Stereospecific alkenylation of carboranes: copper-catalyzed access to pyridylcarboranyl alkenes
Li, Ping; Li, Xiang; Wang, Liyan; Wang, Mengmeng; Tu, Deshuang; Yan, Hong; Lu, Jian; Lu, Ju-You; Chemical Science  (2026) –; doi:10.1039/D5SC10093C

data_1576464
_publ_section_title
;
 Stereospecific alkenylation of carboranes: copper-catalyzed access to
 pyridylcarboranyl alkenes.
;
_journal_issue                   14
_journal_name_full               'Chemical science'
_journal_page_first              7194
_journal_page_last               7202
_journal_paper_doi               10.1039/d5sc10093c
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         '2(C16 H32 B20 Cu2 N2 O3)'
_chemical_formula_sum            'C32 H64 B40 Cu4 N4 O6'
_chemical_formula_weight         1287.43
_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             2024-11-04
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-10-21 deposited with the CCDC.	2026-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                85.791(2)
_cell_angle_beta                 86.643(2)
_cell_angle_gamma                70.673(2)
_cell_formula_units_Z            1
_cell_length_a                   7.3682(3)
_cell_length_b                   10.1761(4)
_cell_length_c                   22.8548(10)
_cell_measurement_reflns_used    9444
_cell_measurement_temperature    170
_cell_measurement_theta_max      63.839
_cell_measurement_theta_min      3.881
_cell_volume                     1611.64(12)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker d8 venture'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13973
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        63.838
_diffrn_reflns_theta_max         63.838
_diffrn_reflns_theta_min         3.881
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.798
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.6174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1249 before and 0.0657 after correction.
The Ratio of minimum to maximum transmission is 0.8206.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         5282
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0581P)^2^+0.9139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4706
_reflns_number_total             5282
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc10093c2.cif
_cod_data_source_block           1_0m
_cod_depositor_comments
'Adding full bibliography for 1576464--1576468.cif.'
_cod_database_code               1576464
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.870
_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 C(H,H,H) groups
2. Restrained distances
 O1-H1
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C3(H3), C14(H14), C4(H4), C16(H16), C15(H15), C2(H2), C1(H1A)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
3.c Boron cage BH refined with riding coordinates:
 B17(H17), B12(H12), B1(H1B), B15(H15A), B5(H5), B16(H16A), B11(H11),
 B13(H13A), B18(H18), B14(H14A), B19(H19), B20(H20), B3(H3A), B4(H4A), B2(H2A),
 B7(H7), B6(H6), B9(H9), B8(H8), B10(H10)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'