# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1940710'
loop_
_audit_author_name
_audit_author_address
'Yury Torubaev' 'Kurnakov Institute of General and Inorganic Chemistry'
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-09-26 downloaded from the CCDC.
;
_audit_creation_date             2019-05-27
_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            ?
_chemical_name_systematic        '4-cyanopyridine 1,4 diiodooctafluorobutane'
_chemical_formula_moiety         'C4 F8 I2, 2(C6 H4 N2)'
_chemical_formula_sum            'C16 H8 F8 I2 N4'
_chemical_formula_weight         662.06
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.166(5)
_cell_length_b                   5.694(6)
_cell_length_c                   17.261(17)
_cell_angle_alpha                98.37(5)
_cell_angle_beta                 93.01(4)
_cell_angle_gamma                98.12(6)
_cell_volume                     495.9(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    242
_cell_measurement_temperature    150
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.909
_exptl_absorpt_coefficient_mu    3.255
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_correction_T_min  0.487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0916 before and 0.0443 after correction.
The Ratio of minimum to maximum transmission is 0.6526.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             310
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7197
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.989
_diffrn_reflns_theta_min         2.392
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2495
_reflns_number_total             2558
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.968
_refine_diff_density_min         -1.567
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.265
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2558
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.265
_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)+(0.0017P)²+0.9061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0577
_refine_ls_wR_factor_ref         0.0581
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
I1 I 0.96264(4) 0.40170(4) 0.19387(2) 0.02078(7) Uani 1 1 d . . . . .
C2 C 0.3243(6) 0.9474(5) 0.37489(18) 0.0196(6) Uani 1 1 d . . . . .
N1 N 0.6795(5) 0.6714(5) 0.30812(16) 0.0235(6) Uani 1 1 d . . . . .
C3 C 0.4247(7) 0.9893(6) 0.30480(19) 0.0236(6) Uani 1 1 d . . . . .
H3 H 0.375938 1.114266 0.278819 0.028 Uiso 1 1 calc R . . . .
C4 C 0.5984(7) 0.8438(6) 0.27351(19) 0.0243(7) Uani 1 1 d . . . . .
H4 H 0.663321 0.868895 0.224412 0.029 Uiso 1 1 calc R . . . .
C1 C 0.1409(7) 1.0940(6) 0.40865(19) 0.0239(6) Uani 1 1 d . . . . .
C6 C 0.4026(6) 0.7651(6) 0.41140(19) 0.0228(6) Uani 1 1 d . . . . .
H6 H 0.334444 0.730613 0.459231 0.027 Uiso 1 1 calc R . . . .
C5 C 0.5834(7) 0.6346(6) 0.37605(19) 0.0243(7) Uani 1 1 d . . . . .
H5 H 0.641647 0.512651 0.401647 0.029 Uiso 1 1 calc R . . . .
N2 N -0.0017(6) 1.2142(6) 0.43484(18) 0.0311(7) Uani 1 1 d . . . . .
C7 C 1.1457(6) 0.2184(6) 0.09866(18) 0.0228(6) Uani 1 1 d . . . . .
C8 C 0.9435(6) 0.0671(6) 0.03591(17) 0.0187(6) Uani 1 1 d . . . . .
F3 F 0.7984(4) -0.0937(4) 0.07072(11) 0.0317(5) Uani 1 1 d . . . . .
F2 F 1.3003(4) 0.3786(4) 0.06594(13) 0.0381(5) Uani 1 1 d . . . . .
F4 F 0.7881(4) 0.2130(4) 0.01036(12) 0.0327(5) Uani 1 1 d . . . . .
F1 F 1.3001(4) 0.0738(4) 0.12655(12) 0.0363(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C7 2.151(3) . ?
C2 C3 1.380(5) . ?
C2 C1 1.440(5) . ?
C2 C6 1.386(5) . ?
N1 C4 1.325(4) . ?
N1 C5 1.330(4) . ?
C3 C4 1.384(5) . ?
C1 N2 1.141(4) . ?
C6 C5 1.386(5) . ?
C7 C8 1.537(4) . ?
C7 F2 1.334(4) . ?
C7 F1 1.344(4) . ?
C8 C8 1.545(6) 2_755 ?
C8 F3 1.332(4) . ?
C8 F4 1.337(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C1 119.4(3) . . ?
C3 C2 C6 119.2(3) . . ?
C6 C2 C1 121.4(3) . . ?
C4 N1 C5 117.6(3) . . ?
C2 C3 C4 118.0(3) . . ?
N1 C4 C3 123.7(3) . . ?
N2 C1 C2 178.6(4) . . ?
C5 C6 C2 118.0(3) . . ?
N1 C5 C6 123.4(3) . . ?
C8 C7 I1 112.1(2) . . ?
F2 C7 I1 109.5(2) . . ?
F2 C7 C8 109.6(3) . . ?
F2 C7 F1 107.0(3) . . ?
F1 C7 I1 109.6(2) . . ?
F1 C7 C8 108.9(3) . . ?
C7 C8 C8 115.9(3) . 2_755 ?
F3 C8 C7 107.5(3) . . ?
F3 C8 C8 108.5(3) . 2_755 ?
F3 C8 F4 108.4(3) . . ?
F4 C8 C7 107.9(3) . . ?
F4 C8 C8 108.3(3) . 2_755 ?

_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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1940714'
loop_
_audit_author_name
_audit_author_address
'Yury Torubaev' 'Kurnakov Institute of General and Inorganic Chemistry'
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-09-26 downloaded from the CCDC.
;
_audit_creation_date             2019-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            ?
_chemical_name_systematic        
'(4-Cyanopyridine)-(h6-p-cymene)-diiodo-ruthenium(ii) 1,4-diiodo-tetrafluorobenzene'
_chemical_formula_moiety         'C16 H18 I2 N2 Ru, 1.5(C6 F4 I2)'
_chemical_formula_sum            'C25 H18 F6 I5 N2 Ru'
_chemical_formula_weight         1195.98
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 '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                   10.2109(10)
_cell_length_b                   12.3421(13)
_cell_length_c                   12.8953(13)
_cell_angle_alpha                101.776(2)
_cell_angle_beta                 99.116(2)
_cell_angle_gamma                92.868(2)
_cell_volume                     1565.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1589
_cell_measurement_temperature    296
_cell_measurement_theta_max      22.91
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.456
_shelx_estimated_absorpt_T_min   0.365
_exptl_absorpt_coefficient_mu    5.487
_exptl_absorpt_correction_T_max  0.447
_exptl_absorpt_correction_T_min  0.372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0665 before and 0.0408 after correction.
The Ratio of minimum to maximum transmission is 0.8246.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.538
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1090
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.1026
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12796
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_min         2.027
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          296
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4811
_reflns_number_total             7945
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         3.465
_refine_diff_density_min         -2.303
_refine_diff_density_rms         0.235
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         7945
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      0.972
_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)+(0.0376P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.1109
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C8(H8), C4(H4), C6(H6), C3(H3), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
I1 I 0.32328(6) 0.06079(5) -0.40249(4) 0.02532(14) Uani 1 1 d . . . . .
I2 I 0.31631(6) 0.05302(5) -0.11325(5) 0.02685(15) Uani 1 1 d . . . . .
Ru1 Ru 0.51705(7) 0.07411(6) -0.22758(5) 0.01935(16) Uani 1 1 d . . . . .
I4 I 1.17461(6) 0.30912(5) -0.30747(5) 0.03425(17) Uani 1 1 d . . . . .
I3F I 0.86172(7) 0.72791(6) -0.01061(5) 0.03959(18) Uani 1 1 d . . . . .
I5 I 1.85436(7) 0.22812(6) 0.40908(7) 0.0517(2) Uani 1 1 d . . . . .
N2 N 0.5113(7) -0.1016(5) -0.2667(5) 0.0191(15) Uani 1 1 d . . . . .
F3 F 1.2632(6) 0.5692(6) -0.2036(6) 0.074(2) Uani 1 1 d . . . . .
F4 F 1.1442(7) 0.7273(6) -0.0930(6) 0.083(3) Uani 1 1 d . . . . .
C9 C 0.6380(9) 0.1776(7) -0.0845(7) 0.025(2) Uani 1 1 d . . . . .
H9 H 0.625903 0.184818 -0.013481 0.030 Uiso 1 1 calc R . . . .
C5 C 0.5172(9) -0.1571(7) -0.3671(7) 0.028(2) Uani 1 1 d . . . . .
H5 H 0.518401 -0.116793 -0.420548 0.033 Uiso 1 1 calc R . . . .
C1 C 0.5114(9) -0.4522(8) -0.3428(7) 0.029(2) Uani 1 1 d . . . . .
C2 C 0.5163(9) -0.3317(7) -0.3169(8) 0.029(2) Uani 1 1 d . . . . .
C10 C 0.5796(9) 0.2507(7) -0.1439(7) 0.027(2) Uani 1 1 d . . . . .
C8 C 0.7142(9) 0.0937(7) -0.1273(7) 0.026(2) Uani 1 1 d . . . . .
H8 H 0.751968 0.047397 -0.084368 0.031 Uiso 1 1 calc R . . . .
C4 C 0.5109(8) -0.1622(7) -0.1914(6) 0.0204(18) Uani 1 1 d . . . . .
H4 H 0.509177 -0.125550 -0.121067 0.024 Uiso 1 1 calc R . . . .
F1 F 0.7728(8) 0.4767(6) -0.1246(9) 0.110(4) Uani 1 1 d . . . . .
C6 C 0.5215(8) -0.2702(7) -0.3945(7) 0.0233(19) Uani 1 1 d . . . . .
H6 H 0.527727 -0.304878 -0.464522 0.028 Uiso 1 1 calc R . . . .
C16 C 0.5051(9) 0.3425(7) -0.0917(7) 0.032(2) Uani 1 1 d . . . . .
H16A H 0.458528 0.376446 -0.145820 0.048 Uiso 1 1 calc GR . . . .
H16B H 0.566685 0.397179 -0.041419 0.048 Uiso 1 1 calc GR . . . .
H16C H 0.442278 0.312644 -0.054616 0.048 Uiso 1 1 calc GR . . . .
C7 C 0.7342(8) 0.0787(7) -0.2365(7) 0.0206(18) Uani 1 1 d . . . . .
C3 C 0.5128(9) -0.2752(7) -0.2130(7) 0.029(2) Uani 1 1 d . . . . .
H3 H 0.511820 -0.313928 -0.158311 0.035 Uiso 1 1 calc R . . . .
N1 N 0.5048(9) -0.5463(7) -0.3641(7) 0.046(2) Uani 1 1 d . . . . .
C17 C 0.9548(9) 0.6051(8) -0.1043(8) 0.033(2) Uani 1 1 d . . . . .
F2 F 0.8894(7) 0.3195(5) -0.2421(8) 0.102(3) Uani 1 1 d . . . . .
C11 C 0.5934(8) 0.2353(7) -0.2512(7) 0.0241(19) Uani 1 1 d . . . . .
H11 H 0.553661 0.281679 -0.293125 0.029 Uiso 1 1 calc R . . . .
C13 C 0.8171(9) -0.0085(7) -0.2880(7) 0.028(2) Uani 1 1 d . . . . .
H13 H 0.763658 -0.050579 -0.355464 0.033 Uiso 1 1 calc R . . . .
C15 C 0.9378(9) 0.0525(7) -0.3150(8) 0.034(2) Uani 1 1 d . . . . .
H15A H 0.907722 0.098912 -0.363789 0.051 Uiso 1 1 calc GR . . . .
H15B H 0.992452 -0.000771 -0.347871 0.051 Uiso 1 1 calc GR . . . .
H15C H 0.988697 0.097575 -0.250180 0.051 Uiso 1 1 calc GR . . . .
C22 C 1.0774(10) 0.6259(8) -0.1271(8) 0.041(3) Uani 1 1 d . . . . .
C20 C 1.0787(9) 0.4382(8) -0.2262(7) 0.028(2) Uani 1 1 d . . . . .
C21 C 1.1399(10) 0.5453(9) -0.1849(9) 0.040(3) Uani 1 1 d . . . . .
C12 C 0.6689(8) 0.1482(6) -0.2984(7) 0.0239(19) Uani 1 1 d . . . . .
H12 H 0.674546 0.137761 -0.370953 0.029 Uiso 1 1 calc R . . . .
C19 C 0.9536(11) 0.4201(8) -0.2038(11) 0.057(3) Uani 1 1 d . . . . .
C18 C 0.8929(11) 0.5006(8) -0.1449(10) 0.050(3) Uani 1 1 d . . . . .
C14 C 0.8620(10) -0.0896(8) -0.2189(8) 0.040(3) Uani 1 1 d . . . . .
H14A H 0.912207 -0.049674 -0.151411 0.060 Uiso 1 1 calc GR . . . .
H14B H 0.916839 -0.140382 -0.255095 0.060 Uiso 1 1 calc GR . . . .
H14C H 0.785599 -0.130338 -0.206370 0.060 Uiso 1 1 calc GR . . . .
F5 F 2.1313(6) 0.3484(5) 0.3830(6) 0.062(2) Uani 1 1 d . . . . .
F6 F 1.7588(6) 0.4461(5) 0.5434(6) 0.068(2) Uani 1 1 d . . . . .
C26 C 1.8778(10) 0.4713(8) 0.5207(8) 0.037(2) Uani 1 1 d . . . . .
C24 C 1.9419(9) 0.3917(8) 0.4603(8) 0.034(2) Uani 1 1 d . . . . .
C25 C 2.0640(10) 0.4234(9) 0.4405(9) 0.041(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Ru1 2.7261(9) . ?
I2 Ru1 2.7392(9) . ?
Ru1 N2 2.119(6) . ?
Ru1 C9 2.173(8) . ?
Ru1 C10 2.238(9) . ?
Ru1 C8 2.186(9) . ?
Ru1 C7 2.236(8) . ?
Ru1 C11 2.197(8) . ?
Ru1 C12 2.173(8) . ?
I4 C20 2.097(9) . ?
I3F C17 2.103(10) . ?
I5 C24 2.097(10) . ?
N2 C5 1.348(10) . ?
N2 C4 1.342(9) . ?
F3 C21 1.348(11) . ?
F4 C22 1.349(11) . ?
C9 H9 0.9300 . ?
C9 C10 1.396(12) . ?
C9 C8 1.402(12) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(11) . ?
C1 C2 1.453(12) . ?
C1 N1 1.133(11) . ?
C2 C6 1.380(12) . ?
C2 C3 1.386(12) . ?
C10 C16 1.500(11) . ?
C10 C11 1.389(11) . ?
C8 H8 0.9300 . ?
C8 C7 1.431(11) . ?
C4 H4 0.9300 . ?
C4 C3 1.368(11) . ?
F1 C18 1.326(11) . ?
C6 H6 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C7 C13 1.515(11) . ?
C7 C12 1.409(11) . ?
C3 H3 0.9300 . ?
C17 C22 1.354(13) . ?
C17 C18 1.369(13) . ?
F2 C19 1.334(12) . ?
C11 H11 0.9300 . ?
C11 C12 1.444(11) . ?
C13 H13 0.9800 . ?
C13 C15 1.536(12) . ?
C13 C14 1.512(12) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C22 C21 1.366(13) . ?
C20 C21 1.395(13) . ?
C20 C19 1.371(13) . ?
C12 H12 0.9300 . ?
C19 C18 1.360(14) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
F5 C25 1.350(10) . ?
F6 C26 1.331(10) . ?
C26 C24 1.383(13) . ?
C26 C25 1.363(14) 2_966 ?
C24 C25 1.366(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I1 Ru1 I2 87.01(3) . . ?
N2 Ru1 I1 88.00(18) . . ?
N2 Ru1 I2 88.09(17) . . ?
N2 Ru1 C9 124.0(3) . . ?
N2 Ru1 C10 160.5(3) . . ?
N2 Ru1 C8 93.8(3) . . ?
N2 Ru1 C7 87.9(3) . . ?
N2 Ru1 C11 148.9(3) . . ?
N2 Ru1 C12 110.8(3) . . ?
C9 Ru1 I1 147.8(2) . . ?
C9 Ru1 I2 89.7(2) . . ?
C9 Ru1 C10 36.9(3) . . ?
C9 Ru1 C8 37.5(3) . . ?
C9 Ru1 C7 67.8(3) . . ?
C9 Ru1 C11 66.1(3) . . ?
C10 Ru1 I1 111.4(2) . . ?
C10 Ru1 I2 94.2(2) . . ?
C8 Ru1 I1 160.5(2) . . ?
C8 Ru1 I2 112.4(2) . . ?
C8 Ru1 C10 67.4(3) . . ?
C8 Ru1 C7 37.7(3) . . ?
C8 Ru1 C11 79.5(3) . . ?
C7 Ru1 I1 123.2(2) . . ?
C7 Ru1 I2 149.4(2) . . ?
C7 Ru1 C10 80.3(3) . . ?
C11 Ru1 I1 89.0(2) . . ?
C11 Ru1 I2 122.6(2) . . ?
C11 Ru1 C10 36.5(3) . . ?
C11 Ru1 C7 68.2(3) . . ?
C12 Ru1 I1 93.9(2) . . ?
C12 Ru1 I2 161.1(2) . . ?
C12 Ru1 C9 79.5(3) . . ?
C12 Ru1 C10 67.9(3) . . ?
C12 Ru1 C8 67.4(3) . . ?
C12 Ru1 C7 37.2(3) . . ?
C12 Ru1 C11 38.6(3) . . ?
C5 N2 Ru1 121.5(5) . . ?
C4 N2 Ru1 121.6(5) . . ?
C4 N2 C5 116.8(7) . . ?
Ru1 C9 H9 127.8 . . ?
C10 C9 Ru1 74.1(5) . . ?
C10 C9 H9 118.6 . . ?
C10 C9 C8 122.8(8) . . ?
C8 C9 Ru1 71.8(5) . . ?
C8 C9 H9 118.6 . . ?
N2 C5 H5 118.3 . . ?
N2 C5 C6 123.4(8) . . ?
C6 C5 H5 118.3 . . ?
N1 C1 C2 178.5(12) . . ?
C6 C2 C1 121.6(9) . . ?
C6 C2 C3 117.9(8) . . ?
C3 C2 C1 120.5(8) . . ?
C9 C10 Ru1 69.0(5) . . ?
C9 C10 C16 120.2(8) . . ?
C16 C10 Ru1 132.5(6) . . ?
C11 C10 Ru1 70.2(5) . . ?
C11 C10 C9 117.8(8) . . ?
C11 C10 C16 122.0(8) . . ?
Ru1 C8 H8 128.9 . . ?
C9 C8 Ru1 70.7(5) . . ?
C9 C8 H8 119.7 . . ?
C9 C8 C7 120.5(8) . . ?
C7 C8 Ru1 73.0(5) . . ?
C7 C8 H8 119.7 . . ?
N2 C4 H4 118.4 . . ?
N2 C4 C3 123.1(8) . . ?
C3 C4 H4 118.4 . . ?
C5 C6 C2 119.1(8) . . ?
C5 C6 H6 120.4 . . ?
C2 C6 H6 120.4 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 C7 Ru1 69.2(5) . . ?
C8 C7 C13 123.7(7) . . ?
C13 C7 Ru1 131.4(6) . . ?
C12 C7 Ru1 68.9(5) . . ?
C12 C7 C8 116.7(7) . . ?
C12 C7 C13 119.5(7) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.6(8) . . ?
C4 C3 H3 120.2 . . ?
C22 C17 I3F 121.6(7) . . ?
C22 C17 C18 117.5(9) . . ?
C18 C17 I3F 120.9(7) . . ?
Ru1 C11 H11 129.8 . . ?
C10 C11 Ru1 73.4(5) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(8) . . ?
C12 C11 Ru1 69.8(5) . . ?
C12 C11 H11 119.6 . . ?
C7 C13 H13 108.3 . . ?
C7 C13 C15 107.5(7) . . ?
C15 C13 H13 108.3 . . ?
C14 C13 C7 113.9(7) . . ?
C14 C13 H13 108.3 . . ?
C14 C13 C15 110.4(7) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F4 C22 C17 121.5(9) . . ?
F4 C22 C21 116.7(9) . . ?
C17 C22 C21 121.8(10) . . ?
C21 C20 I4 122.9(7) . . ?
C19 C20 I4 121.4(7) . . ?
C19 C20 C21 115.5(9) . . ?
F3 C21 C22 119.7(9) . . ?
F3 C21 C20 118.9(9) . . ?
C22 C21 C20 121.4(9) . . ?
Ru1 C12 H12 127.2 . . ?
C7 C12 Ru1 73.8(5) . . ?
C7 C12 C11 121.2(8) . . ?
C7 C12 H12 119.4 . . ?
C11 C12 Ru1 71.6(5) . . ?
C11 C12 H12 119.4 . . ?
F2 C19 C20 118.3(10) . . ?
F2 C19 C18 119.2(10) . . ?
C18 C19 C20 122.5(10) . . ?
F1 C18 C17 119.4(9) . . ?
F1 C18 C19 119.3(9) . . ?
C19 C18 C17 121.2(10) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F6 C26 C24 120.7(9) . . ?
F6 C26 C25 118.6(9) . 2_966 ?
C25 C26 C24 120.7(9) 2_966 . ?
C26 C24 I5 119.7(7) . . ?
C25 C24 I5 122.7(7) . . ?
C25 C24 C26 117.5(9) . . ?
F5 C25 C26 118.5(9) . 2_966 ?
F5 C25 C24 119.7(10) . . ?
C26 C25 C24 121.8(9) 2_966 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ru1 N2 C5 C6 176.1(7) . . . . ?
Ru1 N2 C4 C3 -177.2(7) . . . . ?
Ru1 C9 C10 C16 127.9(8) . . . . ?
Ru1 C9 C10 C11 -52.2(7) . . . . ?
Ru1 C9 C8 C7 55.6(7) . . . . ?
Ru1 C10 C11 C12 -53.3(7) . . . . ?
Ru1 C8 C7 C13 -126.7(8) . . . . ?
Ru1 C8 C7 C12 51.6(7) . . . . ?
Ru1 C7 C13 C15 154.1(6) . . . . ?
Ru1 C7 C13 C14 -83.1(10) . . . . ?
Ru1 C7 C12 C11 56.0(7) . . . . ?
Ru1 C11 C12 C7 -57.0(7) . . . . ?
I4 C20 C21 F3 4.2(14) . . . . ?
I4 C20 C21 C22 -176.2(8) . . . . ?
I4 C20 C19 F2 -4.8(16) . . . . ?
I4 C20 C19 C18 175.4(10) . . . . ?
I3F C17 C22 F4 -1.7(14) . . . . ?
I3F C17 C22 C21 177.8(8) . . . . ?
I3F C17 C18 F1 -0.3(16) . . . . ?
I3F C17 C18 C19 -178.7(10) . . . . ?
I5 C24 C25 F5 2.0(14) . . . . ?
I5 C24 C25 C26 -176.5(8) . . . 2_966 ?
N2 C5 C6 C2 1.6(14) . . . . ?
N2 C4 C3 C2 0.5(14) . . . . ?
F4 C22 C21 F3 1.1(16) . . . . ?
F4 C22 C21 C20 -178.5(10) . . . . ?
C9 C10 C11 Ru1 51.7(7) . . . . ?
C9 C10 C11 C12 -1.6(13) . . . . ?
C9 C8 C7 Ru1 -54.5(7) . . . . ?
C9 C8 C7 C13 178.8(8) . . . . ?
C9 C8 C7 C12 -2.9(12) . . . . ?
C5 N2 C4 C3 -1.6(12) . . . . ?
C1 C2 C6 C5 175.8(9) . . . . ?
C1 C2 C3 C4 -176.7(9) . . . . ?
C10 C9 C8 Ru1 -56.3(8) . . . . ?
C10 C9 C8 C7 -0.7(13) . . . . ?
C10 C11 C12 Ru1 54.9(7) . . . . ?
C10 C11 C12 C7 -2.1(13) . . . . ?
C8 C9 C10 Ru1 55.2(8) . . . . ?
C8 C9 C10 C16 -176.9(8) . . . . ?
C8 C9 C10 C11 3.0(13) . . . . ?
C8 C7 C13 C15 -114.7(9) . . . . ?
C8 C7 C13 C14 8.1(12) . . . . ?
C8 C7 C12 Ru1 -51.7(7) . . . . ?
C8 C7 C12 C11 4.2(12) . . . . ?
C4 N2 C5 C6 0.6(13) . . . . ?
C6 C2 C3 C4 1.8(13) . . . . ?
C16 C10 C11 Ru1 -128.5(9) . . . . ?
C16 C10 C11 C12 178.3(8) . . . . ?
C3 C2 C6 C5 -2.7(13) . . . . ?
C17 C22 C21 F3 -178.5(10) . . . . ?
C17 C22 C21 C20 2.0(17) . . . . ?
F2 C19 C18 F1 2(2) . . . . ?
F2 C19 C18 C17 -179.9(11) . . . . ?
C13 C7 C12 Ru1 126.6(7) . . . . ?
C13 C7 C12 C11 -177.4(8) . . . . ?
C22 C17 C18 F1 180.0(11) . . . . ?
C22 C17 C18 C19 1.6(18) . . . . ?
C20 C19 C18 F1 -178.6(11) . . . . ?
C20 C19 C18 C17 0(2) . . . . ?
C21 C20 C19 F2 179.4(11) . . . . ?
C21 C20 C19 C18 -0.3(17) . . . . ?
C12 C7 C13 C15 67.1(10) . . . . ?
C12 C7 C13 C14 -170.2(8) . . . . ?
C19 C20 C21 F3 179.9(10) . . . . ?
C19 C20 C21 C22 -0.5(15) . . . . ?
C18 C17 C22 F4 178.1(10) . . . . ?
C18 C17 C22 C21 -2.4(16) . . . . ?
F6 C26 C24 I5 -2.5(14) . . . . ?
F6 C26 C24 C25 -179.8(9) . . . . ?
C26 C24 C25 F5 179.2(9) . . . . ?
C26 C24 C25 C26 0.6(18) . . . 2_966 ?
C25 C26 C24 I5 176.6(8) 2_966 . . . ?
C25 C26 C24 C25 -0.6(17) 2_966 . . . ?

_shelx_SHELXL_version_number     2017/1

_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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1955091'
loop_
_audit_author_name
_audit_author_address
'Yury Torubaev'
;Kurnakov Institute of General and Inorganic Chemistry of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2019-09-22 deposited with the CCDC.	2019-09-26 downloaded from the CCDC.
;
_audit_creation_date             2019-09-20
_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            ?
_chemical_name_systematic        '4-cyanopyridine 1,3-diiodo-tetrafluorobenzene'
_chemical_formula_moiety         'C6 F4 I2, C6 H4 N2'
_chemical_formula_sum            'C12 H4 F4 I2 N2'
_chemical_formula_weight         505.97
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.2751(11)
_cell_length_b                   27.919(7)
_cell_length_c                   12.173(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.964(7)
_cell_angle_gamma                90
_cell_volume                     1449.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    940
_cell_measurement_temperature    296
_cell_measurement_theta_max      3
_cell_measurement_theta_min      25
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.373
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1415 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.7050.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1177
_diffrn_reflns_av_unetI/netI     0.1430
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8597
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.223
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1455
_reflns_number_total             2932
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.716
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.163
_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1672
_refine_ls_R_factor_gt           0.0734
_refine_ls_restrained_S_all      0.982
_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)+(0.0528P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1532
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C6(H6), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_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
I1 I 0.3263(2) 0.62622(3) 0.48761(7) 0.0602(4) Uani 1 1 d . . . . .
I2 I 0.4039(2) 0.84102(4) 0.43840(8) 0.0680(4) Uani 1 1 d . . . . .
F1 F 0.2640(19) 0.7375(3) 0.5267(6) 0.075(2) Uani 1 1 d . . . . .
F2 F 0.7513(19) 0.8037(3) 0.2276(6) 0.076(2) Uani 1 1 d . . . . .
F4 F 0.675(2) 0.6381(3) 0.2624(7) 0.084(3) Uani 1 1 d . . . . .
F3 F 0.870(2) 0.7152(3) 0.1570(6) 0.090(3) Uani 1 1 d . . . . .
C8 C 0.501(3) 0.7730(4) 0.3803(11) 0.046(3) Uani 1 1 d . . . . .
N1 N 0.103(3) 0.5485(5) 0.6330(10) 0.074(4) Uani 1 1 d . . . . .
C10 C 0.719(3) 0.7204(6) 0.2479(10) 0.054(4) Uani 1 1 d . . . . .
C9 C 0.659(3) 0.7660(5) 0.2832(11) 0.052(4) Uani 1 1 d . . . . .
C7 C 0.410(3) 0.7310(5) 0.4329(10) 0.046(3) Uani 1 1 d . . . . .
C12 C 0.465(3) 0.6858(5) 0.3995(9) 0.045(3) Uani 1 1 d . . . . .
C4 C -0.043(4) 0.5683(6) 0.7128(13) 0.076(5) Uani 1 1 d . . . . .
H4 H -0.080166 0.601123 0.709149 0.092 Uiso 1 1 calc R . . . .
C3 C -0.147(3) 0.5433(5) 0.8030(11) 0.064(4) Uani 1 1 d . . . . .
H3 H -0.237750 0.558872 0.860453 0.076 Uiso 1 1 calc R . . . .
C11 C 0.621(3) 0.6821(5) 0.3044(10) 0.055(4) Uani 1 1 d . . . . .
C6 C 0.053(4) 0.4729(6) 0.7225(14) 0.076(5) Uani 1 1 d . . . . .
H6 H 0.101963 0.440472 0.725104 0.091 Uiso 1 1 calc R . . . .
C2 C -0.109(3) 0.4943(5) 0.8022(12) 0.063(4) Uani 1 1 d . . . . .
C1 C -0.219(4) 0.4664(6) 0.8923(16) 0.090(6) Uani 1 1 d . . . . .
C5 C 0.138(4) 0.5015(7) 0.6390(13) 0.082(5) Uani 1 1 d . . . . .
H5 H 0.229730 0.486648 0.580859 0.098 Uiso 1 1 calc R . . . .
N2 N -0.305(4) 0.4436(7) 0.9632(14) 0.132(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
I1 C12 2.087(12) . ?
I2 C8 2.079(12) . ?
F1 C7 1.351(13) . ?
F2 C9 1.325(14) . ?
F4 C11 1.357(14) . ?
F3 C10 1.326(13) . ?
C8 C9 1.415(16) . ?
C8 C7 1.403(16) . ?
N1 C4 1.314(17) . ?
N1 C5 1.320(18) . ?
C10 C9 1.374(18) . ?
C10 C11 1.353(18) . ?
C7 C12 1.351(16) . ?
C12 C11 1.379(16) . ?
C4 H4 0.9300 . ?
C4 C3 1.400(19) . ?
C3 H3 0.9300 . ?
C3 C2 1.377(18) . ?
C6 H6 0.9300 . ?
C6 C2 1.37(2) . ?
C6 C5 1.36(2) . ?
C2 C1 1.45(2) . ?
C1 N2 1.15(2) . ?
C5 H5 0.9300 . ?

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
C9 C8 I2 121.9(10) . . ?
C7 C8 I2 122.6(9) . . ?
C7 C8 C9 115.4(11) . . ?
C4 N1 C5 115.9(15) . . ?
F3 C10 C9 118.2(14) . . ?
F3 C10 C11 121.7(13) . . ?
C11 C10 C9 120.0(12) . . ?
F2 C9 C8 119.5(12) . . ?
F2 C9 C10 120.5(12) . . ?
C10 C9 C8 120.0(12) . . ?
F1 C7 C8 115.6(11) . . ?
C12 C7 F1 118.6(11) . . ?
C12 C7 C8 125.7(11) . . ?
C7 C12 I1 121.9(9) . . ?
C7 C12 C11 115.2(12) . . ?
C11 C12 I1 122.9(10) . . ?
N1 C4 H4 117.9 . . ?
N1 C4 C3 124.2(15) . . ?
C3 C4 H4 117.9 . . ?
C4 C3 H3 121.8 . . ?
C2 C3 C4 116.5(14) . . ?
C2 C3 H3 121.8 . . ?
F4 C11 C12 119.3(13) . . ?
C10 C11 F4 117.0(12) . . ?
C10 C11 C12 123.6(13) . . ?
C2 C6 H6 121.7 . . ?
C5 C6 H6 121.7 . . ?
C5 C6 C2 116.6(15) . . ?
C3 C2 C6 120.3(15) . . ?
C3 C2 C1 118.9(16) . . ?
C6 C2 C1 120.6(16) . . ?
N2 C1 C2 179(2) . . ?
N1 C5 C6 126.0(16) . . ?
N1 C5 H5 117.0 . . ?
C6 C5 H5 117.0 . . ?

_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_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1941548'
loop_
_audit_author_name
_audit_author_address
'Yury Torubaev' 'Kurnakov Institute of General and Inorganic Chemistry'
_audit_update_record             
;
2019-07-18 deposited with the CCDC.	2019-09-26 downloaded from the CCDC.
;
_audit_creation_date             2019-07-18
_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            ?
_chemical_name_systematic        '4-cyanopyridine 1,2-diiodoethene'
_chemical_formula_moiety         'C I, C6 H4 N2'
_chemical_formula_sum            'C7 H4 I N2'
_chemical_formula_weight         243.02
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.2421(3)
_cell_length_b                   7.0061(6)
_cell_length_c                   27.717(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.154(3)
_cell_angle_gamma                90
_cell_volume                     822.52(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4694
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.09
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   0.862
_shelx_estimated_absorpt_T_min   0.516
_exptl_absorpt_coefficient_mu    3.819
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0934 before and 0.0553 after correction.
The Ratio of minimum to maximum transmission is 0.7156.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.962
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            15176
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.634
_diffrn_reflns_theta_min         2.944
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1671
_reflns_number_total             2285
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.948
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.179
_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)+(0.0246P)²+1.5771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0947
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(HB), C6(HC), C7(HA), C8(H)
;
_atom_sites_solution_hydrogens   geom
_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
I2 I 0.76615(9) 0.71829(6) 0.44753(2) 0.06042(16) Uani 1 1 d . . . . .
C2 C 0.9478(13) 0.9355(9) 0.4890(2) 0.0595(14) Uani 1 1 d . . . . .
N1 N 0.4863(12) 0.4367(8) 0.38645(19) 0.0688(13) Uani 1 1 d . . . . .
N2 N -0.1849(18) -0.0956(11) 0.2888(2) 0.114(2) Uani 1 1 d . . . . .
C3 C -0.0420(16) 0.0203(11) 0.3079(2) 0.0790(19) Uani 1 1 d . . . . .
C4 C 0.1396(14) 0.1631(9) 0.3350(2) 0.0585(14) Uani 1 1 d . . . . .
C5 C 0.1906(17) 0.3393(10) 0.3149(2) 0.0763(18) Uani 1 1 d . . . . .
HB H 0.109456 0.369037 0.283970 0.092 Uiso 1 1 calc R . . . .
C6 C 0.3680(17) 0.4720(10) 0.3424(3) 0.084(2) Uani 1 1 d . . . . .
HC H 0.404301 0.591159 0.329024 0.101 Uiso 1 1 calc R . . . .
C7 C 0.4319(16) 0.2666(10) 0.4046(2) 0.0714(17) Uani 1 1 d . . . . .
HA H 0.511880 0.240069 0.435769 0.086 Uiso 1 1 calc R . . . .
C8 C 0.2634(14) 0.1264(9) 0.3799(2) 0.0682(16) Uani 1 1 d . . . . .
H H 0.234988 0.007636 0.394010 0.082 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
I2 C2 2.033(5) . ?
C2 C2 1.164(11) 3_776 ?
N1 C6 1.317(8) . ?
N1 C7 1.319(8) . ?
N2 C3 1.128(8) . ?
C3 C4 1.447(9) . ?
C4 C5 1.376(9) . ?
C4 C8 1.349(8) . ?
C5 HB 0.9300 . ?
C5 C6 1.396(9) . ?
C6 HC 0.9300 . ?
C7 HA 0.9300 . ?
C7 C8 1.375(9) . ?
C8 H 0.9300 . ?

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
C2 C2 I2 177.1(8) 3_776 . ?
C6 N1 C7 117.2(6) . . ?
N2 C3 C4 176.8(8) . . ?
C5 C4 C3 120.1(6) . . ?
C8 C4 C3 121.0(6) . . ?
C8 C4 C5 118.8(6) . . ?
C4 C5 HB 121.0 . . ?
C4 C5 C6 117.9(6) . . ?
C6 C5 HB 121.0 . . ?
N1 C6 C5 123.2(6) . . ?
N1 C6 HC 118.4 . . ?
C5 C6 HC 118.4 . . ?
N1 C7 HA 118.2 . . ?
N1 C7 C8 123.6(6) . . ?
C8 C7 HA 118.2 . . ?
C4 C8 C7 119.2(6) . . ?
C4 C8 H 120.4 . . ?
C7 C8 H 120.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'solution in heptane cooling at -10C'
####################################################################### 
# 
# 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_1_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1940712'
loop_
_audit_author_name
_audit_author_address
'Yury Torubaev' 'Kurnakov Institute of General and Inorganic Chemistry'
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'(4-Cyanopyridine)-(h6-p-cymene)-dichloro-ruthenium(ii) 1,4-diiodo-tetrafluorobenzene'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 Cl2 N2 Ru, C6 F4 I2'
_chemical_formula_sum            'C22 H18 Cl2 F4 I2 N2 Ru'
_chemical_formula_weight         812.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   25.095(2)
_cell_length_b                   11.2129(11)
_cell_length_c                   9.1348(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.251(2)
_cell_angle_gamma                90
_cell_volume                     2559.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    887
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.107
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   0.353
_exptl_transmission_factor_max   0.621
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.173
_exptl_absorpt_coefficient_mu    3.276
_shelx_estimated_absorpt_T_min   0.333
_shelx_estimated_absorpt_T_max   0.601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13423
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.940
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6690
_reflns_number_gt                6060
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0161P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.011(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6690
_refine_ls_number_parameters     300
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0469
_refine_ls_wR_factor_gt          0.0451
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.02468(14) 0.6167(3) -0.2814(4) 0.0374(8) Uani 1 1 d . . . . .
I1 I 0.13208(2) 0.47486(3) 0.11477(3) 0.03180(9) Uani 1 1 d . . . . .
I2 I -0.08956(2) 0.38340(3) -0.39109(3) 0.03051(9) Uani 1 1 d . . . . .
F2 F 0.05965(15) 0.6504(3) -0.0872(4) 0.0389(9) Uani 1 1 d . . . . .
F3 F 0.05682(14) 0.2419(3) 0.0395(4) 0.0390(8) Uani 1 1 d . . . . .
F4 F -0.02560(15) 0.2076(3) -0.1616(4) 0.0402(9) Uani 1 1 d . . . . .
C17 C 0.0621(2) 0.4461(5) -0.0222(6) 0.0268(12) Uani 1 1 d . . . . .
C18 C 0.0383(2) 0.3360(5) -0.0425(6) 0.0280(12) Uani 1 1 d . . . . .
C19 C -0.0046(2) 0.3173(5) -0.1463(6) 0.0266(12) Uani 1 1 d . . . . .
C20 C -0.0261(2) 0.4111(5) -0.2303(6) 0.0246(12) Uani 1 1 d . . . . .
C21 C -0.0038(2) 0.5226(5) -0.2047(6) 0.0260(12) Uani 1 1 d . . . . .
C22 C 0.0394(2) 0.5390(5) -0.1032(7) 0.0284(12) Uani 1 1 d . . . . .
Ru1 Ru 0.26871(2) 0.74685(4) 0.15815(4) 0.02046(9) Uani 1 1 d . . . . .
Cl1 Cl 0.30873(5) 0.81268(12) 0.39539(15) 0.0306(3) Uani 1 1 d . . . . .
Cl2 Cl 0.23671(5) 0.57901(13) 0.28971(15) 0.0294(3) Uani 1 1 d . . . . .
N1 N 0.33819(17) 0.6409(4) 0.1423(5) 0.0235(10) Uani 1 1 d . . . . .
N2 N 0.5128(3) 0.4034(6) 0.0068(8) 0.0642(19) Uani 1 1 d . . . . .
C1 C 0.2052(2) 0.8833(5) 0.1374(7) 0.0284(12) Uani 1 1 d . . . . .
C2 C 0.1878(2) 0.7801(5) 0.0575(6) 0.0255(12) Uani 1 1 d . . . . .
H3 H 0.1583 0.7336 0.0918 0.031 Uiso 1 1 calc R U . . .
C3 C 0.2183(2) 0.7288(5) -0.0492(6) 0.0254(12) Uani 1 1 d . . . . .
H4 H 0.2090 0.6487 -0.0863 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2677(2) 0.7793(5) -0.0797(6) 0.0281(12) Uani 1 1 d . . . . .
C5 C 0.2857(2) 0.8838(5) -0.0007(7) 0.0322(13) Uani 1 1 d . . . . .
H6 H 0.3227 0.9106 -0.0052 0.039 Uiso 1 1 calc R U . . .
C6 C 0.2553(2) 0.9323(5) 0.1067(6) 0.0313(13) Uani 1 1 d . . . . .
H1 H 0.2721 0.9923 0.1741 0.038 Uiso 1 1 calc R U . . .
C7 C 0.1742(3) 0.9373(6) 0.2563(7) 0.0435(17) Uani 1 1 d . . . . .
H8 H 0.1999 0.9562 0.3405 0.052 Uiso 1 1 calc R U . . .
C8 C 0.1329(3) 0.8527(8) 0.3092(9) 0.067(2) Uani 1 1 d . . . . .
H10A H 0.1145 0.8911 0.3840 0.100 Uiso 1 1 calc R U . . .
H10B H 0.1076 0.8313 0.2282 0.100 Uiso 1 1 calc R U . . .
H10C H 0.1504 0.7822 0.3490 0.100 Uiso 1 1 calc R U . . .
C9 C 0.1480(3) 1.0544(7) 0.2014(8) 0.060(2) Uani 1 1 d . . . . .
H9A H 0.1747 1.1066 0.1685 0.091 Uiso 1 1 calc R U . . .
H9B H 0.1214 1.0381 0.1214 0.091 Uiso 1 1 calc R U . . .
H9C H 0.1313 1.0918 0.2800 0.091 Uiso 1 1 calc R U . . .
C10 C 0.3003(3) 0.7231(6) -0.1900(6) 0.0391(15) Uani 1 1 d . . . . .
H7A H 0.3375 0.7381 -0.1631 0.059 Uiso 1 1 calc R U . . .
H7B H 0.2902 0.7563 -0.2854 0.059 Uiso 1 1 calc R U . . .
H7C H 0.2940 0.6386 -0.1925 0.059 Uiso 1 1 calc R U . . .
C11 C 0.3336(2) 0.5328(5) 0.0785(6) 0.0277(13) Uani 1 1 d . . . . .
H17 H 0.2996 0.5012 0.0555 0.033 Uiso 1 1 calc R U . . .
C12 C 0.3774(2) 0.4675(5) 0.0461(6) 0.0308(13) Uani 1 1 d . . . . .
H18 H 0.3728 0.3930 0.0019 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4281(2) 0.5130(5) 0.0797(6) 0.0308(12) Uani 1 1 d . . . . .
C14 C 0.4333(2) 0.6238(5) 0.1479(6) 0.0314(13) Uani 1 1 d . . . . .
H20 H 0.4670 0.6564 0.1733 0.038 Uiso 1 1 calc R U . . .
C15 C 0.3880(2) 0.6839(5) 0.1770(6) 0.0291(12) Uani 1 1 d . . . . .
H21 H 0.3917 0.7578 0.2230 0.035 Uiso 1 1 calc R U . . .
C16 C 0.4755(3) 0.4504(6) 0.0402(8) 0.0419(16) 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
F1 C21 1.345(6) . ?
I1 C17 2.087(5) . ?
I2 C20 2.089(5) . ?
F2 C22 1.352(6) . ?
F3 C18 1.351(6) . ?
F4 C19 1.341(6) . ?
C17 C22 1.371(8) . ?
C17 C18 1.375(8) . ?
C18 C19 1.383(7) . ?
C19 C20 1.382(8) . ?
C20 C21 1.381(8) . ?
C21 C22 1.374(8) . ?
Ru1 N1 2.126(4) . ?
Ru1 C6 2.152(5) . ?
Ru1 C5 2.181(6) . ?
Ru1 C2 2.182(5) . ?
Ru1 C3 2.189(5) . ?
Ru1 C4 2.201(5) . ?
Ru1 C1 2.205(6) . ?
Ru1 Cl2 2.4099(14) . ?
Ru1 Cl1 2.4190(13) . ?
N1 C11 1.346(7) . ?
N1 C15 1.349(6) . ?
N2 C16 1.140(8) . ?
C1 C2 1.415(8) . ?
C1 C6 1.424(9) . ?
C1 C7 1.518(9) . ?
C2 C3 1.415(8) . ?
C2 H3 0.9800 . ?
C3 C4 1.412(8) . ?
C3 H4 0.9800 . ?
C4 C5 1.428(8) . ?
C4 C10 1.495(8) . ?
C5 C6 1.405(9) . ?
C5 H6 0.9800 . ?
C6 H1 0.9800 . ?
C7 C8 1.517(11) . ?
C7 C9 1.532(9) . ?
C7 H8 0.9800 . ?
C8 H10A 0.9600 . ?
C8 H10B 0.9600 . ?
C8 H10C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H7A 0.9600 . ?
C10 H7B 0.9600 . ?
C10 H7C 0.9600 . ?
C11 C12 1.375(8) . ?
C11 H17 0.9300 . ?
C12 C13 1.379(8) . ?
C12 H18 0.9300 . ?
C13 C14 1.391(8) . ?
C13 C16 1.455(9) . ?
C14 C15 1.369(8) . ?
C14 H20 0.9300 . ?
C15 H21 0.9300 . ?

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
C22 C17 C18 117.1(5) . . ?
C22 C17 I1 119.4(4) . . ?
C18 C17 I1 123.4(4) . . ?
F3 C18 C17 120.2(5) . . ?
F3 C18 C19 117.9(5) . . ?
C17 C18 C19 121.9(5) . . ?
F4 C19 C20 120.6(5) . . ?
F4 C19 C18 119.0(5) . . ?
C20 C19 C18 120.4(5) . . ?
C21 C20 C19 117.6(5) . . ?
C21 C20 I2 121.6(4) . . ?
C19 C20 I2 120.8(4) . . ?
F1 C21 C22 119.5(5) . . ?
F1 C21 C20 119.4(5) . . ?
C22 C21 C20 121.2(5) . . ?
F2 C22 C17 120.7(5) . . ?
F2 C22 C21 117.5(5) . . ?
C17 C22 C21 121.7(5) . . ?
N1 Ru1 C6 129.6(2) . . ?
N1 Ru1 C5 97.9(2) . . ?
C6 Ru1 C5 37.8(2) . . ?
N1 Ru1 C2 143.51(18) . . ?
C6 Ru1 C2 67.8(2) . . ?
C5 Ru1 C2 80.2(2) . . ?
N1 Ru1 C3 107.59(19) . . ?
C6 Ru1 C3 80.4(2) . . ?
C5 Ru1 C3 67.8(2) . . ?
C2 Ru1 C3 37.8(2) . . ?
N1 Ru1 C4 87.78(19) . . ?
C6 Ru1 C4 68.7(2) . . ?
C5 Ru1 C4 38.0(2) . . ?
C2 Ru1 C4 68.2(2) . . ?
C3 Ru1 C4 37.5(2) . . ?
N1 Ru1 C1 166.6(2) . . ?
C6 Ru1 C1 38.1(2) . . ?
C5 Ru1 C1 68.8(2) . . ?
C2 Ru1 C1 37.6(2) . . ?
C3 Ru1 C1 68.5(2) . . ?
C4 Ru1 C1 81.8(2) . . ?
N1 Ru1 Cl2 84.86(12) . . ?
C6 Ru1 Cl2 144.22(18) . . ?
C5 Ru1 Cl2 167.36(16) . . ?
C2 Ru1 Cl2 90.23(15) . . ?
C3 Ru1 Cl2 99.60(15) . . ?
C4 Ru1 Cl2 130.32(15) . . ?
C1 Ru1 Cl2 108.26(18) . . ?
N1 Ru1 Cl1 87.45(12) . . ?
C6 Ru1 Cl1 86.82(15) . . ?
C5 Ru1 Cl1 106.90(16) . . ?
C2 Ru1 Cl1 128.26(15) . . ?
C3 Ru1 Cl1 164.42(15) . . ?
C4 Ru1 Cl1 143.17(15) . . ?
C1 Ru1 Cl1 95.90(16) . . ?
Cl2 Ru1 Cl1 85.50(5) . . ?
C11 N1 C15 117.6(5) . . ?
C11 N1 Ru1 119.6(4) . . ?
C15 N1 Ru1 122.2(4) . . ?
C2 C1 C6 116.7(6) . . ?
C2 C1 C7 122.8(6) . . ?
C6 C1 C7 120.4(5) . . ?
C2 C1 Ru1 70.3(3) . . ?
C6 C1 Ru1 68.9(3) . . ?
C7 C1 Ru1 129.0(4) . . ?
C3 C2 C1 121.8(5) . . ?
C3 C2 Ru1 71.4(3) . . ?
C1 C2 Ru1 72.1(3) . . ?
C3 C2 H3 118.4 . . ?
C1 C2 H3 118.4 . . ?
Ru1 C2 H3 118.4 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 Ru1 71.7(3) . . ?
C2 C3 Ru1 70.9(3) . . ?
C4 C3 H4 119.0 . . ?
C2 C3 H4 119.0 . . ?
Ru1 C3 H4 119.0 . . ?
C3 C4 C5 118.2(5) . . ?
C3 C4 C10 120.5(5) . . ?
C5 C4 C10 121.3(5) . . ?
C3 C4 Ru1 70.8(3) . . ?
C5 C4 Ru1 70.2(3) . . ?
C10 C4 Ru1 129.6(4) . . ?
C6 C5 C4 120.2(5) . . ?
C6 C5 Ru1 70.0(3) . . ?
C4 C5 Ru1 71.7(3) . . ?
C6 C5 H6 119.2 . . ?
C4 C5 H6 119.2 . . ?
Ru1 C5 H6 119.2 . . ?
C5 C6 C1 122.2(5) . . ?
C5 C6 Ru1 72.2(3) . . ?
C1 C6 Ru1 72.9(3) . . ?
C5 C6 H1 118.4 . . ?
C1 C6 H1 118.4 . . ?
Ru1 C6 H1 118.4 . . ?
C8 C7 C1 112.8(6) . . ?
C8 C7 C9 110.7(6) . . ?
C1 C7 C9 109.9(6) . . ?
C8 C7 H8 107.7 . . ?
C1 C7 H8 107.7 . . ?
C9 C7 H8 107.7 . . ?
C7 C8 H10A 109.5 . . ?
C7 C8 H10B 109.5 . . ?
H10A C8 H10B 109.5 . . ?
C7 C8 H10C 109.5 . . ?
H10A C8 H10C 109.5 . . ?
H10B C8 H10C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H7A 109.5 . . ?
C4 C10 H7B 109.5 . . ?
H7A C10 H7B 109.5 . . ?
C4 C10 H7C 109.5 . . ?
H7A C10 H7C 109.5 . . ?
H7B C10 H7C 109.5 . . ?
N1 C11 C12 122.3(5) . . ?
N1 C11 H17 118.8 . . ?
C12 C11 H17 118.8 . . ?
C11 C12 C13 119.6(5) . . ?
C11 C12 H18 120.2 . . ?
C13 C12 H18 120.2 . . ?
C12 C13 C14 118.5(5) . . ?
C12 C13 C16 121.7(5) . . ?
C14 C13 C16 119.7(5) . . ?
C15 C14 C13 118.7(5) . . ?
C15 C14 H20 120.6 . . ?
C13 C14 H20 120.6 . . ?
N1 C15 C14 123.2(5) . . ?
N1 C15 H21 118.4 . . ?
C14 C15 H21 118.4 . . ?
N2 C16 C13 178.3(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 C17 C18 F3 -176.5(5) . . . . ?
I1 C17 C18 F3 7.1(8) . . . . ?
C22 C17 C18 C19 3.9(8) . . . . ?
I1 C17 C18 C19 -172.6(4) . . . . ?
F3 C18 C19 F4 -0.3(8) . . . . ?
C17 C18 C19 F4 179.4(5) . . . . ?
F3 C18 C19 C20 178.2(5) . . . . ?
C17 C18 C19 C20 -2.1(8) . . . . ?
F4 C19 C20 C21 177.4(5) . . . . ?
C18 C19 C20 C21 -1.0(8) . . . . ?
F4 C19 C20 I2 -3.1(7) . . . . ?
C18 C19 C20 I2 178.4(4) . . . . ?
C19 C20 C21 F1 -178.1(5) . . . . ?
I2 C20 C21 F1 2.4(7) . . . . ?
C19 C20 C21 C22 2.4(8) . . . . ?
I2 C20 C21 C22 -177.1(4) . . . . ?
C18 C17 C22 F2 178.5(5) . . . . ?
I1 C17 C22 F2 -4.9(7) . . . . ?
C18 C17 C22 C21 -2.5(9) . . . . ?
I1 C17 C22 C21 174.1(4) . . . . ?
F1 C21 C22 F2 -1.0(8) . . . . ?
C20 C21 C22 F2 178.4(5) . . . . ?
F1 C21 C22 C17 179.9(5) . . . . ?
C20 C21 C22 C17 -0.6(9) . . . . ?
C6 C1 C2 C3 -0.8(8) . . . . ?
C7 C1 C2 C3 -177.7(5) . . . . ?
Ru1 C1 C2 C3 -53.4(5) . . . . ?
C6 C1 C2 Ru1 52.6(4) . . . . ?
C7 C1 C2 Ru1 -124.3(6) . . . . ?
C1 C2 C3 C4 0.1(8) . . . . ?
Ru1 C2 C3 C4 -53.6(4) . . . . ?
C1 C2 C3 Ru1 53.7(5) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
Ru1 C3 C4 C5 -53.6(4) . . . . ?
C2 C3 C4 C10 178.6(5) . . . . ?
Ru1 C3 C4 C10 125.3(5) . . . . ?
C2 C3 C4 Ru1 53.2(4) . . . . ?
C3 C4 C5 C6 1.5(8) . . . . ?
C10 C4 C5 C6 -177.5(5) . . . . ?
Ru1 C4 C5 C6 -52.4(5) . . . . ?
C3 C4 C5 Ru1 53.9(4) . . . . ?
C10 C4 C5 Ru1 -125.1(5) . . . . ?
C4 C5 C6 C1 -2.3(8) . . . . ?
Ru1 C5 C6 C1 -55.5(5) . . . . ?
C4 C5 C6 Ru1 53.2(5) . . . . ?
C2 C1 C6 C5 1.9(8) . . . . ?
C7 C1 C6 C5 178.9(5) . . . . ?
Ru1 C1 C6 C5 55.2(5) . . . . ?
C2 C1 C6 Ru1 -53.2(4) . . . . ?
C7 C1 C6 Ru1 123.7(5) . . . . ?
C2 C1 C7 C8 16.2(8) . . . . ?
C6 C1 C7 C8 -160.6(6) . . . . ?
Ru1 C1 C7 C8 -74.1(7) . . . . ?
C2 C1 C7 C9 -108.0(7) . . . . ?
C6 C1 C7 C9 75.2(7) . . . . ?
Ru1 C1 C7 C9 161.7(5) . . . . ?
C15 N1 C11 C12 -1.2(8) . . . . ?
Ru1 N1 C11 C12 170.5(4) . . . . ?
N1 C11 C12 C13 0.1(9) . . . . ?
C11 C12 C13 C14 1.0(9) . . . . ?
C11 C12 C13 C16 -176.5(6) . . . . ?
C12 C13 C14 C15 -1.0(9) . . . . ?
C16 C13 C14 C15 176.6(6) . . . . ?
C11 N1 C15 C14 1.2(8) . . . . ?
Ru1 N1 C15 C14 -170.3(4) . . . . ?
C13 C14 C15 N1 -0.2(9) . . . . ?

_refine_diff_density_max         0.779
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.086

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_1_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1940713'
loop_
_audit_author_name
_audit_author_address
'Yury Torubaev' 'Kurnakov Institute of General and Inorganic Chemistry'
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-09-26 downloaded from the CCDC.
;
_audit_creation_date             2019-05-27
_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            ?
_chemical_name_systematic        '1,4-diiodotetrafluorobenzene 4-cyanopyridine'
_chemical_formula_moiety         '2(C3 F2 I), C6 H4 N2'
_chemical_formula_sum            'C12 H4 F4 I2 N2'
_chemical_formula_weight         505.97
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.3341(5)
_cell_length_b                   6.2294(6)
_cell_length_c                   26.005(3)
_cell_angle_alpha                88.445(4)
_cell_angle_beta                 87.480(4)
_cell_angle_gamma                82.788(4)
_cell_volume                     695.72(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4852
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.07
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    4.555
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1246 before and 0.0682 after correction.
The Ratio of minimum to maximum transmission is 0.5588.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            12332
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_min         2.352
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3246
_reflns_number_total             3610
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.907
_refine_diff_density_min         -2.550
_refine_diff_density_rms         0.222
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.291
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0643
_refine_ls_restrained_S_all      1.291
_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)+(0.0360P)²+5.4571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1366
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
I001 I 0.24108(12) 0.20199(9) 0.11406(2) 0.03086(16) Uani 1 1 d . . . A 1
I002 I 1.27033(12) 1.20438(8) 0.39933(2) 0.02838(16) Uani 1 1 d . . . . .
F003 F 1.2017(12) 1.1500(8) 0.52154(19) 0.0358(11) Uani 1 1 d . . . . .
F004 F -0.2880(13) -0.3618(8) 0.0041(2) 0.0388(12) Uani 1 1 d . . . A 1
F005 F 1.6097(13) 1.6335(8) 0.40145(17) 0.0363(11) Uani 1 1 d . . . . .
F006 F -0.0881(13) -0.2162(8) 0.08983(19) 0.0397(12) Uani 1 1 d . . . A 1
C007 C 1.4017(17) 1.3843(12) 0.4590(3) 0.0234(14) Uani 1 1 d . . . . .
N008 N 0.4666(17) 0.4195(12) 0.2017(3) 0.0330(15) Uani 1 1 d . . . . .
C009 C 0.1037(16) 0.0795(12) 0.0459(3) 0.0227(14) Uani 1 1 d . . . A 1
C00A C -0.0442(18) -0.1056(13) 0.0456(3) 0.0273(16) Uani 1 1 d . . . A 1
C00B C 1.3517(17) 1.3211(11) 0.5100(3) 0.0229(14) Uani 1 1 d . . . . .
C00C C -0.1421(17) -0.1833(12) 0.0013(3) 0.0250(15) Uani 1 1 d . . . A 1
C00D C 1.5526(18) 1.5653(12) 0.4501(3) 0.0242(15) Uani 1 1 d . . . . .
C00E C 0.7778(19) 0.6849(13) 0.2588(3) 0.0287(16) Uani 1 1 d . . . . .
N00F N 1.073(2) 0.9408(15) 0.3099(3) 0.048(2) Uani 1 1 d . . . . .
C00G C 0.695(2) 0.7458(15) 0.2094(4) 0.0362(19) Uani 1 1 d . . . . .
H00G H 0.744050 0.878950 0.194399 0.043 Uiso 1 1 calc R . . . .
C00H C 0.540(2) 0.6078(15) 0.1822(3) 0.0359(19) Uani 1 1 d . . . . .
H00H H 0.483837 0.648742 0.148135 0.043 Uiso 1 1 calc R . . . .
C00I C 0.699(2) 0.4904(14) 0.2798(3) 0.0320(17) Uani 1 1 d . . . . .
H00I H 0.749956 0.445516 0.313892 0.038 Uiso 1 1 calc R . . . .
C00J C 0.543(2) 0.3644(14) 0.2493(3) 0.0338(18) Uani 1 1 d . . . . .
H00J H 0.489056 0.231134 0.263266 0.041 Uiso 1 1 calc R . . . .
C00K C 0.947(2) 0.8258(15) 0.2879(4) 0.0369(19) 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
I001 C009 2.088(7) . ?
I002 C007 2.080(7) . ?
F003 C00B 1.337(8) . ?
F004 C00C 1.345(8) . ?
F005 C00D 1.346(8) . ?
F006 C00A 1.344(9) . ?
C007 C00B 1.388(11) . ?
C007 C00D 1.382(11) . ?
N008 C00H 1.336(12) . ?
N008 C00J 1.319(11) . ?
C009 C00A 1.388(11) . ?
C009 C00C 1.385(11) 2 ?
C00A C00C 1.366(11) . ?
C00B C00D 1.378(10) 2_886 ?
C00E C00G 1.381(12) . ?
C00E C00I 1.391(12) . ?
C00E C00K 1.457(11) . ?
N00F C00K 1.136(11) . ?
C00G H00G 0.9500 . ?
C00G C00H 1.381(12) . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00I C00J 1.383(12) . ?
C00J H00J 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00B C007 I002 120.8(5) . . ?
C00D C007 I002 122.1(5) . . ?
C00D C007 C00B 117.1(7) . . ?
C00J N008 C00H 118.2(7) . . ?
C00A C009 I001 121.9(6) . . ?
C00C C009 I001 122.0(5) 2 . ?
C00C C009 C00A 116.1(7) 2 . ?
F006 C00A C009 119.6(7) . . ?
F006 C00A C00C 118.2(7) . . ?
C00C C00A C009 122.2(7) . . ?
F003 C00B C007 120.3(6) . . ?
F003 C00B C00D 118.3(7) . 2_886 ?
C00D C00B C007 121.4(7) 2_886 . ?
F004 C00C C009 119.4(7) . 2 ?
F004 C00C C00A 118.8(7) . . ?
C00A C00C C009 121.7(7) . 2 ?
F005 C00D C007 119.8(7) . . ?
F005 C00D C00B 118.6(7) . 2_886 ?
C00B C00D C007 121.5(7) 2_886 . ?
C00G C00E C00I 119.4(7) . . ?
C00G C00E C00K 119.1(8) . . ?
C00I C00E C00K 121.5(8) . . ?
C00E C00G H00G 120.9 . . ?
C00H C00G C00E 118.1(8) . . ?
C00H C00G H00G 120.9 . . ?
N008 C00H C00G 123.0(8) . . ?
N008 C00H H00H 118.5 . . ?
C00G C00H H00H 118.5 . . ?
C00E C00I H00I 121.1 . . ?
C00J C00I C00E 117.8(7) . . ?
C00J C00I H00I 121.1 . . ?
N008 C00J C00I 123.5(8) . . ?
N008 C00J H00J 118.3 . . ?
C00I C00J H00J 118.3 . . ?
N00F C00K C00E 178.0(11) . . ?

_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_1a
_database_code_depnum_ccdc_archive 'CCDC 1940711'
loop_
_audit_author_name
_audit_author_address
'Yury Torubaev' 'Kurnakov Institute of General and Inorganic Chemistry'
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-09-26 downloaded from the CCDC.
;
_audit_creation_date             2019-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            ?
_chemical_name_systematic        
(4-Cyanopyridine)-(h6-p-cymene)-diiodo-ruthenium(ii)
_chemical_formula_moiety         'C16 H17 I2 N2 Ru'
_chemical_formula_sum            'C16 H17 I2 N2 Ru'
_chemical_formula_weight         592.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 '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                   11.609(8)
_cell_length_b                   13.088(9)
_cell_length_c                   11.893(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.479(10)
_cell_angle_gamma                90
_cell_volume                     1795(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    60
_cell_measurement_temperature    296
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.307
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1301 before and 0.0514 after correction.
The Ratio of minimum to maximum transmission is 0.6662.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21140
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.589
_diffrn_reflns_theta_min         2.322
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3418
_reflns_number_total             4070
_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       'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_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    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         1.344
_refine_diff_density_min         -1.607
_refine_diff_density_rms         0.167
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4070
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.054
_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)+(0.0317P)²+3.3577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0659
_refine_ls_wR_factor_ref         0.0712
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_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. Uiso/Uaniso restraints and constraints
Uanis(C9) = Uanis(C10)
Uanis(C9A) = Uanis(C10A)
3. Others
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=1-
 FVAR(1)
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(C10A)=Sof(H10D)=Sof(H10E)=
 Sof(H10F)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
4.b Me refined with riding coordinates:
 C9(H9A,H9B,H9C), C9A(H9AA,H9AB,H9AC), C10(H10A,H10B,H10C)
4.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15)
4.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C10A(H10D,H10E,H10F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
I1 I 0.20493(2) 0.02310(2) 0.10374(2) 0.02922(8) Uani 1 1 d . . . . .
I2 I 0.42202(3) -0.17395(2) 0.22010(3) 0.03372(9) Uani 1 1 d . . . . .
Ru1 Ru 0.29672(3) -0.14740(2) 0.01390(3) 0.01995(8) Uani 1 1 d . . . . .
N1 N 0.1598(3) -0.2334(2) 0.0738(3) 0.0220(7) Uani 1 1 d . . . . .
N2 N -0.1905(4) -0.4988(3) 0.0921(4) 0.0456(11) Uani 1 1 d . . . . .
C1 C 0.2428(4) -0.0939(4) -0.1607(4) 0.0346(10) Uani 1 1 d . . . . .
C2 C 0.3544(4) -0.0534(3) -0.1216(4) 0.0296(9) Uani 1 1 d . . . . .
H2 H 0.362555 0.020506 -0.109881 0.036 Uiso 1 1 calc R . . . .
C3 C 0.4472(4) -0.1177(3) -0.0803(4) 0.0262(9) Uani 1 1 d . . . . .
H3 H 0.516793 -0.086725 -0.039912 0.031 Uiso 1 1 calc R . . . .
C4 C 0.4328(4) -0.2269(3) -0.0741(4) 0.0282(9) Uani 1 1 d . . . . .
C5 C 0.3223(4) -0.2663(3) -0.1115(4) 0.0318(10) Uani 1 1 d . . . . .
H5 H 0.304899 -0.337460 -0.094116 0.038 Uiso 1 1 calc R . . . .
C6 C 0.2298(4) -0.2007(4) -0.1541(4) 0.0359(11) Uani 1 1 d . . . . .
H6 H 0.151201 -0.229101 -0.164880 0.043 Uiso 1 1 calc R . . . .
C7 C 0.1436(4) -0.0250(5) -0.2026(5) 0.0535(15) Uani 1 1 d . . . . .
H7A H 0.143832 -0.013488 -0.282261 0.080 Uiso 1 1 calc GR . . . .
H7B H 0.151665 0.039090 -0.163202 0.080 Uiso 1 1 calc GR . . . .
H7C H 0.071798 -0.056586 -0.188979 0.080 Uiso 1 1 calc GR . . . .
C8 C 0.5337(4) -0.2961(4) -0.0329(4) 0.0352(10) Uani 1 1 d . . . . .
C9 C 0.5813(13) -0.3504(10) -0.1299(13) 0.046(3) Uani 0.456(10) 1 d . . P A 2
H9A H 0.518508 -0.379406 -0.179087 0.069 Uiso 0.456(10) 1 calc R . P A 2
H9B H 0.622685 -0.302566 -0.171456 0.069 Uiso 0.456(10) 1 calc R . P A 2
H9C H 0.632920 -0.403820 -0.100612 0.069 Uiso 0.456(10) 1 calc R . P A 2
C9A C 0.4975(9) -0.3916(8) 0.0121(9) 0.047(2) Uani 0.544(10) 1 d . . P A 1
H9AA H 0.564436 -0.432214 0.036800 0.071 Uiso 0.544(10) 1 calc R . P A 1
H9AB H 0.454653 -0.378500 0.075136 0.071 Uiso 0.544(10) 1 calc R . P A 1
H9AC H 0.449139 -0.427753 -0.045512 0.071 Uiso 0.544(10) 1 calc R . P A 1
C10 C 0.6342(10) -0.2520(9) 0.0417(11) 0.046(3) Uani 0.456(10) 1 d . . P A 2
H10A H 0.606287 -0.216988 0.104154 0.069 Uiso 0.456(10) 1 calc R . P A 2
H10B H 0.685478 -0.306110 0.069791 0.069 Uiso 0.456(10) 1 calc R . P A 2
H10C H 0.675243 -0.204856 -0.001054 0.069 Uiso 0.456(10) 1 calc R . P A 2
C10A C 0.6045(10) -0.3077(9) -0.1393(10) 0.047(2) Uani 0.544(10) 1 d . . P A 1
H10D H 0.627866 -0.241443 -0.162785 0.071 Uiso 0.544(10) 1 calc GR . P A 1
H10E H 0.556311 -0.339660 -0.200257 0.071 Uiso 0.544(10) 1 calc GR . P A 1
H10F H 0.671884 -0.349086 -0.118955 0.071 Uiso 0.544(10) 1 calc GR . P A 1
C11 C 0.1787(4) -0.3252(3) 0.1226(4) 0.0255(8) Uani 1 1 d . . . . .
H11 H 0.254419 -0.343530 0.148840 0.031 Uiso 1 1 calc R . . . .
C12 C 0.0895(4) -0.3946(3) 0.1356(4) 0.0295(9) Uani 1 1 d . . . . .
H12 H 0.105001 -0.457123 0.171273 0.035 Uiso 1 1 calc R . . . .
C13 C -0.0228(4) -0.3675(3) 0.0936(4) 0.0271(9) Uani 1 1 d . . . . .
C14 C -0.0445(4) -0.2702(3) 0.0466(4) 0.0283(9) Uani 1 1 d . . . . .
H14 H -0.119612 -0.249266 0.021576 0.034 Uiso 1 1 calc R . . . .
C15 C 0.0490(3) -0.2063(3) 0.0385(4) 0.0270(9) Uani 1 1 d . . . . .
H15 H 0.035261 -0.141693 0.007421 0.032 Uiso 1 1 calc R . . . .
C16 C -0.1167(4) -0.4406(3) 0.0948(4) 0.0302(9) 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
I1 Ru1 2.7411(13) . ?
I2 Ru1 2.7285(15) . ?
Ru1 N1 2.135(3) . ?
Ru1 C1 2.214(5) . ?
Ru1 C2 2.192(4) . ?
Ru1 C3 2.214(4) . ?
Ru1 C4 2.246(4) . ?
Ru1 C5 2.198(4) . ?
Ru1 C6 2.176(5) . ?
N1 C11 1.341(5) . ?
N1 C15 1.354(5) . ?
N2 C16 1.144(6) . ?
C1 C2 1.429(6) . ?
C1 C6 1.410(7) . ?
C1 C7 1.502(7) . ?
C2 H2 0.9800 . ?
C2 C3 1.411(6) . ?
C3 H3 0.9800 . ?
C3 C4 1.441(6) . ?
C4 C5 1.408(6) . ?
C4 C8 1.517(6) . ?
C5 H5 0.9800 . ?
C5 C6 1.422(7) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.511(14) . ?
C8 C9A 1.442(11) . ?
C8 C10 1.499(14) . ?
C8 C10A 1.591(11) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10A H10D 0.9600 . ?
C10A H10E 0.9600 . ?
C10A H10F 0.9600 . ?
C11 H11 0.9300 . ?
C11 C12 1.399(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(6) . ?
C13 C14 1.402(6) . ?
C13 C16 1.452(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(6) . ?
C15 H15 0.9300 . ?

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
I2 Ru1 I1 86.83(3) . . ?
N1 Ru1 I1 87.85(10) . . ?
N1 Ru1 I2 88.52(10) . . ?
N1 Ru1 C1 109.74(15) . . ?
N1 Ru1 C2 147.40(15) . . ?
N1 Ru1 C3 157.12(14) . . ?
N1 Ru1 C4 120.03(14) . . ?
N1 Ru1 C5 90.89(14) . . ?
N1 Ru1 C6 86.29(15) . . ?
C1 Ru1 I1 91.53(14) . . ?
C1 Ru1 I2 161.61(12) . . ?
C1 Ru1 C4 81.32(17) . . ?
C2 Ru1 I1 89.66(12) . . ?
C2 Ru1 I2 123.79(12) . . ?
C2 Ru1 C1 37.83(16) . . ?
C2 Ru1 C3 37.36(16) . . ?
C2 Ru1 C4 68.17(16) . . ?
C2 Ru1 C5 79.80(17) . . ?
C3 Ru1 I1 114.71(11) . . ?
C3 Ru1 I2 96.09(12) . . ?
C3 Ru1 C1 68.01(16) . . ?
C3 Ru1 C4 37.70(15) . . ?
C4 Ru1 I1 152.04(10) . . ?
C4 Ru1 I2 91.59(12) . . ?
C5 Ru1 I1 158.25(13) . . ?
C5 Ru1 I2 114.86(14) . . ?
C5 Ru1 C1 68.49(19) . . ?
C5 Ru1 C3 66.82(15) . . ?
C5 Ru1 C4 36.92(15) . . ?
C6 Ru1 I1 120.33(14) . . ?
C6 Ru1 I2 152.06(14) . . ?
C6 Ru1 C1 37.46(19) . . ?
C6 Ru1 C2 67.16(17) . . ?
C6 Ru1 C3 79.16(16) . . ?
C6 Ru1 C4 67.72(17) . . ?
C6 Ru1 C5 37.95(18) . . ?
C11 N1 Ru1 121.7(3) . . ?
C11 N1 C15 118.2(3) . . ?
C15 N1 Ru1 118.4(3) . . ?
C2 C1 Ru1 70.2(2) . . ?
C2 C1 C7 121.2(5) . . ?
C6 C1 Ru1 69.8(3) . . ?
C6 C1 C2 116.7(4) . . ?
C6 C1 C7 122.1(4) . . ?
C7 C1 Ru1 128.7(3) . . ?
Ru1 C2 H2 118.8 . . ?
C1 C2 Ru1 71.9(2) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 Ru1 72.2(2) . . ?
C3 C2 C1 121.4(4) . . ?
C3 C2 H2 118.8 . . ?
Ru1 C3 H3 118.6 . . ?
C2 C3 Ru1 70.5(2) . . ?
C2 C3 H3 118.6 . . ?
C2 C3 C4 121.4(4) . . ?
C4 C3 Ru1 72.4(2) . . ?
C4 C3 H3 118.6 . . ?
C3 C4 Ru1 69.9(2) . . ?
C3 C4 C8 121.3(4) . . ?
C5 C4 Ru1 69.7(2) . . ?
C5 C4 C3 117.0(4) . . ?
C5 C4 C8 121.7(4) . . ?
C8 C4 Ru1 133.2(3) . . ?
Ru1 C5 H5 118.9 . . ?
C4 C5 Ru1 73.4(2) . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 121.1(4) . . ?
C6 C5 Ru1 70.2(3) . . ?
C6 C5 H5 118.9 . . ?
Ru1 C6 H6 118.2 . . ?
C1 C6 Ru1 72.8(3) . . ?
C1 C6 C5 122.5(4) . . ?
C1 C6 H6 118.2 . . ?
C5 C6 Ru1 71.9(3) . . ?
C5 C6 H6 118.2 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 C10A 104.5(5) . . ?
C9 C8 C4 111.7(7) . . ?
C9A C8 C4 113.0(5) . . ?
C9A C8 C10A 114.2(7) . . ?
C10 C8 C4 118.8(5) . . ?
C10 C8 C9 107.8(8) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C9A H9AA 109.5 . . ?
C8 C9A H9AB 109.5 . . ?
C8 C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C10A H10D 109.5 . . ?
C8 C10A H10E 109.5 . . ?
C8 C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
N1 C11 H11 118.6 . . ?
N1 C11 C12 122.8(4) . . ?
C12 C11 H11 118.6 . . ?
C11 C12 H12 120.9 . . ?
C13 C12 C11 118.1(4) . . ?
C13 C12 H12 120.9 . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 C16 120.2(4) . . ?
C14 C13 C16 120.1(4) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 C13 118.0(4) . . ?
C15 C14 H14 121.0 . . ?
N1 C15 C14 123.1(4) . . ?
N1 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
N2 C16 C13 177.7(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ru1 N1 C11 C12 -162.7(3) . . . . ?
Ru1 N1 C15 C14 162.5(3) . . . . ?
Ru1 C1 C2 C3 54.8(4) . . . . ?
Ru1 C1 C6 C5 -54.3(4) . . . . ?
Ru1 C2 C3 C4 53.7(4) . . . . ?
Ru1 C3 C4 C5 53.1(3) . . . . ?
Ru1 C3 C4 C8 -129.1(4) . . . . ?
Ru1 C4 C5 C6 53.6(4) . . . . ?
Ru1 C4 C8 C9 165.8(6) . . . . ?
Ru1 C4 C8 C9A 64.5(7) . . . . ?
Ru1 C4 C8 C10 -67.7(7) . . . . ?
Ru1 C4 C8 C10A -170.7(6) . . . . ?
Ru1 C5 C6 C1 54.7(4) . . . . ?
N1 C11 C12 C13 1.5(7) . . . . ?
C1 C2 C3 Ru1 -54.7(4) . . . . ?
C1 C2 C3 C4 -1.0(6) . . . . ?
C2 C1 C6 Ru1 54.0(3) . . . . ?
C2 C1 C6 C5 -0.3(6) . . . . ?
C2 C3 C4 Ru1 -52.8(4) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C2 C3 C4 C8 178.1(4) . . . . ?
C3 C4 C5 Ru1 -53.2(3) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C3 C4 C8 C9 -103.1(7) . . . . ?
C3 C4 C8 C9A 155.6(6) . . . . ?
C3 C4 C8 C10 23.3(7) . . . . ?
C3 C4 C8 C10A -79.6(7) . . . . ?
C4 C5 C6 Ru1 -55.1(4) . . . . ?
C4 C5 C6 C1 -0.4(7) . . . . ?
C5 C4 C8 C9 74.6(8) . . . . ?
C5 C4 C8 C9A -26.6(7) . . . . ?
C5 C4 C8 C10 -158.9(6) . . . . ?
C5 C4 C8 C10A 98.1(7) . . . . ?
C6 C1 C2 Ru1 -53.8(3) . . . . ?
C6 C1 C2 C3 1.0(6) . . . . ?
C7 C1 C2 Ru1 124.0(4) . . . . ?
C7 C1 C2 C3 178.8(4) . . . . ?
C7 C1 C6 Ru1 -123.8(4) . . . . ?
C7 C1 C6 C5 -178.1(4) . . . . ?
C8 C4 C5 Ru1 129.0(4) . . . . ?
C8 C4 C5 C6 -177.4(4) . . . . ?
C11 N1 C15 C14 -2.5(6) . . . . ?
C11 C12 C13 C14 -4.0(6) . . . . ?
C11 C12 C13 C16 173.9(4) . . . . ?
C12 C13 C14 C15 3.3(6) . . . . ?
C13 C14 C15 N1 0.0(7) . . . . ?
C15 N1 C11 C12 1.7(6) . . . . ?
C16 C13 C14 C15 -174.6(4) . . . . ?

_shelx_SHELXL_version_number     2017/1

_olex2_submission_special_instructions 'No special instructions were received'
