Synthesis and reactions of Biginelli-compounds. Part 14.1 A rhodium-induced cyclization–cycloaddition sequence for the construction of conformationally rigid calcium channel modulators of the dihydropyrimidine type
Jauk, Birgit; Belaj, Ferdinand; Kappe, C. Oliver; Journal of the Chemical Society, Perkin Transactions 1  (1999) 307–; doi:10.1039/a808594c

data_7212980
_publ_section_title
;
 Synthesis and reactions of Biginelli-compounds. Part 14.1 A
 rhodium-induced cyclization--cycloaddition sequence for the construction
 of conformationally rigid calcium channel modulators of the
 dihydropyrimidine type
;
_journal_issue                   3
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              307
_journal_paper_doi               10.1039/a808594c
_journal_year                    1999
_chemical_formula_moiety         'C20 H22 N2 O6'
_chemical_formula_sum            'C20 H22 N2 O6'
_chemical_formula_weight         386.40
_chemical_name_systematic
; 
 4-Ethyl 14-Methyl 3-Methyl-15-oxo-17-oxa-2,16-diazapentacyclo[12.2.1.0^1,12^.
0^5,16^.0^6,11^]heptadeca-6,8,10-triene-4,14-dicarboxylate
;
_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           'manual edited SHELXL-97 .cif file'
_cell_angle_alpha                90.00
_cell_angle_beta                 111.847(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.998(3)
_cell_length_b                   9.397(2)
_cell_length_c                   14.153(4)
_cell_measurement_reflns_used    71
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.47
_cell_measurement_theta_min      12.57
_cell_volume                     1851.4(8)
_computing_cell_refinement       'local program'
_computing_data_collection       'local program'
_computing_data_reduction        'local program'
_computing_molecular_graphics    'ORTEP (Johnson,1965)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe 4-circle'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            5051
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.61
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0065(10)
_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   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0434P)^2^+0.6168P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1238
_reflns_number_gt                2777
_reflns_number_total             4024
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            808594csup1.cif
_cod_data_source_block           20
_cod_database_code               7212980