New enolate-carbodiimide rearrangement in the concise synthesis of 6-amino-2,3-dihydro-4-pyridinones from homoallylamines.
Kuznetsov, N. Yu; Tikhov, R. M.; Godovikov, I. A.; Khrustalev, V. N.; Bubnov, Yu N.; Organic & biomolecular chemistry 14 (2016) 4283–4298; doi:10.1039/c6ob00293e

data_7155054
_publ_section_title
;
 New enolate-carbodiimide rearrangement in the concise synthesis of
 6-amino-2,3-dihydro-4-pyridinones from homoallylamines.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4283
_journal_page_last               4298
_journal_paper_doi               10.1039/c6ob00293e
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C20 H20 Br Cl N2 O'
_chemical_formula_sum            'C20 H20 Br Cl N2 O'
_chemical_formula_weight         419.74
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-12-02 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                89.548(2)
_cell_angle_beta                 69.846(2)
_cell_angle_gamma                82.380(2)
_cell_formula_units_Z            4
_cell_length_a                   10.5960(8)
_cell_length_b                   13.0323(10)
_cell_length_c                   15.0398(11)
_cell_measurement_reflns_used    4988
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.14
_cell_measurement_theta_min      2.42
_cell_volume                     1930.9(3)
_computing_cell_refinement       'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25436
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    2.277
_exptl_absorpt_correction_T_max  0.600
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.861
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         11212
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.059P)^2^+P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                7918
_reflns_number_total             11212
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c6ob00293e2.cif
_cod_data_source_block           NK-2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155054--7155055.cif.
;
_cod_database_code               7155054