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_4088368
_publ_section_title
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 N-Trifluoromethyl NHC Ligands Provide Selective Ruthenium Metathesis
 Catalysts
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_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         'C37 H51 Cl2 F3 N2 P Ru, C H2 Cl2'
_chemical_formula_sum            'C38 H53 Cl4 F3 N2 P Ru'
_chemical_formula_weight         868.66
_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   geom
_audit_creation_date             2015-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                105.2320(10)
_cell_angle_beta                 108.4330(10)
_cell_angle_gamma                98.5070(10)
_cell_formula_units_Z            4
_cell_length_a                   14.4269(11)
_cell_length_b                   16.0783(12)
_cell_length_c                   19.3107(14)
_cell_measurement_reflns_used    9174
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.26
_cell_volume                     3967.5(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SAINT'
_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      100
_diffrn_detector                 'Bruker SMART CCD 1K area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'fixed chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            41906
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         1.177
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  0.4113
_exptl_absorpt_correction_T_min  0.3682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0707 before and 0.0361 after correction.
The Ratio of minimum to maximum transmission is 0.8952.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear orangish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       prism
_exptl_crystal_F_000             1796
_exptl_crystal_size_max          0.372
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.154
_refine_diff_density_max         1.677
_refine_diff_density_min         -1.421
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     885
_refine_ls_number_reflns         19564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+4.4560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16852
_reflns_number_total             19564
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00028_si_004.cif
_cod_data_source_block           pe-nhc-201
_cod_database_code               4088368
_shelx_estimated_absorpt_t_max   0.893
_shelx_estimated_absorpt_t_min   0.768
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C26(H26), C63(H63), C20(H20), C69(H69), C32(H32), C57(H57)
2.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C9(H9A,H9B), C68(H68A,H68B), C27(H27A,H27B), C21(H21A,H21B),
 C46(H46A,H46B), C70(H70A,H70B), C64(H64A,H64B), C62(H62A,H62B), C25(H25A,H25B),
  C37(H37A,H37B), C71(H71A,H71B), C58(H58A,H58B), C10(H10A,H10B), C22(H22A,
 H22B), C11(H11A,H11B), C65(H65A,H65B), C47(H47A,H47B), C74(H74A,H74B),
 C33(H33A,H33B), C48(H48A,H48B), C73(H73A,H73B), C34(H34A,H34B), C30(H30A,H30B),
  C35(H35A,H35B), C36(H36A,H36B), C59(H59A,H59B), C24(H24A,H24B), C60(H60A,
 H60B), C72(H72A,H72B), C23(H23A,H23B), C61(H61A,H61B), C28(H28A,H28B),
 C66(H66A,H66B), C67(H67A,H67B), C29(H29A,H29B), C76(H76A,H76B), C75(H75A,H75B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C43(H43), C56(H56), C6(H6), C3(H3), C19(H19), C42(H42), C15(H15),
 C41(H41), C40(H40), C5(H5), C54(H54), C52(H52), C55(H55), C16(H16), C18(H18),
 C53(H53), C17(H17)
2.d Idealised Me refined as rotating group:
 C49(H49A,H49B,H49C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              49225
_shelx_hkl_checksum              95811
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-10-21
_olex2_submission_special_instructions 'No special instructions were received'