# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
# 
#######################################################################

data_mo_ybb1_0m
_database_code_depnum_ccdc_archive 'CCDC 1846966'
_audit_update_record             
;
2018-06-04 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;
_audit_creation_date             2017-08-22
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 Cl N4 Ru, F6 P, C H2 Cl2'
_chemical_formula_sum            'C22 H24 Cl3 F6 N4 P Ru'
_chemical_formula_weight         696.84
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.1480 0.1590 '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 0.0060 0.0030 '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 -1.2590 0.8360 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1716(4)
_cell_length_b                   30.1115(13)
_cell_length_c                   10.9853(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.159(2)
_cell_angle_gamma                90
_cell_volume                     2692.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.410
_cell_measurement_theta_min      3.058
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.001
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0624 before and 0.0476 after correction.
The Ratio of minimum to maximum transmission is 0.8936.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30775
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_min         2.982
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5165
_reflns_number_total             5494
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.247
_refine_diff_density_min         -1.152
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.266
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         5494
_refine_ls_number_restraints     198
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.304
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0123P)²+11.7502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0986
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F6) \\sim Ueq, Uanis(F5A) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1A)
\\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F4A) \\sim Ueq, Uanis(F6A) \\sim Ueq,
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F5) \\sim
Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of
0.01
3. Rigid body (RIGU) restrains
 P1, F1, F2, F3, F4, F5, F6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 P1, F1, F1A, F2, F2A, F3, F3A, F4, F4A, F5, F5A, F6, F6A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C19(H19)
5.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C16(H16), C17(H17)
5.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.60642(4) 0.41553(2) 0.41260(3) 0.01326(9) Uani 1 1 d . . . . .
Cl1 Cl 0.76148(12) 0.44982(3) 0.58277(9) 0.0213(2) Uani 1 1 d . . . . .
N1 N 0.4520(4) 0.39485(10) 0.5373(3) 0.0151(6) Uani 1 1 d . . . . .
N2 N 0.5050(4) 0.36009(10) 0.6104(3) 0.0161(6) Uani 1 1 d . . . . .
N3 N 0.7151(4) 0.35734(10) 0.4851(3) 0.0166(6) Uani 1 1 d . . . . .
N4 N 0.3114(4) 0.40944(11) 0.5659(3) 0.0187(7) Uani 1 1 d . . . . .
C1 C 0.6501(5) 0.33873(13) 0.5811(4) 0.0182(8) Uani 1 1 d . . . . .
C2 C 0.8545(5) 0.33904(14) 0.4497(4) 0.0245(9) Uani 1 1 d . . . . .
H2 H 0.902700 0.351643 0.382149 0.029 Uiso 1 1 calc R . . . .
C3 C 0.9292(6) 0.30285(15) 0.5079(4) 0.0304(10) Uani 1 1 d . . . . .
H3 H 1.026233 0.290441 0.480361 0.037 Uiso 1 1 calc R . . . .
C4 C 0.8599(6) 0.28498(15) 0.6073(5) 0.0336(11) Uani 1 1 d . . . . .
H4 H 0.910571 0.260399 0.649736 0.040 Uiso 1 1 calc R . . . .
C5 C 0.7171(5) 0.30282(14) 0.6449(4) 0.0262(9) Uani 1 1 d . . . . .
H5 H 0.667034 0.290724 0.712250 0.031 Uiso 1 1 calc R . . . .
C6 C 0.3895(5) 0.35211(12) 0.6919(3) 0.0171(8) Uani 1 1 d . . . . .
C7 C 0.2671(5) 0.38363(13) 0.6610(3) 0.0170(8) Uani 1 1 d . . . . .
C8 C 0.1240(5) 0.38583(14) 0.7215(4) 0.0237(9) Uani 1 1 d . . . . .
H8 H 0.039578 0.406770 0.699280 0.028 Uiso 1 1 calc R . . . .
C9 C 0.1122(6) 0.35609(16) 0.8148(4) 0.0287(10) Uani 1 1 d . . . . .
H9 H 0.017533 0.356563 0.859056 0.034 Uiso 1 1 calc R . . . .
C10 C 0.2371(6) 0.32484(15) 0.8468(4) 0.0314(10) Uani 1 1 d . . . . .
H10 H 0.223318 0.304886 0.912077 0.038 Uiso 1 1 calc R . . . .
C11 C 0.3773(6) 0.32199(14) 0.7878(4) 0.0261(9) Uani 1 1 d . . . . .
H11 H 0.461049 0.300918 0.810477 0.031 Uiso 1 1 calc R . . . .
C12 C 0.4186(5) 0.40984(13) 0.2579(3) 0.0173(8) Uani 1 1 d . . . . .
C13 C 0.4199(5) 0.45445(13) 0.3045(3) 0.0175(8) Uani 1 1 d . . . . .
H13 H 0.320288 0.467325 0.325981 0.021 Uiso 1 1 calc R . . . .
C14 C 0.5646(5) 0.47915(13) 0.3188(3) 0.0194(8) Uani 1 1 d . . . . .
H14 H 0.562539 0.508164 0.352636 0.023 Uiso 1 1 calc R . . . .
C15 C 0.7166(5) 0.46162(13) 0.2834(4) 0.0206(8) Uani 1 1 d . . . . .
C16 C 0.7151(5) 0.41871(14) 0.2359(3) 0.0203(8) Uani 1 1 d . . . . .
H16 H 0.813743 0.406638 0.210279 0.024 Uiso 1 1 calc R . . . .
C17 C 0.5686(5) 0.39230(13) 0.2247(3) 0.0185(8) Uani 1 1 d . . . . .
H17 H 0.572404 0.362756 0.194717 0.022 Uiso 1 1 calc R . . . .
C18 C 0.8714(6) 0.48819(16) 0.3023(5) 0.0342(11) Uani 1 1 d . . . . .
H18A H 0.868264 0.506641 0.375588 0.051 Uiso 1 1 calc GR . . . .
H18B H 0.881379 0.507274 0.231121 0.051 Uiso 1 1 calc GR . . . .
H18C H 0.965855 0.468077 0.312681 0.051 Uiso 1 1 calc GR . . . .
C19 C 0.2594(5) 0.38386(14) 0.2479(4) 0.0229(8) Uani 1 1 d . . . . .
H19 H 0.193409 0.394033 0.315017 0.028 Uiso 1 1 calc R . . . .
C20 C 0.2840(6) 0.33415(16) 0.2614(6) 0.0428(13) Uani 1 1 d . . . . .
H20A H 0.340096 0.322875 0.192531 0.064 Uiso 1 1 calc GR . . . .
H20B H 0.176981 0.319552 0.262468 0.064 Uiso 1 1 calc GR . . . .
H20C H 0.350946 0.327877 0.338066 0.064 Uiso 1 1 calc GR . . . .
C21 C 0.1646(6) 0.39604(18) 0.1265(4) 0.0356(11) Uani 1 1 d . . . . .
H21A H 0.142127 0.428012 0.124728 0.053 Uiso 1 1 calc GR . . . .
H21B H 0.060635 0.379648 0.117678 0.053 Uiso 1 1 calc GR . . . .
H21C H 0.230217 0.388283 0.059179 0.053 Uiso 1 1 calc GR . . . .
P1 P 0.30274(14) 0.21216(4) 0.55370(10) 0.0242(2) Uani 1 1 d . U . . .
F1 F 0.4955(13) 0.2127(5) 0.5467(10) 0.050(2) Uani 0.579(13) 1 d . U P A 1
F1A F 0.475(2) 0.2159(7) 0.5052(15) 0.060(4) Uani 0.421(13) 1 d . U P A 2
F2 F 0.1291(14) 0.2117(4) 0.5988(13) 0.088(3) Uani 0.579(13) 1 d . U P A 1
F2A F 0.1053(13) 0.2057(4) 0.5503(10) 0.040(2) Uani 0.421(13) 1 d . U P A 2
F3 F 0.3046(9) 0.2664(2) 0.5495(8) 0.0432(18) Uani 0.579(13) 1 d . U P A 1
F3A F 0.2926(15) 0.2578(4) 0.6087(13) 0.060(3) Uani 0.421(13) 1 d . U P A 2
F4 F 0.3138(8) 0.1604(2) 0.5660(10) 0.053(2) Uani 0.579(13) 1 d . U P A 1
F4A F 0.2932(13) 0.1635(3) 0.4850(14) 0.060(3) Uani 0.421(13) 1 d . U P A 2
F5 F 0.2705(15) 0.2114(4) 0.4169(8) 0.093(3) Uani 0.579(13) 1 d . U P A 1
F5A F 0.2353(14) 0.2340(4) 0.4214(10) 0.059(3) Uani 0.421(13) 1 d . U P A 2
F6 F 0.3655(16) 0.2152(4) 0.6966(7) 0.106(3) Uani 0.579(13) 1 d . U P A 1
F6A F 0.3357(12) 0.1859(5) 0.6748(10) 0.068(4) Uani 0.421(13) 1 d . U P A 2
Cl3 Cl -0.02131(19) 0.05726(6) 0.42141(14) 0.0538(4) Uani 1 1 d . . . . .
Cl4 Cl 0.3237(2) 0.03248(7) 0.44599(15) 0.0663(5) Uani 1 1 d . . . . .
C22 C 0.1765(8) 0.0720(2) 0.3901(5) 0.0521(15) Uani 1 1 d . . . . .
H22A H 0.204640 0.101226 0.427763 0.063 Uiso 1 1 calc R . . . .
H22B H 0.179891 0.075043 0.300611 0.063 Uiso 1 1 calc R . . . .


_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 Cl1 2.3959(10) . ?
Ru1 N1 2.042(3) . ?
Ru1 N3 2.090(3) . ?
Ru1 C12 2.192(4) . ?
Ru1 C13 2.187(4) . ?
Ru1 C14 2.187(4) . ?
Ru1 C15 2.231(4) . ?
Ru1 C16 2.208(4) . ?
Ru1 C17 2.175(4) . ?
N1 N2 1.366(4) . ?
N1 N4 1.294(4) . ?
N2 C1 1.412(5) . ?
N2 C6 1.379(5) . ?
N3 C1 1.345(5) . ?
N3 C2 1.353(5) . ?
N4 C7 1.376(5) . ?
C1 C5 1.375(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.398(5) . ?
C6 C11 1.400(5) . ?
C7 C8 1.399(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.371(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.409(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.369(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.437(5) . ?
C12 C17 1.412(5) . ?
C12 C19 1.514(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.394(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.435(6) . ?
C15 C16 1.393(6) . ?
C15 C18 1.495(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.433(5) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19 1.0000 . ?
C19 C20 1.516(6) . ?
C19 C21 1.525(6) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
P1 F1 1.584(11) . ?
P1 F1A 1.555(15) . ?
P1 F2 1.545(10) . ?
P1 F2A 1.622(11) . ?
P1 F3 1.635(6) . ?
P1 F3A 1.505(10) . ?
P1 F4 1.567(6) . ?
P1 F4A 1.646(9) . ?
P1 F5 1.502(8) . ?
P1 F5A 1.645(10) . ?
P1 F6 1.610(8) . ?
P1 F6A 1.550(8) . ?
Cl3 C22 1.741(7) . ?
Cl4 C22 1.763(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?

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
N1 Ru1 Cl1 85.62(9) . . ?
N1 Ru1 N3 75.86(12) . . ?
N1 Ru1 C12 93.69(13) . . ?
N1 Ru1 C13 94.87(13) . . ?
N1 Ru1 C14 120.22(14) . . ?
N1 Ru1 C15 157.73(14) . . ?
N1 Ru1 C16 157.63(14) . . ?
N1 Ru1 C17 119.66(14) . . ?
N3 Ru1 Cl1 83.52(9) . . ?
N3 Ru1 C12 118.29(13) . . ?
N3 Ru1 C13 155.24(14) . . ?
N3 Ru1 C14 163.14(14) . . ?
N3 Ru1 C15 125.59(14) . . ?
N3 Ru1 C16 100.41(14) . . ?
N3 Ru1 C17 96.39(14) . . ?
C12 Ru1 Cl1 157.37(11) . . ?
C12 Ru1 C15 81.36(14) . . ?
C12 Ru1 C16 68.31(14) . . ?
C13 Ru1 Cl1 119.12(11) . . ?
C13 Ru1 C12 38.33(14) . . ?
C13 Ru1 C14 37.17(15) . . ?
C13 Ru1 C15 67.84(15) . . ?
C13 Ru1 C16 79.35(15) . . ?
C14 Ru1 Cl1 92.26(11) . . ?
C14 Ru1 C12 68.55(14) . . ?
C14 Ru1 C15 37.88(15) . . ?
C14 Ru1 C16 66.81(15) . . ?
C15 Ru1 Cl1 90.73(11) . . ?
C16 Ru1 Cl1 116.17(11) . . ?
C16 Ru1 C15 36.58(15) . . ?
C17 Ru1 Cl1 154.05(11) . . ?
C17 Ru1 C12 37.73(14) . . ?
C17 Ru1 C13 67.94(14) . . ?
C17 Ru1 C14 80.32(15) . . ?
C17 Ru1 C15 68.14(14) . . ?
C17 Ru1 C16 38.16(14) . . ?
N2 N1 Ru1 116.5(2) . . ?
N4 N1 Ru1 132.4(2) . . ?
N4 N1 N2 111.0(3) . . ?
N1 N2 C1 116.3(3) . . ?
N1 N2 C6 108.4(3) . . ?
C6 N2 C1 135.0(3) . . ?
C1 N3 Ru1 117.6(2) . . ?
C1 N3 C2 117.2(3) . . ?
C2 N3 Ru1 124.9(3) . . ?
N1 N4 C7 107.0(3) . . ?
N3 C1 N2 112.8(3) . . ?
N3 C1 C5 124.0(4) . . ?
C5 C1 N2 123.1(4) . . ?
N3 C2 H2 118.7 . . ?
N3 C2 C3 122.5(4) . . ?
C3 C2 H2 118.7 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.5(4) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
C1 C5 C4 117.5(4) . . ?
C1 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
N2 C6 C7 103.9(3) . . ?
N2 C6 C11 134.4(4) . . ?
C7 C6 C11 121.7(4) . . ?
N4 C7 C6 109.7(3) . . ?
N4 C7 C8 128.5(4) . . ?
C6 C7 C8 121.8(4) . . ?
C7 C8 H8 121.9 . . ?
C9 C8 C7 116.3(4) . . ?
C9 C8 H8 121.9 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.7(4) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 118.6 . . ?
C11 C10 C9 122.8(4) . . ?
C11 C10 H10 118.6 . . ?
C6 C11 H11 122.1 . . ?
C10 C11 C6 115.8(4) . . ?
C10 C11 H11 122.1 . . ?
C13 C12 Ru1 70.6(2) . . ?
C13 C12 C19 119.2(3) . . ?
C17 C12 Ru1 70.5(2) . . ?
C17 C12 C13 117.6(3) . . ?
C17 C12 C19 123.2(4) . . ?
C19 C12 Ru1 129.3(3) . . ?
Ru1 C13 H13 130.9 . . ?
C12 C13 Ru1 71.0(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 Ru1 71.4(2) . . ?
C14 C13 C12 121.2(4) . . ?
C14 C13 H13 119.4 . . ?
Ru1 C14 H14 128.9 . . ?
C13 C14 Ru1 71.4(2) . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.3(4) . . ?
C15 C14 Ru1 72.7(2) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 Ru1 69.4(2) . . ?
C14 C15 C18 120.5(4) . . ?
C16 C15 Ru1 70.8(2) . . ?
C16 C15 C14 117.6(4) . . ?
C16 C15 C18 121.8(4) . . ?
C18 C15 Ru1 129.0(3) . . ?
Ru1 C16 H16 131.5 . . ?
C15 C16 Ru1 72.6(2) . . ?
C15 C16 H16 119.1 . . ?
C15 C16 C17 121.7(4) . . ?
C17 C16 Ru1 69.7(2) . . ?
C17 C16 H16 119.1 . . ?
Ru1 C17 H17 128.6 . . ?
C12 C17 Ru1 71.8(2) . . ?
C12 C17 C16 120.5(4) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 Ru1 72.2(2) . . ?
C16 C17 H17 119.7 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C12 C19 H19 107.8 . . ?
C12 C19 C20 113.4(4) . . ?
C12 C19 C21 107.7(4) . . ?
C20 C19 H19 107.8 . . ?
C20 C19 C21 112.1(4) . . ?
C21 C19 H19 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F1 P1 F3 88.6(6) . . ?
F1 P1 F6 79.4(7) . . ?
F1A P1 F2A 158.6(8) . . ?
F1A P1 F4A 85.1(8) . . ?
F1A P1 F5A 84.8(7) . . ?
F2 P1 F1 164.2(8) . . ?
F2 P1 F3 91.7(5) . . ?
F2 P1 F4 90.7(5) . . ?
F2 P1 F6 84.8(7) . . ?
F2A P1 F4A 82.9(6) . . ?
F2A P1 F5A 76.9(6) . . ?
F3A P1 F1A 98.9(9) . . ?
F3A P1 F2A 91.6(6) . . ?
F3A P1 F4A 173.4(6) . . ?
F3A P1 F5A 87.9(6) . . ?
F3A P1 F6A 97.7(7) . . ?
F4 P1 F1 88.0(5) . . ?
F4 P1 F3 175.1(4) . . ?
F4 P1 F6 87.8(5) . . ?
F5 P1 F1 92.1(6) . . ?
F5 P1 F2 103.7(8) . . ?
F5 P1 F3 89.3(5) . . ?
F5 P1 F4 94.3(5) . . ?
F5 P1 F6 171.2(7) . . ?
F5A P1 F4A 87.2(6) . . ?
F6 P1 F3 88.1(5) . . ?
F6A P1 F1A 103.8(7) . . ?
F6A P1 F2A 93.1(6) . . ?
F6A P1 F4A 86.4(6) . . ?
F6A P1 F5A 168.8(6) . . ?
Cl3 C22 Cl4 112.0(3) . . ?
Cl3 C22 H22A 109.2 . . ?
Cl3 C22 H22B 109.2 . . ?
Cl4 C22 H22A 109.2 . . ?
Cl4 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?

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
Ru1 N1 N2 C1 -8.0(4) . . . . ?
Ru1 N1 N2 C6 177.3(2) . . . . ?
Ru1 N1 N4 C7 -177.2(3) . . . . ?
Ru1 N3 C1 N2 5.8(4) . . . . ?
Ru1 N3 C1 C5 -174.0(3) . . . . ?
Ru1 N3 C2 C3 174.0(3) . . . . ?
Ru1 C12 C13 C14 53.1(3) . . . . ?
Ru1 C12 C17 C16 -55.4(3) . . . . ?
Ru1 C12 C19 C20 -62.4(5) . . . . ?
Ru1 C12 C19 C21 172.9(3) . . . . ?
Ru1 C13 C14 C15 55.1(3) . . . . ?
Ru1 C14 C15 C16 53.6(3) . . . . ?
Ru1 C14 C15 C18 -124.0(4) . . . . ?
Ru1 C15 C16 C17 51.6(3) . . . . ?
Ru1 C16 C17 C12 55.2(3) . . . . ?
N1 N2 C1 N3 1.3(5) . . . . ?
N1 N2 C1 C5 -178.8(4) . . . . ?
N1 N2 C6 C7 0.6(4) . . . . ?
N1 N2 C6 C11 -178.8(4) . . . . ?
N1 N4 C7 C6 0.7(4) . . . . ?
N1 N4 C7 C8 -178.4(4) . . . . ?
N2 N1 N4 C7 -0.3(4) . . . . ?
N2 C1 C5 C4 -179.8(4) . . . . ?
N2 C6 C7 N4 -0.8(4) . . . . ?
N2 C6 C7 C8 178.4(4) . . . . ?
N2 C6 C11 C10 -179.2(4) . . . . ?
N3 C1 C5 C4 0.0(7) . . . . ?
N3 C2 C3 C4 -0.9(7) . . . . ?
N4 N1 N2 C1 174.6(3) . . . . ?
N4 N1 N2 C6 -0.2(4) . . . . ?
N4 C7 C8 C9 -179.3(4) . . . . ?
C1 N2 C6 C7 -172.8(4) . . . . ?
C1 N2 C6 C11 7.8(8) . . . . ?
C1 N3 C2 C3 0.0(6) . . . . ?
C2 N3 C1 N2 -179.8(3) . . . . ?
C2 N3 C1 C5 0.4(6) . . . . ?
C2 C3 C4 C5 1.3(7) . . . . ?
C3 C4 C5 C1 -0.8(7) . . . . ?
C6 N2 C1 N3 174.3(4) . . . . ?
C6 N2 C1 C5 -5.8(7) . . . . ?
C6 C7 C8 C9 1.5(6) . . . . ?
C7 C6 C11 C10 1.4(6) . . . . ?
C7 C8 C9 C10 -0.6(7) . . . . ?
C8 C9 C10 C11 0.1(7) . . . . ?
C9 C10 C11 C6 -0.4(7) . . . . ?
C11 C6 C7 N4 178.7(4) . . . . ?
C11 C6 C7 C8 -2.0(6) . . . . ?
C12 C13 C14 Ru1 -52.9(3) . . . . ?
C12 C13 C14 C15 2.3(6) . . . . ?
C13 C12 C17 Ru1 54.4(3) . . . . ?
C13 C12 C17 C16 -0.9(5) . . . . ?
C13 C12 C19 C20 -150.5(4) . . . . ?
C13 C12 C19 C21 84.8(4) . . . . ?
C13 C14 C15 Ru1 -54.5(3) . . . . ?
C13 C14 C15 C16 -0.9(6) . . . . ?
C13 C14 C15 C18 -178.5(4) . . . . ?
C14 C15 C16 Ru1 -52.9(3) . . . . ?
C14 C15 C16 C17 -1.3(6) . . . . ?
C15 C16 C17 Ru1 -52.9(3) . . . . ?
C15 C16 C17 C12 2.3(6) . . . . ?
C17 C12 C13 Ru1 -54.3(3) . . . . ?
C17 C12 C13 C14 -1.3(5) . . . . ?
C17 C12 C19 C20 28.8(6) . . . . ?
C17 C12 C19 C21 -95.9(5) . . . . ?
C18 C15 C16 Ru1 124.6(4) . . . . ?
C18 C15 C16 C17 176.2(4) . . . . ?
C19 C12 C13 Ru1 125.0(3) . . . . ?
C19 C12 C13 C14 178.0(3) . . . . ?
C19 C12 C17 Ru1 -124.9(4) . . . . ?
C19 C12 C17 C16 179.8(4) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
