . . .
H10A H 0.8268 0.6931 1.0484 0.060 Uiso 1 1 calc R U . . .
C11 C 0.7772(19) 0.5265(17) 0.9750(12) 0.047(3) Uani 1 1 d . U . . .
C12 C 0.7925(18) 0.4520(15) 0.8882(10) 0.038(3) Uani 1 1 d . U . . .
H12A H 0.7562 0.3714 0.8781 0.046 Uiso 1 1 calc R U . . .
C13 C 0.706(2) 0.486(2) 1.0532(13) 0.058(4) Uani 1 1 d . U . . .
C14 C 0.604(3) 0.318(2) 1.1066(15) 0.091(8) Uani 1 1 d . U . . .
H14A H 0.5753 0.2338 1.0840 0.136 Uiso 1 1 calc R U . . .
H14B H 0.6909 0.3288 1.1630 0.136 Uiso 1 1 calc R U . . .
H14C H 0.5085 0.3586 1.1232 0.136 Uiso 1 1 calc R U . . .
C15 C 0.6995(18) 0.2847(15) 0.5902(11) 0.039(3) Uani 1 1 d . U . . .
H15A H 0.5942 0.2759 0.5438 0.047 Uiso 1 1 calc R U . . .
C16 C 0.7698(17) 0.4176(13) 0.6282(10) 0.033(3) Uani 1 1 d . U . . .
H16A H 0.8383 0.4379 0.5830 0.040 Uiso 1 1 calc R U . . .
C17 C 0.8899(17) 0.4089(13) 0.7267(10) 0.032(3) Uani 1 1 d . U . . .
H17A H 1.0033 0.4275 0.7186 0.039 Uiso 1 1 calc R U . . .
C18 C 0.8753(19) 0.2747(15) 0.7292(11) 0.041(3) Uani 1 1 d . U . . .
H18A H 0.9088 0.2549 0.7939 0.050 Uiso 1 1 calc R U . . .
C19 C 0.9521(18) 0.1965(14) 0.6481(11) 0.039(3) Uani 1 1 d . U . . .
H19A H 0.9440 0.1117 0.6539 0.047 Uiso 1 1 calc R U . . .
C20 C 0.8379(19) 0.2150(14) 0.5532(11) 0.041(3) Uani 1 1 d . U . . .
H20A H 0.8972 0.2623 0.5174 0.050 Uiso 1 1 calc R U . . .
C21 C 0.6899(19) 0.2451(14) 0.6843(11) 0.041(3) Uani 1 1 d . U . . .
H21A H 0.6588 0.1600 0.6754 0.049 Uiso 1 1 calc R U . . .
H21B H 0.6168 0.2926 0.7208 0.049 Uiso 1 1 calc R U . . .
C22 C 0.894(2) 0.8390(15) 0.6744(15) 0.060(5) Uani 1 1 d . U . . .
H22A H 0.8501 0.8761 0.7300 0.089 Uiso 1 1 calc R U . . .
H22B H 1.0066 0.8694 0.6805 0.089 Uiso 1 1 calc R U . . .
H22C H 0.8283 0.8573 0.6165 0.089 Uiso 1 1 calc R U . . .
C23 C 0.437(3) 0.108(3) 0.839(3) 0.163(12) Uani 1 1 d . U . . .
H23A H 0.4424 0.1835 0.8844 0.195 Uiso 1 1 calc R U . . .
H23B H 0.4227 0.1268 0.7742 0.195 Uiso 1 1 calc R U . . .
N1 N 0.9851(15) 0.6562(12) 0.7625(10) 0.045(3) Uani 1 1 d . U . . .
O1 O 0.692(2) 0.5469(17) 1.1268(10) 0.096(5) Uani 1 1 d . U . . .
O2 O 0.6618(16) 0.3685(14) 1.0303(9) 0.067(3) Uani 1 1 d . U . . .
O3 O 0.9593(13) 0.6368(10) 0.5822(9) 0.051(3) Uani 1 1 d . U . . .
S1 S 0.8907(5) 0.6828(4) 0.6675(3) 0.0415(10) Uani 1 1 d . U . . .
Br1 Br 0.9814(3) 0.84883(19) 0.94366(19) 0.0844(9) Uani 1 1 d . U . . .
Br2 Br 1.1846(2) 0.24506(17) 0.65064(16) 0.0610(7) Uani 1 1 d . U . . .
Br3 Br 0.7581(3) 0.05954(16) 0.47355(14) 0.0618(7) Uani 1 1 d . U . . .
Cl1 Cl 0.6223(11) 0.0430(11) 0.8615(7) 0.164(4) Uani 1 1 d . U . . .
Cl2 Cl 0.2699(12) 0.0282(11) 0.8457(9) 0.179(5) Uani 1 1 d . U . . .


_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
C1 C2 1.36(2) . ?
C1 C6 1.397(19) . ?
C1 C16 1.54(2) . ?
C2 C3 1.42(2) . ?
C2 S1 1.782(14) . ?
C3 C4 1.36(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.35(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.38(2) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C12 1.39(2) . ?
C7 C8 1.39(2) . ?
C7 C17 1.50(2) . ?
C8 C9 1.39(2) . ?
C8 N1 1.40(2) . ?
C9 C10 1.42(2) . ?
C9 Br1 1.838(18) . ?
C10 C11 1.35(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.39(2) . ?
C11 C13 1.48(2) . ?
C12 H12A 0.9300 . ?
C13 O1 1.17(2) . ?
C13 O2 1.33(2) . ?
C14 O2 1.46(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C21 1.50(2) . ?
C15 C20 1.51(2) . ?
C15 C16 1.56(2) . ?
C15 H15A 0.9800 . ?
C16 C17 1.584(19) . ?
C16 H16A 0.9800 . ?
C17 C18 1.53(2) . ?
C17 H17A 0.9800 . ?
C18 C21 1.54(2) . ?
C18 C19 1.56(2) . ?
C18 H18A 0.9800 . ?
C19 C20 1.55(2) . ?
C19 Br2 1.965(15) . ?
C19 H19A 0.9800 . ?
C20 Br3 1.942(16) . ?
C20 H20A 0.9800 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 S1 1.751(17) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 Cl2 1.65(3) . ?
C23 Cl1 1.71(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
N1 S1 1.517(14) . ?
O3 S1 1.447(11) . ?

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
C2 C1 C6 116.7(14) . . ?
C2 C1 C16 122.4(12) . . ?
C6 C1 C16 120.9(14) . . ?
C1 C2 C3 121.9(13) . . ?
C1 C2 S1 119.1(11) . . ?
C3 C2 S1 118.9(12) . . ?
C4 C3 C2 119.4(15) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C5 C4 C3 119.0(15) . . ?
C5 C4 H4A 120.5 . . ?
C3 C4 H4A 120.5 . . ?
C4 C5 C6 121.8(15) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C5 C6 C1 121.0(16) . . ?
C5 C6 H6A 119.5 . . ?
C1 C6 H6A 119.5 . . ?
C12 C7 C8 117.5(15) . . ?
C12 C7 C17 122.6(15) . . ?
C8 C7 C17 119.7(14) . . ?
C7 C8 C9 121.6(16) . . ?
C7 C8 N1 119.0(15) . . ?
C9 C8 N1 119.2(16) . . ?
C8 C9 C10 117.7(17) . . ?
C8 C9 Br1 121.8(14) . . ?
C10 C9 Br1 120.5(13) . . ?
C11 C10 C9 122.1(16) . . ?
C11 C10 H10A 119.0 . . ?
C9 C10 H10A 119.0 . . ?
C10 C11 C12 118.0(16) . . ?
C10 C11 C13 117.8(17) . . ?
C12 C11 C13 124.2(18) . . ?
C7 C12 C11 123.1(17) . . ?
C7 C12 H12A 118.5 . . ?
C11 C12 H12A 118.5 . . ?
O1 C13 O2 123.3(19) . . ?
O1 C13 C11 125(2) . . ?
O2 C13 C11 111.2(17) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C21 C15 C20 104.4(13) . . ?
C21 C15 C16 100.7(12) . . ?
C20 C15 C16 106.6(11) . . ?
C21 C15 H15A 114.6 . . ?
C20 C15 H15A 114.6 . . ?
C16 C15 H15A 114.6 . . ?
C1 C16 C15 115.5(11) . . ?
C1 C16 C17 115.1(12) . . ?
C15 C16 C17 102.6(11) . . ?
C1 C16 H16A 107.7 . . ?
C15 C16 H16A 107.7 . . ?
C17 C16 H16A 107.7 . . ?
C7 C17 C18 115.4(12) . . ?
C7 C17 C16 116.2(12) . . ?
C18 C17 C16 102.4(12) . . ?
C7 C17 H17A 107.4 . . ?
C18 C17 H17A 107.4 . . ?
C16 C17 H17A 107.4 . . ?
C17 C18 C21 100.8(12) . . ?
C17 C18 C19 112.2(12) . . ?
C21 C18 C19 98.6(12) . . ?
C17 C18 H18A 114.5 . . ?
C21 C18 H18A 114.5 . . ?
C19 C18 H18A 114.5 . . ?
C20 C19 C18 103.3(12) . . ?
C20 C19 Br2 111.6(10) . . ?
C18 C19 Br2 113.3(11) . . ?
C20 C19 H19A 109.5 . . ?
C18 C19 H19A 109.5 . . ?
Br2 C19 H19A 109.5 . . ?
C15 C20 C19 102.9(12) . . ?
C15 C20 Br3 112.2(11) . . ?
C19 C20 Br3 109.7(10) . . ?
C15 C20 H20A 110.6 . . ?
C19 C20 H20A 110.6 . . ?
Br3 C20 H20A 110.6 . . ?
C15 C21 C18 95.4(11) . . ?
C15 C21 H21A 112.7 . . ?
C18 C21 H21A 112.7 . . ?
C15 C21 H21B 112.7 . . ?
C18 C21 H21B 112.7 . . ?
H21A C21 H21B 110.1 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Cl2 C23 Cl1 117(2) . . ?
Cl2 C23 H23A 108.1 . . ?
Cl1 C23 H23A 108.1 . . ?
Cl2 C23 H23B 108.1 . . ?
Cl1 C23 H23B 108.1 . . ?
H23A C23 H23B 107.3 . . ?
C8 N1 S1 124.5(10) . . ?
C13 O2 C14 115.1(17) . . ?
O3 S1 N1 115.6(7) . . ?
O3 S1 C22 104.8(8) . . ?
N1 S1 C22 108.7(9) . . ?
O3 S1 C2 111.9(7) . . ?
N1 S1 C2 108.6(7) . . ?
C22 S1 C2 106.9(8) . . ?

_refine_diff_density_max         1.531
_refine_diff_density_min         -2.170
_refine_diff_density_rms         0.241



