TBAI-catalyzed C-H bond activation to construct the C<sub>(sp3)</sub>-O bond in water: synthesis of indole-3-carboxylic-α-esters under metal-free conditions.
Zhang, Xinyuan; Sun, Yufang; Qu, Yujie; Xie, Shengxing; Yang, Fuchun; Wang, Chengyu; Du, Jiawen; Zhu, Xiaofeng; Kong, Lingkai; Wang, Neng-Fei; Organic & biomolecular chemistry 23 (2025) 10674–10678; doi:10.1039/d5ob01449b

data_7160916
_publ_section_title
;
 TBAI-catalyzed C-H bond activation to construct the C<sub>(sp3)</sub>-O
 bond in water: synthesis of indole-3-carboxylic-&#x3b1;-esters under
 metal-free conditions.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10674
_journal_page_last               10678
_journal_paper_doi               10.1039/d5ob01449b
_journal_volume                  23
_journal_year                    2025
_chemical_formula_sum            'C23.5 H18 Cl N O3'
_chemical_formula_weight         397.84
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-08-06 deposited with the CCDC.	2025-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                92.926(9)
_cell_angle_beta                 110.642(9)
_cell_angle_gamma                98.522(9)
_cell_formula_units_Z            2
_cell_length_a                   9.222(3)
_cell_length_b                   10.291(3)
_cell_length_c                   12.395(4)
_cell_measurement_reflns_used    9852
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.16
_cell_measurement_theta_min      2.40
_cell_volume                     1081.9(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0334
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28182
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.330
_diffrn_reflns_theta_min         2.014
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7151
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       Bloc
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0614
_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^)+(0.1133P)^2^+0.3465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1751
_refine_ls_wR_factor_ref         0.1918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3191
_reflns_number_total             3922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01449b2.cif
_cod_data_source_block           zz
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_cell_volume        1081.8(6)
_cod_original_formula_sum        'C23.50 H18 Cl N O3'
_cod_database_code               7160916
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              88689