Dearomative C2-borylation of indoles.
Begum, Ayesha; Akram, Manjur O.; Martin, Caleb D.; Dalton transactions (Cambridge, England : 2003) 54 (2025) 5664–5667; doi:10.1039/d5dt00579e

data_7718306
_publ_section_title
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 Dearomative C2-borylation of indoles.
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_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5664
_journal_page_last               5667
_journal_paper_doi               10.1039/d5dt00579e
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C H2 Cl2, 2(C15 H36 B21 N)'
_chemical_formula_sum            'C31 H74 B42 Cl2 N2'
_chemical_formula_weight         999.84
_chemical_name_systematic        N-methyl-Indole-BHMeoCb2
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-01-28
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-28 deposited with the CCDC.	2025-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.5145(5)
_cell_length_b                   18.9095(6)
_cell_length_c                   38.3552(12)
_cell_measurement_reflns_used    9779
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.33
_cell_volume                     11252.3(6)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0451
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            94785
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         1.779
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1283 before and 0.0584 after correction.
The Ratio of minimum to maximum transmission is 0.8954.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       needle
_exptl_crystal_F_000             4144
_exptl_crystal_recrystallization_method
'Grown from vapor diffusion of DCM into Toluene at room temperature'
_exptl_crystal_size_max          0.647
_exptl_crystal_size_mid          0.362
_exptl_crystal_size_min          0.322
_refine_diff_density_max         0.807
_refine_diff_density_min         -1.108
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.00221(17)
_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   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     829
_refine_ls_number_reflns         10676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0537
_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^)+(0.0575P)^2^+13.0375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1543
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8221
_reflns_number_total             10676
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt00579e2.cif
_cod_data_source_block           nmethylindole_bhmeocb2
_cod_depositor_comments
'Adding full bibliography for 7718305--7718306.cif.'
_cod_database_code               7718306
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.911
_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 Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C22(H22A,H22B), C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C6(H6), C7(H7), C16(H16A), C17(H17A), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C12(H12A,H12B,H12C), C1(H1A,H1B,H1C), C21(H21A,H21B,
 H21C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              64797
_shelx_hkl_checksum              88974
_olex2_submission_special_instructions 'No special instructions were received'