Microwave-assisted Pd-catalyzed B-N cross-coupling for efficient functionalization of the carbaborate [CB<sub>11</sub>H<sub>12</sub>]<sup/>.
Jin, Yujie; Chen, Lianyu; Jiang, Chennuo; Liu, Jiyong; Zhang, Kang; Duttwyler, Simon; Chemical communications (Cambridge, England) 61 (2025) 16262–16265; doi:10.1039/d5cc04753f

data_1575721
_publ_section_title
;
 Microwave-assisted Pd-catalyzed B-N cross-coupling for efficient
 functionalization of the carbaborate
 [CB<sub>11</sub>H<sub>12</sub>]<sup/>.
;
_journal_issue                   83
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              16262
_journal_page_last               16265
_journal_paper_doi               10.1039/d5cc04753f
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C8 H18 B11 N2 O, C8 H20 N'
_chemical_formula_sum            'C16 H38 B11 N3 O'
_chemical_formula_weight         407.40
_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     dual
_audit_creation_date             2023-03-29
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-08-11 deposited with the CCDC.	2025-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.018(4)
_cell_length_b                   14.127(4)
_cell_length_c                   26.513(8)
_cell_measurement_reflns_used    6035
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      59.794
_cell_measurement_theta_min      2.900
_cell_volume                     4876(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.1287
_diffrn_reflns_av_unetI/netI     0.0881
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_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            56745
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.455
_diffrn_reflns_theta_min         2.900
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1151 before and 0.0878 after correction.
The Ratio of minimum to maximum transmission is 0.8525.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_description       needle
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5561
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0666
_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^)+(0.1145P)^2^+0.5142P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1870
_refine_ls_wR_factor_ref         0.2144
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3593
_reflns_number_total             5561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04753f2.cif
_cod_data_source_block           230328_jyj_760_0m
_cod_depositor_comments
'Adding full bibliography for 1575720--1575723.cif.'
_cod_original_cell_volume        4876(2)
_cod_database_code               1575721
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All B(H,H,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. Restrained distances
 N2-H2B
 0.88 with sigma of 0.02
 N2-H2A
 0.88 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B), C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C7(H7), C8(H8)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C)
3.d Boron cage BH refined with riding coordinates:
 C1(H1A), B1(H1B), B2(H2), B3(H3), B4(H4A), B5(H5A), B6(H6), B7(H7A), B8(H8A),
 B9(H9), B10(H10)
;
_shelx_res_checksum              45874
_olex2_submission_special_instructions 'No special instructions were received'