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_7160087
_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         'C19 H17 N O4'
_chemical_formula_sum            'C19 H17 N O4'
_chemical_formula_weight         323.33
_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             2021-06-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2024-05-03 deposited with the CCDC.	2024-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.207(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.790(2)
_cell_length_b                   9.1114(12)
_cell_length_c                   10.3491(13)
_cell_measurement_reflns_used    9055
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      0.746
_cell_measurement_theta_min      0.607
_cell_volume                     1534.8(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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 0.999
_diffrn_measured_fraction_theta_max 0.992
_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  0.0780
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            31542
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.370
_diffrn_reflns_theta_min         3.020
_diffrn_source                   'fine focused sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1379 before and 0.0700 after correction.
The Ratio of minimum to maximum transmission is 0.8133.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.6065
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0062(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0333P)^2^+1.1378P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1111
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2881
_reflns_number_total             3814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00861h2.cif
_cod_data_source_block           9mara
_cod_depositor_comments
'Adding full bibliography for 7160087--7160088.cif.'
_cod_database_code               7160087
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   28.370
_shelx_estimated_absorpt_t_min   0.992
_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:
 C00E(H00E), C00J(H00J)
2.b Secondary CH2 refined with riding coordinates:
 C00N(H00C,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 N005(H005), C00A(H00A), C00B(H00B), C00G(H00G), C00H(H00H), C00I(H00I),
 C00K(H00K), C00L(H00L), C00M(H00M)
2.d Idealised Me refined as rotating group:
 C00O(H00F,H00N,H00O)
2.e Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_shelx_res_checksum              65195
_olex2_submission_special_instructions 'No special instructions were received'