# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_Complex1
_audit_block_doi                 10.5517/ccdc.csd.cc1yzq6v
_database_code_depnum_ccdc_archive 'CCDC 1816978'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H33 Ir N S, F6 P'
_chemical_formula_sum            'C33 H33 F6 Ir N P S'
_chemical_formula_weight         812.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   8.9391(4)
_cell_length_b                   18.8103(8)
_cell_length_c                   9.2977(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.3090(10)
_cell_angle_gamma                90
_cell_volume                     1507.91(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4151
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      21.93

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_F_000             800.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.164
_exptl_absorpt_coefficient_mu    4.612
_shelx_estimated_absorpt_T_min   0.345
_shelx_estimated_absorpt_T_max   0.468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.345
_exptl_absorpt_correction_T_max  0.468
_exptl_absorpt_process_details   '(SADABS; Bruker; 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            28172
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.165
_diffrn_reflns_theta_max         28.300
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7492
_reflns_number_gt                7280
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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 SMART APEX-II'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    'SHELXT 2014/5 Bruker-AXS, Madison WI'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3.1'
_computing_publication_material  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)+(0.0726P)²+0.1183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.003(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7492
_refine_ls_number_parameters     393
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.61657(2) 0.48674(2) 0.18581(2) 0.01217(9) Uani 1 1 d . . . . .
S1 S 0.6373(2) 0.61001(10) 0.19037(18) 0.0176(3) Uani 1 1 d . . . . .
P1 P 0.2431(2) 0.65220(10) 0.5765(2) 0.0185(3) Uani 1 1 d . . . . .
C3 C 0.1504(9) 0.3095(4) -0.3938(8) 0.0234(15) Uani 1 1 d . . . . .
H3 H 0.0410 0.3040 -0.4160 0.028 Uiso 1 1 calc R U . . .
N1 N 0.4196(7) 0.5093(3) 0.0217(6) 0.0142(10) Uani 1 1 d . . . . .
C25 C 0.8513(10) 0.3476(4) 0.2468(9) 0.0238(15) Uani 1 1 d . . . . .
H25A H 0.9460 0.3750 0.2535 0.036 Uiso 1 1 calc R U . . .
H25B H 0.8051 0.3338 0.1429 0.036 Uiso 1 1 calc R U . . .
H25C H 0.8766 0.3048 0.3087 0.036 Uiso 1 1 calc R U . . .
F5 F 0.2328(7) 0.7341(3) 0.5272(7) 0.0309(12) Uani 1 1 d . . . . .
C24 C 0.7385(8) 0.3920(3) 0.3008(7) 0.0156(12) Uani 1 1 d . . . . .
C4 C 0.2378(10) 0.2647(4) -0.4626(9) 0.0232(17) Uani 1 1 d . . . . .
H4 H 0.1863 0.2297 -0.5316 0.028 Uiso 1 1 calc R U . . .
C21 C 0.9635(15) 0.6912(5) -0.0740(14) 0.044(3) Uani 1 1 d . . . . .
H21 H 1.0341 0.7076 -0.1271 0.052 Uiso 1 1 calc R U . . .
C6 C 0.4725(9) 0.3244(4) -0.3290(7) 0.0178(14) Uani 1 1 d . . . . .
C2 C 0.2226(8) 0.3612(4) -0.2948(7) 0.0184(13) Uani 1 1 d . . . . .
H2 H 0.1621 0.3914 -0.2504 0.022 Uiso 1 1 calc R U . . .
C13 C 0.6309(8) 0.4244(3) -0.1086(7) 0.0131(12) Uani 1 1 d . . . . .
F1 F 0.4289(6) 0.6572(3) 0.6214(7) 0.0338(13) Uani 1 1 d . . . . .
C11 C 0.8706(8) 0.4780(5) 0.0273(7) 0.0190(16) Uani 1 1 d . . . . .
H11 H 0.9265 0.5107 0.0998 0.023 Uiso 1 1 calc R U . . .
C33 C 0.9337(9) 0.4814(7) 0.4681(8) 0.0277(15) Uani 1 1 d . . . . .
H33A H 0.9703 0.4622 0.5692 0.042 Uiso 1 1 calc R U . . .
H33B H 0.9290 0.5334 0.4727 0.042 Uiso 1 1 calc R U . . .
H33C H 1.0053 0.4674 0.4094 0.042 Uiso 1 1 calc R U . . .
F2 F 0.0580(7) 0.6493(3) 0.5339(8) 0.0419(15) Uani 1 1 d . . . . .
F3 F 0.2438(7) 0.6751(3) 0.7424(5) 0.0355(12) Uani 1 1 d . . . . .
C31 C 0.6290(11) 0.5341(5) 0.5384(8) 0.0294(17) Uani 1 1 d . . . . .
H31A H 0.5207 0.5470 0.5292 0.044 Uiso 1 1 calc R U . . .
H31B H 0.6850 0.5757 0.5159 0.044 Uiso 1 1 calc R U . . .
H31C H 0.6773 0.5181 0.6404 0.044 Uiso 1 1 calc R U . . .
C30 C 0.6352(8) 0.4757(4) 0.4313(7) 0.0191(17) Uani 1 1 d . . . . .
C15 C 0.3747(7) 0.4757(4) -0.1021(7) 0.0162(16) Uani 1 1 d . . . . .
H15 H 0.2764 0.4877 -0.1662 0.019 Uiso 1 1 calc R U . . .
C10 C 0.9505(9) 0.4412(5) -0.0630(9) 0.0244(15) Uani 1 1 d . . . . .
H10 H 1.0579 0.4501 -0.0504 0.029 Uiso 1 1 calc R U . . .
F6 F 0.2534(7) 0.5702(3) 0.6241(7) 0.0374(13) Uani 1 1 d . . . . .
F4 F 0.2438(8) 0.6292(4) 0.4113(6) 0.0447(16) Uani 1 1 d . . . . .
C26 C 0.5735(8) 0.3819(4) 0.2644(7) 0.0173(13) Uani 1 1 d . . . . .
C5 C 0.3948(9) 0.2710(4) -0.4314(8) 0.0198(13) Uani 1 1 d . . . . .
H5 H 0.4525 0.2400 -0.4772 0.024 Uiso 1 1 calc R U . . .
C32 C 0.7754(8) 0.4527(4) 0.3960(7) 0.0167(12) Uani 1 1 d . . . . .
C1 C 0.3868(8) 0.3700(4) -0.2579(7) 0.0162(12) Uani 1 1 d . . . . .
C8 C 0.7129(8) 0.3831(4) -0.1930(8) 0.0175(12) Uani 1 1 d . . . . .
C18 C 0.7582(10) 0.6439(4) 0.0804(9) 0.0205(14) Uani 1 1 d . . . . .
C14 C 0.4643(8) 0.4205(3) -0.1511(7) 0.0137(12) Uani 1 1 d . . . . .
C27 C 0.4850(10) 0.3223(4) 0.1738(8) 0.0243(15) Uani 1 1 d . . . . .
H27A H 0.5373 0.3076 0.0983 0.037 Uiso 1 1 calc R U . . .
H27B H 0.3796 0.3383 0.1245 0.037 Uiso 1 1 calc R U . . .
H27C H 0.4802 0.2820 0.2392 0.037 Uiso 1 1 calc R U . . .
C9 C 0.8761(8) 0.3935(5) -0.1672(9) 0.0235(16) Uani 1 1 d . . . . .
H9 H 0.9324 0.3672 -0.2227 0.028 Uiso 1 1 calc R U . . .
C28 C 0.5098(9) 0.4332(4) 0.3503(8) 0.0193(14) Uani 1 1 d . . . . .
C29 C 0.3433(10) 0.4381(5) 0.3502(9) 0.0282(17) Uani 1 1 d . . . . .
H29A H 0.3182 0.3994 0.4105 0.042 Uiso 1 1 calc R U . . .
H29B H 0.2780 0.4342 0.2477 0.042 Uiso 1 1 calc R U . . .
H29C H 0.3242 0.4838 0.3924 0.042 Uiso 1 1 calc R U . . .
C23 C 0.7171(12) 0.6397(5) -0.0745(9) 0.0322(19) Uani 1 1 d . . . . .
H23 H 0.6198 0.6205 -0.1273 0.039 Uiso 1 1 calc R U . . .
C7 C 0.6336(9) 0.3339(5) -0.2982(8) 0.0200(15) Uani 1 1 d . . . . .
H7 H 0.6905 0.3060 -0.3507 0.024 Uiso 1 1 calc R U . . .
C16 C 0.3334(9) 0.5718(4) 0.0529(8) 0.0201(13) Uani 1 1 d . . . . .
H16A H 0.2942 0.5625 0.1412 0.024 Uiso 1 1 calc R U . . .
H16B H 0.2435 0.5813 -0.0333 0.024 Uiso 1 1 calc R U . . .
C20 C 1.0040(12) 0.6942(5) 0.0813(13) 0.037(2) Uani 1 1 d . . . . .
H20 H 1.1022 0.7125 0.1340 0.044 Uiso 1 1 calc R U . . .
C17 C 0.4424(9) 0.6363(4) 0.0820(11) 0.0290(17) Uani 1 1 d . . . . .
H17A H 0.4008 0.6730 0.1374 0.035 Uiso 1 1 calc R U . . .
H17B H 0.4481 0.6571 -0.0142 0.035 Uiso 1 1 calc R U . . .
C19 C 0.9004(10) 0.6703(4) 0.1586(9) 0.0254(15) Uani 1 1 d . . . . .
H19 H 0.9272 0.6722 0.2644 0.030 Uiso 1 1 calc R U . . .
C22 C 0.8219(16) 0.6644(5) -0.1506(10) 0.044(3) Uani 1 1 d . . . . .
H22 H 0.7951 0.6628 -0.2565 0.053 Uiso 1 1 calc R U . . .
C12 C 0.7148(8) 0.4681(3) 0.0136(7) 0.0133(13) 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 N1 2.047(6) . ?
Ir1 C12 2.050(7) . ?
Ir1 C26 2.173(7) . ?
Ir1 C32 2.186(6) . ?
Ir1 C24 2.212(6) . ?
Ir1 C28 2.244(7) . ?
Ir1 C30 2.254(6) . ?
Ir1 S1 2.326(2) . ?
S1 C18 1.790(8) . ?
S1 C17 1.836(8) . ?
P1 F2 1.597(6) . ?
P1 F4 1.598(6) . ?
P1 F3 1.599(5) . ?
P1 F6 1.600(5) . ?
P1 F5 1.604(5) . ?
P1 F1 1.605(6) . ?
C3 C2 1.376(10) . ?
C3 C4 1.412(12) . ?
C3 H3 0.9500 . ?
N1 C15 1.280(9) . ?
N1 C16 1.475(9) . ?
C25 C24 1.494(10) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C24 C32 1.429(9) . ?
C24 C26 1.436(10) . ?
C4 C5 1.360(11) . ?
C4 H4 0.9500 . ?
C21 C22 1.373(18) . ?
C21 C20 1.394(16) . ?
C21 H21 0.9500 . ?
C6 C7 1.404(10) . ?
C6 C1 1.424(10) . ?
C6 C5 1.431(10) . ?
C2 C1 1.427(9) . ?
C2 H2 0.9500 . ?
C13 C8 1.436(9) . ?
C13 C14 1.438(9) . ?
C13 C12 1.441(8) . ?
C11 C12 1.377(9) . ?
C11 C10 1.418(11) . ?
C11 H11 0.9500 . ?
C33 C32 1.497(10) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C31 C30 1.493(10) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C30 C28 1.421(10) . ?
C30 C32 1.443(10) . ?
C15 C14 1.456(10) . ?
C15 H15 0.9500 . ?
C10 C9 1.359(11) . ?
C10 H10 0.9500 . ?
C26 C28 1.460(10) . ?
C26 C27 1.497(10) . ?
C5 H5 0.9500 . ?
C1 C14 1.416(9) . ?
C8 C7 1.396(10) . ?
C8 C9 1.428(9) . ?
C18 C19 1.380(11) . ?
C18 C23 1.392(11) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C9 H9 0.9500 . ?
C28 C29 1.491(11) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C23 C22 1.395(15) . ?
C23 H23 0.9500 . ?
C7 H7 0.9500 . ?
C16 C17 1.536(11) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C20 C19 1.388(13) . ?
C20 H20 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 H19 0.9500 . ?
C22 H22 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
N1 Ir1 C12 85.1(2) . . ?
N1 Ir1 C26 104.2(2) . . ?
C12 Ir1 C26 104.9(3) . . ?
N1 Ir1 C32 162.7(3) . . ?
C12 Ir1 C32 109.7(3) . . ?
C26 Ir1 C32 64.2(3) . . ?
N1 Ir1 C24 138.1(2) . . ?
C12 Ir1 C24 89.0(3) . . ?
C26 Ir1 C24 38.2(3) . . ?
C32 Ir1 C24 37.9(2) . . ?
N1 Ir1 C28 99.4(3) . . ?
C12 Ir1 C28 143.4(2) . . ?
C26 Ir1 C28 38.6(3) . . ?
C32 Ir1 C28 63.4(3) . . ?
C24 Ir1 C28 63.4(3) . . ?
N1 Ir1 C30 126.4(3) . . ?
C12 Ir1 C30 147.5(3) . . ?
C26 Ir1 C30 63.2(3) . . ?
C32 Ir1 C30 37.9(3) . . ?
C24 Ir1 C30 62.7(3) . . ?
C28 Ir1 C30 36.8(3) . . ?
N1 Ir1 S1 81.71(17) . . ?
C12 Ir1 S1 97.85(18) . . ?
C26 Ir1 S1 156.82(19) . . ?
C32 Ir1 S1 104.23(19) . . ?
C24 Ir1 S1 140.17(18) . . ?
C28 Ir1 S1 118.8(2) . . ?
C30 Ir1 S1 95.09(19) . . ?
C18 S1 C17 102.7(4) . . ?
C18 S1 Ir1 113.7(3) . . ?
C17 S1 Ir1 101.5(3) . . ?
F2 P1 F4 91.1(4) . . ?
F2 P1 F3 89.4(4) . . ?
F4 P1 F3 179.5(4) . . ?
F2 P1 F6 90.9(3) . . ?
F4 P1 F6 89.4(3) . . ?
F3 P1 F6 90.4(3) . . ?
F2 P1 F5 89.1(3) . . ?
F4 P1 F5 90.0(3) . . ?
F3 P1 F5 90.1(3) . . ?
F6 P1 F5 179.4(3) . . ?
F2 P1 F1 178.4(4) . . ?
F4 P1 F1 89.9(3) . . ?
F3 P1 F1 89.6(3) . . ?
F6 P1 F1 90.3(3) . . ?
F5 P1 F1 89.7(3) . . ?
C2 C3 C4 120.4(7) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C15 N1 C16 120.9(6) . . ?
C15 N1 Ir1 124.9(5) . . ?
C16 N1 Ir1 114.2(4) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C32 C24 C26 107.9(6) . . ?
C32 C24 C25 126.0(7) . . ?
C26 C24 C25 126.1(6) . . ?
C32 C24 Ir1 70.1(4) . . ?
C26 C24 Ir1 69.4(4) . . ?
C25 C24 Ir1 125.3(5) . . ?
C5 C4 C3 121.0(7) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C22 C21 C20 120.3(9) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C7 C6 C1 118.5(7) . . ?
C7 C6 C5 121.1(7) . . ?
C1 C6 C5 120.4(7) . . ?
C3 C2 C1 120.9(7) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C8 C13 C14 117.6(6) . . ?
C8 C13 C12 120.3(6) . . ?
C14 C13 C12 122.1(6) . . ?
C12 C11 C10 122.3(7) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C28 C30 C32 108.7(6) . . ?
C28 C30 C31 127.2(7) . . ?
C32 C30 C31 124.1(7) . . ?
C28 C30 Ir1 71.2(4) . . ?
C32 C30 Ir1 68.5(4) . . ?
C31 C30 Ir1 127.0(5) . . ?
N1 C15 C14 124.4(6) . . ?
N1 C15 H15 117.8 . . ?
C14 C15 H15 117.8 . . ?
C9 C10 C11 121.1(7) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C24 C26 C28 107.9(6) . . ?
C24 C26 C27 126.1(7) . . ?
C28 C26 C27 125.3(7) . . ?
C24 C26 Ir1 72.4(4) . . ?
C28 C26 Ir1 73.4(4) . . ?
C27 C26 Ir1 127.2(5) . . ?
C4 C5 C6 119.6(7) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C24 C32 C30 107.9(6) . . ?
C24 C32 C33 127.0(7) . . ?
C30 C32 C33 124.4(7) . . ?
C24 C32 Ir1 72.0(4) . . ?
C30 C32 Ir1 73.6(4) . . ?
C33 C32 Ir1 127.5(6) . . ?
C14 C1 C6 120.4(7) . . ?
C14 C1 C2 121.9(6) . . ?
C6 C1 C2 117.6(6) . . ?
C7 C8 C9 121.0(7) . . ?
C7 C8 C13 120.3(6) . . ?
C9 C8 C13 118.7(7) . . ?
C19 C18 C23 121.3(8) . . ?
C19 C18 S1 116.0(6) . . ?
C23 C18 S1 122.5(7) . . ?
C1 C14 C13 120.4(6) . . ?
C1 C14 C15 119.4(6) . . ?
C13 C14 C15 119.5(6) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C10 C9 C8 119.8(7) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C30 C28 C26 107.2(7) . . ?
C30 C28 C29 127.8(7) . . ?
C26 C28 C29 125.0(7) . . ?
C30 C28 Ir1 72.0(4) . . ?
C26 C28 Ir1 68.1(4) . . ?
C29 C28 Ir1 125.2(5) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C18 C23 C22 118.5(9) . . ?
C18 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C8 C7 C6 122.1(7) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
N1 C16 C17 108.9(6) . . ?
N1 C16 H16A 109.9 . . ?
C17 C16 H16A 109.9 . . ?
N1 C16 H16B 109.9 . . ?
C17 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C19 C20 C21 119.8(10) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C16 C17 S1 110.4(5) . . ?
C16 C17 H17A 109.6 . . ?
S1 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
S1 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C18 C19 C20 119.4(8) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C22 C23 120.6(9) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C11 C12 C13 117.0(6) . . ?
C11 C12 Ir1 122.4(5) . . ?
C13 C12 Ir1 118.2(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
C2 C3 C4 C5 0.8(13) . . . . ?
C4 C3 C2 C1 -0.9(12) . . . . ?
C16 N1 C15 C14 170.5(7) . . . . ?
Ir1 N1 C15 C14 -6.0(10) . . . . ?
C12 C11 C10 C9 -0.6(13) . . . . ?
C32 C24 C26 C28 -5.5(7) . . . . ?
C25 C24 C26 C28 175.4(6) . . . . ?
Ir1 C24 C26 C28 -65.2(5) . . . . ?
C32 C24 C26 C27 -176.6(6) . . . . ?
C25 C24 C26 C27 4.3(11) . . . . ?
Ir1 C24 C26 C27 123.6(7) . . . . ?
C32 C24 C26 Ir1 59.7(4) . . . . ?
C25 C24 C26 Ir1 -119.3(7) . . . . ?
C3 C4 C5 C6 -0.9(12) . . . . ?
C7 C6 C5 C4 -177.8(7) . . . . ?
C1 C6 C5 C4 1.2(11) . . . . ?
C26 C24 C32 C30 6.0(7) . . . . ?
C25 C24 C32 C30 -174.9(6) . . . . ?
Ir1 C24 C32 C30 65.3(5) . . . . ?
C26 C24 C32 C33 176.9(7) . . . . ?
C25 C24 C32 C33 -4.1(11) . . . . ?
Ir1 C24 C32 C33 -123.8(8) . . . . ?
C26 C24 C32 Ir1 -59.3(4) . . . . ?
C25 C24 C32 Ir1 119.7(7) . . . . ?
C28 C30 C32 C24 -4.3(8) . . . . ?
C31 C30 C32 C24 174.7(7) . . . . ?
Ir1 C30 C32 C24 -64.3(4) . . . . ?
C28 C30 C32 C33 -175.4(7) . . . . ?
C31 C30 C32 C33 3.6(12) . . . . ?
Ir1 C30 C32 C33 124.5(8) . . . . ?
C28 C30 C32 Ir1 60.0(5) . . . . ?
C31 C30 C32 Ir1 -121.0(7) . . . . ?
C7 C6 C1 C14 -4.1(10) . . . . ?
C5 C6 C1 C14 176.9(6) . . . . ?
C7 C6 C1 C2 177.7(7) . . . . ?
C5 C6 C1 C2 -1.3(10) . . . . ?
C3 C2 C1 C14 -177.0(7) . . . . ?
C3 C2 C1 C6 1.1(10) . . . . ?
C14 C13 C8 C7 -8.5(10) . . . . ?
C12 C13 C8 C7 171.6(7) . . . . ?
C14 C13 C8 C9 171.3(7) . . . . ?
C12 C13 C8 C9 -8.6(10) . . . . ?
C17 S1 C18 C19 143.5(6) . . . . ?
Ir1 S1 C18 C19 -107.8(6) . . . . ?
C17 S1 C18 C23 -40.7(8) . . . . ?
Ir1 S1 C18 C23 68.1(8) . . . . ?
C6 C1 C14 C13 -2.6(10) . . . . ?
C2 C1 C14 C13 175.5(6) . . . . ?
C6 C1 C14 C15 167.8(6) . . . . ?
C2 C1 C14 C15 -14.1(10) . . . . ?
C8 C13 C14 C1 8.8(9) . . . . ?
C12 C13 C14 C1 -171.3(6) . . . . ?
C8 C13 C14 C15 -161.6(6) . . . . ?
C12 C13 C14 C15 18.3(9) . . . . ?
N1 C15 C14 C1 157.2(7) . . . . ?
N1 C15 C14 C13 -32.3(10) . . . . ?
C11 C10 C9 C8 3.8(14) . . . . ?
C7 C8 C9 C10 -179.4(8) . . . . ?
C13 C8 C9 C10 0.9(12) . . . . ?
C32 C30 C28 C26 0.8(8) . . . . ?
C31 C30 C28 C26 -178.1(7) . . . . ?
Ir1 C30 C28 C26 59.2(5) . . . . ?
C32 C30 C28 C29 -179.3(7) . . . . ?
C31 C30 C28 C29 1.7(12) . . . . ?
Ir1 C30 C28 C29 -121.0(7) . . . . ?
C32 C30 C28 Ir1 -58.4(5) . . . . ?
C31 C30 C28 Ir1 122.7(8) . . . . ?
C24 C26 C28 C30 2.9(7) . . . . ?
C27 C26 C28 C30 174.1(6) . . . . ?
Ir1 C26 C28 C30 -61.7(5) . . . . ?
C24 C26 C28 C29 -176.9(6) . . . . ?
C27 C26 C28 C29 -5.7(11) . . . . ?
Ir1 C26 C28 C29 118.5(7) . . . . ?
C24 C26 C28 Ir1 64.6(4) . . . . ?
C27 C26 C28 Ir1 -124.2(7) . . . . ?
C19 C18 C23 C22 -1.3(13) . . . . ?
S1 C18 C23 C22 -177.0(7) . . . . ?
C9 C8 C7 C6 -177.9(8) . . . . ?
C13 C8 C7 C6 1.9(12) . . . . ?
C1 C6 C7 C8 4.5(11) . . . . ?
C5 C6 C7 C8 -176.5(7) . . . . ?
C15 N1 C16 C17 -120.8(8) . . . . ?
Ir1 N1 C16 C17 56.1(7) . . . . ?
C22 C21 C20 C19 -0.3(16) . . . . ?
N1 C16 C17 S1 -38.9(8) . . . . ?
C18 S1 C17 C16 127.4(6) . . . . ?
Ir1 S1 C17 C16 9.6(7) . . . . ?
C23 C18 C19 C20 0.8(12) . . . . ?
S1 C18 C19 C20 176.7(7) . . . . ?
C21 C20 C19 C18 0.0(14) . . . . ?
C20 C21 C22 C23 -0.3(16) . . . . ?
C18 C23 C22 C21 1.0(15) . . . . ?
C10 C11 C12 C13 -6.9(11) . . . . ?
C10 C11 C12 Ir1 155.0(6) . . . . ?
C8 C13 C12 C11 11.4(10) . . . . ?
C14 C13 C12 C11 -168.4(7) . . . . ?
C8 C13 C12 Ir1 -151.2(5) . . . . ?
C14 C13 C12 Ir1 28.9(8) . . . . ?

_refine_diff_density_max         1.366
_refine_diff_density_min         -1.682
_refine_diff_density_rms         0.132

####################################################################### 
# 
# 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_Complex2
_audit_block_doi                 10.5517/ccdc.csd.cc1ptlrv
_database_code_depnum_ccdc_archive 'CCDC 1573738'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H33 Ir N Se, F6 P'
_chemical_formula_sum            'C33 H33 F6 Ir N P Se'
_chemical_formula_weight         859.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   9.0129(17)
_cell_length_b                   18.866(4)
_cell_length_c                   9.4669(19)
_cell_angle_alpha                90
_cell_angle_beta                 104.644(4)
_cell_angle_gamma                90
_cell_volume                     1557.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1655
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.833
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_F_000             836.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_exptl_absorpt_coefficient_mu    5.567
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.156
_exptl_absorpt_correction_T_max  0.200
_exptl_absorpt_process_details   '(SADABS; Bruker; 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            7551
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.159
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.792
_diffrn_reflns_point_group_measured_fraction_full 0.792
_reflns_number_total             5489
_reflns_number_gt                3791
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.538
_reflns_Friedel_fraction_max     0.573
_reflns_Friedel_fraction_full    0.573

_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 SMART APEX-II'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    'SHELXT 2014/5 Bruker-AXS, Madison WI'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3.2'
_computing_publication_material  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)+(0.0067P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1139 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5489
_refine_ls_number_parameters     393
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.59300(5) 0.01832(3) 0.66637(5) 0.04139(17) Uani 1 1 d . . . . .
Se1 Se 0.6192(2) -0.11083(8) 0.67702(19) 0.0607(5) Uani 1 1 d . . . . .
P1 P 0.7894(8) 0.3567(3) 0.9552(7) 0.0753(16) Uani 1 1 d . . . . .
C28 C 0.699(3) 0.1152(9) 0.7767(19) 0.070(5) Uani 1 1 d . . . . .
C15 C 0.3686(15) 0.0289(12) 0.3788(15) 0.048(4) Uani 1 1 d . . . . .
H15 H 0.2743 0.0186 0.3152 0.057 Uiso 1 1 calc R U . . .
C22 C 0.973(3) -0.2034(11) 0.544(3) 0.095(7) Uani 1 1 d . . . . .
H22 H 1.0591 -0.2303 0.5865 0.115 Uiso 1 1 calc R U . . .
C3 C 0.8569(15) 0.0286(14) 0.5240(15) 0.058(4) Uani 1 1 d . . . . .
H3 H 0.9087 -0.0006 0.5995 0.069 Uiso 1 1 calc R U . . .
C2 C 0.7032(16) 0.0375(6) 0.5038(13) 0.038(4) Uani 1 1 d . . . . .
C32 C 0.6048(18) 0.0299(12) 0.9062(14) 0.057(5) Uani 1 1 d . . . . .
C29 C 0.807(3) 0.1628(11) 0.726(2) 0.118(9) Uani 1 1 d . . . . .
H29A H 0.8890 0.1354 0.7068 0.177 Uiso 1 1 calc R U . . .
H29B H 0.8472 0.1974 0.8001 0.177 Uiso 1 1 calc R U . . .
H29C H 0.7527 0.1864 0.6381 0.177 Uiso 1 1 calc R U . . .
N1 N 0.4043(12) -0.0051(5) 0.4993(13) 0.045(3) Uani 1 1 d . . . . .
F1 F 0.8129(19) 0.2774(7) 1.004(2) 0.141(6) Uani 1 1 d . . . . .
C19 C 0.709(2) -0.1315(10) 0.4056(18) 0.074(5) Uani 1 1 d . . . . .
H19 H 0.6182 -0.1091 0.3584 0.088 Uiso 1 1 calc R U . . .
C8 C 0.476(2) 0.1762(8) 0.1562(15) 0.054(4) Uani 1 1 d . . . . .
C9 C 0.407(3) 0.2252(12) 0.052(2) 0.080(6) Uani 1 1 d . . . . .
H9 H 0.4651 0.2507 0.0017 0.096 Uiso 1 1 calc R U . . .
F6 F 0.816(3) 0.3397(10) 0.806(2) 0.188(9) Uani 1 1 d . . . . .
C5 C 0.869(2) 0.1072(12) 0.331(2) 0.076(6) Uani 1 1 d . . . . .
H5 H 0.9259 0.1322 0.2783 0.091 Uiso 1 1 calc R U . . .
C24 C 0.477(2) 0.0680(9) 0.8252(17) 0.055(4) Uani 1 1 d . . . . .
C16 C 0.3144(19) -0.0668(8) 0.5224(19) 0.064(5) Uani 1 1 d . . . . .
H16A H 0.2280 -0.0731 0.4384 0.077 Uiso 1 1 calc R U . . .
H16B H 0.2749 -0.0589 0.6074 0.077 Uiso 1 1 calc R U . . .
C1 C 0.6216(18) 0.0781(7) 0.3782(15) 0.041(4) Uani 1 1 d . . . . .
C4 C 0.941(2) 0.0615(11) 0.436(2) 0.076(5) Uani 1 1 d . . . . .
H4 H 1.0446 0.0521 0.4507 0.091 Uiso 1 1 calc R U . . .
C6 C 0.7092(19) 0.1171(9) 0.3002(19) 0.060(4) Uani 1 1 d . . . . .
C30 C 0.7433(19) 0.0570(8) 0.8715(16) 0.052(4) Uani 1 1 d . . . . .
F2 F 0.7705(19) 0.4367(6) 0.9109(17) 0.145(6) Uani 1 1 d . . . . .
C10 C 0.261(3) 0.2356(11) 0.0254(19) 0.079(7) Uani 1 1 d . . . . .
H10 H 0.2175 0.2731 -0.0349 0.095 Uiso 1 1 calc R U . . .
C14 C 0.4617(18) 0.0815(7) 0.3333(16) 0.043(4) Uani 1 1 d . . . . .
F4 F 0.624(2) 0.3420(13) 0.880(3) 0.208(11) Uani 1 1 d . . . . .
C12 C 0.226(2) 0.1412(10) 0.1839(16) 0.061(4) Uani 1 1 d . . . . .
H12 H 0.1660 0.1129 0.2274 0.073 Uiso 1 1 calc R U . . .
C31 C 0.903(2) 0.0352(16) 0.945(2) 0.098(9) Uani 1 1 d . . . . .
H31A H 0.9629 0.0764 0.9826 0.147 Uiso 1 1 calc R U . . .
H31B H 0.9483 0.0114 0.8767 0.147 Uiso 1 1 calc R U . . .
H31C H 0.9018 0.0037 1.0247 0.147 Uiso 1 1 calc R U . . .
C18 C 0.748(2) -0.1442(9) 0.5539(18) 0.059(4) Uani 1 1 d . . . . .
C7 C 0.635(2) 0.1655(9) 0.1919(18) 0.066(5) Uani 1 1 d . . . . .
H7 H 0.6943 0.1913 0.1422 0.080 Uiso 1 1 calc R U . . .
C33 C 0.605(2) -0.0266(10) 1.0152(18) 0.089(6) Uani 1 1 d . . . . .
H33A H 0.6109 -0.0055 1.1088 0.133 Uiso 1 1 calc R U . . .
H33B H 0.6916 -0.0572 1.0218 0.133 Uiso 1 1 calc R U . . .
H33C H 0.5121 -0.0538 0.9856 0.133 Uiso 1 1 calc R U . . .
C25 C 0.313(2) 0.0597(12) 0.831(2) 0.097(7) Uani 1 1 d . . . . .
H25A H 0.2993 0.0139 0.8696 0.146 Uiso 1 1 calc R U . . .
H25B H 0.2475 0.0643 0.7344 0.146 Uiso 1 1 calc R U . . .
H25C H 0.2884 0.0958 0.8928 0.146 Uiso 1 1 calc R U . . .
C11 C 0.159(3) 0.1895(13) 0.087(2) 0.079(7) Uani 1 1 d . . . . .
H11 H 0.0527 0.1944 0.0599 0.095 Uiso 1 1 calc R U . . .
C17 C 0.413(2) -0.1328(10) 0.545(3) 0.082(6) Uani 1 1 d . . . . .
H17A H 0.4244 -0.1497 0.4516 0.098 Uiso 1 1 calc R U . . .
H17B H 0.3634 -0.1697 0.5879 0.098 Uiso 1 1 calc R U . . .
C13 C 0.3863(18) 0.1311(7) 0.2232(14) 0.045(4) Uani 1 1 d . . . . .
C26 C 0.533(2) 0.1210(9) 0.7415(17) 0.069(5) Uani 1 1 d . . . . .
C27 C 0.433(3) 0.1781(11) 0.649(2) 0.117(10) Uani 1 1 d . . . . .
H27A H 0.3281 0.1627 0.6232 0.175 Uiso 1 1 calc R U . . .
H27B H 0.4668 0.1863 0.5624 0.175 Uiso 1 1 calc R U . . .
H27C H 0.4412 0.2213 0.7047 0.175 Uiso 1 1 calc R U . . .
C23 C 0.878(2) -0.1799(9) 0.6280(19) 0.074(5) Uani 1 1 d . . . . .
H23 H 0.8998 -0.1876 0.7282 0.088 Uiso 1 1 calc R U . . .
C21 C 0.941(3) -0.1877(12) 0.402(3) 0.103(8) Uani 1 1 d . . . . .
H21 H 1.0118 -0.2008 0.3506 0.123 Uiso 1 1 calc R U . . .
C20 C 0.815(4) -0.1545(11) 0.331(2) 0.108(9) Uani 1 1 d . . . . .
H20 H 0.7972 -0.1465 0.2311 0.130 Uiso 1 1 calc R U . . .
F5 F 0.749(3) 0.3728(10) 1.0988(16) 0.224(11) Uani 1 1 d . . . . .
F3 F 0.960(2) 0.3656(12) 1.016(4) 0.260(15) 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 N1 2.057(11) . ?
Ir1 C2 2.064(12) . ?
Ir1 C26 2.178(15) . ?
Ir1 C30 2.192(15) . ?
Ir1 C28 2.200(15) . ?
Ir1 C24 2.240(14) . ?
Ir1 C32 2.256(13) . ?
Ir1 Se1 2.4474(18) . ?
Se1 C18 1.943(15) . ?
Se1 C17 2.01(2) . ?
P1 F3 1.506(19) . ?
P1 F4 1.509(18) . ?
P1 F5 1.525(17) . ?
P1 F6 1.527(17) . ?
P1 F2 1.563(13) . ?
P1 F1 1.565(14) . ?
C28 C30 1.41(2) . ?
C28 C26 1.45(3) . ?
C28 C29 1.49(2) . ?
C15 N1 1.277(18) . ?
C15 C14 1.43(2) . ?
C15 H15 0.9300 . ?
C22 C21 1.33(3) . ?
C22 C23 1.38(2) . ?
C22 H22 0.9300 . ?
C3 C2 1.359(17) . ?
C3 C4 1.40(2) . ?
C3 H3 0.9300 . ?
C2 C1 1.448(19) . ?
C32 C24 1.41(2) . ?
C32 C30 1.46(2) . ?
C32 C33 1.48(2) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
N1 C16 1.465(16) . ?
C19 C18 1.38(2) . ?
C19 C20 1.39(3) . ?
C19 H19 0.9300 . ?
C8 C9 1.38(2) . ?
C8 C7 1.41(2) . ?
C8 C13 1.43(2) . ?
C9 C10 1.29(3) . ?
C9 H9 0.9300 . ?
C5 C4 1.35(3) . ?
C5 C6 1.41(2) . ?
C5 H5 0.9300 . ?
C24 C26 1.44(2) . ?
C24 C25 1.50(3) . ?
C16 C17 1.51(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C14 1.40(2) . ?
C1 C6 1.42(2) . ?
C4 H4 0.9300 . ?
C6 C7 1.41(2) . ?
C30 C31 1.49(2) . ?
C10 C11 1.49(3) . ?
C10 H10 0.9300 . ?
C14 C13 1.44(2) . ?
C12 C11 1.32(3) . ?
C12 C13 1.41(2) . ?
C12 H12 0.9300 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C18 C23 1.38(2) . ?
C7 H7 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C11 H11 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C26 C27 1.53(2) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C23 H23 0.9300 . ?
C21 C20 1.32(3) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir1 C2 85.7(5) . . ?
N1 Ir1 C26 102.5(6) . . ?
C2 Ir1 C26 107.1(6) . . ?
N1 Ir1 C30 163.4(5) . . ?
C2 Ir1 C30 107.2(6) . . ?
C26 Ir1 C30 64.1(6) . . ?
N1 Ir1 C28 136.0(7) . . ?
C2 Ir1 C28 88.5(5) . . ?
C26 Ir1 C28 38.8(7) . . ?
C30 Ir1 C28 37.4(7) . . ?
N1 Ir1 C24 99.8(6) . . ?
C2 Ir1 C24 145.1(6) . . ?
C26 Ir1 C24 38.1(6) . . ?
C30 Ir1 C24 63.6(6) . . ?
C28 Ir1 C24 63.6(6) . . ?
N1 Ir1 C32 127.9(5) . . ?
C2 Ir1 C32 145.5(6) . . ?
C26 Ir1 C32 62.4(7) . . ?
C30 Ir1 C32 38.3(5) . . ?
C28 Ir1 C32 62.4(7) . . ?
C24 Ir1 C32 36.5(6) . . ?
N1 Ir1 Se1 82.5(3) . . ?
C2 Ir1 Se1 98.4(3) . . ?
C26 Ir1 Se1 154.3(5) . . ?
C30 Ir1 Se1 105.2(4) . . ?
C28 Ir1 Se1 141.4(6) . . ?
C24 Ir1 Se1 116.4(5) . . ?
C32 Ir1 Se1 94.3(6) . . ?
C18 Se1 C17 99.1(8) . . ?
C18 Se1 Ir1 111.3(5) . . ?
C17 Se1 Ir1 96.6(5) . . ?
F3 P1 F4 173.0(18) . . ?
F3 P1 F5 95.0(16) . . ?
F4 P1 F5 91.3(14) . . ?
F3 P1 F6 89.6(16) . . ?
F4 P1 F6 84.0(14) . . ?
F5 P1 F6 175.4(16) . . ?
F3 P1 F2 91.5(10) . . ?
F4 P1 F2 91.4(11) . . ?
F5 P1 F2 90.8(9) . . ?
F6 P1 F2 89.3(9) . . ?
F3 P1 F1 86.8(10) . . ?
F4 P1 F1 90.4(11) . . ?
F5 P1 F1 88.4(9) . . ?
F6 P1 F1 91.7(10) . . ?
F2 P1 F1 178.1(11) . . ?
C30 C28 C26 108.2(15) . . ?
C30 C28 C29 125(2) . . ?
C26 C28 C29 127(2) . . ?
C30 C28 Ir1 71.0(9) . . ?
C26 C28 Ir1 69.7(9) . . ?
C29 C28 Ir1 126.1(11) . . ?
N1 C15 C14 125.6(14) . . ?
N1 C15 H15 117.2 . . ?
C14 C15 H15 117.2 . . ?
C21 C22 C23 120(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C2 C3 C4 123.0(18) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C3 C2 C1 117.9(13) . . ?
C3 C2 Ir1 122.6(10) . . ?
C1 C2 Ir1 117.7(10) . . ?
C24 C32 C30 109.1(16) . . ?
C24 C32 C33 127.0(16) . . ?
C30 C32 C33 123.9(16) . . ?
C24 C32 Ir1 71.2(8) . . ?
C30 C32 Ir1 68.5(8) . . ?
C33 C32 Ir1 128.4(15) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C15 N1 C16 120.6(14) . . ?
C15 N1 Ir1 123.5(11) . . ?
C16 N1 Ir1 115.9(10) . . ?
C18 C19 C20 115.8(19) . . ?
C18 C19 H19 122.1 . . ?
C20 C19 H19 122.1 . . ?
C9 C8 C7 121.1(16) . . ?
C9 C8 C13 120.9(18) . . ?
C7 C8 C13 117.8(15) . . ?
C10 C9 C8 119.8(19) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C4 C5 C6 120.7(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C32 C24 C26 107.6(16) . . ?
C32 C24 C25 127.2(17) . . ?
C26 C24 C25 125.1(17) . . ?
C32 C24 Ir1 72.4(9) . . ?
C26 C24 Ir1 68.6(8) . . ?
C25 C24 Ir1 127.7(12) . . ?
N1 C16 C17 110.4(13) . . ?
N1 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
N1 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C14 C1 C6 119.1(15) . . ?
C14 C1 C2 123.0(13) . . ?
C6 C1 C2 117.9(14) . . ?
C5 C4 C3 119.4(18) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C5 C6 C7 120.5(16) . . ?
C5 C6 C1 119.9(17) . . ?
C7 C6 C1 119.7(15) . . ?
C28 C30 C32 107.2(15) . . ?
C28 C30 C31 126.6(18) . . ?
C32 C30 C31 125.3(17) . . ?
C28 C30 Ir1 71.6(9) . . ?
C32 C30 Ir1 73.2(8) . . ?
C31 C30 Ir1 129.1(13) . . ?
C9 C10 C11 122.2(19) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C1 C14 C15 120.9(14) . . ?
C1 C14 C13 120.8(13) . . ?
C15 C14 C13 117.6(14) . . ?
C11 C12 C13 122.5(18) . . ?
C11 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C23 C18 C19 124.3(16) . . ?
C23 C18 Se1 114.3(13) . . ?
C19 C18 Se1 121.4(14) . . ?
C8 C7 C6 122.2(14) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C12 C11 C10 117(2) . . ?
C12 C11 H11 121.6 . . ?
C10 C11 H11 121.6 . . ?
C16 C17 Se1 109.6(12) . . ?
C16 C17 H17A 109.7 . . ?
Se1 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
Se1 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C12 C13 C8 117.2(15) . . ?
C12 C13 C14 123.0(13) . . ?
C8 C13 C14 119.6(15) . . ?
C24 C26 C28 107.7(16) . . ?
C24 C26 C27 124.4(19) . . ?
C28 C26 C27 127(2) . . ?
C24 C26 Ir1 73.3(9) . . ?
C28 C26 Ir1 71.4(8) . . ?
C27 C26 Ir1 126.9(12) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C18 C23 C22 115.8(17) . . ?
C18 C23 H23 122.1 . . ?
C22 C23 H23 122.1 . . ?
C20 C21 C22 124(2) . . ?
C20 C21 H21 118.1 . . ?
C22 C21 H21 118.1 . . ?
C21 C20 C19 120(2) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?

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
C4 C3 C2 C1 5(3) . . . . ?
C4 C3 C2 Ir1 -159.0(14) . . . . ?
C14 C15 N1 C16 -168.3(15) . . . . ?
C14 C15 N1 Ir1 8(2) . . . . ?
C7 C8 C9 C10 -177.7(19) . . . . ?
C13 C8 C9 C10 7(3) . . . . ?
C30 C32 C24 C26 -1.7(18) . . . . ?
C33 C32 C24 C26 175.7(17) . . . . ?
Ir1 C32 C24 C26 -59.8(10) . . . . ?
C30 C32 C24 C25 -177.5(16) . . . . ?
C33 C32 C24 C25 0(3) . . . . ?
Ir1 C32 C24 C25 124.3(17) . . . . ?
C30 C32 C24 Ir1 58.1(11) . . . . ?
C33 C32 C24 Ir1 -124.4(19) . . . . ?
C15 N1 C16 C17 117.1(17) . . . . ?
Ir1 N1 C16 C17 -59.7(16) . . . . ?
C3 C2 C1 C14 169.7(15) . . . . ?
Ir1 C2 C1 C14 -25.1(16) . . . . ?
C3 C2 C1 C6 -11.8(19) . . . . ?
Ir1 C2 C1 C6 153.3(10) . . . . ?
C6 C5 C4 C3 -6(3) . . . . ?
C2 C3 C4 C5 3(3) . . . . ?
C4 C5 C6 C7 179.0(18) . . . . ?
C4 C5 C6 C1 -1(3) . . . . ?
C14 C1 C6 C5 -171.6(15) . . . . ?
C2 C1 C6 C5 10(2) . . . . ?
C14 C1 C6 C7 8(2) . . . . ?
C2 C1 C6 C7 -170.3(13) . . . . ?
C26 C28 C30 C32 -5.0(17) . . . . ?
C29 C28 C30 C32 173.6(14) . . . . ?
Ir1 C28 C30 C32 -65.1(11) . . . . ?
C26 C28 C30 C31 -174.4(15) . . . . ?
C29 C28 C30 C31 4(3) . . . . ?
Ir1 C28 C30 C31 125.6(17) . . . . ?
C26 C28 C30 Ir1 60.1(10) . . . . ?
C29 C28 C30 Ir1 -121.3(15) . . . . ?
C24 C32 C30 C28 4.2(18) . . . . ?
C33 C32 C30 C28 -173.3(16) . . . . ?
Ir1 C32 C30 C28 64.0(11) . . . . ?
C24 C32 C30 C31 173.8(17) . . . . ?
C33 C32 C30 C31 -4(3) . . . . ?
Ir1 C32 C30 C31 -126.5(17) . . . . ?
C24 C32 C30 Ir1 -59.8(11) . . . . ?
C33 C32 C30 Ir1 122.7(18) . . . . ?
C8 C9 C10 C11 -9(3) . . . . ?
C6 C1 C14 C15 161.8(14) . . . . ?
C2 C1 C14 C15 -20(2) . . . . ?
C6 C1 C14 C13 -9(2) . . . . ?
C2 C1 C14 C13 169.9(12) . . . . ?
N1 C15 C14 C1 31(2) . . . . ?
N1 C15 C14 C13 -158.6(15) . . . . ?
C20 C19 C18 C23 -3(3) . . . . ?
C20 C19 C18 Se1 176.3(14) . . . . ?
C9 C8 C7 C6 178.4(16) . . . . ?
C13 C8 C7 C6 -6(2) . . . . ?
C5 C6 C7 C8 179.0(16) . . . . ?
C1 C6 C7 C8 -1(2) . . . . ?
C13 C12 C11 C10 -2(3) . . . . ?
C9 C10 C11 C12 7(3) . . . . ?
N1 C16 C17 Se1 42.7(18) . . . . ?
C11 C12 C13 C8 1(2) . . . . ?
C11 C12 C13 C14 176.6(17) . . . . ?
C9 C8 C13 C12 -3(2) . . . . ?
C7 C8 C13 C12 -178.5(14) . . . . ?
C9 C8 C13 C14 -178.8(15) . . . . ?
C7 C8 C13 C14 6(2) . . . . ?
C1 C14 C13 C12 -174.0(14) . . . . ?
C15 C14 C13 C12 15(2) . . . . ?
C1 C14 C13 C8 1.6(19) . . . . ?
C15 C14 C13 C8 -169.1(13) . . . . ?
C32 C24 C26 C28 -1.4(17) . . . . ?
C25 C24 C26 C28 174.6(15) . . . . ?
Ir1 C24 C26 C28 -63.6(10) . . . . ?
C32 C24 C26 C27 -174.1(15) . . . . ?
C25 C24 C26 C27 2(3) . . . . ?
Ir1 C24 C26 C27 123.6(16) . . . . ?
C32 C24 C26 Ir1 62.3(11) . . . . ?
C25 C24 C26 Ir1 -121.8(16) . . . . ?
C30 C28 C26 C24 4.0(17) . . . . ?
C29 C28 C26 C24 -174.6(14) . . . . ?
Ir1 C28 C26 C24 64.8(10) . . . . ?
C30 C28 C26 C27 176.5(15) . . . . ?
C29 C28 C26 C27 -2(2) . . . . ?
Ir1 C28 C26 C27 -122.7(16) . . . . ?
C30 C28 C26 Ir1 -60.8(10) . . . . ?
C29 C28 C26 Ir1 120.6(15) . . . . ?
C19 C18 C23 C22 0(3) . . . . ?
Se1 C18 C23 C22 -179.0(15) . . . . ?
C21 C22 C23 C18 4(3) . . . . ?
C23 C22 C21 C20 -5(4) . . . . ?
C22 C21 C20 C19 2(4) . . . . ?
C18 C19 C20 C21 2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C23 H23 F3 0.93 2.63 3.43(3) 143.9 2_747
C15 H15 F2 0.93 2.59 3.22(2) 125.9 2_646
C23 H23 F3 0.93 2.63 3.43(3) 143.9 2_747
C15 H15 F2 0.93 2.59 3.22(2) 125.9 2_646

_refine_diff_density_max         1.392
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.117

# start validation Reply Form
_vrf_PLAT342_shelxl              
;
RESPONSE:This alert is due to presence of unresolvable disorder in the hexafluorophosphate molecules.
;
_vrf_PLAT973_shelxl              
;
RESPONSE:This alert is due to presence of  residual positive electron density with highest peak of 1.392 e.A^-3 
in the presence of heavy metal atom.
;
# end validation Reply Form

####################################################################### 
# 
# 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_complex3
_audit_block_doi                 10.5517/ccdc.csd.cc1ptlsw
_database_code_depnum_ccdc_archive 'CCDC 1573739'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H34 Cl Ir N S, F6 P'
_chemical_formula_sum            'C33 H34 Cl F6 Ir N P S'
_chemical_formula_weight         849.31

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.252(2)
_cell_length_b                   13.705(2)
_cell_length_c                   19.940(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.778(4)
_cell_angle_gamma                90
_cell_volume                     3222.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1577
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      18.39

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      1.751
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_F_000             1672.0
_exptl_transmission_factor_min   0.279
_exptl_transmission_factor_max   0.292
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    4.401
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13663
_diffrn_reflns_av_unetI/netI     0.0934
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.727
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5683
_reflns_number_gt                4389
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.6355P] 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         5672
_refine_ls_number_parameters     402
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.1636
_refine_ls_wR_factor_gt          0.1475
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_restrained_S_all      0.938
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.63543(3) 0.38061(3) 0.80174(2) 0.02875(17) Uani 1 1 d . . . . .
Cl1 Cl 0.5960(3) 0.2123(2) 0.77178(16) 0.0459(7) Uani 1 1 d . . . . .
S1 S 0.7586(2) 0.3407(2) 0.91097(14) 0.0413(7) Uani 1 1 d . . . . .
P1 P 0.7778(3) 0.7418(3) 0.54903(17) 0.0493(9) Uani 1 1 d . . . . .
N1 N 0.7813(7) 0.3572(6) 0.7686(5) 0.031(2) Uani 1 1 d . . . . .
F5 F 0.8437(8) 0.8179(7) 0.5128(4) 0.085(3) Uani 1 1 d . . . . .
F2 F 0.7192(8) 0.7002(7) 0.4749(4) 0.091(3) Uani 1 1 d . . . . .
C16 C 0.8889(10) 0.3619(10) 0.8211(6) 0.052(3) Uani 1 1 d . . . . .
H16A H 0.9072 0.4292 0.8345 0.062 Uiso 1 1 calc R U . . .
H16B H 0.9483 0.3359 0.8025 0.062 Uiso 1 1 calc R U . . .
C26 C 0.6083(9) 0.5344(8) 0.8159(5) 0.034(3) Uani 1 1 d . . . . .
C18 C 0.7218(11) 0.2310(9) 0.9486(6) 0.046(3) Uani 1 1 d . . . . .
C32 C 0.4941(9) 0.4445(8) 0.7247(6) 0.036(3) Uani 1 1 d . . . . .
F1 F 0.8408(9) 0.7865(8) 0.6225(4) 0.106(4) Uani 1 1 d . . . . .
F6 F 0.7174(11) 0.6667(10) 0.5838(6) 0.137(5) Uani 1 1 d . . . . .
C15 C 0.7780(9) 0.3342(9) 0.7064(6) 0.041(3) Uani 1 1 d . . . . .
H15 H 0.7057 0.3291 0.6760 0.049 Uiso 1 1 calc R U . . .
C24 C 0.5831(9) 0.5160(8) 0.7418(6) 0.034(3) Uani 1 1 d . . . . .
F3 F 0.8819(9) 0.6712(7) 0.5537(6) 0.107(3) Uani 1 1 d . . . . .
F4 F 0.6803(8) 0.8177(9) 0.5420(6) 0.116(4) Uani 1 1 d . . . . .
C23 C 0.6154(12) 0.2244(11) 0.9565(7) 0.066(4) Uani 1 1 d . . . . .
H23 H 0.5638 0.2747 0.9410 0.079 Uiso 1 1 calc R U . . .
C13 C 0.8769(10) 0.2253(9) 0.6442(6) 0.042(3) Uani 1 1 d . . . . .
C28 C 0.5286(9) 0.4802(9) 0.8409(6) 0.042(3) Uani 1 1 d . . . . .
C30 C 0.4591(9) 0.4220(9) 0.7857(5) 0.036(3) Uani 1 1 d . . . . .
C12 C 0.7941(11) 0.1494(10) 0.6420(7) 0.055(3) Uani 1 1 d . . . . .
H12 H 0.7337 0.1606 0.6609 0.066 Uiso 1 1 calc R U . . .
C19 C 0.8002(11) 0.1588(10) 0.9731(6) 0.053(3) Uani 1 1 d . . . . .
H19 H 0.8738 0.1636 0.9689 0.063 Uiso 1 1 calc R U . . .
C1 C 0.9544(10) 0.3872(9) 0.6725(7) 0.044(3) Uani 1 1 d . . . . .
C3 C 1.0321(13) 0.5513(11) 0.6988(8) 0.068(4) Uani 1 1 d . . . . .
H3 H 1.0282 0.6137 0.7163 0.082 Uiso 1 1 calc R U . . .
C4 C 1.1206(12) 0.5256(12) 0.6705(8) 0.069(4) Uani 1 1 d . . . . .
H4 H 1.1789 0.5700 0.6727 0.083 Uiso 1 1 calc R U . . .
C14 C 0.8717(9) 0.3147(9) 0.6758(6) 0.040(3) Uani 1 1 d . . . . .
C2 C 0.9517(12) 0.4832(10) 0.7004(7) 0.057(4) Uani 1 1 d . . . . .
H2 H 0.8935 0.4996 0.7200 0.068 Uiso 1 1 calc R U . . .
C9 C 0.9687(13) 0.1085(10) 0.5800(7) 0.058(4) Uani 1 1 d . . . . .
H9 H 1.0252 0.0943 0.5584 0.070 Uiso 1 1 calc R U . . .
C6 C 1.0415(11) 0.3648(10) 0.6422(7) 0.051(3) Uani 1 1 d . . . . .
C8 C 0.9657(10) 0.2035(10) 0.6123(6) 0.048(3) Uani 1 1 d . . . . .
C7 C 1.0434(10) 0.2744(9) 0.6115(6) 0.043(3) Uani 1 1 d . . . . .
H7 H 1.0997 0.2616 0.5895 0.051 Uiso 1 1 calc R U . . .
C33 C 0.4377(11) 0.4097(11) 0.6532(6) 0.058(4) Uani 1 1 d . . . . .
H33A H 0.3903 0.3547 0.6557 0.087 Uiso 1 1 calc R U . . .
H33B H 0.4942 0.3906 0.6305 0.087 Uiso 1 1 calc R U . . .
H33C H 0.3921 0.4612 0.6272 0.087 Uiso 1 1 calc R U . . .
C31 C 0.3627(11) 0.3584(12) 0.7909(7) 0.066(4) Uani 1 1 d . . . . .
H31A H 0.2927 0.3935 0.7745 0.098 Uiso 1 1 calc R U . . .
H31B H 0.3728 0.3398 0.8387 0.098 Uiso 1 1 calc R U . . .
H31C H 0.3607 0.3010 0.7630 0.098 Uiso 1 1 calc R U . . .
C11 C 0.8042(13) 0.0607(10) 0.6118(8) 0.063(4) Uani 1 1 d . . . . .
H11 H 0.7514 0.0120 0.6118 0.075 Uiso 1 1 calc R U . . .
C22 C 0.5838(15) 0.1433(12) 0.9874(8) 0.073(4) Uani 1 1 d . . . . .
H22 H 0.5106 0.1379 0.9922 0.088 Uiso 1 1 calc R U . . .
C29 C 0.5180(12) 0.4885(11) 0.9153(6) 0.064(4) Uani 1 1 d . . . . .
H29A H 0.5899 0.4742 0.9477 0.097 Uiso 1 1 calc R U . . .
H29B H 0.4623 0.4429 0.9218 0.097 Uiso 1 1 calc R U . . .
H29C H 0.4953 0.5535 0.9232 0.097 Uiso 1 1 calc R U . . .
C20 C 0.7655(15) 0.0782(12) 1.0044(6) 0.066(4) Uani 1 1 d . . . . .
H20 H 0.8172 0.0283 1.0210 0.079 Uiso 1 1 calc R U . . .
C25 C 0.6373(11) 0.5612(9) 0.6916(7) 0.051(3) Uani 1 1 d . . . . .
H25A H 0.6483 0.5126 0.6594 0.076 Uiso 1 1 calc R U . . .
H25B H 0.7093 0.5882 0.7163 0.076 Uiso 1 1 calc R U . . .
H25C H 0.5894 0.6121 0.6665 0.076 Uiso 1 1 calc R U . . .
C21 C 0.6619(16) 0.0703(11) 1.0112(7) 0.070(5) Uani 1 1 d . . . . .
H21 H 0.6415 0.0152 1.0322 0.084 Uiso 1 1 calc R U . . .
C5 C 1.1239(11) 0.4369(11) 0.6395(7) 0.057(4) Uani 1 1 d . . . . .
H5 H 1.1794 0.4238 0.6169 0.069 Uiso 1 1 calc R U . . .
C10 C 0.8904(14) 0.0424(12) 0.5816(7) 0.067(4) Uani 1 1 d . . . . .
H10 H 0.8939 -0.0184 0.5616 0.080 Uiso 1 1 calc R U . . .
C27 C 0.6923(12) 0.6080(10) 0.8548(8) 0.067(4) Uani 1 1 d . . . . .
H27A H 0.6593 0.6720 0.8472 0.101 Uiso 1 1 calc R U . . .
H27B H 0.7590 0.6060 0.8384 0.101 Uiso 1 1 calc R U . . .
H27C H 0.7123 0.5933 0.9037 0.101 Uiso 1 1 calc R U . . .
C17 C 0.8825(10) 0.3049(11) 0.8824(6) 0.053(4) Uani 1 1 d . . . . .
H17A H 0.9507 0.3154 0.9200 0.064 Uiso 1 1 calc R U . . .
H17B H 0.8778 0.2360 0.8709 0.064 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 2.092(8) . ?
Ir1 C32 2.163(10) . ?
Ir1 C26 2.165(10) . ?
Ir1 C30 2.171(10) . ?
Ir1 C28 2.177(10) . ?
Ir1 C24 2.206(10) . ?
Ir1 S1 2.352(3) . ?
Ir1 Cl1 2.398(3) . ?
S1 C18 1.792(13) . ?
S1 C17 1.828(12) . ?
P1 F6 1.538(9) . ?
P1 F4 1.561(10) . ?
P1 F2 1.565(8) . ?
P1 F1 1.582(9) . ?
P1 F3 1.583(10) . ?
P1 F5 1.605(9) . ?
N1 C15 1.269(14) . ?
N1 C16 1.445(15) . ?
C16 C17 1.470(16) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C26 C28 1.421(15) . ?
C26 C24 1.446(14) . ?
C26 C27 1.498(16) . ?
C18 C23 1.357(18) . ?
C18 C19 1.373(17) . ?
C32 C30 1.428(14) . ?
C32 C24 1.437(15) . ?
C32 C33 1.483(16) . ?
C15 C14 1.465(15) . ?
C15 H15 0.9300 . ?
C24 C25 1.479(14) . ?
C23 C22 1.377(19) . ?
C23 H23 0.9300 . ?
C13 C14 1.388(16) . ?
C13 C8 1.433(15) . ?
C13 C12 1.444(17) . ?
C28 C30 1.436(16) . ?
C28 C29 1.528(15) . ?
C30 C31 1.495(17) . ?
C12 C11 1.378(18) . ?
C12 H12 0.9300 . ?
C19 C20 1.390(19) . ?
C19 H19 0.9300 . ?
C1 C6 1.396(17) . ?
C1 C2 1.432(17) . ?
C1 C14 1.433(16) . ?
C3 C2 1.363(18) . ?
C3 C4 1.40(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.37(2) . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
C9 C10 1.326(19) . ?
C9 C8 1.457(17) . ?
C9 H9 0.9300 . ?
C6 C7 1.385(17) . ?
C6 C5 1.423(18) . ?
C8 C7 1.364(17) . ?
C7 H7 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C11 C10 1.373(19) . ?
C11 H11 0.9300 . ?
C22 C21 1.38(2) . ?
C22 H22 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C20 C21 1.32(2) . ?
C20 H20 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C21 H21 0.9300 . ?
C5 H5 0.9300 . ?
C10 H10 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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 C32 115.2(4) . . ?
N1 Ir1 C26 111.4(4) . . ?
C32 Ir1 C26 65.0(4) . . ?
N1 Ir1 C30 153.5(4) . . ?
C32 Ir1 C30 38.5(4) . . ?
C26 Ir1 C30 65.3(4) . . ?
N1 Ir1 C28 149.1(4) . . ?
C32 Ir1 C28 63.8(4) . . ?
C26 Ir1 C28 38.2(4) . . ?
C30 Ir1 C28 38.6(4) . . ?
N1 Ir1 C24 96.1(4) . . ?
C32 Ir1 C24 38.4(4) . . ?
C26 Ir1 C24 38.6(4) . . ?
C30 Ir1 C24 64.5(4) . . ?
C28 Ir1 C24 63.4(4) . . ?
N1 Ir1 S1 82.4(3) . . ?
C32 Ir1 S1 160.0(3) . . ?
C26 Ir1 S1 100.9(3) . . ?
C30 Ir1 S1 124.0(3) . . ?
C28 Ir1 S1 96.3(3) . . ?
C24 Ir1 S1 135.7(3) . . ?
N1 Ir1 Cl1 84.6(2) . . ?
C32 Ir1 Cl1 98.3(3) . . ?
C26 Ir1 Cl1 160.3(3) . . ?
C30 Ir1 Cl1 95.1(3) . . ?
C28 Ir1 Cl1 126.3(3) . . ?
C24 Ir1 Cl1 131.7(3) . . ?
S1 Ir1 Cl1 92.41(11) . . ?
C18 S1 C17 103.3(6) . . ?
C18 S1 Ir1 114.3(4) . . ?
C17 S1 Ir1 98.7(4) . . ?
F6 P1 F4 92.0(8) . . ?
F6 P1 F2 91.6(6) . . ?
F4 P1 F2 90.8(6) . . ?
F6 P1 F1 90.8(6) . . ?
F4 P1 F1 89.7(6) . . ?
F2 P1 F1 177.4(6) . . ?
F6 P1 F3 92.5(7) . . ?
F4 P1 F3 175.5(7) . . ?
F2 P1 F3 89.3(6) . . ?
F1 P1 F3 90.0(6) . . ?
F6 P1 F5 178.4(8) . . ?
F4 P1 F5 89.6(6) . . ?
F2 P1 F5 88.2(5) . . ?
F1 P1 F5 89.3(5) . . ?
F3 P1 F5 85.9(6) . . ?
C15 N1 C16 120.0(9) . . ?
C15 N1 Ir1 122.9(7) . . ?
C16 N1 Ir1 117.0(7) . . ?
N1 C16 C17 109.5(10) . . ?
N1 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
N1 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C28 C26 C24 106.9(9) . . ?
C28 C26 C27 127.7(11) . . ?
C24 C26 C27 124.8(11) . . ?
C28 C26 Ir1 71.4(6) . . ?
C24 C26 Ir1 72.2(6) . . ?
C27 C26 Ir1 127.9(8) . . ?
C23 C18 C19 120.8(12) . . ?
C23 C18 S1 117.6(10) . . ?
C19 C18 S1 121.5(10) . . ?
C30 C32 C24 109.2(10) . . ?
C30 C32 C33 125.4(10) . . ?
C24 C32 C33 125.0(10) . . ?
C30 C32 Ir1 71.1(6) . . ?
C24 C32 Ir1 72.4(6) . . ?
C33 C32 Ir1 128.7(8) . . ?
N1 C15 C14 129.2(10) . . ?
N1 C15 H15 115.4 . . ?
C14 C15 H15 115.4 . . ?
C32 C24 C26 107.4(9) . . ?
C32 C24 C25 125.1(11) . . ?
C26 C24 C25 127.5(11) . . ?
C32 C24 Ir1 69.2(6) . . ?
C26 C24 Ir1 69.2(6) . . ?
C25 C24 Ir1 126.9(8) . . ?
C18 C23 C22 120.1(15) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C14 C13 C8 121.3(11) . . ?
C14 C13 C12 122.1(11) . . ?
C8 C13 C12 116.6(12) . . ?
C26 C28 C30 110.0(9) . . ?
C26 C28 C29 123.3(11) . . ?
C30 C28 C29 126.6(11) . . ?
C26 C28 Ir1 70.4(6) . . ?
C30 C28 Ir1 70.5(6) . . ?
C29 C28 Ir1 127.8(8) . . ?
C32 C30 C28 106.3(10) . . ?
C32 C30 C31 127.7(11) . . ?
C28 C30 C31 125.8(10) . . ?
C32 C30 Ir1 70.5(6) . . ?
C28 C30 Ir1 70.9(6) . . ?
C31 C30 Ir1 127.7(9) . . ?
C11 C12 C13 120.2(12) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C18 C19 C20 117.5(14) . . ?
C18 C19 H19 121.2 . . ?
C20 C19 H19 121.2 . . ?
C6 C1 C2 118.1(12) . . ?
C6 C1 C14 120.1(11) . . ?
C2 C1 C14 121.9(11) . . ?
C2 C3 C4 118.8(15) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 121.8(13) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C13 C14 C1 118.1(10) . . ?
C13 C14 C15 119.2(10) . . ?
C1 C14 C15 122.5(11) . . ?
C3 C2 C1 121.8(13) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C10 C9 C8 119.6(13) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C7 C6 C1 119.6(12) . . ?
C7 C6 C5 120.5(12) . . ?
C1 C6 C5 119.8(13) . . ?
C7 C8 C13 118.2(12) . . ?
C7 C8 C9 122.0(12) . . ?
C13 C8 C9 119.7(13) . . ?
C8 C7 C6 122.5(11) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C10 C11 C12 121.6(14) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C21 C22 C23 119.1(15) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C21 C20 C19 122.2(15) . . ?
C21 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C20 C21 C22 120.3(14) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C4 C5 C6 119.4(13) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C9 C10 C11 122.2(14) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C16 C17 S1 110.7(9) . . ?
C16 C17 H17A 109.5 . . ?
S1 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?

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
C15 N1 C16 C17 -129.5(12) . . . . ?
Ir1 N1 C16 C17 46.7(13) . . . . ?
C17 S1 C18 C23 -161.2(11) . . . . ?
Ir1 S1 C18 C23 -55.0(12) . . . . ?
C17 S1 C18 C19 23.1(12) . . . . ?
Ir1 S1 C18 C19 129.3(10) . . . . ?
C16 N1 C15 C14 -3.4(19) . . . . ?
Ir1 N1 C15 C14 -179.4(9) . . . . ?
C30 C32 C24 C26 3.1(12) . . . . ?
C33 C32 C24 C26 175.8(11) . . . . ?
Ir1 C32 C24 C26 -58.8(7) . . . . ?
C30 C32 C24 C25 -176.8(10) . . . . ?
C33 C32 C24 C25 -4.1(18) . . . . ?
Ir1 C32 C24 C25 121.3(11) . . . . ?
C30 C32 C24 Ir1 61.9(7) . . . . ?
C33 C32 C24 Ir1 -125.4(12) . . . . ?
C28 C26 C24 C32 -4.5(12) . . . . ?
C27 C26 C24 C32 -176.9(11) . . . . ?
Ir1 C26 C24 C32 58.8(7) . . . . ?
C28 C26 C24 C25 175.4(11) . . . . ?
C27 C26 C24 C25 3.1(17) . . . . ?
Ir1 C26 C24 C25 -121.2(11) . . . . ?
C28 C26 C24 Ir1 -63.4(7) . . . . ?
C27 C26 C24 Ir1 124.3(11) . . . . ?
C19 C18 C23 C22 -2(2) . . . . ?
S1 C18 C23 C22 -177.7(11) . . . . ?
C24 C26 C28 C30 4.4(12) . . . . ?
C27 C26 C28 C30 176.4(11) . . . . ?
Ir1 C26 C28 C30 -59.6(8) . . . . ?
C24 C26 C28 C29 -173.1(10) . . . . ?
C27 C26 C28 C29 -1.0(18) . . . . ?
Ir1 C26 C28 C29 123.0(11) . . . . ?
C24 C26 C28 Ir1 63.9(7) . . . . ?
C27 C26 C28 Ir1 -124.0(12) . . . . ?
C24 C32 C30 C28 -0.4(12) . . . . ?
C33 C32 C30 C28 -173.1(11) . . . . ?
Ir1 C32 C30 C28 62.3(7) . . . . ?
C24 C32 C30 C31 174.2(12) . . . . ?
C33 C32 C30 C31 2(2) . . . . ?
Ir1 C32 C30 C31 -123.0(13) . . . . ?
C24 C32 C30 Ir1 -62.7(8) . . . . ?
C33 C32 C30 Ir1 124.6(12) . . . . ?
C26 C28 C30 C32 -2.5(13) . . . . ?
C29 C28 C30 C32 174.9(11) . . . . ?
Ir1 C28 C30 C32 -62.0(7) . . . . ?
C26 C28 C30 C31 -177.3(11) . . . . ?
C29 C28 C30 C31 0.1(19) . . . . ?
Ir1 C28 C30 C31 123.2(12) . . . . ?
C26 C28 C30 Ir1 59.5(8) . . . . ?
C29 C28 C30 Ir1 -123.1(12) . . . . ?
C14 C13 C12 C11 -178.2(13) . . . . ?
C8 C13 C12 C11 1.6(18) . . . . ?
C23 C18 C19 C20 2(2) . . . . ?
S1 C18 C19 C20 177.1(10) . . . . ?
C2 C3 C4 C5 5(2) . . . . ?
C8 C13 C14 C1 3.3(17) . . . . ?
C12 C13 C14 C1 -177.0(11) . . . . ?
C8 C13 C14 C15 178.8(10) . . . . ?
C12 C13 C14 C15 -1.5(18) . . . . ?
C6 C1 C14 C13 -4.1(18) . . . . ?
C2 C1 C14 C13 176.5(12) . . . . ?
C6 C1 C14 C15 -179.5(11) . . . . ?
C2 C1 C14 C15 1.2(19) . . . . ?
N1 C15 C14 C13 122.2(14) . . . . ?
N1 C15 C14 C1 -62.5(18) . . . . ?
C4 C3 C2 C1 -1(2) . . . . ?
C6 C1 C2 C3 -1(2) . . . . ?
C14 C1 C2 C3 178.3(13) . . . . ?
C2 C1 C6 C7 -176.6(12) . . . . ?
C14 C1 C6 C7 4.0(19) . . . . ?
C2 C1 C6 C5 -0.2(19) . . . . ?
C14 C1 C6 C5 -179.6(12) . . . . ?
C14 C13 C8 C7 -2.3(17) . . . . ?
C12 C13 C8 C7 178.0(11) . . . . ?
C14 C13 C8 C9 179.6(11) . . . . ?
C12 C13 C8 C9 -0.1(17) . . . . ?
C10 C9 C8 C7 -179.3(13) . . . . ?
C10 C9 C8 C13 -1.3(19) . . . . ?
C13 C8 C7 C6 2.2(18) . . . . ?
C9 C8 C7 C6 -179.8(12) . . . . ?
C1 C6 C7 C8 -3.1(19) . . . . ?
C5 C6 C7 C8 -179.5(12) . . . . ?
C13 C12 C11 C10 -2(2) . . . . ?
C18 C23 C22 C21 1(2) . . . . ?
C18 C19 C20 C21 0(2) . . . . ?
C19 C20 C21 C22 0(2) . . . . ?
C23 C22 C21 C20 0(2) . . . . ?
C3 C4 C5 C6 -6(2) . . . . ?
C7 C6 C5 C4 -179.7(12) . . . . ?
C1 C6 C5 C4 4(2) . . . . ?
C8 C9 C10 C11 1(2) . . . . ?
C12 C11 C10 C9 0(2) . . . . ?
N1 C16 C17 S1 -51.2(13) . . . . ?
C18 S1 C17 C16 150.1(10) . . . . ?
Ir1 S1 C17 C16 32.4(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C17 H17A F5 0.97 2.51 3.442(15) 160.6 2_746
C17 H17A F5 0.97 2.51 3.442(15) 160.6 2_746

_refine_diff_density_max         1.207
_refine_diff_density_min         -2.261
_refine_diff_density_rms         0.159

####################################################################### 
# 
# 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_L2
_audit_block_doi                 10.5517/ccdc.csd.cc1ptlnr
_database_code_depnum_ccdc_archive 'CCDC 1573735'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 N Se'
_chemical_formula_sum            'C23 H19 N Se'
_chemical_formula_weight         388.35

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   18.368(5)
_cell_length_b                   5.1780(14)
_cell_length_c                   20.341(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.958(6)
_cell_angle_gamma                90
_cell_volume                     1806.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    742
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      17.71

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             792.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    2.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.498
_exptl_absorpt_correction_T_max  0.557
_exptl_absorpt_process_details   '(SADABS; Bruker; 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7368
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.187
_diffrn_reflns_theta_max         24.982
_diffrn_reflns_theta_full        24.982
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3170
_reflns_number_gt                1933
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.0'
_computing_publication_material  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)+(0.0894P)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         3170
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1661
_refine_ls_wR_factor_gt          0.1322
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_restrained_S_all      0.946
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.46826(4) -0.05887(12) 0.38785(3) 0.0512(3) Uani 1 1 d . . . . .
N1 N 0.3101(3) 0.5653(10) 0.3322(3) 0.0539(13) Uani 1 1 d . . . . .
C8 C 0.0917(4) 1.1215(13) 0.2162(4) 0.0587(19) Uani 1 1 d . . . . .
C18 C 0.5465(3) 0.1811(11) 0.3840(3) 0.0448(15) Uani 1 1 d . . . . .
C9 C 0.0483(4) 1.2310(14) 0.1489(5) 0.072(2) Uani 1 1 d . . . . .
H9 H 0.0136 1.3647 0.1464 0.087 Uiso 1 1 calc R U . . .
C1 C 0.1814(4) 0.9035(11) 0.3474(4) 0.0520(17) Uani 1 1 d . . . . .
C15 C 0.2432(4) 0.5898(11) 0.2873(4) 0.0517(16) Uani 1 1 d . . . . .
H15 H 0.2260 0.4641 0.2525 0.062 Uiso 1 1 calc R U . . .
C14 C 0.1890(4) 0.8056(12) 0.2854(4) 0.0507(16) Uani 1 1 d . . . . .
C7 C 0.0855(4) 1.2126(13) 0.2777(4) 0.066(2) Uani 1 1 d . . . . .
H7 H 0.0507 1.3461 0.2751 0.079 Uiso 1 1 calc R U . . .
C13 C 0.1444(4) 0.9124(12) 0.2196(4) 0.0517(17) Uani 1 1 d . . . . .
C19 C 0.5805(4) 0.3547(13) 0.4373(3) 0.0545(17) Uani 1 1 d . . . . .
H19 H 0.5667 0.3539 0.4770 0.065 Uiso 1 1 calc R U . . .
C2 C 0.2235(4) 0.8063(14) 0.4163(4) 0.065(2) Uani 1 1 d . . . . .
H2 H 0.2579 0.6695 0.4215 0.078 Uiso 1 1 calc R U . . .
C16 C 0.3561(4) 0.3452(12) 0.3240(3) 0.0520(17) Uani 1 1 d . . . . .
H16A H 0.3970 0.4064 0.3082 0.062 Uiso 1 1 calc R U . . .
H16B H 0.3229 0.2297 0.2883 0.062 Uiso 1 1 calc R U . . .
C23 C 0.5690(4) 0.1850(13) 0.3262(3) 0.0571(18) Uani 1 1 d . . . . .
H23 H 0.5462 0.0709 0.2892 0.069 Uiso 1 1 calc R U . . .
C10 C 0.0560(5) 1.1470(17) 0.0895(5) 0.081(2) Uani 1 1 d . . . . .
H10 H 0.0272 1.2224 0.0465 0.097 Uiso 1 1 calc R U . . .
C6 C 0.1291(4) 1.1128(12) 0.3432(4) 0.0564(18) Uani 1 1 d . . . . .
C3 C 0.2146(4) 0.9082(15) 0.4744(4) 0.072(2) Uani 1 1 d . . . . .
H3 H 0.2433 0.8422 0.5186 0.087 Uiso 1 1 calc R U . . .
C17 C 0.3920(4) 0.1995(12) 0.3921(3) 0.0524(17) Uani 1 1 d . . . . .
H17A H 0.3510 0.1140 0.4035 0.063 Uiso 1 1 calc R U . . .
H17B H 0.4175 0.3212 0.4295 0.063 Uiso 1 1 calc R U . . .
C12 C 0.1510(4) 0.8314(14) 0.1552(4) 0.066(2) Uani 1 1 d . . . . .
H12 H 0.1855 0.6986 0.1561 0.080 Uiso 1 1 calc R U . . .
C5 C 0.1207(4) 1.2123(15) 0.4056(5) 0.073(2) Uani 1 1 d . . . . .
H5 H 0.0861 1.3469 0.4026 0.088 Uiso 1 1 calc R U . . .
C4 C 0.1626(5) 1.1117(15) 0.4683(5) 0.079(2) Uani 1 1 d . . . . .
H4 H 0.1570 1.1784 0.5087 0.095 Uiso 1 1 calc R U . . .
C21 C 0.6562(4) 0.5334(14) 0.3747(4) 0.069(2) Uani 1 1 d . . . . .
H21 H 0.6917 0.6554 0.3710 0.083 Uiso 1 1 calc R U . . .
C11 C 0.1089(4) 0.9411(16) 0.0925(4) 0.075(2) Uani 1 1 d . . . . .
H11 H 0.1144 0.8819 0.0513 0.090 Uiso 1 1 calc R U . . .
C22 C 0.6249(4) 0.3563(15) 0.3226(4) 0.069(2) Uani 1 1 d . . . . .
H22 H 0.6413 0.3510 0.2844 0.083 Uiso 1 1 calc R U . . .
C20 C 0.6346(4) 0.5291(14) 0.4326(4) 0.067(2) Uani 1 1 d . . . . .
H20 H 0.6569 0.6456 0.4691 0.081 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
Se1 C18 1.922(6) . ?
Se1 C17 1.961(6) . ?
N1 C15 1.247(8) . ?
N1 C16 1.464(7) . ?
C8 C7 1.379(9) . ?
C8 C9 1.431(9) . ?
C8 C13 1.437(9) . ?
C18 C19 1.374(8) . ?
C18 C23 1.380(8) . ?
C9 C10 1.340(11) . ?
C9 H9 0.9300 . ?
C1 C14 1.413(9) . ?
C1 C2 1.428(9) . ?
C1 C6 1.430(9) . ?
C15 C14 1.488(8) . ?
C15 H15 0.9300 . ?
C14 C13 1.408(9) . ?
C7 C6 1.386(9) . ?
C7 H7 0.9300 . ?
C13 C12 1.422(9) . ?
C19 C20 1.371(9) . ?
C19 H19 0.9300 . ?
C2 C3 1.355(9) . ?
C2 H2 0.9300 . ?
C16 C17 1.506(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C23 C22 1.378(9) . ?
C23 H23 0.9300 . ?
C10 C11 1.428(11) . ?
C10 H10 0.9300 . ?
C6 C5 1.428(9) . ?
C3 C4 1.398(10) . ?
C3 H3 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C12 C11 1.358(10) . ?
C12 H12 0.9300 . ?
C5 C4 1.338(10) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C21 C22 1.364(10) . ?
C21 C20 1.371(10) . ?
C21 H21 0.9300 . ?
C11 H11 0.9300 . ?
C22 H22 0.9300 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 Se1 C17 96.7(3) . . ?
C15 N1 C16 117.0(5) . . ?
C7 C8 C9 122.2(7) . . ?
C7 C8 C13 119.1(7) . . ?
C9 C8 C13 118.7(7) . . ?
C19 C18 C23 118.2(6) . . ?
C19 C18 Se1 121.8(5) . . ?
C23 C18 Se1 120.0(5) . . ?
C10 C9 C8 122.1(8) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C14 C1 C2 123.9(6) . . ?
C14 C1 C6 119.8(7) . . ?
C2 C1 C6 116.3(6) . . ?
N1 C15 C14 124.7(6) . . ?
N1 C15 H15 117.6 . . ?
C14 C15 H15 117.6 . . ?
C13 C14 C1 119.8(6) . . ?
C13 C14 C15 118.4(6) . . ?
C1 C14 C15 121.7(6) . . ?
C8 C7 C6 122.5(7) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C14 C13 C12 123.2(6) . . ?
C14 C13 C8 119.7(6) . . ?
C12 C13 C8 117.1(7) . . ?
C20 C19 C18 120.8(6) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C3 C2 C1 121.7(7) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
N1 C16 C17 111.5(5) . . ?
N1 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N1 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C22 C23 C18 120.7(7) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C9 C10 C11 119.6(8) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C7 C6 C5 120.7(7) . . ?
C7 C6 C1 119.0(7) . . ?
C5 C6 C1 120.2(7) . . ?
C2 C3 C4 120.5(8) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C16 C17 Se1 112.7(4) . . ?
C16 C17 H17A 109.0 . . ?
Se1 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
Se1 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C11 C12 C13 122.3(8) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C4 C5 C6 119.9(7) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C4 C3 121.3(8) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C22 C21 C20 119.0(7) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C12 C11 C10 120.2(8) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C21 C22 C23 120.5(7) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C19 C20 C21 120.7(7) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C8 C9 C10 178.1(7) . . . . ?
C13 C8 C9 C10 -0.9(10) . . . . ?
C16 N1 C15 C14 -177.7(6) . . . . ?
C2 C1 C14 C13 179.4(6) . . . . ?
C6 C1 C14 C13 -0.8(9) . . . . ?
C2 C1 C14 C15 -0.4(10) . . . . ?
C6 C1 C14 C15 179.4(5) . . . . ?
N1 C15 C14 C13 139.6(7) . . . . ?
N1 C15 C14 C1 -40.6(10) . . . . ?
C9 C8 C7 C6 -178.0(6) . . . . ?
C13 C8 C7 C6 1.0(10) . . . . ?
C1 C14 C13 C12 177.5(6) . . . . ?
C15 C14 C13 C12 -2.7(9) . . . . ?
C1 C14 C13 C8 0.3(9) . . . . ?
C15 C14 C13 C8 -179.8(5) . . . . ?
C7 C8 C13 C14 -0.4(9) . . . . ?
C9 C8 C13 C14 178.6(6) . . . . ?
C7 C8 C13 C12 -177.7(6) . . . . ?
C9 C8 C13 C12 1.3(9) . . . . ?
C23 C18 C19 C20 0.8(9) . . . . ?
Se1 C18 C19 C20 -178.2(5) . . . . ?
C14 C1 C2 C3 179.5(7) . . . . ?
C6 C1 C2 C3 -0.4(10) . . . . ?
C15 N1 C16 C17 -131.6(6) . . . . ?
C19 C18 C23 C22 0.9(10) . . . . ?
Se1 C18 C23 C22 179.9(5) . . . . ?
C8 C9 C10 C11 0.3(12) . . . . ?
C8 C7 C6 C5 -179.8(6) . . . . ?
C8 C7 C6 C1 -1.4(10) . . . . ?
C14 C1 C6 C7 1.3(9) . . . . ?
C2 C1 C6 C7 -178.8(6) . . . . ?
C14 C1 C6 C5 179.7(6) . . . . ?
C2 C1 C6 C5 -0.4(9) . . . . ?
C1 C2 C3 C4 0.9(11) . . . . ?
N1 C16 C17 Se1 -170.1(4) . . . . ?
C14 C13 C12 C11 -178.4(7) . . . . ?
C8 C13 C12 C11 -1.2(10) . . . . ?
C7 C6 C5 C4 179.2(7) . . . . ?
C1 C6 C5 C4 0.8(10) . . . . ?
C6 C5 C4 C3 -0.4(12) . . . . ?
C2 C3 C4 C5 -0.4(12) . . . . ?
C13 C12 C11 C10 0.6(11) . . . . ?
C9 C10 C11 C12 -0.1(12) . . . . ?
C20 C21 C22 C23 3.7(11) . . . . ?
C18 C23 C22 C21 -3.2(11) . . . . ?
C18 C19 C20 C21 -0.3(11) . . . . ?
C22 C21 C20 C19 -2.0(11) . . . . ?

_refine_diff_density_max         0.507
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.099

# start validation Reply Form
_vrf_PLAT919_shelxl              
;
RESPONSE:This alert is due to reports the number of reflections with intensities seriously
 effected by the beamstop.
;
# end validation Reply Form

####################################################################### 
# 
# 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_Complex4
_audit_block_doi                 10.5517/ccdc.csd.cc1yzqpb
_database_code_depnum_ccdc_archive 'CCDC 1816993'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H34 Cl Ir N Se, F6 P'
_chemical_formula_sum            'C33 H34 Cl F6 Ir N P Se'
_chemical_formula_weight         896.21

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.2212(6)
_cell_length_b                   13.7085(7)
_cell_length_c                   20.0843(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.1270(10)
_cell_angle_gamma                90
_cell_volume                     3248.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1655
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.833
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_exptl_absorpt_coefficient_mu    5.422
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.164
_exptl_absorpt_correction_T_max  0.207
_exptl_absorpt_process_details   '(SADABS; Bruker; 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            90693
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.819
_diffrn_reflns_theta_max         28.352
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8133
_reflns_number_gt                6926
_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 SMART APEX-II'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    'SHELXT 2014/5 Bruker-AXS, Madison WI'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3.2'
_computing_publication_material  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)+(0.0209P)²+1.1732P] 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         8133
_refine_ls_number_parameters     402
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0192
_refine_ls_wR_factor_ref         0.0431
_refine_ls_wR_factor_gt          0.0404
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.36526(2) 0.61308(2) 0.19865(2) 0.02722(3) Uani 1 1 d . . . . .
Se1 Se 0.23995(2) 0.64763(2) 0.08365(2) 0.03837(6) Uani 1 1 d . . . . .
Cl1 Cl 0.40140(5) 0.78229(5) 0.22460(4) 0.04488(15) Uani 1 1 d . . . . .
P1 P 0.22616(6) 0.25364(6) 0.45315(4) 0.04664(17) Uani 1 1 d . . . . .
F3 F 0.28583(18) 0.29640(17) 0.52619(10) 0.0874(7) Uani 1 1 d . . . . .
F6 F 0.16115(17) 0.17766(16) 0.48918(11) 0.0773(6) Uani 1 1 d . . . . .
N1 N 0.21764(15) 0.63800(14) 0.23165(10) 0.0319(4) Uani 1 1 d . . . . .
F4 F 0.16285(19) 0.20898(19) 0.38074(10) 0.0939(8) Uani 1 1 d . . . . .
C28 C 0.50585(19) 0.55141(19) 0.27673(12) 0.0354(5) Uani 1 1 d . . . . .
C32 C 0.3950(2) 0.45899(18) 0.18755(14) 0.0383(5) Uani 1 1 d . . . . .
C24 C 0.4750(2) 0.51360(19) 0.16083(13) 0.0385(5) Uani 1 1 d . . . . .
C26 C 0.54215(18) 0.57160(19) 0.21476(12) 0.0347(5) Uani 1 1 d . . . . .
C30 C 0.41806(19) 0.48070(18) 0.25978(13) 0.0356(5) Uani 1 1 d . . . . .
C1 C 0.0462(2) 0.60799(19) 0.32682(13) 0.0381(5) Uani 1 1 d . . . . .
C18 C 0.2785(2) 0.7689(2) 0.04661(13) 0.0430(6) Uani 1 1 d . . . . .
C15 C 0.22190(19) 0.66164(19) 0.29347(13) 0.0361(5) Uani 1 1 d . . . . .
H15 H 0.2941 0.6676 0.3231 0.043 Uiso 1 1 calc R U . . .
C13 C 0.12147(19) 0.77352(19) 0.35361(13) 0.0376(5) Uani 1 1 d . . . . .
C12 C 0.2010(2) 0.8491(2) 0.35249(15) 0.0491(7) Uani 1 1 d . . . . .
H12 H 0.2592 0.8380 0.3314 0.059 Uiso 1 1 calc R U . . .
C16 C 0.1082(2) 0.6299(2) 0.17936(14) 0.0437(6) Uani 1 1 d . . . . .
H16A H 0.0476 0.6525 0.1985 0.052 Uiso 1 1 calc R U . . .
H16B H 0.0936 0.5622 0.1658 0.052 Uiso 1 1 calc R U . . .
F5 F 0.2878(3) 0.3285(2) 0.41827(14) 0.1440(13) Uani 1 1 d . . . . .
C8 C 0.0314(2) 0.7943(2) 0.38558(13) 0.0411(6) Uani 1 1 d . . . . .
C14 C 0.12595(19) 0.68100(19) 0.32424(13) 0.0371(5) Uani 1 1 d . . . . .
F2 F 0.32435(19) 0.1782(2) 0.45962(15) 0.1202(10) Uani 1 1 d . . . . .
C29 C 0.5582(2) 0.5904(3) 0.34692(14) 0.0570(8) Uani 1 1 d . . . . .
H29A H 0.5006 0.5997 0.3709 0.086 Uiso 1 1 calc R U . . .
H29B H 0.5941 0.6517 0.3432 0.086 Uiso 1 1 calc R U . . .
H29C H 0.6136 0.5450 0.3719 0.086 Uiso 1 1 calc R U . . .
C2 C 0.0500(2) 0.5115(2) 0.30148(15) 0.0484(7) Uani 1 1 d . . . . .
H2 H 0.1084 0.4942 0.2820 0.058 Uiso 1 1 calc R U . . .
C19 C 0.1993(3) 0.8406(2) 0.02384(14) 0.0514(7) Uani 1 1 d . . . . .
H19 H 0.1258 0.8336 0.0282 0.062 Uiso 1 1 calc R U . . .
F1 F 0.1222(2) 0.32504(19) 0.44819(14) 0.1080(8) Uani 1 1 d . . . . .
C25 C 0.4881(3) 0.5039(3) 0.08869(14) 0.0605(9) Uani 1 1 d . . . . .
H25A H 0.5308 0.5582 0.0787 0.091 Uiso 1 1 calc R U . . .
H25B H 0.4146 0.5030 0.0565 0.091 Uiso 1 1 calc R U . . .
H25C H 0.5273 0.4443 0.0849 0.091 Uiso 1 1 calc R U . . .
C23 C 0.3873(3) 0.7784(3) 0.03960(16) 0.0620(9) Uani 1 1 d . . . . .
H23 H 0.4404 0.7295 0.0555 0.074 Uiso 1 1 calc R U . . .
C6 C -0.0426(2) 0.6313(2) 0.35954(14) 0.0433(6) Uani 1 1 d . . . . .
C31 C 0.3624(2) 0.4343(2) 0.30960(16) 0.0529(7) Uani 1 1 d . . . . .
H31A H 0.4121 0.3860 0.3362 0.079 Uiso 1 1 calc R U . . .
H31B H 0.2930 0.4037 0.2848 0.079 Uiso 1 1 calc R U . . .
H31C H 0.3462 0.4831 0.3399 0.079 Uiso 1 1 calc R U . . .
C33 C 0.3150(3) 0.3834(2) 0.14914(18) 0.0623(9) Uani 1 1 d . . . . .
H33A H 0.2833 0.4049 0.1026 0.094 Uiso 1 1 calc R U . . .
H33B H 0.2553 0.3734 0.1714 0.094 Uiso 1 1 calc R U . . .
H33C H 0.3551 0.3233 0.1487 0.094 Uiso 1 1 calc R U . . .
C9 C 0.0271(2) 0.8883(2) 0.41527(15) 0.0518(7) Uani 1 1 d . . . . .
H9 H -0.0307 0.9023 0.4361 0.062 Uiso 1 1 calc R U . . .
C11 C 0.1930(3) 0.9376(2) 0.38185(18) 0.0586(8) Uani 1 1 d . . . . .
H11 H 0.2460 0.9858 0.3809 0.070 Uiso 1 1 calc R U . . .
C17 C 0.1114(2) 0.6902(2) 0.11765(15) 0.0480(7) Uani 1 1 d . . . . .
H17A H 0.1195 0.7586 0.1302 0.058 Uiso 1 1 calc R U . . .
H17B H 0.0413 0.6821 0.0819 0.058 Uiso 1 1 calc R U . . .
C7 C -0.0472(2) 0.7224(2) 0.38725(14) 0.0451(6) Uani 1 1 d . . . . .
H7 H -0.1053 0.7362 0.4079 0.054 Uiso 1 1 calc R U . . .
C3 C -0.0295(3) 0.4445(2) 0.30510(17) 0.0591(8) Uani 1 1 d . . . . .
H3 H -0.0253 0.3820 0.2880 0.071 Uiso 1 1 calc R U . . .
C10 C 0.1050(3) 0.9569(2) 0.41370(17) 0.0585(8) Uani 1 1 d . . . . .
H10 H 0.1009 1.0175 0.4337 0.070 Uiso 1 1 calc R U . . .
C5 C -0.1237(2) 0.5571(3) 0.36223(17) 0.0567(8) Uani 1 1 d . . . . .
H5 H -0.1810 0.5707 0.3835 0.068 Uiso 1 1 calc R U . . .
C4 C -0.1191(3) 0.4690(3) 0.33489(19) 0.0660(9) Uani 1 1 d . . . . .
H4 H -0.1751 0.4233 0.3354 0.079 Uiso 1 1 calc R U . . .
C21 C 0.3389(4) 0.9333(3) -0.01301(17) 0.0741(10) Uani 1 1 d . . . . .
H21 H 0.3595 0.9893 -0.0329 0.089 Uiso 1 1 calc R U . . .
C27 C 0.6372(2) 0.6381(2) 0.21102(17) 0.0546(8) Uani 1 1 d . . . . .
H27A H 0.7080 0.6040 0.2264 0.082 Uiso 1 1 calc R U . . .
H27B H 0.6374 0.6938 0.2400 0.082 Uiso 1 1 calc R U . . .
H27C H 0.6275 0.6591 0.1643 0.082 Uiso 1 1 calc R U . . .
C20 C 0.2311(3) 0.9243(3) -0.00606(16) 0.0650(9) Uani 1 1 d . . . . .
H20 H 0.1788 0.9740 -0.0213 0.078 Uiso 1 1 calc R U . . .
C22 C 0.4170(3) 0.8609(3) 0.00889(19) 0.0756(11) Uani 1 1 d . . . . .
H22 H 0.4897 0.8672 0.0031 0.091 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 2.1058(17) . ?
Ir1 C32 2.165(2) . ?
Ir1 C28 2.172(2) . ?
Ir1 C26 2.176(2) . ?
Ir1 C24 2.183(2) . ?
Ir1 C30 2.192(2) . ?
Ir1 Cl1 2.3932(6) . ?
Ir1 Se1 2.4614(3) . ?
Se1 C18 1.929(3) . ?
Se1 C17 1.959(2) . ?
P1 F5 1.545(2) . ?
P1 F2 1.564(2) . ?
P1 F3 1.5713(19) . ?
P1 F4 1.582(2) . ?
P1 F1 1.587(2) . ?
P1 F6 1.5937(19) . ?
N1 C15 1.271(3) . ?
N1 C16 1.473(3) . ?
C28 C30 1.420(3) . ?
C28 C26 1.453(3) . ?
C28 C29 1.487(3) . ?
C32 C30 1.435(3) . ?
C32 C24 1.441(3) . ?
C32 C33 1.494(4) . ?
C24 C26 1.420(3) . ?
C24 C25 1.505(3) . ?
C26 C27 1.494(3) . ?
C30 C31 1.491(3) . ?
C1 C14 1.407(3) . ?
C1 C2 1.422(4) . ?
C1 C6 1.444(3) . ?
C18 C19 1.372(4) . ?
C18 C23 1.379(4) . ?
C15 C14 1.485(3) . ?
C15 H15 0.9300 . ?
C13 C14 1.406(3) . ?
C13 C12 1.425(3) . ?
C13 C8 1.440(3) . ?
C12 C11 1.363(4) . ?
C12 H12 0.9300 . ?
C16 C17 1.498(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C8 C7 1.382(4) . ?
C8 C9 1.426(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C2 C3 1.353(4) . ?
C2 H2 0.9300 . ?
C19 C20 1.397(4) . ?
C19 H19 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C23 C22 1.381(4) . ?
C23 H23 0.9300 . ?
C6 C7 1.374(4) . ?
C6 C5 1.431(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C9 C10 1.344(4) . ?
C9 H9 0.9300 . ?
C11 C10 1.412(4) . ?
C11 H11 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C7 H7 0.9300 . ?
C3 C4 1.419(4) . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
C5 C4 1.334(5) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C21 C20 1.366(5) . ?
C21 C22 1.367(5) . ?
C21 H21 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C20 H20 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir1 C32 111.81(9) . . ?
N1 Ir1 C28 114.65(8) . . ?
C32 Ir1 C28 64.67(9) . . ?
N1 Ir1 C26 153.50(8) . . ?
C32 Ir1 C26 64.74(9) . . ?
C28 Ir1 C26 39.03(8) . . ?
N1 Ir1 C24 149.91(9) . . ?
C32 Ir1 C24 38.71(9) . . ?
C28 Ir1 C24 64.29(9) . . ?
C26 Ir1 C24 38.01(9) . . ?
N1 Ir1 C30 96.27(8) . . ?
C32 Ir1 C30 38.46(9) . . ?
C28 Ir1 C30 37.97(9) . . ?
C26 Ir1 C30 64.19(9) . . ?
C24 Ir1 C30 63.89(9) . . ?
N1 Ir1 Cl1 84.19(5) . . ?
C32 Ir1 Cl1 160.36(7) . . ?
C28 Ir1 Cl1 98.84(7) . . ?
C26 Ir1 Cl1 95.80(7) . . ?
C24 Ir1 Cl1 125.88(7) . . ?
C30 Ir1 Cl1 132.06(7) . . ?
N1 Ir1 Se1 83.67(6) . . ?
C32 Ir1 Se1 99.86(7) . . ?
C28 Ir1 Se1 158.98(6) . . ?
C26 Ir1 Se1 122.71(6) . . ?
C24 Ir1 Se1 94.70(7) . . ?
C30 Ir1 Se1 134.84(7) . . ?
Cl1 Ir1 Se1 92.985(19) . . ?
C18 Se1 C17 100.20(12) . . ?
C18 Se1 Ir1 111.89(8) . . ?
C17 Se1 Ir1 95.13(8) . . ?
F5 P1 F2 91.29(19) . . ?
F5 P1 F3 90.75(14) . . ?
F2 P1 F3 90.58(14) . . ?
F5 P1 F4 91.13(14) . . ?
F2 P1 F4 90.06(14) . . ?
F3 P1 F4 178.01(12) . . ?
F5 P1 F1 92.26(18) . . ?
F2 P1 F1 176.42(16) . . ?
F3 P1 F1 89.85(14) . . ?
F4 P1 F1 89.39(14) . . ?
F5 P1 F6 179.13(18) . . ?
F2 P1 F6 89.58(15) . . ?
F3 P1 F6 89.13(11) . . ?
F4 P1 F6 88.99(12) . . ?
F1 P1 F6 86.88(13) . . ?
C15 N1 C16 120.9(2) . . ?
C15 N1 Ir1 121.92(16) . . ?
C16 N1 Ir1 117.14(15) . . ?
C30 C28 C26 107.8(2) . . ?
C30 C28 C29 125.7(2) . . ?
C26 C28 C29 126.3(2) . . ?
C30 C28 Ir1 71.75(13) . . ?
C26 C28 Ir1 70.63(12) . . ?
C29 C28 Ir1 127.44(19) . . ?
C30 C32 C24 107.2(2) . . ?
C30 C32 C33 126.5(3) . . ?
C24 C32 C33 125.7(3) . . ?
C30 C32 Ir1 71.79(14) . . ?
C24 C32 Ir1 71.33(14) . . ?
C33 C32 Ir1 128.70(19) . . ?
C26 C24 C32 108.7(2) . . ?
C26 C24 C25 126.8(2) . . ?
C32 C24 C25 124.4(3) . . ?
C26 C24 Ir1 70.74(13) . . ?
C32 C24 Ir1 69.97(13) . . ?
C25 C24 Ir1 128.31(19) . . ?
C24 C26 C28 107.6(2) . . ?
C24 C26 C27 127.3(2) . . ?
C28 C26 C27 125.1(2) . . ?
C24 C26 Ir1 71.25(13) . . ?
C28 C26 Ir1 70.34(12) . . ?
C27 C26 Ir1 126.07(19) . . ?
C28 C30 C32 108.7(2) . . ?
C28 C30 C31 125.4(2) . . ?
C32 C30 C31 125.9(2) . . ?
C28 C30 Ir1 70.28(13) . . ?
C32 C30 Ir1 69.75(13) . . ?
C31 C30 Ir1 127.60(17) . . ?
C14 C1 C2 124.1(2) . . ?
C14 C1 C6 118.0(2) . . ?
C2 C1 C6 117.9(2) . . ?
C19 C18 C23 120.8(3) . . ?
C19 C18 Se1 121.6(2) . . ?
C23 C18 Se1 117.4(2) . . ?
N1 C15 C14 128.1(2) . . ?
N1 C15 H15 116.0 . . ?
C14 C15 H15 116.0 . . ?
C14 C13 C12 123.2(2) . . ?
C14 C13 C8 118.9(2) . . ?
C12 C13 C8 117.9(2) . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
N1 C16 C17 109.5(2) . . ?
N1 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
N1 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C7 C8 C9 122.1(2) . . ?
C7 C8 C13 119.1(2) . . ?
C9 C8 C13 118.7(3) . . ?
C13 C14 C1 121.5(2) . . ?
C13 C14 C15 117.2(2) . . ?
C1 C14 C15 121.2(2) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C18 C19 C20 118.8(3) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C23 C22 119.7(3) . . ?
C18 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C7 C6 C5 121.9(2) . . ?
C7 C6 C1 120.0(2) . . ?
C5 C6 C1 118.0(3) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C16 C17 Se1 108.67(18) . . ?
C16 C17 H17A 110.0 . . ?
Se1 C17 H17A 110.0 . . ?
C16 C17 H17B 110.0 . . ?
Se1 C17 H17B 110.0 . . ?
H17A C17 H17B 108.3 . . ?
C6 C7 C8 122.4(2) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C20 C21 C22 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C21 C22 C23 119.7(3) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?

_refine_diff_density_max         0.435
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.076

