Synthesis and characterization of non-chelating ruthenium‒indenylidene olefin metathesis catalysts derived from substituted 1,1-diphenyl-2-propyn-1-ols
Yu, Baoyi; Xie, Yu; Hamad, Fatma B.; Leus, Karen; Lyapkov, Alex A.; Van Hecke, Kristof; Verpoort, Francis; New J. Chem. 39 (2015) 1858–; doi:10.1039/C4NJ02034K

data_7054602
_publ_section_title
;
 Synthesis and characterization of non-chelating ruthenium--indenylidene
 olefin metathesis catalysts derived from substituted
 1,1-diphenyl-2-propyn-1-ols
;
_journal_issue                   3
_journal_name_full               'New J. Chem.'
_journal_page_first              1858
_journal_paper_doi               10.1039/C4NJ02034K
_journal_volume                  39
_journal_year                    2015
_chemical_formula_moiety         'C55 H78 Cl2 P2 Ru'
_chemical_formula_sum            'C55 H78 Cl2 P2 Ru'
_chemical_formula_weight         973.08
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2918 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2014-05-27 deposited with the CCDC.
2014-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   46.0420(17)
_cell_length_b                   46.0420(17)
_cell_length_c                   14.0313(3)
_cell_measurement_reflns_used    5005
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.7810
_cell_measurement_theta_min      3.8290
_cell_volume                     25759.5(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega -105.00  -16.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -30.0000  138.0000 89

  2 omega   40.00   90.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  138.0000 50

  3 omega   45.00   90.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -131.0000  118.0000 45

  4 omega   67.00  108.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -98.0000  107.0000 41

  5 omega -112.00  -85.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000 -180.0000 27

  6 omega -113.00  -80.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000   90.0000 33

  7 omega   87.00  145.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000   30.0000 58

  8 omega   41.00   89.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  -90.0000 48

  9 omega   35.00   86.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  120.0000 51

 10 omega   48.00   75.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -150.0000 27

 11 omega  146.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000   30.0000 32

 12 omega   46.00   90.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  -30.0000 44

 13 omega   28.00   53.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  -90.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0345626000
_diffrn_orient_matrix_UB_12      0.0226285000
_diffrn_orient_matrix_UB_13      0.0457575000
_diffrn_orient_matrix_UB_21      -0.0118718000
_diffrn_orient_matrix_UB_22      -0.0212409000
_diffrn_orient_matrix_UB_23      0.0916055000
_diffrn_orient_matrix_UB_31      0.0125130000
_diffrn_orient_matrix_UB_32      -0.0230148000
_diffrn_orient_matrix_UB_33      -0.0396631000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            35274
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         3.840
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.825
_exptl_absorpt_correction_T_max  0.882
_exptl_absorpt_correction_T_min  0.485
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_description       needle
_exptl_crystal_F_000             9288
_exptl_crystal_size_max          0.3899
_exptl_crystal_size_mid          0.0439
_exptl_crystal_size_min          0.0393
_refine_diff_density_max         4.005
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     599
_refine_ls_number_reflns         10053
_refine_ls_number_restraints     784
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.0968
_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^)+800.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2133
_refine_ls_wR_factor_ref         0.2263
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6542
_reflns_number_total             10053
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4nj02034k2.cif
_cod_data_source_block           fv084
_cod_depositor_comments
'Adding full bibliography for 7054596--7054603.cif.'
_cod_original_cell_volume        25760(2)
_cod_database_code               7054602
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C55 H78 Cl2 P2 Ru'
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C2A-C3A
 1.42 with sigma of 0.01
 C3A-C4A
 1.42 with sigma of 0.01
 C4A-C9A
 1.44 with sigma of 0.01
 C9A-C1A
 1.43 with sigma of 0.01
 C1A-C2A
 1.44 with sigma of 0.01
 C4A-C5A
 1.42 with sigma of 0.01
 C5A-C6A
 1.36 with sigma of 0.01
 C6A-C7A
 1.41 with sigma of 0.01
 C7A-C8A
 1.37 with sigma of 0.01
 C8A-C9A
 1.42 with sigma of 0.01
 C2B-C3B
 1.42 with sigma of 0.01
 C3B-C4B
 1.42 with sigma of 0.01
 C4B-C9B
 1.44 with sigma of 0.01
 C9B-C1B
 1.43 with sigma of 0.01
 C1B-C2B
 1.44 with sigma of 0.01
 C4B-C5B
 1.42 with sigma of 0.01
 C5B-C6B
 1.36 with sigma of 0.01
 C6B-C7B
 1.41 with sigma of 0.01
 C7B-C8B
 1.37 with sigma of 0.01
 C8B-C9B
 1.42 with sigma of 0.01
 C3A-C10A
 1.48 with sigma of 0.01
 C10A-C11A = C11A-C12A = C12A-C13A = C13A-C14A = C14A-C19A = C19A-C10A
 1.39 with sigma of 0.01
 C14A-C15A = C15A-C16A = C16A-C17A = C17A-C18A = C18A-C19A
 1.39 with sigma of 0.01
 C3B-C10B
 1.48 with sigma of 0.01
 C10B-C11B = C11B-C12B = C12B-C13B = C13B-C14B = C14B-C19B = C19B-C10B
 1.39 with sigma of 0.01
 C14B-C15B = C15B-C16B = C16B-C17B = C17B-C18B = C18B-C19B
 1.39 with sigma of 0.01
 C2A-C4A
 2.3 with sigma of 0.02
 C3A-C9A
 2.32 with sigma of 0.02
 C4A-C1A
 2.32 with sigma of 0.02
 C9A-C2A
 2.31 with sigma of 0.01
 C1A-C3A
 2.31 with sigma of 0.01
 C4A-C6A
 2.39 with sigma of 0.02
 C5A-C7A
 2.42 with sigma of 0.02
 C6A-C8A
 2.42 with sigma of 0.02
 C7A-C9A
 2.39 with sigma of 0.02
 C8A-C4A
 2.7 with sigma of 0.02
 C9A-C5A
 2.47 with sigma of 0.02
 C2B-C4B
 2.3 with sigma of 0.02
 C3B-C9B
 2.32 with sigma of 0.02
 C4B-C1B
 2.32 with sigma of 0.02
 C9B-C2B
 2.31 with sigma of 0.02
 C1B-C3B
 2.31 with sigma of 0.02
 C4B-C6B
 2.39 with sigma of 0.02
 C5B-C7B
 2.42 with sigma of 0.02
 C6B-C8B
 2.42 with sigma of 0.02
 C7B-C9B
 2.39 with sigma of 0.02
 C8B-C4B
 2.7 with sigma of 0.02
 C9B-C5B
 2.47 with sigma of 0.02
 C3A-C11A = C3A-C19A
 2.5 with sigma of 0.02
 C10A-C12A = C11A-C13A = C12A-C14A = C13A-C19A = C14A-C10A = C19A-C11A
 2.4 with sigma of 0.02
 C13A-C15A = C14A-C16A = C15A-C17A = C16A-C18A = C17A-C19A = C18A-C14A
 2.4 with sigma of 0.02
 C18A-C10A
 2.4 with sigma of 0.02
 C3B-C11B = C3B-C19B
 2.5 with sigma of 0.02
 C10B-C12B = C11B-C13B = C12B-C14B = C13B-C19B = C14B-C10B = C19B-C11B
 2.4 with sigma of 0.02
 C13B-C15B = C14B-C16B = C15B-C17B = C16B-C18B = C17B-C19B = C18B-C14B
 2.4 with sigma of 0.02
 C18B-C10B
 2.4 with sigma of 0.02
3. Restrained planarity
 C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A
 with sigma of 0.02
 C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B
 with sigma of 0.02
 C3A, C10A, C11A, C12A, C13A, C14A, C15A, C16A, C17A, C18A, C19A
 with sigma of 0.02
 C3B, C10B, C11B, C12B, C13B, C14B, C15B, C16B, C17B, C18B, C19B
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.04
Uanis(C1A) = Uanis(C1B)
Uanis(C2A) = Uanis(C2B)
Uanis(C3A) = Uanis(C3B)
Uanis(C4A) = Uanis(C4B)
Uanis(C5A) = Uanis(C5B)
Uanis(C6A) = Uanis(C6B)
Uanis(C7A) = Uanis(C7B)
Uanis(C8A) = Uanis(C8B)
Uanis(C9A) = Uanis(C9B)
Uanis(C10A) = Uanis(C10B)
Uanis(C11A) = Uanis(C11B)
Uanis(C12A) = Uanis(C12B)
Uanis(C13A) = Uanis(C13B)
Uanis(C14A) = Uanis(C14B)
Uanis(C15A) = Uanis(C15B)
Uanis(C16A) = Uanis(C16B)
Uanis(C17A) = Uanis(C17B)
Uanis(C18A) = Uanis(C18B)
Uanis(C19A) = Uanis(C19B)
5. Others
 Sof(C1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(C4B)=Sof(C5B)=Sof(H5B)=Sof(C6B)=
 Sof(H6B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(C10B)=Sof(C11B)=
 Sof(H11B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(C15B)=
 Sof(H15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=Sof(C18B)=Sof(H18B)=
 Sof(C19B)=1-FVAR(1)
 Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(C4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=
 Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(C10A)=Sof(C11A)=
 Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(C15A)=
 Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=
 Sof(C19A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C20(H20), C32(H32), C26(H26), C50(H50), C38(H38), C44(H44)
6.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C33(H33A,H33B), C55(H55A,H55B), C37(H37A,H37B), C27(H27A,
 H27B), C52(H52A,H52B), C36(H36A,H36B), C34(H34A,H34B), C53(H53A,H53B),
 C54(H54A,H54B), C21(H21A,H21B), C35(H35A,H35B), C51(H51A,H51B), C29(H29A,H29B),
  C24(H24A,H24B), C28(H28A,H28B), C31(H31A,H31B), C23(H23A,H23B), C30(H30A,
 H30B), C22(H22A,H22B), C47(H47A,H47B), C49(H49A,H49B), C48(H48A,H48B),
 C45(H45A,H45B), C43(H43A,H43B), C42(H42A,H42B), C41(H41A,H41B), C46(H46A,H46B),
  C39(H39A,H39B), C40(H40A,H40B)
6.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C11A(H11A), C12A(H12A),
 C13A(H13A), C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A), C2B(H2B), C5B(H5B),
  C6B(H6B), C7B(H7B), C8B(H8B), C11B(H11B), C12B(H12B), C13B(H13B), C15B(H15B),
 C16B(H16B), C17B(H17B), C18B(H18B)
;
_shelx_hkl_checksum              83578
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'