#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:35:40 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178906 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/35/4113500.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4113500
loop_
_publ_author_name
'Tina M. Trnka'
'John P. Morgan'
'Melanie S. Sanford'
'Thomas E. Wilhelm'
'Matthias Scholl'
'Tae-Lim Choi'
'Sheng Ding'
'Michael W. Day'
'Robert H. Grubbs'
_publ_contact_author
;       Lawrence M. Henling
        Beckman Institute
        California Institute of Technology
        Pasadena, CA  91125
        USA
;
_publ_contact_author_email       xray@caltech.edu
_publ_contact_author_fax         '(626) 449 4159'
_publ_contact_author_phone       '(626) 395 2735'
_publ_section_title
;
 Synthesis and Activity of Ruthenium Alkylidene Complexes Coordinated with
 Phosphine and N-Heterocyclic Carbene Ligands
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2546
_journal_page_last               2558
_journal_paper_doi               10.1021/ja021146w
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C37 H67 Cl O P2 Ru'
_chemical_formula_weight         726.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.171(1)
_cell_angle_beta                 108.499(1)
_cell_angle_gamma                91.328(1)
_cell_formula_units_Z            1
_cell_length_a                   9.8362(7)
_cell_length_b                   10.2260(7)
_cell_length_c                   10.8212(8)
_cell_measurement_reflns_used    7348
_cell_measurement_temperature    98
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.2
_cell_volume                     926.85(11)
_computing_cell_refinement       'Bruker SMART v5.606'
_computing_data_collection       'Bruker SMART v5.606'
_computing_data_reduction        'Bruker SAINT v6.02'
_computing_molecular_graphics    'Diamond, Bruker SHELXTL v5.1'
_computing_publication_material  'Bruker SHELXTL v5.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      98
_diffrn_measured_fraction_theta_full 0.920
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Bruker SMART 1000 ccd'
_diffrn_measurement_method       'ω scans at 5 fixed φ values'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13967
_diffrn_reflns_theta_full        28.41
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        'within counting statistics'
_diffrn_standards_interval_time  'first 75 scans recollected at end of runs'
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'orange-tinged deep-yellow'
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       'flat wedge'
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.523
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.523
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/σ²(Fo²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0638
_reflns_number_gt                3843
_reflns_number_total             4294
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja021146w_s1_1.cif
_cod_data_source_block           3b
_cod_database_code               4113500
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ru Ru 0.5000 0.5000 0.5000 0.02327(8) Uani 1 2 d S
H H 0.498(4) 0.321(4) 0.412(4) 0.045(12) Uiso 0.50 1 d P
Cl Cl 0.6518(2) 0.5820(2) 0.4008(2) 0.0414(5) Uani 0.50 1 d P
P P 0.29574(5) 0.47138(5) 0.29482(5) 0.02288(11) Uani 1 1 d .
O O 0.3054(7) 0.4007(9) 0.6150(8) 0.0626(19) Uani 0.50 1 d P
C1 C 0.3815(9) 0.4381(9) 0.5692(8) 0.0377(16) Uani 0.50 1 d P
C2 C 0.12502(19) 0.3681(2) 0.2734(2) 0.0269(4) Uani 1 1 d .
H2 H 0.122(2) 0.4025(19) 0.368(2) 0.027(5) Uiso 1 1 d .
C3 C -0.0201(2) 0.3894(2) 0.1847(3) 0.0386(5) Uani 1 1 d .
H3A H -0.028(3) 0.347(2) 0.085(3) 0.054(7) Uiso 1 1 d .
H3B H -0.027(2) 0.499(2) 0.218(2) 0.041(6) Uiso 1 1 d .
C4 C -0.1454(3) 0.3169(3) 0.2023(3) 0.0486(6) Uani 1 1 d .
H4A H -0.140(3) 0.361(3) 0.300(3) 0.057(8) Uiso 1 1 d .
H4B H -0.232(3) 0.337(3) 0.152(3) 0.060(7) Uiso 1 1 d .
C5 C -0.1441(3) 0.1572(3) 0.1590(4) 0.0560(7) Uani 1 1 d .
H5A H -0.160(3) 0.108(3) 0.055(3) 0.080(10) Uiso 1 1 d .
H5B H -0.216(3) 0.116(3) 0.172(3) 0.062(8) Uiso 1 1 d .
C6 C 0.0005(3) 0.1325(3) 0.2411(4) 0.0511(6) Uani 1 1 d .
H6A H 0.001(2) 0.028(3) 0.204(3) 0.055(7) Uiso 1 1 d .
H6B H 0.012(3) 0.169(2) 0.340(3) 0.049(7) Uiso 1 1 d .
C7 C 0.1279(2) 0.2056(2) 0.2265(3) 0.0359(5) Uani 1 1 d .
H7A H 0.118(2) 0.160(2) 0.122(2) 0.039(6) Uiso 1 1 d .
H7B H 0.216(2) 0.189(2) 0.278(2) 0.037(6) Uiso 1 1 d .
C8 C 0.3312(2) 0.3912(2) 0.12284(19) 0.0265(4) Uani 1 1 d .
H8 H 0.404(2) 0.463(2) 0.138(2) 0.032(5) Uiso 1 1 d .
C9 C 0.3975(3) 0.2531(2) 0.0962(2) 0.0368(5) Uani 1 1 d .
H9A H 0.479(2) 0.269(2) 0.179(2) 0.027(5) Uiso 1 1 d .
H9B H 0.332(2) 0.174(2) 0.073(2) 0.035(6) Uiso 1 1 d .
C10 C 0.4475(3) 0.2124(3) -0.0327(3) 0.0443(6) Uani 1 1 d .
H10A H 0.526(3) 0.291(2) -0.005(2) 0.049(7) Uiso 1 1 d .
H10B H 0.481(3) 0.130(3) -0.049(3) 0.052(7) Uiso 1 1 d .
C11 C 0.3264(3) 0.1971(3) -0.1679(2) 0.0427(5) Uani 1 1 d .
H11A H 0.365(2) 0.173(2) -0.249(3) 0.058(7) Uiso 1 1 d .
H11B H 0.256(2) 0.117(2) -0.196(2) 0.041(6) Uiso 1 1 d .
C12 C 0.2591(3) 0.3324(3) -0.1402(2) 0.0405(5) Uani 1 1 d .
H12A H 0.178(2) 0.323(2) -0.222(2) 0.041(6) Uiso 1 1 d .
H12B H 0.329(2) 0.409(2) -0.121(2) 0.030(5) Uiso 1 1 d .
C13 C 0.2054(2) 0.3714(2) -0.0142(2) 0.0337(4) Uani 1 1 d .
H13A H 0.130(2) 0.292(2) -0.039(2) 0.031(5) Uiso 1 1 d .
H13B H 0.164(2) 0.462(2) 0.006(2) 0.039(6) Uiso 1 1 d .
C14 C 0.2416(2) 0.64644(19) 0.3031(2) 0.0261(4) Uani 1 1 d .
H14 H 0.158(2) 0.6234(19) 0.222(2) 0.026(5) Uiso 1 1 d .
C15 C 0.3523(2) 0.7426(2) 0.2902(3) 0.0358(5) Uani 1 1 d .
H15A H 0.442(2) 0.767(2) 0.368(2) 0.045(6) Uiso 1 1 d .
H15B H 0.367(2) 0.695(2) 0.201(3) 0.045(6) Uiso 1 1 d .
C16 C 0.3019(3) 0.8846(2) 0.2974(3) 0.0412(5) Uani 1 1 d .
H16A H 0.369(2) 0.943(2) 0.284(2) 0.050(7) Uiso 1 1 d .
H16B H 0.216(2) 0.861(2) 0.214(2) 0.033(5) Uiso 1 1 d .
C17 C 0.2710(3) 0.9667(2) 0.4348(3) 0.0409(5) Uani 1 1 d .
H17A H 0.360(2) 0.991(2) 0.514(2) 0.043(6) Uiso 1 1 d .
H17B H 0.238(2) 1.056(3) 0.440(2) 0.051(6) Uiso 1 1 d .
C18 C 0.1598(3) 0.8731(2) 0.4476(3) 0.0427(5) Uani 1 1 d .
H18A H 0.067(2) 0.851(2) 0.368(2) 0.040(6) Uiso 1 1 d .
H18B H 0.140(2) 0.925(2) 0.533(3) 0.046(6) Uiso 1 1 d .
C19 C 0.2081(3) 0.7311(2) 0.4413(2) 0.0377(5) Uani 1 1 d .
H19A H 0.136(3) 0.670(2) 0.447(2) 0.050(6) Uiso 1 1 d .
H19B H 0.296(2) 0.747(2) 0.518(3) 0.043(6) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.1300
0.00 1.00 0.00 0.1300
1.00 0.00 -1.00 0.1200
-4.00 1.00 3.00 0.1200
-1.00 1.00 -2.00 0.0700
1.00 0.00 1.00 0.0800
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ru P 90.0(2) . . yes
C1 Ru P 90.0(2) . 2_666 yes
P Ru P 180.0 . 2_666 yes
H Ru H 180.0 . 2_666 yes
C1 Ru Cl 178.1(3) . . yes
P Ru Cl 88.10(5) . . yes
P Ru Cl 91.90(5) 2_666 . yes
C1 Ru H 82.6(14) . . yes
C1 Ru H 97.4(14) 2_666 . yes
P Ru H 87.0(14) . . yes
P Ru H 93.0(14) 2_666 . yes
Cl Ru H 82.6(13) 2_666 . yes
Cl Ru H 97.4(13) . . yes
O Cl C1 164.5(11) 2_666 2_666 ?
C8 P C14 103.04(8) . . ?
C8 P C2 109.66(9) . . ?
C14 P C2 102.43(8) . . ?
C8 P Ru 113.06(6) . . ?
C14 P Ru 113.32(6) . . ?
C2 P Ru 114.27(6) . . ?
O C1 Ru 178.9(11) . . yes
C3 C2 C7 110.05(17) . . ?
C3 C2 P 118.52(14) . . ?
C7 C2 P 113.07(13) . . ?
C3 C2 H2 104.0(12) . . ?
C7 C2 H2 104.1(11) . . ?
P C2 H2 105.5(12) . . ?
C2 C3 C4 110.11(18) . . ?
C2 C3 H3A 107.8(14) . . ?
C4 C3 H3A 110.4(14) . . ?
C2 C3 H3B 111.5(12) . . ?
C4 C3 H3B 107.8(11) . . ?
H3A C3 H3B 109.2(18) . . ?
C5 C4 C3 112.0(2) . . ?
C5 C4 H4A 107.4(15) . . ?
C3 C4 H4A 110.7(15) . . ?
C5 C4 H4B 114.1(15) . . ?
C3 C4 H4B 107.9(15) . . ?
H4A C4 H4B 104(2) . . ?
C4 C5 C6 111.2(2) . . ?
C4 C5 H5A 108.9(17) . . ?
C6 C5 H5A 108.1(17) . . ?
C4 C5 H5B 111.4(16) . . ?
C6 C5 H5B 110.0(17) . . ?
H5A C5 H5B 107(2) . . ?
C5 C6 C7 112.1(2) . . ?
C5 C6 H6A 109.3(14) . . ?
C7 C6 H6A 108.8(14) . . ?
C5 C6 H6B 109.3(15) . . ?
C7 C6 H6B 109.7(14) . . ?
H6A C6 H6B 108(2) . . ?
C6 C7 C2 110.71(18) . . ?
C6 C7 H7A 108.5(12) . . ?
C2 C7 H7A 107.9(12) . . ?
C6 C7 H7B 110.6(13) . . ?
C2 C7 H7B 112.0(13) . . ?
H7A C7 H7B 107.0(17) . . ?
C9 C8 C13 110.48(16) . . ?
C9 C8 P 114.90(13) . . ?
C13 C8 P 116.23(13) . . ?
C9 C8 H8 105.7(12) . . ?
C13 C8 H8 105.9(12) . . ?
P C8 H8 102.2(12) . . ?
C10 C9 C8 110.39(18) . . ?
C10 C9 H9A 108.7(11) . . ?
C8 C9 H9A 109.8(11) . . ?
C10 C9 H9B 105.9(13) . . ?
C8 C9 H9B 112.4(13) . . ?
H9A C9 H9B 109.6(17) . . ?
C11 C10 C9 112.23(19) . . ?
C11 C10 H10A 109.2(14) . . ?
C9 C10 H10A 106.8(13) . . ?
C11 C10 H10B 110.2(16) . . ?
C9 C10 H10B 108.7(16) . . ?
H10A C10 H10B 110(2) . . ?
C12 C11 C10 111.22(18) . . ?
C12 C11 H11A 111.7(13) . . ?
C10 C11 H11A 109.6(14) . . ?
C12 C11 H11B 110.0(13) . . ?
C10 C11 H11B 107.4(13) . . ?
H11A C11 H11B 106.8(18) . . ?
C11 C12 C13 111.72(19) . . ?
C11 C12 H12A 112.7(13) . . ?
C13 C12 H12A 106.8(13) . . ?
C11 C12 H12B 108.4(12) . . ?
C13 C12 H12B 110.2(12) . . ?
H12A C12 H12B 106.9(17) . . ?
C12 C13 C8 110.03(17) . . ?
C12 C13 H13A 108.7(11) . . ?
C8 C13 H13A 108.7(12) . . ?
C12 C13 H13B 112.1(12) . . ?
C8 C13 H13B 108.7(12) . . ?
H13A C13 H13B 108.5(16) . . ?
C15 C14 C19 110.32(16) . . ?
C15 C14 P 113.88(13) . . ?
C19 C14 P 110.93(13) . . ?
C15 C14 H14 105.2(11) . . ?
C19 C14 H14 109.4(11) . . ?
P C14 H14 106.7(11) . . ?
C16 C15 C14 111.52(17) . . ?
C16 C15 H15A 107.2(13) . . ?
C14 C15 H15A 109.7(14) . . ?
C16 C15 H15B 107.5(13) . . ?
C14 C15 H15B 111.2(13) . . ?
H15A C15 H15B 109.7(18) . . ?
C17 C16 C15 111.26(19) . . ?
C17 C16 H16A 112.8(13) . . ?
C15 C16 H16A 111.5(13) . . ?
C17 C16 H16B 110.4(12) . . ?
C15 C16 H16B 107.8(12) . . ?
H16A C16 H16B 102.7(18) . . ?
C16 C17 C18 110.86(18) . . ?
C16 C17 H17A 107.6(13) . . ?
C18 C17 H17A 108.7(13) . . ?
C16 C17 H17B 111.7(13) . . ?
C18 C17 H17B 110.0(13) . . ?
H17A C17 H17B 107.9(17) . . ?
C17 C18 C19 111.54(19) . . ?
C17 C18 H18A 108.9(12) . . ?
C19 C18 H18A 109.1(12) . . ?
C17 C18 H18B 110.9(13) . . ?
C19 C18 H18B 111.1(13) . . ?
H18A C18 H18B 105.2(18) . . ?
C18 C19 C14 111.50(18) . . ?
C18 C19 H19A 111.9(13) . . ?
C14 C19 H19A 109.3(13) . . ?
C18 C19 H19B 112.1(13) . . ?
C14 C19 H19B 105.0(13) . . ?
H19A C19 H19B 106.8(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru C1 1.796(6) . yes
Ru P 2.3795(5) . yes
Ru Cl 2.4045(19) . yes
Ru H 1.68(4) . yes
Cl O 0.552(4) 2_666 ?
Cl C1 0.612(5) 2_666 ?
P C8 1.8526(18) . ?
P C14 1.8547(18) . ?
P C2 1.8597(18) . ?
C1 O 1.154(7) . yes
C2 C3 1.524(3) . ?
C2 C7 1.530(3) . ?
C2 H2 0.942(19) . ?
C3 C4 1.525(3) . ?
C3 H3A 0.96(2) . ?
C3 H3B 1.04(2) . ?
C4 C5 1.504(3) . ?
C4 H4A 0.95(2) . ?
C4 H4B 0.93(3) . ?
C5 C6 1.508(4) . ?
C5 H5A 0.98(3) . ?
C5 H5B 0.90(3) . ?
C6 C7 1.527(3) . ?
C6 H6A 0.97(2) . ?
C6 H6B 0.95(2) . ?
C7 H7A 1.00(2) . ?
C7 H7B 0.93(2) . ?
C8 C9 1.527(3) . ?
C8 C13 1.533(3) . ?
C8 H8 0.93(2) . ?
C9 C10 1.526(3) . ?
C9 H9A 0.95(2) . ?
C9 H9B 0.92(2) . ?
C10 C11 1.511(3) . ?
C10 H10A 0.98(2) . ?
C10 H10B 0.88(2) . ?
C11 C12 1.507(3) . ?
C11 H11A 1.01(2) . ?
C11 H11B 0.94(2) . ?
C12 C13 1.522(3) . ?
C12 H12A 0.95(2) . ?
C12 H12B 0.93(2) . ?
C13 H13A 0.98(2) . ?
C13 H13B 0.99(2) . ?
C14 C15 1.527(3) . ?
C14 C19 1.536(3) . ?
C14 H14 0.935(19) . ?
C15 C16 1.525(3) . ?
C15 H15A 0.94(2) . ?
C15 H15B 0.95(2) . ?
C16 C17 1.511(3) . ?
C16 H16A 0.97(2) . ?
C16 H16B 0.95(2) . ?
C17 C18 1.512(3) . ?
C17 H17A 0.95(2) . ?
C17 H17B 0.97(2) . ?
C18 C19 1.520(3) . ?
C18 H18A 0.98(2) . ?
C18 H18B 0.95(2) . ?
C19 H19A 0.96(2) . ?
C19 H19B 0.94(2) . ?
