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_4102662
_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         'C12 H32 N4 Na +,C15 H22 F3 Zn -'
_chemical_formula_sum            'C27 H54 F3 N4 Na Zn'
_chemical_formula_weight         580.10
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           1
_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                88.910(3)
_cell_angle_beta                 89.721(3)
_cell_angle_gamma                60.559(2)
_cell_formula_units_Z            2
_cell_length_a                   10.4379(4)
_cell_length_b                   10.5920(4)
_cell_length_c                   17.3032(7)
_cell_measurement_reflns_used    3797
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.94
_cell_volume                     1665.65(12)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_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_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type
'Oxford Diffraction Gemini A Ultra diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  none
_diffrn_radiation_source         'sealed tube with Enhance optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0687
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            14089
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.120
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.33(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     633
_refine_ls_number_reflns         5341
_refine_ls_number_restraints     1982
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0712
_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^)+(0.1106P)^2^+1.4459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1874
_refine_ls_wR_factor_ref         0.2021
_reflns_number_gt                3608
_reflns_number_total             5341
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja1038598_si_001_2.cif
_cod_data_source_block           rem527a_compound_4
_cod_original_cell_volume        1665.65(11)
_cod_database_code               4102662