# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 2304134'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology
Poland
;
_audit_update_record             
;
2024-04-28 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;
_audit_creation_date             2024-04-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H10 B F O2 Si'
_chemical_formula_sum            'C10 H10 B F O2 Si'
_chemical_formula_weight         220.08
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9862(2)
_cell_length_b                   7.4451(2)
_cell_length_c                   10.5854(2)
_cell_angle_alpha                92.553(2)
_cell_angle_beta                 97.855(2)
_cell_angle_gamma                91.766(2)
_cell_volume                     544.49(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    17554
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.5780
_cell_measurement_theta_min      1.9200
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.867
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.310
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.76a (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.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       plate
_exptl_crystal_F_000             228
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 10 -5 0.0824
2 -10 2 0.0970
-4 -5 13 0.2559
-4 10 2 0.1714
6 -7 -9 0.2584
9 -1 2 0.2234
-6 -1 13 0.2922
-10 0 0 0.2866
0 1 -15 0.2373
0 10 -2 0.0881
-1 -10 4 0.0710
7 -7 0 0.1774
-5 -8 7 0.0941
-1 -10 -3 0.1412

_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.536
_exptl_crystal_size_min          0.187
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
-0.8085 9.9800 -5.0302 0.2219 0.9255 -0.3069
2.0880 -10.2284 2.2126 -0.2321 -0.9682 0.0935
-3.8522 -5.1324 12.5597 -0.0979 -0.4094 0.9071
-3.8888 9.6317 2.4089 0.2259 0.9417 0.2495
5.6769 -6.6504 -8.6540 -0.1673 -0.6968 -0.6974
9.4981 -0.5685 1.9430 0.8095 -0.4958 -0.3144
-5.9811 -0.8690 12.9477 -0.0553 0.0341 0.9979
-9.7689 0.3999 0.1359 -0.7642 0.4681 0.4438
0.0271 1.2759 -14.7501 -0.4709 0.2882 -0.8338
-0.0597 10.4687 -1.7200 0.4248 0.8913 -0.1585
-0.8282 -10.2155 3.8267 -0.4084 -0.8569 0.3146
7.4501 -7.0580 0.0858 0.2724 -0.9187 -0.2859
-4.8598 -8.0555 7.1678 -0.5114 -0.5393 0.6690
-1.3567 -9.9419 -3.0691 -0.6873 -0.7247 -0.0489

_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.828
_diffrn_reflns_theta_min         1.944
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0013
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -124.00 -37.00   1.00    6.00    --  -29.16 178.00 -30.00   87
  2  ω    -72.00  42.00   1.00    6.00    --  -29.16  77.00   0.00  114
  3  ω   -120.00  62.00   1.00    6.00    --  -29.16   0.00   0.00  182
  4  ω    -14.00  42.00   1.00    6.00    --   29.16  77.00 -90.00   56
  5  ω    -14.00  42.00   1.00    6.00    --   29.16  77.00-150.00   56
  6  ω    -14.00  42.00   1.00    6.00    --   29.16  77.00 -30.00   56
  7  ω    -14.00  42.00   1.00    6.00    --   29.16  77.00-180.00   56
  8  ω   -105.00   9.00   1.00    6.00    --  -29.16 -57.00-120.00  114
  9  ω     -9.00 105.00   1.00    6.00    --   29.16  57.00 -30.00  114
 10  ω    -14.00  42.00   1.00    6.00    --   29.16  77.00  90.00   56
 11  ω     39.00 123.00   1.00    6.00    --   29.16 178.00   0.00   84
 12  ω    -47.00  67.00   1.00    6.00    --   29.16 -57.00 120.00  114
 13  ω    -14.00  42.00   1.00    6.00    --   29.16  77.00  30.00   56
 14  ω    -50.00  77.00   1.00    6.00    --   29.16 -45.00  85.00  127
 15  ω     -9.00 105.00   1.00    6.00    --   29.16  57.00  90.00  114
 16  ω     39.00 123.00   1.00    6.00    --   29.16 178.00 -60.00   84
 17  ω    -14.00  42.00   1.00    6.00    --   29.16  77.00   0.00   56
 18  ω    -62.00 120.00   1.00    6.00    --   29.16   0.00-180.00  182
 19  ω     -9.00 105.00   1.00    6.00    --   29.16  57.00-180.00  114
 20  ω    -62.00 120.00   1.00    6.00    --   29.16   0.00-120.00  182
 21  ω    -62.00 120.00   1.00    6.00    --   29.16   0.00 -90.00  182
 22  ω    -62.00 120.00   1.00    6.00    --   29.16   0.00 -60.00  182
 23  ω    -62.00 120.00   1.00    6.00    --   29.16   0.00 -30.00  182
 24  ω    -62.00  69.00   1.00    6.00    --   29.16   0.00   0.00  131
 25  ω    -62.00 120.00   1.00    6.00    --   29.16   0.00-150.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0806490000
_diffrn_orient_matrix_UB_12      0.0469764000
_diffrn_orient_matrix_UB_13      0.0361346000
_diffrn_orient_matrix_UB_21      -0.0446983000
_diffrn_orient_matrix_UB_22      0.0828366000
_diffrn_orient_matrix_UB_23      -0.0124556000
_diffrn_orient_matrix_UB_31      -0.0449075000
_diffrn_orient_matrix_UB_32      -0.0062151000
_diffrn_orient_matrix_UB_33      0.0559085000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2528
_reflns_number_total             2683
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²+0.2238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0783
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
2.d :
 C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.66283(4) 0.20281(4) 0.21908(3) 0.01544(9) Uani 1 1 d . . . . .
F1 F 0.75361(10) 0.16206(9) 0.53306(6) 0.02543(16) Uani 1 1 d . . . . .
O2 O 0.62255(11) 0.36926(10) 0.11635(7) 0.01830(16) Uani 1 1 d . . . . .
O1 O 0.63111(12) 0.69114(10) 0.10942(7) 0.02170(18) Uani 1 1 d . . . . .
H1 H 0.573046 0.665027 0.035751 0.033 Uiso 1 1 calc R U . . .
C1 C 0.70618(14) 0.53731(14) 0.32388(10) 0.0161(2) Uani 1 1 d . . . . .
C2 C 0.71185(14) 0.35882(14) 0.36416(10) 0.0165(2) Uani 1 1 d . . . . .
C3 C 0.74822(15) 0.33291(14) 0.49307(10) 0.0180(2) Uani 1 1 d . . . . .
C6 C 0.73847(15) 0.68180(14) 0.41382(10) 0.0184(2) Uani 1 1 d . . . . .
H6 H 0.735841 0.801697 0.386620 0.022 Uiso 1 1 calc R U . . .
C4 C 0.77846(15) 0.47421(15) 0.58547(10) 0.0190(2) Uani 1 1 d . . . . .
C9 C 0.87716(16) 0.08284(15) 0.18101(12) 0.0225(2) Uani 1 1 d . . . . .
H9A H 0.844206 0.012844 0.099904 0.034 Uiso 1 1 calc R U . . .
H9B H 0.918550 0.001732 0.249106 0.034 Uiso 1 1 calc R U . . .
H9C H 0.982353 0.170348 0.173840 0.034 Uiso 1 1 calc R U . . .
C7 C 0.80956(16) 0.44097(16) 0.71901(11) 0.0226(2) Uani 1 1 d . . . . .
C5 C 0.77433(15) 0.65027(15) 0.54266(10) 0.0196(2) Uani 1 1 d . . . . .
H5 H 0.796528 0.749347 0.603200 0.024 Uiso 1 1 calc R U . . .
C10 C 0.43929(16) 0.06056(15) 0.20691(12) 0.0226(2) Uani 1 1 d . . . . .
H10A H 0.327871 0.137272 0.207439 0.034 Uiso 1 1 calc R U . . .
H10B H 0.446889 -0.017196 0.279603 0.034 Uiso 1 1 calc R U . . .
H10C H 0.424434 -0.013918 0.127238 0.034 Uiso 1 1 calc R U . . .
C8 C 0.83151(19) 0.41401(18) 0.82976(12) 0.0297(3) Uani 1 1 d . . . . .
H8 H 0.849055 0.392456 0.918301 0.036 Uiso 1 1 calc R U . . .
B1 B 0.65136(17) 0.54097(16) 0.17538(11) 0.0171(2) 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
Si1 O2 1.6897(8) . ?
Si1 C2 1.8701(11) . ?
Si1 C9 1.8487(11) . ?
Si1 C10 1.8461(11) . ?
F1 C3 1.3584(12) . ?
O2 B1 1.3943(13) . ?
O1 H1 0.8400 . ?
O1 B1 1.3453(14) . ?
C1 C2 1.4137(14) . ?
C1 C6 1.3963(14) . ?
C1 B1 1.5679(15) . ?
C2 C3 1.3768(14) . ?
C3 C4 1.3951(15) . ?
C6 H6 0.9500 . ?
C6 C5 1.3844(15) . ?
C4 C7 1.4343(15) . ?
C4 C5 1.4057(15) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C7 C8 1.1882(17) . ?
C5 H5 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C8 H8 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Si1 C2 94.51(4) . . ?
O2 Si1 C9 108.07(5) . . ?
O2 Si1 C10 108.00(5) . . ?
C9 Si1 C2 113.91(5) . . ?
C10 Si1 C2 115.44(5) . . ?
C10 Si1 C9 114.56(5) . . ?
B1 O2 Si1 113.33(7) . . ?
B1 O1 H1 109.5 . . ?
C2 C1 B1 111.16(9) . . ?
C6 C1 C2 120.08(10) . . ?
C6 C1 B1 128.70(10) . . ?
C1 C2 Si1 108.12(7) . . ?
C3 C2 Si1 133.64(8) . . ?
C3 C2 C1 118.24(10) . . ?
F1 C3 C2 118.84(9) . . ?
F1 C3 C4 118.03(9) . . ?
C2 C3 C4 123.13(10) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.97(10) . . ?
C5 C6 H6 120.0 . . ?
C3 C4 C7 121.23(10) . . ?
C3 C4 C5 117.42(10) . . ?
C5 C4 C7 121.34(10) . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C7 C4 178.68(13) . . ?
C6 C5 C4 121.15(10) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
Si1 C10 H10A 109.5 . . ?
Si1 C10 H10B 109.5 . . ?
Si1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C8 H8 180.0 . . ?
O2 B1 C1 112.74(9) . . ?
O1 B1 O2 122.33(10) . . ?
O1 B1 C1 124.93(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Si1 O2 B1 O1 178.36(8) . . . . ?
Si1 O2 B1 C1 -2.31(11) . . . . ?
Si1 C2 C3 F1 0.41(16) . . . . ?
Si1 C2 C3 C4 -179.04(8) . . . . ?
F1 C3 C4 C7 -1.54(15) . . . . ?
F1 C3 C4 C5 179.40(9) . . . . ?
O2 Si1 C2 C1 -3.67(8) . . . . ?
O2 Si1 C2 C3 175.80(11) . . . . ?
C1 C2 C3 F1 179.85(9) . . . . ?
C1 C2 C3 C4 0.40(16) . . . . ?
C1 C6 C5 C4 -0.19(16) . . . . ?
C2 Si1 O2 B1 3.43(8) . . . . ?
C2 C1 C6 C5 -0.59(16) . . . . ?
C2 C1 B1 O2 -0.61(13) . . . . ?
C2 C1 B1 O1 178.70(10) . . . . ?
C2 C3 C4 C7 177.91(10) . . . . ?
C2 C3 C4 C5 -1.14(16) . . . . ?
C3 C4 C5 C6 1.02(16) . . . . ?
C6 C1 C2 Si1 -179.94(8) . . . . ?
C6 C1 C2 C3 0.49(15) . . . . ?
C6 C1 B1 O2 -177.50(10) . . . . ?
C6 C1 B1 O1 1.82(18) . . . . ?
C9 Si1 O2 B1 -113.53(8) . . . . ?
C9 Si1 C2 C1 108.37(8) . . . . ?
C9 Si1 C2 C3 -72.15(12) . . . . ?
C7 C4 C5 C6 -178.03(10) . . . . ?
C10 Si1 O2 B1 122.03(8) . . . . ?
C10 Si1 C2 C1 -116.05(8) . . . . ?
C10 Si1 C2 C3 63.43(12) . . . . ?
B1 C1 C2 Si1 2.87(10) . . . . ?
B1 C1 C2 C3 -176.70(9) . . . . ?
B1 C1 C6 C5 176.05(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.228
_oxdiff_exptl_absorpt_empirical_full_min 0.838
####################################################################### 
# 
# 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_1c_MeCN
_database_code_depnum_ccdc_archive 'CCDC 2304135'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology
Poland
;
_audit_update_record             
;
2023-10-27 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
6-Ethynyl-7-fluoro-1,1-dimethylbenzo[c][1,2,5]oxasilaborol-3(1H)-ol MeCN monosolvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 B F O2 Si, C2 H3 N'
_chemical_formula_sum            'C12 H13 B F N O2 Si'
_chemical_formula_weight         261.13

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'
B B 0.0013 0.0007 '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'
Si Si 0.0817 0.0704 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

_cell_length_a                   8.6127(2)
_cell_length_b                   7.0177(2)
_cell_length_c                   11.1617(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.153(2)
_cell_angle_gamma                90
_cell_volume                     669.38(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7108
_cell_measurement_theta_min      2.3850
_cell_measurement_theta_max      33.3800

_exptl_crystal_description       block
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.179
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.074
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 5 0.0543
-2 5 1 0.0836
-5 1 0 0.0799
-5 -1 0 0.0821
2 -5 -1 0.0968
0 -1 -5 0.0199
5 1 0 0.1122
-1 0 0 0.0749
0 -1 5 0.0281
1 5 -2 0.0907
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
-0.0006 0.9976 5.0010 -0.1162 -0.3084 0.0646
-2.0003 5.0015 1.0066 -0.5329 -0.0140 -0.0183
-5.0034 1.0029 0.0022 -0.2068 0.0198 -0.3734
-5.0040 -0.9975 -0.0003 -0.0127 0.0017 -0.4272
2.0003 -5.0015 -1.0066 0.5329 0.0140 0.0183
0.0006 -0.9976 -5.0010 0.1162 0.3084 -0.0646
5.0040 0.9975 0.0003 0.0127 -0.0017 0.4272
-1.0007 0.0005 0.0002 -0.0220 0.0022 -0.0801
-0.0011 -1.0027 4.9985 0.0779 -0.3265 0.0109
1.0024 5.0014 -1.9938 -0.4556 0.1700 0.1992
_exptl_absorpt_correction_T_min  0.708
_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 0.845
_oxdiff_exptl_absorpt_empirical_full_max 1.211
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_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_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 8.0013
_diffrn_reflns_number            14332
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.383
_diffrn_reflns_theta_max         33.833
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2733
_reflns_number_gt                2374
_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 1.171.39.46 (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_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.1473P] 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         2733
_refine_ls_number_parameters     114
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.084
_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 0.20027(4) 0.2500 0.70191(3) 0.01311(9) Uani 1 2 d S T P . .
F1 F 0.24624(9) 0.2500 0.40784(7) 0.01870(16) Uani 1 2 d S T P . .
O2 O 0.31294(10) 0.2500 0.83497(8) 0.01771(18) Uani 1 2 d S T P . .
O1 O 0.57324(11) 0.2500 0.92786(8) 0.0222(2) Uani 1 2 d DS T P . .
C8 C 0.53078(14) 0.2500 0.31252(10) 0.0149(2) Uani 1 2 d S T P . .
C3 C 0.37946(13) 0.2500 0.48699(10) 0.01289(19) Uani 1 2 d S T P . .
C1 C 0.50759(13) 0.2500 0.69058(10) 0.01286(19) Uani 1 2 d S T P . .
C5 C 0.65964(14) 0.2500 0.52285(10) 0.0149(2) Uani 1 2 d S T P . .
H5 H 0.7587 0.2500 0.4937 0.018 Uiso 1 2 calc R U P . .
C4 C 0.52231(13) 0.2500 0.44007(10) 0.0128(2) Uani 1 2 d S T P . .
C2 C 0.36773(13) 0.2500 0.60938(10) 0.01265(19) Uani 1 2 d S T P . .
B1 B 0.47093(16) 0.2500 0.82542(12) 0.0155(2) Uani 1 2 d S T P . .
C9 C 0.54425(15) 0.2500 0.20698(11) 0.0189(2) Uani 1 2 d S T P . .
H9 H 0.5549 0.2500 0.1233 0.023 Uiso 1 2 calc R U P . .
C6 C 0.65257(14) 0.2500 0.64647(10) 0.0150(2) Uani 1 2 d S T P . .
H6 H 0.7464 0.2500 0.7011 0.018 Uiso 1 2 calc R U P . .
C7 C 0.07800(11) 0.03234(13) 0.68827(9) 0.02049(17) Uani 1 1 d . . . . .
H7A H 0.1455 -0.0804 0.6989 0.031 Uiso 1 1 calc R U . . .
H7B H 0.0166 0.0287 0.6082 0.031 Uiso 1 1 calc R U . . .
H7C H 0.0071 0.0335 0.7505 0.031 Uiso 1 1 calc R U . . .
H1 H 0.6697(12) 0.2500 0.9218(18) 0.031 Uiso 1 2 d DS U P . .
N1 N 0.90706(15) 0.2500 0.95509(12) 0.0275(3) Uani 1 2 d S T P . .
C11 C 1.17786(16) 0.2500 1.08832(13) 0.0230(3) Uani 1 2 d S T P . .
C10 C 1.02588(16) 0.2500 1.01424(12) 0.0213(2) Uani 1 2 d S T P . .
H11B H 1.2329(14) 0.145(2) 1.0669(12) 0.032 Uiso 1 1 d . U . . .
H11A H 1.164(2) 0.2500 1.1768(18) 0.032 Uiso 1 2 d S 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
Si1 O2 1.6699(9) . ?
Si1 C7 1.8508(9) . ?
Si1 C7 1.8508(9) 4_565 ?
Si1 C2 1.8756(12) . ?
F1 C3 1.3582(13) . ?
O2 B1 1.3781(16) . ?
O1 B1 1.3539(16) . ?
O1 H1 0.842(9) . ?
C8 C9 1.1980(17) . ?
C8 C4 1.4345(16) . ?
C3 C2 1.3823(16) . ?
C3 C4 1.3959(16) . ?
C1 C6 1.3981(16) . ?
C1 C2 1.4144(15) . ?
C1 B1 1.5759(17) . ?
C5 C6 1.3887(16) . ?
C5 C4 1.4073(15) . ?
C5 H5 0.9500 . ?
C9 H9 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
N1 C10 1.1467(18) . ?
C11 C10 1.4587(18) . ?
C11 H11B 0.925(14) . ?
C11 H11A 1.01(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
O2 Si1 C7 109.56(4) . . ?
O2 Si1 C7 109.56(4) . 4_565 ?
C7 Si1 C7 111.24(6) . 4_565 ?
O2 Si1 C2 95.06(5) . . ?
C7 Si1 C2 115.05(3) . . ?
C7 Si1 C2 115.05(3) 4_565 . ?
B1 O2 Si1 113.66(8) . . ?
B1 O1 H1 118.5(14) . . ?
C9 C8 C4 177.37(13) . . ?
F1 C3 C2 118.88(10) . . ?
F1 C3 C4 117.95(10) . . ?
C2 C3 C4 123.17(10) . . ?
C6 C1 C2 120.07(10) . . ?
C6 C1 B1 129.07(10) . . ?
C2 C1 B1 110.86(10) . . ?
C6 C5 C4 121.00(11) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C3 C4 C5 117.49(10) . . ?
C3 C4 C8 121.90(10) . . ?
C5 C4 C8 120.61(10) . . ?
C3 C2 C1 118.17(10) . . ?
C3 C2 Si1 134.43(9) . . ?
C1 C2 Si1 107.40(8) . . ?
O1 B1 O2 118.67(11) . . ?
O1 B1 C1 128.31(11) . . ?
O2 B1 C1 113.02(10) . . ?
C8 C9 H9 180.0 . . ?
C5 C6 C1 120.10(10) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
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 C11 H11B 107.8(8) . . ?
C10 C11 H11A 110.1(12) . . ?
H11B C11 H11A 112.4(10) . . ?
N1 C10 C11 179.39(15) . . ?

_refine_diff_density_max         0.466
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.055

_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_2c
_database_code_depnum_ccdc_archive 'CCDC 2304136'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology
Poland
;
_audit_update_record             
;
2023-10-27 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
6-Ethynyl-7-chloro-1,1-dimethylbenzo[c][1,2,5]oxasilaborol-3(1H)-ol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 B Cl O2 Si'
_chemical_formula_sum            'C10 H10 B Cl O2 Si'
_chemical_formula_weight         236.53

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'
Cl Cl 0.3639 0.7018 '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'

_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                   6.9876(3)
_cell_length_b                   7.7137(4)
_cell_length_c                   10.6833(5)
_cell_angle_alpha                85.701(4)
_cell_angle_beta                 81.858(4)
_cell_angle_gamma                89.401(4)
_cell_volume                     568.42(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5112
_cell_measurement_theta_min      4.1990
_cell_measurement_theta_max      77.6380

_exptl_crystal_description       unspecifed
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    3.788
_exptl_absorpt_correction_T_min  0.54861
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.662
_oxdiff_exptl_absorpt_empirical_full_max 1.559
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;


_diffrn_ambient_temperature      100(2)
_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            5118
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.192
_diffrn_reflns_theta_max         77.494
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2404
_reflns_number_gt                2395
_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 1.171.42.70a (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_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+0.2454P] 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         2404
_refine_ls_number_parameters     141
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0773
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
Cl1 Cl 0.24132(5) 0.87132(4) 0.53557(3) 0.02013(11) Uani 1 1 d . . . . .
Si1 Si 0.33205(5) 0.78648(4) 0.21382(3) 0.01236(11) Uani 1 1 d . . . . .
O2 O 0.37225(13) 0.62595(12) 0.11343(8) 0.01587(19) Uani 1 1 d . . . . .
O1 O 0.37393(15) 0.31423(12) 0.11205(9) 0.0202(2) Uani 1 1 d D . . . .
C2 C 0.28654(17) 0.63400(16) 0.36009(11) 0.0132(2) Uani 1 1 d . . . . .
C1 C 0.29419(17) 0.46247(16) 0.32232(12) 0.0137(2) Uani 1 1 d . . . . .
C4 C 0.22316(17) 0.51980(17) 0.58124(12) 0.0145(2) Uani 1 1 d . . . . .
C6 C 0.26441(18) 0.32196(16) 0.41254(12) 0.0156(2) Uani 1 1 d . . . . .
H6 H 0.2686 0.2067 0.3866 0.019 Uiso 1 1 calc R U . . .
C3 C 0.25116(17) 0.65983(16) 0.48864(12) 0.0137(2) Uani 1 1 d . . . . .
C5 C 0.22858(18) 0.35085(17) 0.54059(12) 0.0163(3) Uani 1 1 d . . . . .
H5 H 0.2074 0.2545 0.6017 0.020 Uiso 1 1 calc R U . . .
C9 C 0.19259(19) 0.54736(17) 0.71422(13) 0.0176(3) Uani 1 1 d . . . . .
C10 C 0.1710(2) 0.5694(2) 0.82480(13) 0.0248(3) Uani 1 1 d . . . . .
H10 H 0.1538 0.5870 0.9128 0.030 Uiso 1 1 calc R U . . .
C8 C 0.11793(19) 0.91346(18) 0.17757(13) 0.0202(3) Uani 1 1 d . . . . .
H8B H 0.1491 0.9799 0.0955 0.030 Uiso 1 1 calc R U . . .
H8C H 0.0808 0.9935 0.2439 0.030 Uiso 1 1 calc R U . . .
H8A H 0.0104 0.8342 0.1742 0.030 Uiso 1 1 calc R U . . .
C7 C 0.55403(18) 0.91930(18) 0.19645(13) 0.0189(3) Uani 1 1 d . . . . .
H7C H 0.6655 0.8433 0.2046 0.028 Uiso 1 1 calc R U . . .
H7B H 0.5421 1.0017 0.2626 0.028 Uiso 1 1 calc R U . . .
H7A H 0.5722 0.9834 0.1129 0.028 Uiso 1 1 calc R U . . .
B1 B 0.3488(2) 0.45985(19) 0.17424(13) 0.0154(3) Uani 1 1 d . . . . .
H1 H 0.431(2) 0.335(2) 0.0387(11) 0.023 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
Cl1 C3 1.7401(13) . ?
Si1 O2 1.6937(9) . ?
Si1 C7 1.8476(13) . ?
Si1 C8 1.8505(13) . ?
Si1 C2 1.8756(13) . ?
O2 B1 1.3928(17) . ?
O1 B1 1.3449(17) . ?
O1 H1 0.831(9) . ?
C2 C3 1.3895(17) . ?
C2 C1 1.4103(17) . ?
C1 C6 1.3923(18) . ?
C1 B1 1.5755(18) . ?
C4 C5 1.4028(18) . ?
C4 C3 1.4046(18) . ?
C4 C9 1.4379(17) . ?
C6 C5 1.3896(18) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C9 C10 1.194(2) . ?
C10 H10 0.9500 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 H8A 0.9800 . ?
C7 H7C 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7A 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
O2 Si1 C7 107.85(6) . . ?
O2 Si1 C8 109.12(6) . . ?
C7 Si1 C8 112.98(6) . . ?
O2 Si1 C2 94.48(5) . . ?
C7 Si1 C2 116.06(6) . . ?
C8 Si1 C2 114.35(6) . . ?
B1 O2 Si1 113.37(8) . . ?
B1 O1 H1 111.4(13) . . ?
C3 C2 C1 118.84(11) . . ?
C3 C2 Si1 133.03(10) . . ?
C1 C2 Si1 108.12(9) . . ?
C6 C1 C2 120.36(11) . . ?
C6 C1 B1 128.34(12) . . ?
C2 C1 B1 111.22(11) . . ?
C5 C4 C3 118.12(11) . . ?
C5 C4 C9 120.51(12) . . ?
C3 C4 C9 121.36(12) . . ?
C5 C6 C1 119.82(12) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C2 C3 C4 121.68(12) . . ?
C2 C3 Cl1 118.96(10) . . ?
C4 C3 Cl1 119.36(10) . . ?
C6 C5 C4 121.16(12) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C10 C9 C4 178.69(14) . . ?
C9 C10 H10 180.0 . . ?
Si1 C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
H8B C8 H8A 109.5 . . ?
H8C C8 H8A 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7C C7 H7B 109.5 . . ?
Si1 C7 H7A 109.5 . . ?
H7C C7 H7A 109.5 . . ?
H7B C7 H7A 109.5 . . ?
O1 B1 O2 122.96(12) . . ?
O1 B1 C1 124.34(12) . . ?
O2 B1 C1 112.69(11) . . ?

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
O1 H1 O2 0.831(9) 1.983(10) 2.7931(13) 164.6(18) 2_665

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.075

_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_4d
_database_code_depnum_ccdc_archive 'CCDC 2304138'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology
Poland
;
_audit_update_record             
;
2023-10-27 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
7-Fluoro-1,1-dimethyl-6-(1-(2-fluorophenylsulfonyl)-1H-1,2,3-triazol-4-yl)benzo[c][1,2,5]oxasilaborol-3(1H)-ol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 B F2 N3 O4 S Si, C H Cl3'
_chemical_formula_sum            'C17 H15 B Cl3 F2 N3 O4 S Si'
_chemical_formula_weight         540.63

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.8484(4)
_cell_length_b                   11.1678(4)
_cell_length_c                   12.0146(5)
_cell_angle_alpha                89.089(3)
_cell_angle_beta                 77.254(3)
_cell_angle_gamma                80.690(3)
_cell_volume                     1142.50(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7810
_cell_measurement_theta_min      2.5060
_cell_measurement_theta_max      29.6910

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_F_000             548
_exptl_absorpt_coefficient_mu    0.592
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.104
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 3 3 0.0403
0 5 -1 0.0732
-5 3 -4 0.0900
-5 -3 -3 0.0641
-3 -5 -1 0.0525
5 1 3 0.0487
-1 0 5 0.0427
2 -1 -5 0.0380
0 -1 5 0.0484
1 2 5 0.0290
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
4.9964 3.0053 2.9972 -0.2675 0.2582 0.2174
0.0003 5.0044 -1.0094 -0.1572 0.1705 -0.2300
-4.9962 2.9998 -4.0085 0.0700 -0.0612 -0.4901
-4.9964 -3.0053 -2.9972 0.2675 -0.2582 -0.2174
-2.9982 -5.0061 -0.9923 0.2540 -0.2701 0.0194
4.9967 1.0038 3.0010 -0.1869 0.2052 0.3028
-1.0045 -0.0041 4.9994 -0.2184 -0.2481 0.0233
2.0046 -0.9956 -4.9969 0.2559 0.2800 0.0786
-0.0045 -1.0039 5.0018 -0.1809 -0.2161 0.1252
0.9950 1.9993 4.9967 -0.3045 -0.0781 0.0563
_exptl_absorpt_correction_T_min  0.718
_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 0.865
_oxdiff_exptl_absorpt_empirical_full_max 1.600
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_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_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 8.0013
_diffrn_reflns_number            19660
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.392
_diffrn_reflns_theta_max         30.004
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6007
_reflns_number_gt                4818
_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)+(0.0450P)²+1.0587P] 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         6007
_refine_ls_number_parameters     313
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
Cl2A Cl 0.0791(2) 0.62964(18) 0.9006(2) 0.0874(8) Uani 0.564(2) 1 d . . P A 1
Cl3A Cl 0.3101(3) 0.5313(2) 1.02844(13) 0.0684(7) Uani 0.564(2) 1 d . . P A 1
Cl2B Cl 0.1229(2) 0.5227(2) 0.82749(18) 0.0641(8) Uani 0.436(2) 1 d . . P A 2
Cl3B Cl 0.2141(3) 0.6145(2) 1.02211(18) 0.0643(9) Uani 0.436(2) 1 d . . P A 2
C19 C 0.2723(3) 0.5434(2) 0.8913(2) 0.0340(6) Uani 1 1 d . . . . .
H19 H 0.2747 0.4602 0.8608 0.041 Uiso 1 1 calc R U . A 1
S1 S 0.23871(6) 0.73998(5) 0.44179(4) 0.01890(13) Uani 1 1 d . . . . .
Si1 Si 0.22727(7) 1.00793(5) -0.24102(5) 0.01552(13) Uani 1 1 d . . . . .
F1 F 0.18796(14) 0.92416(11) 0.02969(10) 0.0211(3) Uani 1 1 d . . . . .
O2 O 0.65529(17) 0.95353(14) -0.41991(13) 0.0193(3) Uani 1 1 d D . . . .
F2 F 0.09538(16) 0.60844(11) 0.29059(11) 0.0258(3) Uani 1 1 d . . . . .
O1 O 0.37329(17) 1.00672(13) -0.35837(12) 0.0176(3) Uani 1 1 d . . . . .
O4 O 0.09008(19) 0.81181(14) 0.44525(13) 0.0231(3) Uani 1 1 d . . . . .
O3 O 0.3348(2) 0.76119(15) 0.51719(13) 0.0265(4) Uani 1 1 d . . . . .
N1 N 0.3436(2) 0.75906(16) 0.30736(15) 0.0174(4) Uani 1 1 d . . . . .
C2 C 0.5153(2) 0.91544(17) -0.21475(17) 0.0160(4) Uani 1 1 d . . . . .
C10 C 0.2974(3) 0.82133(18) 0.21931(18) 0.0179(4) Uani 1 1 d . . . . .
H10 H 0.1980 0.8686 0.2192 0.021 Uiso 1 1 calc R U . . .
C4 C 0.6077(2) 0.82199(19) -0.05525(18) 0.0176(4) Uani 1 1 d . . . . .
H4 H 0.6918 0.7823 -0.0240 0.021 Uiso 1 1 calc R U . . .
C1 C 0.3608(2) 0.93747(17) -0.14790(17) 0.0156(4) Uani 1 1 d . . . . .
C16 C 0.1547(3) 0.53570(19) 0.36617(18) 0.0190(4) Uani 1 1 d . . . . .
C11 C 0.2288(2) 0.58492(19) 0.44080(17) 0.0178(4) Uani 1 1 d . . . . .
N2 N 0.4939(2) 0.70030(17) 0.27512(16) 0.0230(4) Uani 1 1 d . . . . .
C3 C 0.6381(2) 0.85826(18) -0.16781(18) 0.0171(4) Uani 1 1 d . . . . .
H3 H 0.7423 0.8442 -0.2128 0.021 Uiso 1 1 calc R U . . .
C5 C 0.4558(2) 0.84266(18) 0.01310(17) 0.0160(4) Uani 1 1 d . . . . .
C9 C 0.4261(2) 0.80051(18) 0.13108(17) 0.0156(4) Uani 1 1 d . . . . .
N3 N 0.5429(2) 0.72582(17) 0.16880(15) 0.0219(4) Uani 1 1 d . . . . .
C6 C 0.3369(2) 0.90179(18) -0.03637(17) 0.0159(4) Uani 1 1 d . . . . .
B1 B 0.5213(3) 0.9600(2) -0.3403(2) 0.0166(5) Uani 1 1 d . . . . .
C14 C 0.2060(3) 0.3408(2) 0.4442(2) 0.0284(5) Uani 1 1 d . . . . .
H14 H 0.1976 0.2570 0.4461 0.034 Uiso 1 1 calc R U . . .
C15 C 0.1431(3) 0.4147(2) 0.3667(2) 0.0245(5) Uani 1 1 d . . . . .
H15 H 0.0927 0.3822 0.3147 0.029 Uiso 1 1 calc R U . . .
C12 C 0.2932(3) 0.5098(2) 0.5182(2) 0.0247(5) Uani 1 1 d . . . . .
H12 H 0.3446 0.5421 0.5696 0.030 Uiso 1 1 calc R U . . .
C13 C 0.2812(3) 0.3880(2) 0.5191(2) 0.0300(5) Uani 1 1 d . . . . .
H13 H 0.3247 0.3362 0.5715 0.036 Uiso 1 1 calc R U . . .
C7 C 0.1312(3) 1.16540(19) -0.2040(2) 0.0223(5) Uani 1 1 d . . . . .
H7A H 0.0843 1.1996 -0.2665 0.033 Uiso 1 1 calc R U . . .
H7B H 0.2092 1.2139 -0.1915 0.033 Uiso 1 1 calc R U . . .
H7C H 0.0490 1.1666 -0.1342 0.033 Uiso 1 1 calc R U . . .
C8 C 0.0843(3) 0.9122(2) -0.2626(2) 0.0241(5) Uani 1 1 d . . . . .
H8A H 0.0375 0.9432 -0.3262 0.036 Uiso 1 1 calc R U . . .
H8B H 0.0017 0.9140 -0.1930 0.036 Uiso 1 1 calc R U . . .
H8C H 0.1379 0.8285 -0.2802 0.036 Uiso 1 1 calc R U . . .
H2 H 0.648(3) 0.971(2) -0.4860(12) 0.036 Uiso 1 1 d D U . . .
Cl1 Cl 0.41162(10) 0.61361(6) 0.79731(6) 0.04431(19) 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
Cl2A C19 1.802(3) . ?
Cl3A C19 1.752(3) . ?
Cl2B C19 1.714(3) . ?
Cl3B C19 1.708(3) . ?
C19 Cl1 1.755(3) . ?
C19 H19 1.0000 . ?
S1 O4 1.4179(17) . ?
S1 O3 1.4181(16) . ?
S1 N1 1.7052(18) . ?
S1 C11 1.748(2) . ?
Si1 O1 1.6877(15) . ?
Si1 C7 1.841(2) . ?
Si1 C8 1.844(2) . ?
Si1 C1 1.877(2) . ?
F1 C6 1.367(2) . ?
O2 B1 1.342(3) . ?
O2 H2 0.830(10) . ?
F2 C16 1.345(2) . ?
O1 B1 1.391(3) . ?
N1 C10 1.359(3) . ?
N1 N2 1.359(3) . ?
C2 C3 1.393(3) . ?
C2 C1 1.409(3) . ?
C2 B1 1.573(3) . ?
C10 C9 1.366(3) . ?
C10 H10 0.9500 . ?
C4 C3 1.387(3) . ?
C4 C5 1.397(3) . ?
C4 H4 0.9500 . ?
C1 C6 1.373(3) . ?
C16 C15 1.372(3) . ?
C16 C11 1.388(3) . ?
C11 C12 1.395(3) . ?
N2 N3 1.298(3) . ?
C3 H3 0.9500 . ?
C5 C6 1.391(3) . ?
C5 C9 1.468(3) . ?
C9 N3 1.373(3) . ?
C14 C15 1.384(3) . ?
C14 C13 1.387(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9500 . ?
C13 H13 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
Cl3B C19 Cl2B 115.2(2) . . ?
Cl3B C19 Cl1 112.20(15) . . ?
Cl2B C19 Cl1 110.32(16) . . ?
Cl3A C19 Cl1 111.98(16) . . ?
Cl3A C19 Cl2A 108.79(18) . . ?
Cl1 C19 Cl2A 109.64(15) . . ?
Cl3A C19 H19 108.8 . . ?
Cl1 C19 H19 108.8 . . ?
Cl2A C19 H19 108.8 . . ?
O4 S1 O3 122.27(10) . . ?
O4 S1 N1 104.01(9) . . ?
O3 S1 N1 106.31(9) . . ?
O4 S1 C11 111.68(10) . . ?
O3 S1 C11 108.37(10) . . ?
N1 S1 C11 102.03(9) . . ?
O1 Si1 C7 109.33(9) . . ?
O1 Si1 C8 111.30(9) . . ?
C7 Si1 C8 111.13(11) . . ?
O1 Si1 C1 94.31(8) . . ?
C7 Si1 C1 116.00(10) . . ?
C8 Si1 C1 113.55(10) . . ?
B1 O2 H2 117(2) . . ?
B1 O1 Si1 113.79(13) . . ?
C10 N1 N2 111.17(17) . . ?
C10 N1 S1 129.53(16) . . ?
N2 N1 S1 119.18(14) . . ?
C3 C2 C1 120.22(19) . . ?
C3 C2 B1 128.46(19) . . ?
C1 C2 B1 111.30(18) . . ?
N1 C10 C9 104.31(18) . . ?
N1 C10 H10 127.8 . . ?
C9 C10 H10 127.8 . . ?
C3 C4 C5 121.31(19) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C1 C2 117.91(19) . . ?
C6 C1 Si1 133.91(17) . . ?
C2 C1 Si1 108.12(14) . . ?
F2 C16 C15 119.48(19) . . ?
F2 C16 C11 118.96(18) . . ?
C15 C16 C11 121.6(2) . . ?
C16 C11 C12 119.4(2) . . ?
C16 C11 S1 121.14(16) . . ?
C12 C11 S1 119.44(17) . . ?
N3 N2 N1 106.44(17) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C6 C5 C4 117.16(18) . . ?
C6 C5 C9 122.61(19) . . ?
C4 C5 C9 120.21(19) . . ?
C10 C9 N3 108.11(18) . . ?
C10 C9 C5 132.28(19) . . ?
N3 C9 C5 119.60(18) . . ?
N2 N3 C9 109.96(18) . . ?
F1 C6 C1 118.42(18) . . ?
F1 C6 C5 117.95(17) . . ?
C1 C6 C5 123.62(19) . . ?
O2 B1 O1 124.43(19) . . ?
O2 B1 C2 123.13(19) . . ?
O1 B1 C2 112.44(18) . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 118.8(2) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
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         0.739
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.075

_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_5b
_database_code_depnum_ccdc_archive 'CCDC 2304139'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology
Poland
;
_audit_update_record             
;
2023-10-27 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H40 F2 N8 O5 S2 Si2'
_chemical_formula_sum            'C36 H40 F2 N8 O5 S2 Si2'
_chemical_formula_weight         823.06

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'
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      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                   12.2547(2)
_cell_length_b                   21.3124(4)
_cell_length_c                   14.7890(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.9810(10)
_cell_angle_gamma                90
_cell_volume                     3860.24(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11609
_cell_measurement_theta_min      3.5590
_cell_measurement_theta_max      76.2120

_exptl_crystal_description       block
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             1720
_exptl_absorpt_coefficient_mu    2.388
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.087
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0903
0 1 5 0.0659
-2 -5 1 0.0628
2 5 0 0.0738
5 -1 0 0.0591
-5 1 0 0.0279
0 -1 -1 0.0984
0 5 -3 0.0852
0 -4 5 0.0500
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
-0.0013 0.0007 -1.0000 0.0069 0.0052 0.1039
0.0056 0.9972 4.9994 0.0204 0.0211 -0.5253
-1.9947 -5.0072 1.0057 -0.1164 -0.4301 -0.0672
1.9960 5.0065 -0.0056 0.1095 0.4250 -0.0367
5.0049 -0.9965 -0.0032 -0.4658 0.4294 -0.0128
-5.0049 0.9965 0.0032 0.4658 -0.4294 0.0128
-0.0002 -1.0002 -0.9992 -0.0479 -0.0417 0.1097
-0.0096 5.0069 -3.0041 0.2945 0.2499 0.2824
0.0111 -4.0074 5.0034 -0.2535 -0.2134 -0.4961
_exptl_absorpt_correction_T_min  0.801
_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 0.852
_oxdiff_exptl_absorpt_empirical_full_max 1.183
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_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_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            22446
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.609
_diffrn_reflns_theta_max         76.700
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8052
_reflns_number_gt                7116
_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 1.171.40.84a (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)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0810P)²+0.9368P] 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         8052
_refine_ls_number_parameters     496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.76451(3) 0.20080(2) 0.19793(2) 0.02018(11) Uani 1 1 d . . . . .
S2 S 0.72730(3) -0.23211(2) 0.35609(3) 0.02173(11) Uani 1 1 d . . . . .
Si3 Si 1.34106(4) -0.02591(2) 0.34285(3) 0.02074(12) Uani 1 1 d . . . . .
Si4 Si 1.33495(4) -0.01842(2) 0.13185(3) 0.01886(11) Uani 1 1 d . . . . .
F1 F 1.10894(8) 0.03577(5) 0.35561(8) 0.0262(2) Uani 1 1 d . . . . .
F2 F 1.10489(8) -0.07385(5) 0.15433(7) 0.0233(2) Uani 1 1 d . . . . .
O4 O 0.67476(11) 0.24172(6) 0.21614(9) 0.0265(3) Uani 1 1 d . . . . .
O5 O 0.81051(11) 0.19952(6) 0.10994(8) 0.0253(3) Uani 1 1 d . . . . .
O2 O 0.69743(12) -0.27735(6) 0.28781(9) 0.0279(3) Uani 1 1 d . . . . .
O3 O 0.83144(11) -0.23616(7) 0.40287(9) 0.0276(3) Uani 1 1 d . . . . .
N1 N 0.80567(12) -0.04687(8) 0.38927(10) 0.0238(3) Uani 1 1 d . . . . .
O1 O 1.35943(11) -0.04124(7) 0.23597(8) 0.0268(3) Uani 1 1 d . . . . .
N8 N 0.72620(12) 0.13001(7) 0.21720(9) 0.0219(3) Uani 1 1 d . . . . .
H8N H 0.7514 0.0995 0.1837 0.026 Uiso 1 1 calc R U . . .
N6 N 0.76205(12) -0.08663(7) 0.14535(9) 0.0194(3) Uani 1 1 d . . . . .
N3 N 0.77477(12) 0.05170(7) 0.38675(9) 0.0206(3) Uani 1 1 d . . . . .
N4 N 0.79754(12) 0.01116(7) 0.13917(10) 0.0221(3) Uani 1 1 d . . . . .
C17 C 1.18711(14) 0.08355(8) 0.09632(11) 0.0204(3) Uani 1 1 d . . . . .
H17 H 1.2513 0.1078 0.0895 0.025 Uiso 1 1 calc R U . . .
C20 C 1.20506(14) -0.06004(9) 0.37235(10) 0.0205(3) Uani 1 1 d . . . . .
N5 N 0.71734(12) -0.02912(7) 0.14557(11) 0.0240(3) Uani 1 1 d . . . . .
C19 C 1.10758(14) -0.02707(8) 0.37321(10) 0.0190(3) Uani 1 1 d . . . . .
C14 C 0.99556(13) 0.01431(8) 0.12013(10) 0.0178(3) Uani 1 1 d . . . . .
C2 C 0.65100(15) -0.21009(9) 0.52443(12) 0.0253(3) Uani 1 1 d . . . . .
H2 H 0.7193 -0.1904 0.5371 0.030 Uiso 1 1 calc R U . . .
C18 C 1.19678(14) 0.01998(8) 0.11975(10) 0.0194(3) Uani 1 1 d . . . . .
C24 C 1.00649(13) -0.05348(8) 0.38960(10) 0.0194(3) Uani 1 1 d . . . . .
C13 C 1.09919(14) -0.01208(8) 0.13077(10) 0.0181(3) Uani 1 1 d . . . . .
C1 C 0.62720(15) -0.23573(8) 0.43942(11) 0.0224(3) Uani 1 1 d . . . . .
N2 N 0.72721(12) -0.00494(8) 0.38836(11) 0.0261(3) Uani 1 1 d . . . . .
C29 C 0.69057(14) -0.14168(8) 0.14824(11) 0.0225(3) Uani 1 1 d . . . . .
H29A H 0.7335 -0.1799 0.1358 0.027 Uiso 1 1 calc R U . . .
H29B H 0.6324 -0.1379 0.1004 0.027 Uiso 1 1 calc R U . . .
N7 N 0.72122(13) -0.16363(8) 0.31042(10) 0.0258(3) Uani 1 1 d . . . . .
H7 H 0.7686 -0.1348 0.3282 0.031 Uiso 1 1 calc R U . . .
C15 C 0.99111(14) 0.07755(8) 0.09358(10) 0.0201(3) Uani 1 1 d . . . . .
H15 H 0.9222 0.0971 0.0829 0.024 Uiso 1 1 calc R U . . .
C27 C 0.89420(13) -0.02026(8) 0.13400(10) 0.0178(3) Uani 1 1 d . . . . .
C26 C 0.88447(13) 0.04650(8) 0.38609(10) 0.0198(3) Uani 1 1 d . . . . .
H26 H 0.9366 0.0795 0.3847 0.024 Uiso 1 1 calc R U . . .
C16 C 1.08562(15) 0.11183(8) 0.08280(11) 0.0221(3) Uani 1 1 d . . . . .
H16 H 1.0812 0.1548 0.0661 0.027 Uiso 1 1 calc R U . . .
C28 C 0.87123(13) -0.08355(8) 0.13914(10) 0.0189(3) Uani 1 1 d . . . . .
H28 H 0.9215 -0.1175 0.1384 0.023 Uiso 1 1 calc R U . . .
C38 C 0.65124(14) 0.11466(9) 0.28812(12) 0.0235(3) Uani 1 1 d . . . . .
H38A H 0.6133 0.0750 0.2720 0.028 Uiso 1 1 calc R U . . .
H38B H 0.5953 0.1481 0.2907 0.028 Uiso 1 1 calc R U . . .
C7 C 0.87065(14) 0.22072(8) 0.27743(11) 0.0204(3) Uani 1 1 d . . . . .
C25 C 0.90434(14) -0.01717(8) 0.38782(10) 0.0190(3) Uani 1 1 d . . . . .
C37 C 0.70635(14) 0.10747(9) 0.38190(11) 0.0234(3) Uani 1 1 d . . . . .
H37A H 0.7516 0.1450 0.3956 0.028 Uiso 1 1 calc R U . . .
H37B H 0.6498 0.1046 0.4279 0.028 Uiso 1 1 calc R U . . .
C30 C 0.63868(14) -0.14824(9) 0.24000(11) 0.0231(3) Uani 1 1 d . . . . .
H30A H 0.6022 -0.1084 0.2555 0.028 Uiso 1 1 calc R U . . .
H30B H 0.5826 -0.1817 0.2368 0.028 Uiso 1 1 calc R U . . .
C3 C 0.57307(17) -0.21382(9) 0.59046(12) 0.0280(4) Uani 1 1 d . . . . .
H3 H 0.5885 -0.1971 0.6490 0.034 Uiso 1 1 calc R U . . .
C22 C 1.09948(16) -0.15323(9) 0.40716(13) 0.0281(4) Uani 1 1 d . . . . .
H22 H 1.0970 -0.1970 0.4191 0.034 Uiso 1 1 calc R U . . .
C23 C 1.00445(15) -0.11795(9) 0.40745(12) 0.0251(3) Uani 1 1 d . . . . .
H23 H 0.9372 -0.1378 0.4199 0.030 Uiso 1 1 calc R U . . .
C60 C 1.43964(15) 0.04051(9) 0.10145(13) 0.0273(4) Uani 1 1 d . . . . .
H60A H 1.4345 0.0771 0.1412 0.041 Uiso 1 1 calc R U . . .
H60B H 1.4270 0.0535 0.0384 0.041 Uiso 1 1 calc R U . . .
H60C H 1.5125 0.0219 0.1088 0.041 Uiso 1 1 calc R U . . .
C8 C 0.84958(15) 0.26271(9) 0.34640(13) 0.0267(4) Uani 1 1 d . . . . .
H8 H 0.7799 0.2819 0.3501 0.032 Uiso 1 1 calc R U . . .
C11 C 1.05509(16) 0.20787(11) 0.33326(14) 0.0332(4) Uani 1 1 d . . . . .
H11 H 1.1254 0.1897 0.3283 0.040 Uiso 1 1 calc R U . . .
C36 C 1.33999(16) -0.08917(9) 0.05899(12) 0.0271(4) Uani 1 1 d . . . . .
H36A H 1.2847 -0.1194 0.0776 0.041 Uiso 1 1 calc R U . . .
H36B H 1.4125 -0.1084 0.0652 0.041 Uiso 1 1 calc R U . . .
H36C H 1.3253 -0.0772 -0.0042 0.041 Uiso 1 1 calc R U . . .
C10 C 1.03466(16) 0.24867(10) 0.40378(12) 0.0265(4) Uani 1 1 d . . . . .
H10 H 1.0906 0.2579 0.4479 0.032 Uiso 1 1 calc R U . . .
C21 C 1.19815(14) -0.12465(9) 0.38950(12) 0.0245(3) Uani 1 1 d . . . . .
H21 H 1.2626 -0.1494 0.3890 0.029 Uiso 1 1 calc R U . . .
C33 C 1.34889(17) 0.05977(10) 0.36397(16) 0.0355(4) Uani 1 1 d . . . . .
H33A H 1.2898 0.0810 0.3296 0.053 Uiso 1 1 calc R U . . .
H33B H 1.4194 0.0757 0.3447 0.053 Uiso 1 1 calc R U . . .
H33C H 1.3416 0.0679 0.4287 0.053 Uiso 1 1 calc R U . . .
C34 C 1.45244(15) -0.06644(11) 0.40890(12) 0.0313(4) Uani 1 1 d . . . . .
H34A H 1.4477 -0.1117 0.3981 0.047 Uiso 1 1 calc R U . . .
H34B H 1.4449 -0.0580 0.4735 0.047 Uiso 1 1 calc R U . . .
H34C H 1.5233 -0.0509 0.3898 0.047 Uiso 1 1 calc R U . . .
C5 C 0.44940(17) -0.26545(10) 0.48576(14) 0.0327(4) Uani 1 1 d . . . . .
H5 H 0.3798 -0.2835 0.4724 0.039 Uiso 1 1 calc R U . . .
C12 C 0.97251(16) 0.19357(10) 0.26993(13) 0.0309(4) Uani 1 1 d . . . . .
H12 H 0.9858 0.1654 0.2218 0.037 Uiso 1 1 calc R U . . .
C9 C 0.93240(17) 0.27608(10) 0.40993(12) 0.0289(4) Uani 1 1 d . . . . .
H9 H 0.9190 0.3043 0.4581 0.035 Uiso 1 1 calc R U . . .
C6 C 0.52673(16) -0.26299(9) 0.41915(12) 0.0283(4) Uani 1 1 d . . . . .
H6 H 0.5109 -0.2798 0.3607 0.034 Uiso 1 1 calc R U . . .
C4 C 0.47299(17) -0.24194(9) 0.57092(13) 0.0297(4) Uani 1 1 d . . . . .
H4 H 0.4205 -0.2450 0.6165 0.036 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 O5 1.4362(12) . ?
S1 O4 1.4364(14) . ?
S1 N8 1.6083(16) . ?
S1 C7 1.7744(17) . ?
S2 O3 1.4331(14) . ?
S2 O2 1.4346(14) . ?
S2 N7 1.6087(16) . ?
S2 C1 1.7704(18) . ?
Si3 O1 1.6371(13) . ?
Si3 C33 1.854(2) . ?
Si3 C34 1.863(2) . ?
Si3 C20 1.8835(17) . ?
Si4 O1 1.6327(12) . ?
Si4 C36 1.8556(19) . ?
Si4 C60 1.8617(19) . ?
Si4 C18 1.8836(18) . ?
F1 C19 1.365(2) . ?
F2 C13 1.3629(19) . ?
N1 N2 1.313(2) . ?
N1 C25 1.366(2) . ?
N8 C38 1.455(2) . ?
N8 H8N 0.8800 . ?
N6 N5 1.343(2) . ?
N6 C28 1.346(2) . ?
N6 C29 1.466(2) . ?
N3 N2 1.341(2) . ?
N3 C26 1.349(2) . ?
N3 C37 1.455(2) . ?
N4 N5 1.311(2) . ?
N4 C27 1.365(2) . ?
C17 C16 1.390(2) . ?
C17 C18 1.402(2) . ?
C17 H17 0.9500 . ?
C20 C19 1.386(2) . ?
C20 C21 1.403(3) . ?
C19 C24 1.390(2) . ?
C14 C13 1.393(2) . ?
C14 C15 1.404(2) . ?
C14 C27 1.465(2) . ?
C2 C3 1.392(3) . ?
C2 C1 1.392(3) . ?
C2 H2 0.9500 . ?
C18 C13 1.392(2) . ?
C24 C23 1.400(2) . ?
C24 C25 1.471(2) . ?
C1 C6 1.385(3) . ?
C29 C30 1.525(2) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
N7 C30 1.464(2) . ?
N7 H7 0.8800 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C27 C28 1.381(2) . ?
C26 C25 1.379(2) . ?
C26 H26 0.9500 . ?
C16 H16 0.9500 . ?
C28 H28 0.9500 . ?
C38 C37 1.529(2) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C7 C12 1.384(3) . ?
C7 C8 1.388(2) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C22 C23 1.386(3) . ?
C22 C21 1.387(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C11 C10 1.387(3) . ?
C11 C12 1.389(3) . ?
C11 H11 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C10 C9 1.389(3) . ?
C10 H10 0.9500 . ?
C21 H21 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C5 C4 1.377(3) . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C12 H12 0.9500 . ?
C9 H9 0.9500 . ?
C6 H6 0.9500 . ?
C4 H4 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
O5 S1 O4 120.56(8) . . ?
O5 S1 N8 105.60(8) . . ?
O4 S1 N8 107.83(8) . . ?
O5 S1 C7 107.65(8) . . ?
O4 S1 C7 106.19(8) . . ?
N8 S1 C7 108.59(8) . . ?
O3 S2 O2 120.04(9) . . ?
O3 S2 N7 106.55(8) . . ?
O2 S2 N7 107.90(8) . . ?
O3 S2 C1 106.75(8) . . ?
O2 S2 C1 107.13(8) . . ?
N7 S2 C1 107.98(9) . . ?
O1 Si3 C33 110.56(9) . . ?
O1 Si3 C34 106.91(8) . . ?
C33 Si3 C34 109.60(11) . . ?
O1 Si3 C20 107.39(7) . . ?
C33 Si3 C20 112.48(9) . . ?
C34 Si3 C20 109.73(8) . . ?
O1 Si4 C36 107.27(8) . . ?
O1 Si4 C60 108.85(8) . . ?
C36 Si4 C60 111.78(9) . . ?
O1 Si4 C18 110.75(7) . . ?
C36 Si4 C18 110.23(8) . . ?
C60 Si4 C18 107.97(8) . . ?
N2 N1 C25 109.45(15) . . ?
Si4 O1 Si3 145.50(10) . . ?
C38 N8 S1 122.28(12) . . ?
C38 N8 H8N 118.9 . . ?
S1 N8 H8N 118.9 . . ?
N5 N6 C28 111.25(14) . . ?
N5 N6 C29 119.11(14) . . ?
C28 N6 C29 129.60(15) . . ?
N2 N3 C26 111.09(15) . . ?
N2 N3 C37 119.09(14) . . ?
C26 N3 C37 129.75(15) . . ?
N5 N4 C27 109.70(15) . . ?
C16 C17 C18 121.46(16) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C20 C21 115.99(15) . . ?
C19 C20 Si3 125.18(14) . . ?
C21 C20 Si3 118.70(13) . . ?
N4 N5 N6 106.89(14) . . ?
F1 C19 C20 118.65(15) . . ?
F1 C19 C24 116.59(15) . . ?
C20 C19 C24 124.76(16) . . ?
C13 C14 C15 116.46(15) . . ?
C13 C14 C27 123.73(15) . . ?
C15 C14 C27 119.81(15) . . ?
C3 C2 C1 118.93(17) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C13 C18 C17 115.95(15) . . ?
C13 C18 Si4 123.28(13) . . ?
C17 C18 Si4 120.75(13) . . ?
C19 C24 C23 116.90(16) . . ?
C19 C24 C25 123.16(16) . . ?
C23 C24 C25 119.94(15) . . ?
F2 C13 C18 117.87(15) . . ?
F2 C13 C14 117.22(14) . . ?
C18 C13 C14 124.91(16) . . ?
C6 C1 C2 121.13(17) . . ?
C6 C1 S2 119.99(14) . . ?
C2 C1 S2 118.87(14) . . ?
N1 N2 N3 107.13(14) . . ?
N6 C29 C30 111.55(14) . . ?
N6 C29 H29A 109.3 . . ?
C30 C29 H29A 109.3 . . ?
N6 C29 H29B 109.3 . . ?
C30 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
C30 N7 S2 121.52(12) . . ?
C30 N7 H7 119.2 . . ?
S2 N7 H7 119.2 . . ?
C16 C15 C14 120.97(16) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
N4 C27 C28 107.29(15) . . ?
N4 C27 C14 120.18(15) . . ?
C28 C27 C14 132.43(15) . . ?
N3 C26 C25 104.84(15) . . ?
N3 C26 H26 127.6 . . ?
C25 C26 H26 127.6 . . ?
C15 C16 C17 120.19(16) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
N6 C28 C27 104.86(15) . . ?
N6 C28 H28 127.6 . . ?
C27 C28 H28 127.6 . . ?
N8 C38 C37 113.97(14) . . ?
N8 C38 H38A 108.8 . . ?
C37 C38 H38A 108.8 . . ?
N8 C38 H38B 108.8 . . ?
C37 C38 H38B 108.8 . . ?
H38A C38 H38B 107.7 . . ?
C12 C7 C8 121.31(17) . . ?
C12 C7 S1 119.31(13) . . ?
C8 C7 S1 119.38(14) . . ?
N1 C25 C26 107.49(15) . . ?
N1 C25 C24 120.61(15) . . ?
C26 C25 C24 131.89(16) . . ?
N3 C37 C38 111.24(14) . . ?
N3 C37 H37A 109.4 . . ?
C38 C37 H37A 109.4 . . ?
N3 C37 H37B 109.4 . . ?
C38 C37 H37B 109.4 . . ?
H37A C37 H37B 108.0 . . ?
N7 C30 C29 110.76(14) . . ?
N7 C30 H30A 109.5 . . ?
C29 C30 H30A 109.5 . . ?
N7 C30 H30B 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 108.1 . . ?
C4 C3 C2 120.14(17) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C23 C22 C21 120.02(18) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 120.76(17) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
Si4 C60 H60A 109.5 . . ?
Si4 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
Si4 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C7 C8 C9 118.65(17) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C10 C11 C12 119.88(18) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
Si4 C36 H36A 109.5 . . ?
Si4 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
Si4 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C11 C10 C9 119.98(17) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C22 C21 C20 121.56(17) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
Si3 C33 H33A 109.5 . . ?
Si3 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
Si3 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
Si3 C34 H34A 109.5 . . ?
Si3 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
Si3 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C4 C5 C6 120.48(19) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C12 C11 119.52(17) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C8 C9 C10 120.63(17) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C1 C6 C5 119.00(18) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C5 C4 C3 120.28(18) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?

_refine_diff_density_max         0.562
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.073

_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_3b
_database_code_depnum_ccdc_archive 'CCDC 2304137'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology
Poland
;
_audit_update_record             
;
2023-10-27 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
4-(7-Fluoro-3-hydroxy-1,1-dimethyl-1,3-dihydrobenzo[c][1,2,5]oxasilaborol-6-yl)-1H-1,2,3-triazol-3-ium 4-chlorophenylsulfonate 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 B F N3 O2 Si, C6 H4 Cl O3 S'
_chemical_formula_sum            'C16 H16 B Cl F N3 O5 S Si'
_chemical_formula_weight         455.73

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'
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           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 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, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   15.7378(4)
_cell_length_b                   5.96710(10)
_cell_length_c                   21.2618(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.318(2)
_cell_angle_gamma                90
_cell_volume                     1980.41(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7792
_cell_measurement_theta_max      72.5340
_cell_measurement_theta_min      2.7900

_exptl_crystal_description       block
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    3.677
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80458
_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.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_reflns_number            15611
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.831
_diffrn_reflns_theta_max         72.690
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3890
_reflns_number_gt                3411
_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_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+0.9917P] 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         3890
_refine_ls_number_parameters     265
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0764
_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
C1 C 0.38277(12) 0.1586(4) 0.33258(9) 0.0316(4) Uani 1 1 d . . . . .
H1C H 0.4156 0.0915 0.3683 0.038 Uiso 1 1 calc R U . . .
C2 C 0.31198(12) 0.0494(3) 0.30145(9) 0.0296(4) Uani 1 1 d . . . . .
H2 H 0.2955 -0.0927 0.3160 0.035 Uiso 1 1 calc R U . . .
C3 C 0.26510(10) 0.1484(3) 0.24886(7) 0.0185(3) Uani 1 1 d . . . . .
C4 C 0.28833(12) 0.3548(3) 0.22777(8) 0.0259(4) Uani 1 1 d . . . . .
H4 H 0.2562 0.4213 0.1917 0.031 Uiso 1 1 calc R U . . .
C5 C 0.35885(13) 0.4661(3) 0.25924(9) 0.0290(4) Uani 1 1 d . . . . .
H5 H 0.3749 0.6091 0.2451 0.035 Uiso 1 1 calc R U . . .
C6 C 0.40516(11) 0.3666(3) 0.31116(8) 0.0247(4) Uani 1 1 d . . . . .
C7 C 0.78423(10) 0.0961(3) 0.51015(7) 0.0187(3) Uani 1 1 d . . . . .
C8 C 0.84912(10) 0.2486(3) 0.49896(7) 0.0182(3) Uani 1 1 d . . . . .
C9 C 0.93206(10) 0.2198(3) 0.52985(7) 0.0184(3) Uani 1 1 d . . . . .
H9 H 0.9758 0.3225 0.5224 0.022 Uiso 1 1 calc R U . . .
C10 C 0.95106(10) 0.0417(3) 0.57144(7) 0.0183(3) Uani 1 1 d . . . . .
H10 H 1.0076 0.0249 0.5925 0.022 Uiso 1 1 calc R U . . .
C11 C 0.88759(10) -0.1137(3) 0.58269(7) 0.0172(3) Uani 1 1 d . . . . .
C12 C 0.80548(10) -0.0794(3) 0.55091(7) 0.0183(3) Uani 1 1 d . . . . .
C13 C 0.63659(12) -0.0216(3) 0.40213(9) 0.0279(4) Uani 1 1 d . . . . .
H13A H 0.6810 -0.0717 0.3769 0.042 Uiso 1 1 calc R U . . .
H13B H 0.5893 0.0466 0.3741 0.042 Uiso 1 1 calc R U . . .
H13C H 0.6152 -0.1503 0.4240 0.042 Uiso 1 1 calc R U . . .
C14 C 0.60160(12) 0.2887(4) 0.51055(9) 0.0319(4) Uani 1 1 d . . . . .
H14A H 0.6281 0.3979 0.5414 0.048 Uiso 1 1 calc R U . . .
H14B H 0.5797 0.1620 0.5330 0.048 Uiso 1 1 calc R U . . .
H14C H 0.5542 0.3600 0.4834 0.048 Uiso 1 1 calc R U . . .
C15 C 0.90714(10) -0.3080(3) 0.62396(7) 0.0175(3) Uani 1 1 d . . . . .
C16 C 0.85694(11) -0.4696(3) 0.64729(7) 0.0192(3) Uani 1 1 d . . . . .
H16 H 0.7962 -0.4807 0.6403 0.023 Uiso 1 1 calc R U . . .
B1 B 0.81346(12) 0.4287(3) 0.44752(8) 0.0189(4) Uani 1 1 d . . . . .
N1 N 0.98851(9) -0.3674(2) 0.64765(6) 0.0187(3) Uani 1 1 d . . . . .
H1N H 1.0341 -0.2911 0.6403 0.022 Uiso 1 1 calc R U . . .
N2 N 0.99219(9) -0.5498(2) 0.68253(7) 0.0220(3) Uani 1 1 d . . . . .
N3 N 0.91171(9) -0.6086(2) 0.68203(6) 0.0199(3) Uani 1 1 d . . . . .
H3 H 0.8953 -0.7264 0.7023 0.024 Uiso 1 1 calc R U . . .
O1 O 0.86323(8) 0.58827(19) 0.42623(5) 0.0222(2) Uani 1 1 d D . . . .
O2 O 0.72694(7) 0.40422(19) 0.42781(5) 0.0205(2) Uani 1 1 d . . . . .
O3 O 0.20220(8) -0.2054(2) 0.18926(6) 0.0265(3) Uani 1 1 d . . . . .
O4 O 0.11447(8) -0.0103(2) 0.25761(5) 0.0231(3) Uani 1 1 d . . . . .
O5 O 0.13971(7) 0.1540(2) 0.15708(5) 0.0221(3) Uani 1 1 d . . . . .
S1 S 0.17338(2) 0.00991(6) 0.20992(2) 0.01751(10) Uani 1 1 d . . . . .
Si2 Si 0.68239(3) 0.18697(8) 0.46114(2) 0.01998(11) Uani 1 1 d . . . . .
F1 F 0.74351(6) -0.23209(16) 0.56005(5) 0.0241(2) Uani 1 1 d . . . . .
Cl1 Cl 0.49344(3) 0.50739(9) 0.35035(2) 0.03543(13) Uani 1 1 d . . . . .
H1O H 0.8374(16) 0.664(4) 0.3967(9) 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
C1 C6 1.383(3) . ?
C1 C2 1.384(3) . ?
C1 H1C 0.9500 . ?
C2 C3 1.390(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(2) . ?
C3 S1 1.7742(17) . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9500 . ?
C6 Cl1 1.7422(18) . ?
C7 C12 1.373(2) . ?
C7 C8 1.410(2) . ?
C7 Si2 1.8770(17) . ?
C8 C9 1.395(2) . ?
C8 B1 1.584(2) . ?
C9 C10 1.390(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.406(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(2) . ?
C11 C15 1.463(2) . ?
C12 F1 1.3666(18) . ?
C13 Si2 1.8472(19) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 Si2 1.8518(18) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N1 1.362(2) . ?
C15 C16 1.378(2) . ?
C16 N3 1.347(2) . ?
C16 H16 0.9500 . ?
B1 O1 1.347(2) . ?
B1 O2 1.380(2) . ?
N1 N2 1.314(2) . ?
N1 H1N 0.8800 . ?
N2 N3 1.313(2) . ?
N3 H3 0.8800 . ?
O1 H1O 0.834(10) . ?
O2 Si2 1.6734(12) . ?
O3 S1 1.4490(12) . ?
O4 S1 1.4637(12) . ?
O5 S1 1.4595(12) . ?

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 119.22(17) . . ?
C6 C1 H1C 120.4 . . ?
C2 C1 H1C 120.4 . . ?
C1 C2 C3 119.80(17) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.44(16) . . ?
C4 C3 S1 119.93(13) . . ?
C2 C3 S1 119.62(13) . . ?
C3 C4 C5 119.98(16) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.26(17) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 121.30(17) . . ?
C5 C6 Cl1 118.94(14) . . ?
C1 C6 Cl1 119.75(14) . . ?
C12 C7 C8 118.36(15) . . ?
C12 C7 Si2 133.86(13) . . ?
C8 C7 Si2 107.77(12) . . ?
C9 C8 C7 119.70(15) . . ?
C9 C8 B1 129.52(15) . . ?
C7 C8 B1 110.72(14) . . ?
C10 C9 C8 120.39(15) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.84(15) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 117.09(15) . . ?
C12 C11 C15 121.19(14) . . ?
C10 C11 C15 121.68(14) . . ?
F1 C12 C7 118.51(14) . . ?
F1 C12 C11 117.85(14) . . ?
C7 C12 C11 123.63(15) . . ?
Si2 C13 H13A 109.5 . . ?
Si2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si2 C14 H14A 109.5 . . ?
Si2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 103.88(14) . . ?
N1 C15 C11 122.96(14) . . ?
C16 C15 C11 133.15(15) . . ?
N3 C16 C15 105.78(14) . . ?
N3 C16 H16 127.1 . . ?
C15 C16 H16 127.1 . . ?
O1 B1 O2 124.48(15) . . ?
O1 B1 C8 122.78(15) . . ?
O2 B1 C8 112.75(14) . . ?
N2 N1 C15 113.33(14) . . ?
N2 N1 H1N 123.3 . . ?
C15 N1 H1N 123.3 . . ?
N3 N2 N1 104.10(13) . . ?
N2 N3 C16 112.90(14) . . ?
N2 N3 H3 123.5 . . ?
C16 N3 H3 123.5 . . ?
B1 O1 H1O 112.6(19) . . ?
B1 O2 Si2 113.81(11) . . ?
O3 S1 O5 112.70(7) . . ?
O3 S1 O4 112.78(7) . . ?
O5 S1 O4 112.45(7) . . ?
O3 S1 C3 106.68(7) . . ?
O5 S1 C3 106.20(7) . . ?
O4 S1 C3 105.35(7) . . ?
O2 Si2 C13 112.50(8) . . ?
O2 Si2 C14 109.95(8) . . ?
C13 Si2 C14 111.68(9) . . ?
O2 Si2 C7 94.87(7) . . ?
C13 Si2 C7 114.46(8) . . ?
C14 Si2 C7 112.29(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 S1 -178.96(15) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
S1 C3 C4 C5 178.33(14) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 Cl1 -179.96(14) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C1 C6 Cl1 179.34(16) . . . . ?
C12 C7 C8 C9 -0.9(2) . . . . ?
Si2 C7 C8 C9 179.92(12) . . . . ?
C12 C7 C8 B1 176.36(14) . . . . ?
Si2 C7 C8 B1 -2.85(16) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
B1 C8 C9 C10 -176.54(15) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C9 C10 C11 C15 177.09(14) . . . . ?
C8 C7 C12 F1 -177.61(13) . . . . ?
Si2 C7 C12 F1 1.3(2) . . . . ?
C8 C7 C12 C11 0.9(2) . . . . ?
Si2 C7 C12 C11 179.89(13) . . . . ?
C10 C11 C12 F1 178.36(13) . . . . ?
C15 C11 C12 F1 0.6(2) . . . . ?
C10 C11 C12 C7 -0.2(2) . . . . ?
C15 C11 C12 C7 -177.92(15) . . . . ?
C12 C11 C15 N1 169.17(15) . . . . ?
C10 C11 C15 N1 -8.4(2) . . . . ?
C12 C11 C15 C16 -9.6(3) . . . . ?
C10 C11 C15 C16 172.76(17) . . . . ?
N1 C15 C16 N3 -0.13(17) . . . . ?
C11 C15 C16 N3 178.84(16) . . . . ?
C9 C8 B1 O1 -0.3(3) . . . . ?
C7 C8 B1 O1 -177.19(15) . . . . ?
C9 C8 B1 O2 -179.91(15) . . . . ?
C7 C8 B1 O2 3.20(19) . . . . ?
C16 C15 N1 N2 0.50(18) . . . . ?
C11 C15 N1 N2 -178.60(14) . . . . ?
C15 N1 N2 N3 -0.66(17) . . . . ?
N1 N2 N3 C16 0.57(17) . . . . ?
C15 C16 N3 N2 -0.28(18) . . . . ?
O1 B1 O2 Si2 178.52(13) . . . . ?
C8 B1 O2 Si2 -1.88(17) . . . . ?
C4 C3 S1 O3 122.43(14) . . . . ?
C2 C3 S1 O3 -58.97(16) . . . . ?
C4 C3 S1 O5 2.00(16) . . . . ?
C2 C3 S1 O5 -179.40(14) . . . . ?
C4 C3 S1 O4 -117.48(14) . . . . ?
C2 C3 S1 O4 61.12(16) . . . . ?
B1 O2 Si2 C13 -118.83(12) . . . . ?
B1 O2 Si2 C14 116.03(12) . . . . ?
B1 O2 Si2 C7 0.19(12) . . . . ?
C12 C7 Si2 O2 -177.32(16) . . . . ?
C8 C7 Si2 O2 1.71(12) . . . . ?
C12 C7 Si2 C13 -59.89(19) . . . . ?
C8 C7 Si2 C13 119.14(12) . . . . ?
C12 C7 Si2 C14 68.79(19) . . . . ?
C8 C7 Si2 C14 -112.18(12) . . . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4


