Dispersion-controlled C6-selective C–H borylation of indoles
Zheng, Tianyu; Jiang, Hao; Ma, Jiawei; Chen, Haochi; Shi, Zhuangzhi; Liang, Yong; Chemical Communications 61 (2025) 8208–8211; doi:10.1039/D5CC01554E

data_7134469
_publ_section_title
;
 Dispersion-controlled C6-selective C--H borylation of indoles
;
_journal_issue                   45
_journal_name_full               'Chemical Communications'
_journal_page_first              8208
_journal_page_last               8211
_journal_paper_doi               10.1039/D5CC01554E
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C23 H37 B N O2 P'
_chemical_formula_sum            'C23 H37 B N O2 P'
_chemical_formula_weight         401.31
_chemical_name_systematic
1-(di-tert-butylphosphaneyl)-3-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-03-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-04-22 deposited with the CCDC.	2025-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                80.546(2)
_cell_angle_beta                 88.085(2)
_cell_angle_gamma                87.299(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7665(3)
_cell_length_b                   11.5656(6)
_cell_length_c                   13.5181(6)
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    193.0
_cell_measurement_theta_max      26.83
_cell_measurement_theta_min      2.63
_cell_volume                     1196.02(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      193.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_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  0.0450
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11404
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.533
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0958 before and 0.0470 after correction. The Ratio of minimum to maximum transmission is 0.8820. 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    1.114
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         5447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0402P)^2^+0.6199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1338
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3730
_reflns_number_total             5447
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01554e2.cif
_cod_data_source_block           1_a
_cod_depositor_comments
'Adding full bibliography for 7134469--7134470.cif.'
_cod_database_code               7134469
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C8(H8), C3(H3)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C17(H17A,H17B,
 H17C), C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C21(H21A,
 H21B,H21C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              71026
_shelx_hkl_checksum              85224
_olex2_submission_special_instructions 'No special instructions were received'