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_1575720
_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 H17 B11 N O, C8 H20 N'
_chemical_formula_sum            'C16 H37 B11 N2 O'
_chemical_formula_weight         392.38
_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             2021-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-08-11 deposited with the CCDC.	2025-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.842(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.6690(14)
_cell_length_b                   7.6686(4)
_cell_length_c                   24.2067(10)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      32.10
_cell_measurement_theta_min      2.30
_cell_volume                     4829.4(4)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10953
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         2.296
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0857 before and 0.0472 after correction.
The Ratio of minimum to maximum transmission is 0.9223.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.079
_exptl_crystal_description       needle
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         10953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0615
_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^)+(0.0767P)^2^+2.4512P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1636
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9414
_reflns_number_total             10953
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04753f2.cif
_cod_data_source_block           mo_210927_jyj_22
_cod_depositor_comments
'Adding full bibliography for 1575720--1575723.cif.'
_cod_database_code               1575720
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8859(8)
 0.1141(8)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C21(H21A,H21B), C23(H23A,H23B), C25(H25A,
 H25B), C27(H27A,H27B), C29(H29A,H29B), C31(H31A,H31B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), N2(H2A), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C32(H32A,
 H32B,H32C)
3.d Boron cage BH refined with riding coordinates:
 C1(H1A), B1(H1B), B2(H2), B3(H3), B4(H4A), B5(H5A), B6(H6A), B7(H7A), B8(H8A),
  B9(H9), B10(H10), C9(H9A), B12(H12A), B13(H13A), B14(H14A), B15(H15A),
 B16(H16A), B17(H17), B18(H18), B19(H19), B20(H20), B21(H21)
;
_shelx_res_checksum              45001
_olex2_submission_special_instructions 'No special instructions were received'