# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1573144'
_audit_update_record             
;
2017-09-07 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H18 F4 Ir N5 O2.50'
_chemical_formula_weight         720.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   I4(1)/a

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/4, x+3/4, z+3/4'
'y+1/4, -x+1/4, z+1/4'
'-x, -y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+5/4'
'y+3/4, -x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-3/4'
'-y-1/4, x-1/4, -z-1/4'
'x, y-1/2, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z-1/4'
'-y+1/4, x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'

_cell_length_a                   27.885(6)
_cell_length_b                   27.885
_cell_length_c                   12.931(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     10055(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3033
_cell_measurement_theta_min      1.27
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             5568
_exptl_absorpt_coefficient_mu    5.379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9798
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_process_details   SADABS(Sheldrick,1996)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28096
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         26.04
_reflns_number_total             4941
_reflns_number_gt                4212
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97(Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0430P)²+29.0830P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4941
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.005
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir01 Ir 0.359145(6) 0.643136(6) 0.324727(13) 0.01564(8) Uani 1 1 d . . .
F4 F 0.55256(10) 0.62086(11) 0.2921(2) 0.0300(7) Uani 1 1 d . . .
F3 F 0.46120(12) 0.49120(10) 0.4129(3) 0.0377(8) Uani 1 1 d . . .
O1 O 0.35489(12) 0.61903(12) 0.1703(2) 0.0247(7) Uani 1 1 d . . .
F1 F 0.35496(11) 0.65375(13) 0.7443(2) 0.0364(8) Uani 1 1 d . . .
O2 O 0.21820(13) 0.68629(14) 0.2347(3) 0.0335(9) Uani 1 1 d . . .
N1 N 0.28846(14) 0.66838(14) 0.3083(3) 0.0211(9) Uani 1 1 d . . .
N2 N 0.38146(14) 0.70978(14) 0.2877(3) 0.0198(8) Uani 1 1 d . . .
F2 F 0.38726(15) 0.79332(12) 0.5557(3) 0.0505(10) Uani 1 1 d . . .
N4 N 0.38508(15) 0.74109(14) 0.3690(3) 0.0238(9) Uani 1 1 d . . .
N3 N 0.33907(14) 0.57696(14) 0.3710(3) 0.0208(8) Uani 1 1 d . . .
C9 C 0.42436(17) 0.61257(16) 0.3370(3) 0.0176(9) Uani 1 1 d . . .
N5 N 0.37600(14) 0.54645(14) 0.3912(3) 0.0208(8) Uani 1 1 d . . .
C1 C 0.29903(18) 0.55361(18) 0.3914(4) 0.0262(11) Uani 1 1 d . . .
H1 H 0.2684 0.5663 0.3842 0.031 Uiso 1 1 calc R . .
C15 C 0.37707(17) 0.72006(18) 0.4673(4) 0.0226(10) Uani 1 1 d . . .
C6 C 0.50839(18) 0.55536(18) 0.3527(4) 0.0256(11) Uani 1 1 d . . .
H6 H 0.5361 0.5370 0.3570 0.031 Uiso 1 1 calc R . .
C10 C 0.36551(16) 0.67085(17) 0.4665(3) 0.0181(9) Uani 1 1 d . . .
C5 C 0.46406(18) 0.53722(16) 0.3793(4) 0.0232(10) Uani 1 1 d . . .
C19 C 0.31768(18) 0.62006(17) 0.1091(3) 0.0212(10) Uani 1 1 d . . .
C8 C 0.46926(18) 0.63105(17) 0.3115(3) 0.0203(10) Uani 1 1 d . . .
H8 H 0.4722 0.6626 0.2892 0.024 Uiso 1 1 calc R . .
C17 C 0.4012(2) 0.7818(2) 0.2290(4) 0.0330(12) Uani 1 1 d . . .
H17 H 0.4092 0.8064 0.1836 0.040 Uiso 1 1 calc R . .
C2 C 0.3090(2) 0.5074(2) 0.4250(4) 0.0326(13) Uani 1 1 d . . .
H2 H 0.2871 0.4838 0.4438 0.039 Uiso 1 1 calc R . .
C18 C 0.39150(18) 0.73491(18) 0.2034(4) 0.0240(11) Uani 1 1 d . . .
H18 H 0.3919 0.7226 0.1366 0.029 Uiso 1 1 calc R . .
C7 C 0.50926(18) 0.60245(18) 0.3194(3) 0.0216(10) Uani 1 1 d . . .
C27 C 0.2627(2) 0.6953(2) 0.3883(4) 0.0354(13) Uani 1 1 d . . .
H27A H 0.2778 0.7261 0.4010 0.043 Uiso 1 1 calc R . .
H27B H 0.2613 0.6774 0.4525 0.043 Uiso 1 1 calc R . .
C26 C 0.2128(2) 0.7017(2) 0.3423(4) 0.0336(13) Uani 1 1 d . . .
H26B H 0.1895 0.6819 0.3782 0.040 Uiso 1 1 calc R . .
H26A H 0.2027 0.7349 0.3460 0.040 Uiso 1 1 calc R . .
C11 C 0.35864(16) 0.64909(18) 0.5623(4) 0.0206(10) Uani 1 1 d . . .
H11 H 0.3517 0.6165 0.5661 0.025 Uiso 1 1 calc R . .
C12 C 0.36224(17) 0.6761(2) 0.6525(3) 0.0251(11) Uani 1 1 d . . .
C14 C 0.3785(2) 0.74570(19) 0.5585(4) 0.0289(12) Uani 1 1 d . . .
C3 C 0.3584(2) 0.50384(19) 0.4248(4) 0.0310(12) Uani 1 1 d . . .
H3 H 0.3763 0.4772 0.4442 0.037 Uiso 1 1 calc R . .
C13 C 0.37147(19) 0.7244(2) 0.6532(4) 0.0309(12) Uani 1 1 d . . .
H13 H 0.3729 0.7417 0.7145 0.037 Uiso 1 1 calc R . .
C16 C 0.3968(2) 0.78517(18) 0.3343(4) 0.0311(12) Uani 1 1 d . . .
H16 H 0.4010 0.8126 0.3742 0.037 Uiso 1 1 calc R . .
C24 C 0.27269(18) 0.64199(18) 0.1295(4) 0.0236(10) Uani 1 1 d . . .
C25 C 0.26203(18) 0.66552(17) 0.2270(4) 0.0236(10) Uani 1 1 d . . .
C4 C 0.42294(17) 0.56415(16) 0.3711(3) 0.0199(10) Uani 1 1 d . . .
C23 C 0.23600(19) 0.6408(2) 0.0537(4) 0.0298(12) Uani 1 1 d . . .
23 H 0.2066 0.6552 0.0672 0.036 Uiso 1 1 calc R . .
C20 C 0.3230(2) 0.59668(19) 0.0118(4) 0.0279(11) Uani 1 1 d . . .
20 H 0.3517 0.5813 -0.0033 0.034 Uiso 1 1 calc R . .
C22 C 0.2435(2) 0.6184(2) -0.0394(4) 0.0405(15) Uani 1 1 d . . .
22 H 0.2193 0.6182 -0.0890 0.049 Uiso 1 1 calc R . .
C21 C 0.2870(2) 0.5961(2) -0.0599(4) 0.0353(13) Uani 1 1 d . . .
21 H 0.2917 0.5807 -0.1229 0.042 Uiso 1 1 calc R . .
O1W O 0.5000 0.7500 0.5590(12) 0.218(8) Uiso 1 2 d S . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir01 C10 1.997(5) . ?
Ir01 C9 2.015(5) . ?
Ir01 N3 2.019(4) . ?
Ir01 N2 2.017(4) . ?
Ir01 N1 2.104(4) . ?
Ir01 O1 2.111(3) . ?
F4 C7 1.359(6) . ?
F3 C5 1.357(5) . ?
O1 C19 1.305(6) . ?
F1 C12 1.357(5) . ?
O2 C25 1.356(6) . ?
O2 C26 1.463(6) . ?
N1 C25 1.286(6) . ?
N1 C27 1.466(6) . ?
N2 C18 1.326(6) . ?
N2 N4 1.370(5) . ?
F2 C14 1.351(6) . ?
N4 C16 1.348(6) . ?
N4 C15 1.418(6) . ?
N3 C1 1.319(6) . ?
N3 N5 1.361(5) . ?
C9 C8 1.394(7) . ?
C9 C4 1.421(6) . ?
N5 C3 1.357(6) . ?
N5 C4 1.423(6) . ?
C1 C2 1.388(7) . ?
C1 H1 0.9300 . ?
C15 C14 1.379(7) . ?
C15 C10 1.410(7) . ?
C6 C5 1.379(7) . ?
C6 C7 1.382(7) . ?
C6 H6 0.9300 . ?
C10 C11 1.393(6) . ?
C5 C4 1.375(7) . ?
C19 C24 1.420(7) . ?
C19 C20 1.425(7) . ?
C8 C7 1.375(7) . ?
C8 H8 0.9300 . ?
C17 C16 1.371(7) . ?
C17 C18 1.376(7) . ?
C17 H17 0.9300 . ?
C2 C3 1.379(8) . ?
C2 H2 0.9300 . ?
C18 H18 0.9300 . ?
C27 C26 1.523(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26A 0.9700 . ?
C11 C12 1.392(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(8) . ?
C14 C13 1.376(7) . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C16 H16 0.9300 . ?
C24 C23 1.417(7) . ?
C24 C25 1.452(7) . ?
C23 C22 1.372(8) . ?
C23 23 0.9300 . ?
C20 C21 1.365(7) . ?
C20 20 0.9300 . ?
C22 C21 1.391(9) . ?
C22 22 0.9300 . ?
C21 21 0.9300 . ?
O1W O1W 1.71(3) 10_577 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 Ir01 C9 90.63(17) . . ?
C10 Ir01 N3 96.10(17) . . ?
C9 Ir01 N3 80.81(17) . . ?
C10 Ir01 N2 80.42(17) . . ?
C9 Ir01 N2 97.47(17) . . ?
N3 Ir01 N2 176.13(15) . . ?
C10 Ir01 N1 92.67(17) . . ?
C9 Ir01 N1 174.41(17) . . ?
N3 Ir01 N1 94.36(16) . . ?
N2 Ir01 N1 87.52(15) . . ?
C10 Ir01 O1 175.35(17) . . ?
C9 Ir01 O1 89.47(15) . . ?
N3 Ir01 O1 88.50(15) . . ?
N2 Ir01 O1 94.96(14) . . ?
N1 Ir01 O1 87.61(14) . . ?
C19 O1 Ir01 127.7(3) . . ?
C25 O2 C26 106.7(4) . . ?
C25 N1 C27 109.1(4) . . ?
C25 N1 Ir01 126.8(3) . . ?
C27 N1 Ir01 124.0(3) . . ?
C18 N2 N4 106.2(4) . . ?
C18 N2 Ir01 138.3(3) . . ?
N4 N2 Ir01 115.3(3) . . ?
C16 N4 N2 110.1(4) . . ?
C16 N4 C15 135.5(4) . . ?
N2 N4 C15 114.4(4) . . ?
C1 N3 N5 107.1(4) . . ?
C1 N3 Ir01 138.2(4) . . ?
N5 N3 Ir01 114.7(3) . . ?
C8 C9 C4 116.7(4) . . ?
C8 C9 Ir01 129.5(4) . . ?
C4 C9 Ir01 113.7(3) . . ?
C3 N5 N3 109.6(4) . . ?
C3 N5 C4 134.0(4) . . ?
N3 N5 C4 116.4(4) . . ?
N3 C1 C2 110.5(5) . . ?
N3 C1 H1 124.7 . . ?
C2 C1 H1 124.7 . . ?
C14 C15 C10 121.2(4) . . ?
C14 C15 N4 123.2(5) . . ?
C10 C15 N4 115.6(4) . . ?
C5 C6 C7 116.2(5) . . ?
C5 C6 H6 121.9 . . ?
C7 C6 H6 121.9 . . ?
C11 C10 C15 116.6(4) . . ?
C11 C10 Ir01 129.5(4) . . ?
C15 C10 Ir01 113.8(3) . . ?
F3 C5 C4 119.5(4) . . ?
F3 C5 C6 118.6(4) . . ?
C4 C5 C6 121.9(4) . . ?
O1 C19 C24 126.8(4) . . ?
O1 C19 C20 116.3(5) . . ?
C24 C19 C20 116.9(4) . . ?
C7 C8 C9 119.8(4) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C16 C17 C18 106.6(5) . . ?
C16 C17 H17 126.7 . . ?
C18 C17 H17 126.7 . . ?
C3 C2 C1 105.5(5) . . ?
C3 C2 H2 127.3 . . ?
C1 C2 H2 127.3 . . ?
N2 C18 C17 110.3(4) . . ?
N2 C18 H18 124.9 . . ?
C17 C18 H18 124.9 . . ?
F4 C7 C8 118.8(4) . . ?
F4 C7 C6 117.1(4) . . ?
C8 C7 C6 124.1(5) . . ?
N1 C27 C26 103.4(4) . . ?
N1 C27 H27A 111.1 . . ?
C26 C27 H27A 111.1 . . ?
N1 C27 H27B 111.1 . . ?
C26 C27 H27B 111.1 . . ?
H27A C27 H27B 109.0 . . ?
O2 C26 C27 104.1(4) . . ?
O2 C26 H26B 110.9 . . ?
C27 C26 H26B 110.9 . . ?
O2 C26 H26A 110.9 . . ?
C27 C26 H26A 110.9 . . ?
H26B C26 H26A 109.0 . . ?
C12 C11 C10 119.9(5) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
F1 C12 C13 118.3(4) . . ?
F1 C12 C11 118.2(5) . . ?
C13 C12 C11 123.5(5) . . ?
F2 C14 C13 118.4(4) . . ?
F2 C14 C15 119.4(4) . . ?
C13 C14 C15 122.2(5) . . ?
N5 C3 C2 107.4(5) . . ?
N5 C3 H3 126.3 . . ?
C2 C3 H3 126.3 . . ?
C12 C13 C14 116.4(5) . . ?
C12 C13 H13 121.8 . . ?
C14 C13 H13 121.8 . . ?
N4 C16 C17 106.9(5) . . ?
N4 C16 H16 126.6 . . ?
C17 C16 H16 126.6 . . ?
C23 C24 C19 119.9(5) . . ?
C23 C24 C25 117.6(5) . . ?
C19 C24 C25 122.5(4) . . ?
N1 C25 O2 115.5(4) . . ?
N1 C25 C24 128.3(5) . . ?
O2 C25 C24 116.2(4) . . ?
C5 C4 C9 121.3(4) . . ?
C5 C4 N5 124.3(4) . . ?
C9 C4 N5 114.3(4) . . ?
C22 C23 C24 120.6(5) . . ?
C22 C23 23 119.7 . . ?
C24 C23 23 119.7 . . ?
C21 C20 C19 122.0(5) . . ?
C21 C20 20 119.0 . . ?
C19 C20 20 119.0 . . ?
C23 C22 C21 120.2(5) . . ?
C23 C22 22 119.9 . . ?
C21 C22 22 119.9 . . ?
C20 C21 C22 120.4(5) . . ?
C20 C21 21 119.8 . . ?
C22 C21 21 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.04
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         2.147
_refine_diff_density_min         -1.218
_refine_diff_density_rms         0.299
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1573147'
_audit_update_record             
;
2017-09-07 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H28 F6 Ir N5 O2'
_chemical_formula_weight         832.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0470(8)
_cell_length_b                   11.1160(8)
_cell_length_c                   16.2570(13)
_cell_angle_alpha                98.7120(13)
_cell_angle_beta                 104.8530(14)
_cell_angle_gamma                98.3260(14)
_cell_volume                     1702.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3033
_cell_measurement_theta_min      1.27
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    3.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4739
_exptl_absorpt_correction_T_max  0.5677
_exptl_absorpt_process_details   SADABS(Sheldrick,1996)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12614
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         28.37
_reflns_number_total             8445
_reflns_number_gt                6682
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97(Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1277P)²+7.2222P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8445
_refine_ls_number_parameters     428
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.2145
_refine_ls_wR_factor_gt          0.1964
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.087
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7834(12) 0.1472(13) 0.3490(12) 0.087(5) Uani 1 1 d . . .
H1A H 0.7849 0.1891 0.4062 0.105 Uiso 1 1 calc R . .
H1B H 0.8254 0.2062 0.3203 0.105 Uiso 1 1 calc R . .
C2 C 0.856(2) 0.0388(17) 0.3541(13) 0.098(5) Uani 1 1 d U . .
H2A H 0.9289 0.0461 0.3248 0.118 Uiso 1 1 calc R . .
H2B H 0.8994 0.0360 0.4143 0.118 Uiso 1 1 calc R . .
C3 C 0.6327(13) -0.0302(11) 0.2806(8) 0.059(3) Uani 1 1 d . . .
C4 C 0.5141(12) -0.1272(10) 0.2335(7) 0.051(2) Uani 1 1 d . . .
C5 C 0.5355(15) -0.2523(11) 0.2219(8) 0.060(3) Uani 1 1 d . . .
H5 H 0.6248 -0.2671 0.2457 0.072 Uiso 1 1 calc R . .
C6 C 0.4329(17) -0.3495(12) 0.1781(8) 0.068(3) Uani 1 1 d . . .
H6 H 0.4504 -0.4298 0.1712 0.082 Uiso 1 1 calc R . .
C7 C 0.2992(18) -0.3263(13) 0.1433(10) 0.076(4) Uani 1 1 d . . .
H7 H 0.2266 -0.3922 0.1126 0.091 Uiso 1 1 calc R . .
C8 C 0.2728(15) -0.2085(12) 0.1534(9) 0.068(3) Uani 1 1 d . . .
H8 H 0.1822 -0.1968 0.1295 0.082 Uiso 1 1 calc R . .
C9 C 0.3785(11) -0.1034(9) 0.1991(7) 0.049(2) Uani 1 1 d . . .
C10 C 0.4006(12) 0.1237(12) 0.4357(8) 0.057(3) Uani 1 1 d . . .
C11 C 0.4453(14) 0.1795(15) 0.5206(8) 0.071(4) Uani 1 1 d . . .
H11 H 0.4167 0.1511 0.5655 0.085 Uiso 1 1 calc R . .
C12 C 0.5405(14) 0.2858(13) 0.5286(7) 0.065(3) Uani 1 1 d . . .
C13 C 0.6238(10) 0.3783(9) 0.4104(6) 0.043(2) Uani 1 1 d . . .
C14 C 0.5916(10) 0.3460(9) 0.3198(6) 0.0409(19) Uani 1 1 d . . .
C15 C 0.6590(12) 0.4283(10) 0.2808(6) 0.051(2) Uani 1 1 d . . .
H15 H 0.6374 0.4124 0.2206 0.061 Uiso 1 1 calc R . .
C16 C 0.7557(12) 0.5316(11) 0.3265(7) 0.055(2) Uani 1 1 d . . .
H16 H 0.8004 0.5833 0.2977 0.066 Uiso 1 1 calc R . .
C17 C 0.7865(11) 0.5587(10) 0.4160(7) 0.053(2) Uani 1 1 d . . .
C18 C 0.7206(11) 0.4823(10) 0.4591(7) 0.052(2) Uani 1 1 d . . .
H18 H 0.7408 0.5002 0.5193 0.062 Uiso 1 1 calc R . .
C19 C 0.2954(16) 0.0057(14) 0.3943(10) 0.078(4) Uani 1 1 d . . .
H19A H 0.2071 0.0252 0.3661 0.117 Uiso 1 1 calc R . .
H19B H 0.2837 -0.0406 0.4380 0.117 Uiso 1 1 calc R . .
H19C H 0.3281 -0.0428 0.3522 0.117 Uiso 1 1 calc R . .
C20 C 0.621(2) 0.3786(16) 0.6077(8) 0.093(5) Uani 1 1 d . . .
H20A H 0.7129 0.3604 0.6287 0.140 Uiso 1 1 calc R . .
H20B H 0.5731 0.3758 0.6516 0.140 Uiso 1 1 calc R . .
H20C H 0.6296 0.4599 0.5940 0.140 Uiso 1 1 calc R . .
C21 C 0.8974(14) 0.6663(13) 0.4654(8) 0.068(3) Uani 1 1 d . . .
C22 C 0.5422(12) 0.1747(10) 0.0867(7) 0.051(2) Uani 1 1 d . . .
C23 C 0.4956(14) 0.2264(13) 0.0139(8) 0.065(3) Uani 1 1 d . . .
H23 H 0.5321 0.2239 -0.0333 0.078 Uiso 1 1 calc R . .
C24 C 0.3845(13) 0.2824(13) 0.0251(7) 0.060(3) Uani 1 1 d . . .
C25 C 0.2719(10) 0.2929(9) 0.1491(6) 0.043(2) Uani 1 1 d . . .
C26 C 0.3016(10) 0.2657(8) 0.2331(6) 0.0392(18) Uani 1 1 d . . .
C27 C 0.2108(12) 0.2946(10) 0.2814(6) 0.050(2) Uani 1 1 d . . .
H27 H 0.2250 0.2748 0.3362 0.060 Uiso 1 1 calc R . .
C28 C 0.1020(11) 0.3507(11) 0.2510(8) 0.056(3) Uani 1 1 d . . .
H28 H 0.0461 0.3730 0.2862 0.067 Uiso 1 1 calc R . .
C29 C 0.0737(11) 0.3751(11) 0.1672(7) 0.053(2) Uani 1 1 d . . .
C30 C 0.1594(10) 0.3474(10) 0.1161(7) 0.049(2) Uani 1 1 d . . .
H30 H 0.1422 0.3649 0.0606 0.059 Uiso 1 1 calc R . .
C31 C 0.6630(15) 0.1081(14) 0.1081(10) 0.074(4) Uani 1 1 d . . .
H31A H 0.7056 0.1262 0.1698 0.110 Uiso 1 1 calc R . .
H31B H 0.7311 0.1353 0.0795 0.110 Uiso 1 1 calc R . .
H31C H 0.6293 0.0204 0.0887 0.110 Uiso 1 1 calc R . .
C32 C 0.3003(18) 0.3525(19) -0.0342(9) 0.092(5) Uani 1 1 d . . .
H32A H 0.2042 0.3100 -0.0547 0.138 Uiso 1 1 calc R . .
H32B H 0.3373 0.3578 -0.0827 0.138 Uiso 1 1 calc R . .
H32C H 0.3056 0.4345 -0.0031 0.138 Uiso 1 1 calc R . .
C33 C -0.0473(16) 0.4349(17) 0.1326(11) 0.081(4) Uani 1 1 d . . .
N1 N 0.6391(9) 0.0866(9) 0.2967(6) 0.051(2) Uani 1 1 d . . .
N2 N 0.4662(9) 0.1898(8) 0.3900(6) 0.0473(19) Uani 1 1 d . . .
N3 N 0.5512(9) 0.2914(8) 0.4480(5) 0.0481(19) Uani 1 1 d . . .
N4 N 0.4655(8) 0.1967(7) 0.1403(5) 0.0419(17) Uani 1 1 d . . .
N5 N 0.3678(9) 0.2628(8) 0.1024(5) 0.0454(18) Uani 1 1 d . . .
O1 O 0.7538(11) -0.0709(10) 0.3133(8) 0.091(3) Uani 1 1 d . . .
O2 O 0.3402(8) 0.0044(7) 0.2088(6) 0.061(2) Uani 1 1 d . . .
F1 F 0.9231(15) 0.6817(13) 0.5482(9) 0.140(4) Uani 1 1 d U . .
F2 F 1.0178(13) 0.6693(12) 0.4541(9) 0.128(4) Uani 1 1 d U . .
F3 F 0.8701(17) 0.7725(15) 0.4529(11) 0.163(5) Uani 1 1 d U . .
F4 F -0.0346(17) 0.5475(16) 0.1835(11) 0.160(5) Uani 1 1 d U . .
F5 F -0.0472(14) 0.4807(13) 0.0656(9) 0.129(4) Uani 1 1 d U . .
F6 F -0.1604(14) 0.3956(13) 0.1477(10) 0.139(4) Uani 1 1 d U . .
Ir1 Ir 0.46791(4) 0.18194(3) 0.26470(2) 0.04194(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
C1 N1 1.480(14) . ?
C1 C2 1.50(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 O1 1.42(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.274(15) . ?
C3 O1 1.367(14) . ?
C3 C4 1.442(17) . ?
C4 C9 1.413(16) . ?
C4 C5 1.431(17) . ?
C5 C6 1.344(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.40(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.37(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.421(15) . ?
C8 H8 0.9300 . ?
C9 O2 1.310(13) . ?
C10 N2 1.343(13) . ?
C10 C11 1.354(19) . ?
C10 C19 1.502(19) . ?
C11 C12 1.375(19) . ?
C11 H11 0.9300 . ?
C12 N3 1.353(13) . ?
C12 C20 1.482(19) . ?
C13 C18 1.383(14) . ?
C13 C14 1.401(13) . ?
C13 N3 1.430(13) . ?
C14 C15 1.382(14) . ?
C14 Ir1 1.988(10) . ?
C15 C16 1.365(15) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(16) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(16) . ?
C17 C21 1.477(17) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 F2 1.266(17) . ?
C21 F1 1.283(18) . ?
C21 F3 1.284(19) . ?
C22 N4 1.321(13) . ?
C22 C23 1.397(17) . ?
C22 C31 1.505(16) . ?
C23 C24 1.391(17) . ?
C23 H23 0.9300 . ?
C24 N5 1.355(13) . ?
C24 C32 1.500(18) . ?
C25 C30 1.385(14) . ?
C25 C26 1.410(12) . ?
C25 N5 1.417(12) . ?
C26 C27 1.389(14) . ?
C26 Ir1 2.020(10) . ?
C27 C28 1.358(16) . ?
C27 H27 0.9300 . ?
C28 C29 1.396(16) . ?
C28 H28 0.9300 . ?
C29 C30 1.376(15) . ?
C29 C33 1.493(17) . ?
C30 H30 0.9300 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 F6 1.255(18) . ?
C33 F5 1.269(18) . ?
C33 F4 1.36(2) . ?
N1 Ir1 2.142(9) . ?
N2 N3 1.370(12) . ?
N2 Ir1 2.031(9) . ?
N4 N5 1.385(11) . ?
N4 Ir1 2.048(8) . ?
O2 Ir1 2.119(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 101.9(12) . . ?
N1 C1 H1A 111.4 . . ?
C2 C1 H1A 111.4 . . ?
N1 C1 H1B 111.4 . . ?
C2 C1 H1B 111.4 . . ?
H1A C1 H1B 109.3 . . ?
O1 C2 C1 107.8(13) . . ?
O1 C2 H2A 110.2 . . ?
C1 C2 H2A 110.2 . . ?
O1 C2 H2B 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
N1 C3 O1 116.3(11) . . ?
N1 C3 C4 129.0(10) . . ?
O1 C3 C4 114.7(10) . . ?
C9 C4 C5 119.1(11) . . ?
C9 C4 C3 122.7(10) . . ?
C5 C4 C3 118.2(11) . . ?
C6 C5 C4 123.1(13) . . ?
C6 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C5 C6 C7 117.9(12) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C8 C7 C6 121.3(13) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 122.5(13) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
O2 C9 C4 126.4(9) . . ?
O2 C9 C8 117.4(11) . . ?
C4 C9 C8 116.1(10) . . ?
N2 C10 C11 109.6(11) . . ?
N2 C10 C19 122.5(11) . . ?
C11 C10 C19 127.9(11) . . ?
C10 C11 C12 107.7(11) . . ?
C10 C11 H11 126.1 . . ?
C12 C11 H11 126.1 . . ?
N3 C12 C11 106.5(11) . . ?
N3 C12 C20 124.3(12) . . ?
C11 C12 C20 129.2(11) . . ?
C18 C13 C14 123.1(9) . . ?
C18 C13 N3 123.1(9) . . ?
C14 C13 N3 113.8(9) . . ?
C15 C14 C13 115.6(9) . . ?
C15 C14 Ir1 128.1(7) . . ?
C13 C14 Ir1 116.1(7) . . ?
C16 C15 C14 123.2(9) . . ?
C16 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
C15 C16 C17 119.3(10) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 120.6(10) . . ?
C18 C17 C21 120.3(10) . . ?
C16 C17 C21 119.0(11) . . ?
C17 C18 C13 118.2(9) . . ?
C17 C18 H18 120.9 . . ?
C13 C18 H18 120.9 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
F2 C21 F1 103.1(13) . . ?
F2 C21 F3 103.4(15) . . ?
F1 C21 F3 100.7(14) . . ?
F2 C21 C17 117.4(12) . . ?
F1 C21 C17 114.9(13) . . ?
F3 C21 C17 115.2(13) . . ?
N4 C22 C23 109.3(9) . . ?
N4 C22 C31 122.1(10) . . ?
C23 C22 C31 128.6(10) . . ?
C24 C23 C22 107.4(10) . . ?
C24 C23 H23 126.3 . . ?
C22 C23 H23 126.3 . . ?
N5 C24 C23 105.8(10) . . ?
N5 C24 C32 126.0(10) . . ?
C23 C24 C32 128.1(11) . . ?
C30 C25 C26 122.2(9) . . ?
C30 C25 N5 123.0(8) . . ?
C26 C25 N5 114.7(8) . . ?
C27 C26 C25 116.7(9) . . ?
C27 C26 Ir1 128.6(7) . . ?
C25 C26 Ir1 114.7(7) . . ?
C28 C27 C26 121.9(9) . . ?
C28 C27 H27 119.1 . . ?
C26 C27 H27 119.1 . . ?
C27 C28 C29 120.3(10) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C30 C29 C28 120.2(10) . . ?
C30 C29 C33 119.1(10) . . ?
C28 C29 C33 120.7(10) . . ?
C29 C30 C25 118.6(9) . . ?
C29 C30 H30 120.7 . . ?
C25 C30 H30 120.7 . . ?
C22 C31 H31A 109.5 . . ?
C22 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C22 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C24 C32 H32A 109.5 . . ?
C24 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C24 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
F6 C33 F5 120.8(16) . . ?
F6 C33 F4 91.1(13) . . ?
F5 C33 F4 93.2(14) . . ?
F6 C33 C29 116.4(13) . . ?
F5 C33 C29 116.7(11) . . ?
F4 C33 C29 110.7(15) . . ?
C3 N1 C1 108.7(10) . . ?
C3 N1 Ir1 126.6(8) . . ?
C1 N1 Ir1 124.4(8) . . ?
C10 N2 N3 106.4(9) . . ?
C10 N2 Ir1 138.1(8) . . ?
N3 N2 Ir1 115.4(6) . . ?
C12 N3 N2 109.6(9) . . ?
C12 N3 C13 135.5(10) . . ?
N2 N3 C13 114.8(8) . . ?
C22 N4 N5 107.1(8) . . ?
C22 N4 Ir1 138.4(7) . . ?
N5 N4 Ir1 113.8(6) . . ?
C24 N5 N4 110.4(8) . . ?
C24 N5 C25 133.6(9) . . ?
N4 N5 C25 116.0(8) . . ?
C3 O1 C2 105.1(11) . . ?
C9 O2 Ir1 128.5(7) . . ?
C14 Ir1 C26 90.0(4) . . ?
C14 Ir1 N2 79.5(4) . . ?
C26 Ir1 N2 94.5(3) . . ?
C14 Ir1 N4 95.3(3) . . ?
C26 Ir1 N4 80.2(3) . . ?
N2 Ir1 N4 172.7(3) . . ?
C14 Ir1 O2 178.2(3) . . ?
C26 Ir1 O2 91.6(3) . . ?
N2 Ir1 O2 99.4(3) . . ?
N4 Ir1 O2 85.8(3) . . ?
C14 Ir1 N1 92.1(4) . . ?
C26 Ir1 N1 177.9(3) . . ?
N2 Ir1 N1 85.5(3) . . ?
N4 Ir1 N1 99.9(3) . . ?
O2 Ir1 N1 86.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O1 -4(2) . . . . ?
N1 C3 C4 C9 -2(2) . . . . ?
O1 C3 C4 C9 176.5(11) . . . . ?
N1 C3 C4 C5 178.0(13) . . . . ?
O1 C3 C4 C5 -3.3(17) . . . . ?
C9 C4 C5 C6 1.2(18) . . . . ?
C3 C4 C5 C6 -179.0(11) . . . . ?
C4 C5 C6 C7 -1(2) . . . . ?
C5 C6 C7 C8 0(2) . . . . ?
C6 C7 C8 C9 0(2) . . . . ?
C5 C4 C9 O2 175.5(11) . . . . ?
C3 C4 C9 O2 -4.3(18) . . . . ?
C5 C4 C9 C8 -1.0(16) . . . . ?
C3 C4 C9 C8 179.2(11) . . . . ?
C7 C8 C9 O2 -176.5(13) . . . . ?
C7 C8 C9 C4 0.3(19) . . . . ?
N2 C10 C11 C12 1.1(16) . . . . ?
C19 C10 C11 C12 -179.4(13) . . . . ?
C10 C11 C12 N3 -0.1(16) . . . . ?
C10 C11 C12 C20 -179.1(16) . . . . ?
C18 C13 C14 C15 -2.6(15) . . . . ?
N3 C13 C14 C15 179.5(9) . . . . ?
C18 C13 C14 Ir1 172.5(8) . . . . ?
N3 C13 C14 Ir1 -5.4(11) . . . . ?
C13 C14 C15 C16 2.9(16) . . . . ?
Ir1 C14 C15 C16 -171.5(9) . . . . ?
C14 C15 C16 C17 -1.7(18) . . . . ?
C15 C16 C17 C18 0.1(18) . . . . ?
C15 C16 C17 C21 176.3(11) . . . . ?
C16 C17 C18 C13 0.2(17) . . . . ?
C21 C17 C18 C13 -175.9(11) . . . . ?
C14 C13 C18 C17 1.1(16) . . . . ?
N3 C13 C18 C17 178.8(10) . . . . ?
C18 C17 C21 F2 120.3(15) . . . . ?
C16 C17 C21 F2 -55.9(18) . . . . ?
C18 C17 C21 F1 -1.1(19) . . . . ?
C16 C17 C21 F1 -177.3(13) . . . . ?
C18 C17 C21 F3 -117.6(16) . . . . ?
C16 C17 C21 F3 66.3(18) . . . . ?
N4 C22 C23 C24 0.0(15) . . . . ?
C31 C22 C23 C24 -177.5(13) . . . . ?
C22 C23 C24 N5 -0.2(15) . . . . ?
C22 C23 C24 C32 178.8(15) . . . . ?
C30 C25 C26 C27 1.0(14) . . . . ?
N5 C25 C26 C27 179.6(9) . . . . ?
C30 C25 C26 Ir1 178.3(8) . . . . ?
N5 C25 C26 Ir1 -3.1(11) . . . . ?
C25 C26 C27 C28 -2.6(16) . . . . ?
Ir1 C26 C27 C28 -179.5(9) . . . . ?
C26 C27 C28 C29 3.5(18) . . . . ?
C27 C28 C29 C30 -2.8(18) . . . . ?
C27 C28 C29 C33 178.9(13) . . . . ?
C28 C29 C30 C25 1.2(17) . . . . ?
C33 C29 C30 C25 179.5(12) . . . . ?
C26 C25 C30 C29 -0.4(16) . . . . ?
N5 C25 C30 C29 -178.8(10) . . . . ?
C30 C29 C33 F6 138.4(15) . . . . ?
C28 C29 C33 F6 -43(2) . . . . ?
C30 C29 C33 F5 -15(2) . . . . ?
C28 C29 C33 F5 163.7(15) . . . . ?
C30 C29 C33 F4 -119.4(14) . . . . ?
C28 C29 C33 F4 58.8(17) . . . . ?
O1 C3 N1 C1 0.0(17) . . . . ?
C4 C3 N1 C1 178.6(14) . . . . ?
O1 C3 N1 Ir1 -174.9(9) . . . . ?
C4 C3 N1 Ir1 3.8(19) . . . . ?
C2 C1 N1 C3 2.7(18) . . . . ?
C2 C1 N1 Ir1 177.7(11) . . . . ?
C11 C10 N2 N3 -1.7(13) . . . . ?
C19 C10 N2 N3 178.8(11) . . . . ?
C11 C10 N2 Ir1 -179.3(9) . . . . ?
C19 C10 N2 Ir1 1.1(19) . . . . ?
C11 C12 N3 N2 -0.9(14) . . . . ?
C20 C12 N3 N2 178.1(14) . . . . ?
C11 C12 N3 C13 176.1(12) . . . . ?
C20 C12 N3 C13 -5(2) . . . . ?
C10 N2 N3 C12 1.6(12) . . . . ?
Ir1 N2 N3 C12 179.9(8) . . . . ?
C10 N2 N3 C13 -176.1(9) . . . . ?
Ir1 N2 N3 C13 2.2(10) . . . . ?
C18 C13 N3 C12 7.3(19) . . . . ?
C14 C13 N3 C12 -174.9(12) . . . . ?
C18 C13 N3 N2 -175.9(9) . . . . ?
C14 C13 N3 N2 2.0(12) . . . . ?
C23 C22 N4 N5 0.2(12) . . . . ?
C31 C22 N4 N5 177.9(11) . . . . ?
C23 C22 N4 Ir1 -169.3(9) . . . . ?
C31 C22 N4 Ir1 8.4(18) . . . . ?
C23 C24 N5 N4 0.3(14) . . . . ?
C32 C24 N5 N4 -178.8(14) . . . . ?
C23 C24 N5 C25 -178.0(11) . . . . ?
C32 C24 N5 C25 3(2) . . . . ?
C22 N4 N5 C24 -0.3(12) . . . . ?
Ir1 N4 N5 C24 172.1(8) . . . . ?
C22 N4 N5 C25 178.3(9) . . . . ?
Ir1 N4 N5 C25 -9.3(10) . . . . ?
C30 C25 N5 C24 4.9(18) . . . . ?
C26 C25 N5 C24 -173.6(12) . . . . ?
C30 C25 N5 N4 -173.3(9) . . . . ?
C26 C25 N5 N4 8.2(12) . . . . ?
N1 C3 O1 C2 -2.9(18) . . . . ?
C4 C3 O1 C2 178.3(13) . . . . ?
C1 C2 O1 C3 4(2) . . . . ?
C4 C9 O2 Ir1 8.2(16) . . . . ?
C8 C9 O2 Ir1 -175.4(8) . . . . ?
C15 C14 Ir1 C26 -86.0(10) . . . . ?
C13 C14 Ir1 C26 99.7(8) . . . . ?
C15 C14 Ir1 N2 179.4(10) . . . . ?
C13 C14 Ir1 N2 5.1(7) . . . . ?
C15 C14 Ir1 N4 -5.8(10) . . . . ?
C13 C14 Ir1 N4 179.9(7) . . . . ?
C15 C14 Ir1 O2 125(11) . . . . ?
C13 C14 Ir1 O2 -50(11) . . . . ?
C15 C14 Ir1 N1 94.3(10) . . . . ?
C13 C14 Ir1 N1 -80.0(8) . . . . ?
C27 C26 Ir1 C14 -89.0(9) . . . . ?
C25 C26 Ir1 C14 94.0(7) . . . . ?
C27 C26 Ir1 N2 -9.5(9) . . . . ?
C25 C26 Ir1 N2 173.5(7) . . . . ?
C27 C26 Ir1 N4 175.5(9) . . . . ?
C25 C26 Ir1 N4 -1.4(7) . . . . ?
C27 C26 Ir1 O2 90.1(9) . . . . ?
C25 C26 Ir1 O2 -86.9(7) . . . . ?
C27 C26 Ir1 N1 83(9) . . . . ?
C25 C26 Ir1 N1 -94(9) . . . . ?
C10 N2 Ir1 C14 173.6(12) . . . . ?
N3 N2 Ir1 C14 -4.0(7) . . . . ?
C10 N2 Ir1 C26 84.4(11) . . . . ?
N3 N2 Ir1 C26 -93.1(7) . . . . ?
C10 N2 Ir1 N4 128(2) . . . . ?
N3 N2 Ir1 N4 -50(3) . . . . ?
C10 N2 Ir1 O2 -7.9(12) . . . . ?
N3 N2 Ir1 O2 174.5(7) . . . . ?
C10 N2 Ir1 N1 -93.5(11) . . . . ?
N3 N2 Ir1 N1 89.0(7) . . . . ?
C22 N4 Ir1 C14 85.7(11) . . . . ?
N5 N4 Ir1 C14 -83.3(6) . . . . ?
C22 N4 Ir1 C26 174.8(11) . . . . ?
N5 N4 Ir1 C26 5.8(6) . . . . ?
C22 N4 Ir1 N2 131(2) . . . . ?
N5 N4 Ir1 N2 -38(3) . . . . ?
C22 N4 Ir1 O2 -92.9(11) . . . . ?
N5 N4 Ir1 O2 98.1(6) . . . . ?
C22 N4 Ir1 N1 -7.4(11) . . . . ?
N5 N4 Ir1 N1 -176.4(6) . . . . ?
C9 O2 Ir1 C14 -36(11) . . . . ?
C9 O2 Ir1 C26 175.1(10) . . . . ?
C9 O2 Ir1 N2 -90.0(10) . . . . ?
C9 O2 Ir1 N4 95.0(10) . . . . ?
C9 O2 Ir1 N1 -5.2(9) . . . . ?
C3 N1 Ir1 C14 178.6(10) . . . . ?
C1 N1 Ir1 C14 4.5(12) . . . . ?
C3 N1 Ir1 C26 7(9) . . . . ?
C1 N1 Ir1 C26 -167(9) . . . . ?
C3 N1 Ir1 N2 99.2(11) . . . . ?
C1 N1 Ir1 N2 -74.9(12) . . . . ?
C3 N1 Ir1 N4 -85.6(11) . . . . ?
C1 N1 Ir1 N4 100.3(12) . . . . ?
C3 N1 Ir1 O2 -0.5(10) . . . . ?
C1 N1 Ir1 O2 -174.6(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         7.167
_refine_diff_density_min         -1.072
_refine_diff_density_rms         0.248
####################################################################### 
# 
# 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_cc
_database_code_depnum_ccdc_archive 'CCDC 1573145'
_audit_update_record             
;
2017-09-07 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H18 Cl4 Ir N5 O2'
_chemical_formula_weight         778.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.546(16)
_cell_length_b                   13.292(19)
_cell_length_c                   13.599(19)
_cell_angle_alpha                109.302(3)
_cell_angle_beta                 110.410(2)
_cell_angle_gamma                103.766(3)
_cell_volume                     1692.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3033
_cell_measurement_theta_min      1.27
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    4.289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9798
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_process_details   SADABS(Sheldrick,1996)

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12649
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.1067
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         28.42
_reflns_number_total             8437
_reflns_number_gt                5826
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1563P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8437
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_ref         0.2491
_refine_ls_wR_factor_gt          0.2119
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3525(13) 0.0611(12) 0.0025(13) 0.042(3) Uani 1 1 d . . .
H1 H 0.3535 0.0232 0.0491 0.050 Uiso 1 1 calc R . .
C2 C 0.3643(15) 0.0183(15) -0.1006(13) 0.053(4) Uani 1 1 d . . .
H2 H 0.3745 -0.0501 -0.1345 0.063 Uiso 1 1 calc R . .
C3 C 0.3567(15) 0.1057(13) -0.1434(13) 0.047(3) Uani 1 1 d . . .
H3 H 0.3634 0.1049 -0.2099 0.057 Uiso 1 1 calc R . .
C4 C 0.3341(12) 0.2965(11) -0.0523(11) 0.035(3) Uani 1 1 d . . .
C5 C 0.3443(12) 0.3663(11) 0.0572(11) 0.034(3) Uani 1 1 d . . .
C6 C 0.3452(13) 0.4782(13) 0.0788(12) 0.044(3) Uani 1 1 d . . .
H6 H 0.3566 0.5279 0.1514 0.053 Uiso 1 1 calc R . .
C7 C 0.3295(14) 0.5121(12) -0.0057(13) 0.043(3) Uani 1 1 d . . .
C8 C 0.3170(16) 0.4447(13) -0.1142(13) 0.050(4) Uani 1 1 d . . .
H8 H 0.3081 0.4719 -0.1701 0.061 Uiso 1 1 calc R . .
C9 C 0.3180(15) 0.3392(15) -0.1361(12) 0.049(3) Uani 1 1 d . . .
C10 C 0.2988(14) 0.4784(15) 0.3317(13) 0.046(3) Uani 1 1 d . . .
H10 H 0.2054 0.4435 0.2972 0.056 Uiso 1 1 calc R . .
C11 C 0.3794(16) 0.5889(13) 0.4300(13) 0.050(3) Uani 1 1 d . . .
H11 H 0.3510 0.6382 0.4732 0.059 Uiso 1 1 calc R . .
C12 C 0.5051(16) 0.6071(13) 0.4472(12) 0.050(3) Uani 1 1 d . . .
H12 H 0.5812 0.6742 0.5045 0.060 Uiso 1 1 calc R . .
C13 C 0.6038(12) 0.4778(12) 0.3459(10) 0.035(3) Uani 1 1 d . . .
C14 C 0.5496(12) 0.3663(10) 0.2486(10) 0.032(2) Uani 1 1 d . . .
C15 C 0.6400(11) 0.3218(12) 0.2220(11) 0.037(3) Uani 1 1 d . . .
H15 H 0.6075 0.2494 0.1586 0.045 Uiso 1 1 calc R . .
C16 C 0.7767(14) 0.3863(15) 0.2908(14) 0.050(4) Uani 1 1 d . . .
C17 C 0.8290(13) 0.4943(13) 0.3847(13) 0.048(3) Uani 1 1 d . . .
H17 H 0.9219 0.5355 0.4288 0.058 Uiso 1 1 calc R . .
C18 C 0.7418(13) 0.5435(13) 0.4151(12) 0.045(3) Uani 1 1 d . . .
C19 C 0.0468(14) 0.2414(16) -0.0029(15) 0.057(4) Uani 1 1 d . . .
H19A H 0.0588 0.2140 -0.0728 0.068 Uiso 1 1 calc R . .
H19B H 0.0667 0.3239 0.0256 0.068 Uiso 1 1 calc R . .
C20 C -0.0928(13) 0.1755(14) -0.0289(13) 0.051(4) Uani 1 1 d . . .
H20A H -0.1379 0.2272 -0.0126 0.061 Uiso 1 1 calc R . .
H20B H -0.1455 0.1169 -0.1105 0.061 Uiso 1 1 calc R . .
C21 C 0.0627(12) 0.1550(11) 0.1096(11) 0.035(3) Uani 1 1 d . . .
C22 C 0.1057(13) 0.1124(12) 0.1988(11) 0.039(3) Uani 1 1 d . . .
C23 C 0.2418(13) 0.1347(11) 0.2661(11) 0.038(3) Uani 1 1 d . . .
C24 C 0.2638(15) 0.0852(13) 0.3440(12) 0.047(3) Uani 1 1 d . . .
H24 H 0.3523 0.0992 0.3913 0.057 Uiso 1 1 calc R . .
C25 C 0.1654(18) 0.0188(16) 0.3549(15) 0.062(4) Uani 1 1 d . . .
H25 H 0.1867 -0.0145 0.4056 0.074 Uiso 1 1 calc R . .
C26 C 0.0370(18) 0.0008(17) 0.2927(15) 0.066(5) Uani 1 1 d . . .
H26 H -0.0305 -0.0438 0.3015 0.080 Uiso 1 1 calc R . .
C27 C 0.0054(17) 0.0463(18) 0.2184(16) 0.070(5) Uani 1 1 d . . .
H27 H -0.0839 0.0351 0.1781 0.084 Uiso 1 1 calc R . .
N1 N 0.3397(10) 0.1629(10) 0.0267(10) 0.040(2) Uani 1 1 d . . .
N2 N 0.3379(11) 0.1882(9) -0.0668(9) 0.038(2) Uani 1 1 d . . .
N3 N 0.3744(10) 0.4309(9) 0.2951(9) 0.035(2) Uani 1 1 d . . .
N4 N 0.5045(10) 0.5119(9) 0.3675(9) 0.036(2) Uani 1 1 d . . .
N5 N 0.1340(10) 0.2192(10) 0.0884(10) 0.041(2) Uani 1 1 d . . .
O1 O 0.3472(9) 0.1927(8) 0.2589(8) 0.040(2) Uani 1 1 d . . .
O2 O -0.0729(9) 0.1215(10) 0.0511(9) 0.051(3) Uani 1 1 d . . .
Ir1 Ir 0.34709(4) 0.28905(4) 0.16092(4) 0.03026(17) Uani 1 1 d . . .
Cl1 Cl 0.3285(5) 0.6511(4) 0.0238(4) 0.0675(12) Uani 1 1 d . . .
Cl2 Cl 0.2952(6) 0.2536(5) -0.2773(4) 0.0788(15) Uani 1 1 d . . .
Cl3 Cl 0.8142(4) 0.6770(4) 0.5297(3) 0.0606(10) Uani 1 1 d . . .
Cl4 Cl 0.8874(4) 0.3289(5) 0.2565(4) 0.0708(12) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.340(17) . ?
C1 C2 1.40(2) . ?
C2 C3 1.47(2) . ?
C3 N2 1.360(17) . ?
C4 N2 1.401(16) . ?
C4 C9 1.409(18) . ?
C4 C5 1.417(18) . ?
C5 C6 1.413(18) . ?
C5 Ir1 1.997(11) . ?
C6 C7 1.339(17) . ?
C7 C8 1.38(2) . ?
C7 Cl1 1.760(14) . ?
C8 C9 1.34(2) . ?
C9 Cl2 1.764(14) . ?
C10 N3 1.328(16) . ?
C10 C11 1.41(2) . ?
C11 C12 1.33(2) . ?
C12 N4 1.364(17) . ?
C13 C18 1.391(17) . ?
C13 N4 1.414(16) . ?
C13 C14 1.422(17) . ?
C14 C15 1.409(17) . ?
C14 Ir1 2.011(12) . ?
C15 C16 1.378(18) . ?
C16 C17 1.38(2) . ?
C16 Cl4 1.754(15) . ?
C17 C18 1.43(2) . ?
C18 Cl3 1.683(16) . ?
C19 N5 1.468(17) . ?
C19 C20 1.49(2) . ?
C20 O2 1.473(17) . ?
C21 N5 1.217(16) . ?
C21 O2 1.359(14) . ?
C21 C22 1.484(17) . ?
C22 C23 1.411(18) . ?
C22 C27 1.439(19) . ?
C23 O1 1.331(15) . ?
C23 C24 1.404(17) . ?
C24 C25 1.35(2) . ?
C25 C26 1.34(2) . ?
C26 C27 1.33(2) . ?
N1 N2 1.412(15) . ?
N1 Ir1 1.988(12) . ?
N3 N4 1.372(14) . ?
N3 Ir1 2.006(11) . ?
N5 Ir1 2.122(10) . ?
O1 Ir1 2.131(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 112.4(12) . . ?
C1 C2 C3 104.4(13) . . ?
N2 C3 C2 106.4(12) . . ?
N2 C4 C9 126.4(12) . . ?
N2 C4 C5 115.0(10) . . ?
C9 C4 C5 118.5(12) . . ?
C6 C5 C4 117.9(11) . . ?
C6 C5 Ir1 127.6(10) . . ?
C4 C5 Ir1 114.5(9) . . ?
C7 C6 C5 119.7(14) . . ?
C6 C7 C8 123.5(13) . . ?
C6 C7 Cl1 118.3(12) . . ?
C8 C7 Cl1 118.2(9) . . ?
C9 C8 C7 118.0(12) . . ?
C8 C9 C4 122.3(14) . . ?
C8 C9 Cl2 116.7(11) . . ?
C4 C9 Cl2 121.0(12) . . ?
N3 C10 C11 110.9(13) . . ?
C12 C11 C10 104.9(13) . . ?
C11 C12 N4 109.3(14) . . ?
C18 C13 N4 124.0(12) . . ?
C18 C13 C14 122.4(12) . . ?
N4 C13 C14 113.5(10) . . ?
C15 C14 C13 118.3(11) . . ?
C15 C14 Ir1 126.7(9) . . ?
C13 C14 Ir1 115.1(9) . . ?
C16 C15 C14 119.5(13) . . ?
C17 C16 C15 122.1(14) . . ?
C17 C16 Cl4 119.1(11) . . ?
C15 C16 Cl4 118.7(13) . . ?
C16 C17 C18 120.6(12) . . ?
C13 C18 C17 117.1(13) . . ?
C13 C18 Cl3 125.5(12) . . ?
C17 C18 Cl3 117.4(10) . . ?
N5 C19 C20 104.8(12) . . ?
O2 C20 C19 103.6(10) . . ?
N5 C21 O2 118.1(11) . . ?
N5 C21 C22 127.8(12) . . ?
O2 C21 C22 114.0(11) . . ?
C23 C22 C27 118.3(13) . . ?
C23 C22 C21 122.6(11) . . ?
C27 C22 C21 119.1(13) . . ?
O1 C23 C24 118.4(12) . . ?
O1 C23 C22 126.5(11) . . ?
C24 C23 C22 115.0(12) . . ?
C25 C24 C23 124.5(14) . . ?
C26 C25 C24 119.9(15) . . ?
C27 C26 C25 120.4(15) . . ?
C26 C27 C22 121.8(16) . . ?
C1 N1 N2 106.2(11) . . ?
C1 N1 Ir1 137.8(10) . . ?
N2 N1 Ir1 115.4(8) . . ?
C3 N2 C4 134.7(11) . . ?
C3 N2 N1 110.5(11) . . ?
C4 N2 N1 114.2(10) . . ?
C10 N3 N4 105.5(11) . . ?
C10 N3 Ir1 137.9(10) . . ?
N4 N3 Ir1 116.3(8) . . ?
C12 N4 N3 109.3(11) . . ?
C12 N4 C13 135.5(12) . . ?
N3 N4 C13 115.2(10) . . ?
C21 N5 C19 108.3(11) . . ?
C21 N5 Ir1 129.0(9) . . ?
C19 N5 Ir1 122.6(9) . . ?
C23 O1 Ir1 126.6(7) . . ?
C21 O2 C20 105.1(10) . . ?
N1 Ir1 C5 80.7(5) . . ?
N1 Ir1 N3 172.2(4) . . ?
C5 Ir1 N3 93.9(5) . . ?
N1 Ir1 C14 94.9(5) . . ?
C5 Ir1 C14 90.4(5) . . ?
N3 Ir1 C14 79.4(5) . . ?
N1 Ir1 N5 91.9(4) . . ?
C5 Ir1 N5 92.8(5) . . ?
N3 Ir1 N5 94.1(4) . . ?
C14 Ir1 N5 172.9(4) . . ?
N1 Ir1 O1 94.1(4) . . ?
C5 Ir1 O1 174.8(4) . . ?
N3 Ir1 O1 91.2(4) . . ?
C14 Ir1 O1 90.6(4) . . ?
N5 Ir1 O1 86.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.42
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         6.279
_refine_diff_density_min         -2.165
_refine_diff_density_rms         0.520
####################################################################### 
# 
# 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_11_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1573146'
_audit_update_record             
;
2017-09-07 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H22 F6 Ir N5 O3'
_chemical_formula_weight         806.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   13.8720(16)
_cell_length_b                   10.0960(12)
_cell_length_c                   22.338(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.767(2)
_cell_angle_gamma                90.00
_cell_volume                     3010.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3033
_cell_measurement_theta_min      1.27
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1568
_exptl_absorpt_coefficient_mu    4.512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3867
_exptl_absorpt_correction_T_max  0.4972
_exptl_absorpt_process_details   SADABS(Sheldrick,1996)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21651
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         28.40
_reflns_number_total             7527
_reflns_number_gt                5149
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97(Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0526P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7527
_refine_ls_number_parameters     422
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1010
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.014
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7065(5) 0.5873(6) 0.2506(3) 0.0491(16) Uani 1 1 d . . .
H1 H 0.7278 0.6647 0.2728 0.059 Uiso 1 1 calc R . .
C2 C 0.7378(6) 0.5438(6) 0.1996(3) 0.0572(19) Uani 1 1 d . . .
H2 H 0.7833 0.5853 0.1819 0.069 Uiso 1 1 calc R . .
C3 C 0.6880(5) 0.4282(7) 0.1810(3) 0.0477(16) Uani 1 1 d . . .
H3 H 0.6928 0.3756 0.1478 0.057 Uiso 1 1 calc R . .
C4 C 0.5655(4) 0.2977(5) 0.2260(3) 0.0360(13) Uani 1 1 d . . .
C5 C 0.5251(4) 0.3104(5) 0.2765(3) 0.0346(13) Uani 1 1 d . . .
C6 C 0.4637(5) 0.2063(6) 0.2844(3) 0.0541(18) Uani 1 1 d . . .
H6 H 0.4355 0.2088 0.3177 0.065 Uiso 1 1 calc R . .
C7 C 0.4438(6) 0.1001(7) 0.2443(3) 0.060(2) Uani 1 1 d . . .
H7 H 0.4019 0.0325 0.2505 0.072 Uiso 1 1 calc R . .
C8 C 0.4857(5) 0.0934(6) 0.1949(3) 0.0469(16) Uani 1 1 d . . .
C9 C 0.5473(5) 0.1926(6) 0.1849(3) 0.0400(14) Uani 1 1 d . . .
H9 H 0.5757 0.1891 0.1517 0.048 Uiso 1 1 calc R . .
C10 C 0.4619(7) -0.0207(8) 0.1514(4) 0.071(2) Uani 1 1 d . . .
C11 C 0.3950(6) 0.4522(7) 0.3955(4) 0.0574(19) Uani 1 1 d . . .
H11 H 0.3438 0.4985 0.3679 0.069 Uiso 1 1 calc R . .
C12 C 0.3875(7) 0.3898(8) 0.4495(4) 0.074(2) Uani 1 1 d . . .
H12 H 0.3317 0.3858 0.4648 0.089 Uiso 1 1 calc R . .
C13 C 0.4795(7) 0.3357(7) 0.4752(4) 0.065(2) Uani 1 1 d . . .
H13 H 0.4981 0.2871 0.5119 0.078 Uiso 1 1 calc R . .
C14 C 0.6379(5) 0.3308(6) 0.4397(3) 0.0440(15) Uani 1 1 d . . .
C15 C 0.6678(5) 0.3769(5) 0.3881(3) 0.0391(14) Uani 1 1 d . . .
C16 C 0.7653(5) 0.3410(6) 0.3877(3) 0.0543(17) Uani 1 1 d . . .
H16 H 0.7900 0.3686 0.3550 0.065 Uiso 1 1 calc R . .
C17 C 0.8259(6) 0.2646(7) 0.4353(4) 0.066(2) Uani 1 1 d . . .
H17 H 0.8900 0.2415 0.4337 0.079 Uiso 1 1 calc R . .
C18 C 0.7920(6) 0.2230(7) 0.4847(3) 0.062(2) Uani 1 1 d . . .
C19 C 0.6962(6) 0.2577(7) 0.4868(3) 0.0580(19) Uani 1 1 d . . .
H19 H 0.6723 0.2315 0.5201 0.070 Uiso 1 1 calc R . .
C20 C 0.8547(10) 0.1354(12) 0.5314(6) 0.109(3) Uani 1 1 d U . .
C23 C 0.4097(5) 0.6986(6) 0.2860(3) 0.0462(15) Uani 1 1 d . . .
C24 C 0.4513(5) 0.7762(6) 0.3408(3) 0.0450(15) Uani 1 1 d . . .
C25 C 0.5531(5) 0.7626(6) 0.3755(3) 0.0443(15) Uani 1 1 d . . .
C26 C 0.5945(6) 0.8628(6) 0.4194(3) 0.0549(18) Uani 1 1 d . . .
H26 H 0.6623 0.8604 0.4403 0.066 Uiso 1 1 calc R . .
C27 C 0.5361(7) 0.9631(6) 0.4317(4) 0.065(2) Uani 1 1 d . . .
H27 H 0.5651 1.0292 0.4598 0.078 Uiso 1 1 calc R . .
C28 C 0.4339(8) 0.9671(7) 0.4023(4) 0.072(2) Uani 1 1 d . . .
H28 H 0.3933 1.0298 0.4140 0.087 Uiso 1 1 calc R . .
C29 C 0.3937(6) 0.8778(7) 0.3561(3) 0.0595(19) Uani 1 1 d . . .
H29 H 0.3265 0.8850 0.3343 0.071 Uiso 1 1 calc R . .
C30 C 0.8551(7) 0.6484(9) 0.4767(4) 0.082(3) Uani 1 1 d D . .
H30A H 0.9228 0.6198 0.4814 0.123 Uiso 1 1 calc R . .
H30B H 0.8165 0.5761 0.4860 0.123 Uiso 1 1 calc R . .
H30C H 0.8547 0.7205 0.5046 0.123 Uiso 1 1 calc R . .
N1 N 0.6421(4) 0.5021(4) 0.2627(2) 0.0365(11) Uani 1 1 d . . .
N2 N 0.6302(4) 0.4038(4) 0.2197(2) 0.0358(11) Uani 1 1 d . . .
N3 N 0.4870(4) 0.4354(5) 0.3895(2) 0.0436(12) Uani 1 1 d . . .
N4 N 0.5385(4) 0.3644(5) 0.4386(2) 0.0461(13) Uani 1 1 d . . .
N5 N 0.4433(4) 0.5898(5) 0.2692(2) 0.0452(12) Uani 1 1 d . . .
O1 O 0.3264(4) 0.7483(5) 0.2455(2) 0.0650(14) Uani 1 1 d . . .
O2 O 0.6117(3) 0.6640(4) 0.37004(19) 0.0466(11) Uani 1 1 d . . .
O3 O 0.8133(4) 0.6898(6) 0.4157(2) 0.0695(15) Uani 1 1 d D . .
H3O H 0.750(2) 0.692(9) 0.395(3) 0.104 Uiso 1 1 d D . .
F1 F 0.3664(5) -0.0503(6) 0.1335(3) 0.1097(19) Uani 1 1 d U . .
F2 F 0.4983(5) -0.0145(5) 0.1044(3) 0.1047(18) Uani 1 1 d U . .
F3 F 0.5004(5) -0.1342(6) 0.1789(3) 0.131(2) Uani 1 1 d U . .
F4 F 0.8245(7) 0.0183(7) 0.5313(4) 0.173(3) Uani 1 1 d U . .
F5 F 0.9470(6) 0.1457(8) 0.5436(4) 0.160(3) Uani 1 1 d U . .
F6 F 0.8445(7) 0.1671(9) 0.5897(4) 0.175(3) Uani 1 1 d U . .
Ir1 Ir 0.562289(18) 0.47814(2) 0.325471(10) 0.03503(9) Uani 1 1 d . . .
C31 C 0.3805(7) 0.5532(9) 0.2070(4) 0.071(2) Uani 1 1 d . . .
H31B H 0.425(7) 0.541(10) 0.183(4) 0.107 Uiso 1 1 d . . .
H31A H 0.345(7) 0.458(9) 0.212(4) 0.107 Uiso 1 1 d . . .
C32 C 0.2980(7) 0.6562(8) 0.1933(4) 0.071(2) Uani 1 1 d . . .
H32A H 0.298(7) 0.709(9) 0.162(4) 0.106 Uiso 1 1 d . . .
H32B H 0.236(7) 0.616(9) 0.194(4) 0.106 Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.319(7) . ?
C1 C2 1.398(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.363(9) . ?
C2 H2 0.9300 . ?
C3 N2 1.350(7) . ?
C3 H3 0.9300 . ?
C4 C9 1.381(8) . ?
C4 C5 1.395(7) . ?
C4 N2 1.429(7) . ?
C5 C6 1.394(8) . ?
C5 Ir1 2.006(5) . ?
C6 C7 1.376(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(8) . ?
C8 C10 1.485(10) . ?
C9 H9 0.9300 . ?
C10 F2 1.284(9) . ?
C10 F1 1.310(10) . ?
C10 F3 1.340(10) . ?
C11 N3 1.329(8) . ?
C11 C12 1.390(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(11) . ?
C12 H12 0.9300 . ?
C13 N4 1.335(7) . ?
C13 H13 0.9300 . ?
C14 C19 1.359(9) . ?
C14 C15 1.405(8) . ?
C14 N4 1.414(8) . ?
C15 C16 1.402(9) . ?
C15 Ir1 2.008(6) . ?
C16 C17 1.395(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(10) . ?
C18 C20 1.461(13) . ?
C19 H19 0.9300 . ?
C20 F5 1.239(12) . ?
C20 F4 1.254(12) . ?
C20 F6 1.386(13) . ?
C23 N5 1.288(8) . ?
C23 O1 1.355(8) . ?
C23 C24 1.437(8) . ?
C24 C29 1.398(8) . ?
C24 C25 1.421(9) . ?
C25 O2 1.312(7) . ?
C25 C26 1.417(8) . ?
C26 C27 1.370(9) . ?
C26 H26 0.9300 . ?
C27 C28 1.391(12) . ?
C27 H27 0.9300 . ?
C28 C29 1.370(10) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 O3 1.392(9) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
N1 N2 1.360(6) . ?
N1 Ir1 2.024(5) . ?
N3 N4 1.343(7) . ?
N3 Ir1 2.033(5) . ?
N5 C31 1.471(9) . ?
N5 Ir1 2.109(5) . ?
O1 C32 1.458(10) . ?
O2 Ir1 2.147(4) . ?
O3 H3O 0.88(2) . ?
C31 C32 1.515(11) . ?
C31 H31B 0.93(10) . ?
C31 H31A 1.10(9) . ?
C32 H32A 0.89(9) . ?
C32 H32B 0.95(9) . ?

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 C1 C2 109.9(6) . . ?
N1 C1 H1 125.1 . . ?
C2 C1 H1 125.1 . . ?
C3 C2 C1 105.7(5) . . ?
C3 C2 H2 127.1 . . ?
C1 C2 H2 127.1 . . ?
N2 C3 C2 107.6(5) . . ?
N2 C3 H3 126.2 . . ?
C2 C3 H3 126.2 . . ?
C9 C4 C5 124.6(5) . . ?
C9 C4 N2 121.1(5) . . ?
C5 C4 N2 114.3(5) . . ?
C6 C5 C4 115.3(5) . . ?
C6 C5 Ir1 130.0(4) . . ?
C4 C5 Ir1 114.7(4) . . ?
C7 C6 C5 121.8(6) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 120.3(6) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.6(6) . . ?
C9 C8 C10 119.8(6) . . ?
C7 C8 C10 119.6(6) . . ?
C8 C9 C4 117.5(5) . . ?
C8 C9 H9 121.3 . . ?
C4 C9 H9 121.3 . . ?
F2 C10 F1 110.5(8) . . ?
F2 C10 F3 102.7(7) . . ?
F1 C10 F3 100.9(7) . . ?
F2 C10 C8 115.5(6) . . ?
F1 C10 C8 113.8(7) . . ?
F3 C10 C8 112.0(8) . . ?
N3 C11 C12 109.3(8) . . ?
N3 C11 H11 125.4 . . ?
C12 C11 H11 125.4 . . ?
C13 C12 C11 105.3(7) . . ?
C13 C12 H12 127.3 . . ?
C11 C12 H12 127.3 . . ?
N4 C13 C12 108.4(7) . . ?
N4 C13 H13 125.8 . . ?
C12 C13 H13 125.8 . . ?
C19 C14 C15 124.7(7) . . ?
C19 C14 N4 121.0(6) . . ?
C15 C14 N4 114.3(6) . . ?
C16 C15 C14 114.8(6) . . ?
C16 C15 Ir1 130.5(5) . . ?
C14 C15 Ir1 114.7(4) . . ?
C17 C16 C15 121.4(7) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 120.9(7) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.3(7) . . ?
C17 C18 C20 119.3(9) . . ?
C19 C18 C20 121.2(8) . . ?
C14 C19 C18 119.0(7) . . ?
C14 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
F5 C20 F4 113.8(12) . . ?
F5 C20 F6 97.9(11) . . ?
F4 C20 F6 95.8(10) . . ?
F5 C20 C18 119.1(10) . . ?
F4 C20 C18 115.8(11) . . ?
F6 C20 C18 109.8(10) . . ?
N5 C23 O1 115.6(6) . . ?
N5 C23 C24 128.3(6) . . ?
O1 C23 C24 116.1(6) . . ?
C29 C24 C25 119.2(6) . . ?
C29 C24 C23 119.0(7) . . ?
C25 C24 C23 121.5(6) . . ?
O2 C25 C26 117.5(6) . . ?
O2 C25 C24 124.9(6) . . ?
C26 C25 C24 117.6(6) . . ?
C27 C26 C25 121.0(8) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 120.6(7) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C29 C28 C27 119.3(7) . . ?
C29 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
C28 C29 C24 121.6(8) . . ?
C28 C29 H29 119.2 . . ?
C24 C29 H29 119.2 . . ?
O3 C30 H30A 109.5 . . ?
O3 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O3 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C1 N1 N2 106.9(5) . . ?
C1 N1 Ir1 138.4(4) . . ?
N2 N1 Ir1 114.7(3) . . ?
C3 N2 N1 109.8(5) . . ?
C3 N2 C4 134.2(5) . . ?
N1 N2 C4 115.9(4) . . ?
C11 N3 N4 107.3(5) . . ?
C11 N3 Ir1 137.3(5) . . ?
N4 N3 Ir1 115.3(4) . . ?
C13 N4 N3 109.7(6) . . ?
C13 N4 C14 134.0(6) . . ?
N3 N4 C14 116.2(5) . . ?
C23 N5 C31 108.7(6) . . ?
C23 N5 Ir1 124.7(4) . . ?
C31 N5 Ir1 126.5(4) . . ?
C23 O1 C32 107.0(5) . . ?
C25 O2 Ir1 125.4(4) . . ?
C30 O3 H3O 128(5) . . ?
C5 Ir1 C15 88.9(2) . . ?
C5 Ir1 N1 80.25(19) . . ?
C15 Ir1 N1 96.4(2) . . ?
C5 Ir1 N3 95.7(2) . . ?
C15 Ir1 N3 79.6(2) . . ?
N1 Ir1 N3 174.36(19) . . ?
C5 Ir1 N5 94.7(2) . . ?
C15 Ir1 N5 172.6(2) . . ?
N1 Ir1 N5 90.6(2) . . ?
N3 Ir1 N5 93.7(2) . . ?
C5 Ir1 O2 173.17(19) . . ?
C15 Ir1 O2 92.36(19) . . ?
N1 Ir1 O2 92.94(17) . . ?
N3 Ir1 O2 91.12(18) . . ?
N5 Ir1 O2 84.76(17) . . ?
N5 C31 C32 103.8(6) . . ?
N5 C31 H31B 105(6) . . ?
C32 C31 H31B 124(6) . . ?
N5 C31 H31A 107(5) . . ?
C32 C31 H31A 106(5) . . ?
H31B C31 H31A 109(7) . . ?
O1 C32 C31 104.5(6) . . ?
O1 C32 H32A 101(6) . . ?
C31 C32 H32A 114(6) . . ?
O1 C32 H32B 108(6) . . ?
C31 C32 H32B 110(6) . . ?
H32A C32 H32B 118(8) . . ?

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
N1 C1 C2 C3 0.6(8) . . . . ?
C1 C2 C3 N2 -0.4(8) . . . . ?
C9 C4 C5 C6 0.8(9) . . . . ?
N2 C4 C5 C6 -178.5(6) . . . . ?
C9 C4 C5 Ir1 -177.9(5) . . . . ?
N2 C4 C5 Ir1 2.8(7) . . . . ?
C4 C5 C6 C7 -0.9(10) . . . . ?
Ir1 C5 C6 C7 177.6(6) . . . . ?
C5 C6 C7 C8 0.7(12) . . . . ?
C6 C7 C8 C9 -0.3(12) . . . . ?
C6 C7 C8 C10 -178.9(8) . . . . ?
C7 C8 C9 C4 0.2(10) . . . . ?
C10 C8 C9 C4 178.8(7) . . . . ?
C5 C4 C9 C8 -0.5(10) . . . . ?
N2 C4 C9 C8 178.8(6) . . . . ?
C9 C8 C10 F2 -3.3(12) . . . . ?
C7 C8 C10 F2 175.3(8) . . . . ?
C9 C8 C10 F1 -132.6(8) . . . . ?
C7 C8 C10 F1 46.0(12) . . . . ?
C9 C8 C10 F3 113.7(8) . . . . ?
C7 C8 C10 F3 -67.7(10) . . . . ?
N3 C11 C12 C13 0.2(8) . . . . ?
C11 C12 C13 N4 0.1(8) . . . . ?
C19 C14 C15 C16 0.6(9) . . . . ?
N4 C14 C15 C16 -178.2(5) . . . . ?
C19 C14 C15 Ir1 178.4(5) . . . . ?
N4 C14 C15 Ir1 -0.4(6) . . . . ?
C14 C15 C16 C17 0.3(9) . . . . ?
Ir1 C15 C16 C17 -177.2(5) . . . . ?
C15 C16 C17 C18 -0.6(11) . . . . ?
C16 C17 C18 C19 0.0(11) . . . . ?
C16 C17 C18 C20 175.7(8) . . . . ?
C15 C14 C19 C18 -1.1(10) . . . . ?
N4 C14 C19 C18 177.6(6) . . . . ?
C17 C18 C19 C14 0.8(10) . . . . ?
C20 C18 C19 C14 -174.8(8) . . . . ?
C17 C18 C20 F5 32.1(16) . . . . ?
C19 C18 C20 F5 -152.3(11) . . . . ?
C17 C18 C20 F4 -109.3(12) . . . . ?
C19 C18 C20 F4 66.3(15) . . . . ?
C17 C18 C20 F6 143.7(9) . . . . ?
C19 C18 C20 F6 -40.7(13) . . . . ?
N5 C23 C24 C29 -168.4(7) . . . . ?
O1 C23 C24 C29 14.3(9) . . . . ?
N5 C23 C24 C25 19.2(10) . . . . ?
O1 C23 C24 C25 -158.1(6) . . . . ?
C29 C24 C25 O2 172.7(6) . . . . ?
C23 C24 C25 O2 -14.9(9) . . . . ?
C29 C24 C25 C26 -7.2(9) . . . . ?
C23 C24 C25 C26 165.2(6) . . . . ?
O2 C25 C26 C27 -174.5(6) . . . . ?
C24 C25 C26 C27 5.4(9) . . . . ?
C25 C26 C27 C28 1.7(11) . . . . ?
C26 C27 C28 C29 -6.9(12) . . . . ?
C27 C28 C29 C24 5.0(11) . . . . ?
C25 C24 C29 C28 2.1(10) . . . . ?
C23 C24 C29 C28 -170.5(7) . . . . ?
C2 C1 N1 N2 -0.6(7) . . . . ?
C2 C1 N1 Ir1 178.3(5) . . . . ?
C2 C3 N2 N1 0.0(8) . . . . ?
C2 C3 N2 C4 -176.7(6) . . . . ?
C1 N1 N2 C3 0.4(7) . . . . ?
Ir1 N1 N2 C3 -178.8(4) . . . . ?
C1 N1 N2 C4 177.8(5) . . . . ?
Ir1 N1 N2 C4 -1.4(6) . . . . ?
C9 C4 N2 C3 -3.7(10) . . . . ?
C5 C4 N2 C3 175.7(6) . . . . ?
C9 C4 N2 N1 179.8(5) . . . . ?
C5 C4 N2 N1 -0.9(7) . . . . ?
C12 C11 N3 N4 -0.4(7) . . . . ?
C12 C11 N3 Ir1 175.1(5) . . . . ?
C12 C13 N4 N3 -0.3(8) . . . . ?
C12 C13 N4 C14 -176.6(7) . . . . ?
C11 N3 N4 C13 0.4(7) . . . . ?
Ir1 N3 N4 C13 -176.2(4) . . . . ?
C11 N3 N4 C14 177.4(5) . . . . ?
Ir1 N3 N4 C14 0.8(6) . . . . ?
C19 C14 N4 C13 -3.1(10) . . . . ?
C15 C14 N4 C13 175.8(6) . . . . ?
C19 C14 N4 N3 -179.2(5) . . . . ?
C15 C14 N4 N3 -0.3(7) . . . . ?
O1 C23 N5 C31 2.3(9) . . . . ?
C24 C23 N5 C31 -175.0(7) . . . . ?
O1 C23 N5 Ir1 -173.7(4) . . . . ?
C24 C23 N5 Ir1 9.0(10) . . . . ?
N5 C23 O1 C32 1.4(8) . . . . ?
C24 C23 O1 C32 179.0(6) . . . . ?
C26 C25 O2 Ir1 164.1(4) . . . . ?
C24 C25 O2 Ir1 -15.8(8) . . . . ?
C6 C5 Ir1 C15 82.1(7) . . . . ?
C4 C5 Ir1 C15 -99.4(5) . . . . ?
C6 C5 Ir1 N1 178.8(7) . . . . ?
C4 C5 Ir1 N1 -2.8(4) . . . . ?
C6 C5 Ir1 N3 2.8(7) . . . . ?
C4 C5 Ir1 N3 -178.8(4) . . . . ?
C6 C5 Ir1 N5 -91.4(6) . . . . ?
C4 C5 Ir1 N5 87.1(4) . . . . ?
C6 C5 Ir1 O2 -177.0(14) . . . . ?
C4 C5 Ir1 O2 1(2) . . . . ?
C16 C15 Ir1 C5 82.1(6) . . . . ?
C14 C15 Ir1 C5 -95.4(4) . . . . ?
C16 C15 Ir1 N1 2.0(6) . . . . ?
C14 C15 Ir1 N1 -175.5(4) . . . . ?
C16 C15 Ir1 N3 178.1(6) . . . . ?
C14 C15 Ir1 N3 0.6(4) . . . . ?
C16 C15 Ir1 N5 -158.1(14) . . . . ?
C14 C15 Ir1 N5 24.4(18) . . . . ?
C16 C15 Ir1 O2 -91.2(6) . . . . ?
C14 C15 Ir1 O2 91.3(4) . . . . ?
C1 N1 Ir1 C5 -176.6(7) . . . . ?
N2 N1 Ir1 C5 2.3(4) . . . . ?
C1 N1 Ir1 C15 -88.8(7) . . . . ?
N2 N1 Ir1 C15 90.1(4) . . . . ?
C1 N1 Ir1 N3 -132.1(18) . . . . ?
N2 N1 Ir1 N3 47(2) . . . . ?
C1 N1 Ir1 N5 88.7(7) . . . . ?
N2 N1 Ir1 N5 -92.4(4) . . . . ?
C1 N1 Ir1 O2 3.9(7) . . . . ?
N2 N1 Ir1 O2 -177.2(4) . . . . ?
C11 N3 Ir1 C5 -88.2(6) . . . . ?
N4 N3 Ir1 C5 87.1(4) . . . . ?
C11 N3 Ir1 C15 -176.0(7) . . . . ?
N4 N3 Ir1 C15 -0.8(4) . . . . ?
C11 N3 Ir1 N1 -132.1(19) . . . . ?
N4 N3 Ir1 N1 43(2) . . . . ?
C11 N3 Ir1 N5 7.0(6) . . . . ?
N4 N3 Ir1 N5 -177.8(4) . . . . ?
C11 N3 Ir1 O2 91.8(6) . . . . ?
N4 N3 Ir1 O2 -93.0(4) . . . . ?
C23 N5 Ir1 C5 160.3(5) . . . . ?
C31 N5 Ir1 C5 -14.9(7) . . . . ?
C23 N5 Ir1 C15 40.9(19) . . . . ?
C31 N5 Ir1 C15 -134.4(16) . . . . ?
C23 N5 Ir1 N1 -119.4(5) . . . . ?
C31 N5 Ir1 N1 65.3(7) . . . . ?
C23 N5 Ir1 N3 64.3(5) . . . . ?
C31 N5 Ir1 N3 -111.0(7) . . . . ?
C23 N5 Ir1 O2 -26.5(5) . . . . ?
C31 N5 Ir1 O2 158.2(7) . . . . ?
C25 O2 Ir1 C5 116.4(16) . . . . ?
C25 O2 Ir1 C15 -142.9(5) . . . . ?
C25 O2 Ir1 N1 120.6(5) . . . . ?
C25 O2 Ir1 N3 -63.4(5) . . . . ?
C25 O2 Ir1 N5 30.2(5) . . . . ?
C23 N5 C31 C32 -4.8(9) . . . . ?
Ir1 N5 C31 C32 171.1(5) . . . . ?
C23 O1 C32 C31 -4.3(9) . . . . ?
N5 C31 C32 O1 5.3(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.567
_refine_diff_density_min         -0.886
_refine_diff_density_rms         0.136
####################################################################### 
# 
# 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_mo_chewl170324_0m
_database_code_depnum_ccdc_archive 'CCDC 1573148'
_audit_update_record             
;
2017-09-07 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H21 F4 Ir N8 O9'
_chemical_formula_weight         941.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   17.161(3)
_cell_length_b                   9.905(2)
_cell_length_c                   23.645(5)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 104.93(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     3883.6(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    283(2)
_cell_measurement_reflns_used    3033
_cell_measurement_theta_min      1.27
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1840
_exptl_absorpt_coefficient_mu    3.517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5254
_exptl_absorpt_correction_T_max  0.6578
_exptl_absorpt_process_details   SADABS(Sheldrick,1996)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      283(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            63748
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         28.30
_reflns_number_total             9610
_reflns_number_gt                7421
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97(Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0778P)²+8.3680P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9610
_refine_ls_number_parameters     496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1606
_refine_ls_wR_factor_gt          0.1390
_refine_ls_goodness_of_fit_ref   1.219
_refine_ls_restrained_S_all      1.219
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir01 Ir 0.493244(14) 0.73503(2) 0.766277(11) 0.03140(10) Uani 1 1 d . . .
O3 O 0.5723(3) 0.6552(5) 0.6241(2) 0.0418(11) Uani 1 1 d . . .
H100 H 0.5664 0.5977 0.6476 0.063 Uiso 1 1 calc R . .
O2 O 0.5864(3) 0.6367(5) 0.7319(2) 0.0395(11) Uani 1 1 d . . .
C23 C 0.6469(4) 0.5505(6) 0.7606(3) 0.0332(14) Uani 1 1 d . . .
C24 C 0.6835(4) 0.4701(7) 0.7270(3) 0.0404(16) Uani 1 1 d . . .
H24 H 0.6662 0.4745 0.6864 0.048 Uiso 1 1 calc R . .
N2 N 0.5110(4) 0.9847(6) 0.7075(3) 0.0452(15) Uani 1 1 d . . .
O1 O 0.6751(4) 0.6136(8) 0.9190(2) 0.0702(19) Uani 1 1 d . . .
O6 O 0.5100(4) 0.4090(6) 0.6415(3) 0.0698(19) Uani 1 1 d . . .
N7 N 0.4477(4) 0.4426(6) 0.6055(3) 0.0471(15) Uani 1 1 d . . .
N5 N 0.5719(3) 0.6921(7) 0.8491(2) 0.0412(13) Uani 1 1 d . . .
O7 O 0.3825(4) 0.3890(6) 0.6022(3) 0.0684(18) Uani 1 1 d . . .
N3 N 0.4324(4) 0.5601(6) 0.7723(3) 0.0471(15) Uani 1 1 d . . .
F2 F 0.4286(4) 1.0919(6) 0.5973(3) 0.091(2) Uani 1 1 d . . .
F1 F 0.2605(3) 0.7112(7) 0.5611(3) 0.0829(18) Uani 1 1 d . . .
C25 C 0.7453(4) 0.3835(8) 0.7531(4) 0.0494(18) Uani 1 1 d . . .
H25 H 0.7692 0.3298 0.7300 0.059 Uiso 1 1 calc R . .
O8 O 0.3309(5) 0.7459(7) 0.3823(3) 0.082(3) Uani 1 1 d . . .
C5 C 0.4255(4) 0.7907(7) 0.6863(3) 0.0330(13) Uani 1 1 d . . .
C4 C 0.4476(4) 0.9164(7) 0.6675(3) 0.0411(16) Uani 1 1 d . . .
N1 N 0.5441(3) 0.9157(5) 0.7580(3) 0.0397(13) Uani 1 1 d . . .
N6 N 0.5805(5) 0.8320(7) 0.5389(3) 0.0518(17) Uani 1 1 d . . .
C28 C 0.5171(4) 0.6439(6) 0.5775(3) 0.0330(13) Uani 1 1 d . . .
O5 O 0.6434(6) 0.7907(10) 0.5318(4) 0.102(3) Uani 1 1 d . . .
N8 N 0.3255(5) 0.6600(8) 0.4187(3) 0.062(2) Uani 1 1 d . . .
N4 N 0.3677(4) 0.5743(8) 0.7947(4) 0.066(2) Uani 1 1 d . . .
C29 C 0.4519(4) 0.5486(7) 0.5636(3) 0.0355(14) Uani 1 1 d . . .
C33 C 0.5137(5) 0.7369(6) 0.5301(3) 0.0375(15) Uani 1 1 d . . .
C22 C 0.6720(4) 0.5439(7) 0.8215(3) 0.0368(15) Uani 1 1 d . . .
C14 C 0.4055(4) 0.8089(9) 0.7993(3) 0.0458(18) Uani 1 1 d . . .
O9 O 0.2697(4) 0.5799(8) 0.4135(3) 0.089(2) Uani 1 1 d . . .
C32 C 0.4539(5) 0.7446(6) 0.4795(3) 0.0415(17) Uani 1 1 d . . .
H32 H 0.4549 0.8094 0.4512 0.050 Uiso 1 1 calc R . .
C30 C 0.3901(4) 0.5537(7) 0.5129(3) 0.0401(15) Uani 1 1 d . . .
H30 H 0.3480 0.4918 0.5065 0.048 Uiso 1 1 calc R . .
F3 F 0.2387(5) 0.6520(10) 0.8439(5) 0.164(4) Uani 1 1 d . . .
C1 C 0.5995(5) 0.9975(8) 0.7912(4) 0.054(2) Uani 1 1 d . . .
H1 H 0.6311 0.9758 0.8283 0.065 Uiso 1 1 calc R . .
C26 C 0.7717(5) 0.3761(9) 0.8129(4) 0.057(2) Uani 1 1 d . . .
H26 H 0.8135 0.3181 0.8304 0.068 Uiso 1 1 calc R . .
F4 F 0.3189(6) 1.1041(8) 0.8498(5) 0.151(4) Uani 1 1 d . . .
C13 C 0.3520(5) 0.7107(10) 0.8101(5) 0.063(3) Uani 1 1 d . . .
C27 C 0.7360(5) 0.4546(8) 0.8464(4) 0.0511(19) Uani 1 1 d . . .
H27 H 0.7544 0.4493 0.8869 0.061 Uiso 1 1 calc R . .
C31 C 0.3918(4) 0.6519(7) 0.4719(3) 0.0424(17) Uani 1 1 d . . .
C6 C 0.3608(4) 0.7236(8) 0.6498(3) 0.0419(16) Uani 1 1 d . . .
H6 H 0.3436 0.6411 0.6610 0.050 Uiso 1 1 calc R . .
C15 C 0.3935(5) 0.9434(10) 0.8135(4) 0.064(3) Uani 1 1 d . . .
H15 H 0.4270 1.0119 0.8065 0.077 Uiso 1 1 calc R . .
C21 C 0.6364(4) 0.6197(8) 0.8611(3) 0.0431(16) Uani 1 1 d . . .
C2 C 0.6033(7) 1.1166(9) 0.7633(5) 0.075(3) Uani 1 1 d . . .
H2 H 0.6376 1.1887 0.7772 0.090 Uiso 1 1 calc R . .
O4 O 0.5722(5) 0.9426(7) 0.5551(5) 0.137(5) Uani 1 1 d . . .
C7 C 0.3217(5) 0.7808(10) 0.5963(4) 0.055(2) Uani 1 1 d . . .
C8 C 0.3431(6) 0.9040(10) 0.5772(4) 0.063(3) Uani 1 1 d . . .
H8 H 0.3159 0.9400 0.5412 0.076 Uiso 1 1 calc R . .
C18 C 0.2900(7) 0.7457(12) 0.8339(8) 0.101(5) Uani 1 1 d . . .
C3 C 0.5457(6) 1.1091(8) 0.7100(5) 0.068(3) Uani 1 1 d . . .
H3 H 0.5333 1.1760 0.6815 0.082 Uiso 1 1 calc R . .
C9 C 0.4060(6) 0.9699(8) 0.6136(4) 0.055(2) Uani 1 1 d . . .
C10 C 0.4397(7) 0.4305(9) 0.7620(4) 0.070(3) Uani 1 1 d . . .
H10 H 0.4798 0.3923 0.7471 0.084 Uiso 1 1 calc R . .
C16 C 0.3309(7) 0.9709(13) 0.8381(6) 0.099(4) Uani 1 1 d . . .
C17 C 0.2784(8) 0.8729(17) 0.8480(8) 0.129(7) Uani 1 1 d . . .
H17 H 0.2361 0.8954 0.8642 0.155 Uiso 1 1 calc R . .
C12 C 0.3356(9) 0.4505(13) 0.7986(7) 0.110(5) Uani 1 1 d . . .
H12 H 0.2918 0.4324 0.8138 0.132 Uiso 1 1 calc R . .
C19 C 0.5589(7) 0.7461(10) 0.9046(4) 0.070(3) Uani 1 1 d . . .
H19A H 0.5086 0.7132 0.9110 0.083 Uiso 1 1 calc R . .
H19B H 0.5581 0.8440 0.9043 0.083 Uiso 1 1 calc R . .
C20 C 0.6300(7) 0.6935(16) 0.9507(4) 0.099(4) Uani 1 1 d . . .
H20A H 0.6626 0.7674 0.9710 0.118 Uiso 1 1 calc R . .
H20B H 0.6124 0.6386 0.9790 0.118 Uiso 1 1 calc R . .
C11 C 0.3771(9) 0.3592(13) 0.7771(7) 0.113(5) Uani 1 1 d . . .
H11 H 0.3668 0.2670 0.7730 0.136 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir01 C14 2.005(8) . ?
Ir01 N1 2.022(6) . ?
Ir01 C5 2.025(6) . ?
Ir01 N3 2.047(6) . ?
Ir01 N5 2.115(5) . ?
Ir01 O2 2.198(5) . ?
O3 C28 1.260(7) . ?
O3 H100 0.8200 . ?
O2 C23 1.380(7) . ?
C23 C24 1.385(10) . ?
C23 C22 1.393(9) . ?
C24 C25 1.380(9) . ?
C24 H24 0.9300 . ?
N2 C3 1.364(10) . ?
N2 N1 1.366(8) . ?
N2 C4 1.416(9) . ?
O1 C21 1.362(8) . ?
O1 C20 1.443(12) . ?
O6 N7 1.229(8) . ?
N7 O7 1.222(8) . ?
N7 C29 1.457(9) . ?
N5 C21 1.288(9) . ?
N5 C19 1.486(11) . ?
N3 C10 1.319(11) . ?
N3 N4 1.355(10) . ?
F2 C9 1.356(9) . ?
F1 C7 1.350(10) . ?
C25 C26 1.371(12) . ?
C25 H25 0.9300 . ?
O8 N8 1.231(11) . ?
C5 C6 1.388(10) . ?
C5 C4 1.406(9) . ?
C4 C9 1.396(10) . ?
N1 C1 1.338(9) . ?
N6 O4 1.180(10) . ?
N6 O5 1.205(11) . ?
N6 C33 1.456(9) . ?
C28 C29 1.437(9) . ?
C28 C33 1.441(9) . ?
N8 O9 1.225(10) . ?
N8 C31 1.464(9) . ?
N4 C12 1.357(13) . ?
N4 C13 1.442(13) . ?
C29 C30 1.382(9) . ?
C33 C32 1.363(10) . ?
C22 C27 1.415(9) . ?
C22 C21 1.452(10) . ?
C14 C15 1.403(13) . ?
C14 C13 1.404(12) . ?
C32 C31 1.383(11) . ?
C32 H32 0.9300 . ?
C30 C31 1.380(10) . ?
C30 H30 0.9300 . ?
F3 C18 1.342(12) . ?
C1 C2 1.361(13) . ?
C1 H1 0.9300 . ?
C26 C27 1.362(12) . ?
C26 H26 0.9300 . ?
F4 C16 1.375(14) . ?
C13 C18 1.371(15) . ?
C27 H27 0.9300 . ?
C6 C7 1.390(10) . ?
C6 H6 0.9300 . ?
C15 C16 1.374(13) . ?
C15 H15 0.9300 . ?
C2 C3 1.388(14) . ?
C2 H2 0.9300 . ?
C7 C8 1.384(13) . ?
C8 C9 1.361(13) . ?
C8 H8 0.9300 . ?
C18 C17 1.332(19) . ?
C3 H3 0.9300 . ?
C10 C11 1.407(16) . ?
C10 H10 0.9300 . ?
C16 C17 1.385(18) . ?
C17 H17 0.9300 . ?
C12 C11 1.33(2) . ?
C12 H12 0.9300 . ?
C19 C20 1.505(13) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C11 H11 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
C14 Ir01 N1 95.8(3) . . ?
C14 Ir01 C5 87.5(3) . . ?
N1 Ir01 C5 80.0(3) . . ?
C14 Ir01 N3 80.4(3) . . ?
N1 Ir01 N3 175.1(2) . . ?
C5 Ir01 N3 96.6(3) . . ?
C14 Ir01 N5 94.4(3) . . ?
N1 Ir01 N5 94.5(3) . . ?
C5 Ir01 N5 174.4(3) . . ?
N3 Ir01 N5 88.9(3) . . ?
C14 Ir01 O2 175.1(3) . . ?
N1 Ir01 O2 89.1(2) . . ?
C5 Ir01 O2 94.2(2) . . ?
N3 Ir01 O2 94.8(2) . . ?
N5 Ir01 O2 84.4(2) . . ?
C28 O3 H100 109.5 . . ?
C23 O2 Ir01 128.2(4) . . ?
O2 C23 C24 117.9(6) . . ?
O2 C23 C22 122.1(6) . . ?
C24 C23 C22 120.0(6) . . ?
C25 C24 C23 120.7(7) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C3 N2 N1 109.6(7) . . ?
C3 N2 C4 135.4(7) . . ?
N1 N2 C4 114.8(5) . . ?
C21 O1 C20 108.0(6) . . ?
O7 N7 O6 122.9(7) . . ?
O7 N7 C29 118.3(6) . . ?
O6 N7 C29 118.7(6) . . ?
C21 N5 C19 108.8(6) . . ?
C21 N5 Ir01 128.5(5) . . ?
C19 N5 Ir01 122.7(5) . . ?
C10 N3 N4 107.5(8) . . ?
C10 N3 Ir01 137.4(7) . . ?
N4 N3 Ir01 115.1(5) . . ?
C26 C25 C24 120.4(8) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C6 C5 C4 117.8(6) . . ?
C6 C5 Ir01 128.7(5) . . ?
C4 C5 Ir01 113.5(5) . . ?
C9 C4 C5 120.5(7) . . ?
C9 C4 N2 123.6(7) . . ?
C5 C4 N2 115.8(6) . . ?
C1 N1 N2 106.4(6) . . ?
C1 N1 Ir01 137.6(6) . . ?
N2 N1 Ir01 115.7(4) . . ?
O4 N6 O5 123.2(9) . . ?
O4 N6 C33 119.4(9) . . ?
O5 N6 C33 117.4(7) . . ?
O3 C28 C29 128.6(6) . . ?
O3 C28 C33 119.7(6) . . ?
C29 C28 C33 111.7(6) . . ?
O8 N8 O9 125.1(8) . . ?
O8 N8 C31 117.2(8) . . ?
O9 N8 C31 117.8(8) . . ?
C12 N4 N3 108.7(10) . . ?
C12 N4 C13 136.4(10) . . ?
N3 N4 C13 114.8(6) . . ?
C30 C29 C28 123.6(6) . . ?
C30 C29 N7 117.0(6) . . ?
C28 C29 N7 119.4(6) . . ?
C32 C33 C28 126.1(7) . . ?
C32 C33 N6 118.5(6) . . ?
C28 C33 N6 115.4(6) . . ?
C23 C22 C27 117.4(7) . . ?
C23 C22 C21 124.8(6) . . ?
C27 C22 C21 117.8(6) . . ?
C15 C14 C13 118.2(8) . . ?
C15 C14 Ir01 127.6(6) . . ?
C13 C14 Ir01 114.1(7) . . ?
C33 C32 C31 117.3(7) . . ?
C33 C32 H32 121.4 . . ?
C31 C32 H32 121.4 . . ?
C31 C30 C29 119.0(6) . . ?
C31 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?
N1 C1 C2 110.9(8) . . ?
N1 C1 H1 124.6 . . ?
C2 C1 H1 124.6 . . ?
C27 C26 C25 119.4(7) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C18 C13 C14 120.8(10) . . ?
C18 C13 N4 123.7(9) . . ?
C14 C13 N4 115.5(8) . . ?
C26 C27 C22 122.1(7) . . ?
C26 C27 H27 118.9 . . ?
C22 C27 H27 118.9 . . ?
C30 C31 C32 122.1(6) . . ?
C30 C31 N8 119.3(7) . . ?
C32 C31 N8 118.6(7) . . ?
C7 C6 C5 119.4(7) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C16 C15 C14 117.9(10) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
N5 C21 O1 114.5(7) . . ?
N5 C21 C22 128.9(6) . . ?
O1 C21 C22 116.6(6) . . ?
C1 C2 C3 106.4(8) . . ?
C1 C2 H2 126.8 . . ?
C3 C2 H2 126.8 . . ?
F1 C7 C8 118.6(7) . . ?
F1 C7 C6 118.0(8) . . ?
C8 C7 C6 123.4(8) . . ?
C9 C8 C7 116.7(7) . . ?
C9 C8 H8 121.6 . . ?
C7 C8 H8 121.6 . . ?
C17 C18 F3 117.5(11) . . ?
C17 C18 C13 121.6(10) . . ?
F3 C18 C13 120.8(12) . . ?
N2 C3 C2 106.7(8) . . ?
N2 C3 H3 126.6 . . ?
C2 C3 H3 126.6 . . ?
F2 C9 C8 119.1(7) . . ?
F2 C9 C4 118.8(8) . . ?
C8 C9 C4 122.1(7) . . ?
N3 C10 C11 109.0(11) . . ?
N3 C10 H10 125.5 . . ?
C11 C10 H10 125.5 . . ?
F4 C16 C15 116.7(11) . . ?
F4 C16 C17 120.1(11) . . ?
C15 C16 C17 123.2(12) . . ?
C18 C17 C16 118.4(10) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C11 C12 N4 108.8(12) . . ?
C11 C12 H12 125.6 . . ?
N4 C12 H12 125.6 . . ?
N5 C19 C20 103.7(8) . . ?
N5 C19 H19A 111.0 . . ?
C20 C19 H19A 111.0 . . ?
N5 C19 H19B 111.0 . . ?
C20 C19 H19B 111.0 . . ?
H19A C19 H19B 109.0 . . ?
O1 C20 C19 104.9(7) . . ?
O1 C20 H20A 110.8 . . ?
C19 C20 H20A 110.8 . . ?
O1 C20 H20B 110.8 . . ?
C19 C20 H20B 110.8 . . ?
H20A C20 H20B 108.8 . . ?
C12 C11 C10 106.0(11) . . ?
C12 C11 H11 127.0 . . ?
C10 C11 H11 127.0 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.847
_refine_diff_density_min         -3.062
_refine_diff_density_rms         0.380
