Study of the Hetero-[4+2]-Cycloaddition Reaction of Aldimines and Alkynes. Synthesis of 1,5-Naphthyridine and Isoindolone Derivatives.
Alonso, Concepción; González, María; Palacios, Francisco; Rubiales, Gloria; The Journal of organic chemistry 82 (2017) 6379–6387; doi:10.1021/acs.joc.7b00977

data_4032758
_publ_section_title
;
 Study of the Hetero-[4+2]-Cycloaddition Reaction of Aldimines and
 Alkynes. Synthesis of 1,5-Naphthyridine and Isoindolone Derivatives.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6379
_journal_page_last               6387
_journal_paper_doi               10.1021/acs.joc.7b00977
_journal_volume                  82
_journal_year                    2017
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H15 F3 N2 O1'
_chemical_formula_sum            'C22 H15 F3 N2 O'
_chemical_formula_weight         380.36
_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_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-22T14:53:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                105.216(11)
_cell_angle_beta                 95.918(12)
_cell_angle_gamma                106.899(12)
_cell_formula_units_Z            6
_cell_length_a                   12.5496(18)
_cell_length_b                   13.4577(15)
_cell_length_c                   16.944(2)
_cell_measurement_reflns_used    1994
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      74.143
_cell_measurement_theta_min      3.589
_cell_measurement_wavelength     1.54184
_cell_volume                     2591.7(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -45.00  30.00   1.00    2.00    --  -39.58  37.00  30.00   75
  2  \w    -86.00  42.00   1.00    2.00    --  -39.58  19.00 -30.00  128
  3  \w     37.00 126.00   1.00    2.00    --   39.58-178.00-150.00   89
  4  \w    -89.00 -28.00   1.00    8.00    --  -83.00 111.00 -90.00   61
  5  \w    -71.00 -12.00   1.00    8.00    --  -83.00  45.00-120.00   59
  6  \w   -109.00 -61.00   1.00    8.00    --  -83.00  61.00 150.00   48
  7  \w     64.00 111.00   1.00    8.00    --  113.00-111.00  60.00   47
  8  \w     40.00  65.00   1.00    8.00    --  113.00 -45.00 150.00   25
  9  \w     83.00 158.00   1.00    8.00    --  113.00  30.00 -60.00   75
 10  \w     41.00  77.00   1.00    8.00    --  113.00 -45.00  30.00   36
 11  \w     36.00  69.00   1.00    8.00    --  113.00 -30.00 -60.00   33
 12  \w     50.00 114.00   1.00    8.00    --  113.00-111.00 150.00   64
 13  \w     35.00  68.00   1.00    8.00    --  113.00 -30.00  90.00   33
 14  \w     59.00 125.00   1.00    8.00    --  113.00 -61.00 -90.00   66
 15  \w     76.00 115.00   1.00    8.00    --  113.00-111.00-120.00   39
 16  \w     52.00  64.00   1.00    8.00    --  113.00 -94.00 -90.00   12
;
_diffrn_measurement_device       'four-circle\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.01127
_diffrn_orient_matrix_UB_12      0.07109
_diffrn_orient_matrix_UB_13      -0.0562544
_diffrn_orient_matrix_UB_21      0.0268523
_diffrn_orient_matrix_UB_22      0.0998564
_diffrn_orient_matrix_UB_23      0.0778295
_diffrn_orient_matrix_UB_31      0.1275077
_diffrn_orient_matrix_UB_32      0.0279478
_diffrn_orient_matrix_UB_33      -0.0022167
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_av_unetI/netI     0.0894
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15487
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.997
_diffrn_reflns_theta_min         2.755
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.957
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.734
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.497
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.1
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     789
_refine_ls_number_reflns         15487
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1563
_refine_ls_R_factor_gt           0.0987
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1842P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2681
_refine_ls_wR_factor_ref         0.3081
_reflns_number_gt                7487
_reflns_number_total             15487
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9535\% 
 around [-0.25 0.92 -0.30] (reciprocal) or [-0.00 1.00 0.00] (direct)
;
_cod_data_source_file            jo7b00977_si_001.cif
_cod_data_source_block           a20160129_naf7macla
_cod_database_code               4032758