# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_ga_80629a_a
_database_code_depnum_ccdc_archive 'CCDC 1852640'
_audit_update_record             
;
2018-06-30 deposited with the CCDC.
2018-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 Cl N O Ru'
_chemical_formula_weight         458.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -0.0760 2.5955 '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                   9.0862(5)
_cell_length_b                   13.8263(8)
_cell_length_c                   16.6951(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.385(3)
_cell_angle_gamma                90
_cell_volume                     2040.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8835
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      59.38

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    5.059
_shelx_estimated_absorpt_T_min   0.389
_shelx_estimated_absorpt_T_max   0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.496
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15188
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.737
_diffrn_reflns_theta_max         59.420
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4501
_reflns_number_gt                3926
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0352P)²+1.4826P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4501
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_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 0.45761(2) 0.54927(2) 0.65456(2) 0.01732(9) Uani 1 1 d . . . . .
Cl1 Cl 0.33954(9) 0.38958(5) 0.63760(5) 0.02880(18) Uani 1 1 d . . . . .
O1 O 0.6552(2) 0.47567(15) 0.65349(14) 0.0240(4) Uani 1 1 d . . . . .
N1 N 0.4959(3) 0.52191(18) 0.78098(15) 0.0198(5) Uani 1 1 d . . . . .
C1 C 0.6190(4) 0.4576(3) 0.9166(2) 0.0376(8) Uani 1 1 d . . . . .
H1A H 0.6730 0.5121 0.9477 0.056 Uiso 1 1 calc R U . . .
H1B H 0.6743 0.3975 0.9344 0.056 Uiso 1 1 calc R U . . .
H1C H 0.5172 0.4531 0.9267 0.056 Uiso 1 1 calc R U . . .
C2 C 0.6076(3) 0.4730(2) 0.8258(2) 0.0239(6) Uani 1 1 d . . . . .
C3 C 0.7262(4) 0.4309(2) 0.7948(2) 0.0268(7) Uani 1 1 d . . . . .
H3 H 0.8001 0.3953 0.8330 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7455(3) 0.4363(2) 0.7156(2) 0.0233(6) Uani 1 1 d . . . . .
C5 C 0.8860(4) 0.3933(2) 0.6959(2) 0.0302(7) Uani 1 1 d . . . . .
H5A H 0.8568 0.3446 0.6524 0.045 Uiso 1 1 calc R U . . .
H5B H 0.9478 0.3628 0.7454 0.045 Uiso 1 1 calc R U . . .
H5C H 0.9445 0.4445 0.6771 0.045 Uiso 1 1 calc R U . . .
C6 C 0.3835(4) 0.5618(2) 0.82036(19) 0.0225(6) Uani 1 1 d . . . . .
C7 C 0.2439(4) 0.5162(2) 0.8090(2) 0.0274(7) Uani 1 1 d . . . . .
H7 H 0.2235 0.4594 0.7763 0.033 Uiso 1 1 calc R U . . .
C8 C 0.1346(4) 0.5543(2) 0.8459(2) 0.0301(7) Uani 1 1 d . . . . .
H8 H 0.0396 0.5225 0.8382 0.036 Uiso 1 1 calc R U . . .
C9 C 0.1602(4) 0.6375(2) 0.8936(2) 0.0295(7) Uani 1 1 d . . . . .
C10 C 0.2996(4) 0.6825(2) 0.9024(2) 0.0309(7) Uani 1 1 d . . . . .
H10 H 0.3195 0.7400 0.9342 0.037 Uiso 1 1 calc R U . . .
C11 C 0.4110(4) 0.6458(2) 0.8659(2) 0.0282(7) Uani 1 1 d . . . . .
H11 H 0.5051 0.6784 0.8723 0.034 Uiso 1 1 calc R U . . .
C12 C 0.0411(4) 0.6765(3) 0.9350(3) 0.0417(9) Uani 1 1 d . . . . .
H12A H -0.0288 0.7181 0.8964 0.062 Uiso 1 1 calc R U . . .
H12B H 0.0899 0.7142 0.9836 0.062 Uiso 1 1 calc R U . . .
H12C H -0.0150 0.6226 0.9517 0.062 Uiso 1 1 calc R U . . .
C13 C 0.5569(3) 0.6758(2) 0.6107(2) 0.0224(6) Uani 1 1 d . . . . .
C14 C 0.4784(4) 0.6219(2) 0.5403(2) 0.0229(6) Uani 1 1 d . . . . .
H14 H 0.530(4) 0.602(3) 0.502(2) 0.030(9) Uiso 1 1 d . . . . .
C15 C 0.3283(4) 0.5938(2) 0.5325(2) 0.0239(6) Uani 1 1 d . . . . .
H15 H 0.278(4) 0.553(2) 0.488(2) 0.025(9) Uiso 1 1 d . . . . .
C16 C 0.2456(3) 0.6214(2) 0.5925(2) 0.0248(6) Uani 1 1 d . . . . .
C17 C 0.3201(3) 0.6786(2) 0.6587(2) 0.0225(6) Uani 1 1 d . . . . .
H17 H 0.271(4) 0.694(2) 0.699(2) 0.027(9) Uiso 1 1 d . . . . .
C18 C 0.4756(3) 0.7057(2) 0.6694(2) 0.0228(6) Uani 1 1 d . . . . .
H18 H 0.523(4) 0.737(3) 0.721(2) 0.030(9) Uiso 1 1 d . . . . .
C19 C 0.7252(4) 0.6943(2) 0.6218(2) 0.0285(7) Uani 1 1 d . . . . .
H19 H 0.7686 0.6365 0.5995 0.034 Uiso 1 1 calc R U . . .
C20 C 0.8094(4) 0.7052(3) 0.7113(2) 0.0369(8) Uani 1 1 d . . . . .
H20A H 0.7741 0.7635 0.7345 0.055 Uiso 1 1 calc R U . . .
H20B H 0.9182 0.7107 0.7145 0.055 Uiso 1 1 calc R U . . .
H20C H 0.7904 0.6485 0.7426 0.055 Uiso 1 1 calc R U . . .
C21 C 0.7486(4) 0.7814(3) 0.5689(3) 0.0422(9) Uani 1 1 d . . . . .
H21A H 0.7041 0.8393 0.5877 0.063 Uiso 1 1 calc R U . . .
H21B H 0.6995 0.7687 0.5112 0.063 Uiso 1 1 calc R U . . .
H21C H 0.8571 0.7918 0.5742 0.063 Uiso 1 1 calc R U . . .
C22 C 0.0862(4) 0.5869(3) 0.5851(2) 0.0338(8) Uani 1 1 d . . . . .
H22A H 0.0561 0.5991 0.6369 0.051 Uiso 1 1 calc R U . . .
H22B H 0.0806 0.5173 0.5734 0.051 Uiso 1 1 calc R U . . .
H22C H 0.0181 0.6216 0.5403 0.051 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 O1 2.068(2) . ?
Ru1 N1 2.093(2) . ?
Ru1 C13 2.172(3) . ?
Ru1 C18 2.179(3) . ?
Ru1 C15 2.192(3) . ?
Ru1 C17 2.192(3) . ?
Ru1 C14 2.202(3) . ?
Ru1 C16 2.203(3) . ?
Ru1 Cl1 2.4425(8) . ?
O1 C4 1.285(4) . ?
N1 C2 1.302(4) . ?
N1 C6 1.446(4) . ?
C1 C2 1.512(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.422(4) . ?
C3 C4 1.375(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.513(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.379(4) . ?
C6 C7 1.390(4) . ?
C7 C8 1.388(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(5) . ?
C9 C12 1.511(4) . ?
C10 C11 1.393(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.418(4) . ?
C13 C14 1.435(4) . ?
C13 C19 1.519(4) . ?
C14 C15 1.395(4) . ?
C14 H14 0.92(4) . ?
C15 C16 1.436(4) . ?
C15 H15 0.97(4) . ?
C16 C17 1.400(4) . ?
C16 C22 1.503(4) . ?
C17 C18 1.432(4) . ?
C17 H17 0.91(4) . ?
C18 H18 0.97(4) . ?
C19 C20 1.519(5) . ?
C19 C21 1.537(5) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
O1 Ru1 N1 88.71(9) . . ?
O1 Ru1 C13 87.95(10) . . ?
N1 Ru1 C13 120.04(11) . . ?
O1 Ru1 C18 116.56(10) . . ?
N1 Ru1 C18 94.27(11) . . ?
C13 Ru1 C18 38.04(10) . . ?
O1 Ru1 C15 114.21(10) . . ?
N1 Ru1 C15 156.46(10) . . ?
C13 Ru1 C15 68.61(12) . . ?
C18 Ru1 C15 80.58(12) . . ?
O1 Ru1 C17 154.74(10) . . ?
N1 Ru1 C17 94.50(11) . . ?
C13 Ru1 C17 68.76(11) . . ?
C18 Ru1 C17 38.25(11) . . ?
C15 Ru1 C17 67.26(12) . . ?
O1 Ru1 C14 88.18(10) . . ?
N1 Ru1 C14 158.21(11) . . ?
C13 Ru1 C14 38.29(12) . . ?
C18 Ru1 C14 68.07(11) . . ?
C15 Ru1 C14 37.01(12) . . ?
C17 Ru1 C14 79.59(11) . . ?
O1 Ru1 C16 152.29(10) . . ?
N1 Ru1 C16 118.64(10) . . ?
C13 Ru1 C16 82.12(11) . . ?
C18 Ru1 C16 68.79(12) . . ?
C15 Ru1 C16 38.15(11) . . ?
C17 Ru1 C16 37.14(12) . . ?
C14 Ru1 C16 68.12(11) . . ?
O1 Ru1 Cl1 85.01(6) . . ?
N1 Ru1 Cl1 85.39(7) . . ?
C13 Ru1 Cl1 153.48(9) . . ?
C18 Ru1 Cl1 158.42(8) . . ?
C15 Ru1 Cl1 91.13(9) . . ?
C17 Ru1 Cl1 120.20(8) . . ?
C14 Ru1 Cl1 115.80(9) . . ?
C16 Ru1 Cl1 92.41(9) . . ?
C4 O1 Ru1 126.48(19) . . ?
C2 N1 C6 118.4(3) . . ?
C2 N1 Ru1 126.8(2) . . ?
C6 N1 Ru1 114.79(19) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 124.0(3) . . ?
N1 C2 C1 120.8(3) . . ?
C3 C2 C1 115.2(3) . . ?
C4 C3 C2 127.1(3) . . ?
C4 C3 H3 116.5 . . ?
C2 C3 H3 116.5 . . ?
O1 C4 C3 126.8(3) . . ?
O1 C4 C5 113.8(3) . . ?
C3 C4 C5 119.4(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 120.1(3) . . ?
C11 C6 N1 121.0(3) . . ?
C7 C6 N1 118.9(3) . . ?
C8 C7 C6 119.4(3) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 121.8(3) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C10 C9 C8 117.4(3) . . ?
C10 C9 C12 121.6(3) . . ?
C8 C9 C12 121.0(3) . . ?
C9 C10 C11 121.9(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C6 C11 C10 119.4(3) . . ?
C6 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 118.5(3) . . ?
C18 C13 C19 122.5(3) . . ?
C14 C13 C19 118.9(3) . . ?
C18 C13 Ru1 71.24(17) . . ?
C14 C13 Ru1 71.99(16) . . ?
C19 C13 Ru1 125.4(2) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 Ru1 71.09(17) . . ?
C13 C14 Ru1 69.73(17) . . ?
C15 C14 H14 120(2) . . ?
C13 C14 H14 119(2) . . ?
Ru1 C14 H14 129(2) . . ?
C14 C15 C16 121.3(3) . . ?
C14 C15 Ru1 71.89(18) . . ?
C16 C15 Ru1 71.35(18) . . ?
C14 C15 H15 121(2) . . ?
C16 C15 H15 118(2) . . ?
Ru1 C15 H15 127(2) . . ?
C17 C16 C15 117.8(3) . . ?
C17 C16 C22 121.7(3) . . ?
C15 C16 C22 120.5(3) . . ?
C17 C16 Ru1 71.01(17) . . ?
C15 C16 Ru1 70.50(17) . . ?
C22 C16 Ru1 128.0(2) . . ?
C16 C17 C18 121.9(3) . . ?
C16 C17 Ru1 71.85(17) . . ?
C18 C17 Ru1 70.38(16) . . ?
C16 C17 H17 119(2) . . ?
C18 C17 H17 119(2) . . ?
Ru1 C17 H17 127(2) . . ?
C13 C18 C17 119.7(3) . . ?
C13 C18 Ru1 70.71(17) . . ?
C17 C18 Ru1 71.37(17) . . ?
C13 C18 H18 123(2) . . ?
C17 C18 H18 117(2) . . ?
Ru1 C18 H18 124(2) . . ?
C13 C19 C20 113.6(3) . . ?
C13 C19 C21 109.3(3) . . ?
C20 C19 C21 112.4(3) . . ?
C13 C19 H19 107.0 . . ?
C20 C19 H19 107.0 . . ?
C21 C19 H19 107.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 -179.3(3) . . . . ?
Ru1 N1 C2 C3 1.4(5) . . . . ?
C6 N1 C2 C1 0.4(4) . . . . ?
Ru1 N1 C2 C1 -178.9(2) . . . . ?
N1 C2 C3 C4 1.7(5) . . . . ?
C1 C2 C3 C4 -178.0(3) . . . . ?
Ru1 O1 C4 C3 3.3(4) . . . . ?
Ru1 O1 C4 C5 -176.3(2) . . . . ?
C2 C3 C4 O1 -4.3(5) . . . . ?
C2 C3 C4 C5 175.2(3) . . . . ?
C2 N1 C6 C11 79.2(4) . . . . ?
Ru1 N1 C6 C11 -101.5(3) . . . . ?
C2 N1 C6 C7 -103.3(4) . . . . ?
Ru1 N1 C6 C7 76.1(3) . . . . ?
C11 C6 C7 C8 -1.9(5) . . . . ?
N1 C6 C7 C8 -179.4(3) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C7 C8 C9 C10 0.9(5) . . . . ?
C7 C8 C9 C12 -178.5(4) . . . . ?
C8 C9 C10 C11 -0.7(5) . . . . ?
C12 C9 C10 C11 178.6(3) . . . . ?
C7 C6 C11 C10 2.0(5) . . . . ?
N1 C6 C11 C10 179.5(3) . . . . ?
C9 C10 C11 C6 -0.7(5) . . . . ?
C18 C13 C14 C15 -4.3(4) . . . . ?
C19 C13 C14 C15 172.6(3) . . . . ?
Ru1 C13 C14 C15 51.6(3) . . . . ?
C18 C13 C14 Ru1 -55.8(2) . . . . ?
C19 C13 C14 Ru1 121.1(3) . . . . ?
C13 C14 C15 C16 2.7(4) . . . . ?
Ru1 C14 C15 C16 53.7(3) . . . . ?
C13 C14 C15 Ru1 -51.0(3) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
Ru1 C15 C16 C17 54.8(2) . . . . ?
C14 C15 C16 C22 -177.3(3) . . . . ?
Ru1 C15 C16 C22 -123.3(3) . . . . ?
C14 C15 C16 Ru1 -53.9(3) . . . . ?
C15 C16 C17 C18 -2.9(4) . . . . ?
C22 C16 C17 C18 175.2(3) . . . . ?
Ru1 C16 C17 C18 51.7(3) . . . . ?
C15 C16 C17 Ru1 -54.5(2) . . . . ?
C22 C16 C17 Ru1 123.5(3) . . . . ?
C14 C13 C18 C17 2.3(4) . . . . ?
C19 C13 C18 C17 -174.5(3) . . . . ?
Ru1 C13 C18 C17 -53.9(3) . . . . ?
C14 C13 C18 Ru1 56.2(2) . . . . ?
C19 C13 C18 Ru1 -120.6(3) . . . . ?
C16 C17 C18 C13 1.3(5) . . . . ?
Ru1 C17 C18 C13 53.6(3) . . . . ?
C16 C17 C18 Ru1 -52.3(3) . . . . ?
C18 C13 C19 C20 25.3(4) . . . . ?
C14 C13 C19 C20 -151.5(3) . . . . ?
Ru1 C13 C19 C20 -63.8(4) . . . . ?
C18 C13 C19 C21 -101.2(4) . . . . ?
C14 C13 C19 C21 82.0(3) . . . . ?
Ru1 C13 C19 C21 169.7(2) . . . . ?

_refine_diff_density_max         0.853
_refine_diff_density_min         -0.789
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_ga_80503h_a
_database_code_depnum_ccdc_archive 'CCDC 1852641'
_audit_update_record             
;
2018-06-30 deposited with the CCDC.
2018-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 Cl F3 N O Ru'
_chemical_formula_weight         512.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -0.0760 2.5955 '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                   9.1752(4)
_cell_length_b                   13.9311(7)
_cell_length_c                   16.7961(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.993(2)
_cell_angle_gamma                90
_cell_volume                     2100.03(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3525
_cell_measurement_theta_min      3.62
_cell_measurement_theta_max      53.71

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    5.097
_shelx_estimated_absorpt_T_min   0.717
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13051
_diffrn_reflns_av_unetI/netI     0.0853
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.683
_diffrn_reflns_theta_max         54.031
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3818
_reflns_number_gt                2840
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3818
_refine_ls_number_parameters     311
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.005
_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 0.45860(4) 0.44909(2) 0.15420(2) 0.01925(14) Uani 1 1 d . . . . .
Cl1 Cl 0.35013(14) 0.60933(8) 0.14010(7) 0.0305(3) Uani 1 1 d . . . . .
O1 O 0.6562(3) 0.5195(2) 0.15279(19) 0.0243(7) Uani 1 1 d . . . . .
N1 N 0.4928(4) 0.4746(3) 0.2791(2) 0.0226(9) Uani 1 1 d . . . . .
F1 F -0.0709(19) 0.304(2) 0.3887(7) 0.101(9) Uani 0.45(2) 1 d D U P A 1
F2 F 0.0889(17) 0.2743(15) 0.4916(14) 0.082(6) Uani 0.45(2) 1 d . U P A 1
F3 F -0.002(3) 0.4098(9) 0.4770(14) 0.079(6) Uani 0.45(2) 1 d . U P A 1
F1' F -0.0814(15) 0.3944(11) 0.4262(12) 0.079(6) Uani 0.55(2) 1 d . U P A 2
F2' F -0.0174(16) 0.2534(8) 0.4139(10) 0.069(5) Uani 0.55(2) 1 d . U P A 2
F3' F 0.0835(13) 0.3308(15) 0.5160(5) 0.071(5) Uani 0.55(2) 1 d . U P A 2
C1 C 0.6121(6) 0.5381(4) 0.4132(3) 0.0351(13) Uani 1 1 d . . . . .
H1A H 0.5111 0.5383 0.4240 0.053 Uiso 1 1 calc R U . . .
H1B H 0.6606 0.5995 0.4302 0.053 Uiso 1 1 calc R U . . .
H1C H 0.6697 0.4858 0.4438 0.053 Uiso 1 1 calc R U . . .
C2 C 0.6041(5) 0.5237(4) 0.3241(3) 0.0265(11) Uani 1 1 d . . . . .
C3 C 0.7202(5) 0.5653(3) 0.2925(3) 0.0270(11) Uani 1 1 d . . . . .
H3 H 0.7916 0.6014 0.3297 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7424(5) 0.5598(3) 0.2134(3) 0.0250(11) Uani 1 1 d . . . . .
C5 C 0.8797(5) 0.6038(4) 0.1933(3) 0.0346(13) Uani 1 1 d . . . . .
H5A H 0.9518 0.5531 0.1891 0.052 Uiso 1 1 calc R U . . .
H5B H 0.9239 0.6489 0.2364 0.052 Uiso 1 1 calc R U . . .
H5C H 0.8531 0.6381 0.1414 0.052 Uiso 1 1 calc R U . . .
C6 C 0.3800(5) 0.4382(3) 0.3182(3) 0.0225(10) Uani 1 1 d . . . . .
C7 C 0.4013(5) 0.3552(3) 0.3650(3) 0.0261(11) Uani 1 1 d . . . . .
H7 H 0.4921 0.3206 0.3706 0.031 Uiso 1 1 calc R U . . .
C8 C 0.2914(6) 0.3228(4) 0.4032(3) 0.0299(12) Uani 1 1 d . . . . .
H8 H 0.3074 0.2664 0.4357 0.036 Uiso 1 1 calc R U . . .
C9 C 0.1573(5) 0.3720(3) 0.3945(3) 0.0257(11) Uani 1 1 d . . . . .
C10 C 0.1338(6) 0.4528(4) 0.3449(3) 0.0308(12) Uani 1 1 d . . . . .
H10 H 0.0410 0.4856 0.3371 0.037 Uiso 1 1 calc R U . . .
C11 C 0.2430(5) 0.4859(4) 0.3070(3) 0.0277(11) Uani 1 1 d . . . . .
H11 H 0.2256 0.5412 0.2732 0.033 Uiso 1 1 calc R U . . .
C12 C 0.0397(6) 0.3398(4) 0.4369(3) 0.0315(12) Uani 1 1 d D . . . .
C13 C 0.5535(5) 0.3231(3) 0.1082(3) 0.0243(11) Uani 1 1 d . . . . .
C14 C 0.4719(5) 0.2932(3) 0.1668(3) 0.0237(11) Uani 1 1 d . . . . .
H14 H 0.515(6) 0.254(4) 0.210(3) 0.037(15) Uiso 1 1 d . . . . .
C15 C 0.3192(6) 0.3223(4) 0.1581(3) 0.0286(11) Uani 1 1 d . . . . .
H15 H 0.274(5) 0.308(3) 0.197(3) 0.021(13) Uiso 1 1 d . . . . .
C16 C 0.2487(5) 0.3805(4) 0.0940(3) 0.0283(11) Uani 1 1 d . . . . .
C17 C 0.3306(6) 0.4078(4) 0.0341(3) 0.0280(11) Uani 1 1 d . . . . .
H17 H 0.295(5) 0.453(3) -0.009(3) 0.021(12) Uiso 1 1 d . . . . .
C18 C 0.4777(5) 0.3777(3) 0.0401(3) 0.0237(11) Uani 1 1 d . . . . .
H18 H 0.535(6) 0.396(4) 0.003(3) 0.043(16) Uiso 1 1 d . . . . .
C19 C 0.7174(5) 0.3017(4) 0.1166(3) 0.0294(11) Uani 1 1 d . . . . .
H19 H 0.7625 0.3578 0.0934 0.035 Uiso 1 1 calc R U . . .
C20 C 0.7365(7) 0.2146(4) 0.0646(4) 0.0489(16) Uani 1 1 d . . . . .
H20A H 0.6875 0.1589 0.0832 0.073 Uiso 1 1 calc R U . . .
H20B H 0.8429 0.2010 0.0698 0.073 Uiso 1 1 calc R U . . .
H20C H 0.6914 0.2279 0.0075 0.073 Uiso 1 1 calc R U . . .
C21 C 0.8005(6) 0.2903(4) 0.2043(4) 0.0438(15) Uani 1 1 d . . . . .
H21A H 0.7830 0.3467 0.2358 0.066 Uiso 1 1 calc R U . . .
H21B H 0.9075 0.2840 0.2058 0.066 Uiso 1 1 calc R U . . .
H21C H 0.7647 0.2327 0.2277 0.066 Uiso 1 1 calc R U . . .
C22 C 0.0930(6) 0.4163(4) 0.0887(4) 0.0386(13) Uani 1 1 d . . . . .
H22A H 0.0253 0.3830 0.0445 0.058 Uiso 1 1 calc R U . . .
H22B H 0.0894 0.4855 0.0778 0.058 Uiso 1 1 calc R U . . .
H22C H 0.0624 0.4039 0.1403 0.058 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 O1 2.066(3) . ?
Ru1 N1 2.087(4) . ?
Ru1 C13 2.171(5) . ?
Ru1 C14 2.183(5) . ?
Ru1 C15 2.190(5) . ?
Ru1 C17 2.190(5) . ?
Ru1 C18 2.197(5) . ?
Ru1 C16 2.199(4) . ?
Ru1 Cl1 2.4356(12) . ?
O1 C4 1.281(5) . ?
N1 C2 1.327(6) . ?
N1 C6 1.429(6) . ?
F1 C12 1.262(11) . ?
F2 C12 1.307(12) . ?
F3 C12 1.286(11) . ?
F1' C12 1.327(9) . ?
F2' C12 1.337(10) . ?
F3' C12 1.311(9) . ?
C1 C2 1.497(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.409(7) . ?
C3 C4 1.387(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.501(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.388(6) . ?
C6 C11 1.400(7) . ?
C7 C8 1.380(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(7) . ?
C9 C12 1.481(7) . ?
C10 C11 1.374(7) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 C14 1.417(6) . ?
C13 C18 1.429(7) . ?
C13 C19 1.511(7) . ?
C14 C15 1.437(7) . ?
C14 H14 0.93(5) . ?
C15 C16 1.395(7) . ?
C15 H15 0.87(5) . ?
C16 C17 1.426(7) . ?
C16 C22 1.499(7) . ?
C17 C18 1.397(7) . ?
C17 H17 0.96(5) . ?
C18 H18 0.92(6) . ?
C19 C21 1.520(7) . ?
C19 C20 1.526(7) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
O1 Ru1 N1 88.94(13) . . ?
O1 Ru1 C13 87.82(15) . . ?
N1 Ru1 C13 120.52(16) . . ?
O1 Ru1 C14 116.22(15) . . ?
N1 Ru1 C14 94.51(16) . . ?
C13 Ru1 C14 37.98(17) . . ?
O1 Ru1 C15 154.55(17) . . ?
N1 Ru1 C15 94.26(17) . . ?
C13 Ru1 C15 68.83(19) . . ?
C14 Ru1 C15 38.38(18) . . ?
O1 Ru1 C17 114.73(16) . . ?
N1 Ru1 C17 155.63(18) . . ?
C13 Ru1 C17 68.78(18) . . ?
C14 Ru1 C17 80.58(19) . . ?
C15 Ru1 C17 67.09(19) . . ?
O1 Ru1 C18 88.61(16) . . ?
N1 Ru1 C18 158.63(16) . . ?
C13 Ru1 C18 38.17(17) . . ?
C14 Ru1 C18 67.76(18) . . ?
C15 Ru1 C18 79.30(19) . . ?
C17 Ru1 C18 37.13(18) . . ?
O1 Ru1 C16 152.61(16) . . ?
N1 Ru1 C16 118.10(17) . . ?
C13 Ru1 C16 82.12(18) . . ?
C14 Ru1 C16 68.80(18) . . ?
C15 Ru1 C16 37.06(19) . . ?
C17 Ru1 C16 37.93(18) . . ?
C18 Ru1 C16 67.87(18) . . ?
O1 Ru1 Cl1 84.58(9) . . ?
N1 Ru1 Cl1 85.09(11) . . ?
C13 Ru1 Cl1 153.17(13) . . ?
C14 Ru1 Cl1 159.20(13) . . ?
C15 Ru1 Cl1 120.84(14) . . ?
C17 Ru1 Cl1 91.21(14) . . ?
C18 Ru1 Cl1 115.78(13) . . ?
C16 Ru1 Cl1 93.01(14) . . ?
C4 O1 Ru1 126.6(3) . . ?
C2 N1 C6 117.9(4) . . ?
C2 N1 Ru1 126.7(3) . . ?
C6 N1 Ru1 115.4(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 123.4(5) . . ?
N1 C2 C1 120.6(5) . . ?
C3 C2 C1 116.0(4) . . ?
C4 C3 C2 127.7(4) . . ?
C4 C3 H3 116.2 . . ?
C2 C3 H3 116.2 . . ?
O1 C4 C3 126.6(4) . . ?
O1 C4 C5 114.1(4) . . ?
C3 C4 C5 119.3(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 119.2(4) . . ?
C7 C6 N1 121.7(4) . . ?
C11 C6 N1 119.0(4) . . ?
C8 C7 C6 120.4(5) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.4(5) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 119.1(5) . . ?
C8 C9 C12 121.2(4) . . ?
C10 C9 C12 119.7(4) . . ?
C11 C10 C9 120.8(5) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C6 120.0(4) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?
F1 C12 F3 110.6(12) . . ?
F1 C12 F2 106.7(11) . . ?
F3 C12 F2 104.9(10) . . ?
F3' C12 F1' 105.3(9) . . ?
F3' C12 F2' 103.0(8) . . ?
F1' C12 F2' 102.2(8) . . ?
F1 C12 C9 112.4(7) . . ?
F3 C12 C9 110.2(6) . . ?
F2 C12 C9 111.7(7) . . ?
F3' C12 C9 114.5(6) . . ?
F1' C12 C9 115.8(5) . . ?
F2' C12 C9 114.5(6) . . ?
C14 C13 C18 118.2(4) . . ?
C14 C13 C19 122.5(4) . . ?
C18 C13 C19 119.3(4) . . ?
C14 C13 Ru1 71.4(3) . . ?
C18 C13 Ru1 71.9(3) . . ?
C19 C13 Ru1 126.3(3) . . ?
C13 C14 C15 119.4(5) . . ?
C13 C14 Ru1 70.6(3) . . ?
C15 C14 Ru1 71.1(3) . . ?
C13 C14 H14 121(3) . . ?
C15 C14 H14 119(3) . . ?
Ru1 C14 H14 132(3) . . ?
C16 C15 C14 121.9(5) . . ?
C16 C15 Ru1 71.8(3) . . ?
C14 C15 Ru1 70.5(3) . . ?
C16 C15 H15 120(3) . . ?
C14 C15 H15 118(3) . . ?
Ru1 C15 H15 125(3) . . ?
C15 C16 C17 118.2(5) . . ?
C15 C16 C22 121.5(5) . . ?
C17 C16 C22 120.3(5) . . ?
C15 C16 Ru1 71.1(3) . . ?
C17 C16 Ru1 70.7(3) . . ?
C22 C16 Ru1 128.0(3) . . ?
C18 C17 C16 120.8(5) . . ?
C18 C17 Ru1 71.7(3) . . ?
C16 C17 Ru1 71.4(3) . . ?
C18 C17 H17 115(3) . . ?
C16 C17 H17 124(3) . . ?
Ru1 C17 H17 123(3) . . ?
C17 C18 C13 121.4(5) . . ?
C17 C18 Ru1 71.1(3) . . ?
C13 C18 Ru1 69.9(3) . . ?
C17 C18 H18 123(3) . . ?
C13 C18 H18 116(3) . . ?
Ru1 C18 H18 128(3) . . ?
C13 C19 C21 113.5(4) . . ?
C13 C19 C20 109.5(4) . . ?
C21 C19 C20 112.1(5) . . ?
C13 C19 H19 107.1 . . ?
C21 C19 H19 107.1 . . ?
C20 C19 H19 107.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 -178.4(4) . . . . ?
Ru1 N1 C2 C3 -1.2(7) . . . . ?
C6 N1 C2 C1 1.4(6) . . . . ?
Ru1 N1 C2 C1 178.6(4) . . . . ?
N1 C2 C3 C4 -2.8(8) . . . . ?
C1 C2 C3 C4 177.4(5) . . . . ?
Ru1 O1 C4 C3 -0.6(7) . . . . ?
Ru1 O1 C4 C5 179.0(3) . . . . ?
C2 C3 C4 O1 3.9(8) . . . . ?
C2 C3 C4 C5 -175.7(5) . . . . ?
C2 N1 C6 C7 -79.3(6) . . . . ?
Ru1 N1 C6 C7 103.2(4) . . . . ?
C2 N1 C6 C11 102.6(5) . . . . ?
Ru1 N1 C6 C11 -74.9(5) . . . . ?
C11 C6 C7 C8 -3.2(7) . . . . ?
N1 C6 C7 C8 178.8(4) . . . . ?
C6 C7 C8 C9 0.8(7) . . . . ?
C7 C8 C9 C10 1.9(7) . . . . ?
C7 C8 C9 C12 -178.3(5) . . . . ?
C8 C9 C10 C11 -2.3(7) . . . . ?
C12 C9 C10 C11 177.9(5) . . . . ?
C9 C10 C11 C6 0.0(8) . . . . ?
C7 C6 C11 C10 2.7(7) . . . . ?
N1 C6 C11 C10 -179.1(4) . . . . ?
C8 C9 C12 F1 -108.4(17) . . . . ?
C10 C9 C12 F1 71.4(18) . . . . ?
C8 C9 C12 F3 127.7(14) . . . . ?
C10 C9 C12 F3 -52.5(15) . . . . ?
C8 C9 C12 F2 11.6(15) . . . . ?
C10 C9 C12 F2 -168.7(15) . . . . ?
C8 C9 C12 F3' 55.0(13) . . . . ?
C10 C9 C12 F3' -125.2(12) . . . . ?
C8 C9 C12 F1' 177.8(12) . . . . ?
C10 C9 C12 F1' -2.5(14) . . . . ?
C8 C9 C12 F2' -63.7(11) . . . . ?
C10 C9 C12 F2' 116.1(11) . . . . ?
C18 C13 C14 C15 -2.9(7) . . . . ?
C19 C13 C14 C15 175.3(4) . . . . ?
Ru1 C13 C14 C15 53.6(4) . . . . ?
C18 C13 C14 Ru1 -56.5(4) . . . . ?
C19 C13 C14 Ru1 121.7(4) . . . . ?
C13 C14 C15 C16 -0.8(7) . . . . ?
Ru1 C14 C15 C16 52.5(4) . . . . ?
C13 C14 C15 Ru1 -53.3(4) . . . . ?
C14 C15 C16 C17 2.6(7) . . . . ?
Ru1 C15 C16 C17 54.6(4) . . . . ?
C14 C15 C16 C22 -175.5(5) . . . . ?
Ru1 C15 C16 C22 -123.6(5) . . . . ?
C14 C15 C16 Ru1 -51.9(4) . . . . ?
C15 C16 C17 C18 -0.6(7) . . . . ?
C22 C16 C17 C18 177.6(4) . . . . ?
Ru1 C16 C17 C18 54.2(4) . . . . ?
C15 C16 C17 Ru1 -54.8(4) . . . . ?
C22 C16 C17 Ru1 123.4(4) . . . . ?
C16 C17 C18 C13 -3.2(7) . . . . ?
Ru1 C17 C18 C13 50.8(4) . . . . ?
C16 C17 C18 Ru1 -54.0(4) . . . . ?
C14 C13 C18 C17 5.0(7) . . . . ?
C19 C13 C18 C17 -173.3(4) . . . . ?
Ru1 C13 C18 C17 -51.3(4) . . . . ?
C14 C13 C18 Ru1 56.3(4) . . . . ?
C19 C13 C18 Ru1 -122.0(4) . . . . ?
C14 C13 C19 C21 -27.2(6) . . . . ?
C18 C13 C19 C21 151.0(5) . . . . ?
Ru1 C13 C19 C21 62.7(6) . . . . ?
C14 C13 C19 C20 99.0(5) . . . . ?
C18 C13 C19 C20 -82.8(6) . . . . ?
Ru1 C13 C19 C20 -171.1(4) . . . . ?

_refine_diff_density_max         0.843
_refine_diff_density_min         -1.149
_refine_diff_density_rms         0.117

