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

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

data_exp_14
_database_code_depnum_ccdc_archive 'CCDC 1972140'
loop_
_audit_author_name
_audit_author_address
'Nozomi Tomioka'
;Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University
Japan
;
_audit_update_record             
;
2019-12-16 deposited with the CCDC.	2021-11-04 downloaded from the CCDC.
;
_audit_creation_date             2019-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
"N1-phenylcyclohexa-3,5-diene-1,2-diiminebis(2,2'-bipyridine)ruthenium hexafulolophosphate"
_chemical_formula_moiety         'C32 H26 N6 Ru, 2(F6 P)'
_chemical_formula_sum            'C32 H26 F12 N6 P2 Ru'
_chemical_formula_weight         885.60
_chemical_oxdiff_formula         C32H26F12N6P2Ru
_chemical_oxdiff_usercomment     '298 K'
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'
F F 0.0727 0.0534 '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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.31180(10)
_cell_length_b                   18.79730(10)
_cell_length_c                   13.97790(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.4170(10)
_cell_angle_gamma                90
_cell_volume                     3468.37(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18776
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      75.5780
_cell_measurement_theta_min      3.3310
_exptl_absorpt_coefficient_mu    5.440
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear blackish black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   1.00000
_exptl_transmission_factor_min   0.93290
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25055
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.608
_diffrn_reflns_theta_min         3.348
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00 -42.00   0.50    0.15    --  -42.55 113.00 150.00   76
  2  ω     52.00  78.00   0.50    0.15    --   42.55-113.00  58.00   52
  3  ω   -116.00 -91.00   0.50    0.60    --  -90.25-113.00  58.00   50
  4  ω    -81.00 -42.00   0.50    0.60    --  -90.25 113.00 150.00   78
  5  ω     70.00  98.00   0.50    0.60    --  109.88-113.00  58.00   56
  6  ω    105.00 152.00   0.50    0.60    --  109.88 113.00 150.00   94
  7  ω    -21.00  37.00   0.50    0.15    --  -42.55  19.00-180.00  116
  8  ω    -22.00  36.00   0.50    0.15    --  -42.55  19.00  60.00  116
  9  ω    -22.00  32.00   0.50    0.15    --  -42.55  19.00 -90.00  108
 10  ω    -33.00  32.00   0.50    0.15    --  -42.55  37.00 -60.00  130
 11  ω     95.00 120.00   0.50    0.15    --   42.55 178.00-120.00   50
 12  ω    -41.00 -14.00   0.50    0.60    --  -90.25  45.00-120.00   54
 13  ω    -43.00 -18.00   0.50    0.60    --  -90.25  45.00  60.00   50
 14  ω    -42.00 -15.00   0.50    0.60    --  -90.25  45.00   0.00   54
 15  ω    -43.00 -17.00   0.50    0.60    --  -90.25  45.00 -90.00   52
 16  ω    -41.00 -14.00   0.50    0.60    --  -90.25  45.00 -30.00   54
 17  ω    -43.00 -18.00   0.50    0.60    --  -90.25  45.00 -60.00   50
 18  ω    -43.00 -17.00   0.50    0.60    --  -90.25  45.00  90.00   52
 19  ω     34.00  59.00   0.50    0.60    --  109.88 -45.00 -90.00   50
 20  ω     34.00  59.00   0.50    0.60    --  109.88 -45.00-120.00   50
 21  ω     34.00  59.00   0.50    0.60    --  109.88 -45.00 -60.00   50
 22  ω     46.00  79.00   0.50    0.60    --  109.88 -61.00   0.00   66
 23  ω     38.00  64.00   0.50    0.60    --  109.88 -61.00  90.00   52
 24  ω     35.00  61.00   0.50    0.60    --  109.88 -45.00-150.00   52
 25  ω     35.00  61.00   0.50    0.60    --  109.88 -45.00 -30.00   52
 26  ω     91.00 151.00   0.50    0.60    --  109.88  30.00-120.00  120
 27  ω     37.00 109.00   0.50    0.60    --  109.88 -77.00  90.00  144
 28  ω     39.00  78.00   0.50    0.60    --  109.88 -61.00-150.00   78
 29  ω     34.00  61.00   0.50    0.60    --  109.88 -45.00 120.00   54
 30  ω     40.00 101.00   0.50    0.60    --  109.88 -94.00 -60.00  122
 31  ω     34.00  59.00   0.50    0.60    --  109.88 -45.00 150.00   50
 32  ω     53.00 104.00   0.50    0.60    --  109.88 -94.00  90.00  102
 33  ω     36.00  61.00   0.50    0.60    --  109.88 -45.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0534730000
_diffrn_orient_matrix_UB_12      -0.0199646000
_diffrn_orient_matrix_UB_13      0.0876338000
_diffrn_orient_matrix_UB_21      -0.0321749000
_diffrn_orient_matrix_UB_22      0.0781098000
_diffrn_orient_matrix_UB_23      0.0097059000
_diffrn_orient_matrix_UB_31      -0.0986435000
_diffrn_orient_matrix_UB_32      -0.0146895000
_diffrn_orient_matrix_UB_33      -0.0676570000
_diffrn_oxdiff_digest_frames     
;
012453944d8e9f8c05bbf566d29a4d71e8000410b70
;
_diffrn_oxdiff_digest_hkl        
;
019a6e6e2700455525ffb7962a37564e3e8d37
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6425
_reflns_number_total             6959
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         6959
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0532P)²+1.8550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0976
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C29(H23), C32(H26), C6(H5), C5(H4), C3(H2), C22(H18), C30(H24), C4(H3),
 C31(H25), C12(H10), C8(H6), C26(H22), C19(H15), C13(H11), C23(H19), C11(H9),
 C21(H17), C14(H12), C24(H20), C25(H21), C16(H14), C15(H13), C10(H8), C20(H16),
 C9(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
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 0.28435(2) 0.49233(2) 0.73592(2) 0.04174(8) Uani 1 1 d . . . . .
P1 P 0.08217(6) 0.77508(5) 0.66178(6) 0.0656(2) Uani 1 1 d . . . . .
P2 P 0.40037(8) 0.36485(6) 0.42292(6) 0.0741(2) Uani 1 1 d . . . . .
N6 N 0.32439(16) 0.59114(11) 0.79407(15) 0.0454(4) Uani 1 1 d . . . . .
N1 N 0.37322(16) 0.44085(11) 0.84526(14) 0.0437(4) Uani 1 1 d . . . . .
N3 N 0.21191(17) 0.52952(13) 0.60416(16) 0.0508(5) Uani 1 1 d . . . . .
N2 N 0.40911(18) 0.47250(13) 0.67757(16) 0.0497(5) Uani 1 1 d . . . . .
N4 N 0.21638(17) 0.40076(12) 0.67650(16) 0.0495(5) Uani 1 1 d . . . . .
F4 F 0.19263(18) 0.74471(13) 0.69017(19) 0.0970(7) Uani 1 1 d . . . . .
N5 N 0.15943(17) 0.51792(12) 0.80721(16) 0.0455(4) Uani 1 1 d . . . . .
F6 F 0.0900(2) 0.75639(16) 0.55228(16) 0.1018(7) Uani 1 1 d . . . . .
F9 F 0.3980(2) 0.40865(17) 0.32593(16) 0.1046(8) Uani 1 1 d . . . . .
C28 C 0.25737(19) 0.62238(13) 0.84549(17) 0.0436(5) Uani 1 1 d . . . . .
F3 F 0.0373(3) 0.69900(18) 0.6724(2) 0.1301(11) Uani 1 1 d . . . . .
F1 F 0.1307(2) 0.85082(13) 0.6459(3) 0.1321(12) Uani 1 1 d . . . . .
C27 C 0.1631(2) 0.58287(13) 0.84919(18) 0.0459(5) Uani 1 1 d . . . . .
C2 C 0.46055(19) 0.41659(14) 0.82305(18) 0.0461(5) Uani 1 1 d . . . . .
C1 C 0.4812(2) 0.43586(14) 0.72681(18) 0.0478(5) Uani 1 1 d . . . . .
C18 C 0.16149(19) 0.40805(16) 0.5885(2) 0.0533(6) Uani 1 1 d . . . . .
C7 C 0.3434(2) 0.42484(15) 0.93799(18) 0.0486(6) Uani 1 1 d . . . . .
C17 C 0.1642(2) 0.47886(17) 0.5458(2) 0.0541(6) Uani 1 1 d . . . . .
F2 F -0.02639(19) 0.8058(2) 0.6301(3) 0.1446(13) Uani 1 1 d . . . . .
F8 F 0.3658(3) 0.4335(2) 0.4749(2) 0.1434(13) Uani 1 1 d . . . . .
C29 C 0.2801(2) 0.68569(15) 0.8938(2) 0.0552(6) Uani 1 1 d . . . . .
H29 H 0.233650 0.706047 0.929861 0.066 Uiso 1 1 calc R . . . .
C32 C 0.4136(2) 0.62392(17) 0.7887(2) 0.0604(7) Uani 1 1 d . . . . .
H32 H 0.459758 0.602987 0.752789 0.072 Uiso 1 1 calc R . . . .
C6 C 0.5742(2) 0.41429(17) 0.6934(2) 0.0577(7) Uani 1 1 d . . . . .
H6 H 0.588524 0.427602 0.632565 0.069 Uiso 1 1 calc R . . . .
C5 C 0.6399(2) 0.37462(19) 0.7515(2) 0.0652(8) Uani 1 1 d . . . . .
H5 H 0.699778 0.359725 0.730104 0.078 Uiso 1 1 calc R . . . .
C3 C 0.5349(2) 0.37505(18) 0.8818(2) 0.0605(7) Uani 1 1 d . . . . .
H3 H 0.524665 0.362226 0.944036 0.073 Uiso 1 1 calc R . . . .
C22 C 0.2180(3) 0.33755(16) 0.7205(2) 0.0626(7) Uani 1 1 d . . . . .
H22 H 0.256813 0.332558 0.780375 0.075 Uiso 1 1 calc R . . . .
F11 F 0.5123(2) 0.3907(3) 0.4480(3) 0.1613(16) Uani 1 1 d . . . . .
C30 C 0.3715(3) 0.71858(16) 0.8884(2) 0.0632(7) Uani 1 1 d . . . . .
H30 H 0.387464 0.761206 0.920605 0.076 Uiso 1 1 calc R . . . .
C4 C 0.6194(2) 0.3548(2) 0.8462(2) 0.0708(9) Uani 1 1 d . . . . .
H4 H 0.666332 0.326853 0.884356 0.085 Uiso 1 1 calc R . . . .
C31 C 0.4384(3) 0.68743(18) 0.8349(3) 0.0673(8) Uani 1 1 d . . . . .
H31 H 0.500306 0.709014 0.829673 0.081 Uiso 1 1 calc R . . . .
F7 F 0.4085(3) 0.3260(2) 0.5232(3) 0.1629(15) Uani 1 1 d . . . . .
C12 C 0.3320(3) 0.35451(18) 0.9662(2) 0.0649(8) Uani 1 1 d . . . . .
H12 H 0.344875 0.317463 0.925372 0.078 Uiso 1 1 calc R . . . .
C8 C 0.3266(3) 0.47915(19) 0.9994(2) 0.0651(8) Uani 1 1 d . . . . .
H8 H 0.335378 0.526152 0.981426 0.078 Uiso 1 1 calc R . . . .
F5 F 0.0763(3) 0.7926(3) 0.7690(2) 0.189(2) Uani 1 1 d . . . . .
C26 C 0.0833(2) 0.60826(18) 0.8940(2) 0.0657(8) Uani 1 1 d . . . . .
H26 H 0.086461 0.653333 0.921671 0.079 Uiso 1 1 calc R . . . .
C19 C 0.1081(2) 0.3507(2) 0.5456(3) 0.0725(9) Uani 1 1 d . . . . .
H19 H 0.071096 0.355632 0.484819 0.087 Uiso 1 1 calc R . . . .
C13 C 0.2197(3) 0.59539(17) 0.5698(2) 0.0666(8) Uani 1 1 d . . . . .
H13 H 0.252140 0.630259 0.609739 0.080 Uiso 1 1 calc R . . . .
C23 C 0.0771(2) 0.47738(17) 0.8127(2) 0.0610(7) Uani 1 1 d . . . . .
H23 H 0.074713 0.432177 0.785429 0.073 Uiso 1 1 calc R . . . .
C11 C 0.3016(3) 0.3400(2) 1.0549(3) 0.0784(10) Uani 1 1 d . . . . .
H11 H 0.293726 0.293107 1.073960 0.094 Uiso 1 1 calc R . . . .
C21 C 0.1649(3) 0.27975(18) 0.6813(3) 0.0714(9) Uani 1 1 d . . . . .
H21 H 0.166494 0.236825 0.714554 0.086 Uiso 1 1 calc R . . . .
C14 C 0.1804(3) 0.6129(2) 0.4757(3) 0.0814(11) Uani 1 1 d . . . . .
H14 H 0.186845 0.659019 0.453058 0.098 Uiso 1 1 calc R . . . .
C24 C -0.0034(3) 0.4999(2) 0.8567(3) 0.0761(10) Uani 1 1 d . . . . .
H24 H -0.059209 0.470475 0.858942 0.091 Uiso 1 1 calc R . . . .
C25 C -0.0008(3) 0.5661(2) 0.8971(3) 0.0807(10) Uani 1 1 d . . . . .
H25 H -0.055225 0.582545 0.926482 0.097 Uiso 1 1 calc R . . . .
F12 F 0.2882(3) 0.3429(3) 0.3987(3) 0.191(2) Uani 1 1 d . . . . .
C16 C 0.1234(3) 0.4951(2) 0.4516(3) 0.0768(10) Uani 1 1 d . . . . .
H16 H 0.090082 0.460300 0.412157 0.092 Uiso 1 1 calc R . . . .
C15 C 0.1328(3) 0.5626(3) 0.4174(3) 0.0864(12) Uani 1 1 d . . . . .
H15 H 0.106484 0.573812 0.354351 0.104 Uiso 1 1 calc R . . . .
C10 C 0.2826(3) 0.3955(3) 1.1158(2) 0.0809(11) Uani 1 1 d . . . . .
H10 H 0.260523 0.385968 1.174983 0.097 Uiso 1 1 calc R . . . .
C20 C 0.1097(3) 0.2866(2) 0.5925(3) 0.0803(10) Uani 1 1 d . . . . .
H20 H 0.073523 0.248062 0.564054 0.096 Uiso 1 1 calc R . . . .
F10 F 0.4312(5) 0.2986(2) 0.3699(4) 0.211(2) Uani 1 1 d . . . . .
C9 C 0.2965(3) 0.4637(3) 1.0887(2) 0.0835(11) Uani 1 1 d . . . . .
H9 H 0.285688 0.500665 1.130399 0.100 Uiso 1 1 calc R . . . .
H2 H 0.425(3) 0.4811(19) 0.616(3) 0.065(10) Uiso 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 N6 2.069(2) . Y
Ru1 N1 2.051(2) . Y
Ru1 N3 2.086(2) . Y
Ru1 N2 1.978(2) . Y
Ru1 N4 2.068(2) . Y
Ru1 N5 2.102(2) . Y
P1 F4 1.579(2) . N
P1 F6 1.587(2) . N
P1 F3 1.564(3) . N
P1 F1 1.591(3) . N
P1 F2 1.566(3) . N
P1 F5 1.546(3) . N
P2 F9 1.583(3) . N
P2 F8 1.578(3) . N
P2 F11 1.564(3) . N
P2 F7 1.571(3) . N
P2 F12 1.544(3) . N
P2 F10 1.532(4) . N
N6 C28 1.350(3) . N
N6 C32 1.348(4) . N
N1 C2 1.322(3) . Y
N1 C7 1.436(3) . Y
N3 C17 1.357(4) . N
N3 C13 1.337(4) . N
N2 C1 1.303(3) . Y
N4 C18 1.354(4) . N
N4 C22 1.337(4) . N
N5 C27 1.353(3) . N
N5 C23 1.345(4) . N
C28 C27 1.465(4) . N
C28 C29 1.382(4) . N
C27 C26 1.386(4) . N
C2 C1 1.453(4) . Y
C2 C3 1.433(4) . N
C1 C6 1.436(4) . N
C18 C17 1.461(4) . N
C18 C19 1.385(4) . N
C7 C12 1.393(4) . N
C7 C8 1.371(4) . N
C17 C16 1.393(5) . N
C29 C30 1.375(4) . N
C32 C31 1.377(5) . N
C6 C5 1.341(4) . N
C5 C4 1.435(5) . N
C3 C4 1.342(4) . N
C22 C21 1.371(4) . N
C30 C31 1.366(5) . N
C12 C11 1.381(5) . N
C8 C9 1.390(5) . N
C26 C25 1.376(5) . N
C19 C20 1.371(6) . N
C13 C14 1.391(5) . N
C23 C24 1.370(5) . N
C11 C10 1.391(6) . N
C21 C20 1.364(5) . N
C14 C15 1.353(6) . N
C24 C25 1.366(5) . N
C16 C15 1.366(6) . N
C10 C9 1.356(6) . N

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
N6 Ru1 N3 96.44(9) . . N
N6 Ru1 N5 77.75(8) . . Y
N1 Ru1 N6 92.08(8) . . N
N1 Ru1 N3 166.55(8) . . N
N1 Ru1 N4 94.99(8) . . N
N1 Ru1 N5 99.81(8) . . N
N3 Ru1 N5 92.18(9) . . N
N2 Ru1 N6 98.26(9) . . N
N2 Ru1 N1 77.53(9) . . Y
N2 Ru1 N3 90.92(9) . . N
N2 Ru1 N4 91.41(9) . . N
N2 Ru1 N5 175.20(9) . . N
N4 Ru1 N6 169.07(8) . . N
N4 Ru1 N3 78.22(9) . . Y
N4 Ru1 N5 92.81(9) . . N
F4 P1 F6 89.25(15) . . N
F4 P1 F1 88.65(14) . . N
F6 P1 F1 89.15(19) . . N
F3 P1 F4 89.99(17) . . N
F3 P1 F6 87.86(17) . . N
F3 P1 F1 176.7(2) . . N
F3 P1 F2 90.8(2) . . N
F2 P1 F4 178.1(2) . . N
F2 P1 F6 89.01(18) . . N
F2 P1 F1 90.45(19) . . N
F5 P1 F4 89.7(2) . . N
F5 P1 F6 179.0(2) . . N
F5 P1 F3 92.0(2) . . N
F5 P1 F1 90.9(3) . . N
F5 P1 F2 92.0(2) . . N
F8 P2 F9 89.65(17) . . N
F11 P2 F9 86.74(17) . . N
F11 P2 F8 88.2(3) . . N
F11 P2 F7 89.5(2) . . N
F7 P2 F9 175.5(2) . . N
F7 P2 F8 87.7(2) . . N
F12 P2 F9 92.3(2) . . N
F12 P2 F8 89.4(3) . . N
F12 P2 F11 177.4(3) . . N
F12 P2 F7 91.4(3) . . N
F10 P2 F9 89.2(2) . . N
F10 P2 F8 178.2(3) . . N
F10 P2 F11 93.1(3) . . N
F10 P2 F7 93.5(3) . . N
F10 P2 F12 89.3(3) . . N
C28 N6 Ru1 116.42(17) . . N
C32 N6 Ru1 124.92(19) . . N
C32 N6 C28 118.5(2) . . N
C2 N1 Ru1 115.34(16) . . Y
C2 N1 C7 119.6(2) . . N
C7 N1 Ru1 124.87(16) . . N
C17 N3 Ru1 114.99(19) . . N
C13 N3 Ru1 125.4(2) . . N
C13 N3 C17 119.1(3) . . N
C1 N2 Ru1 118.82(18) . . Y
C18 N4 Ru1 115.94(19) . . N
C22 N4 Ru1 125.09(19) . . N
C22 N4 C18 118.8(2) . . N
C27 N5 Ru1 115.19(17) . . N
C23 N5 Ru1 126.70(19) . . N
C23 N5 C27 118.1(2) . . N
N6 C28 C27 115.2(2) . . N
N6 C28 C29 121.1(2) . . N
C29 C28 C27 123.7(2) . . N
N5 C27 C28 115.2(2) . . N
N5 C27 C26 121.3(3) . . N
C26 C27 C28 123.5(2) . . N
N1 C2 C1 114.1(2) . . Y
N1 C2 C3 128.1(2) . . N
C3 C2 C1 117.8(2) . . N
N2 C1 C2 114.0(2) . . N
N2 C1 C6 125.8(2) . . N
C6 C1 C2 120.3(2) . . N
N4 C18 C17 115.1(2) . . N
N4 C18 C19 120.1(3) . . N
C19 C18 C17 124.8(3) . . N
C12 C7 N1 120.5(3) . . N
C8 C7 N1 119.7(3) . . N
C8 C7 C12 119.8(3) . . N
N3 C17 C18 115.4(2) . . N
N3 C17 C16 120.6(3) . . N
C16 C17 C18 124.0(3) . . N
C30 C29 C28 120.0(3) . . N
N6 C32 C31 122.0(3) . . N
C5 C6 C1 118.9(3) . . N
C6 C5 C4 121.1(3) . . N
C4 C3 C2 119.5(3) . . N
N4 C22 C21 122.9(3) . . N
C31 C30 C29 118.7(3) . . N
C3 C4 C5 122.4(3) . . N
C30 C31 C32 119.6(3) . . N
C11 C12 C7 119.8(3) . . N
C7 C8 C9 119.7(3) . . N
C25 C26 C27 119.4(3) . . N
C20 C19 C18 120.1(3) . . N
N3 C13 C14 121.5(3) . . N
N5 C23 C24 122.7(3) . . N
C12 C11 C10 119.9(4) . . N
C20 C21 C22 118.6(4) . . N
C15 C14 C13 119.6(4) . . N
C25 C24 C23 119.2(3) . . N
C24 C25 C26 119.2(3) . . N
C15 C16 C17 119.5(4) . . N
C14 C15 C16 119.8(3) . . N
C9 C10 C11 119.8(3) . . N
C21 C20 C19 119.4(3) . . N
C10 C9 C8 121.0(4) . . N

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.154
_oxdiff_exptl_absorpt_empirical_full_min 0.883
####################################################################### 
# 
# 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_dianiline
_database_code_depnum_ccdc_archive 'CCDC 2101320'
loop_
_audit_author_name
_audit_author_address
'Nozomi Tomioka'
;University
Japan
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2021-11-04 downloaded from the CCDC.
;
_audit_creation_date             2021-08-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
"dianilinebis(2,2'-bipyridine)ruthenium bis(trifluoromethanesulfonate)"
_chemical_formula_moiety         'C32 H30 N6 Ru, 2(C F3 O3 S)'
_chemical_formula_sum            'C34 H30 F6 N6 O6 Ru S2'
_chemical_formula_weight         897.83
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'
F F 0.0727 0.0534 '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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.25790(10)
_cell_length_b                   17.1076(2)
_cell_length_c                   19.0176(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.9820(10)
_cell_angle_gamma                90
_cell_volume                     3642.76(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17804
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      75.1600
_cell_measurement_theta_min      3.4590
_shelx_estimated_absorpt_T_max   0.619
_shelx_estimated_absorpt_T_min   0.619
_exptl_absorpt_coefficient_mu    5.311
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1816
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   1.00000
_exptl_transmission_factor_min   0.85671
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25740
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.471
_diffrn_reflns_theta_min         3.484
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6731
_reflns_number_total             7325
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.818
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         7325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0418P)²+2.0504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0857
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Others
 Fixed Sof: F1AA(0.5) F3(0.5) F2(0.5) F0AA(0.5)
3.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C19(H19), C12(H12), C23(H23), C26(H26), C7(H7), C2(H2), C8(H8),
 C32(H32), C9(H9), C13(H13), C24(H24), C21(H21), C25(H25), C10(H10), C20(H20),
 C11(H11), C31(H31), C16(H16), C4(H4), C29(H29), C30(H30), C6(H6), C14(H14),
 C15(H15), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
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 0.46078(2) 0.71291(2) 0.39144(2) 0.03337(7) Uani 1 1 d . . . . .
S1 S 0.36720(6) 0.58560(4) 0.63003(3) 0.04868(15) Uani 1 1 d . . . . .
S2 S -0.06373(7) 0.38131(4) 0.85519(4) 0.05539(17) Uani 1 1 d . . . . .
N4 N 0.61948(17) 0.77158(11) 0.38030(10) 0.0363(4) Uani 1 1 d . . . . .
N6 N 0.29898(18) 0.65500(12) 0.38693(10) 0.0407(4) Uani 1 1 d . . . . .
N5 N 0.35546(17) 0.78506(11) 0.32623(10) 0.0362(4) Uani 1 1 d . . . . .
N3 N 0.51228(18) 0.66070(12) 0.30282(10) 0.0404(4) Uani 1 1 d . . . . .
O5 O -0.0737(2) 0.38444(15) 0.92990(11) 0.0670(6) Uani 1 1 d . . . . .
N1 N 0.55869(18) 0.63012(12) 0.46421(11) 0.0423(4) Uani 1 1 d . . . . .
H1A H 0.510932 0.616633 0.496656 0.051 Uiso 1 1 calc R . . . .
H1B H 0.571992 0.587181 0.439807 0.051 Uiso 1 1 calc R . . . .
F6 F 0.16107(18) 0.42155(16) 0.87802(12) 0.0902(7) Uani 1 1 d . . . . .
N2 N 0.40989(18) 0.77306(12) 0.48611(10) 0.0390(4) Uani 1 1 d . . . . .
H2A H 0.395735 0.736820 0.517759 0.047 Uiso 1 1 calc R . . . .
H2B H 0.472461 0.800789 0.504492 0.047 Uiso 1 1 calc R . . . .
O1 O 0.4160(2) 0.61110(19) 0.69682(13) 0.0831(8) Uani 1 1 d . . . . .
O4 O -0.1608(2) 0.41505(17) 0.81155(14) 0.0828(8) Uani 1 1 d . . . . .
F1 F 0.1500(2) 0.5523(2) 0.57799(15) 0.1170(10) Uani 1 1 d . . . . .
F5 F 0.0418(2) 0.51591(13) 0.8733(2) 0.1180(10) Uani 1 1 d . . . . .
C18 C 0.6741(2) 0.75064(15) 0.32259(13) 0.0415(5) Uani 1 1 d . . . . .
C27 C 0.2380(2) 0.76564(15) 0.31593(12) 0.0402(5) Uani 1 1 d . . . . .
C28 C 0.2069(2) 0.69192(16) 0.34885(12) 0.0411(5) Uani 1 1 d . . . . .
F4 F 0.0755(3) 0.4567(2) 0.77891(14) 0.1344(13) Uani 1 1 d . . . . .
C1 C 0.6716(2) 0.65473(14) 0.50093(13) 0.0415(5) Uani 1 1 d . . . . .
C22 C 0.6706(2) 0.82711(15) 0.42264(13) 0.0431(5) Uani 1 1 d . . . . .
H22 H 0.634808 0.840856 0.462782 0.052 Uiso 1 1 calc R . . . .
C3 C 0.3072(2) 0.82492(15) 0.47724(12) 0.0387(5) Uani 1 1 d . . . . .
C17 C 0.6127(2) 0.68909(16) 0.27850(13) 0.0440(5) Uani 1 1 d . . . . .
C19 C 0.7782(3) 0.78668(18) 0.30699(16) 0.0540(7) Uani 1 1 d . . . . .
H19 H 0.813985 0.771762 0.267165 0.065 Uiso 1 1 calc R . . . .
C12 C 0.3217(2) 0.90133(16) 0.45560(14) 0.0473(6) Uani 1 1 d . . . . .
H12 H 0.397102 0.919617 0.448054 0.057 Uiso 1 1 calc R . . . .
O6 O -0.0199(3) 0.30864(15) 0.83172(16) 0.0976(10) Uani 1 1 d . . . . .
C23 C 0.3923(2) 0.84984(14) 0.29549(13) 0.0436(5) Uani 1 1 d . . . . .
H23 H 0.473270 0.861944 0.300934 0.052 Uiso 1 1 calc R . . . .
C26 C 0.1565(2) 0.81318(18) 0.27658(15) 0.0516(6) Uani 1 1 d . . . . .
H26 H 0.076122 0.799543 0.270201 0.062 Uiso 1 1 calc R . . . .
C7 C 0.7772(2) 0.64260(18) 0.47047(16) 0.0535(6) Uani 1 1 d . . . . .
H7 H 0.775957 0.617116 0.427203 0.064 Uiso 1 1 calc R . . . .
C2 C 0.6742(3) 0.69261(17) 0.56490(14) 0.0506(6) Uani 1 1 d . . . . .
H2 H 0.603952 0.700232 0.585735 0.061 Uiso 1 1 calc R . . . .
C8 C 0.1954(2) 0.79783(17) 0.48938(14) 0.0469(6) Uani 1 1 d . . . . .
H8 H 0.185594 0.746649 0.504227 0.056 Uiso 1 1 calc R . . . .
C32 C 0.2789(3) 0.58458(17) 0.41481(15) 0.0537(7) Uani 1 1 d . . . . .
H32 H 0.342044 0.558786 0.440441 0.064 Uiso 1 1 calc R . . . .
C9 C 0.0985(3) 0.8475(2) 0.47925(16) 0.0587(7) Uani 1 1 d . . . . .
H9 H 0.023157 0.829680 0.487456 0.070 Uiso 1 1 calc R . . . .
C13 C 0.4492(3) 0.60607(18) 0.26428(16) 0.0556(7) Uani 1 1 d . . . . .
H13 H 0.380375 0.586324 0.280865 0.067 Uiso 1 1 calc R . . . .
C24 C 0.3151(3) 0.89919(17) 0.25617(15) 0.0536(6) Uani 1 1 d . . . . .
H24 H 0.343334 0.944225 0.236132 0.064 Uiso 1 1 calc R . . . .
C21 C 0.7741(2) 0.86490(18) 0.40945(16) 0.0526(6) Uani 1 1 d . . . . .
H21 H 0.806895 0.903596 0.439886 0.063 Uiso 1 1 calc R . . . .
C25 C 0.1954(3) 0.88089(18) 0.24693(16) 0.0567(7) Uani 1 1 d . . . . .
H25 H 0.141515 0.913751 0.221034 0.068 Uiso 1 1 calc R . . . .
C10 C 0.1127(3) 0.9234(2) 0.45705(17) 0.0624(8) Uani 1 1 d . . . . .
H10 H 0.046849 0.956398 0.450046 0.075 Uiso 1 1 calc R . . . .
C20 C 0.8283(3) 0.8443(2) 0.35029(17) 0.0604(7) Uani 1 1 d . . . . .
H20 H 0.897850 0.869273 0.340005 0.072 Uiso 1 1 calc R . . . .
C11 C 0.2241(3) 0.95027(18) 0.44527(16) 0.0578(7) Uani 1 1 d . . . . .
H11 H 0.233556 1.001449 0.430344 0.069 Uiso 1 1 calc R . . . .
C31 C 0.1681(3) 0.5491(2) 0.40679(16) 0.0635(8) Uani 1 1 d . . . . .
H31 H 0.157052 0.500256 0.426465 0.076 Uiso 1 1 calc R . . . .
C16 C 0.6500(3) 0.6627(2) 0.21554(17) 0.0631(8) Uani 1 1 d . . . . .
H16 H 0.719158 0.682681 0.199561 0.076 Uiso 1 1 calc R . . . .
C4 C 0.7824(3) 0.71947(19) 0.59831(17) 0.0605(7) Uani 1 1 d . . . . .
H4 H 0.784093 0.745902 0.641136 0.073 Uiso 1 1 calc R . . . .
C29 C 0.0936(2) 0.6587(2) 0.34015(15) 0.0562(7) Uani 1 1 d . . . . .
H29 H 0.030829 0.684973 0.314620 0.067 Uiso 1 1 calc R . . . .
C30 C 0.0749(3) 0.5871(2) 0.36942(17) 0.0662(9) Uani 1 1 d . . . . .
H30 H -0.000645 0.564509 0.363933 0.079 Uiso 1 1 calc R . . . .
C6 C 0.8837(3) 0.6687(2) 0.50493(19) 0.0658(8) Uani 1 1 d . . . . .
H6 H 0.954446 0.660039 0.484870 0.079 Uiso 1 1 calc R . . . .
O3 O 0.3716(4) 0.6364(3) 0.5739(2) 0.152(2) Uani 1 1 d . . . . .
C14 C 0.4820(3) 0.5783(2) 0.20169(18) 0.0684(9) Uani 1 1 d . . . . .
H14 H 0.435885 0.540711 0.176279 0.082 Uiso 1 1 calc R . . . .
C34 C 0.0596(3) 0.4472(2) 0.84536(17) 0.0611(7) Uani 1 1 d . . . . .
C15 C 0.5841(3) 0.6067(2) 0.17671(18) 0.0725(9) Uani 1 1 d . . . . .
H15 H 0.608162 0.588465 0.134375 0.087 Uiso 1 1 calc R . . . .
C5 C 0.8867(3) 0.7072(2) 0.5684(2) 0.0672(9) Uani 1 1 d . . . . .
H5 H 0.958983 0.724799 0.591048 0.081 Uiso 1 1 calc R . . . .
F1AA F 0.1615(6) 0.6088(7) 0.6744(6) 0.127(4) Uani 0.5 1 d . . P A 2
C33 C 0.2109(4) 0.5767(4) 0.6356(2) 0.1046(19) Uani 1 1 d . . . . .
O2 O 0.4018(4) 0.5125(3) 0.6117(3) 0.204(3) Uani 1 1 d . . . . .
F3 F 0.1695(8) 0.5593(7) 0.6890(5) 0.121(4) Uani 0.5 1 d . . P A 1
F2 F 0.1748(5) 0.6668(4) 0.6362(4) 0.0987(18) Uani 0.5 1 d . . P A 1
F0AA F 0.2215(6) 0.4916(5) 0.6741(3) 0.119(2) Uani 0.5 1 d . . 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 N4 2.0794(19) . Y
Ru1 N6 2.067(2) . Y
Ru1 N5 2.0398(19) . Y
Ru1 N3 2.044(2) . Y
Ru1 N1 2.195(2) . Y
Ru1 N2 2.2009(19) . Y
S1 O1 1.400(2) . N
S1 O3 1.382(3) . N
S1 C33 1.780(4) . N
S1 O2 1.366(3) . N
S2 O5 1.438(2) . N
S2 O4 1.424(3) . N
S2 O6 1.426(3) . N
S2 C34 1.814(3) . N
N4 C18 1.360(3) . N
N4 C22 1.336(3) . N
N6 C28 1.357(3) . N
N6 C32 1.345(3) . N
N5 C27 1.358(3) . N
N5 C23 1.339(3) . N
N3 C17 1.355(3) . N
N3 C13 1.344(3) . N
N1 C1 1.448(3) . Y
F6 C34 1.318(4) . N
N2 C3 1.453(3) . Y
F1 C33 1.300(4) . N
F5 C34 1.313(4) . N
C18 C17 1.473(4) . N
C18 C19 1.384(4) . N
C27 C28 1.466(4) . N
C27 C26 1.385(4) . N
C28 C29 1.390(4) . N
F4 C34 1.305(4) . N
C1 C7 1.391(4) . N
C1 C2 1.376(4) . Y
C22 C21 1.378(4) . N
C3 C12 1.385(4) . N
C3 C8 1.383(4) . N
C17 C16 1.385(4) . N
C19 C20 1.368(4) . N
C12 C11 1.379(4) . N
C23 C24 1.375(4) . N
C26 C25 1.380(4) . N
C7 C6 1.379(4) . N
C2 C4 1.392(4) . N
C8 C9 1.380(4) . N
C32 C31 1.381(4) . N
C9 C10 1.379(5) . N
C13 C14 1.367(4) . N
C24 C25 1.376(4) . N
C21 C20 1.380(4) . N
C10 C11 1.376(5) . N
C31 C30 1.369(5) . N
C16 C15 1.378(5) . N
C4 C5 1.373(5) . N
C29 C30 1.371(5) . N
C6 C5 1.373(5) . N
C14 C15 1.377(5) . N
F1AA C33 1.113(8) . N
C33 F3 1.197(8) . N
C33 F2 1.594(9) . N
C33 F0AA 1.628(10) . N

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 Ru1 N1 89.73(7) . . N
N4 Ru1 N2 99.05(8) . . N
N6 Ru1 N4 171.81(8) . . N
N6 Ru1 N1 95.70(8) . . N
N6 Ru1 N2 87.40(8) . . N
N5 Ru1 N4 95.57(8) . . N
N5 Ru1 N6 79.10(8) . . Y
N5 Ru1 N3 87.71(8) . . N
N5 Ru1 N1 174.64(8) . . N
N5 Ru1 N2 91.72(8) . . N
N3 Ru1 N4 78.83(8) . . Y
N3 Ru1 N6 94.64(8) . . N
N3 Ru1 N1 94.07(8) . . N
N3 Ru1 N2 177.74(8) . . N
N1 Ru1 N2 86.69(8) . . Y
O1 S1 C33 105.61(17) . . N
O3 S1 O1 117.6(2) . . N
O3 S1 C33 102.4(3) . . N
O2 S1 O1 115.0(3) . . N
O2 S1 O3 110.1(4) . . N
O2 S1 C33 104.3(3) . . N
O5 S2 C34 102.62(15) . . N
O4 S2 O5 115.23(16) . . N
O4 S2 O6 116.13(19) . . N
O4 S2 C34 103.73(15) . . N
O6 S2 O5 114.01(16) . . N
O6 S2 C34 102.50(19) . . N
C18 N4 Ru1 114.85(16) . . N
C22 N4 Ru1 127.06(16) . . N
C22 N4 C18 118.1(2) . . N
C28 N6 Ru1 114.83(16) . . N
C32 N6 Ru1 126.60(19) . . N
C32 N6 C28 118.5(2) . . N
C27 N5 Ru1 115.81(16) . . N
C23 N5 Ru1 125.42(17) . . N
C23 N5 C27 118.7(2) . . N
C17 N3 Ru1 116.31(17) . . N
C13 N3 Ru1 125.05(18) . . N
C13 N3 C17 118.4(2) . . N
C1 N1 Ru1 118.33(15) . . Y
C3 N2 Ru1 117.53(14) . . N
N4 C18 C17 115.0(2) . . N
N4 C18 C19 121.3(2) . . N
C19 C18 C17 123.7(2) . . N
N5 C27 C28 114.9(2) . . N
N5 C27 C26 120.9(2) . . N
C26 C27 C28 124.2(2) . . N
N6 C28 C27 115.2(2) . . N
N6 C28 C29 120.9(3) . . N
C29 C28 C27 123.8(3) . . N
C7 C1 N1 120.1(2) . . N
C2 C1 N1 120.0(2) . . Y
C2 C1 C7 119.9(3) . . N
N4 C22 C21 122.9(2) . . N
C12 C3 N2 119.6(2) . . N
C8 C3 N2 120.2(2) . . N
C8 C3 C12 120.2(2) . . N
N3 C17 C18 114.9(2) . . N
N3 C17 C16 121.1(3) . . N
C16 C17 C18 124.0(3) . . N
C20 C19 C18 119.8(3) . . N
C11 C12 C3 119.9(3) . . N
N5 C23 C24 122.6(2) . . N
C25 C26 C27 119.5(3) . . N
C6 C7 C1 119.5(3) . . N
C1 C2 C4 119.7(3) . . N
C9 C8 C3 119.3(3) . . N
N6 C32 C31 122.4(3) . . N
C10 C9 C8 120.5(3) . . N
N3 C13 C14 122.7(3) . . N
C23 C24 C25 119.0(3) . . N
C22 C21 C20 118.9(3) . . N
C24 C25 C26 119.2(3) . . N
C11 C10 C9 120.0(3) . . N
C19 C20 C21 119.0(3) . . N
C10 C11 C12 120.0(3) . . N
C30 C31 C32 119.0(3) . . N
C15 C16 C17 119.7(3) . . N
C5 C4 C2 120.4(3) . . N
C30 C29 C28 119.6(3) . . N
C31 C30 C29 119.5(3) . . N
C5 C6 C7 120.9(3) . . N
C13 C14 C15 119.2(3) . . N
F6 C34 S2 112.3(2) . . N
F5 C34 S2 111.3(2) . . N
F5 C34 F6 105.6(3) . . N
F4 C34 S2 111.1(3) . . N
F4 C34 F6 107.3(3) . . N
F4 C34 F5 108.9(3) . . N
C14 C15 C16 118.8(3) . . N
C6 C5 C4 119.6(3) . . N
F1 C33 S1 114.5(3) . . N
F1 C33 F2 101.8(5) . . N
F1 C33 F0AA 95.7(5) . . N
F1AA C33 S1 124.2(5) . . N
F1AA C33 F1 117.4(6) . . N
F1AA C33 F0AA 99.3(8) . . N
F3 C33 S1 123.1(6) . . N
F3 C33 F1 114.6(6) . . N
F3 C33 F2 96.4(7) . . N
F2 C33 S1 99.9(3) . . N
F0AA C33 S1 94.4(4) . . N

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_difluoroaniline
_database_code_depnum_ccdc_archive 'CCDC 2101323'
loop_
_audit_author_name
_audit_author_address
'Nozomi Tomioka'
;University
Japan
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2021-11-04 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
"di(2,6-difluoroaniline)bis(2,2'-bipyridine)ruthenium bis(trifluoromethanesulfonate)"
_chemical_formula_moiety         'C32 H26 F4 N6 Ru, 2(C F3 O3 S)'
_chemical_formula_sum            'C34 H26 F10 N6 O6 Ru S2'
_chemical_formula_weight         969.80
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.00630(10)
_cell_length_b                   10.2443(2)
_cell_length_c                   10.4305(2)
_cell_angle_alpha                114.725(2)
_cell_angle_beta                 93.0320(10)
_cell_angle_gamma                100.1520(10)
_cell_volume                     946.35(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9159
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      75.5590
_cell_measurement_theta_min      4.5030
_shelx_estimated_absorpt_T_max   0.618
_shelx_estimated_absorpt_T_min   0.545
_exptl_absorpt_coefficient_mu    5.321
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             486
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   1.00000
_exptl_transmission_factor_min   0.32571
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9898
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.740
_diffrn_reflns_theta_min         4.535
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3688
_reflns_number_total             3755
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.076
_refine_diff_density_min         -1.938
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3755
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1184P)²+0.3246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.1547
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C10(H10), C14(H14), C15(H15), C7(H7), C8(H8), C9(H9),
 C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
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 0.500000 0.500000 0.02917(17) Uani 1 2 d S T P . .
S1 S 0.27026(11) 0.76043(11) 0.27197(11) 0.0447(3) Uani 1 1 d . . . . .
N3 N 0.3977(3) 0.3761(3) 0.5961(3) 0.0337(6) Uani 1 1 d . . . . .
F2 F 0.1274(3) 0.4772(4) 0.5401(4) 0.0735(9) Uani 1 1 d . . . . .
O1 O 0.3171(4) 0.6339(4) 0.1779(4) 0.0652(10) Uani 1 1 d . . . . .
F1 F 0.2906(4) 0.2232(4) 0.1155(4) 0.0840(11) Uani 1 1 d . . . . .
N2 N 0.4332(3) 0.6577(3) 0.6712(3) 0.0345(6) Uani 1 1 d . . . . .
O3 O 0.2722(4) 0.7757(4) 0.4158(4) 0.0588(8) Uani 1 1 d . . . . .
N1 N 0.3196(3) 0.4790(3) 0.3661(3) 0.0371(6) Uani 1 1 d . . . . .
H1A H 0.286386 0.559341 0.409042 0.044 Uiso 1 1 calc R . . . .
H1B H 0.344978 0.478388 0.285358 0.044 Uiso 1 1 calc R . . . .
O2 O 0.3182(4) 0.8931(4) 0.2573(5) 0.0710(10) Uani 1 1 d . . . . .
C12 C 0.3812(4) 0.4570(4) 0.7334(4) 0.0349(7) Uani 1 1 d . . . . .
C11 C 0.3964(4) 0.6156(4) 0.7740(4) 0.0371(7) Uani 1 1 d . . . . .
C16 C 0.3594(4) 0.2283(4) 0.5436(4) 0.0408(8) Uani 1 1 d . . . . .
H16 H 0.362499 0.171239 0.447619 0.049 Uiso 1 1 calc R . . . .
C13 C 0.3401(4) 0.3929(4) 0.8217(5) 0.0443(9) Uani 1 1 d . . . . .
H13 H 0.333148 0.451306 0.916369 0.053 Uiso 1 1 calc R . . . .
F4 F 0.0305(5) 0.5864(6) 0.2108(7) 0.1246(18) Uani 1 1 d . . . . .
F3 F 0.0260(5) 0.8142(7) 0.2957(7) 0.1278(19) Uani 1 1 d . . . . .
C10 C 0.3620(5) 0.7114(5) 0.8998(5) 0.0500(10) Uani 1 1 d . . . . .
H10 H 0.340637 0.680987 0.970080 0.060 Uiso 1 1 calc R . . . .
C14 C 0.3093(5) 0.2415(5) 0.7688(5) 0.0516(10) Uani 1 1 d . . . . .
H14 H 0.284917 0.196817 0.828121 0.062 Uiso 1 1 calc R . . . .
C1 C 0.2111(4) 0.3543(4) 0.3300(4) 0.0395(8) Uani 1 1 d . . . . .
C15 C 0.3152(5) 0.1578(4) 0.6275(5) 0.0498(10) Uani 1 1 d . . . . .
H15 H 0.290134 0.055583 0.588265 0.060 Uiso 1 1 calc R . . . .
C7 C 0.4257(4) 0.7953(4) 0.6926(4) 0.0418(8) Uani 1 1 d . . . . .
H7 H 0.445985 0.824513 0.621277 0.050 Uiso 1 1 calc R . . . .
C8 C 0.3895(5) 0.8940(5) 0.8151(5) 0.0531(10) Uani 1 1 d . . . . .
H8 H 0.385422 0.987901 0.825619 0.064 Uiso 1 1 calc R . . . .
F5 F 0.0639(6) 0.7020(7) 0.0798(6) 0.133(2) Uani 1 1 d . . . . .
C9 C 0.3596(5) 0.8540(5) 0.9207(5) 0.0558(11) Uani 1 1 d . . . . .
H9 H 0.337954 0.920841 1.005587 0.067 Uiso 1 1 calc R . . . .
C2 C 0.1152(5) 0.3535(6) 0.4213(5) 0.0526(10) Uani 1 1 d . . . . .
C6 C 0.1990(5) 0.2258(5) 0.2063(6) 0.0577(12) Uani 1 1 d . . . . .
C3 C 0.0115(6) 0.2327(8) 0.3906(9) 0.0791(18) Uani 1 1 d . . . . .
H3 H -0.052772 0.235348 0.452441 0.095 Uiso 1 1 calc R . . . .
C4 C 0.0048(6) 0.1076(7) 0.2663(10) 0.093(2) Uani 1 1 d . . . . .
H4 H -0.065332 0.025563 0.244076 0.112 Uiso 1 1 calc R . . . .
C17 C 0.0883(7) 0.7122(8) 0.2094(8) 0.0821(17) Uani 1 1 d . . . . .
C5 C 0.0982(6) 0.1016(6) 0.1755(9) 0.093(3) Uani 1 1 d . . . . .
H5 H 0.094570 0.015217 0.093803 0.112 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 N3 2.092(3) 2_666 Y
Ru1 N3 2.092(3) . Y
Ru1 N2 2.083(3) 2_666 Y
Ru1 N2 2.083(3) . Y
Ru1 N1 2.145(3) 2_666 Y
Ru1 N1 2.145(3) . Y
S1 O1 1.436(3) . N
S1 O3 1.441(3) . N
S1 O2 1.433(3) . N
S1 C17 1.809(7) . N
N3 C12 1.358(5) . N
N3 C16 1.349(4) . N
F2 C2 1.331(6) . N
F1 C6 1.348(6) . N
N2 C11 1.358(5) . N
N2 C7 1.348(4) . N
N1 C1 1.420(5) . Y
C12 C11 1.474(5) . N
C12 C13 1.379(5) . N
C11 C10 1.376(5) . N
C16 C15 1.392(6) . N
C13 C14 1.379(6) . N
F4 C17 1.323(8) . N
F3 C17 1.339(9) . N
C10 C9 1.389(6) . N
C14 C15 1.372(7) . N
C1 C2 1.390(6) . N
C1 C6 1.385(6) . N
C7 C8 1.373(6) . N
C8 C9 1.357(7) . N
F5 C17 1.317(9) . N
C2 C3 1.375(7) . N
C6 C5 1.383(8) . N
C3 C4 1.378(11) . N
C4 C5 1.356(11) . N

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
N3 Ru1 N3 180.00(12) 2_666 . N
N3 Ru1 N1 85.47(12) 2_666 . N
N3 Ru1 N1 94.53(12) . . N
N3 Ru1 N1 85.47(12) . 2_666 N
N3 Ru1 N1 94.53(12) 2_666 2_666 N
N2 Ru1 N3 77.16(11) . . Y
N2 Ru1 N3 77.16(11) 2_666 2_666 N
N2 Ru1 N3 102.84(11) . 2_666 N
N2 Ru1 N3 102.84(11) 2_666 . N
N2 Ru1 N2 180.0 2_666 . N
N2 Ru1 N1 88.99(12) 2_666 2_666 N
N2 Ru1 N1 91.01(12) . 2_666 N
N2 Ru1 N1 91.01(12) 2_666 . N
N2 Ru1 N1 88.99(12) . . N
N1 Ru1 N1 180.0 . 2_666 N
O1 S1 O3 113.7(2) . . N
O1 S1 C17 103.0(3) . . N
O3 S1 C17 102.0(3) . . N
O2 S1 O1 115.5(2) . . N
O2 S1 O3 116.1(2) . . N
O2 S1 C17 104.0(3) . . N
C12 N3 Ru1 114.2(2) . . N
C16 N3 Ru1 128.1(3) . . N
C16 N3 C12 117.4(3) . . N
C11 N2 Ru1 114.9(2) . . N
C7 N2 Ru1 127.9(3) . . N
C7 N2 C11 117.3(3) . . N
C1 N1 Ru1 117.7(2) . . Y
N3 C12 C11 114.4(3) . . N
N3 C12 C13 122.2(3) . . N
C13 C12 C11 123.2(3) . . N
N2 C11 C12 114.7(3) . . N
N2 C11 C10 122.0(3) . . N
C10 C11 C12 122.9(3) . . N
N3 C16 C15 122.6(4) . . N
C14 C13 C12 119.5(4) . . N
C11 C10 C9 119.3(4) . . N
C15 C14 C13 119.0(4) . . N
C2 C1 N1 121.1(4) . . N
C6 C1 N1 122.2(4) . . N
C6 C1 C2 116.7(4) . . N
C14 C15 C16 119.0(4) . . N
N2 C7 C8 122.8(4) . . N
C9 C8 C7 119.7(4) . . N
C8 C9 C10 118.8(4) . . N
F2 C2 C1 116.4(4) . . N
F2 C2 C3 121.4(5) . . N
C3 C2 C1 122.2(5) . . N
F1 C6 C1 118.1(4) . . N
F1 C6 C5 119.9(5) . . N
C5 C6 C1 122.1(6) . . N
C2 C3 C4 118.5(6) . . N
C5 C4 C3 121.5(5) . . N
F4 C17 S1 110.7(5) . . N
F4 C17 F3 106.4(7) . . N
F3 C17 S1 110.5(5) . . N
F5 C17 S1 111.6(6) . . N
F5 C17 F4 109.4(7) . . N
F5 C17 F3 108.0(6) . . N
C4 C5 C6 119.0(6) . . N

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_methyldiimine
_database_code_depnum_ccdc_archive 'CCDC 2101328'
loop_
_audit_author_name
_audit_author_address
'Nozomi Tomioka'
;University
Japan
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2021-11-04 downloaded from the CCDC.
;
_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
"methylphenylcyclohexa-3,5-diene-1,2-diiminebis(2,2'-bipyridine)ruthenium bis(hexafulolophosphate)"
_chemical_formula_moiety         'C34 H30 N6 Ru, 2(F6 P)'
_chemical_formula_sum            'C34 H30 F12 N6 P2 Ru'
_chemical_formula_weight         913.65
_chemical_oxdiff_formula         C34H30F12N6P2Ru
_chemical_oxdiff_usercomment     '298 K'
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'
F F 0.0727 0.0534 '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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.27250(10)
_cell_length_b                   13.51310(10)
_cell_length_c                   13.79670(10)
_cell_angle_alpha                104.5820(10)
_cell_angle_beta                 103.0590(10)
_cell_angle_gamma                116.3090(10)
_cell_volume                     1977.56(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16683
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      75.2040
_cell_measurement_theta_min      3.5670
_shelx_estimated_absorpt_T_max   0.646
_shelx_estimated_absorpt_T_min   0.646
_exptl_absorpt_coefficient_mu    4.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   1.00000
_exptl_transmission_factor_min   0.53776
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23385
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.382
_diffrn_reflns_theta_min         3.593
_diffrn_ambient_temperature      298.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00  30.00   0.50    0.15    --  -44.30  87.00  17.00  212
  2  ω    -19.00  55.00   0.50    0.15    --   44.30 -87.00 -99.00  148
  3  ω    -71.00 -46.00   0.50    0.60    --  -90.25  87.00  17.00   50
  4  ω   -140.00-106.00   0.50    0.60    --  -90.25 -87.00 -99.00   68
  5  ω     60.00  86.00   0.50    0.60    --  109.26 -87.00 -99.00   52
  6  ω    125.00 173.00   0.50    0.60    --  109.26  87.00  17.00   96
  7  ω    -11.00  33.00   0.50    0.15    --  -44.30  37.00 -60.00   88
  8  ω     -1.00  24.00   0.50    0.15    --  -44.30  19.00 -90.00   50
  9  ω    -34.00  29.00   0.50    0.15    --  -44.30  37.00  90.00  126
 10  ω    -35.00  27.00   0.50    0.15    --  -44.30  37.00-180.00  124
 11  ω     63.00 113.00   0.50    0.15    --   44.30  57.00   0.00  100
 12  ω     44.00  97.00   0.50    0.15    --   44.30-125.00-120.00  106
 13  ω     25.00  58.00   0.50    0.15    --   44.30  57.00   0.00   66
 14  ω    -43.00 -17.00   0.50    0.60    --  -90.25  45.00-120.00   52
 15  ω    -43.00 -14.00   0.50    0.60    --  -90.25  45.00-180.00   58
 16  ω    -42.00 -15.00   0.50    0.60    --  -90.25  45.00  30.00   54
 17  ω    -42.00 -16.00   0.50    0.60    --  -90.25  45.00-150.00   52
 18  ω    -43.00 -15.00   0.50    0.60    --  -90.25  45.00 -60.00   56
 19  ω    -42.00 -15.00   0.50    0.60    --  -90.25  45.00   0.00   54
 20  ω     38.00  67.00   0.50    0.60    --  109.26 -94.00-150.00   58
 21  ω     50.00 100.00   0.50    0.60    --  109.26 -94.00 -60.00  100
 22  ω     34.00  61.00   0.50    0.60    --  109.26 -45.00 -60.00   54
 23  ω     74.00  99.00   0.50    0.60    --  109.26-125.00-120.00   50
 24  ω     47.00 103.00   0.50    0.60    --  109.26 -94.00 150.00  112
 25  ω     36.00  62.00   0.50    0.60    --  109.26-125.00-120.00   52
 26  ω     34.00  59.00   0.50    0.60    --  109.26 -45.00  30.00   50
 27  ω    101.00 178.00   0.50    0.60    --  109.26  30.00 150.00  154
 28  ω     60.00  85.00   0.50    0.60    --  109.26 -94.00   0.00   50
 29  ω     42.00  68.00   0.50    0.60    --  109.26 -61.00-180.00   52
 30  ω     34.00  59.00   0.50    0.60    --  109.26 -45.00 -90.00   50
 31  ω     36.00 106.00   0.50    0.60    --  109.26 -77.00   0.00  140
 32  ω     87.00 176.00   0.50    0.60    --  109.26  30.00  90.00  178
 33  ω    142.00 167.00   0.50    0.60    --  109.26  30.00 120.00   50
 34  ω     38.00  76.00   0.50    0.60    --  109.26 -77.00  90.00   76
 35  ω     38.00 102.00   0.50    0.60    --  109.26 -94.00 -30.00  128
 36  ω     74.00 100.00   0.50    0.60    --  109.26 -94.00-150.00   52
 37  ω     37.00  63.00   0.50    0.60    --  109.26 -61.00-120.00   52
 38  ω     86.00 134.00   0.50    0.60    --  109.26  30.00 120.00   96
 39  ω    145.00 173.00   0.50    0.60    --  109.26  61.00  30.00   56
 40  ω     95.00 126.00   0.50    0.60    --  109.26  61.00  30.00   62
 41  ω     35.00  60.00   0.50    0.60    --  109.26 -45.00-180.00   50
 42  ω     68.00 103.00   0.50    0.60    --  109.26 -94.00-120.00   70
 43  ω     74.00 103.00   0.50    0.60    --  109.26 -94.00  60.00   58
 44  ω     42.00  67.00   0.50    0.60    --  109.26 -61.00 120.00   50
 45  ω     42.00  98.00   0.50    0.60    --  109.26 -94.00 120.00  112
 46  ω     73.00 102.00   0.50    0.60    --  109.26 -94.00  30.00   58
 47  ω    113.00 176.00   0.50    0.60    --  109.26  30.00-180.00  126
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0067705000
_diffrn_orient_matrix_UB_12      -0.0935504000
_diffrn_orient_matrix_UB_13      -0.0845864000
_diffrn_orient_matrix_UB_21      0.1335107000
_diffrn_orient_matrix_UB_22      0.0538923000
_diffrn_orient_matrix_UB_23      0.0737030000
_diffrn_orient_matrix_UB_31      -0.0434267000
_diffrn_orient_matrix_UB_32      -0.0874895000
_diffrn_orient_matrix_UB_33      0.0556768000
_diffrn_oxdiff_digest_frames     
;
01c3c23d364c9d1eb8ad7dae6e5cdffc81000409d84
;
_diffrn_oxdiff_digest_hkl        
;
01b8d6831a03230ec15e0b855477e0987ce2aa
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7425
_reflns_number_total             7921
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.176
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     502
_refine_ls_number_reflns         7921
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0927P)²+1.6642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1445
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C34(H34), C16(H16), C15(H15), C9(H9), C18(H18), C24(H24), C23(H23), C3(H3),
 C21(H21), C17(H17), C22(H22), C13(H13), C31(H31), C25(H25), C33(H33), C12(H12),
  C32(H32), C6(H6), C10(H10), C26(H26), C5(H5), C28(H28), C27(H27)
2.b Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C14(H14a,H14b,H14c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru01 Ru 0.37779(2) 0.66656(2) 0.70341(2) 0.03937(11) Uani 1 1 d . . . . .
P2 P 0.50934(18) 0.34395(15) 0.71714(12) 0.0872(4) Uani 1 1 d . . . . .
P1 P 0.91495(13) 1.05577(14) 0.81440(14) 0.0933(5) Uani 1 1 d . . . . .
N2 N 0.2451(3) 0.6128(2) 0.5572(2) 0.0415(6) Uani 1 1 d . . . . .
N6 N 0.4760(3) 0.8153(3) 0.6717(2) 0.0458(6) Uani 1 1 d . . . . .
N3 N 0.5194(3) 0.7056(3) 0.8372(2) 0.0435(6) Uani 1 1 d . . . . .
N4 N 0.2878(3) 0.5467(3) 0.7645(3) 0.0473(6) Uani 1 1 d . . . . .
N1 N 0.3880(3) 0.5401(3) 0.6032(3) 0.0499(7) Uani 1 1 d . . . . .
N5 N 0.3574(3) 0.7976(3) 0.8014(3) 0.0491(7) Uani 1 1 d . . . . .
C8 C 0.1867(3) 0.6780(3) 0.5419(3) 0.0446(7) Uani 1 1 d . . . . .
C2 C 0.2344(3) 0.5303(3) 0.4724(3) 0.0466(7) Uani 1 1 d . . . . .
F2 F 0.8832(5) 1.1274(5) 0.7534(4) 0.1384(18) Uani 1 1 d . . . . .
C20 C 0.3544(4) 0.5624(3) 0.8641(3) 0.0504(8) Uani 1 1 d . . . . .
C34 C 0.5300(4) 0.8159(4) 0.6005(3) 0.0573(9) Uani 1 1 d . . . . .
H34 H 0.530020 0.747410 0.565571 0.069 Uiso 1 1 calc R . . . .
C19 C 0.4867(3) 0.6501(3) 0.9033(3) 0.0486(8) Uani 1 1 d . . . . .
C30 C 0.4755(4) 0.9155(3) 0.7209(3) 0.0544(8) Uani 1 1 d . . . . .
C16 C 0.7285(4) 0.8020(4) 0.9524(4) 0.0596(10) Uani 1 1 d . . . . .
H16 H 0.810589 0.852256 0.966965 0.072 Uiso 1 1 calc R . . . .
F5 F 1.0086(4) 1.1732(4) 0.9169(3) 0.1303(16) Uani 1 1 d . . . . .
C15 C 0.6391(3) 0.7797(3) 0.8609(3) 0.0514(8) Uani 1 1 d . . . . .
H15 H 0.661887 0.816556 0.814455 0.062 Uiso 1 1 calc R . . . .
C9 C 0.1107(4) 0.6802(4) 0.5945(3) 0.0571(9) Uani 1 1 d . . . . .
H9 H 0.092799 0.634679 0.635657 0.068 Uiso 1 1 calc R . . . .
C1 C 0.3107(4) 0.4827(3) 0.5016(3) 0.0501(8) Uani 1 1 d . . . . .
C29 C 0.4115(4) 0.9058(4) 0.7941(4) 0.0618(10) Uani 1 1 d . . . . .
C18 C 0.5734(4) 0.6724(4) 0.9969(4) 0.0629(10) Uani 1 1 d . . . . .
H18 H 0.549669 0.635630 1.043136 0.076 Uiso 1 1 calc R . . . .
C24 C 0.1681(4) 0.4608(4) 0.7187(4) 0.0589(9) Uani 1 1 d . . . . .
H24 H 0.122698 0.446034 0.648880 0.071 Uiso 1 1 calc R . . . .
C23 C 0.1103(5) 0.3938(5) 0.7711(5) 0.0766(14) Uani 1 1 d . . . . .
H23 H 0.027232 0.335879 0.737691 0.092 Uiso 1 1 calc R . . . .
C3 C 0.1568(4) 0.4833(4) 0.3614(3) 0.0601(9) Uani 1 1 d . . . . .
H3 H 0.110956 0.515833 0.340700 0.072 Uiso 1 1 calc R . . . .
C21 C 0.3012(4) 0.4987(4) 0.9208(4) 0.0655(11) Uani 1 1 d . . . . .
H21 H 0.347892 0.512650 0.989769 0.079 Uiso 1 1 calc R . . . .
C17 C 0.6943(4) 0.7489(4) 1.0212(4) 0.0674(11) Uani 1 1 d . . . . .
H17 H 0.753194 0.764795 1.084317 0.081 Uiso 1 1 calc R . . . .
C22 C 0.1772(5) 0.4138(5) 0.8736(5) 0.0781(14) Uani 1 1 d . . . . .
H22 H 0.139457 0.370644 0.910869 0.094 Uiso 1 1 calc R . . . .
C13 C 0.2141(4) 0.7474(4) 0.4817(4) 0.0565(9) Uani 1 1 d . . . . .
H13 H 0.265555 0.746579 0.446004 0.068 Uiso 1 1 calc R . . . .
C31 C 0.5292(5) 1.0168(4) 0.6985(4) 0.0718(12) Uani 1 1 d . . . . .
H31 H 0.527123 1.084470 0.731872 0.086 Uiso 1 1 calc R . . . .
C4 C 0.1495(5) 0.3911(5) 0.2855(4) 0.0741(13) Uani 1 1 d . . . . .
C25 C 0.2981(5) 0.7832(5) 0.8678(4) 0.0666(11) Uani 1 1 d . . . . .
H25 H 0.261231 0.708884 0.872540 0.080 Uiso 1 1 calc R . . . .
C33 C 0.5857(5) 0.9164(5) 0.5779(5) 0.0761(14) Uani 1 1 d . . . . .
H33 H 0.623499 0.915020 0.528902 0.091 Uiso 1 1 calc R . . . .
C12 C 0.1648(5) 0.8177(4) 0.4752(4) 0.0693(12) Uani 1 1 d . . . . .
H12 H 0.184041 0.864543 0.435324 0.083 Uiso 1 1 calc R . . . .
C32 C 0.5856(5) 1.0159(5) 0.6262(5) 0.0772(14) Uani 1 1 d . . . . .
H32 H 0.623241 1.083382 0.611003 0.093 Uiso 1 1 calc R . . . .
C6 C 0.2967(5) 0.3823(4) 0.4204(4) 0.0711(12) Uani 1 1 d . . . . .
H6 H 0.340758 0.347402 0.438527 0.085 Uiso 1 1 calc R . . . .
F6 F 0.8243(6) 0.9344(5) 0.7100(6) 0.200(3) Uani 1 1 d . . . . .
C10 C 0.0609(5) 0.7500(5) 0.5864(5) 0.0728(12) Uani 1 1 d . . . . .
H10 H 0.008729 0.750135 0.621430 0.087 Uiso 1 1 calc R . . . .
C26 C 0.2894(7) 0.8745(6) 0.9300(6) 0.101(2) Uani 1 1 d . . . . .
H26 H 0.247980 0.862242 0.976124 0.121 Uiso 1 1 calc R . . . .
F3 F 0.8060(5) 1.0341(5) 0.8522(5) 0.158(2) Uani 1 1 d . . . . .
C11 C 0.0876(5) 0.8199(5) 0.5266(5) 0.0737(13) Uani 1 1 d . . . . .
C5 C 0.2198(5) 0.3396(5) 0.3185(4) 0.0797(14) Uani 1 1 d . . . . .
H5 H 0.210806 0.273983 0.266315 0.096 Uiso 1 1 calc R . . . .
C28 C 0.4027(9) 0.9989(6) 0.8534(7) 0.116(3) Uani 1 1 d . . . . .
H28 H 0.437414 1.072114 0.846364 0.140 Uiso 1 1 calc R . . . .
F4 F 0.9455(7) 0.9806(6) 0.8720(7) 0.204(3) Uani 1 1 d . . . . .
C7 C 0.0682(8) 0.3367(8) 0.1673(5) 0.123(3) Uani 1 1 d . . . . .
H7A H 0.005682 0.355273 0.159796 0.184 Uiso 1 1 calc GR . . . .
H7B H 0.031332 0.250798 0.138796 0.184 Uiso 1 1 calc GR . . . .
H7C H 0.115844 0.369407 0.127719 0.184 Uiso 1 1 calc GR . . . .
F1 F 1.0246(5) 1.0804(7) 0.7754(5) 0.190(3) Uani 1 1 d . . . . .
C27 C 0.3430(10) 0.9829(7) 0.9220(8) 0.135(3) Uani 1 1 d . . . . .
H27 H 0.338820 1.045980 0.963346 0.162 Uiso 1 1 calc R . . . .
C14 C 0.0347(9) 0.8981(8) 0.5188(8) 0.123(3) Uani 1 1 d . . . . .
H14A H 0.083009 0.959537 0.497638 0.184 Uiso 1 1 calc GR . . . .
H14B H 0.035095 0.935084 0.588253 0.184 Uiso 1 1 calc GR . . . .
H14C H -0.047621 0.849053 0.465640 0.184 Uiso 1 1 calc GR . . . .
F7 F 0.5048(7) 0.3971(7) 0.6364(5) 0.169(3) Uani 1 1 d . . . . .
F8 F 0.5757(6) 0.2856(6) 0.6747(5) 0.161(2) Uani 1 1 d . . . . .
F9 F 0.504(2) 0.2737(16) 0.7987(13) 0.437(13) Uani 1 1 d . . . . .
F11 F 0.5971(18) 0.4408(9) 0.8068(7) 0.364(10) Uani 1 1 d . . . . .
H1 H 0.437(5) 0.515(5) 0.631(5) 0.080(16) Uiso 1 1 d . . . . .
F10 F 0.393(2) 0.3568(19) 0.7534(13) 0.459(13) Uani 1 1 d . . . . .
F12 F 0.3502(15) 0.2096(12) 0.6279(13) 0.334(7) 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
Ru01 N2 2.055(3) . Y
Ru01 N6 2.075(3) . Y
Ru01 N3 2.069(3) . Y
Ru01 N4 2.046(3) . Y
Ru01 N1 1.987(3) . Y
Ru01 N5 2.103(3) . Y
P2 F7 1.474(5) . N
P2 F8 1.536(6) . N
P2 F9 1.640(9) . N
P2 F11 1.335(11) . N
P2 F10 1.786(15) . N
P2 F12 1.891(17) . N
P1 F2 1.560(5) . N
P1 F5 1.546(4) . N
P1 F6 1.578(5) . N
P1 F3 1.578(6) . N
P1 F4 1.566(5) . N
P1 F1 1.591(7) . N
N2 C8 1.431(4) . N
N2 C2 1.327(5) . Y
N6 C34 1.340(5) . N
N6 C30 1.358(5) . N
N3 C19 1.348(5) . N
N3 C15 1.350(5) . N
N4 C20 1.361(5) . N
N4 C24 1.346(5) . N
N1 C1 1.310(5) . Y
N5 C29 1.357(5) . N
N5 C25 1.332(5) . N
C8 C9 1.376(5) . N
C8 C13 1.387(5) . N
C2 C1 1.458(5) . Y
C2 C3 1.424(5) . N
C20 C19 1.478(5) . N
C20 C21 1.379(6) . N
C34 C33 1.384(7) . N
C19 C18 1.381(5) . N
C30 C29 1.453(6) . N
C30 C31 1.388(6) . N
C16 C15 1.381(6) . N
C16 C17 1.368(7) . N
C9 C10 1.383(6) . N
C1 C6 1.431(6) . N
C29 C28 1.386(7) . N
C18 C17 1.367(7) . N
C24 C23 1.377(6) . N
C23 C22 1.373(8) . N
C3 C4 1.360(7) . N
C21 C22 1.383(7) . N
C13 C12 1.382(6) . N
C31 C32 1.377(8) . N
C4 C5 1.452(8) . N
C4 C7 1.504(8) . N
C25 C26 1.382(7) . N
C33 C32 1.342(8) . N
C12 C11 1.377(8) . N
C6 C5 1.331(8) . N
C10 C11 1.387(7) . N
C26 C27 1.363(10) . N
C11 C14 1.516(7) . N
C28 C27 1.365(11) . N

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 Ru01 N6 83.60(11) . . N
N2 Ru01 N3 171.42(11) . . N
N2 Ru01 N5 99.05(12) . . N
N6 Ru01 N5 77.87(13) . . Y
N3 Ru01 N6 96.79(12) . . N
N3 Ru01 N5 89.39(12) . . N
N4 Ru01 N2 103.01(12) . . N
N4 Ru01 N6 167.83(12) . . N
N4 Ru01 N3 78.22(12) . . Y
N4 Ru01 N5 90.89(13) . . N
N1 Ru01 N2 77.42(13) . . Y
N1 Ru01 N6 101.96(13) . . N
N1 Ru01 N3 94.15(13) . . N
N1 Ru01 N4 89.55(13) . . N
N1 Ru01 N5 176.44(12) . . N
F7 P2 F8 94.3(3) . . N
F7 P2 F9 174.9(9) . . N
F7 P2 F10 95.8(4) . . N
F7 P2 F12 90.4(6) . . N
F8 P2 F9 85.1(5) . . N
F8 P2 F10 159.6(8) . . N
F8 P2 F12 95.6(5) . . N
F9 P2 F10 83.2(7) . . N
F9 P2 F12 84.7(10) . . N
F11 P2 F7 101.5(6) . . N
F11 P2 F8 103.8(9) . . N
F11 P2 F9 83.5(9) . . N
F11 P2 F10 91.5(9) . . N
F11 P2 F12 156.3(9) . . N
F10 P2 F12 66.7(9) . . N
F2 P1 F6 90.5(3) . . N
F2 P1 F3 89.1(3) . . N
F2 P1 F4 178.1(4) . . N
F2 P1 F1 89.4(4) . . N
F5 P1 F2 91.3(3) . . N
F5 P1 F6 177.2(4) . . N
F5 P1 F3 93.1(3) . . N
F5 P1 F4 90.4(4) . . N
F5 P1 F1 86.5(3) . . N
F6 P1 F3 89.1(4) . . N
F6 P1 F1 91.4(4) . . N
F3 P1 F1 178.5(4) . . N
F4 P1 F6 87.8(4) . . N
F4 P1 F3 91.6(4) . . N
F4 P1 F1 89.9(5) . . N
C8 N2 Ru01 122.1(2) . . N
C2 N2 Ru01 115.9(2) . . N
C2 N2 C8 120.5(3) . . N
C34 N6 Ru01 125.0(3) . . N
C34 N6 C30 118.5(3) . . N
C30 N6 Ru01 116.2(3) . . N
C19 N3 Ru01 115.9(2) . . N
C19 N3 C15 119.1(3) . . N
C15 N3 Ru01 125.0(2) . . N
C20 N4 Ru01 116.0(2) . . N
C24 N4 Ru01 125.8(3) . . N
C24 N4 C20 118.0(3) . . N
C1 N1 Ru01 118.5(3) . . Y
C29 N5 Ru01 114.7(3) . . N
C25 N5 Ru01 126.3(3) . . N
C25 N5 C29 119.1(4) . . N
C9 C8 N2 119.8(3) . . N
C9 C8 C13 119.6(3) . . N
C13 C8 N2 120.4(3) . . N
N2 C2 C1 113.3(3) . . Y
N2 C2 C3 127.8(4) . . N
C3 C2 C1 118.8(3) . . N
N4 C20 C19 114.3(3) . . N
N4 C20 C21 121.8(4) . . N
C21 C20 C19 123.9(4) . . N
N6 C34 C33 121.4(4) . . N
N3 C19 C20 114.5(3) . . N
N3 C19 C18 120.9(4) . . N
C18 C19 C20 124.6(4) . . N
N6 C30 C29 115.0(3) . . N
N6 C30 C31 121.3(4) . . N
C31 C30 C29 123.8(4) . . N
C17 C16 C15 118.9(4) . . N
N3 C15 C16 121.6(4) . . N
C8 C9 C10 120.1(4) . . N
N1 C1 C2 114.2(3) . . Y
N1 C1 C6 126.6(4) . . N
C6 C1 C2 119.2(4) . . N
N5 C29 C30 116.2(3) . . N
N5 C29 C28 120.1(5) . . N
C28 C29 C30 123.7(5) . . N
C17 C18 C19 119.6(4) . . N
N4 C24 C23 122.5(4) . . N
C22 C23 C24 119.0(4) . . N
C4 C3 C2 120.1(4) . . N
C20 C21 C22 119.0(4) . . N
C18 C17 C16 119.8(4) . . N
C23 C22 C21 119.5(4) . . N
C12 C13 C8 119.7(4) . . N
C32 C31 C30 119.2(5) . . N
C3 C4 C5 119.6(4) . . N
C3 C4 C7 122.7(6) . . N
C5 C4 C7 117.7(5) . . N
N5 C25 C26 122.6(5) . . N
C32 C33 C34 120.5(5) . . N
C11 C12 C13 121.4(4) . . N
C33 C32 C31 119.2(4) . . N
C5 C6 C1 119.1(5) . . N
C9 C10 C11 120.9(4) . . N
C27 C26 C25 118.3(6) . . N
C12 C11 C10 118.3(4) . . N
C12 C11 C14 120.6(5) . . N
C10 C11 C14 121.1(6) . . N
C6 C5 C4 122.8(4) . . N
C27 C28 C29 119.9(6) . . N
C26 C27 C28 119.9(5) . . N

loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.171 -0.005 0.233 24.5 1.0 ?
2 0.000 0.500 0.000 165.5 35.3 ?
3 0.171 0.005 0.767 24.5 1.0 ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.914
_oxdiff_exptl_absorpt_empirical_full_min 0.715
####################################################################### 
# 
# 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_4-methylaniline
_database_code_depnum_ccdc_archive 'CCDC 2101321'
loop_
_audit_author_name
_audit_author_address
'Nozomi Tomioka'
;University
Japan
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2021-11-04 downloaded from the CCDC.
;
_audit_creation_date             2021-03-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
"di(4-methylaniline)bis(2,2'-bipyridine)ruthenium bis(trifluoromethanesulfonate)"
_chemical_formula_moiety         'C34 H34 N6 Ru, 2(C F3 O3 S)'
_chemical_formula_sum            'C36 H34 F6 N6 O6 Ru S2'
_chemical_formula_weight         925.88
_chemical_oxdiff_formula         C36H34F6N6O6S2Ru
_chemical_oxdiff_usercomment     '298 K'
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'
F F 0.0727 0.0534 '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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.23880(10)
_cell_length_b                   22.2125(3)
_cell_length_c                   15.9788(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.1880(10)
_cell_angle_gamma                90
_cell_volume                     3988.12(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21405
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      75.2570
_cell_measurement_theta_min      3.3420
_shelx_estimated_absorpt_T_max   1.00000
_shelx_estimated_absorpt_T_min   0.80411
_exptl_absorpt_coefficient_mu    4.869
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1880
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   1.00000
_exptl_transmission_factor_min   0.80411
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29966
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.482
_diffrn_reflns_theta_min         3.408
_diffrn_ambient_temperature      298.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  33.00   0.50    0.50    --  -44.30  19.00   0.00  112
  2  ω     -8.00  36.00   0.50    0.50    --  -44.30  19.00-120.00   88
  3  ω    -20.00  33.00   0.50    0.50    --  -44.30  19.00-150.00  106
  4  ω    -43.00 -14.00   0.50    2.00    --  -90.25  45.00  60.00   58
  5  ω    -42.00 -15.00   0.50    2.00    --  -90.25  45.00  90.00   54
  6  ω    -22.00  34.00   0.50    0.50    --  -44.30  19.00 150.00  112
  7  ω     50.00  90.00   0.50    0.50    --   44.30-133.00 158.00   80
  8  ω     53.00  78.00   0.50    2.00    --  109.26-133.00 158.00   50
  9  ω     79.00 104.00   0.50    2.00    --  109.26 -95.00 114.01   50
 10  ω     49.00  74.00   0.50    0.50    --   44.30-135.00 -20.00   50
 11  ω     42.00 116.00   0.50    2.00    --  109.26-135.00 -20.00  148
 12  ω     47.00  72.00   0.50    2.00    --  109.26 -94.00 -60.00   50
 13  ω     43.00 105.00   0.50    2.00    --  109.26 -77.00 -30.00  124
 14  ω     72.00 104.00   0.50    2.00    --  109.26 -99.00-138.77   64
 15  ω     36.00  66.00   0.50    2.00    --  109.26 -61.00 -30.00   60
 16  ω     36.00  88.00   0.50    2.00    --  109.26 -94.00 -30.00  104
 17  ω     33.00 105.00   0.50    2.00    --  109.26-105.00  95.80  144
 18  ω     41.00 108.00   0.50    2.00    --  109.26-125.00  90.00  134
 19  ω     88.00 170.00   0.50    2.00    --  109.26  30.00 120.00  164
 20  ω    110.00 135.00   0.50    2.00    --  109.26 135.00  45.00   50
 21  ω     89.00 178.00   0.50    2.00    --  109.26  61.00 -30.00  178
 22  ω    118.00 144.00   0.50    2.00    --  109.26 133.00-133.00   52
 23  ω     91.00 177.00   0.50    2.00    --  109.26  61.00  30.00  172
 24  ω    -78.00 -53.00   0.50    2.00    --  -90.25 133.00-133.00   50
 25  ω    -87.00 -60.00   0.50    0.50    --  -44.30 133.00-133.00   54
 26  ω   -117.00 -73.00   0.50    0.50    --  -44.30-135.00 -20.00   88
 27  ω   -103.00 -72.00   0.50    2.00    --  -90.25-135.00 -20.00   62
 28  ω   -116.00 -77.00   0.50    0.50    --  -44.30-133.00 158.00   78
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0091775000
_diffrn_orient_matrix_UB_12      -0.0675723000
_diffrn_orient_matrix_UB_13      0.0208876000
_diffrn_orient_matrix_UB_21      -0.0452094000
_diffrn_orient_matrix_UB_22      -0.0155941000
_diffrn_orient_matrix_UB_23      -0.0890797000
_diffrn_orient_matrix_UB_31      0.1290472000
_diffrn_orient_matrix_UB_32      -0.0006520000
_diffrn_orient_matrix_UB_33      -0.0306116000
_diffrn_oxdiff_digest_frames     
;
017b5f5a67fb37692e3af5569d495bdbfb000295a4e
;
_diffrn_oxdiff_digest_hkl        
;
0143ecd6f679cba7ccda5bde9bb66575f50352
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6872
_reflns_number_total             8005
_reflns_odcompleteness_completeness 99.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         3.087
_refine_diff_density_min         -1.263
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         8005
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1058P)²+4.8005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1846
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), N1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C15(H15), C24(H24), C9(H9), C18(H18), C27(H27), C26(H26), C6(H6),
 C28(H28), C10(H10), C34(H34), C31(H31), C23(H23), C33(H33), C32(H32), C2(H2),
 C22(H22), C16(H16), C13(H13), C5(H5), C21(H21), C12(H12), C17(H17), C3(H3)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
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 0.28404(3) 0.37279(2) 0.35383(2) 0.03934(14) Uani 1 1 d . . . . .
S2 S 0.62753(10) 0.39396(5) 0.57263(7) 0.0474(3) Uani 1 1 d . . . . .
C35 C 0.2109(8) 0.3487(5) 0.8026(7) 0.108(3) Uani 1 1 d . . . . .
O4 O 0.5810(4) 0.45376(17) 0.5803(3) 0.0717(10) Uani 1 1 d . . . . .
N3 N 0.2178(3) 0.43752(16) 0.2755(2) 0.0437(8) Uani 1 1 d . . . . .
N4 N 0.3133(3) 0.33468(17) 0.2375(2) 0.0468(8) Uani 1 1 d . . . . .
N5 N 0.1139(3) 0.33844(17) 0.3596(2) 0.0451(8) Uani 1 1 d . . . . .
N6 N 0.2246(3) 0.41114(17) 0.4639(2) 0.0439(8) Uani 1 1 d . . . . .
O6 O 0.7522(3) 0.3875(2) 0.5878(3) 0.0706(10) Uani 1 1 d . . . . .
N2 N 0.3618(3) 0.30063(17) 0.4309(2) 0.0489(8) Uani 1 1 d . . . . .
H2A H 0.421242 0.284039 0.403054 0.059 Uiso 1 1 calc R . . . .
H2B H 0.392829 0.316896 0.477360 0.059 Uiso 1 1 calc R . . . .
N1 N 0.4542(3) 0.41936(17) 0.3598(2) 0.0451(8) Uani 1 1 d . . . . .
H1A H 0.438676 0.456978 0.375391 0.054 Uiso 1 1 calc R . . . .
H1B H 0.495714 0.402664 0.401776 0.054 Uiso 1 1 calc R . . . .
O5 O 0.5825(4) 0.3624(2) 0.5009(3) 0.0784(12) Uani 1 1 d . . . . .
C30 C 0.1079(4) 0.4018(2) 0.4792(3) 0.0474(9) Uani 1 1 d . . . . .
F3 F 0.2228(5) 0.3070(3) 0.7390(3) 0.138(2) Uani 1 1 d . . . . .
C29 C 0.0463(4) 0.3616(2) 0.4206(3) 0.0459(9) Uani 1 1 d . . . . .
C25 C 0.0644(4) 0.2987(2) 0.3064(3) 0.0547(11) Uani 1 1 d . . . . .
H25 H 0.110940 0.282388 0.264608 0.066 Uiso 1 1 calc R . . . .
O3 O 0.0892(5) 0.2713(2) 0.8793(4) 0.1050(18) Uani 1 1 d . . . . .
C19 C 0.2053(4) 0.4213(2) 0.1932(3) 0.0535(11) Uani 1 1 d . . . . .
C1 C 0.5334(4) 0.4235(2) 0.2908(3) 0.0490(10) Uani 1 1 d . . . . .
O1 O -0.0083(5) 0.3416(3) 0.7889(5) 0.123(2) Uani 1 1 d . . . . .
F6 F 0.5801(6) 0.2976(2) 0.6583(4) 0.154(3) Uani 1 1 d . . . . .
C15 C 0.1841(4) 0.4937(2) 0.2981(3) 0.0537(10) Uani 1 1 d . . . . .
H15 H 0.193368 0.505332 0.353737 0.064 Uiso 1 1 calc R . . . .
C8 C 0.2803(4) 0.2535(2) 0.4544(3) 0.0506(10) Uani 1 1 d . . . . .
F4 F 0.4430(5) 0.3599(3) 0.6524(5) 0.150(3) Uani 1 1 d . . . . .
C24 C 0.3667(4) 0.2818(2) 0.2223(3) 0.0550(11) Uani 1 1 d . . . . .
H24 H 0.414520 0.264491 0.263971 0.066 Uiso 1 1 calc R . . . .
C9 C 0.2593(5) 0.2047(2) 0.4028(4) 0.0649(13) Uani 1 1 d . . . . .
H9 H 0.302317 0.200315 0.354068 0.078 Uiso 1 1 calc R . . . .
F2 F 0.2117(5) 0.4046(3) 0.7732(4) 0.146(2) Uani 1 1 d . . . . .
C18 C 0.1571(6) 0.4608(3) 0.1348(4) 0.0708(15) Uani 1 1 d . . . . .
H18 H 0.147887 0.448968 0.079174 0.085 Uiso 1 1 calc R . . . .
C20 C 0.2521(5) 0.3616(2) 0.1736(3) 0.0520(10) Uani 1 1 d . . . . .
O2 O 0.0815(7) 0.3791(3) 0.9214(4) 0.114(2) Uani 1 1 d . . . . .
C27 C -0.1223(4) 0.3037(3) 0.3734(4) 0.0640(13) Uani 1 1 d . . . . .
H27 H -0.200987 0.291429 0.378235 0.077 Uiso 1 1 calc R . . . .
C26 C -0.0514(5) 0.2811(3) 0.3111(4) 0.0654(14) Uani 1 1 d . . . . .
H26 H -0.082749 0.253921 0.272314 0.078 Uiso 1 1 calc R . . . .
C6 C 0.6189(5) 0.3810(3) 0.2786(4) 0.0711(15) Uani 1 1 d . . . . .
H6 H 0.621345 0.346623 0.311911 0.085 Uiso 1 1 calc R . . . .
C28 C -0.0729(4) 0.3450(3) 0.4281(3) 0.0600(12) Uani 1 1 d . . . . .
H28 H -0.118672 0.361760 0.469901 0.072 Uiso 1 1 calc R . . . .
F1 F 0.3048(5) 0.3431(3) 0.8570(5) 0.150(3) Uani 1 1 d . . . . .
C10 C 0.1740(6) 0.1620(3) 0.4232(4) 0.0783(17) Uani 1 1 d . . . . .
H10 H 0.160149 0.129581 0.387560 0.094 Uiso 1 1 calc R . . . .
C34 C 0.2876(4) 0.4453(2) 0.5189(3) 0.0520(10) Uani 1 1 d . . . . .
H34 H 0.368487 0.450619 0.510221 0.062 Uiso 1 1 calc R . . . .
C31 C 0.0546(5) 0.4281(3) 0.5479(4) 0.0676(14) Uani 1 1 d . . . . .
H31 H -0.025763 0.421655 0.557526 0.081 Uiso 1 1 calc R . . . .
C23 C 0.3525(6) 0.2524(3) 0.1464(4) 0.0708(15) Uani 1 1 d . . . . .
H23 H 0.389052 0.215360 0.138024 0.085 Uiso 1 1 calc R . . . .
F5 F 0.5895(8) 0.3768(4) 0.7298(3) 0.167(3) Uani 1 1 d . . . . .
C11 C 0.1095(5) 0.1670(3) 0.4959(4) 0.0741(16) Uani 1 1 d . . . . .
C33 C 0.2380(5) 0.4726(3) 0.5872(3) 0.0669(14) Uani 1 1 d . . . . .
H33 H 0.283902 0.496642 0.622869 0.080 Uiso 1 1 calc R . . . .
C32 C 0.1209(5) 0.4637(4) 0.6015(4) 0.0811(19) Uani 1 1 d . . . . .
H32 H 0.085557 0.481587 0.647321 0.097 Uiso 1 1 calc R . . . .
C2 C 0.5275(5) 0.4736(3) 0.2393(4) 0.0666(14) Uani 1 1 d . . . . .
H2 H 0.467741 0.502094 0.245735 0.080 Uiso 1 1 calc R . . . .
C22 C 0.2851(7) 0.2776(3) 0.0840(4) 0.0848(19) Uani 1 1 d . . . . .
H22 H 0.272737 0.257538 0.033467 0.102 Uiso 1 1 calc R . . . .
C16 C 0.1366(5) 0.5341(3) 0.2415(4) 0.0684(14) Uani 1 1 d . . . . .
H16 H 0.114153 0.572298 0.258940 0.082 Uiso 1 1 calc R . . . .
C13 C 0.2179(5) 0.2578(3) 0.5279(4) 0.0654(13) Uani 1 1 d . . . . .
H13 H 0.232645 0.289794 0.564236 0.079 Uiso 1 1 calc R . . . .
C5 C 0.7024(6) 0.3890(4) 0.2164(5) 0.093(2) Uani 1 1 d . . . . .
H5 H 0.760328 0.359721 0.208426 0.112 Uiso 1 1 calc R . . . .
C4 C 0.7006(7) 0.4397(4) 0.1663(5) 0.093(2) Uani 1 1 d . . . . .
C21 C 0.2356(6) 0.3334(3) 0.0974(4) 0.0715(15) Uani 1 1 d . . . . .
H21 H 0.191125 0.352079 0.055015 0.086 Uiso 1 1 calc R . . . .
C12 C 0.1336(5) 0.2148(3) 0.5479(4) 0.0778(17) Uani 1 1 d . . . . .
H12 H 0.092612 0.218502 0.597640 0.093 Uiso 1 1 calc R . . . .
C17 C 0.1226(6) 0.5178(3) 0.1590(4) 0.0780(17) Uani 1 1 d . . . . .
H17 H 0.090429 0.544637 0.120035 0.094 Uiso 1 1 calc R . . . .
C3 C 0.6125(8) 0.4809(4) 0.1776(4) 0.091(2) Uani 1 1 d . . . . .
H3 H 0.608885 0.514662 0.143261 0.110 Uiso 1 1 calc R . . . .
C36 C 0.5568(6) 0.3549(3) 0.6579(4) 0.0796(18) Uani 1 1 d . . . . .
C14 C 0.0150(7) 0.1210(4) 0.5163(7) 0.105(3) Uani 1 1 d . . . . .
H14A H -0.059068 0.132341 0.489732 0.157 Uiso 1 1 calc GR . . . .
H14B H 0.005312 0.119391 0.575828 0.157 Uiso 1 1 calc GR . . . .
H14C H 0.038787 0.082174 0.496348 0.157 Uiso 1 1 calc GR . . . .
S1 S 0.07903(16) 0.33324(7) 0.85893(11) 0.0786(4) Uani 1 1 d . . . . .
C7 C 0.7953(9) 0.4484(6) 0.0991(6) 0.146(5) Uani 1 1 d . . . . .
H7A H 0.848433 0.480230 0.115876 0.219 Uiso 1 1 calc GR . . . .
H7B H 0.757000 0.458645 0.046785 0.219 Uiso 1 1 calc GR . . . .
H7C H 0.839443 0.411749 0.092872 0.219 Uiso 1 1 calc GR . . . .


_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 N3 2.037(4) . Y
Ru1 N4 2.074(4) . Y
Ru1 N5 2.063(3) . Y
Ru1 N6 2.077(4) . Y
Ru1 N2 2.192(4) . Y
Ru1 N1 2.174(3) . Y
S2 O4 1.434(4) . N
S2 O6 1.424(4) . N
S2 O5 1.428(4) . N
S2 C36 1.813(6) . N
C35 F3 1.383(12) . N
C35 F2 1.329(10) . N
C35 F1 1.358(10) . N
C35 S1 1.784(9) . N
N3 C19 1.368(6) . N
N3 C15 1.356(6) . N
N4 C24 1.343(6) . N
N4 C20 1.358(6) . N
N5 C29 1.350(6) . N
N5 C25 1.338(6) . N
N6 C30 1.356(6) . N
N6 C34 1.350(6) . N
N2 C8 1.446(6) . Y
N1 C1 1.435(6) . Y
C30 C29 1.458(7) . N
C30 C31 1.390(7) . N
C29 C28 1.397(7) . N
C25 C26 1.362(7) . N
O3 S1 1.418(5) . N
C19 C18 1.383(7) . N
C19 C20 1.462(7) . N
C1 C6 1.365(8) . N
C1 C2 1.384(7) . Y
O1 S1 1.485(6) . N
F6 C36 1.298(9) . N
C15 C16 1.373(7) . N
C8 C9 1.380(7) . N
C8 C13 1.384(7) . N
F4 C36 1.285(8) . N
C24 C23 1.385(8) . N
C9 C10 1.392(8) . N
C18 C17 1.381(9) . N
C20 C21 1.379(7) . N
O2 S1 1.425(6) . N
C27 C26 1.383(8) . N
C27 C28 1.375(8) . N
C6 C5 1.393(9) . N
C10 C11 1.386(10) . N
C34 C33 1.377(7) . N
C31 C32 1.373(8) . N
C23 C22 1.359(10) . N
F5 C36 1.294(10) . N
C11 C12 1.373(10) . N
C11 C14 1.514(9) . N
C33 C32 1.354(8) . N
C2 C3 1.397(9) . N
C22 C21 1.379(10) . N
C16 C17 1.373(9) . N
C13 C12 1.387(8) . N
C5 C4 1.383(12) . N
C4 C3 1.361(12) . N
C4 C7 1.539(9) . N

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
N3 Ru1 N4 78.48(15) . . Y
N3 Ru1 N5 87.76(14) . . N
N3 Ru1 N6 96.37(14) . . N
N3 Ru1 N2 176.12(14) . . N
N3 Ru1 N1 90.07(14) . . N
N4 Ru1 N6 170.29(14) . . N
N4 Ru1 N2 97.83(15) . . N
N4 Ru1 N1 94.49(14) . . N
N5 Ru1 N4 93.04(14) . . N
N5 Ru1 N6 78.44(14) . . Y
N5 Ru1 N2 93.66(14) . . N
N5 Ru1 N1 171.59(14) . . N
N6 Ru1 N2 87.45(14) . . N
N6 Ru1 N1 93.75(14) . . N
N1 Ru1 N2 89.03(14) . . Y
O4 S2 C36 102.3(3) . . N
O6 S2 O4 116.0(3) . . N
O6 S2 O5 114.8(3) . . N
O6 S2 C36 105.6(3) . . N
O5 S2 O4 113.5(3) . . N
O5 S2 C36 102.4(3) . . N
F3 C35 S1 109.7(6) . . N
F2 C35 F3 111.5(8) . . N
F2 C35 F1 107.5(8) . . N
F2 C35 S1 111.7(7) . . N
F1 C35 F3 108.9(8) . . N
F1 C35 S1 107.6(7) . . N
C19 N3 Ru1 115.7(3) . . N
C15 N3 Ru1 126.0(3) . . N
C15 N3 C19 118.3(4) . . N
C24 N4 Ru1 126.8(3) . . N
C24 N4 C20 118.0(4) . . N
C20 N4 Ru1 114.0(3) . . N
C29 N5 Ru1 115.3(3) . . N
C25 N5 Ru1 126.1(3) . . N
C25 N5 C29 118.5(4) . . N
C30 N6 Ru1 114.8(3) . . N
C34 N6 Ru1 127.5(3) . . N
C34 N6 C30 117.7(4) . . N
C8 N2 Ru1 115.3(3) . . N
C1 N1 Ru1 123.8(3) . . Y
N6 C30 C29 115.2(4) . . N
N6 C30 C31 120.8(4) . . N
C31 C30 C29 123.9(4) . . N
N5 C29 C30 115.5(4) . . N
N5 C29 C28 121.0(4) . . N
C28 C29 C30 123.4(4) . . N
N5 C25 C26 122.6(5) . . N
N3 C19 C18 120.8(5) . . N
N3 C19 C20 114.5(4) . . N
C18 C19 C20 124.6(5) . . N
C6 C1 N1 120.9(5) . . N
C6 C1 C2 119.8(5) . . N
C2 C1 N1 119.1(5) . . N
N3 C15 C16 122.2(5) . . N
C9 C8 N2 121.0(4) . . N
C9 C8 C13 118.6(5) . . N
C13 C8 N2 120.4(5) . . N
N4 C24 C23 121.8(5) . . N
C8 C9 C10 120.3(6) . . N
C17 C18 C19 120.0(6) . . N
N4 C20 C19 114.7(4) . . N
N4 C20 C21 121.4(5) . . N
C21 C20 C19 123.9(5) . . N
C28 C27 C26 117.9(5) . . N
C25 C26 C27 120.1(5) . . N
C1 C6 C5 120.0(7) . . N
C27 C28 C29 119.8(5) . . N
C11 C10 C9 121.1(6) . . N
N6 C34 C33 123.2(5) . . N
C32 C31 C30 119.8(5) . . N
C22 C23 C24 120.0(6) . . N
C10 C11 C14 120.5(7) . . N
C12 C11 C10 118.0(6) . . N
C12 C11 C14 121.5(7) . . N
C32 C33 C34 118.7(5) . . N
C33 C32 C31 119.7(5) . . N
C1 C2 C3 119.2(6) . . N
C23 C22 C21 118.5(6) . . N
C17 C16 C15 119.7(6) . . N
C8 C13 C12 120.6(6) . . N
C4 C5 C6 121.0(7) . . N
C5 C4 C7 120.2(9) . . N
C3 C4 C5 118.2(6) . . N
C3 C4 C7 121.6(9) . . N
C22 C21 C20 119.9(6) . . N
C11 C12 C13 121.3(6) . . N
C16 C17 C18 118.9(5) . . N
C4 C3 C2 121.7(7) . . N
F6 C36 S2 112.4(5) . . N
F4 C36 S2 111.0(5) . . N
F4 C36 F6 106.7(7) . . N
F4 C36 F5 106.9(7) . . N
F5 C36 S2 111.5(6) . . N
F5 C36 F6 108.0(7) . . N
O3 S1 C35 103.8(4) . . N
O3 S1 O1 110.1(4) . . N
O3 S1 O2 122.1(4) . . N
O1 S1 C35 98.0(4) . . N
O2 S1 C35 102.2(5) . . N
O2 S1 O1 116.2(4) . . N

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.831
