Cu(I)-Catalyzed Oxygen and Nitrogen Nucleophiles Triggered Regioselective Synthesis of Furo/Pyrrolo-Annulated Quinolines.
Kumar, Ritush; Chandra, Atish; Mir, Bilal Ahmad; Shukla, Gaurav; The Journal of organic chemistry 84 (2019) 10710–10723; doi:10.1021/acs.joc.9b00662

data_4033809
_publ_section_title
;
 Cu(I)-Catalyzed Oxygen and Nitrogen Nucleophiles Triggered Regioselective
 Synthesis of Furo/Pyrrolo-Annulated Quinolines.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10710
_journal_page_last               10723
_journal_paper_doi               10.1021/acs.joc.9b00662
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C22 H18 N2 O'
_chemical_formula_sum            'C22 H18 N2 O'
_chemical_formula_weight         326.40
_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'
_symmetry_Int_Tables_number      14
_audit_creation_date             2019-01-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.943(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8279(4)
_cell_length_b                   11.0895(5)
_cell_length_c                   16.9907(7)
_cell_measurement_reflns_used    4919
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.10
_cell_measurement_theta_min      2.19
_cell_volume                     1659.40(13)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27662
_diffrn_reflns_theta_full        24.9966
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.081
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.3064
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             688.2843
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.1549
_refine_diff_density_min         -0.2122
_refine_diff_density_rms         0.0545
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             9.2799
_refine_ls_goodness_of_fit_ref   1.0614
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0614
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.3112P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2500
_reflns_number_total             2914
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b00662_si_005.cif
_cod_data_source_block           1
_cod_database_code               4033809
_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:
 C19(H19a,H19b), C16(H16a,H16b), C17(H17a,H17b), C18(H18a,H18b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C15(H15), C12(H12), C1(H1), C13(H13), C5(H5), C14(H14), C4(H4),
 C2(H2), C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'