Scope and Limitations of an Efficient Four-Component Reaction for Dihydropyridin-2-ones
Rachel Scheffelaar; Monica Paravidino; Anass Znabet; Rob F. Schmitz; Frans J. J. de Kanter; Martin Lutz; Anthony L. Spek; Célia Fonseca Guerra; F. Matthias Bickelhaupt; Marinus B. Groen; Eelco Ruijter; Romano V. A. Orru; Journal of Organic Chemistry 75 (2010) 1723–1732; doi:10.1021/jo902613j

data_4025274
_publ_contact_author_address
; Bijvoet Center for Biomolecular Research
  Crystal and Structural Chemistry
  Utrecht University
  Padualaan 8
  3584 CH Utrecht
  The Netherlands
;
_publ_contact_author_email       m.lutz@uu.nl
_publ_contact_author_fax         '[+31] 30 2533940'
_publ_contact_author_name        'Martin Lutz'
_publ_contact_author_phone       '[+31] 30 2533902'
_publ_section_title
;
 Scope and Limitations of an Efficient Four-Component Reaction for
 Dihydropyridin-2-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1723
_journal_page_last               1732
_journal_paper_doi               10.1021/jo902613j
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C25 H20 N2 O'
_chemical_formula_sum            'C25 H20 N2 O'
_chemical_formula_weight         364.43
_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
_cell_angle_alpha                76.1128(5)
_cell_angle_beta                 80.0207(5)
_cell_angle_gamma                78.4123(5)
_cell_formula_units_Z            2
_cell_length_a                   9.2509(1)
_cell_length_b                   10.0044(1)
_cell_length_c                   11.2360(2)
_cell_measurement_reflns_used    24901
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.02
_cell_volume                     980.33(2)
_computing_cell_refinement       HKL2000
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'HKL2000, SortAV'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24790
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0439P)^2^+0.1284P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                3248
_reflns_number_total             4493
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo902613j_si_002.cif
_cod_data_source_block           s3782a
_cod_database_code               4025274