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_7054601
_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         'C53 H80 Cl2 P2 Ru'
_chemical_formula_sum            'C53 H80 Cl2 P2 Ru'
_chemical_formula_weight         951.08
_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             2014-05-16
_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                   47.1514(15)
_cell_length_b                   47.1514(15)
_cell_length_c                   13.6692(3)
_cell_measurement_reflns_used    8790
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      72.6930
_cell_measurement_theta_min      3.2030
_cell_volume                     26318.6(13)
_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_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -68.00   -5.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   55.0000  -45.0000 63

  2 omega   89.00  164.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  159.0000  -19.0000 75

  3 omega   34.00  111.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -99.0000  -57.0000 77

  4 omega  -94.00  -55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798 -159.0000  -52.0000 39

  5 omega   97.00  132.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  120.0000   22.0000 35

  6 omega  150.00  176.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  120.0000   22.0000 26

  7 omega  109.00  161.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000  150.0000 52

  8 omega   35.00   84.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  -30.0000 49

  9 omega   66.00   93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000    0.0000 27

 10 omega   37.00   86.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  -90.0000 49

 11 omega -115.00  -14.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  -57.0000  -30.0000 101

 12 omega -116.00  -16.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -55.0000  171.0000 100

 13 omega   58.00  178.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000   90.0000 120

 14 omega   58.00  178.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000  -90.0000 120

 15 omega   82.00  178.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000  -30.0000 96

 16 omega   83.00  108.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000  150.0000 25

 17 omega   35.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   60.0000 56
;
_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      -0.0135815000
_diffrn_orient_matrix_UB_12      0.0219861000
_diffrn_orient_matrix_UB_13      0.0347959000
_diffrn_orient_matrix_UB_21      -0.0248563000
_diffrn_orient_matrix_UB_22      -0.0279229000
_diffrn_orient_matrix_UB_23      0.0657520000
_diffrn_orient_matrix_UB_31      0.0249007000
_diffrn_orient_matrix_UB_32      0.0126469000
_diffrn_orient_matrix_UB_33      0.0846739000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1012
_diffrn_reflns_av_unetI/netI     0.0995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       56
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_k_max       56
_diffrn_reflns_limit_k_min       -56
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            54435
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         3.247
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.731
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_T_min  0.527
_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    1.080
_exptl_crystal_description       needle
_exptl_crystal_F_000             9108
_exptl_crystal_size_max          0.4192
_exptl_crystal_size_mid          0.0443
_exptl_crystal_size_min          0.0318
_refine_diff_density_max         2.128
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       0.0000054(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     682
_refine_ls_number_reflns         10305
_refine_ls_number_restraints     698
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0720
_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^)+300.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1715
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7324
_reflns_number_total             10305
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4nj02034k2.cif
_cod_data_source_block           fv083
_cod_depositor_comments
'Adding full bibliography for 7054596--7054603.cif.'
_cod_original_cell_volume        26319(2)
_cod_database_code               7054601
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'Ru1 P2 Cl2 C40 H60'
_reflns_odcompleteness_completeness 99.90
_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
 At 1.5 times of:
  All C(H,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
 C10B-C11B = C11B-C12B = C12B-C13B = C13B-C14B
 1.39 with sigma of 0.01
 C14B-C15B = C15B-C10B
 1.39 with sigma of 0.01
 C10A-C11A = C11A-C12A = C12A-C13A = C13A-C14A
 1.39 with sigma of 0.01
 C14A-C15A = C15A-C10A
 1.39 with sigma of 0.01
 C11A-C16A = C15A-C17A
 1.5 with sigma of 0.01
 C11B-C16B = C15B-C17B
 1.5 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 0.02
 C1A-C3A
 2.31 with sigma of 0.02
 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
 C10B-C12B = C11B-C13B = C12B-C14B = C13B-C15B = C14B-C10B
 2.4 with sigma of 0.02
 C10A-C12A = C11A-C13A = C12A-C14A = C13A-C15A = C14A-C10A
 2.4 with sigma of 0.02
3. Restrained planarity
 C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A
 with sigma of 0.01
 C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B
 with sigma of 0.01
 C3B, C10B, C11B, C12B, C13B, C14B, C15B, C16B, C17B
 with sigma of 0.01
 C3A, C10A, C11A, C12A, C13A, C14A, C15A, C16A, C17A
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.02
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(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=
 Sof(C16B)=Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C17B)=Sof(H17D)=Sof(H17E)=
 Sof(H17F)=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(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17A)=Sof(H17A)=Sof(H17B)=
 Sof(H17C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C42(H42), C24(H24), C18(H18), C30(H30), C36(H36), C48(H48)
6.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26A,H26B), C29(H29A,H29B), C27(H27A,H27B), C28(H28A,
 H28B), C23(H23A,H23B), C21(H21A,H21B), C22(H22A,H22B), C19(H19A,H19B),
 C20(H20A,H20B), C31(H31A,H31B), C35(H35A,H35B), C32(H32A,H32B), C33(H33A,H33B),
  C34(H34A,H34B), C41(H41A,H41B), C40(H40A,H40B), C37(H37A,H37B), C39(H39A,
 H39B), C38(H38A,H38B), C53(H53A,H53B), C49(H49A,H49B), C51(H51A,H51B),
 C52(H52A,H52B), C50(H50A,H50B), C45(H45A,H45B), C47(H47A,H47B), C46(H46A,H46B),
  C43(H43A,H43B), C44(H44A,H44B)
6.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C12A(H12A), C13A(H13A),
 C14A(H14A), C2B(H2B), C5B(H5B), C6B(H6B), C7B(H7B), C8B(H8B), C12B(H12B),
 C13B(H13B), C14B(H14B)
6.d Idealised Me refined as rotating group:
 C16A(H16A,H16B,H16C), C17A(H17A,H17B,H17C), C16B(H16D,H16E,H16F), C17B(H17D,
 H17E,H17F)
;
_shelx_hkl_checksum              8818
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'