Oxidation-induced nucleophilic substitution at the electron-rich B(12) vertex in [CB<sub>11</sub>H<sub>12</sub>]<sup>-</sup> under catalyst-free conditions.
Sun, Wanqi; Jin, Yujie; Wang, Yongtao; Wen, Zeyu; Sun, Jizeng; Yao, Jia; Duttwyler, Simon; Li, Haoran; Chemical science 16 (2025) 5942–5947; doi:10.1039/d5sc00234f

data_1573988
_publ_section_title
;
 Oxidation-induced nucleophilic substitution at the electron-rich B(12)
 vertex in [CB<sub>11</sub>H<sub>12</sub>]<sup>-</sup> under catalyst-free
 conditions.
;
_journal_issue                   14
_journal_name_full               'Chemical science'
_journal_page_first              5942
_journal_page_last               5947
_journal_paper_doi               10.1039/d5sc00234f
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C13 H34 B11 N2 O2, C8 H20 N'
_chemical_formula_sum            'C21 H54 B11 N3 O2'
_chemical_formula_weight         499.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-12-03 deposited with the CCDC.	2025-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.836(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.1967(5)
_cell_length_b                   22.4636(8)
_cell_length_c                   20.8837(8)
_cell_measurement_reflns_used    9142
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.580
_cell_measurement_theta_min      3.382
_cell_volume                     6183.3(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III M28'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'ZJU Bruker D8 VENTURE Metaljet PHOTON III'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            67077
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.633
_diffrn_reflns_theta_min         2.917
_diffrn_source                   'liquid Metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_type              'Bruker Excillum Metaljet D2+'
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0677 before and 0.0557 after correction.
The Ratio of minimum to maximum transmission is 0.8939.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.073
_exptl_crystal_description       block
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     687
_refine_ls_number_reflns         14162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0659P)^2^+1.4468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11519
_reflns_number_total             14162
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00234f2.cif
_cod_data_source_block           241017_or_ch3_tempo
_cod_depositor_comments
'Adding full bibliography for 1573985--1573988.cif.'
_cod_database_code               1573988
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.963
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C17(H17A,H17B), C19(H19A,H19B), C27(H27A,H27B),
 C29(H29A,H29B), C31(H31A,H31B), C33(H33A,H33B), C35(H35A,H35B), C37(H37A,H37B),
  C39(H39A,H39B), C41(H41A,H41B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4C)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,
 H26B,H26C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C),
 C34(H34A,H34B,H34C), C36(H36A,H36B,H36C), C38(H38A,H38B,H38C), C40(H40A,H40B,
 H40C), C42(H42A,H42B,H42C)
2.e Boron cage BH refined with riding coordinates:
 C1(H1), B1(H1A), B2(H2D), B3(H3), B4(H4), B5(H5A), B7(H7), B8(H8), B9(H9),
 B10(H10), C14(H14), B12(H12), B13(H13), B14(H14A), B15(H15), B16(H16),
 B17(H17), B18(H18A), B19(H19), B20(H20)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_olex2_submission_special_instructions 'No special instructions were received'