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_4123074
_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         'C21 H18 B Cl N2 O5, C2 H3 N'
_chemical_formula_sum            'C23 H21 B Cl N3 O5'
_chemical_formula_weight         465.69
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                96.420(7)
_cell_angle_beta                 102.856(7)
_cell_angle_gamma                114.267(7)
_cell_formula_units_Z            2
_cell_length_a                   10.159(3)
_cell_length_b                   11.241(3)
_cell_length_c                   11.273(3)
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.29
_cell_volume                     1113.9(5)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18723
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.411
_diffrn_reflns_theta_min         1.903
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       Block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.4282P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0891
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4608
_reflns_number_total             5067
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja510963k_si_004.cif
_cod_data_source_block           d1472_a
_cod_original_cell_volume        1113.9(6)
_cod_database_code               4123074
_shelx_estimated_absorpt_t_min   0.916
_shelx_estimated_absorpt_t_max   0.955
_shelxl_version_number           2013-4
_shelx_res_checksum              72335
_shelx_hkl_checksum              81008