# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_1e
_database_code_depnum_ccdc_archive 'CCDC 2190658'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
5,7-difluoro-6-mercapto-1,1-dimethylbenzo[c][1,2,5]oxasilaborol-3(1H)-ol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 B F O2 S Si'
_chemical_formula_sum            'C8 H10 B F O2 S Si'
_chemical_formula_weight         228.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.0854(2)
_cell_length_b                   12.6784(2)
_cell_length_c                   15.9392(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2240.18(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6845
_cell_measurement_theta_min      5.5370
_cell_measurement_theta_max      76.4730

_exptl_crystal_description       block
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.081
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -5 0 0.0837
-3 -5 2 0.0752
-5 3 0 0.1062
5 5 -2 0.0782
1 5 -1 0.0804
0 1 5 0.0508
0 -1 -5 0.0299
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.9981 -5.0040 -0.0159 0.0828 0.4377 0.6929
-3.0001 -5.0001 2.0046 0.2104 0.6850 -0.2596
-5.0005 3.0047 0.0166 -0.0738 -0.1669 -0.7635
5.0014 4.9983 -2.0100 -0.1918 -0.7587 0.5271
1.0019 5.0008 -0.9984 -0.1327 -0.6166 -0.0160
0.0161 0.9948 5.0045 0.4721 -0.1432 -0.0718
-0.0161 -0.9948 -5.0045 -0.4721 0.1432 0.0718
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.817
_oxdiff_exptl_absorpt_empirical_full_max 1.493
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    3.504
_exptl_absorpt_correction_T_min  0.612
_exptl_absorpt_correction_T_max  1.000
_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2195

_diffrn_reflns_number            10110
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.551
_diffrn_reflns_theta_max         76.559
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2331
_reflns_number_gt                2177
_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+0.9746P] 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         2331
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_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
Si1 Si 0.22934(4) 0.31901(3) 0.50191(2) 0.02360(13) Uani 1 1 d . . . . .
S2 S 0.25754(4) -0.01457(3) 0.73980(3) 0.03293(14) Uani 1 1 d . . . . .
H2 H 0.1991 -0.0508 0.7962 0.049 Uiso 1 1 calc R U . . .
F1 F 0.34407(8) 0.11335(7) 0.60289(6) 0.0331(2) Uani 1 1 d . . . . .
O2 O -0.05979(9) 0.43919(8) 0.59874(6) 0.0263(2) Uani 1 1 d . . . . .
H2A H -0.0653 0.4895 0.5646 0.039 Uiso 1 1 calc R U . . .
O1 O 0.11123(9) 0.40246(8) 0.51157(7) 0.0260(2) Uani 1 1 d . . . . .
C4 C 0.02239(13) 0.22662(11) 0.69564(9) 0.0241(3) Uani 1 1 d . . . . .
H4 H -0.0509 0.2533 0.7181 0.029 Uiso 1 1 calc R U . . .
C6 C 0.18711(13) 0.23871(11) 0.59560(9) 0.0224(3) Uani 1 1 d . . . . .
C5 C 0.07781(12) 0.27856(11) 0.62866(9) 0.0216(3) Uani 1 1 d . . . . .
C1 C 0.23671(13) 0.15095(12) 0.63251(9) 0.0242(3) Uani 1 1 d . . . . .
C2 C 0.18336(13) 0.09731(11) 0.69881(9) 0.0246(3) Uani 1 1 d . . . . .
C3 C 0.07365(13) 0.13621(12) 0.72970(9) 0.0250(3) Uani 1 1 d . . . . .
H3 H 0.0340 0.1005 0.7743 0.030 Uiso 1 1 calc R U . . .
C7 C 0.21449(15) 0.24476(14) 0.40295(10) 0.0314(3) Uani 1 1 d . . . . .
H7A H 0.1373 0.2070 0.4025 0.047 Uiso 1 1 calc R U . . .
H7B H 0.2808 0.1940 0.3983 0.047 Uiso 1 1 calc R U . . .
H7C H 0.2174 0.2938 0.3555 0.047 Uiso 1 1 calc R U . . .
B1 B 0.03722(14) 0.37983(12) 0.57942(10) 0.0231(3) Uani 1 1 d . . . . .
C8 C 0.37180(15) 0.39405(14) 0.50897(12) 0.0369(4) Uani 1 1 d . . . . .
H8A H 0.3749 0.4316 0.5627 0.055 Uiso 1 1 calc R U . . .
H8B H 0.3759 0.4450 0.4629 0.055 Uiso 1 1 calc R U . . .
H8C H 0.4402 0.3453 0.5051 0.055 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
Si1 O1 1.6903(11) . ?
Si1 C7 1.8443(16) . ?
Si1 C8 1.8471(17) . ?
Si1 C6 1.8671(14) . ?
S2 C2 1.7650(14) . ?
S2 H2 1.2000 . ?
F1 C1 1.3662(16) . ?
O2 B1 1.3482(19) . ?
O2 H2A 0.8400 . ?
O1 B1 1.3874(19) . ?
C4 C3 1.390(2) . ?
C4 C5 1.397(2) . ?
C4 H4 0.9500 . ?
C6 C1 1.373(2) . ?
C6 C5 1.4146(19) . ?
C5 B1 1.571(2) . ?
C1 C2 1.389(2) . ?
C2 C3 1.402(2) . ?
C3 H3 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
O1 Si1 C7 109.16(7) . . ?
O1 Si1 C8 109.53(7) . . ?
C7 Si1 C8 113.04(8) . . ?
O1 Si1 C6 94.26(6) . . ?
C7 Si1 C6 112.54(7) . . ?
C8 Si1 C6 116.52(8) . . ?
C2 S2 H2 109.5 . . ?
B1 O2 H2A 109.5 . . ?
B1 O1 Si1 113.55(9) . . ?
C3 C4 C5 120.50(13) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C1 C6 C5 118.21(13) . . ?
C1 C6 Si1 133.16(11) . . ?
C5 C6 Si1 108.54(10) . . ?
C4 C5 C6 119.54(13) . . ?
C4 C5 B1 129.89(13) . . ?
C6 C5 B1 110.56(12) . . ?
F1 C1 C6 118.90(13) . . ?
F1 C1 C2 117.59(13) . . ?
C6 C1 C2 123.51(13) . . ?
C1 C2 C3 117.68(13) . . ?
C1 C2 S2 118.47(11) . . ?
C3 C2 S2 123.85(11) . . ?
C4 C3 C2 120.52(13) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 B1 O1 122.30(13) . . ?
O2 B1 C5 124.79(13) . . ?
O1 B1 C5 112.90(12) . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_1f
_database_code_depnum_ccdc_archive 'CCDC 2190659'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
1,2-bis(4-bromo-2,6-difluorophenyl)disulfane
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H4 Br2 F4 S2'
_chemical_formula_sum            'C12 H4 Br2 F4 S2'
_chemical_formula_weight         448.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.26620(10)
_cell_length_b                   10.23010(10)
_cell_length_c                   18.6721(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1387.97(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14026
_cell_measurement_theta_min      2.3080
_cell_measurement_theta_max      73.8510

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.144
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    10.552
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.083
_exptl_absorpt_correction_T_min  0.69226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.821
_oxdiff_exptl_absorpt_empirical_full_max 1.254
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2195

_diffrn_reflns_number            15762
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.736
_diffrn_reflns_theta_max         73.963
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2781
_reflns_number_gt                2767
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.999

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0169P)²+0.3343P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1144 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.022(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2781
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0126
_refine_ls_R_factor_gt           0.0125
_refine_ls_wR_factor_ref         0.0316
_refine_ls_wR_factor_gt          0.0315
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.003
_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
C12 C 1.0639(3) 0.0746(2) 0.89750(11) 0.0142(4) Uani 1 1 d . . . . .
Br1 Br 0.21631(3) -0.39062(2) 0.87754(2) 0.02031(6) Uani 1 1 d . . . . .
Br2 Br 1.32618(3) 0.08963(2) 1.12580(2) 0.02046(6) Uani 1 1 d . . . . .
S3 S 0.98224(7) -0.12282(5) 0.78499(3) 0.01485(10) Uani 1 1 d . . . . .
S4 S 0.96573(7) 0.07232(5) 0.81088(3) 0.01589(11) Uani 1 1 d . . . . .
F1 F 0.77694(17) 0.11683(13) 0.95078(7) 0.0199(3) Uani 1 1 d . . . . .
C11 C 0.9600(3) 0.0998(2) 0.95834(11) 0.0146(4) Uani 1 1 d . . . . .
F2 F 0.6691(2) -0.20049(14) 0.69186(6) 0.0222(3) Uani 1 1 d . . . . .
F3 F 0.84745(19) -0.18054(14) 0.93358(7) 0.0215(3) Uani 1 1 d . . . . .
F4 F 1.35800(19) 0.02519(14) 0.85181(7) 0.0218(3) Uani 1 1 d . . . . .
C6 C 0.7239(3) -0.2139(2) 0.88289(11) 0.0151(4) Uani 1 1 d . . . . .
C8 C 1.2201(3) 0.0830(2) 1.03357(11) 0.0153(4) Uani 1 1 d . . . . .
C9 C 1.3320(3) 0.0552(2) 0.97540(12) 0.0169(4) Uani 1 1 d . . . . .
H9 H 1.4598 0.0386 0.9813 0.020 Uiso 1 1 calc R U . . .
C2 C 0.4710(3) -0.2831(2) 0.77939(12) 0.0184(4) Uani 1 1 d . . . . .
H2 H 0.3844 -0.3075 0.7437 0.022 Uiso 1 1 calc R U . . .
C1 C 0.4373(3) -0.3059(2) 0.85133(12) 0.0164(4) Uani 1 1 d . . . . .
C7 C 1.0326(3) 0.1064(2) 1.02654(11) 0.0155(4) Uani 1 1 d . . . . .
H7 H 0.9578 0.1261 1.0668 0.019 Uiso 1 1 calc R U . . .
C10 C 1.2509(3) 0.0525(2) 0.90872(11) 0.0152(4) Uani 1 1 d . . . . .
C3 C 0.6350(3) -0.2235(2) 0.76165(11) 0.0161(4) Uani 1 1 d . . . . .
C4 C 0.7678(3) -0.1871(2) 0.81147(11) 0.0144(4) Uani 1 1 d . . . . .
C5 C 0.5617(3) -0.2706(2) 0.90456(12) 0.0164(4) Uani 1 1 d . . . . .
H5 H 0.5357 -0.2851 0.9538 0.020 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
C12 C11 1.388(3) . ?
C12 C10 1.393(3) . ?
C12 S4 1.768(2) . ?
Br1 C1 1.889(2) . ?
Br2 C8 1.888(2) . ?
S3 C4 1.762(2) . ?
S3 S4 2.0575(7) . ?
F1 C11 1.349(2) . ?
C11 C7 1.380(3) . ?
F2 C3 1.347(2) . ?
F3 C6 1.349(2) . ?
F4 C10 1.347(2) . ?
C6 C5 1.374(3) . ?
C6 C4 1.398(3) . ?
C8 C9 1.386(3) . ?
C8 C7 1.390(3) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C2 C3 1.379(3) . ?
C2 C1 1.385(3) . ?
C2 H2 0.9500 . ?
C1 C5 1.391(3) . ?
C7 H7 0.9500 . ?
C3 C4 1.391(3) . ?
C5 H5 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
C11 C12 C10 115.94(19) . . ?
C11 C12 S4 122.11(16) . . ?
C10 C12 S4 121.94(17) . . ?
C4 S3 S4 104.15(8) . . ?
C12 S4 S3 101.79(8) . . ?
F1 C11 C7 117.84(19) . . ?
F1 C11 C12 118.34(18) . . ?
C7 C11 C12 123.8(2) . . ?
F3 C6 C5 118.10(19) . . ?
F3 C6 C4 117.86(19) . . ?
C5 C6 C4 124.0(2) . . ?
C9 C8 C7 122.45(19) . . ?
C9 C8 Br2 118.85(17) . . ?
C7 C8 Br2 118.70(16) . . ?
C10 C9 C8 117.4(2) . . ?
C10 C9 H9 121.3 . . ?
C8 C9 H9 121.3 . . ?
C3 C2 C1 117.4(2) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C1 C5 122.3(2) . . ?
C2 C1 Br1 118.60(17) . . ?
C5 C1 Br1 119.09(17) . . ?
C11 C7 C8 117.0(2) . . ?
C11 C7 H7 121.5 . . ?
C8 C7 H7 121.5 . . ?
F4 C10 C9 118.02(19) . . ?
F4 C10 C12 118.61(19) . . ?
C9 C10 C12 123.4(2) . . ?
F2 C3 C2 117.9(2) . . ?
F2 C3 C4 118.2(2) . . ?
C2 C3 C4 123.9(2) . . ?
C3 C4 C6 115.2(2) . . ?
C3 C4 S3 121.72(17) . . ?
C6 C4 S3 122.88(17) . . ?
C6 C5 C1 117.1(2) . . ?
C6 C5 H5 121.4 . . ?
C1 C5 H5 121.4 . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_1g
_database_code_depnum_ccdc_archive 'CCDC 2190660'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
bis((4-bromo-2,6-difluorophenyl)thio)methane
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H6 Br2 F4 S2'
_chemical_formula_sum            ' C13 H6 Br2 F4 S2'
_chemical_formula_weight         462.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   14.4495(2)
_cell_length_b                   7.50810(10)
_cell_length_c                   13.6340(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1479.13(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    12497
_cell_measurement_theta_min      3.2350
_cell_measurement_theta_max      73.7860

_exptl_crystal_description       shapeless
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.075
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    9.926
_exptl_absorpt_correction_T_min  0.75115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.833
_oxdiff_exptl_absorpt_empirical_full_max 1.218
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2195

_diffrn_reflns_number            15232
_diffrn_reflns_av_unetI/netI     0.0082
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         6.125
_diffrn_reflns_theta_max         73.900
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1501
_reflns_number_gt                1486
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0278P)²+1.6268P] 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         1501
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0209
_refine_ls_wR_factor_ref         0.0544
_refine_ls_wR_factor_gt          0.0543
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.001
_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
C7 C 0.2500 0.7500 0.13405(18) 0.0147(5) Uani 1 2 d S T P . .
H7A H 0.2082 0.8160 0.0919 0.018 Uiso 0.5 1 calc R U P . .
H7B H 0.2918 0.6840 0.0919 0.018 Uiso 0.5 1 calc R U P . .
Br1 Br 0.50642(2) 0.23515(3) 0.46208(2) 0.02548(9) Uani 1 1 d . . . . .
S1 S 0.18236(3) 0.59120(6) 0.20409(3) 0.01434(11) Uani 1 1 d . . . . .
F2 F 0.19717(7) 0.57119(15) 0.42059(7) 0.0194(2) Uani 1 1 d . . . . .
F1 F 0.34818(8) 0.38975(15) 0.13241(8) 0.0232(3) Uani 1 1 d . . . . .
C1 C 0.27088(13) 0.4902(2) 0.27338(13) 0.0135(3) Uani 1 1 d . . . . .
C6 C 0.34563(13) 0.4024(2) 0.23133(13) 0.0166(4) Uani 1 1 d . . . . .
C4 C 0.41125(12) 0.3376(2) 0.38577(14) 0.0175(4) Uani 1 1 d . . . . .
C5 C 0.41695(13) 0.3275(2) 0.28408(13) 0.0184(4) Uani 1 1 d . . . . .
H5 H 0.4667 0.2727 0.2531 0.022 Uiso 1 1 calc R U . . .
C3 C 0.33750(13) 0.4169(2) 0.43300(13) 0.0166(3) Uani 1 1 d . . . . .
H3 H 0.3338 0.4195 0.5011 0.020 Uiso 1 1 calc R U . . .
C2 C 0.26970(12) 0.4920(2) 0.37563(13) 0.0139(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
C7 S1 1.8135(13) . ?
C7 S1 1.8136(13) 2_565 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
Br1 C4 1.8882(18) . ?
S1 C1 1.7617(18) . ?
F2 C2 1.352(2) . ?
F1 C6 1.353(2) . ?
C1 C6 1.389(3) . ?
C1 C2 1.394(2) . ?
C6 C5 1.377(3) . ?
C4 C3 1.380(3) . ?
C4 C5 1.391(3) . ?
C5 H5 0.9300 . ?
C3 C2 1.375(3) . ?
C3 H3 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
S1 C7 S1 116.45(13) . 2_565 ?
S1 C7 H7A 108.2 . . ?
S1 C7 H7A 108.2 2_565 . ?
S1 C7 H7B 108.2 . . ?
S1 C7 H7B 108.2 2_565 . ?
H7A C7 H7B 107.3 . . ?
C1 S1 C7 100.03(7) . . ?
C6 C1 C2 115.27(17) . . ?
C6 C1 S1 123.19(14) . . ?
C2 C1 S1 121.54(14) . . ?
F1 C6 C5 118.15(16) . . ?
F1 C6 C1 117.78(16) . . ?
C5 C6 C1 124.07(17) . . ?
C3 C4 C5 122.29(17) . . ?
C3 C4 Br1 118.75(14) . . ?
C5 C4 Br1 118.95(14) . . ?
C6 C5 C4 117.01(17) . . ?
C6 C5 H5 121.5 . . ?
C4 C5 H5 121.5 . . ?
C2 C3 C4 117.50(17) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
F2 C2 C3 118.35(15) . . ?
F2 C2 C1 117.85(16) . . ?
C3 C2 C1 123.80(17) . . ?

_refine_diff_density_max         0.653
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.081

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 2190664'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
3-((5,7-difluoro-3-hydroxy-1,1-dimethyl-1,3-dihydrobenzo[c][1,2,5]oxasilaborol-6-yl)thio)-1-(4-fluorophenyl)pyrrolidine-2,5-dione 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 B F3 N O4 S Si'
_chemical_formula_sum            'C18 H15 B F3 N O4 S Si'
_chemical_formula_weight         437.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.9609(2)
_cell_length_b                   6.79220(10)
_cell_length_c                   25.2398(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.8800(10)
_cell_angle_gamma                90
_cell_volume                     1998.91(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    17462
_cell_measurement_theta_min      3.5510
_cell_measurement_theta_max      72.7290

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    2.500
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.084
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 0 5 0.0478
2 0 -5 0.0411
-1 -2 0 0.0801
1 2 0 0.0874
4 1 5 0.0462
-3 0 -5 0.0299
1 0 5 0.0451
1 0 -1 0.0366
1 -2 5 0.0710
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0034 0.0022 5.0063 -0.0563 -0.1202 0.3373
2.0034 -0.0022 -5.0063 0.0563 0.1202 -0.3373
-1.0092 -2.0017 -0.0091 0.0753 0.4050 0.2329
1.0092 2.0017 0.0091 -0.0753 -0.4050 -0.2329
4.0062 0.9922 5.0145 -0.6383 -0.1912 -0.2428
-3.0012 0.0077 -5.0097 0.5511 0.0007 0.0842
0.9993 -0.0037 5.0083 -0.3532 -0.0485 0.0844
1.0012 -0.0016 -1.0009 -0.0481 0.0384 -0.1181
0.9910 -2.0074 5.0000 -0.3768 0.3804 0.2329
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.844
_oxdiff_exptl_absorpt_empirical_full_max 1.275
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2195
_diffrn_reflns_number            24573
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.593
_diffrn_reflns_theta_max         72.946
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3948
_reflns_number_gt                3736
_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'

_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)+(0.0369P)²+0.9212P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3948
_refine_ls_number_parameters     265
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Si1 Si 0.73945(3) 0.66619(5) 0.09545(2) 0.01844(9) Uani 1 1 d . U . . .
S2 S 1.18998(2) 0.35032(4) 0.09792(2) 0.01993(9) Uani 1 1 d . . . . .
F2 F 1.05332(6) 0.16701(11) -0.00086(3) 0.02300(16) Uani 1 1 d . . . . .
F1 F 1.02180(6) 0.61505(11) 0.13666(3) 0.02160(16) Uani 1 1 d . . . . .
O3 O 1.24128(7) 0.51980(13) 0.22175(4) 0.02273(19) Uani 1 1 d . . . . .
O4 O 0.95804(8) 0.06909(14) 0.22090(4) 0.0270(2) Uani 1 1 d . . . . .
F3 F 0.99861(8) 0.73681(13) 0.40289(3) 0.0350(2) Uani 1 1 d . . . . .
O1 O 0.63293(7) 0.57313(13) 0.04642(4) 0.02188(19) Uani 1 1 d . . . . .
O2 O 0.59943(8) 0.34740(15) -0.02889(4) 0.0290(2) Uani 1 1 d . . . . .
N1 N 1.08879(8) 0.32281(14) 0.22895(4) 0.0174(2) Uani 1 1 d . . . . .
C3 C 0.97103(10) 0.50240(17) 0.09340(5) 0.0179(2) Uani 1 1 d . . . . .
C8 C 1.08755(11) 0.34220(18) 0.32539(5) 0.0223(3) Uani 1 1 d . . . . .
H8 H 1.1201 0.2142 0.3306 0.027 Uiso 1 1 calc R U . . .
C7 C 1.06109(10) 0.42607(18) 0.27387(5) 0.0186(2) Uani 1 1 d . . . . .
C12 C 1.01468(10) 0.61377(18) 0.26565(5) 0.0206(2) Uani 1 1 d . . . . .
H12 H 0.9977 0.6694 0.2302 0.025 Uiso 1 1 calc R U . . .
C2 C 0.85414(10) 0.51833(17) 0.07406(5) 0.0176(2) Uani 1 1 d . . . . .
C16 C 1.18053(10) 0.37904(18) 0.20704(5) 0.0177(2) Uani 1 1 d . . . . .
C19 C 1.03764(10) 0.14685(17) 0.20715(5) 0.0195(2) Uani 1 1 d . . . . .
C18 C 1.09902(10) 0.07663(18) 0.16431(5) 0.0203(2) Uani 1 1 d . . . . .
H18A H 1.0450 0.0667 0.1284 0.024 Uiso 1 1 calc R U . . .
H18B H 1.1344 -0.0539 0.1741 0.024 Uiso 1 1 calc R U . . .
C6 C 0.87030(10) 0.28543(18) 0.00264(5) 0.0196(2) Uani 1 1 d . . . . .
H6 H 0.8366 0.2119 -0.0289 0.023 Uiso 1 1 calc R U . . .
C4 C 1.04105(10) 0.37838(18) 0.07122(5) 0.0181(2) Uani 1 1 d . . . . .
C1 C 0.80335(10) 0.40561(18) 0.02804(5) 0.0188(2) Uani 1 1 d . . . . .
C5 C 0.98662(10) 0.27631(17) 0.02453(5) 0.0185(2) Uani 1 1 d . . . . .
C11 C 0.99312(11) 0.7202(2) 0.30930(5) 0.0242(3) Uani 1 1 d . . . . .
H11 H 0.9614 0.8489 0.3044 0.029 Uiso 1 1 calc R U . . .
C9 C 1.06578(11) 0.4478(2) 0.36926(5) 0.0259(3) Uani 1 1 d . . . . .
H9 H 1.0827 0.3932 0.4048 0.031 Uiso 1 1 calc R U . . .
C17 C 1.19085(10) 0.23184(18) 0.16307(5) 0.0185(2) Uani 1 1 d . . . . .
H17 H 1.2669 0.1655 0.1750 0.022 Uiso 1 1 calc R U . . .
B1 B 0.66920(12) 0.4393(2) 0.01235(6) 0.0216(3) Uani 1 1 d . . . . .
C10 C 1.01905(11) 0.6334(2) 0.35986(5) 0.0251(3) Uani 1 1 d . . . . .
C13 C 0.71830(12) 0.6024(2) 0.16352(6) 0.0320(3) Uani 1 1 d . U . . .
H13A H 0.7129 0.4591 0.1666 0.048 Uiso 1 1 calc R U . . .
H13B H 0.6474 0.6633 0.1689 0.048 Uiso 1 1 calc R U . . .
H13C H 0.7834 0.6509 0.1912 0.048 Uiso 1 1 calc R U . . .
C14 C 0.75016(12) 0.9340(2) 0.08571(7) 0.0315(3) Uani 1 1 d . . . . .
H14A H 0.7615 0.9602 0.0491 0.047 Uiso 1 1 calc R U . . .
H14B H 0.8153 0.9863 0.1127 0.047 Uiso 1 1 calc R U . . .
H14C H 0.6793 0.9978 0.0902 0.047 Uiso 1 1 calc R U . . .
H2A H 0.5335(19) 0.374(3) -0.0313(8) 0.047 Uiso 1 1 d . 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
Si1 O1 1.6886(9) . ?
Si1 C13 1.8431(14) . ?
Si1 C14 1.8437(14) . ?
Si1 C2 1.8740(12) . ?
S2 C4 1.7688(12) . ?
S2 C17 1.8285(12) . ?
F2 C5 1.3514(14) . ?
F1 C3 1.3604(13) . ?
O3 C16 1.2082(15) . ?
O4 C19 1.2054(15) . ?
F3 C10 1.3604(15) . ?
O1 B1 1.3855(17) . ?
O2 B1 1.3352(17) . ?
O2 H2A 0.80(2) . ?
N1 C16 1.3879(15) . ?
N1 C19 1.3983(15) . ?
N1 C7 1.4334(16) . ?
C3 C2 1.3785(16) . ?
C3 C4 1.3905(17) . ?
C8 C7 1.3901(18) . ?
C8 C9 1.3916(19) . ?
C8 H8 0.9500 . ?
C7 C12 1.3874(17) . ?
C12 C11 1.3892(18) . ?
C12 H12 0.9500 . ?
C2 C1 1.4106(17) . ?
C16 C17 1.5190(17) . ?
C19 C18 1.5132(17) . ?
C18 C17 1.5277(16) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C6 C5 1.3792(17) . ?
C6 C1 1.3955(17) . ?
C6 H6 0.9500 . ?
C4 C5 1.3968(17) . ?
C1 B1 1.5813(18) . ?
C11 C10 1.3768(19) . ?
C11 H11 0.9500 . ?
C9 C10 1.378(2) . ?
C9 H9 0.9500 . ?
C17 H17 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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
O1 Si1 C13 110.93(6) . . ?
O1 Si1 C14 109.58(6) . . ?
C13 Si1 C14 112.59(7) . . ?
O1 Si1 C2 93.98(5) . . ?
C13 Si1 C2 113.82(6) . . ?
C14 Si1 C2 114.41(6) . . ?
C4 S2 C17 101.15(5) . . ?
B1 O1 Si1 114.26(8) . . ?
B1 O2 H2A 112.9(15) . . ?
C16 N1 C19 113.20(10) . . ?
C16 N1 C7 121.55(10) . . ?
C19 N1 C7 124.85(10) . . ?
F1 C3 C2 118.43(10) . . ?
F1 C3 C4 117.56(10) . . ?
C2 C3 C4 124.01(11) . . ?
C7 C8 C9 119.29(12) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C12 C7 C8 121.10(12) . . ?
C12 C7 N1 119.13(11) . . ?
C8 C7 N1 119.66(11) . . ?
C7 C12 C11 119.90(12) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C3 C2 C1 117.75(11) . . ?
C3 C2 Si1 133.61(9) . . ?
C1 C2 Si1 108.64(8) . . ?
O3 C16 N1 124.75(11) . . ?
O3 C16 C17 127.17(11) . . ?
N1 C16 C17 108.07(10) . . ?
O4 C19 N1 124.45(12) . . ?
O4 C19 C18 127.43(11) . . ?
N1 C19 C18 108.12(10) . . ?
C19 C18 C17 105.23(10) . . ?
C19 C18 H18A 110.7 . . ?
C17 C18 H18A 110.7 . . ?
C19 C18 H18B 110.7 . . ?
C17 C18 H18B 110.7 . . ?
H18A C18 H18B 108.8 . . ?
C5 C6 C1 118.23(11) . . ?
C5 C6 H6 120.9 . . ?
C1 C6 H6 120.9 . . ?
C3 C4 C5 115.53(11) . . ?
C3 C4 S2 123.90(9) . . ?
C5 C4 S2 120.56(9) . . ?
C6 C1 C2 120.66(11) . . ?
C6 C1 B1 128.59(11) . . ?
C2 C1 B1 110.75(11) . . ?
F2 C5 C6 118.95(11) . . ?
F2 C5 C4 117.35(10) . . ?
C6 C5 C4 123.68(11) . . ?
C10 C11 C12 117.97(12) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C10 C9 C8 118.37(12) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C16 C17 C18 105.27(10) . . ?
C16 C17 S2 112.47(8) . . ?
C18 C17 S2 117.52(8) . . ?
C16 C17 H17 107.0 . . ?
C18 C17 H17 107.0 . . ?
S2 C17 H17 107.0 . . ?
O2 B1 O1 124.25(12) . . ?
O2 B1 C1 123.40(12) . . ?
O1 B1 C1 112.35(11) . . ?
F3 C10 C11 118.38(12) . . ?
F3 C10 C9 118.23(12) . . ?
C11 C10 C9 123.38(12) . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si1 C14 H14A 109.5 . . ?
Si1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2190661'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
3-((5,7-difluoro-3-hydroxy-1,1-dimethyl-1,3-dihydrobenzo[c][1,2,5]oxasilaborol-6-yl)thio)propanenitrile 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 B F2 N O2 S Si'
_chemical_formula_sum            'C11 H12 B F2 N O2 S Si'
_chemical_formula_weight         299.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           6
_space_group_name_H-M_alt        'P m'
_space_group_name_Hall           'P -2y'

_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                   8.7169(3)
_cell_length_b                   7.4368(3)
_cell_length_c                   10.3692(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.038(3)
_cell_angle_gamma                90
_cell_volume                     654.86(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2047
_cell_measurement_theta_min      4.3330
_cell_measurement_theta_max      72.3950

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.083
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -2 0.0692
4 3 -1 0.0431
4 0 -5 0.0534
-5 -2 2 0.0626
0 1 0 0.0279
0 -1 0 0.0550
-1 -1 5 0.1044
-3 1 -4 0.0706
2 -1 1 0.0904
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0008 -1.0004 -1.9982 0.0233 0.0870 0.3574
3.9995 2.9923 -1.0016 -0.2826 -0.8869 -0.1349
3.9999 -0.0084 -4.9963 -0.0662 -0.6356 0.6701
-4.9980 -1.9903 1.9990 0.1111 0.9698 -0.0895
0.0012 0.9999 -0.0017 -0.1697 -0.0772 -0.0902
-0.0012 -0.9999 0.0017 0.1697 0.0772 0.0902
-1.0049 -0.9970 5.0006 0.4608 0.2178 -0.5783
-2.9910 1.0045 -4.0042 -0.6875 0.4374 0.4425
1.9953 -1.0034 1.0034 0.3929 -0.2577 -0.0423
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.780
_oxdiff_exptl_absorpt_empirical_full_max 1.457
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2195

_diffrn_reflns_number            1720
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.377
_diffrn_reflns_theta_max         72.527
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1720
_reflns_number_gt                1623
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_max     0.967
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 _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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+1.4978P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 324 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.06(4)
_refine_ls_number_reflns         1720
_refine_ls_number_parameters     234
_refine_ls_number_restraints     148
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0.01

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
C24 C 0.961(2) 0.0000 0.167(2) 0.036(4) Uani 1 2 d S TU P . .
C21 C 0.8064(11) 0.0921(13) 0.0817(11) 0.011(3) Uani 0.5 1 d . U P . .
H21A H 0.7606 0.1787 0.1351 0.014 Uiso 0.5 1 calc R U P . .
H21B H 0.8275 0.1541 0.0030 0.014 Uiso 0.5 1 calc R U P . .
C20 C 0.7058(12) 0.0621(12) 0.0449(10) 0.008(2) Uani 0.5 1 d D U P . .
H20A H 0.7577 0.1477 -0.0047 0.010 Uiso 0.5 1 calc R U P . .
H20B H 0.6915 0.1235 0.1262 0.010 Uiso 0.5 1 calc R U P . .
C15 C 0.5041(19) 0.0000 -0.5058(16) 0.012(2) Uani 1 2 d S TU P . .
B2 B 0.5158(19) 0.5000 0.0676(17) 0.011(3) Uani 1 2 d S TU P . .
C16 C 0.6688(19) 0.5000 -0.1317(15) 0.013(3) Uani 1 2 d S TU P . .
H16 H 0.7684 0.5000 -0.0712 0.016 Uiso 1 2 calc R U P . .
N1 N 1.0831(19) 0.0000 0.2204(15) 0.020(2) Uani 1 2 d S TU P . .
N2 N -0.039(2) 0.5000 -0.8118(16) 0.028(3) Uani 1 2 d S TU P . .
C26 C 0.082(3) 0.5000 -0.748(3) 0.068(7) Uani 1 2 d S TU P . .
C31 C 0.3515 0.4173 -0.6159 0.019(3) Uani 0.5 1 d D U P . .
H31A H 0.3679 0.3361 -0.6873 0.022 Uiso 0.5 1 calc R U P . .
H31B H 0.2979 0.3491 -0.5569 0.022 Uiso 0.5 1 calc R U P . .
C33 C 0.2423 0.4066 -0.6805 0.018(3) Uani 0.5 1 d . U P . .
H33A H 0.2479 0.3454 -0.5948 0.022 Uiso 0.5 1 calc R U P . .
H33B H 0.3010 0.3454 -0.7392 0.022 Uiso 0.5 1 calc R U P . .
S1 S 0.5075(10) 0.0000 -0.0594(10) 0.0182(7) Uani 1 2 d DS T P . .
Si4 Si 0.8110(10) 0.0000 -0.5094(10) 0.0174(8) Uani 1 2 d S T P . .
F1 F 0.2483(14) 0.0000 -0.2750(12) 0.024(2) Uani 1 2 d S T P . .
O3 O 0.4192(16) 0.0000 -0.7655(14) 0.019(2) Uani 1 2 d DS TU P . .
F3 F 0.8029(14) 0.0000 -0.1949(12) 0.025(2) Uani 1 2 d S TU P . .
C5 C 0.3651(19) 0.0000 -0.4592(15) 0.018(3) Uani 1 2 d S T P . .
H5 H 0.2640 0.0000 -0.5176 0.021 Uiso 1 2 calc R U P . .
O2 O 0.6837(16) 0.0000 -0.6574(13) 0.021(2) Uani 1 2 d S TU P . .
B1 B 0.532(2) 0.0000 -0.6489(19) 0.024(3) Uani 1 2 d S TU P . .
C4 C 0.654(2) 0.0000 -0.4072(16) 0.013(2) Uani 1 2 d S TU P . .
C14 C 0.9333(16) 0.2053(12) -0.4963(14) 0.021(2) Uani 1 1 d . . . . .
H14A H 0.8654 0.3117 -0.5045 0.031 Uiso 1 1 calc R U . . .
H14B H 0.9909 0.2059 -0.5673 0.031 Uiso 1 1 calc R U . . .
H14C H 1.0083 0.2071 -0.4103 0.031 Uiso 1 1 calc R U . . .
C3 C 0.658(2) 0.0000 -0.2783(15) 0.013(3) Uani 1 2 d S T P . .
C2 C 0.524(2) 0.0000 -0.2291(17) 0.022(3) Uani 1 2 d S TU P . .
C1 C 0.384(2) 0.0000 -0.3231(16) 0.017(3) Uani 1 2 d S TU P . .
H3A H 0.326(4) 0.0000 -0.751(12) 0.025 Uiso 1 2 d DS U P . .
Si2 Si 0.2298(10) 0.5000 -0.0740(9) 0.0160(8) Uani 1 2 d S T P . .
S2 S 0.5335(10) 0.5000 -0.5258(10) 0.0166(7) Uani 1 2 d DS T P . .
F2 F 0.7930(14) 0.5000 -0.3090(12) 0.0235(18) Uani 1 2 d S TU P . .
C8 C 0.381(2) 0.5000 -0.3055(17) 0.019(3) Uani 1 2 d S TU P . .
C10 C 0.661(2) 0.5000 -0.2649(16) 0.015(3) Uani 1 2 d S TU P . .
F4 F 0.2392(14) 0.5000 -0.3917(12) 0.0244(19) Uani 1 2 d S TU P . .
C6 C 0.531(2) 0.5000 -0.0847(17) 0.019(3) Uani 1 2 d S TU P . .
C9 C 0.516(2) 0.5000 -0.3611(14) 0.009(2) Uani 1 2 d S T P . .
O1 O 0.3567(15) 0.5000 0.0734(12) 0.017(2) Uani 1 2 d S T P . .
C13 C 0.1109(16) 0.2937(14) -0.0903(14) 0.025(2) Uani 1 1 d . . . . .
H13A H 0.0328 0.3038 -0.0359 0.037 Uiso 1 1 calc R U . . .
H13B H 0.1796 0.1904 -0.0604 0.037 Uiso 1 1 calc R U . . .
H13C H 0.0570 0.2767 -0.1832 0.037 Uiso 1 1 calc R U . . .
C7 C 0.387(2) 0.5000 -0.1669(16) 0.018(3) Uani 1 2 d S T P . .
O4 O 0.6256(17) 0.5000 0.1798(14) 0.023(2) Uani 1 2 d DS TU P . .
H4A H 0.725(7) 0.5000 0.179(13) 0.035 Uiso 1 2 d DS 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
C24 N1 1.08(2) . ?
C24 C21 1.591(19) 2 ?
C24 C21 1.591(19) . ?
C21 C20 1.442(14) 2 ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C20 C21 1.442(14) 2 ?
C20 S1 1.879(10) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C15 C5 1.40(2) . ?
C15 C4 1.466(19) . ?
C15 B1 1.56(2) . ?
B2 O4 1.329(18) . ?
B2 O1 1.402(18) . ?
B2 C6 1.61(2) . ?
C16 C10 1.366(18) . ?
C16 C6 1.40(2) . ?
C16 H16 0.9500 . ?
N2 C26 1.12(3) . ?
C26 C33 1.57(3) 2_565 ?
C26 C33 1.57(3) . ?
C31 C33 1.66800(10) 2_565 ?
C31 S2 1.761(7) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C33 C33 1.38920(10) 2_565 ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
S1 C2 1.798(16) . ?
S1 C20 1.879(10) 2 ?
Si4 O2 1.679(10) . ?
Si4 C14 1.849(10) . ?
Si4 C14 1.849(10) 2 ?
Si4 C4 1.912(16) . ?
F1 C1 1.385(16) . ?
O3 B1 1.38(2) . ?
O3 H3A 0.86(3) . ?
F3 C3 1.363(16) . ?
C5 C1 1.384(17) . ?
C5 H5 0.9500 . ?
O2 B1 1.34(2) . ?
C4 C3 1.330(19) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C3 C2 1.37(2) . ?
C2 C1 1.38(2) . ?
Si2 O1 1.672(9) . ?
Si2 C13 1.838(11) . ?
Si2 C13 1.838(11) 2_565 ?
Si2 C7 1.842(17) . ?
S2 C9 1.749(12) . ?
S2 C31 1.761(7) 2_565 ?
F2 C10 1.335(17) . ?
C8 F4 1.352(18) . ?
C8 C9 1.42(2) . ?
C8 C7 1.43(2) . ?
C10 C9 1.42(2) . ?
C6 C7 1.35(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O4 H4A 0.87(3) . ?

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
N1 C24 C21 153.6(7) . 2 ?
N1 C24 C21 153.6(7) . . ?
C21 C24 C21 51.0(9) 2 . ?
C20 C21 C24 101.1(7) 2 . ?
C20 C21 H21A 111.6 2 . ?
C24 C21 H21A 110.0 . . ?
C20 C21 H21B 111.6 2 . ?
C24 C21 H21B 112.9 . . ?
H21A C21 H21B 109.4 . . ?
C21 C20 S1 112.5(6) 2 . ?
C21 C20 H20A 109.1 2 . ?
S1 C20 H20A 109.1 . . ?
C21 C20 H20B 109.2 2 . ?
S1 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C5 C15 C4 117.5(12) . . ?
C5 C15 B1 131.5(13) . . ?
C4 C15 B1 110.9(13) . . ?
O4 B2 O1 119.2(13) . . ?
O4 B2 C6 130.9(14) . . ?
O1 B2 C6 110.0(11) . . ?
C10 C16 C6 120.0(14) . . ?
C10 C16 H16 119.8 . . ?
C6 C16 H16 120.2 . . ?
N2 C26 C33 153.0(7) . 2_565 ?
N2 C26 C33 153.0(7) . . ?
C33 C26 C33 52.4(9) 2_565 . ?
C33 C31 S2 107.65(9) 2_565 . ?
C33 C31 H31A 110.2 2_565 . ?
S2 C31 H31A 110.1 . . ?
C33 C31 H31B 110.2 2_565 . ?
S2 C31 H31B 110.2 . . ?
H31A C31 H31B 108.5 . . ?
C33 C33 C26 63.8(5) 2_565 . ?
C33 C33 H33A 117.3 2_565 . ?
C26 C33 H33A 115.0 . . ?
C33 C33 H33B 117.3 2_565 . ?
C26 C33 H33B 119.9 . . ?
H33A C33 H33B 114.4 . . ?
C2 S1 C20 107.2(6) . . ?
C2 S1 C20 107.2(6) . 2 ?
C20 S1 C20 28.5(6) . 2 ?
O2 Si4 C14 108.6(4) . . ?
O2 Si4 C14 108.6(4) . 2 ?
C14 Si4 C14 111.3(6) . 2 ?
O2 Si4 C4 95.7(6) . . ?
C14 Si4 C4 115.6(4) . . ?
C14 Si4 C4 115.6(4) 2 . ?
B1 O3 H3A 111(8) . . ?
C1 C5 C15 115.9(13) . . ?
C1 C5 H5 122.2 . . ?
C15 C5 H5 121.9 . . ?
B1 O2 Si4 113.4(10) . . ?
O2 B1 O3 117.6(15) . . ?
O2 B1 C15 115.6(14) . . ?
O3 B1 C15 126.8(16) . . ?
C3 C4 C15 121.2(14) . . ?
C3 C4 Si4 134.4(12) . . ?
C15 C4 Si4 104.5(9) . . ?
Si4 C14 H14A 109.5 . . ?
Si4 C14 H14B 109.4 . . ?
H14A C14 H14B 109.5 . . ?
Si4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C3 F3 116.5(14) . . ?
C4 C3 C2 122.9(13) . . ?
F3 C3 C2 120.6(12) . . ?
C3 C2 C1 115.3(13) . . ?
C3 C2 S1 128.8(11) . . ?
C1 C2 S1 115.9(13) . . ?
C2 C1 C5 127.2(15) . . ?
C2 C1 F1 116.0(11) . . ?
C5 C1 F1 116.9(13) . . ?
O1 Si2 C13 109.1(4) . . ?
O1 Si2 C13 109.1(4) . 2_565 ?
C13 Si2 C13 113.2(7) . 2_565 ?
O1 Si2 C7 93.5(6) . . ?
C13 Si2 C7 114.9(4) . . ?
C13 Si2 C7 114.9(4) 2_565 . ?
C9 S2 C31 104.5(6) . . ?
C9 S2 C31 104.5(6) . 2_565 ?
C31 S2 C31 40.87(18) . 2_565 ?
F4 C8 C9 116.7(12) . . ?
F4 C8 C7 118.9(15) . . ?
C9 C8 C7 124.4(14) . . ?
F2 C10 C16 119.6(13) . . ?
F2 C10 C9 117.3(11) . . ?
C16 C10 C9 123.1(14) . . ?
C7 C6 C16 122.2(13) . . ?
C7 C6 B2 110.3(13) . . ?
C16 C6 B2 127.5(13) . . ?
C8 C9 C10 113.5(11) . . ?
C8 C9 S2 131.3(10) . . ?
C10 C9 S2 115.2(10) . . ?
B2 O1 Si2 114.7(9) . . ?
Si2 C13 H13A 109.5 . . ?
Si2 C13 H13B 109.4 . . ?
H13A C13 H13B 109.5 . . ?
Si2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C7 C8 116.8(15) . . ?
C6 C7 Si2 111.4(10) . . ?
C8 C7 Si2 131.8(13) . . ?
B2 O4 H4A 121(9) . . ?

_refine_diff_density_max         1.756
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.089

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 2190663'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
3-((5,7-difluoro-3-hydroxy-1,1-dimethyl-1,3-dihydrobenzo[c][1,2,5]oxasilaborol-6-yl)thio)pyrrolidine-2,5-dione 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 B F2 N O4 S Si, H2 O'
_chemical_formula_sum            'C12 H14 B F2 N O5 S Si'
_chemical_formula_weight         361.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.9983(14)
_cell_length_b                   8.38700(10)
_cell_length_c                   16.1371(5)
_cell_angle_alpha                90
_cell_angle_beta                 119.051(5)
_cell_angle_gamma                90
_cell_volume                     3194.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10214
_cell_measurement_theta_min      3.0950
_cell_measurement_theta_max      76.4290

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    2.945
_cell_oxdiff_measurement_reflns_used 10302
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.091
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 -1 0.0610
-1 1 1 0.0787
12 0 -10 0.0382
-12 -1 10 0.0469
0 1 8 0.0374
10 -2 -9 0.0475
-12 0 -2 0.0469
15 -1 0 0.0295
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0010 -0.9992 -1.0024 -0.0272 -0.1171 0.1690
-1.0010 0.9992 1.0024 0.0272 0.1171 -0.1690
11.9930 0.0062 -10.0038 0.0962 0.4258 0.8493
-11.9910 -1.0060 10.0015 -0.1455 -0.5817 -0.7655
0.0203 0.9939 7.9935 -0.6273 -0.0031 -0.7792
9.9965 -1.9940 -9.0068 0.0379 0.0564 0.9332
-12.0266 0.0026 -1.9831 0.9187 -0.1875 0.1939
15.0284 -1.0013 -0.0206 -0.9863 0.1281 0.0587
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.790
_oxdiff_exptl_absorpt_empirical_full_max 1.552
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2195

_diffrn_reflns_number            14650
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.746
_diffrn_reflns_theta_max         76.652
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3361
_reflns_number_gt                3215
_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'

_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)+(0.0395P)²+3.4713P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3361
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_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
H1 H 0.0164(9) 1.092(3) 0.4305(14) 0.038(5) Uiso 1 1 d . . . . .
H5A H 0.5181(11) 1.150(3) 0.9893(18) 0.057(7) Uiso 1 1 d . . . . .
H5B H 0.4642(11) 1.155(3) 0.9053(18) 0.057(7) Uiso 1 1 d . . . . .
H2 H 0.3930(10) 0.767(3) 0.9125(16) 0.043(6) Uiso 1 1 d . . . . .
S1 S 0.15797(2) 0.80411(4) 0.44790(2) 0.02016(9) Uani 1 1 d . . . . .
Si1 Si 0.35484(2) 1.15673(4) 0.70492(2) 0.01940(10) Uani 1 1 d . . . . .
F1 F 0.20506(3) 0.58894(9) 0.61666(6) 0.02481(18) Uani 1 1 d . . . . .
F2 F 0.23427(4) 1.08502(10) 0.51151(5) 0.02656(19) Uani 1 1 d . . . . .
O2 O 0.40356(4) 0.85253(13) 0.90831(7) 0.0268(2) Uani 1 1 d . . . . .
O3 O 0.11960(4) 1.05017(13) 0.56040(7) 0.0274(2) Uani 1 1 d . . . . .
O1 O 0.39640(4) 1.06732(12) 0.81044(7) 0.0253(2) Uani 1 1 d . . . . .
O5 O 0.48848(5) 1.21631(13) 0.95147(8) 0.0289(2) Uani 1 1 d . . . . .
C4 C 0.28457(6) 0.74071(16) 0.72003(9) 0.0193(3) Uani 1 1 d . . . . .
H4 H 0.2953 0.6620 0.7681 0.023 Uiso 1 1 calc R U . . .
O4 O -0.04354(5) 0.88338(17) 0.30391(9) 0.0402(3) Uani 1 1 d . . . . .
N1 N 0.03292(5) 1.00038(15) 0.42956(8) 0.0232(2) Uani 1 1 d . . . . .
C1 C 0.25062(6) 0.97228(15) 0.57985(9) 0.0191(2) Uani 1 1 d . . . . .
C5 C 0.23635(5) 0.72264(15) 0.63315(9) 0.0191(3) Uani 1 1 d . . . . .
C6 C 0.21727(5) 0.83618(16) 0.56044(9) 0.0184(2) Uani 1 1 d . . . . .
C9 C 0.08714(6) 0.96320(16) 0.49638(9) 0.0201(3) Uani 1 1 d . . . . .
C2 C 0.29995(5) 0.99599(15) 0.66383(9) 0.0185(2) Uani 1 1 d . . . . .
C10 C 0.10045(5) 0.79608(16) 0.47639(9) 0.0194(3) Uani 1 1 d . . . . .
H10 H 0.1101 0.7235 0.5313 0.023 Uiso 1 1 calc R U . . .
C3 C 0.31696(5) 0.87795(15) 0.73495(9) 0.0179(2) Uani 1 1 d . . . . .
B1 B 0.37476(6) 0.92650(18) 0.82411(11) 0.0209(3) Uani 1 1 d . . . . .
C11 C 0.04614(6) 0.74151(18) 0.38821(10) 0.0244(3) Uani 1 1 d . . . . .
H11A H 0.0534 0.7216 0.3346 0.029 Uiso 1 1 calc R U . . .
H11B H 0.0312 0.6427 0.4015 0.029 Uiso 1 1 calc R U . . .
C12 C 0.00507(6) 0.87820(19) 0.36612(10) 0.0260(3) Uani 1 1 d . . . . .
C7 C 0.33281(6) 1.35409(16) 0.72494(10) 0.0243(3) Uani 1 1 d . . . . .
H7A H 0.3131 1.3422 0.7620 0.037 Uiso 1 1 calc R U . . .
H7B H 0.3073 1.4036 0.6638 0.037 Uiso 1 1 calc R U . . .
H7C H 0.3663 1.4216 0.7597 0.037 Uiso 1 1 calc R U . . .
C8 C 0.39242(7) 1.17122(19) 0.63516(13) 0.0334(3) Uani 1 1 d . . . . .
H8A H 0.4036 1.0644 0.6259 0.050 Uiso 1 1 calc R U . . .
H8B H 0.4263 1.2376 0.6693 0.050 Uiso 1 1 calc R U . . .
H8C H 0.3673 1.2194 0.5734 0.050 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
S1 C6 1.7634(13) . ?
S1 C10 1.8224(13) . ?
Si1 O1 1.6927(10) . ?
Si1 C7 1.8398(15) . ?
Si1 C8 1.8496(16) . ?
Si1 C2 1.8705(14) . ?
F1 C5 1.3505(15) . ?
F2 C1 1.3536(15) . ?
O2 B1 1.3452(18) . ?
O2 H2 0.79(3) . ?
O3 C9 1.2199(17) . ?
O1 B1 1.3820(18) . ?
O5 H5A 0.92(3) . ?
O5 H5B 0.88(3) . ?
C4 C5 1.3823(19) . ?
C4 C3 1.3939(18) . ?
C4 H4 0.9500 . ?
O4 C12 1.2051(18) . ?
N1 C9 1.3674(17) . ?
N1 C12 1.3842(19) . ?
N1 H1 0.89(2) . ?
C1 C2 1.3772(18) . ?
C1 C6 1.3922(18) . ?
C5 C6 1.4006(19) . ?
C9 C10 1.5200(18) . ?
C2 C3 1.4129(18) . ?
C10 C11 1.5355(18) . ?
C10 H10 1.0000 . ?
C3 B1 1.5782(19) . ?
C11 C12 1.512(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
C6 S1 C10 101.80(6) . . ?
O1 Si1 C7 109.56(6) . . ?
O1 Si1 C8 110.48(7) . . ?
C7 Si1 C8 111.56(7) . . ?
O1 Si1 C2 93.52(5) . . ?
C7 Si1 C2 116.27(6) . . ?
C8 Si1 C2 113.95(7) . . ?
B1 O2 H2 116.9(17) . . ?
B1 O1 Si1 114.46(9) . . ?
H5A O5 H5B 105(2) . . ?
C5 C4 C3 117.95(12) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C9 N1 C12 113.80(12) . . ?
C9 N1 H1 122.3(13) . . ?
C12 N1 H1 123.7(13) . . ?
F2 C1 C2 118.54(12) . . ?
F2 C1 C6 118.03(11) . . ?
C2 C1 C6 123.41(12) . . ?
F1 C5 C4 118.81(12) . . ?
F1 C5 C6 117.32(11) . . ?
C4 C5 C6 123.86(12) . . ?
C1 C6 C5 115.74(12) . . ?
C1 C6 S1 121.42(10) . . ?
C5 C6 S1 122.67(10) . . ?
O3 C9 N1 125.82(13) . . ?
O3 C9 C10 125.76(12) . . ?
N1 C9 C10 108.41(11) . . ?
C1 C2 C3 118.41(12) . . ?
C1 C2 Si1 132.37(10) . . ?
C3 C2 Si1 109.14(9) . . ?
C9 C10 C11 104.70(11) . . ?
C9 C10 S1 109.73(9) . . ?
C11 C10 S1 108.93(9) . . ?
C9 C10 H10 111.1 . . ?
C11 C10 H10 111.1 . . ?
S1 C10 H10 111.1 . . ?
C4 C3 C2 120.60(12) . . ?
C4 C3 B1 129.07(12) . . ?
C2 C3 B1 110.32(11) . . ?
O2 B1 O1 118.27(12) . . ?
O2 B1 C3 129.24(13) . . ?
O1 B1 C3 112.49(12) . . ?
C12 C11 C10 104.68(11) . . ?
C12 C11 H11A 110.8 . . ?
C10 C11 H11A 110.8 . . ?
C12 C11 H11B 110.8 . . ?
C10 C11 H11B 110.8 . . ?
H11A C11 H11B 108.9 . . ?
O4 C12 N1 124.76(14) . . ?
O4 C12 C11 126.93(14) . . ?
N1 C12 C11 108.30(12) . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.556
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_24
_database_code_depnum_ccdc_archive 'CCDC 2258836'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 B Cl F2 O4 S Si'
_chemical_formula_sum            'C8 H8 B Cl F2 O4 S Si'
_chemical_formula_weight         312.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.2732(3)
_cell_length_b                   10.00400(10)
_cell_length_c                   11.9960(3)
_cell_angle_alpha                90
_cell_angle_beta                 119.008(3)
_cell_angle_gamma                90
_cell_volume                     1288.11(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9585
_cell_measurement_theta_min      4.0910
_cell_measurement_theta_max      76.4040


_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    5.328
_exptl_crystal_size_max          0.112
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.068
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 6 1 0.0523
0 -6 0 0.0509
8 0 -2 0.0301
-8 0 2 0.0419
4 5 1 0.0485
-5 -6 2 0.0563
0 0 -7 0.0318
0 0 7 0.0366
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.4991 5.9922 1.0287 -0.4540 -0.4630 0.6851
-0.0009 -5.9933 -0.0265 0.4045 0.2991 -0.7743
8.0113 -0.0091 -2.0188 0.6480 0.5841 0.5638
-8.0113 0.0091 2.0188 -0.6480 -0.5841 -0.5638
3.5123 4.9820 1.0099 0.1623 -0.1568 0.9415
-4.5041 -5.9921 1.9822 0.1408 -0.1056 -1.0682
-0.0247 0.0316 -6.9851 -0.8062 0.6089 -0.1853
0.0247 -0.0316 6.9851 0.8062 -0.6089 0.1853
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.814
_oxdiff_exptl_absorpt_empirical_full_max 1.308
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      99.99(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2195

_diffrn_reflns_number            13035
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.119
_diffrn_reflns_theta_max         76.578
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2660
_reflns_number_gt                2522
_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'

_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)+(0.0346P)²+0.6733P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2660
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0668
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_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
C1 C 0.79303(12) 0.65321(13) 0.33154(12) 0.0152(3) Uani 1 1 d . . . . .
C2 C 0.92156(12) 0.66649(13) 0.37368(12) 0.0157(3) Uani 1 1 d . . . . .
C3 C 0.99022(12) 0.56128(13) 0.36331(13) 0.0171(3) Uani 1 1 d . . . . .
H3 H 1.0764 0.5716 0.3901 0.021 Uiso 1 1 calc R U . . .
C4 C 0.93055(12) 0.44161(13) 0.31326(12) 0.0167(3) Uani 1 1 d . . . . .
C5 C 0.80302(12) 0.42369(13) 0.26996(12) 0.0158(3) Uani 1 1 d . . . . .
C6 C 0.73713(12) 0.53320(13) 0.27945(12) 0.0160(3) Uani 1 1 d . . . . .
C7 C 0.68816(15) 0.79142(16) 0.48942(15) 0.0261(3) Uani 1 1 d . . . . .
H7A H 0.7533 0.7420 0.5615 0.039 Uiso 1 1 calc R U . . .
H7B H 0.6097 0.7415 0.4543 0.039 Uiso 1 1 calc R U . . .
H7C H 0.6771 0.8793 0.5185 0.039 Uiso 1 1 calc R U . . .
C8 C 0.61816(13) 0.90483(14) 0.22485(14) 0.0219(3) Uani 1 1 d . . . . .
H8A H 0.6476 0.9130 0.1624 0.033 Uiso 1 1 calc R U . . .
H8B H 0.6063 0.9941 0.2508 0.033 Uiso 1 1 calc R U . . .
H8C H 0.5388 0.8564 0.1865 0.033 Uiso 1 1 calc R U . . .
O1 O 1.08796(9) 0.84918(11) 0.48242(11) 0.0247(2) Uani 1 1 d D . . . .
O2 O 0.87397(9) 0.88946(9) 0.42734(9) 0.0196(2) Uani 1 1 d . . . . .
O3 O 0.63377(10) 0.24993(10) 0.24409(10) 0.0229(2) Uani 1 1 d . . . . .
O4 O 0.80870(10) 0.16997(10) 0.21529(12) 0.0276(2) Uani 1 1 d . . . . .
B1 B 0.96908(15) 0.81083(15) 0.43235(15) 0.0180(3) Uani 1 1 d . . . . .
Si1 Si 0.73400(3) 0.81293(3) 0.36512(3) 0.01592(10) Uani 1 1 d . . . . .
F1 F 0.61309(7) 0.52119(8) 0.23307(8) 0.02173(18) Uani 1 1 d . . . . .
F2 F 0.99895(8) 0.33898(8) 0.30862(8) 0.02276(19) Uani 1 1 d . . . . .
S1 S 0.72404(3) 0.27213(3) 0.20424(3) 0.01830(9) Uani 1 1 d . . . . .
H1A H 1.1023(17) 0.9243(12) 0.5153(17) 0.027 Uiso 1 1 d D U . . .
Cl1 Cl 0.62839(4) 0.32266(4) 0.01673(3) 0.03077(11) 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
C1 C6 1.3737(18) . ?
C1 C2 1.4101(18) . ?
C1 Si1 1.8770(14) . ?
C2 C3 1.3911(19) . ?
C2 B1 1.5881(19) . ?
C3 C4 1.3798(19) . ?
C3 H3 0.9500 . ?
C4 F2 1.3443(15) . ?
C4 C5 1.4012(18) . ?
C5 C6 1.3986(18) . ?
C5 S1 1.7660(13) . ?
C6 F1 1.3491(15) . ?
C7 Si1 1.8438(16) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 Si1 1.8378(15) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O1 B1 1.3368(19) . ?
O1 H1A 0.827(9) . ?
O2 B1 1.3845(18) . ?
O2 Si1 1.6885(10) . ?
O3 S1 1.4209(11) . ?
O4 S1 1.4171(11) . ?
S1 Cl1 2.0328(5) . ?

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
C6 C1 C2 118.07(12) . . ?
C6 C1 Si1 133.01(10) . . ?
C2 C1 Si1 108.90(9) . . ?
C3 C2 C1 121.17(12) . . ?
C3 C2 B1 128.27(12) . . ?
C1 C2 B1 110.55(12) . . ?
C4 C3 C2 118.60(12) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
F2 C4 C3 118.06(12) . . ?
F2 C4 C5 119.65(12) . . ?
C3 C4 C5 122.28(12) . . ?
C6 C5 C4 117.11(12) . . ?
C6 C5 S1 119.67(10) . . ?
C4 C5 S1 123.23(10) . . ?
F1 C6 C1 118.69(12) . . ?
F1 C6 C5 118.56(11) . . ?
C1 C6 C5 122.73(12) . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
B1 O1 H1A 114.1(13) . . ?
B1 O2 Si1 114.66(9) . . ?
O1 B1 O2 124.75(13) . . ?
O1 B1 C2 123.11(13) . . ?
O2 B1 C2 112.13(12) . . ?
O2 Si1 C8 110.33(6) . . ?
O2 Si1 C7 109.85(6) . . ?
C8 Si1 C7 113.26(7) . . ?
O2 Si1 C1 93.72(5) . . ?
C8 Si1 C1 115.91(6) . . ?
C7 Si1 C1 112.03(7) . . ?
O4 S1 O3 120.78(7) . . ?
O4 S1 C5 111.01(6) . . ?
O3 S1 C5 109.44(6) . . ?
O4 S1 Cl1 106.65(5) . . ?
O3 S1 Cl1 106.56(5) . . ?
C5 S1 Cl1 100.25(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 O4 0.95 2.51 3.2277(17) 132.7 2_755
O1 H1A O2 0.827(9) 1.958(10) 2.7814(14) 173.3(19) 3_776

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_22
_database_code_depnum_ccdc_archive 'CCDC 2190667'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
S-(5,7-difluoro-3-hydroxy-1,1-dimethyl-1,3-dihydrobenzo[c][1,2,5]oxasilaborol-6-yl) O,O-diethyl phosphorothioate 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 B F2 O5 P S Si'
_chemical_formula_sum            'C12 H18 B F2 O5 P S Si'
_chemical_formula_weight         382.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.0595(14)
_cell_length_b                   7.3061(7)
_cell_length_c                   18.839(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.507(16)
_cell_angle_gamma                90
_cell_volume                     1796.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3585
_cell_measurement_theta_min      4.1220
_cell_measurement_theta_max      76.0480

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    3.443
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.060
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 -1 14 0.0383
7 1 -14 0.0221
-7 0 0 0.0697
6 0 2 0.0529
-2 1 13 0.0469
3 -3 -12 0.0290
0 5 0 0.0286
0 -5 0 0.0334
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7.0649 -0.9005 14.0681 -0.2049 -0.6500 0.7550
7.0649 0.9005 -14.0681 0.2049 0.6500 -0.7550
-7.0128 0.0610 0.0040 -0.2958 -0.8983 -0.3780
6.0079 -0.0476 1.9989 0.2394 0.8168 0.4799
-1.9927 1.0427 12.9690 -0.3663 0.1275 0.8647
2.9315 -3.0382 -11.8735 0.7812 -0.1350 -0.6504
0.1537 4.9729 -0.2374 -0.9494 0.3982 -0.2058
-0.1537 -4.9729 0.2374 0.9494 -0.3982 0.2058
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.759
_oxdiff_exptl_absorpt_empirical_full_max 1.427
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2195

_diffrn_reflns_number            10700
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.069
_diffrn_reflns_theta_max         76.810
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3683
_reflns_number_gt                3030
_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'

_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)+(0.0702P)²+1.5143P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3683
_refine_ls_number_parameters     211
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1354
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_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
C11 C 1.1031(2) 0.9684(4) 0.29157(14) 0.0300(6) Uani 1 1 d . . . . .
H11A H 1.1584 0.8857 0.3087 0.036 Uiso 1 1 calc R U . . .
H11B H 1.0875 1.0547 0.3304 0.036 Uiso 1 1 calc R U . . .
C12 C 1.1385(2) 1.0736(5) 0.22830(14) 0.0324(6) Uani 1 1 d . . . . .
H12A H 1.1996 1.1448 0.2417 0.049 Uiso 1 1 calc R U . . .
H12B H 1.0840 1.1565 0.2117 0.049 Uiso 1 1 calc R U . . .
H12C H 1.1550 0.9880 0.1902 0.049 Uiso 1 1 calc R U . . .
C14 C 0.8762(2) 0.4438(4) 0.19735(14) 0.0286(6) Uani 1 1 d . . . . .
H14A H 0.9039 0.3377 0.2244 0.034 Uiso 1 1 calc R U . . .
H14B H 0.9053 0.4421 0.1494 0.034 Uiso 1 1 calc R U . . .
C15 C 0.7616(2) 0.4330(5) 0.19196(17) 0.0369(7) Uani 1 1 d . . . . .
H15A H 0.7413 0.3194 0.1678 0.055 Uiso 1 1 calc R U . . .
H15B H 0.7350 0.5380 0.1649 0.055 Uiso 1 1 calc R U . . .
H15C H 0.7336 0.4345 0.2397 0.055 Uiso 1 1 calc R U . . .
O3 O 1.01017(14) 0.8592(3) 0.27301(9) 0.0249(4) Uani 1 1 d . . . . .
O4 O 0.90378(14) 0.6144(3) 0.23378(9) 0.0245(4) Uani 1 1 d . . . . .
O5 O 1.09159(15) 0.6091(3) 0.19390(9) 0.0282(4) Uani 1 1 d . . . . .
P1 P 1.01995(5) 0.65542(10) 0.25023(3) 0.02169(18) Uani 1 1 d . . . . .
C1 C 0.80808(19) 0.5250(4) 0.45401(13) 0.0227(5) Uani 1 1 d . . . . .
C2 C 0.8798(2) 0.4783(4) 0.40524(12) 0.0224(5) Uani 1 1 d . . . . .
C3 C 0.97287(19) 0.5696(4) 0.39938(12) 0.0213(5) Uani 1 1 d . . . . .
C4 C 0.9914(2) 0.7133(4) 0.44688(13) 0.0229(5) Uani 1 1 d . . . . .
C5 C 0.9228(2) 0.7668(4) 0.49698(12) 0.0232(5) Uani 1 1 d . . . . .
H5 H 0.9380 0.8653 0.5284 0.028 Uiso 1 1 calc R U . . .
C6 C 0.83025(19) 0.6722(4) 0.50026(12) 0.0209(5) Uani 1 1 d . . . . .
C7 C 0.6666(3) 0.2059(5) 0.50563(18) 0.0385(7) Uani 1 1 d . . . . .
H7A H 0.7158 0.1884 0.5452 0.058 Uiso 1 1 calc R U . . .
H7B H 0.6823 0.1207 0.4672 0.058 Uiso 1 1 calc R U . . .
H7C H 0.5971 0.1827 0.5219 0.058 Uiso 1 1 calc R U . . .
C8 C 0.5849(2) 0.4868(5) 0.39790(14) 0.0322(6) Uani 1 1 d . . . . .
H8A H 0.5921 0.6138 0.3821 0.048 Uiso 1 1 calc R U . . .
H8B H 0.5146 0.4661 0.4132 0.048 Uiso 1 1 calc R U . . .
H8C H 0.5998 0.4039 0.3586 0.048 Uiso 1 1 calc R U . . .
O1 O 0.74320(15) 0.8343(3) 0.60360(9) 0.0268(4) Uani 1 1 d D . . . .
O2 O 0.65706(14) 0.5926(3) 0.53899(9) 0.0273(4) Uani 1 1 d . . . . .
Si1 Si 0.67528(5) 0.44256(11) 0.47287(3) 0.02435(19) Uani 1 1 d . . . . .
B1 B 0.7382(2) 0.7070(5) 0.55251(14) 0.0234(6) Uani 1 1 d . . . . .
F1 F 0.86078(13) 0.3354(2) 0.36112(8) 0.0302(4) Uani 1 1 d . . . . .
F2 F 1.08182(12) 0.8018(2) 0.44340(8) 0.0272(4) Uani 1 1 d . . . . .
S1 S 1.06637(5) 0.49987(10) 0.33802(3) 0.02329(17) Uani 1 1 d . . . . .
H1 H 0.6920(18) 0.846(5) 0.6291(16) 0.035 Uiso 1 1 d D 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
C11 O3 1.486(3) . ?
C11 C12 1.501(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 O4 1.463(3) . ?
C14 C15 1.500(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O3 P1 1.555(2) . ?
O4 P1 1.5695(19) . ?
O5 P1 1.4723(19) . ?
P1 S1 2.0836(9) . ?
C1 C2 1.372(4) . ?
C1 C6 1.410(4) . ?
C1 Si1 1.879(3) . ?
C2 F1 1.353(3) . ?
C2 C3 1.393(4) . ?
C3 C4 1.397(4) . ?
C3 S1 1.778(2) . ?
C4 F2 1.349(3) . ?
C4 C5 1.375(4) . ?
C5 C6 1.395(4) . ?
C5 H5 0.9500 . ?
C6 B1 1.595(4) . ?
C7 Si1 1.840(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 Si1 1.845(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O1 B1 1.338(4) . ?
O1 H1 0.838(10) . ?
O2 B1 1.368(4) . ?
O2 Si1 1.681(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
O3 C11 C12 110.8(2) . . ?
O3 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C14 C15 108.0(2) . . ?
O4 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
O4 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 O3 P1 120.43(18) . . ?
C14 O4 P1 118.68(18) . . ?
O5 P1 O3 118.50(12) . . ?
O5 P1 O4 116.30(11) . . ?
O3 P1 O4 98.71(11) . . ?
O5 P1 S1 105.64(9) . . ?
O3 P1 S1 109.10(7) . . ?
O4 P1 S1 108.18(8) . . ?
C2 C1 C6 118.1(2) . . ?
C2 C1 Si1 134.2(2) . . ?
C6 C1 Si1 107.65(19) . . ?
F1 C2 C1 119.0(2) . . ?
F1 C2 C3 117.8(2) . . ?
C1 C2 C3 123.1(2) . . ?
C2 C3 C4 116.5(2) . . ?
C2 C3 S1 122.0(2) . . ?
C4 C3 S1 121.4(2) . . ?
F2 C4 C5 119.0(2) . . ?
F2 C4 C3 117.8(2) . . ?
C5 C4 C3 123.3(2) . . ?
C4 C5 C6 118.1(3) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C5 C6 C1 121.0(2) . . ?
C5 C6 B1 128.1(2) . . ?
C1 C6 B1 110.9(2) . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
B1 O1 H1 117(3) . . ?
B1 O2 Si1 114.37(17) . . ?
O2 Si1 C7 110.67(13) . . ?
O2 Si1 C8 110.65(13) . . ?
C7 Si1 C8 112.17(15) . . ?
O2 Si1 C1 94.62(11) . . ?
C7 Si1 C1 115.46(14) . . ?
C8 Si1 C1 111.99(12) . . ?
O1 B1 O2 125.6(2) . . ?
O1 B1 C6 122.1(2) . . ?
O2 B1 C6 112.4(2) . . ?
C3 S1 P1 99.75(9) . . ?

_refine_diff_density_max         0.477
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.090

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2190662'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
3-((5,7-difluoro-3-hydroxy-1,1-dimethyl-1,3-dihydrobenzo[c][1,2,5]oxasilaborol-6-yl)thio)-N-(5-methylisoxazol-3-yl)propanamide 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 B F2 N2 O4 S Si'
_chemical_formula_sum            'C15 H17 B F2 N2 O4 S Si'
_chemical_formula_weight         398.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 '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                   8.6314(4)
_cell_length_b                   10.5815(4)
_cell_length_c                   20.2719(10)
_cell_angle_alpha                80.173(4)
_cell_angle_beta                 80.300(4)
_cell_angle_gamma                82.873(4)
_cell_volume                     1789.57(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5107
_cell_measurement_theta_min      4.2170
_cell_measurement_theta_max      68.9280

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    2.660
_cell_oxdiff_measurement_reflns_used 5107
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0391
0 1 0 0.0427
0 -1 0 0.0427
-2 0 5 0.0768
2 0 -5 0.0591
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0026 -1.0007 0.0021 -0.0177 -0.0763 0.1262
0.0026 1.0007 -0.0021 0.0177 0.0763 -0.1262
-0.0026 -1.0007 0.0021 -0.0177 -0.0763 0.1262
-2.0045 0.0087 5.0043 0.1442 0.4515 0.3220
2.0045 -0.0087 -5.0043 -0.1442 -0.4515 -0.3220
_exptl_absorpt_correction_T_min  0.86567
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.848
_oxdiff_exptl_absorpt_empirical_full_max 1.456
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2195

_diffrn_reflns_number            11958
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.237
_diffrn_reflns_theta_max         69.753
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             6540
_reflns_number_gt                5418
_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'

_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)+(0.0504P)²+2.2533P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6540
_refine_ls_number_parameters     481
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_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
S1 S -0.26316(8) 0.90226(6) 0.23046(4) 0.02443(16) Uani 1 1 d . . . . .
S2 S 0.70249(9) 0.31247(8) 0.79478(4) 0.03114(18) Uani 1 1 d . . . . .
Si1 Si 0.02809(9) 0.40503(7) 0.34345(4) 0.02265(18) Uani 1 1 d . . . . .
Si2 Si 0.59713(9) 0.03628(7) 0.58660(4) 0.02334(18) Uani 1 1 d . . . . .
F3 F -0.18444(19) 0.61441(15) 0.24092(8) 0.0253(3) Uani 1 1 d . . . . .
F1 F 0.7420(2) 0.08689(16) 0.72041(8) 0.0287(4) Uani 1 1 d . . . . .
F4 F -0.1212(2) 0.97181(15) 0.34105(9) 0.0315(4) Uani 1 1 d . . . . .
F2 F 0.5033(2) 0.51395(17) 0.71420(10) 0.0358(4) Uani 1 1 d . . . . .
O5 O 0.1332(2) 0.41087(18) 0.40571(10) 0.0253(4) Uani 1 1 d . . . . .
O10 O -0.0289(2) 0.48581(18) 1.12568(10) 0.0265(4) Uani 1 1 d . . . . .
O6 O 0.1766(2) 0.5572(2) 0.47851(10) 0.0272(4) Uani 1 1 d D . . . .
O3 O 0.2991(2) 0.23151(18) 0.96769(10) 0.0265(4) Uani 1 1 d . . . . .
O2 O 0.3613(3) 0.3332(2) 0.49850(11) 0.0316(5) Uani 1 1 d D . . . .
O8 O 0.4919(2) 0.73483(18) -0.08994(10) 0.0265(4) Uani 1 1 d . . . . .
O1 O 0.4833(2) 0.12003(18) 0.53111(10) 0.0261(4) Uani 1 1 d . . . . .
O7 O 0.1263(3) 1.00162(18) 0.05187(11) 0.0302(5) Uani 1 1 d . . . . .
N1 N 0.2647(3) 0.4377(2) 0.98985(12) 0.0230(5) Uani 1 1 d D . . . .
N2 N 0.1717(3) 0.7927(2) 0.03381(12) 0.0224(5) Uani 1 1 d D . . . .
N4 N 0.3652(3) 0.6970(2) -0.03958(12) 0.0255(5) Uani 1 1 d . . . . .
N5 N 0.0935(3) 0.5253(2) 1.07396(12) 0.0256(5) Uani 1 1 d . . . . .
C12 C 0.1446(3) 0.4236(2) 1.04419(14) 0.0215(6) Uani 1 1 d . . . . .
C20 C -0.1265(3) 0.6642(3) 0.28808(14) 0.0208(5) Uani 1 1 d . . . . .
C28 C 0.2998(3) 0.8034(3) -0.01667(14) 0.0221(6) Uani 1 1 d . . . . .
C15 C -0.0455(3) 0.3602(3) 1.12427(14) 0.0231(6) Uani 1 1 d . . . . .
C4 C 0.6246(3) 0.3007(3) 0.72100(14) 0.0240(6) Uani 1 1 d . . . . .
C27 C 0.0911(3) 0.8916(2) 0.06562(14) 0.0213(6) Uani 1 1 d . . . . .
C1 C 0.5038(3) 0.2819(3) 0.60277(14) 0.0226(6) Uani 1 1 d . . . . .
C30 C 0.4956(3) 0.8634(3) -0.09434(14) 0.0237(6) Uani 1 1 d . . . . .
C5 C 0.6526(3) 0.1880(3) 0.69131(14) 0.0237(6) Uani 1 1 d . . . . .
C19 C -0.0417(3) 0.5825(3) 0.33211(14) 0.0214(6) Uani 1 1 d . . . . .
C22 C -0.0979(3) 0.8430(3) 0.33911(15) 0.0233(6) Uani 1 1 d . . . . .
C29 C 0.3782(3) 0.9128(3) -0.04984(14) 0.0230(6) Uani 1 1 d . . . . .
H29 H 0.3540 0.9998 -0.0425 0.028 Uiso 1 1 calc R U . . .
C50 C 0.0609(3) 0.3155(3) 1.07435(14) 0.0228(6) Uani 1 1 d . . . . .
H50 H 0.0760 0.2315 1.0623 0.027 Uiso 1 1 calc R U . . .
C2 C 0.4765(3) 0.3976(3) 0.62921(15) 0.0249(6) Uani 1 1 d . . . . .
H2 H 0.4184 0.4705 0.6075 0.030 Uiso 1 1 calc R U . . .
C21 C -0.1570(3) 0.7972(3) 0.28861(14) 0.0222(6) Uani 1 1 d . . . . .
C6 C 0.5925(3) 0.1749(3) 0.63454(14) 0.0219(6) Uani 1 1 d . . . . .
C11 C 0.3332(3) 0.3421(3) 0.95357(14) 0.0230(6) Uani 1 1 d . . . . .
C26 C -0.0430(3) 0.8492(3) 0.11916(14) 0.0225(6) Uani 1 1 d . . . . .
H26A H -0.0076 0.7675 0.1467 0.027 Uiso 1 1 calc R U . . .
H26B H -0.1312 0.8329 0.0972 0.027 Uiso 1 1 calc R U . . .
C25 C -0.1009(3) 0.9500(3) 0.16496(14) 0.0244(6) Uani 1 1 d . . . . .
H25A H -0.1356 1.0316 0.1371 0.029 Uiso 1 1 calc R U . . .
H25B H -0.0122 0.9662 0.1866 0.029 Uiso 1 1 calc R U . . .
C23 C -0.0177(3) 0.7661(3) 0.38652(14) 0.0238(6) Uani 1 1 d . . . . .
H23 H 0.0162 0.8013 0.4212 0.029 Uiso 1 1 calc R U . . .
C10 C 0.4547(4) 0.3864(3) 0.89324(15) 0.0272(6) Uani 1 1 d . . . . .
H10A H 0.4020 0.4485 0.8596 0.033 Uiso 1 1 calc R U . . .
H10B H 0.5341 0.4307 0.9083 0.033 Uiso 1 1 calc R U . . .
C16 C -0.1697(4) 0.3031(3) 1.17696(15) 0.0278(6) Uani 1 1 d . . . . .
H16A H -0.2223 0.3688 1.2041 0.042 Uiso 1 1 calc R U . . .
H16B H -0.1213 0.2311 1.2064 0.042 Uiso 1 1 calc R U . . .
H16C H -0.2474 0.2718 1.1551 0.042 Uiso 1 1 calc R U . . .
C9 C 0.5362(3) 0.2720(3) 0.86070(14) 0.0258(6) Uani 1 1 d . . . . .
H9A H 0.4582 0.2352 0.8407 0.031 Uiso 1 1 calc R U . . .
H9B H 0.5747 0.2049 0.8962 0.031 Uiso 1 1 calc R U . . .
C3 C 0.5359(3) 0.4033(3) 0.68746(16) 0.0262(6) Uani 1 1 d . . . . .
C8 C 0.5032(4) -0.1043(3) 0.63692(16) 0.0289(6) Uani 1 1 d . . . . .
H8A H 0.3986 -0.0756 0.6597 0.043 Uiso 1 1 calc R U . . .
H8B H 0.5689 -0.1470 0.6709 0.043 Uiso 1 1 calc R U . . .
H8C H 0.4922 -0.1651 0.6069 0.043 Uiso 1 1 calc R U . . .
C24 C 0.0128(3) 0.6349(3) 0.38248(14) 0.0222(6) Uani 1 1 d . . . . .
C17 C -0.1356(4) 0.3017(3) 0.37571(16) 0.0290(6) Uani 1 1 d . . . . .
H17A H -0.2029 0.3350 0.4142 0.043 Uiso 1 1 calc R U . . .
H17B H -0.0918 0.2133 0.3903 0.043 Uiso 1 1 calc R U . . .
H17C H -0.1984 0.3022 0.3396 0.043 Uiso 1 1 calc R U . . .
C31 C 0.6233(4) 0.9192(3) -0.14501(16) 0.0303(7) Uani 1 1 d . . . . .
H31A H 0.6855 0.8509 -0.1679 0.046 Uiso 1 1 calc R U . . .
H31B H 0.6918 0.9589 -0.1222 0.046 Uiso 1 1 calc R U . . .
H31C H 0.5770 0.9846 -0.1784 0.046 Uiso 1 1 calc R U . . .
C7 C 0.7956(4) -0.0081(3) 0.54130(17) 0.0328(7) Uani 1 1 d . . . . .
H7A H 0.8401 0.0697 0.5157 0.049 Uiso 1 1 calc R U . . .
H7B H 0.7874 -0.0674 0.5101 0.049 Uiso 1 1 calc R U . . .
H7C H 0.8644 -0.0502 0.5741 0.049 Uiso 1 1 calc R U . . .
C18 C 0.1603(4) 0.3476(3) 0.27042(16) 0.0294(6) Uani 1 1 d . . . . .
H18A H 0.2449 0.4043 0.2548 0.044 Uiso 1 1 calc R U . . .
H18B H 0.0996 0.3484 0.2336 0.044 Uiso 1 1 calc R U . . .
H18C H 0.2063 0.2596 0.2842 0.044 Uiso 1 1 calc R U . . .
B2 B 0.1134(4) 0.5313(3) 0.42677(16) 0.0247(7) Uani 1 1 d . . . . .
B1 B 0.4441(4) 0.2463(3) 0.54002(17) 0.0253(7) Uani 1 1 d . . . . .
H1N H 0.303(4) 0.509(2) 0.9791(19) 0.038 Uiso 1 1 d D U . . .
H2N H 0.137(4) 0.7203(19) 0.0459(18) 0.038 Uiso 1 1 d D U . . .
H6A H 0.230(4) 0.492(2) 0.4948(18) 0.038 Uiso 1 1 d D U . . .
H2A H 0.319(4) 0.306(3) 0.4700(14) 0.038 Uiso 1 1 d D 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
S1 C21 1.769(3) . ?
S1 C25 1.816(3) . ?
S2 C4 1.768(3) . ?
S2 C9 1.827(3) . ?
Si1 O5 1.687(2) . ?
Si1 C18 1.852(3) . ?
Si1 C17 1.857(3) . ?
Si1 C19 1.887(3) . ?
Si2 O1 1.683(2) . ?
Si2 C7 1.848(3) . ?
Si2 C8 1.848(3) . ?
Si2 C6 1.886(3) . ?
F3 C20 1.357(3) . ?
F1 C5 1.350(3) . ?
F4 C22 1.359(3) . ?
F2 C3 1.352(3) . ?
O5 B2 1.393(4) . ?
O10 C15 1.360(3) . ?
O10 N5 1.406(3) . ?
O6 B2 1.342(4) . ?
O6 H6A 0.837(10) . ?
O3 C11 1.217(3) . ?
O2 B1 1.357(4) . ?
O2 H2A 0.837(10) . ?
O8 C30 1.352(3) . ?
O8 N4 1.411(3) . ?
O1 B1 1.372(4) . ?
O7 C27 1.214(3) . ?
N1 C11 1.368(4) . ?
N1 C12 1.381(4) . ?
N1 H1N 0.837(10) . ?
N2 C28 1.376(4) . ?
N2 C27 1.376(4) . ?
N2 H2N 0.841(10) . ?
N4 C28 1.316(4) . ?
N5 C12 1.316(4) . ?
C12 C50 1.421(4) . ?
C20 C19 1.371(4) . ?
C20 C21 1.401(4) . ?
C28 C29 1.423(4) . ?
C15 C50 1.354(4) . ?
C15 C16 1.487(4) . ?
C4 C3 1.395(4) . ?
C4 C5 1.402(4) . ?
C27 C26 1.503(4) . ?
C1 C2 1.396(4) . ?
C1 C6 1.409(4) . ?
C1 B1 1.568(4) . ?
C30 C29 1.355(4) . ?
C30 C31 1.480(4) . ?
C5 C6 1.374(4) . ?
C19 C24 1.411(4) . ?
C22 C23 1.372(4) . ?
C22 C21 1.396(4) . ?
C29 H29 0.9500 . ?
C50 H50 0.9500 . ?
C2 C3 1.377(4) . ?
C2 H2 0.9500 . ?
C11 C10 1.520(4) . ?
C26 C25 1.516(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C23 C24 1.395(4) . ?
C23 H23 0.9500 . ?
C10 C9 1.517(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C24 B2 1.566(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C21 S1 C25 99.89(13) . . ?
C4 S2 C9 101.27(13) . . ?
O5 Si1 C18 109.86(13) . . ?
O5 Si1 C17 110.29(13) . . ?
C18 Si1 C17 111.80(14) . . ?
O5 Si1 C19 94.95(11) . . ?
C18 Si1 C19 115.82(13) . . ?
C17 Si1 C19 112.84(13) . . ?
O1 Si2 C7 109.58(14) . . ?
O1 Si2 C8 111.74(13) . . ?
C7 Si2 C8 112.82(14) . . ?
O1 Si2 C6 94.06(11) . . ?
C7 Si2 C6 112.92(13) . . ?
C8 Si2 C6 114.23(13) . . ?
B2 O5 Si1 112.84(19) . . ?
C15 O10 N5 108.3(2) . . ?
B2 O6 H6A 110(3) . . ?
B1 O2 H2A 118(3) . . ?
C30 O8 N4 108.0(2) . . ?
B1 O1 Si2 113.41(19) . . ?
C11 N1 C12 125.1(2) . . ?
C11 N1 H1N 117(3) . . ?
C12 N1 H1N 118(3) . . ?
C28 N2 C27 125.8(2) . . ?
C28 N2 H2N 118(3) . . ?
C27 N2 H2N 116(3) . . ?
C28 N4 O8 105.6(2) . . ?
C12 N5 O10 105.5(2) . . ?
N5 C12 N1 117.2(2) . . ?
N5 C12 C50 112.0(3) . . ?
N1 C12 C50 130.8(2) . . ?
F3 C20 C19 118.6(2) . . ?
F3 C20 C21 117.6(2) . . ?
C19 C20 C21 123.8(3) . . ?
N4 C28 N2 117.3(2) . . ?
N4 C28 C29 112.0(3) . . ?
N2 C28 C29 130.8(2) . . ?
C50 C15 O10 110.2(2) . . ?
C50 C15 C16 134.9(3) . . ?
O10 C15 C16 115.0(2) . . ?
C3 C4 C5 115.7(3) . . ?
C3 C4 S2 122.5(2) . . ?
C5 C4 S2 121.8(2) . . ?
O7 C27 N2 123.0(3) . . ?
O7 C27 C26 123.8(3) . . ?
N2 C27 C26 113.2(2) . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 B1 129.2(3) . . ?
C6 C1 B1 110.3(2) . . ?
O8 C30 C29 110.8(2) . . ?
O8 C30 C31 115.1(2) . . ?
C29 C30 C31 134.1(3) . . ?
F1 C5 C6 118.3(2) . . ?
F1 C5 C4 118.3(3) . . ?
C6 C5 C4 123.4(3) . . ?
C20 C19 C24 117.9(2) . . ?
C20 C19 Si1 135.1(2) . . ?
C24 C19 Si1 106.9(2) . . ?
F4 C22 C23 118.2(2) . . ?
F4 C22 C21 117.7(2) . . ?
C23 C22 C21 124.0(3) . . ?
C30 C29 C28 103.6(2) . . ?
C30 C29 H29 128.2 . . ?
C28 C29 H29 128.2 . . ?
C15 C50 C12 103.9(2) . . ?
C15 C50 H50 128.0 . . ?
C12 C50 H50 128.0 . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C22 C21 C20 115.3(3) . . ?
C22 C21 S1 121.3(2) . . ?
C20 C21 S1 123.5(2) . . ?
C5 C6 C1 118.4(3) . . ?
C5 C6 Si2 133.5(2) . . ?
C1 C6 Si2 108.1(2) . . ?
O3 C11 N1 123.2(3) . . ?
O3 C11 C10 122.7(3) . . ?
N1 C11 C10 114.1(2) . . ?
C27 C26 C25 111.5(2) . . ?
C27 C26 H26A 109.3 . . ?
C25 C26 H26A 109.3 . . ?
C27 C26 H26B 109.3 . . ?
C25 C26 H26B 109.3 . . ?
H26A C26 H26B 108.0 . . ?
C26 C25 S1 112.89(19) . . ?
C26 C25 H25A 109.0 . . ?
S1 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
S1 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C22 C23 C24 118.2(3) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
C9 C10 C11 110.3(2) . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C9 S2 113.5(2) . . ?
C10 C9 H9A 108.9 . . ?
S2 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
S2 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
F2 C3 C2 117.9(3) . . ?
F2 C3 C4 118.4(3) . . ?
C2 C3 C4 123.7(3) . . ?
Si2 C8 H8A 109.5 . . ?
Si2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C23 C24 C19 120.7(3) . . ?
C23 C24 B2 127.3(3) . . ?
C19 C24 B2 112.0(2) . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
Si2 C7 H7A 109.5 . . ?
Si2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O6 B2 O5 123.9(3) . . ?
O6 B2 C24 123.2(3) . . ?
O5 B2 C24 112.9(3) . . ?
O2 B1 O1 123.3(3) . . ?
O2 B1 C1 122.7(3) . . ?
O1 B1 C1 114.0(3) . . ?

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2296881'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology
Poland
;
_audit_update_record             
;
2023-09-22 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H14 B F O3 S Si'
_chemical_formula_sum            'C11 H14 B F O3 S Si'
_chemical_formula_weight         284.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   6.8604(4)
_cell_length_b                   9.1623(4)
_cell_length_c                   11.9467(5)
_cell_angle_alpha                101.758(4)
_cell_angle_beta                 103.715(4)
_cell_angle_gamma                105.684(4)
_cell_volume                     672.94(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3449
_cell_measurement_theta_min      5.2270
_cell_measurement_theta_max      77.1210

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    3.088
_exptl_crystal_size_max          0.482
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.066
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 5 0 0.1021
0 -1 0 0.0635
-2 5 0 0.1438
4 -1 -2 0.1587
0 -1 -5 0.0341
0 1 5 0.0324
-4 -1 3 0.2875
1 0 -5 0.0875
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9941 5.0001 0.0068 0.1715 0.8118 0.2304
-0.0009 -1.0000 -0.0018 -0.0211 -0.1556 -0.0928
-1.9926 5.0002 0.0045 0.2376 0.8455 -0.0031
3.9929 -0.9982 -1.9941 -0.0321 -0.3973 0.8073
-0.0010 -0.9947 -5.0052 0.6123 -0.4233 -0.1781
0.0010 0.9947 5.0052 -0.6123 0.4233 0.1781
-3.9946 -1.0029 2.9912 -0.1368 0.1396 -0.9758
0.9983 0.0053 -5.0011 0.5673 -0.3013 0.1482
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.641
_oxdiff_exptl_absorpt_empirical_full_max 1.715
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000

_diffrn_reflns_number            6224
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.975
_diffrn_reflns_theta_max         77.517
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.935
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.935
_reflns_number_total             2603
_reflns_number_gt                2243
_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.
;

# start Validation Reply Form
_vrf_PLAT029_3                   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.935 Why?  
RESPONSE: Only very weak diffraction was observed below 0.95
;
_vrf_PLAT097_3                   
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       2.71 eA-3  
RESPONSE: The structure is affected by disorder.
The residual peaks appear close to sulfur and silicon atoms.
Due to the small contribution of the disordered fractions
it was not included in the final refinement.
;
_vrf_PLAT971_3                   
;
PROBLEM: Check Calcd Resid. Dens.  1.12Ang From S1              2.86 eA-3  
RESPONSE:  The structure is affected by disorder.
The residual peaks appear close to sulfur and silicon atoms.
Due to the small contribution of the disordered fractions
it was not included in the final refinement.
;
# end Validation Reply Form

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'

_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2603
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.1077
_refine_ls_wR_factor_ref         0.325
_refine_ls_wR_factor_gt          0.317
_refine_ls_goodness_of_fit_ref   1.451
_refine_ls_restrained_S_all      1.451
_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
S1 S 0.31933(16) 0.15580(11) 0.54288(8) 0.0271(4) Uani 1 1 d . . . . .
Si1 Si 0.80350(18) 0.76054(12) 0.87124(10) 0.0265(5) Uani 1 1 d . . . . .
F1 F 0.4960(4) 0.4908(3) 0.6121(2) 0.0334(7) Uani 1 1 d . . . . .
O1 O 0.8951(5) 0.6058(3) 1.1494(3) 0.0280(7) Uani 1 1 d . . . . .
H1 H 0.9713 0.6934 1.1996 0.042 Uiso 1 1 calc R U . . .
O2 O 0.8969(5) 0.7713(3) 1.0163(3) 0.0288(8) Uani 1 1 d . . . . .
O3 O 0.1357(6) -0.1286(4) 0.3493(3) 0.0330(8) Uani 1 1 d . . . . .
C5 C 0.5340(7) 0.4377(5) 0.7117(4) 0.0245(9) Uani 1 1 d . . . . .
C6 C 0.6520(7) 0.5444(5) 0.8209(4) 0.0266(9) Uani 1 1 d . . . . .
C1 C 0.4506(7) 0.2741(5) 0.6934(4) 0.0269(9) Uani 1 1 d . . . . .
C3 C 0.6029(7) 0.3251(5) 0.9083(4) 0.0267(9) Uani 1 1 d . . . . .
H3 H 0.6242 0.2865 0.9766 0.032 Uiso 1 1 calc R U . . .
C2 C 0.4863(7) 0.2202(5) 0.7955(4) 0.0266(9) Uani 1 1 d . . . . .
H2 H 0.4300 0.1104 0.7874 0.032 Uiso 1 1 calc R U . . .
C4 C 0.6892(6) 0.4869(5) 0.9226(4) 0.0251(9) Uani 1 1 d . . . . .
C10 C 0.1648(7) -0.1635(5) 0.4438(4) 0.0289(10) Uani 1 1 d . . . . .
C9 C 0.2654(7) -0.0384(5) 0.5635(4) 0.0274(9) Uani 1 1 d . . . . .
H9A H 0.3998 -0.0503 0.6067 0.033 Uiso 1 1 calc R U . . .
H9B H 0.1684 -0.0522 0.6130 0.033 Uiso 1 1 calc R U . . .
C11 C 0.1067(8) -0.3335(5) 0.4487(4) 0.0340(11) Uani 1 1 d . . . . .
H11A H 0.0425 -0.4052 0.3668 0.051 Uiso 1 1 calc R U . . .
H11B H 0.0048 -0.3521 0.4938 0.051 Uiso 1 1 calc R U . . .
H11C H 0.2354 -0.3532 0.4886 0.051 Uiso 1 1 calc R U . . .
B1 B 0.8347(8) 0.6262(6) 1.0392(4) 0.0266(10) Uani 1 1 d . . . . .
C8 C 1.0220(8) 0.8116(6) 0.8050(4) 0.0382(11) Uani 1 1 d . . . . .
H8A H 1.1061 0.7414 0.8152 0.057 Uiso 1 1 calc R U . . .
H8B H 1.1137 0.9216 0.8455 0.057 Uiso 1 1 calc R U . . .
H8C H 0.9618 0.7988 0.7191 0.057 Uiso 1 1 calc R U . . .
C7 C 0.6394(8) 0.8887(5) 0.8511(5) 0.0386(11) Uani 1 1 d . . . . .
H7A H 0.5262 0.8616 0.8879 0.058 Uiso 1 1 calc R U . . .
H7B H 0.5757 0.8728 0.7650 0.058 Uiso 1 1 calc R U . . .
H7C H 0.7290 0.9996 0.8895 0.058 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
S1 C1 1.769(4) . ?
S1 C9 1.797(4) . ?
Si1 O2 1.671(3) . ?
Si1 C7 1.846(5) . ?
Si1 C8 1.851(5) . ?
Si1 C6 1.863(4) . ?
F1 C5 1.370(5) . ?
O1 B1 1.350(5) . ?
O1 H1 0.8400 . ?
O2 B1 1.387(5) . ?
O3 C10 1.221(5) . ?
C5 C6 1.366(6) . ?
C5 C1 1.402(6) . ?
C6 C4 1.416(5) . ?
C1 C2 1.400(6) . ?
C3 C2 1.388(6) . ?
C3 C4 1.397(5) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?
C4 B1 1.578(6) . ?
C10 C9 1.507(6) . ?
C10 C11 1.517(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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 S1 C9 100.42(19) . . ?
O2 Si1 C7 111.0(2) . . ?
O2 Si1 C8 111.5(2) . . ?
C7 Si1 C8 110.5(2) . . ?
O2 Si1 C6 95.59(17) . . ?
C7 Si1 C6 115.1(2) . . ?
C8 Si1 C6 112.5(2) . . ?
B1 O1 H1 109.5 . . ?
B1 O2 Si1 113.1(3) . . ?
C6 C5 F1 119.1(4) . . ?
C6 C5 C1 124.1(4) . . ?
F1 C5 C1 116.8(4) . . ?
C5 C6 C4 118.1(4) . . ?
C5 C6 Si1 134.1(3) . . ?
C4 C6 Si1 107.6(3) . . ?
C2 C1 C5 116.8(4) . . ?
C2 C1 S1 126.5(3) . . ?
C5 C1 S1 116.6(3) . . ?
C2 C3 C4 120.8(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C3 C4 C6 119.3(4) . . ?
C3 C4 B1 129.9(4) . . ?
C6 C4 B1 110.7(4) . . ?
O3 C10 C9 121.5(4) . . ?
O3 C10 C11 122.7(4) . . ?
C9 C10 C11 115.8(4) . . ?
C10 C9 S1 110.5(3) . . ?
C10 C9 H9A 109.5 . . ?
S1 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
S1 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 B1 O2 123.5(4) . . ?
O1 B1 C4 123.6(4) . . ?
O2 B1 C4 112.9(4) . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_refine_diff_density_max         2.711
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.268

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_27
_database_code_depnum_ccdc_archive 'CCDC 2190668'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
7-fluoro-N-(4-fluorophenyl)-3-hydroxy-1,1-dimethyl-1,3-dihydrobenzo[c][1,2,5]oxasilaborole-6-sulfonamide 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 B F3 N O4 S Si'
_chemical_formula_sum            'C14 H13 B F3 N O4 S Si'
_chemical_formula_weight         387.21

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'
N N 0.0061 0.0033 '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'
Si Si 0.0817 0.0704 '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'
B B 0.0013 0.0007 '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                   6.5260(5)
_cell_length_b                   10.5500(5)
_cell_length_c                   13.1827(7)
_cell_angle_alpha                101.774(4)
_cell_angle_beta                 90.259(5)
_cell_angle_gamma                106.776(6)
_cell_volume                     848.76(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2613
_cell_measurement_theta_min      2.8460
_cell_measurement_theta_max      28.8730

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    0.311
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.023
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 1 0.0568
-1 4 -5 0.0792
-2 -4 -5 0.0118
1 0 0 0.0096
-1 5 0 0.0382
-8 -4 0 0.0023
-5 4 4 0.0197
3 7 11 0.0315
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0004 -1.0002 1.0000 -0.0543 0.0179 0.0569
-1.0009 3.9997 -4.9999 0.2629 -0.1700 -0.1563
-1.9978 -4.0025 -4.9989 0.2486 -0.1319 0.4607
0.9991 0.0012 -0.0002 0.0079 0.0974 -0.0581
-1.0005 4.9995 -0.0003 -0.0040 -0.1820 -0.2912
-7.7928 -3.8205 0.4913 -0.0911 -0.6947 0.7135
-4.9961 3.9944 4.0002 -0.2505 -0.5508 -0.0407
2.9969 7.0037 10.9980 -0.5594 0.1843 -0.8065
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.900
_oxdiff_exptl_absorpt_empirical_full_max 1.116
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0026

_diffrn_reflns_number            6440
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.064
_diffrn_reflns_theta_max         29.099
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3897
_reflns_number_gt                3022
_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'

_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)+(0.0365P)²+0.4916P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3897
_refine_ls_number_parameters     234
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_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
H1A H 0.549(5) 0.892(3) 0.524(2) 0.035(8) Uiso 1 1 d D . . . .
H2A H 1.543(5) 1.466(3) 0.903(2) 0.033(9) Uiso 1 1 d D . . . .
S1 S 0.44484(9) 0.96835(6) 0.67231(4) 0.01864(15) Uani 1 1 d . . . . .
Si1 Si 1.02458(11) 1.26641(6) 1.03587(5) 0.01633(15) Uani 1 1 d . . . . .
F3 F 0.5718(2) 1.06092(13) 0.90798(10) 0.0225(3) Uani 1 1 d . . . . .
F2 F 0.8260(2) 1.10252(13) 0.57752(9) 0.0252(3) Uani 1 1 d . . . . .
O2 O 1.4694(3) 1.40988(17) 0.85976(13) 0.0225(4) Uani 1 1 d D . . . .
O1 O 1.2587(3) 1.36958(14) 1.00652(12) 0.0194(4) Uani 1 1 d . . . . .
O3 O 0.3205(3) 0.89857(16) 0.74360(12) 0.0245(4) Uani 1 1 d . . . . .
O4 O 0.3629(3) 1.05260(16) 0.62027(12) 0.0235(4) Uani 1 1 d . . . . .
C1 C 0.9244(4) 1.1947(2) 0.89631(16) 0.0155(4) Uani 1 1 d . . . . .
F1 F 0.8719(3) 0.46341(15) 0.63205(12) 0.0435(5) Uani 1 1 d . . . . .
N1 N 0.4980(3) 0.85679(19) 0.57970(15) 0.0194(4) Uani 1 1 d D . . . .
C5 C 0.6923(4) 1.0734(2) 0.73971(17) 0.0160(5) Uani 1 1 d . . . . .
C3 C 1.0551(4) 1.2157(2) 0.72556(17) 0.0180(5) Uani 1 1 d . . . . .
H3 H 1.1649 1.2522 0.6834 0.022 Uiso 1 1 calc R U . . .
C6 C 0.7305(4) 1.1091(2) 0.84762(16) 0.0159(5) Uani 1 1 d . . . . .
C2 C 1.0878(4) 1.2470(2) 0.83352(17) 0.0161(5) Uani 1 1 d . . . . .
C7 C 1.0920(4) 1.1484(2) 1.10649(18) 0.0220(5) Uani 1 1 d . . . . .
H7A H 1.1804 1.0999 1.0644 0.033 Uiso 1 1 calc R U . . .
H7B H 0.9598 1.0832 1.1202 0.033 Uiso 1 1 calc R U . . .
H7C H 1.1718 1.1995 1.1725 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5966(4) 0.7578(2) 0.59874(17) 0.0182(5) Uani 1 1 d . . . . .
C4 C 0.8615(4) 1.1313(2) 0.68230(16) 0.0183(5) Uani 1 1 d . . . . .
C13 C 0.5795(5) 0.5533(2) 0.65593(19) 0.0291(6) Uani 1 1 d . . . . .
H13 H 0.5068 0.4810 0.6874 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4850(4) 0.6519(2) 0.64417(18) 0.0239(5) Uani 1 1 d . . . . .
H14 H 0.3456 0.6473 0.6668 0.029 Uiso 1 1 calc R U . . .
B1 B 1.2901(4) 1.3488(2) 0.9011(2) 0.0179(5) Uani 1 1 d . . . . .
C10 C 0.8006(4) 0.7647(2) 0.56592(18) 0.0229(5) Uani 1 1 d . . . . .
H10 H 0.8767 0.8383 0.5365 0.027 Uiso 1 1 calc R U . . .
C12 C 0.7805(5) 0.5623(2) 0.62111(19) 0.0295(6) Uani 1 1 d . . . . .
C11 C 0.8938(4) 0.6650(2) 0.57575(19) 0.0267(6) Uani 1 1 d . . . . .
H11 H 1.0318 0.6676 0.5519 0.032 Uiso 1 1 calc R U . . .
C8 C 0.8636(4) 1.3673(2) 1.10838(19) 0.0267(6) Uani 1 1 d . . . . .
H8A H 0.8356 1.4286 1.0670 0.040 Uiso 1 1 calc R U . . .
H8B H 0.9423 1.4205 1.1741 0.040 Uiso 1 1 calc R U . . .
H8C H 0.7271 1.3066 1.1226 0.040 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
S1 O3 1.4241(16) . ?
S1 O4 1.4378(17) . ?
S1 N1 1.6276(19) . ?
S1 C5 1.782(2) . ?
Si1 O1 1.6987(17) . ?
Si1 C8 1.842(2) . ?
Si1 C7 1.842(2) . ?
Si1 C1 1.876(2) . ?
F3 C6 1.354(2) . ?
F2 C4 1.356(2) . ?
O2 B1 1.339(3) . ?
O2 H2A 0.77(3) . ?
O1 B1 1.388(3) . ?
C1 C6 1.387(3) . ?
C1 C2 1.408(3) . ?
F1 C12 1.373(3) . ?
N1 C9 1.435(3) . ?
N1 H1A 0.91(3) . ?
C5 C6 1.397(3) . ?
C5 C4 1.404(3) . ?
C3 C4 1.361(3) . ?
C3 C2 1.395(3) . ?
C3 H3 0.9500 . ?
C2 B1 1.571(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C10 1.388(3) . ?
C9 C14 1.395(3) . ?
C13 C12 1.376(4) . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C12 C11 1.373(3) . ?
C11 H11 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
O3 S1 O4 120.66(11) . . ?
O3 S1 N1 108.31(10) . . ?
O4 S1 N1 105.11(10) . . ?
O3 S1 C5 107.69(10) . . ?
O4 S1 C5 106.56(10) . . ?
N1 S1 C5 107.95(11) . . ?
O1 Si1 C8 110.44(10) . . ?
O1 Si1 C7 107.52(10) . . ?
C8 Si1 C7 113.77(11) . . ?
O1 Si1 C1 93.81(9) . . ?
C8 Si1 C1 113.26(11) . . ?
C7 Si1 C1 115.98(10) . . ?
B1 O2 H2A 109(2) . . ?
B1 O1 Si1 113.65(15) . . ?
C6 C1 C2 118.1(2) . . ?
C6 C1 Si1 133.59(17) . . ?
C2 C1 Si1 108.32(16) . . ?
C9 N1 S1 122.98(16) . . ?
C9 N1 H1A 112.4(17) . . ?
S1 N1 H1A 112.7(17) . . ?
C6 C5 C4 116.0(2) . . ?
C6 C5 S1 124.98(17) . . ?
C4 C5 S1 118.93(17) . . ?
C4 C3 C2 118.1(2) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
F3 C6 C1 118.09(19) . . ?
F3 C6 C5 119.2(2) . . ?
C1 C6 C5 122.7(2) . . ?
C3 C2 C1 121.1(2) . . ?
C3 C2 B1 127.4(2) . . ?
C1 C2 B1 111.34(19) . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 C9 C14 120.3(2) . . ?
C10 C9 N1 118.9(2) . . ?
C14 C9 N1 120.7(2) . . ?
F2 C4 C3 118.7(2) . . ?
F2 C4 C5 117.3(2) . . ?
C3 C4 C5 124.0(2) . . ?
C12 C13 C14 118.7(2) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C9 119.4(2) . . ?
C13 C14 H14 120.3 . . ?
C9 C14 H14 120.3 . . ?
O2 B1 O1 124.7(2) . . ?
O2 B1 C2 122.9(2) . . ?
O1 B1 C2 112.4(2) . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
F1 C12 C11 118.4(3) . . ?
F1 C12 C13 118.3(2) . . ?
C11 C12 C13 123.2(2) . . ?
C12 C11 C10 117.9(2) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.473
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.072

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_15
_database_code_depnum_ccdc_archive 'CCDC 2190665'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
3-((7-fluoro-3-hydroxy-1,1-dimethyl-1,3-dihydrobenzo[c][1,2,5]oxasilaborol-6-yl)thio)-1-(4-fluorophenyl)pyrrolidine-2,5-dione 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 B F2 N O4 S Si'
_chemical_formula_sum            'C18 H16 B F2 N O4 S Si'
_chemical_formula_weight         419.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.9955(4)
_cell_length_b                   6.7688(2)
_cell_length_c                   24.8601(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.673(3)
_cell_angle_gamma                90
_cell_volume                     1969.34(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2684
_cell_measurement_theta_min      3.7800
_cell_measurement_theta_max      72.1810

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    2.436
_exptl_absorpt_correction_T_min  0.91470
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.880
_oxdiff_exptl_absorpt_empirical_full_max 1.221
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2195

_diffrn_reflns_number            7478
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.645
_diffrn_reflns_theta_max         72.690
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3812
_reflns_number_gt                2949
_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'

_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)+(0.0437P)²+0.5692P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3812
_refine_ls_number_parameters     256
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
S1 S 0.18684(4) 0.66126(8) 0.09387(2) 0.01986(13) Uani 1 1 d . . . . .
Si1 Si -0.25825(5) 0.33368(9) 0.09446(2) 0.01934(15) Uani 1 1 d . . . . .
F1 F 0.02416(11) 0.38192(19) 0.13231(5) 0.0217(3) Uani 1 1 d . . . . .
O3 O 0.24212(13) 0.4817(2) 0.21935(6) 0.0224(3) Uani 1 1 d . . . . .
O4 O -0.04375(14) 0.9262(3) 0.21969(7) 0.0272(4) Uani 1 1 d . . . . .
F2 F -0.00511(13) 0.2544(2) 0.40233(6) 0.0354(4) Uani 1 1 d . . . . .
O2 O -0.36597(13) 0.4251(2) 0.04558(6) 0.0226(3) Uani 1 1 d . . . . .
O1 O -0.40321(14) 0.6554(3) -0.02989(7) 0.0307(4) Uani 1 1 d D . . . .
N1 N 0.08939(15) 0.6760(3) 0.22758(7) 0.0171(4) Uani 1 1 d . . . . .
C12 C -0.02880(18) 0.5004(3) 0.08976(8) 0.0175(4) Uani 1 1 d . . . . .
C9 C -0.13351(19) 0.7258(3) 0.00080(9) 0.0214(5) Uani 1 1 d . . . . .
H9 H -0.1690 0.8003 -0.0307 0.026 Uiso 1 1 calc R U . . .
C19 C 0.18117(18) 0.6228(3) 0.20504(8) 0.0175(4) Uani 1 1 d . . . . .
C2 C 0.01647(18) 0.3801(3) 0.26384(9) 0.0206(5) Uani 1 1 d . . . . .
H2 H 0.0020 0.3243 0.2279 0.025 Uiso 1 1 calc R U . . .
C1 C 0.06066(18) 0.5691(3) 0.27271(8) 0.0190(4) Uani 1 1 d . . . . .
C10 C -0.01677(19) 0.7442(3) 0.02231(8) 0.0200(4) Uani 1 1 d . . . . .
H10 H 0.0266 0.8339 0.0058 0.024 Uiso 1 1 calc R U . . .
C18 C 0.03726(19) 0.8526(3) 0.20615(9) 0.0194(4) Uani 1 1 d . . . . .
C6 C 0.08477(19) 0.6544(4) 0.32515(9) 0.0219(5) Uani 1 1 d . . . . .
H6 H 0.1166 0.7832 0.3307 0.026 Uiso 1 1 calc R U . . .
C7 C -0.14528(18) 0.4817(3) 0.07108(8) 0.0180(4) Uani 1 1 d . . . . .
C11 C 0.03782(18) 0.6326(3) 0.06796(8) 0.0182(4) Uani 1 1 d . . . . .
C17 C 0.09999(19) 0.9299(3) 0.16400(8) 0.0206(4) Uani 1 1 d . . . . .
H17A H 0.1359 1.0592 0.1757 0.025 Uiso 1 1 calc R U . . .
H17B H 0.0470 0.9458 0.1277 0.025 Uiso 1 1 calc R U . . .
C5 C 0.0612(2) 0.5467(4) 0.36913(9) 0.0261(5) Uani 1 1 d . . . . .
H5 H 0.0754 0.6014 0.4052 0.031 Uiso 1 1 calc R U . . .
C8 C -0.19830(19) 0.5981(3) 0.02553(8) 0.0197(4) Uani 1 1 d . . . . .
C3 C -0.0066(2) 0.2723(4) 0.30770(9) 0.0244(5) Uani 1 1 d . . . . .
H3 H -0.0375 0.1428 0.3024 0.029 Uiso 1 1 calc R U . . .
B1 B -0.3315(2) 0.5618(4) 0.01095(10) 0.0224(5) Uani 1 1 d . . . . .
C16 C 0.19097(18) 0.7746(3) 0.16103(8) 0.0188(4) Uani 1 1 d . . . . .
H16 H 0.2671 0.8402 0.1729 0.023 Uiso 1 1 calc R U . . .
C4 C 0.0168(2) 0.3588(4) 0.35911(9) 0.0256(5) Uani 1 1 d . . . . .
C14 C -0.2761(2) 0.4016(5) 0.16386(10) 0.0336(6) Uani 1 1 d . . . . .
H14A H -0.3358 0.3191 0.1737 0.050 Uiso 1 1 calc R U . . .
H14B H -0.2983 0.5409 0.1641 0.050 Uiso 1 1 calc R U . . .
H14C H -0.2039 0.3809 0.1906 0.050 Uiso 1 1 calc R U . . .
C13 C -0.2491(2) 0.0643(4) 0.08560(12) 0.0352(6) Uani 1 1 d . . . . .
H13A H -0.2402 0.0353 0.0482 0.053 Uiso 1 1 calc R U . . .
H13B H -0.3191 0.0019 0.0916 0.053 Uiso 1 1 calc R U . . .
H13C H -0.1832 0.0125 0.1124 0.053 Uiso 1 1 calc R U . . .
H1A H -0.4721(11) 0.625(5) -0.0337(13) 0.053 Uiso 1 1 d D 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
S1 C11 1.773(2) . ?
S1 C16 1.828(2) . ?
Si1 O2 1.6853(16) . ?
Si1 C13 1.843(3) . ?
Si1 C14 1.843(3) . ?
Si1 C7 1.877(2) . ?
F1 C12 1.368(2) . ?
O3 C19 1.208(3) . ?
O4 C18 1.204(3) . ?
F2 C4 1.359(3) . ?
O2 B1 1.387(3) . ?
O1 B1 1.337(3) . ?
O1 H1A 0.836(10) . ?
N1 C19 1.388(3) . ?
N1 C18 1.400(3) . ?
N1 C1 1.439(3) . ?
C12 C7 1.378(3) . ?
C12 C11 1.386(3) . ?
C9 C10 1.391(3) . ?
C9 C8 1.392(3) . ?
C9 H9 0.9500 . ?
C19 C16 1.524(3) . ?
C2 C1 1.384(3) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C1 C6 1.397(3) . ?
C10 C11 1.401(3) . ?
C10 H10 0.9500 . ?
C18 C17 1.511(3) . ?
C6 C5 1.394(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.411(3) . ?
C17 C16 1.529(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C5 C4 1.380(4) . ?
C5 H5 0.9500 . ?
C8 B1 1.578(3) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9500 . ?
C16 H16 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C11 S1 C16 101.59(10) . . ?
O2 Si1 C13 109.48(11) . . ?
O2 Si1 C14 110.79(10) . . ?
C13 Si1 C14 112.39(14) . . ?
O2 Si1 C7 94.14(9) . . ?
C13 Si1 C7 115.17(11) . . ?
C14 Si1 C7 113.39(11) . . ?
B1 O2 Si1 114.00(14) . . ?
B1 O1 H1A 115(2) . . ?
C19 N1 C18 113.29(18) . . ?
C19 N1 C1 122.12(18) . . ?
C18 N1 C1 124.25(18) . . ?
F1 C12 C7 118.11(19) . . ?
F1 C12 C11 118.09(18) . . ?
C7 C12 C11 123.81(19) . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
O3 C19 N1 124.6(2) . . ?
O3 C19 C16 127.4(2) . . ?
N1 C19 C16 107.95(18) . . ?
C1 C2 C3 119.7(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C1 C6 121.6(2) . . ?
C2 C1 N1 119.29(19) . . ?
C6 C1 N1 119.0(2) . . ?
C9 C10 C11 121.0(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
O4 C18 N1 124.6(2) . . ?
O4 C18 C17 127.3(2) . . ?
N1 C18 C17 108.10(18) . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C12 C7 C8 117.7(2) . . ?
C12 C7 Si1 133.81(17) . . ?
C8 C7 Si1 108.52(15) . . ?
C12 C11 C10 117.24(19) . . ?
C12 C11 S1 123.40(16) . . ?
C10 C11 S1 119.35(17) . . ?
C18 C17 C16 105.36(17) . . ?
C18 C17 H17A 110.7 . . ?
C16 C17 H17A 110.7 . . ?
C18 C17 H17B 110.7 . . ?
C16 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 B1 129.1(2) . . ?
C7 C8 B1 110.7(2) . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
O1 B1 O2 123.9(2) . . ?
O1 B1 C8 123.4(2) . . ?
O2 B1 C8 112.68(19) . . ?
C19 C16 C17 105.11(17) . . ?
C19 C16 S1 112.44(15) . . ?
C17 C16 S1 117.13(15) . . ?
C19 C16 H16 107.2 . . ?
C17 C16 H16 107.2 . . ?
S1 C16 H16 107.2 . . ?
F2 C4 C3 118.5(2) . . ?
F2 C4 C5 118.1(2) . . ?
C3 C4 C5 123.5(2) . . ?
Si1 C14 H14A 109.5 . . ?
Si1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_28
_database_code_depnum_ccdc_archive 'CCDC 2190669'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
7-fluoro-1,1-dimethyl-6-(morpholinosulfonyl)benzo[c][1,2,5]oxasilaborol-3(1H)-ol 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 B F2 N O5 S Si'
_chemical_formula_sum            'C12 H16 B F2 N O5 S Si'
_chemical_formula_weight         363.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3865(4)
_cell_length_b                   16.0059(5)
_cell_length_c                   10.0154(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.281(4)
_cell_angle_gamma                90
_cell_volume                     1529.44(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4571
_cell_measurement_theta_min      5.3860
_cell_measurement_theta_max      72.5270

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    3.076
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.100
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 2 2 0.0709
0 5 -2 0.0608
1 5 0 0.0631
-1 -5 0 0.0366
5 -4 -2 0.0603
-5 4 3 0.0994
-1 4 -5 0.0545
-2 -1 5 0.1134
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0003 2.0088 2.0035 -0.3380 -0.1086 0.3047
-0.0008 4.9942 -2.0024 -0.3051 -0.0633 -0.4964
1.0000 5.0024 0.0008 -0.4861 -0.0946 -0.1119
-1.0000 -5.0024 -0.0008 0.4861 0.0946 0.1119
5.0080 -4.0038 -2.0025 -0.0655 0.7774 0.3021
-5.0082 4.0074 3.0040 0.0217 -0.8423 -0.1538
-1.0011 3.9819 -5.0073 -0.0019 0.0716 -0.9894
-2.0035 -0.9839 5.0071 0.0466 -0.4832 0.6061
_exptl_absorpt_correction_T_min  0.457
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.499
_oxdiff_exptl_absorpt_empirical_full_max 2.216
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2195

_diffrn_reflns_number            5846
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.397
_diffrn_reflns_theta_max         72.661
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2948
_reflns_number_gt                2744
_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'

_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)+(0.0448P)²+0.8898P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2948
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_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
F2 F 0.70966(10) 0.10523(6) 0.53750(11) 0.0173(2) Uani 1 1 d . . . . .
S1 S 0.51276(4) 0.15766(2) 0.67808(4) 0.01014(11) Uani 1 1 d . . . . .
Si2 Si 0.77372(4) 0.47175(3) 0.64321(4) 0.01100(12) Uani 1 1 d . . . . .
F1 F 0.56279(10) 0.34484(6) 0.71634(10) 0.0138(2) Uani 1 1 d . . . . .
O3 O 0.13987(12) 0.15749(7) 0.25926(13) 0.0174(3) Uani 1 1 d . . . . .
O2 O 0.57273(12) 0.07590(7) 0.71012(12) 0.0147(2) Uani 1 1 d . . . . .
O1 O 0.48016(12) 0.20151(7) 0.78535(12) 0.0143(2) Uani 1 1 d . . . . .
O5 O 0.98263(12) 0.37752(7) 0.43691(13) 0.0168(3) Uani 1 1 d . . . . .
H5 H 1.0250 0.4219 0.4348 0.025 Uiso 1 1 calc R U . . .
O4 O 0.90079(12) 0.46586(7) 0.57944(12) 0.0142(2) Uani 1 1 d . . . . .
C1 C 0.64177(15) 0.30757(10) 0.65443(16) 0.0104(3) Uani 1 1 d . . . . .
N1 N 0.36776(13) 0.15044(8) 0.53314(14) 0.0107(3) Uani 1 1 d . . . . .
C2 C 0.63057(15) 0.22125(10) 0.63137(16) 0.0101(3) Uani 1 1 d . . . . .
C3 C 0.71610(16) 0.18781(10) 0.56597(17) 0.0120(3) Uani 1 1 d . . . . .
C12 C 0.8459(2) 0.50621(12) 0.83397(19) 0.0222(4) Uani 1 1 d . . . . .
H12A H 0.9119 0.4642 0.8943 0.033 Uiso 1 1 calc R U . . .
H12B H 0.7695 0.5133 0.8670 0.033 Uiso 1 1 calc R U . . .
H12C H 0.8948 0.5595 0.8422 0.033 Uiso 1 1 calc R U . . .
C6 C 0.80772(16) 0.23496(10) 0.52767(17) 0.0128(3) Uani 1 1 d . . . . .
H6 H 0.8640 0.2094 0.4839 0.015 Uiso 1 1 calc R U . . .
C7 C 0.27989(17) 0.22626(10) 0.48768(18) 0.0145(3) Uani 1 1 d . . . . .
H7A H 0.3212 0.2660 0.4399 0.017 Uiso 1 1 calc R U . . .
H7B H 0.2741 0.2541 0.5734 0.017 Uiso 1 1 calc R U . . .
C9 C 0.22437(17) 0.08405(10) 0.30479(18) 0.0158(3) Uani 1 1 d . . . . .
H9A H 0.2255 0.0545 0.2184 0.019 Uiso 1 1 calc R U . . .
H9B H 0.1830 0.0461 0.3552 0.019 Uiso 1 1 calc R U . . .
C4 C 0.73150(16) 0.35771(10) 0.61872(16) 0.0106(3) Uani 1 1 d . . . . .
C5 C 0.81613(15) 0.32042(10) 0.55425(16) 0.0112(3) Uani 1 1 d . . . . .
C11 C 0.64744(18) 0.54779(11) 0.52457(19) 0.0183(3) Uani 1 1 d . . . . .
H11A H 0.6085 0.5267 0.4246 0.028 Uiso 1 1 calc R U . . .
H11B H 0.6950 0.6011 0.5278 0.028 Uiso 1 1 calc R U . . .
H11C H 0.5716 0.5561 0.5581 0.028 Uiso 1 1 calc R U . . .
C10 C 0.37324(16) 0.10561(10) 0.40603(17) 0.0138(3) Uani 1 1 d . . . . .
H10A H 0.4297 0.0540 0.4381 0.017 Uiso 1 1 calc R U . . .
H10B H 0.4172 0.1414 0.3552 0.017 Uiso 1 1 calc R U . . .
C8 C 0.13483(17) 0.19973(11) 0.38239(18) 0.0182(4) Uani 1 1 d . . . . .
H8A H 0.0928 0.1623 0.4330 0.022 Uiso 1 1 calc R U . . .
H8B H 0.0743 0.2497 0.3495 0.022 Uiso 1 1 calc R U . . .
B1 B 0.91123(19) 0.38822(12) 0.5225(2) 0.0132(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
F2 C3 1.3482(18) . ?
S1 O2 1.4303(12) . ?
S1 O1 1.4314(12) . ?
S1 N1 1.6311(13) . ?
S1 C2 1.7900(15) . ?
Si2 O4 1.6809(12) . ?
Si2 C11 1.8389(18) . ?
Si2 C12 1.8396(18) . ?
Si2 C4 1.8705(16) . ?
F1 C1 1.3473(17) . ?
O3 C8 1.425(2) . ?
O3 C9 1.4295(19) . ?
O5 B1 1.348(2) . ?
O5 H5 0.8400 . ?
O4 B1 1.389(2) . ?
C1 C4 1.380(2) . ?
C1 C2 1.398(2) . ?
N1 C7 1.4779(19) . ?
N1 C10 1.482(2) . ?
C2 C3 1.402(2) . ?
C3 C6 1.382(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C6 C5 1.390(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.519(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C10 1.516(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C4 C5 1.412(2) . ?
C5 B1 1.582(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.44(7) . . ?
O2 S1 N1 107.57(7) . . ?
O1 S1 N1 107.07(7) . . ?
O2 S1 C2 107.27(7) . . ?
O1 S1 C2 107.83(7) . . ?
N1 S1 C2 107.08(7) . . ?
O4 Si2 C11 104.96(7) . . ?
O4 Si2 C12 110.63(7) . . ?
C11 Si2 C12 111.50(9) . . ?
O4 Si2 C4 94.25(6) . . ?
C11 Si2 C4 119.39(7) . . ?
C12 Si2 C4 114.02(8) . . ?
C8 O3 C9 109.99(12) . . ?
B1 O5 H5 109.5 . . ?
B1 O4 Si2 113.99(10) . . ?
F1 C1 C4 117.28(13) . . ?
F1 C1 C2 119.17(13) . . ?
C4 C1 C2 123.55(14) . . ?
C7 N1 C10 111.20(12) . . ?
C7 N1 S1 117.17(10) . . ?
C10 N1 S1 117.60(10) . . ?
C1 C2 C3 115.33(14) . . ?
C1 C2 S1 122.66(12) . . ?
C3 C2 S1 122.00(12) . . ?
F2 C3 C6 117.30(14) . . ?
F2 C3 C2 119.05(14) . . ?
C6 C3 C2 123.65(15) . . ?
Si2 C12 H12A 109.5 . . ?
Si2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C6 C5 118.83(15) . . ?
C3 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
N1 C7 C8 107.86(13) . . ?
N1 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
N1 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
O3 C9 C10 111.19(13) . . ?
O3 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
O3 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C1 C4 C5 118.61(14) . . ?
C1 C4 Si2 132.91(12) . . ?
C5 C4 Si2 108.45(11) . . ?
C6 C5 C4 120.02(14) . . ?
C6 C5 B1 129.31(14) . . ?
C4 C5 B1 110.66(14) . . ?
Si2 C11 H11A 109.5 . . ?
Si2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Si2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C10 C9 108.02(13) . . ?
N1 C10 H10A 110.1 . . ?
C9 C10 H10A 110.1 . . ?
N1 C10 H10B 110.1 . . ?
C9 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
O3 C8 C7 111.58(14) . . ?
O3 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
O3 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
O5 B1 O4 121.79(15) . . ?
O5 B1 C5 125.79(15) . . ?
O4 B1 C5 112.00(14) . . ?

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_20
_database_code_depnum_ccdc_archive 'CCDC 2190666'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 5,7-difluoro-1,1-dimethyl-6-((2-(phenylsulfonyl)ethyl)thio)benzo[c][1,2,5]oxasilaborol-3(1H)-ol 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 B F2 O4 S2 Si'
_chemical_formula_sum            'C16 H17 B F2 O4 S2 Si'
_chemical_formula_weight         414.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   9.4513(4)
_cell_length_b                   9.8968(4)
_cell_length_c                   12.2922(6)
_cell_angle_alpha                91.269(4)
_cell_angle_beta                 112.587(4)
_cell_angle_gamma                118.044(4)
_cell_volume                     907.49(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10074
_cell_measurement_theta_min      3.9940
_cell_measurement_theta_max      76.4590

_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    3.661
_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.082
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -4 1 0.0661
-5 0 0 0.0524
5 0 0 0.0295
-1 4 -1 0.0410
4 -3 -6 0.0405
-3 0 5 0.0545
0 -1 -4 0.0377
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0017 -4.0029 0.9871 0.0291 -0.0428 0.6400
-4.9927 0.4980 0.4882 -0.2001 -0.9363 0.0446
4.9927 -0.4980 -0.4882 0.2001 0.9363 -0.0446
-1.0007 3.5034 -1.4893 0.0418 -0.0381 -0.5707
4.0020 -2.9920 -6.0032 0.8670 0.0876 0.2602
-3.0005 0.4918 5.4958 -0.7122 -0.1283 0.1070
0.0047 -0.9950 -4.0056 0.4801 -0.4025 0.0740
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.837
_oxdiff_exptl_absorpt_empirical_full_max 1.314
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(13)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2195
_diffrn_reflns_number            12561
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.021
_diffrn_reflns_theta_max         76.679
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3714
_reflns_number_gt                3564
_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       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'

_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)+(0.0436P)²+0.6833P] 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         3714
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0769
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.001
_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
F2 F 0.37251(12) 0.11849(10) 0.12588(8) 0.02115(19) Uani 1 1 d . . . . .
F1 F 0.95434(11) 0.21108(10) 0.34780(8) 0.01911(19) Uani 1 1 d . . . . .
S1 S 0.74015(5) 0.36591(4) 0.31259(3) 0.01562(9) Uani 1 1 d . . . . .
S2 S 0.55388(5) 0.20307(4) 0.58979(3) 0.01578(10) Uani 1 1 d . . . . .
Si1 Si 0.84752(5) -0.14497(4) 0.22206(3) 0.01319(10) Uani 1 1 d . . . . .
O3 O 0.35736(14) -0.40975(12) -0.02721(9) 0.0177(2) Uani 1 1 d . . . . .
H3 H 0.3652 -0.4874 -0.0456 0.027 Uiso 1 1 calc R U . . .
O4 O 0.66522(13) -0.31005(12) 0.11549(9) 0.0156(2) Uani 1 1 d . . . . .
O2 O 0.37037(15) 0.13093(14) 0.56984(10) 0.0247(2) Uani 1 1 d . . . . .
O1 O 0.64607(15) 0.11779(12) 0.62619(10) 0.0219(2) Uani 1 1 d . . . . .
C14 C 0.56002(19) 0.25589(16) 0.45299(12) 0.0158(3) Uani 1 1 d . . . . .
H14A H 0.4810 0.1591 0.3855 0.019 Uiso 1 1 calc R U . . .
H14B H 0.5117 0.3267 0.4337 0.019 Uiso 1 1 calc R U . . .
C2 C 0.42771(19) -0.08322(16) 0.09582(13) 0.0154(3) Uani 1 1 d . . . . .
H2 H 0.3057 -0.1504 0.0384 0.018 Uiso 1 1 calc R U . . .
C13 C 0.74722(19) 0.33808(17) 0.46047(13) 0.0171(3) Uani 1 1 d . . . . .
H13A H 0.8023 0.2739 0.4894 0.021 Uiso 1 1 calc R U . . .
H13B H 0.8227 0.4422 0.5200 0.021 Uiso 1 1 calc R U . . .
C5 C 0.78215(19) 0.11490(16) 0.26485(12) 0.0141(3) Uani 1 1 d . . . . .
C6 C 0.72890(19) -0.03443(16) 0.20814(12) 0.0139(3) Uani 1 1 d . . . . .
C3 C 0.48939(19) 0.06808(17) 0.15511(13) 0.0149(3) Uani 1 1 d . . . . .
C4 C 0.66638(19) 0.17190(16) 0.24103(12) 0.0139(3) Uani 1 1 d . . . . .
C1 C 0.54823(19) -0.13459(16) 0.12214(12) 0.0137(3) Uani 1 1 d . . . . .
C8 C 0.68352(19) 0.38384(17) 0.70112(13) 0.0156(3) Uani 1 1 d . . . . .
C16 C 0.92674(19) -0.18988(17) 0.37058(13) 0.0172(3) Uani 1 1 d . . . . .
H16A H 0.8310 -0.2318 0.3961 0.026 Uiso 1 1 calc R U . . .
H16B H 1.0314 -0.0931 0.4310 0.026 Uiso 1 1 calc R U . . .
H16C H 0.9600 -0.2686 0.3637 0.026 Uiso 1 1 calc R U . . .
C9 C 0.6053(2) 0.46793(18) 0.71530(14) 0.0199(3) Uani 1 1 d . . . . .
H9 H 0.4825 0.4300 0.6640 0.024 Uiso 1 1 calc R U . . .
B1 B 0.5144(2) -0.29771(18) 0.06413(14) 0.0145(3) Uani 1 1 d . . . . .
C10 C 0.7083(2) 0.6069(2) 0.80480(16) 0.0248(3) Uani 1 1 d . . . . .
H10 H 0.6567 0.6656 0.8154 0.030 Uiso 1 1 calc R U . . .
C15 C 1.0245(2) -0.05789(19) 0.17119(15) 0.0210(3) Uani 1 1 d . . . . .
H15A H 0.9794 -0.0309 0.0940 0.031 Uiso 1 1 calc R U . . .
H15B H 1.0590 -0.1344 0.1599 0.031 Uiso 1 1 calc R U . . .
H15C H 1.1291 0.0379 0.2327 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8628(2) 0.43709(18) 0.77581(14) 0.0203(3) Uani 1 1 d . . . . .
H7 H 0.9144 0.3783 0.7658 0.024 Uiso 1 1 calc R U . . .
C12 C 0.9645(2) 0.57678(19) 0.86475(15) 0.0249(3) Uani 1 1 d . . . . .
H12 H 1.0874 0.6152 0.9160 0.030 Uiso 1 1 calc R U . . .
C11 C 0.8875(2) 0.66112(19) 0.87948(15) 0.0258(3) Uani 1 1 d . . . . .
H11 H 0.9580 0.7568 0.9412 0.031 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
F2 C3 1.3489(16) . ?
F1 C5 1.3491(16) . ?
S1 C4 1.7726(14) . ?
S1 C13 1.8249(14) . ?
S2 O2 1.4419(12) . ?
S2 O1 1.4424(11) . ?
S2 C8 1.7656(15) . ?
S2 C14 1.7859(14) . ?
Si1 O4 1.6966(10) . ?
Si1 C16 1.8411(15) . ?
Si1 C15 1.8447(15) . ?
Si1 C6 1.8701(14) . ?
O3 B1 1.3455(19) . ?
O3 H3 0.8400 . ?
O4 B1 1.3860(19) . ?
C14 C13 1.523(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C2 C3 1.385(2) . ?
C2 C1 1.389(2) . ?
C2 H2 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C5 C6 1.3816(19) . ?
C5 C4 1.394(2) . ?
C6 C1 1.4111(19) . ?
C3 C4 1.396(2) . ?
C1 B1 1.583(2) . ?
C8 C7 1.391(2) . ?
C8 C9 1.393(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C9 C10 1.379(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C7 C12 1.381(2) . ?
C7 H7 0.9500 . ?
C12 C11 1.387(2) . ?
C12 H12 0.9500 . ?
C11 H11 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
C4 S1 C13 100.07(7) . . ?
O2 S2 O1 119.73(7) . . ?
O2 S2 C8 108.54(7) . . ?
O1 S2 C8 106.83(7) . . ?
O2 S2 C14 107.03(7) . . ?
O1 S2 C14 108.52(7) . . ?
C8 S2 C14 105.32(7) . . ?
O4 Si1 C16 110.67(6) . . ?
O4 Si1 C15 109.76(6) . . ?
C16 Si1 C15 111.78(7) . . ?
O4 Si1 C6 94.67(6) . . ?
C16 Si1 C6 115.23(7) . . ?
C15 Si1 C6 113.44(7) . . ?
B1 O3 H3 109.5 . . ?
B1 O4 Si1 113.39(9) . . ?
C13 C14 S2 113.54(10) . . ?
C13 C14 H14A 108.9 . . ?
S2 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
S2 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C3 C2 C1 118.50(13) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C14 C13 S1 111.20(10) . . ?
C14 C13 H13A 109.4 . . ?
S1 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
S1 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
F1 C5 C6 118.86(13) . . ?
F1 C5 C4 117.88(12) . . ?
C6 C5 C4 123.26(13) . . ?
C5 C6 C1 118.45(13) . . ?
C5 C6 Si1 133.41(11) . . ?
C1 C6 Si1 108.13(10) . . ?
F2 C3 C2 117.95(13) . . ?
F2 C3 C4 118.49(12) . . ?
C2 C3 C4 123.54(13) . . ?
C5 C4 C3 115.90(12) . . ?
C5 C4 S1 122.16(11) . . ?
C3 C4 S1 121.93(11) . . ?
C2 C1 C6 120.36(13) . . ?
C2 C1 B1 128.52(13) . . ?
C6 C1 B1 111.10(12) . . ?
C7 C8 C9 121.26(14) . . ?
C7 C8 S2 118.48(11) . . ?
C9 C8 S2 120.23(12) . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C9 C8 119.14(15) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
O3 B1 O4 124.05(13) . . ?
O3 B1 C1 123.32(13) . . ?
O4 B1 C1 112.60(12) . . ?
C9 C10 C11 119.94(15) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
Si1 C15 H15A 109.5 . . ?
Si1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
Si1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C7 C8 118.95(15) . . ?
C12 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C7 C12 C11 120.13(15) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C11 C10 120.58(15) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?

_refine_diff_density_max         0.425
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
