Cu(OTf)<sub>2</sub>/HFIP catalyzed regioselective cycloisomerization of indole-C3-functionalized alkynols to carbazoles.
Yaragorla, Srinivasarao; Khan, Tabassum; Chakroborty, Sayonika; Organic & biomolecular chemistry 22 (2024) 3622–3629; doi:10.1039/d4ob00421c

data_7159897
_publ_section_title
;
 Cu(OTf)<sub>2</sub>/HFIP catalyzed regioselective cycloisomerization of
 indole-C3-functionalized alkynols to carbazoles.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3622
_journal_page_last               3629
_journal_paper_doi               10.1039/d4ob00421c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C37 H27 N'
_chemical_formula_sum            'C37 H27 N'
_chemical_formula_weight         485.59
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-14
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-09-14 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                66.465(4)
_cell_angle_beta                 77.764(5)
_cell_angle_gamma                82.339(5)
_cell_formula_units_Z            2
_cell_length_a                   9.6614(12)
_cell_length_b                   12.3016(17)
_cell_length_c                   12.4047(16)
_cell_measurement_reflns_used    7342
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.70
_cell_measurement_theta_min      2.57
_cell_volume                     1319.0(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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.891
_diffrn_measured_fraction_theta_max 0.892
_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  0.0938
_diffrn_reflns_av_unetI/netI     0.2231
_diffrn_reflns_Laue_measured_fraction_full 0.891
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20603
_diffrn_reflns_point_group_measured_fraction_full 0.891
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         1.808
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1798 before and 0.1053 after correction.
The Ratio of minimum to maximum transmission is 0.8163.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.1829
_refine_ls_R_factor_gt           0.1040
_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^)+(0.0752P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2546
_refine_ls_wR_factor_ref         0.2919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2010
_reflns_number_total             4319
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00421c2.cif
_cod_data_source_block           ysr014_0m
_cod_depositor_comments
'Adding full bibliography for 7159896--7159898.cif.'
_cod_database_code               7159897
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C11(H11), C26(H26), C23(H23), C9(H9), C29(H29), C27(H27),
 C8(H8), C36(H36), C10(H10), C30(H30), C14(H14), C35(H35), C20(H20), C15(H15),
 C16(H16), C18(H18), C21(H21), C34(H34), C22(H22), C32(H32), C17(H17), C33(H33)
2.b Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C)
;
_shelx_res_checksum              23650
_shelx_hkl_checksum              54472
_olex2_submission_special_instructions 'No special instructions were received'