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_4123075
_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         'C28 H25 B Br Cl N2 O5'
_chemical_formula_sum            'C28 H25 B Br Cl N2 O5'
_chemical_formula_weight         595.67
_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-2013
_cell_angle_alpha                90
_cell_angle_beta                 96.064(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1823(7)
_cell_length_b                   16.881(2)
_cell_length_c                   22.071(2)
_cell_measurement_reflns_used    3142
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      22.91
_cell_measurement_theta_min      2.85
_cell_volume                     2661.0(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)'
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_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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  0.0681
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            22195
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.655
_diffrn_reflns_theta_min         1.522
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_exptl_absorpt_coefficient_mu    1.687
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       needle
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.123
_refine_diff_density_min         -1.159
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         6164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0561
_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^)+(0.0549P)^2^+3.3882P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1364
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3926
_reflns_number_total             6164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja510963k_si_002.cif
_cod_data_source_block           d1483
_cod_original_cell_volume        2661.1(5)
_cod_database_code               4123075
_shelx_estimated_absorpt_t_min   0.698
_shelx_estimated_absorpt_t_max   0.906
_shelxl_version_number           2013-4
_shelx_res_checksum              14836
_shelx_hkl_checksum              65664