Regio- and Enantioselective C-H Cyclization of Pyridines with Alkenes Enabled by a Nickel/N-Heterocyclic Carbene Catalysis.
Zhang, Wu-Bin; Yang, Xin-Tuo; Ma, Jun-Bao; Su, Zhi-Ming; Shi, Shi-Liang; Journal of the American Chemical Society 141 (2019) 5628–5634; doi:10.1021/jacs.9b00931

data_4128427
_publ_section_title
;
 Regio- and Enantioselective C-H Cyclization of Pyridines with Alkenes
 Enabled by a Nickel/N-Heterocyclic Carbene Catalysis.
;
_journal_issue                   14
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5628
_journal_page_last               5634
_journal_paper_doi               10.1021/jacs.9b00931
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H17 N'
_chemical_formula_weight         259.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 112.865(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3155(7)
_cell_length_b                   8.4154(6)
_cell_length_c                   9.8563(7)
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      140.489
_cell_measurement_theta_min      10.295
_cell_volume                     711.96(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11303
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.951
_diffrn_reflns_theta_min         4.869
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.085
_refine_diff_density_rms         0.019
_refine_ls_abs_structure_details
; 
 Flack x determined using 1065 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       0.072(12)
_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   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2449
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0381P)^2^+0.0585P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0779
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                2392
_reflns_number_total             2449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b00931_si_002.cif
_cod_data_source_block           cu_d8v19148_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4128427
_shelx_estimated_absorpt_t_min   0.910
_shelx_estimated_absorpt_t_max   0.944
_shelxl_version_number           2013-4
_shelx_res_checksum              59994
_shelx_hkl_checksum              85051