# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

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

data_Jude1_0m
_database_code_depnum_ccdc_archive 'CCDC 1510765'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7TC02976D 2017
_audit_update_record             
;
2016-10-19 deposited with the CCDC.
2017-11-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT020_Jude1_0m            
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.311 Report
RESPONSE: Poor crystallinity and weak diffraction signals affect Rint considerably
;
# Added during the CSD deposition process: Wednesday 19 October 2016 08:18 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-(4-Fluorophenyl)pyridine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 F N'
_chemical_formula_weight         173.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   20.810(5)
_cell_length_b                   5.7364(13)
_cell_length_c                   14.397(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.967(7)
_cell_angle_gamma                90
_cell_volume                     1697.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11653
_cell_measurement_theta_min      2.865
_cell_measurement_theta_max      23.996

_exptl_crystal_description       'irregular frament'
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   0.99
_exptl_transmission_factor_max   0.99
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11653
_diffrn_reflns_av_unetI/netI     0.1441
_diffrn_reflns_av_R_equivalents  0.3113
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.865
_diffrn_reflns_theta_max         23.996
_diffrn_reflns_theta_full        23.996
_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             1341
_reflns_number_gt                655
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0636P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1341
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1734
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.1660
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.06499(9) 0.6628(4) 0.39224(17) 0.0597(9) Uani 1 1 d . . . . .
N1 N 0.36436(14) 0.4822(5) 0.4053(2) 0.0353(9) Uani 1 1 d . . . . .
C1 C 0.13022(17) 0.6657(7) 0.3867(3) 0.0352(11) Uani 1 1 d . . . . .
C2 C 0.16714(16) 0.4805(7) 0.4217(3) 0.0381(11) Uani 1 1 d . . . . .
H9 H 0.1491 0.3556 0.4498 0.046 Uiso 1 1 calc R U . . .
C3 C 0.23265(16) 0.4852(6) 0.4140(2) 0.0317(10) Uani 1 1 d . . . . .
H2 H 0.2587 0.3582 0.4351 0.038 Uiso 1 1 calc R U . . .
C4 C 0.26037(16) 0.6753(6) 0.3753(2) 0.0259(9) Uani 1 1 d . . . . .
C5 C 0.33159(16) 0.6738(6) 0.3711(2) 0.0271(10) Uani 1 1 d . . . . .
C6 C 0.36297(16) 0.8592(6) 0.3345(3) 0.0369(11) Uani 1 1 d . . . . .
H4 H 0.3396 0.9909 0.3117 0.044 Uiso 1 1 calc R U . . .
C7 C 0.42857(18) 0.8458(7) 0.3325(3) 0.0464(12) Uani 1 1 d . . . . .
H5 H 0.4500 0.9676 0.3077 0.056 Uiso 1 1 calc R U . . .
C8 C 0.46232(19) 0.6498(7) 0.3677(3) 0.0474(12) Uani 1 1 d . . . . .
H1 H 0.5068 0.6369 0.3674 0.057 Uiso 1 1 calc R U . . .
C10 C 0.42838(17) 0.4746(7) 0.4030(3) 0.0450(11) Uani 1 1 d . . . . .
H6 H 0.4512 0.3426 0.4267 0.054 Uiso 1 1 calc R U . . .
C11 C 0.22008(17) 0.8578(6) 0.3415(3) 0.0325(10) Uani 1 1 d . . . . .
H8 H 0.2377 0.9860 0.3149 0.039 Uiso 1 1 calc R U . . .
C12 C 0.15445(17) 0.8542(6) 0.3462(3) 0.0387(11) Uani 1 1 d . . . . .
H7 H 0.1275 0.9767 0.3224 0.046 Uiso 1 1 calc R U . . .


_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 C1 1.372(4) . ?
N1 C10 1.338(4) . ?
N1 C5 1.345(4) . ?
C1 C2 1.361(4) . ?
C1 C12 1.362(5) . ?
C2 C3 1.385(4) . ?
C2 H9 0.9300 . ?
C3 C4 1.390(4) . ?
C3 H2 0.9300 . ?
C4 C11 1.382(4) . ?
C4 C5 1.493(5) . ?
C5 C6 1.394(4) . ?
C6 C7 1.372(4) . ?
C6 H4 0.9300 . ?
C7 C8 1.379(5) . ?
C7 H5 0.9300 . ?
C8 C10 1.371(5) . ?
C8 H1 0.9300 . ?
C10 H6 0.9300 . ?
C11 C12 1.378(4) . ?
C11 H8 0.9300 . ?
C12 H7 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
C10 N1 C5 117.9(3) . . ?
C2 C1 C12 123.6(3) . . ?
C2 C1 F1 118.4(3) . . ?
C12 C1 F1 118.1(3) . . ?
C1 C2 C3 117.4(4) . . ?
C1 C2 H9 121.3 . . ?
C3 C2 H9 121.3 . . ?
C2 C3 C4 121.5(4) . . ?
C2 C3 H2 119.3 . . ?
C4 C3 H2 119.3 . . ?
C11 C4 C3 118.0(3) . . ?
C11 C4 C5 122.8(3) . . ?
C3 C4 C5 119.2(3) . . ?
N1 C5 C6 121.4(3) . . ?
N1 C5 C4 116.1(3) . . ?
C6 C5 C4 122.5(3) . . ?
C7 C6 C5 119.4(3) . . ?
C7 C6 H4 120.3 . . ?
C5 C6 H4 120.3 . . ?
C6 C7 C8 119.3(4) . . ?
C6 C7 H5 120.4 . . ?
C8 C7 H5 120.4 . . ?
C10 C8 C7 118.1(4) . . ?
C10 C8 H1 120.9 . . ?
C7 C8 H1 120.9 . . ?
N1 C10 C8 123.9(4) . . ?
N1 C10 H6 118.1 . . ?
C8 C10 H6 118.1 . . ?
C12 C11 C4 121.5(3) . . ?
C12 C11 H8 119.2 . . ?
C4 C11 H8 119.2 . . ?
C1 C12 C11 117.9(3) . . ?
C1 C12 H7 121.0 . . ?
C11 C12 H7 121.0 . . ?

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
C12 C1 C2 C3 -0.9(6) . . . . ?
F1 C1 C2 C3 178.9(3) . . . . ?
C1 C2 C3 C4 2.5(5) . . . . ?
C2 C3 C4 C11 -2.3(5) . . . . ?
C2 C3 C4 C5 178.3(3) . . . . ?
C10 N1 C5 C6 -0.1(5) . . . . ?
C10 N1 C5 C4 -179.8(3) . . . . ?
C11 C4 C5 N1 -178.8(3) . . . . ?
C3 C4 C5 N1 0.6(5) . . . . ?
C11 C4 C5 C6 1.4(5) . . . . ?
C3 C4 C5 C6 -179.2(3) . . . . ?
N1 C5 C6 C7 0.5(6) . . . . ?
C4 C5 C6 C7 -179.7(3) . . . . ?
C5 C6 C7 C8 -0.7(6) . . . . ?
C6 C7 C8 C10 0.4(6) . . . . ?
C5 N1 C10 C8 -0.2(6) . . . . ?
C7 C8 C10 N1 0.1(6) . . . . ?
C3 C4 C11 C12 0.5(5) . . . . ?
C5 C4 C11 C12 179.9(4) . . . . ?
C2 C1 C12 C11 -0.7(6) . . . . ?
F1 C1 C12 C11 179.4(3) . . . . ?
C4 C11 C12 C1 1.0(6) . . . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_Jude2a_0m
_database_code_depnum_ccdc_archive 'CCDC 1510766'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7TC02976D 2017
_audit_update_record             
;
2016-10-19 deposited with the CCDC.
2017-11-15 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT340_Jude2a_0m           
;
PROBLEM: Low Bond Precision on  C-C Bonds
RESPONSE: Poor Crystal quality did not allow a for high angle measurment
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        6-phenyl-2,2'-bipyridine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 N2'
_chemical_formula_weight         232.28

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   22.148(16)
_cell_length_b                   5.489(4)
_cell_length_c                   11.950(9)
_cell_angle_alpha                90
_cell_angle_beta                 122.238(18)
_cell_angle_gamma                90
_cell_volume                     1228.9(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3131
_cell_measurement_theta_min      3.410
_cell_measurement_theta_max      23.532

_exptl_crystal_description       'irregular frament'
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   0.99
_exptl_transmission_factor_max   0.99
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   'Blessing, 1995'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3131
_diffrn_reflns_av_unetI/netI     0.1129
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.410
_diffrn_reflns_theta_max         23.532
_diffrn_reflns_theta_full        23.532
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.942
_reflns_number_total             1719
_reflns_number_gt                919
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     0.892
_reflns_Friedel_fraction_full    0.892

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0105(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 262 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.6(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1719
_refine_ls_number_parameters     164
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1455
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.973
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3653(2) 0.6028(9) 0.3972(5) 0.0462(15) Uani 1 1 d . . . . .
N2 N 0.3755(3) 0.4071(11) 0.1195(5) 0.0699(19) Uani 1 1 d . . . . .
C1 C 0.4547(3) 0.0598(16) 0.1814(8) 0.071(2) Uani 1 1 d . . . . .
H1 H 0.4778 -0.0539 0.1593 0.085 Uiso 1 1 calc R U . . .
C2 C 0.4634(3) 0.0637(15) 0.3036(7) 0.069(2) Uani 1 1 d . . . . .
H2 H 0.4927 -0.0514 0.3665 0.083 Uiso 1 1 calc R U . . .
C3 C 0.4296(4) 0.2349(15) 0.3346(6) 0.062(2) Uani 1 1 d . . . . .
H3 H 0.4362 0.2376 0.4182 0.075 Uiso 1 1 calc R U . . .
C4 C 0.3857(3) 0.4034(12) 0.2401(6) 0.0495(17) Uani 1 1 d . . . . .
C5 C 0.3481(3) 0.5932(13) 0.2704(7) 0.0487(17) Uani 1 1 d . . . . .
C6 C 0.3337(3) 0.7748(13) 0.4303(6) 0.0466(17) Uani 1 1 d . . . . .
C7 C 0.3539(3) 0.7639(15) 0.5715(6) 0.0431(17) Uani 1 1 d . . . . .
C8 C 0.3962(3) 0.5815(13) 0.6540(6) 0.0590(19) Uani 1 1 d . . . . .
H8 H 0.4133 0.4631 0.6220 0.071 Uiso 1 1 calc R U . . .
C9 C 0.4144(3) 0.5688(13) 0.7849(6) 0.062(2) Uani 1 1 d . . . . .
H9 H 0.4438 0.4439 0.8393 0.074 Uiso 1 1 calc R U . . .
C10 C 0.3890(3) 0.7412(16) 0.8342(6) 0.063(2) Uani 1 1 d . . . . .
H10 H 0.3999 0.7305 0.9207 0.075 Uiso 1 1 calc R U . . .
C11 C 0.3481(3) 0.9257(14) 0.7545(7) 0.070(2) Uani 1 1 d . . . . .
H11 H 0.3320 1.0449 0.7878 0.084 Uiso 1 1 calc R U . . .
C12 C 0.3297(3) 0.9398(12) 0.6242(7) 0.063(2) Uani 1 1 d . . . . .
H12 H 0.3011 1.0672 0.5711 0.075 Uiso 1 1 calc R U . . .
C13 C 0.2849(3) 0.9367(12) 0.3378(7) 0.0562(19) Uani 1 1 d . . . . .
H13 H 0.2640 1.0549 0.3624 0.067 Uiso 1 1 calc R U . . .
C14 C 0.2676(3) 0.9220(15) 0.2109(7) 0.066(2) Uani 1 1 d . . . . .
H14 H 0.2346 1.0301 0.1480 0.079 Uiso 1 1 calc R U . . .
C15 C 0.2987(4) 0.7475(15) 0.1747(6) 0.060(2) Uani 1 1 d . . . . .
H15 H 0.2866 0.7344 0.0875 0.072 Uiso 1 1 calc R U . . .
C16 C 0.4096(5) 0.2349(18) 0.0926(7) 0.082(3) Uani 1 1 d . . . . .
H16 H 0.4023 0.2339 0.0083 0.098 Uiso 1 1 calc R U . . .


_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
N1 C5 1.352(6) . ?
N1 C6 1.354(7) . ?
N2 C4 1.335(7) . ?
N2 C16 1.352(9) . ?
C1 C2 1.367(8) . ?
C1 C16 1.385(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.370(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.495(8) . ?
C5 C15 1.374(8) . ?
C6 C13 1.380(8) . ?
C6 C7 1.499(7) . ?
C7 C8 1.366(8) . ?
C7 C12 1.405(8) . ?
C8 C9 1.393(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.354(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.354(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(9) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16 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
C5 N1 C6 118.3(6) . . ?
C4 N2 C16 116.9(6) . . ?
C2 C1 C16 116.2(8) . . ?
C2 C1 H1 121.9 . . ?
C16 C1 H1 121.9 . . ?
C1 C2 C3 120.9(8) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 119.1(7) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
N2 C4 C3 122.3(7) . . ?
N2 C4 C5 117.1(6) . . ?
C3 C4 C5 120.6(6) . . ?
N1 C5 C15 122.2(7) . . ?
N1 C5 C4 116.0(6) . . ?
C15 C5 C4 121.8(6) . . ?
N1 C6 C13 121.4(6) . . ?
N1 C6 C7 114.2(6) . . ?
C13 C6 C7 124.3(7) . . ?
C8 C7 C12 117.3(6) . . ?
C8 C7 C6 121.3(6) . . ?
C12 C7 C6 121.4(7) . . ?
C7 C8 C9 121.5(7) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 120.3(7) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 119.0(6) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 121.1(7) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C7 120.8(7) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C14 C13 C6 119.4(7) . . ?
C14 C13 H13 120.3 . . ?
C6 C13 H13 120.3 . . ?
C13 C14 C15 120.2(7) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C5 C15 C14 118.4(6) . . ?
C5 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
N2 C16 C1 124.7(7) . . ?
N2 C16 H16 117.7 . . ?
C1 C16 H16 117.7 . . ?

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
C16 C1 C2 C3 -0.8(11) . . . . ?
C1 C2 C3 C4 0.7(11) . . . . ?
C16 N2 C4 C3 0.8(10) . . . . ?
C16 N2 C4 C5 -180.0(6) . . . . ?
C2 C3 C4 N2 -0.7(10) . . . . ?
C2 C3 C4 C5 -179.9(6) . . . . ?
C6 N1 C5 C15 -1.6(9) . . . . ?
C6 N1 C5 C4 178.8(5) . . . . ?
N2 C4 C5 N1 -173.0(6) . . . . ?
C3 C4 C5 N1 6.2(8) . . . . ?
N2 C4 C5 C15 7.3(8) . . . . ?
C3 C4 C5 C15 -173.4(7) . . . . ?
C5 N1 C6 C13 0.2(8) . . . . ?
C5 N1 C6 C7 177.6(6) . . . . ?
N1 C6 C7 C8 -5.0(8) . . . . ?
C13 C6 C7 C8 172.3(6) . . . . ?
N1 C6 C7 C12 175.5(6) . . . . ?
C13 C6 C7 C12 -7.2(10) . . . . ?
C12 C7 C8 C9 0.4(9) . . . . ?
C6 C7 C8 C9 -179.2(6) . . . . ?
C7 C8 C9 C10 0.8(10) . . . . ?
C8 C9 C10 C11 -2.0(11) . . . . ?
C9 C10 C11 C12 1.9(11) . . . . ?
C10 C11 C12 C7 -0.7(10) . . . . ?
C8 C7 C12 C11 -0.5(10) . . . . ?
C6 C7 C12 C11 179.1(6) . . . . ?
N1 C6 C13 C14 0.7(9) . . . . ?
C7 C6 C13 C14 -176.4(6) . . . . ?
C6 C13 C14 C15 -0.3(10) . . . . ?
N1 C5 C15 C14 2.0(10) . . . . ?
C4 C5 C15 C14 -178.4(6) . . . . ?
C13 C14 C15 C5 -1.0(10) . . . . ?
C4 N2 C16 C1 -1.0(11) . . . . ?
C2 C1 C16 N2 1.1(12) . . . . ?

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.034


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_[Ir(4Fppy)2(pbpy)][PF6]
_database_code_depnum_ccdc_archive 'CCDC 1576024'
_audit_update_record             
;
2017-09-22 deposited with the CCDC.
2017-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 F8 Ir N4 P'
_chemical_formula_weight         887.59

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5928(10)
_cell_length_b                   13.4434(13)
_cell_length_c                   14.3298(14)
_cell_angle_alpha                109.173(6)
_cell_angle_beta                 103.075(6)
_cell_angle_gamma                94.939(7)
_cell_volume                     1674.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    20717
_cell_measurement_theta_min      2.213
_cell_measurement_theta_max      24.822

_exptl_crystal_description       'irregular fragment'
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    4.114
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8
_exptl_absorpt_correction_T_max  0.9
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker, Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20717
_diffrn_reflns_av_unetI/netI     0.0790
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.213
_diffrn_reflns_theta_max         24.822
_diffrn_reflns_theta_full        24.822
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             5723
_reflns_number_gt                4749
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5723
_refine_ls_number_parameters     255
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.1434
_refine_ls_R_factor_gt           0.1244
_refine_ls_wR_factor_ref         0.3447
_refine_ls_wR_factor_gt          0.3307
_refine_ls_goodness_of_fit_ref   1.466
_refine_ls_restrained_S_all      1.468
_refine_ls_shift/su_max          0.048
_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
Ir01 Ir 0.43372(8) 0.71831(5) 0.71855(5) 0.0226(4) Uani 1 1 d . . . . .
N1 N 0.580(4) 0.615(2) 0.749(2) 0.089(5) Uani 1 1 d D . . . .
C1 C 0.381(5) 0.735(3) 0.924(2) 0.097(5) Uani 1 1 d D . . . .
F1 F 0.046(9) 0.316(4) 0.865(3) 0.44(6) Uani 1 1 d . . . . .
P002 P -0.0292(9) 0.2315(7) 0.7742(8) 0.067(2) Uani 1 1 d . . . . .
C2 C 0.271(5) 0.582(3) 0.793(2) 0.097(5) Uani 1 1 d D . . . .
C4 C 0.783(5) 0.497(3) 0.827(3) 0.089(5) Uani 1 1 d . . . . .
F4 F 0.141(4) 0.401(3) 0.377(3) 0.170(12) Uiso 1 1 d . . . . .
C12 C 0.177(3) 0.815(3) 0.743(2) 0.076(4) Uani 1 1 d D . . . .
F00F F 0.028(4) 0.1388(17) 0.811(3) 0.148(12) Uani 1 1 d . . . . .
F00E F 0.097(5) 0.233(3) 0.731(4) 0.21(2) Uani 1 1 d . . . . .
C9 C 0.288(4) 0.810(3) 0.690(2) 0.076(4) Uani 1 1 d D . . . .
N003 N 0.618(3) 0.836(2) 0.8334(19) 0.067(3) Uani 1 1 d . . . . .
F3 F -0.078(4) 0.876(3) 0.756(3) 0.153(11) Uiso 1 1 d . . . . .
C3 C 0.639(4) 0.940(2) 0.869(2) 0.067(3) Uani 1 1 d . . . . .
C7 C 0.128(3) 0.428(3) 0.609(3) 0.079(4) Uani 1 1 d . . . . .
C6 C 0.202(5) 0.551(3) 0.857(3) 0.097(5) Uani 1 1 d . . . . .
C5 C 0.052(4) 0.901(3) 0.626(2) 0.076(4) Uani 1 1 d D . . . .
C8 C 0.257(5) 0.604(3) 0.960(3) 0.097(5) Uani 1 1 d . . . . .
N00N N 0.333(4) 0.674(2) 0.817(2) 0.097(5) Uani 1 1 d D . . . .
N00P N 0.497(4) 0.757(2) 0.608(2) 0.088(5) Uani 1 1 d . . . . .
C00W C 0.776(4) 1.009(2) 0.959(2) 0.067(3) Uani 1 1 d . . . . .
C00X C 0.259(3) 0.531(3) 0.525(2) 0.079(4) Uani 1 1 d D . . . .
C01G C 0.704(4) 0.669(3) 0.830(3) 0.089(5) Uani 1 1 d D . . . .
C1J C 0.257(4) 0.822(3) 0.608(2) 0.076(4) Uani 1 1 d D . . . .
C01K C 0.155(4) 0.461(3) 0.463(3) 0.079(4) Uani 1 1 d . . . . .
C1K C 0.155(3) 0.879(3) 0.571(2) 0.076(4) Uani 1 1 d D . . . .
C01M C 0.388(5) 0.810(3) 0.563(3) 0.088(5) Uani 1 1 d D . . . .
C01O C 0.626(4) 0.763(3) 0.484(3) 0.088(5) Uani 1 1 d D . . . .
C01P C 0.089(4) 0.393(3) 0.513(3) 0.079(4) Uani 1 1 d . . . . .
F1Q F -0.152(8) 0.223(4) 0.814(6) 0.40(5) Uani 1 1 d . . . . .
C01T C 0.403(4) 0.844(3) 0.485(3) 0.095(12) Uani 1 1 d D . . . .
C1R C 0.831(4) 0.9506(19) 1.006(2) 0.067(3) Uani 1 1 d D . . . .
F1T F -0.100(5) 0.145(4) 0.675(3) 0.24(3) Uani 1 1 d . . . . .
C01U C 0.673(5) 0.469(3) 0.745(3) 0.089(5) Uani 1 1 d . . . . .
F2Q F -0.066(7) 0.318(5) 0.736(7) 0.40(6) Uani 1 1 d . . . . .
C15 C 0.334(5) 0.689(3) 0.988(3) 0.097(5) Uani 1 1 d . . . . .
C23 C 0.570(5) 0.725(3) 0.552(3) 0.088(5) Uani 1 1 d . . . . .
C22 C 0.285(4) 0.599(2) 0.625(2) 0.079(4) Uani 1 1 d D . . . .
C21 C 0.792(5) 0.610(3) 0.883(3) 0.089(5) Uani 1 1 d . . . . .
C20 C 0.549(5) 0.991(3) 0.819(4) 0.097(5) Uani 1 1 d . . . . .
C010 C 0.841(4) 0.8417(19) 0.964(2) 0.067(3) Uani 1 1 d D . . . .
C10 C 0.536(4) 0.825(3) 0.458(3) 0.088(5) Uani 1 1 d D . . . .
C015 C 0.724(4) 0.789(2) 0.880(2) 0.067(3) Uani 1 1 d . . . . .
C14 C 0.395(4) 1.132(3) 0.741(3) 0.097(5) Uani 1 1 d . . . . .
C13 C 0.613(5) 0.535(3) 0.713(3) 0.089(5) Uani 1 1 d . . . . .
C11 C 0.059(4) 0.859(2) 0.703(2) 0.076(4) Uani 1 1 d D . . . .
C019 C 0.223(3) 0.536(2) 0.675(2) 0.079(4) Uani 1 1 d D . . . .
C18 C 0.591(4) 1.033(3) 0.737(3) 0.097(5) Uani 1 1 d D . . . .
C19 C 0.336(4) 1.094(3) 0.803(3) 0.097(5) Uani 1 1 d D . . . .
C17 C 0.423(4) 1.029(3) 0.842(3) 0.097(5) Uani 1 1 d D . . . .
C16 C 0.517(4) 1.100(3) 0.706(3) 0.097(5) Uani 1 1 d 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
Ir01 C22 1.93(3) . ?
Ir01 C9 2.00(3) . ?
Ir01 N00P 2.02(2) . ?
Ir01 N00N 2.08(3) . ?
Ir01 N1 2.13(3) . ?
Ir01 N003 2.19(3) . ?
N1 C13 1.14(4) . ?
N1 C01G 1.406(19) . ?
C1 C15 1.38(5) . ?
C1 N00N 1.424(19) . ?
F1 P002 1.40(3) . ?
P002 F1Q 1.44(4) . ?
P002 F1T 1.47(4) . ?
P002 F00E 1.48(3) . ?
P002 F2Q 1.48(3) . ?
P002 F00F 1.60(2) . ?
C2 N00N 1.23(4) . ?
C2 C6 1.39(4) . ?
C2 C019 1.531(19) . ?
C4 C01U 1.31(5) . ?
C4 C21 1.45(5) . ?
F4 C01K 1.19(4) . ?
C12 C11 1.408(19) . ?
C12 C9 1.434(19) . ?
C9 C1J 1.22(4) . ?
N003 C3 1.30(4) . ?
N003 C015 1.40(4) . ?
F3 C11 1.65(4) . ?
C3 C20 1.37(5) . ?
C3 C00W 1.58(5) . ?
C7 C01P 1.25(5) . ?
C7 C019 1.53(4) . ?
C6 C8 1.36(5) . ?
C5 C11 1.389(19) . ?
C5 C1K 1.399(19) . ?
C8 C15 1.20(5) . ?
N00P C23 1.18(4) . ?
N00P C01M 1.47(5) . ?
C00W C1R 1.26(4) . ?
C00X C01K 1.25(4) . ?
C00X C22 1.377(19) . ?
C01G C21 1.45(4) . ?
C01G C015 1.51(4) . ?
C01G C13 1.98(5) . ?
C1J C1K 1.409(19) . ?
C1J C01M 1.53(5) . ?
C01K C01P 1.52(5) . ?
C01M C01T 1.368(14) . ?
C01O C10 1.320(19) . ?
C01O C23 1.41(4) . ?
C01T C10 1.431(19) . ?
C1R C010 1.410(18) . ?
C01U C13 1.26(5) . ?
C22 C019 1.443(19) . ?
C20 C17 1.42(5) . ?
C20 C18 1.57(6) . ?
C010 C015 1.38(4) . ?
C14 C19 1.36(6) . ?
C14 C16 1.42(5) . ?
C18 C16 1.322(19) . ?
C19 C17 1.422(19) . ?

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 Ir01 C9 85.5(15) . . ?
C22 Ir01 N00P 95.6(13) . . ?
C9 Ir01 N00P 80.0(13) . . ?
C22 Ir01 N00N 77.3(12) . . ?
C9 Ir01 N00N 93.0(14) . . ?
N00P Ir01 N00N 170.5(13) . . ?
C22 Ir01 N1 92.2(14) . . ?
C9 Ir01 N1 177.1(12) . . ?
N00P Ir01 N1 102.0(14) . . ?
N00N Ir01 N1 84.7(15) . . ?
C22 Ir01 N003 171.2(12) . . ?
C9 Ir01 N003 102.7(12) . . ?
N00P Ir01 N003 89.1(12) . . ?
N00N Ir01 N003 98.8(11) . . ?
N1 Ir01 N003 79.5(11) . . ?
C13 N1 C01G 102(4) . . ?
C13 N1 Ir01 143(3) . . ?
C01G N1 Ir01 113(2) . . ?
C15 C1 N00N 116(3) . . ?
F1 P002 F1Q 90(4) . . ?
F1 P002 F1T 176(3) . . ?
F1Q P002 F1T 94(4) . . ?
F1 P002 F00E 92(4) . . ?
F1Q P002 F00E 176(2) . . ?
F1T P002 F00E 84(3) . . ?
F1 P002 F2Q 84(5) . . ?
F1Q P002 F2Q 97(3) . . ?
F1T P002 F2Q 94(4) . . ?
F00E P002 F2Q 86(2) . . ?
F1 P002 F00F 96(3) . . ?
F1Q P002 F00F 90(3) . . ?
F1T P002 F00F 85(2) . . ?
F00E P002 F00F 86.7(19) . . ?
F2Q P002 F00F 173(2) . . ?
N00N C2 C6 121(3) . . ?
N00N C2 C019 106(3) . . ?
C6 C2 C019 125(3) . . ?
C01U C4 C21 107(3) . . ?
C11 C12 C9 113(3) . . ?
C1J C9 C12 118(3) . . ?
C1J C9 Ir01 120(2) . . ?
C12 C9 Ir01 115(2) . . ?
C3 N003 C015 116(3) . . ?
C3 N003 Ir01 131(3) . . ?
C015 N003 Ir01 113.2(19) . . ?
N003 C3 C20 119(3) . . ?
N003 C3 C00W 122(3) . . ?
C20 C3 C00W 119(3) . . ?
C01P C7 C019 124(4) . . ?
C8 C6 C2 117(3) . . ?
C11 C5 C1K 117(3) . . ?
C15 C8 C6 117(4) . . ?
C2 N00N C1 116(3) . . ?
C2 N00N Ir01 121(2) . . ?
C1 N00N Ir01 119(2) . . ?
C23 N00P C01M 110(3) . . ?
C23 N00P Ir01 136(3) . . ?
C01M N00P Ir01 109(2) . . ?
C1R C00W C3 109(3) . . ?
C01K C00X C22 135(3) . . ?
N1 C01G C21 120(3) . . ?
N1 C01G C015 119(3) . . ?
C21 C01G C015 119(3) . . ?
N1 C01G C13 34.2(18) . . ?
C21 C01G C13 91(2) . . ?
C015 C01G C13 150(3) . . ?
C9 C1J C1K 130(3) . . ?
C9 C1J C01M 109(3) . . ?
C1K C1J C01M 117(3) . . ?
F4 C01K C00X 132(4) . . ?
F4 C01K C01P 104(3) . . ?
C00X C01K C01P 112(4) . . ?
C5 C1K C1J 113(3) . . ?
C01T C01M N00P 121(3) . . ?
C01T C01M C1J 124(3) . . ?
N00P C01M C1J 115(2) . . ?
C10 C01O C23 106(3) . . ?
C7 C01P C01K 116(3) . . ?
C01M C01T C10 112(3) . . ?
C00W C1R C010 128(3) . . ?
C13 C01U C4 123(4) . . ?
C8 C15 C1 126(4) . . ?
N00P C23 C01O 134(3) . . ?
C00X C22 C019 105(3) . . ?
C00X C22 Ir01 135(3) . . ?
C019 C22 Ir01 113.6(19) . . ?
C01G C21 C4 117(3) . . ?
C3 C20 C17 127(4) . . ?
C3 C20 C18 122(4) . . ?
C17 C20 C18 110(4) . . ?
C015 C010 C1R 110(3) . . ?
C01O C10 C01T 129(3) . . ?
C010 C015 N003 126(3) . . ?
C010 C015 C01G 119(3) . . ?
N003 C015 C01G 115(3) . . ?
C19 C14 C16 125(4) . . ?
N1 C13 C01U 136(4) . . ?
N1 C13 C01G 44(2) . . ?
C01U C13 C01G 100(3) . . ?
C5 C11 C12 125(3) . . ?
C5 C11 F3 113(2) . . ?
C12 C11 F3 121(3) . . ?
C22 C019 C7 118(3) . . ?
C22 C019 C2 116(2) . . ?
C7 C019 C2 126(3) . . ?
C16 C18 C20 120(4) . . ?
C14 C19 C17 112(4) . . ?
C20 C17 C19 130(4) . . ?
C18 C16 C14 122(4) . . ?

_refine_diff_density_max         10.476
_refine_diff_density_min         -2.208
_refine_diff_density_rms         0.496

