# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_btp-L1
_database_code_depnum_ccdc_archive 'CCDC 2300731'
loop_
_audit_author_name
_audit_author_address
'Thomas Teets'
;University of Houston
United States of America
;
_audit_update_record             
;
2023-10-11 deposited with the CCDC.	2024-01-19 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            'C36 H28 Ir N3 O S2'
_chemical_formula_weight         774.93

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   36.2343(15)
_cell_length_b                   36.2343(15)
_cell_length_c                   15.9108(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     18091.0(17)
_cell_formula_units_Z            18
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9872
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      28.09

_exptl_crystal_description       Needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             6876
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    3.451
_shelx_estimated_absorpt_T_min   0.312
_shelx_estimated_absorpt_T_max   0.560
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5080
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(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            31337
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.823
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             8981
_reflns_number_gt                7614
_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. 
  
 Structure factors included contributions from the .fab file. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0103P)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         8981
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0474
_refine_ls_wR_factor_gt          0.0467
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_refine_ls_shift/su_max          0.004
_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
O1 O 0.37842(5) 0.32651(5) 0.38183(10) 0.0173(4) Uani 1 1 d . . . . .
Ir1 Ir 0.43020(2) 0.36827(2) 0.30524(2) 0.01416(3) Uani 1 1 d . . . . .
S1 S 0.47891(2) 0.44537(2) 0.54316(4) 0.02626(16) Uani 1 1 d . . . . .
S2 S 0.55250(2) 0.40928(2) 0.16437(5) 0.02802(17) Uani 1 1 d . . . . .
N1 N 0.41465(6) 0.41480(6) 0.32552(13) 0.0162(5) Uani 1 1 d . . . . .
N2 N 0.44708(6) 0.32284(6) 0.28370(13) 0.0172(5) Uani 1 1 d . . . . .
N3 N 0.39015(6) 0.34301(6) 0.19871(13) 0.0154(5) Uani 1 1 d . . . . .
C1 C 0.34981(8) 0.31601(7) 0.20246(15) 0.0152(5) Uani 1 1 d . . . . .
H1 H 0.335597 0.306961 0.149926 0.018 Uiso 1 1 calc R U . . .
C12 C 0.39082(8) 0.42432(8) 0.27402(17) 0.0198(6) Uani 1 1 d . . . . .
H12 H 0.379444 0.407980 0.224287 0.024 Uiso 1 1 calc R U . . .
C13 C 0.38240(8) 0.45654(8) 0.29058(17) 0.0225(6) Uani 1 1 d . . . . .
H13 H 0.366499 0.463062 0.251900 0.027 Uiso 1 1 calc R U . . .
C14 C 0.39750(8) 0.47953(8) 0.36491(18) 0.0257(7) Uani 1 1 d . . . . .
H14 H 0.391854 0.501825 0.377933 0.031 Uiso 1 1 calc R U . . .
C15 C 0.42081(8) 0.46948(8) 0.41951(17) 0.0221(6) Uani 1 1 d . . . . .
H15 H 0.430710 0.484384 0.471180 0.026 Uiso 1 1 calc R U . . .
C16 C 0.42973(8) 0.43757(8) 0.39868(16) 0.0182(6) Uani 1 1 d . . . . .
C21 C 0.46215(7) 0.39304(8) 0.41409(15) 0.0168(5) Uani 1 1 d . . . . .
C22 C 0.48820(8) 0.38519(8) 0.47130(17) 0.0207(6) Uani 1 1 d . . . . .
C23 C 0.50137(8) 0.35510(8) 0.46668(18) 0.0271(7) Uani 1 1 d . . . . .
H23 H 0.493628 0.336689 0.419402 0.033 Uiso 1 1 calc R U . . .
C24 C 0.52559(9) 0.35176(9) 0.5302(2) 0.0335(7) Uani 1 1 d . . . . .
H24 H 0.534534 0.331243 0.526193 0.040 Uiso 1 1 calc R U . . .
C25 C 0.53699(9) 0.37859(10) 0.6006(2) 0.0366(8) Uani 1 1 d . . . . .
H25 H 0.553682 0.376085 0.643866 0.044 Uiso 1 1 calc R U . . .
C26 C 0.52436(9) 0.40846(9) 0.60791(19) 0.0321(7) Uani 1 1 d . . . . .
H26 H 0.532300 0.426691 0.655503 0.039 Uiso 1 1 calc R U . . .
C27 C 0.49963(8) 0.41144(8) 0.54393(17) 0.0249(6) Uani 1 1 d . . . . .
C28 C 0.45550(8) 0.42474(8) 0.44558(16) 0.0203(6) Uani 1 1 d . . . . .
C32 C 0.42392(8) 0.28158(8) 0.30566(16) 0.0197(6) Uani 1 1 d . . . . .
H32 H 0.398337 0.272389 0.336525 0.024 Uiso 1 1 calc R U . . .
C33 C 0.43588(9) 0.25211(8) 0.28508(17) 0.0239(6) Uani 1 1 d . . . . .
H33 H 0.418487 0.223066 0.300624 0.029 Uiso 1 1 calc R U . . .
C34 C 0.47323(9) 0.26514(9) 0.24184(18) 0.0287(7) Uani 1 1 d . . . . .
H34 H 0.482385 0.245384 0.228803 0.034 Uiso 1 1 calc R U . . .
C35 C 0.49740(9) 0.30737(9) 0.21747(18) 0.0261(6) Uani 1 1 d . . . . .
H35 H 0.522979 0.316711 0.186503 0.031 Uiso 1 1 calc R U . . .
C36 C 0.48388(8) 0.33611(8) 0.23875(16) 0.0198(6) Uani 1 1 d . . . . .
C41 C 0.48512(8) 0.40338(8) 0.24234(15) 0.0172(5) Uani 1 1 d . . . . .
C42 C 0.51126(8) 0.44761(8) 0.21678(16) 0.0182(6) Uani 1 1 d . . . . .
C43 C 0.50540(8) 0.48257(8) 0.23020(17) 0.0225(6) Uani 1 1 d . . . . .
H43 H 0.480986 0.478793 0.259828 0.027 Uiso 1 1 calc R U . . .
C44 C 0.53499(8) 0.52263(9) 0.20055(18) 0.0274(7) Uani 1 1 d . . . . .
H44 H 0.530722 0.546123 0.209957 0.033 Uiso 1 1 calc R U . . .
C45 C 0.57109(9) 0.52864(9) 0.15684(18) 0.0276(7) Uani 1 1 d . . . . .
H45 H 0.590982 0.556221 0.136535 0.033 Uiso 1 1 calc R U . . .
C46 C 0.57826(8) 0.49544(8) 0.14280(17) 0.0262(7) Uani 1 1 d . . . . .
H46 H 0.602887 0.499724 0.113301 0.031 Uiso 1 1 calc R U . . .
C47 C 0.54841(8) 0.45507(8) 0.17298(17) 0.0219(6) Uani 1 1 d . . . . .
C48 C 0.50415(8) 0.38054(8) 0.21839(17) 0.0206(6) Uani 1 1 d . . . . .
C51 C 0.33859(8) 0.30226(7) 0.35928(16) 0.0151(5) Uani 1 1 d . . . . .
C52 C 0.30863(8) 0.27759(8) 0.42257(16) 0.0165(5) Uani 1 1 d . . . . .
H52 H 0.318167 0.279304 0.478811 0.020 Uiso 1 1 calc R U . . .
C53 C 0.26605(8) 0.25121(8) 0.40433(17) 0.0193(6) Uani 1 1 d . . . . .
H53 H 0.246828 0.235019 0.447944 0.023 Uiso 1 1 calc R U . . .
C54 C 0.25095(8) 0.24808(8) 0.32248(17) 0.0212(6) Uani 1 1 d . . . . .
H54 H 0.221468 0.230552 0.310465 0.025 Uiso 1 1 calc R U . . .
C55 C 0.27938(8) 0.27077(8) 0.25924(17) 0.0185(6) Uani 1 1 d . . . . .
H55 H 0.269258 0.268277 0.203268 0.022 Uiso 1 1 calc R U . . .
C56 C 0.32340(8) 0.29774(8) 0.27601(15) 0.0150(5) Uani 1 1 d . . . . .
C61 C 0.40914(8) 0.35347(8) 0.11361(16) 0.0192(6) Uani 1 1 d . . . . .
H61A H 0.388344 0.332723 0.073202 0.023 Uiso 1 1 calc R U . . .
H61B H 0.434604 0.350074 0.113028 0.023 Uiso 1 1 calc R U . . .
C62 C 0.42211(8) 0.39825(8) 0.08385(16) 0.0212(6) Uani 1 1 d . . . . .
H62A H 0.396314 0.399916 0.070281 0.025 Uiso 1 1 calc R U . . .
H62B H 0.437676 0.418939 0.129298 0.025 Uiso 1 1 calc R U . . .
C63 C 0.45036(10) 0.40960(10) 0.00643(19) 0.0395(8) Uani 1 1 d . . . . .
H63A H 0.475626 0.407438 0.019695 0.059 Uiso 1 1 calc R U . . .
H63B H 0.459193 0.438800 -0.011004 0.059 Uiso 1 1 calc R U . . .
H63C H 0.434463 0.389860 -0.039290 0.059 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
O1 C51 1.310(3) . ?
O1 Ir1 2.1108(16) . ?
Ir1 C41 2.012(2) . ?
Ir1 C21 2.026(2) . ?
Ir1 N2 2.051(2) . ?
Ir1 N1 2.053(2) . ?
Ir1 N3 2.119(2) . ?
S1 C27 1.732(3) . ?
S1 C28 1.748(3) . ?
S2 C47 1.744(3) . ?
S2 C48 1.752(3) . ?
N1 C12 1.354(3) . ?
N1 C16 1.372(3) . ?
N2 C32 1.344(3) . ?
N2 C36 1.371(3) . ?
N3 C1 1.291(3) . ?
N3 C61 1.480(3) . ?
C1 C56 1.446(3) . ?
C12 C13 1.372(3) . ?
C13 C14 1.391(4) . ?
C14 C15 1.381(4) . ?
C15 C16 1.387(3) . ?
C16 C28 1.442(4) . ?
C21 C28 1.380(3) . ?
C21 C22 1.438(3) . ?
C22 C23 1.393(4) . ?
C22 C27 1.420(4) . ?
C23 C24 1.383(4) . ?
C24 C25 1.403(4) . ?
C25 C26 1.374(4) . ?
C26 C27 1.396(4) . ?
C32 C33 1.378(3) . ?
C33 C34 1.374(4) . ?
C34 C35 1.385(4) . ?
C35 C36 1.396(3) . ?
C36 C48 1.433(3) . ?
C41 C48 1.370(3) . ?
C41 C42 1.454(3) . ?
C42 C43 1.402(3) . ?
C42 C47 1.417(3) . ?
C43 C44 1.387(4) . ?
C44 C45 1.399(4) . ?
C45 C46 1.370(4) . ?
C46 C47 1.399(4) . ?
C51 C56 1.412(3) . ?
C51 C52 1.422(3) . ?
C52 C53 1.380(3) . ?
C53 C54 1.395(4) . ?
C54 C55 1.379(4) . ?
C55 C56 1.418(3) . ?
C61 C62 1.522(3) . ?
C62 C63 1.521(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
C51 O1 Ir1 127.52(15) . . ?
C41 Ir1 C21 88.84(10) . . ?
C41 Ir1 N2 80.03(9) . . ?
C21 Ir1 N2 99.48(9) . . ?
C41 Ir1 N1 98.61(9) . . ?
C21 Ir1 N1 80.36(9) . . ?
N2 Ir1 N1 178.64(8) . . ?
C41 Ir1 O1 169.73(8) . . ?
C21 Ir1 O1 86.00(8) . . ?
N2 Ir1 O1 92.06(7) . . ?
N1 Ir1 O1 89.28(7) . . ?
C41 Ir1 N3 97.04(9) . . ?
C21 Ir1 N3 172.46(9) . . ?
N2 Ir1 N3 86.24(8) . . ?
N1 Ir1 N3 94.04(8) . . ?
O1 Ir1 N3 88.90(7) . . ?
C27 S1 C28 89.58(13) . . ?
C47 S2 C48 89.51(12) . . ?
C12 N1 C16 118.2(2) . . ?
C12 N1 Ir1 125.86(17) . . ?
C16 N1 Ir1 115.90(17) . . ?
C32 N2 C36 118.9(2) . . ?
C32 N2 Ir1 125.33(18) . . ?
C36 N2 Ir1 115.69(16) . . ?
C1 N3 C61 116.2(2) . . ?
C1 N3 Ir1 124.18(17) . . ?
C61 N3 Ir1 119.40(16) . . ?
N3 C1 C56 128.6(2) . . ?
N1 C12 C13 122.8(3) . . ?
C12 C13 C14 119.0(3) . . ?
C15 C14 C13 119.1(2) . . ?
C14 C15 C16 119.8(3) . . ?
N1 C16 C15 121.0(2) . . ?
N1 C16 C28 111.9(2) . . ?
C15 C16 C28 127.1(2) . . ?
C28 C21 C22 109.9(2) . . ?
C28 C21 Ir1 112.33(18) . . ?
C22 C21 Ir1 137.7(2) . . ?
C23 C22 C27 117.9(2) . . ?
C23 C22 C21 129.5(3) . . ?
C27 C22 C21 112.5(2) . . ?
C24 C23 C22 120.7(3) . . ?
C23 C24 C25 120.2(3) . . ?
C26 C25 C24 121.0(3) . . ?
C25 C26 C27 118.6(3) . . ?
C26 C27 C22 121.7(3) . . ?
C26 C27 S1 125.7(2) . . ?
C22 C27 S1 112.6(2) . . ?
C21 C28 C16 119.4(2) . . ?
C21 C28 S1 115.4(2) . . ?
C16 C28 S1 125.2(2) . . ?
N2 C32 C33 122.5(2) . . ?
C34 C33 C32 119.4(2) . . ?
C33 C34 C35 119.3(3) . . ?
C34 C35 C36 119.5(3) . . ?
N2 C36 C35 120.5(2) . . ?
N2 C36 C48 112.0(2) . . ?
C35 C36 C48 127.5(2) . . ?
C48 C41 C42 109.9(2) . . ?
C48 C41 Ir1 113.20(18) . . ?
C42 C41 Ir1 136.85(19) . . ?
C43 C42 C47 117.5(2) . . ?
C43 C42 C41 130.1(2) . . ?
C47 C42 C41 112.4(2) . . ?
C44 C43 C42 120.5(3) . . ?
C43 C44 C45 120.4(3) . . ?
C46 C45 C44 121.2(3) . . ?
C45 C46 C47 118.4(3) . . ?
C46 C47 C42 122.2(3) . . ?
C46 C47 S2 125.4(2) . . ?
C42 C47 S2 112.45(19) . . ?
C41 C48 C36 119.0(2) . . ?
C41 C48 S2 115.69(19) . . ?
C36 C48 S2 125.3(2) . . ?
O1 C51 C56 124.7(2) . . ?
O1 C51 C52 117.8(2) . . ?
C56 C51 C52 117.4(2) . . ?
C53 C52 C51 121.6(2) . . ?
C52 C53 C54 120.7(2) . . ?
C55 C54 C53 119.1(2) . . ?
C54 C55 C56 121.4(2) . . ?
C51 C56 C55 119.7(2) . . ?
C51 C56 C1 125.2(2) . . ?
C55 C56 C1 115.0(2) . . ?
N3 C61 C62 114.5(2) . . ?
C63 C62 C61 110.3(2) . . ?

_refine_diff_density_max         1.009
_refine_diff_density_min         -1.176
_refine_diff_density_rms         0.082



####################################################################### 
# 
# 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_btp-L2
_database_code_depnum_ccdc_archive 'CCDC 2300732'
loop_
_audit_author_name
_audit_author_address
'Thomas Teets'
;University of Houston
United States of America
;
_audit_update_record             
;
2023-10-11 deposited with the CCDC.	2024-01-19 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            'C40 H28 Ir N3 O S2'
_chemical_formula_weight         822.97

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'
O O 0.0106 0.0060 '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'

_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                   10.7907(11)
_cell_length_b                   11.0742(11)
_cell_length_c                   14.2844(14)
_cell_angle_alpha                107.0870(10)
_cell_angle_beta                 102.3680(10)
_cell_angle_gamma                93.3970(10)
_cell_volume                     1580.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4618
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      21.75

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_F_000             812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    4.396
_shelx_estimated_absorpt_T_min   0.522
_shelx_estimated_absorpt_T_max   0.693
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6132
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(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            28181
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.537
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7275
_reflns_number_gt                6228
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0265P)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         7275
_refine_ls_number_parameters     425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0699
_refine_ls_wR_factor_gt          0.0672
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.002
_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
O1 O 0.9229(3) 0.2188(3) 0.8855(2) 0.0228(7) Uani 1 1 d . . . . .
Ir1 Ir 0.77042(2) 0.26394(2) 0.78616(2) 0.01537(6) Uani 1 1 d . . . . .
S1 S 0.57938(12) 0.24596(10) 1.03266(9) 0.0235(3) Uani 1 1 d . . . . .
S2 S 0.54612(11) 0.50479(10) 0.62556(9) 0.0213(2) Uani 1 1 d . . . . .
N1 N 0.6810(3) 0.0891(3) 0.7743(3) 0.0171(8) Uani 1 1 d . . . . .
N2 N 0.8589(3) 0.4419(3) 0.8038(3) 0.0189(8) Uani 1 1 d . . . . .
N3 N 0.8694(3) 0.1934(3) 0.6687(3) 0.0195(8) Uani 1 1 d . . . . .
C1 C 0.9646(4) 0.1270(4) 0.6778(3) 0.0233(10) Uani 1 1 d . . . . .
H1 H 1.001033 0.101897 0.621192 0.028 Uiso 1 1 calc R U . . .
C12 C 0.6763(4) -0.0201(4) 0.7005(3) 0.0191(9) Uani 1 1 d . . . . .
H12 H 0.710366 -0.017559 0.644902 0.023 Uiso 1 1 calc R U . . .
C13 C 0.6243(4) -0.1352(4) 0.7021(3) 0.0244(10) Uani 1 1 d . . . . .
H13 H 0.622379 -0.210940 0.648623 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5745(5) -0.1395(4) 0.7829(4) 0.0281(11) Uani 1 1 d . . . . .
H14 H 0.539411 -0.218544 0.785986 0.034 Uiso 1 1 calc R U . . .
C15 C 0.5763(4) -0.0284(4) 0.8587(3) 0.0217(10) Uani 1 1 d . . . . .
H15 H 0.541232 -0.029937 0.913984 0.026 Uiso 1 1 calc R U . . .
C16 C 0.6301(4) 0.0866(4) 0.8536(3) 0.0175(9) Uani 1 1 d . . . . .
C21 C 0.6901(4) 0.3149(4) 0.9048(3) 0.0181(9) Uani 1 1 d . . . . .
C22 C 0.6830(4) 0.4308(4) 0.9826(3) 0.0163(9) Uani 1 1 d . . . . .
C23 C 0.7240(4) 0.5603(4) 0.9941(3) 0.0183(9) Uani 1 1 d . . . . .
H23 H 0.761650 0.580307 0.945295 0.022 Uiso 1 1 calc R U . . .
C24 C 0.7091(4) 0.6560(4) 1.0759(4) 0.0253(11) Uani 1 1 d . . . . .
H24 H 0.737542 0.741916 1.083457 0.030 Uiso 1 1 calc R U . . .
C25 C 0.6536(4) 0.6294(4) 1.1474(3) 0.0263(11) Uani 1 1 d . . . . .
H25 H 0.645062 0.697329 1.203512 0.032 Uiso 1 1 calc R U . . .
C26 C 0.6103(4) 0.5059(4) 1.1389(3) 0.0230(10) Uani 1 1 d . . . . .
H26 H 0.571082 0.488517 1.187882 0.028 Uiso 1 1 calc R U . . .
C27 C 0.6252(4) 0.4079(4) 1.0572(3) 0.0194(9) Uani 1 1 d . . . . .
C28 C 0.6373(4) 0.2108(4) 0.9235(3) 0.0173(9) Uani 1 1 d . . . . .
C32 C 0.9768(4) 0.4912(4) 0.8598(3) 0.0223(10) Uani 1 1 d . . . . .
H32 H 1.025561 0.441438 0.894035 0.027 Uiso 1 1 calc R U . . .
C33 C 1.0301(4) 0.6112(4) 0.8696(3) 0.0257(11) Uani 1 1 d . . . . .
H33 H 1.112846 0.645473 0.912211 0.031 Uiso 1 1 calc R U . . .
C34 C 0.9602(4) 0.6817(4) 0.8158(3) 0.0251(11) Uani 1 1 d . . . . .
H34 H 0.996129 0.764144 0.820026 0.030 Uiso 1 1 calc R U . . .
C35 C 0.8398(4) 0.6321(4) 0.7569(3) 0.0242(11) Uani 1 1 d . . . . .
H35 H 0.792078 0.679329 0.719511 0.029 Uiso 1 1 calc R U . . .
C36 C 0.7879(4) 0.5115(4) 0.7523(3) 0.0181(9) Uani 1 1 d . . . . .
C41 C 0.6294(4) 0.3259(4) 0.7029(3) 0.0150(9) Uani 1 1 d . . . . .
C42 C 0.4989(4) 0.2780(4) 0.6431(3) 0.0159(9) Uani 1 1 d . . . . .
C43 C 0.4252(4) 0.1607(4) 0.6247(3) 0.0207(10) Uani 1 1 d . . . . .
H43 H 0.460387 0.099349 0.653515 0.025 Uiso 1 1 calc R U . . .
C44 C 0.3026(4) 0.1345(4) 0.5654(3) 0.0229(10) Uani 1 1 d . . . . .
H44 H 0.253097 0.055695 0.554730 0.027 Uiso 1 1 calc R U . . .
C45 C 0.2495(4) 0.2219(4) 0.5205(3) 0.0243(10) Uani 1 1 d . . . . .
H45 H 0.165068 0.201048 0.478556 0.029 Uiso 1 1 calc R U . . .
C46 C 0.3183(4) 0.3380(4) 0.5364(3) 0.0190(9) Uani 1 1 d . . . . .
H46 H 0.281937 0.398233 0.506906 0.023 Uiso 1 1 calc R U . . .
C47 C 0.4425(4) 0.3646(4) 0.5968(3) 0.0178(9) Uani 1 1 d . . . . .
C48 C 0.6617(4) 0.4455(4) 0.6990(3) 0.0179(9) Uani 1 1 d . . . . .
C51 C 0.8483(4) 0.2367(4) 0.5822(3) 0.0213(10) Uani 1 1 d . . . . .
C52 C 0.7289(4) 0.2138(4) 0.5151(3) 0.0222(10) Uani 1 1 d . . . . .
H52 H 0.658947 0.167569 0.525644 0.027 Uiso 1 1 calc R U . . .
C53 C 0.7124(5) 0.2582(4) 0.4333(3) 0.0281(11) Uani 1 1 d . . . . .
H53 H 0.629895 0.242675 0.388756 0.034 Uiso 1 1 calc R U . . .
C54 C 0.8113(5) 0.3247(4) 0.4135(4) 0.0284(11) Uani 1 1 d . . . . .
C55 C 0.9310(5) 0.3439(5) 0.4802(4) 0.0310(12) Uani 1 1 d . . . . .
H55 H 1.001900 0.386197 0.467647 0.037 Uiso 1 1 calc R U . . .
C56 C 0.9492(4) 0.3029(4) 0.5644(4) 0.0265(11) Uani 1 1 d . . . . .
H56 H 1.031126 0.320165 0.610058 0.032 Uiso 1 1 calc R U . . .
C57 C 0.7910(5) 0.3726(5) 0.3254(4) 0.0371(13) Uani 1 1 d . . . . .
H57A H 0.773492 0.300372 0.263018 0.056 Uiso 1 1 calc R U . . .
H57B H 0.867983 0.427683 0.329915 0.056 Uiso 1 1 calc R U . . .
H57C H 0.718101 0.421332 0.325053 0.056 Uiso 1 1 calc R U . . .
C61 C 0.9988(4) 0.1350(4) 0.8595(3) 0.0210(10) Uani 1 1 d . . . . .
C62 C 1.0692(4) 0.0910(4) 0.9370(4) 0.0248(11) Uani 1 1 d . . . . .
H62 H 1.054637 0.119756 1.002779 0.030 Uiso 1 1 calc R U . . .
C63 C 1.1573(5) 0.0083(4) 0.9187(4) 0.0328(12) Uani 1 1 d . . . . .
H63 H 1.201553 -0.020198 0.971584 0.039 Uiso 1 1 calc R U . . .
C64 C 1.1831(4) -0.0348(4) 0.8233(4) 0.0295(12) Uani 1 1 d . . . . .
H64 H 1.246844 -0.089248 0.811841 0.035 Uiso 1 1 calc R U . . .
C65 C 1.1151(4) 0.0027(4) 0.7473(4) 0.0268(11) Uani 1 1 d . . . . .
H65 H 1.130703 -0.028479 0.681995 0.032 Uiso 1 1 calc R U . . .
C66 C 1.0213(4) 0.0870(4) 0.7621(4) 0.0235(10) 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
O1 C61 1.299(5) . ?
O1 Ir1 2.118(3) . ?
Ir1 C41 2.007(4) . ?
Ir1 C21 2.016(4) . ?
Ir1 N1 2.055(3) . ?
Ir1 N2 2.060(3) . ?
Ir1 N3 2.160(4) . ?
S1 C27 1.742(4) . ?
S1 C28 1.751(4) . ?
S2 C48 1.740(4) . ?
S2 C47 1.747(4) . ?
N1 C12 1.340(5) . ?
N1 C16 1.367(5) . ?
N2 C32 1.335(5) . ?
N2 C36 1.372(5) . ?
N3 C1 1.305(5) . ?
N3 C51 1.431(5) . ?
C1 C66 1.432(6) . ?
C12 C13 1.371(6) . ?
C13 C14 1.384(6) . ?
C14 C15 1.375(6) . ?
C15 C16 1.396(5) . ?
C16 C28 1.429(6) . ?
C21 C28 1.377(5) . ?
C21 C22 1.449(6) . ?
C22 C27 1.419(6) . ?
C22 C23 1.427(5) . ?
C23 C24 1.374(6) . ?
C24 C25 1.381(6) . ?
C25 C26 1.380(6) . ?
C26 C27 1.387(6) . ?
C32 C33 1.371(6) . ?
C33 C34 1.395(6) . ?
C34 C35 1.369(6) . ?
C35 C36 1.395(5) . ?
C36 C48 1.442(6) . ?
C41 C48 1.370(5) . ?
C41 C42 1.457(6) . ?
C42 C43 1.406(5) . ?
C42 C47 1.413(6) . ?
C43 C44 1.372(6) . ?
C44 C45 1.396(6) . ?
C45 C46 1.378(6) . ?
C46 C47 1.391(6) . ?
C51 C56 1.386(6) . ?
C51 C52 1.389(6) . ?
C52 C53 1.378(6) . ?
C53 C54 1.386(7) . ?
C54 C55 1.394(7) . ?
C54 C57 1.484(6) . ?
C55 C56 1.387(6) . ?
C61 C66 1.415(6) . ?
C61 C62 1.429(6) . ?
C62 C63 1.371(6) . ?
C63 C64 1.399(7) . ?
C64 C65 1.360(6) . ?
C65 C66 1.424(6) . ?

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
C61 O1 Ir1 125.9(3) . . ?
C41 Ir1 C21 90.50(16) . . ?
C41 Ir1 N1 100.31(15) . . ?
C21 Ir1 N1 80.29(15) . . ?
C41 Ir1 N2 80.23(15) . . ?
C21 Ir1 N2 97.50(15) . . ?
N1 Ir1 N2 177.72(14) . . ?
C41 Ir1 O1 173.75(14) . . ?
C21 Ir1 O1 86.05(14) . . ?
N1 Ir1 O1 84.26(12) . . ?
N2 Ir1 O1 95.04(13) . . ?
C41 Ir1 N3 96.48(15) . . ?
C21 Ir1 N3 172.58(14) . . ?
N1 Ir1 N3 95.91(13) . . ?
N2 Ir1 N3 86.21(13) . . ?
O1 Ir1 N3 87.23(12) . . ?
C27 S1 C28 90.2(2) . . ?
C48 S2 C47 89.5(2) . . ?
C12 N1 C16 119.1(4) . . ?
C12 N1 Ir1 125.8(3) . . ?
C16 N1 Ir1 114.9(3) . . ?
C32 N2 C36 119.7(4) . . ?
C32 N2 Ir1 125.0(3) . . ?
C36 N2 Ir1 115.3(3) . . ?
C1 N3 C51 115.2(4) . . ?
C1 N3 Ir1 123.5(3) . . ?
C51 N3 Ir1 120.5(3) . . ?
N3 C1 C66 128.4(4) . . ?
N1 C12 C13 122.5(4) . . ?
C12 C13 C14 119.0(4) . . ?
C15 C14 C13 119.5(4) . . ?
C14 C15 C16 119.4(4) . . ?
N1 C16 C15 120.5(4) . . ?
N1 C16 C28 112.3(4) . . ?
C15 C16 C28 127.2(4) . . ?
C28 C21 C22 110.0(4) . . ?
C28 C21 Ir1 112.0(3) . . ?
C22 C21 Ir1 137.6(3) . . ?
C27 C22 C23 117.1(4) . . ?
C27 C22 C21 113.0(4) . . ?
C23 C22 C21 130.0(4) . . ?
C24 C23 C22 119.9(4) . . ?
C23 C24 C25 121.1(4) . . ?
C26 C25 C24 121.2(4) . . ?
C25 C26 C27 118.5(4) . . ?
C26 C27 C22 122.1(4) . . ?
C26 C27 S1 126.1(4) . . ?
C22 C27 S1 111.8(3) . . ?
C21 C28 C16 119.4(4) . . ?
C21 C28 S1 115.0(3) . . ?
C16 C28 S1 125.6(3) . . ?
N2 C32 C33 122.4(4) . . ?
C32 C33 C34 118.6(4) . . ?
C35 C34 C33 119.9(4) . . ?
C34 C35 C36 119.3(4) . . ?
N2 C36 C35 120.1(4) . . ?
N2 C36 C48 112.1(4) . . ?
C35 C36 C48 127.8(4) . . ?
C48 C41 C42 109.1(4) . . ?
C48 C41 Ir1 113.5(3) . . ?
C42 C41 Ir1 137.4(3) . . ?
C43 C42 C47 117.4(4) . . ?
C43 C42 C41 129.7(4) . . ?
C47 C42 C41 112.9(3) . . ?
C44 C43 C42 120.2(4) . . ?
C43 C44 C45 121.1(4) . . ?
C46 C45 C44 120.7(4) . . ?
C45 C46 C47 118.2(4) . . ?
C46 C47 C42 122.4(4) . . ?
C46 C47 S2 125.6(3) . . ?
C42 C47 S2 112.1(3) . . ?
C41 C48 C36 118.8(4) . . ?
C41 C48 S2 116.4(3) . . ?
C36 C48 S2 124.7(3) . . ?
C56 C51 C52 119.0(4) . . ?
C56 C51 N3 119.4(4) . . ?
C52 C51 N3 121.7(4) . . ?
C53 C52 C51 119.8(4) . . ?
C52 C53 C54 122.6(5) . . ?
C53 C54 C55 116.7(4) . . ?
C53 C54 C57 121.7(5) . . ?
C55 C54 C57 121.6(5) . . ?
C56 C55 C54 121.7(5) . . ?
C51 C56 C55 120.2(4) . . ?
O1 C61 C66 125.8(4) . . ?
O1 C61 C62 117.0(4) . . ?
C66 C61 C62 117.2(4) . . ?
C63 C62 C61 121.5(5) . . ?
C62 C63 C64 121.1(5) . . ?
C65 C64 C63 118.7(4) . . ?
C64 C65 C66 122.3(5) . . ?
C61 C66 C65 119.1(4) . . ?
C61 C66 C1 124.2(4) . . ?
C65 C66 C1 116.4(4) . . ?

_refine_diff_density_max         0.904
_refine_diff_density_min         -0.933
_refine_diff_density_rms         0.153


####################################################################### 
# 
# 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_piq-L6
_database_code_depnum_ccdc_archive 'CCDC 2300733'
loop_
_audit_author_name
_audit_author_address
'Thomas Teets'
;University of Houston
United States of America
;
_audit_update_record             
;
2023-10-11 deposited with the CCDC.	2024-01-19 downloaded from the CCDC.
;
_audit_creation_date             2023-06-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H29 F3 Ir N3 O'
_chemical_formula_sum            'C44 H29 F3 Ir N3 O'
_chemical_formula_weight         864.90
_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'
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'
O O 0.0106 0.0060 '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                   18.3303(17)
_cell_length_b                   11.9159(11)
_cell_length_c                   15.9378(15)
_cell_angle_alpha                90
_cell_angle_beta                 106.9370(10)
_cell_angle_gamma                90
_cell_volume                     3330.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5369
_cell_measurement_temperature    123.21
_cell_measurement_theta_max      26.57
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.792
_shelx_estimated_absorpt_T_min   0.395
_exptl_absorpt_coefficient_mu    4.068
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0844 before and 0.0468 after correction.
The Ratio of minimum to maximum transmission is 0.8063.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20714
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.583
_diffrn_reflns_theta_min         2.066
_diffrn_ambient_temperature      123.21
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6321
_reflns_number_total             7708
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.801
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         7708
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      0.968
_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)+(0.0276P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0614
_refine_ls_wR_factor_ref         0.0653
_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:
 C43(H43), C5(H5), C9(H9), C20(H20), C39(H39), C17(H17), C2(H2), C14(H14),
 C35(H35), C24(H24), C30(H30), C29(H29), C37(H37), C40(H40), C3(H3), C10(H10),
 C32(H32), C4(H4), C12(H12), C18(H18), C42(H42), C33(H33), C27(H27), C19(H19),
 C34(H34), C25(H25), C15(H15), C11(H11), C26(H26)
;
_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
Ir1 Ir 0.20836(2) 0.40774(2) 0.29896(2) 0.01282(5) Uani 1 1 d . . . . .
O1 O 0.11352(14) 0.49781(19) 0.21640(16) 0.0182(6) Uani 1 1 d . . . . .
N2 N 0.26582(17) 0.5551(2) 0.3322(2) 0.0152(6) Uani 1 1 d . . . . .
N3 N 0.24283(17) 0.3741(2) 0.1833(2) 0.0162(7) Uani 1 1 d . . . . .
N1 N 0.15540(16) 0.2560(2) 0.27718(19) 0.0140(6) Uani 1 1 d . . . . .
F3 F 0.41587(17) -0.09032(19) 0.2168(2) 0.0570(9) Uani 1 1 d . . . . .
F2 F 0.50854(16) 0.0124(2) 0.2822(2) 0.0666(10) Uani 1 1 d . . . . .
C1 C 0.2872(2) 0.3131(3) 0.3798(2) 0.0146(7) Uani 1 1 d . . . . .
C16 C 0.1731(2) 0.4522(3) 0.4019(2) 0.0146(7) Uani 1 1 d . . . . .
F1 F 0.47583(19) -0.0028(2) 0.1443(2) 0.0719(11) Uani 1 1 d . . . . .
C7 C 0.1982(2) 0.1656(3) 0.3130(2) 0.0137(7) Uani 1 1 d . . . . .
C21 C 0.2000(2) 0.5574(3) 0.4385(2) 0.0150(7) Uani 1 1 d . . . . .
C38 C 0.2962(2) 0.2848(3) 0.1869(2) 0.0173(8) Uani 1 1 d . . . . .
C22 C 0.2594(2) 0.6080(3) 0.4054(2) 0.0158(8) Uani 1 1 d . . . . .
C43 C 0.3708(2) 0.2938(3) 0.2397(2) 0.0186(8) Uani 1 1 d . . . . .
H43 H 0.387786 0.361529 0.270750 0.022 Uiso 1 1 calc R U . . .
C8 C 0.1682(2) 0.0555(3) 0.2869(2) 0.0145(7) Uani 1 1 d . . . . .
C5 C 0.3172(2) 0.1223(3) 0.4380(3) 0.0195(8) Uani 1 1 d . . . . .
H5 H 0.304374 0.044948 0.436989 0.023 Uiso 1 1 calc R U . . .
C6 C 0.2705(2) 0.1961(3) 0.3769(2) 0.0146(7) Uani 1 1 d . . . . .
C9 C 0.2140(2) -0.0434(3) 0.2996(2) 0.0198(8) Uani 1 1 d . . . . .
H9 H 0.267745 -0.038064 0.324123 0.024 Uiso 1 1 calc R U . . .
C20 C 0.1668(2) 0.6095(3) 0.4979(3) 0.0211(8) Uani 1 1 d . . . . .
H20 H 0.180950 0.683910 0.517410 0.025 Uiso 1 1 calc R U . . .
C36 C 0.1527(2) 0.5021(3) 0.0832(2) 0.0181(8) Uani 1 1 d . . . . .
C39 C 0.2712(2) 0.1851(3) 0.1430(2) 0.0208(8) Uani 1 1 d . . . . .
H39 H 0.219944 0.178535 0.107034 0.025 Uiso 1 1 calc R U . . .
C17 C 0.1218(2) 0.3952(3) 0.4370(2) 0.0164(8) Uani 1 1 d . . . . .
H17 H 0.106393 0.321168 0.417637 0.020 Uiso 1 1 calc R U . . .
C2 C 0.3544(2) 0.3485(3) 0.4423(2) 0.0189(8) Uani 1 1 d . . . . .
H2 H 0.368072 0.425610 0.444521 0.023 Uiso 1 1 calc R U . . .
C14 C 0.0459(2) 0.1435(3) 0.2127(2) 0.0185(8) Uani 1 1 d . . . . .
H14 H -0.007196 0.138970 0.183738 0.022 Uiso 1 1 calc R U . . .
C23 C 0.3116(2) 0.6962(3) 0.4443(2) 0.0180(8) Uani 1 1 d . . . . .
C35 C 0.1376(2) 0.5495(3) -0.0015(3) 0.0244(9) Uani 1 1 d . . . . .
H35 H 0.169785 0.529914 -0.036385 0.029 Uiso 1 1 calc R U . . .
C24 C 0.3208(2) 0.7403(3) 0.5299(3) 0.0249(9) Uani 1 1 d . . . . .
H24 H 0.289940 0.712087 0.563818 0.030 Uiso 1 1 calc R U . . .
C30 C 0.3149(2) 0.5967(3) 0.2891(3) 0.0207(8) Uani 1 1 d . . . . .
H30 H 0.317670 0.559996 0.237241 0.025 Uiso 1 1 calc R U . . .
C29 C 0.3595(2) 0.6874(3) 0.3172(3) 0.0213(9) Uani 1 1 d . . . . .
H29 H 0.389534 0.716874 0.282842 0.026 Uiso 1 1 calc R U . . .
C31 C 0.1057(2) 0.5331(3) 0.1370(2) 0.0150(7) Uani 1 1 d . . . . .
C37 C 0.2124(2) 0.4192(3) 0.1071(3) 0.0200(8) Uani 1 1 d . . . . .
H37 H 0.232035 0.394582 0.061225 0.024 Uiso 1 1 calc R U . . .
C28 C 0.3614(2) 0.7384(3) 0.3979(3) 0.0201(8) Uani 1 1 d . . . . .
C40 C 0.3208(2) 0.0947(3) 0.1516(3) 0.0231(9) Uani 1 1 d . . . . .
H40 H 0.303469 0.026319 0.121769 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4013(2) 0.2745(3) 0.5009(2) 0.0217(8) Uani 1 1 d . . . . .
H3 H 0.446687 0.300708 0.542009 0.026 Uiso 1 1 calc R U . . .
C10 C 0.1804(2) -0.1465(3) 0.2762(3) 0.0226(9) Uani 1 1 d . . . . .
H10 H 0.211574 -0.211588 0.283364 0.027 Uiso 1 1 calc R U . . .
C13 C 0.0891(2) 0.0440(3) 0.2421(2) 0.0161(8) Uani 1 1 d . . . . .
C32 C 0.0430(2) 0.6050(3) 0.0978(3) 0.0186(8) Uani 1 1 d . . . . .
H32 H 0.008521 0.623503 0.130051 0.022 Uiso 1 1 calc R U . . .
C4 C 0.3816(2) 0.1614(3) 0.4993(3) 0.0222(9) Uani 1 1 d . . . . .
H4 H 0.412728 0.111074 0.540711 0.027 Uiso 1 1 calc R U . . .
C12 C 0.0567(2) -0.0638(3) 0.2245(2) 0.0200(8) Uani 1 1 d . . . . .
H12 H 0.003055 -0.071453 0.200029 0.024 Uiso 1 1 calc R U . . .
C18 C 0.0930(2) 0.4446(3) 0.4993(2) 0.0218(8) Uani 1 1 d . . . . .
H18 H 0.058818 0.404014 0.522736 0.026 Uiso 1 1 calc R U . . .
C42 C 0.4208(2) 0.2047(3) 0.2475(2) 0.0204(8) Uani 1 1 d . . . . .
H42 H 0.472266 0.211818 0.282622 0.024 Uiso 1 1 calc R U . . .
C33 C 0.0307(2) 0.6482(3) 0.0157(3) 0.0224(9) Uani 1 1 d . . . . .
H33 H -0.011458 0.696837 -0.007482 0.027 Uiso 1 1 calc R U . . .
C27 C 0.4128(2) 0.8245(3) 0.4344(3) 0.0251(9) Uani 1 1 d . . . . .
H27 H 0.443869 0.855090 0.401569 0.030 Uiso 1 1 calc R U . . .
C19 C 0.1138(2) 0.5526(3) 0.5275(3) 0.0236(9) Uani 1 1 d . . . . .
H19 H 0.091510 0.587736 0.567583 0.028 Uiso 1 1 calc R U . . .
C34 C 0.0790(2) 0.6222(3) -0.0351(3) 0.0250(9) Uani 1 1 d . . . . .
H34 H 0.071251 0.654424 -0.091544 0.030 Uiso 1 1 calc R U . . .
C25 C 0.3728(2) 0.8219(3) 0.5641(3) 0.0272(9) Uani 1 1 d . . . . .
H25 H 0.377604 0.849622 0.621309 0.033 Uiso 1 1 calc R U . . .
C15 C 0.0813(2) 0.2439(3) 0.2263(2) 0.0172(8) Uani 1 1 d . . . . .
H15 H 0.053859 0.308671 0.199754 0.021 Uiso 1 1 calc R U . . .
C41 C 0.3955(2) 0.1048(3) 0.2037(3) 0.0218(9) Uani 1 1 d . . . . .
C11 C 0.1016(2) -0.1574(3) 0.2424(2) 0.0219(9) Uani 1 1 d . . . . .
H11 H 0.079166 -0.229799 0.231769 0.026 Uiso 1 1 calc R U . . .
C26 C 0.4192(2) 0.8655(3) 0.5165(3) 0.0282(10) Uani 1 1 d . . . . .
H26 H 0.454903 0.923171 0.540788 0.034 Uiso 1 1 calc R U . . .
C44 C 0.4484(2) 0.0078(3) 0.2118(3) 0.0271(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
Ir1 O1 2.138(2) . ?
Ir1 N2 2.036(3) . ?
Ir1 N3 2.153(3) . ?
Ir1 N1 2.033(3) . ?
Ir1 C1 1.984(4) . ?
Ir1 C16 2.002(3) . ?
O1 C31 1.302(4) . ?
N2 C22 1.361(4) . ?
N2 C30 1.374(4) . ?
N3 C38 1.436(4) . ?
N3 C37 1.297(5) . ?
N1 C7 1.357(4) . ?
N1 C15 1.372(4) . ?
F3 C44 1.325(4) . ?
F2 C44 1.325(5) . ?
C1 C6 1.426(5) . ?
C1 C2 1.403(5) . ?
C16 C21 1.410(5) . ?
C16 C17 1.403(5) . ?
F1 C44 1.320(5) . ?
C7 C8 1.437(5) . ?
C7 C6 1.463(5) . ?
C21 C22 1.471(5) . ?
C21 C20 1.409(5) . ?
C38 C43 1.386(5) . ?
C38 C39 1.387(5) . ?
C22 C23 1.435(5) . ?
C43 H43 0.9500 . ?
C43 C42 1.385(5) . ?
C8 C9 1.427(5) . ?
C8 C13 1.423(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.403(5) . ?
C5 C4 1.375(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.376(5) . ?
C20 H20 0.9500 . ?
C20 C19 1.376(5) . ?
C36 C35 1.414(5) . ?
C36 C31 1.430(5) . ?
C36 C37 1.441(5) . ?
C39 H39 0.9500 . ?
C39 C40 1.390(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(5) . ?
C14 H14 0.9500 . ?
C14 C13 1.427(5) . ?
C14 C15 1.348(5) . ?
C23 C24 1.425(5) . ?
C23 C28 1.424(5) . ?
C35 H35 0.9500 . ?
C35 C34 1.362(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.359(5) . ?
C30 H30 0.9500 . ?
C30 C29 1.350(5) . ?
C29 H29 0.9500 . ?
C29 C28 1.414(5) . ?
C31 C32 1.423(5) . ?
C37 H37 0.9500 . ?
C28 C27 1.400(5) . ?
C40 H40 0.9500 . ?
C40 C41 1.386(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(5) . ?
C13 C12 1.409(5) . ?
C32 H32 0.9500 . ?
C32 C33 1.363(5) . ?
C4 H4 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.367(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(5) . ?
C42 H42 0.9500 . ?
C42 C41 1.389(5) . ?
C33 H33 0.9500 . ?
C33 C34 1.397(5) . ?
C27 H27 0.9500 . ?
C27 C26 1.369(6) . ?
C19 H19 0.9500 . ?
C34 H34 0.9500 . ?
C25 H25 0.9500 . ?
C25 C26 1.395(6) . ?
C15 H15 0.9500 . ?
C41 C44 1.490(5) . ?
C11 H11 0.9500 . ?
C26 H26 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
O1 Ir1 N3 87.44(10) . . ?
N2 Ir1 O1 89.62(10) . . ?
N2 Ir1 N3 97.16(11) . . ?
N1 Ir1 O1 94.53(10) . . ?
N1 Ir1 N2 174.81(12) . . ?
N1 Ir1 N3 86.15(11) . . ?
C1 Ir1 O1 173.12(11) . . ?
C1 Ir1 N2 95.58(13) . . ?
C1 Ir1 N3 96.34(12) . . ?
C1 Ir1 N1 80.04(13) . . ?
C1 Ir1 C16 88.05(14) . . ?
C16 Ir1 O1 88.44(12) . . ?
C16 Ir1 N2 79.90(13) . . ?
C16 Ir1 N3 174.95(12) . . ?
C16 Ir1 N1 97.08(13) . . ?
C31 O1 Ir1 126.9(2) . . ?
C22 N2 Ir1 117.1(2) . . ?
C22 N2 C30 119.6(3) . . ?
C30 N2 Ir1 123.1(2) . . ?
C38 N3 Ir1 118.1(2) . . ?
C37 N3 Ir1 124.9(2) . . ?
C37 N3 C38 116.5(3) . . ?
C7 N1 Ir1 116.4(2) . . ?
C7 N1 C15 121.1(3) . . ?
C15 N1 Ir1 122.4(2) . . ?
C6 C1 Ir1 115.2(3) . . ?
C2 C1 Ir1 127.8(3) . . ?
C2 C1 C6 116.9(3) . . ?
C21 C16 Ir1 114.7(2) . . ?
C17 C16 Ir1 127.8(3) . . ?
C17 C16 C21 117.4(3) . . ?
N1 C7 C8 118.5(3) . . ?
N1 C7 C6 113.0(3) . . ?
C8 C7 C6 128.4(3) . . ?
C16 C21 C22 114.9(3) . . ?
C20 C21 C16 120.2(3) . . ?
C20 C21 C22 124.8(3) . . ?
C43 C38 N3 120.5(3) . . ?
C43 C38 C39 119.7(3) . . ?
C39 C38 N3 119.6(3) . . ?
N2 C22 C21 112.1(3) . . ?
N2 C22 C23 119.8(3) . . ?
C23 C22 C21 127.9(3) . . ?
C38 C43 H43 119.8 . . ?
C42 C43 C38 120.3(3) . . ?
C42 C43 H43 119.8 . . ?
C9 C8 C7 123.6(3) . . ?
C13 C8 C7 118.7(3) . . ?
C13 C8 C9 117.6(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C1 C6 C7 114.1(3) . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 C7 125.0(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 119.9(3) . . ?
C19 C20 H20 120.0 . . ?
C35 C36 C31 119.0(3) . . ?
C35 C36 C37 116.6(3) . . ?
C31 C36 C37 124.3(3) . . ?
C38 C39 H39 119.9 . . ?
C38 C39 C40 120.2(4) . . ?
C40 C39 H39 119.9 . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 H17 119.3 . . ?
C1 C2 H2 119.0 . . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 H2 119.0 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C15 C14 C13 119.3(3) . . ?
C24 C23 C22 124.2(3) . . ?
C28 C23 C22 118.8(3) . . ?
C28 C23 C24 116.8(3) . . ?
C36 C35 H35 118.6 . . ?
C34 C35 C36 122.8(4) . . ?
C34 C35 H35 118.6 . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.4(4) . . ?
C25 C24 H24 119.3 . . ?
N2 C30 H30 118.5 . . ?
C29 C30 N2 123.0(3) . . ?
C29 C30 H30 118.5 . . ?
C30 C29 H29 120.1 . . ?
C30 C29 C28 119.9(3) . . ?
C28 C29 H29 120.1 . . ?
O1 C31 C36 125.8(3) . . ?
O1 C31 C32 117.9(3) . . ?
C32 C31 C36 116.3(3) . . ?
N3 C37 C36 128.2(3) . . ?
N3 C37 H37 115.9 . . ?
C36 C37 H37 115.9 . . ?
C29 C28 C23 118.1(3) . . ?
C27 C28 C23 120.0(4) . . ?
C27 C28 C29 121.8(3) . . ?
C39 C40 H40 120.1 . . ?
C41 C40 C39 119.7(3) . . ?
C41 C40 H40 120.1 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.3(4) . . ?
C11 C10 H10 119.3 . . ?
C8 C13 C14 118.2(3) . . ?
C12 C13 C8 119.8(3) . . ?
C12 C13 C14 122.0(3) . . ?
C31 C32 H32 118.8 . . ?
C33 C32 C31 122.4(3) . . ?
C33 C32 H32 118.8 . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C13 C12 H12 119.7 . . ?
C11 C12 C13 120.5(4) . . ?
C11 C12 H12 119.7 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C43 C42 H42 120.1 . . ?
C43 C42 C41 119.8(4) . . ?
C41 C42 H42 120.1 . . ?
C32 C33 H33 119.5 . . ?
C32 C33 C34 121.1(4) . . ?
C34 C33 H33 119.5 . . ?
C28 C27 H27 119.4 . . ?
C26 C27 C28 121.2(4) . . ?
C26 C27 H27 119.4 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C35 C34 C33 118.3(4) . . ?
C35 C34 H34 120.9 . . ?
C33 C34 H34 120.9 . . ?
C24 C25 H25 119.4 . . ?
C24 C25 C26 121.1(4) . . ?
C26 C25 H25 119.4 . . ?
N1 C15 H15 118.8 . . ?
C14 C15 N1 122.3(3) . . ?
C14 C15 H15 118.8 . . ?
C40 C41 C42 120.2(3) . . ?
C40 C41 C44 119.3(3) . . ?
C42 C41 C44 120.5(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C27 C26 C25 119.4(4) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
F3 C44 F2 105.3(3) . . ?
F3 C44 C41 113.4(4) . . ?
F2 C44 C41 113.6(3) . . ?
F1 C44 F3 104.5(3) . . ?
F1 C44 F2 105.9(4) . . ?
F1 C44 C41 113.3(3) . . ?

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
Ir1 O1 C31 C36 11.6(5) . . . . ?
Ir1 O1 C31 C32 -171.4(2) . . . . ?
Ir1 N2 C22 C21 -10.3(4) . . . . ?
Ir1 N2 C22 C23 165.2(3) . . . . ?
Ir1 N2 C30 C29 -172.2(3) . . . . ?
Ir1 N3 C38 C43 -67.6(4) . . . . ?
Ir1 N3 C38 C39 106.8(3) . . . . ?
Ir1 N3 C37 C36 2.3(5) . . . . ?
Ir1 N1 C7 C8 -169.0(2) . . . . ?
Ir1 N1 C7 C6 12.5(4) . . . . ?
Ir1 N1 C15 C14 -179.3(3) . . . . ?
Ir1 C1 C6 C7 1.2(4) . . . . ?
Ir1 C1 C6 C5 -172.4(3) . . . . ?
Ir1 C1 C2 C3 173.6(3) . . . . ?
Ir1 C16 C21 C22 -10.0(4) . . . . ?
Ir1 C16 C21 C20 166.1(3) . . . . ?
Ir1 C16 C17 C18 -169.3(3) . . . . ?
O1 C31 C32 C33 178.6(3) . . . . ?
N2 C22 C23 C24 -165.9(3) . . . . ?
N2 C22 C23 C28 9.6(5) . . . . ?
N2 C30 C29 C28 5.1(6) . . . . ?
N3 C38 C43 C42 175.7(3) . . . . ?
N3 C38 C39 C40 -174.8(3) . . . . ?
N1 C7 C8 C9 161.8(3) . . . . ?
N1 C7 C8 C13 -15.0(5) . . . . ?
N1 C7 C6 C1 -8.8(4) . . . . ?
N1 C7 C6 C5 164.5(3) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C16 C21 C22 N2 13.1(4) . . . . ?
C16 C21 C22 C23 -162.0(3) . . . . ?
C16 C21 C20 C19 7.1(6) . . . . ?
C16 C17 C18 C19 0.8(6) . . . . ?
C7 N1 C15 C14 3.3(5) . . . . ?
C7 C8 C9 C10 177.1(3) . . . . ?
C7 C8 C13 C14 10.0(5) . . . . ?
C7 C8 C13 C12 -173.0(3) . . . . ?
C21 C16 C17 C18 6.0(5) . . . . ?
C21 C22 C23 C24 8.8(6) . . . . ?
C21 C22 C23 C28 -175.6(3) . . . . ?
C21 C20 C19 C18 -0.1(6) . . . . ?
C38 N3 C37 C36 173.7(3) . . . . ?
C38 C43 C42 C41 -1.5(5) . . . . ?
C38 C39 C40 C41 -0.3(6) . . . . ?
C22 N2 C30 C29 1.7(6) . . . . ?
C22 C21 C20 C19 -177.2(4) . . . . ?
C22 C23 C24 C25 178.1(4) . . . . ?
C22 C23 C28 C29 -2.9(5) . . . . ?
C22 C23 C28 C27 180.0(3) . . . . ?
C43 C38 C39 C40 -0.4(5) . . . . ?
C43 C42 C41 C40 0.8(6) . . . . ?
C43 C42 C41 C44 -179.6(3) . . . . ?
C8 C7 C6 C1 172.9(3) . . . . ?
C8 C7 C6 C5 -13.8(6) . . . . ?
C8 C9 C10 C11 -1.8(5) . . . . ?
C8 C13 C12 C11 -6.4(5) . . . . ?
C6 C1 C2 C3 -2.2(5) . . . . ?
C6 C7 C8 C9 -19.9(5) . . . . ?
C6 C7 C8 C13 163.3(3) . . . . ?
C6 C5 C4 C3 -0.5(6) . . . . ?
C9 C8 C13 C14 -167.0(3) . . . . ?
C9 C8 C13 C12 10.1(5) . . . . ?
C9 C10 C11 C12 5.8(6) . . . . ?
C20 C21 C22 N2 -162.7(3) . . . . ?
C20 C21 C22 C23 22.2(6) . . . . ?
C36 C35 C34 C33 -1.8(6) . . . . ?
C36 C31 C32 C33 -4.1(5) . . . . ?
C39 C38 C43 C42 1.3(5) . . . . ?
C39 C40 C41 C42 0.1(6) . . . . ?
C39 C40 C41 C44 -179.4(3) . . . . ?
C17 C16 C21 C22 174.1(3) . . . . ?
C17 C16 C21 C20 -9.8(5) . . . . ?
C17 C18 C19 C20 -3.9(6) . . . . ?
C2 C1 C6 C7 177.5(3) . . . . ?
C2 C1 C6 C5 3.9(5) . . . . ?
C2 C3 C4 C5 2.2(6) . . . . ?
C14 C13 C12 C11 170.6(3) . . . . ?
C23 C24 C25 C26 0.0(6) . . . . ?
C23 C28 C27 C26 3.5(6) . . . . ?
C35 C36 C31 O1 -178.8(3) . . . . ?
C35 C36 C31 C32 4.2(5) . . . . ?
C35 C36 C37 N3 170.9(4) . . . . ?
C24 C23 C28 C29 173.0(3) . . . . ?
C24 C23 C28 C27 -4.2(5) . . . . ?
C24 C25 C26 C27 -0.8(6) . . . . ?
C30 N2 C22 C21 175.4(3) . . . . ?
C30 N2 C22 C23 -9.1(5) . . . . ?
C30 C29 C28 C23 -4.3(5) . . . . ?
C30 C29 C28 C27 172.8(4) . . . . ?
C29 C28 C27 C26 -173.5(4) . . . . ?
C31 C36 C35 C34 -1.4(6) . . . . ?
C31 C36 C37 N3 -13.0(6) . . . . ?
C31 C32 C33 C34 1.0(6) . . . . ?
C37 N3 C38 C43 120.3(4) . . . . ?
C37 N3 C38 C39 -65.3(4) . . . . ?
C37 C36 C35 C34 174.8(4) . . . . ?
C37 C36 C31 O1 5.3(6) . . . . ?
C37 C36 C31 C32 -171.7(3) . . . . ?
C28 C23 C24 C25 2.5(5) . . . . ?
C28 C27 C26 C25 -1.0(6) . . . . ?
C40 C41 C44 F3 -39.4(5) . . . . ?
C40 C41 C44 F2 -159.6(4) . . . . ?
C40 C41 C44 F1 79.5(5) . . . . ?
C13 C8 C9 C10 -6.0(5) . . . . ?
C13 C14 C15 N1 -8.4(5) . . . . ?
C13 C12 C11 C10 -1.6(5) . . . . ?
C32 C33 C34 C35 2.0(6) . . . . ?
C4 C5 C6 C1 -2.6(5) . . . . ?
C4 C5 C6 C7 -175.5(3) . . . . ?
C42 C41 C44 F3 141.0(4) . . . . ?
C42 C41 C44 F2 20.8(5) . . . . ?
C42 C41 C44 F1 -100.1(5) . . . . ?
C15 N1 C7 C8 8.5(5) . . . . ?
C15 N1 C7 C6 -170.0(3) . . . . ?
C15 C14 C13 C8 1.5(5) . . . . ?
C15 C14 C13 C12 -175.6(3) . . . . ?

_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_piq-L8
_database_code_depnum_ccdc_archive 'CCDC 2300735'
loop_
_audit_author_name
_audit_author_address
'Thomas Teets'
;University of Houston
United States of America
;
_audit_update_record             
;
2023-10-11 deposited with the CCDC.	2024-01-19 downloaded from the CCDC.
;
_audit_creation_date             2023-10-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C51 H39 Ir N4'
_chemical_formula_sum            'C51 H39 Ir N4'
_chemical_formula_weight         900.06
_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'
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'

_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                   10.4288(18)
_cell_length_b                   12.298(2)
_cell_length_c                   15.903(3)
_cell_angle_alpha                70.259(2)
_cell_angle_beta                 83.748(2)
_cell_angle_gamma                84.374(2)
_cell_volume                     1904.4(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.675
_shelx_estimated_absorpt_T_min   0.416
_exptl_absorpt_coefficient_mu    3.549
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0771 before and 0.0410 after correction.
The Ratio of minimum to maximum transmission is 0.8360.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27082
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.654
_diffrn_reflns_theta_min         1.365
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8057
_reflns_number_total             8813
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.461
_refine_diff_density_min         -0.987
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         8813
_refine_ls_number_restraints     508
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0240P)²+2.1754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0588
_refine_ls_wR_factor_ref         0.0604
_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. Restrained distances
 H5-H14
 2.1 with sigma of 0.01
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C23(H23), C2(H2), C3(H3), C24(H24), C11(H11), C39(H39), C9(H9),
 C18(H18), C37(H37), C14(H14), C8(H8), C5(H5), C50(H50), C28(H28), C4(H4),
 C43(H43), C20(H20), C19(H19), C29(H29), C26(H26), C42(H42), C46(H46), C27(H27),
  C32(H32), C12(H12), C47(H47), C49(H49), C33(H33), C34(H34), C35(H35),
 C13(H13), C40(H40)
4.b Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C44(H44A,H44B,H44C)
;
_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
Ir1 Ir 0.72813(2) 0.54394(2) 0.72376(2) 0.01989(4) Uani 1 1 d . . . . .
N1 N 0.5510(2) 0.6237(2) 0.68998(17) 0.0217(5) Uani 1 1 d . . . . .
N2 N 0.9046(2) 0.4589(2) 0.75501(16) 0.0215(5) Uani 1 1 d . . . . .
N4 N 0.7920(2) 0.7164(2) 0.68693(19) 0.0270(5) Uani 1 1 d . . . . .
C16 C 0.6846(3) 0.3791(3) 0.75485(19) 0.0208(6) Uani 1 1 d . . . . .
N3 N 0.7178(2) 0.5400(2) 0.86219(17) 0.0266(5) Uani 1 1 d . . . . .
C1 C 0.7302(3) 0.5431(3) 0.5973(2) 0.0205(5) Uani 1 1 d . . . . .
C7 C 0.5225(3) 0.6491(3) 0.6040(2) 0.0219(5) Uani 1 1 d . . . . .
C17 C 0.5681(3) 0.3396(3) 0.7436(2) 0.0264(6) Uani 1 1 d . . . . .
H17 H 0.497661 0.392565 0.727176 0.032 Uiso 1 1 calc R U . . .
C23 C 1.0118(3) 0.5175(3) 0.7500(2) 0.0230(6) Uani 1 1 d . . . . .
H23 H 1.006374 0.597784 0.724755 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6194(3) 0.5971(3) 0.5514(2) 0.0214(5) Uani 1 1 d . . . . .
C2 C 0.8256(3) 0.4884(3) 0.5537(2) 0.0245(6) Uani 1 1 d . . . . .
H2 H 0.898242 0.451211 0.582957 0.029 Uiso 1 1 calc R U . . .
C21 C 0.7881(3) 0.2945(3) 0.7821(2) 0.0239(6) Uani 1 1 d . . . . .
C30 C 1.0216(3) 0.2801(3) 0.8323(2) 0.0249(6) Uani 1 1 d . . . . .
C15 C 0.4068(3) 0.7195(3) 0.5741(2) 0.0243(6) Uani 1 1 d . . . . .
C3 C 0.8138(3) 0.4887(3) 0.4676(2) 0.0279(6) Uani 1 1 d . . . . .
H3 H 0.879671 0.454283 0.438883 0.033 Uiso 1 1 calc R U . . .
C24 C 1.1254(3) 0.4631(3) 0.7804(2) 0.0256(6) Uani 1 1 d . . . . .
H24 H 1.197668 0.505162 0.772913 0.031 Uiso 1 1 calc R U . . .
C11 C 0.1960(3) 0.8057(3) 0.6134(3) 0.0327(7) Uani 1 1 d . . . . .
H11 H 0.134046 0.817180 0.656824 0.039 Uiso 1 1 calc R U . . .
C39 C 0.5499(3) 0.4059(3) 0.9371(2) 0.0306(7) Uani 1 1 d . . . . .
H39 H 0.491105 0.454878 0.899221 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3492(3) 0.7115(3) 0.7287(2) 0.0282(6) Uani 1 1 d . . . . .
H9 H 0.291148 0.726794 0.772695 0.034 Uiso 1 1 calc R U . . .
C18 C 0.5544(3) 0.2241(3) 0.7560(2) 0.0319(7) Uani 1 1 d . . . . .
H18 H 0.475339 0.200452 0.749182 0.038 Uiso 1 1 calc R U . . .
C22 C 0.9084(3) 0.3423(3) 0.7905(2) 0.0219(6) Uani 1 1 d . . . . .
C25 C 1.1334(3) 0.3418(3) 0.8236(2) 0.0259(6) Uani 1 1 d . . . . .
C38 C 0.6767(3) 0.4365(3) 0.9305(2) 0.0276(6) Uani 1 1 d . . . . .
C45 C 0.7837(3) 0.7821(3) 0.5944(2) 0.0281(6) Uani 1 1 d . . . . .
C37 C 0.7758(3) 0.6106(3) 0.8885(2) 0.0306(7) Uani 1 1 d . . . . .
H37 H 0.781309 0.589274 0.949982 0.037 Uiso 1 1 calc R U . . .
C14 C 0.3788(3) 0.7725(3) 0.4831(2) 0.0311(7) Uani 1 1 d . . . . .
H14 H 0.440551 0.765620 0.438105 0.037 Uiso 1 1 calc DR U . . .
C8 C 0.4666(3) 0.6583(3) 0.7500(2) 0.0257(6) Uani 1 1 d . . . . .
H8 H 0.491142 0.644692 0.807403 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6074(3) 0.5909(3) 0.4662(2) 0.0253(6) Uani 1 1 d . . . . .
H5 H 0.532169 0.621771 0.437885 0.030 Uiso 1 1 calc DR U . . .
C50 C 0.8724(3) 0.7596(3) 0.5293(2) 0.0313(7) Uani 1 1 d . . . . .
H50 H 0.943486 0.707843 0.546893 0.038 Uiso 1 1 calc R U . . .
C36 C 0.8314(3) 0.7149(3) 0.8365(2) 0.0320(6) Uani 1 1 d . . . . .
C28 C 1.1387(3) 0.1065(3) 0.9223(2) 0.0375(8) Uani 1 1 d . . . . .
H28 H 1.139863 0.028576 0.957047 0.045 Uiso 1 1 calc R U . . .
C4 C 0.7040(3) 0.5403(3) 0.4241(2) 0.0284(7) Uani 1 1 d . . . . .
H4 H 0.696272 0.540352 0.366371 0.034 Uiso 1 1 calc R U . . .
C31 C 0.8318(3) 0.7692(3) 0.7409(2) 0.0279(6) Uani 1 1 d . . . . .
C43 C 0.7628(3) 0.3607(3) 0.9876(2) 0.0348(7) Uani 1 1 d . . . . .
H43 H 0.847734 0.379567 0.984524 0.042 Uiso 1 1 calc R U . . .
C10 C 0.3146(3) 0.7441(3) 0.6393(2) 0.0263(6) Uani 1 1 d . . . . .
C20 C 0.7751(3) 0.1792(3) 0.7907(2) 0.0306(7) Uani 1 1 d . . . . .
H20 H 0.845527 0.125519 0.804653 0.037 Uiso 1 1 calc R U . . .
C19 C 0.6585(3) 0.1441(3) 0.7786(2) 0.0337(7) Uani 1 1 d . . . . .
H19 H 0.650029 0.066854 0.785649 0.040 Uiso 1 1 calc R U . . .
C29 C 1.0270(3) 0.1615(3) 0.8861(2) 0.0328(7) Uani 1 1 d . . . . .
H29 H 0.953338 0.120324 0.896963 0.039 Uiso 1 1 calc R U . . .
C26 C 1.2479(3) 0.2820(3) 0.8610(2) 0.0347(8) Uani 1 1 d . . . . .
H26 H 1.321691 0.322152 0.853719 0.042 Uiso 1 1 calc R U . . .
C42 C 0.7227(4) 0.2577(3) 1.0488(3) 0.0407(8) Uani 1 1 d . . . . .
H42 H 0.781683 0.208009 1.086129 0.049 Uiso 1 1 calc R U . . .
C46 C 0.6811(3) 0.8640(3) 0.5655(3) 0.0336(7) Uani 1 1 d . . . . .
H46 H 0.622196 0.882920 0.607478 0.040 Uiso 1 1 calc R U . . .
C41 C 0.5966(4) 0.2268(3) 1.0560(2) 0.0375(7) Uani 1 1 d . . . . .
C27 C 1.2510(3) 0.1660(3) 0.9078(3) 0.0391(8) Uani 1 1 d . . . . .
H27 H 1.327592 0.126704 0.929835 0.047 Uiso 1 1 calc R U . . .
C32 C 0.8827(3) 0.8809(3) 0.7050(2) 0.0316(7) Uani 1 1 d . . . . .
H32 H 0.878480 0.921606 0.644253 0.038 Uiso 1 1 calc R U . . .
C12 C 0.1712(3) 0.8486(3) 0.5252(3) 0.0354(7) Uani 1 1 d . . . . .
H12 H 0.092330 0.888255 0.508666 0.043 Uiso 1 1 calc R U . . .
C47 C 0.6662(3) 0.9173(3) 0.4747(3) 0.0382(7) Uani 1 1 d . . . . .
H47 H 0.597174 0.971396 0.456957 0.046 Uiso 1 1 calc R U . . .
C49 C 0.8567(3) 0.8129(3) 0.4388(2) 0.0366(7) Uani 1 1 d . . . . .
H49 H 0.916954 0.795964 0.396656 0.044 Uiso 1 1 calc R U . . .
C33 C 0.9372(3) 0.9302(3) 0.7566(3) 0.0367(7) Uani 1 1 d . . . . .
H33 H 0.971817 1.001965 0.729799 0.044 Uiso 1 1 calc R U . . .
C48 C 0.7517(4) 0.8918(3) 0.4101(3) 0.0382(7) Uani 1 1 d . . . . .
C34 C 0.9419(4) 0.8743(3) 0.8496(3) 0.0415(8) Uani 1 1 d . . . . .
H34 H 0.980724 0.907607 0.884094 0.050 Uiso 1 1 calc R U . . .
C35 C 0.8888(3) 0.7712(3) 0.8875(3) 0.0373(8) Uani 1 1 d . . . . .
H35 H 0.889445 0.735171 0.949137 0.045 Uiso 1 1 calc R U . . .
C13 C 0.2649(3) 0.8327(3) 0.4601(3) 0.0367(8) Uani 1 1 d . . . . .
H13 H 0.248851 0.863884 0.399909 0.044 Uiso 1 1 calc R U . . .
C40 C 0.5110(3) 0.3035(3) 0.9993(2) 0.0344(7) Uani 1 1 d . . . . .
H40 H 0.425511 0.285315 1.003495 0.041 Uiso 1 1 calc R U . . .
C51 C 0.7303(4) 0.9458(4) 0.3122(3) 0.0536(11) Uani 1 1 d . . . . .
H51A H 0.639508 0.963435 0.305462 0.080 Uiso 1 1 calc R U . . .
H51B H 0.762794 0.892696 0.281236 0.080 Uiso 1 1 calc R U . . .
H51C H 0.774985 1.015739 0.287467 0.080 Uiso 1 1 calc R U . . .
C44 C 0.5512(5) 0.1150(4) 1.1220(3) 0.0573(12) Uani 1 1 d . . . . .
H44A H 0.624428 0.061585 1.140573 0.086 Uiso 1 1 calc R U . . .
H44B H 0.494768 0.082551 1.094262 0.086 Uiso 1 1 calc R U . . .
H44C H 0.505427 0.129483 1.173277 0.086 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
Ir1 N1 2.041(2) . ?
Ir1 N2 2.049(2) . ?
Ir1 N4 2.154(3) . ?
Ir1 C16 2.004(3) . ?
Ir1 N3 2.177(3) . ?
Ir1 C1 2.012(3) . ?
N1 C7 1.355(4) . ?
N1 C8 1.374(4) . ?
N2 C23 1.369(4) . ?
N2 C22 1.351(4) . ?
N4 C45 1.428(4) . ?
N4 C31 1.355(4) . ?
C16 C17 1.403(4) . ?
C16 C21 1.419(4) . ?
N3 C38 1.433(4) . ?
N3 C37 1.303(4) . ?
C1 C6 1.419(4) . ?
C1 C2 1.399(4) . ?
C7 C6 1.477(4) . ?
C7 C15 1.441(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.356(4) . ?
C6 C5 1.403(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(4) . ?
C21 C22 1.473(4) . ?
C21 C20 1.397(4) . ?
C30 C22 1.439(4) . ?
C30 C25 1.422(4) . ?
C30 C29 1.419(5) . ?
C15 C14 1.421(5) . ?
C15 C10 1.424(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.414(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.411(4) . ?
C11 C12 1.366(5) . ?
C39 H39 0.9300 . ?
C39 C38 1.394(5) . ?
C39 C40 1.378(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.351(4) . ?
C9 C10 1.419(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(5) . ?
C25 C26 1.416(4) . ?
C38 C43 1.393(5) . ?
C45 C50 1.392(5) . ?
C45 C46 1.398(5) . ?
C37 H37 0.9300 . ?
C37 C36 1.411(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.354(5) . ?
C8 H8 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.365(4) . ?
C50 H50 0.9300 . ?
C50 C49 1.386(5) . ?
C36 C31 1.439(5) . ?
C36 C35 1.436(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.369(5) . ?
C28 C27 1.398(5) . ?
C4 H4 0.9300 . ?
C31 C32 1.428(5) . ?
C43 H43 0.9300 . ?
C43 C42 1.381(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.383(5) . ?
C19 H19 0.9300 . ?
C29 H29 0.9300 . ?
C26 H26 0.9300 . ?
C26 C27 1.368(5) . ?
C42 H42 0.9300 . ?
C42 C41 1.387(5) . ?
C46 H46 0.9300 . ?
C46 C47 1.388(5) . ?
C41 C40 1.392(5) . ?
C41 C44 1.503(5) . ?
C27 H27 0.9300 . ?
C32 H32 0.9300 . ?
C32 C33 1.368(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.395(5) . ?
C47 H47 0.9300 . ?
C47 C48 1.383(6) . ?
C49 H49 0.9300 . ?
C49 C48 1.396(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.409(5) . ?
C48 C51 1.504(5) . ?
C34 H34 0.9300 . ?
C34 C35 1.353(5) . ?
C35 H35 0.9300 . ?
C13 H13 0.9300 . ?
C40 H40 0.9300 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?

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
N1 Ir1 N2 177.54(10) . . ?
N1 Ir1 N4 85.51(10) . . ?
N1 Ir1 N3 99.48(10) . . ?
N2 Ir1 N4 96.33(10) . . ?
N2 Ir1 N3 82.28(10) . . ?
N4 Ir1 N3 86.79(11) . . ?
C16 Ir1 N1 98.90(11) . . ?
C16 Ir1 N2 79.19(11) . . ?
C16 Ir1 N4 174.95(11) . . ?
C16 Ir1 N3 94.87(11) . . ?
C16 Ir1 C1 83.05(11) . . ?
C1 Ir1 N1 79.14(11) . . ?
C1 Ir1 N2 99.02(11) . . ?
C1 Ir1 N4 95.43(11) . . ?
C1 Ir1 N3 177.27(10) . . ?
C7 N1 Ir1 117.77(19) . . ?
C7 N1 C8 120.5(3) . . ?
C8 N1 Ir1 121.6(2) . . ?
C23 N2 Ir1 121.7(2) . . ?
C22 N2 Ir1 117.20(19) . . ?
C22 N2 C23 120.7(3) . . ?
C45 N4 Ir1 113.8(2) . . ?
C31 N4 Ir1 128.1(2) . . ?
C31 N4 C45 118.0(3) . . ?
C17 C16 Ir1 127.2(2) . . ?
C17 C16 C21 116.8(3) . . ?
C21 C16 Ir1 115.7(2) . . ?
C38 N3 Ir1 117.4(2) . . ?
C37 N3 Ir1 123.8(2) . . ?
C37 N3 C38 116.4(3) . . ?
C6 C1 Ir1 115.8(2) . . ?
C2 C1 Ir1 126.1(2) . . ?
C2 C1 C6 117.9(3) . . ?
N1 C7 C6 112.8(3) . . ?
N1 C7 C15 119.6(3) . . ?
C15 C7 C6 127.6(3) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 C16 122.1(3) . . ?
C18 C17 H17 118.9 . . ?
N2 C23 H23 118.7 . . ?
C24 C23 N2 122.5(3) . . ?
C24 C23 H23 118.7 . . ?
C1 C6 C7 113.9(3) . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C7 126.5(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C16 C21 C22 114.0(3) . . ?
C20 C21 C16 120.5(3) . . ?
C20 C21 C22 125.2(3) . . ?
C25 C30 C22 118.5(3) . . ?
C29 C30 C22 124.1(3) . . ?
C29 C30 C25 117.3(3) . . ?
C14 C15 C7 125.2(3) . . ?
C14 C15 C10 116.2(3) . . ?
C10 C15 C7 118.5(3) . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.5(3) . . ?
C25 C24 H24 120.2 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C12 C11 C10 120.6(3) . . ?
C38 C39 H39 119.7 . . ?
C40 C39 H39 119.7 . . ?
C40 C39 C38 120.5(3) . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
N2 C22 C21 112.7(3) . . ?
N2 C22 C30 119.5(3) . . ?
C30 C22 C21 127.8(3) . . ?
C24 C25 C30 118.6(3) . . ?
C24 C25 C26 121.5(3) . . ?
C26 C25 C30 119.8(3) . . ?
C39 C38 N3 119.9(3) . . ?
C43 C38 N3 121.6(3) . . ?
C43 C38 C39 118.3(3) . . ?
C50 C45 N4 120.6(3) . . ?
C50 C45 C46 117.8(3) . . ?
C46 C45 N4 121.4(3) . . ?
N3 C37 H37 115.5 . . ?
N3 C37 C36 128.9(3) . . ?
C36 C37 H37 115.5 . . ?
C15 C14 H14 119.0 . . ?
C13 C14 C15 122.0(3) . . ?
C13 C14 H14 119.0 . . ?
N1 C8 H8 118.8 . . ?
C9 C8 N1 122.3(3) . . ?
C9 C8 H8 118.8 . . ?
C6 C5 H5 119.4 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C45 C50 H50 119.4 . . ?
C49 C50 C45 121.2(3) . . ?
C49 C50 H50 119.4 . . ?
C37 C36 C31 126.7(3) . . ?
C37 C36 C35 114.3(3) . . ?
C35 C36 C31 119.0(3) . . ?
C29 C28 H28 119.6 . . ?
C29 C28 C27 120.8(3) . . ?
C27 C28 H28 119.6 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
N4 C31 C36 122.6(3) . . ?
N4 C31 C32 121.4(3) . . ?
C32 C31 C36 115.9(3) . . ?
C38 C43 H43 119.8 . . ?
C42 C43 C38 120.5(3) . . ?
C42 C43 H43 119.8 . . ?
C11 C10 C15 120.2(3) . . ?
C11 C10 C9 121.6(3) . . ?
C9 C10 C15 118.1(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.7 . . ?
C18 C19 C20 119.8(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C30 C29 H29 119.4 . . ?
C28 C29 C30 121.2(3) . . ?
C28 C29 H29 119.4 . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.6(3) . . ?
C27 C26 H26 119.7 . . ?
C43 C42 H42 119.2 . . ?
C43 C42 C41 121.6(4) . . ?
C41 C42 H42 119.2 . . ?
C45 C46 H46 119.7 . . ?
C47 C46 C45 120.6(3) . . ?
C47 C46 H46 119.7 . . ?
C42 C41 C40 117.6(3) . . ?
C42 C41 C44 122.4(4) . . ?
C40 C41 C44 120.0(4) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 C28 119.8(3) . . ?
C26 C27 H27 120.1 . . ?
C31 C32 H32 118.7 . . ?
C33 C32 C31 122.6(3) . . ?
C33 C32 H32 118.7 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C46 C47 H47 119.2 . . ?
C48 C47 C46 121.6(3) . . ?
C48 C47 H47 119.2 . . ?
C50 C49 H49 119.5 . . ?
C50 C49 C48 120.9(4) . . ?
C48 C49 H49 119.5 . . ?
C32 C33 H33 119.4 . . ?
C32 C33 C34 121.2(3) . . ?
C34 C33 H33 119.4 . . ?
C47 C48 C49 117.8(3) . . ?
C47 C48 C51 120.8(4) . . ?
C49 C48 C51 121.3(4) . . ?
C33 C34 H34 120.8 . . ?
C35 C34 C33 118.5(4) . . ?
C35 C34 H34 120.8 . . ?
C36 C35 H35 118.7 . . ?
C34 C35 C36 122.7(4) . . ?
C34 C35 H35 118.7 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C39 C40 C41 121.5(3) . . ?
C39 C40 H40 119.2 . . ?
C41 C40 H40 119.2 . . ?
C48 C51 H51A 109.5 . . ?
C48 C51 H51B 109.5 . . ?
C48 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

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
Ir1 N1 C7 C6 9.2(3) . . . . ?
Ir1 N1 C7 C15 -171.3(2) . . . . ?
Ir1 N1 C8 C9 179.8(2) . . . . ?
Ir1 N2 C23 C24 171.9(2) . . . . ?
Ir1 N2 C22 C21 12.7(3) . . . . ?
Ir1 N2 C22 C30 -165.9(2) . . . . ?
Ir1 N4 C45 C50 -74.6(3) . . . . ?
Ir1 N4 C45 C46 100.0(3) . . . . ?
Ir1 N4 C31 C36 -2.8(4) . . . . ?
Ir1 N4 C31 C32 174.2(2) . . . . ?
Ir1 C16 C17 C18 171.0(2) . . . . ?
Ir1 C16 C21 C22 5.0(3) . . . . ?
Ir1 C16 C21 C20 -169.1(2) . . . . ?
Ir1 N3 C38 C39 -67.5(3) . . . . ?
Ir1 N3 C38 C43 108.3(3) . . . . ?
Ir1 N3 C37 C36 14.6(5) . . . . ?
Ir1 C1 C6 C7 2.3(3) . . . . ?
Ir1 C1 C6 C5 -174.0(2) . . . . ?
Ir1 C1 C2 C3 176.7(2) . . . . ?
N1 C7 C6 C1 -7.3(4) . . . . ?
N1 C7 C6 C5 168.7(3) . . . . ?
N1 C7 C15 C14 166.1(3) . . . . ?
N1 C7 C15 C10 -10.5(4) . . . . ?
N2 C23 C24 C25 -3.6(5) . . . . ?
N4 C45 C50 C49 172.2(3) . . . . ?
N4 C45 C46 C47 -172.4(3) . . . . ?
N4 C31 C32 C33 -172.2(3) . . . . ?
C16 C17 C18 C19 -1.3(5) . . . . ?
C16 C21 C22 N2 -11.4(4) . . . . ?
C16 C21 C22 C30 167.1(3) . . . . ?
C16 C21 C20 C19 -4.4(5) . . . . ?
N3 C38 C43 C42 -175.6(3) . . . . ?
N3 C37 C36 C31 2.4(6) . . . . ?
N3 C37 C36 C35 -179.5(3) . . . . ?
C1 C6 C5 C4 -4.2(5) . . . . ?
C1 C2 C3 C4 -2.3(5) . . . . ?
C7 N1 C8 C9 4.6(5) . . . . ?
C7 C6 C5 C4 -180.0(3) . . . . ?
C7 C15 C14 C13 176.5(3) . . . . ?
C7 C15 C10 C11 -175.5(3) . . . . ?
C7 C15 C10 C9 8.5(4) . . . . ?
C17 C16 C21 C22 178.5(3) . . . . ?
C17 C16 C21 C20 4.4(4) . . . . ?
C17 C18 C19 C20 1.5(5) . . . . ?
C23 N2 C22 C21 -174.5(3) . . . . ?
C23 N2 C22 C30 6.9(4) . . . . ?
C23 C24 C25 C30 1.2(5) . . . . ?
C23 C24 C25 C26 -176.3(3) . . . . ?
C6 C1 C2 C3 1.3(4) . . . . ?
C6 C7 C15 C14 -14.5(5) . . . . ?
C6 C7 C15 C10 168.9(3) . . . . ?
C6 C5 C4 C3 3.2(5) . . . . ?
C2 C1 C6 C7 178.2(3) . . . . ?
C2 C1 C6 C5 1.9(4) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C21 C16 C17 C18 -1.6(4) . . . . ?
C21 C20 C19 C18 1.4(5) . . . . ?
C30 C25 C26 C27 -1.9(5) . . . . ?
C15 C7 C6 C1 173.3(3) . . . . ?
C15 C7 C6 C5 -10.8(5) . . . . ?
C15 C14 C13 C12 2.2(5) . . . . ?
C24 C25 C26 C27 175.6(3) . . . . ?
C11 C12 C13 C14 1.8(5) . . . . ?
C39 C38 C43 C42 0.3(5) . . . . ?
C22 N2 C23 C24 -0.6(4) . . . . ?
C22 C21 C20 C19 -177.8(3) . . . . ?
C22 C30 C25 C24 4.9(4) . . . . ?
C22 C30 C25 C26 -177.6(3) . . . . ?
C22 C30 C29 C28 178.5(3) . . . . ?
C25 C30 C22 N2 -9.0(4) . . . . ?
C25 C30 C22 C21 172.6(3) . . . . ?
C25 C30 C29 C28 -5.1(5) . . . . ?
C25 C26 C27 C28 -2.9(6) . . . . ?
C38 N3 C37 C36 176.7(3) . . . . ?
C38 C39 C40 C41 -1.2(5) . . . . ?
C38 C43 C42 C41 -0.5(6) . . . . ?
C45 N4 C31 C36 173.7(3) . . . . ?
C45 N4 C31 C32 -9.3(4) . . . . ?
C45 C50 C49 C48 0.5(5) . . . . ?
C45 C46 C47 C48 -0.1(5) . . . . ?
C37 N3 C38 C39 129.2(3) . . . . ?
C37 N3 C38 C43 -55.0(4) . . . . ?
C37 C36 C31 N4 -9.1(5) . . . . ?
C37 C36 C31 C32 173.7(3) . . . . ?
C37 C36 C35 C34 -177.2(3) . . . . ?
C14 C15 C10 C11 7.6(4) . . . . ?
C14 C15 C10 C9 -168.4(3) . . . . ?
C8 N1 C7 C6 -175.4(3) . . . . ?
C8 N1 C7 C15 4.1(4) . . . . ?
C8 C9 C10 C15 -0.3(5) . . . . ?
C8 C9 C10 C11 -176.3(3) . . . . ?
C50 C45 C46 C47 2.4(5) . . . . ?
C50 C49 C48 C47 1.8(5) . . . . ?
C50 C49 C48 C51 -177.0(3) . . . . ?
C36 C31 C32 C33 5.0(5) . . . . ?
C31 N4 C45 C50 108.4(3) . . . . ?
C31 N4 C45 C46 -77.0(4) . . . . ?
C31 C36 C35 C34 1.0(5) . . . . ?
C31 C32 C33 C34 -2.3(5) . . . . ?
C43 C42 C41 C40 -0.2(6) . . . . ?
C43 C42 C41 C44 179.8(4) . . . . ?
C10 C15 C14 C13 -6.8(5) . . . . ?
C10 C11 C12 C13 -0.9(5) . . . . ?
C10 C9 C8 N1 -6.5(5) . . . . ?
C20 C21 C22 N2 162.4(3) . . . . ?
C20 C21 C22 C30 -19.1(5) . . . . ?
C29 C30 C22 N2 167.5(3) . . . . ?
C29 C30 C22 C21 -10.9(5) . . . . ?
C29 C30 C25 C24 -171.8(3) . . . . ?
C29 C30 C25 C26 5.8(5) . . . . ?
C29 C28 C27 C26 3.7(6) . . . . ?
C42 C41 C40 C39 1.1(5) . . . . ?
C46 C45 C50 C49 -2.6(5) . . . . ?
C46 C47 C48 C49 -2.0(5) . . . . ?
C46 C47 C48 C51 176.8(3) . . . . ?
C27 C28 C29 C30 0.4(6) . . . . ?
C32 C33 C34 C35 -1.3(5) . . . . ?
C12 C11 C10 C15 -4.0(5) . . . . ?
C12 C11 C10 C9 171.9(3) . . . . ?
C33 C34 C35 C36 1.9(6) . . . . ?
C35 C36 C31 N4 172.9(3) . . . . ?
C35 C36 C31 C32 -4.3(4) . . . . ?
C40 C39 C38 N3 176.5(3) . . . . ?
C40 C39 C38 C43 0.5(5) . . . . ?
C44 C41 C40 C39 -179.0(4) . . . . ?

_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_pphen_L5-B
_database_code_depnum_ccdc_archive 'CCDC 2300734'
loop_
_audit_author_name
_audit_author_address
'Thomas Teets'
;University of Houston
United States of America
;
_audit_update_record             
;
2023-10-11 deposited with the CCDC.	2024-01-19 downloaded from the CCDC.
;
_audit_creation_date             2023-10-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C51 H32 F3 Ir N4 O, 2(C4 H8 O)'
_chemical_formula_sum            'C59 H48 F3 Ir N4 O3'
_chemical_formula_weight         1110.21
_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'
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'
O O 0.0106 0.0060 '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                   10.916(4)
_cell_length_b                   13.168(4)
_cell_length_c                   18.015(6)
_cell_angle_alpha                82.060(5)
_cell_angle_beta                 78.545(5)
_cell_angle_gamma                78.258(5)
_cell_volume                     2472.0(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3910
_cell_measurement_temperature    123.20
_cell_measurement_theta_max      18.83
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.682
_exptl_absorpt_coefficient_mu    2.762
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0744 before and 0.0610 after correction.
The Ratio of minimum to maximum transmission is 0.8680.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1116
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            32112
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.559
_diffrn_reflns_theta_min         1.588
_diffrn_ambient_temperature      123.20
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7894
_reflns_number_total             10180
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.124
_refine_diff_density_min         -1.479
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         10180
_refine_ls_number_restraints     1291
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      0.944
_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)+(0.0520P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1118
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
5.a Secondary CH2 refined with riding coordinates:
 C101(H10A,H10B), C102(H10C,H10D), C103(H10E,H10F), C91(H91A,H91B), C104(H10G,
 H10H), C93(H93A,H93B), C92(H92A,H92B), C94(H94A,H94B)
5.b Aromatic/amide H refined with riding coordinates:
 C71(H71), C52(H52), C82(H82), C42(H42), C43(H43), C72(H72), C74(H74),
 C60(H60), C12(H12), C55(H55), C33(H33), C45(H45), C63(H63), C53(H53), C85(H85),
  C86(H86), C44(H44), C22(H22), C54(H54), C15(H15), C13(H13), C83(H83),
 C30(H30), C73(H73), C32(H32), C31(H31), C14(H14), C62(H62), C61(H61), C25(H25),
  C23(H23), C24(H24)
;
_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
Ir1 Ir 0.76611(2) 0.39021(2) 0.26018(2) 0.02205(8) Uani 1 1 d . U . . .
O1 O 0.6178(4) 0.5263(3) 0.2497(2) 0.0241(7) Uani 1 1 d . U . . .
N2 N 0.7888(4) 0.4189(4) 0.1425(3) 0.0233(7) Uani 1 1 d . U . . .
N3 N 0.5931(4) 0.3270(4) 0.2784(3) 0.0230(7) Uani 1 1 d . U . . .
F2 F 0.5364(4) 1.0181(3) 0.0708(3) 0.0653(12) Uani 1 1 d . U . . .
F3 F 0.3326(4) 1.0446(3) 0.0809(3) 0.0666(12) Uani 1 1 d . U . . .
N1 N 0.7525(4) 0.3627(4) 0.3763(3) 0.0275(8) Uani 1 1 d . U . . .
N4 N 0.4138(5) 0.5750(4) 0.2225(3) 0.0277(9) Uani 1 1 d . U . . .
F1 F 0.4164(6) 1.0600(3) 0.1760(3) 0.0830(15) Uani 1 1 d . U . . .
C41 C 0.9063(5) 0.4712(4) 0.2384(3) 0.0239(8) Uani 1 1 d . U . . .
C50 C 0.8426(5) 0.5018(4) 0.1151(3) 0.0229(9) Uani 1 1 d . U . . .
C11 C 0.8873(6) 0.2587(5) 0.2698(3) 0.0280(10) Uani 1 1 d . U . . .
C46 C 0.9258(5) 0.5223(4) 0.1643(3) 0.0252(10) Uani 1 1 d . U . . .
C75 C 0.4891(5) 0.3966(5) 0.2620(3) 0.0253(10) Uani 1 1 d . U . . .
C20 C 0.7918(6) 0.2627(5) 0.4007(3) 0.0297(11) Uani 1 1 d . U . . .
C58 C 0.7303(5) 0.3752(5) 0.0956(3) 0.0244(10) Uani 1 1 d . U . . .
C16 C 0.8806(6) 0.2038(5) 0.3431(4) 0.0319(12) Uani 1 1 d . U . . .
C71 C 0.5796(6) 0.2268(5) 0.3013(3) 0.0292(11) Uani 1 1 d . U . . .
H71 H 0.650662 0.177917 0.314779 0.035 Uiso 1 1 calc R U . . .
C81 C 0.4282(6) 0.6791(5) 0.1978(3) 0.0286(11) Uani 1 1 d . U . . .
C52 C 0.8422(6) 0.6655(5) 0.0264(4) 0.0326(11) Uani 1 1 d . U . . .
H52 H 0.888447 0.691770 0.056604 0.039 Uiso 1 1 calc R U . . .
C57 C 0.7050(6) 0.4262(5) 0.0258(3) 0.0281(10) Uani 1 1 d . U . . .
C51 C 0.8130(6) 0.5637(5) 0.0460(3) 0.0262(10) Uani 1 1 d . U . . .
C28 C 0.7019(6) 0.4375(5) 0.4292(3) 0.0297(11) Uani 1 1 d . U . . .
C82 C 0.3168(6) 0.7550(5) 0.2097(4) 0.0346(13) Uani 1 1 d . U . . .
H82 H 0.239978 0.734328 0.236138 0.041 Uiso 1 1 calc R U . . .
C21 C 0.7445(6) 0.2227(6) 0.4782(4) 0.0378(12) Uani 1 1 d . U . . .
C42 C 0.9852(6) 0.4859(5) 0.2881(4) 0.0314(11) Uani 1 1 d . U . . .
H42 H 0.972361 0.455489 0.339364 0.038 Uiso 1 1 calc R U . . .
C76 C 0.5091(6) 0.5081(5) 0.2415(3) 0.0257(10) Uani 1 1 d . U . . .
C43 C 1.0803(6) 0.5434(5) 0.2633(4) 0.0368(12) Uani 1 1 d . U . . .
H43 H 1.132026 0.552126 0.297716 0.044 Uiso 1 1 calc R U . . .
C72 C 0.4668(6) 0.1933(5) 0.3058(4) 0.0350(12) Uani 1 1 d . U . . .
H72 H 0.459918 0.122681 0.322251 0.042 Uiso 1 1 calc R U . . .
C56 C 0.7405(6) 0.5281(5) 0.0014(3) 0.0294(10) Uani 1 1 d . U . . .
C74 C 0.3737(6) 0.3669(5) 0.2632(4) 0.0319(12) Uani 1 1 d . U . . .
H74 H 0.303766 0.416154 0.248686 0.038 Uiso 1 1 calc R U . . .
C60 C 0.6465(6) 0.3770(5) -0.0192(4) 0.0381(13) Uani 1 1 d . U . . .
H60 H 0.627073 0.411351 -0.066518 0.046 Uiso 1 1 calc R U . . .
C12 C 0.9791(6) 0.2124(5) 0.2113(4) 0.0345(13) Uani 1 1 d . U . . .
H12 H 0.983514 0.245211 0.160684 0.041 Uiso 1 1 calc R U . . .
C27 C 0.6778(6) 0.4044(6) 0.5073(3) 0.0360(12) Uani 1 1 d . U . . .
C55 C 0.7034(6) 0.5921(5) -0.0626(3) 0.0368(12) Uani 1 1 d . U . . .
H55 H 0.654599 0.568328 -0.092528 0.044 Uiso 1 1 calc R U . . .
C33 C 0.6863(6) 0.5428(5) 0.4022(4) 0.0342(12) Uani 1 1 d . U . . .
H33 H 0.700911 0.563680 0.349059 0.041 Uiso 1 1 calc R U . . .
C84 C 0.4291(6) 0.8898(5) 0.1445(4) 0.0357(12) Uani 1 1 d . U . . .
C45 C 1.0259(6) 0.5783(5) 0.1397(4) 0.0332(12) Uani 1 1 d . U . . .
H45 H 1.040874 0.608971 0.088624 0.040 Uiso 1 1 calc R U . . .
C63 C 0.7017(6) 0.2755(5) 0.1187(4) 0.0334(12) Uani 1 1 d . U . . .
H63 H 0.721146 0.239820 0.165681 0.040 Uiso 1 1 calc R U . . .
C53 C 0.8042(6) 0.7250(5) -0.0353(4) 0.0379(13) Uani 1 1 d . U . . .
H53 H 0.823388 0.793165 -0.047255 0.046 Uiso 1 1 calc R U . . .
C85 C 0.5399(6) 0.8153(5) 0.1324(4) 0.0364(13) Uani 1 1 d . U . . .
H85 H 0.616749 0.835575 0.105630 0.044 Uiso 1 1 calc R U . . .
C86 C 0.5382(6) 0.7123(5) 0.1594(4) 0.0344(12) Uani 1 1 d . U . . .
H86 H 0.614725 0.662626 0.151234 0.041 Uiso 1 1 calc R U . . .
C44 C 1.1016(6) 0.5887(5) 0.1893(4) 0.0387(13) Uani 1 1 d . U . . .
H44 H 1.168769 0.626988 0.172695 0.046 Uiso 1 1 calc R U . . .
C22 C 0.7434(7) 0.1151(6) 0.4987(4) 0.0480(15) Uani 1 1 d . U . . .
H22 H 0.778172 0.066670 0.462128 0.058 Uiso 1 1 calc R U . . .
C54 C 0.7372(7) 0.6890(5) -0.0824(4) 0.0423(13) Uani 1 1 d . U . . .
H54 H 0.715492 0.730663 -0.126924 0.051 Uiso 1 1 calc R U . . .
C26 C 0.6867(6) 0.2945(6) 0.5320(4) 0.0397(12) Uani 1 1 d . U . . .
C15 C 0.9658(7) 0.1120(5) 0.3583(4) 0.0414(15) Uani 1 1 d . U . . .
H15 H 0.961599 0.078002 0.408551 0.050 Uiso 1 1 calc R U . . .
C13 C 1.0631(7) 0.1204(5) 0.2254(4) 0.0454(16) Uani 1 1 d . U . . .
H13 H 1.124560 0.091269 0.185158 0.054 Uiso 1 1 calc R U . . .
C87 C 0.4297(8) 1.0014(5) 0.1186(4) 0.0472(12) Uani 1 1 d . U . . .
C83 C 0.3167(6) 0.8593(5) 0.1837(4) 0.0378(13) Uani 1 1 d . U . . .
H83 H 0.240749 0.909385 0.192580 0.045 Uiso 1 1 calc R U . . .
C30 C 0.6393(6) 0.4826(6) 0.5588(4) 0.0439(14) Uani 1 1 d . U . . .
H30 H 0.622586 0.463018 0.612079 0.053 Uiso 1 1 calc R U . . .
C73 C 0.3629(6) 0.2646(5) 0.2858(4) 0.0365(13) Uani 1 1 d . U . . .
H73 H 0.284603 0.242612 0.287688 0.044 Uiso 1 1 calc R U . . .
C32 C 0.6489(6) 0.6170(6) 0.4543(4) 0.0407(14) Uani 1 1 d . U . . .
H32 H 0.638762 0.689111 0.436557 0.049 Uiso 1 1 calc R U . . .
C31 C 0.6264(7) 0.5866(6) 0.5314(4) 0.0470(15) Uani 1 1 d . U . . .
H31 H 0.601674 0.638107 0.566197 0.056 Uiso 1 1 calc R U . . .
C14 C 1.0558(7) 0.0712(5) 0.3000(4) 0.0478(17) Uani 1 1 d . U . . .
H14 H 1.113809 0.008807 0.310255 0.057 Uiso 1 1 calc R U . . .
C62 C 0.6461(7) 0.2291(6) 0.0741(4) 0.0424(14) Uani 1 1 d . U . . .
H62 H 0.626546 0.161501 0.090343 0.051 Uiso 1 1 calc R U . . .
C61 C 0.6180(7) 0.2803(6) 0.0053(4) 0.0450(15) Uani 1 1 d . U . . .
H61 H 0.578500 0.247809 -0.025095 0.054 Uiso 1 1 calc R U . . .
C25 C 0.6358(8) 0.2545(7) 0.6055(4) 0.0550(16) Uani 1 1 d . U . . .
H25 H 0.597519 0.301281 0.642753 0.066 Uiso 1 1 calc R U . . .
C23 C 0.6918(8) 0.0806(7) 0.5719(4) 0.0634(19) Uani 1 1 d . U . . .
H23 H 0.692200 0.008296 0.585808 0.076 Uiso 1 1 calc R U . . .
C24 C 0.6400(8) 0.1501(7) 0.6246(4) 0.0641(19) Uani 1 1 d . U . . .
H24 H 0.606645 0.125233 0.675140 0.077 Uiso 1 1 calc R U . . .
O3 O 0.9165(11) 0.8528(9) 0.4570(7) 0.162(3) Uani 1 1 d . U . . .
C101 C 0.8431(14) 0.7971(11) 0.5166(9) 0.136(3) Uani 1 1 d . U . . .
H10A H 0.760713 0.792751 0.503187 0.163 Uiso 1 1 calc R U . . .
H10B H 0.827165 0.829836 0.564663 0.163 Uiso 1 1 calc R U . . .
C102 C 0.9285(12) 0.6888(11) 0.5229(8) 0.121(3) Uani 1 1 d . U . . .
H10C H 0.993121 0.686788 0.554878 0.145 Uiso 1 1 calc R U . . .
H10D H 0.877990 0.633500 0.543726 0.145 Uiso 1 1 calc R U . . .
C103 C 0.9871(12) 0.6790(12) 0.4423(8) 0.129(3) Uani 1 1 d . U . . .
H10E H 1.070873 0.632019 0.438892 0.155 Uiso 1 1 calc R U . . .
H10F H 0.932176 0.649525 0.416597 0.155 Uiso 1 1 calc R U . . .
C91 C 0.7215(19) 0.8341(14) 0.3223(12) 0.192(5) Uani 1 1 d . U . . .
H91A H 0.769610 0.804941 0.363908 0.230 Uiso 1 1 calc R U . . .
H91B H 0.640304 0.807891 0.336586 0.230 Uiso 1 1 calc R U . . .
C104 C 1.0023(14) 0.7828(13) 0.4061(9) 0.145(4) Uani 1 1 d . U . . .
H10G H 1.091129 0.792798 0.401119 0.174 Uiso 1 1 calc R U . . .
H10H H 0.978502 0.794352 0.354910 0.174 Uiso 1 1 calc R U . . .
C93 C 0.8600(19) 0.8576(13) 0.2127(11) 0.198(5) Uani 1 1 d . U . . .
H93A H 0.869183 0.850503 0.157798 0.238 Uiso 1 1 calc R U . . .
H93B H 0.945161 0.850839 0.226079 0.238 Uiso 1 1 calc R U . . .
O2 O 0.6821(13) 0.9547(9) 0.3326(8) 0.209(4) Uani 1 1 d . U . . .
C92 C 0.7873(19) 0.7801(13) 0.2606(12) 0.192(5) Uani 1 1 d . U . . .
H92A H 0.727889 0.760116 0.232570 0.230 Uiso 1 1 calc R U . . .
H92B H 0.845132 0.716691 0.277386 0.230 Uiso 1 1 calc R U . . .
C94 C 0.7740(19) 0.9609(13) 0.2343(12) 0.200(5) Uani 1 1 d . U . . .
H94A H 0.713721 0.983014 0.198177 0.240 Uiso 1 1 calc R U . . .
H94B H 0.827414 1.014936 0.228252 0.240 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
Ir1 O1 2.172(4) . ?
Ir1 N2 2.075(5) . ?
Ir1 N3 2.164(5) . ?
Ir1 N1 2.053(5) . ?
Ir1 C41 1.986(6) . ?
Ir1 C11 1.963(6) . ?
O1 C76 1.297(7) . ?
N2 C50 1.332(7) . ?
N2 C58 1.397(7) . ?
N3 C75 1.361(7) . ?
N3 C71 1.357(7) . ?
F2 C87 1.341(8) . ?
F3 C87 1.357(9) . ?
N1 C20 1.340(7) . ?
N1 C28 1.419(7) . ?
N4 C81 1.411(8) . ?
N4 C76 1.288(7) . ?
F1 C87 1.343(8) . ?
C41 C46 1.407(8) . ?
C41 C42 1.414(8) . ?
C50 C46 1.474(8) . ?
C50 C51 1.447(8) . ?
C11 C16 1.411(8) . ?
C11 C12 1.413(8) . ?
C46 C45 1.406(8) . ?
C75 C76 1.513(8) . ?
C75 C74 1.389(8) . ?
C20 C16 1.462(8) . ?
C20 C21 1.454(8) . ?
C58 C57 1.392(8) . ?
C58 C63 1.399(8) . ?
C16 C15 1.398(8) . ?
C71 H71 0.9500 . ?
C71 C72 1.374(8) . ?
C81 C82 1.408(8) . ?
C81 C86 1.383(8) . ?
C52 H52 0.9500 . ?
C52 C51 1.422(8) . ?
C52 C53 1.354(9) . ?
C57 C56 1.458(8) . ?
C57 C60 1.415(8) . ?
C51 C56 1.413(8) . ?
C28 C27 1.402(8) . ?
C28 C33 1.392(9) . ?
C82 H82 0.9500 . ?
C82 C83 1.388(9) . ?
C21 C22 1.416(9) . ?
C21 C26 1.414(9) . ?
C42 H42 0.9500 . ?
C42 C43 1.376(9) . ?
C43 H43 0.9500 . ?
C43 C44 1.379(10) . ?
C72 H72 0.9500 . ?
C72 C73 1.390(9) . ?
C56 C55 1.407(8) . ?
C74 H74 0.9500 . ?
C74 C73 1.374(9) . ?
C60 H60 0.9500 . ?
C60 C61 1.366(9) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(8) . ?
C27 C26 1.444(10) . ?
C27 C30 1.425(9) . ?
C55 H55 0.9500 . ?
C55 C54 1.380(9) . ?
C33 H33 0.9500 . ?
C33 C32 1.394(8) . ?
C84 C85 1.394(9) . ?
C84 C87 1.480(9) . ?
C84 C83 1.395(9) . ?
C45 H45 0.9500 . ?
C45 C44 1.368(9) . ?
C63 H63 0.9500 . ?
C63 C62 1.367(8) . ?
C53 H53 0.9500 . ?
C53 C54 1.405(9) . ?
C85 H85 0.9500 . ?
C85 C86 1.379(9) . ?
C86 H86 0.9500 . ?
C44 H44 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.381(10) . ?
C54 H54 0.9500 . ?
C26 C25 1.405(9) . ?
C15 H15 0.9500 . ?
C15 C14 1.374(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.403(10) . ?
C83 H83 0.9500 . ?
C30 H30 0.9500 . ?
C30 C31 1.379(10) . ?
C73 H73 0.9500 . ?
C32 H32 0.9500 . ?
C32 C31 1.379(10) . ?
C31 H31 0.9500 . ?
C14 H14 0.9500 . ?
C62 H62 0.9500 . ?
C62 C61 1.386(9) . ?
C61 H61 0.9500 . ?
C25 H25 0.9500 . ?
C25 C24 1.365(11) . ?
C23 H23 0.9500 . ?
C23 C24 1.368(11) . ?
C24 H24 0.9500 . ?
O3 C101 1.419(16) . ?
O3 C104 1.452(16) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
C101 C102 1.540(17) . ?
C102 H10C 0.9900 . ?
C102 H10D 0.9900 . ?
C102 C103 1.478(17) . ?
C103 H10E 0.9900 . ?
C103 H10F 0.9900 . ?
C103 C104 1.458(17) . ?
C91 H91A 0.9900 . ?
C91 H91B 0.9900 . ?
C91 O2 1.585(19) . ?
C91 C92 1.40(2) . ?
C104 H10G 0.9900 . ?
C104 H10H 0.9900 . ?
C93 H93A 0.9900 . ?
C93 H93B 0.9900 . ?
C93 C92 1.49(2) . ?
C93 C94 1.54(2) . ?
O2 C94 1.85(2) . ?
C92 H92A 0.9900 . ?
C92 H92B 0.9900 . ?
C94 H94A 0.9900 . ?
C94 H94B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ir1 O1 80.01(16) . . ?
N2 Ir1 N3 97.60(18) . . ?
N3 Ir1 O1 75.71(16) . . ?
N1 Ir1 O1 101.38(17) . . ?
N1 Ir1 N2 177.25(19) . . ?
N1 Ir1 N3 85.06(18) . . ?
C41 Ir1 O1 94.57(19) . . ?
C41 Ir1 N2 79.0(2) . . ?
C41 Ir1 N3 170.2(2) . . ?
C41 Ir1 N1 98.5(2) . . ?
C11 Ir1 O1 174.3(2) . . ?
C11 Ir1 N2 100.1(2) . . ?
C11 Ir1 N3 98.6(2) . . ?
C11 Ir1 N1 78.8(2) . . ?
C11 Ir1 C41 91.1(2) . . ?
C76 O1 Ir1 115.9(3) . . ?
C50 N2 Ir1 113.1(4) . . ?
C50 N2 C58 119.7(5) . . ?
C58 N2 Ir1 125.6(4) . . ?
C75 N3 Ir1 114.8(4) . . ?
C71 N3 Ir1 127.1(4) . . ?
C71 N3 C75 118.0(5) . . ?
C20 N1 Ir1 113.7(4) . . ?
C20 N1 C28 120.3(5) . . ?
C28 N1 Ir1 125.9(4) . . ?
C76 N4 C81 119.5(5) . . ?
C46 C41 Ir1 114.7(4) . . ?
C46 C41 C42 116.8(5) . . ?
C42 C41 Ir1 128.5(5) . . ?
N2 C50 C46 112.6(5) . . ?
N2 C50 C51 120.6(5) . . ?
C51 C50 C46 126.7(5) . . ?
C16 C11 Ir1 116.3(4) . . ?
C16 C11 C12 116.5(6) . . ?
C12 C11 Ir1 127.2(5) . . ?
C41 C46 C50 114.0(5) . . ?
C45 C46 C41 120.9(6) . . ?
C45 C46 C50 124.8(6) . . ?
N3 C75 C76 115.1(5) . . ?
N3 C75 C74 122.2(6) . . ?
C74 C75 C76 122.7(6) . . ?
N1 C20 C16 113.8(5) . . ?
N1 C20 C21 119.8(6) . . ?
C21 C20 C16 126.4(6) . . ?
N2 C58 C63 118.4(5) . . ?
C57 C58 N2 121.8(5) . . ?
C57 C58 C63 119.8(5) . . ?
C11 C16 C20 112.2(5) . . ?
C15 C16 C11 121.9(6) . . ?
C15 C16 C20 125.1(6) . . ?
N3 C71 H71 118.8 . . ?
N3 C71 C72 122.3(6) . . ?
C72 C71 H71 118.8 . . ?
C82 C81 N4 116.0(6) . . ?
C86 C81 N4 126.4(6) . . ?
C86 C81 C82 117.5(6) . . ?
C51 C52 H52 120.0 . . ?
C53 C52 H52 120.0 . . ?
C53 C52 C51 119.9(6) . . ?
C58 C57 C56 118.8(5) . . ?
C58 C57 C60 118.9(6) . . ?
C60 C57 C56 122.4(6) . . ?
C52 C51 C50 121.2(6) . . ?
C56 C51 C50 119.6(5) . . ?
C56 C51 C52 118.7(6) . . ?
C27 C28 N1 119.6(6) . . ?
C33 C28 N1 118.5(5) . . ?
C33 C28 C27 121.7(6) . . ?
C81 C82 H82 119.2 . . ?
C83 C82 C81 121.5(6) . . ?
C83 C82 H82 119.2 . . ?
C22 C21 C20 121.5(6) . . ?
C26 C21 C20 118.7(6) . . ?
C26 C21 C22 119.5(6) . . ?
C41 C42 H42 119.5 . . ?
C43 C42 C41 121.0(6) . . ?
C43 C42 H42 119.5 . . ?
O1 C76 C75 115.9(5) . . ?
N4 C76 O1 127.5(6) . . ?
N4 C76 C75 116.5(5) . . ?
C42 C43 H43 119.5 . . ?
C42 C43 C44 121.1(6) . . ?
C44 C43 H43 119.5 . . ?
C71 C72 H72 120.6 . . ?
C71 C72 C73 118.9(6) . . ?
C73 C72 H72 120.6 . . ?
C51 C56 C57 117.4(5) . . ?
C55 C56 C57 123.0(6) . . ?
C55 C56 C51 119.5(6) . . ?
C75 C74 H74 120.7 . . ?
C73 C74 C75 118.5(6) . . ?
C73 C74 H74 120.7 . . ?
C57 C60 H60 119.9 . . ?
C61 C60 C57 120.1(6) . . ?
C61 C60 H60 119.9 . . ?
C11 C12 H12 119.0 . . ?
C13 C12 C11 122.1(6) . . ?
C13 C12 H12 119.0 . . ?
C28 C27 C26 119.5(6) . . ?
C28 C27 C30 117.7(7) . . ?
C30 C27 C26 122.8(6) . . ?
C56 C55 H55 119.6 . . ?
C54 C55 C56 120.8(6) . . ?
C54 C55 H55 119.6 . . ?
C28 C33 H33 120.5 . . ?
C28 C33 C32 119.0(6) . . ?
C32 C33 H33 120.5 . . ?
C85 C84 C87 121.1(6) . . ?
C85 C84 C83 119.5(6) . . ?
C83 C84 C87 119.4(6) . . ?
C46 C45 H45 119.9 . . ?
C44 C45 C46 120.2(6) . . ?
C44 C45 H45 119.9 . . ?
C58 C63 H63 119.8 . . ?
C62 C63 C58 120.4(6) . . ?
C62 C63 H63 119.8 . . ?
C52 C53 H53 118.9 . . ?
C52 C53 C54 122.1(6) . . ?
C54 C53 H53 118.9 . . ?
C84 C85 H85 119.9 . . ?
C86 C85 C84 120.1(6) . . ?
C86 C85 H85 119.9 . . ?
C81 C86 H86 119.1 . . ?
C85 C86 C81 121.9(6) . . ?
C85 C86 H86 119.1 . . ?
C43 C44 H44 120.1 . . ?
C45 C44 C43 119.8(6) . . ?
C45 C44 H44 120.1 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.9(7) . . ?
C23 C22 H22 120.1 . . ?
C55 C54 C53 118.8(6) . . ?
C55 C54 H54 120.6 . . ?
C53 C54 H54 120.6 . . ?
C21 C26 C27 118.3(6) . . ?
C25 C26 C21 117.8(7) . . ?
C25 C26 C27 123.9(7) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 C16 119.5(6) . . ?
C14 C15 H15 120.2 . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 119.1(6) . . ?
C14 C13 H13 120.5 . . ?
F2 C87 F3 106.0(6) . . ?
F2 C87 F1 106.4(6) . . ?
F2 C87 C84 113.3(6) . . ?
F3 C87 C84 112.0(6) . . ?
F1 C87 F3 105.3(6) . . ?
F1 C87 C84 113.2(6) . . ?
C82 C83 C84 119.4(6) . . ?
C82 C83 H83 120.3 . . ?
C84 C83 H83 120.3 . . ?
C27 C30 H30 120.0 . . ?
C31 C30 C27 120.1(6) . . ?
C31 C30 H30 120.0 . . ?
C72 C73 H73 120.0 . . ?
C74 C73 C72 119.9(6) . . ?
C74 C73 H73 120.0 . . ?
C33 C32 H32 119.8 . . ?
C31 C32 C33 120.4(7) . . ?
C31 C32 H32 119.8 . . ?
C30 C31 H31 119.4 . . ?
C32 C31 C30 121.1(6) . . ?
C32 C31 H31 119.4 . . ?
C15 C14 C13 120.8(6) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C63 C62 H62 119.9 . . ?
C63 C62 C61 120.2(7) . . ?
C61 C62 H62 119.9 . . ?
C60 C61 C62 120.7(6) . . ?
C60 C61 H61 119.7 . . ?
C62 C61 H61 119.7 . . ?
C26 C25 H25 119.2 . . ?
C24 C25 C26 121.5(8) . . ?
C24 C25 H25 119.2 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.4(8) . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 120.8(7) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C101 O3 C104 111.3(13) . . ?
O3 C101 H10A 111.3 . . ?
O3 C101 H10B 111.3 . . ?
O3 C101 C102 102.5(12) . . ?
H10A C101 H10B 109.2 . . ?
C102 C101 H10A 111.3 . . ?
C102 C101 H10B 111.3 . . ?
C101 C102 H10C 111.6 . . ?
C101 C102 H10D 111.6 . . ?
H10C C102 H10D 109.4 . . ?
C103 C102 C101 101.0(12) . . ?
C103 C102 H10C 111.6 . . ?
C103 C102 H10D 111.6 . . ?
C102 C103 H10E 110.1 . . ?
C102 C103 H10F 110.1 . . ?
H10E C103 H10F 108.5 . . ?
C104 C103 C102 107.8(12) . . ?
C104 C103 H10E 110.1 . . ?
C104 C103 H10F 110.1 . . ?
H91A C91 H91B 105.5 . . ?
O2 C91 H91A 104.2 . . ?
O2 C91 H91B 104.2 . . ?
C92 C91 H91A 104.2 . . ?
C92 C91 H91B 104.2 . . ?
C92 C91 O2 132.3(17) . . ?
O3 C104 C103 104.1(13) . . ?
O3 C104 H10G 110.9 . . ?
O3 C104 H10H 110.9 . . ?
C103 C104 H10G 110.9 . . ?
C103 C104 H10H 110.9 . . ?
H10G C104 H10H 108.9 . . ?
H93A C93 H93B 109.3 . . ?
C92 C93 H93A 111.5 . . ?
C92 C93 H93B 111.5 . . ?
C92 C93 C94 101.3(17) . . ?
C94 C93 H93A 111.5 . . ?
C94 C93 H93B 111.5 . . ?
C91 O2 C94 80.0(12) . . ?
C91 C92 C93 103.0(17) . . ?
C91 C92 H92A 111.2 . . ?
C91 C92 H92B 111.2 . . ?
C93 C92 H92A 111.2 . . ?
C93 C92 H92B 111.2 . . ?
H92A C92 H92B 109.1 . . ?
C93 C94 O2 114.4(13) . . ?
C93 C94 H94A 108.7 . . ?
C93 C94 H94B 108.7 . . ?
O2 C94 H94A 108.7 . . ?
O2 C94 H94B 108.7 . . ?
H94A C94 H94B 107.6 . . ?

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
Ir1 O1 C76 N4 -168.3(5) . . . . ?
Ir1 O1 C76 C75 16.3(6) . . . . ?
Ir1 N2 C50 C46 27.4(6) . . . . ?
Ir1 N2 C50 C51 -149.9(4) . . . . ?
Ir1 N2 C58 C57 152.4(4) . . . . ?
Ir1 N2 C58 C63 -30.2(7) . . . . ?
Ir1 N3 C75 C76 -5.9(6) . . . . ?
Ir1 N3 C75 C74 173.4(4) . . . . ?
Ir1 N3 C71 C72 -175.1(4) . . . . ?
Ir1 N1 C20 C16 23.5(7) . . . . ?
Ir1 N1 C20 C21 -156.0(5) . . . . ?
Ir1 N1 C28 C27 168.8(4) . . . . ?
Ir1 N1 C28 C33 -15.9(8) . . . . ?
Ir1 C41 C46 C50 -3.0(6) . . . . ?
Ir1 C41 C46 C45 -176.8(4) . . . . ?
Ir1 C41 C42 C43 178.9(5) . . . . ?
Ir1 C11 C16 C20 -6.4(7) . . . . ?
Ir1 C11 C16 C15 -176.7(5) . . . . ?
Ir1 C11 C12 C13 177.8(5) . . . . ?
N2 C50 C46 C41 -16.5(7) . . . . ?
N2 C50 C46 C45 157.0(5) . . . . ?
N2 C50 C51 C52 163.6(5) . . . . ?
N2 C50 C51 C56 -8.9(8) . . . . ?
N2 C58 C57 C56 -0.1(8) . . . . ?
N2 C58 C57 C60 179.5(5) . . . . ?
N2 C58 C63 C62 -179.1(6) . . . . ?
N3 C75 C76 O1 -7.0(7) . . . . ?
N3 C75 C76 N4 177.1(5) . . . . ?
N3 C75 C74 C73 3.6(9) . . . . ?
N3 C71 C72 C73 0.3(9) . . . . ?
N1 C20 C16 C11 -11.5(8) . . . . ?
N1 C20 C16 C15 158.3(6) . . . . ?
N1 C20 C21 C22 156.4(6) . . . . ?
N1 C20 C21 C26 -17.0(9) . . . . ?
N1 C28 C27 C26 -9.2(9) . . . . ?
N1 C28 C27 C30 173.7(6) . . . . ?
N1 C28 C33 C32 -173.6(6) . . . . ?
N4 C81 C82 C83 -175.9(6) . . . . ?
N4 C81 C86 C85 174.8(6) . . . . ?
C41 C46 C45 C44 -3.7(9) . . . . ?
C41 C42 C43 C44 0.0(9) . . . . ?
C50 N2 C58 C57 -12.3(8) . . . . ?
C50 N2 C58 C63 165.0(5) . . . . ?
C50 C46 C45 C44 -176.8(6) . . . . ?
C50 C51 C56 C57 -3.4(8) . . . . ?
C50 C51 C56 C55 175.1(5) . . . . ?
C11 C16 C15 C14 -2.7(11) . . . . ?
C11 C12 C13 C14 0.7(11) . . . . ?
C46 C41 C42 C43 -3.1(8) . . . . ?
C46 C50 C51 C52 -13.3(9) . . . . ?
C46 C50 C51 C56 174.2(5) . . . . ?
C46 C45 C44 C43 0.5(9) . . . . ?
C75 N3 C71 C72 2.3(8) . . . . ?
C75 C74 C73 C72 -0.9(9) . . . . ?
C20 N1 C28 C27 -8.2(9) . . . . ?
C20 N1 C28 C33 167.2(6) . . . . ?
C20 C16 C15 C14 -171.6(7) . . . . ?
C20 C21 C22 C23 -176.6(7) . . . . ?
C20 C21 C26 C27 -0.2(10) . . . . ?
C20 C21 C26 C25 176.7(6) . . . . ?
C58 N2 C50 C46 -166.0(5) . . . . ?
C58 N2 C50 C51 16.7(8) . . . . ?
C58 C57 C56 C51 7.6(8) . . . . ?
C58 C57 C56 C55 -170.9(6) . . . . ?
C58 C57 C60 C61 -1.2(9) . . . . ?
C58 C63 C62 C61 0.3(10) . . . . ?
C16 C11 C12 C13 -3.2(10) . . . . ?
C16 C20 C21 C22 -23.0(10) . . . . ?
C16 C20 C21 C26 163.6(6) . . . . ?
C16 C15 C14 C13 -0.1(11) . . . . ?
C71 N3 C75 C76 176.4(5) . . . . ?
C71 N3 C75 C74 -4.3(8) . . . . ?
C71 C72 C73 C74 -1.0(9) . . . . ?
C81 N4 C76 O1 8.8(9) . . . . ?
C81 N4 C76 C75 -175.9(5) . . . . ?
C81 C82 C83 C84 0.4(10) . . . . ?
C52 C51 C56 C57 -176.1(5) . . . . ?
C52 C51 C56 C55 2.4(8) . . . . ?
C52 C53 C54 C55 3.5(10) . . . . ?
C57 C58 C63 C62 -1.7(9) . . . . ?
C57 C56 C55 C54 178.6(6) . . . . ?
C57 C60 C61 C62 -0.2(11) . . . . ?
C51 C50 C46 C41 160.6(5) . . . . ?
C51 C50 C46 C45 -25.9(9) . . . . ?
C51 C52 C53 C54 -0.9(9) . . . . ?
C51 C56 C55 C54 0.1(9) . . . . ?
C28 N1 C20 C16 -159.2(5) . . . . ?
C28 N1 C20 C21 21.3(9) . . . . ?
C28 C27 C26 C21 12.8(9) . . . . ?
C28 C27 C26 C25 -163.9(7) . . . . ?
C28 C27 C30 C31 0.3(10) . . . . ?
C28 C33 C32 C31 -0.7(10) . . . . ?
C82 C81 C86 C85 -0.8(9) . . . . ?
C21 C20 C16 C11 167.9(6) . . . . ?
C21 C20 C16 C15 -22.3(11) . . . . ?
C21 C22 C23 C24 0.9(13) . . . . ?
C21 C26 C25 C24 -0.8(11) . . . . ?
C42 C41 C46 C50 178.6(5) . . . . ?
C42 C41 C46 C45 4.8(8) . . . . ?
C42 C43 C44 C45 1.3(10) . . . . ?
C76 N4 C81 C82 -153.2(6) . . . . ?
C76 N4 C81 C86 31.1(9) . . . . ?
C76 C75 C74 C73 -177.2(5) . . . . ?
C56 C57 C60 C61 178.3(6) . . . . ?
C56 C55 C54 C53 -3.0(9) . . . . ?
C74 C75 C76 O1 173.8(5) . . . . ?
C74 C75 C76 N4 -2.2(8) . . . . ?
C60 C57 C56 C51 -172.0(6) . . . . ?
C60 C57 C56 C55 9.6(9) . . . . ?
C12 C11 C16 C20 174.4(6) . . . . ?
C12 C11 C16 C15 4.2(10) . . . . ?
C12 C13 C14 C15 1.0(11) . . . . ?
C27 C28 C33 C32 1.7(9) . . . . ?
C27 C26 C25 C24 175.9(7) . . . . ?
C27 C30 C31 C32 0.7(11) . . . . ?
C33 C28 C27 C26 175.6(6) . . . . ?
C33 C28 C27 C30 -1.5(9) . . . . ?
C33 C32 C31 C30 -0.5(11) . . . . ?
C84 C85 C86 C81 0.8(10) . . . . ?
C63 C58 C57 C56 -177.4(5) . . . . ?
C63 C58 C57 C60 2.2(9) . . . . ?
C63 C62 C61 C60 0.6(11) . . . . ?
C53 C52 C51 C50 -174.6(6) . . . . ?
C53 C52 C51 C56 -2.1(9) . . . . ?
C85 C84 C87 F2 12.8(10) . . . . ?
C85 C84 C87 F3 132.6(7) . . . . ?
C85 C84 C87 F1 -108.5(8) . . . . ?
C85 C84 C83 C82 -0.4(10) . . . . ?
C86 C81 C82 C83 0.2(9) . . . . ?
C22 C21 C26 C27 -173.8(6) . . . . ?
C22 C21 C26 C25 3.2(10) . . . . ?
C22 C23 C24 C25 1.5(14) . . . . ?
C26 C21 C22 C23 -3.2(11) . . . . ?
C26 C27 C30 C31 -176.7(6) . . . . ?
C26 C25 C24 C23 -1.5(13) . . . . ?
C87 C84 C85 C86 177.8(6) . . . . ?
C87 C84 C83 C82 -178.4(6) . . . . ?
C83 C84 C85 C86 -0.2(10) . . . . ?
C83 C84 C87 F2 -169.2(6) . . . . ?
C83 C84 C87 F3 -49.3(9) . . . . ?
C83 C84 C87 F1 69.5(9) . . . . ?
C30 C27 C26 C21 -170.2(6) . . . . ?
C30 C27 C26 C25 13.1(11) . . . . ?
O3 C101 C102 C103 -35.2(13) . . . . ?
C101 O3 C104 C103 -5.8(16) . . . . ?
C101 C102 C103 C104 33.2(13) . . . . ?
C102 C103 C104 O3 -18.3(15) . . . . ?
C91 O2 C94 C93 -17.0(15) . . . . ?
C104 O3 C101 C102 26.0(15) . . . . ?
O2 C91 C92 C93 22(3) . . . . ?
C92 C91 O2 C94 -3(2) . . . . ?
C92 C93 C94 O2 30.1(19) . . . . ?
C94 C93 C92 C91 -28(2) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 165.7 37.7 ?
2 0.500 0.000 0.500 52.8 3.8 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
