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#$Date: 2024-03-21 02:58:21 +0200 (Thu, 21 Mar 2024) $
#$Revision: 290568 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/83/7248328.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_7248328
loop_
_publ_author_name
'Nowicki, Krzysztof'
'Krajewska, Joanna'
'Stępniewski, Tomasz'
'Wielechowska, Monika'
'Wińska, Patrycja'
'Kaczmarczyk, Anna'
'Korpowska, Julia'
'Selent, Jana'
'Marek-Urban, Paulina H.'
'Durka, Krzysztof'
'Wozniak, Krzysztof'
'Laudy, Agnieszka E.'
'Luliński, Sergiusz'
_publ_section_title
;
 Exploiting thiol-functionalized benzosiloxaboroles for achieving diverse
 substitution patterns -- synthesis, characterization and biological
 evaluation of promising antibacterial agents
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D4MD00061G
_journal_year                    2024
_chemical_formula_moiety         'C14 H13 B F3 N O4 S Si'
_chemical_formula_sum            'C14 H13 B F3 N O4 S Si'
_chemical_formula_weight         387.21
_chemical_name_systematic
;
7-fluoro-N-(4-fluorophenyl)-3-hydroxy-1,1-dimethyl-1,3-dihydrobenzo[c][1,2,5]oxasilaborole-6-sulfonamide 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-07-15 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                101.774(4)
_cell_angle_beta                 90.259(5)
_cell_angle_gamma                106.776(6)
_cell_formula_units_Z            2
_cell_length_a                   6.5260(5)
_cell_length_b                   10.5500(5)
_cell_length_c                   13.1827(7)
_cell_measurement_reflns_used    2613
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.8730
_cell_measurement_theta_min      2.8460
_cell_volume                     848.76(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       '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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0026
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6440
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.099
_diffrn_reflns_theta_min         2.064
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.900
_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.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3897
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0365P)²+0.4916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1060
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3022
_reflns_number_total             3897
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4md00061g2.cif
_cod_data_source_block           27
_cod_database_code               7248328
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.900
_oxdiff_exptl_absorpt_empirical_full_max 1.116
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
H1A H 0.549(5) 0.892(3) 0.524(2) 0.035(8) Uiso 1 1 d D . . . .
H2A H 1.543(5) 1.466(3) 0.903(2) 0.033(9) Uiso 1 1 d D . . . .
S1 S 0.44484(9) 0.96835(6) 0.67231(4) 0.01864(15) Uani 1 1 d . . . . .
Si1 Si 1.02458(11) 1.26641(6) 1.03587(5) 0.01633(15) Uani 1 1 d . . . . .
F3 F 0.5718(2) 1.06092(13) 0.90798(10) 0.0225(3) Uani 1 1 d . . . . .
F2 F 0.8260(2) 1.10252(13) 0.57752(9) 0.0252(3) Uani 1 1 d . . . . .
O2 O 1.4694(3) 1.40988(17) 0.85976(13) 0.0225(4) Uani 1 1 d D . . . .
O1 O 1.2587(3) 1.36958(14) 1.00652(12) 0.0194(4) Uani 1 1 d . . . . .
O3 O 0.3205(3) 0.89857(16) 0.74360(12) 0.0245(4) Uani 1 1 d . . . . .
O4 O 0.3629(3) 1.05260(16) 0.62027(12) 0.0235(4) Uani 1 1 d . . . . .
C1 C 0.9244(4) 1.1947(2) 0.89631(16) 0.0155(4) Uani 1 1 d . . . . .
F1 F 0.8719(3) 0.46341(15) 0.63205(12) 0.0435(5) Uani 1 1 d . . . . .
N1 N 0.4980(3) 0.85679(19) 0.57970(15) 0.0194(4) Uani 1 1 d D . . . .
C5 C 0.6923(4) 1.0734(2) 0.73971(17) 0.0160(5) Uani 1 1 d . . . . .
C3 C 1.0551(4) 1.2157(2) 0.72556(17) 0.0180(5) Uani 1 1 d . . . . .
H3 H 1.1649 1.2522 0.6834 0.022 Uiso 1 1 calc R U . . .
C6 C 0.7305(4) 1.1091(2) 0.84762(16) 0.0159(5) Uani 1 1 d . . . . .
C2 C 1.0878(4) 1.2470(2) 0.83352(17) 0.0161(5) Uani 1 1 d . . . . .
C7 C 1.0920(4) 1.1484(2) 1.10649(18) 0.0220(5) Uani 1 1 d . . . . .
H7A H 1.1804 1.0999 1.0644 0.033 Uiso 1 1 calc R U . . .
H7B H 0.9598 1.0832 1.1202 0.033 Uiso 1 1 calc R U . . .
H7C H 1.1718 1.1995 1.1725 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5966(4) 0.7578(2) 0.59874(17) 0.0182(5) Uani 1 1 d . . . . .
C4 C 0.8615(4) 1.1313(2) 0.68230(16) 0.0183(5) Uani 1 1 d . . . . .
C13 C 0.5795(5) 0.5533(2) 0.65593(19) 0.0291(6) Uani 1 1 d . . . . .
H13 H 0.5068 0.4810 0.6874 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4850(4) 0.6519(2) 0.64417(18) 0.0239(5) Uani 1 1 d . . . . .
H14 H 0.3456 0.6473 0.6668 0.029 Uiso 1 1 calc R U . . .
B1 B 1.2901(4) 1.3488(2) 0.9011(2) 0.0179(5) Uani 1 1 d . . . . .
C10 C 0.8006(4) 0.7647(2) 0.56592(18) 0.0229(5) Uani 1 1 d . . . . .
H10 H 0.8767 0.8383 0.5365 0.027 Uiso 1 1 calc R U . . .
C12 C 0.7805(5) 0.5623(2) 0.62111(19) 0.0295(6) Uani 1 1 d . . . . .
C11 C 0.8938(4) 0.6650(2) 0.57575(19) 0.0267(6) Uani 1 1 d . . . . .
H11 H 1.0318 0.6676 0.5519 0.032 Uiso 1 1 calc R U . . .
C8 C 0.8636(4) 1.3673(2) 1.10838(19) 0.0267(6) Uani 1 1 d . . . . .
H8A H 0.8356 1.4286 1.0670 0.040 Uiso 1 1 calc R U . . .
H8B H 0.9423 1.4205 1.1741 0.040 Uiso 1 1 calc R U . . .
H8C H 0.7271 1.3066 1.1226 0.040 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 1 0.0568
-1 4 -5 0.0792
-2 -4 -5 0.0118
1 0 0 0.0096
-1 5 0 0.0382
-8 -4 0 0.0023
-5 4 4 0.0197
3 7 11 0.0315
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 120.66(11) . . ?
O3 S1 N1 108.31(10) . . ?
O4 S1 N1 105.11(10) . . ?
O3 S1 C5 107.69(10) . . ?
O4 S1 C5 106.56(10) . . ?
N1 S1 C5 107.95(11) . . ?
O1 Si1 C8 110.44(10) . . ?
O1 Si1 C7 107.52(10) . . ?
C8 Si1 C7 113.77(11) . . ?
O1 Si1 C1 93.81(9) . . ?
C8 Si1 C1 113.26(11) . . ?
C7 Si1 C1 115.98(10) . . ?
B1 O2 H2A 109(2) . . ?
B1 O1 Si1 113.65(15) . . ?
C6 C1 C2 118.1(2) . . ?
C6 C1 Si1 133.59(17) . . ?
C2 C1 Si1 108.32(16) . . ?
C9 N1 S1 122.98(16) . . ?
C9 N1 H1A 112.4(17) . . ?
S1 N1 H1A 112.7(17) . . ?
C6 C5 C4 116.0(2) . . ?
C6 C5 S1 124.98(17) . . ?
C4 C5 S1 118.93(17) . . ?
C4 C3 C2 118.1(2) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
F3 C6 C1 118.09(19) . . ?
F3 C6 C5 119.2(2) . . ?
C1 C6 C5 122.7(2) . . ?
C3 C2 C1 121.1(2) . . ?
C3 C2 B1 127.4(2) . . ?
C1 C2 B1 111.34(19) . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 C9 C14 120.3(2) . . ?
C10 C9 N1 118.9(2) . . ?
C14 C9 N1 120.7(2) . . ?
F2 C4 C3 118.7(2) . . ?
F2 C4 C5 117.3(2) . . ?
C3 C4 C5 124.0(2) . . ?
C12 C13 C14 118.7(2) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C9 119.4(2) . . ?
C13 C14 H14 120.3 . . ?
C9 C14 H14 120.3 . . ?
O2 B1 O1 124.7(2) . . ?
O2 B1 C2 122.9(2) . . ?
O1 B1 C2 112.4(2) . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
F1 C12 C11 118.4(3) . . ?
F1 C12 C13 118.3(2) . . ?
C11 C12 C13 123.2(2) . . ?
C12 C11 C10 117.9(2) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4241(16) . ?
S1 O4 1.4378(17) . ?
S1 N1 1.6276(19) . ?
S1 C5 1.782(2) . ?
Si1 O1 1.6987(17) . ?
Si1 C8 1.842(2) . ?
Si1 C7 1.842(2) . ?
Si1 C1 1.876(2) . ?
F3 C6 1.354(2) . ?
F2 C4 1.356(2) . ?
O2 B1 1.339(3) . ?
O2 H2A 0.77(3) . ?
O1 B1 1.388(3) . ?
C1 C6 1.387(3) . ?
C1 C2 1.408(3) . ?
F1 C12 1.373(3) . ?
N1 C9 1.435(3) . ?
N1 H1A 0.91(3) . ?
C5 C6 1.397(3) . ?
C5 C4 1.404(3) . ?
C3 C4 1.361(3) . ?
C3 C2 1.395(3) . ?
C3 H3 0.9500 . ?
C2 B1 1.571(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C10 1.388(3) . ?
C9 C14 1.395(3) . ?
C13 C12 1.376(4) . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C12 C11 1.373(3) . ?
C11 H11 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0004 -1.0002 1.0000 -0.0543 0.0179 0.0569
-1.0009 3.9997 -4.9999 0.2629 -0.1700 -0.1563
-1.9978 -4.0025 -4.9989 0.2486 -0.1319 0.4607
0.9991 0.0012 -0.0002 0.0079 0.0974 -0.0581
-1.0005 4.9995 -0.0003 -0.0040 -0.1820 -0.2912
-7.7928 -3.8205 0.4913 -0.0911 -0.6947 0.7135
-4.9961 3.9944 4.0002 -0.2505 -0.5508 -0.0407
2.9969 7.0037 10.9980 -0.5594 0.1843 -0.8065
