# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_CrystalClear_a
_database_code_depnum_ccdc_archive 'CCDC 1517553'
_audit_update_record             
;
2016-11-24 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H21 F6 N6 O4 P Ru'
_chemical_formula_weight         811.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.5554(3)
_cell_length_b                   14.010
_cell_length_c                   14.658
_cell_angle_alpha                68.476(11)
_cell_angle_beta                 75.226(14)
_cell_angle_gamma                77.465(15)
_cell_volume                     1565.38(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    6059
_cell_measurement_theta_min      2.4856
_cell_measurement_theta_max      31.3022

_exptl_crystal_description       Block
_exptl_crystal_colour            'Dark Red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_F_000             812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.1500
_exptl_absorpt_coefficient_mu    0.639
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8936
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      163(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'RIGAKU/MSC Meacury CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12236
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.486
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             6769
_reflns_number_gt                5834
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0753P)²+2.2492P] 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         6769
_refine_ls_number_parameters     460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
C1 C 0.4120(4) 0.5577(3) 0.8662(3) 0.0234(7) Uani 1 1 d . . . . .
H1 H 0.449523 0.491873 0.861443 0.028 Uiso 1 1 calc R U . . .
C2 C 0.3076(5) 0.5673(3) 0.9529(3) 0.0295(8) Uani 1 1 d . . . . .
H2 H 0.276436 0.508790 1.005587 0.035 Uiso 1 1 calc R U . . .
C3 C 0.2508(5) 0.6642(3) 0.9600(3) 0.0317(9) Uani 1 1 d . . . . .
H3 H 0.178189 0.672110 1.016744 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3022(5) 0.7500(3) 0.8823(3) 0.0299(8) Uani 1 1 d . . . . .
H4 H 0.266000 0.816086 0.886407 0.036 Uiso 1 1 calc R U . . .
C5 C 0.4089(4) 0.7360(3) 0.7978(3) 0.0225(7) Uani 1 1 d . . . . .
C6 C 0.4824(4) 0.8207(3) 0.7150(3) 0.0215(7) Uani 1 1 d . . . . .
C7 C 0.4612(4) 0.9223(3) 0.7187(3) 0.0255(7) Uani 1 1 d . . . . .
H7 H 0.387170 0.940413 0.770312 0.031 Uiso 1 1 calc R U . . .
C8 C 0.5501(5) 0.9928(3) 0.6461(3) 0.0272(8) Uani 1 1 d . . . . .
H8 H 0.539962 1.059338 0.648529 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6587(4) 0.9651(3) 0.5663(3) 0.0222(7) Uani 1 1 d . . . . .
C10 C 0.6648(4) 0.8643(3) 0.5611(2) 0.0192(7) Uani 1 1 d . . . . .
C11 C 0.7541(4) 0.8410(3) 0.4758(2) 0.0197(7) Uani 1 1 d . . . . .
C12 C 0.8490(4) 0.9153(3) 0.4028(3) 0.0230(7) Uani 1 1 d . . . . .
C13 C 0.8471(5) 1.0102(3) 0.4203(3) 0.0252(7) Uani 1 1 d . . . . .
C14 C 0.9474(5) 1.0836(3) 0.3497(3) 0.0334(9) Uani 1 1 d . . . . .
H14 H 0.948040 1.144768 0.360752 0.040 Uiso 1 1 calc R U . . .
C15 C 1.0417(5) 1.0663(3) 0.2670(3) 0.0381(10) Uani 1 1 d . . . . .
H15 H 1.108044 1.114807 0.222332 0.046 Uiso 1 1 calc R U . . .
C16 C 1.0406(5) 0.9753(3) 0.2475(3) 0.0361(9) Uani 1 1 d . . . . .
H16 H 1.103470 0.965278 0.188998 0.043 Uiso 1 1 calc R U . . .
C17 C 0.9473(5) 0.9012(3) 0.3142(3) 0.0299(8) Uani 1 1 d . . . . .
H17 H 0.949062 0.841043 0.300785 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3145(4) 0.7084(3) 0.5552(3) 0.0241(7) Uani 1 1 d . . . . .
H18 H 0.327646 0.775952 0.544942 0.029 Uiso 1 1 calc R U . . .
C19 C 0.1867(5) 0.6927(3) 0.5235(3) 0.0279(8) Uani 1 1 d . . . . .
H19 H 0.114425 0.748768 0.493657 0.033 Uiso 1 1 calc R U . . .
C20 C 0.1672(4) 0.5935(3) 0.5363(3) 0.0279(8) Uani 1 1 d . . . . .
H20 H 0.081483 0.581426 0.515468 0.034 Uiso 1 1 calc R U . . .
C21 C 0.2778(4) 0.5112(3) 0.5810(3) 0.0243(7) Uani 1 1 d . . . . .
H21 H 0.267869 0.443444 0.589657 0.029 Uiso 1 1 calc R U . . .
C22 C 0.4024(4) 0.5317(3) 0.6121(2) 0.0196(7) Uani 1 1 d . . . . .
C23 C 0.5241(4) 0.4503(3) 0.6616(2) 0.0206(7) Uani 1 1 d . . . . .
C24 C 0.5320(5) 0.3438(3) 0.6848(3) 0.0263(8) Uani 1 1 d . . . . .
H24 H 0.455602 0.316846 0.669475 0.032 Uiso 1 1 calc R U . . .
C25 C 0.6564(5) 0.2791(3) 0.7313(3) 0.0297(8) Uani 1 1 d . . . . .
H25 H 0.663590 0.207782 0.747335 0.036 Uiso 1 1 calc R U . . .
C26 C 0.7701(5) 0.3190(3) 0.7543(3) 0.0270(8) Uani 1 1 d . . . . .
H26 H 0.853953 0.275388 0.785115 0.032 Uiso 1 1 calc R U . . .
C27 C 0.7562(4) 0.4254(3) 0.7303(3) 0.0221(7) Uani 1 1 d . . . . .
C28 C 0.8588(4) 0.4826(3) 0.7528(2) 0.0211(7) Uani 1 1 d . . . . .
C29 C 0.9921(5) 0.4356(3) 0.7979(3) 0.0283(8) Uani 1 1 d . . . . .
H29 H 1.026218 0.364831 0.811830 0.034 Uiso 1 1 calc R U . . .
C30 C 1.0739(5) 0.4951(3) 0.8219(3) 0.0332(9) Uani 1 1 d . . . . .
H30 H 1.162471 0.464698 0.853502 0.040 Uiso 1 1 calc R U . . .
C31 C 1.0231(5) 0.5999(3) 0.7987(3) 0.0326(9) Uani 1 1 d . . . . .
H31 H 1.077040 0.641113 0.814270 0.039 Uiso 1 1 calc R U . . .
C32 C 0.8905(4) 0.6435(3) 0.7517(3) 0.0264(8) Uani 1 1 d . . . . .
H32 H 0.856549 0.714328 0.736295 0.032 Uiso 1 1 calc R U . . .
C33 C 0.7428(4) 0.7441(3) 0.4542(3) 0.0218(7) Uani 1 1 d . . . . .
O1 O 0.7140(4) 0.7577(2) 0.3729(2) 0.0395(7) Uani 1 1 d . . . . .
O2 O 0.7685(3) 0.65548(18) 0.52037(18) 0.0236(5) Uani 1 1 d . . . . .
RU1 Ru 0.61076(3) 0.63783(2) 0.65901(2) 0.01813(10) Uani 1 1 d . . . . .
P1 P 0.33237(15) 0.22162(10) 1.00064(9) 0.0418(3) Uani 1 1 d . . . . .
N1 N 0.4201(3) 0.6311(2) 0.6000(2) 0.0195(6) Uani 1 1 d . . . . .
N2 N 0.6355(3) 0.4877(2) 0.6854(2) 0.0189(6) Uani 1 1 d . . . . .
N3 N 0.5794(3) 0.7920(2) 0.6398(2) 0.0180(6) Uani 1 1 d . . . . .
N4 N 0.8101(3) 0.5872(2) 0.7279(2) 0.0211(6) Uani 1 1 d . . . . .
N5 N 0.4605(3) 0.6405(2) 0.7889(2) 0.0193(6) Uani 1 1 d . . . . .
N6 N 0.7491(4) 1.0355(2) 0.4976(2) 0.0260(7) Uani 1 1 d . . . . .
F1 F 0.3522(4) 0.2022(3) 1.1090(2) 0.0728(10) Uani 1 1 d . . . . .
F2 F 0.3020(5) 0.2445(5) 0.8925(3) 0.138(2) Uani 1 1 d . . . . .
O3 O 0.9869(4) 0.1542(3) 0.9197(3) 0.0541(9) Uani 1 1 d . . . . .
F3 F 0.5079(6) 0.1719(4) 0.9737(3) 0.143(3) Uani 1 1 d . . . . .
O4 O 0.7681(5) 0.0294(3) 1.0682(3) 0.0634(10) Uani 1 1 d . . . . .
F4 F 0.3920(9) 0.3261(4) 0.9605(4) 0.157(3) Uani 1 1 d . . . . .
F5 F 0.1498(6) 0.2636(7) 1.0279(3) 0.192(4) Uani 1 1 d . . . . .
F6 F 0.2700(10) 0.1143(5) 1.0400(4) 0.168(3) 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
C1 N5 1.344(4) . ?
C1 C2 1.388(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(5) . ?
C4 H4 0.9300 . ?
C5 N5 1.358(4) . ?
C5 C6 1.467(5) . ?
C6 N3 1.334(4) . ?
C6 C7 1.415(5) . ?
C7 C8 1.352(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.415(5) . ?
C8 H8 0.9300 . ?
C9 N6 1.338(4) . ?
C9 C10 1.430(5) . ?
C10 N3 1.388(4) . ?
C10 C11 1.399(5) . ?
C11 C12 1.412(5) . ?
C11 C33 1.530(5) . ?
C12 C17 1.412(5) . ?
C12 C13 1.440(5) . ?
C13 N6 1.339(5) . ?
C13 C14 1.419(5) . ?
C14 C15 1.346(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.406(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N1 1.333(5) . ?
C18 C19 1.378(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.394(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(5) . ?
C21 H21 0.9300 . ?
C22 N1 1.375(4) . ?
C22 C23 1.474(5) . ?
C23 N2 1.351(4) . ?
C23 C24 1.393(5) . ?
C24 C25 1.384(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.385(5) . ?
C26 H26 0.9300 . ?
C27 N2 1.341(5) . ?
C27 C28 1.472(5) . ?
C28 N4 1.369(5) . ?
C28 C29 1.383(5) . ?
C29 C30 1.380(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.376(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.386(5) . ?
C31 H31 0.9300 . ?
C32 N4 1.333(4) . ?
C32 H32 0.9300 . ?
C33 O1 1.216(4) . ?
C33 O2 1.280(4) . ?
O2 RU1 2.095(2) . ?
RU1 N2 1.968(3) . ?
RU1 N5 2.016(3) . ?
RU1 N3 2.039(3) . ?
RU1 N4 2.064(3) . ?
RU1 N1 2.065(3) . ?
P1 F4 1.513(4) . ?
P1 F3 1.530(4) . ?
P1 F5 1.549(5) . ?
P1 F1 1.558(3) . ?
P1 F6 1.560(5) . ?
P1 F2 1.576(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
N5 C1 C2 122.0(3) . . ?
N5 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.6(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N5 C5 C4 121.6(3) . . ?
N5 C5 C6 114.9(3) . . ?
C4 C5 C6 123.3(3) . . ?
N3 C6 C7 123.1(3) . . ?
N3 C6 C5 114.3(3) . . ?
C7 C6 C5 122.4(3) . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
N6 C9 C8 118.3(3) . . ?
N6 C9 C10 122.7(3) . . ?
C8 C9 C10 119.0(3) . . ?
N3 C10 C11 121.0(3) . . ?
N3 C10 C9 119.5(3) . . ?
C11 C10 C9 119.4(3) . . ?
C10 C11 C12 117.7(3) . . ?
C10 C11 C33 123.4(3) . . ?
C12 C11 C33 118.7(3) . . ?
C17 C12 C11 123.8(3) . . ?
C17 C12 C13 118.0(3) . . ?
C11 C12 C13 118.2(3) . . ?
N6 C13 C14 117.8(3) . . ?
N6 C13 C12 123.3(3) . . ?
C14 C13 C12 118.8(3) . . ?
C15 C14 C13 121.2(4) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 120.5(4) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C12 120.9(4) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
N1 C18 C19 123.0(3) . . ?
N1 C18 H18 118.5 . . ?
C19 C18 H18 118.5 . . ?
C20 C19 C18 119.3(4) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 119.0(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C22 C21 C20 119.0(3) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
N1 C22 C21 121.7(3) . . ?
N1 C22 C23 115.0(3) . . ?
C21 C22 C23 123.3(3) . . ?
N2 C23 C24 119.8(3) . . ?
N2 C23 C22 113.4(3) . . ?
C24 C23 C22 126.8(3) . . ?
C25 C24 C23 118.4(3) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C26 C25 C24 120.9(3) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 118.5(3) . . ?
C25 C26 H26 120.7 . . ?
C27 C26 H26 120.7 . . ?
N2 C27 C26 120.3(3) . . ?
N2 C27 C28 112.7(3) . . ?
C26 C27 C28 127.0(3) . . ?
N4 C28 C29 121.6(3) . . ?
N4 C28 C27 114.9(3) . . ?
C29 C28 C27 123.4(3) . . ?
C30 C29 C28 119.0(4) . . ?
C30 C29 H29 120.5 . . ?
C28 C29 H29 120.5 . . ?
C31 C30 C29 119.4(4) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C30 C31 C32 119.2(4) . . ?
C30 C31 H31 120.4 . . ?
C32 C31 H31 120.4 . . ?
N4 C32 C31 122.2(4) . . ?
N4 C32 H32 118.9 . . ?
C31 C32 H32 118.9 . . ?
O1 C33 O2 124.8(3) . . ?
O1 C33 C11 116.6(3) . . ?
O2 C33 C11 118.6(3) . . ?
C33 O2 RU1 114.2(2) . . ?
N2 RU1 N5 97.45(11) . . ?
N2 RU1 N3 176.84(11) . . ?
N5 RU1 N3 79.46(11) . . ?
N2 RU1 N4 79.01(12) . . ?
N5 RU1 N4 90.95(11) . . ?
N3 RU1 N4 100.29(11) . . ?
N2 RU1 N1 79.97(11) . . ?
N5 RU1 N1 91.74(11) . . ?
N3 RU1 N1 100.69(11) . . ?
N4 RU1 N1 158.98(12) . . ?
N2 RU1 O2 89.97(10) . . ?
N5 RU1 O2 172.51(10) . . ?
N3 RU1 O2 93.11(10) . . ?
N4 RU1 O2 89.46(11) . . ?
N1 RU1 O2 90.55(10) . . ?
F4 P1 F3 89.0(4) . . ?
F4 P1 F5 95.6(5) . . ?
F3 P1 F5 175.1(5) . . ?
F4 P1 F1 93.1(3) . . ?
F3 P1 F1 91.7(3) . . ?
F5 P1 F1 89.8(2) . . ?
F4 P1 F6 178.9(3) . . ?
F3 P1 F6 91.1(4) . . ?
F5 P1 F6 84.3(4) . . ?
F1 P1 F6 87.9(2) . . ?
F4 P1 F2 86.8(3) . . ?
F3 P1 F2 91.6(3) . . ?
F5 P1 F2 86.9(3) . . ?
F1 P1 F2 176.7(3) . . ?
F6 P1 F2 92.1(3) . . ?
C18 N1 C22 118.0(3) . . ?
C18 N1 RU1 128.8(2) . . ?
C22 N1 RU1 113.2(2) . . ?
C27 N2 C23 122.1(3) . . ?
C27 N2 RU1 119.6(2) . . ?
C23 N2 RU1 118.3(2) . . ?
C6 N3 C10 119.1(3) . . ?
C6 N3 RU1 115.8(2) . . ?
C10 N3 RU1 124.7(2) . . ?
C32 N4 C28 118.5(3) . . ?
C32 N4 RU1 127.7(3) . . ?
C28 N4 RU1 113.8(2) . . ?
C1 N5 C5 118.5(3) . . ?
C1 N5 RU1 126.2(2) . . ?
C5 N5 RU1 115.2(2) . . ?
C9 N6 C13 118.1(3) . . ?

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
N5 C1 C2 C3 0.5(6) . . . . ?
C1 C2 C3 C4 -1.9(6) . . . . ?
C2 C3 C4 C5 0.9(6) . . . . ?
C3 C4 C5 N5 1.6(6) . . . . ?
C3 C4 C5 C6 -174.3(3) . . . . ?
N5 C5 C6 N3 5.0(4) . . . . ?
C4 C5 C6 N3 -178.9(3) . . . . ?
N5 C5 C6 C7 -170.6(3) . . . . ?
C4 C5 C6 C7 5.6(6) . . . . ?
N3 C6 C7 C8 -4.1(6) . . . . ?
C5 C6 C7 C8 171.0(3) . . . . ?
C6 C7 C8 C9 1.9(6) . . . . ?
C7 C8 C9 N6 -177.7(3) . . . . ?
C7 C8 C9 C10 3.7(5) . . . . ?
N6 C9 C10 N3 173.9(3) . . . . ?
C8 C9 C10 N3 -7.5(5) . . . . ?
N6 C9 C10 C11 -7.4(5) . . . . ?
C8 C9 C10 C11 171.2(3) . . . . ?
N3 C10 C11 C12 -174.7(3) . . . . ?
C9 C10 C11 C12 6.6(5) . . . . ?
N3 C10 C11 C33 10.6(5) . . . . ?
C9 C10 C11 C33 -168.1(3) . . . . ?
C10 C11 C12 C17 178.8(3) . . . . ?
C33 C11 C12 C17 -6.2(5) . . . . ?
C10 C11 C12 C13 -0.4(5) . . . . ?
C33 C11 C12 C13 174.6(3) . . . . ?
C17 C12 C13 N6 174.7(4) . . . . ?
C11 C12 C13 N6 -6.1(6) . . . . ?
C17 C12 C13 C14 -2.0(5) . . . . ?
C11 C12 C13 C14 177.2(3) . . . . ?
N6 C13 C14 C15 -176.0(4) . . . . ?
C12 C13 C14 C15 0.8(6) . . . . ?
C13 C14 C15 C16 1.2(7) . . . . ?
C14 C15 C16 C17 -2.1(7) . . . . ?
C15 C16 C17 C12 0.9(7) . . . . ?
C11 C12 C17 C16 -178.1(4) . . . . ?
C13 C12 C17 C16 1.1(6) . . . . ?
N1 C18 C19 C20 -1.2(6) . . . . ?
C18 C19 C20 C21 -0.2(5) . . . . ?
C19 C20 C21 C22 0.8(5) . . . . ?
C20 C21 C22 N1 -0.1(5) . . . . ?
C20 C21 C22 C23 179.0(3) . . . . ?
N1 C22 C23 N2 -1.1(4) . . . . ?
C21 C22 C23 N2 179.7(3) . . . . ?
N1 C22 C23 C24 178.6(3) . . . . ?
C21 C22 C23 C24 -0.6(6) . . . . ?
N2 C23 C24 C25 -0.6(5) . . . . ?
C22 C23 C24 C25 179.8(3) . . . . ?
C23 C24 C25 C26 0.0(6) . . . . ?
C24 C25 C26 C27 0.4(6) . . . . ?
C25 C26 C27 N2 -0.4(5) . . . . ?
C25 C26 C27 C28 176.7(3) . . . . ?
N2 C27 C28 N4 2.4(4) . . . . ?
C26 C27 C28 N4 -174.8(3) . . . . ?
N2 C27 C28 C29 -179.2(3) . . . . ?
C26 C27 C28 C29 3.6(6) . . . . ?
N4 C28 C29 C30 2.6(5) . . . . ?
C27 C28 C29 C30 -175.7(3) . . . . ?
C28 C29 C30 C31 -1.3(6) . . . . ?
C29 C30 C31 C32 0.1(6) . . . . ?
C30 C31 C32 N4 -0.1(6) . . . . ?
C10 C11 C33 O1 127.3(4) . . . . ?
C12 C11 C33 O1 -47.4(5) . . . . ?
C10 C11 C33 O2 -54.6(5) . . . . ?
C12 C11 C33 O2 130.7(3) . . . . ?
O1 C33 O2 RU1 -123.3(3) . . . . ?
C11 C33 O2 RU1 58.7(3) . . . . ?
C19 C18 N1 C22 1.9(5) . . . . ?
C19 C18 N1 RU1 -176.6(3) . . . . ?
C21 C22 N1 C18 -1.2(5) . . . . ?
C23 C22 N1 C18 179.6(3) . . . . ?
C21 C22 N1 RU1 177.5(3) . . . . ?
C23 C22 N1 RU1 -1.7(4) . . . . ?
C26 C27 N2 C23 -0.1(5) . . . . ?
C28 C27 N2 C23 -177.6(3) . . . . ?
C26 C27 N2 RU1 176.5(3) . . . . ?
C28 C27 N2 RU1 -0.9(4) . . . . ?
C24 C23 N2 C27 0.6(5) . . . . ?
C22 C23 N2 C27 -179.7(3) . . . . ?
C24 C23 N2 RU1 -176.1(2) . . . . ?
C22 C23 N2 RU1 3.6(4) . . . . ?
C7 C6 N3 C10 0.3(5) . . . . ?
C5 C6 N3 C10 -175.2(3) . . . . ?
C7 C6 N3 RU1 173.1(3) . . . . ?
C5 C6 N3 RU1 -2.4(4) . . . . ?
C11 C10 N3 C6 -173.2(3) . . . . ?
C9 C10 N3 C6 5.5(5) . . . . ?
C11 C10 N3 RU1 14.7(4) . . . . ?
C9 C10 N3 RU1 -166.6(2) . . . . ?
C31 C32 N4 C28 1.4(5) . . . . ?
C31 C32 N4 RU1 179.7(3) . . . . ?
C29 C28 N4 C32 -2.6(5) . . . . ?
C27 C28 N4 C32 175.8(3) . . . . ?
C29 C28 N4 RU1 178.8(3) . . . . ?
C27 C28 N4 RU1 -2.7(4) . . . . ?
C2 C1 N5 C5 1.9(5) . . . . ?
C2 C1 N5 RU1 -179.9(3) . . . . ?
C4 C5 N5 C1 -3.0(5) . . . . ?
C6 C5 N5 C1 173.2(3) . . . . ?
C4 C5 N5 RU1 178.6(3) . . . . ?
C6 C5 N5 RU1 -5.2(4) . . . . ?
C8 C9 N6 C13 -177.5(3) . . . . ?
C10 C9 N6 C13 1.0(5) . . . . ?
C14 C13 N6 C9 -177.6(3) . . . . ?
C12 C13 N6 C9 5.8(6) . . . . ?

_refine_diff_density_max         1.618
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.108

####################################################################### 
# 
# 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_SHELXT_a
_database_code_depnum_ccdc_archive 'CCDC 1517503'
_audit_update_record             
;
2016-11-16 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H24 B F10 N6 O P Ru'
_chemical_formula_weight         853.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   16.9299(4)
_cell_length_b                   16.5148(3)
_cell_length_c                   11.3820(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.740(2)
_cell_angle_gamma                90
_cell_volume                     3126.59(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    93
_cell_measurement_reflns_used    16206
_cell_measurement_theta_min      2.4470
_cell_measurement_theta_max      28.2380

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_F_000             1704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.655
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26116
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7145
_reflns_number_gt                6565
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0727P)²+22.4749P] 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         7145
_refine_ls_number_parameters     478
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1624
_refine_ls_wR_factor_gt          0.1592
_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
C1 C 0.3878(3) 0.4092(3) 0.8679(4) 0.0201(8) Uani 1 1 d . . . . .
H1 H 0.391527 0.367656 0.814083 0.024 Uiso 1 1 calc R U . . .
C2 C 0.4348(3) 0.4057(3) 0.9804(4) 0.0229(9) Uani 1 1 d . . . . .
H2 H 0.470463 0.363073 1.001841 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4278(3) 0.4670(3) 1.0611(4) 0.0252(9) Uani 1 1 d . . . . .
H3 H 0.457052 0.464553 1.138735 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3771(3) 0.5319(3) 1.0258(4) 0.0229(9) Uani 1 1 d . . . . .
H4 H 0.372415 0.573678 1.078754 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3331(3) 0.5333(2) 0.9090(4) 0.0179(8) Uani 1 1 d . . . . .
C6 C 0.2837(3) 0.6017(3) 0.8589(4) 0.0188(8) Uani 1 1 d . . . . .
C7 C 0.2914(3) 0.6777(3) 0.9116(4) 0.0229(9) Uani 1 1 d . . . . .
H7 H 0.323224 0.684624 0.986801 0.028 Uiso 1 1 calc R U . . .
C8 C 0.2520(3) 0.7426(3) 0.8527(4) 0.0243(9) Uani 1 1 d . . . . .
H8 H 0.257414 0.793827 0.887087 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2036(3) 0.7310(3) 0.7407(4) 0.0210(9) Uani 1 1 d . . . . .
C10 C 0.1934(3) 0.6523(2) 0.6929(4) 0.0173(8) Uani 1 1 d . . . . .
C11 C 0.1357(3) 0.6373(3) 0.5780(4) 0.0206(8) Uani 1 1 d . . . . .
H11 H 0.090202 0.606923 0.595206 0.025 Uiso 1 1 calc R U . . .
H11A H 0.162159 0.604134 0.526508 0.025 Uiso 1 1 calc R U . . .
C12 C 0.1053(3) 0.7135(3) 0.5116(4) 0.0202(8) Uani 1 1 d . . . . .
C13 C 0.1220(3) 0.7897(3) 0.5631(4) 0.0211(8) Uani 1 1 d . . . . .
C14 C 0.0948(3) 0.8596(3) 0.4996(4) 0.0232(9) Uani 1 1 d . . . . .
H14 H 0.106196 0.910221 0.534477 0.028 Uiso 1 1 calc R U . . .
C15 C 0.0509(3) 0.8537(3) 0.3850(4) 0.0253(9) Uani 1 1 d . . . . .
H15 H 0.032962 0.900406 0.342627 0.030 Uiso 1 1 calc R U . . .
C16 C 0.0334(3) 0.7787(3) 0.3327(4) 0.0264(9) Uani 1 1 d . . . . .
H16 H 0.003595 0.774769 0.255531 0.032 Uiso 1 1 calc R U . . .
C17 C 0.0608(3) 0.7090(3) 0.3963(4) 0.0233(9) Uani 1 1 d . . . . .
H17 H 0.049045 0.658572 0.360999 0.028 Uiso 1 1 calc R U . . .
C18 C 0.1399(3) 0.4359(3) 0.8846(4) 0.0233(9) Uani 1 1 d . . . . .
H18 H 0.138264 0.491749 0.894066 0.028 Uiso 1 1 calc R U . . .
C19 C 0.1007(3) 0.3874(3) 0.9543(4) 0.0277(10) Uani 1 1 d . . . . .
H19 H 0.073501 0.410323 1.009840 0.033 Uiso 1 1 calc R U . . .
C20 C 0.1026(3) 0.3048(3) 0.9404(4) 0.0272(10) Uani 1 1 d . . . . .
H20 H 0.075323 0.271229 0.985006 0.033 Uiso 1 1 calc R U . . .
C21 C 0.1455(3) 0.2720(3) 0.8590(4) 0.0235(9) Uani 1 1 d . . . . .
H21 H 0.148277 0.216215 0.849729 0.028 Uiso 1 1 calc R U . . .
C22 C 0.1841(3) 0.3232(3) 0.7922(4) 0.0191(8) Uani 1 1 d . . . . .
C23 C 0.2329(3) 0.2951(3) 0.7049(4) 0.0199(8) Uani 1 1 d . . . . .
C24 C 0.2505(3) 0.2158(3) 0.6815(5) 0.0279(10) Uani 1 1 d . . . . .
H24 H 0.230352 0.173105 0.720291 0.033 Uiso 1 1 calc R U . . .
C25 C 0.2994(3) 0.2019(3) 0.5976(5) 0.0354(12) Uani 1 1 d . . . . .
H25 H 0.311484 0.148905 0.579528 0.043 Uiso 1 1 calc R U . . .
C26 C 0.3302(3) 0.2650(3) 0.5411(5) 0.0310(11) Uani 1 1 d . . . . .
H26 H 0.363461 0.254988 0.486373 0.037 Uiso 1 1 calc R U . . .
C27 C 0.3107(3) 0.3436(3) 0.5672(4) 0.0217(9) Uani 1 1 d . . . . .
C28 C 0.3395(3) 0.4194(3) 0.5198(4) 0.0206(8) Uani 1 1 d . . . . .
C29 C 0.3897(3) 0.4209(3) 0.4369(4) 0.0279(10) Uani 1 1 d . . . . .
H29 H 0.406309 0.372930 0.406144 0.033 Uiso 1 1 calc R U . . .
C30 C 0.4146(3) 0.4946(4) 0.4006(5) 0.0323(11) Uani 1 1 d . . . . .
H30 H 0.448356 0.496597 0.344904 0.039 Uiso 1 1 calc R U . . .
C31 C 0.3897(3) 0.5655(3) 0.4466(4) 0.0298(10) Uani 1 1 d . . . . .
H31 H 0.405935 0.615573 0.422308 0.036 Uiso 1 1 calc R U . . .
C32 C 0.3398(3) 0.5597(3) 0.5302(4) 0.0234(9) Uani 1 1 d . . . . .
H32 H 0.323493 0.607103 0.562841 0.028 Uiso 1 1 calc R U . . .
C33 C 0.1423(3) 0.4610(2) 0.5744(4) 0.0205(8) Uani 1 1 d . . . . .
RU1 Ru 0.23889(2) 0.46849(2) 0.68760(3) 0.01468(12) Uani 1 1 d . . . . .
P1 P 0.53663(12) 0.23455(12) 0.78841(18) 0.0527(4) Uani 1 1 d . . . . .
F1 F 0.18862(19) 0.94063(16) 0.8269(3) 0.0306(6) Uani 1 1 d . . . . .
F2 F 0.1828(2) 1.07759(17) 0.8350(3) 0.0360(7) Uani 1 1 d . . . . .
F3 F 0.2119(2) 1.0155(2) 0.6702(3) 0.0420(8) Uani 1 1 d . . . . .
F4 F 0.0865(2) 1.0067(2) 0.7098(3) 0.0459(8) Uani 1 1 d . . . . .
O1 O 0.0821(2) 0.4475(2) 0.5147(3) 0.0288(7) Uani 1 1 d . . . . .
N1 N 0.3143(2) 0.4891(2) 0.5653(3) 0.0195(7) Uani 1 1 d . . . . .
N2 N 0.2621(2) 0.3558(2) 0.6468(3) 0.0179(7) Uani 1 1 d . . . . .
N3 N 0.1800(2) 0.4054(2) 0.8042(3) 0.0183(7) Uani 1 1 d . . . . .
N4 N 0.3365(2) 0.4708(2) 0.8330(3) 0.0165(7) Uani 1 1 d . . . . .
N5 N 0.2342(2) 0.5891(2) 0.7504(3) 0.0162(7) Uani 1 1 d . . . . .
N6 N 0.1673(3) 0.7957(2) 0.6778(4) 0.0244(8) Uani 1 1 d . . . . .
H6 H 0.172732 0.842657 0.711064 0.029 Uiso 1 1 calc R U . . .
F5 F 0.5320(3) 0.1442(4) 0.7675(6) 0.101(2) Uani 1 1 d . . . . .
F6 F 0.6209(4) 0.2372(4) 0.8342(5) 0.107(3) Uani 1 1 d . . . . .
F7 F 0.5377(4) 0.3292(4) 0.7831(9) 0.131(3) Uani 1 1 d . . . . .
F8 F 0.5317(5) 0.2467(6) 0.6568(6) 0.156(4) Uani 1 1 d . . . . .
F9 F 0.4504(4) 0.2385(3) 0.7955(10) 0.147(4) Uani 1 1 d . . . . .
B1 B 0.1664(4) 1.0108(3) 0.7600(5) 0.0265(11) Uani 1 1 d . . . . .
F10 F 0.5347(6) 0.2320(4) 0.9260(7) 0.119(3) 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
C1 N4 1.349(5) . ?
C1 C2 1.377(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(6) . ?
C4 H4 0.9300 . ?
C5 N4 1.354(5) . ?
C5 C6 1.458(6) . ?
C6 N5 1.373(6) . ?
C6 C7 1.387(6) . ?
C7 C8 1.369(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.394(6) . ?
C8 H8 0.9300 . ?
C9 N6 1.367(6) . ?
C9 C10 1.407(6) . ?
C10 N5 1.352(5) . ?
C10 C11 1.499(6) . ?
C11 C12 1.508(6) . ?
C11 H11 0.9700 . ?
C11 H11A 0.9700 . ?
C12 C17 1.388(6) . ?
C12 C13 1.395(6) . ?
C13 N6 1.389(6) . ?
C13 C14 1.394(6) . ?
C14 C15 1.379(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.392(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N3 1.336(6) . ?
C18 C19 1.380(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.390(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(6) . ?
C21 H21 0.9300 . ?
C22 N3 1.368(5) . ?
C22 C23 1.480(6) . ?
C23 N2 1.344(6) . ?
C23 C24 1.381(6) . ?
C24 C25 1.394(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.386(6) . ?
C26 H26 0.9300 . ?
C27 N2 1.348(6) . ?
C27 C28 1.481(6) . ?
C28 N1 1.364(6) . ?
C28 C29 1.383(6) . ?
C29 C30 1.376(8) . ?
C29 H29 0.9300 . ?
C30 C31 1.380(8) . ?
C30 H30 0.9300 . ?
C31 C32 1.389(6) . ?
C31 H31 0.9300 . ?
C32 N1 1.330(6) . ?
C32 H32 0.9300 . ?
C33 O1 1.137(6) . ?
C33 RU1 1.888(5) . ?
RU1 N2 1.975(3) . ?
RU1 N3 2.082(4) . ?
RU1 N1 2.085(4) . ?
RU1 N4 2.110(4) . ?
RU1 N5 2.122(3) . ?
P1 F6 1.425(6) . ?
P1 F9 1.479(6) . ?
P1 F8 1.498(6) . ?
P1 F5 1.511(6) . ?
P1 F7 1.565(6) . ?
P1 F10 1.573(7) . ?
F1 B1 1.399(6) . ?
F2 B1 1.390(6) . ?
F3 B1 1.393(7) . ?
F4 B1 1.369(7) . ?
N6 H6 0.8600 . ?

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
N4 C1 C2 122.3(4) . . ?
N4 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 118.7(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N4 C5 C4 121.1(4) . . ?
N4 C5 C6 115.5(4) . . ?
C4 C5 C6 123.4(4) . . ?
N5 C6 C7 121.2(4) . . ?
N5 C6 C5 116.4(4) . . ?
C7 C6 C5 122.1(4) . . ?
C8 C7 C6 119.9(4) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 119.3(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
N6 C9 C8 120.1(4) . . ?
N6 C9 C10 120.6(4) . . ?
C8 C9 C10 119.3(4) . . ?
N5 C10 C9 120.8(4) . . ?
N5 C10 C11 119.0(4) . . ?
C9 C10 C11 120.2(4) . . ?
C10 C11 C12 113.9(4) . . ?
C10 C11 H11 108.8 . . ?
C12 C11 H11 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
H11 C11 H11A 107.7 . . ?
C17 C12 C13 118.5(4) . . ?
C17 C12 C11 120.2(4) . . ?
C13 C12 C11 121.2(4) . . ?
N6 C13 C14 119.9(4) . . ?
N6 C13 C12 119.5(4) . . ?
C14 C13 C12 120.5(4) . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.3(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 119.5(4) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C12 C17 C16 121.1(4) . . ?
C12 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
N3 C18 C19 122.4(4) . . ?
N3 C18 H18 118.8 . . ?
C19 C18 H18 118.8 . . ?
C20 C19 C18 119.1(4) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 119.3(4) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C22 C21 C20 119.3(4) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
N3 C22 C21 121.0(4) . . ?
N3 C22 C23 115.0(4) . . ?
C21 C22 C23 124.0(4) . . ?
N2 C23 C24 120.0(4) . . ?
N2 C23 C22 113.5(4) . . ?
C24 C23 C22 126.5(4) . . ?
C23 C24 C25 117.8(5) . . ?
C23 C24 H24 121.1 . . ?
C25 C24 H24 121.1 . . ?
C26 C25 C24 121.3(4) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C25 C26 C27 118.9(4) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 H26 120.5 . . ?
N2 C27 C26 118.9(4) . . ?
N2 C27 C28 113.7(4) . . ?
C26 C27 C28 127.3(4) . . ?
N1 C28 C29 121.3(4) . . ?
N1 C28 C27 115.3(4) . . ?
C29 C28 C27 123.3(4) . . ?
C30 C29 C28 118.8(5) . . ?
C30 C29 H29 120.6 . . ?
C28 C29 H29 120.6 . . ?
C29 C30 C31 120.3(4) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C30 C31 C32 118.0(5) . . ?
C30 C31 H31 121.0 . . ?
C32 C31 H31 121.0 . . ?
N1 C32 C31 122.6(5) . . ?
N1 C32 H32 118.7 . . ?
C31 C32 H32 118.7 . . ?
O1 C33 RU1 170.8(4) . . ?
C33 RU1 N2 87.85(16) . . ?
C33 RU1 N3 86.85(17) . . ?
N2 RU1 N3 79.53(14) . . ?
C33 RU1 N1 96.64(17) . . ?
N2 RU1 N1 79.86(15) . . ?
N3 RU1 N1 158.94(14) . . ?
C33 RU1 N4 171.35(16) . . ?
N2 RU1 N4 92.34(14) . . ?
N3 RU1 N4 84.68(14) . . ?
N1 RU1 N4 91.90(14) . . ?
C33 RU1 N5 102.08(16) . . ?
N2 RU1 N5 170.03(14) . . ?
N3 RU1 N5 101.66(13) . . ?
N1 RU1 N5 97.91(14) . . ?
N4 RU1 N5 77.98(13) . . ?
F6 P1 F9 155.5(6) . . ?
F6 P1 F8 103.1(4) . . ?
F9 P1 F8 100.2(6) . . ?
F6 P1 F5 96.1(3) . . ?
F9 P1 F5 91.7(3) . . ?
F8 P1 F5 89.0(5) . . ?
F6 P1 F7 88.0(4) . . ?
F9 P1 F7 88.7(3) . . ?
F8 P1 F7 80.0(5) . . ?
F5 P1 F7 168.9(5) . . ?
F6 P1 F10 80.9(4) . . ?
F9 P1 F10 75.1(5) . . ?
F8 P1 F10 172.5(6) . . ?
F5 P1 F10 96.9(4) . . ?
F7 P1 F10 93.9(5) . . ?
C32 N1 C28 118.9(4) . . ?
C32 N1 RU1 128.1(3) . . ?
C28 N1 RU1 112.9(3) . . ?
C23 N2 C27 123.0(4) . . ?
C23 N2 RU1 118.7(3) . . ?
C27 N2 RU1 118.2(3) . . ?
C18 N3 C22 119.0(4) . . ?
C18 N3 RU1 127.9(3) . . ?
C22 N3 RU1 113.2(3) . . ?
C1 N4 C5 119.2(4) . . ?
C1 N4 RU1 125.7(3) . . ?
C5 N4 RU1 113.3(3) . . ?
C10 N5 C6 119.3(3) . . ?
C10 N5 RU1 127.6(3) . . ?
C6 N5 RU1 113.0(3) . . ?
C9 N6 C13 123.5(4) . . ?
C9 N6 H6 118.3 . . ?
C13 N6 H6 118.3 . . ?
F4 B1 F2 111.3(4) . . ?
F4 B1 F3 109.6(4) . . ?
F2 B1 F3 109.4(4) . . ?
F4 B1 F1 109.3(4) . . ?
F2 B1 F1 108.7(4) . . ?
F3 B1 F1 108.4(4) . . ?

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
N4 C1 C2 C3 1.3(7) . . . . ?
C1 C2 C3 C4 -3.0(7) . . . . ?
C2 C3 C4 C5 0.8(7) . . . . ?
C3 C4 C5 N4 3.3(7) . . . . ?
C3 C4 C5 C6 -174.3(4) . . . . ?
N4 C5 C6 N5 12.5(5) . . . . ?
C4 C5 C6 N5 -169.8(4) . . . . ?
N4 C5 C6 C7 -161.6(4) . . . . ?
C4 C5 C6 C7 16.1(7) . . . . ?
N5 C6 C7 C8 -3.0(7) . . . . ?
C5 C6 C7 C8 170.8(4) . . . . ?
C6 C7 C8 C9 0.9(7) . . . . ?
C7 C8 C9 N6 -176.5(4) . . . . ?
C7 C8 C9 C10 2.8(7) . . . . ?
N6 C9 C10 N5 174.7(4) . . . . ?
C8 C9 C10 N5 -4.6(7) . . . . ?
N6 C9 C10 C11 -6.3(7) . . . . ?
C8 C9 C10 C11 174.4(4) . . . . ?
N5 C10 C11 C12 -169.8(4) . . . . ?
C9 C10 C11 C12 11.3(6) . . . . ?
C10 C11 C12 C17 170.8(4) . . . . ?
C10 C11 C12 C13 -8.1(6) . . . . ?
C17 C12 C13 N6 -179.2(4) . . . . ?
C11 C12 C13 N6 -0.3(6) . . . . ?
C17 C12 C13 C14 -0.2(7) . . . . ?
C11 C12 C13 C14 178.7(4) . . . . ?
N6 C13 C14 C15 179.0(4) . . . . ?
C12 C13 C14 C15 0.0(7) . . . . ?
C13 C14 C15 C16 0.2(7) . . . . ?
C14 C15 C16 C17 -0.3(7) . . . . ?
C13 C12 C17 C16 0.2(7) . . . . ?
C11 C12 C17 C16 -178.7(4) . . . . ?
C15 C16 C17 C12 0.1(7) . . . . ?
N3 C18 C19 C20 -0.3(8) . . . . ?
C18 C19 C20 C21 1.7(8) . . . . ?
C19 C20 C21 C22 -1.3(7) . . . . ?
C20 C21 C22 N3 -0.6(7) . . . . ?
C20 C21 C22 C23 178.7(4) . . . . ?
N3 C22 C23 N2 -3.2(6) . . . . ?
C21 C22 C23 N2 177.5(4) . . . . ?
N3 C22 C23 C24 175.9(4) . . . . ?
C21 C22 C23 C24 -3.4(7) . . . . ?
N2 C23 C24 C25 0.6(7) . . . . ?
C22 C23 C24 C25 -178.4(5) . . . . ?
C23 C24 C25 C26 0.9(8) . . . . ?
C24 C25 C26 C27 -1.1(9) . . . . ?
C25 C26 C27 N2 -0.2(8) . . . . ?
C25 C26 C27 C28 177.7(5) . . . . ?
N2 C27 C28 N1 1.4(6) . . . . ?
C26 C27 C28 N1 -176.6(5) . . . . ?
N2 C27 C28 C29 -179.8(4) . . . . ?
C26 C27 C28 C29 2.2(8) . . . . ?
N1 C28 C29 C30 0.3(7) . . . . ?
C27 C28 C29 C30 -178.4(4) . . . . ?
C28 C29 C30 C31 0.0(8) . . . . ?
C29 C30 C31 C32 0.4(8) . . . . ?
C30 C31 C32 N1 -1.2(8) . . . . ?
C31 C32 N1 C28 1.5(7) . . . . ?
C31 C32 N1 RU1 -179.4(4) . . . . ?
C29 C28 N1 C32 -1.0(7) . . . . ?
C27 C28 N1 C32 177.8(4) . . . . ?
C29 C28 N1 RU1 179.7(3) . . . . ?
C27 C28 N1 RU1 -1.4(5) . . . . ?
C24 C23 N2 C27 -1.9(7) . . . . ?
C22 C23 N2 C27 177.2(4) . . . . ?
C24 C23 N2 RU1 -177.7(4) . . . . ?
C22 C23 N2 RU1 1.4(5) . . . . ?
C26 C27 N2 C23 1.7(7) . . . . ?
C28 C27 N2 C23 -176.5(4) . . . . ?
C26 C27 N2 RU1 177.5(4) . . . . ?
C28 C27 N2 RU1 -0.7(5) . . . . ?
C19 C18 N3 C22 -1.6(7) . . . . ?
C19 C18 N3 RU1 177.7(4) . . . . ?
C21 C22 N3 C18 2.0(7) . . . . ?
C23 C22 N3 C18 -177.3(4) . . . . ?
C21 C22 N3 RU1 -177.3(3) . . . . ?
C23 C22 N3 RU1 3.3(5) . . . . ?
C2 C1 N4 C5 2.8(6) . . . . ?
C2 C1 N4 RU1 -161.0(3) . . . . ?
C4 C5 N4 C1 -5.0(6) . . . . ?
C6 C5 N4 C1 172.7(4) . . . . ?
C4 C5 N4 RU1 160.7(3) . . . . ?
C6 C5 N4 RU1 -21.6(4) . . . . ?
C9 C10 N5 C6 2.5(6) . . . . ?
C11 C10 N5 C6 -176.5(4) . . . . ?
C9 C10 N5 RU1 -172.6(3) . . . . ?
C11 C10 N5 RU1 8.5(6) . . . . ?
C7 C6 N5 C10 1.3(6) . . . . ?
C5 C6 N5 C10 -172.8(4) . . . . ?
C7 C6 N5 RU1 177.1(3) . . . . ?
C5 C6 N5 RU1 2.9(5) . . . . ?
C8 C9 N6 C13 176.2(4) . . . . ?
C10 C9 N6 C13 -3.1(7) . . . . ?
C14 C13 N6 C9 -172.5(4) . . . . ?
C12 C13 N6 C9 6.5(7) . . . . ?

_refine_diff_density_max         2.007
_refine_diff_density_min         -2.172
_refine_diff_density_rms         0.159


_chemical_properties_physical    ', Air-sensitive'
####################################################################### 
# 
# 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_RutpyCOb_a
_database_code_depnum_ccdc_archive 'CCDC 1517504'
_audit_update_record             
;
2016-11-16 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H21 Cl N6 O6.50 Ru'
_chemical_formula_weight         742.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.4666(11)
_cell_length_b                   11.6275(14)
_cell_length_c                   16.1049(19)
_cell_angle_alpha                90.226(5)
_cell_angle_beta                 98.860(8)
_cell_angle_gamma                97.136(7)
_cell_volume                     1554.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5863
_cell_measurement_theta_min      2.4543
_cell_measurement_theta_max      31.0447

_exptl_crystal_description       Block
_exptl_crystal_colour            'Dark Red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_F_000             748
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.1500
_exptl_absorpt_coefficient_mu    0.649
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'RIGAKU/MSC Meacury CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12223
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.561
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             6747
_reflns_number_gt                5862
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0687P)²+2.2893P] 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         6747
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
C1 C 0.3795(4) 0.9439(3) 0.0863(2) 0.0296(8) Uani 1 1 d . . . . .
H1 H 0.378960 0.876179 0.055340 0.035 Uiso 1 1 calc R U . . .
C2 C 0.3169(5) 1.0371(4) 0.0465(3) 0.0382(10) Uani 1 1 d . . . . .
H2 H 0.275195 1.031675 -0.010483 0.046 Uiso 1 1 calc R U . . .
C3 C 0.3165(5) 1.1377(4) 0.0914(3) 0.0416(10) Uani 1 1 d . . . . .
H3 H 0.271599 1.200002 0.065577 0.050 Uiso 1 1 calc R U . . .
C4 C 0.3833(5) 1.1453(3) 0.1750(3) 0.0374(10) Uani 1 1 d . . . . .
H4 H 0.386375 1.213208 0.206189 0.045 Uiso 1 1 calc R U . . .
C5 C 0.4462(4) 1.0495(3) 0.2119(2) 0.0282(8) Uani 1 1 d . . . . .
C6 C 0.5255(5) 1.0495(3) 0.2992(2) 0.0275(8) Uani 1 1 d . . . . .
C7 C 0.5562(5) 1.1451(4) 0.3571(3) 0.0373(9) Uani 1 1 d . . . . .
H7 H 0.520620 1.215408 0.341104 0.045 Uiso 1 1 calc R U . . .
C8 C 0.6368(6) 1.1343(3) 0.4355(3) 0.0397(10) Uani 1 1 d . . . . .
H8 H 0.656017 1.196930 0.473345 0.048 Uiso 1 1 calc R U . . .
C9 C 0.6922(5) 1.0265(3) 0.4599(2) 0.0329(9) Uani 1 1 d . . . . .
C10 C 0.6574(4) 0.9351(3) 0.4000(2) 0.0264(8) Uani 1 1 d . . . . .
C11 C 0.7052(4) 0.8260(3) 0.4165(2) 0.0250(7) Uani 1 1 d . . . . .
C12 C 0.7945(5) 0.8132(4) 0.4964(2) 0.0311(8) Uani 1 1 d . . . . .
C13 C 0.8267(5) 0.9118(4) 0.5533(3) 0.0382(10) Uani 1 1 d . . . . .
C14 C 0.9175(7) 0.9017(5) 0.6338(3) 0.0581(14) Uani 1 1 d . . . . .
H14 H 0.935551 0.964392 0.671600 0.070 Uiso 1 1 calc R U . . .
C15 C 0.9785(8) 0.8023(5) 0.6568(3) 0.0685(17) Uani 1 1 d . . . . .
H15 H 1.038999 0.797546 0.709740 0.082 Uiso 1 1 calc R U . . .
C16 C 0.9502(7) 0.7056(5) 0.6004(3) 0.0603(15) Uani 1 1 d . . . . .
H16 H 0.993078 0.637875 0.616788 0.072 Uiso 1 1 calc R U . . .
C17 C 0.8619(6) 0.7099(4) 0.5230(3) 0.0443(11) Uani 1 1 d . . . . .
H17 H 0.844967 0.645311 0.486936 0.053 Uiso 1 1 calc R U . . .
C18 C 0.2239(5) 0.7816(3) 0.3210(2) 0.0311(8) Uani 1 1 d . . . . .
H18 H 0.259453 0.854483 0.345739 0.037 Uiso 1 1 calc R U . . .
C19 C 0.0780(5) 0.7249(4) 0.3360(3) 0.0393(10) Uani 1 1 d . . . . .
H19 H 0.016750 0.758970 0.370151 0.047 Uiso 1 1 calc R U . . .
C20 C 0.0252(5) 0.6169(4) 0.2994(3) 0.0416(10) Uani 1 1 d . . . . .
H20 H -0.072539 0.577038 0.308577 0.050 Uiso 1 1 calc R U . . .
C21 C 0.1181(5) 0.5684(4) 0.2491(3) 0.0368(9) Uani 1 1 d . . . . .
H21 H 0.083575 0.495580 0.224058 0.044 Uiso 1 1 calc R U . . .
C22 C 0.2638(4) 0.6292(3) 0.2360(2) 0.0266(8) Uani 1 1 d . . . . .
C23 C 0.3734(5) 0.5854(3) 0.1845(2) 0.0270(8) Uani 1 1 d . . . . .
C24 C 0.3547(5) 0.4776(3) 0.1451(3) 0.0387(10) Uani 1 1 d . . . . .
H24 H 0.262835 0.425384 0.147022 0.046 Uiso 1 1 calc R U . . .
C25 C 0.4748(6) 0.4488(4) 0.1030(3) 0.0419(10) Uani 1 1 d . . . . .
H25 H 0.463978 0.376501 0.076433 0.050 Uiso 1 1 calc R U . . .
C26 C 0.6118(5) 0.5270(3) 0.0999(3) 0.0364(9) Uani 1 1 d . . . . .
H26 H 0.694008 0.507233 0.072548 0.044 Uiso 1 1 calc R U . . .
C27 C 0.6229(5) 0.6343(3) 0.1383(2) 0.0263(7) Uani 1 1 d . . . . .
C28 C 0.7566(4) 0.7276(3) 0.1411(2) 0.0262(7) Uani 1 1 d . . . . .
C29 C 0.8861(5) 0.7244(4) 0.0987(3) 0.0352(9) Uani 1 1 d . . . . .
H29 H 0.894615 0.658590 0.067481 0.042 Uiso 1 1 calc R U . . .
C30 C 1.0021(5) 0.8188(4) 0.1028(3) 0.0425(10) Uani 1 1 d . . . . .
H30 H 1.090111 0.817311 0.074793 0.051 Uiso 1 1 calc R U . . .
C31 C 0.9866(5) 0.9155(4) 0.1488(3) 0.0390(10) Uani 1 1 d . . . . .
H31 H 1.063931 0.980236 0.152210 0.047 Uiso 1 1 calc R U . . .
C32 C 0.8554(5) 0.9154(3) 0.1896(2) 0.0305(8) Uani 1 1 d . . . . .
H32 H 0.845201 0.981653 0.219888 0.037 Uiso 1 1 calc R U . . .
C33 C 0.6506(4) 0.7357(3) 0.3446(2) 0.0248(7) Uani 1 1 d . . . . .
RU1 Ru 0.53780(3) 0.80833(2) 0.24515(2) 0.02196(11) Uani 1 1 d . . . . .
CL1 Cl 0.85103(13) 0.27334(9) 0.10486(7) 0.0398(2) Uani 1 1 d . . . . .
N1 N 0.5045(4) 0.6617(2) 0.17942(18) 0.0230(6) Uani 1 1 d . . . . .
O1 O 0.6816(4) 0.6363(2) 0.35603(18) 0.0360(6) Uani 1 1 d . . . . .
N2 N 0.4410(4) 0.9483(3) 0.16840(19) 0.0254(6) Uani 1 1 d . . . . .
N3 N 0.5757(4) 0.9483(2) 0.32111(18) 0.0233(6) Uani 1 1 d . . . . .
N4 N 0.3163(4) 0.7362(3) 0.27238(19) 0.0249(6) Uani 1 1 d . . . . .
N5 N 0.7413(4) 0.8237(3) 0.18749(18) 0.0241(6) Uani 1 1 d . . . . .
N6 N 0.7753(5) 1.0152(3) 0.5360(2) 0.0413(9) Uani 1 1 d . . . . .
O2 O 0.7539(7) 0.3024(4) 0.0309(2) 0.0954(18) Uani 1 1 d . . . . .
O3 O 0.6393(7) 0.4020(4) 0.3045(3) 0.0930(16) Uani 1 1 d . . . . .
O4 O 0.8308(6) 0.3405(5) 0.1752(3) 0.0947(17) Uani 1 1 d . . . . .
O5 O 0.4277(12) 0.5542(8) 0.4871(6) 0.103(4) Uani 0.5 1 d . . P . .
O6 O 0.8163(12) 0.1600(5) 0.1148(5) 0.204(5) Uani 1 1 d . . . . .
O7 O 1.0086(7) 0.2949(10) 0.0987(5) 0.214(5) 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
C1 N2 1.343(5) . ?
C1 C2 1.381(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(5) . ?
C4 H4 0.9300 . ?
C5 N2 1.359(5) . ?
C5 C6 1.461(5) . ?
C6 N3 1.331(4) . ?
C6 C7 1.421(5) . ?
C7 C8 1.354(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.428(6) . ?
C8 H8 0.9300 . ?
C9 N6 1.332(5) . ?
C9 C10 1.406(5) . ?
C10 N3 1.368(5) . ?
C10 C11 1.392(5) . ?
C11 C12 1.407(5) . ?
C11 C33 1.536(5) . ?
C12 C17 1.433(6) . ?
C12 C13 1.437(6) . ?
C13 N6 1.345(6) . ?
C13 C14 1.416(6) . ?
C14 C15 1.353(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.416(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.356(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N4 1.338(5) . ?
C18 C19 1.382(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.377(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.389(5) . ?
C21 H21 0.9300 . ?
C22 N4 1.366(5) . ?
C22 C23 1.470(5) . ?
C23 N1 1.346(5) . ?
C23 C24 1.383(5) . ?
C24 C25 1.378(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.389(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.378(5) . ?
C26 H26 0.9300 . ?
C27 N1 1.351(5) . ?
C27 C28 1.463(5) . ?
C28 N5 1.372(5) . ?
C28 C29 1.383(5) . ?
C29 C30 1.373(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.375(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.375(6) . ?
C31 H31 0.9300 . ?
C32 N5 1.344(5) . ?
C32 H32 0.9300 . ?
C33 O1 1.226(4) . ?
C33 RU1 1.983(4) . ?
RU1 N1 1.970(3) . ?
RU1 N3 1.995(3) . ?
RU1 N4 2.069(3) . ?
RU1 N5 2.069(3) . ?
RU1 N2 2.210(3) . ?
CL1 O6 1.330(5) . ?
CL1 O7 1.345(6) . ?
CL1 O2 1.407(4) . ?
CL1 O4 1.416(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
N2 C1 C2 121.9(4) . . ?
N2 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.3(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 118.7(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N2 C5 C4 122.0(4) . . ?
N2 C5 C6 114.6(3) . . ?
C4 C5 C6 123.3(4) . . ?
N3 C6 C7 120.5(3) . . ?
N3 C6 C5 112.9(3) . . ?
C7 C6 C5 126.5(3) . . ?
C8 C7 C6 120.4(4) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.8(4) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
N6 C9 C10 122.3(4) . . ?
N6 C9 C8 120.6(4) . . ?
C10 C9 C8 117.1(4) . . ?
N3 C10 C11 115.8(3) . . ?
N3 C10 C9 121.9(3) . . ?
C11 C10 C9 122.4(3) . . ?
C10 C11 C12 116.0(3) . . ?
C10 C11 C33 115.0(3) . . ?
C12 C11 C33 129.0(3) . . ?
C11 C12 C17 124.1(4) . . ?
C11 C12 C13 117.9(4) . . ?
C17 C12 C13 118.0(4) . . ?
N6 C13 C14 116.3(4) . . ?
N6 C13 C12 124.6(4) . . ?
C14 C13 C12 119.2(4) . . ?
C15 C14 C13 121.1(5) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.1(5) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 121.3(5) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C12 120.4(4) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
N4 C18 C19 122.9(4) . . ?
N4 C18 H18 118.5 . . ?
C19 C18 H18 118.5 . . ?
C20 C19 C18 118.6(4) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C21 C20 C19 119.6(4) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 119.5(4) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
N4 C22 C21 121.0(4) . . ?
N4 C22 C23 114.9(3) . . ?
C21 C22 C23 124.1(3) . . ?
N1 C23 C24 120.3(4) . . ?
N1 C23 C22 112.9(3) . . ?
C24 C23 C22 126.8(4) . . ?
C25 C24 C23 118.8(4) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C24 C25 C26 120.6(4) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C27 C26 C25 118.4(4) . . ?
C27 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
N1 C27 C26 120.6(4) . . ?
N1 C27 C28 113.3(3) . . ?
C26 C27 C28 126.2(4) . . ?
N5 C28 C29 121.2(4) . . ?
N5 C28 C27 114.3(3) . . ?
C29 C28 C27 124.4(3) . . ?
C30 C29 C28 119.7(4) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C31 119.2(4) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 H30 120.4 . . ?
C32 C31 C30 119.3(4) . . ?
C32 C31 H31 120.4 . . ?
C30 C31 H31 120.4 . . ?
N5 C32 C31 122.7(4) . . ?
N5 C32 H32 118.6 . . ?
C31 C32 H32 118.6 . . ?
O1 C33 C11 118.7(3) . . ?
O1 C33 RU1 131.3(3) . . ?
C11 C33 RU1 110.1(2) . . ?
N1 RU1 C33 91.77(13) . . ?
N1 RU1 N3 174.75(11) . . ?
C33 RU1 N3 83.21(13) . . ?
N1 RU1 N4 78.97(12) . . ?
C33 RU1 N4 91.01(13) . . ?
N3 RU1 N4 99.53(12) . . ?
N1 RU1 N5 78.70(12) . . ?
C33 RU1 N5 91.77(13) . . ?
N3 RU1 N5 102.90(12) . . ?
N4 RU1 N5 157.56(12) . . ?
N1 RU1 N2 110.73(12) . . ?
C33 RU1 N2 157.44(13) . . ?
N3 RU1 N2 74.34(12) . . ?
N4 RU1 N2 94.83(11) . . ?
N5 RU1 N2 91.07(11) . . ?
O6 CL1 O7 107.8(7) . . ?
O6 CL1 O2 107.3(4) . . ?
O7 CL1 O2 111.4(5) . . ?
O6 CL1 O4 113.0(5) . . ?
O7 CL1 O4 105.4(4) . . ?
O2 CL1 O4 111.9(2) . . ?
C23 N1 C27 121.3(3) . . ?
C23 N1 RU1 119.2(2) . . ?
C27 N1 RU1 119.0(2) . . ?
C1 N2 C5 118.2(3) . . ?
C1 N2 RU1 127.8(3) . . ?
C5 N2 RU1 114.0(2) . . ?
C6 N3 C10 120.3(3) . . ?
C6 N3 RU1 123.8(2) . . ?
C10 N3 RU1 115.9(2) . . ?
C18 N4 C22 118.5(3) . . ?
C18 N4 RU1 127.6(3) . . ?
C22 N4 RU1 113.9(2) . . ?
C32 N5 C28 117.9(3) . . ?
C32 N5 RU1 127.9(3) . . ?
C28 N5 RU1 114.3(2) . . ?
C9 N6 C13 116.9(3) . . ?

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
N2 C1 C2 C3 -0.1(6) . . . . ?
C1 C2 C3 C4 2.0(6) . . . . ?
C2 C3 C4 C5 -1.4(6) . . . . ?
C3 C4 C5 N2 -1.1(6) . . . . ?
C3 C4 C5 C6 177.5(4) . . . . ?
N2 C5 C6 N3 -1.5(5) . . . . ?
C4 C5 C6 N3 179.7(4) . . . . ?
N2 C5 C6 C7 176.0(4) . . . . ?
C4 C5 C6 C7 -2.7(7) . . . . ?
N3 C6 C7 C8 0.0(6) . . . . ?
C5 C6 C7 C8 -177.4(4) . . . . ?
C6 C7 C8 C9 0.4(7) . . . . ?
C7 C8 C9 N6 178.2(4) . . . . ?
C7 C8 C9 C10 -0.7(7) . . . . ?
N6 C9 C10 N3 -178.2(4) . . . . ?
C8 C9 C10 N3 0.7(6) . . . . ?
N6 C9 C10 C11 1.1(6) . . . . ?
C8 C9 C10 C11 180.0(4) . . . . ?
N3 C10 C11 C12 177.7(3) . . . . ?
C9 C10 C11 C12 -1.7(6) . . . . ?
N3 C10 C11 C33 -3.0(5) . . . . ?
C9 C10 C11 C33 177.6(3) . . . . ?
C10 C11 C12 C17 -176.3(4) . . . . ?
C33 C11 C12 C17 4.5(7) . . . . ?
C10 C11 C12 C13 0.6(6) . . . . ?
C33 C11 C12 C13 -178.6(4) . . . . ?
C11 C12 C13 N6 1.0(7) . . . . ?
C17 C12 C13 N6 178.1(4) . . . . ?
C11 C12 C13 C14 -179.5(4) . . . . ?
C17 C12 C13 C14 -2.4(7) . . . . ?
N6 C13 C14 C15 -178.3(6) . . . . ?
C12 C13 C14 C15 2.2(9) . . . . ?
C13 C14 C15 C16 -0.8(10) . . . . ?
C14 C15 C16 C17 -0.3(10) . . . . ?
C15 C16 C17 C12 -0.1(9) . . . . ?
C11 C12 C17 C16 178.3(5) . . . . ?
C13 C12 C17 C16 1.4(7) . . . . ?
N4 C18 C19 C20 0.0(6) . . . . ?
C18 C19 C20 C21 0.0(7) . . . . ?
C19 C20 C21 C22 0.0(7) . . . . ?
C20 C21 C22 N4 0.0(6) . . . . ?
C20 C21 C22 C23 179.2(4) . . . . ?
N4 C22 C23 N1 -2.7(5) . . . . ?
C21 C22 C23 N1 178.1(4) . . . . ?
N4 C22 C23 C24 175.8(4) . . . . ?
C21 C22 C23 C24 -3.4(6) . . . . ?
N1 C23 C24 C25 1.9(6) . . . . ?
C22 C23 C24 C25 -176.4(4) . . . . ?
C23 C24 C25 C26 -0.2(7) . . . . ?
C24 C25 C26 C27 -1.4(7) . . . . ?
C25 C26 C27 N1 1.3(6) . . . . ?
C25 C26 C27 C28 -179.6(4) . . . . ?
N1 C27 C28 N5 2.5(5) . . . . ?
C26 C27 C28 N5 -176.6(4) . . . . ?
N1 C27 C28 C29 -174.9(4) . . . . ?
C26 C27 C28 C29 6.0(6) . . . . ?
N5 C28 C29 C30 0.0(6) . . . . ?
C27 C28 C29 C30 177.3(4) . . . . ?
C28 C29 C30 C31 -0.5(7) . . . . ?
C29 C30 C31 C32 0.0(7) . . . . ?
C30 C31 C32 N5 0.9(6) . . . . ?
C10 C11 C33 O1 -176.6(3) . . . . ?
C12 C11 C33 O1 2.6(6) . . . . ?
C10 C11 C33 RU1 3.8(4) . . . . ?
C12 C11 C33 RU1 -177.0(3) . . . . ?
C24 C23 N1 C27 -2.0(6) . . . . ?
C22 C23 N1 C27 176.5(3) . . . . ?
C24 C23 N1 RU1 -174.1(3) . . . . ?
C22 C23 N1 RU1 4.5(4) . . . . ?
C26 C27 N1 C23 0.4(5) . . . . ?
C28 C27 N1 C23 -178.8(3) . . . . ?
C26 C27 N1 RU1 172.4(3) . . . . ?
C28 C27 N1 RU1 -6.8(4) . . . . ?
C2 C1 N2 C5 -2.4(5) . . . . ?
C2 C1 N2 RU1 177.4(3) . . . . ?
C4 C5 N2 C1 3.0(5) . . . . ?
C6 C5 N2 C1 -175.7(3) . . . . ?
C4 C5 N2 RU1 -176.8(3) . . . . ?
C6 C5 N2 RU1 4.5(4) . . . . ?
C7 C6 N3 C10 0.0(6) . . . . ?
C5 C6 N3 C10 177.7(3) . . . . ?
C7 C6 N3 RU1 179.5(3) . . . . ?
C5 C6 N3 RU1 -2.8(5) . . . . ?
C11 C10 N3 C6 -179.7(3) . . . . ?
C9 C10 N3 C6 -0.4(6) . . . . ?
C11 C10 N3 RU1 0.7(4) . . . . ?
C9 C10 N3 RU1 -179.9(3) . . . . ?
C19 C18 N4 C22 0.0(6) . . . . ?
C19 C18 N4 RU1 -179.0(3) . . . . ?
C21 C22 N4 C18 -0.1(5) . . . . ?
C23 C22 N4 C18 -179.3(3) . . . . ?
C21 C22 N4 RU1 179.1(3) . . . . ?
C23 C22 N4 RU1 -0.1(4) . . . . ?
C31 C32 N5 C28 -1.3(5) . . . . ?
C31 C32 N5 RU1 179.8(3) . . . . ?
C29 C28 N5 C32 0.8(5) . . . . ?
C27 C28 N5 C32 -176.7(3) . . . . ?
C29 C28 N5 RU1 179.9(3) . . . . ?
C27 C28 N5 RU1 2.4(4) . . . . ?
C10 C9 N6 C13 0.6(7) . . . . ?
C8 C9 N6 C13 -178.3(4) . . . . ?
C14 C13 N6 C9 178.9(5) . . . . ?
C12 C13 N6 C9 -1.7(7) . . . . ?

_refine_diff_density_max         1.328
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1517697'
_audit_update_record             
;
2016-11-17 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H22 F12 N6 O P2 Ru'
_chemical_formula_weight         909.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   11.4581(5)
_cell_length_b                   32.7007(12)
_cell_length_c                   21.7230(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.480(5)
_cell_angle_gamma                90
_cell_volume                     8124.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    8902
_cell_measurement_theta_min      2.1870
_cell_measurement_theta_max      27.4920

_exptl_crystal_description       nONE
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             3616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.554
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65908
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34141
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.091
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9267
_reflns_number_gt                5547
_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.
 
 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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0941P)²+86.1521P] 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         9267
_refine_ls_number_parameters     499
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1324
_refine_ls_R_factor_gt           0.0818
_refine_ls_wR_factor_ref         0.2429
_refine_ls_wR_factor_gt          0.2087
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
RU1 Ru 0.72222(5) 0.60006(2) 0.25909(3) 0.0405(2) Uani 1 1 d . . . . .
P1 P 0.1780(2) 0.64524(9) 0.2161(2) 0.0958(11) Uani 1 1 d . . . . .
P2 P 0.250000 0.50686(7) 0.500000 0.0378(6) Uani 1 2 d S T P . .
P3 P 1.250000 0.79881(9) 0.000000 0.0718(11) Uani 1 2 d S T P . .
F4 F 0.3107(5) 0.50646(13) 0.5673(2) 0.0661(13) Uani 1 1 d . . . . .
F8 F 1.1117(4) 0.79957(16) -0.0098(3) 0.0881(19) Uani 1 1 d . . . . .
F9 F 0.3089(7) 0.6385(4) 0.2131(8) 0.243(8) Uani 1 1 d . . . . .
F17 F 1.250000 0.8472(2) 0.000000 0.104(3) Uani 1 2 d S T P . .
F19 F 0.3732(6) 0.5111(4) 0.4775(3) 0.159(4) Uani 1 1 d . . . . .
F20 F 1.250000 0.75088(19) 0.000000 0.100(3) Uani 1 2 d S T P . .
F21 F 1.2388(5) 0.79946(18) 0.0724(3) 0.097(2) Uani 1 1 d . . . . .
F35 F 0.250000 0.4616(2) 0.500000 0.182(7) Uani 1 2 d S T P . .
F53 F 0.1979(9) 0.6851(3) 0.2488(10) 0.302(11) Uani 1 1 d . . . . .
F54 F 0.1692(10) 0.6018(3) 0.1792(4) 0.157(4) Uani 1 1 d . . . . .
F55 F 0.1829(15) 0.6220(3) 0.2744(5) 0.243(8) Uani 1 1 d . . . . .
F56 F 0.0493(6) 0.6534(5) 0.2226(4) 0.215(6) Uani 1 1 d . . . . .
F57 F 0.250000 0.5542(3) 0.500000 0.156(6) Uani 1 2 d S T P . .
F58 F 0.1663(14) 0.6647(5) 0.1538(8) 0.337(13) Uani 1 1 d . . . . .
O1 O 0.8581(6) 0.59104(17) 0.1458(3) 0.0729(19) Uani 1 1 d . . . . .
N1 N 0.6529(5) 0.66013(14) 0.2493(3) 0.0363(13) Uani 1 1 d . . . . .
N2 N 0.6156(5) 0.60540(15) 0.3336(3) 0.0381(13) Uani 1 1 d . . . . .
N3 N 0.7696(6) 0.54274(16) 0.2804(3) 0.0495(17) Uani 1 1 d . . . . .
N4 N 0.5873(6) 0.56737(17) 0.2119(3) 0.0465(16) Uani 1 1 d . . . . .
N5 N 0.8696(5) 0.61072(18) 0.3180(3) 0.0464(16) Uani 1 1 d . . . . .
N6 N 0.6473(5) 0.75580(17) 0.1608(3) 0.0466(15) Uani 1 1 d . . . . .
C1 C 0.6121(6) 0.57997(19) 0.3809(3) 0.0440(18) Uani 1 1 d . . . . .
H1 H 0.666951 0.558167 0.383734 0.053 Uiso 1 1 calc R U . . .
C2 C 0.5328(7) 0.5834(2) 0.4265(4) 0.0489(19) Uani 1 1 d . . . . .
H2 H 0.535880 0.565549 0.461075 0.059 Uiso 1 1 calc R U . . .
C3 C 0.4486(7) 0.6139(2) 0.4193(4) 0.0476(19) Uani 1 1 d . . . . .
H3 H 0.388794 0.616099 0.447554 0.057 Uiso 1 1 calc R U . . .
C4 C 0.4525(6) 0.6409(2) 0.3710(3) 0.0433(17) Uani 1 1 d . . . . .
H4 H 0.396913 0.662389 0.366342 0.052 Uiso 1 1 calc R U . . .
C5 C 0.5379(6) 0.63652(18) 0.3295(3) 0.0348(15) Uani 1 1 d . . . . .
C6 C 0.5591(6) 0.66699(18) 0.2813(3) 0.0388(16) Uani 1 1 d . . . . .
C7 C 0.4896(6) 0.7020(2) 0.2733(4) 0.0458(18) Uani 1 1 d . . . . .
H7 H 0.423478 0.705429 0.297195 0.055 Uiso 1 1 calc R U . . .
C8 C 0.5155(6) 0.7307(2) 0.2321(4) 0.0489(19) Uani 1 1 d . . . . .
H8 H 0.465437 0.753578 0.224624 0.059 Uiso 1 1 calc R U . . .
C9 C 0.6194(6) 0.7264(2) 0.1999(3) 0.0427(17) Uani 1 1 d . . . . .
C10 C 0.6882(6) 0.69080(18) 0.2103(3) 0.0367(15) Uani 1 1 d . . . . .
C11 C 0.7938(6) 0.6891(2) 0.1835(3) 0.0430(17) Uani 1 1 d . . . . .
H11 H 0.845626 0.666942 0.192552 0.052 Uiso 1 1 calc R U . . .
C12 C 0.8249(6) 0.7196(2) 0.1432(3) 0.0414(16) Uani 1 1 d . . . . .
C13 C 0.7479(7) 0.7523(2) 0.1326(3) 0.0457(17) Uani 1 1 d . . . . .
C14 C 0.7778(7) 0.7831(2) 0.0903(4) 0.054(2) Uani 1 1 d . . . . .
H14 H 0.725619 0.805274 0.081767 0.065 Uiso 1 1 calc R U . . .
C15 C 0.8792(8) 0.7814(3) 0.0622(4) 0.058(2) Uani 1 1 d . . . . .
H15 H 0.897640 0.802199 0.033909 0.069 Uiso 1 1 calc R U . . .
C16 C 0.9588(7) 0.7487(3) 0.0743(4) 0.061(2) Uani 1 1 d . . . . .
H16 H 1.030586 0.748007 0.054643 0.073 Uiso 1 1 calc R U . . .
C17 C 0.9327(7) 0.7185(2) 0.1140(4) 0.057(2) Uani 1 1 d . . . . .
H17 H 0.986149 0.696650 0.122239 0.068 Uiso 1 1 calc R U . . .
C18 C 0.4973(7) 0.5811(2) 0.1782(4) 0.054(2) Uani 1 1 d . . . . .
H18 H 0.486215 0.609820 0.175358 0.065 Uiso 1 1 calc R U . . .
C19 C 0.4175(8) 0.5559(3) 0.1465(4) 0.065(2) Uani 1 1 d . . . . .
H19 H 0.354258 0.567056 0.121597 0.078 Uiso 1 1 calc R U . . .
C20 C 0.4326(10) 0.5138(3) 0.1523(5) 0.074(3) Uani 1 1 d . . . . .
H20 H 0.378892 0.495569 0.131563 0.089 Uiso 1 1 calc R U . . .
C21 C 0.5248(9) 0.4989(3) 0.1877(5) 0.068(3) Uani 1 1 d . . . . .
H21 H 0.536018 0.470256 0.191653 0.082 Uiso 1 1 calc R U . . .
C22 C 0.6022(8) 0.5254(2) 0.2180(4) 0.054(2) Uani 1 1 d . . . . .
C23 C 0.7025(8) 0.5127(2) 0.2578(4) 0.057(2) Uani 1 1 d . . . . .
C24 C 0.7375(10) 0.4718(2) 0.2745(5) 0.070(3) Uani 1 1 d . . . . .
H24 H 0.693685 0.449037 0.258779 0.084 Uiso 1 1 calc R U . . .
C25 C 0.8332(11) 0.4661(3) 0.3126(5) 0.075(3) Uani 1 1 d . . . . .
H25 H 0.856305 0.439093 0.323685 0.090 Uiso 1 1 calc R U . . .
C26 C 0.8975(9) 0.4982(2) 0.3358(4) 0.068(3) Uani 1 1 d . . . . .
H26 H 0.964966 0.493584 0.362490 0.081 Uiso 1 1 calc R U . . .
C27 C 0.8630(8) 0.5379(2) 0.3197(4) 0.054(2) Uani 1 1 d . . . . .
C28 C 0.9202(7) 0.5760(2) 0.3411(4) 0.056(2) Uani 1 1 d . . . . .
C29 C 1.0172(8) 0.5778(3) 0.3816(5) 0.071(3) Uani 1 1 d . . . . .
H29 H 1.053105 0.553381 0.396982 0.085 Uiso 1 1 calc R U . . .
C30 C 1.0612(9) 0.6146(3) 0.3994(5) 0.079(3) Uani 1 1 d . . . . .
H30 H 1.125894 0.616470 0.428757 0.095 Uiso 1 1 calc R U . . .
C31 C 1.0105(8) 0.6493(3) 0.3742(5) 0.071(3) Uani 1 1 d . . . . .
H31 H 1.042479 0.675369 0.384793 0.085 Uiso 1 1 calc R U . . .
C32 C 0.9166(7) 0.6467(2) 0.3351(4) 0.056(2) Uani 1 1 d . . . . .
H32 H 0.881971 0.671099 0.318875 0.068 Uiso 1 1 calc R U . . .
C33 C 0.8093(6) 0.5964(2) 0.1880(3) 0.0437(17) 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 C33 1.893(7) . ?
RU1 N3 1.998(5) . ?
RU1 N5 2.086(7) . ?
RU1 N2 2.094(5) . ?
RU1 N4 2.095(7) . ?
RU1 N1 2.125(5) . ?
P1 F55 1.475(10) . ?
P1 F58 1.494(14) . ?
P1 F53 1.496(10) . ?
P1 F56 1.514(7) . ?
P1 F9 1.520(8) . ?
P1 F54 1.631(10) . ?
P2 F35 1.481(7) . ?
P2 F19 1.528(6) 2_556 ?
P2 F19 1.528(6) . ?
P2 F57 1.549(9) . ?
P2 F4 1.580(5) . ?
P2 F4 1.580(5) 2_556 ?
P3 F20 1.567(7) . ?
P3 F17 1.581(8) . ?
P3 F8 1.586(5) 2_755 ?
P3 F8 1.586(5) . ?
P3 F21 1.587(7) . ?
P3 F21 1.587(7) 2_755 ?
O1 C33 1.115(8) . ?
N1 C6 1.334(8) . ?
N1 C10 1.388(8) . ?
N2 C1 1.323(9) . ?
N2 C5 1.351(8) . ?
N3 C23 1.323(11) . ?
N3 C27 1.338(11) . ?
N4 C18 1.307(10) . ?
N4 C22 1.387(9) . ?
N5 C32 1.336(10) . ?
N5 C28 1.357(9) . ?
N6 C9 1.335(8) . ?
N6 C13 1.343(9) . ?
C1 C2 1.389(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.475(9) . ?
C6 C7 1.399(9) . ?
C7 C8 1.344(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.424(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.416(9) . ?
C10 C11 1.376(9) . ?
C11 C12 1.388(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(10) . ?
C12 C17 1.423(10) . ?
C13 C14 1.420(10) . ?
C14 C15 1.346(11) . ?
C14 H14 0.9500 . ?
C15 C16 1.419(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.357(10) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.382(12) . ?
C18 H18 0.9500 . ?
C19 C20 1.394(13) . ?
C19 H19 0.9500 . ?
C20 C21 1.359(14) . ?
C20 H20 0.9500 . ?
C21 C22 1.378(12) . ?
C21 H21 0.9500 . ?
C22 C23 1.456(13) . ?
C23 C24 1.436(11) . ?
C24 C25 1.347(14) . ?
C24 H24 0.9500 . ?
C25 C26 1.359(14) . ?
C25 H25 0.9500 . ?
C26 C27 1.395(10) . ?
C26 H26 0.9500 . ?
C27 C28 1.470(12) . ?
C28 C29 1.377(13) . ?
C29 C30 1.352(14) . ?
C29 H29 0.9500 . ?
C30 C31 1.372(13) . ?
C30 H30 0.9500 . ?
C31 C32 1.333(12) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

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
C33 RU1 N3 88.9(3) . . ?
C33 RU1 N5 93.7(3) . . ?
N3 RU1 N5 79.4(3) . . ?
C33 RU1 N2 175.9(3) . . ?
N3 RU1 N2 93.6(2) . . ?
N5 RU1 N2 90.0(2) . . ?
C33 RU1 N4 88.7(3) . . ?
N3 RU1 N4 79.4(3) . . ?
N5 RU1 N4 158.6(2) . . ?
N2 RU1 N4 88.5(2) . . ?
C33 RU1 N1 100.9(2) . . ?
N3 RU1 N1 170.1(2) . . ?
N5 RU1 N1 101.0(2) . . ?
N2 RU1 N1 76.59(19) . . ?
N4 RU1 N1 99.3(2) . . ?
F55 P1 F58 173.4(11) . . ?
F55 P1 F53 92.7(10) . . ?
F58 P1 F53 93.6(11) . . ?
F55 P1 F56 89.8(7) . . ?
F58 P1 F56 88.6(6) . . ?
F53 P1 F56 85.5(7) . . ?
F55 P1 F9 88.7(9) . . ?
F58 P1 F9 93.3(9) . . ?
F53 P1 F9 91.4(6) . . ?
F56 P1 F9 176.5(8) . . ?
F55 P1 F54 88.3(6) . . ?
F58 P1 F54 85.7(9) . . ?
F53 P1 F54 174.7(6) . . ?
F56 P1 F54 99.7(7) . . ?
F9 P1 F54 83.4(6) . . ?
F35 P2 F19 95.2(5) . 2_556 ?
F35 P2 F19 95.2(5) . . ?
F19 P2 F19 169.6(9) 2_556 . ?
F35 P2 F57 180.0 . . ?
F19 P2 F57 84.8(5) 2_556 . ?
F19 P2 F57 84.8(5) . . ?
F35 P2 F4 89.52(17) . . ?
F19 P2 F4 93.9(3) 2_556 . ?
F19 P2 F4 86.2(3) . . ?
F57 P2 F4 90.48(17) . . ?
F35 P2 F4 89.52(17) . 2_556 ?
F19 P2 F4 86.2(3) 2_556 2_556 ?
F19 P2 F4 93.9(3) . 2_556 ?
F57 P2 F4 90.48(17) . 2_556 ?
F4 P2 F4 179.0(3) . 2_556 ?
F20 P3 F17 180.0 . . ?
F20 P3 F8 90.9(2) . 2_755 ?
F17 P3 F8 89.1(2) . 2_755 ?
F20 P3 F8 90.9(2) . . ?
F17 P3 F8 89.1(2) . . ?
F8 P3 F8 178.2(4) 2_755 . ?
F20 P3 F21 90.8(2) . . ?
F17 P3 F21 89.2(2) . . ?
F8 P3 F21 90.4(3) 2_755 . ?
F8 P3 F21 89.6(3) . . ?
F20 P3 F21 90.8(2) . 2_755 ?
F17 P3 F21 89.2(2) . 2_755 ?
F8 P3 F21 89.6(3) 2_755 2_755 ?
F8 P3 F21 90.4(3) . 2_755 ?
F21 P3 F21 178.5(5) . 2_755 ?
C6 N1 C10 118.0(5) . . ?
C6 N1 RU1 114.3(4) . . ?
C10 N1 RU1 127.4(4) . . ?
C1 N2 C5 118.3(5) . . ?
C1 N2 RU1 126.4(4) . . ?
C5 N2 RU1 115.1(4) . . ?
C23 N3 C27 125.0(7) . . ?
C23 N3 RU1 117.8(6) . . ?
C27 N3 RU1 117.1(5) . . ?
C18 N4 C22 118.7(7) . . ?
C18 N4 RU1 129.2(5) . . ?
C22 N4 RU1 112.0(6) . . ?
C32 N5 C28 118.6(8) . . ?
C32 N5 RU1 128.0(5) . . ?
C28 N5 RU1 113.5(6) . . ?
C9 N6 C13 118.3(6) . . ?
N2 C1 C2 123.7(6) . . ?
N2 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 117.2(7) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C4 C3 C2 119.5(6) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.4(6) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N2 C5 C4 121.7(6) . . ?
N2 C5 C6 114.8(5) . . ?
C4 C5 C6 123.2(6) . . ?
N1 C6 C7 122.9(6) . . ?
N1 C6 C5 115.4(5) . . ?
C7 C6 C5 121.6(6) . . ?
C8 C7 C6 120.5(6) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 118.9(6) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
N6 C9 C10 122.8(6) . . ?
N6 C9 C8 118.7(6) . . ?
C10 C9 C8 118.5(6) . . ?
C11 C10 N1 121.7(6) . . ?
C11 C10 C9 117.4(6) . . ?
N1 C10 C9 120.8(6) . . ?
C10 C11 C12 120.3(6) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 118.0(6) . . ?
C11 C12 C17 121.7(7) . . ?
C13 C12 C17 120.2(6) . . ?
N6 C13 C12 122.8(6) . . ?
N6 C13 C14 118.8(7) . . ?
C12 C13 C14 118.4(7) . . ?
C15 C14 C13 120.8(8) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.7(7) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 120.2(8) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C12 119.7(8) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?
N4 C18 C19 123.4(8) . . ?
N4 C18 H18 118.3 . . ?
C19 C18 H18 118.3 . . ?
C18 C19 C20 117.9(10) . . ?
C18 C19 H19 121.0 . . ?
C20 C19 H19 121.0 . . ?
C21 C20 C19 119.5(9) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 120.1(9) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 N4 120.3(9) . . ?
C21 C22 C23 124.4(8) . . ?
N4 C22 C23 115.3(7) . . ?
N3 C23 C24 116.7(9) . . ?
N3 C23 C22 115.3(7) . . ?
C24 C23 C22 127.9(9) . . ?
C25 C24 C23 119.2(9) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 121.6(8) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C25 C26 C27 119.1(10) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 H26 120.5 . . ?
N3 C27 C26 118.3(9) . . ?
N3 C27 C28 115.1(6) . . ?
C26 C27 C28 126.6(9) . . ?
N5 C28 C29 120.6(8) . . ?
N5 C28 C27 114.9(8) . . ?
C29 C28 C27 124.5(8) . . ?
C30 C29 C28 119.6(8) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C29 C30 C31 118.7(10) . . ?
C29 C30 H30 120.6 . . ?
C31 C30 H30 120.6 . . ?
C32 C31 C30 120.4(10) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C31 C32 N5 122.0(8) . . ?
C31 C32 H32 119.0 . . ?
N5 C32 H32 119.0 . . ?
O1 C33 RU1 174.5(6) . . ?

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
C5 N2 C1 C2 0.2(11) . . . . ?
RU1 N2 C1 C2 -174.6(6) . . . . ?
N2 C1 C2 C3 3.9(12) . . . . ?
C1 C2 C3 C4 -4.8(12) . . . . ?
C2 C3 C4 C5 1.8(11) . . . . ?
C1 N2 C5 C4 -3.5(10) . . . . ?
RU1 N2 C5 C4 171.9(5) . . . . ?
C1 N2 C5 C6 171.0(6) . . . . ?
RU1 N2 C5 C6 -13.6(7) . . . . ?
C3 C4 C5 N2 2.5(11) . . . . ?
C3 C4 C5 C6 -171.5(7) . . . . ?
C10 N1 C6 C7 5.8(11) . . . . ?
RU1 N1 C6 C7 -169.2(6) . . . . ?
C10 N1 C6 C5 -169.9(6) . . . . ?
RU1 N1 C6 C5 15.1(8) . . . . ?
N2 C5 C6 N1 -1.2(9) . . . . ?
C4 C5 C6 N1 173.2(7) . . . . ?
N2 C5 C6 C7 -176.9(7) . . . . ?
C4 C5 C6 C7 -2.6(11) . . . . ?
N1 C6 C7 C8 -0.2(12) . . . . ?
C5 C6 C7 C8 175.2(7) . . . . ?
C6 C7 C8 C9 -4.3(12) . . . . ?
C13 N6 C9 C10 -3.2(11) . . . . ?
C13 N6 C9 C8 177.3(7) . . . . ?
C7 C8 C9 N6 -177.3(7) . . . . ?
C7 C8 C9 C10 3.1(11) . . . . ?
C6 N1 C10 C11 169.2(7) . . . . ?
RU1 N1 C10 C11 -16.5(10) . . . . ?
C6 N1 C10 C9 -6.8(10) . . . . ?
RU1 N1 C10 C9 167.4(5) . . . . ?
N6 C9 C10 C11 6.7(11) . . . . ?
C8 C9 C10 C11 -173.7(7) . . . . ?
N6 C9 C10 N1 -177.1(7) . . . . ?
C8 C9 C10 N1 2.5(11) . . . . ?
N1 C10 C11 C12 177.9(7) . . . . ?
C9 C10 C11 C12 -5.9(11) . . . . ?
C10 C11 C12 C13 2.0(11) . . . . ?
C10 C11 C12 C17 -179.2(7) . . . . ?
C9 N6 C13 C12 -1.1(11) . . . . ?
C9 N6 C13 C14 179.2(7) . . . . ?
C11 C12 C13 N6 1.7(12) . . . . ?
C17 C12 C13 N6 -177.1(7) . . . . ?
C11 C12 C13 C14 -178.6(7) . . . . ?
C17 C12 C13 C14 2.6(11) . . . . ?
N6 C13 C14 C15 178.2(8) . . . . ?
C12 C13 C14 C15 -1.5(12) . . . . ?
C13 C14 C15 C16 -0.3(13) . . . . ?
C14 C15 C16 C17 0.9(14) . . . . ?
C15 C16 C17 C12 0.2(13) . . . . ?
C11 C12 C17 C16 179.2(8) . . . . ?
C13 C12 C17 C16 -2.0(12) . . . . ?
C22 N4 C18 C19 -2.1(11) . . . . ?
RU1 N4 C18 C19 176.2(6) . . . . ?
N4 C18 C19 C20 1.7(12) . . . . ?
C18 C19 C20 C21 -0.8(13) . . . . ?
C19 C20 C21 C22 0.4(13) . . . . ?
C20 C21 C22 N4 -0.9(12) . . . . ?
C20 C21 C22 C23 179.0(8) . . . . ?
C18 N4 C22 C21 1.7(10) . . . . ?
RU1 N4 C22 C21 -176.9(6) . . . . ?
C18 N4 C22 C23 -178.2(6) . . . . ?
RU1 N4 C22 C23 3.2(7) . . . . ?
C27 N3 C23 C24 -3.6(10) . . . . ?
RU1 N3 C23 C24 -179.2(5) . . . . ?
C27 N3 C23 C22 177.2(6) . . . . ?
RU1 N3 C23 C22 1.6(8) . . . . ?
C21 C22 C23 N3 176.9(7) . . . . ?
N4 C22 C23 N3 -3.2(9) . . . . ?
C21 C22 C23 C24 -2.2(12) . . . . ?
N4 C22 C23 C24 177.7(7) . . . . ?
N3 C23 C24 C25 1.6(11) . . . . ?
C22 C23 C24 C25 -179.4(7) . . . . ?
C23 C24 C25 C26 0.0(13) . . . . ?
C24 C25 C26 C27 0.3(12) . . . . ?
C23 N3 C27 C26 3.9(10) . . . . ?
RU1 N3 C27 C26 179.5(5) . . . . ?
C23 N3 C27 C28 -176.8(6) . . . . ?
RU1 N3 C27 C28 -1.2(8) . . . . ?
C25 C26 C27 N3 -2.0(11) . . . . ?
C25 C26 C27 C28 178.7(7) . . . . ?
C32 N5 C28 C29 0.5(11) . . . . ?
RU1 N5 C28 C29 -178.8(6) . . . . ?
C32 N5 C28 C27 -179.8(6) . . . . ?
RU1 N5 C28 C27 0.8(7) . . . . ?
N3 C27 C28 N5 0.2(9) . . . . ?
C26 C27 C28 N5 179.5(7) . . . . ?
N3 C27 C28 C29 179.8(7) . . . . ?
C26 C27 C28 C29 -0.9(12) . . . . ?
N5 C28 C29 C30 1.2(13) . . . . ?
C27 C28 C29 C30 -178.4(8) . . . . ?
C28 C29 C30 C31 -2.9(14) . . . . ?
C29 C30 C31 C32 2.9(15) . . . . ?
C30 C31 C32 N5 -1.2(14) . . . . ?
C28 N5 C32 C31 -0.5(12) . . . . ?
RU1 N5 C32 C31 178.8(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 F4_$1 0.95 2.37 3.149(8) 138.7 5_666
C1 H1 N3 0.95 2.64 3.159(8) 114.4 .
C2 H2 F19 0.95 2.62 3.224(11) 122.1 .
C4 H4 F21_$2 0.95 2.45 3.232(8) 139.7 7_665
C11 H11 F56_$3 0.95 2.43 3.218(11) 140.7 1_655
C18 H18 F9 0.95 2.43 2.994(11) 118.2 .
C24 H24 F54_$4 0.95 2.40 3.239(13) 146.8 6_665
C24 H24 F55_$4 0.95 2.35 3.130(12) 138.9 6_665
C29 H29 F4_$5 0.95 2.29 3.209(9) 162.6 2_656
C31 H31 F8_$6 0.95 2.51 3.182(12) 127.4 8_565
C32 H32 N6_$2 0.95 2.46 3.274(10) 144.1 7_665

_refine_diff_density_max         1.839
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.122



