An "Anti-Baldwin" 3-Exo-Dig Cyclization: Preparation of Vinylidene Cyclopropanes from Electron-Poor Alkenes
Matthew J. Campbell; Patrick D. Pohlhaus; Geanna Min; Kohsuke Ohmatsu; Jeffrey S. Johnson; Journal of the American Chemical Society 130 (2008) 9180–9181; doi:10.1021/ja803553a

data_4108090
_publ_section_title
;
 An "Anti-Baldwin" 3-Exo-Dig Cyclization: Preparation of Vinylidene
 Cyclopropanes from Electron-Poor Alkenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9180
_journal_page_last               9181
_journal_paper_doi               10.1021/ja803553a
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C17 H16 N4 O6'
_chemical_formula_sum            'C17 H16 N4 O6'
_chemical_formula_weight         372.34
_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           SHELXL-97
_cell_angle_alpha                83.025(1)
_cell_angle_beta                 89.369(1)
_cell_angle_gamma                89.672(1)
_cell_formula_units_Z            2
_cell_length_a                   7.3557(2)
_cell_length_b                   8.7509(2)
_cell_length_c                   13.5113(3)
_cell_measurement_reflns_used    5753
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.01
_cell_measurement_theta_min      3.30
_cell_volume                     863.21(4)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker-AXS SMART APEX-II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9619
_diffrn_reflns_theta_full        66.42
_diffrn_reflns_theta_max         66.42
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    0.939
_exptl_absorpt_correction_T_max  0.9545
_exptl_absorpt_correction_T_min  0.8719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       plate
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0034(6)
_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   1.055
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0444P)^2^+0.2097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0823
_reflns_number_gt                2698
_reflns_number_total             2917
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja803553a-file001.cif
_cod_data_source_block           c07298
_cod_database_code               4108090