A Pd-catalyzed route to carborane-fused boron heterocycles.
Zhu, Mengjie; Wang, Puzhao; Wu, Zhengqiu; Zhong, Yangfa; Su, Laiman; Xin, Yuquan; Spokoyny, Alexander M.; Zou, Chao; Mu, Xin; Chemical science 15 (2024) 10392–10401; doi:10.1039/d4sc02214a

data_1571744
_publ_section_title
;
 A Pd-catalyzed route to carborane-fused boron heterocycles.
;
_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              10392
_journal_page_last               10401
_journal_paper_doi               10.1039/d4sc02214a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C17 H24 B10 N2 O3'
_chemical_formula_sum            'C17 H24 B10 N2 O3'
_chemical_formula_weight         412.48
_chemical_name_systematic        123
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-11-01
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-04 deposited with the CCDC.	2024-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.430(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.712(2)
_cell_length_b                   11.259(3)
_cell_length_c                   19.629(3)
_cell_measurement_reflns_used    238
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      67.60
_cell_measurement_theta_min      28.29
_cell_volume                     2146.3(8)
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15785
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.031
_diffrn_reflns_theta_min         4.527
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1428 before and 0.0837 after correction.
The Ratio of minimum to maximum transmission is 0.6611.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.0030(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         3870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1262P)^2^+0.2895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.2056
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2780
_reflns_number_total             3870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02214a2.cif
_cod_data_source_block           cu_20231031_zm_hdlg_wpz_0m
_cod_depositor_comments
'Adding full bibliography for 1571739--1571749.cif.'
_cod_original_cell_volume        2146.4(8)
_cod_database_code               1571744
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.926
_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. Uiso/Uaniso restraints and constraints
O3A: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002 within
2A
3. Others
 Sof(O3A)=1-FVAR(1)
 Sof(O3)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4a), C5(H5a), C9(H9a), C10(H10), C13(H13), C14(H14), C16(H16)
4.b Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C17(H17a,H17b,H17c)
4.c Boron cage BH refined with riding coordinates:
 C1(H1), B1(H1a), C2(H2), B2(H2a), B3(H3a), B4(H4), B5(H5), B6(H6), B7(H7),
 B9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'