Synthesis of Unsymmetrical Substituted 1,4-Dihydropyridines through Thermal and Microwave Assisted [4+2] Cycloadditions of 1-Azadienes and Allenic Esters
Lakhwinder Singh; M. P. Singh Ishar; Munusamy Elango; Venkatesan Subramanian; Vivek Gupta; Priyanka Kanwal; Journal of Organic Chemistry 73 (2008) 2224–2233; doi:10.1021/jo702548b

data_4023341
_publ_section_title
;
 Synthesis of Unsymmetrical Substituted 1,4-Dihydropyridines
 through Thermal and Microwave Assisted [4+2] Cycloadditions
 of 1-Azadienes and Allenic Esters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2224
_journal_page_last               2233
_journal_paper_doi               10.1021/jo702548b
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C21 H20 N2 O4'
_chemical_formula_sum            'C21 H20 N2 O4'
_chemical_formula_weight         364.39
_chemical_name_systematic
;
 3-Ethoxycarbonyl-2-methyl-4-(2'-nitrophenyl)-1-phenyl-1,4-dihydropyridine
;
_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                 95.853(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.495(2)
_cell_length_b                   9.281(2)
_cell_length_c                   17.236(3)
_cell_measurement_reflns_used    1800
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.83
_cell_measurement_theta_min      2.38
_cell_volume                     1829.2(6)
_computing_cell_refinement       'SAINT 6.45  (Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'PLATON(Spek,1999)$ PARST(1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0843
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12131
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellowish
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0130P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0741
_reflns_number_gt                2930
_reflns_number_total             4526
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702548b-File002.cif
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_cell_measurement_temperature' value '-173(2)' was changed to
'100(2)' - it was converted from degrees Celsius(C) to
Kelvins(K).

'_diffrn_ambient_temperature' value '-173(2)' was
changed to '100(2)' - it was converted from degrees Celsius(C) to
Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023341