# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_a
#TrackingRef '16531_web_deposit_cif_file_0_xicunGao_1357117742.Ir(ppy)3D24.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H24 Ir N3'
_chemical_formula_weight         219.23

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'
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   P-4

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

_cell_length_a                   23.504(3)
_cell_length_b                   23.504(3)
_cell_length_c                   9.1114(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5033.3(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    4.990
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             6279
_exptl_absorpt_coefficient_mu    45.419
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            38998
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.50
_reflns_number_total             9354
_reflns_number_gt                8849
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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^)+(0.0202P)^2^+4.0353P] 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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         9354
_refine_ls_number_parameters     658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_ref         0.0531
_refine_ls_wR_factor_gt          0.0522
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.273
_refine_ls_shift/su_mean         0.040

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 0.971661(7) 0.245917(6) 0.37556(3) 0.02762(5) Uani 1 1 d . . .
Ir2 Ir 0.471652(7) 0.254073(6) 0.12446(3) 0.02759(5) Uani 1 1 d . . .
C5 C 0.8492(2) 0.2166(2) 0.3480(6) 0.0353(12) Uani 1 1 d . . .
C6 C 0.8665(2) 0.2406(2) 0.2076(6) 0.0351(12) Uani 1 1 d . . .
C11 C 0.9229(2) 0.2590(2) 0.1965(6) 0.0310(11) Uani 1 1 d . . .
C49 C 0.3491(2) 0.2835(2) 0.1515(6) 0.0373(13) Uani 1 1 d . . .
C50 C 0.3664(2) 0.2592(2) 0.2934(6) 0.0350(12) Uani 1 1 d . . .
C55 C 0.4226(2) 0.2409(2) 0.3057(6) 0.0327(11) Uani 1 1 d . . .
C48 C 0.2950(2) 0.3037(2) 0.1124(9) 0.0450(13) Uani 1 1 d . . .
H48A H 0.2657 0.3019 0.1808 0.054 Uiso 1 1 calc R . .
C4 C 0.7949(2) 0.1967(2) 0.3850(9) 0.0457(13) Uani 1 1 d . . .
H4A H 0.7658 0.1984 0.3161 0.055 Uiso 1 1 calc R . .
N5 N 0.39197(17) 0.28692(17) 0.0509(5) 0.0328(9) Uani 1 1 d . . .
N1 N 0.89195(17) 0.21307(16) 0.4485(5) 0.0310(9) Uani 1 1 d . . .
C46 C 0.3277(2) 0.3277(2) -0.1223(10) 0.0517(13) Uani 1 1 d . . .
H46 H 0.3213 0.3421 -0.2160 0.062 Uiso 1 1 calc R . .
C51 C 0.3291(3) 0.2559(3) 0.4129(7) 0.0527(18) Uani 1 1 d . . .
H51A H 0.2916 0.2679 0.4026 0.063 Uiso 1 1 calc R . .
C54 C 0.4399(3) 0.2192(3) 0.4394(6) 0.0442(14) Uani 1 1 d . . .
H54A H 0.4770 0.2061 0.4503 0.053 Uiso 1 1 calc R . .
C45 C 0.3810(2) 0.3080(2) -0.0815(6) 0.0390(13) Uani 1 1 d . . .
H45A H 0.4104 0.3096 -0.1497 0.047 Uiso 1 1 calc R . .
C2 C 0.8278(2) 0.1722(2) 0.6204(9) 0.0502(13) Uani 1 1 d . . .
H2A H 0.8217 0.1575 0.7138 0.060 Uiso 1 1 calc R . .
C7 C 0.8289(2) 0.2442(3) 0.0868(7) 0.0501(17) Uani 1 1 d . . .
H7A H 0.7914 0.2322 0.0968 0.060 Uiso 1 1 calc R . .
C1 C 0.8808(2) 0.1919(2) 0.5802(6) 0.0421(13) Uani 1 1 d . . .
H1A H 0.9101 0.1902 0.6487 0.051 Uiso 1 1 calc R . .
C52 C 0.3474(3) 0.2352(3) 0.5440(7) 0.0611(18) Uani 1 1 d . . .
H52A H 0.3226 0.2335 0.6235 0.073 Uiso 1 1 calc R . .
C47 C 0.2844(3) 0.3253(2) -0.0203(8) 0.0505(15) Uani 1 1 d . . .
H47A H 0.2482 0.3386 -0.0437 0.061 Uiso 1 1 calc R . .
N6 N 0.51761(18) 0.28401(18) -0.0631(4) 0.0311(10) Uani 1 1 d . . .
C64 C 0.5125(2) 0.4085(2) 0.3690(9) 0.0501(13) Uani 1 1 d . . .
H64A H 0.5078 0.4230 0.4632 0.060 Uiso 1 1 calc R . .
C61 C 0.52689(19) 0.3644(2) 0.0914(5) 0.0316(12) Uani 1 1 d . . .
C65 C 0.4899(2) 0.3560(2) 0.3351(5) 0.0375(12) Uani 1 1 d . . .
H65A H 0.4697 0.3364 0.4065 0.045 Uiso 1 1 calc R . .
C66 C 0.4967(2) 0.3313(2) 0.1949(6) 0.0298(10) Uani 1 1 d . . .
C60 C 0.5371(2) 0.3382(2) -0.0509(6) 0.0314(11) Uani 1 1 d . . .
N4 N 0.45941(18) 0.17210(18) 0.0326(5) 0.0344(10) Uani 1 1 d . . .
C38 C 0.5036(2) 0.1350(2) 0.0520(7) 0.0413(13) Uani 1 1 d . . .
C43 C 0.5814(2) 0.2328(2) 0.3027(6) 0.0379(12) Uani 1 1 d . . .
H43A H 0.5783 0.2695 0.3395 0.046 Uiso 1 1 calc R . .
C44 C 0.5410(2) 0.2135(2) 0.2039(5) 0.0298(10) Uani 1 1 d . . .
C39 C 0.5480(2) 0.1566(2) 0.1518(6) 0.0412(13) Uani 1 1 d . . .
C34 C 0.4168(2) 0.1560(2) -0.0560(6) 0.0431(13) Uani 1 1 d . . .
H34A H 0.3863 0.1808 -0.0678 0.052 Uiso 1 1 calc R . .
C62 C 0.5485(2) 0.4176(2) 0.1254(9) 0.0467(12) Uani 1 1 d . . .
H62A H 0.5676 0.4385 0.0539 0.056 Uiso 1 1 calc R . .
C63 C 0.5420(3) 0.4400(2) 0.2655(8) 0.0552(16) Uani 1 1 d . . .
H63A H 0.5571 0.4754 0.2893 0.066 Uiso 1 1 calc R . .
C59 C 0.5645(2) 0.3635(3) -0.1697(6) 0.0432(14) Uani 1 1 d . . .
H59A H 0.5770 0.4009 -0.1620 0.052 Uiso 1 1 calc R . .
C58 C 0.5735(3) 0.3342(3) -0.2977(7) 0.0568(18) Uani 1 1 d . . .
H58A H 0.5921 0.3514 -0.3761 0.068 Uiso 1 1 calc R . .
C57 C 0.5542(3) 0.2788(3) -0.3081(7) 0.0560(17) Uani 1 1 d . . .
H57 H 0.5597 0.2577 -0.3932 0.067 Uiso 1 1 calc R . .
C35 C 0.4152(3) 0.1052(2) -0.1303(10) 0.0555(14) Uani 1 1 d . . .
H35 H 0.3850 0.0957 -0.1916 0.067 Uiso 1 1 calc R . .
C37 C 0.5045(3) 0.0835(3) -0.0196(8) 0.0623(18) Uani 1 1 d . . .
H37A H 0.5350 0.0588 -0.0064 0.075 Uiso 1 1 calc R . .
C42 C 0.6262(2) 0.1992(3) 0.3479(7) 0.0497(15) Uani 1 1 d . . .
H42A H 0.6522 0.2138 0.4150 0.060 Uiso 1 1 calc R . .
C40 C 0.5939(3) 0.1234(3) 0.1972(8) 0.0611(18) Uani 1 1 d . . .
H40A H 0.5983 0.0867 0.1609 0.073 Uiso 1 1 calc R . .
C41 C 0.6333(3) 0.1452(3) 0.2969(8) 0.0654(19) Uani 1 1 d . . .
H41A H 0.6639 0.1233 0.3281 0.079 Uiso 1 1 calc R . .
C3 C 0.7843(3) 0.1748(2) 0.5210(8) 0.0513(15) Uani 1 1 d . . .
H3A H 0.7482 0.1619 0.5456 0.062 Uiso 1 1 calc R . .
C10 C 0.9397(3) 0.2806(3) 0.0604(6) 0.0452(14) Uani 1 1 d . . .
H10A H 0.9769 0.2935 0.0489 0.054 Uiso 1 1 calc R . .
C8 C 0.8474(3) 0.2651(3) -0.0442(7) 0.0626(19) Uani 1 1 d . . .
H8A H 0.8227 0.2671 -0.1236 0.075 Uiso 1 1 calc R . .
C9 C 0.9026(3) 0.2834(3) -0.0589(7) 0.0597(18) Uani 1 1 d . . .
H9A H 0.9152 0.2977 -0.1484 0.072 Uiso 1 1 calc R . .
C23 C 1.0266(2) 0.2444(3) 0.6886(6) 0.0445(14) Uani 1 1 d . . .
H23A H 1.0137 0.2817 0.6959 0.053 Uiso 1 1 calc R . .
N3 N 1.01769(18) 0.21633(18) 0.5630(4) 0.0310(10) Uani 1 1 d . . .
C56 C 0.5265(2) 0.2559(3) -0.1874(6) 0.0435(14) Uani 1 1 d . . .
H56A H 0.5133 0.2186 -0.1939 0.052 Uiso 1 1 calc R . .
C31 C 1.0122(2) 0.0913(2) 0.1318(9) 0.0489(13) Uani 1 1 d . . .
H31A H 1.0075 0.0767 0.0377 0.059 Uiso 1 1 calc R . .
C32 C 0.9897(2) 0.1439(2) 0.1657(6) 0.0414(14) Uani 1 1 d . . .
H32A H 0.9694 0.1636 0.0945 0.050 Uiso 1 1 calc R . .
C28 C 1.02678(19) 0.1357(2) 0.4083(6) 0.0322(13) Uani 1 1 d . . .
C27 C 1.03708(19) 0.1616(2) 0.5511(6) 0.0316(11) Uani 1 1 d . . .
C33 C 0.99670(19) 0.1684(2) 0.3057(5) 0.0292(10) Uani 1 1 d . . .
C26 C 1.0645(2) 0.1367(3) 0.6696(6) 0.0438(14) Uani 1 1 d . . .
H26A H 1.0771 0.0993 0.6617 0.053 Uiso 1 1 calc R . .
C24 C 1.0541(3) 0.2209(3) 0.8077(7) 0.0558(16) Uani 1 1 d . . .
H24A H 1.0594 0.2418 0.8932 0.067 Uiso 1 1 calc R . .
N2 N 0.95946(18) 0.32786(17) 0.4676(5) 0.0342(9) Uani 1 1 d . . .
C17 C 1.0480(2) 0.3435(2) 0.3480(6) 0.0395(13) Uani 1 1 d . . .
C12 C 0.9162(2) 0.3436(2) 0.5551(6) 0.0417(13) Uani 1 1 d . . .
H12A H 0.8854 0.3190 0.5642 0.050 Uiso 1 1 calc R . .
C21 C 1.0813(2) 0.2672(2) 0.1973(6) 0.0374(12) Uani 1 1 d . . .
H21A H 1.0783 0.2303 0.1613 0.045 Uiso 1 1 calc R . .
C22 C 1.0404(2) 0.2865(2) 0.2965(5) 0.0305(10) Uani 1 1 d . . .
C16 C 1.0039(3) 0.3649(2) 0.4479(7) 0.0422(13) Uani 1 1 d . . .
C13 C 0.9151(2) 0.3946(2) 0.6330(9) 0.0530(14) Uani 1 1 d . . .
H13A H 0.8849 0.4038 0.6945 0.064 Uiso 1 1 calc R . .
C20 C 1.1264(2) 0.3011(3) 0.1501(7) 0.0519(16) Uani 1 1 d . . .
H20A H 1.1521 0.2868 0.0818 0.062 Uiso 1 1 calc R . .
C14 C 0.9604(3) 0.4309(3) 0.6152(12) 0.075(2) Uani 1 1 d . . .
H14A H 0.9615 0.4650 0.6667 0.090 Uiso 1 1 calc R . .
C15 C 1.0049(3) 0.4169(3) 0.5204(8) 0.0625(18) Uani 1 1 d . . .
H15A H 1.0349 0.4421 0.5059 0.075 Uiso 1 1 calc R . .
C19 C 1.1329(3) 0.3549(3) 0.2032(8) 0.0628(18) Uani 1 1 d . . .
H19A H 1.1636 0.3769 0.1731 0.075 Uiso 1 1 calc R . .
C29 C 1.0488(2) 0.0822(2) 0.3744(9) 0.0480(12) Uani 1 1 d . . .
H29A H 1.0683 0.0616 0.4454 0.058 Uiso 1 1 calc R . .
C30 C 1.0416(3) 0.0599(3) 0.2357(8) 0.0551(16) Uani 1 1 d . . .
H30A H 1.0562 0.0242 0.2122 0.066 Uiso 1 1 calc R . .
C25 C 1.0734(3) 0.1656(3) 0.7978(7) 0.0574(18) Uani 1 1 d . . .
H25A H 1.0920 0.1484 0.8763 0.069 Uiso 1 1 calc R . .
C53 C 0.4024(3) 0.2167(3) 0.5588(7) 0.0613(19) Uani 1 1 d . . .
H53A H 0.4149 0.2025 0.6484 0.074 Uiso 1 1 calc R . .
C36 C 0.4609(3) 0.0688(3) -0.1094(10) 0.0659(17) Uiso 1 1 d . . .
H36A H 0.4617 0.0339 -0.1575 0.079 Uiso 1 1 calc R . .
C18 C 1.0942(3) 0.3766(3) 0.3015(8) 0.0575(16) Uiso 1 1 d . . .
H18A H 1.0986 0.4134 0.3373 0.069 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 0.02913(9) 0.02919(9) 0.02455(10) 0.00238(9) -0.00112(10) 0.00063(6)
Ir2 0.02918(9) 0.02914(9) 0.02445(10) 0.00230(9) 0.00116(10) -0.00050(6)
C5 0.033(2) 0.034(2) 0.039(4) -0.007(2) -0.006(2) 0.002(2)
C6 0.035(3) 0.035(3) 0.035(3) -0.005(2) -0.007(2) 0.009(2)
C11 0.034(3) 0.022(2) 0.037(3) 0.002(2) -0.002(2) 0.010(2)
C49 0.036(3) 0.036(2) 0.040(4) -0.006(2) 0.006(2) -0.004(2)
C50 0.038(3) 0.034(3) 0.033(3) -0.002(2) 0.010(2) -0.012(2)
C55 0.031(3) 0.027(2) 0.041(3) 0.003(2) 0.001(2) -0.007(2)
C48 0.030(2) 0.051(3) 0.054(4) -0.013(3) 0.005(3) 0.000(2)
C4 0.035(2) 0.048(3) 0.055(4) -0.004(3) -0.008(3) 0.004(2)
N5 0.034(2) 0.030(2) 0.035(2) -0.0015(18) -0.0017(18) 0.0025(18)
N1 0.031(2) 0.027(2) 0.035(2) -0.0012(18) 0.0040(18) -0.0027(17)
C46 0.054(3) 0.049(3) 0.051(3) 0.003(4) -0.017(4) 0.007(2)
C51 0.040(3) 0.064(4) 0.055(5) -0.010(3) 0.015(3) -0.012(3)
C54 0.049(3) 0.055(4) 0.029(3) 0.007(3) 0.004(2) -0.013(3)
C45 0.044(3) 0.043(3) 0.031(3) 0.004(2) -0.001(2) 0.010(2)
C2 0.054(3) 0.050(3) 0.047(3) -0.001(4) 0.013(4) -0.006(2)
C7 0.041(3) 0.057(3) 0.052(5) -0.010(3) -0.012(3) 0.008(3)
C1 0.046(3) 0.043(3) 0.038(3) 0.004(2) 0.001(2) -0.003(2)
C52 0.058(4) 0.084(5) 0.041(4) 0.005(3) 0.019(3) -0.022(4)
C47 0.041(3) 0.044(3) 0.066(4) -0.001(3) -0.014(3) 0.003(3)
N6 0.031(2) 0.036(2) 0.026(2) 0.0013(18) 0.0030(17) 0.0023(19)
C64 0.057(3) 0.045(3) 0.048(3) -0.015(3) 0.005(4) 0.003(2)
C61 0.027(2) 0.033(2) 0.035(4) 0.004(2) -0.0009(19) 0.0052(19)
C65 0.045(3) 0.036(3) 0.031(3) -0.005(2) 0.008(2) -0.002(2)
C66 0.029(2) 0.029(2) 0.031(3) 0.004(2) -0.004(2) 0.006(2)
C60 0.022(2) 0.038(3) 0.034(3) 0.006(2) -0.002(2) 0.002(2)
N4 0.040(2) 0.034(2) 0.030(2) 0.0005(18) 0.0013(19) -0.0045(19)
C38 0.050(3) 0.031(3) 0.042(3) 0.001(2) 0.000(3) 0.003(2)
C43 0.034(3) 0.049(3) 0.031(3) 0.004(2) 0.000(2) -0.003(2)
C44 0.030(2) 0.034(3) 0.025(3) 0.002(2) 0.002(2) -0.002(2)
C39 0.049(3) 0.038(3) 0.037(4) 0.005(2) 0.000(3) 0.004(2)
C34 0.045(3) 0.046(3) 0.038(3) 0.007(2) -0.001(2) -0.011(3)
C62 0.050(3) 0.037(3) 0.053(3) 0.009(3) 0.003(4) -0.001(2)
C63 0.061(4) 0.034(3) 0.070(5) -0.010(3) 0.001(3) -0.008(3)
C59 0.042(3) 0.053(3) 0.035(3) 0.016(2) 0.002(2) 0.001(3)
C58 0.043(3) 0.086(5) 0.042(4) 0.027(3) 0.001(3) -0.009(3)
C57 0.058(4) 0.083(5) 0.027(3) -0.002(3) 0.005(3) -0.002(3)
C35 0.064(4) 0.047(3) 0.056(4) -0.006(4) 0.005(4) -0.015(3)
C37 0.072(4) 0.043(3) 0.072(5) -0.007(3) -0.016(4) 0.013(3)
C42 0.044(3) 0.066(4) 0.039(4) 0.005(3) -0.012(3) 0.004(3)
C40 0.072(4) 0.047(4) 0.064(4) 0.001(3) -0.020(3) 0.020(3)
C41 0.055(4) 0.065(4) 0.076(5) 0.004(4) -0.017(3) 0.025(3)
C3 0.038(3) 0.044(3) 0.072(5) -0.007(3) 0.011(3) -0.007(3)
C10 0.051(3) 0.052(4) 0.033(3) 0.005(3) -0.004(3) 0.013(3)
C8 0.063(4) 0.090(5) 0.035(4) -0.005(3) -0.022(3) 0.027(4)
C9 0.065(4) 0.087(5) 0.027(3) 0.010(3) -0.005(3) 0.030(4)
C23 0.042(3) 0.054(4) 0.037(3) 0.003(3) 0.004(3) 0.012(3)
N3 0.031(2) 0.038(2) 0.025(2) 0.0007(18) -0.0033(17) -0.0023(19)
C56 0.045(3) 0.055(4) 0.031(3) 0.003(3) -0.002(2) -0.010(3)
C31 0.059(3) 0.041(3) 0.046(3) -0.015(3) -0.004(4) -0.003(2)
C32 0.046(3) 0.037(3) 0.041(4) -0.001(2) -0.007(2) 0.000(2)
C28 0.027(2) 0.030(2) 0.039(4) 0.008(2) 0.002(2) -0.0045(19)
C27 0.020(2) 0.041(3) 0.034(3) 0.006(2) 0.001(2) -0.002(2)
C33 0.028(2) 0.030(2) 0.029(3) -0.003(2) 0.006(2) -0.004(2)
C26 0.039(3) 0.053(3) 0.039(4) 0.017(2) 0.000(2) 0.000(3)
C24 0.058(4) 0.084(5) 0.026(3) -0.002(3) -0.003(3) 0.001(3)
N2 0.038(2) 0.031(2) 0.034(2) 0.0029(18) -0.0013(19) 0.0079(19)
C17 0.043(3) 0.032(2) 0.043(4) 0.003(2) 0.001(2) -0.005(2)
C12 0.043(3) 0.042(3) 0.040(3) 0.004(2) 0.001(2) 0.011(2)
C21 0.039(3) 0.048(3) 0.025(3) 0.003(2) -0.001(2) 0.003(2)
C22 0.032(2) 0.034(3) 0.026(3) 0.002(2) 0.002(2) 0.001(2)
C16 0.055(3) 0.029(3) 0.043(3) -0.001(2) 0.001(3) 0.000(2)
C13 0.057(3) 0.048(3) 0.054(4) -0.012(4) 0.002(4) 0.010(3)
C20 0.043(3) 0.068(4) 0.044(4) 0.008(3) 0.013(3) -0.005(3)
C14 0.090(5) 0.044(3) 0.093(6) -0.025(4) 0.025(6) 0.004(3)
C15 0.078(5) 0.043(3) 0.067(5) -0.004(3) 0.010(4) -0.013(3)
C19 0.051(4) 0.069(4) 0.069(5) 0.001(4) 0.015(3) -0.022(3)
C29 0.050(3) 0.038(3) 0.056(3) 0.007(4) -0.008(4) 0.000(2)
C30 0.065(4) 0.036(3) 0.064(4) -0.007(3) -0.002(3) 0.007(3)
C25 0.045(3) 0.088(5) 0.039(4) 0.022(3) -0.005(3) 0.008(3)
C53 0.070(4) 0.088(5) 0.027(3) 0.006(3) 0.003(3) -0.026(4)

_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 C22 2.011(5) . ?
Ir1 C11 2.017(5) . ?
Ir1 C33 2.018(5) . ?
Ir1 N2 2.120(4) . ?
Ir1 N1 2.133(4) . ?
Ir1 N3 2.138(4) . ?
Ir2 C66 2.012(5) . ?
Ir2 C44 2.022(5) . ?
Ir2 C55 2.038(5) . ?
Ir2 N4 2.120(4) . ?
Ir2 N5 2.134(4) . ?
Ir2 N6 2.140(4) . ?
C5 N1 1.362(6) . ?
C5 C4 1.400(7) . ?
C5 C6 1.456(8) . ?
C6 C11 1.399(7) . ?
C6 C7 1.414(7) . ?
C11 C10 1.397(7) . ?
C49 N5 1.364(6) . ?
C49 C48 1.404(7) . ?
C49 C50 1.472(8) . ?
C50 C55 1.392(7) . ?
C50 C51 1.400(7) . ?
C55 C54 1.382(7) . ?
C48 C47 1.334(10) . ?
C4 C3 1.365(10) . ?
N5 C45 1.329(6) . ?
N1 C1 1.326(7) . ?
C46 C47 1.379(10) . ?
C46 C45 1.387(7) . ?
C51 C52 1.359(9) . ?
C54 C53 1.402(8) . ?
C2 C3 1.366(9) . ?
C2 C1 1.377(8) . ?
C7 C8 1.362(9) . ?
C52 C53 1.369(10) . ?
N6 C56 1.328(7) . ?
N6 C60 1.358(7) . ?
C64 C65 1.376(7) . ?
C64 C63 1.386(9) . ?
C61 C62 1.386(7) . ?
C61 C66 1.414(7) . ?
C61 C60 1.456(7) . ?
C65 C66 1.413(7) . ?
C60 C59 1.393(7) . ?
N4 C34 1.342(7) . ?
N4 C38 1.368(7) . ?
C38 C37 1.375(8) . ?
C38 C39 1.475(8) . ?
C43 C44 1.386(7) . ?
C43 C42 1.378(8) . ?
C44 C39 1.428(7) . ?
C39 C40 1.394(8) . ?
C34 C35 1.372(8) . ?
C62 C63 1.389(10) . ?
C59 C58 1.370(9) . ?
C58 C57 1.382(10) . ?
C57 C56 1.389(8) . ?
C35 C36 1.388(9) . ?
C37 C36 1.357(10) . ?
C42 C41 1.361(9) . ?
C40 C41 1.395(10) . ?
C10 C9 1.397(8) . ?
C8 C9 1.372(10) . ?
C23 N3 1.338(7) . ?
C23 C24 1.378(9) . ?
N3 C27 1.368(7) . ?
C31 C32 1.378(7) . ?
C31 C30 1.386(9) . ?
C32 C33 1.409(7) . ?
C28 C29 1.395(7) . ?
C28 C33 1.401(7) . ?
C28 C27 1.456(7) . ?
C27 C26 1.387(7) . ?
C26 C25 1.367(9) . ?
C24 C25 1.379(10) . ?
N2 C12 1.344(7) . ?
N2 C16 1.371(7) . ?
C17 C18 1.400(8) . ?
C17 C22 1.430(7) . ?
C17 C16 1.468(8) . ?
C12 C13 1.395(8) . ?
C21 C22 1.394(7) . ?
C21 C20 1.393(8) . ?
C16 C15 1.390(8) . ?
C13 C14 1.374(9) . ?
C20 C19 1.363(9) . ?
C14 C15 1.396(10) . ?
C19 C18 1.376(9) . ?
C29 C30 1.379(10) . ?

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
C22 Ir1 C11 95.4(2) . . ?
C22 Ir1 C33 94.67(19) . . ?
C11 Ir1 C33 92.8(2) . . ?
C22 Ir1 N2 79.58(18) . . ?
C11 Ir1 N2 96.00(18) . . ?
C33 Ir1 N2 169.91(18) . . ?
C22 Ir1 N1 171.80(17) . . ?
C11 Ir1 N1 78.96(19) . . ?
C33 Ir1 N1 91.58(17) . . ?
N2 Ir1 N1 94.98(16) . . ?
C22 Ir1 N3 91.94(18) . . ?
C11 Ir1 N3 169.46(18) . . ?
C33 Ir1 N3 79.08(19) . . ?
N2 Ir1 N3 92.75(16) . . ?
N1 Ir1 N3 94.46(16) . . ?
C66 Ir2 C44 94.36(19) . . ?
C66 Ir2 C55 92.5(2) . . ?
C44 Ir2 C55 95.4(2) . . ?
C66 Ir2 N4 170.02(18) . . ?
C44 Ir2 N4 79.73(18) . . ?
C55 Ir2 N4 96.05(18) . . ?
C66 Ir2 N5 91.74(17) . . ?
C44 Ir2 N5 172.05(17) . . ?
C55 Ir2 N5 79.21(19) . . ?
N4 Ir2 N5 94.92(16) . . ?
C66 Ir2 N6 79.09(18) . . ?
C44 Ir2 N6 91.96(17) . . ?
C55 Ir2 N6 169.21(18) . . ?
N4 Ir2 N6 92.99(16) . . ?
N5 Ir2 N6 94.19(16) . . ?
N1 C5 C4 119.4(5) . . ?
N1 C5 C6 114.1(4) . . ?
C4 C5 C6 126.5(5) . . ?
C11 C6 C7 121.2(5) . . ?
C11 C6 C5 116.6(4) . . ?
C7 C6 C5 122.2(5) . . ?
C6 C11 C10 116.4(5) . . ?
C6 C11 Ir1 115.6(4) . . ?
C10 C11 Ir1 127.8(4) . . ?
N5 C49 C48 118.6(6) . . ?
N5 C49 C50 114.1(4) . . ?
C48 C49 C50 127.2(5) . . ?
C55 C50 C51 120.9(5) . . ?
C55 C50 C49 116.9(4) . . ?
C51 C50 C49 122.1(5) . . ?
C54 C55 C50 117.6(5) . . ?
C54 C55 Ir2 127.1(4) . . ?
C50 C55 Ir2 115.1(4) . . ?
C47 C48 C49 121.8(6) . . ?
C3 C4 C5 120.7(6) . . ?
C45 N5 C49 119.2(4) . . ?
C45 N5 Ir2 126.2(4) . . ?
C49 N5 Ir2 114.6(3) . . ?
C1 N1 C5 119.0(4) . . ?
C1 N1 Ir1 126.3(4) . . ?
C5 N1 Ir1 114.6(3) . . ?
C47 C46 C45 118.1(7) . . ?
C52 C51 C50 120.3(6) . . ?
C55 C54 C53 120.9(6) . . ?
N5 C45 C46 122.9(6) . . ?
C3 C2 C1 119.0(7) . . ?
C8 C7 C6 120.2(6) . . ?
N1 C1 C2 123.1(6) . . ?
C51 C52 C53 119.8(6) . . ?
C48 C47 C46 119.3(6) . . ?
C56 N6 C60 118.9(5) . . ?
C56 N6 Ir2 126.6(4) . . ?
C60 N6 Ir2 114.4(3) . . ?
C65 C64 C63 121.2(7) . . ?
C62 C61 C66 122.2(5) . . ?
C62 C61 C60 121.3(5) . . ?
C66 C61 C60 116.3(4) . . ?
C64 C65 C66 121.9(5) . . ?
C65 C66 C61 115.6(4) . . ?
C65 C66 Ir2 128.9(4) . . ?
C61 C66 Ir2 115.5(4) . . ?
N6 C60 C59 119.5(5) . . ?
N6 C60 C61 114.4(4) . . ?
C59 C60 C61 126.0(5) . . ?
C34 N4 C38 117.7(5) . . ?
C34 N4 Ir2 126.6(4) . . ?
C38 N4 Ir2 115.2(3) . . ?
N4 C38 C37 120.9(6) . . ?
N4 C38 C39 113.4(5) . . ?
C37 C38 C39 125.7(5) . . ?
C44 C43 C42 122.0(5) . . ?
C43 C44 C39 116.3(5) . . ?
C43 C44 Ir2 129.1(4) . . ?
C39 C44 Ir2 114.6(4) . . ?
C40 C39 C44 121.0(5) . . ?
C40 C39 C38 122.5(5) . . ?
C44 C39 C38 116.5(4) . . ?
N4 C34 C35 124.3(6) . . ?
C61 C62 C63 120.4(6) . . ?
C64 C63 C62 118.6(5) . . ?
C58 C59 C60 121.2(6) . . ?
C59 C58 C57 118.8(5) . . ?
C58 C57 C56 117.8(6) . . ?
C34 C35 C36 116.6(7) . . ?
C36 C37 C38 119.9(6) . . ?
C41 C42 C43 121.7(6) . . ?
C41 C40 C39 120.1(6) . . ?
C42 C41 C40 118.9(6) . . ?
C2 C3 C4 118.8(6) . . ?
C9 C10 C11 122.1(6) . . ?
C7 C8 C9 120.1(6) . . ?
C8 C9 C10 120.0(6) . . ?
N3 C23 C24 123.3(6) . . ?
C23 N3 C27 118.7(4) . . ?
C23 N3 Ir1 127.0(4) . . ?
C27 N3 Ir1 114.3(3) . . ?
N6 C56 C57 123.8(6) . . ?
C32 C31 C30 121.1(6) . . ?
C31 C32 C33 121.6(6) . . ?
C29 C28 C33 122.2(5) . . ?
C29 C28 C27 120.9(5) . . ?
C33 C28 C27 116.8(4) . . ?
N3 C27 C26 119.3(5) . . ?
N3 C27 C28 114.1(4) . . ?
C26 C27 C28 126.6(5) . . ?
C28 C33 C32 116.0(4) . . ?
C28 C33 Ir1 115.6(4) . . ?
C32 C33 Ir1 128.4(4) . . ?
C27 C26 C25 121.8(6) . . ?
C23 C24 C25 118.7(6) . . ?
C12 N2 C16 118.7(5) . . ?
C12 N2 Ir1 125.9(4) . . ?
C16 N2 Ir1 114.9(3) . . ?
C18 C17 C22 121.1(5) . . ?
C18 C17 C16 123.0(5) . . ?
C22 C17 C16 115.9(4) . . ?
N2 C12 C13 123.6(6) . . ?
C22 C21 C20 122.5(5) . . ?
C21 C22 C17 115.6(5) . . ?
C21 C22 Ir1 129.1(4) . . ?
C17 C22 Ir1 115.3(4) . . ?
N2 C16 C15 120.6(6) . . ?
N2 C16 C17 113.7(4) . . ?
C15 C16 C17 125.6(6) . . ?
C14 C13 C12 117.3(6) . . ?
C19 C20 C21 120.4(6) . . ?
C13 C14 C15 120.6(6) . . ?
C16 C15 C14 119.2(6) . . ?
C20 C19 C18 120.0(6) . . ?
C30 C29 C28 120.1(6) . . ?
C29 C30 C31 118.9(6) . . ?
C24 C25 C26 118.3(6) . . ?
C52 C53 C54 120.3(6) . . ?
C37 C36 C35 120.7(7) . . ?
C19 C18 C17 120.3(6) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.077


_database_code_depnum_ccdc_archive 'CCDC 917827'