Water-Stable Helical Structure of Tertiary Amides of Bicyclic β-Amino Acid Bearing 7-Azabicyclo[2.2.1]heptane. Full Control of Amide Cis-Trans Equilibrium by Bridgehead Substitution
Masahiro Hosoya; Yuko Otani; Masatoshi Kawahata; Kentaro Yamaguchi; Tomohiko Ohwada; Journal of the American Chemical Society 132 (2010) 14780–14789; doi:10.1021/ja1017877

data_4103344
_publ_section_title
;
 Water-Stable Helical Structure of Tertiary Amides of Bicyclic \b-Amino
 Acid Bearing 7-Azabicyclo[2.2.1]heptane. Full Control of Amide Cis-Trans
 Equilibrium by Bridgehead Substitution
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14780
_journal_page_last               14789
_journal_paper_doi               10.1021/ja1017877
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C10 H14 Br N O3'
_chemical_formula_weight         276.13
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.979(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7129(14)
_cell_length_b                   10.4699(16)
_cell_length_c                   12.4154(19)
_cell_measurement_reflns_used    2050
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.19
_cell_measurement_theta_min      2.55
_cell_volume                     1131.0(3)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5486
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.25
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.622
_exptl_absorpt_correction_T_max  0.7364
_exptl_absorpt_correction_T_min  0.3998
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         2.646
_refine_diff_density_min         -1.754
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0955
_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^)+(0.0285P)^2^+12.4519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1921
_refine_ls_wR_factor_ref         0.2007
_reflns_number_gt                1828
_reflns_number_total             2298
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja1017877_si_002_6.cif
_cod_data_source_block           45-a1001121kwh
_cod_database_code               4103344