# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_rf2357_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2145616'
loop_
_audit_author_name
_audit_author_address
'Roland Fischer'
;Graz University of Technology
Austria
;
_audit_update_record             
;
2022-01-31 deposited with the CCDC.	2025-03-11 downloaded from the CCDC.
;
_audit_creation_date             2021-10-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 Cl O2, C F3 O3 S'
_chemical_formula_sum            'C14 H8 Cl F3 O5 S'
_chemical_formula_weight         380.71
_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'
Cl Cl 0.1484 0.1585 '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'
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                   6.6746(4)
_cell_length_b                   8.0822(6)
_cell_length_c                   13.7840(10)
_cell_angle_alpha                95.756(2)
_cell_angle_beta                 99.723(2)
_cell_angle_gamma                97.231(2)
_cell_volume                     721.43(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    99.99
_cell_measurement_theta_max      30.16
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.469
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6209
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1574 before and 0.0783 after correction.
The Ratio of minimum to maximum transmission is 0.8323.
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    1.753
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39301
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.189
_diffrn_reflns_theta_min         1.511
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.89
_diffrn_source_power             0.0445
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3895
_reflns_number_total             4150
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)²+0.9578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0925
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C11(H11), C10(H10), C9(H9), C8(H8)
2.b Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O2(H2)
;
_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
Cl1 Cl 0.26279(6) 0.81039(4) 0.30416(3) 0.01238(9) Uani 1 1 d . . . . .
S1 S 0.30411(6) -0.13422(4) 0.75893(3) 0.01095(9) Uani 1 1 d . . . . .
F1 F 0.00202(16) -0.03527(15) 0.83869(9) 0.0258(2) Uani 1 1 d . . . . .
F2 F 0.23641(17) 0.16510(12) 0.82530(8) 0.0193(2) Uani 1 1 d . . . . .
F3 F 0.29386(19) 0.00403(15) 0.93918(8) 0.0250(2) Uani 1 1 d . . . . .
O1 O 0.2526(2) 0.05771(15) 0.45883(9) 0.0198(3) Uani 1 1 d . . . . .
O2 O 0.2175(2) 0.20731(15) 0.59890(9) 0.0174(2) Uani 1 1 d . . . . .
H2 H 0.214(4) 0.113(3) 0.6201(9) 0.026 Uiso 1 1 calc R U . . .
C1 C 0.2543(2) 0.63733(18) 0.37396(11) 0.0103(3) Uani 1 1 d . . . . .
O3 O 0.52270(18) -0.07773(15) 0.78179(10) 0.0173(2) Uani 1 1 d . . . . .
O4 O 0.2029(2) -0.09556(15) 0.66389(9) 0.0175(2) Uani 1 1 d . . . . .
O5 O 0.23804(19) -0.29991(15) 0.78119(9) 0.0176(2) Uani 1 1 d . . . . .
C2 C 0.2559(2) 0.48886(18) 0.31370(11) 0.0097(3) Uani 1 1 d . . . . .
C3 C 0.2515(2) 0.34251(18) 0.35902(11) 0.0104(3) Uani 1 1 d . . . . .
H3 H 0.2535 0.2376 0.3217 0.012 Uiso 1 1 calc R U . . .
C4 C 0.2440(2) 0.35160(18) 0.45984(11) 0.0100(3) Uani 1 1 d . . . . .
C5 C 0.2441(2) 0.50518(19) 0.51674(11) 0.0103(3) Uani 1 1 d . . . . .
H5 H 0.2402 0.5077 0.5854 0.012 Uiso 1 1 calc R U . . .
C6 C 0.2497(2) 0.65494(19) 0.47390(11) 0.0107(3) Uani 1 1 d . . . . .
H6 H 0.2503 0.7607 0.5109 0.013 Uiso 1 1 calc R U . . .
C7 C 0.2608(2) 0.51200(19) 0.21081(11) 0.0103(3) Uani 1 1 d . . . . .
C12 C 0.2618(2) 0.67792(19) 0.19258(11) 0.0111(3) Uani 1 1 d . . . . .
C11 C 0.2625(2) 0.7374(2) 0.10253(12) 0.0128(3) Uani 1 1 d . . . . .
H11 H 0.2621 0.8529 0.0949 0.015 Uiso 1 1 calc R U . . .
C10 C 0.2639(2) 0.6164(2) 0.02338(12) 0.0137(3) Uani 1 1 d . . . . .
H10 H 0.2635 0.6488 -0.0410 0.016 Uiso 1 1 calc R U . . .
C9 C 0.2660(2) 0.4478(2) 0.03772(12) 0.0140(3) Uani 1 1 d . . . . .
H9 H 0.2682 0.3677 -0.0174 0.017 Uiso 1 1 calc R U . . .
C8 C 0.2649(2) 0.39415(19) 0.13006(12) 0.0129(3) Uani 1 1 d . . . . .
H8 H 0.2669 0.2790 0.1383 0.015 Uiso 1 1 calc R U . . .
C13 C 0.2382(2) 0.19007(19) 0.50424(11) 0.0114(3) Uani 1 1 d . . . . .
C14 C 0.2042(2) 0.0065(2) 0.84536(12) 0.0137(3) Uani 1 1 d . . . . .


_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
Cl1 C1 1.7759(15) . ?
Cl1 C12 1.7823(15) . ?
S1 O3 1.4438(12) . ?
S1 O4 1.4513(12) . ?
S1 O5 1.4357(12) . ?
S1 C14 1.8289(16) . ?
F1 C14 1.3346(19) . ?
F2 C14 1.3369(19) . ?
F3 C14 1.3333(19) . ?
O1 C13 1.2073(19) . ?
O2 H2 0.84(3) . ?
O2 C13 1.3305(19) . ?
C1 C2 1.392(2) . ?
C1 C6 1.376(2) . ?
C2 C3 1.391(2) . ?
C2 C7 1.454(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(2) . ?
C4 C5 1.400(2) . ?
C4 C13 1.495(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(2) . ?
C6 H6 0.9500 . ?
C7 C12 1.388(2) . ?
C7 C8 1.397(2) . ?
C12 C11 1.376(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.392(2) . ?
C10 H10 0.9500 . ?
C10 C9 1.398(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.386(2) . ?
C8 H8 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
C1 Cl1 C12 92.12(7) . . ?
O3 S1 O4 114.38(8) . . ?
O3 S1 C14 103.07(7) . . ?
O4 S1 C14 101.56(7) . . ?
O5 S1 O3 116.06(7) . . ?
O5 S1 O4 114.59(7) . . ?
O5 S1 C14 104.67(7) . . ?
C13 O2 H2 109.5 . . ?
C2 C1 Cl1 110.40(11) . . ?
C6 C1 Cl1 122.72(11) . . ?
C6 C1 C2 126.88(14) . . ?
C1 C2 C7 113.62(13) . . ?
C3 C2 C1 116.65(13) . . ?
C3 C2 C7 129.72(13) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.26(13) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 121.39(14) . . ?
C3 C4 C13 116.82(13) . . ?
C5 C4 C13 121.79(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.95(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 114.85(13) . . ?
C1 C6 H6 122.6 . . ?
C5 C6 H6 122.6 . . ?
C12 C7 C2 113.35(13) . . ?
C12 C7 C8 116.75(14) . . ?
C8 C7 C2 129.89(14) . . ?
C7 C12 Cl1 110.48(11) . . ?
C11 C12 Cl1 123.02(12) . . ?
C11 C12 C7 126.50(14) . . ?
C12 C11 H11 122.4 . . ?
C12 C11 C10 115.27(14) . . ?
C10 C11 H11 122.4 . . ?
C11 C10 H10 119.7 . . ?
C11 C10 C9 120.68(14) . . ?
C9 C10 H10 119.7 . . ?
C10 C9 H9 119.1 . . ?
C8 C9 C10 121.81(15) . . ?
C8 C9 H9 119.1 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.97(14) . . ?
C9 C8 H8 120.5 . . ?
O1 C13 O2 123.50(14) . . ?
O1 C13 C4 123.26(14) . . ?
O2 C13 C4 113.24(13) . . ?
F1 C14 S1 111.20(11) . . ?
F1 C14 F2 107.20(13) . . ?
F2 C14 S1 110.75(11) . . ?
F3 C14 S1 111.96(11) . . ?
F3 C14 F1 108.00(13) . . ?
F3 C14 F2 107.53(13) . . ?

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
Cl1 C1 C2 C3 179.48(11) . . . . ?
Cl1 C1 C2 C7 -0.92(16) . . . . ?
Cl1 C1 C6 C5 -179.74(11) . . . . ?
Cl1 C12 C11 C10 179.32(11) . . . . ?
C1 Cl1 C12 C7 -1.57(12) . . . . ?
C1 Cl1 C12 C11 178.55(14) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C1 C2 C7 C12 -0.27(19) . . . . ?
C1 C2 C7 C8 179.55(15) . . . . ?
O3 S1 C14 F1 -176.05(11) . . . . ?
O3 S1 C14 F2 64.86(12) . . . . ?
O3 S1 C14 F3 -55.14(13) . . . . ?
O4 S1 C14 F1 65.26(13) . . . . ?
O4 S1 C14 F2 -53.83(12) . . . . ?
O4 S1 C14 F3 -173.83(12) . . . . ?
O5 S1 C14 F1 -54.25(13) . . . . ?
O5 S1 C14 F2 -173.34(11) . . . . ?
O5 S1 C14 F3 66.66(13) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C2 C3 C4 C13 179.63(13) . . . . ?
C2 C7 C12 Cl1 1.33(16) . . . . ?
C2 C7 C12 C11 -178.79(15) . . . . ?
C2 C7 C8 C9 179.02(15) . . . . ?
C3 C2 C7 C12 179.26(15) . . . . ?
C3 C2 C7 C8 -0.9(3) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C3 C4 C13 O1 4.8(2) . . . . ?
C3 C4 C13 O2 -175.80(13) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C5 C4 C13 O1 -174.60(15) . . . . ?
C5 C4 C13 O2 4.8(2) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
C6 C1 C2 C7 179.94(14) . . . . ?
C7 C2 C3 C4 -179.00(14) . . . . ?
C7 C12 C11 C10 -0.5(2) . . . . ?
C12 Cl1 C1 C2 1.41(11) . . . . ?
C12 Cl1 C1 C6 -179.41(13) . . . . ?
C12 C7 C8 C9 -1.2(2) . . . . ?
C12 C11 C10 C9 -0.4(2) . . . . ?
C11 C10 C9 C8 0.6(2) . . . . ?
C10 C9 C8 C7 0.3(2) . . . . ?
C8 C7 C12 Cl1 -178.52(11) . . . . ?
C8 C7 C12 C11 1.4(2) . . . . ?
C13 C4 C5 C6 179.96(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_rf2354_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2145617'
loop_
_audit_author_name
_audit_author_address
'Roland Fischer'
;Graz University of Technology
Austria
;
_audit_update_record             
;
2022-01-31 deposited with the CCDC.	2025-03-11 downloaded from the CCDC.
;
_audit_creation_date             2021-10-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 I O2, C F3 O3 S'
_chemical_formula_sum            'C14 H8 F3 I O5 S'
_chemical_formula_weight         472.16
_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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   7.0091(7)
_cell_length_b                   10.6673(11)
_cell_length_c                   11.7572(12)
_cell_angle_alpha                63.230(5)
_cell_angle_beta                 75.790(5)
_cell_angle_gamma                85.689(5)
_cell_volume                     760.20(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100.03
_cell_measurement_theta_max      30.12
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.301
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5788
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1473 before and 0.0701 after correction.
The Ratio of minimum to maximum transmission is 0.7759.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.063
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1267
_diffrn_reflns_av_unetI/netI     0.0992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            40453
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.161
_diffrn_reflns_theta_min         1.997
_diffrn_ambient_temperature      100.03
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.88
_diffrn_source_power             0.044
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3409
_reflns_number_total             4407
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         3.136
_refine_diff_density_min         -2.844
_refine_diff_density_rms         0.294
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0253P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0535
_refine_ls_wR_factor_ref         0.0609
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C11(H11), C10(H10), C9(H9), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_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
I1 I 0.56800(2) 0.43922(2) 0.23053(2) 0.00928(6) Uani 1 1 d . . . . .
H2 H 1.355(6) 0.006(4) 0.593(4) 0.055(13) Uiso 1 1 d . . . . .
O1 O 1.4254(2) 0.08359(19) 0.36999(19) 0.0151(4) Uani 1 1 d . . . . .
C1 C 0.8098(3) 0.3251(3) 0.2907(3) 0.0108(6) Uani 1 1 d . . . . .
F1 F 0.1955(3) 0.9038(2) 0.0752(2) 0.0492(6) Uani 1 1 d . . . . .
S1 S 0.18645(9) 0.65420(7) 0.08700(7) 0.01274(15) Uani 1 1 d . . . . .
C3 C 0.9422(3) 0.1943(3) 0.4766(3) 0.0094(6) Uani 1 1 d . . . . .
H3 H 0.9342 0.1554 0.5680 0.011 Uiso 1 1 calc R U . . .
F3 F 0.4751(3) 0.8399(2) -0.0031(2) 0.0509(6) Uani 1 1 d . . . . .
O3 O 0.2313(3) 0.5990(2) 0.21436(19) 0.0182(5) Uani 1 1 d . . . . .
F2 F 0.2511(3) 0.9030(2) -0.1124(2) 0.0457(6) Uani 1 1 d . . . . .
O2 O 1.2527(3) 0.04587(19) 0.5714(2) 0.0125(4) Uani 1 1 d . . . . .
C2 C 0.7865(3) 0.2692(3) 0.4254(3) 0.0088(6) Uani 1 1 d . . . . .
C4 C 1.1090(3) 0.1768(3) 0.3932(3) 0.0109(6) Uani 1 1 d . . . . .
O4 O -0.0195(3) 0.6659(2) 0.08889(19) 0.0175(4) Uani 1 1 d . . . . .
C5 C 1.1247(3) 0.2334(3) 0.2586(3) 0.0117(6) Uani 1 1 d . . . . .
H5 H 1.2394 0.2193 0.2035 0.014 Uiso 1 1 calc R U . . .
O5 O 0.3004(3) 0.5946(2) 0.0044(2) 0.0195(5) Uani 1 1 d . . . . .
C6 C 0.9747(3) 0.3097(3) 0.2050(3) 0.0113(6) Uani 1 1 d . . . . .
H6 H 0.9839 0.3501 0.1134 0.014 Uiso 1 1 calc R U . . .
C7 C 0.5998(3) 0.2925(3) 0.5023(3) 0.0087(6) Uani 1 1 d . . . . .
C11 C 0.2825(3) 0.4047(3) 0.4904(3) 0.0120(6) Uani 1 1 d . . . . .
H11 H 0.1954 0.4624 0.4394 0.014 Uiso 1 1 calc R U . . .
C12 C 0.4660(3) 0.3757(3) 0.4321(3) 0.0090(6) Uani 1 1 d . . . . .
C10 C 0.2313(4) 0.3462(3) 0.6258(3) 0.0130(6) Uani 1 1 d . . . . .
H10 H 0.1061 0.3633 0.6690 0.016 Uiso 1 1 calc R U . . .
C9 C 0.3608(4) 0.2625(3) 0.6998(3) 0.0132(6) Uani 1 1 d . . . . .
H9 H 0.3234 0.2235 0.7928 0.016 Uiso 1 1 calc R U . . .
C8 C 0.5437(4) 0.2361(3) 0.6384(3) 0.0121(6) Uani 1 1 d . . . . .
H8 H 0.6313 0.1791 0.6895 0.015 Uiso 1 1 calc R U . . .
C13 C 1.2771(3) 0.0973(3) 0.4448(3) 0.0116(6) Uani 1 1 d . . . . .
C14 C 0.2819(5) 0.8353(3) 0.0069(4) 0.0305(8) Uani 1 1 d . . . . .


_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
I1 C1 2.087(2) . ?
I1 C12 2.094(3) . ?
O1 C13 1.233(3) . ?
C1 C2 1.389(4) . ?
C1 C6 1.388(4) . ?
F1 C14 1.331(4) . ?
S1 O3 1.448(2) . ?
S1 O4 1.4354(18) . ?
S1 O5 1.444(2) . ?
S1 C14 1.820(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.396(3) . ?
C3 C4 1.390(3) . ?
F3 C14 1.333(4) . ?
F2 C14 1.322(4) . ?
O2 H2 0.84(4) . ?
O2 C13 1.304(3) . ?
C2 C7 1.472(3) . ?
C4 C5 1.394(4) . ?
C4 C13 1.488(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(3) . ?
C6 H6 0.9500 . ?
C7 C12 1.394(4) . ?
C7 C8 1.391(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C11 C10 1.382(4) . ?
C10 H10 0.9500 . ?
C10 C9 1.395(4) . ?
C9 H9 0.9500 . ?
C9 C8 1.385(3) . ?
C8 H8 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
C1 I1 C12 81.91(10) . . ?
C2 C1 I1 111.92(17) . . ?
C6 C1 I1 123.6(2) . . ?
C6 C1 C2 124.5(2) . . ?
O3 S1 C14 103.06(14) . . ?
O4 S1 O3 114.98(11) . . ?
O4 S1 O5 115.43(12) . . ?
O4 S1 C14 104.29(14) . . ?
O5 S1 O3 113.48(11) . . ?
O5 S1 C14 103.52(15) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C4 C3 C2 119.7(3) . . ?
C13 O2 H2 109(3) . . ?
C1 C2 C3 117.0(2) . . ?
C1 C2 C7 117.5(2) . . ?
C3 C2 C7 125.5(3) . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 C13 120.9(3) . . ?
C5 C4 C13 117.8(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 121.4 . . ?
C5 C6 C1 117.2(3) . . ?
C5 C6 H6 121.4 . . ?
C12 C7 C2 116.7(2) . . ?
C8 C7 C2 125.8(2) . . ?
C8 C7 C12 117.5(2) . . ?
C12 C11 H11 121.4 . . ?
C10 C11 H11 121.4 . . ?
C10 C11 C12 117.3(2) . . ?
C7 C12 I1 111.89(18) . . ?
C11 C12 I1 124.3(2) . . ?
C11 C12 C7 123.6(3) . . ?
C11 C10 H10 119.5 . . ?
C11 C10 C9 121.0(2) . . ?
C9 C10 H10 119.5 . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H9 119.9 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 H8 119.8 . . ?
O1 C13 O2 124.6(2) . . ?
O1 C13 C4 120.5(3) . . ?
O2 C13 C4 114.9(2) . . ?
F1 C14 S1 110.8(2) . . ?
F1 C14 F3 107.8(3) . . ?
F3 C14 S1 110.7(2) . . ?
F2 C14 F1 108.1(3) . . ?
F2 C14 S1 111.2(2) . . ?
F2 C14 F3 108.2(3) . . ?

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
I1 C1 C2 C3 -178.03(17) . . . . ?
I1 C1 C2 C7 2.6(3) . . . . ?
I1 C1 C6 C5 178.89(18) . . . . ?
C1 C2 C7 C12 -3.4(3) . . . . ?
C1 C2 C7 C8 174.9(2) . . . . ?
C3 C2 C7 C12 177.2(2) . . . . ?
C3 C2 C7 C8 -4.5(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C3 C4 C13 O1 -179.2(2) . . . . ?
C3 C4 C13 O2 0.8(3) . . . . ?
O3 S1 C14 F1 -59.1(3) . . . . ?
O3 S1 C14 F3 60.4(3) . . . . ?
O3 S1 C14 F2 -179.4(2) . . . . ?
C2 C1 C6 C5 0.0(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C2 C3 C4 C13 -179.9(2) . . . . ?
C2 C7 C12 I1 2.4(3) . . . . ?
C2 C7 C12 C11 178.5(2) . . . . ?
C2 C7 C8 C9 -178.0(2) . . . . ?
C4 C3 C2 C1 -1.1(3) . . . . ?
C4 C3 C2 C7 178.3(2) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
O4 S1 C14 F1 61.3(3) . . . . ?
O4 S1 C14 F3 -179.2(2) . . . . ?
O4 S1 C14 F2 -58.9(3) . . . . ?
C5 C4 C13 O1 0.6(3) . . . . ?
C5 C4 C13 O2 -179.4(2) . . . . ?
O5 S1 C14 F1 -177.5(2) . . . . ?
O5 S1 C14 F3 -58.1(3) . . . . ?
O5 S1 C14 F2 62.2(3) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C6 C1 C2 C7 -178.5(2) . . . . ?
C11 C10 C9 C8 -0.3(4) . . . . ?
C12 C7 C8 C9 0.2(4) . . . . ?
C12 C11 C10 C9 0.5(4) . . . . ?
C10 C11 C12 I1 175.16(18) . . . . ?
C10 C11 C12 C7 -0.4(4) . . . . ?
C10 C9 C8 C7 -0.1(4) . . . . ?
C8 C7 C12 I1 -176.01(17) . . . . ?
C8 C7 C12 C11 0.1(4) . . . . ?
C13 C4 C5 C6 -179.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_rf2314_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2149555'
loop_
_audit_author_name
_audit_author_address
'Roland Fischer'
;Graz University of Technology
Austria
;
_audit_update_record             
;
2022-02-01 deposited with the CCDC.	2025-03-11 downloaded from the CCDC.
;
_audit_creation_date             2022-02-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 Br O2, C F3 O3 S'
_chemical_formula_sum            'C14 H8 Br F3 O5 S'
_chemical_formula_weight         425.17
_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'
F F 0.0171 0.0103 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   6.4902(3)
_cell_length_b                   18.8943(9)
_cell_length_c                   12.3367(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.462(2)
_cell_angle_gamma                90
_cell_volume                     1505.95(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9617
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.04
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   0.759
_shelx_estimated_absorpt_T_min   0.553
_exptl_absorpt_coefficient_mu    2.926
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1435 before and 0.0737 after correction.
The Ratio of minimum to maximum transmission is 0.7479.
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    1.875
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            61285
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.158
_diffrn_reflns_theta_min         1.978
_diffrn_ambient_temperature      99.98
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.89
_diffrn_source_power             0.0445
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4093
_reflns_number_total             4391
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0237
_refine_ls_restrained_S_all      1.011
_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)+(0.0299P)²+1.2150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0620
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
2.b Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O2(H2)
;
_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 1.20017(2) 0.88000(2) 0.47309(2) 0.01636(5) Uani 1 1 d . . . . .
O1 O 0.37169(18) 0.76974(6) 0.73493(10) 0.0218(2) Uani 1 1 d . . . . .
S1 S 0.17461(5) 0.53760(2) 0.81979(3) 0.01451(7) Uani 1 1 d . . . . .
F1 F 0.0005(2) 0.51596(8) 0.62232(10) 0.0473(3) Uani 1 1 d . . . . .
C1 C 0.9781(2) 0.84176(7) 0.54735(11) 0.0142(2) Uani 1 1 d . . . . .
F2 F 0.1526(2) 0.42417(6) 0.69692(10) 0.0406(3) Uani 1 1 d . . . . .
O2 O 0.53765(17) 0.66764(6) 0.70837(9) 0.0192(2) Uani 1 1 d . . . . .
H2 H 0.448(3) 0.6518(5) 0.7323(19) 0.029 Uiso 1 1 calc R U . . .
C2 C 0.9843(2) 0.76803(7) 0.54776(11) 0.0138(2) Uani 1 1 d . . . . .
F3 F 0.3331(2) 0.50877(6) 0.63750(10) 0.0445(3) Uani 1 1 d . . . . .
O3 O 0.34706(19) 0.50479(7) 0.88191(11) 0.0270(3) Uani 1 1 d . . . . .
C3 C 0.8324(2) 0.73328(7) 0.60030(11) 0.0143(2) Uani 1 1 d . . . . .
H3 H 0.8314 0.6831 0.6046 0.017 Uiso 1 1 calc R U . . .
C4 C 0.6822(2) 0.77273(7) 0.64635(11) 0.0139(2) Uani 1 1 d . . . . .
O4 O 0.21012(19) 0.61087(6) 0.79146(11) 0.0244(2) Uani 1 1 d . . . . .
C5 C 0.6822(2) 0.84677(7) 0.64225(11) 0.0153(3) Uani 1 1 d . . . . .
H5 H 0.5774 0.8724 0.6740 0.018 Uiso 1 1 calc R U . . .
O5 O -0.02526(17) 0.52447(6) 0.85653(10) 0.0230(2) Uani 1 1 d . . . . .
C6 C 0.8334(2) 0.88329(7) 0.59236(12) 0.0163(3) Uani 1 1 d . . . . .
H6 H 0.8369 0.9335 0.5894 0.020 Uiso 1 1 calc R U . . .
C7 C 1.1496(2) 0.73645(7) 0.49216(11) 0.0144(3) Uani 1 1 d . . . . .
C8 C 1.1927(2) 0.66451(8) 0.48010(12) 0.0179(3) Uani 1 1 d . . . . .
H8 H 1.1087 0.6298 0.5100 0.022 Uiso 1 1 calc R U . . .
C9 C 1.3587(2) 0.64412(8) 0.42422(13) 0.0205(3) Uani 1 1 d . . . . .
H9 H 1.3875 0.5952 0.4164 0.025 Uiso 1 1 calc R U . . .
C00K C 0.5136(2) 0.73767(8) 0.70154(11) 0.0152(3) Uani 1 1 d . . . . .
C10 C 1.4841(2) 0.69407(9) 0.37940(12) 0.0195(3) Uani 1 1 d . . . . .
H10 H 1.5968 0.6787 0.3415 0.023 Uiso 1 1 calc R U . . .
C11 C 1.4464(2) 0.76622(8) 0.38938(12) 0.0179(3) Uani 1 1 d . . . . .
H11 H 1.5299 0.8011 0.3594 0.021 Uiso 1 1 calc R U . . .
C12 C 1.2798(2) 0.78386(7) 0.44566(11) 0.0148(2) Uani 1 1 d . . . . .
C13 C 0.1643(3) 0.49418(9) 0.68695(14) 0.0276(4) Uani 1 1 d . . . . .


_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 1.9208(14) . ?
Br1 C12 1.9273(14) . ?
O1 C00K 1.2075(19) . ?
S1 O3 1.4357(12) . ?
S1 O4 1.4515(11) . ?
S1 O5 1.4358(11) . ?
S1 C13 1.8282(17) . ?
F1 C13 1.332(2) . ?
C1 C2 1.3936(19) . ?
C1 C6 1.380(2) . ?
F2 C13 1.3313(19) . ?
O2 H2 0.74(2) . ?
O2 C00K 1.3341(17) . ?
C2 C3 1.3950(19) . ?
C2 C7 1.455(2) . ?
F3 C13 1.333(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
C4 C5 1.3999(19) . ?
C4 C00K 1.4970(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.399(2) . ?
C7 C12 1.392(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.393(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(2) . ?

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 C12 87.43(6) . . ?
O3 S1 O4 114.00(8) . . ?
O3 S1 O5 116.02(7) . . ?
O3 S1 C13 104.17(8) . . ?
O4 S1 C13 101.84(8) . . ?
O5 S1 O4 114.18(7) . . ?
O5 S1 C13 104.38(8) . . ?
C2 C1 Br1 110.79(10) . . ?
C6 C1 Br1 123.24(11) . . ?
C6 C1 C2 125.97(13) . . ?
C00K O2 H2 109.5 . . ?
C1 C2 C3 116.79(13) . . ?
C1 C2 C7 115.51(13) . . ?
C3 C2 C7 127.70(13) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.44(13) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 121.23(13) . . ?
C3 C4 C00K 121.30(12) . . ?
C5 C4 C00K 117.47(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.97(13) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 115.58(13) . . ?
C1 C6 H6 122.2 . . ?
C5 C6 H6 122.2 . . ?
C8 C7 C2 127.78(13) . . ?
C12 C7 C2 115.72(12) . . ?
C12 C7 C8 116.50(13) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.68(14) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.28(14) . . ?
C10 C9 H9 119.4 . . ?
O1 C00K O2 124.36(14) . . ?
O1 C00K C4 123.20(13) . . ?
O2 C00K C4 112.44(12) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.88(14) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 122.1 . . ?
C12 C11 C10 115.71(14) . . ?
C12 C11 H11 122.1 . . ?
C7 C12 Br1 110.52(10) . . ?
C11 C12 Br1 123.51(11) . . ?
C11 C12 C7 125.96(14) . . ?
F1 C13 S1 110.91(13) . . ?
F1 C13 F3 107.83(15) . . ?
F2 C13 S1 111.14(12) . . ?
F2 C13 F1 108.25(15) . . ?
F2 C13 F3 107.72(15) . . ?
F3 C13 S1 110.86(12) . . ?

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
Br1 C1 C2 C3 179.35(10) . . . . ?
Br1 C1 C2 C7 -1.03(15) . . . . ?
Br1 C1 C6 C5 179.45(10) . . . . ?
C1 C2 C3 C4 1.55(19) . . . . ?
C1 C2 C7 C8 179.88(14) . . . . ?
C1 C2 C7 C12 -0.08(18) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C2 C3 C4 C00K 178.75(12) . . . . ?
C2 C7 C8 C9 -179.80(14) . . . . ?
C2 C7 C12 Br1 1.14(15) . . . . ?
C2 C7 C12 C11 179.85(13) . . . . ?
O3 S1 C13 F1 175.50(12) . . . . ?
O3 S1 C13 F2 55.03(15) . . . . ?
O3 S1 C13 F3 -64.75(14) . . . . ?
C3 C2 C7 C8 -0.5(2) . . . . ?
C3 C2 C7 C12 179.50(13) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C3 C4 C00K O1 -174.05(14) . . . . ?
C3 C4 C00K O2 5.36(18) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
O4 S1 C13 F1 -65.71(13) . . . . ?
O4 S1 C13 F2 173.82(13) . . . . ?
O4 S1 C13 F3 54.05(15) . . . . ?
C5 C4 C00K O1 5.5(2) . . . . ?
C5 C4 C00K O2 -175.04(12) . . . . ?
O5 S1 C13 F1 53.36(13) . . . . ?
O5 S1 C13 F2 -67.11(15) . . . . ?
O5 S1 C13 F3 173.12(13) . . . . ?
C6 C1 C2 C3 -1.2(2) . . . . ?
C6 C1 C2 C7 178.38(13) . . . . ?
C7 C2 C3 C4 -178.02(13) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C7 C12 Br1 -178.83(10) . . . . ?
C8 C7 C12 C11 -0.1(2) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C00K C4 C5 C6 -179.94(13) . . . . ?
C10 C11 C12 Br1 178.56(10) . . . . ?
C10 C11 C12 C7 0.0(2) . . . . ?
C12 C7 C8 C9 0.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
