# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2011


data_global

_journal_coden_Cambridge         222

loop_
_publ_author_name
'Fetzer, Ludivine'
'Boff, Bastien'
'Ali, Moussa'
'Xiangjun, Meng'
'Collin, Jean-Paul'
'Sirlin, Claude'
'Gaiddon, Christian'
'Pfeffer, Michel'

_publ_contact_author_name        'Pfeffer, Michel'
_publ_contact_author_email       pfeffer@unistra.fr

_publ_section_title              
;
Library of Second Generation Cycloruthenated Compounds and
Evaluation of their Biological Properties as Potential
Anticancer Drugs: Passing the nanomolar barrier
;

# Attachment '- mpam100325.cif'

data_mpam100325
_database_code_depnum_ccdc_archive 'CCDC 814874'
#TrackingRef '- mpam100325.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H26 N3 Ru, F6 P'
_chemical_formula_sum            'C23 H26 F6 N3 P Ru'
_chemical_formula_weight         590.51

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.3585(3)
_cell_length_b                   10.3118(3)
_cell_length_c                   26.0322(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.7030(10)
_cell_angle_gamma                90.00
_cell_volume                     2418.42(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      32.52

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1192
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7734
_exptl_absorpt_correction_T_max  0.8733
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24784
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         32.53
_reflns_number_total             8733
_reflns_number_gt                7812
_reflns_threshold_expression     I>2sigma(I)

_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+2.9389P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8733
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0677
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_restrained_S_all      1.240
_refine_ls_shift/su_max          0.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.329431(14) -0.026412(13) 0.833845(5) 0.01822(3) Uani 1 1 d . . .
N1 N 0.49771(16) 0.09455(14) 0.87774(6) 0.0205(3) Uani 1 1 d . . .
N2 N 0.8370(2) 0.3395(2) 0.95786(10) 0.0459(5) Uani 1 1 d . . .
N3 N 0.44927(17) -0.17963(16) 0.87432(7) 0.0262(3) Uani 1 1 d . . .
C1 C 0.4953(2) 0.15350(19) 0.92374(8) 0.0257(3) Uani 1 1 d . . .
H1 H 0.4132 0.1373 0.9377 0.031 Uiso 1 1 calc R . .
C2 C 0.6042(2) 0.2352(2) 0.95141(8) 0.0289(4) Uani 1 1 d . . .
H2 H 0.5971 0.2744 0.9837 0.035 Uiso 1 1 calc R . .
C3 C 0.7264(2) 0.26036(19) 0.93153(8) 0.0274(4) Uani 1 1 d . . .
C4 C 0.7302(2) 0.19914(19) 0.88398(7) 0.0250(3) Uani 1 1 d . . .
H4 H 0.8116 0.2138 0.8694 0.030 Uiso 1 1 calc R . .
C5 C 0.61608(18) 0.11727(16) 0.85797(7) 0.0196(3) Uani 1 1 d . . .
C6 C 0.60867(18) 0.04588(16) 0.80877(7) 0.0203(3) Uani 1 1 d . . .
C7 C 0.7189(2) 0.05181(19) 0.78155(8) 0.0269(4) Uani 1 1 d . . .
H7 H 0.8031 0.1060 0.7944 0.032 Uiso 1 1 calc R . .
C8 C 0.7049(2) -0.0217(2) 0.73569(8) 0.0316(4) Uani 1 1 d . . .
H8 H 0.7783 -0.0165 0.7167 0.038 Uiso 1 1 calc R . .
C9 C 0.5832(2) -0.1028(2) 0.71777(8) 0.0314(4) Uani 1 1 d . . .
H9 H 0.5739 -0.1537 0.6866 0.038 Uiso 1 1 calc R . .
C10 C 0.4747(2) -0.11006(19) 0.74516(8) 0.0273(4) Uani 1 1 d . . .
H10 H 0.3935 -0.1678 0.7329 0.033 Uiso 1 1 calc R . .
C11 C 0.48282(18) -0.03400(17) 0.79046(7) 0.0198(3) Uani 1 1 d . . .
C12 C 0.16031(19) 0.04637(18) 0.76318(7) 0.0246(3) Uani 1 1 d . . .
C13 C 0.13773(19) -0.08937(19) 0.76958(8) 0.0263(4) Uani 1 1 d . . .
H13 H 0.1326 -0.1473 0.7407 0.032 Uiso 1 1 calc R . .
C14 C 0.1230(2) -0.13720(18) 0.81872(8) 0.0260(3) Uani 1 1 d . . .
H14 H 0.1166 -0.2283 0.8232 0.031 Uiso 1 1 calc R . .
C15 C 0.11739(19) -0.05336(17) 0.86211(8) 0.0234(3) Uani 1 1 d . . .
C16 C 0.14054(18) 0.07844(17) 0.85539(8) 0.0226(3) Uani 1 1 d . . .
H16 H 0.1399 0.1369 0.8835 0.027 Uiso 1 1 calc R . .
C17 C 0.16530(19) 0.12770(17) 0.80708(8) 0.0237(3) Uani 1 1 d . . .
H17 H 0.1856 0.2174 0.8046 0.028 Uiso 1 1 calc R . .
C18 C 0.1824(2) 0.0991(2) 0.71216(8) 0.0336(4) Uani 1 1 d . . .
H18A H 0.0856 0.1150 0.6868 0.050 Uiso 1 1 calc R . .
H18B H 0.2380 0.0362 0.6969 0.050 Uiso 1 1 calc R . .
H18C H 0.2381 0.1806 0.7194 0.050 Uiso 1 1 calc R . .
C19 C 0.0946(2) -0.11046(19) 0.91313(8) 0.0280(4) Uani 1 1 d . . .
H19 H 0.1540 -0.1923 0.9210 0.034 Uiso 1 1 calc R . .
C20 C -0.0689(2) -0.1463(2) 0.90476(10) 0.0387(5) Uani 1 1 d . . .
H20A H -0.1293 -0.0673 0.8989 0.058 Uiso 1 1 calc R . .
H20B H -0.0810 -0.1915 0.9364 0.058 Uiso 1 1 calc R . .
H20C H -0.1011 -0.2031 0.8736 0.058 Uiso 1 1 calc R . .
C21 C 0.1458(3) -0.0221(3) 0.96148(9) 0.0416(5) Uani 1 1 d . . .
H21A H 0.2517 -0.0032 0.9677 0.062 Uiso 1 1 calc R . .
H21B H 0.1293 -0.0653 0.9929 0.062 Uiso 1 1 calc R . .
H21C H 0.0892 0.0590 0.9550 0.062 Uiso 1 1 calc R . .
C22 C 0.5144(2) -0.2695(2) 0.89234(9) 0.0300(4) Uani 1 1 d . . .
C23 C 0.5980(3) -0.3858(2) 0.91392(12) 0.0457(6) Uani 1 1 d . . .
H23A H 0.5375 -0.4627 0.9010 0.068 Uiso 1 1 calc R . .
H23B H 0.6236 -0.3834 0.9530 0.068 Uiso 1 1 calc R . .
H23C H 0.6892 -0.3894 0.9023 0.068 Uiso 1 1 calc R . .
P1 P 0.17942(6) 0.45449(5) 0.91160(2) 0.02740(10) Uani 1 1 d . . .
F1 F 0.1779(2) 0.33591(15) 0.95095(6) 0.0526(4) Uani 1 1 d . . .
F2 F 0.29712(16) 0.38068(14) 0.88857(6) 0.0408(3) Uani 1 1 d . . .
F3 F 0.30951(17) 0.52200(17) 0.95642(6) 0.0523(4) Uani 1 1 d . . .
F4 F 0.05866(17) 0.52921(16) 0.93430(7) 0.0524(4) Uani 1 1 d . . .
F5 F 0.04726(16) 0.38610(14) 0.86803(6) 0.0481(4) Uani 1 1 d . . .
F6 F 0.17913(19) 0.57243(14) 0.87245(6) 0.0489(4) Uani 1 1 d . . .
H2N H 0.909(3) 0.356(3) 0.9443(12) 0.051(8) Uiso 1 1 d . . .
H1N H 0.833(3) 0.373(3) 0.9873(13) 0.055(9) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ru1 0.01690(5) 0.01620(6) 0.02136(6) -0.00043(5) 0.00482(4) -0.00070(5)
N1 0.0189(6) 0.0208(7) 0.0218(6) -0.0013(5) 0.0054(5) -0.0003(5)
N2 0.0364(10) 0.0556(14) 0.0471(12) -0.0241(10) 0.0137(9) -0.0221(10)
N3 0.0236(7) 0.0253(7) 0.0303(8) 0.0034(6) 0.0080(6) -0.0001(6)
C1 0.0228(8) 0.0294(9) 0.0256(8) -0.0054(7) 0.0077(6) -0.0026(7)
C2 0.0262(8) 0.0331(10) 0.0264(9) -0.0092(7) 0.0056(7) -0.0033(7)
C3 0.0242(8) 0.0265(9) 0.0288(9) -0.0051(7) 0.0026(7) -0.0051(7)
C4 0.0214(7) 0.0266(8) 0.0266(8) -0.0006(7) 0.0056(6) -0.0055(6)
C5 0.0183(7) 0.0187(7) 0.0212(7) 0.0019(6) 0.0043(6) 0.0005(5)
C6 0.0202(7) 0.0188(7) 0.0221(7) 0.0011(6) 0.0062(6) 0.0011(6)
C7 0.0235(8) 0.0297(9) 0.0293(9) 0.0005(7) 0.0101(7) -0.0013(7)
C8 0.0291(9) 0.0404(11) 0.0298(9) -0.0005(8) 0.0158(7) 0.0017(8)
C9 0.0334(10) 0.0356(10) 0.0274(9) -0.0064(8) 0.0118(8) 0.0034(8)
C10 0.0259(8) 0.0281(9) 0.0284(9) -0.0069(7) 0.0081(7) -0.0017(7)
C11 0.0199(7) 0.0189(7) 0.0205(7) 0.0002(6) 0.0053(5) 0.0004(6)
C12 0.0195(7) 0.0252(8) 0.0261(8) 0.0013(6) 0.0009(6) -0.0001(6)
C13 0.0199(7) 0.0269(9) 0.0296(9) -0.0067(7) 0.0022(6) -0.0034(6)
C14 0.0211(7) 0.0200(8) 0.0370(10) -0.0029(7) 0.0078(7) -0.0045(6)
C15 0.0186(7) 0.0199(8) 0.0334(9) 0.0023(6) 0.0101(6) -0.0002(6)
C16 0.0194(7) 0.0191(7) 0.0304(9) -0.0003(6) 0.0087(6) 0.0023(6)
C17 0.0197(7) 0.0197(7) 0.0305(9) 0.0042(6) 0.0048(6) 0.0012(6)
C18 0.0331(10) 0.0397(11) 0.0247(9) 0.0056(8) 0.0022(7) 0.0021(8)
C19 0.0266(8) 0.0236(8) 0.0373(10) 0.0071(7) 0.0147(8) 0.0025(7)
C20 0.0338(10) 0.0441(13) 0.0436(12) -0.0037(10) 0.0196(9) -0.0116(9)
C21 0.0443(12) 0.0488(13) 0.0304(10) 0.0058(10) 0.0080(9) -0.0108(11)
C22 0.0277(9) 0.0278(9) 0.0344(10) 0.0066(8) 0.0081(8) -0.0002(7)
C23 0.0411(12) 0.0347(12) 0.0596(16) 0.0201(11) 0.0107(11) 0.0106(10)
P1 0.0342(2) 0.0221(2) 0.0278(2) -0.00228(18) 0.01185(19) -0.00175(18)
F1 0.0753(11) 0.0434(8) 0.0438(8) 0.0152(7) 0.0242(8) -0.0047(8)
F2 0.0441(7) 0.0388(7) 0.0441(8) -0.0005(6) 0.0199(6) 0.0110(6)
F3 0.0499(8) 0.0610(10) 0.0434(8) -0.0167(7) 0.0082(7) -0.0164(8)
F4 0.0530(9) 0.0439(8) 0.0718(11) -0.0197(8) 0.0367(8) -0.0041(7)
F5 0.0435(8) 0.0372(8) 0.0544(9) -0.0138(7) -0.0027(7) -0.0010(6)
F6 0.0713(10) 0.0280(7) 0.0526(9) 0.0119(6) 0.0256(8) 0.0065(7)

_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 C11 2.0543(16) . ?
Ru1 N3 2.0553(16) . ?
Ru1 N1 2.0899(15) . ?
Ru1 C14 2.1863(18) . ?
Ru1 C17 2.1888(17) . ?
Ru1 C13 2.1942(18) . ?
Ru1 C12 2.2083(18) . ?
Ru1 C16 2.2683(17) . ?
Ru1 C15 2.3123(17) . ?
N1 C1 1.348(2) . ?
N1 C5 1.362(2) . ?
N2 C3 1.350(3) . ?
N2 H2N 0.86(3) . ?
N2 H1N 0.85(3) . ?
N3 C22 1.138(3) . ?
C1 C2 1.368(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.401(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(3) . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.463(2) . ?
C6 C7 1.402(2) . ?
C6 C11 1.410(2) . ?
C7 C8 1.390(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.401(2) . ?
C10 H10 0.9500 . ?
C12 C17 1.408(3) . ?
C12 C13 1.432(3) . ?
C12 C18 1.500(3) . ?
C13 C14 1.412(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.435(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(2) . ?
C15 C19 1.519(3) . ?
C16 C17 1.432(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C21 1.522(3) . ?
C19 C20 1.532(3) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.459(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
P1 F2 1.5841(14) . ?
P1 F6 1.5863(15) . ?
P1 F1 1.5977(15) . ?
P1 F5 1.5982(15) . ?
P1 F3 1.5998(15) . ?
P1 F4 1.6068(15) . ?

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
C11 Ru1 N3 83.51(6) . . ?
C11 Ru1 N1 77.76(6) . . ?
N3 Ru1 N1 87.29(6) . . ?
C11 Ru1 C14 126.58(7) . . ?
N3 Ru1 C14 91.35(7) . . ?
N1 Ru1 C14 155.32(7) . . ?
C11 Ru1 C17 112.78(7) . . ?
N3 Ru1 C17 163.70(7) . . ?
N1 Ru1 C17 95.78(6) . . ?
C14 Ru1 C17 79.18(7) . . ?
C11 Ru1 C13 96.80(7) . . ?
N3 Ru1 C13 112.55(7) . . ?
N1 Ru1 C13 158.93(7) . . ?
C14 Ru1 C13 37.61(7) . . ?
C17 Ru1 C13 67.27(7) . . ?
C11 Ru1 C12 90.28(7) . . ?
N3 Ru1 C12 148.97(7) . . ?
N1 Ru1 C12 121.11(6) . . ?
C14 Ru1 C12 68.19(7) . . ?
C17 Ru1 C12 37.35(7) . . ?
C13 Ru1 C12 37.96(7) . . ?
C11 Ru1 C16 149.47(7) . . ?
N3 Ru1 C16 126.39(7) . . ?
N1 Ru1 C16 95.89(6) . . ?
C14 Ru1 C16 65.42(7) . . ?
C17 Ru1 C16 37.43(7) . . ?
C13 Ru1 C16 78.38(7) . . ?
C12 Ru1 C16 67.25(7) . . ?
C11 Ru1 C15 163.32(7) . . ?
N3 Ru1 C15 98.09(6) . . ?
N1 Ru1 C15 118.84(6) . . ?
C14 Ru1 C15 37.06(7) . . ?
C17 Ru1 C15 66.41(6) . . ?
C13 Ru1 C15 67.17(7) . . ?
C12 Ru1 C15 79.78(7) . . ?
C16 Ru1 C15 35.44(6) . . ?
C1 N1 C5 117.95(15) . . ?
C1 N1 Ru1 124.29(12) . . ?
C5 N1 Ru1 117.75(11) . . ?
C3 N2 H2N 119(2) . . ?
C3 N2 H1N 119(2) . . ?
H2N N2 H1N 121(3) . . ?
C22 N3 Ru1 173.81(18) . . ?
N1 C1 C2 123.80(17) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 119.06(18) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
N2 C3 C4 121.51(19) . . ?
N2 C3 C2 120.95(19) . . ?
C4 C3 C2 117.54(17) . . ?
C5 C4 C3 120.42(17) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
N1 C5 C4 121.22(16) . . ?
N1 C5 C6 113.18(15) . . ?
C4 C5 C6 125.59(16) . . ?
C7 C6 C11 121.06(16) . . ?
C7 C6 C5 123.62(16) . . ?
C11 C6 C5 115.30(14) . . ?
C8 C7 C6 119.95(18) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 119.66(17) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 120.42(18) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 121.35(18) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C6 117.50(15) . . ?
C10 C11 Ru1 126.67(13) . . ?
C6 C11 Ru1 115.84(12) . . ?
C17 C12 C13 117.46(17) . . ?
C17 C12 C18 121.35(18) . . ?
C13 C12 C18 121.16(18) . . ?
C17 C12 Ru1 70.57(10) . . ?
C13 C12 Ru1 70.48(11) . . ?
C18 C12 Ru1 128.40(13) . . ?
C14 C13 C12 120.03(17) . . ?
C14 C13 Ru1 70.89(10) . . ?
C12 C13 Ru1 71.55(10) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
Ru1 C13 H13 130.1 . . ?
C13 C14 C15 122.42(17) . . ?
C13 C14 Ru1 71.50(10) . . ?
C15 C14 Ru1 76.25(10) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
Ru1 C14 H14 125.2 . . ?
C16 C15 C14 116.64(17) . . ?
C16 C15 C19 123.39(17) . . ?
C14 C15 C19 119.89(16) . . ?
C16 C15 Ru1 70.56(10) . . ?
C14 C15 Ru1 66.69(9) . . ?
C19 C15 Ru1 131.30(13) . . ?
C15 C16 C17 121.55(17) . . ?
C15 C16 Ru1 74.00(10) . . ?
C17 C16 Ru1 68.27(10) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
Ru1 C16 H16 131.4 . . ?
C12 C17 C16 121.59(17) . . ?
C12 C17 Ru1 72.07(10) . . ?
C16 C17 Ru1 74.30(10) . . ?
C12 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
Ru1 C17 H17 126.4 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 C21 113.82(17) . . ?
C15 C19 C20 109.89(17) . . ?
C21 C19 C20 109.89(18) . . ?
C15 C19 H19 107.7 . . ?
C21 C19 H19 107.7 . . ?
C20 C19 H19 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 C23 178.4(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
F2 P1 F6 90.32(8) . . ?
F2 P1 F1 90.16(9) . . ?
F6 P1 F1 179.40(10) . . ?
F2 P1 F5 90.18(8) . . ?
F6 P1 F5 90.91(9) . . ?
F1 P1 F5 88.73(9) . . ?
F2 P1 F3 90.88(9) . . ?
F6 P1 F3 90.21(9) . . ?
F1 P1 F3 90.14(9) . . ?
F5 P1 F3 178.45(9) . . ?
F2 P1 F4 179.34(9) . . ?
F6 P1 F4 89.40(9) . . ?
F1 P1 F4 90.11(9) . . ?
F5 P1 F4 89.22(9) . . ?
F3 P1 F4 89.72(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 Ru1 N1 C1 -177.83(16) . . . . ?
N3 Ru1 N1 C1 -93.88(16) . . . . ?
C14 Ru1 N1 C1 -6.6(3) . . . . ?
C17 Ru1 N1 C1 70.06(16) . . . . ?
C13 Ru1 N1 C1 105.2(2) . . . . ?
C12 Ru1 N1 C1 99.36(16) . . . . ?
C16 Ru1 N1 C1 32.43(16) . . . . ?
C15 Ru1 N1 C1 3.86(17) . . . . ?
C11 Ru1 N1 C5 3.53(12) . . . . ?
N3 Ru1 N1 C5 87.48(13) . . . . ?
C14 Ru1 N1 C5 174.81(15) . . . . ?
C17 Ru1 N1 C5 -108.57(13) . . . . ?
C13 Ru1 N1 C5 -73.4(2) . . . . ?
C12 Ru1 N1 C5 -79.28(14) . . . . ?
C16 Ru1 N1 C5 -146.21(13) . . . . ?
C15 Ru1 N1 C5 -174.78(12) . . . . ?
C5 N1 C1 C2 0.4(3) . . . . ?
Ru1 N1 C1 C2 -178.19(16) . . . . ?
N1 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 N2 -179.4(2) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
N2 C3 C4 C5 179.4(2) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C1 N1 C5 C4 -0.5(3) . . . . ?
Ru1 N1 C5 C4 178.24(13) . . . . ?
C1 N1 C5 C6 178.54(16) . . . . ?
Ru1 N1 C5 C6 -2.74(19) . . . . ?
C3 C4 C5 N1 0.2(3) . . . . ?
C3 C4 C5 C6 -178.72(17) . . . . ?
N1 C5 C6 C7 -178.84(16) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
N1 C5 C6 C11 -0.4(2) . . . . ?
C4 C5 C6 C11 178.56(17) . . . . ?
C11 C6 C7 C8 0.1(3) . . . . ?
C5 C6 C7 C8 178.42(18) . . . . ?
C6 C7 C8 C9 -1.4(3) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 C11 1.6(3) . . . . ?
C9 C10 C11 C6 -2.9(3) . . . . ?
C9 C10 C11 Ru1 177.31(15) . . . . ?
C7 C6 C11 C10 2.0(3) . . . . ?
C5 C6 C11 C10 -176.46(16) . . . . ?
C7 C6 C11 Ru1 -178.15(14) . . . . ?
C5 C6 C11 Ru1 3.38(19) . . . . ?
N3 Ru1 C11 C10 87.58(17) . . . . ?
N1 Ru1 C11 C10 176.19(17) . . . . ?
C14 Ru1 C11 C10 0.7(2) . . . . ?
C17 Ru1 C11 C10 -92.62(17) . . . . ?
C13 Ru1 C11 C10 -24.46(17) . . . . ?
C12 Ru1 C11 C10 -61.95(17) . . . . ?
C16 Ru1 C11 C10 -103.07(19) . . . . ?
C15 Ru1 C11 C10 -9.0(3) . . . . ?
N3 Ru1 C11 C6 -92.24(13) . . . . ?
N1 Ru1 C11 C6 -3.62(12) . . . . ?
C14 Ru1 C11 C6 -179.10(12) . . . . ?
C17 Ru1 C11 C6 87.57(14) . . . . ?
C13 Ru1 C11 C6 155.72(13) . . . . ?
C12 Ru1 C11 C6 118.23(13) . . . . ?
C16 Ru1 C11 C6 77.11(18) . . . . ?
C15 Ru1 C11 C6 171.22(18) . . . . ?
C11 Ru1 C12 C17 -129.19(11) . . . . ?
N3 Ru1 C12 C17 153.00(12) . . . . ?
N1 Ru1 C12 C17 -53.35(12) . . . . ?
C14 Ru1 C12 C17 101.02(12) . . . . ?
C13 Ru1 C12 C17 130.08(16) . . . . ?
C16 Ru1 C12 C17 29.57(10) . . . . ?
C15 Ru1 C12 C17 64.27(11) . . . . ?
C11 Ru1 C12 C13 100.73(11) . . . . ?
N3 Ru1 C12 C13 22.92(18) . . . . ?
N1 Ru1 C12 C13 176.57(10) . . . . ?
C14 Ru1 C12 C13 -29.06(11) . . . . ?
C17 Ru1 C12 C13 -130.08(16) . . . . ?
C16 Ru1 C12 C13 -100.51(12) . . . . ?
C15 Ru1 C12 C13 -65.81(11) . . . . ?
C11 Ru1 C12 C18 -14.08(18) . . . . ?
N3 Ru1 C12 C18 -91.9(2) . . . . ?
N1 Ru1 C12 C18 61.8(2) . . . . ?
C14 Ru1 C12 C18 -143.9(2) . . . . ?
C17 Ru1 C12 C18 115.1(2) . . . . ?
C13 Ru1 C12 C18 -114.8(2) . . . . ?
C16 Ru1 C12 C18 144.7(2) . . . . ?
C15 Ru1 C12 C18 179.38(19) . . . . ?
C17 C12 C13 C14 -0.7(3) . . . . ?
C18 C12 C13 C14 177.51(17) . . . . ?
Ru1 C12 C13 C14 53.74(15) . . . . ?
C17 C12 C13 Ru1 -54.41(14) . . . . ?
C18 C12 C13 Ru1 123.77(17) . . . . ?
C11 Ru1 C13 C14 145.96(11) . . . . ?
N3 Ru1 C13 C14 60.18(12) . . . . ?
N1 Ru1 C13 C14 -140.57(17) . . . . ?
C17 Ru1 C13 C14 -102.15(12) . . . . ?
C12 Ru1 C13 C14 -132.37(16) . . . . ?
C16 Ru1 C13 C14 -64.60(11) . . . . ?
C15 Ru1 C13 C14 -29.27(11) . . . . ?
C11 Ru1 C13 C12 -81.67(11) . . . . ?
N3 Ru1 C13 C12 -167.45(10) . . . . ?
N1 Ru1 C13 C12 -8.2(2) . . . . ?
C14 Ru1 C13 C12 132.37(16) . . . . ?
C17 Ru1 C13 C12 30.22(11) . . . . ?
C16 Ru1 C13 C12 67.77(11) . . . . ?
C15 Ru1 C13 C12 103.10(12) . . . . ?
C12 C13 C14 C15 5.3(3) . . . . ?
Ru1 C13 C14 C15 59.37(16) . . . . ?
C12 C13 C14 Ru1 -54.05(15) . . . . ?
C11 Ru1 C14 C13 -43.80(14) . . . . ?
N3 Ru1 C14 C13 -126.73(12) . . . . ?
N1 Ru1 C14 C13 146.84(15) . . . . ?
C17 Ru1 C14 C13 66.63(12) . . . . ?
C12 Ru1 C14 C13 29.31(11) . . . . ?
C16 Ru1 C14 C13 103.35(12) . . . . ?
C15 Ru1 C14 C13 131.60(16) . . . . ?
C11 Ru1 C14 C15 -175.41(10) . . . . ?
N3 Ru1 C14 C15 101.67(11) . . . . ?
N1 Ru1 C14 C15 15.2(2) . . . . ?
C17 Ru1 C14 C15 -64.97(11) . . . . ?
C13 Ru1 C14 C15 -131.60(16) . . . . ?
C12 Ru1 C14 C15 -102.29(12) . . . . ?
C16 Ru1 C14 C15 -28.26(10) . . . . ?
C13 C14 C15 C16 -5.6(3) . . . . ?
Ru1 C14 C15 C16 51.56(15) . . . . ?
C13 C14 C15 C19 177.31(17) . . . . ?
Ru1 C14 C15 C19 -125.54(16) . . . . ?
C13 C14 C15 Ru1 -57.15(15) . . . . ?
C11 Ru1 C15 C16 -119.1(2) . . . . ?
N3 Ru1 C15 C16 146.49(11) . . . . ?
N1 Ru1 C15 C16 55.13(13) . . . . ?
C14 Ru1 C15 C16 -132.06(17) . . . . ?
C17 Ru1 C15 C16 -28.26(11) . . . . ?
C13 Ru1 C15 C16 -102.38(13) . . . . ?
C12 Ru1 C15 C16 -64.88(12) . . . . ?
C11 Ru1 C15 C14 13.0(3) . . . . ?
N3 Ru1 C15 C14 -81.45(12) . . . . ?
N1 Ru1 C15 C14 -172.81(10) . . . . ?
C17 Ru1 C15 C14 103.80(12) . . . . ?
C13 Ru1 C15 C14 29.68(11) . . . . ?
C12 Ru1 C15 C14 67.18(12) . . . . ?
C16 Ru1 C15 C14 132.06(17) . . . . ?
C11 Ru1 C15 C19 123.1(2) . . . . ?
N3 Ru1 C15 C19 28.66(18) . . . . ?
N1 Ru1 C15 C19 -62.69(18) . . . . ?
C14 Ru1 C15 C19 110.1(2) . . . . ?
C17 Ru1 C15 C19 -146.09(19) . . . . ?
C13 Ru1 C15 C19 139.79(19) . . . . ?
C12 Ru1 C15 C19 177.30(18) . . . . ?
C16 Ru1 C15 C19 -117.8(2) . . . . ?
C14 C15 C16 C17 1.4(3) . . . . ?
C19 C15 C16 C17 178.37(16) . . . . ?
Ru1 C15 C16 C17 51.10(15) . . . . ?
C14 C15 C16 Ru1 -49.72(14) . . . . ?
C19 C15 C16 Ru1 127.27(17) . . . . ?
C11 Ru1 C16 C15 150.42(13) . . . . ?
N3 Ru1 C16 C15 -42.76(14) . . . . ?
N1 Ru1 C16 C15 -133.73(11) . . . . ?
C14 Ru1 C16 C15 29.48(11) . . . . ?
C17 Ru1 C16 C15 134.44(17) . . . . ?
C13 Ru1 C16 C15 66.79(12) . . . . ?
C12 Ru1 C16 C15 104.93(12) . . . . ?
C11 Ru1 C16 C17 15.98(18) . . . . ?
N3 Ru1 C16 C17 -177.21(10) . . . . ?
N1 Ru1 C16 C17 91.82(11) . . . . ?
C14 Ru1 C16 C17 -104.97(12) . . . . ?
C13 Ru1 C16 C17 -67.65(11) . . . . ?
C12 Ru1 C16 C17 -29.51(11) . . . . ?
C15 Ru1 C16 C17 -134.44(17) . . . . ?
C13 C12 C17 C16 -3.4(3) . . . . ?
C18 C12 C17 C16 178.39(17) . . . . ?
Ru1 C12 C17 C16 -57.80(15) . . . . ?
C13 C12 C17 Ru1 54.37(14) . . . . ?
C18 C12 C17 Ru1 -123.81(17) . . . . ?
C15 C16 C17 C12 3.1(3) . . . . ?
Ru1 C16 C17 C12 56.75(15) . . . . ?
C15 C16 C17 Ru1 -53.64(15) . . . . ?
C11 Ru1 C17 C12 57.20(12) . . . . ?
N3 Ru1 C17 C12 -123.5(2) . . . . ?
N1 Ru1 C17 C12 136.34(11) . . . . ?
C14 Ru1 C17 C12 -68.09(11) . . . . ?
C13 Ru1 C17 C12 -30.69(11) . . . . ?
C16 Ru1 C17 C12 -131.52(16) . . . . ?
C15 Ru1 C17 C12 -104.66(12) . . . . ?
C11 Ru1 C17 C16 -171.28(10) . . . . ?
N3 Ru1 C17 C16 8.0(3) . . . . ?
N1 Ru1 C17 C16 -92.14(11) . . . . ?
C14 Ru1 C17 C16 63.43(11) . . . . ?
C13 Ru1 C17 C16 100.83(12) . . . . ?
C12 Ru1 C17 C16 131.52(16) . . . . ?
C15 Ru1 C17 C16 26.85(10) . . . . ?
C16 C15 C19 C21 -18.0(3) . . . . ?
C14 C15 C19 C21 158.93(18) . . . . ?
Ru1 C15 C19 C21 74.8(2) . . . . ?
C16 C15 C19 C20 105.8(2) . . . . ?
C14 C15 C19 C20 -77.3(2) . . . . ?
Ru1 C15 C19 C20 -161.46(15) . . . . ?

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
N2 H2N F4 0.86(3) 2.33(3) 3.032(3) 139(3) 1_655
N2 H2N F1 0.86(3) 2.48(3) 3.244(3) 148(3) 1_655
N2 H1N F4 0.85(3) 2.25(3) 3.030(3) 151(3) 3_667
N2 H1N F3 0.85(3) 2.48(3) 3.249(3) 151(3) 3_667

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        32.53
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.799
_refine_diff_density_min         -1.700
_refine_diff_density_rms         0.077