# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_(2-tfppy)2IrPyS
_database_code_depnum_ccdc_archive 'CCDC 1937037'
loop_
_audit_author_name
_audit_author_address
'Lin Zhang'
;Nanjing University
China
;
_audit_update_record             
;
2019-06-28 deposited with the CCDC.	2019-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H18 F6 Ir N3 O3 S'
_chemical_formula_weight         794.72

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'
S S 0.1246 0.1234 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   9.0788(8)
_cell_length_b                   19.4903(17)
_cell_length_c                   31.615(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5594.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2711
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      24.41

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_F_000             3072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    4.925
_shelx_estimated_absorpt_T_min   0.455
_shelx_estimated_absorpt_T_max   0.613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5363
_exptl_absorpt_correction_T_max  0.7456
_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'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13367
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.090
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_full        25.007
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4851
_reflns_number_gt                3623
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+72.6709P] 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_number_reflns         4851
_refine_ls_number_parameters     376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_restrained_S_all      1.177
_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
C1 C 0.7678(12) 0.3765(5) 0.3917(3) 0.036(3) Uani 1 1 d . . . . .
C2 C 0.8841(14) 0.3543(6) 0.3662(4) 0.053(3) Uani 1 1 d . . . . .
H2 H 0.876504 0.358095 0.336938 0.063 Uiso 1 1 calc R U . . .
C3 C 1.0084(15) 0.3271(8) 0.3836(5) 0.071(4) Uani 1 1 d . . . . .
H3 H 1.085365 0.313812 0.365998 0.086 Uiso 1 1 calc R U . . .
C4 C 1.0224(17) 0.3188(8) 0.4265(5) 0.074(5) Uani 1 1 d . . . . .
H4 H 1.108218 0.300421 0.437908 0.089 Uiso 1 1 calc R U . . .
C5 C 0.9090(16) 0.3379(7) 0.4522(4) 0.057(3) Uani 1 1 d . . . . .
C6 C 0.7748(14) 0.3660(6) 0.4358(3) 0.044(3) Uani 1 1 d . . . . .
C7 C 0.6390(14) 0.3864(6) 0.4583(3) 0.044(3) Uani 1 1 d . . . . .
C8 C 0.6002(19) 0.3752(8) 0.5003(4) 0.078(5) Uani 1 1 d . . . . .
H8 H 0.666226 0.353890 0.518525 0.094 Uiso 1 1 calc R U . . .
C9 C 0.466(2) 0.3954(9) 0.5147(4) 0.080(5) Uani 1 1 d . . . . .
H9 H 0.441235 0.387035 0.542842 0.096 Uiso 1 1 calc R U . . .
C10 C 0.3668(17) 0.4272(8) 0.4895(4) 0.067(4) Uani 1 1 d . . . . .
H10 H 0.275016 0.440651 0.499565 0.080 Uiso 1 1 calc R U . . .
C11 C 0.4085(15) 0.4387(6) 0.4480(4) 0.050(3) Uani 1 1 d . . . . .
H11 H 0.343656 0.461427 0.429980 0.059 Uiso 1 1 calc R U . . .
C12 C 0.5971(14) 0.3640(6) 0.2859(3) 0.042(3) Uani 1 1 d . . . . .
C13 C 0.6286(16) 0.3628(8) 0.2430(4) 0.064(4) Uani 1 1 d . . . . .
H13 H 0.600600 0.324626 0.227299 0.077 Uiso 1 1 calc R U . . .
C14 C 0.6991(17) 0.4152(8) 0.2229(4) 0.072(4) Uani 1 1 d . . . . .
H14 H 0.716496 0.412691 0.193971 0.086 Uiso 1 1 calc R U . . .
C15 C 0.7441(16) 0.4716(8) 0.2451(4) 0.067(4) Uani 1 1 d . . . . .
H15 H 0.793696 0.507456 0.231991 0.081 Uiso 1 1 calc R U . . .
C16 C 0.7134(15) 0.4732(6) 0.2877(3) 0.053(4) Uani 1 1 d . . . . .
H16 H 0.743233 0.511188 0.303266 0.064 Uiso 1 1 calc R U . . .
C17 C 0.5196(12) 0.3136(6) 0.3121(3) 0.036(3) Uani 1 1 d . . . . .
C18 C 0.4599(13) 0.2496(6) 0.2997(3) 0.042(3) Uani 1 1 d . . . . .
C19 C 0.3787(13) 0.2114(6) 0.3273(4) 0.048(3) Uani 1 1 d . . . . .
H19 H 0.338958 0.169547 0.318919 0.057 Uiso 1 1 calc R U . . .
C20 C 0.3560(13) 0.2359(6) 0.3685(4) 0.051(3) Uani 1 1 d . . . . .
H20 H 0.293888 0.211810 0.386526 0.061 Uiso 1 1 calc R U . . .
C21 C 0.4206(13) 0.2926(6) 0.3823(3) 0.042(3) Uani 1 1 d . . . . .
H21 H 0.412332 0.304661 0.410686 0.051 Uiso 1 1 calc R U . . .
C22 C 0.5017(12) 0.3348(5) 0.3547(3) 0.032(2) Uani 1 1 d . . . . .
C23 C 0.482(2) 0.2180(9) 0.2559(5) 0.082(5) Uani 1 1 d . . . . .
C24 C 0.8229(8) 0.5411(4) 0.3912(2) 0.054(3) Uani 1 1 d G . . . .
H24 H 0.885298 0.505304 0.398746 0.064 Uiso 1 1 calc R U . . .
C25 C 0.8753(8) 0.6081(5) 0.3906(3) 0.092(6) Uani 1 1 d G . . . .
H25 H 0.972829 0.617124 0.397740 0.111 Uiso 1 1 calc R U . . .
C26 C 0.7821(12) 0.6617(3) 0.3794(3) 0.085(5) Uani 1 1 d G . . . .
H26 H 0.817155 0.706477 0.378974 0.102 Uiso 1 1 calc R U . . .
C27 C 0.6364(11) 0.6482(3) 0.3687(3) 0.062(4) Uani 1 1 d G . . . .
H27 H 0.573949 0.684009 0.361213 0.075 Uiso 1 1 calc R U . . .
C28 C 0.5839(7) 0.5812(4) 0.3693(2) 0.050(3) Uani 1 1 d G . . . .
N2 N 0.6772(8) 0.5277(3) 0.3806(2) 0.039(2) Uani 1 1 d G . . . .
C29 C 0.938(2) 0.3307(13) 0.4990(6) 0.102(7) Uani 1 1 d . . . . .
F1 F 0.4167(11) 0.2508(6) 0.2245(3) 0.102(3) Uani 1 1 d . . . . .
F2 F 0.6255(10) 0.2136(5) 0.2461(3) 0.105(4) Uani 1 1 d . . . . .
F3 F 0.4317(13) 0.1530(5) 0.2552(3) 0.124(4) Uani 1 1 d . . . . .
F4 F 0.9119(14) 0.3863(7) 0.5214(3) 0.129(4) Uani 1 1 d . . . . .
F5 F 1.0774(12) 0.3123(8) 0.5072(3) 0.153(5) Uani 1 1 d . . . . .
F6 F 0.8559(13) 0.2803(7) 0.5167(3) 0.127(4) Uani 1 1 d . . . . .
Ir1 Ir 0.59099(5) 0.42529(2) 0.37068(2) 0.02991(13) Uani 1 1 d . . . . .
N1 N 0.6418(10) 0.4220(5) 0.3080(2) 0.035(2) Uani 1 1 d . . . . .
N3 N 0.5391(10) 0.4182(5) 0.4329(2) 0.038(2) Uani 1 1 d . . . . .
O1 O 0.3670(11) 0.5960(5) 0.3194(3) 0.069(3) Uani 1 1 d . . . . .
O2 O 0.3961(9) 0.4856(4) 0.3530(2) 0.049(2) Uani 1 1 d . . . . .
O3 O 0.3162(10) 0.5829(5) 0.3946(3) 0.069(3) Uani 1 1 d . . . . .
S1 S 0.3996(4) 0.56050(14) 0.35814(9) 0.0463(8) 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
C1 C2 1.398(16) . ?
C1 C6 1.410(14) . ?
C1 Ir1 1.981(11) . ?
C2 C3 1.363(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.433(17) . ?
C5 C29 1.51(2) . ?
C6 C7 1.479(16) . ?
C7 N3 1.363(14) . ?
C7 C8 1.389(17) . ?
C8 C9 1.36(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.35(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(16) . ?
C10 H10 0.9300 . ?
C11 N3 1.340(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(15) . ?
C12 N1 1.390(14) . ?
C12 C17 1.465(15) . ?
C13 C14 1.363(18) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(19) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(16) . ?
C15 H15 0.9300 . ?
C16 N1 1.351(14) . ?
C16 H16 0.9300 . ?
C17 C18 1.415(15) . ?
C17 C22 1.418(13) . ?
C18 C19 1.364(16) . ?
C18 C23 1.526(18) . ?
C19 C20 1.402(16) . ?
C19 H19 0.9300 . ?
C20 C21 1.325(16) . ?
C20 H20 0.9300 . ?
C21 C22 1.407(14) . ?
C21 H21 0.9300 . ?
C22 Ir1 2.007(10) . ?
C23 F1 1.32(2) . ?
C23 F3 1.347(17) . ?
C23 F2 1.346(18) . ?
C24 C25 1.3900 . ?
C24 N2 1.3900 . ?
C24 H24 0.9300 . ?
C25 C26 1.3900 . ?
C25 H25 0.9300 . ?
C26 C27 1.3900 . ?
C26 H26 0.9300 . ?
C27 C28 1.3900 . ?
C27 H27 0.9300 . ?
C28 N2 1.3900 . ?
C28 S1 1.758(7) . ?
N2 Ir1 2.166(5) . ?
C29 F4 1.32(2) . ?
C29 F5 1.34(2) . ?
C29 F6 1.36(2) . ?
Ir1 N3 2.026(8) . ?
Ir1 N1 2.037(8) . ?
Ir1 O2 2.196(8) . ?
O1 S1 1.437(8) . ?
O2 S1 1.469(8) . ?
O3 S1 1.446(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.5(11) . . ?
C2 C1 Ir1 124.5(8) . . ?
C6 C1 Ir1 116.0(8) . . ?
C3 C2 C1 120.8(12) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 121.5(14) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 119.2(13) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 122.0(12) . . ?
C4 C5 C29 115.2(14) . . ?
C6 C5 C29 122.7(14) . . ?
C1 C6 C5 116.9(12) . . ?
C1 C6 C7 113.5(10) . . ?
C5 C6 C7 129.6(11) . . ?
N3 C7 C8 117.8(12) . . ?
N3 C7 C6 113.1(9) . . ?
C8 C7 C6 129.0(12) . . ?
C9 C8 C7 120.2(14) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 122.0(14) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C11 116.9(14) . . ?
C9 C10 H10 121.5 . . ?
C11 C10 H10 121.5 . . ?
N3 C11 C10 122.1(13) . . ?
N3 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C13 C12 N1 116.4(11) . . ?
C13 C12 C17 129.8(11) . . ?
N1 C12 C17 113.8(9) . . ?
C14 C13 C12 122.7(13) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C13 C14 C15 120.2(12) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 117.5(13) . . ?
C14 C15 H15 121.3 . . ?
C16 C15 H15 121.3 . . ?
N1 C16 C15 123.0(12) . . ?
N1 C16 H16 118.5 . . ?
C15 C16 H16 118.5 . . ?
C18 C17 C22 118.4(10) . . ?
C18 C17 C12 128.2(9) . . ?
C22 C17 C12 113.4(9) . . ?
C19 C18 C17 120.7(10) . . ?
C19 C18 C23 115.4(11) . . ?
C17 C18 C23 123.8(11) . . ?
C18 C19 C20 119.2(11) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C21 C20 C19 121.8(12) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 120.8(11) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C17 118.7(10) . . ?
C21 C22 Ir1 124.6(8) . . ?
C17 C22 Ir1 116.7(8) . . ?
F1 C23 F3 107.1(14) . . ?
F1 C23 F2 106.9(14) . . ?
F3 C23 F2 105.1(15) . . ?
F1 C23 C18 115.5(15) . . ?
F3 C23 C18 110.6(13) . . ?
F2 C23 C18 111.1(13) . . ?
C25 C24 N2 120.0 . . ?
C25 C24 H24 120.0 . . ?
N2 C24 H24 120.0 . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C27 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C28 120.0 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 N2 120.0 . . ?
C27 C28 S1 122.6(5) . . ?
N2 C28 S1 117.3(5) . . ?
C28 N2 C24 120.0 . . ?
C28 N2 Ir1 115.8(4) . . ?
C24 N2 Ir1 123.6(4) . . ?
F4 C29 F5 106.6(17) . . ?
F4 C29 F6 105.8(18) . . ?
F5 C29 F6 104.2(16) . . ?
F4 C29 C5 114.8(16) . . ?
F5 C29 C5 112.5(17) . . ?
F6 C29 C5 112.0(16) . . ?
C1 Ir1 C22 89.4(4) . . ?
C1 Ir1 N3 80.2(4) . . ?
C22 Ir1 N3 95.2(4) . . ?
C1 Ir1 N1 97.4(4) . . ?
C22 Ir1 N1 79.6(4) . . ?
N3 Ir1 N1 174.3(4) . . ?
C1 Ir1 N2 95.8(4) . . ?
C22 Ir1 N2 172.9(3) . . ?
N3 Ir1 N2 90.4(3) . . ?
N1 Ir1 N2 95.0(3) . . ?
C1 Ir1 O2 174.3(4) . . ?
C22 Ir1 O2 94.6(4) . . ?
N3 Ir1 O2 95.5(3) . . ?
N1 Ir1 O2 87.2(3) . . ?
N2 Ir1 O2 80.5(3) . . ?
C16 N1 C12 120.2(9) . . ?
C16 N1 Ir1 123.2(7) . . ?
C12 N1 Ir1 116.6(7) . . ?
C11 N3 C7 121.0(10) . . ?
C11 N3 Ir1 122.1(8) . . ?
C7 N3 Ir1 116.7(8) . . ?
S1 O2 Ir1 119.1(5) . . ?
O1 S1 O3 115.3(6) . . ?
O1 S1 O2 112.3(5) . . ?
O3 S1 O2 112.1(6) . . ?
O1 S1 C28 104.9(5) . . ?
O3 S1 C28 105.6(5) . . ?
O2 S1 C28 105.7(4) . . ?

_refine_diff_density_max         1.653
_refine_diff_density_min         -4.176
_refine_diff_density_rms         0.150

