Hydrogen Bond-Assisted 6π-Azaelectrocyclization of Penta-2,4-dienamides: Synthesis of Dihydropyridin-2(3H)-ones
Xu Liu; Ning Zhang; Jiming Yang; Yongjiu Liang; Rui Zhang; Dewen Dong; Journal of Organic Chemistry 78 (2013) 3323–3328; doi:10.1021/jo4001959

data_4028126
_publ_section_title
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 Hydrogen Bond-Assisted 6\p-Azaelectrocyclization of Penta-2,4-dienamides:
 Synthesis of Dihydropyridin-2(3H)-ones
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3323
_journal_page_last               3328
_journal_paper_doi               10.1021/jo4001959
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C20 H18 Cl N O3'
_chemical_formula_sum            'C20 H18 Cl N O3'
_chemical_formula_weight         355.80
_chemical_melting_point          392(2)
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.462(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.269(4)
_cell_length_b                   12.814(4)
_cell_length_c                   11.380(3)
_cell_measurement_reflns_used    6670
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.28
_cell_volume                     1769.6(9)
_computing_cell_refinement       'SMART(Bruker, 1998)'
_computing_data_collection       'SMART(Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0797
_diffrn_reflns_av_sigmaI/netI    0.0927
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9823
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.760
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            'light blue'
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.2018
_refine_ls_R_factor_gt           0.0909
_refine_ls_shift/su_max          0.075
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1630P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2448
_refine_ls_wR_factor_ref         0.3123
_reflns_number_gt                1267
_reflns_number_total             3109
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4001959_si_001.cif
_cod_data_source_block           lx005
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1769.7(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028126