NMR Spectroscopic Characterization and DFT Calculations of Zirconium(IV)-3,3'-Br2-BINOLate and Related Complexes Used in an Enantioselective Friedel-Crafts Alkylation of Indoles with α,β-Unsaturated Ketones
Gonzalo Blay; Joan Cano; Luz Cardona; Isabel Fernández; M. Carmen Muñoz; José R. Pedro; Carlos Vila; Journal of Organic Chemistry 77 (2012) 10545–10556; doi:10.1021/jo3013594

data_4027742
_publ_section_title
;
 NMR Spectroscopic Characterization and DFT Calculations of
 Zirconium(IV)-3,3'-Br2-BINOLate and Related Complexes Used in an
 Enantioselective Friedel-Crafts Alkylation of Indoles with
 \a,\b-Unsaturated Ketones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10545
_journal_page_last               10556
_journal_paper_doi               10.1021/jo3013594
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H16 Cl N O'
_chemical_formula_weight         297.77
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0000(10)
_cell_angle_beta                 90.0000(10)
_cell_angle_gamma                90.0000(10)
_cell_formula_units_Z            4
_cell_length_a                   5.43900(10)
_cell_length_b                   13.8840(3)
_cell_length_c                   19.5350(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1475.19(6)
_computing_cell_refinement       'HKL DENZO'
_computing_data_collection       COLLECT
_computing_data_reduction        'HKL DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0615
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10468
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_correction_T_min  0.9870
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'empirical absorption correction:XABS2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.871
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0861P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                1746
_reflns_number_total             2696
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3013594_si_002.cif
_cod_data_source_block           ja513
_cod_database_code               4027742