Highly stereoselective and catalyst-free synthesis of annulated tetrahydropyridines by intramolecular imino-Diels–Alder reaction under microwave irradiation in water
Lezana, Nicolás; Matus-Pérez, Massiel; Galdámez, Antonio; Lühr, Susan; Vilches-Herrera, Marcelo; Green Chem. 18 (2016) 3712–; doi:10.1039/C6GC00912C

data_7225274
_publ_section_title
;
 Highly stereoselective and catalyst-free synthesis of annulated
 tetrahydropyridines by intramolecular imino-Diels--Alder reaction under
 microwave irradiation in water
;
_journal_issue                   13
_journal_name_full               'Green Chem.'
_journal_page_first              3712
_journal_paper_doi               10.1039/C6GC00912C
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C19 H21 N3 O'
_chemical_formula_weight         307.39
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-10-27 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.789(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.725(2)
_cell_length_b                   17.259(3)
_cell_length_c                   16.041(3)
_cell_measurement_temperature    293(2)
_cell_volume                     3245.8(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0717
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17002
_diffrn_reflns_theta_full        20.82
_diffrn_reflns_theta_max         20.82
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.080
_exptl_crystal_colour            yellow-brown
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         1690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0982
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0617P)^2^+23.4816P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2434
_refine_ls_wR_factor_ref         0.2486
_reflns_number_gt                1451
_reflns_number_total             1690
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6gc00912c2.cif
_cod_data_source_block           scd_80_2_0m
_cod_depositor_comments          'Adding full bibliography for 7225274.cif.'
_cod_database_code               7225274