# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2011

data_global
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Ping Lian'
_publ_contact_author_email       lianping001@yahoo.com.cn
loop_
_publ_author_name
'Zu-Qiang Bian'
'Ping Lian'
'Hui-Bo Wei'
'Chen Zheng'
'Yi-Fan Nie'
'Jiang Bian'
'Chunhui Huang'

data_m100109e1
_database_code_depnum_ccdc_archive 'CCDC 781090'
#TrackingRef 'M100109E1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H31 Ir N4 O4'
_chemical_formula_weight         715.80

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'
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)/c

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

_cell_length_a                   15.967(3)
_cell_length_b                   12.373(2)
_cell_length_c                   15.562(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.475(4)
_cell_angle_gamma                90.00
_cell_volume                     2819.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    116(2)
_cell_measurement_reflns_used    10426
_cell_measurement_theta_min      1.4
_cell_measurement_theta_max      27.9

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1416
_exptl_absorpt_coefficient_mu    4.778
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.4483
_exptl_absorpt_correction_T_max  0.7011
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      116(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean 14.63
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20719
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4964
_reflns_number_gt                4384
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0210P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4964
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0536
_refine_ls_wR_factor_gt          0.0527
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.003
_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
Ir1 Ir 0.280091(8) 0.401108(11) 0.207306(8) 0.01105(6) Uani 1 1 d . . .
O1 O 0.18572(15) 0.2730(2) 0.13287(15) 0.0181(6) Uani 1 1 d . . .
O2 O 0.06940(18) 0.1765(2) 0.13712(17) 0.0328(7) Uani 1 1 d . . .
N1 N 0.23186(17) 0.3411(2) 0.30795(18) 0.0127(6) Uani 1 1 d . . .
N2 N 0.14070(18) 0.2023(2) 0.33138(19) 0.0186(7) Uani 1 1 d . . .
N3 N 0.17645(17) 0.5061(2) 0.14064(18) 0.0144(6) Uani 1 1 d . . .
N4 N 0.39122(17) 0.3049(2) 0.27117(17) 0.0133(6) Uani 1 1 d . . .
C1 C 0.2624(2) 0.3688(3) 0.3991(2) 0.0169(8) Uani 1 1 d . . .
H1 H 0.3023 0.4268 0.4213 0.020 Uiso 1 1 calc R . .
C2 C 0.2353(2) 0.3123(3) 0.4592(2) 0.0195(8) Uani 1 1 d . . .
H2 H 0.2571 0.3298 0.5225 0.023 Uiso 1 1 calc R . .
C3 C 0.1749(2) 0.2290(3) 0.4229(2) 0.0200(8) Uani 1 1 d . . .
H3 H 0.1568 0.1892 0.4632 0.024 Uiso 1 1 calc R . .
C4 C 0.1713(2) 0.2592(3) 0.2783(2) 0.0144(7) Uani 1 1 d . . .
C5 C 0.1375(2) 0.2326(3) 0.1743(2) 0.0188(8) Uani 1 1 d . . .
C6 C 0.1124(2) 0.5359(3) 0.1718(2) 0.0198(8) Uani 1 1 d . . .
H6 H 0.1159 0.5082 0.2287 0.024 Uiso 1 1 calc R . .
C7 C 0.0424(3) 0.6053(3) 0.1238(3) 0.0269(10) Uani 1 1 d . . .
H7 H -0.0006 0.6239 0.1476 0.032 Uiso 1 1 calc R . .
C8 C 0.0368(2) 0.6469(3) 0.0393(3) 0.0288(9) Uani 1 1 d . . .
H8 H -0.0104 0.6935 0.0050 0.035 Uiso 1 1 calc R . .
C9 C 0.1028(2) 0.6180(3) 0.0064(3) 0.0242(9) Uani 1 1 d . . .
H9 H 0.1002 0.6459 -0.0501 0.029 Uiso 1 1 calc R . .
C10 C 0.1724(2) 0.5479(3) 0.0573(2) 0.0168(8) Uani 1 1 d . . .
C11 C 0.2480(2) 0.5116(3) 0.0334(2) 0.0164(8) Uani 1 1 d . . .
C12 C 0.2573(2) 0.5418(3) -0.0492(2) 0.0211(8) Uani 1 1 d . . .
H12 H 0.2149 0.5878 -0.0918 0.025 Uiso 1 1 calc R . .
C13 C 0.3303(2) 0.5028(3) -0.0670(2) 0.0252(9) Uani 1 1 d . . .
H13 H 0.3367 0.5218 -0.1220 0.030 Uiso 1 1 calc R . .
C14 C 0.3936(3) 0.4354(3) -0.0029(2) 0.0218(9) Uani 1 1 d . . .
H14 H 0.4424 0.4094 -0.0149 0.026 Uiso 1 1 calc R . .
C15 C 0.3851(2) 0.4061(3) 0.0795(2) 0.0162(8) Uani 1 1 d . . .
H15 H 0.4289 0.3614 0.1221 0.019 Uiso 1 1 calc R . .
C16 C 0.3113(2) 0.4428(3) 0.0995(2) 0.0138(7) Uani 1 1 d . . .
C17 C 0.3935(2) 0.1976(3) 0.2560(2) 0.0164(8) Uani 1 1 d . . .
H17 H 0.3416 0.1646 0.2127 0.020 Uiso 1 1 calc R . .
C18 C 0.4692(2) 0.1357(3) 0.3019(2) 0.0195(8) Uani 1 1 d . . .
H18 H 0.4685 0.0620 0.2900 0.023 Uiso 1 1 calc R . .
C19 C 0.5467(2) 0.1844(3) 0.3664(2) 0.0202(8) Uani 1 1 d . . .
H19 H 0.5992 0.1440 0.3977 0.024 Uiso 1 1 calc R . .
C20 C 0.5452(2) 0.2937(3) 0.3836(2) 0.0195(8) Uani 1 1 d . . .
H20 H 0.5965 0.3272 0.4277 0.023 Uiso 1 1 calc R . .
C21 C 0.4669(2) 0.3535(3) 0.3349(2) 0.0135(7) Uani 1 1 d . . .
C22 C 0.4549(2) 0.4693(3) 0.3453(2) 0.0146(8) Uani 1 1 d . . .
C23 C 0.5228(2) 0.5355(3) 0.4082(2) 0.0190(8) Uani 1 1 d . . .
H23 H 0.5799 0.5068 0.4443 0.023 Uiso 1 1 calc R . .
C24 C 0.5051(2) 0.6432(3) 0.4166(2) 0.0209(8) Uani 1 1 d . . .
H24 H 0.5499 0.6873 0.4587 0.025 Uiso 1 1 calc R . .
C25 C 0.4198(2) 0.6853(3) 0.3617(2) 0.0219(8) Uani 1 1 d . . .
H25 H 0.4076 0.7578 0.3674 0.026 Uiso 1 1 calc R . .
C26 C 0.3525(2) 0.6204(3) 0.2984(2) 0.0188(8) Uani 1 1 d . . .
H26 H 0.2962 0.6507 0.2620 0.023 Uiso 1 1 calc R . .
C27 C 0.3670(2) 0.5105(3) 0.2878(2) 0.0163(8) Uani 1 1 d . . .
O3 O 0.2369(2) 0.9206(3) 0.0054(3) 0.0637(11) Uani 1 1 d . . .
H3A H 0.1884 0.9349 -0.0382 0.096 Uiso 1 1 calc R . .
C28 C 0.2194(4) 0.8727(5) 0.0782(4) 0.0707(18) Uani 1 1 d . . .
H28A H 0.2402 0.7983 0.0851 0.085 Uiso 1 1 calc R . .
H28B H 0.1539 0.8717 0.0609 0.085 Uiso 1 1 calc R . .
C29 C 0.2618(4) 0.9257(6) 0.1656(5) 0.098(3) Uani 1 1 d . . .
H29A H 0.3264 0.9298 0.1821 0.148 Uiso 1 1 calc R . .
H29B H 0.2503 0.8860 0.2127 0.148 Uiso 1 1 calc R . .
H29C H 0.2373 0.9974 0.1611 0.148 Uiso 1 1 calc R . .
O4 O -0.0638(2) 1.0391(3) 0.1344(2) 0.0492(8) Uani 1 1 d . . .
H4 H -0.0304 1.0919 0.1527 0.074 Uiso 1 1 calc R . .
C30 C -0.0117(3) 0.9482(4) 0.1228(3) 0.0483(13) Uani 1 1 d . . .
H30A H 0.0256 0.9716 0.0900 0.058 Uiso 1 1 calc R . .
H30B H -0.0530 0.8925 0.0856 0.058 Uiso 1 1 calc R . .
C31 C 0.0483(3) 0.9032(4) 0.2164(3) 0.0525(14) Uani 1 1 d . . .
H31A H 0.0850 0.9601 0.2552 0.079 Uiso 1 1 calc R . .
H31B H 0.0871 0.8484 0.2085 0.079 Uiso 1 1 calc R . .
H31C H 0.0110 0.8723 0.2456 0.079 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ir1 0.00951(9) 0.01195(9) 0.01146(8) 0.00018(6) 0.00393(6) -0.00029(5)
O1 0.0179(13) 0.0206(15) 0.0158(11) -0.0003(11) 0.0066(11) -0.0017(11)
O2 0.0314(16) 0.041(2) 0.0234(13) -0.0077(14) 0.0084(13) -0.0258(14)
N1 0.0102(15) 0.0128(17) 0.0158(14) 0.0020(13) 0.0061(12) 0.0020(12)
N2 0.0160(16) 0.0206(18) 0.0209(15) 0.0055(15) 0.0093(13) -0.0009(14)
N3 0.0095(15) 0.0169(17) 0.0157(14) -0.0013(13) 0.0038(12) -0.0021(13)
N4 0.0146(15) 0.0154(17) 0.0125(13) 0.0016(13) 0.0080(12) 0.0007(13)
C1 0.0131(19) 0.020(2) 0.0165(17) -0.0011(16) 0.0051(15) -0.0020(15)
C2 0.0190(19) 0.027(2) 0.0126(16) 0.0010(17) 0.0062(15) 0.0015(17)
C3 0.0171(19) 0.026(2) 0.0200(18) 0.0070(17) 0.0103(16) 0.0024(16)
C4 0.0100(17) 0.015(2) 0.0165(17) 0.0008(15) 0.0033(14) 0.0006(14)
C5 0.018(2) 0.020(2) 0.0178(18) 0.0003(17) 0.0066(16) -0.0008(16)
C6 0.0177(19) 0.021(2) 0.0223(18) 0.0036(17) 0.0095(17) 0.0035(16)
C7 0.020(2) 0.029(2) 0.032(2) 0.0064(19) 0.0109(18) 0.0093(17)
C8 0.019(2) 0.032(2) 0.030(2) 0.008(2) 0.0040(18) 0.0108(18)
C9 0.022(2) 0.026(2) 0.0206(19) 0.0102(17) 0.0046(17) 0.0024(17)
C10 0.0138(18) 0.017(2) 0.0151(17) -0.0005(16) 0.0016(15) -0.0050(16)
C11 0.0176(19) 0.016(2) 0.0153(16) -0.0028(16) 0.0056(15) -0.0062(16)
C12 0.021(2) 0.022(2) 0.0164(18) 0.0041(17) 0.0033(16) -0.0050(17)
C13 0.033(2) 0.031(2) 0.0153(18) -0.0015(18) 0.0133(17) -0.0090(19)
C14 0.027(2) 0.023(2) 0.0222(19) -0.0016(18) 0.0169(18) -0.0056(17)
C15 0.0141(19) 0.016(2) 0.0200(18) -0.0029(16) 0.0086(16) -0.0024(15)
C16 0.0144(18) 0.0114(18) 0.0167(17) -0.0018(15) 0.0073(15) -0.0033(15)
C17 0.0182(19) 0.016(2) 0.0183(17) -0.0027(17) 0.0107(15) -0.0016(16)
C18 0.025(2) 0.016(2) 0.0213(18) -0.0007(17) 0.0128(17) 0.0055(16)
C19 0.019(2) 0.024(2) 0.0207(18) 0.0064(18) 0.0108(16) 0.0112(16)
C20 0.0130(18) 0.026(2) 0.0164(17) 0.0036(18) 0.0025(15) 0.0002(16)
C21 0.0121(18) 0.017(2) 0.0131(16) 0.0026(16) 0.0066(15) 0.0004(15)
C22 0.0155(18) 0.018(2) 0.0123(16) 0.0030(15) 0.0081(15) -0.0001(15)
C23 0.0163(19) 0.021(2) 0.0176(17) 0.0004(17) 0.0042(16) -0.0029(16)
C24 0.023(2) 0.020(2) 0.0196(18) -0.0072(17) 0.0085(17) -0.0102(17)
C25 0.026(2) 0.015(2) 0.0249(19) -0.0015(17) 0.0107(17) -0.0039(17)
C26 0.019(2) 0.016(2) 0.0203(18) 0.0013(16) 0.0065(17) 0.0017(15)
C27 0.0157(19) 0.021(2) 0.0136(16) 0.0053(16) 0.0068(15) 0.0010(16)
O3 0.037(2) 0.092(3) 0.060(2) 0.042(2) 0.0168(18) 0.004(2)
C28 0.052(4) 0.098(5) 0.060(4) -0.001(4) 0.020(3) -0.031(3)
C29 0.062(4) 0.152(8) 0.084(5) -0.061(5) 0.031(4) -0.040(4)
O4 0.0357(18) 0.048(2) 0.064(2) 0.008(2) 0.0193(18) -0.0096(16)
C30 0.034(3) 0.042(3) 0.063(3) -0.008(3) 0.013(3) -0.016(2)
C31 0.047(3) 0.056(4) 0.053(3) 0.005(3) 0.017(3) -0.002(3)

_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 C27 1.985(4) . ?
Ir1 C16 1.999(3) . ?
Ir1 N3 2.033(3) . ?
Ir1 N4 2.037(3) . ?
Ir1 N1 2.135(2) . ?
Ir1 O1 2.175(2) . ?
O1 C5 1.286(4) . ?
O2 C5 1.224(4) . ?
N1 C1 1.347(4) . ?
N1 C4 1.350(4) . ?
N2 C4 1.318(4) . ?
N2 C3 1.348(4) . ?
N3 C6 1.346(4) . ?
N3 C10 1.375(4) . ?
N4 C17 1.351(4) . ?
N4 C21 1.360(4) . ?
C1 C2 1.370(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.524(4) . ?
C6 C7 1.372(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.390(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.467(4) . ?
C11 C12 1.403(4) . ?
C11 C16 1.405(5) . ?
C12 C13 1.389(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.389(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.409(4) . ?
C15 H15 0.9300 . ?
C17 C18 1.367(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.389(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.463(5) . ?
C22 C23 1.399(5) . ?
C22 C27 1.425(4) . ?
C23 C24 1.380(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.390(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.387(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.400(5) . ?
C26 H26 0.9300 . ?
O3 C28 1.402(5) . ?
O3 H3A 0.8200 . ?
C28 C29 1.416(7) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
O4 C30 1.453(5) . ?
O4 H4 0.8200 . ?
C30 C31 1.495(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C27 Ir1 C16 90.48(13) . . ?
C27 Ir1 N3 96.24(13) . . ?
C16 Ir1 N3 80.27(12) . . ?
C27 Ir1 N4 80.60(13) . . ?
C16 Ir1 N4 95.78(12) . . ?
N3 Ir1 N4 174.96(10) . . ?
C27 Ir1 N1 98.05(11) . . ?
C16 Ir1 N1 171.44(12) . . ?
N3 Ir1 N1 97.95(10) . . ?
N4 Ir1 N1 86.42(10) . . ?
C27 Ir1 O1 173.88(10) . . ?
C16 Ir1 O1 95.29(11) . . ?
N3 Ir1 O1 86.75(10) . . ?
N4 Ir1 O1 96.77(10) . . ?
N1 Ir1 O1 76.21(9) . . ?
C5 O1 Ir1 116.3(2) . . ?
C1 N1 C4 117.4(3) . . ?
C1 N1 Ir1 126.8(2) . . ?
C4 N1 Ir1 115.4(2) . . ?
C4 N2 C3 115.9(3) . . ?
C6 N3 C10 118.7(3) . . ?
C6 N3 Ir1 124.9(2) . . ?
C10 N3 Ir1 116.4(2) . . ?
C17 N4 C21 118.9(3) . . ?
C17 N4 Ir1 124.6(2) . . ?
C21 N4 Ir1 116.4(2) . . ?
N1 C1 C2 120.6(3) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 117.7(3) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
N2 C3 C2 122.9(3) . . ?
N2 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
N2 C4 N1 125.5(3) . . ?
N2 C4 C5 119.2(3) . . ?
N1 C4 C5 115.3(3) . . ?
O2 C5 O1 125.5(3) . . ?
O2 C5 C4 119.7(3) . . ?
O1 C5 C4 114.8(3) . . ?
N3 C6 C7 123.1(3) . . ?
N3 C6 H6 118.4 . . ?
C7 C6 H6 118.4 . . ?
C6 C7 C8 118.8(3) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C7 C8 C9 119.0(4) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
N3 C10 C9 120.1(3) . . ?
N3 C10 C11 112.9(3) . . ?
C9 C10 C11 127.0(3) . . ?
C12 C11 C16 121.6(3) . . ?
C12 C11 C10 123.3(3) . . ?
C16 C11 C10 115.1(3) . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 119.7(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.9(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C16 121.1(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C11 C16 C15 117.0(3) . . ?
C11 C16 Ir1 115.1(2) . . ?
C15 C16 Ir1 127.8(3) . . ?
N4 C17 C18 122.6(3) . . ?
N4 C17 H17 118.7 . . ?
C18 C17 H17 118.7 . . ?
C17 C18 C19 119.0(4) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C20 C19 C18 119.2(3) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
N4 C21 C20 120.5(3) . . ?
N4 C21 C22 113.4(3) . . ?
C20 C21 C22 126.2(3) . . ?
C23 C22 C27 121.7(3) . . ?
C23 C22 C21 123.5(3) . . ?
C27 C22 C21 114.8(3) . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.4(3) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 120.8(4) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 121.9(3) . . ?
C25 C26 H26 119.0 . . ?
C27 C26 H26 119.0 . . ?
C26 C27 C22 116.1(3) . . ?
C26 C27 Ir1 129.0(3) . . ?
C22 C27 Ir1 114.8(3) . . ?
C28 O3 H3A 109.5 . . ?
O3 C28 C29 114.0(5) . . ?
O3 C28 H28A 108.7 . . ?
C29 C28 H28A 108.7 . . ?
O3 C28 H28B 108.7 . . ?
C29 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
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 . . ?
C30 O4 H4 109.5 . . ?
O4 C30 C31 110.1(4) . . ?
O4 C30 H30A 109.6 . . ?
C31 C30 H30A 109.6 . . ?
O4 C30 H30B 109.6 . . ?
C31 C30 H30B 109.6 . . ?
H30A C30 H30B 108.2 . . ?
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 . . ?

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
C27 Ir1 O1 C5 29.4(11) . . . . ?
C16 Ir1 O1 C5 -170.0(2) . . . . ?
N3 Ir1 O1 C5 -90.1(2) . . . . ?
N4 Ir1 O1 C5 93.5(2) . . . . ?
N1 Ir1 O1 C5 8.9(2) . . . . ?
C27 Ir1 N1 C1 -5.0(3) . . . . ?
C16 Ir1 N1 C1 -179.9(7) . . . . ?
N3 Ir1 N1 C1 -102.5(3) . . . . ?
N4 Ir1 N1 C1 75.0(3) . . . . ?
O1 Ir1 N1 C1 172.8(3) . . . . ?
C27 Ir1 N1 C4 -177.7(2) . . . . ?
C16 Ir1 N1 C4 7.5(9) . . . . ?
N3 Ir1 N1 C4 84.8(2) . . . . ?
N4 Ir1 N1 C4 -97.7(2) . . . . ?
O1 Ir1 N1 C4 0.2(2) . . . . ?
C27 Ir1 N3 C6 -87.5(3) . . . . ?
C16 Ir1 N3 C6 -176.9(3) . . . . ?
N4 Ir1 N3 C6 -138.3(11) . . . . ?
N1 Ir1 N3 C6 11.6(3) . . . . ?
O1 Ir1 N3 C6 87.2(3) . . . . ?
C27 Ir1 N3 C10 93.1(2) . . . . ?
C16 Ir1 N3 C10 3.7(2) . . . . ?
N4 Ir1 N3 C10 42.3(13) . . . . ?
N1 Ir1 N3 C10 -167.8(2) . . . . ?
O1 Ir1 N3 C10 -92.2(2) . . . . ?
C27 Ir1 N4 C17 179.3(3) . . . . ?
C16 Ir1 N4 C17 -91.2(3) . . . . ?
N3 Ir1 N4 C17 -129.3(11) . . . . ?
N1 Ir1 N4 C17 80.5(2) . . . . ?
O1 Ir1 N4 C17 4.9(2) . . . . ?
C27 Ir1 N4 C21 0.9(2) . . . . ?
C16 Ir1 N4 C21 90.5(2) . . . . ?
N3 Ir1 N4 C21 52.3(12) . . . . ?
N1 Ir1 N4 C21 -97.8(2) . . . . ?
O1 Ir1 N4 C21 -173.5(2) . . . . ?
C4 N1 C1 C2 2.6(5) . . . . ?
Ir1 N1 C1 C2 -169.9(2) . . . . ?
N1 C1 C2 C3 -1.4(5) . . . . ?
C4 N2 C3 C2 2.3(5) . . . . ?
C1 C2 C3 N2 -1.1(5) . . . . ?
C3 N2 C4 N1 -1.0(5) . . . . ?
C3 N2 C4 C5 178.7(3) . . . . ?
C1 N1 C4 N2 -1.4(5) . . . . ?
Ir1 N1 C4 N2 172.0(3) . . . . ?
C1 N1 C4 C5 178.9(3) . . . . ?
Ir1 N1 C4 C5 -7.8(4) . . . . ?
Ir1 O1 C5 O2 164.7(3) . . . . ?
Ir1 O1 C5 C4 -15.4(4) . . . . ?
N2 C4 C5 O2 15.7(5) . . . . ?
N1 C4 C5 O2 -164.5(3) . . . . ?
N2 C4 C5 O1 -164.2(3) . . . . ?
N1 C4 C5 O1 15.5(4) . . . . ?
C10 N3 C6 C7 0.8(5) . . . . ?
Ir1 N3 C6 C7 -178.6(3) . . . . ?
N3 C6 C7 C8 0.0(6) . . . . ?
C6 C7 C8 C9 -0.6(6) . . . . ?
C7 C8 C9 C10 0.5(6) . . . . ?
C6 N3 C10 C9 -0.9(5) . . . . ?
Ir1 N3 C10 C9 178.5(3) . . . . ?
C6 N3 C10 C11 178.0(3) . . . . ?
Ir1 N3 C10 C11 -2.5(4) . . . . ?
C8 C9 C10 N3 0.2(6) . . . . ?
C8 C9 C10 C11 -178.5(4) . . . . ?
N3 C10 C11 C12 178.7(3) . . . . ?
C9 C10 C11 C12 -2.5(6) . . . . ?
N3 C10 C11 C16 -1.0(4) . . . . ?
C9 C10 C11 C16 177.9(4) . . . . ?
C16 C11 C12 C13 0.4(5) . . . . ?
C10 C11 C12 C13 -179.2(3) . . . . ?
C11 C12 C13 C14 -0.7(6) . . . . ?
C12 C13 C14 C15 0.1(6) . . . . ?
C13 C14 C15 C16 0.9(5) . . . . ?
C12 C11 C16 C15 0.5(5) . . . . ?
C10 C11 C16 C15 -179.9(3) . . . . ?
C12 C11 C16 Ir1 -175.6(3) . . . . ?
C10 C11 C16 Ir1 4.0(4) . . . . ?
C14 C15 C16 C11 -1.1(5) . . . . ?
C14 C15 C16 Ir1 174.4(3) . . . . ?
C27 Ir1 C16 C11 -100.4(3) . . . . ?
N3 Ir1 C16 C11 -4.1(3) . . . . ?
N4 Ir1 C16 C11 179.0(3) . . . . ?
N1 Ir1 C16 C11 74.5(9) . . . . ?
O1 Ir1 C16 C11 81.6(3) . . . . ?
C27 Ir1 C16 C15 84.0(3) . . . . ?
N3 Ir1 C16 C15 -179.7(3) . . . . ?
N4 Ir1 C16 C15 3.4(3) . . . . ?
N1 Ir1 C16 C15 -101.0(8) . . . . ?
O1 Ir1 C16 C15 -93.9(3) . . . . ?
C21 N4 C17 C18 -0.4(4) . . . . ?
Ir1 N4 C17 C18 -178.7(2) . . . . ?
N4 C17 C18 C19 -0.1(5) . . . . ?
C17 C18 C19 C20 0.9(5) . . . . ?
C18 C19 C20 C21 -1.3(5) . . . . ?
C17 N4 C21 C20 0.0(4) . . . . ?
Ir1 N4 C21 C20 178.4(2) . . . . ?
C17 N4 C21 C22 -179.3(3) . . . . ?
Ir1 N4 C21 C22 -0.9(3) . . . . ?
C19 C20 C21 N4 0.8(5) . . . . ?
C19 C20 C21 C22 -180.0(3) . . . . ?
N4 C21 C22 C23 178.6(3) . . . . ?
C20 C21 C22 C23 -0.6(5) . . . . ?
N4 C21 C22 C27 0.2(4) . . . . ?
C20 C21 C22 C27 -179.1(3) . . . . ?
C27 C22 C23 C24 0.9(5) . . . . ?
C21 C22 C23 C24 -177.4(3) . . . . ?
C22 C23 C24 C25 -0.5(5) . . . . ?
C23 C24 C25 C26 -0.3(5) . . . . ?
C24 C25 C26 C27 0.7(5) . . . . ?
C25 C26 C27 C22 -0.3(5) . . . . ?
C25 C26 C27 Ir1 176.7(2) . . . . ?
C23 C22 C27 C26 -0.5(4) . . . . ?
C21 C22 C27 C26 178.0(3) . . . . ?
C23 C22 C27 Ir1 -177.9(2) . . . . ?
C21 C22 C27 Ir1 0.6(3) . . . . ?
C16 Ir1 C27 C26 86.4(3) . . . . ?
N3 Ir1 C27 C26 6.2(3) . . . . ?
N4 Ir1 C27 C26 -177.8(3) . . . . ?
N1 Ir1 C27 C26 -92.8(3) . . . . ?
O1 Ir1 C27 C26 -112.9(10) . . . . ?
C16 Ir1 C27 C22 -96.6(2) . . . . ?
N3 Ir1 C27 C22 -176.9(2) . . . . ?
N4 Ir1 C27 C22 -0.8(2) . . . . ?
N1 Ir1 C27 C22 84.2(2) . . . . ?
O1 Ir1 C27 C22 64.1(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.110
_refine_diff_density_min         -0.898
_refine_diff_density_rms         0.100

# Attachment 'sa.cif'

data_sa
_database_code_depnum_ccdc_archive 'CCDC 781091'
#TrackingRef 'sa.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H15 F4 Ir N4 O2'
_chemical_formula_sum            'C27 H15 F4 Ir N4 O2'
_chemical_formula_weight         695.63

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   'P 1 21/c 1'

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

_cell_length_a                   15.839(3)
_cell_length_b                   12.784(3)
_cell_length_c                   15.651(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.72(3)
_cell_angle_gamma                90.00
_cell_volume                     3065.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    10828
_cell_measurement_theta_min      1.3
_cell_measurement_theta_max      27.9

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336
_exptl_absorpt_coefficient_mu    4.407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2999
_exptl_absorpt_correction_T_max  0.4727
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 14.63
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            27470
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.33
_diffrn_reflns_theta_max         27.89
_reflns_number_total             7274
_reflns_number_gt                6220
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'CrystalStructure 3.8'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0410P)^2^+9.4382P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00163(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         7274
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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
Ir1 Ir 0.288231(13) 0.630446(16) 0.250344(14) 0.01753(9) Uani 1 1 d . . .
F1 F 0.5947(2) 0.5048(3) 0.4388(3) 0.0444(10) Uani 1 1 d . . .
F2 F 0.3806(3) 0.2434(3) 0.3754(3) 0.0593(13) Uani 1 1 d . . .
F3 F 0.2127(3) 0.4354(3) -0.0566(3) 0.0463(11) Uani 1 1 d . . .
F4 F 0.4766(3) 0.6154(3) 0.0064(3) 0.0477(12) Uani 1 1 d . . .
N1 N 0.3988(3) 0.7155(4) 0.2965(3) 0.0199(10) Uani 1 1 d . . .
N2 N 0.1834(3) 0.5384(4) 0.1949(3) 0.0233(10) Uani 1 1 d . . .
N3 N 0.2422(3) 0.6777(4) 0.3616(3) 0.0217(10) Uani 1 1 d . . .
N4 N 0.1527(3) 0.8027(4) 0.4077(3) 0.0267(11) Uani 1 1 d . . .
O1 O 0.2074(3) 0.7652(3) 0.2010(3) 0.0240(9) Uani 1 1 d . . .
O2 O 0.1258(3) 0.8892(4) 0.2398(3) 0.0372(11) Uani 1 1 d . . .
C1 C 0.3675(4) 0.5158(4) 0.3115(4) 0.0219(12) Uani 1 1 d . . .
C2 C 0.4529(4) 0.5491(5) 0.3527(4) 0.0264(13) Uani 1 1 d . . .
C3 C 0.5114(4) 0.4762(5) 0.4001(4) 0.0312(14) Uani 1 1 d . . .
C4 C 0.4897(5) 0.3721(6) 0.4081(5) 0.0409(18) Uani 1 1 d . . .
H4 H 0.5308 0.3233 0.4404 0.049 Uiso 1 1 calc R . .
C5 C 0.4053(5) 0.3434(5) 0.3667(4) 0.0377(16) Uani 1 1 d . . .
C6 C 0.3439(4) 0.4122(5) 0.3175(4) 0.0278(13) Uani 1 1 d . . .
H6 H 0.2869 0.3887 0.2886 0.033 Uiso 1 1 calc R . .
C7 C 0.4711(4) 0.6601(5) 0.3434(4) 0.0244(12) Uani 1 1 d . . .
C8 C 0.5500(4) 0.7129(6) 0.3718(4) 0.0366(16) Uani 1 1 d . . .
H8 H 0.6006 0.6767 0.4038 0.044 Uiso 1 1 calc R . .
C9 C 0.5548(5) 0.8189(6) 0.3534(5) 0.0411(18) Uani 1 1 d . . .
H9 H 0.6087 0.8550 0.3733 0.049 Uiso 1 1 calc R . .
C10 C 0.4835(5) 0.8707(5) 0.3074(4) 0.0333(16) Uani 1 1 d . . .
H10 H 0.4869 0.9425 0.2931 0.040 Uiso 1 1 calc R . .
C11 C 0.4062(4) 0.8175(5) 0.2816(4) 0.0279(13) Uani 1 1 d . . .
H11 H 0.3555 0.8550 0.2517 0.034 Uiso 1 1 calc R . .
C12 C 0.3191(4) 0.5908(4) 0.1368(4) 0.0212(11) Uani 1 1 d . . .
C13 C 0.2564(4) 0.5283(5) 0.0804(4) 0.0260(13) Uani 1 1 d . . .
C14 C 0.2710(4) 0.4973(5) -0.0009(4) 0.0321(14) Uani 1 1 d . . .
C15 C 0.3448(4) 0.5254(5) -0.0263(4) 0.0329(15) Uani 1 1 d . . .
H15 H 0.3545 0.5038 -0.0812 0.040 Uiso 1 1 calc R . .
C16 C 0.4029(4) 0.5857(5) 0.0315(4) 0.0321(14) Uani 1 1 d . . .
C17 C 0.3934(4) 0.6185(4) 0.1111(4) 0.0246(13) Uani 1 1 d . . .
H17 H 0.4373 0.6600 0.1487 0.029 Uiso 1 1 calc R . .
C18 C 0.1787(4) 0.4999(5) 0.1114(4) 0.0230(12) Uani 1 1 d . . .
C19 C 0.1069(4) 0.4443(5) 0.0669(5) 0.0367(16) Uani 1 1 d . . .
H19 H 0.1043 0.4181 0.0095 0.044 Uiso 1 1 calc R . .
C20 C 0.0391(4) 0.4261(6) 0.1042(5) 0.0451(18) Uani 1 1 d . . .
H20 H -0.0108 0.3882 0.0728 0.054 Uiso 1 1 calc R . .
C21 C 0.0439(5) 0.4637(6) 0.1885(5) 0.0457(19) Uani 1 1 d . . .
H21 H -0.0020 0.4510 0.2161 0.055 Uiso 1 1 calc R . .
C22 C 0.1156(4) 0.5189(5) 0.2306(4) 0.0322(14) Uani 1 1 d . . .
H22 H 0.1184 0.5451 0.2880 0.039 Uiso 1 1 calc R . .
C23 C 0.1721(4) 0.8111(5) 0.2556(4) 0.0246(12) Uani 1 1 d . . .
C24 C 0.1892(4) 0.7626(4) 0.3478(4) 0.0208(11) Uani 1 1 d . . .
C25 C 0.2605(4) 0.6318(5) 0.4413(4) 0.0279(14) Uani 1 1 d . . .
H25 H 0.2973 0.5721 0.4524 0.033 Uiso 1 1 calc R . .
C26 C 0.2261(4) 0.6708(5) 0.5070(4) 0.0314(14) Uani 1 1 d . . .
H26 H 0.2398 0.6406 0.5644 0.038 Uiso 1 1 calc R . .
C27 C 0.1715(4) 0.7546(5) 0.4866(4) 0.0296(14) Uani 1 1 d . . .
H27 H 0.1453 0.7805 0.5306 0.036 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ir1 0.01253(13) 0.02412(14) 0.01689(13) 0.00128(8) 0.00549(9) 0.00222(7)
F1 0.016(2) 0.070(3) 0.042(2) 0.007(2) -0.0033(18) 0.0116(18)
F2 0.069(3) 0.025(2) 0.067(3) 0.005(2) -0.014(3) 0.007(2)
F3 0.044(3) 0.065(3) 0.030(2) -0.0205(19) 0.010(2) -0.024(2)
F4 0.046(3) 0.065(3) 0.046(3) -0.020(2) 0.036(2) -0.027(2)
N1 0.012(2) 0.029(3) 0.017(2) -0.0025(19) 0.0025(19) -0.0046(17)
N2 0.015(2) 0.030(3) 0.025(3) 0.004(2) 0.004(2) -0.0023(18)
N3 0.017(2) 0.034(3) 0.014(2) 0.0034(19) 0.0032(19) 0.0046(19)
N4 0.027(3) 0.035(3) 0.021(3) 0.000(2) 0.012(2) 0.007(2)
O1 0.022(2) 0.030(2) 0.022(2) 0.0107(17) 0.0091(18) 0.0143(16)
O2 0.036(3) 0.046(3) 0.032(3) 0.008(2) 0.013(2) 0.021(2)
C1 0.016(3) 0.032(3) 0.019(3) 0.002(2) 0.005(2) 0.004(2)
C2 0.008(3) 0.049(4) 0.022(3) 0.000(3) 0.003(2) 0.009(2)
C3 0.018(3) 0.046(4) 0.029(3) -0.001(3) 0.006(3) 0.012(3)
C4 0.035(4) 0.052(5) 0.033(4) 0.003(3) 0.005(3) 0.024(3)
C5 0.045(4) 0.035(4) 0.027(4) 0.001(3) -0.001(3) 0.013(3)
C6 0.024(3) 0.023(3) 0.032(3) 0.000(3) 0.000(3) 0.004(2)
C7 0.014(3) 0.041(3) 0.019(3) -0.006(2) 0.006(2) 0.003(2)
C8 0.018(3) 0.064(5) 0.028(4) -0.009(3) 0.005(3) -0.003(3)
C9 0.032(4) 0.058(5) 0.036(4) -0.015(3) 0.011(3) -0.023(3)
C10 0.039(4) 0.039(4) 0.026(3) -0.007(3) 0.016(3) -0.017(3)
C11 0.032(4) 0.029(3) 0.027(3) -0.002(2) 0.013(3) -0.005(2)
C12 0.020(3) 0.028(3) 0.015(3) 0.005(2) 0.003(2) 0.002(2)
C13 0.018(3) 0.030(3) 0.030(3) 0.000(2) 0.008(3) 0.004(2)
C14 0.025(3) 0.042(4) 0.026(3) -0.003(3) 0.002(3) -0.006(3)
C15 0.029(4) 0.050(4) 0.022(3) -0.007(3) 0.012(3) -0.007(3)
C16 0.031(4) 0.041(4) 0.030(4) -0.008(3) 0.017(3) -0.007(3)
C17 0.021(3) 0.033(3) 0.023(3) -0.006(2) 0.012(3) -0.003(2)
C18 0.012(3) 0.032(3) 0.024(3) 0.000(2) 0.004(2) -0.001(2)
C19 0.025(4) 0.049(4) 0.033(4) -0.006(3) 0.001(3) -0.010(3)
C20 0.020(4) 0.062(5) 0.051(5) -0.005(4) 0.006(3) -0.015(3)
C21 0.020(4) 0.067(5) 0.055(5) 0.001(4) 0.017(4) -0.008(3)
C22 0.019(3) 0.050(4) 0.029(4) 0.000(3) 0.010(3) -0.003(3)
C23 0.017(3) 0.029(3) 0.028(3) 0.004(2) 0.007(3) 0.005(2)
C24 0.014(3) 0.031(3) 0.019(3) -0.001(2) 0.007(2) 0.002(2)
C25 0.024(3) 0.038(4) 0.025(3) 0.006(2) 0.010(3) 0.013(2)
C26 0.034(4) 0.045(4) 0.016(3) 0.000(3) 0.009(3) 0.008(3)
C27 0.024(3) 0.042(4) 0.025(3) -0.003(3) 0.011(3) 0.004(3)

_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 C1 2.007(6) . ?
Ir1 C12 2.024(5) . ?
Ir1 N1 2.031(4) . ?
Ir1 N2 2.041(5) . ?
Ir1 N3 2.139(4) . ?
Ir1 O1 2.168(4) . ?
F1 C3 1.355(7) . ?
F2 C5 1.353(8) . ?
F3 C14 1.353(7) . ?
F4 C16 1.376(7) . ?
N1 C11 1.336(7) . ?
N1 C7 1.388(7) . ?
N2 C22 1.354(7) . ?
N2 C18 1.380(7) . ?
N3 C25 1.342(7) . ?
N3 C24 1.355(7) . ?
N4 C24 1.323(7) . ?
N4 C27 1.343(8) . ?
O1 C23 1.278(7) . ?
O2 C23 1.226(7) . ?
C1 C6 1.386(8) . ?
C1 C2 1.409(8) . ?
C2 C3 1.388(8) . ?
C2 C7 1.463(9) . ?
C3 C4 1.388(9) . ?
C4 C5 1.379(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(8) . ?
C8 C9 1.391(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.349(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.369(8) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.384(7) . ?
C12 C13 1.399(8) . ?
C13 C14 1.407(8) . ?
C13 C18 1.478(7) . ?
C14 C15 1.375(8) . ?
C15 C16 1.355(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.360(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.372(8) . ?
C19 C20 1.366(9) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(10) . ?
C20 H20 0.9500 . ?
C21 C22 1.357(9) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.531(8) . ?
C25 C26 1.374(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.363(9) . ?
C26 H26 0.9500 . ?
C27 H27 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
C1 Ir1 C12 88.6(2) . . ?
C1 Ir1 N1 81.0(2) . . ?
C12 Ir1 N1 93.9(2) . . ?
C1 Ir1 N2 97.2(2) . . ?
C12 Ir1 N2 80.4(2) . . ?
N1 Ir1 N2 174.09(18) . . ?
C1 Ir1 N3 96.9(2) . . ?
C12 Ir1 N3 173.8(2) . . ?
N1 Ir1 N3 90.05(18) . . ?
N2 Ir1 N3 95.75(18) . . ?
C1 Ir1 O1 172.38(19) . . ?
C12 Ir1 O1 97.92(18) . . ?
N1 Ir1 O1 94.53(17) . . ?
N2 Ir1 O1 87.91(18) . . ?
N3 Ir1 O1 76.90(16) . . ?
C11 N1 C7 119.5(5) . . ?
C11 N1 Ir1 124.5(4) . . ?
C7 N1 Ir1 115.9(4) . . ?
C22 N2 C18 117.9(5) . . ?
C22 N2 Ir1 125.1(4) . . ?
C18 N2 Ir1 116.7(3) . . ?
C25 N3 C24 118.5(5) . . ?
C25 N3 Ir1 126.6(4) . . ?
C24 N3 Ir1 115.0(3) . . ?
C24 N4 C27 116.1(5) . . ?
C23 O1 Ir1 116.5(3) . . ?
C6 C1 C2 120.1(5) . . ?
C6 C1 Ir1 125.7(4) . . ?
C2 C1 Ir1 114.2(4) . . ?
C3 C2 C1 118.4(6) . . ?
C3 C2 C7 125.6(6) . . ?
C1 C2 C7 116.0(5) . . ?
F1 C3 C4 117.0(6) . . ?
F1 C3 C2 120.0(6) . . ?
C4 C3 C2 123.0(6) . . ?
C5 C4 C3 116.5(6) . . ?
C5 C4 H4 121.8 . . ?
C3 C4 H4 121.8 . . ?
F2 C5 C4 118.3(6) . . ?
F2 C5 C6 118.3(6) . . ?
C4 C5 C6 123.4(7) . . ?
C1 C6 C5 118.7(6) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N1 C7 C8 118.4(6) . . ?
N1 C7 C2 112.9(5) . . ?
C8 C7 C2 128.6(6) . . ?
C7 C8 C9 119.9(6) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.4(6) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 118.6(6) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
N1 C11 C10 123.1(6) . . ?
N1 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C17 C12 C13 118.9(5) . . ?
C17 C12 Ir1 127.1(4) . . ?
C13 C12 Ir1 113.9(4) . . ?
C12 C13 C14 118.5(5) . . ?
C12 C13 C18 116.8(5) . . ?
C14 C13 C18 124.7(6) . . ?
F3 C14 C15 117.2(6) . . ?
F3 C14 C13 120.4(5) . . ?
C15 C14 C13 122.4(6) . . ?
C16 C15 C14 116.0(6) . . ?
C16 C15 H15 122.0 . . ?
C14 C15 H15 122.0 . . ?
C15 C16 C17 125.0(6) . . ?
C15 C16 F4 116.6(5) . . ?
C17 C16 F4 118.4(6) . . ?
C16 C17 C12 119.2(6) . . ?
C16 C17 H17 120.4 . . ?
C12 C17 H17 120.4 . . ?
C19 C18 N2 120.1(5) . . ?
C19 C18 C13 127.9(6) . . ?
N2 C18 C13 112.0(5) . . ?
C20 C19 C18 120.8(6) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 119.2(7) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C22 C21 C20 118.6(6) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
N2 C22 C21 123.3(6) . . ?
N2 C22 H22 118.4 . . ?
C21 C22 H22 118.4 . . ?
O2 C23 O1 125.5(5) . . ?
O2 C23 C24 118.3(5) . . ?
O1 C23 C24 116.2(5) . . ?
N4 C24 N3 124.2(5) . . ?
N4 C24 C23 120.4(5) . . ?
N3 C24 C23 115.4(4) . . ?
N3 C25 C26 120.3(5) . . ?
N3 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 117.3(6) . . ?
C27 C26 H26 121.4 . . ?
C25 C26 H26 121.4 . . ?
N4 C27 C26 123.7(5) . . ?
N4 C27 H27 118.2 . . ?
C26 C27 H27 118.2 . . ?

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
C1 Ir1 N1 C11 178.0(5) . . . . ?
C12 Ir1 N1 C11 90.1(5) . . . . ?
N2 Ir1 N1 C11 106.0(18) . . . . ?
N3 Ir1 N1 C11 -85.1(4) . . . . ?
O1 Ir1 N1 C11 -8.2(4) . . . . ?
C1 Ir1 N1 C7 0.7(4) . . . . ?
C12 Ir1 N1 C7 -87.2(4) . . . . ?
N2 Ir1 N1 C7 -71.3(19) . . . . ?
N3 Ir1 N1 C7 97.6(4) . . . . ?
O1 Ir1 N1 C7 174.5(4) . . . . ?
C1 Ir1 N2 C22 94.4(5) . . . . ?
C12 Ir1 N2 C22 -178.3(5) . . . . ?
N1 Ir1 N2 C22 165.6(16) . . . . ?
N3 Ir1 N2 C22 -3.3(5) . . . . ?
O1 Ir1 N2 C22 -79.9(5) . . . . ?
C1 Ir1 N2 C18 -90.7(4) . . . . ?
C12 Ir1 N2 C18 -3.4(4) . . . . ?
N1 Ir1 N2 C18 -20(2) . . . . ?
N3 Ir1 N2 C18 171.6(4) . . . . ?
O1 Ir1 N2 C18 95.0(4) . . . . ?
C1 Ir1 N3 C25 -4.8(5) . . . . ?
C12 Ir1 N3 C25 145.3(17) . . . . ?
N1 Ir1 N3 C25 -85.7(5) . . . . ?
N2 Ir1 N3 C25 93.1(5) . . . . ?
O1 Ir1 N3 C25 179.6(5) . . . . ?
C1 Ir1 N3 C24 175.4(4) . . . . ?
C12 Ir1 N3 C24 -35(2) . . . . ?
N1 Ir1 N3 C24 94.5(4) . . . . ?
N2 Ir1 N3 C24 -86.7(4) . . . . ?
O1 Ir1 N3 C24 -0.2(4) . . . . ?
C1 Ir1 O1 C23 -34.3(16) . . . . ?
C12 Ir1 O1 C23 177.6(4) . . . . ?
N1 Ir1 O1 C23 -87.8(4) . . . . ?
N2 Ir1 O1 C23 97.6(4) . . . . ?
N3 Ir1 O1 C23 1.2(4) . . . . ?
C12 Ir1 C1 C6 -87.5(5) . . . . ?
N1 Ir1 C1 C6 178.3(5) . . . . ?
N2 Ir1 C1 C6 -7.4(5) . . . . ?
N3 Ir1 C1 C6 89.4(5) . . . . ?
O1 Ir1 C1 C6 124.1(13) . . . . ?
C12 Ir1 C1 C2 94.4(4) . . . . ?
N1 Ir1 C1 C2 0.3(4) . . . . ?
N2 Ir1 C1 C2 174.6(4) . . . . ?
N3 Ir1 C1 C2 -88.7(4) . . . . ?
O1 Ir1 C1 C2 -53.9(16) . . . . ?
C6 C1 C2 C3 -1.0(8) . . . . ?
Ir1 C1 C2 C3 177.2(4) . . . . ?
C6 C1 C2 C7 -179.3(5) . . . . ?
Ir1 C1 C2 C7 -1.2(6) . . . . ?
C1 C2 C3 F1 178.3(5) . . . . ?
C7 C2 C3 F1 -3.5(9) . . . . ?
C1 C2 C3 C4 0.4(9) . . . . ?
C7 C2 C3 C4 178.6(6) . . . . ?
F1 C3 C4 C5 -178.5(6) . . . . ?
C2 C3 C4 C5 -0.5(10) . . . . ?
C3 C4 C5 F2 -177.7(6) . . . . ?
C3 C4 C5 C6 1.2(10) . . . . ?
C2 C1 C6 C5 1.6(9) . . . . ?
Ir1 C1 C6 C5 -176.3(5) . . . . ?
F2 C5 C6 C1 177.2(6) . . . . ?
C4 C5 C6 C1 -1.8(10) . . . . ?
C11 N1 C7 C8 -1.4(8) . . . . ?
Ir1 N1 C7 C8 176.0(4) . . . . ?
C11 N1 C7 C2 -178.9(5) . . . . ?
Ir1 N1 C7 C2 -1.5(6) . . . . ?
C3 C2 C7 N1 -176.5(5) . . . . ?
C1 C2 C7 N1 1.7(7) . . . . ?
C3 C2 C7 C8 6.3(10) . . . . ?
C1 C2 C7 C8 -175.4(6) . . . . ?
N1 C7 C8 C9 0.4(8) . . . . ?
C2 C7 C8 C9 177.4(6) . . . . ?
C7 C8 C9 C10 -0.6(10) . . . . ?
C8 C9 C10 C11 1.9(10) . . . . ?
C7 N1 C11 C10 2.8(8) . . . . ?
Ir1 N1 C11 C10 -174.4(4) . . . . ?
C9 C10 C11 N1 -3.0(9) . . . . ?
C1 Ir1 C12 C17 -80.2(5) . . . . ?
N1 Ir1 C12 C17 0.6(5) . . . . ?
N2 Ir1 C12 C17 -177.7(6) . . . . ?
N3 Ir1 C12 C17 129.5(17) . . . . ?
O1 Ir1 C12 C17 95.7(5) . . . . ?
C1 Ir1 C12 C13 99.5(4) . . . . ?
N1 Ir1 C12 C13 -179.6(4) . . . . ?
N2 Ir1 C12 C13 2.0(4) . . . . ?
N3 Ir1 C12 C13 -51(2) . . . . ?
O1 Ir1 C12 C13 -84.5(4) . . . . ?
C17 C12 C13 C14 -0.9(9) . . . . ?
Ir1 C12 C13 C14 179.3(5) . . . . ?
C17 C12 C13 C18 179.3(5) . . . . ?
Ir1 C12 C13 C18 -0.5(7) . . . . ?
C12 C13 C14 F3 178.9(6) . . . . ?
C18 C13 C14 F3 -1.3(10) . . . . ?
C12 C13 C14 C15 0.6(10) . . . . ?
C18 C13 C14 C15 -179.6(6) . . . . ?
F3 C14 C15 C16 -178.8(6) . . . . ?
C13 C14 C15 C16 -0.4(10) . . . . ?
C14 C15 C16 C17 0.5(11) . . . . ?
C14 C15 C16 F4 -179.3(6) . . . . ?
C15 C16 C17 C12 -0.8(11) . . . . ?
F4 C16 C17 C12 178.9(6) . . . . ?
C13 C12 C17 C16 1.0(9) . . . . ?
Ir1 C12 C17 C16 -179.3(5) . . . . ?
C22 N2 C18 C19 0.3(9) . . . . ?
Ir1 N2 C18 C19 -174.9(5) . . . . ?
C22 N2 C18 C13 179.2(5) . . . . ?
Ir1 N2 C18 C13 4.0(6) . . . . ?
C12 C13 C18 C19 176.5(6) . . . . ?
C14 C13 C18 C19 -3.3(10) . . . . ?
C12 C13 C18 N2 -2.3(8) . . . . ?
C14 C13 C18 N2 177.9(6) . . . . ?
N2 C18 C19 C20 0.0(10) . . . . ?
C13 C18 C19 C20 -178.7(7) . . . . ?
C18 C19 C20 C21 -0.7(12) . . . . ?
C19 C20 C21 C22 1.0(12) . . . . ?
C18 N2 C22 C21 0.0(10) . . . . ?
Ir1 N2 C22 C21 174.8(6) . . . . ?
C20 C21 C22 N2 -0.7(12) . . . . ?
Ir1 O1 C23 O2 178.7(5) . . . . ?
Ir1 O1 C23 C24 -1.9(7) . . . . ?
C27 N4 C24 N3 0.6(9) . . . . ?
C27 N4 C24 C23 179.9(5) . . . . ?
C25 N3 C24 N4 -1.2(9) . . . . ?
Ir1 N3 C24 N4 178.6(5) . . . . ?
C25 N3 C24 C23 179.5(5) . . . . ?
Ir1 N3 C24 C23 -0.7(6) . . . . ?
O2 C23 C24 N4 1.8(9) . . . . ?
O1 C23 C24 N4 -177.6(5) . . . . ?
O2 C23 C24 N3 -178.8(6) . . . . ?
O1 C23 C24 N3 1.8(8) . . . . ?
C24 N3 C25 C26 -0.2(9) . . . . ?
Ir1 N3 C25 C26 -180.0(5) . . . . ?
N3 C25 C26 C27 2.0(10) . . . . ?
C24 N4 C27 C26 1.4(9) . . . . ?
C25 C26 C27 N4 -2.7(10) . . . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 -0.006 -0.006 959 304 ' '
_platon_squeeze_details          
;
;

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.89
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.829
_refine_diff_density_min         -2.318
_refine_diff_density_rms         0.163