Synthesis of 4-Substituted 3,5-Dinitro-1,4-dihydropyridines by the Self-Condensation of β-Formyl-β-nitroenamine.
Nakaike, Yumi; Nishiwaki, Nagatoshi; Ariga, Masahiro; Tobe, Yoshito; The Journal of organic chemistry 79 (2014) 2163–2169; doi:10.1021/jo5000187

data_4029108
_publ_section_title
;
 Synthesis of 4-Substituted 3,5-Dinitro-1,4-dihydropyridines by the
 Self-Condensation of \b-Formyl-\b-nitroenamine.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2163
_journal_page_last               2169
_journal_paper_doi               10.1021/jo5000187
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C13 H19 N5 O6 '
_chemical_formula_sum            'C13 H19 N5 O6'
_chemical_formula_weight         341.33
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.508(8)
_cell_angle_beta                 74.901(8)
_cell_angle_gamma                69.292(10)
_cell_formula_units_Z            2
_cell_length_a                   8.125(3)
_cell_length_b                   10.053(4)
_cell_length_c                   10.461(4)
_cell_measurement_reflns_used    3214
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     770.5(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12542
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    no
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.1785P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                3189
_reflns_number_total             3533
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5000187_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        770.6(5)
_cod_original_sg_symbol_H-M      'P -1         '
_cod_database_code               4029108