Ethynyl-substituted benzosiloxaboroles: the role of C(π)⋯B interactions in their crystal packing and use in Cu(i)-catalyzed 1,3-dipolar cycloaddition
Pacholak, P.; Durka, K.; Woźniak, K.; Krajewska, J.; Laudy, A. E.; Luliński, S.; RSC Advances 14 (2024) 16069–16082; doi:10.1039/D4RA02137A

data_7248641
_publ_section_title
;
 Ethynyl-substituted benzosiloxaboroles: the role of C(\p)&#x22EF;B
 interactions in their crystal packing and use in Cu(i)-catalyzed
 1,3-dipolar cycloaddition
;
_journal_issue                   23
_journal_name_full               'RSC Advances'
_journal_page_first              16069
_journal_page_last               16082
_journal_paper_doi               10.1039/D4RA02137A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C10 H10 B F O2 Si'
_chemical_formula_sum            'C10 H10 B F O2 Si'
_chemical_formula_weight         220.08
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-04-28 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                92.553(2)
_cell_angle_beta                 97.855(2)
_cell_angle_gamma                91.766(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9862(2)
_cell_length_b                   7.4451(2)
_cell_length_c                   10.5854(2)
_cell_measurement_reflns_used    17554
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.5780
_cell_measurement_theta_min      1.9200
_cell_volume                     544.49(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.76a (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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0013
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -124.00 -37.00   1.00    6.00    --  -29.16 178.00 -30.00   87
  2  \w    -72.00  42.00   1.00    6.00    --  -29.16  77.00   0.00  114
  3  \w   -120.00  62.00   1.00    6.00    --  -29.16   0.00   0.00  182
  4  \w    -14.00  42.00   1.00    6.00    --   29.16  77.00 -90.00   56
  5  \w    -14.00  42.00   1.00    6.00    --   29.16  77.00-150.00   56
  6  \w    -14.00  42.00   1.00    6.00    --   29.16  77.00 -30.00   56
  7  \w    -14.00  42.00   1.00    6.00    --   29.16  77.00-180.00   56
  8  \w   -105.00   9.00   1.00    6.00    --  -29.16 -57.00-120.00  114
  9  \w     -9.00 105.00   1.00    6.00    --   29.16  57.00 -30.00  114
 10  \w    -14.00  42.00   1.00    6.00    --   29.16  77.00  90.00   56
 11  \w     39.00 123.00   1.00    6.00    --   29.16 178.00   0.00   84
 12  \w    -47.00  67.00   1.00    6.00    --   29.16 -57.00 120.00  114
 13  \w    -14.00  42.00   1.00    6.00    --   29.16  77.00  30.00   56
 14  \w    -50.00  77.00   1.00    6.00    --   29.16 -45.00  85.00  127
 15  \w     -9.00 105.00   1.00    6.00    --   29.16  57.00  90.00  114
 16  \w     39.00 123.00   1.00    6.00    --   29.16 178.00 -60.00   84
 17  \w    -14.00  42.00   1.00    6.00    --   29.16  77.00   0.00   56
 18  \w    -62.00 120.00   1.00    6.00    --   29.16   0.00-180.00  182
 19  \w     -9.00 105.00   1.00    6.00    --   29.16  57.00-180.00  114
 20  \w    -62.00 120.00   1.00    6.00    --   29.16   0.00-120.00  182
 21  \w    -62.00 120.00   1.00    6.00    --   29.16   0.00 -90.00  182
 22  \w    -62.00 120.00   1.00    6.00    --   29.16   0.00 -60.00  182
 23  \w    -62.00 120.00   1.00    6.00    --   29.16   0.00 -30.00  182
 24  \w    -62.00  69.00   1.00    6.00    --   29.16   0.00   0.00  131
 25  \w    -62.00 120.00   1.00    6.00    --   29.16   0.00-150.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0806490000
_diffrn_orient_matrix_UB_12      0.0469764000
_diffrn_orient_matrix_UB_13      0.0361346000
_diffrn_orient_matrix_UB_21      -0.0446983000
_diffrn_orient_matrix_UB_22      0.0828366000
_diffrn_orient_matrix_UB_23      -0.0124556000
_diffrn_orient_matrix_UB_31      -0.0449075000
_diffrn_orient_matrix_UB_32      -0.0062151000
_diffrn_orient_matrix_UB_33      0.0559085000
_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  0.0255
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.828
_diffrn_reflns_theta_min         1.944
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.310
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.76a (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    1.342
_exptl_crystal_description       plate
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.536
_exptl_crystal_size_min          0.187
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0284
_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/[\s^2^(Fo^2^)+(0.0396P)^2^+0.2238P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0783
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2528
_reflns_number_total             2683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra02137a2.cif
_cod_data_source_block           1c
_cod_database_code               7248641
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.867
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
2.d :
 C8(H8)
;
_shelx_res_checksum              18672
_shelx_hkl_checksum              46885
_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 1.228
_oxdiff_exptl_absorpt_empirical_full_min 0.838