Nucleophilic Additions to Fused Bicyclic Five-Membered Ring Oxocarbenium Ions: Evidence for Preferential Attack on the Inside Face
Deborah M. Smith; Michelle B. Tran; K. A. Woerpel; Journal of the American Chemical Society 125 (2003) 14149–14152; doi:10.1021/ja0375176

data_4114360
_publ_section_title
;
 Nucleophilic Additions to Fused Bicyclic Five-Membered Ring Oxocarbenium
 Ions: Evidence for Preferential Attack on the Inside Face
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14149
_journal_page_last               14152
_journal_paper_doi               10.1021/ja0375176
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C20 H28 N2 O5'
_chemical_formula_weight         376.44
_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           SHELXTL
_cell_angle_alpha                98.3240(10)
_cell_angle_beta                 103.4480(10)
_cell_angle_gamma                101.1760(10)
_cell_formula_units_Z            2
_cell_length_a                   6.1314(3)
_cell_length_b                   12.8797(7)
_cell_length_c                   13.1406(7)
_cell_measurement_temperature    163(2)
_cell_volume                     970.33(9)
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      163(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10529
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.63
_diffrn_standards_decay_%        '< 1.0'
_diffrn_standards_interval_count 'initial 50 frames recollected'
_diffrn_standards_number         '50 frames'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9728
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_description       multi-faceted-polyhedra
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0033(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         4597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0354P)^2^+0.7115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                3102
_reflns_number_total             4597
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0375176si20030729_071505.cif
_cod_data_source_block           kaw24
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4114360