# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_170731a
_database_code_depnum_ccdc_archive 'CCDC 1888213'
loop_
_audit_author_name
_audit_author_address
'Bo Jiang'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2019-01-01 deposited with the CCDC.	2019-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 Br O2 S'
_chemical_formula_weight         435.32

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4326(7)
_cell_length_b                   11.5349(9)
_cell_length_c                   18.9409(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.0070(10)
_cell_angle_gamma                90.00
_cell_volume                     1842.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3652
_cell_measurement_theta_min      2.627
_cell_measurement_theta_max      27.308

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    2.361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4372
_exptl_absorpt_correction_T_max  0.7335
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9016
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3240
_reflns_number_gt                2391
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0380P)²+0.4487P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3240
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.82109(4) 1.24766(2) 0.188163(17) 0.04878(13) Uani 1 1 d . . .
S1 S 0.90536(9) 1.02046(6) 0.25600(4) 0.03793(19) Uani 1 1 d . . .
O1 O 0.7566(2) 0.99586(17) 0.28798(11) 0.0488(5) Uani 1 1 d . . .
O2 O 1.0162(3) 1.08828(19) 0.29638(12) 0.0586(6) Uani 1 1 d . . .
C1 C 0.8634(3) 1.0899(2) 0.17473(15) 0.0343(7) Uani 1 1 d . . .
C2 C 0.8430(3) 1.0289(2) 0.11520(14) 0.0316(6) Uani 1 1 d . . .
C3 C 0.8724(3) 0.9024(2) 0.11033(14) 0.0314(6) Uani 1 1 d . . .
C4 C 0.9633(3) 0.8401(2) 0.16457(14) 0.0328(6) Uani 1 1 d . . .
C5 C 0.9957(3) 0.8904(2) 0.23054(15) 0.0357(7) Uani 1 1 d . . .
C6 C 1.0922(3) 0.8384(3) 0.28122(16) 0.0465(8) Uani 1 1 d . . .
H6 H 1.1112 0.8747 0.3244 0.056 Uiso 1 1 calc R . .
C7 C 1.1595(4) 0.7328(3) 0.26720(18) 0.0536(9) Uani 1 1 d . . .
H7 H 1.2256 0.6973 0.3006 0.064 Uiso 1 1 calc R . .
C8 C 1.1287(4) 0.6795(3) 0.20320(17) 0.0494(8) Uani 1 1 d . . .
H8 H 1.1723 0.6071 0.1941 0.059 Uiso 1 1 calc R . .
C9 C 1.0335(4) 0.7325(2) 0.15238(16) 0.0416(7) Uani 1 1 d . . .
H9 H 1.0159 0.6957 0.1093 0.050 Uiso 1 1 calc R . .
C10 C 0.7741(3) 1.0652(2) 0.04654(15) 0.0352(7) Uani 1 1 d . . .
C11 C 0.7521(3) 0.9636(2) 0.00627(14) 0.0329(6) Uani 1 1 d . . .
C12 C 0.6802(3) 0.9675(2) -0.05933(15) 0.0381(7) Uani 1 1 d . . .
H12 H 0.6636 0.8994 -0.0847 0.046 Uiso 1 1 calc R . .
C13 C 0.6317(3) 1.0741(3) -0.08812(16) 0.0407(7) Uani 1 1 d . . .
C14 C 0.6549(3) 1.1730(3) -0.04778(17) 0.0449(8) Uani 1 1 d . . .
H14 H 0.6228 1.2440 -0.0664 0.054 Uiso 1 1 calc R . .
C15 C 0.7236(3) 1.1707(2) 0.01901(16) 0.0417(7) Uani 1 1 d . . .
H15 H 0.7357 1.2386 0.0450 0.050 Uiso 1 1 calc R . .
C16 C 0.5566(4) 1.0805(3) -0.16033(17) 0.0538(9) Uani 1 1 d . . .
H16A H 0.4970 1.1511 -0.1647 0.081 Uiso 1 1 calc R . .
H16B H 0.4871 1.0154 -0.1672 0.081 Uiso 1 1 calc R . .
H16C H 0.6377 1.0790 -0.1952 0.081 Uiso 1 1 calc R . .
C17 C 0.8135(3) 0.8640(2) 0.04673(14) 0.0312(6) Uani 1 1 d . . .
C18 C 0.8016(3) 0.7441(2) 0.01974(14) 0.0320(6) Uani 1 1 d . . .
C19 C 0.8706(3) 0.7137(3) -0.04423(15) 0.0388(7) Uani 1 1 d . . .
H19 H 0.9241 0.7696 -0.0700 0.047 Uiso 1 1 calc R . .
C20 C 0.8605(4) 0.6027(3) -0.06949(16) 0.0472(8) Uani 1 1 d . . .
H20 H 0.9085 0.5834 -0.1117 0.057 Uiso 1 1 calc R . .
C21 C 0.7791(4) 0.5196(3) -0.03246(18) 0.0543(9) Uani 1 1 d . . .
H21 H 0.7713 0.4444 -0.0499 0.065 Uiso 1 1 calc R . .
C22 C 0.7095(4) 0.5480(3) 0.03028(18) 0.0516(9) Uani 1 1 d . . .
H22 H 0.6543 0.4919 0.0552 0.062 Uiso 1 1 calc R . .
C23 C 0.7210(4) 0.6593(2) 0.05656(16) 0.0419(7) Uani 1 1 d . . .
H23 H 0.6744 0.6776 0.0993 0.050 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 C1 1.873(3) . ?
S1 O2 1.430(2) . ?
S1 O1 1.4309(19) . ?
S1 C5 1.754(3) . ?
S1 C1 1.766(3) . ?
C1 C2 1.338(4) . ?
C2 C10 1.476(4) . ?
C2 C3 1.483(3) . ?
C3 C17 1.368(4) . ?
C3 C4 1.460(4) . ?
C4 C9 1.396(4) . ?
C4 C5 1.400(4) . ?
C5 C6 1.384(4) . ?
C6 C7 1.372(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.388(4) . ?
C10 C11 1.408(4) . ?
C11 C12 1.374(4) . ?
C11 C17 1.470(4) . ?
C12 C13 1.403(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(4) . ?
C13 C16 1.499(4) . ?
C14 C15 1.382(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.477(3) . ?
C18 C23 1.386(4) . ?
C18 C19 1.398(4) . ?
C19 C20 1.369(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.374(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.380(4) . ?
C22 H22 0.9300 . ?
C23 H23 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
O2 S1 O1 116.84(13) . . ?
O2 S1 C5 109.39(14) . . ?
O1 S1 C5 109.58(12) . . ?
O2 S1 C1 109.70(13) . . ?
O1 S1 C1 107.19(13) . . ?
C5 S1 C1 103.28(13) . . ?
C2 C1 S1 121.1(2) . . ?
C2 C1 Br1 127.1(2) . . ?
S1 C1 Br1 110.99(14) . . ?
C1 C2 C10 129.5(3) . . ?
C1 C2 C3 123.4(3) . . ?
C10 C2 C3 106.7(2) . . ?
C17 C3 C4 129.7(2) . . ?
C17 C3 C2 108.3(2) . . ?
C4 C3 C2 121.8(2) . . ?
C9 C4 C5 116.0(3) . . ?
C9 C4 C3 122.7(3) . . ?
C5 C4 C3 121.1(2) . . ?
C6 C5 C4 122.9(3) . . ?
C6 C5 S1 115.7(2) . . ?
C4 C5 S1 121.4(2) . . ?
C7 C6 C5 119.4(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 119.6(3) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C4 121.3(3) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
C15 C10 C11 119.3(3) . . ?
C15 C10 C2 133.9(3) . . ?
C11 C10 C2 106.7(2) . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 C17 130.0(3) . . ?
C10 C11 C17 109.0(2) . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 118.0(3) . . ?
C14 C13 C16 121.1(3) . . ?
C12 C13 C16 120.9(3) . . ?
C15 C14 C13 122.8(3) . . ?
C15 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
C14 C15 C10 118.8(3) . . ?
C14 C15 H15 120.6 . . ?
C10 C15 H15 120.6 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C17 C11 109.0(2) . . ?
C3 C17 C18 129.0(2) . . ?
C11 C17 C18 122.0(2) . . ?
C23 C18 C19 118.3(2) . . ?
C23 C18 C17 121.2(2) . . ?
C19 C18 C17 120.6(2) . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 119.9(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.3(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.5(3) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C1 C2 142.3(2) . . . . ?
O1 S1 C1 C2 -89.9(2) . . . . ?
C5 S1 C1 C2 25.7(3) . . . . ?
O2 S1 C1 Br1 -46.90(17) . . . . ?
O1 S1 C1 Br1 80.88(15) . . . . ?
C5 S1 C1 Br1 -163.44(13) . . . . ?
S1 C1 C2 C10 165.0(2) . . . . ?
Br1 C1 C2 C10 -4.2(4) . . . . ?
S1 C1 C2 C3 -7.6(4) . . . . ?
Br1 C1 C2 C3 -176.84(19) . . . . ?
C1 C2 C3 C17 169.2(2) . . . . ?
C10 C2 C3 C17 -4.9(3) . . . . ?
C1 C2 C3 C4 -15.9(4) . . . . ?
C10 C2 C3 C4 170.0(2) . . . . ?
C17 C3 C4 C9 13.7(4) . . . . ?
C2 C3 C4 C9 -160.0(2) . . . . ?
C17 C3 C4 C5 -171.6(3) . . . . ?
C2 C3 C4 C5 14.7(4) . . . . ?
C9 C4 C5 C6 0.5(4) . . . . ?
C3 C4 C5 C6 -174.6(2) . . . . ?
C9 C4 C5 S1 -175.5(2) . . . . ?
C3 C4 C5 S1 9.4(4) . . . . ?
O2 S1 C5 C6 40.3(3) . . . . ?
O1 S1 C5 C6 -88.9(2) . . . . ?
C1 S1 C5 C6 157.1(2) . . . . ?
O2 S1 C5 C4 -143.4(2) . . . . ?
O1 S1 C5 C4 87.3(2) . . . . ?
C1 S1 C5 C4 -26.6(2) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
S1 C5 C6 C7 176.0(2) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C6 C7 C8 C9 1.5(5) . . . . ?
C7 C8 C9 C4 -1.2(5) . . . . ?
C5 C4 C9 C8 0.3(4) . . . . ?
C3 C4 C9 C8 175.2(3) . . . . ?
C1 C2 C10 C15 6.9(5) . . . . ?
C3 C2 C10 C15 -179.5(3) . . . . ?
C1 C2 C10 C11 -168.9(3) . . . . ?
C3 C2 C10 C11 4.7(3) . . . . ?
C15 C10 C11 C12 -0.6(4) . . . . ?
C2 C10 C11 C12 175.9(2) . . . . ?
C15 C10 C11 C17 -179.5(2) . . . . ?
C2 C10 C11 C17 -2.9(3) . . . . ?
C10 C11 C12 C13 1.9(4) . . . . ?
C17 C11 C12 C13 -179.5(3) . . . . ?
C11 C12 C13 C14 -1.7(4) . . . . ?
C11 C12 C13 C16 178.5(2) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C16 C13 C14 C15 180.0(3) . . . . ?
C13 C14 C15 C10 1.1(4) . . . . ?
C11 C10 C15 C14 -0.9(4) . . . . ?
C2 C10 C15 C14 -176.3(3) . . . . ?
C4 C3 C17 C11 -171.2(2) . . . . ?
C2 C3 C17 C11 3.1(3) . . . . ?
C4 C3 C17 C18 11.4(4) . . . . ?
C2 C3 C17 C18 -174.2(2) . . . . ?
C12 C11 C17 C3 -178.8(3) . . . . ?
C10 C11 C17 C3 -0.1(3) . . . . ?
C12 C11 C17 C18 -1.2(4) . . . . ?
C10 C11 C17 C18 177.5(2) . . . . ?
C3 C17 C18 C23 56.5(4) . . . . ?
C11 C17 C18 C23 -120.5(3) . . . . ?
C3 C17 C18 C19 -124.0(3) . . . . ?
C11 C17 C18 C19 59.0(4) . . . . ?
C23 C18 C19 C20 -0.7(4) . . . . ?
C17 C18 C19 C20 179.8(3) . . . . ?
C18 C19 C20 C21 1.1(5) . . . . ?
C19 C20 C21 C22 -0.7(5) . . . . ?
C20 C21 C22 C23 -0.2(5) . . . . ?
C21 C22 C23 C18 0.6(5) . . . . ?
C19 C18 C23 C22 -0.1(4) . . . . ?
C17 C18 C23 C22 179.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.060
