Comparison of Reactivity and Enantioselectivity between Chiral Bimetallic Catalysts: Bismuth‒Rhodium- and Dirhodium-Catalyzed Carbene Chemistry
Ren, Zhi; Sunderland, Travis L.; Tortoreto, Cecilia; Yang, Tzuhsiung; Berry, John F.; Musaev, Djamaladdin G.; Davies, Huw M. L.; ACS Catalysis 8 (2018) 10676–; doi:10.1021/acscatal.8b03054

data_4515768
_publ_section_title
;
 Comparison of Reactivity and Enantioselectivity between Chiral Bimetallic
 Catalysts: Bismuth--Rhodium- and Dirhodium-Catalyzed Carbene Chemistry
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              10676
_journal_paper_doi               10.1021/acscatal.8b03054
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C38 H51 Bi O8 P Rh'
_chemical_formula_sum            'C38 H51 Bi O8 P Rh'
_chemical_formula_weight         978.64
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                91.294(2)
_cell_angle_beta                 92.227(3)
_cell_angle_gamma                91.361(2)
_cell_formula_units_Z            2
_cell_length_a                   10.4797(4)
_cell_length_b                   13.5923(5)
_cell_length_c                   13.9879(6)
_cell_measurement_reflns_used    4726
_cell_measurement_temperature    100(2)
_cell_volume                     1989.86(14)
_computing_data_collection       'APEX2 Ver. 2014.11-0 (Bruker-AXS, 2014)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            41907
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.351
_diffrn_reflns_theta_min         1.457
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    4.918
_exptl_absorpt_correction_T_max  0.8815
_exptl_absorpt_correction_T_min  0.7426
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             972
_refine_diff_density_max         1.793
_refine_diff_density_min         -1.596
_refine_diff_density_rms         0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     458
_refine_ls_number_reflns         9875
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0368P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7749
_reflns_number_total             9875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b03054_si_003.cif
_cod_data_source_block           berry682
_cod_database_code               4515768
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2A-C1 \\sim C2-C1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C2) = Uanis(C2A)
Uanis(C3) = Uanis(C5) = Uanis(C4) = Uanis(C3A) = Uanis(C4A) = Uanis(C5A)
4. Others
 Sof(C2A)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=
 Sof(H4AC)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(H5AC)=1-FVAR(1)
 Sof(C2)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H4C)=
 Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(H5C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29),
 C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38)
5.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C3A(H3AA,H3AB,H3AC), C4(H4A,H4B,H4C), C4A(H4AA,H4AB,H4AC),
 C5(H5A,H5B,H5C), C5A(H5AA,H5AB,H5AC), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C),
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              97626
_shelx_hkl_checksum              97782
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'