Exploiting thiol-functionalized benzosiloxaboroles for achieving diverse substitution patterns – synthesis, characterization and biological evaluation of promising antibacterial agents
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; RSC Medicinal Chemistry  (2024) –; doi:10.1039/D4MD00061G

data_7248322
_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         'C11 H12 B F2 N O2 S Si'
_chemical_formula_sum            'C11 H12 B F2 N O2 S Si'
_chemical_formula_weight         299.18
_chemical_name_systematic
;
3-((5,7-difluoro-3-hydroxy-1,1-dimethyl-1,3-dihydrobenzo[c][1,2,5]oxasilaborol-6-yl)thio)propanenitrile 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           6
_space_group_name_Hall           'P -2y'
_space_group_name_H-M_alt        'P 1 m 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                90
_cell_angle_beta                 103.038(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7169(3)
_cell_length_b                   7.4368(3)
_cell_length_c                   10.3692(3)
_cell_measurement_reflns_used    2047
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.3950
_cell_measurement_theta_min      4.3330
_cell_volume                     654.86(4)
_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_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 0.995
_diffrn_measured_fraction_theta_max 0.965
_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_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1720
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.527
_diffrn_reflns_theta_min         4.377
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.697
_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_density_diffrn    1.517
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.083
_refine_diff_density_max         1.756
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Flack x determined using 324 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         1720
_refine_ls_number_restraints     148
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0.01
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+1.4978P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1195
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                1623
_reflns_number_total             1720
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4md00061g2.cif
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      'P m'
_cod_database_code               7248322
_oxdiff_exptl_absorpt_empirical_full_min 0.780
_oxdiff_exptl_absorpt_empirical_full_max 1.457
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelxl_version_number           2013-4
_shelx_res_checksum              7724
_shelx_hkl_checksum              41477