Effect of the bulkiness of indenylidene moieties on the catalytic initiation and efficiency of second-generation ruthenium-based olefin metathesis catalysts
Yu, Baoyi; Luo, Zhixiong; Hamad, Fatma B.; Leus, Karen; van Hecke, Kristof; Verpoort, Francis; Catal. Sci. Technol. 6 (2016) 2092–; doi:10.1039/C5CY01506E

data_1540418
_publ_section_title
;
 Effect of the bulkiness of indenylidene moieties on the catalytic
 initiation and efficiency of second-generation ruthenium-based olefin
 metathesis catalysts
;
_journal_issue                   7
_journal_name_full               'Catal. Sci. Technol.'
_journal_page_first              2092
_journal_paper_doi               10.1039/C5CY01506E
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C54 H68 Cl2 F N2 P Ru, C7 H8'
_chemical_formula_sum            'C61 H76 Cl2 F N2 P Ru'
_chemical_formula_weight         1059.18
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-01-04
_audit_creation_method
;
  Olex2 1.2
  (compiled 2013.04.25 svn.r2679, GUI svn.r4466)
;
_audit_update_record
;
2015-07-23 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.428(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.3485(7)
_cell_length_b                   16.9164(7)
_cell_length_c                   17.4629(8)
_cell_measurement_reflns_used    3941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.7150
_cell_measurement_theta_min      3.6500
_cell_volume                     5330.8(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector_area_resol_mean 10.4839
_diffrn_measured_fraction_theta_full 0.9953
_diffrn_measured_fraction_theta_max 0.9953
_diffrn_measurement_details
;
  1 omega  -91.00  -64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000 -142.0000   -7.0000 27

  2 omega  -96.00  -17.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  128.0000 -163.0000 79

  3 omega -112.00  -63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000 -142.0000  -49.0000 49

  4 omega   46.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -142.0000  130.0000 73

  5 omega   47.00   96.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -142.0000  173.0000 49

  6 omega  114.00  141.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  142.0000    7.0000 27

  7 omega   93.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  128.0000   58.0000 31

  8 omega -114.00  -84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  -57.0000   60.0000 30

  9 omega  -68.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6798  -57.0000   60.0000 54

 10 omega -126.00 -101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000   30.0000 25

 11 omega -109.00  -80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000 -120.0000 29

 12 omega -119.00  -80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000  120.0000 39

 13 omega   48.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  -30.0000 29

 14 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  -60.0000 27

 15 omega   81.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000  -90.0000 28

 16 omega   81.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   30.0000 -120.0000 96

 17 omega   26.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000  -30.0000 83

 18 omega   38.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000  -60.0000 61

 19 omega   34.00   60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000   60.0000 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0041189000
_diffrn_orient_matrix_UB_12      -0.0849832000
_diffrn_orient_matrix_UB_13      -0.0323473000
_diffrn_orient_matrix_UB_21      -0.0017873000
_diffrn_orient_matrix_UB_22      -0.0324984000
_diffrn_orient_matrix_UB_23      0.0820350000
_diffrn_orient_matrix_UB_31      -0.0852122000
_diffrn_orient_matrix_UB_32      0.0048988000
_diffrn_orient_matrix_UB_33      -0.0166353000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26706
_diffrn_reflns_theta_full        70.07
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_min         3.58
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.920
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2232
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.056
_refine_diff_density_max         1.014
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     643
_refine_ls_number_reflns         10093
_refine_ls_number_restraints     120
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0753P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1688
_reflns_number_gt                6286
_reflns_number_total             10093
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cy01506e2.cif
_cod_data_source_block           fv039
_cod_depositor_comments
'Adding full bibliography for 1540417--1540419.cif.'
_cod_database_code               1540418
_chemical_oxdiff_formula         'C10 H10 N2 F1 Cl2 Ru1'
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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
 C55A-C56A = C56A-C57A = C57A-C58A = C58A-C59A = C59A-C60A = C60A-C55A
 1.39 with sigma of 0.01
 C55B-C56B = C56B-C57B = C57B-C58B = C58B-C59B = C59B-C60B = C60B-C55B
 1.39 with sigma of 0.01
 C61A-C55A
 1.5 with sigma of 0.01
 C61B-C55B
 1.5 with sigma of 0.01
 C55A-C57A = C56A-C58A = C57A-C59A = C58A-C60A = C59A-C55A
 2.4 with sigma of 0.02
 C55B-C57B = C56B-C58B = C57B-C59B = C58B-C60B = C59B-C55B
 2.4 with sigma of 0.02
 C61A-C56A = C61A-C60A
 2.5 with sigma of 0.02
 C61B-C56B = C61B-C60B
 2.5 with sigma of 0.02
3. Restrained planarity
 C55A, C56A, C57A, C58A, C59A, C60A, C61A
 with sigma of 0.03
 C55B, C56B, C57B, C58B, C59B, C60B, C61B
 with sigma of 0.03
4. Uiso/Uaniso restraints and constraints
C55A \\sim C56A \\sim C57A \\sim C58A \\sim C59A \\sim C60A \\sim C61A: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
C55B \\sim C56B \\sim C57B \\sim C58B \\sim C59B \\sim C60B \\sim C61B: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C55A) = Uanis(C55B)
Uanis(C56A) = Uanis(C56B)
Uanis(C57A) = Uanis(C57B)
Uanis(C58A) = Uanis(C58B)
Uanis(C59A) = Uanis(C59B)
Uanis(C60A) = Uanis(C60B)
Uanis(C61A) = Uanis(C61B)
5. Others
 Sof(C55B)=Sof(C56B)=Sof(H56B)=Sof(C57B)=Sof(H57B)=Sof(C58B)=Sof(H58B)=
 Sof(C59B)=Sof(H59B)=Sof(C60B)=Sof(H60B)=Sof(C61B)=Sof(H61D)=Sof(H61E)=
 Sof(H61F)=1-FVAR(1)
 Sof(C55A)=Sof(C56A)=Sof(H56A)=Sof(C57A)=Sof(H57A)=Sof(C58A)=Sof(H58A)=
 Sof(C59A)=Sof(H59A)=Sof(C60A)=Sof(H60A)=Sof(C61A)=Sof(H61A)=Sof(H61B)=
 Sof(H61C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C37(H37), C43(H43), C49(H49)
6.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,
 H40B), C41(H41A,H41B), C42(H42A,H42B), C44(H44A,H44B), C45(H45A,H45B),
 C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C50(H50A,H50B), C51(H51A,H51B),
  C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14),
 C15(H15), C21(H21), C23(H23), C30(H30), C32(H32), C56A(H56A), C57A(H57A),
 C58A(H58A), C59A(H59A), C60A(H60A), C56B(H56B), C57B(H57B), C58B(H58B),
 C59B(H59B), C60B(H60B)
6.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C34(H34A,H34B,
 H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C61A(H61A,H61B,H61C),
 C61B(H61D,H61E,H61F)
;