# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2g
_database_code_depnum_ccdc_archive 'CCDC 1415870'
_audit_update_record             
;
2015-07-30 deposited with the CCDC.
2016-02-03 downloaded from the CCDC.
;
#=============================================================================== 

_audit_creation_method           SHELXL97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H36 Cl3 P Ru'
_chemical_formula_weight         538.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru 0.0552 3.2960 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6344(3)
_cell_length_b                   10.5128(3)
_cell_length_c                   15.3514(6)
_cell_angle_alpha                103.182(3)
_cell_angle_beta                 92.237(3)
_cell_angle_gamma                90.962(3)
_cell_volume                     1198.29(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6203
_cell_measurement_theta_min      4.2900
_cell_measurement_theta_max      69.5410

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    9.030
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.44180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9679
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.321
_diffrn_reflns_theta_max         69.679
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4410
_reflns_number_gt                3951
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlis Pro CCD (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis Pro RED (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis Pro RED (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SUPERFLIP (Palatinus et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.0973P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4410
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.57027(3) 0.28612(2) 0.34310(2) 0.03657(10) Uani 1 1 d . . . . .
Cl3 Cl 0.70194(11) 0.06921(8) 0.13434(6) 0.0477(2) Uani 1 1 d . . . . .
Cl2 Cl 0.36367(11) 0.44423(7) 0.31596(6) 0.0475(2) Uani 1 1 d . . . . .
P1 P 0.48620(10) 0.14309(7) 0.20706(5) 0.03457(17) Uani 1 1 d . . . . .
Cl1 Cl 0.33071(14) 0.19678(9) 0.41024(6) 0.0596(2) Uani 1 1 d . . . . .
C18 C 0.4832(5) -0.0833(3) 0.2726(2) 0.0494(8) Uani 1 1 d . . . . .
H18A H 0.5913 -0.1116 0.2438 0.059 Uiso 1 1 calc R U . . .
H18B H 0.5136 -0.0242 0.3298 0.059 Uiso 1 1 calc R U . . .
C21 C 0.2230(7) -0.2246(4) 0.1395(3) 0.0682(12) Uani 1 1 d . . . . .
H21A H 0.1119 -0.1998 0.1662 0.082 Uiso 1 1 calc R U . . .
H21B H 0.1982 -0.2846 0.0821 0.082 Uiso 1 1 calc R U . . .
C16 C 0.1699(4) 0.2161(4) 0.1370(2) 0.0455(7) Uani 1 1 d . . . . .
H16A H 0.1625 0.2870 0.1896 0.055 Uiso 1 1 calc R U . . .
H16B H 0.1186 0.1380 0.1503 0.055 Uiso 1 1 calc R U . . .
C17 C 0.3754(5) -0.0115(3) 0.2141(2) 0.0410(7) Uani 1 1 d . . . . .
H17 H 0.2676 0.0133 0.2456 0.049 Uiso 1 1 calc R U . . .
C12 C 0.4459(5) 0.3109(3) 0.0880(2) 0.0434(7) Uani 1 1 d . . . . .
H12A H 0.4503 0.3859 0.1384 0.052 Uiso 1 1 calc R U . . .
H12B H 0.5651 0.2910 0.0708 0.052 Uiso 1 1 calc R U . . .
C1 C 0.7669(6) 0.2103(4) 0.4284(3) 0.0546(9) Uani 1 1 d . . . . .
C13 C 0.3403(5) 0.3432(4) 0.0096(3) 0.0533(9) Uani 1 1 d . . . . .
H13A H 0.3918 0.4203 -0.0051 0.064 Uiso 1 1 calc R U . . .
H13B H 0.3461 0.2712 -0.0424 0.064 Uiso 1 1 calc R U . . .
C14 C 0.1506(6) 0.3677(4) 0.0313(3) 0.0563(9) Uani 1 1 d . . . . .
H14A H 0.0865 0.3842 -0.0207 0.068 Uiso 1 1 calc R U . . .
H14B H 0.1437 0.4445 0.0798 0.068 Uiso 1 1 calc R U . . .
C15 C 0.0670(5) 0.2498(4) 0.0583(3) 0.0510(8) Uani 1 1 d . . . . .
H15A H -0.0526 0.2691 0.0748 0.061 Uiso 1 1 calc R U . . .
H15B H 0.0637 0.1751 0.0077 0.061 Uiso 1 1 calc R U . . .
C9 C 0.9273(7) 0.6569(5) 0.3783(4) 0.0752(13) Uani 1 1 d . . . . .
H9A H 0.9327 0.7362 0.3574 0.113 Uiso 1 1 calc R U . . .
H9B H 0.8986 0.6767 0.4402 0.113 Uiso 1 1 calc R U . . .
H9C H 1.0389 0.6159 0.3720 0.113 Uiso 1 1 calc R U . . .
C22 C 0.3179(6) -0.1031(3) 0.1248(3) 0.0522(9) Uani 1 1 d . . . . .
H22A H 0.2407 -0.0575 0.0913 0.063 Uiso 1 1 calc R U . . .
H22B H 0.4200 -0.1287 0.0899 0.063 Uiso 1 1 calc R U . . .
C11 C 0.3613(4) 0.1934(3) 0.1154(2) 0.0387(7) Uani 1 1 d . . . . .
H11 H 0.3625 0.1199 0.0631 0.046 Uiso 1 1 calc R U . . .
C19 C 0.3817(7) -0.2015(4) 0.2880(3) 0.0611(10) Uani 1 1 d . . . . .
H19A H 0.4541 -0.2471 0.3238 0.073 Uiso 1 1 calc R U . . .
H19B H 0.2779 -0.1729 0.3207 0.073 Uiso 1 1 calc R U . . .
C4 C 0.7809(5) 0.4401(3) 0.3575(2) 0.0464(8) Uani 1 1 d . . . . .
C6 C 0.7100(6) 0.3337(4) 0.4783(3) 0.0544(9) Uani 1 1 d . . . . .
H6 H 0.6418 0.3356 0.5314 0.065 Uiso 1 1 calc R U . . .
C3 C 0.8416(4) 0.3190(4) 0.3081(3) 0.0496(8) Uani 1 1 d . . . . .
H3 H 0.8692 0.3094 0.2451 0.059 Uiso 1 1 calc R U . . .
C5 C 0.7175(5) 0.4444(3) 0.4440(2) 0.0473(8) Uani 1 1 d . . . . .
H5 H 0.6538 0.5213 0.4737 0.057 Uiso 1 1 calc R U . . .
C2 C 0.8343(5) 0.2073(4) 0.3449(3) 0.0523(9) Uani 1 1 d . . . . .
H2 H 0.8549 0.1219 0.3055 0.063 Uiso 1 1 calc R U . . .
C8 C 0.7869(5) 0.5646(4) 0.3232(3) 0.0558(9) Uani 1 1 d . . . . .
H8 H 0.6736 0.6065 0.3342 0.067 Uiso 1 1 calc R U . . .
C20 C 0.3282(7) -0.2936(4) 0.1994(3) 0.0690(12) Uani 1 1 d . . . . .
H20A H 0.4324 -0.3287 0.1694 0.083 Uiso 1 1 calc R U . . .
H20B H 0.2589 -0.3661 0.2103 0.083 Uiso 1 1 calc R U . . .
C10 C 0.8168(8) 0.5430(5) 0.2234(3) 0.0821(15) Uani 1 1 d . . . . .
H10A H 0.8190 0.6257 0.2068 0.123 Uiso 1 1 calc R U . . .
H10B H 0.9267 0.5012 0.2105 0.123 Uiso 1 1 calc R U . . .
H10C H 0.7236 0.4885 0.1900 0.123 Uiso 1 1 calc R U . . .
C7 C 0.7600(8) 0.0914(4) 0.4679(3) 0.0787(15) Uani 1 1 d . . . . .
H7A H 0.7093 0.1139 0.5254 0.118 Uiso 1 1 calc R U . . .
H7B H 0.6898 0.0237 0.4288 0.118 Uiso 1 1 calc R U . . .
H7C H 0.8767 0.0611 0.4744 0.118 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Ru1 C2 2.194(4) . ?
Ru1 C3 2.202(4) . ?
Ru1 C1 2.228(4) . ?
Ru1 C4 2.231(3) . ?
Ru1 C6 2.243(4) . ?
Ru1 C5 2.249(3) . ?
Ru1 P1 2.3377(8) . ?
Ru1 Cl2 2.4035(8) . ?
Ru1 Cl1 2.4125(9) . ?
Cl3 P1 2.0865(11) . ?
P1 C17 1.847(3) . ?
P1 C11 1.849(3) . ?
C18 C19 1.523(5) . ?
C18 C17 1.524(5) . ?
C21 C20 1.510(7) . ?
C21 C22 1.524(5) . ?
C16 C11 1.522(5) . ?
C16 C15 1.527(5) . ?
C17 C22 1.529(5) . ?
C12 C13 1.528(5) . ?
C12 C11 1.534(4) . ?
C1 C2 1.393(6) . ?
C1 C6 1.432(5) . ?
C1 C7 1.509(6) . ?
C13 C14 1.512(6) . ?
C14 C15 1.532(5) . ?
C9 C8 1.525(6) . ?
C19 C20 1.516(6) . ?
C4 C3 1.421(5) . ?
C4 C5 1.423(5) . ?
C4 C8 1.518(5) . ?
C6 C5 1.383(6) . ?
C3 C2 1.416(6) . ?
C8 C10 1.523(7) . ?

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
C2 Ru1 C3 37.59(16) . . ?
C2 Ru1 C1 36.72(15) . . ?
C3 Ru1 C1 67.54(16) . . ?
C2 Ru1 C4 67.34(14) . . ?
C3 Ru1 C4 37.38(13) . . ?
C1 Ru1 C4 80.09(15) . . ?
C2 Ru1 C6 65.82(14) . . ?
C3 Ru1 C6 78.39(15) . . ?
C1 Ru1 C6 37.34(14) . . ?
C4 Ru1 C6 66.34(15) . . ?
C2 Ru1 C5 77.72(13) . . ?
C3 Ru1 C5 66.35(13) . . ?
C1 Ru1 C5 66.47(13) . . ?
C4 Ru1 C5 37.05(14) . . ?
C6 Ru1 C5 35.87(15) . . ?
C2 Ru1 P1 93.17(10) . . ?
C3 Ru1 P1 95.97(10) . . ?
C1 Ru1 P1 115.53(10) . . ?
C4 Ru1 P1 123.60(10) . . ?
C6 Ru1 P1 152.46(10) . . ?
C5 Ru1 P1 160.59(10) . . ?
C2 Ru1 Cl2 153.07(12) . . ?
C3 Ru1 Cl2 115.52(11) . . ?
C1 Ru1 Cl2 152.90(10) . . ?
C4 Ru1 Cl2 88.17(10) . . ?
C6 Ru1 Cl2 115.57(10) . . ?
C5 Ru1 Cl2 89.54(10) . . ?
P1 Ru1 Cl2 91.32(3) . . ?
C2 Ru1 Cl1 121.33(12) . . ?
C3 Ru1 Cl1 158.52(11) . . ?
C1 Ru1 Cl1 91.58(12) . . ?
C4 Ru1 Cl1 147.53(10) . . ?
C6 Ru1 Cl1 88.05(12) . . ?
C5 Ru1 Cl1 111.02(10) . . ?
P1 Ru1 Cl1 88.37(3) . . ?
Cl2 Ru1 Cl1 85.31(3) . . ?
C17 P1 C11 103.57(15) . . ?
C17 P1 Cl3 99.81(11) . . ?
C11 P1 Cl3 97.51(11) . . ?
C17 P1 Ru1 116.38(11) . . ?
C11 P1 Ru1 123.60(10) . . ?
Cl3 P1 Ru1 112.02(4) . . ?
C19 C18 C17 111.1(3) . . ?
C20 C21 C22 112.6(4) . . ?
C11 C16 C15 110.8(3) . . ?
C18 C17 C22 111.1(3) . . ?
C18 C17 P1 111.2(2) . . ?
C22 C17 P1 115.9(2) . . ?
C13 C12 C11 110.2(3) . . ?
C2 C1 C6 117.2(4) . . ?
C2 C1 C7 122.5(4) . . ?
C6 C1 C7 120.3(4) . . ?
C2 C1 Ru1 70.3(2) . . ?
C6 C1 Ru1 71.9(2) . . ?
C7 C1 Ru1 130.7(3) . . ?
C14 C13 C12 111.7(3) . . ?
C13 C14 C15 110.7(3) . . ?
C16 C15 C14 111.2(3) . . ?
C21 C22 C17 110.9(3) . . ?
C16 C11 C12 111.7(3) . . ?
C16 C11 P1 111.7(2) . . ?
C12 C11 P1 113.1(2) . . ?
C20 C19 C18 110.4(3) . . ?
C3 C4 C5 117.8(3) . . ?
C3 C4 C8 122.8(4) . . ?
C5 C4 C8 119.3(3) . . ?
C3 C4 Ru1 70.2(2) . . ?
C5 C4 Ru1 72.2(2) . . ?
C8 C4 Ru1 130.5(3) . . ?
C5 C6 C1 121.3(4) . . ?
C5 C6 Ru1 72.3(2) . . ?
C1 C6 Ru1 70.7(2) . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 Ru1 70.9(2) . . ?
C4 C3 Ru1 72.4(2) . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 Ru1 71.8(2) . . ?
C4 C5 Ru1 70.79(18) . . ?
C1 C2 C3 122.5(3) . . ?
C1 C2 Ru1 73.0(2) . . ?
C3 C2 Ru1 71.5(2) . . ?
C4 C8 C10 114.3(4) . . ?
C4 C8 C9 108.5(4) . . ?
C10 C8 C9 111.0(4) . . ?
C21 C20 C19 111.3(3) . . ?

_refine_diff_density_max         0.645
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.076
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4c
_database_code_depnum_ccdc_archive 'CCDC 1415871'
_audit_update_record             
;
2015-07-30 deposited with the CCDC.
2016-02-03 downloaded from the CCDC.
;
#=============================================================================== 

_audit_creation_method           SHELXL97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H23 Cl2 F6 O P Ru'
_chemical_formula_weight         644.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru 0.0552 3.2960 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.82310(10)
_cell_length_b                   11.2772(2)
_cell_length_c                   33.5183(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.0310(10)
_cell_angle_gamma                90
_cell_volume                     2578.66(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11045
_cell_measurement_theta_min      4.1220
_cell_measurement_theta_max      69.2890

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear light red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    7.961
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62494
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.2640
_diffrn_reflns_number            21368
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         4.136
_diffrn_reflns_theta_max         69.488
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4804
_reflns_number_gt                4495
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlis Pro CCD (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis Pro RED (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis Pro RED (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'DIRDIF-2008 (Beurskens et al., 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0203P)²+12.0241P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4804
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C7 C 0.0193(12) 0.4073(7) 0.1807(2) 0.074(2) Uani 1 1 d . . . . .
H7A H 0.1381 0.4525 0.1789 0.111 Uiso 1 1 calc R U . . .
H7B H -0.0883 0.4598 0.1857 0.111 Uiso 1 1 calc R U . . .
H7C H 0.0317 0.3512 0.2021 0.111 Uiso 1 1 calc R U . . .
C24 C -0.3590(16) -0.4090(8) 0.0643(3) 0.090(3) Uani 1 1 d . . . . .
C2 C -0.1811(8) 0.2699(5) 0.13657(18) 0.0446(13) Uani 1 1 d . . . . .
H2 H -0.2603 0.2489 0.1596 0.054 Uiso 1 1 calc R U . . .
C1 C -0.0175(9) 0.3428(6) 0.1423(2) 0.0539(15) Uani 1 1 d . . . . .
C15 C -0.4211(9) -0.0330(6) 0.24572(19) 0.0543(15) Uani 1 1 d . . . . .
H15 H -0.5210 -0.0848 0.2526 0.065 Uiso 1 1 calc R U . . .
C18 C -0.1089(8) -0.1267(5) 0.13276(17) 0.0447(13) Uani 1 1 d . . . . .
C19 C -0.2989(9) -0.1182(6) 0.11798(18) 0.0506(14) Uani 1 1 d . . . . .
H19 H -0.3727 -0.0509 0.1233 0.061 Uiso 1 1 calc R U . . .
C5 C 0.0827(10) 0.2962(6) 0.0744(2) 0.0576(16) Uani 1 1 d . . . . .
H5 H 0.1895 0.2930 0.0552 0.069 Uiso 1 1 calc R U . . .
C13 C -0.2371(10) 0.1426(6) 0.25853(19) 0.0544(15) Uani 1 1 d . . . . .
H13 H -0.2127 0.2097 0.2740 0.065 Uiso 1 1 calc R U . . .
C23 C 0.0004(10) -0.2264(6) 0.1245(2) 0.0580(16) Uani 1 1 d . . . . .
H23 H 0.1293 -0.2321 0.1339 0.070 Uiso 1 1 calc R U . . .
C20 C -0.3800(10) -0.2088(6) 0.09540(19) 0.0555(15) Uani 1 1 d . . . . .
H20 H -0.5075 -0.2021 0.0854 0.067 Uiso 1 1 calc R U . . .
C6 C 0.1147(10) 0.3558(6) 0.1099(2) 0.0621(18) Uani 1 1 d . . . . .
H6 H 0.2418 0.3940 0.1148 0.075 Uiso 1 1 calc R U . . .
C12 C -0.1228(10) 0.1199(6) 0.22590(18) 0.0547(15) Uani 1 1 d . . . . .
H12 H -0.0210 0.1711 0.2196 0.066 Uiso 1 1 calc R U . . .
C8 C -0.1090(12) 0.1573(7) 0.0288(2) 0.0689(19) Uani 1 1 d . . . . .
H8 H 0.0217 0.1347 0.0198 0.083 Uiso 1 1 calc R U . . .
C4 C -0.0818(9) 0.2180(6) 0.06845(18) 0.0499(14) Uani 1 1 d . . . . .
C17 C -0.5102(11) 0.0933(7) 0.3034(2) 0.0668(18) Uani 1 1 d . . . . .
C3 C -0.2124(8) 0.2081(5) 0.10006(17) 0.0448(13) Uani 1 1 d . . . . .
H3 H -0.3122 0.1457 0.0989 0.054 Uiso 1 1 calc R U . . .
C22 C -0.0822(11) -0.3183(6) 0.1023(2) 0.0672(19) Uani 1 1 d . . . . .
H22 H -0.0093 -0.3861 0.0972 0.081 Uiso 1 1 calc R U . . .
C11 C -0.1598(8) 0.0203(5) 0.20235(17) 0.0444(13) Uani 1 1 d . . . . .
C14 C -0.3861(9) 0.0675(6) 0.26834(18) 0.0486(14) Uani 1 1 d . . . . .
C10 C -0.2266(16) 0.0487(11) 0.0298(3) 0.112(4) Uani 1 1 d . . . . .
H10A H -0.2366 0.0158 0.0034 0.168 Uiso 1 1 calc R U . . .
H10B H -0.1649 -0.0077 0.0474 0.168 Uiso 1 1 calc R U . . .
H10C H -0.3552 0.0669 0.0392 0.168 Uiso 1 1 calc R U . . .
C9 C -0.189(2) 0.2476(12) -0.0006(3) 0.157(6) Uani 1 1 d . . . . .
H9A H -0.1065 0.3168 -0.0001 0.235 Uiso 1 1 calc R U . . .
H9B H -0.1901 0.2142 -0.0270 0.235 Uiso 1 1 calc R U . . .
H9C H -0.3194 0.2692 0.0065 0.235 Uiso 1 1 calc R U . . .
C16 C -0.3077(9) -0.0564(5) 0.21295(18) 0.0508(14) Uani 1 1 d . . . . .
H16 H -0.3310 -0.1244 0.1979 0.061 Uiso 1 1 calc R U . . .
C21 C -0.2721(11) -0.3091(6) 0.0878(2) 0.0588(16) Uani 1 1 d . . . . .
F1 F -0.4375(9) 0.1726(7) 0.32734(18) 0.151(3) Uani 1 1 d . . . . .
F2 F -0.6869(8) 0.1335(5) 0.29298(17) 0.1070(18) Uani 1 1 d . . . . .
F3 F -0.5513(9) -0.0023(5) 0.32451(15) 0.1055(18) Uani 1 1 d . . . . .
F4 F -0.5526(11) -0.4155(6) 0.0665(2) 0.145(3) Uani 1 1 d . . . . .
F5 F -0.2957(15) -0.5092(5) 0.0723(3) 0.231(6) Uani 1 1 d . . . . .
F6 F -0.3483(13) -0.3917(7) 0.0261(2) 0.161(3) Uani 1 1 d . . . . .
Cl2 Cl 0.3570(2) 0.17641(17) 0.17028(5) 0.0655(4) Uani 1 1 d . . . . .
Cl1 Cl 0.2695(2) 0.02614(16) 0.08623(5) 0.0642(4) Uani 1 1 d . . . . .
Ru1 Ru 0.08149(6) 0.16391(4) 0.12379(2) 0.04139(14) Uani 1 1 d . . . . .
P1 P 0.0006(2) -0.00360(13) 0.15995(4) 0.0427(3) Uani 1 1 d . . . . .
O1 O 0.1876(6) -0.0659(4) 0.18070(14) 0.0571(11) Uani 1 1 d . . . . .
H1O H 0.2844 -0.0238 0.1779 0.086 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C7 C1 1.494(9) . ?
C24 F5 1.237(10) . ?
C24 F6 1.299(11) . ?
C24 F4 1.327(12) . ?
C24 C21 1.491(11) . ?
C2 C1 1.397(8) . ?
C2 C3 1.421(8) . ?
C2 Ru1 2.202(5) . ?
C1 C6 1.433(10) . ?
C1 Ru1 2.220(6) . ?
C15 C16 1.381(9) . ?
C15 C14 1.382(9) . ?
C18 C23 1.380(8) . ?
C18 C19 1.383(8) . ?
C18 P1 1.814(6) . ?
C19 C20 1.381(9) . ?
C5 C6 1.381(10) . ?
C5 C4 1.439(9) . ?
C5 Ru1 2.230(6) . ?
C13 C14 1.368(9) . ?
C13 C12 1.379(9) . ?
C23 C22 1.390(10) . ?
C20 C21 1.376(9) . ?
C6 Ru1 2.226(6) . ?
C12 C11 1.394(8) . ?
C8 C10 1.464(13) . ?
C8 C4 1.503(10) . ?
C8 C9 1.512(12) . ?
C4 C3 1.401(8) . ?
C4 Ru1 2.232(6) . ?
C17 F1 1.293(9) . ?
C17 F3 1.322(9) . ?
C17 F2 1.329(9) . ?
C17 C14 1.491(9) . ?
C3 Ru1 2.201(5) . ?
C22 C21 1.380(10) . ?
C11 C16 1.380(8) . ?
C11 P1 1.829(6) . ?
Cl2 Ru1 2.4239(15) . ?
Cl1 Ru1 2.3880(16) . ?
Ru1 P1 2.3163(15) . ?
P1 O1 1.604(4) . ?

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
F5 C24 F6 109.0(10) . . ?
F5 C24 F4 106.4(11) . . ?
F6 C24 F4 97.9(8) . . ?
F5 C24 C21 116.2(7) . . ?
F6 C24 C21 112.3(9) . . ?
F4 C24 C21 113.5(8) . . ?
C1 C2 C3 121.0(6) . . ?
C1 C2 Ru1 72.3(3) . . ?
C3 C2 Ru1 71.1(3) . . ?
C2 C1 C6 117.9(6) . . ?
C2 C1 C7 121.8(6) . . ?
C6 C1 C7 120.3(6) . . ?
C2 C1 Ru1 70.9(3) . . ?
C6 C1 Ru1 71.5(4) . . ?
C7 C1 Ru1 129.5(5) . . ?
C16 C15 C14 120.0(6) . . ?
C23 C18 C19 119.4(6) . . ?
C23 C18 P1 120.3(5) . . ?
C19 C18 P1 120.2(5) . . ?
C20 C19 C18 120.6(6) . . ?
C6 C5 C4 121.9(6) . . ?
C6 C5 Ru1 71.8(4) . . ?
C4 C5 Ru1 71.3(3) . . ?
C14 C13 C12 120.6(6) . . ?
C18 C23 C22 119.9(6) . . ?
C21 C20 C19 119.9(6) . . ?
C5 C6 C1 120.8(6) . . ?
C5 C6 Ru1 72.1(4) . . ?
C1 C6 Ru1 71.0(4) . . ?
C13 C12 C11 120.0(6) . . ?
C10 C8 C4 114.9(6) . . ?
C10 C8 C9 112.8(9) . . ?
C4 C8 C9 107.9(7) . . ?
C3 C4 C5 116.7(6) . . ?
C3 C4 C8 124.2(6) . . ?
C5 C4 C8 119.0(6) . . ?
C3 C4 Ru1 70.4(3) . . ?
C5 C4 Ru1 71.1(3) . . ?
C8 C4 Ru1 131.4(5) . . ?
F1 C17 F3 108.4(7) . . ?
F1 C17 F2 105.3(7) . . ?
F3 C17 F2 102.7(6) . . ?
F1 C17 C14 114.0(6) . . ?
F3 C17 C14 113.0(6) . . ?
F2 C17 C14 112.6(6) . . ?
C4 C3 C2 121.6(6) . . ?
C4 C3 Ru1 72.8(3) . . ?
C2 C3 Ru1 71.2(3) . . ?
C21 C22 C23 120.1(6) . . ?
C16 C11 C12 119.0(6) . . ?
C16 C11 P1 123.9(5) . . ?
C12 C11 P1 117.0(4) . . ?
C13 C14 C15 119.9(6) . . ?
C13 C14 C17 120.2(6) . . ?
C15 C14 C17 119.9(6) . . ?
C11 C16 C15 120.5(6) . . ?
C20 C21 C22 119.9(6) . . ?
C20 C21 C24 120.6(7) . . ?
C22 C21 C24 119.4(7) . . ?
C3 Ru1 C2 37.7(2) . . ?
C3 Ru1 C1 67.4(2) . . ?
C2 Ru1 C1 36.8(2) . . ?
C3 Ru1 C6 78.4(2) . . ?
C2 Ru1 C6 66.4(2) . . ?
C1 Ru1 C6 37.6(3) . . ?
C3 Ru1 C5 66.1(2) . . ?
C2 Ru1 C5 78.2(2) . . ?
C1 Ru1 C5 66.7(3) . . ?
C6 Ru1 C5 36.1(3) . . ?
C3 Ru1 C4 36.8(2) . . ?
C2 Ru1 C4 67.5(2) . . ?
C1 Ru1 C4 80.5(2) . . ?
C6 Ru1 C4 67.1(3) . . ?
C5 Ru1 C4 37.6(2) . . ?
C3 Ru1 P1 98.61(16) . . ?
C2 Ru1 P1 97.97(16) . . ?
C1 Ru1 P1 121.20(18) . . ?
C6 Ru1 P1 158.2(2) . . ?
C5 Ru1 P1 159.82(19) . . ?
C4 Ru1 P1 122.53(17) . . ?
C3 Ru1 Cl1 116.82(16) . . ?
C2 Ru1 Cl1 154.45(16) . . ?
C1 Ru1 Cl1 155.23(18) . . ?
C6 Ru1 Cl1 117.7(2) . . ?
C5 Ru1 Cl1 91.97(19) . . ?
C4 Ru1 Cl1 90.25(16) . . ?
P1 Ru1 Cl1 83.14(6) . . ?
C3 Ru1 Cl2 155.51(16) . . ?
C2 Ru1 Cl2 117.88(16) . . ?
C1 Ru1 Cl2 90.20(17) . . ?
C6 Ru1 Cl2 89.85(19) . . ?
C5 Ru1 Cl2 115.18(19) . . ?
C4 Ru1 Cl2 152.65(17) . . ?
P1 Ru1 Cl2 84.29(6) . . ?
Cl1 Ru1 Cl2 87.66(6) . . ?
O1 P1 C18 101.5(3) . . ?
O1 P1 C11 102.1(3) . . ?
C18 P1 C11 104.8(3) . . ?
O1 P1 Ru1 112.88(18) . . ?
C18 P1 Ru1 117.47(19) . . ?
C11 P1 Ru1 116.0(2) . . ?

_refine_diff_density_max         0.784
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.091

