One-pot synthesis of pyranoquinolin-1-ones via Rh(iii)-catalysed redox annulation of 3-carboxyquinolines and alkynes
Yang, Zhijia; Pi, Chao; Cui, Xiuling; Wu, Yangjie; Organic Chemistry Frontiers 6 (2019) 2897–; doi:10.1039/C9QO00710E

data_1555023
_publ_section_title
;
 One-pot synthesis of pyranoquinolin-1-ones via Rh(iii)-catalysed redox
 annulation of 3-carboxyquinolines and alkynes
;
_journal_issue                   16
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2897
_journal_paper_doi               10.1039/C9QO00710E
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C24 H17 N O2'
_chemical_formula_sum            'C24 H17 N O2'
_chemical_formula_weight         351.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-06-19 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                75.764(3)
_cell_angle_beta                 84.604(3)
_cell_angle_gamma                89.194(3)
_cell_formula_units_Z            4
_cell_length_a                   11.0804(3)
_cell_length_b                   12.2799(5)
_cell_length_c                   13.6018(4)
_cell_measurement_reflns_used    4823
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2630
_cell_measurement_theta_min      3.7570
_cell_volume                     1785.88(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -25.00   24.00   0.5000   10.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  -99.0000  -90.0000 98

  2 omega  -49.00    3.00   0.5000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -57.0000    0.0000 104

  3 omega  -47.00   45.00   0.5000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -77.0000  150.0000 184

  4 omega  -24.00   57.00   0.5000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -99.0000   60.0000 162

  5 omega  -22.00    4.00   0.5000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -99.0000  150.0000 52

  6 omega    4.00   81.00   0.5000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661   57.0000  -90.0000 154

  7 omega   52.00   86.00   0.5000   10.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0661   77.0000  -90.0000 68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0168554000
_diffrn_orient_matrix_UB_12      -0.0471350000
_diffrn_orient_matrix_UB_13      -0.0172568000
_diffrn_orient_matrix_UB_21      -0.0564190000
_diffrn_orient_matrix_UB_22      0.0254176000
_diffrn_orient_matrix_UB_23      -0.0118962000
_diffrn_orient_matrix_UB_31      0.0258355000
_diffrn_orient_matrix_UB_32      0.0261471000
_diffrn_orient_matrix_UB_33      -0.0498054000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14984
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.394
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         7283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0431P)^2^+0.0782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5251
_reflns_number_total             7283
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00710e2.cif
_cod_data_source_block           20180140
_cod_database_code               1555023
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H30N3O5
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.985
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C10'(H10'), C11'(H11')
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C1'(H1'),
  C2'(H2'), C3'(H3'), C4'(H4'), C7'(H7'), C14'(H14'), C15'(H15'), C16'(H16'),
 C17'(H17'), C18'(H18'), C20'(H20'), C21'(H21'), C22'(H22'), C23'(H23'),
 C24'(H24')
;
_olex2_submission_special_instructions 'No special instructions were received'