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_7159898
_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         'C35 H28 N2'
_chemical_formula_sum            'C35 H28 N2'
_chemical_formula_weight         476.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                90
_cell_angle_beta                 98.298(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7077(8)
_cell_length_b                   9.2729(7)
_cell_length_c                   25.954(2)
_cell_measurement_reflns_used    9251
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.34
_cell_volume                     2550.0(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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0548
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            50346
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.539
_diffrn_reflns_theta_min         1.586
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1429 before and 0.0730 after correction.
The Ratio of minimum to maximum transmission is 0.6736.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0703P)^2^+0.6734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4500
_reflns_number_total             5871
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00421c2.cif
_cod_data_source_block           ysr032_0m_a
_cod_depositor_comments
'Adding full bibliography for 7159896--7159898.cif.'
_cod_database_code               7159898
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.985
_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:
 C3(H3), C25(H25), C24(H24), C14(H14), C20(H20), C11(H11), C18(H18), C23(H23),
 C8(H8), C31(H31), C21(H21), C15(H15), C9(H9), C10(H10), C28(H28), C17(H17),
 C30(H30), C16(H16), C29(H29)
2.b Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              63261
_shelx_hkl_checksum              76974
_olex2_submission_special_instructions 'No special instructions were received'