Direct access to benzofuro[2,3-b]quinoline and 6H-chromeno[3,4-b]quinoline cores through gold-catalyzed annulation of anthranils with arenoxyethynes and aryl propargyl ethers.
Patil, Manoj D.; Liu, Rai-Shung; Organic & biomolecular chemistry 17 (2019) 4452–4455; doi:10.1039/c9ob00468h

data_7156776
_publ_section_title
;
 Direct access to benzofuro[2,3-b]quinoline and
 6H-chromeno[3,4-b]quinoline cores through gold-catalyzed annulation of
 anthranils with arenoxyethynes and aryl propargyl ethers.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4452
_journal_page_last               4455
_journal_paper_doi               10.1039/c9ob00468h
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C15 H9 N O'
_chemical_formula_sum            'C15 H9 N O'
_chemical_formula_weight         219.23
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-02-14 deposited with the CCDC.    2019-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   23.736(4)
_cell_length_b                   5.9771(6)
_cell_length_c                   21.990(3)
_cell_measurement_reflns_used    1127
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      20.133
_cell_measurement_theta_min      2.523
_cell_volume                     3119.8(7)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0949
_diffrn_reflns_av_sigmaI/netI    0.1367
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12552
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(4)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         5380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.2074
_refine_ls_R_factor_gt           0.0820
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0988P)^2^+2.3106P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1809
_refine_ls_wR_factor_ref         0.2602
_reflns_number_gt                2478
_reflns_number_total             5380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob00468h2.cif
_cod_data_source_block           d20681
_cod_depositor_comments          'Adding full bibliography for 7156776.cif.'
_cod_original_cell_volume        3119.7(7)
_cod_database_code               7156776