Boron-Containing Enamine and Enamide Linchpins in the Synthesis of Nitrogen Heterocycles.
St Denis, Jeffrey D.; Zajdlik, Adam; Tan, Joanne; Trinchera, Piera; Lee, C. Frank; He, Zhi; Adachi, Shinya; Yudin, Andrei K.; Journal of the American Chemical Society  (2014) 141205135107007–; doi:10.1021/ja510963k

data_4123076
_publ_section_title
;
 Boron-Containing Enamine and Enamide Linchpins in the Synthesis of
 Nitrogen Heterocycles.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              141205135107007
_journal_paper_doi               10.1021/ja510963k
_journal_year                    2014
_chemical_formula_moiety         'C18 H14 F3 N O'
_chemical_formula_sum            'C18 H14 F3 N O'
_chemical_formula_weight         317.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 99.001(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0723(6)
_cell_length_b                   14.5531(6)
_cell_length_c                   7.3488(3)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      67.08
_cell_measurement_theta_min      3.18
_cell_volume                     1486.47(11)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2630
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.376
_diffrn_reflns_theta_min         3.179
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    0.968
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.5650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0352P)^2^+1.4095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1211
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2495
_reflns_number_total             2630
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja510963k_si_003.cif
_cod_data_source_block           d14140twin
_cod_database_code               4123076
_shelx_estimated_absorpt_t_min   0.698
_shelx_estimated_absorpt_t_max   0.927
_shelxl_version_number           2014/6
_shelx_res_checksum              57769
_shelx_hkl_checksum              99711