Regioselective C(sp<sup>3</sup>)-H borylation <i>via</i> a diarylboryl anion surrogate in sp<sup>2</sup>-sp<sup>3</sup> diboranes(5).
Mao, Xiaofeng; Zhang, Jie; Xie, Zuowei; Chemical science 16 (2025) 22314–22321; doi:10.1039/d5sc07180a

data_1576176
_publ_section_title
;
 Regioselective C(sp<sup>3</sup>)-H borylation <i>via</i> a diarylboryl
 anion surrogate in sp<sup>2</sup>-sp<sup>3</sup> diboranes(5).
;
_journal_issue                   47
_journal_name_full               'Chemical science'
_journal_page_first              22314
_journal_page_last               22321
_journal_paper_doi               10.1039/d5sc07180a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C32 H39 B2 Si, C16 H32 Li O4'
_chemical_formula_sum            'C48 H71 B2 Li O4 Si'
_chemical_formula_weight         768.69
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-07-26 deposited with the CCDC.	2025-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.434(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2790(6)
_cell_length_b                   14.9402(8)
_cell_length_c                   27.9641(15)
_cell_measurement_reflns_used    9697
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      56.89
_cell_measurement_theta_min      2.93
_cell_volume                     4618.7(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2014'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON III area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            73555
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         56.976
_diffrn_reflns_theta_min         2.805
_diffrn_source                   'microfocus Metaljet'
_diffrn_source_current           2.5
_diffrn_source_power             0.174525
_diffrn_source_type              'Incoatec Metaljet'
_diffrn_source_voltage           69.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.482
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1250 before and 0.0656 after correction.
The Ratio of minimum to maximum transmission is 0.8582.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_description       block
_exptl_crystal_F_000             1672
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         9424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0496P)^2^+1.1759P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8130
_reflns_number_total             9424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc07180a2.cif
_cod_data_source_block           '[2b]Li'
_cod_depositor_comments
'Adding full bibliography for 1576174--1576180.cif.'
_cod_database_code               1576176
_shelx_shelxl_version_number     2018/3
_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 Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C36(H36A,H36B), C39(H39A,H39B), C40(H40A,H40B), C41(H41A,
 H41B), C42(H42A,H42B), C43(H43A,H43B), C45(H45A,H45B), C47(H47A,H47B),
 C48(H48A,H48B), C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B),
  C53(H53A,H53B), C54(H54A,H54B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C19(H19), C20(H20),
 C21(H21), C22(H22), C24(H24), C25(H25), C28(H28), C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C23(H23A,H23B,
 H23C), C26(H26A,H26B,H26C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              77183
_olex2_submission_special_instructions 'No special instructions were received'