Synthesis of indol-3-yl-benzofurans and carbazoles <i>via</i> Cu(OTf)<sub>2</sub>-catalyzed [3 + 2] and [4 + 2] cycloaddition.
Chauhan, Amar Nath Singh; Vini, Vikrant; Kumar, Akhilesh; Erande, Rohan D.; Organic & biomolecular chemistry 22 (2024) 6690–6694; doi:10.1039/d4ob00861h

data_7160088
_publ_section_title
;
 Synthesis of indol-3-yl-benzofurans and carbazoles <i>via</i>
 Cu(OTf)<sub>2</sub>-catalyzed [3 + 2] and [4 + 2] cycloaddition.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6690
_journal_page_last               6694
_journal_paper_doi               10.1039/d4ob00861h
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         '0.5(C26 H23 N2 O4), 0.5(C26 H22 N2 O4)'
_chemical_formula_sum            'C26 H22.5 N2 O4'
_chemical_formula_weight         426.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-01
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-03 deposited with the CCDC.	2024-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.499(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.203(3)
_cell_length_b                   12.372(3)
_cell_length_c                   25.592(5)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.23
_cell_volume                     4353.8(16)
_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 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_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  0.0790
_diffrn_reflns_av_unetI/netI     0.0943
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            38332
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.310
_diffrn_reflns_theta_min         2.214
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1568 before and 0.0802 after correction.
The Ratio of minimum to maximum transmission is 0.8019.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1796
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.5980
_refine_diff_density_max         2.159
_refine_diff_density_min         -1.087
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.590
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     555
_refine_ls_number_reflns         10772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.590
_refine_ls_R_factor_all          0.2916
_refine_ls_R_factor_gt           0.1811
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4490
_refine_ls_wR_factor_ref         0.5306
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4648
_reflns_number_total             10772
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00861h2.cif
_cod_data_source_block           3mare_0m
_cod_depositor_comments
'Adding full bibliography for 7160087--7160088.cif.'
_cod_original_cell_volume        4353.7(15)
_cod_original_formula_sum        'C26 H22.50 N2 O4'
_cod_database_code               7160088
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.746
_shelx_estimated_absorpt_t_min   0.598
_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
2. Uiso/Uaniso restraints and constraints
Uanis(O00A) = Uanis(O00N) = Uanis(C3) = Uanis(C2)
Uanis(O00A) = Uanis(O00N)
Uanis(C01I) = Uanis(O00A)
3.a Ternary CH refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00L(H00L), C00U(H00U), C011(H011), C015(H015)
3.b Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00B), C01D(H01A,H01C), C01G(H01L,H01N), C01L(H01Q,H01R)
3.c Aromatic/amide H refined with riding coordinates:
 N005(H005), N006(H006), N007(H007), N009(H009), C00G(H00G), C00S(H00S),
 C00V(H00V), C00W(H00W), C00Z(H00Z), C013(H013), C014(H014), C016(H016),
 C018(H018), C01A(H01H), C01B(H01B), C01C(H01I), C01E(H01J), C01F(H01F),
 C01H(H01P), C01K(H01K), C01M(H01M), C01N(H01S), C01O(H01O), C2(H2)
3.d Idealised Me refined as rotating group:
 C01J(H01D,H01E,H01G), C01P(H01T,H01U,H01V)
3.e :
 C3(H3)
;
_shelx_res_checksum              26974
_olex2_submission_special_instructions 'No special instructions were received'