# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_sh3785
_database_code_depnum_ccdc_archive 'CCDC 1904703'
loop_
_audit_author_name
_audit_author_address
'Volker Huch'
;Uni des Saarlandes
Germany
;
_audit_update_record             
;
2019-03-21 deposited with the CCDC.	2019-10-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_sh3785              
;
PROBLEM: D-H Without Acceptor       O1       --H1       .     Please Check
RESPONSE: alternate occupation OH/Br
;
# Added during the CSD deposition process: Thursday 21 March 2019 09:38 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H11 Br F6 O7 S2, C4 H8 O2'
_chemical_formula_sum            'C24 H19 Br F6 O9 S2'
_chemical_formula_weight         709.42

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'
F F 0.0171 0.0103 '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'

_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                   5.3792(7)
_cell_length_b                   10.8315(14)
_cell_length_c                   13.1574(17)
_cell_angle_alpha                108.397(6)
_cell_angle_beta                 97.733(6)
_cell_angle_gamma                98.586(6)
_cell_volume                     705.67(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    152(2)
_cell_measurement_reflns_used    4078
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.406
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.694
_shelx_estimated_absorpt_T_min   0.546
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6698
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      152(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12193
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.663
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3213
_reflns_number_gt                2568
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0884P)²+0.9389P] 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         3213
_refine_ls_number_parameters     229
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1608
_refine_ls_wR_factor_gt          0.1476
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.056
_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_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 0.50070(16) 0.17507(9) 0.52287(6) 0.0335(2) Uani 0.5 1 d . . P A 1
O1 O 0.4507(12) 0.2305(7) 0.5303(5) 0.0382(15) Uani 0.5 1 d . . P A 2
H1 H 0.3651 0.1581 0.4850 0.057 Uiso 0.5 1 calc R U P A 2
S1 S 0.01481(14) 0.44299(8) 0.83614(6) 0.0230(2) Uani 1 1 d . . . . .
O2 O 0.1605(4) 0.3695(2) 0.88471(18) 0.0290(5) Uani 1 1 d . . . . .
O3 O -0.2545(4) 0.4250(3) 0.83196(18) 0.0317(5) Uani 1 1 d . . . . .
O4 O 0.1149(4) 0.5971(2) 0.90134(17) 0.0260(5) Uani 1 1 d . . . . .
C1 C 0.2978(6) 0.3075(3) 0.5668(2) 0.0241(6) Uani 1 1 d . . . . .
C2 C 0.2370(6) 0.3313(3) 0.6694(2) 0.0236(6) Uani 1 1 d . . . . .
H2 H 0.3002 0.2858 0.7152 0.028 Uiso 1 1 calc R U . . .
C3 C 0.0835(6) 0.4220(3) 0.7048(2) 0.0221(6) Uani 1 1 d . . . . .
C4 C -0.0173(5) 0.4908(3) 0.6397(2) 0.0207(6) Uani 1 1 d . . . . .
C5 C -0.1788(6) 0.5845(3) 0.6732(2) 0.0247(6) Uani 1 1 d . . . . .
H5 H -0.2233 0.6018 0.7431 0.030 Uiso 1 1 calc R U . . .
C6 C -0.2688(6) 0.6484(3) 0.6078(2) 0.0245(6) Uani 1 1 d . . . . .
H6 H -0.3766 0.7090 0.6323 0.029 Uiso 1 1 calc R U . . .
C7 C 0.0473(5) 0.4659(3) 0.5348(2) 0.0191(6) Uani 1 1 d . . . . .
C8 C 0.2053(6) 0.3733(3) 0.4975(2) 0.0219(6) Uani 1 1 d . . . . .
C9 C 0.3851(6) 0.6442(4) 0.9414(3) 0.0340(8) Uani 1 1 d . . . . .
H9A H 0.4806 0.5803 0.9003 0.041 Uiso 1 1 calc R U . . .
H9B H 0.4281 0.6547 1.0196 0.041 Uiso 1 1 calc R U . . .
C10 C 0.4531(9) 0.7728(5) 0.9264(5) 0.0564(12) Uani 1 1 d . . . . .
F1 F 0.7001(5) 0.8263(3) 0.9644(3) 0.0790(10) Uani 1 1 d . . . . .
F2 F 0.3226(7) 0.8621(3) 0.9713(4) 0.0953(12) Uani 1 1 d . . . . .
F3 F 0.4077(7) 0.7538(4) 0.8171(3) 0.0975(13) Uani 1 1 d . . . . .
O5 O 0.6595(13) 0.1186(6) 0.6662(5) 0.0524(15) Uani 0.5 1 d . U P . .
O6 O 0.6827(14) -0.0373(7) 0.7405(6) 0.0665(18) Uani 0.5 1 d . U P . .
C11 C 0.279(2) -0.0421(13) 0.6480(12) 0.081(3) Uani 0.5 1 d . U P . .
H11A H 0.1835 0.0007 0.7029 0.121 Uiso 0.5 1 calc R U P A .
H11B H 0.2571 -0.1368 0.6386 0.121 Uiso 0.5 1 calc R U P . .
H11C H 0.2146 -0.0322 0.5784 0.121 Uiso 0.5 1 calc R U P . .
C12 C 0.562(2) 0.0229(9) 0.6857(8) 0.056(2) Uani 0.5 1 d . U P A .
C13 C 0.9437(19) 0.0203(9) 0.7869(8) 0.057(2) Uani 0.5 1 d . U P A .
H13A H 0.9982 -0.0124 0.8470 0.069 Uiso 0.5 1 calc R U P . .
H13B H 0.9637 0.1179 0.8184 0.069 Uiso 0.5 1 calc R U P . .
C14 C 1.109(2) -0.0111(11) 0.7072(11) 0.072(3) Uani 0.5 1 d . U P . .
H14A H 1.0859 -0.1078 0.6743 0.109 Uiso 0.5 1 calc R U P A .
H14B H 1.2878 0.0270 0.7435 0.109 Uiso 0.5 1 calc R U P . .
H14C H 1.0633 0.0264 0.6502 0.109 Uiso 0.5 1 calc R U P . .


_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 1.923(3) . ?
Br1 O5 2.261(6) . ?
O1 C1 1.289(7) . ?
O1 H1 0.8400 . ?
S1 O3 1.424(2) . ?
S1 O2 1.424(2) . ?
S1 O4 1.586(2) . ?
S1 C3 1.768(3) . ?
O4 C9 1.433(4) . ?
C1 C2 1.387(4) . ?
C1 C8 1.406(4) . ?
C2 C3 1.385(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.408(4) . ?
C4 C7 1.421(4) . ?
C4 C5 1.436(4) . ?
C5 C6 1.348(4) . ?
C5 H5 0.9500 . ?
C6 C8 1.427(4) 2_566 ?
C6 H6 0.9500 . ?
C7 C8 1.423(4) . ?
C7 C7 1.435(5) 2_566 ?
C8 C6 1.427(4) 2_566 ?
C9 C10 1.468(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 F2 1.315(6) . ?
C10 F1 1.326(5) . ?
C10 F3 1.369(6) . ?
O5 C12 1.207(11) . ?
O6 C12 1.289(11) . ?
O6 C13 1.414(11) . ?
C11 C12 1.523(15) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.455(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C1 Br1 O5 110.69(19) . . ?
C1 O1 H1 109.5 . . ?
O3 S1 O2 119.85(14) . . ?
O3 S1 O4 103.37(14) . . ?
O2 S1 O4 109.33(13) . . ?
O3 S1 C3 110.44(14) . . ?
O2 S1 C3 108.55(14) . . ?
O4 S1 C3 104.10(13) . . ?
C9 O4 S1 117.8(2) . . ?
O1 C1 C2 123.3(4) . . ?
O1 C1 C8 115.4(4) . . ?
C2 C1 C8 121.2(3) . . ?
C2 C1 Br1 116.3(2) . . ?
C8 C1 Br1 122.4(2) . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 122.5(3) . . ?
C2 C3 S1 115.7(2) . . ?
C4 C3 S1 121.8(2) . . ?
C3 C4 C7 117.4(3) . . ?
C3 C4 C5 124.1(3) . . ?
C7 C4 C5 118.5(3) . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C8 121.3(3) . 2_566 ?
C5 C6 H6 119.3 . . ?
C8 C6 H6 119.3 2_566 . ?
C4 C7 C8 120.7(2) . . ?
C4 C7 C7 120.0(3) . 2_566 ?
C8 C7 C7 119.3(3) . 2_566 ?
C1 C8 C7 118.7(3) . . ?
C1 C8 C6 122.0(3) . 2_566 ?
C7 C8 C6 119.3(3) . 2_566 ?
O4 C9 C10 107.1(3) . . ?
O4 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
O4 C9 H9B 110.3 . . ?
C10 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
F2 C10 F1 107.6(4) . . ?
F2 C10 F3 106.2(4) . . ?
F1 C10 F3 107.0(4) . . ?
F2 C10 C9 115.2(4) . . ?
F1 C10 C9 111.5(3) . . ?
F3 C10 C9 109.0(4) . . ?
C12 O5 Br1 124.0(7) . . ?
C12 O6 C13 116.5(7) . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C12 O6 124.9(10) . . ?
O5 C12 C11 123.8(9) . . ?
O6 C12 C11 111.4(9) . . ?
O6 C13 C14 112.2(9) . . ?
O6 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
O6 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         1.040
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.097

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetic ester'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_sh3982
_database_code_depnum_ccdc_archive 'CCDC 1904704'
loop_
_audit_author_name
_audit_author_address
'Volker Huch'
;Uni des Saarlandes
Germany
;
_audit_update_record             
;
2019-03-21 deposited with the CCDC.	2019-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 Br F6 O7 S2'
_chemical_formula_sum            'C23 H15 Br F6 O7 S2'
_chemical_formula_weight         661.38

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'
F F 0.0171 0.0103 '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                   5.4124(3)
_cell_length_b                   13.1343(7)
_cell_length_c                   17.3655(10)
_cell_angle_alpha                87.330(4)
_cell_angle_beta                 87.521(4)
_cell_angle_gamma                83.123(4)
_cell_volume                     1223.38(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    142(2)
_cell_measurement_reflns_used    3538
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.36

_exptl_crystal_description       cuboid
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_F_000             660
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.049
_exptl_absorpt_coefficient_mu    1.941
_shelx_estimated_absorpt_T_min   0.652
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7768
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      142(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22922
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.175
_diffrn_reflns_theta_max         28.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5875
_reflns_number_gt                4312
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0589P)²+1.0998P] 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         5875
_refine_ls_number_parameters     362
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.050
_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_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 1.30610(7) 0.40572(3) 0.04474(2) 0.02629(13) Uani 1 1 d . . . . .
S1 S 0.68884(16) 0.15736(6) 0.19684(5) 0.0194(2) Uani 1 1 d . . . . .
O1 O 0.7176(5) 0.13167(19) 0.28610(15) 0.0240(6) Uani 1 1 d . . . . .
O2 O 0.8632(5) 0.09022(18) 0.15491(16) 0.0250(6) Uani 1 1 d . . . . .
O3 O 0.4290(5) 0.15785(19) 0.18693(16) 0.0269(6) Uani 1 1 d . . . . .
C23 C 0.9635(7) 0.0968(3) 0.3125(2) 0.0307(9) Uani 1 1 d . . . . .
H23A H 1.0913 0.1203 0.2755 0.037 Uiso 1 1 calc R U . . .
H23B H 0.9889 0.0209 0.3170 0.037 Uiso 1 1 calc R U . . .
C24 C 0.9838(10) 0.1401(5) 0.3881(3) 0.0543(14) Uani 1 1 d . . . . .
F1 F 0.9575(7) 0.2447(3) 0.3808(2) 0.0757(11) Uani 1 1 d . . . . .
F2 F 0.8185(7) 0.1181(3) 0.43984(18) 0.0819(12) Uani 1 1 d . . . . .
F3 F 1.2071(6) 0.1103(3) 0.4162(2) 0.0837(12) Uani 1 1 d . . . . .
S2 S 0.59275(17) 0.86108(6) 0.24844(6) 0.0207(2) Uani 1 1 d . . . . .
O4 O 0.4140(5) 0.92726(19) 0.29030(16) 0.0261(6) Uani 1 1 d . . . . .
O5 O 0.8514(5) 0.86214(19) 0.26005(17) 0.0286(6) Uani 1 1 d . . . . .
O6 O 0.5666(5) 0.88633(18) 0.15947(15) 0.0230(6) Uani 1 1 d . . . . .
C21 C 0.3230(7) 0.9195(3) 0.1306(2) 0.0254(8) Uani 1 1 d . . . . .
H21A H 0.3040 0.9943 0.1182 0.030 Uiso 1 1 calc R U . . .
H21B H 0.1921 0.9043 0.1696 0.030 Uiso 1 1 calc R U . . .
C22 C 0.3017(8) 0.8613(3) 0.0590(3) 0.0346(10) Uani 1 1 d . . . . .
F4 F 0.3242(5) 0.75982(19) 0.07487(16) 0.0456(7) Uani 1 1 d . . . . .
F5 F 0.4740(5) 0.8791(2) 0.00480(15) 0.0503(7) Uani 1 1 d . . . . .
F6 F 0.0795(5) 0.8881(3) 0.03000(17) 0.0588(8) Uani 1 1 d . . . . .
O7 O 0.0575(5) 0.60544(19) 0.38028(16) 0.0265(6) Uani 1 1 d . . . . .
C17 C -0.0512(8) 0.6859(3) 0.4262(2) 0.0303(9) Uani 1 1 d . . . . .
H17A H -0.1300 0.7430 0.3930 0.036 Uiso 1 1 calc R U . . .
H17B H 0.0780 0.7122 0.4558 0.036 Uiso 1 1 calc R U . . .
C18 C -0.2415(9) 0.6457(3) 0.4797(3) 0.0399(11) Uani 1 1 d D . . . .
H18A H -0.3054 0.6898 0.5195 0.048 Uiso 0.487(9) 1 calc R U P A 1
H18B H -0.2145 0.5755 0.4966 0.048 Uiso 0.513(9) 1 calc R U P A 2
C19A C -0.3321(16) 0.5594(6) 0.4798(5) 0.037(2) Uani 0.487(9) 1 d D U P A 1
H19A H -0.2767 0.5114 0.4416 0.045 Uiso 0.487(9) 1 calc R U P A 1
H19B H -0.4543 0.5437 0.5180 0.045 Uiso 0.487(9) 1 calc R U P A 1
C19B C -0.4335(14) 0.6977(7) 0.5038(5) 0.037(2) Uani 0.513(9) 1 d D U P A 2
H19C H -0.4661 0.7681 0.4880 0.045 Uiso 0.513(9) 1 calc R U P A 2
H19D H -0.5478 0.6672 0.5380 0.045 Uiso 0.513(9) 1 calc R U P A 2
C1 C 1.0357(6) 0.3934(3) 0.1162(2) 0.0188(7) Uani 1 1 d . . . . .
C2 C 0.9649(6) 0.2965(3) 0.1314(2) 0.0183(7) Uani 1 1 d . . . . .
H2 H 1.0495 0.2393 0.1059 0.022 Uiso 1 1 calc R U . . .
C3 C 0.7715(7) 0.2831(3) 0.1837(2) 0.0194(7) Uani 1 1 d . . . . .
C4 C 0.6377(6) 0.3664(3) 0.2226(2) 0.0186(7) Uani 1 1 d . . . . .
C5 C 0.7121(6) 0.4653(3) 0.2058(2) 0.0159(7) Uani 1 1 d . . . . .
C6 C 0.9129(6) 0.4799(3) 0.1521(2) 0.0174(7) Uani 1 1 d . . . . .
C7 C 0.9834(7) 0.5806(3) 0.1373(2) 0.0199(7) Uani 1 1 d . . . . .
H7 H 1.1203 0.5902 0.1028 0.024 Uiso 1 1 calc R U . . .
C8 C 0.8584(7) 0.6620(3) 0.1717(2) 0.0207(8) Uani 1 1 d . . . . .
H8 H 0.9076 0.7282 0.1600 0.025 Uiso 1 1 calc R U . . .
C9 C 0.6545(6) 0.6521(2) 0.2250(2) 0.0170(7) Uani 1 1 d . . . . .
C10 C 0.5815(6) 0.5525(2) 0.24207(19) 0.0155(7) Uani 1 1 d . . . . .
C11 C 0.3792(6) 0.5388(3) 0.2949(2) 0.0177(7) Uani 1 1 d . . . . .
C12 C 0.3105(7) 0.4385(3) 0.3108(2) 0.0203(7) Uani 1 1 d . . . . .
H12 H 0.1749 0.4295 0.3461 0.024 Uiso 1 1 calc R U . . .
C13 C 0.4342(7) 0.3558(3) 0.2769(2) 0.0205(7) Uani 1 1 d . . . . .
H13 H 0.3856 0.2896 0.2892 0.025 Uiso 1 1 calc R U . . .
C14 C 0.5169(6) 0.7341(3) 0.2626(2) 0.0177(7) Uani 1 1 d . . . . .
C16 C 0.2501(6) 0.6242(3) 0.3303(2) 0.0179(7) Uani 1 1 d . . . . .
C15 C 0.3196(7) 0.7211(3) 0.3144(2) 0.0194(7) Uani 1 1 d . . . . .
H15 H 0.2324 0.7787 0.3388 0.023 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 C1 1.895(3) . ?
S1 O2 1.414(3) . ?
S1 O3 1.424(3) . ?
S1 O1 1.581(3) . ?
S1 C3 1.765(3) . ?
O1 C23 1.442(5) . ?
C23 C24 1.468(7) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 F2 1.288(6) . ?
C24 F3 1.331(6) . ?
C24 F1 1.365(7) . ?
S2 O4 1.420(3) . ?
S2 O5 1.425(3) . ?
S2 O6 1.574(3) . ?
S2 C14 1.769(3) . ?
O6 C21 1.442(4) . ?
C21 C22 1.505(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 F6 1.326(5) . ?
C22 F5 1.329(5) . ?
C22 F4 1.340(5) . ?
O7 C16 1.366(4) . ?
O7 C17 1.410(5) . ?
C17 C18 1.485(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19B 1.242(7) . ?
C18 C19A 1.288(6) . ?
C18 H18A 0.9500 . ?
C18 H18B 0.9500 . ?
C19A H19A 0.9500 . ?
C19A H19B 0.9500 . ?
C19B H19C 0.9500 . ?
C19B H19D 0.9500 . ?
C1 C2 1.383(5) . ?
C1 C6 1.403(5) . ?
C2 C3 1.378(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.419(5) . ?
C4 C5 1.419(5) . ?
C4 C13 1.434(5) . ?
C5 C6 1.426(5) . ?
C5 C10 1.430(5) . ?
C6 C7 1.429(5) . ?
C7 C8 1.344(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.424(5) . ?
C8 H8 0.9500 . ?
C9 C14 1.404(5) . ?
C9 C10 1.425(5) . ?
C10 C11 1.420(5) . ?
C11 C16 1.402(5) . ?
C11 C12 1.423(5) . ?
C12 C13 1.352(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.387(5) . ?
C16 C15 1.382(5) . ?
C15 H15 0.9500 . ?

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 O3 120.26(16) . . ?
O2 S1 O1 109.12(15) . . ?
O3 S1 O1 103.44(15) . . ?
O2 S1 C3 108.67(16) . . ?
O3 S1 C3 110.03(16) . . ?
O1 S1 C3 104.04(15) . . ?
C23 O1 S1 117.8(2) . . ?
O1 C23 C24 107.4(4) . . ?
O1 C23 H23A 110.2 . . ?
C24 C23 H23A 110.2 . . ?
O1 C23 H23B 110.2 . . ?
C24 C23 H23B 110.2 . . ?
H23A C23 H23B 108.5 . . ?
F2 C24 F3 107.8(5) . . ?
F2 C24 F1 105.3(5) . . ?
F3 C24 F1 107.4(5) . . ?
F2 C24 C23 115.5(5) . . ?
F3 C24 C23 110.7(4) . . ?
F1 C24 C23 109.8(5) . . ?
O4 S2 O5 119.87(16) . . ?
O4 S2 O6 109.39(15) . . ?
O5 S2 O6 104.00(16) . . ?
O4 S2 C14 108.41(17) . . ?
O5 S2 C14 109.30(16) . . ?
O6 S2 C14 104.83(15) . . ?
C21 O6 S2 118.9(2) . . ?
O6 C21 C22 106.7(3) . . ?
O6 C21 H21A 110.4 . . ?
C22 C21 H21A 110.4 . . ?
O6 C21 H21B 110.4 . . ?
C22 C21 H21B 110.4 . . ?
H21A C21 H21B 108.6 . . ?
F6 C22 F5 108.3(4) . . ?
F6 C22 F4 107.6(4) . . ?
F5 C22 F4 107.5(4) . . ?
F6 C22 C21 109.5(4) . . ?
F5 C22 C21 112.6(4) . . ?
F4 C22 C21 111.2(4) . . ?
C16 O7 C17 118.1(3) . . ?
O7 C17 C18 108.4(3) . . ?
O7 C17 H17A 110.0 . . ?
C18 C17 H17A 110.0 . . ?
O7 C17 H17B 110.0 . . ?
C18 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C19B C18 C17 124.3(6) . . ?
C19A C18 C17 129.1(5) . . ?
C19A C18 H18A 115.4 . . ?
C17 C18 H18A 115.4 . . ?
C19B C18 H18B 117.9 . . ?
C17 C18 H18B 117.9 . . ?
C18 C19A H19A 120.0 . . ?
C18 C19A H19B 120.0 . . ?
H19A C19A H19B 120.0 . . ?
C18 C19B H19C 120.0 . . ?
C18 C19B H19D 120.0 . . ?
H19C C19B H19D 120.0 . . ?
C2 C1 C6 121.7(3) . . ?
C2 C1 Br1 117.5(3) . . ?
C6 C1 Br1 120.8(3) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 S1 116.4(3) . . ?
C4 C3 S1 121.4(3) . . ?
C5 C4 C3 117.2(3) . . ?
C5 C4 C13 119.1(3) . . ?
C3 C4 C13 123.8(3) . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 C10 119.8(3) . . ?
C6 C5 C10 119.0(3) . . ?
C1 C6 C5 118.0(3) . . ?
C1 C6 C7 122.6(3) . . ?
C5 C6 C7 119.4(3) . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 122.0(3) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C14 C9 C8 124.6(3) . . ?
C14 C9 C10 116.8(3) . . ?
C8 C9 C10 118.6(3) . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 C5 119.4(3) . . ?
C9 C10 C5 120.0(3) . . ?
C16 C11 C10 119.5(3) . . ?
C16 C11 C12 121.1(3) . . ?
C10 C11 C12 119.4(3) . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C4 121.0(3) . . ?
C12 C13 H13 119.5 . . ?
C4 C13 H13 119.5 . . ?
C15 C14 C9 122.9(3) . . ?
C15 C14 S2 115.7(3) . . ?
C9 C14 S2 121.4(3) . . ?
O7 C16 C15 123.2(3) . . ?
O7 C16 C11 116.4(3) . . ?
C15 C16 C11 120.4(3) . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?

_refine_diff_density_max         1.810
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.105

_shelxl_version_number           2014/6

