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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_x16219
_database_code_depnum_ccdc_archive 'CCDC 1856425'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2016). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2018-07-17 deposited with the CCDC.
2018-10-19 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         'C28 H24 N8 Ru, 2(F6 P)'
_chemical_formula_sum            'C28 H24 F12 N8 P2 Ru'
_chemical_formula_weight         863.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru 0.0552 3.2960 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   13.5829(4)
_cell_length_b                   20.0799(5)
_cell_length_c                   11.5630(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.845(1)
_cell_angle_gamma                90
_cell_volume                     3153.39(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    9571
_cell_measurement_theta_min      3.93
_cell_measurement_theta_max      68.30

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_F_000             1720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    5.981
_shelx_estimated_absorpt_T_min   0.559
_shelx_estimated_absorpt_T_max   0.680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.520
_exptl_absorpt_correction_T_max  0.661
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus rotating anode'
_diffrn_measurement_device_type  'Bruker X8 Proteum diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 5.6
_diffrn_reflns_number            21425
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.929
_diffrn_reflns_theta_max         68.294
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996

_reflns_number_total             2884
_reflns_number_gt                2865
_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       'APEX2 (Bruker-AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker-AXS, 2006)'
_computing_data_reduction        'APEX2 (Bruker-AXS, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+6.5271P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.000085(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2884
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0608
_refine_ls_wR_factor_gt          0.0605
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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
RU1 Ru 0.500000 0.75667(2) 0.750000 0.01049(9) Uani 1 2 d S T P . .
N1 N 0.49310(12) 0.82908(8) 0.87648(14) 0.0142(3) Uani 1 1 d . . . . .
N2 N 0.64628(12) 0.76390(8) 0.80100(15) 0.0135(3) Uani 1 1 d . . . . .
N3 N 0.51868(12) 0.68512(8) 0.62233(14) 0.0134(3) Uani 1 1 d . . . . .
N4 N 0.58865(12) 0.69760(8) 0.54321(14) 0.0163(3) Uani 1 1 d . . . . .
C1 C 0.41054(15) 0.85906(10) 0.91173(18) 0.0186(4) Uani 1 1 d . . . . .
H1A H 0.349825 0.847572 0.875099 0.022 Uiso 1 1 calc R U . . .
C2 C 0.41023(16) 0.90588(11) 0.99898(19) 0.0222(4) Uani 1 1 d . . . . .
H2A H 0.350469 0.926344 1.021619 0.027 Uiso 1 1 calc R U . . .
C3 C 0.49851(16) 0.92258(10) 1.05307(18) 0.0215(4) Uani 1 1 d . . . . .
H3A H 0.500089 0.953954 1.114576 0.026 Uiso 1 1 calc R U . . .
C4 C 0.58439(15) 0.8928(1) 1.01601(17) 0.0187(4) Uani 1 1 d . . . . .
H4A H 0.645788 0.904072 1.051215 0.022 Uiso 1 1 calc R U . . .
C5 C 0.58027(14) 0.84646(9) 0.92729(16) 0.0143(4) Uani 1 1 d . . . . .
C6 C 0.66656(14) 0.81068(9) 0.88295(16) 0.0138(4) Uani 1 1 d . . . . .
C7 C 0.76240(15) 0.82273(10) 0.92111(17) 0.0172(4) Uani 1 1 d . . . . .
H7A H 0.775462 0.856529 0.976742 0.021 Uiso 1 1 calc R U . . .
C8 C 0.83855(15) 0.78514(10) 0.87745(18) 0.0188(4) Uani 1 1 d . . . . .
H8A H 0.904439 0.792696 0.902867 0.023 Uiso 1 1 calc R U . . .
C9 C 0.81755(16) 0.73624(10) 0.79605(19) 0.0191(4) Uani 1 1 d . . . . .
H9A H 0.868602 0.709312 0.765821 0.023 Uiso 1 1 calc R U . . .
C10 C 0.72127(14) 0.72738(10) 0.75974(17) 0.0161(4) Uani 1 1 d . . . . .
H10A H 0.707214 0.694188 0.703328 0.019 Uiso 1 1 calc R U . . .
C11 C 0.59962(15) 0.65435(10) 0.45772(17) 0.0187(4) Uani 1 1 d . . . . .
H11A H 0.649943 0.662802 0.403446 0.022 Uiso 1 1 calc R U . . .
C12 C 0.54232(15) 0.59721(10) 0.44194(17) 0.0188(4) Uani 1 1 d . . . . .
H12A H 0.551624 0.568144 0.378201 0.023 Uiso 1 1 calc R U . . .
C13 C 0.47194(15) 0.58521(10) 0.52321(18) 0.0178(4) Uani 1 1 d . . . . .
H13A H 0.430455 0.547211 0.517887 0.021 Uiso 1 1 calc R U . . .
C14 C 0.46318(14) 0.63032(9) 0.61347(16) 0.0147(4) Uani 1 1 d . . . . .
H14A H 0.415803 0.621900 0.671300 0.018 Uiso 1 1 calc R U . . .
P1 P 0.27188(4) 0.50546(2) 0.77019(4) 0.01540(13) Uani 1 1 d . . . . .
F1 F 0.15544(10) 0.51266(8) 0.75833(12) 0.0361(3) Uani 1 1 d . . . . .
F2 F 0.38933(9) 0.49911(7) 0.78138(11) 0.0284(3) Uani 1 1 d . . . . .
F3 F 0.26037(10) 0.47773(6) 0.89820(11) 0.0280(3) Uani 1 1 d . . . . .
F4 F 0.28412(10) 0.53438(8) 0.64219(11) 0.0327(3) Uani 1 1 d . . . . .
F5 F 0.27976(11) 0.57969(6) 0.82137(12) 0.0338(3) Uani 1 1 d . . . . .
F6 F 0.26658(11) 0.43168(7) 0.71946(12) 0.0332(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
RU1 N1 2.0654(16) . ?
RU1 N1 2.0654(16) 2_656 ?
RU1 N2 2.0693(17) 2_656 ?
RU1 N2 2.0693(17) . ?
RU1 N3 2.0782(16) 2_656 ?
RU1 N3 2.0783(16) . ?
N1 C1 1.341(3) . ?
N1 C5 1.360(3) . ?
N2 C10 1.348(3) . ?
N2 C6 1.360(3) . ?
N3 C14 1.337(3) . ?
N3 N4 1.352(2) . ?
N4 C11 1.326(3) . ?
C1 C2 1.379(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.385(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.473(3) . ?
C6 C7 1.390(3) . ?
C7 C8 1.382(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.387(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.379(3) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.397(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.372(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.388(3) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
P1 F3 1.5913(12) . ?
P1 F1 1.5921(14) . ?
P1 F6 1.5946(13) . ?
P1 F4 1.6009(13) . ?
P1 F2 1.6037(13) . ?
P1 F5 1.6067(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 RU1 N1 90.50(9) . 2_656 ?
N1 RU1 N2 95.68(6) . 2_656 ?
N1 RU1 N2 78.59(7) 2_656 2_656 ?
N1 RU1 N2 78.60(7) . . ?
N1 RU1 N2 95.68(6) 2_656 . ?
N2 RU1 N2 171.96(9) 2_656 . ?
N1 RU1 N3 88.65(7) . 2_656 ?
N1 RU1 N3 175.54(6) 2_656 2_656 ?
N2 RU1 N3 97.13(6) 2_656 2_656 ?
N2 RU1 N3 88.44(6) . 2_656 ?
N1 RU1 N3 175.54(6) . . ?
N1 RU1 N3 88.65(7) 2_656 . ?
N2 RU1 N3 88.44(6) 2_656 . ?
N2 RU1 N3 97.13(6) . . ?
N3 RU1 N3 92.53(9) 2_656 . ?
C1 N1 C5 118.70(17) . . ?
C1 N1 RU1 125.31(14) . . ?
C5 N1 RU1 115.99(13) . . ?
C10 N2 C6 118.44(17) . . ?
C10 N2 RU1 126.04(14) . . ?
C6 N2 RU1 115.52(13) . . ?
C14 N3 N4 120.13(16) . . ?
C14 N3 RU1 123.28(13) . . ?
N4 N3 RU1 116.54(12) . . ?
C11 N4 N3 118.08(17) . . ?
N1 C1 C2 122.67(19) . . ?
N1 C1 H1A 118.7 . . ?
C2 C1 H1A 118.7 . . ?
C1 C2 C3 118.9(2) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
C4 C3 C2 118.90(19) . . ?
C4 C3 H3A 120.6 . . ?
C2 C3 H3A 120.6 . . ?
C3 C4 C5 119.63(19) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
N1 C5 C4 121.17(18) . . ?
N1 C5 C6 114.63(17) . . ?
C4 C5 C6 124.17(18) . . ?
N2 C6 C7 121.39(18) . . ?
N2 C6 C5 115.18(17) . . ?
C7 C6 C5 123.43(18) . . ?
C8 C7 C6 119.45(19) . . ?
C8 C7 H7A 120.3 . . ?
C6 C7 H7A 120.3 . . ?
C7 C8 C9 119.14(19) . . ?
C7 C8 H8A 120.4 . . ?
C9 C8 H8A 120.4 . . ?
C10 C9 C8 118.9(2) . . ?
C10 C9 H9A 120.6 . . ?
C8 C9 H9A 120.6 . . ?
N2 C10 C9 122.70(19) . . ?
N2 C10 H10A 118.7 . . ?
C9 C10 H10A 118.7 . . ?
N4 C11 C12 124.54(19) . . ?
N4 C11 H11A 117.7 . . ?
C12 C11 H11A 117.7 . . ?
C13 C12 C11 116.57(18) . . ?
C13 C12 H12A 121.7 . . ?
C11 C12 H12A 121.7 . . ?
C12 C13 C14 117.96(19) . . ?
C12 C13 H13A 121.0 . . ?
C14 C13 H13A 121.0 . . ?
N3 C14 C13 122.69(18) . . ?
N3 C14 H14A 118.7 . . ?
C13 C14 H14A 118.7 . . ?
F3 P1 F1 90.05(8) . . ?
F3 P1 F6 90.72(7) . . ?
F1 P1 F6 90.76(8) . . ?
F3 P1 F4 179.14(8) . . ?
F1 P1 F4 90.23(8) . . ?
F6 P1 F4 90.09(8) . . ?
F3 P1 F2 90.48(7) . . ?
F1 P1 F2 179.28(9) . . ?
F6 P1 F2 89.73(8) . . ?
F4 P1 F2 89.24(7) . . ?
F3 P1 F5 89.36(7) . . ?
F1 P1 F5 90.47(8) . . ?
F6 P1 F5 178.76(8) . . ?
F4 P1 F5 89.81(8) . . ?
F2 P1 F5 89.04(8) . . ?

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
C14 N3 N4 C11 0.3(3) . . . . ?
RU1 N3 N4 C11 -177.18(14) . . . . ?
C5 N1 C1 C2 -1.3(3) . . . . ?
RU1 N1 C1 C2 178.18(16) . . . . ?
N1 C1 C2 C3 -0.3(3) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C1 N1 C5 C4 1.8(3) . . . . ?
RU1 N1 C5 C4 -177.74(14) . . . . ?
C1 N1 C5 C6 179.83(17) . . . . ?
RU1 N1 C5 C6 0.3(2) . . . . ?
C3 C4 C5 N1 -0.7(3) . . . . ?
C3 C4 C5 C6 -178.54(18) . . . . ?
C10 N2 C6 C7 2.3(3) . . . . ?
RU1 N2 C6 C7 -177.10(14) . . . . ?
C10 N2 C6 C5 -177.46(16) . . . . ?
RU1 N2 C6 C5 3.2(2) . . . . ?
N1 C5 C6 N2 -2.3(2) . . . . ?
C4 C5 C6 N2 175.68(18) . . . . ?
N1 C5 C6 C7 177.98(17) . . . . ?
C4 C5 C6 C7 -4.0(3) . . . . ?
N2 C6 C7 C8 -1.9(3) . . . . ?
C5 C6 C7 C8 177.79(18) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
C6 N2 C10 C9 -0.9(3) . . . . ?
RU1 N2 C10 C9 178.32(15) . . . . ?
C8 C9 C10 N2 -0.7(3) . . . . ?
N3 N4 C11 C12 1.5(3) . . . . ?
N4 C11 C12 C13 -1.7(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
N4 N3 C14 C13 -1.8(3) . . . . ?
RU1 N3 C14 C13 175.46(14) . . . . ?
C12 C13 C14 N3 1.6(3) . . . . ?

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_x16240
_database_code_depnum_ccdc_archive 'CCDC 1856426'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2016). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2018-07-17 deposited with the CCDC.
2018-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6

_shelx_SHELXL_version_number     2016/6

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H24 N8 Ru, 2(F6 P)'
_chemical_formula_sum            'C28 H24 F12 N8 P2 Ru'
_chemical_formula_weight         863.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru 0.0552 3.2960 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   21.4835(4)
_cell_length_b                   10.2495(2)
_cell_length_c                   17.1972(4)
_cell_angle_alpha                90
_cell_angle_beta                 125.539(1)
_cell_angle_gamma                90
_cell_volume                     3081.34(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      5.00
_cell_measurement_theta_max      68.30

_exptl_crystal_description       flake
_exptl_crystal_colour            orange-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_F_000             1720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    6.121
_shelx_estimated_absorpt_T_min   0.674
_shelx_estimated_absorpt_T_max   0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.529
_exptl_absorpt_correction_T_max  0.661
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus rotating anode'
_diffrn_measurement_device_type  'Bruker X8 Proteum diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 5.6
_diffrn_reflns_number            20116
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.002
_diffrn_reflns_theta_max         68.298
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999

_reflns_number_total             2816
_reflns_number_gt                2487
_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       'APEX2 (Bruker-AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker-AXS, 2006)'
_computing_data_reduction        'APEX2 (Bruker-AXS, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²+3.6968P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2816
_refine_ls_number_parameters     277
_refine_ls_number_restraints     171
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0911
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.053
_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
Ru1 Ru 0.500000 0.53390(3) 0.250000 0.02190(13) Uani 1 2 d S T P . .
N1 N 0.44357(14) 0.3904(2) 0.27068(18) 0.0236(5) Uani 1 1 d . . . . .
N2 N 0.56790(15) 0.5220(3) 0.39768(19) 0.0242(5) Uani 1 1 d . . . . .
C1 C 0.37930(18) 0.3293(3) 0.2017(2) 0.0294(7) Uani 1 1 d . . . . .
H1 H 0.358294 0.348790 0.136871 0.035 Uiso 1 1 calc R U . . .
C2 C 0.34266(19) 0.2394(3) 0.2216(2) 0.0321(7) Uani 1 1 d . . . . .
H2 H 0.296682 0.199094 0.171173 0.038 Uiso 1 1 calc R U . . .
C3 C 0.37336(19) 0.2084(3) 0.3154(3) 0.0317(7) Uani 1 1 d . . . . .
H3 H 0.348241 0.148349 0.330559 0.038 Uiso 1 1 calc R U . . .
C4 C 0.44205(19) 0.2669(3) 0.3876(2) 0.0289(7) Uani 1 1 d . . . . .
H4 H 0.465345 0.244379 0.452580 0.035 Uiso 1 1 calc R U . . .
C5 C 0.47592(17) 0.3578(3) 0.3637(2) 0.0253(7) Uani 1 1 d . . . . .
C6 C 0.54612(17) 0.4304(3) 0.4346(2) 0.0244(6) Uani 1 1 d . . . . .
C7 C 0.58855(19) 0.4099(3) 0.5320(2) 0.0303(7) Uani 1 1 d . . . . .
H7 H 0.573704 0.343752 0.556853 0.036 Uiso 1 1 calc R U . . .
C8 C 0.65263(19) 0.4852(4) 0.5937(2) 0.0330(8) Uani 1 1 d . . . . .
H8 H 0.682364 0.470853 0.660738 0.040 Uiso 1 1 calc R U . . .
C9 C 0.67235(18) 0.5817(4) 0.5554(2) 0.0311(7) Uani 1 1 d . . . . .
H9 H 0.715160 0.636566 0.595981 0.037 Uiso 1 1 calc R U . . .
C10 C 0.62903(17) 0.5971(3) 0.4578(2) 0.0272(7) Uani 1 1 d . . . . .
H10 H 0.642860 0.663367 0.431809 0.033 Uiso 1 1 calc R U . . .
N3 N 0.56200(14) 0.6784(3) 0.23473(18) 0.0240(5) Uani 1 1 d . . . . .
N4 N 0.67810(15) 0.7443(3) 0.25849(19) 0.0314(6) Uani 1 1 d . . . . .
C11 C 0.63629(18) 0.6640(3) 0.2712(2) 0.0284(7) Uani 1 1 d . . . . .
H11 H 0.661373 0.589315 0.309895 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6432(2) 0.8500(3) 0.2058(2) 0.0344(8) Uani 1 1 d . . . . .
H12 H 0.671282 0.909717 0.195042 0.041 Uiso 1 1 calc R U . . .
C13 C 0.5670(2) 0.8753(3) 0.1663(2) 0.0348(8) Uani 1 1 d . . . . .
H13 H 0.542725 0.951568 0.129241 0.042 Uiso 1 1 calc R U . . .
C14 C 0.52796(19) 0.7873(3) 0.1822(2) 0.0302(7) Uani 1 1 d . . . . .
H14 H 0.475612 0.802842 0.155748 0.036 Uiso 1 1 calc R U . . .
P1 P 0.66194(11) 0.00940(19) 0.49211(13) 0.0299(3) Uani 0.874(8) 1 d D . P A 1
F1 F 0.60456(18) -0.0788(4) 0.5010(2) 0.0469(9) Uani 0.874(8) 1 d D . P A 1
F2 F 0.72088(17) 0.0935(3) 0.4851(2) 0.0454(8) Uani 0.874(8) 1 d D . P A 1
F3 F 0.6074(2) -0.0069(4) 0.37969(19) 0.0686(15) Uani 0.874(8) 1 d D . P A 1
F4 F 0.71729(18) 0.0216(3) 0.60645(19) 0.0413(8) Uani 0.874(8) 1 d D . P A 1
F5 F 0.6185(2) 0.1365(4) 0.4867(3) 0.0704(12) Uani 0.874(8) 1 d D . P A 1
F6 F 0.7071(2) -0.1201(3) 0.5009(3) 0.0571(11) Uani 0.874(8) 1 d D . P A 1
P1' P 0.6501(7) 0.0283(12) 0.4800(9) 0.0299(3) Uani 0.126(8) 1 d D . P A 2
F1' F 0.5931(11) -0.030(2) 0.5029(15) 0.0469(9) Uani 0.126(8) 1 d D . P A 2
F2' F 0.7077(11) 0.085(2) 0.4583(17) 0.0454(8) Uani 0.126(8) 1 d D . P A 2
F3' F 0.5789(9) 0.068(3) 0.3772(10) 0.062(6) Uani 0.126(8) 1 d D U P A 2
F4' F 0.7208(10) -0.016(3) 0.5843(13) 0.065(7) Uani 0.126(8) 1 d D U P A 2
F5' F 0.6486(16) 0.1649(15) 0.5210(18) 0.062(6) Uani 0.126(8) 1 d D U P A 2
F6' F 0.6539(14) -0.1094(15) 0.4400(18) 0.066(6) Uani 0.126(8) 1 d D U P A 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 N1 2.064(3) . ?
Ru1 N1 2.064(3) 2_655 ?
Ru1 N2 2.070(3) 2_655 ?
Ru1 N2 2.070(3) . ?
Ru1 N3 2.108(3) . ?
Ru1 N3 2.108(3) 2_655 ?
N1 C1 1.342(4) . ?
N1 C5 1.364(4) . ?
N2 C10 1.344(4) . ?
N2 C6 1.360(4) . ?
C1 C2 1.378(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.378(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.475(4) . ?
C6 C7 1.381(4) . ?
C7 C8 1.385(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
N3 C11 1.341(4) . ?
N3 C14 1.353(4) . ?
N4 C11 1.327(4) . ?
N4 C12 1.329(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.364(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
P1 F5 1.573(3) . ?
P1 F3 1.583(3) . ?
P1 F2 1.593(3) . ?
P1 F6 1.598(3) . ?
P1 F4 1.606(3) . ?
P1 F1 1.606(3) . ?
P1' F5' 1.577(9) . ?
P1' F3' 1.577(9) . ?
P1' F6' 1.592(9) . ?
P1' F2' 1.596(8) . ?
P1' F4' 1.602(9) . ?
P1' F1' 1.606(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ru1 N1 89.12(14) . 2_655 ?
N1 Ru1 N2 95.96(10) . 2_655 ?
N1 Ru1 N2 79.19(10) 2_655 2_655 ?
N1 Ru1 N2 79.18(10) . . ?
N1 Ru1 N2 95.96(10) 2_655 . ?
N2 Ru1 N2 173.26(14) 2_655 . ?
N1 Ru1 N3 177.51(10) . . ?
N1 Ru1 N3 90.12(10) 2_655 . ?
N2 Ru1 N3 86.22(10) 2_655 . ?
N2 Ru1 N3 98.54(10) . . ?
N1 Ru1 N3 90.12(10) . 2_655 ?
N1 Ru1 N3 177.51(10) 2_655 2_655 ?
N2 Ru1 N3 98.54(10) 2_655 2_655 ?
N2 Ru1 N3 86.22(10) . 2_655 ?
N3 Ru1 N3 90.74(14) . 2_655 ?
C1 N1 C5 118.9(3) . . ?
C1 N1 Ru1 125.9(2) . . ?
C5 N1 Ru1 115.2(2) . . ?
C10 N2 C6 119.0(3) . . ?
C10 N2 Ru1 125.9(2) . . ?
C6 N2 Ru1 115.1(2) . . ?
N1 C1 C2 122.4(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 121.0(3) . . ?
N1 C5 C6 115.1(3) . . ?
C4 C5 C6 123.8(3) . . ?
N2 C6 C7 120.5(3) . . ?
N2 C6 C5 115.2(3) . . ?
C7 C6 C5 124.2(3) . . ?
C6 C7 C8 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 118.5(3) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C10 C9 C8 119.0(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
N2 C10 C9 122.5(3) . . ?
N2 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C11 N3 C14 115.9(3) . . ?
C11 N3 Ru1 122.1(2) . . ?
C14 N3 Ru1 121.9(2) . . ?
C11 N4 C12 116.8(3) . . ?
N4 C11 N3 126.2(3) . . ?
N4 C11 H11 116.9 . . ?
N3 C11 H11 116.9 . . ?
N4 C12 C13 121.7(3) . . ?
N4 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 117.9(3) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
N3 C14 C13 121.5(3) . . ?
N3 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
F5 P1 F3 91.3(2) . . ?
F5 P1 F2 91.0(2) . . ?
F3 P1 F2 91.27(16) . . ?
F5 P1 F6 178.3(2) . . ?
F3 P1 F6 90.3(2) . . ?
F2 P1 F6 89.50(17) . . ?
F5 P1 F4 90.0(2) . . ?
F3 P1 F4 178.4(2) . . ?
F2 P1 F4 89.71(16) . . ?
F6 P1 F4 88.40(18) . . ?
F5 P1 F1 90.58(19) . . ?
F3 P1 F1 89.57(16) . . ?
F2 P1 F1 178.21(18) . . ?
F6 P1 F1 88.91(17) . . ?
F4 P1 F1 89.42(16) . . ?
F5' P1' F3' 90.7(9) . . ?
F5' P1' F6' 178.6(10) . . ?
F3' P1' F6' 90.2(9) . . ?
F5' P1' F2' 90.0(9) . . ?
F3' P1' F2' 91.3(9) . . ?
F6' P1' F2' 89.0(8) . . ?
F5' P1' F4' 90.4(9) . . ?
F3' P1' F4' 178.(1) . . ?
F6' P1' F4' 88.7(9) . . ?
F2' P1' F4' 90.4(9) . . ?
F5' P1' F1' 90.4(9) . . ?
F3' P1' F1' 89.4(8) . . ?
F6' P1' F1' 90.7(8) . . ?
F2' P1' F1' 179.2(11) . . ?
F4' P1' F1' 88.9(8) . . ?

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 N1 C1 C2 3.2(5) . . . . ?
Ru1 N1 C1 C2 -176.3(2) . . . . ?
N1 C1 C2 C3 -1.3(5) . . . . ?
C1 C2 C3 C4 -1.7(5) . . . . ?
C2 C3 C4 C5 2.5(5) . . . . ?
C1 N1 C5 C4 -2.3(4) . . . . ?
Ru1 N1 C5 C4 177.3(2) . . . . ?
C1 N1 C5 C6 -179.7(3) . . . . ?
Ru1 N1 C5 C6 0.0(3) . . . . ?
C3 C4 C5 N1 -0.6(5) . . . . ?
C3 C4 C5 C6 176.6(3) . . . . ?
C10 N2 C6 C7 -3.5(4) . . . . ?
Ru1 N2 C6 C7 177.6(2) . . . . ?
C10 N2 C6 C5 176.6(3) . . . . ?
Ru1 N2 C6 C5 -2.3(3) . . . . ?
N1 C5 C6 N2 1.6(4) . . . . ?
C4 C5 C6 N2 -175.7(3) . . . . ?
N1 C5 C6 C7 -178.3(3) . . . . ?
C4 C5 C6 C7 4.4(5) . . . . ?
N2 C6 C7 C8 2.0(5) . . . . ?
C5 C6 C7 C8 -178.2(3) . . . . ?
C6 C7 C8 C9 0.7(5) . . . . ?
C7 C8 C9 C10 -1.7(5) . . . . ?
C6 N2 C10 C9 2.5(5) . . . . ?
Ru1 N2 C10 C9 -178.7(2) . . . . ?
C8 C9 C10 N2 0.2(5) . . . . ?
C12 N4 C11 N3 1.2(5) . . . . ?
C14 N3 C11 N4 -1.8(5) . . . . ?
Ru1 N3 C11 N4 174.0(2) . . . . ?
C11 N4 C12 C13 0.1(5) . . . . ?
N4 C12 C13 C14 -0.6(5) . . . . ?
C11 N3 C14 C13 1.2(5) . . . . ?
Ru1 N3 C14 C13 -174.7(3) . . . . ?
C12 C13 C14 N3 -0.1(5) . . . . ?

_refine_diff_density_max         0.555
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.084

