Reactivity divergence in the cyclization of terminal epoxides all-carbon-tethered to indoles.
Deka, Upasana; Gogoi, Abhijit; Das, Sajal Kumar; Chemical communications (Cambridge, England) 62 (2026) 2222–2225; doi:10.1039/d5cc06074e

data_7135537
_publ_section_title
;
 Reactivity divergence in the cyclization of terminal epoxides
 all-carbon-tethered to indoles.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2222
_journal_page_last               2225
_journal_paper_doi               10.1039/d5cc06074e
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C19 H16 F N'
_chemical_formula_sum            'C19 H16 F N'
_chemical_formula_weight         277.33
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-10-24
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-10-24 deposited with the CCDC.	2025-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.44(11)
_cell_length_b                   7.72(6)
_cell_length_c                   26.4(2)
_cell_measurement_reflns_used    414
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      11.29
_cell_measurement_theta_min      3.86
_cell_volume                     2943(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.6334
_diffrn_reflns_av_unetI/netI     0.2316
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            80177
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.784
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3116
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1679 before and 0.1063 after correction.
The Ratio of minimum to maximum transmission is 0.4179.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       cube
_exptl_crystal_F_000             1168
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate/ hexane'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.2662
_refine_ls_R_factor_gt           0.0901
_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^)+(0.0125P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.2323
_reflns_Friedel_coverage         0.000
_reflns_number_gt                989
_reflns_number_total             3004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06074e2.cif
_cod_data_source_block           ud_d
_cod_original_cell_volume        2943(39)
_cod_database_code               7135537
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.988
_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 Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C15(H15), C8(H8), C2(H2), C16(H16), C7(H7), C6(H6), C19(H19),
 C18(H18)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              71781
_olex2_submission_original_sample_id UD_381
_olex2_submission_special_instructions 'No special instructions were received'