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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/7/24/75/7247544.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_7247544
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 F O3 Si'
_chemical_formula_sum            'C9 H10 B F O3 Si'
_chemical_formula_weight         224.07
_chemical_name_systematic
;
1,1-dimethyl-7-fluoro-6-formylo-2,1,3-benzoxasilaborol-3(1H)-ol
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-10-13 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.474(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5415(2)
_cell_length_b                   6.9154(2)
_cell_length_c                   10.0942(2)
_cell_measurement_reflns_used    11063
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.3040
_cell_measurement_theta_min      2.6900
_cell_volume                     524.04(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.0026
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23568
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.747
_diffrn_reflns_theta_min         2.027
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         2182
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0333
_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)+(0.0503P)²+0.1659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1969
_reflns_number_total             2182
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00880k2.cif
_cod_data_source_block           6-CHO-7F
_cod_depositor_comments
'Adding full bibliography for 7247541--7247563.cif.'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7247544
_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.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
O3 O 0.57824(13) 0.2500 0.79886(9) 0.0247(2) Uani 1 2 d S T P . .
C8 C 0.44731(17) 0.2500 0.71834(11) 0.0189(2) Uani 1 2 d S T P . .
H8A H 0.3327 0.2500 0.7500 0.023 Uiso 1 2 calc R U P . .
Si1 Si 0.14419(4) 0.2500 0.19911(3) 0.01560(9) Uani 1 2 d S T P . .
F1 F 0.14639(10) 0.2500 0.53055(8) 0.02428(18) Uani 1 2 d S T P . .
O1 O 0.61001(13) 0.2500 0.07075(9) 0.0240(2) Uani 1 2 d DS T P . .
O2 O 0.29304(12) 0.2500 0.08608(8) 0.01895(18) Uani 1 2 d S T P . .
C1 C 0.48597(15) 0.2500 0.29846(11) 0.0156(2) Uani 1 2 d S T P . .
C6 C 0.64054(15) 0.2500 0.38743(11) 0.0170(2) Uani 1 2 d S T P . .
H6 H 0.7544 0.2500 0.3544 0.020 Uiso 1 2 calc R U P . .
C2 C 0.31653(15) 0.2500 0.34635(11) 0.0154(2) Uani 1 2 d S T P . .
C4 C 0.46006(16) 0.2500 0.57367(11) 0.0161(2) Uani 1 2 d S T P . .
C3 C 0.30874(16) 0.2500 0.48246(11) 0.0166(2) Uani 1 2 d S T P . .
C5 C 0.62740(16) 0.2500 0.52344(11) 0.0170(2) Uani 1 2 d S T P . .
H5 H 0.7326 0.2500 0.5833 0.020 Uiso 1 2 calc R U P . .
B1 B 0.46769(18) 0.2500 0.14090(12) 0.0173(2) Uani 1 2 d S T P . .
C7 C 0.01105(12) 0.02549(14) 0.18774(9) 0.02200(17) Uani 1 1 d . . . . .
H7A H 0.0848(6) -0.0800(9) 0.1681(8) 0.033 Uiso 1 1 calc R U . . .
H7B H -0.0836(10) 0.0383(5) 0.1192(8) 0.033 Uiso 1 1 calc R U . . .
H7C H -0.0365(10) 0.0028(7) 0.2701(7) 0.033 Uiso 1 1 calc R U . . .
H1 H 0.592(3) 0.2500 -0.0123(9) 0.033 Uiso 1 2 d DS U P . .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C8 C4 122.44(11) . . ?
O3 C8 H8A 118.8 . . ?
C4 C8 H8A 118.8 . . ?
O2 Si1 C7 110.69(3) . 4_565 ?
O2 Si1 C7 110.69(3) . . ?
C7 Si1 C7 114.45(6) 4_565 . ?
O2 Si1 C2 94.64(5) . . ?
C7 Si1 C2 112.35(3) 4_565 . ?
C7 Si1 C2 112.35(3) . . ?
B1 O1 H1 117.8(14) . . ?
B1 O2 Si1 113.77(8) . . ?
C6 C1 C2 120.41(10) . . ?
C6 C1 B1 129.11(10) . . ?
C2 C1 B1 110.47(10) . . ?
C5 C6 C1 120.06(10) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C3 C2 C1 117.87(10) . . ?
C3 C2 Si1 134.05(9) . . ?
C1 C2 Si1 108.08(8) . . ?
C3 C4 C5 117.91(10) . . ?
C3 C4 C8 121.82(11) . . ?
C5 C4 C8 120.27(11) . . ?
F1 C3 C2 118.72(10) . . ?
F1 C3 C4 118.16(10) . . ?
C2 C3 C4 123.12(11) . . ?
C6 C5 C4 120.62(11) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
O1 B1 O2 124.74(11) . . ?
O1 B1 C1 122.21(11) . . ?
O2 B1 C1 113.04(10) . . ?
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 . . ?
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
O3 C8 1.2175(15) . ?
C8 C4 1.4727(16) . ?
C8 H8A 0.9500 . ?
Si1 O2 1.6752(9) . ?
Si1 C7 1.8466(9) 4_565 ?
Si1 C7 1.8466(9) . ?
Si1 C2 1.8787(12) . ?
F1 C3 1.3595(13) . ?
O1 B1 1.3411(15) . ?
O1 H1 0.836(9) . ?
O2 B1 1.3792(16) . ?
C1 C6 1.4020(16) . ?
C1 C2 1.4087(16) . ?
C1 B1 1.5833(16) . ?
C6 C5 1.3859(15) . ?
C6 H6 0.9500 . ?
C2 C3 1.3808(15) . ?
C4 C3 1.3962(16) . ?
C4 C5 1.4042(16) . ?
C5 H5 0.9500 . ?
C7 H7A 0.950(8) . ?
C7 H7B 0.950(8) . ?
C7 H7C 0.950(8) . ?
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 O3 0.836(9) 1.899(10) 2.7320(13) 174(2) 1_554
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
C7 Si1 O2 B1 116.00(3) 4_565 . . . ?
C7 Si1 O2 B1 -116.00(3) . . . . ?
C2 Si1 O2 B1 0.0 . . . . ?
C2 C1 C6 C5 0.000(0) . . . . ?
B1 C1 C6 C5 180.000(0) . . . . ?
C6 C1 C2 C3 0.000(0) . . . . ?
B1 C1 C2 C3 180.000(0) . . . . ?
C6 C1 C2 Si1 180.000(0) . . . . ?
B1 C1 C2 Si1 0.000(0) . . . . ?
O2 Si1 C2 C3 180.000(0) . . . . ?
C7 Si1 C2 C3 65.37(4) 4_565 . . . ?
C7 Si1 C2 C3 -65.37(4) . . . . ?
O2 Si1 C2 C1 0.000(0) . . . . ?
C7 Si1 C2 C1 -114.63(4) 4_565 . . . ?
C7 Si1 C2 C1 114.63(4) . . . . ?
O3 C8 C4 C3 180.000(0) . . . . ?
O3 C8 C4 C5 0.000(0) . . . . ?
C1 C2 C3 F1 180.000(0) . . . . ?
Si1 C2 C3 F1 0.000(0) . . . . ?
C1 C2 C3 C4 0.000(0) . . . . ?
Si1 C2 C3 C4 180.000(0) . . . . ?
C5 C4 C3 F1 180.000(0) . . . . ?
C8 C4 C3 F1 0.000(0) . . . . ?
C5 C4 C3 C2 0.000(0) . . . . ?
C8 C4 C3 C2 180.000(0) . . . . ?
C1 C6 C5 C4 0.000(0) . . . . ?
C3 C4 C5 C6 0.000(0) . . . . ?
C8 C4 C5 C6 180.000(0) . . . . ?
Si1 O2 B1 O1 180.0 . . . . ?
Si1 O2 B1 C1 0.000(0) . . . . ?
C6 C1 B1 O1 0.000(0) . . . . ?
C2 C1 B1 O1 180.000(0) . . . . ?
C6 C1 B1 O2 180.000(0) . . . . ?
C2 C1 B1 O2 0.000(0) . . . . ?
