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_1555025
_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         'C26 H18 F3 N O2'
_chemical_formula_sum            'C26 H18 F3 N O2'
_chemical_formula_weight         433.41
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2018-06-19 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                79.201(4)
_cell_angle_beta                 85.566(5)
_cell_angle_gamma                73.057(7)
_cell_formula_units_Z            2
_cell_length_a                   6.4787(5)
_cell_length_b                   10.7989(7)
_cell_length_c                   16.2052(6)
_cell_measurement_reflns_used    1693
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      59.4060
_cell_measurement_theta_min      4.3420
_cell_volume                     1065.03(12)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
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omega____ theta____ kappa____ phi______ frames
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  2 omega  -49.00   37.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
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  3 omega -108.00  -32.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
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  4 omega -108.00  -32.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
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  5 omega  -89.00    2.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
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  6 omega   58.00   95.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
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  7 omega   36.00   91.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.5437 -126.0000   33.0000 110

  8 omega  -36.00   72.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
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  9 omega   10.00   46.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.5437  -57.0000 -150.0000 72

 10 omega  -28.00    2.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
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 11 omega   22.00   55.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.5437  -37.0000 -150.0000 66

 12 omega   -7.00   19.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.5437  -37.0000 -150.0000 52

 13 omega   42.00   93.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
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 14 omega   78.00  109.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
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 15 omega    1.00   54.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
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 16 omega   62.00   90.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
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 17 omega   39.00   66.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
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 18 omega  112.00  157.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 90

 19 omega   37.00   91.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 108

 20 omega   88.00  133.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 90

 21 omega   50.00  128.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -30.0000 156

 22 omega   40.00   84.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 88

 23 omega   54.00   99.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 90

 24 omega   39.00   96.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
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 25 omega   42.00   72.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -30.0000 60

 26 omega   99.00  152.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -30.0000 106

 27 omega   38.00   84.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 92

 28 omega   77.00  115.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 76

 29 omega   38.00   87.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 98

 30 omega   37.00   84.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 94

 31 omega   66.00  128.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 124

 32 omega  108.00  135.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 54

 33 omega   92.00  170.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
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 34 omega   72.00  108.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
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 35 omega   84.00  130.00   0.5000   13.5000
omega____ theta____ kappa____ phi______ frames
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;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1295426000
_diffrn_orient_matrix_UB_12      -0.1435144000
_diffrn_orient_matrix_UB_13      0.0309291000
_diffrn_orient_matrix_UB_21      -0.0586682000
_diffrn_orient_matrix_UB_22      0.0189156000
_diffrn_orient_matrix_UB_23      0.0916531000
_diffrn_orient_matrix_UB_31      -0.2039716000
_diffrn_orient_matrix_UB_32      -0.0443940000
_diffrn_orient_matrix_UB_33      -0.0038676000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7706
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         4.345
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.868
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94928
_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    1.352
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3782
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0857
_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^)+(0.1714P)^2^+0.1087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2528
_refine_ls_wR_factor_ref         0.2922
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2257
_reflns_number_total             3782
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00710e2.cif
_cod_data_source_block           2018062556
_cod_database_code               1555025
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N4F1
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.903
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 C8A-C7A
 1.39 with sigma of 0.02
 C8A-C10A
 1.39 with sigma of 0.02
 C9-C8A
 1.39 with sigma of 0.02
 C7A-C6A
 1.39 with sigma of 0.02
 C8-C7
 1.39 with sigma of 0.02
 C5A-C6A
 1.39 with sigma of 0.02
 C13-C11A
 1.55 with sigma of 0.02
 C12A-O1
 1.45 with sigma of 0.02
3. Rigid bond restraints
 C18, C13
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(F3) = Uanis(F3A)
Uanis(F2) = Uanis(F2A)
Uanis(F1) = Uanis(F1A)
Uanis(C2) = Uanis(C2A)
Uanis(C1) = Uanis(C1A)
Uanis(C3) = Uanis(C3A)
Uanis(C4) = Uanis(C4A)
Uanis(C5) = Uanis(C5A)
Uanis(C6) = Uanis(C6A)
Uanis(N1) = Uanis(N1A)
Uanis(C10) = Uanis(C10A)
Uanis(C11) = Uanis(C11A)
Uanis(C12) = Uanis(C12A)
Uanis(C8) = Uanis(C8A)
Uanis(C7) = Uanis(C7A)
5. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(C5A)=Sof(C4A)=Sof(H4A)=Sof(C3A)=Sof(H3A)=Sof(C2A)=Sof(H2A)=Sof(C1A)=
 Sof(H1A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C10A)=Sof(C11A)=Sof(H11A)=
 Sof(C12A)=Sof(H12A)=Sof(N1A)=1-FVAR(2)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=
 Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(C10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=
 Sof(N1)=FVAR(2)
6.a Riding coordinates:
 C11A(H11A)
6.b Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C12A(H12A)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C4A(H4A), C3A(H3A), C2A(H2A), C1A(H1A),
 C7(H7), C7A(H7A), C14(H14), C15(H15), C17(H17), C18(H18), C21(H21), C22(H22),
 C24(H24), C25(H25)
6.d Fitted hexagon refined as free rotating group:
 C5A(C4A,C3A,C2A,C1A,C6A)
6.e Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'