Aerobic Synthesis of Substituted Quinoline from Aldehyde and Aniline: Copper-Catalyzed Intermolecular C–H Active and C–C Formative Cyclization
Yan, Rulong; Liu, Xingxing; Pan, Congming; Zhou, Xiaoqiang; Li, Xiaoni; Kang, Xing; Huang, Guosheng; Organic Letters 15 (2013) 4876–; doi:10.1021/ol402312h

data_1512371
_publ_section_title
;
 Aerobic Synthesis of Substituted Quinoline from Aldehyde and Aniline:
 Copper-Catalyzed Intermolecular C--H Active and C--C Formative
 Cyclization
;
_journal_issue                   18
_journal_name_full               'Organic Letters'
_journal_page_first              4876
_journal_paper_doi               10.1021/ol402312h
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C17 H15 N'
_chemical_formula_sum            'C17 H15 N'
_chemical_formula_weight         233.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-07
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.282(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.1022(7)
_cell_length_b                   7.4395(3)
_cell_length_c                   20.7424(10)
_cell_measurement_reflns_used    3572
_cell_measurement_temperature    295.4(4)
_cell_measurement_theta_max      25.3380
_cell_measurement_theta_min      3.4910
_cell_volume                     2611.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      295.4(4)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9167
_diffrn_measurement_details
;
  1 omega  -44.00   -8.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137   38.0000 -120.0000 36

  2 omega  -50.00  -23.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137   77.0000 -120.0000 27

  3 omega   14.00   44.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137   38.0000 -120.0000 30

  4 omega  -19.00   27.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  -99.0000 -180.0000 46

  5 omega    6.00   40.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137   77.0000 -120.0000 34

  6 omega  -44.00   34.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000  -90.0000 78

  7 omega   23.00   49.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000    0.0000 26

  8 omega    1.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000  150.0000 92

  9 omega    0.00   84.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000   30.0000 84

 10 omega  -52.00    2.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -38.0000 -150.0000 54
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0225253000
_diffrn_orient_matrix_UB_12      -0.0201273000
_diffrn_orient_matrix_UB_13      0.0252544000
_diffrn_orient_matrix_UB_21      -0.0352341000
_diffrn_orient_matrix_UB_22      0.0055324000
_diffrn_orient_matrix_UB_23      -0.0226014000
_diffrn_orient_matrix_UB_31      0.0027790000
_diffrn_orient_matrix_UB_32      -0.0929826000
_diffrn_orient_matrix_UB_33      -0.0068270000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20612
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.91
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0019(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0643
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0758P)^2^+0.9569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1830
_refine_ls_wR_factor_ref         0.2133
_reflns_number_gt                3023
_reflns_number_total             5129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402312h_si_001.cif
_cod_data_source_block           yanrl0604_1
_cod_original_cell_volume        2611.57(19)
_cod_database_code               1512371
_reflns_odcompleteness_completeness 99.79
_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 Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15),
 C16(H16), C18(H18), C20(H20), C22(H22), C24(H24), C25(H25), C29(H29), C30(H30),
  C32(H32), C33(H33)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C17(H17A,H17B,H17C), C27(H27A,H27B,H27C), C34(H34A,H34B,
 H34C)
;