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_1574489
_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         'C16 H21 B10 N O3'
_chemical_formula_sum            'C16 H21 B10 N O3'
_chemical_formula_weight         383.44
_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             2022-06-02
_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                103.664(3)
_cell_angle_beta                 111.893(4)
_cell_angle_gamma                96.953(3)
_cell_formula_units_Z            2
_cell_length_a                   10.0973(4)
_cell_length_b                   10.5194(3)
_cell_length_c                   10.8504(5)
_cell_measurement_reflns_used    4543
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2540
_cell_measurement_theta_min      4.6170
_cell_volume                     1010.78(8)
_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 2019/2 (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 0.997
_diffrn_measured_fraction_theta_max 0.975
_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    -56.00  31.00   1.00    1.00    --  -35.62  65.00 -20.00   87
  2  \w   -102.00 -16.00   1.00    1.00    --  -35.62 -65.00-155.00   86
  3  \w     16.00 102.00   1.00    1.00    --   35.62  65.00 -20.00   86
  4  \w    -31.00  56.00   1.00    1.00    --   35.62 -65.00-155.00   87
  5  \w     87.00 174.00   1.00    1.84    --  107.12  65.00 -20.00   87
  6  \w     41.00 127.00   1.00    1.84    --  107.12 -65.00-155.00   86
  7  \w      6.00 107.00   1.00    1.00    --   35.62  19.00 -30.00  101
  8  \w      1.00  75.00   1.00    1.00    --   35.62 -99.00 -30.00   74
  9  \w      1.00  75.00   1.00    1.00    --   35.62 -99.00 -90.00   74
 10  \w    -32.00   5.00   1.00    1.00    --   35.62 -38.00 -30.00   37
 11  \w     14.00  40.00   1.00    1.00    --   35.62 -38.00 -30.00   26
 12  \w      2.00  73.00   1.00    1.00    --   35.62 -99.00 150.00   71
 13  \w     20.00  91.00   1.00    1.00    --   35.62  57.00  90.00   71
 14  \w     39.00 108.00   1.00    1.84    --  107.12-111.00 -90.00   69
 15  \w     91.00 133.00   1.00    1.84    --  107.12  45.00-120.00   42
 16  \w     90.00 177.00   1.00    1.84    --  107.12  30.00  60.00   87
 17  \w    100.00 131.00   1.00    1.84    --  107.12 111.00 150.00   31
 18  \w    148.00 173.00   1.00    1.84    --  107.12  45.00-120.00   25
 19  \w     51.00 109.00   1.00    1.84    --  107.12 -95.00   0.00   58
 20  \w     40.00 125.00   1.00    1.84    --  107.12 -45.00-120.00   85
 21  \w     40.00 100.00   1.00    1.84    --  107.12 -95.00 150.00   60
 22  \w    104.00 171.00   1.00    1.84    --  107.12  45.00 -60.00   67
 23  \w     70.00 125.00   1.00    1.84    --  107.12 -61.00 150.00   55
 24  \w     47.00 120.00   1.00    1.84    --  107.12 -45.00 -30.00   73
 25  \w     69.00 110.00   1.00    1.84    --  107.12-111.00  90.00   41
 26  \w     72.00 105.00   1.00    1.84    --  107.12 -95.00 -90.00   33
 27  \w    125.00 176.00   1.00    1.84    --  107.12 111.00 -60.00   51
 28  \w     37.00  95.00   1.00    1.84    --  107.12-111.00 150.00   58
 29  \w     98.00 125.00   1.00    1.84    --  107.12 178.00-150.00   27
 30  \w     62.00  88.00   1.00    1.84    --  107.12 178.00-150.00   26
;
_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      -0.0739293000
_diffrn_orient_matrix_UB_12      0.0047153000
_diffrn_orient_matrix_UB_13      0.1016516000
_diffrn_orient_matrix_UB_21      -0.1277095000
_diffrn_orient_matrix_UB_22      -0.1163190000
_diffrn_orient_matrix_UB_23      -0.1109143000
_diffrn_orient_matrix_UB_31      0.0824579000
_diffrn_orient_matrix_UB_32      -0.1022478000
_diffrn_orient_matrix_UB_33      0.0564743000
_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  0.0148
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8588
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.498
_diffrn_reflns_theta_min         4.447
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83921
_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    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0629
_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^)+(0.0966P)^2^+0.2125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.1813
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3227
_reflns_number_total             3849
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01576f2.cif
_cod_data_source_block           3l
_cod_depositor_comments
'Adding full bibliography for 1574487--1574490.cif.'
_cod_original_cell_volume        1010.78(7)
_cod_database_code               1574489
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C1 H1 B1 O1'
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.928
_reflns_odcompleteness_completeness 99.69
_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
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 Boron cage BH refined with riding coordinates:
 C1(H1)
;
_shelx_res_checksum              10190
_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 1.503
_oxdiff_exptl_absorpt_empirical_full_min 0.742