# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_exp_1714
_database_code_depnum_ccdc_archive 'CCDC 2110859'
loop_
_audit_author_name
_audit_author_address
'yang wang '
;ocean univercity of china
China
;
_audit_update_record             
;
2021-09-20 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H39 Br N2 O4 S'
_chemical_formula_weight         687.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   11.0140(4)
_cell_length_b                   11.3559(5)
_cell_length_c                   14.3441(7)
_cell_angle_alpha                83.796(4)
_cell_angle_beta                 86.279(4)
_cell_angle_gamma                75.024(4)
_cell_volume                     1721.70(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    2.519
_shelx_estimated_absorpt_T_min   0.519
_shelx_estimated_absorpt_T_max   0.519
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10358
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.101
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             6079
_reflns_number_gt                5464
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0637P)²+0.7464P] 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         6079
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.33794(4) 0.45988(3) 1.06381(2) 0.08081(15) Uani 1 1 d . . . . .
S1 S 0.43368(5) 0.31102(5) 0.67654(4) 0.04673(15) Uani 1 1 d . . . . .
O1 O 1.15902(16) -0.0642(2) 0.7881(2) 0.0780(7) Uani 1 1 d . . . . .
H1 H 1.1884 -0.0092 0.8015 0.117 Uiso 1 1 calc R U . . .
O2 O 0.37867(16) 0.01148(19) 0.78408(15) 0.0625(5) Uani 1 1 d . . . . .
O3 O 0.41562(19) 0.23973(17) 0.60497(13) 0.0627(5) Uani 1 1 d . . . . .
O4 O 0.32952(17) 0.39638(17) 0.71554(13) 0.0591(4) Uani 1 1 d . . . . .
N1 N 0.5181(2) -0.0609(2) 0.66499(17) 0.0593(6) Uani 1 1 d . . . . .
N2 N 0.49932(18) 0.21276(17) 0.76264(13) 0.0431(4) Uani 1 1 d . . . . .
C1 C 0.4730(2) 0.0096(2) 0.73569(18) 0.0464(5) Uani 1 1 d . . . . .
C2 C 0.56780(19) 0.08472(19) 0.74825(15) 0.0390(4) Uani 1 1 d . . . . .
C3 C 0.6545(2) 0.0609(2) 0.66299(16) 0.0465(5) Uani 1 1 d . . . . .
C4 C 0.7551(2) 0.1058(3) 0.62938(18) 0.0585(6) Uani 1 1 d . . . . .
H4 H 0.7764 0.1669 0.6581 0.070 Uiso 1 1 calc R U . . .
C5 C 0.8246(3) 0.0574(4) 0.5509(2) 0.0843(11) Uani 1 1 d . . . . .
H5 H 0.8929 0.0868 0.5273 0.101 Uiso 1 1 calc R U . . .
C6 C 0.7940(4) -0.0318(5) 0.5089(3) 0.1008(15) Uani 1 1 d . . . . .
H6 H 0.8421 -0.0626 0.4571 0.121 Uiso 1 1 calc R U . . .
C7 C 0.6928(4) -0.0780(4) 0.5413(2) 0.0886(12) Uani 1 1 d . . . . .
H7 H 0.6715 -0.1386 0.5120 0.106 Uiso 1 1 calc R U . . .
C8 C 0.6246(2) -0.0302(3) 0.61936(19) 0.0568(6) Uani 1 1 d . . . . .
C9 C 0.4581(4) -0.1508(3) 0.6369(3) 0.0909(12) Uani 1 1 d . . . . .
H9A H 0.5151 -0.2307 0.6443 0.136 Uiso 1 1 calc R U . . .
H9B H 0.4362 -0.1309 0.5724 0.136 Uiso 1 1 calc R U . . .
H9C H 0.3834 -0.1501 0.6755 0.136 Uiso 1 1 calc R U . . .
C10 C 0.49223(19) 0.2323(2) 0.85922(15) 0.0387(4) Uani 1 1 d . . . . .
C11 C 0.4221(2) 0.3321(2) 0.90396(17) 0.0478(5) Uani 1 1 d . . . . .
H11 H 0.3699 0.3994 0.8712 0.057 Uiso 1 1 calc R U . . .
C12 C 0.4344(2) 0.3259(2) 0.99990(17) 0.0494(5) Uani 1 1 d . . . . .
C13 C 0.5112(2) 0.2281(3) 1.05026(17) 0.0538(6) Uani 1 1 d . . . . .
H13 H 0.5180 0.2284 1.1145 0.065 Uiso 1 1 calc R U . . .
C14 C 0.5782(2) 0.1296(2) 1.00402(16) 0.0496(5) Uani 1 1 d . . . . .
H14 H 0.6301 0.0624 1.0371 0.060 Uiso 1 1 calc R U . . .
C15 C 0.56768(18) 0.1311(2) 0.90847(15) 0.0397(4) Uani 1 1 d . . . . .
C16 C 0.63242(19) 0.03407(19) 0.84582(15) 0.0392(4) Uani 1 1 d . . . . .
H16 H 0.6095 -0.0421 0.8686 0.047 Uiso 1 1 calc R U . . .
C17 C 0.77426(18) 0.00855(19) 0.83944(15) 0.0380(4) Uani 1 1 d . . . . .
C18 C 0.83405(19) 0.10070(19) 0.84461(15) 0.0398(4) Uani 1 1 d . . . . .
H18 H 0.7864 0.1772 0.8594 0.048 Uiso 1 1 calc R U . . .
C19 C 0.9632(2) 0.0827(2) 0.82844(16) 0.0424(5) Uani 1 1 d . . . . .
C20 C 1.0320(2) -0.0352(2) 0.80805(18) 0.0472(5) Uani 1 1 d . . . . .
C21 C 0.9751(2) -0.1322(2) 0.80493(17) 0.0450(5) Uani 1 1 d . . . . .
C22 C 0.8454(2) -0.10649(19) 0.82094(15) 0.0409(4) Uani 1 1 d . . . . .
H22 H 0.8053 -0.1688 0.8191 0.049 Uiso 1 1 calc R U . . .
C23 C 1.0247(2) 0.1891(2) 0.8316(2) 0.0553(6) Uani 1 1 d . . . . .
C24 C 1.1211(3) 0.1590(3) 0.9093(3) 0.0797(10) Uani 1 1 d . . . . .
H24A H 1.0791 0.1480 0.9691 0.120 Uiso 1 1 calc R U . . .
H24B H 1.1607 0.2250 0.9092 0.120 Uiso 1 1 calc R U . . .
H24C H 1.1837 0.0850 0.8981 0.120 Uiso 1 1 calc R U . . .
C25 C 0.9274(3) 0.3066(3) 0.8540(3) 0.0782(10) Uani 1 1 d . . . . .
H25A H 0.8647 0.3282 0.8073 0.117 Uiso 1 1 calc R U . . .
H25B H 0.9682 0.3717 0.8541 0.117 Uiso 1 1 calc R U . . .
H25C H 0.8881 0.2937 0.9146 0.117 Uiso 1 1 calc R U . . .
C26 C 1.0859(3) 0.2179(3) 0.7354(3) 0.0804(9) Uani 1 1 d . . . . .
H26A H 1.1504 0.1474 0.7195 0.121 Uiso 1 1 calc R U . . .
H26B H 1.1224 0.2856 0.7379 0.121 Uiso 1 1 calc R U . . .
H26C H 1.0233 0.2385 0.6887 0.121 Uiso 1 1 calc R U . . .
C27 C 1.0515(3) -0.2609(2) 0.7824(2) 0.0620(7) Uani 1 1 d . . . . .
C28 C 1.1557(4) -0.3143(4) 0.8524(3) 0.1112(16) Uani 1 1 d . . . . .
H28A H 1.2122 -0.2621 0.8492 0.167 Uiso 1 1 calc R U . . .
H28B H 1.2012 -0.3945 0.8371 0.167 Uiso 1 1 calc R U . . .
H28C H 1.1189 -0.3198 0.9148 0.167 Uiso 1 1 calc R U . . .
C29 C 0.9687(4) -0.3497(3) 0.7868(4) 0.1132(17) Uani 1 1 d . . . . .
H29A H 0.9341 -0.3593 0.8495 0.170 Uiso 1 1 calc R U . . .
H29B H 1.0180 -0.4276 0.7694 0.170 Uiso 1 1 calc R U . . .
H29C H 0.9016 -0.3183 0.7442 0.170 Uiso 1 1 calc R U . . .
C30 C 1.1082(4) -0.2549(4) 0.6827(3) 0.0922(11) Uani 1 1 d . . . . .
H30A H 1.0423 -0.2208 0.6395 0.138 Uiso 1 1 calc R U . . .
H30B H 1.1516 -0.3359 0.6678 0.138 Uiso 1 1 calc R U . . .
H30C H 1.1663 -0.2042 0.6779 0.138 Uiso 1 1 calc R U . . .
C31 C 0.5483(2) 0.3885(2) 0.63508(16) 0.0496(5) Uani 1 1 d . . . . .
C32 C 0.5834(3) 0.4631(3) 0.6929(2) 0.0635(7) Uani 1 1 d . . . . .
H32 H 0.5448 0.4741 0.7520 0.076 Uiso 1 1 calc R U . . .
C33 C 0.6758(3) 0.5207(3) 0.6618(3) 0.0772(9) Uani 1 1 d . . . . .
H33 H 0.7007 0.5694 0.7011 0.093 Uiso 1 1 calc R U . . .
C34 C 0.7327(3) 0.5080(3) 0.5734(3) 0.0754(9) Uani 1 1 d . . . . .
C35 C 0.6949(3) 0.4346(3) 0.5169(2) 0.0805(10) Uani 1 1 d . . . . .
H35 H 0.7320 0.4253 0.4571 0.097 Uiso 1 1 calc R U . . .
C36 C 0.6033(3) 0.3744(3) 0.5467(2) 0.0677(8) Uani 1 1 d . . . . .
H36 H 0.5790 0.3251 0.5076 0.081 Uiso 1 1 calc R U . . .
C37 C 0.8338(4) 0.5717(5) 0.5397(4) 0.1220(18) Uani 1 1 d . . . . .
H37A H 0.9081 0.5359 0.5745 0.183 Uiso 1 1 calc R U . . .
H37B H 0.8050 0.6571 0.5489 0.183 Uiso 1 1 calc R U . . .
H37C H 0.8529 0.5628 0.4741 0.183 Uiso 1 1 calc R 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
Br1 C12 1.904(2) . ?
S1 O4 1.4240(19) . ?
S1 O3 1.4277(18) . ?
S1 N2 1.6414(19) . ?
S1 C31 1.756(3) . ?
O1 C20 1.371(3) . ?
O2 C1 1.208(3) . ?
N1 C1 1.349(3) . ?
N1 C8 1.411(4) . ?
N1 C9 1.453(4) . ?
N2 C10 1.420(3) . ?
N2 C2 1.484(3) . ?
C1 C2 1.539(3) . ?
C2 C3 1.506(3) . ?
C2 C16 1.594(3) . ?
C3 C4 1.375(4) . ?
C3 C8 1.383(4) . ?
C4 C5 1.400(4) . ?
C5 C6 1.355(6) . ?
C6 C7 1.384(6) . ?
C7 C8 1.387(4) . ?
C10 C15 1.384(3) . ?
C10 C11 1.391(3) . ?
C11 C12 1.384(3) . ?
C12 C13 1.375(4) . ?
C13 C14 1.381(4) . ?
C14 C15 1.381(3) . ?
C15 C16 1.502(3) . ?
C16 C17 1.512(3) . ?
C17 C22 1.382(3) . ?
C17 C18 1.383(3) . ?
C18 C19 1.391(3) . ?
C19 C20 1.408(3) . ?
C19 C23 1.537(3) . ?
C20 C21 1.407(3) . ?
C21 C22 1.391(3) . ?
C21 C27 1.542(3) . ?
C23 C25 1.530(4) . ?
C23 C26 1.536(4) . ?
C23 C24 1.540(4) . ?
C27 C29 1.520(5) . ?
C27 C30 1.525(5) . ?
C27 C28 1.534(5) . ?
C31 C36 1.376(4) . ?
C31 C32 1.385(4) . ?
C32 C33 1.373(4) . ?
C33 C34 1.383(5) . ?
C34 C35 1.376(5) . ?
C34 C37 1.506(5) . ?
C35 C36 1.380(5) . ?

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
O4 S1 O3 120.37(12) . . ?
O4 S1 N2 107.73(10) . . ?
O3 S1 N2 106.12(10) . . ?
O4 S1 C31 108.46(12) . . ?
O3 S1 C31 108.22(12) . . ?
N2 S1 C31 104.89(11) . . ?
C1 N1 C8 111.2(2) . . ?
C1 N1 C9 123.4(3) . . ?
C8 N1 C9 125.2(3) . . ?
C10 N2 C2 110.78(17) . . ?
C10 N2 S1 126.68(15) . . ?
C2 N2 S1 122.39(14) . . ?
O2 C1 N1 127.4(2) . . ?
O2 C1 C2 125.0(2) . . ?
N1 C1 C2 107.5(2) . . ?
N2 C2 C3 118.91(19) . . ?
N2 C2 C1 109.68(17) . . ?
C3 C2 C1 102.29(18) . . ?
N2 C2 C16 103.61(16) . . ?
C3 C2 C16 114.70(17) . . ?
C1 C2 C16 107.24(18) . . ?
C4 C3 C8 119.8(2) . . ?
C4 C3 C2 132.1(2) . . ?
C8 C3 C2 107.9(2) . . ?
C3 C4 C5 118.4(3) . . ?
C6 C5 C4 121.0(3) . . ?
C5 C6 C7 121.6(3) . . ?
C6 C7 C8 117.2(3) . . ?
C3 C8 C7 122.0(3) . . ?
C3 C8 N1 109.9(2) . . ?
C7 C8 N1 128.1(3) . . ?
C15 C10 C11 121.7(2) . . ?
C15 C10 N2 109.20(18) . . ?
C11 C10 N2 129.1(2) . . ?
C12 C11 C10 116.3(2) . . ?
C13 C12 C11 123.3(2) . . ?
C13 C12 Br1 119.25(18) . . ?
C11 C12 Br1 117.47(19) . . ?
C12 C13 C14 119.0(2) . . ?
C15 C14 C13 119.7(2) . . ?
C14 C15 C10 120.0(2) . . ?
C14 C15 C16 127.8(2) . . ?
C10 C15 C16 112.23(19) . . ?
C15 C16 C17 115.02(17) . . ?
C15 C16 C2 102.36(16) . . ?
C17 C16 C2 113.60(17) . . ?
C22 C17 C18 119.06(19) . . ?
C22 C17 C16 119.57(19) . . ?
C18 C17 C16 121.19(18) . . ?
C17 C18 C19 122.16(19) . . ?
C18 C19 C20 117.0(2) . . ?
C18 C19 C23 120.2(2) . . ?
C20 C19 C23 122.8(2) . . ?
O1 C20 C21 114.6(2) . . ?
O1 C20 C19 122.9(2) . . ?
C21 C20 C19 122.5(2) . . ?
C22 C21 C20 117.0(2) . . ?
C22 C21 C27 121.0(2) . . ?
C20 C21 C27 122.0(2) . . ?
C17 C22 C21 122.3(2) . . ?
C25 C23 C26 106.5(3) . . ?
C25 C23 C19 111.4(2) . . ?
C26 C23 C19 110.3(2) . . ?
C25 C23 C24 106.9(3) . . ?
C26 C23 C24 111.3(3) . . ?
C19 C23 C24 110.4(2) . . ?
C29 C27 C30 106.6(3) . . ?
C29 C27 C28 107.4(4) . . ?
C30 C27 C28 110.1(3) . . ?
C29 C27 C21 111.5(2) . . ?
C30 C27 C21 109.9(3) . . ?
C28 C27 C21 111.2(3) . . ?
C36 C31 C32 120.4(3) . . ?
C36 C31 S1 120.5(2) . . ?
C32 C31 S1 119.1(2) . . ?
C33 C32 C31 119.2(3) . . ?
C32 C33 C34 121.5(3) . . ?
C35 C34 C33 118.1(3) . . ?
C35 C34 C37 120.7(4) . . ?
C33 C34 C37 121.2(4) . . ?
C34 C35 C36 121.7(3) . . ?
C31 C36 C35 119.1(3) . . ?

_refine_diff_density_max         0.500
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.062

_shelxl_version_number           2014-1

