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_7134470
_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         'C37 H53 B N O2 P'
_chemical_formula_sum            'C37 H53 B N O2 P'
_chemical_formula_weight         585.58
_chemical_name_systematic
1-(Di(adamantan-1-yl)phosphaneyl)-3-isopropyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
_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
_audit_creation_date             2023-03-08
_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                90
_cell_angle_beta                 108.194(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0888(7)
_cell_length_b                   12.8677(6)
_cell_length_c                   20.7793(11)
_cell_measurement_reflns_used    8222
_cell_measurement_temperature    193.0
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.28
_cell_volume                     3324.7(3)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.0520
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            31263
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.063
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0875 before and 0.0570 after correction. The Ratio of minimum to maximum transmission is 0.9262. 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    1.170
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         7584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0422P)^2^+1.9638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1267
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5542
_reflns_number_total             7584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01554e2.cif
_cod_data_source_block           230303lu_ly
_cod_depositor_comments
'Adding full bibliography for 7134469--7134470.cif.'
_cod_database_code               7134470
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  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:
 C15(H15), C34(H34), C20(H20), C22(H22), C24(H24), C32(H32), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C26(H26A,H26B), C25(H25A,H25B), C35(H35A,H35B), C36(H36A,
 H36B), C33(H33A,H33B), C21(H21A,H21B), C23(H23A,H23B), C29(H29A,H29B),
 C37(H37A,H37B), C27(H27A,H27B), C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C6(H6A,H6B,H6C), C16(H16A,H16B,H16C), C3(H3A,H3B,H3C),
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              38806
_shelx_hkl_checksum              4538
_olex2_submission_special_instructions 'No special instructions were received'