Metal-free stereoselective C(sp3)–H indolation of N-heterocycles to potent antimicrobial non-canonical tryp–pro hybrids
Saha, Subhajit; Bag, Soumya Ranjan; Akhir, Abdul; Saxena, Deepanshi; Maitra, Rahul; Chopra, Sidharth; Jana, Chandan K.; Green Chemistry 28 (2026) 365–374; doi:10.1039/D5GC04622J

data_7251220
_publ_section_title
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 Metal-free stereoselective C(sp3)--H indolation of N-heterocycles to
 potent antimicrobial non-canonical tryp--pro hybrids
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              365
_journal_page_last               374
_journal_paper_doi               10.1039/D5GC04622J
_journal_volume                  28
_journal_year                    2026
_chemical_absolute_configuration 2S,5R
_chemical_formula_moiety         'C27 H26 N2 O'
_chemical_formula_sum            'C27 H26 N2 O'
_chemical_formula_weight         394.50
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_Hall           'P 4cw'
_space_group_name_H-M_alt        'P 43'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-01-29 deposited with the CCDC.	2025-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5803(14)
_cell_length_b                   13.5803(14)
_cell_length_c                   11.6172(17)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.66
_cell_measurement_theta_min      3.00
_cell_volume                     2142.5(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0349
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            50204
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.000
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1397 before and 0.0501 after correction.
The Ratio of minimum to maximum transmission is 0.9597.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1481 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3730
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0847P)^2^+0.3970P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1467
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3348
_reflns_number_total             3730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc04622j2.cif
_cod_data_source_block           ckj_1_0ma_a
_cod_depositor_comments
'Adding full bibliography for 7251220--7251223.cif.'
_cod_original_cell_volume        2142.5(5)
_cod_database_code               7251220
_shelx_shelxl_version_number     2019/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C15(H15), C2(H2a)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C3(H3a,H3b), C1(H1a,H1b)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C8(H8), C17(H17), C18(H18), C11(H11), C9(H9), C10(H10), C19(H19),
 C20(H20), C26(H26), C23(H23), C25(H25), C24(H24)
2.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              51129
_shelx_hkl_checksum              9763
_olex2_submission_special_instructions 'No special instructions were received'