# 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_d8v17425_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1zhl9c
_database_code_depnum_ccdc_archive 'CCDC 1832233'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-06-06 downloaded from the CCDC.
;
_audit_creation_date             2017-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 Br O4 S'
_chemical_formula_sum            'C20 H19 Br O4 S'
_chemical_formula_weight         435.32
_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                   7.5123(3)
_cell_length_b                   12.1628(6)
_cell_length_c                   12.1719(4)
_cell_angle_alpha                63.5220(10)
_cell_angle_beta                 79.7360(10)
_cell_angle_gamma                89.681(2)
_cell_volume                     976.11(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4510
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      27.073
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   0.842
_shelx_estimated_absorpt_T_min   0.730
_exptl_absorpt_coefficient_mu    2.234
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0695 before and 0.0399 after correction. The Ratio of minimum to maximum transmission is 0.7051. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13882
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.514
_diffrn_reflns_theta_min         2.765
_diffrn_ambient_temperature      303.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker D8 Venture'
_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                3288
_reflns_number_total             5858
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5858
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²+0.1999P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1121
_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 Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C15(H15),
 C16(H16), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
;
_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 0.07525(4) 0.71541(3) 0.70191(3) 0.07268(14) Uani 1 1 d . . . . .
S1 S 0.54607(9) 0.26167(6) 0.10265(6) 0.05240(17) Uani 1 1 d . . . . .
O1 O 0.3012(3) 0.06923(18) 0.32813(18) 0.0794(6) Uani 1 1 d . . . . .
O2 O 0.3378(3) 0.15132(17) 0.45454(16) 0.0748(6) Uani 1 1 d . . . . .
O3 O 0.6462(3) 0.15474(18) 0.13425(18) 0.0692(5) Uani 1 1 d . . . . .
O4 O 0.6408(2) 0.37999(17) 0.01752(15) 0.0611(5) Uani 1 1 d . . . . .
C1 C 0.3541(4) 0.1531(2) 0.3437(2) 0.0555(6) Uani 1 1 d . . . . .
C2 C 0.4438(3) 0.2710(2) 0.2411(2) 0.0475(5) Uani 1 1 d . . . . .
C3 C 0.4514(3) 0.3819(2) 0.2393(2) 0.0493(6) Uani 1 1 d . . . . .
H3 H 0.515187 0.445659 0.165727 0.059 Uiso 1 1 calc R . . . .
C4 C 0.3743(3) 0.4155(2) 0.3358(2) 0.0524(6) Uani 1 1 d . . . . .
H4 H 0.308216 0.355075 0.410898 0.063 Uiso 1 1 calc R . . . .
C5 C 0.3943(4) 0.5303(2) 0.3215(2) 0.0529(6) Uani 1 1 d . . . . .
H5 H 0.462355 0.588452 0.245901 0.064 Uiso 1 1 calc R . . . .
C6 C 0.3196(3) 0.5729(2) 0.4128(2) 0.0484(5) Uani 1 1 d . . . . .
C7 C 0.3467(4) 0.6961(2) 0.3850(2) 0.0607(7) Uani 1 1 d . . . . .
H7 H 0.415717 0.750187 0.307713 0.073 Uiso 1 1 calc R . . . .
C8 C 0.2745(4) 0.7412(3) 0.4682(3) 0.0632(7) Uani 1 1 d . . . . .
H8 H 0.292920 0.824425 0.446896 0.076 Uiso 1 1 calc R . . . .
C9 C 0.1757(3) 0.6607(2) 0.5823(2) 0.0515(6) Uani 1 1 d . . . . .
C10 C 0.1450(4) 0.5378(3) 0.6144(2) 0.0626(7) Uani 1 1 d . . . . .
H10 H 0.075968 0.484391 0.691929 0.075 Uiso 1 1 calc R . . . .
C11 C 0.2183(4) 0.4947(2) 0.5298(2) 0.0610(7) Uani 1 1 d . . . . .
H11 H 0.199185 0.411426 0.551834 0.073 Uiso 1 1 calc R . . . .
C12 C 0.2406(6) 0.0423(3) 0.5621(3) 0.1011(13) Uani 1 1 d . . . . .
H12A H 0.148711 0.008243 0.536403 0.121 Uiso 1 1 calc R . . . .
H12B H 0.324686 -0.019853 0.593928 0.121 Uiso 1 1 calc R . . . .
C13 C 0.1573(6) 0.0725(4) 0.6578(3) 0.1119(14) Uani 1 1 d . . . . .
H13A H 0.072609 0.132960 0.626607 0.168 Uiso 1 1 calc GR . . . .
H13B H 0.248461 0.105239 0.683834 0.168 Uiso 1 1 calc GR . . . .
H13C H 0.094272 -0.000248 0.727800 0.168 Uiso 1 1 calc GR . . . .
C14 C 0.3627(3) 0.2427(2) 0.0385(2) 0.0501(6) Uani 1 1 d . . . . .
C15 C 0.3542(4) 0.1477(3) 0.0064(3) 0.0678(7) Uani 1 1 d . . . . .
H15 H 0.439872 0.089802 0.024108 0.081 Uiso 1 1 calc R . . . .
C16 C 0.2170(5) 0.1395(3) -0.0522(3) 0.0733(8) Uani 1 1 d . . . . .
H16 H 0.212805 0.076404 -0.075330 0.088 Uiso 1 1 calc R . . . .
C17 C 0.0858(4) 0.2228(3) -0.0774(2) 0.0620(7) Uani 1 1 d . . . . .
C18 C 0.0957(4) 0.3160(3) -0.0425(2) 0.0590(6) Uani 1 1 d . . . . .
H18 H 0.006927 0.371715 -0.056552 0.071 Uiso 1 1 calc R . . . .
C19 C 0.2347(3) 0.3279(2) 0.0127(2) 0.0530(6) Uani 1 1 d . . . . .
H19 H 0.242167 0.393053 0.032546 0.064 Uiso 1 1 calc R . . . .
C20 C -0.0656(4) 0.2134(3) -0.1402(3) 0.0830(10) Uani 1 1 d . . . . .
H20A H -0.177515 0.229436 -0.099926 0.125 Uiso 1 1 calc GR . . . .
H20B H -0.076773 0.132018 -0.133619 0.125 Uiso 1 1 calc GR . . . .
H20C H -0.038675 0.272769 -0.226828 0.125 Uiso 1 1 calc GR . . . .


_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 1.897(2) . ?
S1 O3 1.4324(19) . ?
S1 O4 1.4387(18) . ?
S1 C2 1.775(2) . ?
S1 C14 1.763(3) . ?
O1 C1 1.199(3) . ?
O2 C1 1.323(3) . ?
O2 C12 1.459(4) . ?
C1 C2 1.477(3) . ?
C2 C3 1.341(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.437(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.333(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.452(3) . ?
C6 C7 1.388(3) . ?
C6 C11 1.387(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.385(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.367(4) . ?
C9 C10 1.374(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(4) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.415(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.380(3) . ?
C14 C19 1.380(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(4) . ?
C17 C18 1.383(4) . ?
C17 C20 1.510(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(4) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 O4 118.28(12) . . ?
O3 S1 C2 109.66(11) . . ?
O3 S1 C14 108.78(12) . . ?
O4 S1 C2 107.11(11) . . ?
O4 S1 C14 107.30(11) . . ?
C14 S1 C2 104.88(11) . . ?
C1 O2 C12 116.8(2) . . ?
O1 C1 O2 124.0(3) . . ?
O1 C1 C2 123.9(2) . . ?
O2 C1 C2 112.1(2) . . ?
C1 C2 S1 114.24(18) . . ?
C3 C2 S1 117.49(18) . . ?
C3 C2 C1 128.2(2) . . ?
C2 C3 H3 115.7 . . ?
C2 C3 C4 128.7(2) . . ?
C4 C3 H3 115.7 . . ?
C3 C4 H4 118.9 . . ?
C5 C4 C3 122.3(2) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 H5 116.9 . . ?
C4 C5 C6 126.1(2) . . ?
C6 C5 H5 116.9 . . ?
C7 C6 C5 120.4(2) . . ?
C11 C6 C5 122.5(2) . . ?
C11 C6 C7 117.1(2) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 C6 122.4(2) . . ?
C8 C7 H7 118.8 . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.4(2) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 Br1 120.8(2) . . ?
C8 C9 C10 121.4(2) . . ?
C10 C9 Br1 117.75(19) . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.1(2) . . ?
C11 C10 H10 120.4 . . ?
C6 C11 H11 119.2 . . ?
C10 C11 C6 121.5(2) . . ?
C10 C11 H11 119.2 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 O2 110.6(3) . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 S1 120.0(2) . . ?
C19 C14 S1 119.70(19) . . ?
C19 C14 C15 120.2(3) . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.2(3) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C20 121.8(3) . . ?
C18 C17 C16 118.0(3) . . ?
C18 C17 C20 120.2(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.2(3) . . ?
C19 C18 H18 119.4 . . ?
C14 C19 H19 120.1 . . ?
C18 C19 C14 119.7(2) . . ?
C18 C19 H19 120.1 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
