# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_test_b_sq
_database_code_depnum_ccdc_archive 'CCDC 2108084'
loop_
_audit_author_name
_audit_author_address
'Taniyuki FURUYAMA'
;Kanazawa University
Japan
;
_audit_update_record             
;
2021-09-07 deposited with the CCDC.	2021-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'Phthalocyaninato ruthenium bis(p-trifluoromethylpyridyl)'
_chemical_name_common            (p-CF3pyridyl)2RuPc
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H24 F6 N10 Ru'
_chemical_formula_sum            'C44 H24 F6 N10 Ru'
_chemical_formula_weight         907.80

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'
N N 0.0311 0.0180 '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'
Ru Ru 0.0552 3.2960 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   20.1094(18)
_cell_length_b                   22.559(2)
_cell_length_c                   10.5878(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.370(2)
_cell_angle_gamma                90
_cell_volume                     4558.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9865
_cell_measurement_theta_min      4.40
_cell_measurement_theta_max      70.77

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.351
_shelx_estimated_absorpt_T_min   0.554
_shelx_estimated_absorpt_T_max   0.730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5191
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   
'Sheldrick, G. M. (2008) SADABS. University of Göttingen, Germany.'
_exptl_special_details           
; 
 SADABS (Sheldrick, 1997) 
;
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            14260
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.920
_diffrn_reflns_theta_max         66.497
_diffrn_reflns_theta_full        66.497
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.782
_diffrn_reflns_point_group_measured_fraction_full 0.782
_reflns_number_total             6274
_reflns_number_gt                6211
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.591
_reflns_Friedel_fraction_max     0.582
_reflns_Friedel_fraction_full    0.582

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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    
;Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)
;
_computing_publication_material  
;Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)
;
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²+15.6747P] 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_abs_structure_details 
;
 Flack x determined using 2270 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.227(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6274
_refine_ls_number_parameters     550
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.077
_refine_ls_shift/su_mean         0.001

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.187 1.000 0.061 570 212 ' '
2 0.687 0.500 0.061 570 212 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

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 0.78511(4) 0.19251(2) 0.78459(6) 0.02408(14) Uani 1 1 d . . . . .
N1 N 0.8660(3) 0.2416(2) 0.7816(5) 0.0268(12) Uani 1 1 d . . . . .
C1 C 0.8998(3) 0.2398(3) 0.6860(7) 0.0260(14) Uani 1 1 d . . . . .
C2 C 0.9567(4) 0.2838(3) 0.7187(7) 0.0333(16) Uani 1 1 d . . . . .
C3 C 1.0068(4) 0.2977(3) 0.6622(7) 0.0352(17) Uani 1 1 d . . . . .
H1 H 1.0084 0.2776 0.5843 0.042 Uiso 1 1 calc R U . . .
C4 C 1.0549(4) 0.3409(4) 0.7184(12) 0.061(3) Uani 1 1 d . . . . .
H2 H 1.0889 0.3522 0.6778 0.073 Uiso 1 1 calc R U . . .
C5 C 1.0535(4) 0.3690(3) 0.8400(8) 0.0345(17) Uani 1 1 d . . . . .
H3 H 1.0868 0.3990 0.8790 0.041 Uiso 1 1 calc R U . . .
C6 C 1.0053(4) 0.3535(3) 0.8997(7) 0.0347(16) Uani 1 1 d . . . . .
H4 H 1.0059 0.3711 0.9815 0.042 Uiso 1 1 calc R U . . .
C7 C 0.9548(4) 0.3108(3) 0.8379(7) 0.0298(15) Uani 1 1 d . . . . .
C8 C 0.8983(4) 0.2838(3) 0.8766(7) 0.0286(15) Uani 1 1 d . . . . .
N2 N 0.8813(3) 0.2989(3) 0.9836(6) 0.0314(13) Uani 1 1 d . . . . .
N3 N 0.7823(3) 0.2331(2) 0.9527(6) 0.0268(12) Uani 1 1 d . . . . .
C9 C 0.8291(4) 0.2754(3) 1.0208(7) 0.0320(15) Uani 1 1 d . . . . .
C10 C 0.8154(4) 0.2893(3) 1.1407(8) 0.0331(16) Uani 1 1 d . . . . .
C11 C 0.8480(5) 0.3271(4) 1.2473(8) 0.0418(19) Uani 1 1 d . . . . .
H5 H 0.8866 0.3511 1.2460 0.050 Uiso 1 1 calc R U . . .
C12 C 0.8230(5) 0.3287(4) 1.3535(9) 0.045(2) Uani 1 1 d . . . . .
H6 H 0.8457 0.3531 1.4277 0.055 Uiso 1 1 calc R U . . .
C13 C 0.7651(5) 0.2954(4) 1.3548(10) 0.0441(19) Uani 1 1 d . . . . .
H7 H 0.7493 0.2972 1.4304 0.053 Uiso 1 1 calc R U . . .
C14 C 0.7296(4) 0.2593(3) 1.2476(8) 0.0349(16) Uani 1 1 d . . . . .
H8 H 0.6891 0.2377 1.2476 0.042 Uiso 1 1 calc R U . . .
C15 C 0.7555(4) 0.2563(3) 1.1419(7) 0.0311(15) Uani 1 1 d . . . . .
C16 C 0.7362(4) 0.2202(3) 1.0185(7) 0.0285(15) Uani 1 1 d . . . . .
N4 N 0.6822(4) 0.1828(3) 0.9862(7) 0.0259(14) Uani 1 1 d . . . . .
N5 N 0.7035(3) 0.1429(2) 0.7899(6) 0.0314(13) Uani 1 1 d . . . . .
C17 C 0.6683(4) 0.1472(3) 0.8803(7) 0.0287(14) Uani 1 1 d . . . . .
C18 C 0.6106(4) 0.1054(3) 0.8426(7) 0.0310(15) Uani 1 1 d . . . . .
C19 C 0.5556(4) 0.0920(4) 0.8969(8) 0.0407(18) Uani 1 1 d . . . . .
H9 H 0.5521 0.1120 0.9735 0.049 Uiso 1 1 calc R U . . .
C20 C 0.5073(4) 0.0486(4) 0.8340(9) 0.0418(18) Uani 1 1 d . . . . .
H10 H 0.4708 0.0386 0.8691 0.050 Uiso 1 1 calc R U . . .
C21 C 0.5115(4) 0.0193(4) 0.7199(9) 0.0425(19) Uani 1 1 d . . . . .
H11 H 0.4773 -0.0098 0.6791 0.051 Uiso 1 1 calc R U . . .
C22 C 0.5638(4) 0.0318(3) 0.6654(8) 0.0331(16) Uani 1 1 d . . . . .
H12 H 0.5667 0.0114 0.5888 0.040 Uiso 1 1 calc R U . . .
C23 C 0.6127(4) 0.0758(3) 0.7275(7) 0.0309(15) Uani 1 1 d . . . . .
C24 C 0.6722(4) 0.1001(3) 0.6933(7) 0.0275(14) Uani 1 1 d . . . . .
N6 N 0.6901(3) 0.0853(2) 0.5892(6) 0.0271(12) Uani 1 1 d . . . . .
N7 N 0.7877(3) 0.1532(2) 0.6176(6) 0.0262(12) Uani 1 1 d . . . . .
C25 C 0.7407(3) 0.1088(3) 0.5520(7) 0.0255(14) Uani 1 1 d . . . . .
C26 C 0.7554(4) 0.0944(3) 0.4303(7) 0.0276(15) Uani 1 1 d . . . . .
C27 C 0.7212(4) 0.0574(3) 0.3226(7) 0.0278(14) Uani 1 1 d . . . . .
H13 H 0.6833 0.0328 0.3253 0.033 Uiso 1 1 calc R U . . .
C28 C 0.7441(4) 0.0576(3) 0.2135(8) 0.0369(17) Uani 1 1 d . . . . .
H14 H 0.7209 0.0337 0.1389 0.044 Uiso 1 1 calc R U . . .
C29 C 0.8012(5) 0.0926(3) 0.2101(8) 0.0352(17) Uani 1 1 d . . . . .
H15 H 0.8168 0.0910 0.1343 0.042 Uiso 1 1 calc R U . . .
C30 C 0.8354(4) 0.1297(3) 0.3156(8) 0.0328(16) Uani 1 1 d . . . . .
H16 H 0.8742 0.1533 0.3131 0.039 Uiso 1 1 calc R U . . .
C31 C 0.8114(4) 0.1311(3) 0.4235(7) 0.0280(14) Uani 1 1 d . . . . .
C32 C 0.8300(4) 0.1658(3) 0.5466(6) 0.0258(14) Uani 1 1 d . . . . .
N8 N 0.8819(4) 0.2060(3) 0.5769(7) 0.0299(15) Uani 1 1 d . . . . .
N9 N 0.7164(3) 0.2550(2) 0.6704(6) 0.0274(12) Uani 1 1 d . . . . .
C33 C 0.7262(4) 0.3144(3) 0.6920(8) 0.0340(16) Uani 1 1 d . . . . .
H17 H 0.7642 0.3275 0.7656 0.041 Uiso 1 1 calc R U . . .
C34 C 0.6829(5) 0.3563(3) 0.6107(9) 0.0436(19) Uani 1 1 d . . . . .
H18 H 0.6914 0.3973 0.6293 0.052 Uiso 1 1 calc R U . . .
C35 C 0.6289(4) 0.3393(3) 0.5058(8) 0.0380(17) Uani 1 1 d . . . . .
C36 C 0.6165(4) 0.2794(3) 0.4784(9) 0.0372(17) Uani 1 1 d . . . . .
H19 H 0.5792 0.2662 0.4038 0.045 Uiso 1 1 calc R U . . .
C37 C 0.6614(4) 0.2393(3) 0.5660(7) 0.0333(16) Uani 1 1 d . . . . .
H20 H 0.6522 0.1982 0.5503 0.040 Uiso 1 1 calc R U . . .
C38 C 0.5845(5) 0.3815(4) 0.4037(9) 0.045(2) Uani 1 1 d . . . . .
F1 F 0.6103(4) 0.3933(4) 0.3121(7) 0.094(3) Uani 1 1 d . . . . .
F2 F 0.5777(3) 0.4342(2) 0.4671(7) 0.0703(18) Uani 1 1 d . . . . .
F3 F 0.5202(3) 0.3634(2) 0.3485(6) 0.0672(17) Uani 1 1 d . . . . .
N10 N 0.8532(3) 0.1293(2) 0.9006(5) 0.0251(12) Uani 1 1 d . . . . .
C39 C 0.8421(4) 0.0715(3) 0.8703(7) 0.0316(15) Uani 1 1 d . . . . .
H21 H 0.8039 0.0606 0.7947 0.038 Uiso 1 1 calc R U . . .
C40 C 0.8842(4) 0.0270(3) 0.9456(7) 0.0312(15) Uani 1 1 d . . . . .
H22 H 0.8752 -0.0135 0.9219 0.037 Uiso 1 1 calc R U . . .
C41 C 0.9399(4) 0.0432(3) 1.0564(8) 0.0392(18) Uani 1 1 d . . . . .
C42 C 0.9520(4) 0.1029(3) 1.0868(8) 0.0343(16) Uani 1 1 d . . . . .
H23 H 0.9899 0.1155 1.1612 0.041 Uiso 1 1 calc R U . . .
C43 C 0.9072(4) 0.1433(3) 1.0056(7) 0.0326(15) Uani 1 1 d . . . . .
H24 H 0.9155 0.1842 1.0263 0.039 Uiso 1 1 calc R U . . .
C44 C 0.9850(6) -0.0066(4) 1.1422(9) 0.056(3) Uani 1 1 d . . . . .
F4 F 1.0026(5) -0.0447(3) 1.0672(8) 0.105(3) Uani 1 1 d . . . . .
F5 F 0.9514(5) -0.0359(4) 1.2011(10) 0.118(4) Uani 1 1 d . . . . .
F6 F 1.0431(5) 0.0144(3) 1.2184(10) 0.123(4) Uani 1 1 d . . . . .


_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 N1 1.977(6) . ?
Ru1 N7 1.993(6) . ?
Ru1 N5 2.001(6) . ?
Ru1 N3 2.017(6) . ?
Ru1 N9 2.075(6) . ?
Ru1 N10 2.088(5) . ?
N1 C1 1.385(10) . ?
N1 C8 1.388(9) . ?
C1 N8 1.335(10) . ?
C1 C2 1.472(10) . ?
C2 C3 1.360(12) . ?
C2 C7 1.412(11) . ?
C3 C4 1.371(12) . ?
C4 C5 1.444(15) . ?
C5 C6 1.359(12) . ?
C6 C7 1.404(10) . ?
C7 C8 1.457(11) . ?
C8 N2 1.327(10) . ?
N2 C9 1.340(10) . ?
N3 C16 1.356(10) . ?
N3 C9 1.375(9) . ?
C9 C10 1.416(12) . ?
C10 C11 1.401(11) . ?
C10 C15 1.422(11) . ?
C11 C12 1.369(13) . ?
C12 C13 1.390(14) . ?
C13 C14 1.397(12) . ?
C14 C15 1.377(12) . ?
C15 C16 1.484(10) . ?
C16 N4 1.331(10) . ?
N4 C17 1.336(10) . ?
N5 C17 1.361(10) . ?
N5 C24 1.404(9) . ?
C17 C18 1.449(10) . ?
C18 C23 1.403(11) . ?
C18 C19 1.430(12) . ?
C19 C20 1.391(11) . ?
C20 C21 1.401(13) . ?
C21 C22 1.380(12) . ?
C22 C23 1.407(10) . ?
C23 C24 1.462(10) . ?
C24 N6 1.306(10) . ?
N6 C25 1.311(9) . ?
N7 C32 1.331(9) . ?
N7 C25 1.403(8) . ?
C25 C26 1.446(11) . ?
C26 C27 1.406(10) . ?
C26 C31 1.418(10) . ?
C27 C28 1.371(11) . ?
C28 C29 1.403(12) . ?
C29 C30 1.392(10) . ?
C30 C31 1.374(11) . ?
C31 C32 1.465(9) . ?
C32 N8 1.343(10) . ?
N9 C37 1.342(10) . ?
N9 C33 1.363(9) . ?
C33 C34 1.387(11) . ?
C34 C35 1.340(12) . ?
C35 C36 1.387(11) . ?
C35 C38 1.505(10) . ?
C36 C37 1.402(10) . ?
C38 F1 1.264(11) . ?
C38 F3 1.306(11) . ?
C38 F2 1.393(10) . ?
N10 C43 1.324(9) . ?
N10 C39 1.344(9) . ?
C39 C40 1.391(10) . ?
C40 C41 1.392(11) . ?
C41 C42 1.388(11) . ?
C41 C44 1.547(10) . ?
C42 C43 1.376(10) . ?
C44 F5 1.245(13) . ?
C44 F6 1.284(12) . ?
C44 F4 1.293(13) . ?

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 N7 89.0(2) . . ?
N1 Ru1 N5 179.3(3) . . ?
N7 Ru1 N5 91.6(2) . . ?
N1 Ru1 N3 90.7(2) . . ?
N7 Ru1 N3 179.4(2) . . ?
N5 Ru1 N3 88.7(2) . . ?
N1 Ru1 N9 90.6(2) . . ?
N7 Ru1 N9 89.1(2) . . ?
N5 Ru1 N9 89.7(2) . . ?
N3 Ru1 N9 90.4(2) . . ?
N1 Ru1 N10 90.1(2) . . ?
N7 Ru1 N10 91.3(2) . . ?
N5 Ru1 N10 89.6(2) . . ?
N3 Ru1 N10 89.2(2) . . ?
N9 Ru1 N10 179.2(3) . . ?
C1 N1 C8 109.0(6) . . ?
C1 N1 Ru1 126.1(4) . . ?
C8 N1 Ru1 124.9(5) . . ?
N8 C1 N1 126.1(6) . . ?
N8 C1 C2 124.4(7) . . ?
N1 C1 C2 109.4(6) . . ?
C3 C2 C7 121.7(7) . . ?
C3 C2 C1 133.0(7) . . ?
C7 C2 C1 105.2(6) . . ?
C2 C3 C4 119.5(8) . . ?
C3 C4 C5 119.3(8) . . ?
C6 C5 C4 121.3(6) . . ?
C5 C6 C7 118.5(7) . . ?
C6 C7 C2 119.6(7) . . ?
C6 C7 C8 132.0(7) . . ?
C2 C7 C8 108.4(6) . . ?
N2 C8 N1 127.3(7) . . ?
N2 C8 C7 124.6(6) . . ?
N1 C8 C7 108.1(6) . . ?
C8 N2 C9 125.9(6) . . ?
C16 N3 C9 110.2(6) . . ?
C16 N3 Ru1 124.8(4) . . ?
C9 N3 Ru1 125.0(5) . . ?
N2 C9 N3 126.1(7) . . ?
N2 C9 C10 124.5(7) . . ?
N3 C9 C10 109.3(6) . . ?
C11 C10 C9 133.1(8) . . ?
C11 C10 C15 119.6(8) . . ?
C9 C10 C15 107.2(7) . . ?
C12 C11 C10 118.6(8) . . ?
C11 C12 C13 121.3(8) . . ?
C12 C13 C14 121.5(9) . . ?
C15 C14 C13 117.5(8) . . ?
C14 C15 C10 121.3(7) . . ?
C14 C15 C16 133.0(7) . . ?
C10 C15 C16 105.5(7) . . ?
N4 C16 N3 129.7(7) . . ?
N4 C16 C15 122.6(7) . . ?
N3 C16 C15 107.7(6) . . ?
C16 N4 C17 122.4(7) . . ?
C17 N5 C24 110.4(6) . . ?
C17 N5 Ru1 126.4(5) . . ?
C24 N5 Ru1 123.2(5) . . ?
N4 C17 N5 127.9(7) . . ?
N4 C17 C18 124.1(7) . . ?
N5 C17 C18 108.1(6) . . ?
C23 C18 C19 119.2(6) . . ?
C23 C18 C17 107.9(6) . . ?
C19 C18 C17 132.9(7) . . ?
C20 C19 C18 117.9(8) . . ?
C19 C20 C21 121.4(8) . . ?
C22 C21 C20 121.7(8) . . ?
C21 C22 C23 117.5(8) . . ?
C18 C23 C22 122.3(7) . . ?
C18 C23 C24 106.8(6) . . ?
C22 C23 C24 130.9(7) . . ?
N6 C24 N5 127.7(6) . . ?
N6 C24 C23 125.4(6) . . ?
N5 C24 C23 106.9(6) . . ?
C24 N6 C25 126.6(6) . . ?
C32 N7 C25 108.9(6) . . ?
C32 N7 Ru1 127.3(4) . . ?
C25 N7 Ru1 123.7(5) . . ?
N6 C25 N7 127.3(6) . . ?
N6 C25 C26 124.9(6) . . ?
N7 C25 C26 107.8(6) . . ?
C27 C26 C31 119.8(7) . . ?
C27 C26 C25 132.2(7) . . ?
C31 C26 C25 107.7(6) . . ?
C28 C27 C26 118.2(7) . . ?
C27 C28 C29 121.2(7) . . ?
C30 C29 C28 121.3(8) . . ?
C31 C30 C29 117.8(7) . . ?
C30 C31 C26 121.5(6) . . ?
C30 C31 C32 133.9(7) . . ?
C26 C31 C32 104.5(6) . . ?
N7 C32 N8 126.6(6) . . ?
N7 C32 C31 111.0(6) . . ?
N8 C32 C31 122.3(7) . . ?
C1 N8 C32 124.7(7) . . ?
C37 N9 C33 115.8(6) . . ?
C37 N9 Ru1 121.7(4) . . ?
C33 N9 Ru1 122.4(5) . . ?
N9 C33 C34 122.4(7) . . ?
C35 C34 C33 120.4(8) . . ?
C34 C35 C36 119.8(7) . . ?
C34 C35 C38 123.8(7) . . ?
C36 C35 C38 116.0(8) . . ?
C35 C36 C37 117.0(7) . . ?
N9 C37 C36 124.5(6) . . ?
F1 C38 F3 108.1(8) . . ?
F1 C38 F2 108.4(8) . . ?
F3 C38 F2 104.4(7) . . ?
F1 C38 C35 112.9(7) . . ?
F3 C38 C35 113.8(7) . . ?
F2 C38 C35 108.7(7) . . ?
C43 N10 C39 117.6(6) . . ?
C43 N10 Ru1 122.8(5) . . ?
C39 N10 Ru1 119.5(4) . . ?
N10 C39 C40 122.5(7) . . ?
C39 C40 C41 118.5(7) . . ?
C42 C41 C40 119.1(6) . . ?
C42 C41 C44 122.8(7) . . ?
C40 C41 C44 118.1(7) . . ?
C43 C42 C41 117.7(7) . . ?
N10 C43 C42 124.6(7) . . ?
F5 C44 F6 114.3(10) . . ?
F5 C44 F4 104.6(10) . . ?
F6 C44 F4 105.2(10) . . ?
F5 C44 C41 111.7(9) . . ?
F6 C44 C41 110.4(8) . . ?
F4 C44 C41 110.3(7) . . ?

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
C8 N1 C1 N8 -177.6(6) . . . . ?
Ru1 N1 C1 N8 2.6(9) . . . . ?
C8 N1 C1 C2 -0.9(7) . . . . ?
Ru1 N1 C1 C2 179.3(4) . . . . ?
N8 C1 C2 C3 -6.8(12) . . . . ?
N1 C1 C2 C3 176.4(7) . . . . ?
N8 C1 C2 C7 177.2(6) . . . . ?
N1 C1 C2 C7 0.5(7) . . . . ?
C7 C2 C3 C4 -3.0(11) . . . . ?
C1 C2 C3 C4 -178.4(7) . . . . ?
C2 C3 C4 C5 2.7(12) . . . . ?
C3 C4 C5 C6 0.0(12) . . . . ?
C4 C5 C6 C7 -2.4(11) . . . . ?
C5 C6 C7 C2 2.2(10) . . . . ?
C5 C6 C7 C8 178.2(7) . . . . ?
C3 C2 C7 C6 0.5(11) . . . . ?
C1 C2 C7 C6 177.1(6) . . . . ?
C3 C2 C7 C8 -176.4(7) . . . . ?
C1 C2 C7 C8 0.1(7) . . . . ?
C1 N1 C8 N2 179.7(6) . . . . ?
Ru1 N1 C8 N2 -0.4(9) . . . . ?
C1 N1 C8 C7 1.0(7) . . . . ?
Ru1 N1 C8 C7 -179.2(4) . . . . ?
C6 C7 C8 N2 4.1(12) . . . . ?
C2 C7 C8 N2 -179.5(6) . . . . ?
C6 C7 C8 N1 -177.1(7) . . . . ?
C2 C7 C8 N1 -0.7(7) . . . . ?
N1 C8 N2 C9 0.5(11) . . . . ?
C7 C8 N2 C9 179.1(7) . . . . ?
C8 N2 C9 N3 -2.5(11) . . . . ?
C8 N2 C9 C10 175.2(7) . . . . ?
C16 N3 C9 N2 -179.3(7) . . . . ?
Ru1 N3 C9 N2 3.9(10) . . . . ?
C16 N3 C9 C10 2.8(8) . . . . ?
Ru1 N3 C9 C10 -174.0(4) . . . . ?
N2 C9 C10 C11 -0.5(14) . . . . ?
N3 C9 C10 C11 177.4(8) . . . . ?
N2 C9 C10 C15 178.9(7) . . . . ?
N3 C9 C10 C15 -3.1(8) . . . . ?
C9 C10 C11 C12 -177.2(8) . . . . ?
C15 C10 C11 C12 3.3(12) . . . . ?
C10 C11 C12 C13 -2.2(13) . . . . ?
C11 C12 C13 C14 -0.6(14) . . . . ?
C12 C13 C14 C15 2.2(13) . . . . ?
C13 C14 C15 C10 -1.0(11) . . . . ?
C13 C14 C15 C16 174.3(7) . . . . ?
C11 C10 C15 C14 -1.7(11) . . . . ?
C9 C10 C15 C14 178.7(7) . . . . ?
C11 C10 C15 C16 -178.2(7) . . . . ?
C9 C10 C15 C16 2.2(8) . . . . ?
C9 N3 C16 N4 178.7(7) . . . . ?
Ru1 N3 C16 N4 -4.5(10) . . . . ?
C9 N3 C16 C15 -1.3(7) . . . . ?
Ru1 N3 C16 C15 175.5(4) . . . . ?
C14 C15 C16 N4 3.5(12) . . . . ?
C10 C15 C16 N4 179.4(6) . . . . ?
C14 C15 C16 N3 -176.5(8) . . . . ?
C10 C15 C16 N3 -0.6(7) . . . . ?
N3 C16 N4 C17 5.1(12) . . . . ?
C15 C16 N4 C17 -174.9(6) . . . . ?
C16 N4 C17 N5 -0.9(11) . . . . ?
C16 N4 C17 C18 179.3(6) . . . . ?
C24 N5 C17 N4 180.0(7) . . . . ?
Ru1 N5 C17 N4 -3.2(10) . . . . ?
C24 N5 C17 C18 -0.2(7) . . . . ?
Ru1 N5 C17 C18 176.6(4) . . . . ?
N4 C17 C18 C23 -179.7(6) . . . . ?
N5 C17 C18 C23 0.4(7) . . . . ?
N4 C17 C18 C19 2.1(12) . . . . ?
N5 C17 C18 C19 -177.7(7) . . . . ?
C23 C18 C19 C20 1.5(11) . . . . ?
C17 C18 C19 C20 179.5(7) . . . . ?
C18 C19 C20 C21 -0.8(12) . . . . ?
C19 C20 C21 C22 0.6(13) . . . . ?
C20 C21 C22 C23 -1.0(11) . . . . ?
C19 C18 C23 C22 -2.0(10) . . . . ?
C17 C18 C23 C22 179.5(6) . . . . ?
C19 C18 C23 C24 178.0(6) . . . . ?
C17 C18 C23 C24 -0.5(7) . . . . ?
C21 C22 C23 C18 1.7(10) . . . . ?
C21 C22 C23 C24 -178.3(7) . . . . ?
C17 N5 C24 N6 177.6(6) . . . . ?
Ru1 N5 C24 N6 0.6(9) . . . . ?
C17 N5 C24 C23 -0.1(7) . . . . ?
Ru1 N5 C24 C23 -177.1(4) . . . . ?
C18 C23 C24 N6 -177.4(6) . . . . ?
C22 C23 C24 N6 2.6(11) . . . . ?
C18 C23 C24 N5 0.4(7) . . . . ?
C22 C23 C24 N5 -179.6(6) . . . . ?
N5 C24 N6 C25 -1.6(10) . . . . ?
C23 C24 N6 C25 175.7(6) . . . . ?
C24 N6 C25 N7 2.2(10) . . . . ?
C24 N6 C25 C26 -174.9(6) . . . . ?
C32 N7 C25 N6 -178.6(6) . . . . ?
Ru1 N7 C25 N6 -1.8(9) . . . . ?
C32 N7 C25 C26 -1.1(7) . . . . ?
Ru1 N7 C25 C26 175.8(4) . . . . ?
N6 C25 C26 C27 3.8(11) . . . . ?
N7 C25 C26 C27 -173.8(6) . . . . ?
N6 C25 C26 C31 177.1(6) . . . . ?
N7 C25 C26 C31 -0.5(7) . . . . ?
C31 C26 C27 C28 0.6(9) . . . . ?
C25 C26 C27 C28 173.3(6) . . . . ?
C26 C27 C28 C29 1.6(10) . . . . ?
C27 C28 C29 C30 -2.0(11) . . . . ?
C28 C29 C30 C31 -0.1(10) . . . . ?
C29 C30 C31 C26 2.5(9) . . . . ?
C29 C30 C31 C32 -175.8(7) . . . . ?
C27 C26 C31 C30 -2.8(9) . . . . ?
C25 C26 C31 C30 -177.0(6) . . . . ?
C27 C26 C31 C32 176.0(6) . . . . ?
C25 C26 C31 C32 1.7(6) . . . . ?
C25 N7 C32 N8 180.0(6) . . . . ?
Ru1 N7 C32 N8 3.2(10) . . . . ?
C25 N7 C32 C31 2.3(7) . . . . ?
Ru1 N7 C32 C31 -174.5(4) . . . . ?
C30 C31 C32 N7 176.0(7) . . . . ?
C26 C31 C32 N7 -2.5(7) . . . . ?
C30 C31 C32 N8 -1.8(12) . . . . ?
C26 C31 C32 N8 179.7(6) . . . . ?
N1 C1 N8 C32 -3.8(11) . . . . ?
C2 C1 N8 C32 180.0(6) . . . . ?
N7 C32 N8 C1 0.7(11) . . . . ?
C31 C32 N8 C1 178.2(6) . . . . ?
C37 N9 C33 C34 -0.8(12) . . . . ?
Ru1 N9 C33 C34 175.8(6) . . . . ?
N9 C33 C34 C35 -0.2(13) . . . . ?
C33 C34 C35 C36 -0.1(13) . . . . ?
C33 C34 C35 C38 -172.7(8) . . . . ?
C34 C35 C36 C37 1.3(12) . . . . ?
C38 C35 C36 C37 174.5(8) . . . . ?
C33 N9 C37 C36 2.2(12) . . . . ?
Ru1 N9 C37 C36 -174.5(6) . . . . ?
C35 C36 C37 N9 -2.5(13) . . . . ?
C34 C35 C38 F1 85.3(11) . . . . ?
C36 C35 C38 F1 -87.6(11) . . . . ?
C34 C35 C38 F3 -150.9(9) . . . . ?
C36 C35 C38 F3 36.2(11) . . . . ?
C34 C35 C38 F2 -35.0(12) . . . . ?
C36 C35 C38 F2 152.1(8) . . . . ?
C43 N10 C39 C40 0.8(11) . . . . ?
Ru1 N10 C39 C40 -178.2(6) . . . . ?
N10 C39 C40 C41 0.1(11) . . . . ?
C39 C40 C41 C42 -0.9(12) . . . . ?
C39 C40 C41 C44 178.0(8) . . . . ?
C40 C41 C42 C43 0.7(13) . . . . ?
C44 C41 C42 C43 -178.1(9) . . . . ?
C39 N10 C43 C42 -1.0(12) . . . . ?
Ru1 N10 C43 C42 178.0(6) . . . . ?
C41 C42 C43 N10 0.2(13) . . . . ?
C42 C41 C44 F5 111.1(11) . . . . ?
C40 C41 C44 F5 -67.7(12) . . . . ?
C42 C41 C44 F6 -17.3(15) . . . . ?
C40 C41 C44 F6 163.9(10) . . . . ?
C42 C41 C44 F4 -133.0(10) . . . . ?
C40 C41 C44 F4 48.1(13) . . . . ?

_refine_diff_density_max         1.635
_refine_diff_density_min         -0.861
_refine_diff_density_rms         0.082



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/ethanol'
_chemical_properties_physical    Light-sensitive
