Remote Exo/Endo Selectivity in Selective Monohydrolysis of Dialkyl Bicyclo[2.2.1]heptane-2,3-dicarboxylate Derivatives
Satomi Niwayama; Hanjoung Cho; Masoud Zabet-Moghaddam; Bruce R. Whittlesey; Journal of Organic Chemistry 75 (2010) 3775–3780; doi:10.1021/jo100564e

data_4025462
_publ_section_title
;
 Remote Exo/Endo Selectivity in Selective Monohydrolysis of Dialkyl
 Bicyclo[2.2.1]heptane-2,3-dicarboxylate Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3775
_journal_page_last               3780
_journal_paper_doi               10.1021/jo100564e
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C12 H18 O4'
_chemical_formula_weight         226.26
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.8100(10)
_cell_angle_beta                 101.1500(10)
_cell_angle_gamma                109.2290(10)
_cell_formula_units_Z            2
_cell_length_a                   6.9411(8)
_cell_length_b                   9.2660(11)
_cell_length_c                   10.4142(12)
_cell_measurement_temperature    293(2)
_cell_volume                     603.26(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6879
_diffrn_reflns_theta_full        27.09
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.093
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_crystal_size_max          1.056
_exptl_crystal_size_mid          0.712
_exptl_crystal_size_min          0.434
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.000(7)
_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   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          1.385
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0724P)^2^+0.1576P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1544
_reflns_number_gt                2058
_reflns_number_total             2643
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100564e_si_002.cif
_cod_data_source_block           2009010901hc2brw_0m
_cod_database_code               4025462