# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_20181106ZYX_MEPN_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1885951'
loop_
_audit_author_name
_audit_author_address
'Ning Su'
;Nanjing university
China
;
_audit_update_record             
;
2018-12-18 deposited with the CCDC.	2020-04-21 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            'C45 H30 F6 Ir N5 S2'
_chemical_formula_weight         1011.06

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'
Ir Ir -1.4442 7.9887 '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'
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'

_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                   10.442(11)
_cell_length_b                   23.68(3)
_cell_length_c                   15.834(16)
_cell_angle_alpha                90
_cell_angle_beta                 106.52(2)
_cell_angle_gamma                90
_cell_volume                     3754(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3220
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.50

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_F_000             1992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    3.741
_shelx_estimated_absorpt_T_min   0.493
_shelx_estimated_absorpt_T_max   0.604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4272
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(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            4585
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.264
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.010
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3294
_reflns_number_gt                2817
_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 2014/5 (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)+(0.0918P)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_number_reflns         3294
_refine_ls_number_parameters     269
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.129
_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
C1 C 0.3748(8) 0.4340(4) 0.7708(5) 0.0361(17) Uani 1 1 d . . . . .
C2 C 0.3889(8) 0.4052(4) 0.8488(5) 0.0378(18) Uani 1 1 d . . . . .
H2 H 0.466827 0.410324 0.896835 0.045 Uiso 1 1 calc R U . . .
C3 C 0.2916(8) 0.3697(3) 0.8567(5) 0.0373(18) Uani 1 1 d . . . . .
C4 C 0.1788(9) 0.3615(4) 0.7897(6) 0.056(3) Uani 1 1 d . . . . .
H4 H 0.109656 0.337517 0.796812 0.068 Uiso 1 1 calc R U . . .
C5 C 0.1682(9) 0.3864(4) 0.7176(5) 0.061(3) Uani 1 1 d . . . . .
H5 H 0.091265 0.378283 0.670263 0.073 Uiso 1 1 calc DR U . . .
C6 C 0.2580(8) 0.4244(3) 0.7016(5) 0.0392(19) Uani 1 1 d . . . . .
C7 C 0.3077(10) 0.3394(4) 0.9392(6) 0.052(2) Uani 1 1 d . . . . .
C8 C 0.2594(8) 0.4524(3) 0.6219(5) 0.0386(18) Uani 1 1 d . . . . .
C9 C 0.1642(9) 0.4481(4) 0.5384(5) 0.047(2) Uani 1 1 d . . . . .
C10 C 0.0344(11) 0.4255(6) 0.5105(6) 0.083(4) Uani 1 1 d . . . . .
H10 H -0.002599 0.413607 0.555802 0.100 Uiso 1 1 calc DR U . . .
C11 C -0.0387(13) 0.4192(6) 0.4330(7) 0.089(4) Uani 1 1 d . . . . .
H11 H -0.118440 0.397536 0.421378 0.106 Uiso 1 1 calc R U . . .
C12 C -0.0021(12) 0.4433(7) 0.3676(7) 0.086(4) Uani 1 1 d . . . . .
H12 H -0.058355 0.441013 0.308841 0.103 Uiso 1 1 calc R U . . .
C13 C 0.1116(12) 0.4702(6) 0.3847(6) 0.076(3) Uani 1 1 d . . . . .
H13 H 0.136696 0.487484 0.337684 0.091 Uiso 1 1 calc R U . . .
C14 C 0.1966(10) 0.4741(5) 0.4691(6) 0.059(3) Uani 1 1 d . . . . .
C15 C 0.3857(11) 0.5090(4) 0.5601(7) 0.057(3) Uani 1 1 d . . . . .
H15 H 0.462573 0.532221 0.568763 0.069 Uiso 1 1 calc R U . . .
C16 C 0.500000 0.6111(5) 0.750000 0.043(3) Uani 1 2 d S T P . .
C17 C 0.5885(9) 0.6988(4) 0.7173(6) 0.049(2) Uani 1 1 d . . . . .
C18 C 0.7199(10) 0.6982(5) 0.7586(9) 0.077(3) Uani 1 1 d . . . . .
H18 H 0.754567 0.676888 0.810929 0.093 Uiso 1 1 calc R U . . .
C19 C 0.8023(12) 0.7292(6) 0.7235(10) 0.094(4) Uani 1 1 d . . . . .
H19 H 0.895629 0.729276 0.751965 0.113 Uiso 1 1 calc R U . . .
C20 C 0.7552(14) 0.7592(5) 0.6501(10) 0.081(4) Uani 1 1 d . . . . .
C21 C 0.6207(14) 0.7596(5) 0.6099(7) 0.076(3) Uani 1 1 d . . . . .
H21 H 0.585753 0.781103 0.557710 0.091 Uiso 1 1 calc R U . . .
C22 C 0.5380(10) 0.7297(4) 0.6438(6) 0.057(2) Uani 1 1 d . . . . .
H22 H 0.444390 0.730338 0.616327 0.069 Uiso 1 1 calc R U . . .
C23 C 0.8472(13) 0.7935(7) 0.6135(10) 0.114(5) Uani 1 1 d . . . . .
H23A H 0.846789 0.832750 0.632944 0.171 Uiso 1 1 calc R U . . .
H23B H 0.817057 0.791965 0.549007 0.171 Uiso 1 1 calc R U . . .
H23C H 0.937900 0.778197 0.634544 0.171 Uiso 1 1 calc R U . . .
F1 F 0.2007(8) 0.3373(4) 0.9624(5) 0.122(3) Uani 1 1 d . . . . .
F2 F 0.3374(9) 0.2865(3) 0.9342(4) 0.100(2) Uani 1 1 d . . . . .
F3 F 0.4017(9) 0.3589(3) 1.0039(4) 0.112(3) Uani 1 1 d . . . . .
Ir1 Ir 0.500000 0.49010(2) 0.750000 0.0374(2) Uani 1 2 d S T P . .
N1 N 0.3650(7) 0.4841(3) 0.6316(4) 0.0355(15) Uani 1 1 d . . . . .
N2 N 0.3098(10) 0.5039(4) 0.4818(6) 0.067(3) Uani 1 1 d . . . . .
N3 N 0.500000 0.6665(4) 0.750000 0.049(3) Uani 1 2 d S T P . .
S1 S 0.6137(2) 0.57296(10) 0.71954(16) 0.0484(6) 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 1.383(11) . ?
C1 C6 1.407(11) . ?
C1 Ir1 1.955(8) . ?
C2 C3 1.352(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.357(11) . ?
C3 C7 1.457(11) . ?
C4 C5 1.262(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(12) . ?
C5 H5 0.9500 . ?
C6 C8 1.429(10) . ?
C7 F1 1.273(11) . ?
C7 F3 1.285(11) . ?
C7 F2 1.299(12) . ?
C8 N1 1.307(10) . ?
C8 C9 1.413(11) . ?
C9 C10 1.407(14) . ?
C9 C14 1.382(13) . ?
C10 C11 1.255(13) . ?
C10 H10 0.9500 . ?
C11 C12 1.331(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.306(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(14) . ?
C13 H13 0.9500 . ?
C14 N2 1.341(14) . ?
C15 N2 1.273(15) . ?
C15 N1 1.348(12) . ?
C15 H15 0.9500 . ?
C16 N3 1.312(16) . ?
C16 S1 1.669(7) 2_656 ?
C16 S1 1.669(7) . ?
C17 C22 1.348(13) . ?
C17 C18 1.342(13) . ?
C17 N3 1.407(11) . ?
C18 C19 1.364(17) . ?
C18 H18 0.9500 . ?
C19 C20 1.331(18) . ?
C19 H19 0.9500 . ?
C20 C21 1.367(17) . ?
C20 C23 1.495(15) . ?
C21 C22 1.342(14) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
Ir1 N1 2.004(7) 2_656 ?
Ir1 N1 2.005(7) . ?
Ir1 S1 2.412(3) . ?
Ir1 S1 2.412(3) 2_656 ?

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 117.7(7) . . ?
C2 C1 Ir1 125.4(6) . . ?
C6 C1 Ir1 116.9(6) . . ?
C3 C2 C1 119.9(7) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.7(7) . . ?
C2 C3 C7 119.4(8) . . ?
C4 C3 C7 119.0(8) . . ?
C5 C4 C3 118.3(9) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 125.8(8) . . ?
C4 C5 H5 117.1 . . ?
C6 C5 H5 117.1 . . ?
C5 C6 C1 116.6(7) . . ?
C5 C6 C8 130.2(7) . . ?
C1 C6 C8 112.9(7) . . ?
F1 C7 F3 108.6(9) . . ?
F1 C7 F2 102.9(9) . . ?
F3 C7 F2 104.7(9) . . ?
F1 C7 C3 113.0(8) . . ?
F3 C7 C3 113.9(8) . . ?
F2 C7 C3 112.8(8) . . ?
N1 C8 C9 119.8(7) . . ?
N1 C8 C6 112.4(7) . . ?
C9 C8 C6 127.7(8) . . ?
C10 C9 C14 110.5(8) . . ?
C10 C9 C8 132.9(8) . . ?
C14 C9 C8 116.4(9) . . ?
C11 C10 C9 128.1(10) . . ?
C11 C10 H10 115.9 . . ?
C9 C10 H10 115.9 . . ?
C10 C11 C12 118.6(12) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C13 C12 C11 119.5(10) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 122.0(11) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
N2 C14 C9 121.3(9) . . ?
N2 C14 C13 118.5(10) . . ?
C9 C14 C13 120.2(10) . . ?
N2 C15 N1 124.9(10) . . ?
N2 C15 H15 117.5 . . ?
N1 C15 H15 117.5 . . ?
N3 C16 S1 122.8(3) . 2_656 ?
N3 C16 S1 122.8(3) . . ?
S1 C16 S1 114.4(7) 2_656 . ?
C22 C17 C18 121.4(10) . . ?
C22 C17 N3 118.4(8) . . ?
C18 C17 N3 120.2(9) . . ?
C17 C18 C19 118.2(12) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C20 C19 C18 121.5(13) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 119.2(11) . . ?
C19 C20 C23 120.6(14) . . ?
C21 C20 C23 120.2(14) . . ?
C22 C21 C20 120.1(12) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 119.5(11) . . ?
C21 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 Ir1 C1 94.5(5) . 2_656 ?
C1 Ir1 N1 96.9(3) . 2_656 ?
C1 Ir1 N1 77.5(3) 2_656 2_656 ?
C1 Ir1 N1 77.5(3) . . ?
C1 Ir1 N1 96.9(3) 2_656 . ?
N1 Ir1 N1 171.8(4) 2_656 . ?
C1 Ir1 S1 167.6(2) . . ?
C1 Ir1 S1 97.3(3) 2_656 . ?
N1 Ir1 S1 89.4(2) 2_656 . ?
N1 Ir1 S1 97.2(2) . . ?
C1 Ir1 S1 97.3(3) . 2_656 ?
C1 Ir1 S1 167.6(2) 2_656 2_656 ?
N1 Ir1 S1 97.2(2) 2_656 2_656 ?
N1 Ir1 S1 89.4(2) . 2_656 ?
S1 Ir1 S1 71.14(13) . 2_656 ?
C8 N1 C15 119.0(8) . . ?
C8 N1 Ir1 119.8(5) . . ?
C15 N1 Ir1 121.1(6) . . ?
C15 N2 C14 118.3(9) . . ?
C16 N3 C17 122.9(5) . . ?
C16 N3 C17 122.9(5) . 2_656 ?
C17 N3 C17 114.2(11) . 2_656 ?
C16 S1 Ir1 87.2(3) . . ?

_refine_diff_density_max         3.650
_refine_diff_density_min         -1.547
_refine_diff_density_rms         0.198

