Silver-catalyzed tandem 5- and 6-endo-cyclizations via concomitant yne-ol-imine activation: selective entry to 2-aryldihydrofuroquinolines
Karmakar, Swastik; Das, Prasanta; Kundu, Sandip; New Journal of Chemistry 45 (2021) 16112–16118; doi:10.1039/D1NJ02643G

data_7060906
_publ_section_title
;
 Silver-catalyzed tandem 5- and 6-endo-cyclizations via concomitant
 yne-ol-imine activation: selective entry to 2-aryldihydrofuroquinolines
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16112
_journal_page_last               16118
_journal_paper_doi               10.1039/D1NJ02643G
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C26 H20 N2 O'
_chemical_formula_sum            'C26 H20 N2 O'
_chemical_formula_weight         376.44
_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
_audit_creation_date             2019-09-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-09 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.6475(8)
_cell_length_b                   12.5986(10)
_cell_length_c                   26.1644(19)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      53.344
_cell_measurement_theta_min      3.796
_cell_volume                     3839.4(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26950
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        53.383
_diffrn_reflns_theta_max         53.383
_diffrn_reflns_theta_min         5.084
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  0.7505
_exptl_absorpt_correction_T_min  0.6629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1015 before and 0.0754 after correction. The Ratio of minimum to maximum transmission is 0.8833. 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    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl Acetate-Hexane'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0527P)^2^+1.5340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1064
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2143
_reflns_number_total             2202
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj02643g2.cif
_cod_data_source_block           d8_n_0m_a
_cod_depositor_comments          'Adding full bibliography for 7060906.cif.'
_cod_database_code               7060906
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.885
_shelx_estimated_absorpt_t_min   0.825
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C8(H8), C17(H17), C10(H10), C14(H14), C7(H7), C9(H9), C15(H15),
 C26(H26), C25(H25), C22(H22), C16(H16), C24(H24), C23(H23)
;
_shelx_res_checksum              83146
_olex2_submission_special_instructions 'No special instructions were received'