Structural Basis for Regioisomerization in the Alkali-Metal-Mediated Zincation (AMMZn) of Trifluoromethyl Benzene by Isolation of Kinetic and Thermodynamic Intermediates
David R. Armstrong; Victoria L. Blair; William Clegg; Sophie H. Dale; Joaquin Garcia-Alvarez; Gordon W. Honeyman; Eva Hevia; Robert E. Mulvey; Luca Russo; Journal of the American Chemical Society 132 (2010) 9480–9487; doi:10.1021/ja1038598

data_4102661
_publ_section_title
;
 Structural Basis for Regioisomerization in the Alkali-Metal-Mediated
 Zincation (AMMZn) of Trifluoromethyl Benzene by Isolation of Kinetic and
 Thermodynamic Intermediates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9480
_journal_page_last               9487
_journal_paper_doi               10.1021/ja1038598
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C26 H47 F3 N3 Na Zn'
_chemical_formula_sum            'C26 H47 F3 N3 Na Zn'
_chemical_formula_weight         547.03
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 103.88(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.935(4)
_cell_length_b                   10.6904(9)
_cell_length_c                   30.382(6)
_cell_measurement_reflns_used    960
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_cell_volume                     5970.4(19)
_computing_cell_refinement       EvalCCD
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '\f and \w 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  0.0762
_diffrn_reflns_av_sigmaI/netI    0.0816
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            36191
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         4.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  0.888
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     831
_refine_ls_number_reflns         7682
_refine_ls_number_restraints     1171
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.1487
_refine_ls_R_factor_gt           0.1020
_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^)+(0.0364P)^2^+41.6766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1871
_refine_ls_wR_factor_ref         0.2046
_reflns_number_gt                5340
_reflns_number_total             7682
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja1038598_si_001_1.cif
_cod_data_source_block           rem348_compound_3
_cod_original_cell_volume        5970.4(18)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4102661