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_1574490
_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 Br O'
_chemical_formula_sum            'C16 H21 B10 Br O'
_chemical_formula_weight         417.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-09
_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                 98.262(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5191(2)
_cell_length_b                   10.8321(3)
_cell_length_c                   18.0396(4)
_cell_measurement_reflns_used    4453
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1890
_cell_measurement_theta_min      4.5990
_cell_volume                     2034.17(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (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    'SHELXT 2014/5 (Sheldrick, 2014)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.982
_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    -78.00   3.00   1.00    1.11    --  -35.62 113.00 -75.00   81
  2  \w     31.00  79.00   1.00    1.11    --   35.62-113.00-167.00   48
  3  \w    110.00 165.00   1.00    4.44    --  106.81 113.00 -75.00   55
  4  \w     70.00  96.00   1.00    4.44    --  106.81-113.00-167.00   26
  5  \w   -102.00 -19.00   1.00    1.11    --  -35.62 -57.00-180.00   83
  6  \w    -98.00 -68.00   1.00    1.11    --  -35.62 -19.00  60.00   30
  7  \w    -36.00  -8.00   1.00    1.11    --  -35.62 -19.00  60.00   28
  8  \w    -29.00  21.00   1.00    1.11    --   35.62 -19.00-150.00   50
  9  \w     29.00  62.00   1.00    1.11    --   35.62 -19.00-150.00   33
 10  \w     61.00 107.00   1.00    1.11    --   35.62 178.00 120.00   46
 11  \w     38.00  65.00   1.00    1.11    --   35.62  57.00 120.00   27
 12  \w     70.00  97.00   1.00    4.44    --  106.81 -61.00-180.00   27
 13  \w     89.00 115.00   1.00    4.44    --  106.81  45.00  90.00   26
 14  \w     44.00 104.00   1.00    4.44    --  106.81-111.00   0.00   60
 15  \w     37.00 106.00   1.00    4.44    --  106.81 -95.00-150.00   69
 16  \w    131.00 168.00   1.00    4.44    --  106.81  45.00  90.00   37
 17  \w    104.00 167.00   1.00    4.44    --  106.81  77.00-180.00   63
 18  \w     98.00 125.00   1.00    4.44    --  106.81 -61.00-180.00   27
 19  \w     89.00 175.00   1.00    4.44    --  106.81  45.00 -30.00   86
 20  \w     38.00 124.00   1.00    4.44    --  106.81 -30.00 150.00   86
;
_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      -0.0128691000
_diffrn_orient_matrix_UB_12      0.0714947000
_diffrn_orient_matrix_UB_13      0.0723620000
_diffrn_orient_matrix_UB_21      0.0406388000
_diffrn_orient_matrix_UB_22      0.1197722000
_diffrn_orient_matrix_UB_23      -0.0362664000
_diffrn_orient_matrix_UB_31      -0.1417011000
_diffrn_orient_matrix_UB_32      0.0278763000
_diffrn_orient_matrix_UB_33      -0.0298920000
_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  0.0234
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8822
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.345
_diffrn_reflns_theta_min         4.599
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
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    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0702P)^2^+1.0042P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3365
_reflns_number_total             3881
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01576f2.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 1574487--1574490.cif.'
_cod_database_code               1574490
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 B1 Br1 O1'
_shelx_estimated_absorpt_t_max   0.771
_shelx_estimated_absorpt_t_min   0.717
_reflns_odcompleteness_completeness 99.90
_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
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.c Boron cage BH refined with riding coordinates:
 C1(H1), B3(H3A), B5(H5), B6(H6A), B7(H7A), B8(H8A), B9(H9A), B10(H10A),
 B11(H11), B12(H12A)
;
_shelx_res_checksum              3785
_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 1.531
_oxdiff_exptl_absorpt_empirical_full_min 0.598