# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


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#
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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
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#  fide research purposes only. It may contain copyright material 
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data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 909214'
#TrackingRef 'web_deposit_cif_file_0_YuyangZhou_1352100411.shelxl.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H22 Ir N7 O3,0.75(N C2 H3)'
_chemical_formula_sum            'C30.50 H24.25 Ir N7.75 O3'
_chemical_formula_weight         739.53
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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   9.3412(7)
_cell_length_b                   17.4760(13)
_cell_length_c                   17.6846(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.040(2)
_cell_angle_gamma                90.00
_cell_volume                     2886.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      25.3
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1450
_exptl_absorpt_coefficient_mu    4.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1659
_exptl_absorpt_correction_T_max  0.4551
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27366
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         25.35
_reflns_number_total             5271
_reflns_number_gt                4820
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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^)+(0.0319P)^2^+4.3992P] 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         5271
_refine_ls_number_parameters     385
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.123
_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 0.494527(18) 0.290032(10) 0.174758(10) 0.02616(8) Uani 1 1 d . . .
O1 O 0.6963(3) 0.2338(2) 0.19279(19) 0.0362(8) Uani 1 1 d . . .
O2 O 0.8303(4) 0.1746(2) 0.2798(2) 0.0485(10) Uani 1 1 d . . .
O3 O 0.3439(4) 0.3359(3) 0.4666(2) 0.0645(12) Uani 1 1 d . . .
N1 N 0.6257(4) 0.4583(2) 0.1836(2) 0.0353(10) Uani 1 1 d . . .
N2 N 0.6160(4) 0.4038(2) 0.0758(2) 0.0356(10) Uani 1 1 d . . .
N3 N 0.4316(9) 0.1073(4) -0.1465(4) 0.097(2) Uani 1 1 d . . .
N4 N 0.3817(4) 0.1196(2) 0.2005(3) 0.0409(10) Uani 1 1 d . . .
N5 N 0.2272(4) 0.2094(2) 0.1934(2) 0.0332(10) Uani 1 1 d . . .
N6 N 0.0529(7) 0.5683(4) 0.0949(5) 0.099(2) Uani 1 1 d . . .
N7 N 0.5173(4) 0.2885(2) 0.2956(2) 0.0302(10) Uani 1 1 d . . .
C1 C 0.5900(5) 0.3913(3) 0.1505(3) 0.0309(11) Uani 1 1 d . . .
C2 C 0.6183(6) 0.4742(3) 0.2642(3) 0.0516(15) Uani 1 1 d . . .
H2A H 0.5234 0.4637 0.2813 0.077 Uiso 1 1 calc R . .
H2B H 0.6411 0.5270 0.2733 0.077 Uiso 1 1 calc R . .
H2C H 0.6856 0.4423 0.2911 0.077 Uiso 1 1 calc R . .
C3 C 0.6721(6) 0.5110(3) 0.1309(3) 0.0487(14) Uani 1 1 d . . .
H3 H 0.7020 0.5608 0.1409 0.058 Uiso 1 1 calc R . .
C4 C 0.6661(6) 0.4773(3) 0.0630(3) 0.0499(15) Uani 1 1 d . . .
H4 H 0.6905 0.4987 0.0168 0.060 Uiso 1 1 calc R . .
C5 C 0.5775(5) 0.3439(3) 0.0247(3) 0.0348(11) Uani 1 1 d . . .
C6 C 0.6109(6) 0.3450(3) -0.0507(3) 0.0470(14) Uani 1 1 d . . .
H6 H 0.6579 0.3868 -0.0712 0.056 Uiso 1 1 calc R . .
C7 C 0.5740(7) 0.2834(3) -0.0952(3) 0.0475(15) Uani 1 1 d . . .
H7 H 0.5958 0.2830 -0.1463 0.057 Uiso 1 1 calc R . .
C8 C 0.5045(6) 0.2225(3) -0.0635(3) 0.0427(14) Uani 1 1 d . . .
C9 C 0.4709(6) 0.2216(3) 0.0139(3) 0.0380(12) Uani 1 1 d . . .
H9 H 0.4234 0.1797 0.0339 0.046 Uiso 1 1 calc R . .
C10 C 0.5080(5) 0.2829(3) 0.0605(3) 0.0292(11) Uani 1 1 d . . .
C11 C 0.4652(7) 0.1585(4) -0.1096(3) 0.0593(17) Uani 1 1 d . . .
C12 C 0.3705(5) 0.1956(3) 0.1885(3) 0.0329(11) Uani 1 1 d . . .
C13 C 0.5149(6) 0.0760(3) 0.1991(4) 0.0624(18) Uani 1 1 d . . .
H13A H 0.5834 0.1025 0.1689 0.094 Uiso 1 1 calc R . .
H13B H 0.4966 0.0263 0.1778 0.094 Uiso 1 1 calc R . .
H13C H 0.5523 0.0703 0.2497 0.094 Uiso 1 1 calc R . .
C14 C 0.2477(6) 0.0878(3) 0.2137(3) 0.0529(15) Uani 1 1 d . . .
H14 H 0.2289 0.0366 0.2236 0.063 Uiso 1 1 calc R . .
C15 C 0.1509(6) 0.1439(3) 0.2094(3) 0.0459(14) Uani 1 1 d . . .
H15 H 0.0526 0.1398 0.2160 0.055 Uiso 1 1 calc R . .
C16 C 0.1813(5) 0.2856(3) 0.1783(3) 0.0320(11) Uani 1 1 d . . .
C17 C 0.0389(6) 0.3068(3) 0.1753(3) 0.0428(14) Uani 1 1 d . . .
H17 H -0.0322 0.2718 0.1872 0.051 Uiso 1 1 calc R . .
C18 C 0.0041(5) 0.3799(3) 0.1544(3) 0.0475(14) Uani 1 1 d . . .
H18 H -0.0913 0.3949 0.1511 0.057 Uiso 1 1 calc R . .
C19 C 0.1117(5) 0.4312(3) 0.1384(3) 0.0436(13) Uani 1 1 d . . .
C20 C 0.2560(5) 0.4094(3) 0.1441(3) 0.0358(12) Uani 1 1 d . . .
H20 H 0.3262 0.4455 0.1340 0.043 Uiso 1 1 calc R . .
C21 C 0.2978(5) 0.3360(3) 0.1641(2) 0.0285(10) Uani 1 1 d . . .
C22 C 0.0770(6) 0.5078(4) 0.1139(4) 0.0618(18) Uani 1 1 d . . .
C23 C 0.7278(5) 0.2153(3) 0.2609(3) 0.0333(12) Uani 1 1 d . . .
C24 C 0.6302(5) 0.2456(3) 0.3202(3) 0.0337(11) Uani 1 1 d . . .
C25 C 0.6509(6) 0.2297(3) 0.3955(3) 0.0453(14) Uani 1 1 d . . .
H25 H 0.7279 0.1994 0.4110 0.054 Uiso 1 1 calc R . .
C26 C 0.5560(6) 0.2588(4) 0.4497(3) 0.0568(17) Uani 1 1 d . . .
H26 H 0.5691 0.2491 0.5011 0.068 Uiso 1 1 calc R . .
C27 C 0.4446(6) 0.3019(3) 0.4231(3) 0.0448(14) Uani 1 1 d . . .
C28 C 0.4265(6) 0.3158(3) 0.3461(3) 0.0394(12) Uani 1 1 d . . .
H28 H 0.3489 0.3449 0.3294 0.047 Uiso 1 1 calc R . .
C29 C 0.3432(8) 0.3148(5) 0.5456(3) 0.079(2) Uani 1 1 d . . .
H29A H 0.3344 0.2603 0.5500 0.119 Uiso 1 1 calc R . .
H29B H 0.2637 0.3390 0.5697 0.119 Uiso 1 1 calc R . .
H29C H 0.4309 0.3312 0.5697 0.119 Uiso 1 1 calc R . .
N8 N 0.0000 0.0000 1.0000 0.111(4) Uiso 0.50 2 d SPD . 1
C30 C 0.1129(15) 0.016(2) 0.9840(19) 0.094(11) Uiso 0.25 1 d PD A 1
C31 C 0.268(3) 0.005(2) 1.0116(19) 0.091(10) Uiso 0.25 1 d PD A 1
N8A N -0.0139(18) 0.0016(10) 1.0777(9) 0.111(4) Uiso 0.50 1 d PD B 2
C30A C 0.053(2) 0.0185(16) 1.0313(12) 0.149(9) Uiso 0.50 1 d PD . 2
C31A C 0.1880(16) 0.0500(9) 1.0013(9) 0.079(4) Uiso 0.50 1 d PD C 2
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 0.02256(13) 0.02967(13) 0.02630(13) 0.00004(7) 0.00172(8) -0.00004(7)
O1 0.0269(18) 0.044(2) 0.038(2) 0.0023(17) 0.0026(15) 0.0074(16)
O2 0.037(2) 0.053(2) 0.056(2) 0.011(2) -0.0023(18) 0.0118(19)
O3 0.055(3) 0.104(4) 0.035(2) -0.008(2) 0.0168(19) -0.001(2)
N1 0.033(2) 0.029(2) 0.044(3) -0.005(2) -0.0029(19) -0.0009(18)
N2 0.035(2) 0.033(2) 0.039(2) 0.0035(19) -0.0006(19) -0.0063(18)
N3 0.153(7) 0.071(4) 0.065(4) -0.028(4) -0.008(4) -0.001(4)
N4 0.038(2) 0.031(2) 0.054(3) 0.002(2) 0.003(2) -0.001(2)
N5 0.030(2) 0.035(2) 0.034(2) 0.0017(18) 0.0033(19) -0.0061(17)
N6 0.069(4) 0.067(4) 0.161(7) 0.033(5) 0.013(4) 0.022(3)
N7 0.033(2) 0.032(2) 0.026(2) 0.0020(17) 0.0038(18) -0.0037(17)
C1 0.021(2) 0.039(3) 0.033(3) -0.002(2) -0.0010(19) 0.003(2)
C2 0.058(4) 0.048(3) 0.048(4) -0.014(3) -0.002(3) -0.004(3)
C3 0.052(4) 0.034(3) 0.061(4) 0.005(3) -0.001(3) -0.011(3)
C4 0.060(4) 0.039(3) 0.051(4) 0.011(3) 0.002(3) -0.014(3)
C5 0.034(3) 0.039(3) 0.032(3) 0.002(2) -0.001(2) 0.000(2)
C6 0.055(4) 0.054(4) 0.032(3) 0.010(3) 0.005(3) -0.007(3)
C7 0.060(4) 0.061(4) 0.021(3) 0.001(3) 0.005(3) 0.004(3)
C8 0.046(3) 0.050(3) 0.032(3) -0.007(3) -0.006(3) 0.011(3)
C9 0.039(3) 0.040(3) 0.035(3) -0.003(2) -0.002(2) 0.003(2)
C10 0.024(3) 0.037(3) 0.027(3) 0.000(2) 0.000(2) 0.005(2)
C11 0.082(5) 0.059(4) 0.037(3) -0.010(3) 0.003(3) 0.007(4)
C12 0.031(3) 0.038(3) 0.030(3) 0.001(2) -0.001(2) -0.003(2)
C13 0.051(4) 0.035(3) 0.101(5) 0.002(3) 0.012(4) 0.010(3)
C14 0.055(4) 0.035(3) 0.069(4) 0.009(3) 0.000(3) -0.014(3)
C15 0.038(3) 0.044(3) 0.056(4) 0.008(3) 0.003(3) -0.013(3)
C16 0.030(3) 0.037(3) 0.029(3) 0.003(2) 0.001(2) 0.000(2)
C17 0.023(3) 0.053(3) 0.053(4) 0.001(3) 0.004(2) -0.008(3)
C18 0.025(3) 0.057(4) 0.061(4) 0.003(3) 0.000(2) 0.010(3)
C19 0.033(3) 0.045(3) 0.053(3) 0.006(3) 0.005(2) 0.008(2)
C20 0.030(3) 0.037(3) 0.041(3) 0.001(2) 0.006(2) 0.001(2)
C21 0.026(2) 0.035(3) 0.024(2) -0.002(2) 0.0026(19) 0.000(2)
C22 0.036(3) 0.053(4) 0.096(5) 0.014(4) 0.005(3) 0.012(3)
C23 0.025(3) 0.036(3) 0.039(3) 0.008(2) -0.001(2) -0.004(2)
C24 0.032(3) 0.034(3) 0.034(3) 0.003(2) -0.003(2) -0.006(2)
C25 0.042(3) 0.056(3) 0.037(3) 0.009(3) -0.003(3) -0.009(3)
C26 0.048(4) 0.087(5) 0.035(3) 0.018(3) -0.011(3) -0.027(4)
C27 0.046(3) 0.058(4) 0.031(3) -0.006(3) 0.008(3) -0.015(3)
C28 0.031(3) 0.053(3) 0.034(3) -0.005(3) 0.007(2) -0.004(3)
C29 0.075(5) 0.130(7) 0.033(4) -0.007(4) 0.015(3) -0.021(5)
_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 C21 2.012(5) . ?
Ir1 C10 2.030(5) . ?
Ir1 C1 2.031(5) . ?
Ir1 C12 2.033(5) . ?
Ir1 N7 2.144(4) . ?
Ir1 O1 2.144(3) . ?
O1 C23 1.277(6) . ?
O2 C23 1.233(6) . ?
O3 C27 1.362(7) . ?
O3 C29 1.445(7) . ?
N1 C1 1.347(6) . ?
N1 C3 1.386(7) . ?
N1 C2 1.455(7) . ?
N2 C1 1.365(6) . ?
N2 C4 1.388(6) . ?
N2 C5 1.425(6) . ?
N3 C11 1.149(8) . ?
N4 C12 1.349(6) . ?
N4 C14 1.394(7) . ?
N4 C13 1.460(7) . ?
N5 C12 1.364(6) . ?
N5 C15 1.380(6) . ?
N5 C16 1.422(6) . ?
N6 C22 1.132(8) . ?
N7 C28 1.331(6) . ?
N7 C24 1.358(6) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.337(8) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.375(7) . ?
C5 C10 1.404(7) . ?
C6 C7 1.374(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.409(8) . ?
C8 C11 1.427(8) . ?
C9 C10 1.392(7) . ?
C9 H9 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.335(8) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.381(7) . ?
C16 C21 1.425(7) . ?
C17 C18 1.367(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.402(7) . ?
C19 C22 1.442(8) . ?
C20 C21 1.385(7) . ?
C20 H20 0.9300 . ?
C23 C24 1.499(7) . ?
C24 C25 1.371(7) . ?
C25 C26 1.412(9) . ?
C25 H25 0.9300 . ?
C26 C27 1.362(9) . ?
C26 H26 0.9300 . ?
C27 C28 1.391(8) . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
N8 C30 1.130(10) 3_557 ?
N8 C30 1.130(10) . ?
C30 C31 1.528(10) . ?
N8A C30A 1.084(10) . ?
C30A C31A 1.480(10) . ?
C30A C30A 1.61(5) 3_557 ?
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
C21 Ir1 C10 90.28(18) . . ?
C21 Ir1 C1 92.08(18) . . ?
C10 Ir1 C1 78.95(19) . . ?
C21 Ir1 C12 79.24(19) . . ?
C10 Ir1 C12 96.61(19) . . ?
C1 Ir1 C12 170.30(19) . . ?
C21 Ir1 N7 99.91(17) . . ?
C10 Ir1 N7 169.81(17) . . ?
C1 Ir1 N7 100.68(16) . . ?
C12 Ir1 N7 85.22(17) . . ?
C21 Ir1 O1 174.94(16) . . ?
C10 Ir1 O1 92.84(16) . . ?
C1 Ir1 O1 92.42(16) . . ?
C12 Ir1 O1 96.43(17) . . ?
N7 Ir1 O1 76.99(14) . . ?
C23 O1 Ir1 116.3(3) . . ?
C27 O3 C29 116.8(5) . . ?
C1 N1 C3 111.4(4) . . ?
C1 N1 C2 125.1(4) . . ?
C3 N1 C2 123.6(4) . . ?
C1 N2 C4 111.9(4) . . ?
C1 N2 C5 116.7(4) . . ?
C4 N2 C5 131.2(4) . . ?
C12 N4 C14 110.6(4) . . ?
C12 N4 C13 125.2(4) . . ?
C14 N4 C13 124.2(5) . . ?
C12 N5 C15 112.2(4) . . ?
C12 N5 C16 116.5(4) . . ?
C15 N5 C16 131.3(4) . . ?
C28 N7 C24 118.9(5) . . ?
C28 N7 Ir1 127.7(4) . . ?
C24 N7 Ir1 112.9(3) . . ?
N1 C1 N2 103.5(4) . . ?
N1 C1 Ir1 140.5(4) . . ?
N2 C1 Ir1 115.4(3) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N1 107.6(5) . . ?
C4 C3 H3 126.2 . . ?
N1 C3 H3 126.2 . . ?
C3 C4 N2 105.6(5) . . ?
C3 C4 H4 127.2 . . ?
N2 C4 H4 127.2 . . ?
C6 C5 C10 124.2(5) . . ?
C6 C5 N2 123.1(5) . . ?
C10 C5 N2 112.6(4) . . ?
C7 C6 C5 119.1(5) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C6 119.2(5) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 121.4(5) . . ?
C7 C8 C11 119.5(5) . . ?
C9 C8 C11 119.1(5) . . ?
C10 C9 C8 120.6(5) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C5 115.4(5) . . ?
C9 C10 Ir1 128.2(4) . . ?
C5 C10 Ir1 116.1(3) . . ?
N3 C11 C8 179.0(8) . . ?
N4 C12 N5 103.7(4) . . ?
N4 C12 Ir1 140.8(4) . . ?
N5 C12 Ir1 115.2(3) . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N4 107.9(5) . . ?
C15 C14 H14 126.1 . . ?
N4 C14 H14 126.1 . . ?
C14 C15 N5 105.6(5) . . ?
C14 C15 H15 127.2 . . ?
N5 C15 H15 127.2 . . ?
C17 C16 N5 123.0(5) . . ?
C17 C16 C21 124.4(5) . . ?
N5 C16 C21 112.6(4) . . ?
C18 C17 C16 119.1(5) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 119.4(5) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C20 120.8(5) . . ?
C18 C19 C22 120.3(5) . . ?
C20 C19 C22 119.0(5) . . ?
C21 C20 C19 122.4(5) . . ?
C21 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?
C20 C21 C16 113.9(4) . . ?
C20 C21 Ir1 130.3(4) . . ?
C16 C21 Ir1 115.8(3) . . ?
N6 C22 C19 178.5(7) . . ?
O2 C23 O1 124.5(5) . . ?
O2 C23 C24 119.6(5) . . ?
O1 C23 C24 115.9(4) . . ?
N7 C24 C25 121.2(5) . . ?
N7 C24 C23 116.7(4) . . ?
C25 C24 C23 122.0(5) . . ?
C24 C25 C26 120.5(6) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C27 C26 C25 116.7(5) . . ?
C27 C26 H26 121.6 . . ?
C25 C26 H26 121.6 . . ?
C26 C27 O3 125.2(5) . . ?
C26 C27 C28 120.9(6) . . ?
O3 C27 C28 113.9(5) . . ?
N7 C28 C27 121.8(5) . . ?
N7 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
O3 C29 H29A 109.5 . . ?
O3 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O3 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C30 N8 C30 180.000(5) 3_557 . ?
N8 C30 C31 141(3) . . ?
N8A C30A C31A 152(3) . . ?
N8A C30A C30A 92.9(19) . 3_557 ?
C31A C30A C30A 114.9(19) . 3_557 ?
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
C21 Ir1 O1 C23 -42.9(19) . . . . ?
C10 Ir1 O1 C23 -170.9(4) . . . . ?
C1 Ir1 O1 C23 110.0(4) . . . . ?
C12 Ir1 O1 C23 -73.9(4) . . . . ?
N7 Ir1 O1 C23 9.6(3) . . . . ?
C21 Ir1 N7 C28 -3.8(4) . . . . ?
C10 Ir1 N7 C28 177.2(9) . . . . ?
C1 Ir1 N7 C28 90.2(4) . . . . ?
C12 Ir1 N7 C28 -82.0(4) . . . . ?
O1 Ir1 N7 C28 -179.7(4) . . . . ?
C21 Ir1 N7 C24 167.4(3) . . . . ?
C10 Ir1 N7 C24 -11.6(11) . . . . ?
C1 Ir1 N7 C24 -98.5(3) . . . . ?
C12 Ir1 N7 C24 89.3(3) . . . . ?
O1 Ir1 N7 C24 -8.5(3) . . . . ?
C3 N1 C1 N2 0.2(5) . . . . ?
C2 N1 C1 N2 -179.4(4) . . . . ?
C3 N1 C1 Ir1 -170.5(4) . . . . ?
C2 N1 C1 Ir1 9.9(8) . . . . ?
C4 N2 C1 N1 -0.3(5) . . . . ?
C5 N2 C1 N1 -175.4(4) . . . . ?
C4 N2 C1 Ir1 173.2(3) . . . . ?
C5 N2 C1 Ir1 -1.9(5) . . . . ?
C21 Ir1 C1 N1 79.5(5) . . . . ?
C10 Ir1 C1 N1 169.4(6) . . . . ?
C12 Ir1 C1 N1 105.9(12) . . . . ?
N7 Ir1 C1 N1 -21.0(5) . . . . ?
O1 Ir1 C1 N1 -98.2(5) . . . . ?
C21 Ir1 C1 N2 -90.5(3) . . . . ?
C10 Ir1 C1 N2 -0.7(3) . . . . ?
C12 Ir1 C1 N2 -64.1(12) . . . . ?
N7 Ir1 C1 N2 169.0(3) . . . . ?
O1 Ir1 C1 N2 91.8(3) . . . . ?
C1 N1 C3 C4 0.0(6) . . . . ?
C2 N1 C3 C4 179.5(5) . . . . ?
N1 C3 C4 N2 -0.2(6) . . . . ?
C1 N2 C4 C3 0.3(6) . . . . ?
C5 N2 C4 C3 174.5(5) . . . . ?
C1 N2 C5 C6 -173.0(5) . . . . ?
C4 N2 C5 C6 13.1(8) . . . . ?
C1 N2 C5 C10 4.5(6) . . . . ?
C4 N2 C5 C10 -169.5(5) . . . . ?
C10 C5 C6 C7 0.6(8) . . . . ?
N2 C5 C6 C7 177.7(5) . . . . ?
C5 C6 C7 C8 0.1(9) . . . . ?
C6 C7 C8 C9 -0.3(9) . . . . ?
C6 C7 C8 C11 179.7(6) . . . . ?
C7 C8 C9 C10 -0.2(8) . . . . ?
C11 C8 C9 C10 179.8(5) . . . . ?
C8 C9 C10 C5 0.9(7) . . . . ?
C8 C9 C10 Ir1 -171.7(4) . . . . ?
C6 C5 C10 C9 -1.1(7) . . . . ?
N2 C5 C10 C9 -178.5(4) . . . . ?
C6 C5 C10 Ir1 172.4(4) . . . . ?
N2 C5 C10 Ir1 -5.0(5) . . . . ?
C21 Ir1 C10 C9 -92.3(5) . . . . ?
C1 Ir1 C10 C9 175.6(5) . . . . ?
C12 Ir1 C10 C9 -13.1(5) . . . . ?
N7 Ir1 C10 C9 86.7(11) . . . . ?
O1 Ir1 C10 C9 83.7(5) . . . . ?
C21 Ir1 C10 C5 95.2(4) . . . . ?
C1 Ir1 C10 C5 3.2(4) . . . . ?
C12 Ir1 C10 C5 174.4(4) . . . . ?
N7 Ir1 C10 C5 -85.7(10) . . . . ?
O1 Ir1 C10 C5 -88.7(4) . . . . ?
C7 C8 C11 N3 -118(43) . . . . ?
C9 C8 C11 N3 62(43) . . . . ?
C14 N4 C12 N5 -0.9(6) . . . . ?
C13 N4 C12 N5 178.4(5) . . . . ?
C14 N4 C12 Ir1 172.9(5) . . . . ?
C13 N4 C12 Ir1 -7.8(10) . . . . ?
C15 N5 C12 N4 1.1(6) . . . . ?
C16 N5 C12 N4 -176.2(4) . . . . ?
C15 N5 C12 Ir1 -174.6(4) . . . . ?
C16 N5 C12 Ir1 8.1(6) . . . . ?
C21 Ir1 C12 N4 179.0(6) . . . . ?
C10 Ir1 C12 N4 90.0(6) . . . . ?
C1 Ir1 C12 N4 152.2(9) . . . . ?
N7 Ir1 C12 N4 -79.9(6) . . . . ?
O1 Ir1 C12 N4 -3.6(6) . . . . ?
C21 Ir1 C12 N5 -7.6(4) . . . . ?
C10 Ir1 C12 N5 -96.6(4) . . . . ?
C1 Ir1 C12 N5 -34.5(13) . . . . ?
N7 Ir1 C12 N5 93.4(4) . . . . ?
O1 Ir1 C12 N5 169.7(4) . . . . ?
C12 N4 C14 C15 0.5(7) . . . . ?
C13 N4 C14 C15 -178.9(6) . . . . ?
N4 C14 C15 N5 0.2(6) . . . . ?
C12 N5 C15 C14 -0.8(6) . . . . ?
C16 N5 C15 C14 175.9(5) . . . . ?
C12 N5 C16 C17 174.8(5) . . . . ?
C15 N5 C16 C17 -1.9(9) . . . . ?
C12 N5 C16 C21 -3.1(6) . . . . ?
C15 N5 C16 C21 -179.8(5) . . . . ?
N5 C16 C17 C18 -174.8(5) . . . . ?
C21 C16 C17 C18 2.8(9) . . . . ?
C16 C17 C18 C19 -1.3(9) . . . . ?
C17 C18 C19 C20 -0.7(9) . . . . ?
C17 C18 C19 C22 177.9(6) . . . . ?
C18 C19 C20 C21 1.4(8) . . . . ?
C22 C19 C20 C21 -177.3(5) . . . . ?
C19 C20 C21 C16 0.0(7) . . . . ?
C19 C20 C21 Ir1 179.0(4) . . . . ?
C17 C16 C21 C20 -2.1(7) . . . . ?
N5 C16 C21 C20 175.8(4) . . . . ?
C17 C16 C21 Ir1 178.7(4) . . . . ?
N5 C16 C21 Ir1 -3.4(5) . . . . ?
C10 Ir1 C21 C20 -76.4(5) . . . . ?
C1 Ir1 C21 C20 2.5(5) . . . . ?
C12 Ir1 C21 C20 -173.1(5) . . . . ?
N7 Ir1 C21 C20 103.8(5) . . . . ?
O1 Ir1 C21 C20 155.5(16) . . . . ?
C10 Ir1 C21 C16 102.6(4) . . . . ?
C1 Ir1 C21 C16 -178.5(4) . . . . ?
C12 Ir1 C21 C16 5.9(4) . . . . ?
N7 Ir1 C21 C16 -77.3(4) . . . . ?
O1 Ir1 C21 C16 -26(2) . . . . ?
C18 C19 C22 N6 168(100) . . . . ?
C20 C19 C22 N6 -13(33) . . . . ?
Ir1 O1 C23 O2 170.6(4) . . . . ?
Ir1 O1 C23 C24 -8.8(5) . . . . ?
C28 N7 C24 C25 0.7(7) . . . . ?
Ir1 N7 C24 C25 -171.4(4) . . . . ?
C28 N7 C24 C23 179.1(4) . . . . ?
Ir1 N7 C24 C23 7.0(5) . . . . ?
O2 C23 C24 N7 -178.4(4) . . . . ?
O1 C23 C24 N7 1.1(6) . . . . ?
O2 C23 C24 C25 0.0(8) . . . . ?
O1 C23 C24 C25 179.5(5) . . . . ?
N7 C24 C25 C26 -1.2(8) . . . . ?
C23 C24 C25 C26 -179.5(5) . . . . ?
C24 C25 C26 C27 0.8(9) . . . . ?
C25 C26 C27 O3 -178.7(5) . . . . ?
C25 C26 C27 C28 0.1(9) . . . . ?
C29 O3 C27 C26 -10.0(9) . . . . ?
C29 O3 C27 C28 171.0(5) . . . . ?
C24 N7 C28 C27 0.3(7) . . . . ?
Ir1 N7 C28 C27 171.0(4) . . . . ?
C26 C27 C28 N7 -0.7(9) . . . . ?
O3 C27 C28 N7 178.3(5) . . . . ?
C30 N8 C30 C31 -12(100) 3_557 . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.665
_refine_diff_density_min         -1.077
_refine_diff_density_rms         0.113