Chiral N-Heterocyclic Carbene Ligands Derived from 2,2‘-Bipiperidine and Partially Reduced Biisoquinoline: Rhodium and Iridium Complexes in Asymmetric Catalysis†
Herrmann, Wolfgang A.; Baskakov, Denys; Herdtweck, Eberhardt; Hoffmann, Stephan D.; Bunlaksananusorn, Tanasri; Rampf, Florian; Rodefeld, Lars; Organometallics 25 (2006) 2449–; doi:10.1021/om060098b

data_4075184
_publ_section_title
;
 Chiral N-Heterocyclic Carbene Ligands Derived from
 2,2&#x2018;-Bipiperidine and Partially Reduced Biisoquinoline:&#x00A0;
 Rhodium and Iridium Complexes in Asymmetric Catalysis&#x2020;
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              2449
_journal_paper_doi               10.1021/om060098b
_journal_volume                  25
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H37 N2 O P S'
_chemical_formula_sum            'C20 H37 N2 O P S'
_chemical_formula_weight         384.56
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 110.1033(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3294(1)
_cell_length_b                   10.0515(2)
_cell_length_c                   12.3944(2)
_cell_measurement_reflns_used    2125
_cell_measurement_temperature    123(1)
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      1.75
_cell_volume                     1091.47(3)
_computing_cell_refinement       'DENZO (Nonius, 2001b)'
_computing_data_collection       'Kappa-CCD Control Software (Nonius, 2001a)'
_computing_data_reduction        'DENZO (Nonius, 2001b)'
_computing_molecular_graphics    'PLATON (Spek, 2001)'
_computing_publication_material  'PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1998)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_diffrn_ambient_temperature      123(1)
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       ' \k-geometry diffractometer '
_diffrn_measurement_device_type  ' Nonius \k-CCD diffractometer'
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'NONIUS FR 591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25947
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(applied during the scaling procedure; Nonius, 2001b)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3992
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(Fo^2^)+(0.0525P)^2^+0.5193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                3835
_reflns_number_total             3992
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            om060098bsi20060201_054503.cif
_cod_data_source_block           BASF-4463-123
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4075184