# 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. 
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#######################################################################

data_1_a
_database_code_depnum_ccdc_archive 'CCDC 2074239'
_audit_update_record             
;
2021-03-30 deposited with the CCDC.	2021-06-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-25
_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         'C24 H21 Br O3 S'
_chemical_formula_sum            'C24 H21 Br O3 S'
_chemical_formula_weight         469.38
_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'
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      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                   9.2058(16)
_cell_length_b                   10.3794(18)
_cell_length_c                   12.708(2)
_cell_angle_alpha                107.378(2)
_cell_angle_beta                 109.996(2)
_cell_angle_gamma                97.756(2)
_cell_volume                     1050.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4880
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.081
_cell_measurement_theta_min      2.441
_shelx_estimated_absorpt_T_max   0.681
_shelx_estimated_absorpt_T_min   0.658
_exptl_absorpt_coefficient_mu    2.079
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1183 before and 0.0518 after correction. The Ratio of minimum to maximum transmission is 0.6168. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12292
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         1.836
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3475
_reflns_number_total             4749
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4749
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.1944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0995
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C17(H17), C13(H13), C19(H19), C2(H2), C3(H3), C20(H20),
 C16(H16), C14(H14), C15(H15), C23(H23), C22(H22)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.29876(3) 0.35323(3) -0.09288(3) 0.07207(14) Uani 1 1 d . . . . .
S1 S 0.62821(6) 0.81835(6) 0.43604(5) 0.03965(14) Uani 1 1 d . . . . .
O3 O 0.6561(2) 0.69946(17) 0.35968(15) 0.0542(4) Uani 1 1 d . . . . .
O2 O 0.55008(19) 0.90740(17) 0.38161(15) 0.0519(4) Uani 1 1 d . . . . .
O1 O 0.1241(2) 0.51440(17) 0.43257(14) 0.0523(4) Uani 1 1 d . . . . .
C7 C 0.2565(2) 0.4097(2) 0.26471(18) 0.0344(4) Uani 1 1 d . . . . .
C6 C 0.0903(2) 0.4253(2) 0.22528(19) 0.0367(5) Uani 1 1 d . . . . .
C8 C 0.3757(2) 0.5133(2) 0.35785(18) 0.0355(5) Uani 1 1 d . . . . .
H8 H 0.477010 0.498103 0.384920 0.043 Uiso 1 1 calc R . . . .
C12 C 0.2902(2) 0.2782(2) 0.20223(18) 0.0369(5) Uani 1 1 d . . . . .
C9 C 0.3550(2) 0.6527(2) 0.42113(19) 0.0371(5) Uani 1 1 d . . . . .
H9 H 0.301246 0.689730 0.360104 0.044 Uiso 1 1 calc R . . . .
C5 C -0.0101(3) 0.3850(2) 0.1041(2) 0.0397(5) Uani 1 1 d . . . . .
H5 H 0.024593 0.343720 0.044665 0.048 Uiso 1 1 calc R . . . .
C17 C 0.4354(3) 0.2828(2) 0.1911(2) 0.0445(5) Uani 1 1 d . . . . .
H17 H 0.506007 0.369099 0.214303 0.053 Uiso 1 1 calc R . . . .
C1 C 0.0328(3) 0.4840(2) 0.3120(2) 0.0429(5) Uani 1 1 d . . . . .
C18 C 0.8127(2) 0.9204(2) 0.5556(2) 0.0412(5) Uani 1 1 d . . . . .
C11 C 0.5156(3) 0.7600(2) 0.51012(19) 0.0384(5) Uani 1 1 d . . . . .
H11A H 0.578442 0.718010 0.562210 0.046 Uiso 1 1 calc R . . . .
H11B H 0.495131 0.839958 0.560422 0.046 Uiso 1 1 calc R . . . .
C4 C -0.1620(3) 0.4065(2) 0.0725(2) 0.0465(6) Uani 1 1 d . . . . .
C10 C 0.2518(3) 0.6400(2) 0.4918(2) 0.0484(6) Uani 1 1 d . . . . .
H10A H 0.319448 0.642772 0.570524 0.058 Uiso 1 1 calc R . . . .
H10B H 0.206897 0.719846 0.504056 0.058 Uiso 1 1 calc R . . . .
C13 C 0.1834(3) 0.1487(2) 0.1611(2) 0.0480(6) Uani 1 1 d . . . . .
H13 H 0.083669 0.143095 0.164733 0.058 Uiso 1 1 calc R . . . .
C21 C 1.1009(3) 1.0844(3) 0.7453(2) 0.0526(6) Uani 1 1 d . . . . .
C19 C 0.8219(3) 1.0524(2) 0.6291(2) 0.0540(6) Uani 1 1 d . . . . .
H19 H 0.731693 1.086760 0.615418 0.065 Uiso 1 1 calc R . . . .
C2 C -0.1202(3) 0.5029(3) 0.2784(3) 0.0544(6) Uani 1 1 d . . . . .
H2 H -0.157236 0.541243 0.337090 0.065 Uiso 1 1 calc R . . . .
C3 C -0.2175(3) 0.4654(3) 0.1587(3) 0.0554(6) Uani 1 1 d . . . . .
H3 H -0.319649 0.479472 0.136059 0.067 Uiso 1 1 calc R . . . .
C20 C 0.9660(3) 1.1330(3) 0.7228(2) 0.0569(7) Uani 1 1 d . . . . .
H20 H 0.972013 1.222042 0.771930 0.068 Uiso 1 1 calc R . . . .
C16 C 0.4770(3) 0.1615(3) 0.1461(2) 0.0588(7) Uani 1 1 d . . . . .
H16 H 0.576228 0.166623 0.141685 0.071 Uiso 1 1 calc R . . . .
C14 C 0.2250(4) 0.0271(3) 0.1144(3) 0.0644(7) Uani 1 1 d . . . . .
H14 H 0.153089 -0.059642 0.087101 0.077 Uiso 1 1 calc R . . . .
C15 C 0.3728(4) 0.0343(3) 0.1083(3) 0.0681(8) Uani 1 1 d . . . . .
H15 H 0.401021 -0.047317 0.078400 0.082 Uiso 1 1 calc R . . . .
C23 C 0.9452(3) 0.8690(3) 0.5780(3) 0.0644(8) Uani 1 1 d . . . . .
H23 H 0.938972 0.779106 0.530388 0.077 Uiso 1 1 calc R . . . .
C24 C 1.2575(3) 1.1730(3) 0.8487(3) 0.0742(9) Uani 1 1 d . . . . .
H24A H 1.324257 1.217813 0.819069 0.111 Uiso 1 1 calc GR . . . .
H24B H 1.310817 1.114734 0.885818 0.111 Uiso 1 1 calc GR . . . .
H24C H 1.237039 1.242870 0.907011 0.111 Uiso 1 1 calc GR . . . .
C22 C 1.0882(3) 0.9527(3) 0.6725(3) 0.0689(8) Uani 1 1 d . . . . .
H22 H 1.178316 0.918196 0.686892 0.083 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 C4 1.901(2) . ?
S1 O3 1.4389(16) . ?
S1 O2 1.4391(16) . ?
S1 C18 1.762(2) . ?
S1 C11 1.779(2) . ?
O1 C1 1.383(3) . ?
O1 C10 1.429(3) . ?
C7 C6 1.486(3) . ?
C7 C8 1.340(3) . ?
C7 C12 1.491(3) . ?
C6 C5 1.392(3) . ?
C6 C1 1.397(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.504(3) . ?
C12 C17 1.388(3) . ?
C12 C13 1.385(3) . ?
C9 H9 0.9800 . ?
C9 C11 1.538(3) . ?
C9 C10 1.532(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.386(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.381(3) . ?
C1 C2 1.385(3) . ?
C18 C19 1.381(3) . ?
C18 C23 1.371(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C4 C3 1.379(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C13 H13 0.9300 . ?
C13 C14 1.389(3) . ?
C21 C20 1.375(4) . ?
C21 C24 1.508(3) . ?
C21 C22 1.366(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(4) . ?
C3 H3 0.9300 . ?
C20 H20 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.363(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(4) . ?
C15 H15 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.385(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C22 H22 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 O2 117.96(11) . . ?
O3 S1 C18 108.44(10) . . ?
O3 S1 C11 109.12(10) . . ?
O2 S1 C18 109.07(10) . . ?
O2 S1 C11 108.05(10) . . ?
C18 S1 C11 103.20(10) . . ?
C1 O1 C10 115.64(18) . . ?
C6 C7 C12 120.18(17) . . ?
C8 C7 C6 119.77(18) . . ?
C8 C7 C12 120.05(18) . . ?
C5 C6 C7 122.11(19) . . ?
C5 C6 C1 118.5(2) . . ?
C1 C6 C7 119.35(19) . . ?
C7 C8 H8 118.2 . . ?
C7 C8 C9 123.69(19) . . ?
C9 C8 H8 118.2 . . ?
C17 C12 C7 120.06(19) . . ?
C13 C12 C7 121.4(2) . . ?
C13 C12 C17 118.4(2) . . ?
C8 C9 H9 108.3 . . ?
C8 C9 C11 112.61(17) . . ?
C8 C9 C10 111.85(18) . . ?
C11 C9 H9 108.3 . . ?
C10 C9 H9 108.3 . . ?
C10 C9 C11 107.48(17) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.1 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.1(2) . . ?
C16 C17 H17 119.4 . . ?
O1 C1 C6 120.0(2) . . ?
O1 C1 C2 119.0(2) . . ?
C2 C1 C6 120.8(2) . . ?
C19 C18 S1 119.10(17) . . ?
C23 C18 S1 120.89(19) . . ?
C23 C18 C19 120.0(2) . . ?
S1 C11 H11A 109.1 . . ?
S1 C11 H11B 109.1 . . ?
C9 C11 S1 112.55(15) . . ?
C9 C11 H11A 109.1 . . ?
C9 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C5 C4 Br1 119.87(19) . . ?
C3 C4 Br1 118.75(18) . . ?
C3 C4 C5 121.4(2) . . ?
O1 C10 C9 113.14(17) . . ?
O1 C10 H10A 109.0 . . ?
O1 C10 H10B 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.1(2) . . ?
C14 C13 H13 119.9 . . ?
C20 C21 C24 120.9(3) . . ?
C22 C21 C20 118.0(2) . . ?
C22 C21 C24 121.0(2) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.4(2) . . ?
C20 C19 H19 120.3 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C4 C3 H3 120.4 . . ?
C2 C3 C4 119.2(2) . . ?
C2 C3 H3 120.4 . . ?
C21 C20 C19 121.4(2) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C17 C16 H16 119.9 . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 H16 119.9 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C18 C23 H23 120.4 . . ?
C18 C23 C22 119.1(2) . . ?
C22 C23 H23 120.4 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C22 C23 121.9(2) . . ?
C21 C22 H22 119.0 . . ?
C23 C22 H22 119.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
