#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:48:43 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178964 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/93/4119315.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_4119315
loop_
_publ_author_name
'David G. Johnson'
'Jason M. Lynam'
'Neetisha S. Mistry'
'John M. Slattery'
'Robert J. Thatcher'
'Adrian C. Whitwood'
_publ_contact_author_address
;Department of Chemistry
University of York
Heslington
York
YO10 5DD
UK
;
_publ_contact_author_email       jason.lynam@york.ac.uk
_publ_contact_author_fax         +44(0)1904322516
_publ_contact_author_name        'Jason M Lynam'
_publ_contact_author_phone       +44(0)1904322534
_publ_section_title
;
 Ruthenium-Mediated C-H Functionalization of Pyridine: The Role of
 Vinylidene and Pyridylidene Ligands
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2222
_journal_page_last               2234
_journal_paper_doi               10.1021/ja3097256
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C37 H29 F3 N P Ru, C3 H7'
_chemical_formula_sum            'C40 H36 F3 N P Ru'
_chemical_formula_weight         719.74
_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             2012-07-26
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.724(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3602(11)
_cell_length_b                   15.4872(11)
_cell_length_c                   17.2133(10)
_cell_measurement_reflns_used    7576
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      30.5491
_cell_measurement_theta_min      3.2572
_cell_volume                     3272.4(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_details
;
  1 omega  -92.00   46.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.4240    0.0000  150.0000 138

  2 omega   -7.00   93.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6740   77.0000  120.0000 100
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0540061000
_diffrn_orient_matrix_UB_12      -0.0145298000
_diffrn_orient_matrix_UB_13      0.0110748000
_diffrn_orient_matrix_UB_21      -0.0177864000
_diffrn_orient_matrix_UB_22      -0.0227460000
_diffrn_orient_matrix_UB_23      0.0320712000
_diffrn_orient_matrix_UB_31      -0.0103132000
_diffrn_orient_matrix_UB_32      -0.0370860000
_diffrn_orient_matrix_UB_33      -0.0239233000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17427
_diffrn_reflns_theta_full        28.22
_diffrn_reflns_theta_max         30.59
_diffrn_reflns_theta_min         3.26
_diffrn_source                   'SuperNova (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
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    1.461
_exptl_crystal_description       block
_exptl_crystal_F_000             1476
_exptl_crystal_recrystallization_method 'Hexane at -15degC'
_exptl_crystal_size_max          0.1905
_exptl_crystal_size_mid          0.0984
_exptl_crystal_size_min          0.0429
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         8791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0343P)²+1.7017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0879
_reflns_number_gt                7264
_reflns_number_total             8791
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3097256_si_002_5.cif
_cod_data_source_block           '[10b].CH2Cl2'
_cod_database_code               4119315
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         'C37 H29 F9 N1 P2 Ru1'
_chemical_oxdiff_usercomment     'Neetisha's NM233'
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
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
C1 C 0.87573(19) 0.62154(16) 0.52685(13) 0.0243(5) Uani 1 1 d .
H1 H 0.9461 0.6029 0.5172 0.029 Uiso 1 1 calc R
C2 C 0.8351(2) 0.70712(15) 0.52026(13) 0.0236(5) Uani 1 1 d .
H2 H 0.8732 0.7557 0.5035 0.028 Uiso 1 1 calc R
C3 C 0.7281(2) 0.70838(15) 0.54286(13) 0.0231(5) Uani 1 1 d .
H3 H 0.6832 0.7578 0.5457 0.028 Uiso 1 1 calc R
C4 C 0.7010(2) 0.62239(15) 0.56022(13) 0.0233(5) Uani 1 1 d .
H4 H 0.6335 0.6037 0.5757 0.028 Uiso 1 1 calc R
C5 C 0.7912(2) 0.56876(16) 0.55062(12) 0.0236(5) Uani 1 1 d .
H5 H 0.7948 0.5081 0.5586 0.028 Uiso 1 1 calc R
C6 C 0.73493(18) 0.51748(13) 0.37086(12) 0.0164(4) Uani 1 1 d .
C7 C 0.8270(2) 0.46638(15) 0.35909(13) 0.0221(5) Uani 1 1 d .
H7 H 0.896(2) 0.4873(17) 0.3825(16) 0.030(7) Uiso 1 1 d .
C8 C 0.8187(2) 0.39111(16) 0.31642(15) 0.0286(6) Uani 1 1 d .
H8 H 0.880(3) 0.363(2) 0.3155(19) 0.049(10) Uiso 1 1 d .
C9 C 0.7166(2) 0.36413(15) 0.27987(15) 0.0298(6) Uani 1 1 d .
H9 H 0.715(2) 0.3112(18) 0.2469(15) 0.029(7) Uiso 1 1 d .
C10 C 0.6276(2) 0.41205(15) 0.28935(14) 0.0258(5) Uani 1 1 d .
H10 H 0.556(2) 0.3998(18) 0.2624(16) 0.034(8) Uiso 1 1 d .
C11 C 0.54449(19) 0.53342(14) 0.35004(13) 0.0191(4) Uani 1 1 d .
H11 H 0.479(2) 0.5135(16) 0.3280(15) 0.025(7) Uiso 1 1 d .
C12 C 0.56708(17) 0.60312(13) 0.39502(12) 0.0162(4) Uani 1 1 d .
C13 C 0.47538(17) 0.65196(14) 0.42189(12) 0.0156(4) Uani 1 1 d .
C14 C 0.41029(18) 0.61379(14) 0.47373(13) 0.0196(4) Uani 1 1 d .
H14 H 0.4232 0.5555 0.4893 0.024 Uiso 1 1 calc R
C15 C 0.32730(18) 0.65960(15) 0.50283(13) 0.0213(5) Uani 1 1 d .
H15 H 0.2843 0.6327 0.5382 0.026 Uiso 1 1 calc R
C16 C 0.30719(18) 0.74457(14) 0.48035(13) 0.0194(4) Uani 1 1 d .
C17 C 0.2217(2) 0.79402(16) 0.51558(15) 0.0262(5) Uani 1 1 d .
C18 C 0.36890(19) 0.78282(15) 0.42733(14) 0.0229(5) Uani 1 1 d .
H18 H 0.3541 0.8405 0.4106 0.027 Uiso 1 1 calc R
C19 C 0.45190(19) 0.73708(14) 0.39894(13) 0.0213(5) Uani 1 1 d .
H19 H 0.4939 0.7641 0.3630 0.026 Uiso 1 1 calc R
C20 C 0.73188(17) 0.81554(13) 0.32199(12) 0.0166(4) Uani 1 1 d .
C21 C 0.68621(19) 0.85357(14) 0.38376(13) 0.0218(5) Uani 1 1 d .
H21 H 0.6708 0.8191 0.4268 0.026 Uiso 1 1 calc R
C22 C 0.6627(2) 0.94176(15) 0.38325(14) 0.0256(5) Uani 1 1 d .
H22 H 0.6314 0.9668 0.4258 0.031 Uiso 1 1 calc R
C23 C 0.6848(2) 0.99260(15) 0.32121(14) 0.0250(5) Uani 1 1 d .
H23 H 0.6684 1.0525 0.3207 0.030 Uiso 1 1 calc R
C24 C 0.7311(2) 0.95557(14) 0.25967(13) 0.0225(5) Uani 1 1 d .
H24 H 0.7470 0.9904 0.2170 0.027 Uiso 1 1 calc R
C25 C 0.75438(19) 0.86817(14) 0.25987(13) 0.0200(4) Uani 1 1 d .
H25 H 0.7860 0.8436 0.2173 0.024 Uiso 1 1 calc R
C26 C 0.89287(17) 0.68989(13) 0.29171(12) 0.0155(4) Uani 1 1 d .
C27 C 0.98147(18) 0.67069(14) 0.34744(13) 0.0207(4) Uani 1 1 d .
H27 H 0.9699 0.6623 0.4005 0.025 Uiso 1 1 calc R
C28 C 1.08625(19) 0.66373(15) 0.32611(14) 0.0236(5) Uani 1 1 d .
H28 H 1.1456 0.6510 0.3646 0.028 Uiso 1 1 calc R
C29 C 1.10419(19) 0.67532(15) 0.24910(14) 0.0233(5) Uani 1 1 d .
H29 H 1.1756 0.6696 0.2344 0.028 Uiso 1 1 calc R
C30 C 1.01751(19) 0.69532(14) 0.19319(13) 0.0216(5) Uani 1 1 d .
H30 H 1.0298 0.7040 0.1403 0.026 Uiso 1 1 calc R
C31 C 0.91290(18) 0.70261(13) 0.21434(12) 0.0176(4) Uani 1 1 d .
H31 H 0.8542 0.7164 0.1757 0.021 Uiso 1 1 calc R
C32 C 0.67156(17) 0.66511(13) 0.23255(12) 0.0160(4) Uani 1 1 d .
C33 C 0.57793(18) 0.71058(15) 0.20444(13) 0.0211(4) Uani 1 1 d .
H33 H 0.5577 0.7602 0.2318 0.025 Uiso 1 1 calc R
C34 C 0.5136(2) 0.68440(17) 0.13683(14) 0.0282(5) Uani 1 1 d .
H34 H 0.4499 0.7161 0.1185 0.034 Uiso 1 1 calc R
C35 C 0.5421(2) 0.61250(16) 0.09618(14) 0.0301(6) Uani 1 1 d .
H35 H 0.4987 0.5950 0.0496 0.036 Uiso 1 1 calc R
C36 C 0.6343(2) 0.56622(15) 0.12379(13) 0.0272(5) Uani 1 1 d .
H36 H 0.6537 0.5164 0.0964 0.033 Uiso 1 1 calc R
C37 C 0.69876(19) 0.59217(14) 0.19149(12) 0.0201(4) Uani 1 1 d .
H37 H 0.7619 0.5599 0.2099 0.024 Uiso 1 1 calc R
F1 F 0.21052(15) 0.87433(10) 0.48917(12) 0.0503(5) Uani 1 1 d .
F2 F 0.12362(12) 0.75579(11) 0.50408(10) 0.0402(4) Uani 1 1 d .
F3 F 0.24254(13) 0.80089(11) 0.59375(9) 0.0397(4) Uani 1 1 d .
N1 N 0.63662(16) 0.48509(11) 0.33437(10) 0.0183(4) Uani 1 1 d .
P1 P 0.75539(4) 0.69773(3) 0.32333(3) 0.01331(11) Uani 1 1 d .
Ru1 Ru 0.727526(13) 0.624766(10) 0.434240(9) 0.01316(5) Uani 1 1 d .
C38 C 0.0179(2) 1.00592(16) 0.45917(15) 0.0304(6) Uani 1 1 d .
H38A H -0.0104 1.0617 0.4373 0.037 Uiso 1 1 calc R
H38B H 0.0984 1.0083 0.4638 0.037 Uiso 1 1 calc R
C39 C -0.0218(2) 0.93408(18) 0.40343(15) 0.0327(6) Uani 1 1 d .
H39A H -0.1022 0.9373 0.3926 0.039 Uiso 1 1 calc R
H39B H -0.0030 0.8778 0.4288 0.039 Uiso 1 1 calc R
C40 C 0.0270(3) 0.9383(2) 0.32629(17) 0.0423(7) Uani 1 1 d .
H40A H -0.0023 0.8911 0.2922 0.063 Uiso 1 1 calc R
H40B H 0.1064 0.9328 0.3363 0.063 Uiso 1 1 calc R
H40C H 0.0084 0.9937 0.3007 0.063 Uiso 1 1 calc R
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 3 -1 0.0210 0.0000 3.0000 -1.0000 -0.0551 -0.1003 -0.0867
-4 -21 5 0.0116 -4.0000 -21.0000 5.0000 0.1473 0.7105 0.6965
-1 6 23 0.0896 -1.0000 6.0000 23.0000 0.1183 0.6145 -0.7694
1 -1 -24 0.0692 1.0000 -1.0000 -24.0000 -0.2026 -0.7604 0.6087
14 2 -16 0.0450 14.0000 2.0000 -16.0000 0.5456 -0.8092 0.1711
13 14 -4 0.0377 13.0000 14.0000 -4.0000 0.4520 -0.6821 -0.5537
-15 -7 13 0.0411 -15.0000 -7.0000 13.0000 -0.5605 0.8457 0.0969
-14 -12 -3 0.0594 -14.0000 -12.0000 -3.0000 -0.6143 0.4315 0.6596
-1 22 3 0.0382 -1.0000 22.0000 3.0000 -0.3413 -0.3878 -0.8765
-17 -5 -1 0.0478 -17.0000 -5.0000 -1.0000 -0.8558 0.3900 0.3827
-12 16 5 0.0436 -12.0000 16.0000 5.0000 -0.8248 0.0120 -0.5907
17 -6 1 0.0639 17.0000 -6.0000 1.0000 1.0164 -0.1393 0.0242
13 -14 -6 0.0433 13.0000 -14.0000 -6.0000 0.8383 -0.1076 0.5308
-11 16 8 0.0418 -11.0000 16.0000 8.0000 -0.7369 0.0895 -0.6737
8 15 -14 0.0259 8.0000 15.0000 -14.0000 0.0545 -0.9331 -0.2972
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
C2 C1 H1 126.4 . .
C2 C1 C5 107.2(2) . .
C2 C1 Ru1 71.10(12) . .
C5 C1 H1 126.4 . .
C5 C1 Ru1 69.98(13) . .
Ru1 C1 H1 124.1 . .
C1 C2 H2 125.6 . .
C1 C2 C3 108.8(2) . .
C1 C2 Ru1 72.59(13) . .
C3 C2 H2 125.6 . .
C3 C2 Ru1 72.10(13) . .
Ru1 C2 H2 121.4 . .
C2 C3 H3 126.4 . .
C2 C3 Ru1 71.39(12) . .
C4 C3 C2 107.2(2) . .
C4 C3 H3 126.4 . .
C4 C3 Ru1 70.08(12) . .
Ru1 C3 H3 123.8 . .
C3 C4 H4 125.7 . .
C3 C4 C5 108.6(2) . .
C3 C4 Ru1 73.35(13) . .
C5 C4 H4 125.7 . .
C5 C4 Ru1 71.87(13) . .
Ru1 C4 H4 120.8 . .
C1 C5 H5 125.9 . .
C1 C5 Ru1 73.35(13) . .
C4 C5 C1 108.1(2) . .
C4 C5 H5 125.9 . .
C4 C5 Ru1 71.22(12) . .
Ru1 C5 H5 121.2 . .
C7 C6 Ru1 129.12(17) . .
N1 C6 C7 113.94(19) . .
N1 C6 Ru1 116.90(15) . .
C6 C7 H7 116.2(17) . .
C8 C7 C6 122.5(2) . .
C8 C7 H7 121.3(17) . .
C7 C8 H8 115(2) . .
C7 C8 C9 119.8(2) . .
C9 C8 H8 125(2) . .
C8 C9 H9 117.2(16) . .
C10 C9 C8 118.9(2) . .
C10 C9 H9 123.9(16) . .
C9 C10 H10 123.2(17) . .
C9 C10 N1 120.5(2) . .
N1 C10 H10 116.2(17) . .
C12 C11 H11 129.0(17) . .
C12 C11 N1 114.8(2) . .
N1 C11 H11 116.2(17) . .
C11 C12 C13 118.5(2) . .
C11 C12 Ru1 116.83(16) . .
C13 C12 Ru1 124.12(15) . .
C14 C13 C12 120.08(19) . .
C19 C13 C12 122.33(19) . .
C19 C13 C14 117.6(2) . .
C13 C14 H14 119.4 . .
C15 C14 C13 121.2(2) . .
C15 C14 H14 119.4 . .
C14 C15 H15 120.0 . .
C16 C15 C14 120.0(2) . .
C16 C15 H15 120.0 . .
C15 C16 C17 119.1(2) . .
C15 C16 C18 119.6(2) . .
C18 C16 C17 121.2(2) . .
F1 C17 C16 113.1(2) . .
F1 C17 F2 107.9(2) . .
F1 C17 F3 105.6(2) . .
F2 C17 C16 112.6(2) . .
F2 C17 F3 104.3(2) . .
F3 C17 C16 112.67(19) . .
C16 C18 H18 120.0 . .
C19 C18 C16 120.1(2) . .
C19 C18 H18 120.0 . .
C13 C19 H19 119.3 . .
C18 C19 C13 121.5(2) . .
C18 C19 H19 119.3 . .
C21 C20 C25 118.19(19) . .
C21 C20 P1 119.07(16) . .
C25 C20 P1 122.70(16) . .
C20 C21 H21 119.6 . .
C20 C21 C22 120.8(2) . .
C22 C21 H21 119.6 . .
C21 C22 H22 119.9 . .
C23 C22 C21 120.2(2) . .
C23 C22 H22 119.9 . .
C22 C23 H23 120.3 . .
C22 C23 C24 119.5(2) . .
C24 C23 H23 120.3 . .
C23 C24 H24 119.8 . .
C25 C24 C23 120.5(2) . .
C25 C24 H24 119.8 . .
C20 C25 H25 119.6 . .
C24 C25 C20 120.8(2) . .
C24 C25 H25 119.6 . .
C27 C26 P1 118.97(16) . .
C31 C26 C27 118.1(2) . .
C31 C26 P1 122.91(16) . .
C26 C27 H27 119.6 . .
C28 C27 C26 120.9(2) . .
C28 C27 H27 119.6 . .
C27 C28 H28 119.9 . .
C29 C28 C27 120.2(2) . .
C29 C28 H28 119.9 . .
C28 C29 H29 120.1 . .
C28 C29 C30 119.8(2) . .
C30 C29 H29 120.1 . .
C29 C30 H30 119.9 . .
C31 C30 C29 120.2(2) . .
C31 C30 H30 119.9 . .
C26 C31 H31 119.6 . .
C30 C31 C26 120.9(2) . .
C30 C31 H31 119.6 . .
C33 C32 C37 118.3(2) . .
C33 C32 P1 121.22(17) . .
C37 C32 P1 120.48(17) . .
C32 C33 H33 119.5 . .
C34 C33 C32 120.9(2) . .
C34 C33 H33 119.5 . .
C33 C34 H34 119.9 . .
C35 C34 C33 120.3(2) . .
C35 C34 H34 119.9 . .
C34 C35 H35 120.3 . .
C36 C35 C34 119.5(2) . .
C36 C35 H35 120.3 . .
C35 C36 H36 119.8 . .
C35 C36 C37 120.4(2) . .
C37 C36 H36 119.8 . .
C32 C37 H37 119.7 . .
C36 C37 C32 120.7(2) . .
C36 C37 H37 119.7 . .
C6 N1 C11 113.72(18) . .
C10 N1 C6 124.2(2) . .
C10 N1 C11 122.1(2) . .
C20 P1 C26 102.12(10) . .
C20 P1 Ru1 117.46(7) . .
C26 P1 Ru1 116.65(7) . .
C32 P1 C20 100.86(9) . .
C32 P1 C26 100.22(10) . .
C32 P1 Ru1 116.72(7) . .
C2 Ru1 C1 36.31(8) . .
C2 Ru1 C3 36.51(9) . .
C2 Ru1 P1 97.69(6) . .
C3 Ru1 C1 60.88(9) . .
C3 Ru1 P1 114.85(6) . .
C4 Ru1 C1 61.21(9) . .
C4 Ru1 C2 61.03(9) . .
C4 Ru1 C3 36.57(8) . .
C4 Ru1 C5 36.92(9) . .
C4 Ru1 P1 151.19(6) . .
C5 Ru1 C1 36.67(9) . .
C5 Ru1 C2 61.00(9) . .
C5 Ru1 C3 61.19(8) . .
C5 Ru1 P1 150.40(7) . .
C6 Ru1 C1 106.20(9) . .
C6 Ru1 C2 139.95(9) . .
C6 Ru1 C3 158.09(8) . .
C6 Ru1 C4 122.61(8) . .
C6 Ru1 C5 97.63(8) . .
C6 Ru1 C12 77.76(9) . .
C6 Ru1 P1 86.20(6) . .
C12 Ru1 C1 153.36(8) . .
C12 Ru1 C2 141.29(9) . .
C12 Ru1 C3 105.92(9) . .
C12 Ru1 C4 94.07(9) . .
C12 Ru1 C5 117.21(9) . .
C12 Ru1 P1 92.32(6) . .
P1 Ru1 C1 114.08(6) . .
C38 C38 H38A 109.0 3_576 .
C38 C38 H38B 109.0 3_576 .
H38A C38 H38B 107.8 . .
C39 C38 C38 112.7(3) . 3_576
C39 C38 H38A 109.0 . .
C39 C38 H38B 109.0 . .
C38 C39 H39A 109.0 . .
C38 C39 H39B 109.0 . .
C38 C39 C40 112.9(2) . .
H39A C39 H39B 107.8 . .
C40 C39 H39A 109.0 . .
C40 C39 H39B 109.0 . .
C39 C40 H40A 109.5 . .
C39 C40 H40B 109.5 . .
C39 C40 H40C 109.5 . .
H40A C40 H40B 109.5 . .
H40A C40 H40C 109.5 . .
H40B C40 H40C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 0.9500 .
C1 C2 1.417(3) .
C1 C5 1.424(3) .
C1 Ru1 2.284(2) .
C2 H2 0.9500 .
C2 C3 1.422(3) .
C2 Ru1 2.264(2) .
C3 H3 0.9500 .
C3 C4 1.414(3) .
C3 Ru1 2.274(2) .
C4 H4 0.9500 .
C4 C5 1.416(3) .
C4 Ru1 2.231(2) .
C5 H5 0.9500 .
C5 Ru1 2.240(2) .
C6 C7 1.420(3) .
C6 N1 1.394(3) .
C6 Ru1 1.996(2) .
C7 H7 0.96(3) .
C7 C8 1.375(3) .
C8 H8 0.88(3) .
C8 C9 1.406(4) .
C9 H9 1.00(3) .
C9 C10 1.353(4) .
C10 H10 0.97(3) .
C10 N1 1.368(3) .
C11 H11 0.91(3) .
C11 C12 1.339(3) .
C11 N1 1.415(3) .
C12 C13 1.481(3) .
C12 Ru1 2.046(2) .
C13 C14 1.400(3) .
C13 C19 1.397(3) .
C14 H14 0.9500 .
C14 C15 1.388(3) .
C15 H15 0.9500 .
C15 C16 1.386(3) .
C16 C17 1.491(3) .
C16 C18 1.389(3) .
C17 F1 1.326(3) .
C17 F2 1.342(3) .
C17 F3 1.344(3) .
C18 H18 0.9500 .
C18 C19 1.382(3) .
C19 H19 0.9500 .
C20 C21 1.392(3) .
C20 C25 1.398(3) .
C20 P1 1.847(2) .
C21 H21 0.9500 .
C21 C22 1.396(3) .
C22 H22 0.9500 .
C22 C23 1.380(3) .
C23 H23 0.9500 .
C23 C24 1.386(3) .
C24 H24 0.9500 .
C24 C25 1.384(3) .
C25 H25 0.9500 .
C26 C27 1.401(3) .
C26 C31 1.397(3) .
C26 P1 1.848(2) .
C27 H27 0.9500 .
C27 C28 1.391(3) .
C28 H28 0.9500 .
C28 C29 1.381(3) .
C29 H29 0.9500 .
C29 C30 1.389(3) .
C30 H30 0.9500 .
C30 C31 1.388(3) .
C31 H31 0.9500 .
C32 C33 1.392(3) .
C32 C37 1.394(3) .
C32 P1 1.842(2) .
C33 H33 0.9500 .
C33 C34 1.391(3) .
C34 H34 0.9500 .
C34 C35 1.382(4) .
C35 H35 0.9500 .
C35 C36 1.382(4) .
C36 H36 0.9500 .
C36 C37 1.392(3) .
C37 H37 0.9500 .
P1 Ru1 2.2791(5) .
C38 C38 1.533(5) 3_576
C38 H38A 0.9900 .
C38 H38B 0.9900 .
C38 C39 1.513(4) .
C39 H39A 0.9900 .
C39 H39B 0.9900 .
C39 C40 1.523(4) .
C40 H40A 0.9800 .
C40 H40B 0.9800 .
C40 H40C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
C1 C2 C3 C4 -2.5(2) .
C1 C2 C3 Ru1 -63.74(15) .
C1 C2 Ru1 C3 117.2(2) .
C1 C2 Ru1 C4 79.85(15) .
C1 C2 Ru1 C5 37.41(13) .
C1 C2 Ru1 C6 -27.5(2) .
C1 C2 Ru1 C12 135.70(15) .
C1 C2 Ru1 P1 -120.78(13) .
C1 C5 Ru1 C2 -37.03(14) .
C1 C5 Ru1 C3 -78.97(15) .
C1 C5 Ru1 C4 -116.4(2) .
C1 C5 Ru1 C6 106.95(15) .
C1 C5 Ru1 C12 -172.94(14) .
C1 C5 Ru1 P1 11.2(2) .
C2 C1 C5 C4 -1.4(2) .
C2 C1 C5 Ru1 61.75(15) .
C2 C1 Ru1 C3 -37.29(14) .
C2 C1 Ru1 C4 -79.31(15) .
C2 C1 Ru1 C5 -117.2(2) .
C2 C1 Ru1 C6 161.96(14) .
C2 C1 Ru1 C12 -103.1(2) .
C2 C1 Ru1 P1 68.85(14) .
C2 C3 C4 C5 1.6(2) .
C2 C3 C4 Ru1 -62.11(15) .
C2 C3 Ru1 C1 37.07(13) .
C2 C3 Ru1 C4 117.0(2) .
C2 C3 Ru1 C5 79.22(15) .
C2 C3 Ru1 C6 95.1(3) .
C2 C3 Ru1 C12 -168.09(13) .
C2 C3 Ru1 P1 -67.80(14) .
C3 C2 Ru1 C1 -117.2(2) .
C3 C2 Ru1 C4 -37.35(13) .
C3 C2 Ru1 C5 -79.79(15) .
C3 C2 Ru1 C6 -144.73(14) .
C3 C2 Ru1 C12 18.5(2) .
C3 C2 Ru1 P1 122.03(13) .
C3 C4 C5 C1 -0.1(3) .
C3 C4 C5 Ru1 -64.66(15) .
C3 C4 Ru1 C1 78.98(15) .
C3 C4 Ru1 C2 37.29(14) .
C3 C4 Ru1 C5 116.6(2) .
C3 C4 Ru1 C6 170.48(14) .
C3 C4 Ru1 C12 -111.46(15) .
C3 C4 Ru1 P1 -9.1(2) .
C4 C3 Ru1 C1 -79.96(15) .
C4 C3 Ru1 C2 -117.0(2) .
C4 C3 Ru1 C5 -37.81(14) .
C4 C3 Ru1 C6 -21.9(3) .
C4 C3 Ru1 C12 74.88(15) .
C4 C3 Ru1 P1 175.17(12) .
C4 C5 Ru1 C1 116.4(2) .
C4 C5 Ru1 C2 79.39(15) .
C4 C5 Ru1 C3 37.45(14) .
C4 C5 Ru1 C6 -136.64(15) .
C4 C5 Ru1 C12 -56.52(16) .
C4 C5 Ru1 P1 127.60(14) .
C5 C1 C2 C3 2.4(2) .
C5 C1 C2 Ru1 -61.02(15) .
C5 C1 Ru1 C2 117.2(2) .
C5 C1 Ru1 C3 79.89(15) .
C5 C1 Ru1 C4 37.87(14) .
C5 C1 Ru1 C6 -80.87(15) .
C5 C1 Ru1 C12 14.1(3) .
C5 C1 Ru1 P1 -173.98(12) .
C5 C4 Ru1 C1 -37.62(14) .
C5 C4 Ru1 C2 -79.30(15) .
C5 C4 Ru1 C3 -116.6(2) .
C5 C4 Ru1 C6 53.89(17) .
C5 C4 Ru1 C12 131.95(15) .
C5 C4 Ru1 P1 -125.72(15) .
C6 C7 C8 C9 2.6(4) .
C7 C6 N1 C10 -1.6(3) .
C7 C6 N1 C11 176.49(18) .
C7 C6 Ru1 C1 -24.3(2) .
C7 C6 Ru1 C2 -7.7(3) .
C7 C6 Ru1 C3 -74.8(3) .
C7 C6 Ru1 C4 -90.1(2) .
C7 C6 Ru1 C5 -60.8(2) .
C7 C6 Ru1 C12 -177.1(2) .
C7 C6 Ru1 P1 89.73(19) .
C7 C8 C9 C10 -1.8(4) .
C8 C9 C10 N1 -0.6(4) .
C9 C10 N1 C6 2.4(3) .
C9 C10 N1 C11 -175.5(2) .
C11 C12 C13 C14 66.1(3) .
C11 C12 C13 C19 -115.5(2) .
C11 C12 Ru1 C1 -101.3(2) .
C11 C12 Ru1 C2 -168.59(15) .
C11 C12 Ru1 C3 -157.26(16) .
C11 C12 Ru1 C4 -122.05(17) .
C11 C12 Ru1 C5 -91.90(18) .
C11 C12 Ru1 C6 0.46(16) .
C11 C12 Ru1 P1 86.07(16) .
C12 C11 N1 C6 1.9(3) .
C12 C11 N1 C10 180.0(2) .
C12 C13 C14 C15 176.8(2) .
C12 C13 C19 C18 -177.1(2) .
C13 C12 Ru1 C1 69.9(3) .
C13 C12 Ru1 C2 2.6(2) .
C13 C12 Ru1 C3 13.96(19) .
C13 C12 Ru1 C4 49.18(18) .
C13 C12 Ru1 C5 79.33(18) .
C13 C12 Ru1 C6 171.69(18) .
C13 C12 Ru1 P1 -102.71(16) .
C13 C14 C15 C16 0.4(3) .
C14 C13 C19 C18 1.2(3) .
C14 C15 C16 C17 -176.8(2) .
C14 C15 C16 C18 1.4(3) .
C15 C16 C17 F1 -180.0(2) .
C15 C16 C17 F2 -57.3(3) .
C15 C16 C17 F3 60.3(3) .
C15 C16 C18 C19 -1.8(3) .
C16 C18 C19 C13 0.5(4) .
C17 C16 C18 C19 176.3(2) .
C18 C16 C17 F1 1.9(3) .
C18 C16 C17 F2 124.6(2) .
C18 C16 C17 F3 -117.8(2) .
C19 C13 C14 C15 -1.7(3) .
C20 C21 C22 C23 -0.1(4) .
C20 P1 Ru1 C1 -86.77(10) .
C20 P1 Ru1 C2 -52.91(10) .
C20 P1 Ru1 C3 -19.13(11) .
C20 P1 Ru1 C4 -13.15(16) .
C20 P1 Ru1 C5 -94.05(15) .
C20 P1 Ru1 C6 167.18(10) .
C20 P1 Ru1 C12 89.61(10) .
C21 C20 C25 C24 -0.4(3) .
C21 C20 P1 C26 -136.51(19) .
C21 C20 P1 C32 120.42(19) .
C21 C20 P1 Ru1 -7.6(2) .
C21 C22 C23 C24 -0.4(4) .
C22 C23 C24 C25 0.5(4) .
C23 C24 C25 C20 -0.1(4) .
C25 C20 C21 C22 0.5(3) .
C25 C20 P1 C26 45.9(2) .
C25 C20 P1 C32 -57.2(2) .
C25 C20 P1 Ru1 174.85(16) .
C26 C27 C28 C29 -0.3(4) .
C26 P1 Ru1 C1 34.94(10) .
C26 P1 Ru1 C2 68.80(10) .
C26 P1 Ru1 C3 102.57(10) .
C26 P1 Ru1 C4 108.55(15) .
C26 P1 Ru1 C5 27.65(15) .
C26 P1 Ru1 C6 -71.12(10) .
C26 P1 Ru1 C12 -148.68(9) .
C27 C26 C31 C30 0.8(3) .
C27 C26 P1 C20 105.30(18) .
C27 C26 P1 C32 -151.14(17) .
C27 C26 P1 Ru1 -24.16(19) .
C27 C28 C29 C30 1.0(4) .
C28 C29 C30 C31 -0.8(3) .
C29 C30 C31 C26 -0.1(3) .
C31 C26 C27 C28 -0.6(3) .
C31 C26 P1 C20 -74.45(19) .
C31 C26 P1 C32 29.11(19) .
C31 C26 P1 Ru1 156.10(15) .
C32 C33 C34 C35 -0.2(4) .
C32 P1 Ru1 C1 153.29(10) .
C32 P1 Ru1 C2 -172.85(10) .
C32 P1 Ru1 C3 -139.08(10) .
C32 P1 Ru1 C4 -133.10(15) .
C32 P1 Ru1 C5 146.00(15) .
C32 P1 Ru1 C6 47.23(10) .
C32 P1 Ru1 C12 -30.33(10) .
C33 C32 C37 C36 0.6(3) .
C33 C32 P1 C20 -30.4(2) .
C33 C32 P1 C26 -134.95(18) .
C33 C32 P1 Ru1 98.12(18) .
C33 C34 C35 C36 0.8(4) .
C34 C35 C36 C37 -0.7(4) .
C35 C36 C37 C32 0.0(4) .
C37 C32 C33 C34 -0.5(3) .
C37 C32 P1 C20 151.71(18) .
C37 C32 P1 C26 47.12(19) .
C37 C32 P1 Ru1 -79.82(18) .
N1 C6 C7 C8 -1.0(3) .
N1 C6 Ru1 C1 153.42(15) .
N1 C6 Ru1 C2 169.98(13) .
N1 C6 Ru1 C3 102.9(3) .
N1 C6 Ru1 C4 87.60(17) .
N1 C6 Ru1 C5 116.91(16) .
N1 C6 Ru1 C12 0.62(15) .
N1 C6 Ru1 P1 -92.59(15) .
N1 C11 C12 C13 -173.17(18) .
N1 C11 C12 Ru1 -1.4(3) .
P1 C20 C21 C22 -177.15(18) .
P1 C20 C25 C24 177.16(18) .
P1 C26 C27 C28 179.66(17) .
P1 C26 C31 C30 -179.44(16) .
P1 C32 C33 C34 -178.49(17) .
P1 C32 C37 C36 178.58(17) .
Ru1 C1 C2 C3 63.42(15) .
Ru1 C1 C5 C4 -63.15(15) .
Ru1 C2 C3 C4 61.26(15) .
Ru1 C3 C4 C5 63.70(15) .
Ru1 C4 C5 C1 64.54(15) .
Ru1 C6 C7 C8 176.78(18) .
Ru1 C6 N1 C10 -179.59(16) .
Ru1 C6 N1 C11 -1.5(2) .
Ru1 C12 C13 C14 -104.9(2) .
Ru1 C12 C13 C19 73.4(2) .
C38 C38 C39 C40 -171.6(3) 3_576
