Organometallic Enantiomeric Scaffolding: General Access to 2-Substituted Oxa- and Azabicyclo[3.2.1]octenes via a Brønsted Acid Catalyzed [5 + 2] Cycloaddition Reaction
Ethel C. Garnier; Lanny S. Liebeskind; Journal of the American Chemical Society 130 (2008) 7449–7458; doi:10.1021/ja800664v

data_4107875
_publ_section_title
;
 Organometallic Enantiomeric Scaffolding: General Access to 2-Substituted
 Oxa- and Azabicyclo[3.2.1]octenes via a Br\/onsted Acid Catalyzed [5 + 2]
 Cycloaddition Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7449
_journal_page_last               7458
_journal_paper_doi               10.1021/ja800664v
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C21 H18 B F3 Mo N6 O4'
_chemical_formula_sum            'C21 H18 B F3 Mo N6 O4'
_chemical_formula_weight         582.16
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.697(2)
_cell_length_b                   11.7074(16)
_cell_length_c                   14.558(2)
_cell_measurement_reflns_used    5142
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.284
_cell_measurement_theta_min      2.233
_cell_volume                     2334.5(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1475
_diffrn_reflns_av_sigmaI/netI    0.1207
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30577
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  0.9633
_exptl_absorpt_correction_T_min  0.8743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_description       cubic
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.789
_refine_diff_density_min         -1.580
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5809
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0753
_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^)+(0.0682P)^2^+0.7109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1564
_reflns_number_gt                4387
_reflns_number_total             5809
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja800664v-file002.cif
_cod_data_source_block           305bt
_cod_original_cell_volume        2334.4(6)
_cod_database_code               4107875