Asymmetric Synthesis of Axially Chiral 1-Aryl-5,6,7,8-tetrahydroquinolines by Cobalt-Catalyzed [2 + 2 + 2] Cycloaddition Reaction of 1-Aryl-1,7-octadiynes and Nitriles
Marko Hapke; Karolin Kral; Christine Fischer; Anke Spannenberg; Andrey Gutnov; Dmitry Redkin; Barbara Heller; Journal of Organic Chemistry 75 (2010) 3993–4003; doi:10.1021/jo100122d

data_4025485
_publ_section_title
;
 Asymmetric Synthesis of Axially Chiral
 1-Aryl-5,6,7,8-tetrahydroquinolines by Cobalt-Catalyzed [2 + 2 + 2]
 Cycloaddition Reaction of 1-Aryl-1,7-octadiynes and Nitriles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3993
_journal_page_last               4003
_journal_paper_doi               10.1021/jo100122d
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C15 H13 Co N2'
_chemical_formula_weight         280.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.171(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7530(5)
_cell_length_b                   10.7244(4)
_cell_length_c                   12.2426(6)
_cell_measurement_reflns_used    7873
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.43
_cell_measurement_theta_min      1.77
_cell_volume                     1185.84(10)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        X-AREA
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17565
_diffrn_reflns_theta_full        27.93
_diffrn_reflns_theta_max         27.93
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    1.427
_exptl_absorpt_correction_T_max  0.9017
_exptl_absorpt_correction_T_min  0.5699
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'X-SHAPE and X-RED32 (Stoe & Cie, 2005)'
_exptl_crystal_colour            dark-violet
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.052
_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     163
_refine_ls_number_reflns         2834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0654
_reflns_number_gt                2388
_reflns_number_total             2834
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100122d_si_001.cif
_cod_data_source_block           ks1053
_cod_database_code               4025485