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_1565422
_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         'C22 H34 B10 N2 O3 S, C Cl3 D'
_chemical_formula_sum            'C23 H34 B10 Cl3 D N2 O3 S'
_chemical_formula_weight         635.04
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-08-24
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-25 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                71.811(3)
_cell_angle_beta                 76.438(3)
_cell_angle_gamma                65.487(3)
_cell_formula_units_Z            2
_cell_length_a                   10.5400(11)
_cell_length_b                   12.1568(14)
_cell_length_c                   14.1284(14)
_cell_measurement_reflns_used    5927
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.30
_cell_volume                     1553.3(3)
_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  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13290
_diffrn_reflns_point_group_measured_fraction_full 0.679
_diffrn_reflns_point_group_measured_fraction_max 0.664
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.411
_diffrn_reflns_theta_min         2.128
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0699 before and 0.0444 after correction. The Ratio of minimum to maximum transmission is 0.8243. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CDCl3'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1733 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     761
_refine_ls_number_reflns         9387
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0433P)^2^+0.5010P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.346
_reflns_Friedel_fraction_full    0.367
_reflns_Friedel_fraction_max     0.342
_reflns_number_gt                7860
_reflns_number_total             9387
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05296a2.cif
_cod_data_source_block           11_a
_cod_database_code               1565422
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.933
_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.a Ternary CH refined with riding coordinates:
 C11(H11), C11A(H11B), C23(D23), C23A(D23A)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C15A(H15C,H15D), C15(H15A,H15B), C13A(H13C,H13D), C12(H12A,H12B),
  C13(H13A,H13B), C12A(H12C,H12D), C14(H14A,H14B), C9A(H9AA,H9AB), C14A(H14C,
 H14D)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C17(H17), C5A(H5AA), C5(H5), C18(H18), C18A(H18A), C20(H20),
 C19A(H19A), C20A(H20A), C17A(H17A), C7(H7), C6(H6), C6A(H6AA), C8(H8),
 C7A(H7AA), C8A(H8AB)
2.d Idealised Me refined as rotating group:
 C3A(H3AA,H3AB,H3AC), C3(H3A,H3B,H3C), C22A(H22D,H22E,H22F), C22(H22A,H22B,H22C)
2.e Boron cage BH refined with riding coordinates:
 B5A(H5AB), B7(H7A), B5(H5A), B3A(H3AD), B3(H3), B8A(H8AA), B7A(H7AB),
 B6A(H6AB), B10A(H10A), B11(H11A), B9A(H9AC), B12A(H12E), B11A(H11C), B9(H9),
 B12(H12), B6(H6A), B8(H8A), B10(H10)
;
_shelx_res_checksum              86453
_olex2_submission_special_instructions 'No special instructions were received'