Post-coordination of Ru(ii) controlled regioselective B(4)–H acylmethylation of o-carboranes with sulfoxonium ylides
Cao, Hou-Ji; Li, Jia-Xin; Yan, Jia-Hui; Liu, Miao-Xin; Zhao, Qianyi; Zhang, Jie; Zhang, Ju; Yan, Hong; Chemical Science 16 (2025) 9406–9412; doi:10.1039/D5SC01576F

data_1574487
_publ_section_title
;
 Post-coordination of Ru(ii) controlled regioselective B(4)--H
 acylmethylation of o-carboranes with sulfoxonium ylides
;
_journal_issue                   21
_journal_name_full               'Chemical Science'
_journal_page_first              9406
_journal_page_last               9412
_journal_paper_doi               10.1039/D5SC01576F
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C17 H24 B10 O'
_chemical_formula_sum            'C17 H24 B10 O'
_chemical_formula_weight         352.46
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-02-25 deposited with the CCDC.	2025-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                95.963(7)
_cell_angle_beta                 114.424(10)
_cell_angle_gamma                96.569(8)
_cell_formula_units_Z            2
_cell_length_a                   10.2082(11)
_cell_length_b                   10.3206(9)
_cell_length_c                   10.8736(9)
_cell_measurement_reflns_used    3488
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5290
_cell_measurement_theta_min      4.5280
_cell_volume                     1021.64(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_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   -103.00 -19.00   1.00    2.10    --  -35.62 -52.00  75.00   84
  2  \w    -52.00  32.00   1.00    2.10    --  -35.62  52.00-140.00   84
  3  \w     19.00 103.00   1.00    2.10    --   35.62  52.00-140.00   84
  4  \w    -32.00  52.00   1.00    2.10    --   35.62 -52.00  75.00   84
  5  \w     90.00 175.00   1.00    8.41    --  107.12  52.00-140.00   85
  6  \w     39.00 124.00   1.00    8.41    --  107.12 -52.00  75.00   85
  7  \w      9.00 103.00   1.00    2.10    --   35.62  77.00 120.00   94
  8  \w      1.00  75.00   1.00    2.10    --   35.62 -99.00 120.00   74
  9  \w      1.00  75.00   1.00    2.10    --   35.62 -99.00 -60.00   74
 10  \w    -36.00  65.00   1.00    2.10    --   35.62 -19.00-150.00  101
 11  \w    -32.00  62.00   1.00    2.10    --   35.62 -77.00   0.00   94
 12  \w      1.00  75.00   1.00    2.10    --   35.62 -99.00 -90.00   74
 13  \w     57.00 108.00   1.00    2.10    --   35.62 178.00 -90.00   51
 14  \w     37.00 113.00   1.00    8.41    --  107.12-111.00  60.00   76
 15  \w     97.00 177.00   1.00    8.41    --  107.12  30.00 120.00   80
 16  \w     43.00  84.00   1.00    8.41    --  107.12 -95.00  60.00   41
 17  \w     72.00 113.00   1.00    8.41    --  107.12-111.00 120.00   41
 18  \w     43.00  71.00   1.00    8.41    --  107.12-111.00 120.00   28
 19  \w     58.00 117.00   1.00    8.41    --  107.12 -61.00-150.00   59
 20  \w     70.00 110.00   1.00    8.41    --  107.12 -95.00-150.00   40
 21  \w     89.00 171.00   1.00    8.41    --  107.12  61.00-180.00   82
 22  \w     59.00 123.00   1.00    8.41    --  107.12 -61.00 120.00   64
 23  \w     86.00 113.00   1.00    8.41    --  107.12 178.00  60.00   27
 24  \w    125.00 150.00   1.00    8.41    --  107.12 178.00  60.00   25
 25  \w     90.00 170.00   1.00    8.41    --  107.12  61.00 150.00   80
 26  \w     66.00  93.00   1.00    8.41    --  107.12 -95.00-180.00   27
 27  \w     45.00 124.00   1.00    8.41    --  107.12 -30.00-180.00   79
 28  \w    122.00 149.00   1.00    8.41    --  107.12 111.00-120.00   27
 29  \w     78.00 142.00   1.00    8.41    --  107.12 178.00  90.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1562538000
_diffrn_orient_matrix_UB_12      0.0802263000
_diffrn_orient_matrix_UB_13      0.0649220000
_diffrn_orient_matrix_UB_21      0.0201794000
_diffrn_orient_matrix_UB_22      -0.0515024000
_diffrn_orient_matrix_UB_23      -0.1280895000
_diffrn_orient_matrix_UB_31      -0.0592032000
_diffrn_orient_matrix_UB_32      0.1189002000
_diffrn_orient_matrix_UB_33      -0.0654746000
_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  0.0285
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8499
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.002
_diffrn_reflns_theta_min         4.374
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.146
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0701
_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^)+(0.0942P)^2^+0.4491P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2045
_refine_ls_wR_factor_ref         0.2243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2845
_reflns_number_total             3893
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01576f2.cif
_cod_data_source_block           3b
_cod_depositor_comments
'Adding full bibliography for 1574487--1574490.cif.'
_cod_original_cell_volume        1021.64(18)
_cod_database_code               1574487
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'B1 C1 N1 O1'
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.953
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.d Boron cage BH refined with riding coordinates:
 C1(H1)
;
_shelx_res_checksum              51484
_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 1.601
_oxdiff_exptl_absorpt_empirical_full_min 0.310