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_4106137
_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         'C45 H42 F6 Ir N2 P3 '
_chemical_formula_sum            'C45 H42 F6 Ir N2 P3'
_chemical_formula_weight         1009.97
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   10.950(4)
_cell_length_b                   18.517(7)
_cell_length_c                   21.354(7)
_cell_measurement_reflns_used    11790
_cell_measurement_temperature    223.1
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      3.0
_cell_volume                     4330(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 6.85
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.096
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            40514
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_exptl_absorpt_coefficient_mu    3.262
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             2008.00
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.64
_refine_diff_density_min         -0.96
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  4381 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.000(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     515
_refine_ls_number_reflns         9819
_refine_ls_R_factor_gt           0.0690
_refine_ls_shift/su_max          0.0030
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0290P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1040
_reflns_number_gt                7195
_reflns_number_total             9819
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja2014983_si_001_2.cif
_cod_data_source_block           (PPh3)2IrH2(Me2Benzimid)PF6
_cod_original_formula_sum        'C45 H42 F6 Ir N2 P3 '
_cod_database_code               4106137