#------------------------------------------------------------------------------
#$Date: 2024-03-21 02:58:21 +0200 (Thu, 21 Mar 2024) $
#$Revision: 290568 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/83/7248331.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_7248331
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         'C16 H17 B F2 O4 S2 Si'
_chemical_formula_sum            'C16 H17 B F2 O4 S2 Si'
_chemical_formula_weight         414.31
_chemical_name_systematic
;
 5,7-difluoro-1,1-dimethyl-6-((2-(phenylsulfonyl)ethyl)thio)benzo[c][1,2,5]oxasilaborol-3(1H)-ol 
;
_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   geom
_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                91.269(4)
_cell_angle_beta                 112.587(4)
_cell_angle_gamma                118.044(4)
_cell_formula_units_Z            2
_cell_length_a                   9.4513(4)
_cell_length_b                   9.8968(4)
_cell_length_c                   12.2922(6)
_cell_measurement_reflns_used    10074
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.4590
_cell_measurement_theta_min      3.9940
_cell_volume                     907.49(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.971
_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  0.0185
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12561
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.679
_diffrn_reflns_theta_min         4.021
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.661
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.837
_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.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_description       irregular
_exptl_crystal_F_000             428
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0273
_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)+(0.0436P)²+0.6833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0769
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3564
_reflns_number_total             3714
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4md00061g2.cif
_cod_data_source_block           20
_cod_original_cell_volume        907.49(8)
_cod_database_code               7248331
_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 0.837
_oxdiff_exptl_absorpt_empirical_full_max 1.314
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_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
F2 F 0.37251(12) 0.11849(10) 0.12588(8) 0.02115(19) Uani 1 1 d . . . . .
F1 F 0.95434(11) 0.21108(10) 0.34780(8) 0.01911(19) Uani 1 1 d . . . . .
S1 S 0.74015(5) 0.36591(4) 0.31259(3) 0.01562(9) Uani 1 1 d . . . . .
S2 S 0.55388(5) 0.20307(4) 0.58979(3) 0.01578(10) Uani 1 1 d . . . . .
Si1 Si 0.84752(5) -0.14497(4) 0.22206(3) 0.01319(10) Uani 1 1 d . . . . .
O3 O 0.35736(14) -0.40975(12) -0.02721(9) 0.0177(2) Uani 1 1 d . . . . .
H3 H 0.3652 -0.4874 -0.0456 0.027 Uiso 1 1 calc R U . . .
O4 O 0.66522(13) -0.31005(12) 0.11549(9) 0.0156(2) Uani 1 1 d . . . . .
O2 O 0.37037(15) 0.13093(14) 0.56984(10) 0.0247(2) Uani 1 1 d . . . . .
O1 O 0.64607(15) 0.11779(12) 0.62619(10) 0.0219(2) Uani 1 1 d . . . . .
C14 C 0.56002(19) 0.25589(16) 0.45299(12) 0.0158(3) Uani 1 1 d . . . . .
H14A H 0.4810 0.1591 0.3855 0.019 Uiso 1 1 calc R U . . .
H14B H 0.5117 0.3267 0.4337 0.019 Uiso 1 1 calc R U . . .
C2 C 0.42771(19) -0.08322(16) 0.09582(13) 0.0154(3) Uani 1 1 d . . . . .
H2 H 0.3057 -0.1504 0.0384 0.018 Uiso 1 1 calc R U . . .
C13 C 0.74722(19) 0.33808(17) 0.46047(13) 0.0171(3) Uani 1 1 d . . . . .
H13A H 0.8023 0.2739 0.4894 0.021 Uiso 1 1 calc R U . . .
H13B H 0.8227 0.4422 0.5200 0.021 Uiso 1 1 calc R U . . .
C5 C 0.78215(19) 0.11490(16) 0.26485(12) 0.0141(3) Uani 1 1 d . . . . .
C6 C 0.72890(19) -0.03443(16) 0.20814(12) 0.0139(3) Uani 1 1 d . . . . .
C3 C 0.48939(19) 0.06808(17) 0.15511(13) 0.0149(3) Uani 1 1 d . . . . .
C4 C 0.66638(19) 0.17190(16) 0.24103(12) 0.0139(3) Uani 1 1 d . . . . .
C1 C 0.54823(19) -0.13459(16) 0.12214(12) 0.0137(3) Uani 1 1 d . . . . .
C8 C 0.68352(19) 0.38384(17) 0.70112(13) 0.0156(3) Uani 1 1 d . . . . .
C16 C 0.92674(19) -0.18988(17) 0.37058(13) 0.0172(3) Uani 1 1 d . . . . .
H16A H 0.8310 -0.2318 0.3961 0.026 Uiso 1 1 calc R U . . .
H16B H 1.0314 -0.0931 0.4310 0.026 Uiso 1 1 calc R U . . .
H16C H 0.9600 -0.2686 0.3637 0.026 Uiso 1 1 calc R U . . .
C9 C 0.6053(2) 0.46793(18) 0.71530(14) 0.0199(3) Uani 1 1 d . . . . .
H9 H 0.4825 0.4300 0.6640 0.024 Uiso 1 1 calc R U . . .
B1 B 0.5144(2) -0.29771(18) 0.06413(14) 0.0145(3) Uani 1 1 d . . . . .
C10 C 0.7083(2) 0.6069(2) 0.80480(16) 0.0248(3) Uani 1 1 d . . . . .
H10 H 0.6567 0.6656 0.8154 0.030 Uiso 1 1 calc R U . . .
C15 C 1.0245(2) -0.05789(19) 0.17119(15) 0.0210(3) Uani 1 1 d . . . . .
H15A H 0.9794 -0.0309 0.0940 0.031 Uiso 1 1 calc R U . . .
H15B H 1.0590 -0.1344 0.1599 0.031 Uiso 1 1 calc R U . . .
H15C H 1.1291 0.0379 0.2327 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8628(2) 0.43709(18) 0.77581(14) 0.0203(3) Uani 1 1 d . . . . .
H7 H 0.9144 0.3783 0.7658 0.024 Uiso 1 1 calc R U . . .
C12 C 0.9645(2) 0.57678(19) 0.86475(15) 0.0249(3) Uani 1 1 d . . . . .
H12 H 1.0874 0.6152 0.9160 0.030 Uiso 1 1 calc R U . . .
C11 C 0.8875(2) 0.66112(19) 0.87948(15) 0.0258(3) Uani 1 1 d . . . . .
H11 H 0.9580 0.7568 0.9412 0.031 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -4 1 0.0661
-5 0 0 0.0524
5 0 0 0.0295
-1 4 -1 0.0410
4 -3 -6 0.0405
-3 0 5 0.0545
0 -1 -4 0.0377
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 S1 C13 100.07(7) . . ?
O2 S2 O1 119.73(7) . . ?
O2 S2 C8 108.54(7) . . ?
O1 S2 C8 106.83(7) . . ?
O2 S2 C14 107.03(7) . . ?
O1 S2 C14 108.52(7) . . ?
C8 S2 C14 105.32(7) . . ?
O4 Si1 C16 110.67(6) . . ?
O4 Si1 C15 109.76(6) . . ?
C16 Si1 C15 111.78(7) . . ?
O4 Si1 C6 94.67(6) . . ?
C16 Si1 C6 115.23(7) . . ?
C15 Si1 C6 113.44(7) . . ?
B1 O3 H3 109.5 . . ?
B1 O4 Si1 113.39(9) . . ?
C13 C14 S2 113.54(10) . . ?
C13 C14 H14A 108.9 . . ?
S2 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
S2 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C3 C2 C1 118.50(13) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C14 C13 S1 111.20(10) . . ?
C14 C13 H13A 109.4 . . ?
S1 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
S1 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
F1 C5 C6 118.86(13) . . ?
F1 C5 C4 117.88(12) . . ?
C6 C5 C4 123.26(13) . . ?
C5 C6 C1 118.45(13) . . ?
C5 C6 Si1 133.41(11) . . ?
C1 C6 Si1 108.13(10) . . ?
F2 C3 C2 117.95(13) . . ?
F2 C3 C4 118.49(12) . . ?
C2 C3 C4 123.54(13) . . ?
C5 C4 C3 115.90(12) . . ?
C5 C4 S1 122.16(11) . . ?
C3 C4 S1 121.93(11) . . ?
C2 C1 C6 120.36(13) . . ?
C2 C1 B1 128.52(13) . . ?
C6 C1 B1 111.10(12) . . ?
C7 C8 C9 121.26(14) . . ?
C7 C8 S2 118.48(11) . . ?
C9 C8 S2 120.23(12) . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C9 C8 119.14(15) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
O3 B1 O4 124.05(13) . . ?
O3 B1 C1 123.32(13) . . ?
O4 B1 C1 112.60(12) . . ?
C9 C10 C11 119.94(15) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
Si1 C15 H15A 109.5 . . ?
Si1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
Si1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C7 C8 118.95(15) . . ?
C12 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C7 C12 C11 120.13(15) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C11 C10 120.58(15) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C3 1.3489(16) . ?
F1 C5 1.3491(16) . ?
S1 C4 1.7726(14) . ?
S1 C13 1.8249(14) . ?
S2 O2 1.4419(12) . ?
S2 O1 1.4424(11) . ?
S2 C8 1.7656(15) . ?
S2 C14 1.7859(14) . ?
Si1 O4 1.6966(10) . ?
Si1 C16 1.8411(15) . ?
Si1 C15 1.8447(15) . ?
Si1 C6 1.8701(14) . ?
O3 B1 1.3455(19) . ?
O3 H3 0.8400 . ?
O4 B1 1.3860(19) . ?
C14 C13 1.523(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C2 C3 1.385(2) . ?
C2 C1 1.389(2) . ?
C2 H2 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C5 C6 1.3816(19) . ?
C5 C4 1.394(2) . ?
C6 C1 1.4111(19) . ?
C3 C4 1.396(2) . ?
C1 B1 1.583(2) . ?
C8 C7 1.391(2) . ?
C8 C9 1.393(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C9 C10 1.379(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C7 C12 1.381(2) . ?
C7 H7 0.9500 . ?
C12 C11 1.387(2) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0017 -4.0029 0.9871 0.0291 -0.0428 0.6400
-4.9927 0.4980 0.4882 -0.2001 -0.9363 0.0446
4.9927 -0.4980 -0.4882 0.2001 0.9363 -0.0446
-1.0007 3.5034 -1.4893 0.0418 -0.0381 -0.5707
4.0020 -2.9920 -6.0032 0.8670 0.0876 0.2602
-3.0005 0.4918 5.4958 -0.7122 -0.1283 0.1070
0.0047 -0.9950 -4.0056 0.4801 -0.4025 0.0740
