# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_dd20109_0m
_database_code_depnum_ccdc_archive 'CCDC 2016445'
loop_
_audit_author_name
_audit_author_address
'rui Liu'
;shanghai normal university
China
;
_audit_update_record             
;
2020-07-15 deposited with the CCDC.	2021-11-05 downloaded from the CCDC.
;
_audit_creation_date             2020-07-15
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
; 
 ? 
;
_chemical_formula_moiety         'C17 H18 Br N O4 S'
_chemical_formula_sum            'C17 H18 Br N O4 S'
_chemical_formula_weight         412.29
_chemical_absolute_configuration ad
_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'
Br Br -0.2901 2.4595 '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           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                   12.101(3)
_cell_length_b                   5.7244(15)
_cell_length_c                   14.736(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.005(7)
_cell_angle_gamma                90
_cell_volume                     976.1(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2930
_cell_measurement_temperature    293
_cell_measurement_theta_max      53.912
_cell_measurement_theta_min      5.167
_shelx_estimated_absorpt_T_max   0.897
_shelx_estimated_absorpt_T_min   0.703
_exptl_absorpt_coefficient_mu    2.231
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_special_details           
; 
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.1101
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11811
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.565
_diffrn_reflns_theta_min         2.584
_diffrn_ambient_temperature      293.44
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2192
_reflns_number_total             4493
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _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       'Bruker APEX2'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
; 
 Flack x determined using 709 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.038(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.811
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4493
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      0.811
_refine_ls_shift/su_max          0.078
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1696
_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, All O(H) groups 
2.a Ternary CH refined with riding coordinates: 
 C4(H4) 
2.b Secondary CH2 refined with riding coordinates: 
 C2(H2A,H2B), C3(H3A,H3B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C16(H16), 
 C17(H17) 
2.d Tetrahedral OH refined with riding coordinates: 
 O2(H2) 
2.e Idealised Me refined as rotating group: 
 C11(H11A,H11B,H11C) 
;
_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 0.70229(10) 0.9647(2) 0.73860(8) 0.0932(5) Uani 1 1 d . . . . .
S1 S 0.77048(19) 0.1997(4) 0.44267(15) 0.0509(5) Uani 1 1 d . . . . .
O1 O 0.7307(5) 0.6682(10) 0.1957(4) 0.0543(15) Uani 1 1 d . . . . .
O2 O 0.8751(5) 0.3854(12) 0.2014(4) 0.077(2) Uani 1 1 d . . . . .
H2 H 0.8830 0.2721 0.2368 0.116 Uiso 1 1 calc R . . . .
O3 O 0.8875(5) 0.1130(11) 0.4732(4) 0.0620(16) Uani 1 1 d . . . . .
O4 O 0.6739(5) 0.0407(9) 0.4219(4) 0.0618(16) Uani 1 1 d . . . . .
N1 N 0.7583(6) 0.3508(11) 0.3462(5) 0.0450(16) Uani 1 1 d . . . . .
C1 C 0.8459(8) 0.5879(17) 0.2479(7) 0.060(2) Uani 1 1 d . . . . .
C2 C 0.8469(7) 0.5234(15) 0.3489(5) 0.052(2) Uani 1 1 d . . . . .
H2A H 0.9220 0.4612 0.3833 0.063 Uiso 1 1 calc R . . . .
H2B H 0.8330 0.6620 0.3819 0.063 Uiso 1 1 calc R . . . .
C3 C 0.6432(6) 0.4471(16) 0.2954(5) 0.0477(19) Uani 1 1 d . . . . .
H3A H 0.6280 0.5853 0.3279 0.057 Uiso 1 1 calc R . . . .
H3B H 0.5838 0.3325 0.2942 0.057 Uiso 1 1 calc R . . . .
C4 C 0.6408(7) 0.5090(14) 0.1955(5) 0.048(2) Uani 1 1 d . . . . .
H4 H 0.6525 0.3659 0.1629 0.058 Uiso 1 1 calc R . . . .
C5 C 0.5279(7) 0.6151(13) 0.1411(5) 0.046(2) Uani 1 1 d . . . . .
C6 C 0.4926(8) 0.8243(15) 0.1681(6) 0.057(2) Uani 1 1 d . . . . .
H6 H 0.5407 0.9051 0.2193 0.068 Uiso 1 1 calc R . . . .
C7 C 0.3863(9) 0.9163(16) 0.1199(8) 0.072(3) Uani 1 1 d . . . . .
H7 H 0.3638 1.0588 0.1392 0.086 Uiso 1 1 calc R . . . .
C8 C 0.3131(9) 0.802(2) 0.0444(9) 0.077(3) Uani 1 1 d . . . . .
H8 H 0.2416 0.8656 0.0123 0.093 Uiso 1 1 calc R . . . .
C9 C 0.3476(8) 0.5912(18) 0.0172(6) 0.058(2) Uani 1 1 d . . . . .
H9 H 0.2988 0.5096 -0.0334 0.069 Uiso 1 1 calc R . . . .
C10 C 0.4556(6) 0.4996(16) 0.0651(5) 0.050(2) Uani 1 1 d . . . . .
H10 H 0.4789 0.3584 0.0454 0.060 Uiso 1 1 calc R . . . .
C11 C 0.9235(9) 0.787(2) 0.2443(9) 0.096(4) Uani 1 1 d . . . . .
H11A H 0.9142 0.8283 0.1794 0.143 Uiso 1 1 calc GR . . . .
H11B H 1.0022 0.7429 0.2743 0.143 Uiso 1 1 calc GR . . . .
H11C H 0.9040 0.9187 0.2770 0.143 Uiso 1 1 calc GR . . . .
C12 C 0.7534(7) 0.4034(13) 0.5284(5) 0.044(2) Uani 1 1 d . . . . .
C13 C 0.8446(7) 0.5404(15) 0.5749(6) 0.055(2) Uani 1 1 d . . . . .
H13 H 0.9163 0.5220 0.5644 0.065 Uiso 1 1 calc R . . . .
C14 C 0.8289(7) 0.7066(18) 0.6375(6) 0.057(2) Uani 1 1 d . . . . .
H14 H 0.8904 0.8019 0.6690 0.068 Uiso 1 1 calc R . . . .
C15 C 0.7224(9) 0.7346(17) 0.6547(6) 0.057(2) Uani 1 1 d . . . . .
C16 C 0.6324(8) 0.592(2) 0.6083(7) 0.068(3) Uani 1 1 d . . . . .
H16 H 0.5611 0.6070 0.6197 0.082 Uiso 1 1 calc R . . . .
C17 C 0.6467(7) 0.427(2) 0.5455(6) 0.063(3) Uani 1 1 d . . . . .
H17 H 0.5853 0.3313 0.5142 0.075 Uiso 1 1 calc R . . . .


_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 C15 1.871(9) . ?
S1 O3 1.443(6) . ?
S1 O4 1.442(6) . ?
S1 N1 1.634(7) . ?
S1 C12 1.775(8) . ?
O1 C1 1.456(11) . ?
O1 C4 1.418(9) . ?
O2 H2 0.8200 . ?
O2 C1 1.442(11) . ?
N1 C2 1.450(10) . ?
N1 C3 1.481(10) . ?
C1 C2 1.530(12) . ?
C1 C11 1.488(14) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.506(10) . ?
C4 H4 0.9800 . ?
C4 C5 1.496(11) . ?
C5 C6 1.369(11) . ?
C5 C10 1.372(11) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(13) . ?
C7 H7 0.9300 . ?
C7 C8 1.368(15) . ?
C8 H8 0.9300 . ?
C8 C9 1.375(14) . ?
C9 H9 0.9300 . ?
C9 C10 1.393(11) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.364(10) . ?
C12 C17 1.393(11) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(12) . ?
C14 H14 0.9300 . ?
C14 C15 1.393(12) . ?
C15 C16 1.374(13) . ?
C16 H16 0.9300 . ?
C16 C17 1.366(13) . ?
C17 H17 0.9300 . ?

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 106.5(4) . . ?
O3 S1 C12 108.1(4) . . ?
O4 S1 O3 120.7(4) . . ?
O4 S1 N1 106.8(3) . . ?
O4 S1 C12 108.0(4) . . ?
N1 S1 C12 105.8(3) . . ?
C4 O1 C1 114.4(6) . . ?
C1 O2 H2 109.5 . . ?
C2 N1 S1 117.3(5) . . ?
C2 N1 C3 109.8(6) . . ?
C3 N1 S1 118.0(5) . . ?
O1 C1 C2 108.9(7) . . ?
O1 C1 C11 104.8(8) . . ?
O2 C1 O1 109.4(7) . . ?
O2 C1 C2 109.6(7) . . ?
O2 C1 C11 110.7(8) . . ?
C11 C1 C2 113.2(9) . . ?
N1 C2 C1 110.0(7) . . ?
N1 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N1 C3 H3A 109.8 . . ?
N1 C3 H3B 109.8 . . ?
N1 C3 C4 109.2(6) . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
O1 C4 C3 110.7(6) . . ?
O1 C4 H4 108.5 . . ?
O1 C4 C5 108.7(6) . . ?
C3 C4 H4 108.5 . . ?
C5 C4 C3 111.9(6) . . ?
C5 C4 H4 108.5 . . ?
C6 C5 C4 120.9(8) . . ?
C6 C5 C10 118.7(8) . . ?
C10 C5 C4 120.4(7) . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.5(9) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.3(9) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 120.8 . . ?
C7 C8 C9 118.5(10) . . ?
C9 C8 H8 120.7 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.2(10) . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 120.8(8) . . ?
C5 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 S1 119.3(6) . . ?
C13 C12 C17 120.7(8) . . ?
C17 C12 S1 120.0(7) . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 118.9(8) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.1(9) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 Br1 120.4(7) . . ?
C16 C15 Br1 120.7(7) . . ?
C16 C15 C14 118.9(9) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(9) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 H17 120.1 . . ?
C16 C17 C12 119.8(9) . . ?
C16 C17 H17 120.1 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.447 0.000 144.2 36.8 ?

_olex2_submission_special_instructions 'No special instructions were received'
