Proline Derived Spirobarbiturates as Highly Effective β-Turn Mimetics Incorporating Polar and Functionalizable Constraint Elements
Luelak Lomlim; Juergen Einsiedel; Frank W. Heinemann; Karsten Meyer; Peter Gmeiner; Journal of Organic Chemistry 73 (2008) 3608–3611; doi:10.1021/jo702573z

data_4023371
_publ_contact_author
;                                                                               
        Prof. Dr. P. GMEINER       
        Department of Chemistry and Pharmacy 
        Emil Fischer Center
        Universit\"at Erlangen-N\"urnberg                   
        Schuhstr. 19 
        D-91052 Erlangen                               
        Bundesrepublik Deutschland                             
;
_publ_contact_author_email       Gmeiner@pharmazie.uni-erlangen.de
_publ_contact_author_fax         '049 9131 852-2585'
_publ_contact_author_phone       '049 9131 852-2584'
_publ_section_title
;
 Proline Derived Spirobarbiturates as Highly Effective \b-Turn
 Mimetics Incorporating Polar and Functionalizable Constraint Elements
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3608
_journal_page_last               3611
_journal_paper_doi               10.1021/jo702573z
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C22 H28 N4 O6'
_chemical_formula_sum            'C22 H28 N4 O6'
_chemical_formula_weight         444.48
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.269(1)
_cell_length_b                   13.329(1)
_cell_length_c                   16.469(1)
_cell_measurement_reflns_used    369
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.00
_cell_measurement_theta_min      6.00
_cell_volume                     2254.2(3)
_computing_cell_refinement       'EVALCCD (Duisenberg, 2003)'
_computing_data_collection       'COLLECT (Bruker-Nonius, 2002)'
_computing_data_reduction        'EVALCCD (Duisenberg, 2003)'
_computing_molecular_graphics    'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_publication_material  'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_structure_refinement  'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_structure_solution    'SHELXTL 6.12 (Bruker AXS, 2002)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method
;
 \f- and \w-rotations with 2.00 \% and 240 sec per frame
;
_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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33511
_diffrn_reflns_theta_full        28.70
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         3.64
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       octahedron
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         3259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0342P)^2^+0.3646P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0645
_refine_ls_wR_factor_ref         0.0680
_reflns_number_gt                2940
_reflns_number_total             3259
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702573z-File001.cif
_cod_data_source_block           ll0601
_cod_original_sg_symbol_Hall     P2ac2ab
_cod_database_code               4023371