Metal-catalyzed B–H acylmethylation of pyridylcarboranes: access to carborane-fused indoliziniums and quinoliziniums
Cao, Hou-Ji; Wei, Xing; Sun, Fangxiang; Zhang, Xiaolei; Lu, Changsheng; Yan, Hong; Chemical Science  (2021) –; doi:10.1039/D1SC05296A

data_1565424
_publ_section_title
;
 Metal-catalyzed B--H acylmethylation of pyridylcarboranes: access to
 carborane-fused indoliziniums and quinoliziniums
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC05296A
_journal_year                    2021
_chemical_formula_moiety         'C16 H28 B10 Br N O'
_chemical_formula_sum            'C16 H28 B10 Br N O'
_chemical_formula_weight         438.40
_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     dual
_audit_creation_date             2021-03-19
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-12 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.06
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.829
_cell_length_b                   29.804
_cell_length_c                   9.584
_cell_measurement_reflns_used    4472
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.24
_cell_volume                     2233.099
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0976
_diffrn_reflns_av_unetI/netI     0.0997
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17903
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_min         2.235
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.848
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1331 before and 0.1000 after correction. The Ratio of minimum to maximum transmission is 0.4473. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.991
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5074
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1473
_refine_ls_R_factor_gt           0.0942
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1627P)^2^+3.2729P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2705
_refine_ls_wR_factor_ref         0.3114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2991
_reflns_number_total             5074
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05296a2.cif
_cod_data_source_block           11
_cod_original_cell_volume        2233.1
_cod_database_code               1565424
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.756
_shelx_estimated_absorpt_t_min   0.709
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
N1 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8: within 2.7A with sigma of 0.01
and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B),
 C16(H16A,H16B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8A)
3.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
3.d Boron cage BH refined with riding coordinates:
 B3(H3), B5(H5A), B6(H6A), B7(H7A), B8(H8), B9(H9), B10(H10), B11(H11), B12(H12)
;
_shelx_res_checksum              65594
_olex2_submission_special_instructions 'No special instructions were received'