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#$Date: 2024-01-06 10:04:15 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247542.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7247542
loop_
_publ_author_name
'Durka, Krzysztof'
'Zuba, Adam'
'Marek-Urban, Paulina H.'
'Nowicki, Krzysztof'
'Drapała, Jakub'
'Woźniak, Krzysztof'
'Luliński, Sergiusz'
_publ_section_title
;
 Exploring the effect of substitution patterns on the symmetry of
 hydrogen-bonded supramolecular motifs in functionalized
 benzosiloxaboroles
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              6329
_journal_page_last               6342
_journal_paper_doi               10.1039/D3CE00880K
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C9 H10 B F3 O2 Si'
_chemical_formula_sum            'C9 H10 B F3 O2 Si'
_chemical_formula_weight         246.07
_chemical_name_systematic
;
1,1-dimethyl-4-(trifluoromethyl)-3-hydroxybenzo[c][1,2,3]siloxaborole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-04-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-10-01 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.988(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3772(3)
_cell_length_b                   11.1912(3)
_cell_length_c                   12.2672(4)
_cell_measurement_reflns_used    3493
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.5770
_cell_measurement_theta_min      5.3760
_cell_volume                     1120.64(6)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4353
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.730
_diffrn_reflns_theta_min         5.415
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.116
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.574
_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.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.181
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2151
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0351
_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)+(0.0530P)²+0.6945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2026
_reflns_number_total             2151
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00880k2.cif
_cod_data_source_block           4-CF3
_cod_depositor_comments
'Adding full bibliography for 7247541--7247563.cif.'
_cod_database_code               7247542
_shelxl_version_number           2013-4
_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.
;
_olex2_refinement_description
;
1. Restrained distances
 O2-H2A
 0.84 with sigma of 0.01
2.a Me refined with riding coordinates:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C5(H5)
;
_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 2.238
_oxdiff_exptl_absorpt_empirical_full_min 0.686
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'
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 0.19400(5) 0.19559(4) 0.48530(3) 0.01397(14) Uani 1 1 d . . . . .
F1 F 0.66232(13) 0.28903(9) 0.25576(9) 0.0282(3) Uani 1 1 d . . . . .
F2 F 0.78740(11) 0.34428(9) 0.42117(9) 0.0267(2) Uani 1 1 d . . . . .
F3 F 0.72820(14) 0.47356(10) 0.28887(11) 0.0363(3) Uani 1 1 d . . . . .
O2 O 0.62349(14) 0.12262(10) 0.43924(10) 0.0220(3) Uani 1 1 d D . . . .
O1 O 0.36927(13) 0.11824(9) 0.49558(9) 0.0173(2) Uani 1 1 d . . . . .
C6 C 0.19746(19) 0.44365(14) 0.40002(12) 0.0167(3) Uani 1 1 d . . . . .
H6 H 0.0915 0.4589 0.4125 0.020 Uiso 1 1 calc R U . . .
C2 C 0.42813(18) 0.30797(13) 0.40820(12) 0.0149(3) Uani 1 1 d . . . . .
C3 C 0.50693(19) 0.39845(14) 0.36023(12) 0.0165(3) Uani 1 1 d . . . . .
C9 C 0.6699(2) 0.37655(14) 0.33209(14) 0.0212(3) Uani 1 1 d . . . . .
C4 C 0.43340(19) 0.50927(14) 0.33486(12) 0.0180(3) Uani 1 1 d . . . . .
H4 H 0.4883 0.5697 0.3030 0.022 Uiso 1 1 calc R U . . .
C1 C 0.27028(18) 0.33210(14) 0.42612(12) 0.0144(3) Uani 1 1 d . . . . .
C5 C 0.27975(19) 0.53225(14) 0.35584(13) 0.0185(3) Uani 1 1 d . . . . .
H5 H 0.2312 0.6088 0.3398 0.022 Uiso 1 1 calc R U . . .
C7 C 0.1485(2) 0.21940(15) 0.62421(13) 0.0221(4) Uani 1 1 d . . . . .
H7A H 0.2385 0.2639 0.6719 0.033 Uiso 1 1 calc R U . . .
H7B H 0.1362 0.1419 0.6587 0.033 Uiso 1 1 calc R U . . .
H7C H 0.0465 0.2650 0.6158 0.033 Uiso 1 1 calc R U . . .
C8 C 0.03204(19) 0.11217(15) 0.38742(13) 0.0203(3) Uani 1 1 d . . . . .
H8A H 0.0631 0.1029 0.3155 0.030 Uiso 1 1 calc R U . . .
H8B H -0.0714 0.1563 0.3763 0.030 Uiso 1 1 calc R U . . .
H8C H 0.0186 0.0332 0.4186 0.030 Uiso 1 1 calc R U . . .
B1 B 0.4840(2) 0.17656(16) 0.44887(15) 0.0161(3) Uani 1 1 d . . . . .
H2A H 0.625(3) 0.0525(10) 0.4622(16) 0.024 Uiso 1 1 d D U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 2 5 0.0919
-1 -1 -5 0.1043
1 -1 -5 0.1003
-5 -1 4 0.1157
5 1 -2 0.1012
-3 5 3 0.0631
1 -4 -5 0.0848
5 -3 1 0.0869
-2 -5 4 0.1054
0 -2 5 0.0983
-3 -4 -4 0.0944
2 5 -5 0.1150
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Si1 C1 94.64(6) . . ?
O1 Si1 C7 111.24(7) . . ?
O1 Si1 C8 106.80(7) . . ?
C7 Si1 C1 113.63(7) . . ?
C7 Si1 C8 113.47(8) . . ?
C8 Si1 C1 115.23(7) . . ?
B1 O2 H2A 110.1(15) . . ?
B1 O1 Si1 113.60(10) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C1 119.99(14) . . ?
C3 C2 C1 118.05(14) . . ?
C3 C2 B1 131.61(14) . . ?
C1 C2 B1 110.34(13) . . ?
C2 C3 C9 120.97(14) . . ?
C4 C3 C2 120.66(14) . . ?
C4 C3 C9 118.34(14) . . ?
F1 C9 F3 106.09(13) . . ?
F1 C9 C3 112.04(13) . . ?
F2 C9 F1 106.33(13) . . ?
F2 C9 F3 105.80(13) . . ?
F2 C9 C3 113.21(13) . . ?
F3 C9 C3 112.81(13) . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.37(14) . . ?
C5 C4 H4 119.8 . . ?
C6 C1 Si1 130.70(12) . . ?
C6 C1 C2 120.74(14) . . ?
C2 C1 Si1 108.55(11) . . ?
C6 C5 C4 120.13(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 B1 O1 121.44(14) . . ?
O2 B1 C2 126.06(14) . . ?
O1 B1 C2 112.48(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 O1 1.6846(11) . ?
Si1 C1 1.8649(16) . ?
Si1 C7 1.8473(16) . ?
Si1 C8 1.8498(16) . ?
F1 C9 1.3467(19) . ?
F2 C9 1.345(2) . ?
F3 C9 1.3471(19) . ?
O2 B1 1.344(2) . ?
O2 H2A 0.833(9) . ?
O1 B1 1.388(2) . ?
C6 H6 0.9500 . ?
C6 C1 1.395(2) . ?
C6 C5 1.386(2) . ?
C2 C3 1.408(2) . ?
C2 C1 1.414(2) . ?
C2 B1 1.589(2) . ?
C3 C9 1.502(2) . ?
C3 C4 1.389(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(2) . ?
C5 H5 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_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
O2 H2A O1 0.833(9) 1.978(10) 2.8083(16) 175(2) 3_656
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.9919 1.9700 5.0073 0.0407 -0.0087 0.8588
-0.9940 -0.9742 -5.0050 0.0127 -0.1583 -0.7054
1.0037 -0.9769 -5.0009 -0.1342 -0.4159 -0.4725
-4.9964 -1.0076 3.9918 0.1876 0.9424 -0.1775
4.9949 0.9990 -1.9907 -0.2139 -0.8122 0.3983
-3.0040 4.9773 2.9968 0.8143 0.3906 0.1668
1.0068 -3.9686 -5.0017 -0.5143 -0.3013 -0.5835
4.9966 -3.0029 1.0100 -0.7604 -0.4643 0.5816
-1.9958 -5.0007 3.9969 -0.5396 0.7087 0.0239
-0.0018 -2.0161 5.0023 -0.3194 0.4017 0.4780
-2.9895 -3.9674 -4.0093 -0.2339 0.2789 -0.9387
1.9965 5.0050 -4.9975 0.5527 -0.7738 -0.1343
