N-Trifluoromethyl NHC Ligands Provide Selective Ruthenium Metathesis Catalysts
Engl, Pascal S.; Fedorov, Alexey; Copéret, Christophe; Togni, Antonio; Organometallics 35 (2016) 887–; doi:10.1021/acs.organomet.6b00028

data_4088370
_publ_section_title
;
 N-Trifluoromethyl NHC Ligands Provide Selective Ruthenium Metathesis
 Catalysts
;
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              887
_journal_paper_doi               10.1021/acs.organomet.6b00028
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C40 H47 Cl2 F6 N2 P Ru, C H2 Cl2'
_chemical_formula_sum            'C41 H49 Cl4 F6 N2 P Ru'
_chemical_formula_weight         957.66
_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   mixed
_audit_creation_date             2015-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                86.204(2)
_cell_angle_beta                 75.373(2)
_cell_angle_gamma                75.216(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3182(6)
_cell_length_b                   13.8690(7)
_cell_length_c                   15.4984(9)
_cell_measurement_reflns_used    9825
_cell_measurement_temperature    103
_cell_measurement_theta_max      32.36
_cell_measurement_theta_min      2.72
_cell_volume                     2074.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      103.1
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'focusing graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            107909
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         2.271
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  0.6579
_exptl_absorpt_correction_T_min  0.5925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0838 before and 0.0689 after correction.
The Ratio of minimum to maximum transmission is 0.9006.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear greenish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       prism
_exptl_crystal_F_000             980
_exptl_crystal_recrystallization_method CH2Cl2/hexane
_exptl_crystal_size_max          0.506
_exptl_crystal_size_mid          0.446
_exptl_crystal_size_min          0.259
_refine_diff_density_max         1.100
_refine_diff_density_min         -1.300
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     665
_refine_ls_number_reflns         12662
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0233P)^2^+4.4203P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10176
_reflns_number_total             12662
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00028_si_003.cif
_cod_data_source_block           pe-nhc-146
_cod_database_code               4088370
_shelx_estimated_absorpt_t_max   0.833
_shelx_estimated_absorpt_t_min   0.708
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 C17, C18, C19, C20, C21, C22, C17A, C18A, C19A, C20A, C21A, C22A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C12)=Sof(C11)=Sof(H11)=Sof(C10)=
 Sof(H10)=Sof(C15)=Sof(F6)=Sof(F5)=Sof(F4)=1-FVAR(1)
 Sof(F6A)=Sof(F5A)=Sof(C12A)=Sof(F4A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=
 Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(C13A)=Sof(H13A)=FVAR(1)
 Sof(C18A)=Sof(H18A)=Sof(C22A)=Sof(H22A)=Sof(C17A)=Sof(C20A)=Sof(H20A)=
 Sof(C21A)=Sof(H21A)=Sof(C19A)=Sof(H19A)=1-FVAR(2)
 Sof(C17)=Sof(C22)=Sof(H22)=Sof(C21)=Sof(H21)=Sof(C18)=Sof(H18)=Sof(C20)=
 Sof(H20)=Sof(C19)=Sof(H19)=FVAR(2)
 Sof(Cl4A)=Sof(C41A)=Sof(H41C)=Sof(H41D)=Sof(Cl3A)=1-FVAR(3)
 Sof(Cl3)=Sof(Cl4)=Sof(C41)=Sof(H41A)=Sof(H41B)=FVAR(3)
4.a Ternary CH refined with riding coordinates:
 C29(H29), C23(H23), C35(H35)
4.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C24(H24A,H24B), C28(H28A,H28B), C40(H40A,H40B), C26(H26A,
 H26B), C31(H31A,H31B), C34(H34A,H34B), C36(H36A,H36B), C27(H27A,H27B),
 C39(H39A,H39B), C25(H25A,H25B), C38(H38A,H38B), C33(H33A,H33B), C32(H32A,H32B),
  C37(H37A,H37B), C41(H41A,H41B), C41A(H41C,H41D)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C4(H4), C3(H3), C22(H22), C21(H21), C10A(H10A), C18(H18),
 C20(H20), C11A(H11A), C14A(H14A), C13A(H13A), C19(H19), C13(H13), C14(H14),
 C11(H11), C10(H10), C18A(H18A), C22A(H22A), C20A(H20A), C21A(H21A), C19A(H19A)
;
_shelx_res_checksum              2690
_shelx_hkl_checksum              70954
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'