Origins of Enantioselectivity during Allylic Substitution Reactions Catalyzed by Metallacyclic Iridium Complexes
Sherzod T. Madrahimov; John F. Hartwig; Journal of the American Chemical Society 134 (2012) 8136–8147; doi:10.1021/ja212217j

data_4117924
_publ_section_title
;
 Origins of Enantioselectivity during Allylic Substitution Reactions
 Catalyzed by Metallacyclic Iridium Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8136
_journal_page_last               8147
_journal_paper_doi               10.1021/ja212217j
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C53 H50 Ir N O2 P, C6 H6, B F4'
_chemical_formula_sum            'C59 H56 B F4 Ir N O2 P'
_chemical_formula_weight         1121.03
_chemical_name_systematic
; 
? 
;
_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
_audit_update_record
; 
? 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6967(7)
_cell_length_b                   17.9618(10)
_cell_length_c                   23.3919(14)
_cell_measurement_reflns_used    6690
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      20.90
_cell_measurement_theta_min      2.25
_cell_volume                     4914.5(5)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.0-1 (Bruker, 2004)'
_computing_data_reduction
; 
SAINT V7.23A, XPREP V2005/2, SADABS V2007/4, TWINABS V2007/5 
(Bruker, 2005 & 2007) 
;
_computing_molecular_graphics
; 
SHELXTL V6.12 (Bruker, 2005), CrystalMaker v2.1.3 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from \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_radiation_wavelength_id  ba34has
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            58387
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    2.810
_exptl_absorpt_correction_T_max  0.9150
_exptl_absorpt_correction_T_min  0.6713
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       column
_exptl_crystal_F_000             2264
_exptl_crystal_id                ba34has
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (-1 -2 -2) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 'Flack (1983),  4012 Friedels'
_refine_ls_abs_structure_Flack   0.014(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     724
_refine_ls_number_reflns         9033
_refine_ls_number_restraints     582
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0278P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0664
_reflns_number_gt                7911
_reflns_number_total             9033
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja212217j_si_001.cif
_cod_data_source_block           ba34has
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4117924