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_4033810
_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         'C20 H16 N2 O'
_chemical_formula_sum            'C20 H16 N2 O'
_chemical_formula_weight         300.36
_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'
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Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
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CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
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CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
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_diffrn_measurement_details
;
  1 omega  -59.00  -19.00   1.0000    2.8100
omega____ theta____ kappa____ phi______ frames
    -      -18.5423  114.0000 -139.0000 40

  2 omega  -54.00   62.00   1.0000    2.8100
omega____ theta____ kappa____ phi______ frames
    -       19.9486    0.0000   60.0000 116
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_diffrn_orient_matrix_UB_22      -0.0180792000
_diffrn_orient_matrix_UB_23      0.0434580000
_diffrn_orient_matrix_UB_31      0.0171227000
_diffrn_orient_matrix_UB_32      0.0687258000
_diffrn_orient_matrix_UB_33      0.0041863000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -9
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_diffrn_reflns_theta_max         29.16
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
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_exptl_absorpt_correction_T_min  0.75825
_exptl_absorpt_correction_type   multi-scan
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CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2825
_exptl_crystal_F_000             632.2633
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_refine_ls_goodness_of_fit_ref   1.1542
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_constraints    28
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2862
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_refine_ls_restrained_S_all      1.1542
_refine_ls_R_factor_all          0.1147
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_refine_ls_shift/su_mean         0.1924
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0947P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1703
_refine_ls_wR_factor_ref         0.2288
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                1692
_reflns_number_total             2862
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b00662_si_003.cif
_cod_data_source_block           rk-3-tolcy1
_cod_depositor_comments
;

2020-09-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1555.5(8)
_cod_original_formula_moiety     '0.5(C20 H16 N2 O)'
_cod_original_formula_sum        'C10 H8 N O0.5'
_cod_original_formula_units_Z    8
_cod_original_formula_weight     150.18
_cod_database_code               4033810
_chemical_oxdiff_formula         'C20 H16 N2 O1'
_reflns_odcompleteness_completeness 79.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C19(H19a,H19b,H19c), C20(H20a,H20b,H20c)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C7(H7), C1(H1), C14(H14), C3(H3), C4(H4), C18(H18), C16(H16),
 C17(H17), C2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'