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_1574488
_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         'C24 H38 B20 O5 Ru'
_chemical_formula_sum            'C24 H38 B20 O5 Ru'
_chemical_formula_weight         723.81
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-08-22
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.4669(2)
_cell_length_b                   12.00586(15)
_cell_length_c                   28.6857(3)
_cell_measurement_reflns_used    8036
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4790
_cell_measurement_theta_min      4.5260
_cell_volume                     7048.73(13)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_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   -102.00 -17.00   0.50   17.00    --  -33.50 -57.00   0.00  170
  2  \w   -107.00 -75.00   0.50   17.00    --  -33.50 178.00 150.00   64
  3  \w    -25.00   1.00   0.50   17.00    --  -33.50 -19.00  60.00   52
  4  \w   -102.00 -30.00   0.50   17.00    --  -33.50 -19.00  60.00  144
  5  \w      4.00  29.00   0.50   17.00    --   36.47 -99.00 150.00   50
  6  \w     31.00  76.00   0.50   17.00    --   36.47 -99.00   0.00   90
  7  \w     40.00  69.00   0.50   17.00    --   36.47 -99.00 150.00   58
  8  \w     77.00 106.00   0.50   40.00    --  108.00-111.00 150.00   58
  9  \w     44.00  70.00   0.50   40.00    --  108.00-111.00 150.00   52
 10  \w    106.00 177.00   0.50   40.00    --  108.00  77.00  30.00  142
 11  \w    152.00 177.00   0.50   40.00    --  108.00  77.00 -90.00   50
 12  \w     45.00 109.00   0.50   40.00    --  108.00-111.00  60.00  128
 13  \w     41.00 123.00   0.50   40.00    --  108.00 -61.00  30.00  164
 14  \w     45.00 130.00   0.50   40.00    --  108.00 -30.00 -90.00  170
 15  \w     40.00  95.00   0.50   40.00    --  108.00-111.00   0.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0203865000
_diffrn_orient_matrix_UB_12      -0.0999568000
_diffrn_orient_matrix_UB_13      -0.0303685000
_diffrn_orient_matrix_UB_21      -0.0724782000
_diffrn_orient_matrix_UB_22      0.0296767000
_diffrn_orient_matrix_UB_23      0.0076292000
_diffrn_orient_matrix_UB_31      0.0014985000
_diffrn_orient_matrix_UB_32      0.0747031000
_diffrn_orient_matrix_UB_33      -0.0436271000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            22139
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.445
_diffrn_reflns_theta_min         3.763
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.863
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       plate
_exptl_crystal_F_000             2928
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.395
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         6568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0527
_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/[\s^2^(Fo^2^)+(0.0974P)^2^+3.1100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1612
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5056
_reflns_number_total             6568
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01576f2.cif
_cod_data_source_block           A2_H2O
_cod_depositor_comments
'Adding full bibliography for 1574487--1574490.cif.'
_cod_original_cell_volume        7048.75(14)
_cod_database_code               1574488
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20B6O5Ru1
_shelx_estimated_absorpt_t_max   0.861
_shelx_estimated_absorpt_t_min   0.634
_reflns_odcompleteness_completeness 98.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C4A(H4A), C5(H5), C5A(H5A), C6(H6), C6A(H6A), C7(H7), C7A(H7A),
 C8(H8), C8A(H8A), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Boron cage BH refined with riding coordinates:
 B3(H3), B3A(H3AA), B4(H4B), B4A(H4AA), B5(H5B), B5A(H5AA), B6(H6B), B6A(H6AA),
  B7(H7B), B7A(H7AA), B8(H8B), B8A(H8AA), B9(H9), B9A(H9A), B10(H10A),
 B10A(H10B), B11(H11A), B11A(H11B), B12(H12A), B12A(H12B)
;
_shelx_res_checksum              97214
_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 1.430
_oxdiff_exptl_absorpt_empirical_full_min 0.786