Frustrated β-Chloride Elimination. Selective Arene Alkylation by α-Chloronorbornene Catalyzed by Electrophilic Metallocenium Ion Pairs
Aswini K. Dash; Tryg R. Jensen; Charlotte L. Stern; Tobin J. Marks; Journal of the American Chemical Society 126 (2004) 12528–12540; doi:10.1021/ja047828w

data_4113014
_publ_section_title
;
 Frustrated \b-Chloride Elimination. Selective Arene Alkylation by
 \a-Chloronorbornene Catalyzed by Electrophilic Metallocenium Ion Pairs
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12528
_journal_page_last               12540
_journal_paper_doi               10.1021/ja047828w
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C20 H24 Cl2'
_chemical_formula_weight         335.29
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   11.931(3)
_cell_length_b                   11.152(2)
_cell_length_c                   12.3422(13)
_cell_measurement_temperature    153(2)
_cell_volume                     1642.2(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      153(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14374
_diffrn_reflns_theta_full        29.04
_diffrn_reflns_theta_max         29.04
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.390
_exptl_absorpt_correction_T_max  0.9387
_exptl_absorpt_correction_T_min  0.9036
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         2066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+0.4960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                1761
_reflns_number_total             2066
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja047828wrom20040415_122918.cif
_cod_data_source_block           2a
_cod_database_code               4113014