# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_20110714a_0m
_database_code_depnum_ccdc_archive 'CCDC 896943'
_audit_update_record             
;
2018-01-13 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 Br O3 S'
_chemical_formula_sum            'C15 H11 Br O3 S'
_chemical_formula_weight         351.21

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7178(7)
_cell_length_b                   9.2215(9)
_cell_length_c                   9.9594(10)
_cell_angle_alpha                84.587(2)
_cell_angle_beta                 86.687(3)
_cell_angle_gamma                78.032(3)
_cell_volume                     689.78(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3435
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      28.13

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    3.134
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5326
_exptl_absorpt_correction_T_max  0.7243
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_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  'Bruker APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5705
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2509
_reflns_number_gt                2180
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.1277P)²+0.2938P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2509
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1643
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.44306(6) 0.41283(5) 0.35877(4) 0.0531(2) Uani 1 1 d . . .
S1 S 0.28682(13) 0.82253(10) 0.26189(10) 0.0394(3) Uani 1 1 d . . .
O1 O 0.2158(4) 0.6968(3) 0.0500(3) 0.0406(6) Uani 1 1 d . . .
O2 O 0.3830(4) 0.7726(4) 0.3809(3) 0.0542(8) Uani 1 1 d . . .
O3 O 0.3433(4) 0.9302(3) 0.1670(4) 0.0561(8) Uani 1 1 d . . .
C1 C 0.0526(8) 0.7093(7) 0.5092(6) 0.0682(14) Uani 1 1 d . . .
H1A H 0.1225 0.6300 0.4617 0.102 Uiso 1 1 calc R . .
H1B H -0.0385 0.6727 0.5637 0.102 Uiso 1 1 calc R . .
H1C H 0.1271 0.7461 0.5661 0.102 Uiso 1 1 calc R . .
C2 C -0.0301(6) 0.8317(5) 0.4105(4) 0.0446(9) Uani 1 1 d . . .
C3 C -0.2111(7) 0.8921(6) 0.4285(6) 0.0586(12) Uani 1 1 d . . .
H3 H -0.2738 0.8566 0.5026 0.070 Uiso 1 1 calc R . .
C4 C -0.2997(8) 1.0036(6) 0.3386(6) 0.0631(13) Uani 1 1 d . . .
H4 H -0.4205 1.0406 0.3514 0.076 Uiso 1 1 calc R . .
C5 C -0.2054(7) 1.0596(6) 0.2287(6) 0.0585(12) Uani 1 1 d . . .
H5 H -0.2626 1.1355 0.1687 0.070 Uiso 1 1 calc R . .
C6 C -0.0291(6) 1.0023(5) 0.2098(5) 0.0504(10) Uani 1 1 d . . .
H6 H 0.0342 1.0383 0.1362 0.060 Uiso 1 1 calc R . .
C7 C 0.0564(6) 0.8895(5) 0.3010(4) 0.0425(9) Uani 1 1 d . . .
C8 C 0.2855(5) 0.6652(4) 0.1761(4) 0.0368(8) Uani 1 1 d . . .
C9 C 0.3397(5) 0.5148(4) 0.2059(4) 0.0365(8) Uani 1 1 d . . .
C10 C 0.2997(5) 0.4463(5) 0.0908(4) 0.0405(9) Uani 1 1 d . . .
C11 C 0.2259(5) 0.5612(5) -0.0002(4) 0.0397(9) Uani 1 1 d . . .
C12 C 0.1687(7) 0.5416(7) -0.1257(5) 0.0578(12) Uani 1 1 d . . .
H12 H 0.1184 0.6211 -0.1851 0.069 Uiso 1 1 calc R . .
C13 C 0.1921(7) 0.3965(8) -0.1554(6) 0.0657(16) Uani 1 1 d . . .
H13 H 0.1540 0.3765 -0.2374 0.079 Uiso 1 1 calc R . .
C14 C 0.2719(8) 0.2761(7) -0.0660(7) 0.0702(17) Uani 1 1 d . . .
H14 H 0.2895 0.1798 -0.0921 0.084 Uiso 1 1 calc R . .
C15 C 0.3240(6) 0.2986(5) 0.0584(6) 0.0537(12) Uani 1 1 d . . .
H15 H 0.3732 0.2195 0.1185 0.064 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 C9 1.843(4) . ?
S1 O3 1.423(3) . ?
S1 O2 1.423(4) . ?
S1 C8 1.754(4) . ?
S1 C7 1.791(5) . ?
O1 C8 1.376(5) . ?
O1 C11 1.376(5) . ?
C1 C2 1.488(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.369(6) . ?
C2 C3 1.401(7) . ?
C3 C4 1.390(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.363(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(7) . ?
C6 H6 0.9300 . ?
C8 C9 1.372(6) . ?
C9 C10 1.438(6) . ?
C10 C11 1.377(6) . ?
C10 C15 1.401(6) . ?
C11 C12 1.389(6) . ?
C12 C13 1.371(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.414(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(8) . ?
C14 H14 0.9300 . ?
C15 H15 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 119.6(2) . . ?
O3 S1 C8 107.3(2) . . ?
O2 S1 C8 107.2(2) . . ?
O3 S1 C7 107.2(2) . . ?
O2 S1 C7 111.4(2) . . ?
C8 S1 C7 102.73(19) . . ?
C8 O1 C11 105.6(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 116.7(5) . . ?
C7 C2 C1 125.1(4) . . ?
C3 C2 C1 118.2(5) . . ?
C4 C3 C2 121.8(5) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.3(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 119.6(5) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 119.9(5) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C6 122.6(4) . . ?
C2 C7 S1 122.3(4) . . ?
C6 C7 S1 115.0(3) . . ?
C9 C8 O1 111.5(3) . . ?
C9 C8 S1 134.3(3) . . ?
O1 C8 S1 114.3(3) . . ?
C8 C9 C10 105.8(4) . . ?
C8 C9 Br1 129.4(3) . . ?
C10 C9 Br1 124.7(3) . . ?
C11 C10 C15 120.2(4) . . ?
C11 C10 C9 106.0(4) . . ?
C15 C10 C9 133.8(4) . . ?
O1 C11 C10 111.1(3) . . ?
O1 C11 C12 124.8(4) . . ?
C10 C11 C12 124.1(4) . . ?
C13 C12 C11 115.0(5) . . ?
C13 C12 H12 122.5 . . ?
C11 C12 H12 122.5 . . ?
C12 C13 C14 122.4(5) . . ?
C12 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
C15 C14 C13 121.3(5) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C10 117.0(5) . . ?
C14 C15 H15 121.5 . . ?
C10 C15 H15 121.5 . . ?

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
C7 C2 C3 C4 1.0(7) . . . . ?
C1 C2 C3 C4 -178.1(5) . . . . ?
C2 C3 C4 C5 -1.4(8) . . . . ?
C3 C4 C5 C6 1.2(8) . . . . ?
C4 C5 C6 C7 -0.7(7) . . . . ?
C3 C2 C7 C6 -0.5(6) . . . . ?
C1 C2 C7 C6 178.5(5) . . . . ?
C3 C2 C7 S1 -178.9(3) . . . . ?
C1 C2 C7 S1 0.1(6) . . . . ?
C5 C6 C7 C2 0.4(7) . . . . ?
C5 C6 C7 S1 178.9(4) . . . . ?
O3 S1 C7 C2 -164.6(3) . . . . ?
O2 S1 C7 C2 -32.0(4) . . . . ?
C8 S1 C7 C2 82.5(4) . . . . ?
O3 S1 C7 C6 16.8(4) . . . . ?
O2 S1 C7 C6 149.5(3) . . . . ?
C8 S1 C7 C6 -96.0(3) . . . . ?
C11 O1 C8 C9 0.4(4) . . . . ?
C11 O1 C8 S1 -179.9(3) . . . . ?
O3 S1 C8 C9 136.8(4) . . . . ?
O2 S1 C8 C9 7.1(5) . . . . ?
C7 S1 C8 C9 -110.4(5) . . . . ?
O3 S1 C8 O1 -42.8(3) . . . . ?
O2 S1 C8 O1 -172.5(3) . . . . ?
C7 S1 C8 O1 70.0(3) . . . . ?
O1 C8 C9 C10 -0.6(5) . . . . ?
S1 C8 C9 C10 179.7(3) . . . . ?
O1 C8 C9 Br1 179.4(3) . . . . ?
S1 C8 C9 Br1 -0.2(7) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
Br1 C9 C10 C11 -179.5(3) . . . . ?
C8 C9 C10 C15 179.2(4) . . . . ?
Br1 C9 C10 C15 -0.9(7) . . . . ?
C8 O1 C11 C10 0.0(4) . . . . ?
C8 O1 C11 C12 179.7(4) . . . . ?
C15 C10 C11 O1 -179.2(4) . . . . ?
C9 C10 C11 O1 -0.4(4) . . . . ?
C15 C10 C11 C12 1.1(6) . . . . ?
C9 C10 C11 C12 179.9(4) . . . . ?
O1 C11 C12 C13 179.8(4) . . . . ?
C10 C11 C12 C13 -0.5(7) . . . . ?
C11 C12 C13 C14 -1.3(7) . . . . ?
C12 C13 C14 C15 2.7(8) . . . . ?
C13 C14 C15 C10 -2.0(7) . . . . ?
C11 C10 C15 C14 0.2(6) . . . . ?
C9 C10 C15 C14 -178.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.162
