Rh-Catalyzed Construction of Quinolin-2(1H)-ones via C-H Bond Activation of Simple Anilines with CO and Alkynes.
Li, Xinyao; Li, Xinwei; Jiao, Ning; Journal of the American Chemical Society 137 (2015) 9246–9249; doi:10.1021/jacs.5b05843

data_4124181
_publ_section_title
;
 Rh-Catalyzed Construction of Quinolin-2(1H)-ones via C-H Bond Activation
 of Simple Anilines with CO and Alkynes.
;
_journal_issue                   29
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9246
_journal_page_last               9249
_journal_paper_doi               10.1021/jacs.5b05843
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C46 H40 N O3 P2 Rh'
_chemical_formula_sum            'C46 H40 N O3 P2 Rh'
_chemical_formula_weight         819.64
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-13
_audit_creation_method
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Olex2 1.2
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_cell_length_b                   11.1645(7)
_cell_length_c                   19.3961(13)
_cell_measurement_reflns_used    1528
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      22.8280
_cell_measurement_theta_min      3.5390
_cell_volume                     1894.1(2)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.818
_diffrn_measurement_details
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  1 omega  -58.00   39.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -57.0000 -120.0000 97

  2 omega  -12.00   81.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454   57.0000   30.0000 93

  3 omega  -20.00   53.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -99.0000  150.0000 73
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0374722000
_diffrn_orient_matrix_UB_12      0.0541033000
_diffrn_orient_matrix_UB_13      0.0159825000
_diffrn_orient_matrix_UB_21      0.0232558000
_diffrn_orient_matrix_UB_22      -0.0420114000
_diffrn_orient_matrix_UB_23      0.0341494000
_diffrn_orient_matrix_UB_31      0.0645805000
_diffrn_orient_matrix_UB_32      0.0163688000
_diffrn_orient_matrix_UB_33      -0.0041469000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_unetI/netI     0.1725
_diffrn_reflns_laue_measured_fraction_full 0.995
_diffrn_reflns_laue_measured_fraction_max 0.818
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13003
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.125
_diffrn_reflns_theta_min         3.091
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour
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_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description
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_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.492
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         8341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1553
_refine_ls_R_factor_gt           0.0755
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0209P)^2^+0.4827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1413
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4697
_reflns_number_total             8341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b05843_si_002.cif
_cod_data_source_block           exp_5592
_cod_depositor_comments          'Adding full bibliography for 4124181.cif.'
_cod_database_code               4124181
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C46 H40 N1 O3 P2 Rh1'
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.944
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32), C33(H33),
 C34(H34), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C42(H42), C43(H43),
  C44(H44), C45(H45), C46(H46)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'