Iridium-Catalyzed Hydrogenation of N-Heterocyclic Compounds under Mild Conditions by an Outer-Sphere Pathway
Graham E. Dobereiner; Ainara Nova; Nathan D. Schley; Nilay Hazari; Scott J. Miller; Odile Eisenstein; Robert H. Crabtree; Journal of the American Chemical Society 133 (2011) 7547–7562; doi:10.1021/ja2014983

data_4106139
_publ_contact_author_address
;    Department of Chemistry
     Yale University
     225 Prospect St
     PO Box 208107
     New Haven, CT 06520-8107
     USA
;
_publ_contact_author_email       robert.crabtree@yale.edu
_publ_contact_author_fax         '+203 432 6144'
_publ_contact_author_name        'Dr. Robert H Crabtree'
_publ_contact_author_phone       '+203 432 3925'
_publ_section_title
;
 Iridium-Catalyzed Hydrogenation of N-Heterocyclic Compounds under Mild
 Conditions by an Outer-Sphere Pathway
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7547
_journal_page_last               7562
_journal_paper_doi               10.1021/ja2014983
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'Ir P2 F6 N2 C35 H37'
_chemical_formula_sum            'C35 H37 F6 Ir N2 P2'
_chemical_formula_weight         853.85
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.965(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.8963(11)
_cell_length_b                   23.617(3)
_cell_length_c                   14.7431(16)
_cell_measurement_reflns_used    24791
_cell_measurement_temperature    223
_cell_measurement_theta_max      25.74
_cell_measurement_theta_min      3.13
_cell_volume                     3357.9(7)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD (SCX mini)'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28894
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.144
_exptl_absorpt_correction_T_max  0.537
_exptl_absorpt_correction_T_min  0.361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1688.00
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.570
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     415
_refine_ls_number_reflns         6351
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0252P)^2^+5.3075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                5023
_reflns_number_total             6504
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja2014983_si_001_4.cif
_cod_data_source_block           (cod)Ir(Me2Benzimid)(PPh3)PF6
_cod_original_cell_volume        3358.0(6)
_cod_original_formula_sum        'Ir P2 F6 N2 C35 H37'
_cod_database_code               4106139