Chiral bicyclic NHC/Ir complexes for catalytic asymmetric transfer hydrogenation of ketones
Kazuhiro Yoshida; Takumi Kamimura; Hiroshi Kuwabara; Akira Yanagisawa; Chem.Commun. 51 (2015) 15442–; doi:10.1039/C5cc05318H

data_7117912
_publ_section_title
;
 Chiral bicyclic NHC/Ir complexes for catalytic asymmetric transfer
 hydrogenation of ketones
;
_journal_name_full               Chem.Commun.
_journal_page_first              15442
_journal_paper_doi               10.1039/C5cc05318H
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C33 H34 Cl Ir N2'
_chemical_formula_weight         686.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2015-04-14 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9592(12)
_cell_length_b                   11.0891(12)
_cell_length_c                   22.818(3)
_cell_measurement_reflns_used    3007
_cell_measurement_temperature    173
_cell_measurement_theta_max      22.8895
_cell_measurement_theta_min      2.5614
_cell_volume                     2773.0(6)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0883
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16350
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.773
_diffrn_reflns_theta_min         1.78
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    4.936
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.335
_refine_diff_density_min         -1.008
_refine_ls_abs_structure_details
;
Flack x determined using 2005 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(8)
_refine_ls_extinction_coef       0.0032(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         6583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0397P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0938
_reflns_number_gt                5376
_reflns_number_total             6583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc05318h2.cif
_cod_data_source_block           I
_cod_original_cell_volume        2773.0(5)
_cod_database_code               7117912
_shelx_res_checksum              64069