# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 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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data_wy2076wc
_database_code_depnum_ccdc_archive 'CCDC 898069'
#TrackingRef 'WY2076WC.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H42 Ir N3 O3'
_chemical_formula_weight         973.11

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)/n

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

_cell_length_a                   10.7639(6)
_cell_length_b                   28.0012(15)
_cell_length_c                   14.6392(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.031(10)
_cell_angle_gamma                90.00
_cell_volume                     4412.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    27679
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1952
_exptl_absorpt_coefficient_mu    3.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7505
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Smart CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27679
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         28.30
_reflns_number_total             10641
_reflns_number_gt                8013
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        SAINT
_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^)+(0.0341P)^2^+1.4578P] 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         10641
_refine_ls_number_parameters     550
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0731
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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
C1 C 0.2073(4) 0.69153(13) 0.4089(2) 0.0566(9) Uani 1 1 d . . .
H1A H 0.2793 0.6874 0.3747 0.068 Uiso 1 1 calc R . .
C2 C 0.1938(4) 0.66542(14) 0.4884(3) 0.0665(11) Uani 1 1 d . . .
C3 C 0.0854(5) 0.67212(16) 0.5368(3) 0.0785(13) Uani 1 1 d . . .
H3A H 0.0723 0.6550 0.5904 0.094 Uiso 1 1 calc R . .
C4 C -0.0033(4) 0.70363(15) 0.5074(2) 0.0701(11) Uani 1 1 d . . .
H4A H -0.0761 0.7076 0.5407 0.084 Uiso 1 1 calc R . .
C5 C 0.0156(3) 0.72989(13) 0.4270(2) 0.0517(8) Uani 1 1 d . . .
C6 C 0.2959(5) 0.63144(18) 0.5182(3) 0.1005(17) Uani 1 1 d . . .
H6A H 0.3623 0.6322 0.4745 0.151 Uiso 1 1 calc R . .
H6B H 0.2632 0.5996 0.5220 0.151 Uiso 1 1 calc R . .
H6C H 0.3268 0.6410 0.5769 0.151 Uiso 1 1 calc R . .
C7 C -0.0666(3) 0.76635(12) 0.3890(2) 0.0481(8) Uani 1 1 d . . .
C8 C -0.0280(3) 0.78706(12) 0.30536(19) 0.0426(7) Uani 1 1 d . . .
C9 C -0.0979(3) 0.82558(14) 0.2744(2) 0.0536(8) Uani 1 1 d . . .
H9A H -0.0766 0.8402 0.2196 0.064 Uiso 1 1 calc R . .
C10 C -0.1983(3) 0.84258(14) 0.3232(3) 0.0615(10) Uani 1 1 d . . .
C11 C -0.2388(4) 0.82053(16) 0.4020(3) 0.0687(11) Uani 1 1 d . . .
H11A H -0.3091 0.8314 0.4324 0.082 Uiso 1 1 calc R . .
C12 C -0.1729(4) 0.78217(16) 0.4342(3) 0.0658(10) Uani 1 1 d . . .
H12A H -0.1993 0.7665 0.4868 0.079 Uiso 1 1 calc R . .
C13 C -0.2063(4) 0.92285(17) 0.2699(3) 0.0704(11) Uani 1 1 d . . .
C14 C -0.0982(4) 0.93725(18) 0.3103(4) 0.0886(14) Uani 1 1 d . . .
H14A H -0.0598 0.9182 0.3541 0.106 Uiso 1 1 calc R . .
C15 C -0.0467(6) 0.9804(2) 0.2852(6) 0.128(3) Uani 1 1 d . . .
H15A H 0.0272 0.9904 0.3119 0.154 Uiso 1 1 calc R . .
C16 C -0.1040(9) 1.0087(3) 0.2211(7) 0.166(5) Uani 1 1 d . . .
H16A H -0.0688 1.0376 0.2035 0.199 Uiso 1 1 calc R . .
C17 C -0.2130(10) 0.9937(3) 0.1837(5) 0.147(4) Uani 1 1 d . . .
H17A H -0.2524 1.0129 0.1407 0.176 Uiso 1 1 calc R . .
C18 C -0.2661(6) 0.9512(2) 0.2077(3) 0.1051(19) Uani 1 1 d . . .
H18A H -0.3414 0.9417 0.1823 0.126 Uiso 1 1 calc R . .
C19 C -0.0369(3) 0.66904(12) 0.2249(2) 0.0528(8) Uani 1 1 d . . .
H19A H -0.0158 0.6625 0.2852 0.063 Uiso 1 1 calc R . .
C20 C -0.1200(4) 0.63900(13) 0.1820(2) 0.0574(9) Uani 1 1 d . . .
C21 C -0.1478(4) 0.64950(15) 0.0922(2) 0.0642(10) Uani 1 1 d . . .
H21A H -0.2023 0.6299 0.0602 0.077 Uiso 1 1 calc R . .
C22 C -0.0970(3) 0.68809(14) 0.0496(2) 0.0575(9) Uani 1 1 d . . .
H22A H -0.1171 0.6948 -0.0108 0.069 Uiso 1 1 calc R . .
C23 C -0.0148(3) 0.71754(12) 0.0969(2) 0.0452(7) Uani 1 1 d . . .
C24 C -0.1779(5) 0.59758(17) 0.2323(3) 0.0904(15) Uani 1 1 d . . .
H24A H -0.1452 0.5962 0.2933 0.136 Uiso 1 1 calc R . .
H24B H -0.1591 0.5684 0.2009 0.136 Uiso 1 1 calc R . .
H24C H -0.2664 0.6018 0.2348 0.136 Uiso 1 1 calc R . .
C25 C 0.0440(3) 0.76071(12) 0.0621(2) 0.0451(7) Uani 1 1 d . . .
C26 C 0.1111(3) 0.78856(12) 0.12559(19) 0.0441(7) Uani 1 1 d . . .
C27 C 0.1642(4) 0.83092(14) 0.0931(2) 0.0646(10) Uani 1 1 d . . .
H27A H 0.2062 0.8511 0.1329 0.077 Uiso 1 1 calc R . .
C28 C 0.1538(5) 0.84274(16) 0.0008(3) 0.0874(15) Uani 1 1 d . . .
C29 C 0.0910(5) 0.81541(17) -0.0596(2) 0.0837(14) Uani 1 1 d . . .
H29A H 0.0855 0.8245 -0.1206 0.100 Uiso 1 1 calc R . .
C30 C 0.0356(4) 0.77418(15) -0.0302(2) 0.0627(10) Uani 1 1 d . . .
H30A H -0.0076 0.7551 -0.0713 0.075 Uiso 1 1 calc R . .
C31 C 0.2402(6) 0.92144(18) 0.0160(3) 0.0822(14) Uani 1 1 d . . .
C32 C 0.1545(7) 0.9500(4) 0.0478(5) 0.135(3) Uani 1 1 d . . .
H32A H 0.0707 0.9424 0.0422 0.162 Uiso 1 1 calc R . .
C33 C 0.1915(15) 0.9917(4) 0.0897(7) 0.203(7) Uani 1 1 d . . .
H33A H 0.1325 1.0129 0.1124 0.244 Uiso 1 1 calc R . .
C34 C 0.3069(19) 1.0011(5) 0.0973(8) 0.219(11) Uani 1 1 d . . .
H34A H 0.3292 1.0299 0.1244 0.262 Uiso 1 1 calc R . .
C35 C 0.3951(12) 0.9732(6) 0.0696(8) 0.210(8) Uani 1 1 d . . .
H35A H 0.4783 0.9810 0.0783 0.252 Uiso 1 1 calc R . .
C36 C 0.3605(8) 0.9315(3) 0.0268(5) 0.124(2) Uani 1 1 d . . .
H36A H 0.4206 0.9104 0.0055 0.149 Uiso 1 1 calc R . .
C37 C 0.3309(4) 0.69179(14) 0.1716(2) 0.0611(9) Uani 1 1 d . . .
H37A H 0.2640 0.6724 0.1560 0.073 Uiso 1 1 calc R . .
C38 C 0.4482(4) 0.67588(17) 0.1504(3) 0.0738(12) Uani 1 1 d . . .
C39 C 0.5449(4) 0.70514(18) 0.1764(3) 0.0752(12) Uani 1 1 d . . .
H39A H 0.6261 0.6956 0.1643 0.090 Uiso 1 1 calc R . .
C40 C 0.5248(4) 0.74778(16) 0.2195(3) 0.0681(11) Uani 1 1 d . . .
H40A H 0.5912 0.7668 0.2374 0.082 Uiso 1 1 calc R . .
C41 C 0.4025(3) 0.76222(13) 0.2364(2) 0.0506(8) Uani 1 1 d . . .
C42 C 0.4683(5) 0.6298(2) 0.0995(4) 0.1123(19) Uani 1 1 d . . .
H42A H 0.3896 0.6150 0.0875 0.168 Uiso 1 1 calc R . .
H42B H 0.5186 0.6088 0.1357 0.168 Uiso 1 1 calc R . .
H42C H 0.5097 0.6363 0.0427 0.168 Uiso 1 1 calc R . .
C43 C 0.3652(3) 0.80669(13) 0.2810(2) 0.0470(8) Uani 1 1 d . . .
C44 C 0.2365(3) 0.81167(11) 0.29957(18) 0.0418(7) Uani 1 1 d . . .
C45 C 0.2002(3) 0.85317(12) 0.3458(2) 0.0488(8) Uani 1 1 d . . .
H45A H 0.1170 0.8573 0.3610 0.059 Uiso 1 1 calc R . .
C46 C 0.2852(3) 0.88824(13) 0.3696(2) 0.0532(8) Uani 1 1 d . . .
C47 C 0.4106(3) 0.88362(15) 0.3472(2) 0.0630(10) Uani 1 1 d . . .
H47A H 0.4672 0.9076 0.3613 0.076 Uiso 1 1 calc R . .
C48 C 0.4480(3) 0.84273(15) 0.3036(2) 0.0595(9) Uani 1 1 d . . .
H48A H 0.5314 0.8391 0.2888 0.071 Uiso 1 1 calc R . .
C49 C 0.2885(4) 0.97075(14) 0.4196(3) 0.0602(9) Uani 1 1 d . . .
C50 C 0.2906(4) 0.99482(16) 0.5006(3) 0.0765(12) Uani 1 1 d . . .
H50A H 0.2628 0.9802 0.5538 0.092 Uiso 1 1 calc R . .
C51 C 0.3348(5) 1.04144(18) 0.5028(4) 0.0973(17) Uani 1 1 d . . .
H51A H 0.3368 1.0580 0.5579 0.117 Uiso 1 1 calc R . .
C52 C 0.3748(6) 1.06292(19) 0.4260(5) 0.112(2) Uani 1 1 d . . .
H52A H 0.4048 1.0940 0.4282 0.135 Uiso 1 1 calc R . .
C53 C 0.3711(6) 1.0392(2) 0.3457(4) 0.114(2) Uani 1 1 d . . .
H53A H 0.3974 1.0545 0.2928 0.137 Uiso 1 1 calc R . .
C54 C 0.3285(5) 0.99190(18) 0.3406(3) 0.0953(16) Uani 1 1 d . . .
H54A H 0.3275 0.9755 0.2854 0.114 Uiso 1 1 calc R . .
Ir1 Ir 0.127335(11) 0.759498(5) 0.251420(7) 0.03965(5) Uani 1 1 d . . .
N1 N 0.1212(3) 0.72281(11) 0.37847(16) 0.0479(6) Uani 1 1 d . . .
N2 N 0.0152(2) 0.70712(9) 0.18480(16) 0.0428(6) Uani 1 1 d . . .
N3 N 0.3065(3) 0.73320(10) 0.21328(18) 0.0490(7) Uani 1 1 d . . .
O1 O -0.2673(3) 0.88148(12) 0.2924(2) 0.0857(9) Uani 1 1 d . . .
O2 O 0.2116(6) 0.88284(16) -0.0355(2) 0.183(3) Uani 1 1 d . . .
O3 O 0.2367(3) 0.92547(9) 0.42133(18) 0.0676(7) Uani 1 1 d . . .

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
C1 0.066(2) 0.061(2) 0.0432(18) 0.0085(15) -0.0134(16) -0.0071(18)
C2 0.093(3) 0.056(2) 0.050(2) 0.0141(17) -0.019(2) -0.013(2)
C3 0.120(4) 0.070(3) 0.045(2) 0.0177(19) -0.005(2) -0.024(3)
C4 0.091(3) 0.075(3) 0.0438(19) 0.0052(18) 0.0147(19) -0.020(2)
C5 0.061(2) 0.060(2) 0.0346(16) -0.0041(14) 0.0027(15) -0.0194(17)
C6 0.126(5) 0.090(4) 0.085(3) 0.038(3) -0.028(3) 0.000(3)
C7 0.0468(19) 0.060(2) 0.0371(16) -0.0055(14) 0.0056(13) -0.0146(15)
C8 0.0353(16) 0.055(2) 0.0377(15) -0.0014(13) -0.0020(12) -0.0129(14)
C9 0.0380(18) 0.075(2) 0.0481(18) 0.0024(16) -0.0016(14) -0.0076(16)
C10 0.0370(19) 0.068(3) 0.079(3) -0.006(2) -0.0096(17) -0.0016(17)
C11 0.047(2) 0.087(3) 0.072(3) -0.012(2) 0.0148(19) -0.007(2)
C12 0.059(2) 0.085(3) 0.053(2) -0.005(2) 0.0143(18) -0.016(2)
C13 0.067(3) 0.080(3) 0.064(2) 0.001(2) 0.011(2) 0.029(2)
C14 0.059(3) 0.078(3) 0.129(4) 0.013(3) 0.008(3) 0.004(2)
C15 0.086(4) 0.072(4) 0.227(8) -0.001(4) 0.040(5) 0.008(3)
C16 0.186(9) 0.062(4) 0.250(12) 0.028(6) 0.134(9) 0.035(5)
C17 0.242(10) 0.102(6) 0.097(5) 0.027(4) 0.060(6) 0.081(7)
C18 0.148(5) 0.096(4) 0.071(3) -0.014(3) -0.011(3) 0.057(4)
C19 0.062(2) 0.056(2) 0.0405(17) -0.0025(14) 0.0029(15) -0.0104(17)
C20 0.063(2) 0.055(2) 0.054(2) -0.0090(16) 0.0082(17) -0.0104(17)
C21 0.063(2) 0.075(3) 0.055(2) -0.0205(19) -0.0038(18) -0.016(2)
C22 0.056(2) 0.075(3) 0.0412(18) -0.0118(16) -0.0063(15) -0.0031(18)
C23 0.0411(17) 0.057(2) 0.0371(15) -0.0054(14) 0.0015(12) 0.0047(15)
C24 0.116(4) 0.072(3) 0.084(3) -0.011(2) 0.014(3) -0.043(3)
C25 0.0447(18) 0.058(2) 0.0328(15) -0.0018(13) 0.0015(13) 0.0054(15)
C26 0.0391(16) 0.062(2) 0.0315(14) 0.0029(13) 0.0040(12) -0.0016(14)
C27 0.079(3) 0.076(3) 0.0385(18) 0.0084(16) -0.0017(17) -0.022(2)
C28 0.137(4) 0.079(3) 0.046(2) 0.017(2) 0.006(2) -0.034(3)
C29 0.131(4) 0.088(3) 0.0322(18) 0.0152(19) -0.003(2) -0.012(3)
C30 0.078(3) 0.075(3) 0.0346(17) 0.0021(16) -0.0079(17) 0.004(2)
C31 0.116(4) 0.079(3) 0.052(2) 0.031(2) 0.002(3) -0.024(3)
C32 0.104(5) 0.193(8) 0.107(5) 0.046(5) 0.033(4) 0.019(6)
C33 0.36(2) 0.118(8) 0.128(8) 0.028(6) 0.119(11) 0.070(10)
C34 0.40(3) 0.160(11) 0.095(6) 0.021(6) 0.017(12) -0.157(16)
C35 0.165(11) 0.33(2) 0.138(11) 0.082(11) -0.048(8) -0.135(12)
C36 0.115(6) 0.148(6) 0.110(5) 0.042(5) 0.007(4) 0.032(5)
C37 0.062(2) 0.073(3) 0.0482(19) 0.0004(17) -0.0044(17) 0.0055(19)
C38 0.072(3) 0.090(3) 0.060(2) 0.000(2) 0.000(2) 0.027(2)
C39 0.052(2) 0.110(4) 0.064(2) 0.001(2) 0.0030(19) 0.025(2)
C40 0.047(2) 0.100(3) 0.057(2) 0.011(2) 0.0031(18) 0.006(2)
C41 0.0407(18) 0.077(3) 0.0342(16) 0.0120(15) 0.0003(13) 0.0001(16)
C42 0.102(4) 0.117(5) 0.118(4) -0.031(4) -0.002(3) 0.044(4)
C43 0.0388(17) 0.069(2) 0.0332(14) 0.0080(14) -0.0019(12) -0.0049(15)
C44 0.0380(16) 0.057(2) 0.0298(14) 0.0074(12) -0.0042(12) -0.0075(14)
C45 0.0417(18) 0.065(2) 0.0399(16) 0.0064(15) -0.0043(13) -0.0104(15)
C46 0.058(2) 0.058(2) 0.0437(18) 0.0039(15) -0.0054(15) -0.0133(17)
C47 0.049(2) 0.080(3) 0.060(2) 0.0055(19) -0.0081(17) -0.0249(19)
C48 0.0378(18) 0.086(3) 0.055(2) 0.0071(19) -0.0022(15) -0.0093(18)
C49 0.058(2) 0.058(2) 0.065(2) 0.0034(18) -0.0098(18) -0.0145(18)
C50 0.087(3) 0.068(3) 0.075(3) -0.005(2) 0.005(2) -0.020(2)
C51 0.099(4) 0.077(3) 0.116(4) -0.031(3) 0.013(3) -0.024(3)
C52 0.119(5) 0.065(3) 0.153(6) -0.009(4) 0.025(4) -0.031(3)
C53 0.149(6) 0.086(4) 0.108(4) 0.025(3) 0.015(4) -0.038(4)
C54 0.135(5) 0.081(3) 0.070(3) 0.014(2) -0.008(3) -0.030(3)
Ir1 0.03720(7) 0.05300(8) 0.02876(6) 0.00389(5) -0.00115(4) -0.00610(5)
N1 0.0542(17) 0.0565(16) 0.0329(13) 0.0026(12) -0.0030(11) -0.0112(14)
N2 0.0424(14) 0.0504(16) 0.0357(13) -0.0021(11) -0.0017(10) -0.0018(12)
N3 0.0478(16) 0.065(2) 0.0342(13) 0.0024(12) -0.0012(11) 0.0031(13)
O1 0.0432(16) 0.086(2) 0.128(3) 0.0034(19) -0.0082(16) 0.0085(15)
O2 0.370(8) 0.124(3) 0.054(2) 0.018(2) 0.023(3) -0.128(4)
O3 0.0713(18) 0.0607(16) 0.0708(17) -0.0065(13) 0.0066(13) -0.0226(14)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.351(4) . ?
C1 C2 1.381(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.379(6) . ?
C2 C6 1.518(6) . ?
C3 C4 1.369(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.402(5) . ?
C4 H4A 0.9300 . ?
C5 N1 1.355(4) . ?
C5 C7 1.461(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C12 1.395(5) . ?
C7 C8 1.417(4) . ?
C8 C9 1.391(5) . ?
C8 Ir1 2.004(3) . ?
C9 C10 1.380(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.379(5) . ?
C10 O1 1.393(5) . ?
C11 C12 1.371(6) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.366(6) . ?
C13 C18 1.368(6) . ?
C13 O1 1.372(5) . ?
C14 C15 1.379(7) . ?
C14 H14A 0.9300 . ?
C15 C16 1.373(11) . ?
C15 H15A 0.9300 . ?
C16 C17 1.361(12) . ?
C16 H16A 0.9300 . ?
C17 C18 1.367(10) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 N2 1.340(4) . ?
C19 C20 1.379(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.380(5) . ?
C20 C24 1.509(5) . ?
C21 C22 1.362(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.394(5) . ?
C22 H22A 0.9300 . ?
C23 N2 1.358(4) . ?
C23 C25 1.457(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C30 1.406(4) . ?
C25 C26 1.411(4) . ?
C26 C27 1.400(5) . ?
C26 Ir1 2.021(3) . ?
C27 C28 1.396(5) . ?
C27 H27A 0.9300 . ?
C28 C29 1.350(6) . ?
C28 O2 1.389(5) . ?
C29 C30 1.369(6) . ?
C29 H29A 0.9300 . ?
C30 H30A 0.9300 . ?
C31 C32 1.307(9) . ?
C31 C36 1.334(9) . ?
C31 O2 1.353(6) . ?
C32 C33 1.378(13) . ?
C32 H32A 0.9300 . ?
C33 C34 1.274(19) . ?
C33 H33A 0.9300 . ?
C34 C35 1.296(19) . ?
C34 H34A 0.9300 . ?
C35 C36 1.378(15) . ?
C35 H35A 0.9300 . ?
C36 H36A 0.9300 . ?
C37 N3 1.336(5) . ?
C37 C38 1.375(5) . ?
C37 H37A 0.9300 . ?
C38 C39 1.378(6) . ?
C38 C42 1.505(6) . ?
C39 C40 1.368(6) . ?
C39 H39A 0.9300 . ?
C40 C41 1.399(5) . ?
C40 H40A 0.9300 . ?
C41 N3 1.357(4) . ?
C41 C43 1.462(5) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 C48 1.387(5) . ?
C43 C44 1.419(4) . ?
C44 C45 1.401(5) . ?
C44 Ir1 2.003(3) . ?
C45 C46 1.386(4) . ?
C45 H45A 0.9300 . ?
C46 O3 1.390(4) . ?
C46 C47 1.396(5) . ?
C47 C48 1.371(5) . ?
C47 H47A 0.9300 . ?
C48 H48A 0.9300 . ?
C49 C50 1.365(5) . ?
C49 C54 1.369(6) . ?
C49 O3 1.386(4) . ?
C50 C51 1.390(6) . ?
C50 H50A 0.9300 . ?
C51 C52 1.346(7) . ?
C51 H51A 0.9300 . ?
C52 C53 1.350(7) . ?
C52 H52A 0.9300 . ?
C53 C54 1.403(7) . ?
C53 H53A 0.9300 . ?
C54 H54A 0.9300 . ?
Ir1 N1 2.126(3) . ?
Ir1 N2 2.135(3) . ?
Ir1 N3 2.139(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.3(4) . . ?
N1 C1 H1A 118.4 . . ?
C2 C1 H1A 118.4 . . ?
C3 C2 C1 116.8(4) . . ?
C3 C2 C6 123.4(4) . . ?
C1 C2 C6 119.8(4) . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
N1 C5 C4 119.0(4) . . ?
N1 C5 C7 114.2(3) . . ?
C4 C5 C7 126.7(3) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 121.4(3) . . ?
C12 C7 C5 122.5(3) . . ?
C8 C7 C5 116.0(3) . . ?
C9 C8 C7 116.2(3) . . ?
C9 C8 Ir1 128.4(2) . . ?
C7 C8 Ir1 115.3(2) . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 H9A 119.3 . . ?
C8 C9 H9A 119.3 . . ?
C11 C10 C9 121.8(4) . . ?
C11 C10 O1 116.9(4) . . ?
C9 C10 O1 121.3(4) . . ?
C12 C11 C10 118.3(4) . . ?
C12 C11 H11A 120.8 . . ?
C10 C11 H11A 120.8 . . ?
C11 C12 C7 120.7(4) . . ?
C11 C12 H12A 119.7 . . ?
C7 C12 H12A 119.7 . . ?
C14 C13 C18 121.2(5) . . ?
C14 C13 O1 123.6(4) . . ?
C18 C13 O1 115.1(5) . . ?
C13 C14 C15 119.0(6) . . ?
C13 C14 H14A 120.5 . . ?
C15 C14 H14A 120.5 . . ?
C16 C15 C14 120.4(7) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C17 C16 C15 118.9(7) . . ?
C17 C16 H16A 120.5 . . ?
C15 C16 H16A 120.5 . . ?
C16 C17 C18 121.7(8) . . ?
C16 C17 H17A 119.1 . . ?
C18 C17 H17A 119.1 . . ?
C17 C18 C13 118.6(7) . . ?
C17 C18 H18A 120.7 . . ?
C13 C18 H18A 120.7 . . ?
N2 C19 C20 123.9(3) . . ?
N2 C19 H19A 118.1 . . ?
C20 C19 H19A 118.1 . . ?
C19 C20 C21 116.4(3) . . ?
C19 C20 C24 121.0(4) . . ?
C21 C20 C24 122.6(4) . . ?
C22 C21 C20 121.2(3) . . ?
C22 C21 H21A 119.4 . . ?
C20 C21 H21A 119.4 . . ?
C21 C22 C23 119.8(3) . . ?
C21 C22 H22A 120.1 . . ?
C23 C22 H22A 120.1 . . ?
N2 C23 C22 119.6(3) . . ?
N2 C23 C25 114.0(3) . . ?
C22 C23 C25 126.4(3) . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C30 C25 C26 121.1(3) . . ?
C30 C25 C23 122.1(3) . . ?
C26 C25 C23 116.8(3) . . ?
C27 C26 C25 117.0(3) . . ?
C27 C26 Ir1 128.0(2) . . ?
C25 C26 Ir1 114.9(2) . . ?
C28 C27 C26 119.8(4) . . ?
C28 C27 H27A 120.1 . . ?
C26 C27 H27A 120.1 . . ?
C29 C28 O2 115.6(4) . . ?
C29 C28 C27 122.7(4) . . ?
O2 C28 C27 121.7(4) . . ?
C28 C29 C30 119.3(3) . . ?
C28 C29 H29A 120.3 . . ?
C30 C29 H29A 120.3 . . ?
C29 C30 C25 120.1(4) . . ?
C29 C30 H30A 120.0 . . ?
C25 C30 H30A 120.0 . . ?
C32 C31 C36 120.9(7) . . ?
C32 C31 O2 121.8(8) . . ?
C36 C31 O2 117.0(7) . . ?
C31 C32 C33 118.3(9) . . ?
C31 C32 H32A 120.9 . . ?
C33 C32 H32A 120.9 . . ?
C34 C33 C32 119.7(12) . . ?
C34 C33 H33A 120.2 . . ?
C32 C33 H33A 120.2 . . ?
C33 C34 C35 124.3(15) . . ?
C33 C34 H34A 117.9 . . ?
C35 C34 H34A 117.9 . . ?
C34 C35 C36 117.1(13) . . ?
C34 C35 H35A 121.4 . . ?
C36 C35 H35A 121.4 . . ?
C31 C36 C35 119.7(9) . . ?
C31 C36 H36A 120.2 . . ?
C35 C36 H36A 120.2 . . ?
N3 C37 C38 124.4(4) . . ?
N3 C37 H37A 117.8 . . ?
C38 C37 H37A 117.8 . . ?
C37 C38 C39 116.0(4) . . ?
C37 C38 C42 121.5(5) . . ?
C39 C38 C42 122.5(4) . . ?
C40 C39 C38 121.7(4) . . ?
C40 C39 H39A 119.1 . . ?
C38 C39 H39A 119.1 . . ?
C39 C40 C41 118.9(4) . . ?
C39 C40 H40A 120.5 . . ?
C41 C40 H40A 120.5 . . ?
N3 C41 C40 119.9(4) . . ?
N3 C41 C43 114.3(3) . . ?
C40 C41 C43 125.7(4) . . ?
C38 C42 H42A 109.5 . . ?
C38 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C38 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C48 C43 C44 120.7(3) . . ?
C48 C43 C41 123.3(3) . . ?
C44 C43 C41 116.0(3) . . ?
C45 C44 C43 116.5(3) . . ?
C45 C44 Ir1 127.7(2) . . ?
C43 C44 Ir1 115.7(2) . . ?
C46 C45 C44 121.7(3) . . ?
C46 C45 H45A 119.2 . . ?
C44 C45 H45A 119.2 . . ?
C45 C46 O3 114.8(3) . . ?
C45 C46 C47 120.9(4) . . ?
O3 C46 C47 124.2(3) . . ?
C48 C47 C46 118.1(3) . . ?
C48 C47 H47A 121.0 . . ?
C46 C47 H47A 121.0 . . ?
C47 C48 C43 122.0(3) . . ?
C47 C48 H48A 119.0 . . ?
C43 C48 H48A 119.0 . . ?
C50 C49 C54 121.0(4) . . ?
C50 C49 O3 116.2(3) . . ?
C54 C49 O3 122.6(4) . . ?
C49 C50 C51 119.3(4) . . ?
C49 C50 H50A 120.3 . . ?
C51 C50 H50A 120.3 . . ?
C52 C51 C50 120.6(5) . . ?
C52 C51 H51A 119.7 . . ?
C50 C51 H51A 119.7 . . ?
C51 C52 C53 119.9(5) . . ?
C51 C52 H52A 120.1 . . ?
C53 C52 H52A 120.1 . . ?
C52 C53 C54 121.4(5) . . ?
C52 C53 H53A 119.3 . . ?
C54 C53 H53A 119.3 . . ?
C49 C54 C53 117.8(5) . . ?
C49 C54 H54A 121.1 . . ?
C53 C54 H54A 121.1 . . ?
C44 Ir1 C8 94.01(12) . . ?
C44 Ir1 C26 94.45(12) . . ?
C8 Ir1 C26 97.59(12) . . ?
C44 Ir1 N1 93.62(11) . . ?
C8 Ir1 N1 79.35(12) . . ?
C26 Ir1 N1 171.56(11) . . ?
C44 Ir1 N2 173.40(10) . . ?
C8 Ir1 N2 88.44(11) . . ?
C26 Ir1 N2 79.14(11) . . ?
N1 Ir1 N2 92.86(10) . . ?
C44 Ir1 N3 79.28(12) . . ?
C8 Ir1 N3 171.14(11) . . ?
C26 Ir1 N3 88.77(11) . . ?
N1 Ir1 N3 95.18(11) . . ?
N2 Ir1 N3 98.86(10) . . ?
C1 N1 C5 119.8(3) . . ?
C1 N1 Ir1 125.5(2) . . ?
C5 N1 Ir1 114.5(2) . . ?
C19 N2 C23 119.1(3) . . ?
C19 N2 Ir1 125.7(2) . . ?
C23 N2 Ir1 114.8(2) . . ?
C37 N3 C41 119.0(3) . . ?
C37 N3 Ir1 126.5(3) . . ?
C41 N3 Ir1 114.5(2) . . ?
C13 O1 C10 118.9(3) . . ?
C31 O2 C28 122.4(4) . . ?
C49 O3 C46 121.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.960
_refine_diff_density_min         -1.204
_refine_diff_density_rms         0.072


data_wy2104wc
_database_code_depnum_ccdc_archive 'CCDC 898070'
#TrackingRef 'WY2104WC.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H35 Ir N2 O4'
_chemical_formula_weight         811.91

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                   10.1672(11)
_cell_length_b                   11.4723(13)
_cell_length_c                   29.660(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.018(2)
_cell_angle_gamma                90.00
_cell_volume                     3446.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    21390
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      28.36

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    3.919
_exptl_absorpt_correction_type   multi-scans
_exptl_absorpt_correction_T_min  0.7483
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Smart CCD'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21390
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         28.36
_reflns_number_total             8302
_reflns_number_gt                6396
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        SAINT
_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^)+(0.0357P)^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         8302
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0790
_refine_ls_wR_factor_gt          0.0725
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2597(6) 0.2749(5) 0.1497(2) 0.0842(17) Uani 1 1 d . . .
H1A H 1.2337 0.2621 0.1193 0.101 Uiso 1 1 calc R . .
C2 C 1.3168(8) 0.1867(6) 0.1768(3) 0.119(3) Uani 1 1 d . . .
H2A H 1.3313 0.1142 0.1641 0.143 Uiso 1 1 calc R . .
C3 C 1.3510(7) 0.2040(7) 0.2205(3) 0.110(2) Uani 1 1 d . . .
H3A H 1.3842 0.1423 0.2384 0.132 Uiso 1 1 calc R . .
C4 C 1.3379(7) 0.3111(7) 0.2394(2) 0.105(2) Uani 1 1 d . . .
H4A H 1.3665 0.3241 0.2696 0.126 Uiso 1 1 calc R . .
C5 C 1.2819(6) 0.3992(5) 0.2131(2) 0.0862(17) Uani 1 1 d . . .
H5A H 1.2707 0.4724 0.2257 0.103 Uiso 1 1 calc R . .
C6 C 1.2430(4) 0.3805(4) 0.16910(18) 0.0594(12) Uani 1 1 d . . .
C7 C 1.0610(4) 0.5012(3) 0.14081(15) 0.0509(10) Uani 1 1 d . . .
C8 C 1.0200(4) 0.5870(3) 0.11013(14) 0.0484(10) Uani 1 1 d . . .
H8A H 1.0806 0.6196 0.0920 0.058 Uiso 1 1 calc R . .
C9 C 0.8905(4) 0.6253(3) 0.10577(12) 0.0403(8) Uani 1 1 d . . .
C10 C 0.8026(4) 0.5723(3) 0.13458(13) 0.0442(9) Uani 1 1 d . . .
C11 C 0.8464(4) 0.4849(3) 0.16486(14) 0.0511(10) Uani 1 1 d . . .
H11A H 0.7875 0.4507 0.1832 0.061 Uiso 1 1 calc R . .
C12 C 0.9756(4) 0.4486(3) 0.16806(14) 0.0550(11) Uani 1 1 d . . .
H12A H 1.0047 0.3899 0.1882 0.066 Uiso 1 1 calc R . .
C13 C 0.6684(4) 0.6194(3) 0.13113(12) 0.0418(8) Uani 1 1 d . . .
C14 C 0.5690(4) 0.5925(3) 0.15858(14) 0.0515(10) Uani 1 1 d . . .
H14A H 0.5816 0.5337 0.1801 0.062 Uiso 1 1 calc R . .
C15 C 0.4529(4) 0.6524(4) 0.15401(14) 0.0538(10) Uani 1 1 d . . .
H15A H 0.3873 0.6352 0.1730 0.065 Uiso 1 1 calc R . .
C16 C 0.4311(4) 0.7382(3) 0.12163(16) 0.0498(10) Uani 1 1 d . . .
C17 C 0.5312(4) 0.7578(3) 0.09432(15) 0.0462(9) Uani 1 1 d . . .
H17A H 0.5179 0.8139 0.0717 0.055 Uiso 1 1 calc R . .
C18 C 0.3059(4) 0.8085(5) 0.11606(19) 0.0774(15) Uani 1 1 d . . .
H18A H 0.3108 0.8631 0.0918 0.116 Uiso 1 1 calc R . .
H18B H 0.2948 0.8499 0.1436 0.116 Uiso 1 1 calc R . .
H18C H 0.2321 0.7573 0.1093 0.116 Uiso 1 1 calc R . .
C19 C 0.7364(6) 1.2371(4) 0.22959(18) 0.0674(13) Uani 1 1 d . . .
H19A H 0.6526 1.2407 0.2143 0.081 Uiso 1 1 calc R . .
C20 C 0.7747(7) 1.3179(4) 0.26322(19) 0.0813(16) Uani 1 1 d . . .
H20A H 0.7157 1.3749 0.2710 0.098 Uiso 1 1 calc R . .
C21 C 0.8980(7) 1.3136(5) 0.28474(18) 0.0828(17) Uani 1 1 d . . .
H21A H 0.9238 1.3690 0.3066 0.099 Uiso 1 1 calc R . .
C22 C 0.9839(7) 1.2293(5) 0.2746(2) 0.0836(17) Uani 1 1 d . . .
H22A H 1.0675 1.2259 0.2900 0.100 Uiso 1 1 calc R . .
C23 C 0.9471(5) 1.1477(4) 0.24104(17) 0.0731(14) Uani 1 1 d . . .
H23A H 1.0063 1.0905 0.2335 0.088 Uiso 1 1 calc R . .
C24 C 0.8234(5) 1.1526(4) 0.21935(15) 0.0591(11) Uani 1 1 d . . .
C25 C 0.8475(4) 1.0276(3) 0.15437(15) 0.0529(10) Uani 1 1 d . . .
C26 C 0.8014(4) 0.9245(3) 0.13505(14) 0.0504(10) Uani 1 1 d . . .
H26A H 0.7311 0.8865 0.1468 0.060 Uiso 1 1 calc R . .
C27 C 0.8580(4) 0.8764(3) 0.09840(12) 0.0387(8) Uani 1 1 d . . .
C28 C 0.9679(4) 0.9355(3) 0.08275(13) 0.0409(9) Uani 1 1 d . . .
C29 C 1.0139(4) 1.0382(3) 0.10353(14) 0.0487(10) Uani 1 1 d . . .
H29A H 1.0865 1.0758 0.0932 0.058 Uiso 1 1 calc R . .
C30 C 0.9533(4) 1.0846(3) 0.13909(15) 0.0548(11) Uani 1 1 d . . .
H30A H 0.9838 1.1538 0.1526 0.066 Uiso 1 1 calc R . .
C31 C 1.0238(3) 0.8814(3) 0.04421(12) 0.0389(8) Uani 1 1 d . . .
C32 C 1.1283(4) 0.9243(3) 0.02215(14) 0.0497(10) Uani 1 1 d . . .
H32A H 1.1666 0.9953 0.0308 0.060 Uiso 1 1 calc R . .
C33 C 1.1754(4) 0.8617(4) -0.01263(15) 0.0534(10) Uani 1 1 d . . .
H33A H 1.2445 0.8916 -0.0277 0.064 Uiso 1 1 calc R . .
C34 C 1.1209(5) 0.7545(3) -0.02551(15) 0.0515(10) Uani 1 1 d . . .
C35 C 1.0149(4) 0.7189(3) -0.00322(14) 0.0474(9) Uani 1 1 d . . .
H35A H 0.9747 0.6486 -0.0118 0.057 Uiso 1 1 calc R . .
C36 C 1.1718(5) 0.6813(5) -0.06251(16) 0.0710(13) Uani 1 1 d . . .
H36A H 1.1211 0.6108 -0.0660 0.107 Uiso 1 1 calc R . .
H36B H 1.2629 0.6624 -0.0546 0.107 Uiso 1 1 calc R . .
H36C H 1.1638 0.7242 -0.0904 0.107 Uiso 1 1 calc R . .
C37 C 0.6409(5) 0.4814(4) -0.04021(17) 0.0719(14) Uani 1 1 d . . .
H37A H 0.6877 0.4208 -0.0232 0.108 Uiso 1 1 calc R . .
H37B H 0.6695 0.4841 -0.0702 0.108 Uiso 1 1 calc R . .
H37C H 0.5478 0.4657 -0.0420 0.108 Uiso 1 1 calc R . .
C38 C 0.6686(4) 0.5972(4) -0.01700(15) 0.0505(10) Uani 1 1 d . . .
C39 C 0.6088(5) 0.6961(4) -0.03612(16) 0.0618(12) Uani 1 1 d . . .
H39A H 0.5529 0.6837 -0.0622 0.074 Uiso 1 1 calc R . .
C40 C 0.6207(4) 0.8117(4) -0.02177(14) 0.0497(10) Uani 1 1 d . . .
C41 C 0.5510(5) 0.9037(4) -0.05058(16) 0.0697(13) Uani 1 1 d . . .
H41A H 0.5669 0.9786 -0.0367 0.105 Uiso 1 1 calc R . .
H41B H 0.4579 0.8881 -0.0535 0.105 Uiso 1 1 calc R . .
H41C H 0.5836 0.9035 -0.0800 0.105 Uiso 1 1 calc R . .
Ir1 Ir 0.801393(14) 0.736967(11) 0.061656(5) 0.03847(6) Uani 1 1 d . . .
N1 N 0.6462(3) 0.7013(2) 0.09826(10) 0.0378(7) Uani 1 1 d . . .
N2 N 0.9657(3) 0.7802(2) 0.03036(11) 0.0387(7) Uani 1 1 d . . .
O1 O 1.1937(3) 0.4713(3) 0.14129(12) 0.0811(11) Uani 1 1 d . . .
O2 O 0.7747(3) 1.0694(3) 0.18858(12) 0.0784(10) Uani 1 1 d . . .
O3 O 0.7475(3) 0.5926(2) 0.01807(9) 0.0479(7) Uani 1 1 d . . .
O4 O 0.6880(3) 0.8471(2) 0.01349(9) 0.0483(7) Uani 1 1 d . . .

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
C1 0.102(5) 0.075(4) 0.072(4) 0.005(3) -0.010(3) -0.003(3)
C2 0.179(8) 0.066(4) 0.116(6) 0.014(4) 0.031(6) 0.041(4)
C3 0.110(5) 0.128(6) 0.093(6) 0.040(5) 0.010(5) 0.044(5)
C4 0.107(5) 0.147(6) 0.059(4) 0.019(4) -0.008(4) 0.016(5)
C5 0.102(5) 0.094(4) 0.064(4) -0.002(3) 0.015(3) 0.007(3)
C6 0.042(2) 0.069(3) 0.068(3) 0.019(2) 0.006(2) 0.005(2)
C7 0.046(2) 0.051(2) 0.056(3) 0.0103(19) 0.007(2) 0.0018(17)
C8 0.044(2) 0.049(2) 0.053(3) 0.0123(18) 0.007(2) -0.0080(17)
C9 0.050(2) 0.0348(18) 0.036(2) -0.0005(14) 0.0002(17) -0.0078(15)
C10 0.050(2) 0.040(2) 0.043(2) 0.0035(16) 0.0045(19) -0.0071(16)
C11 0.062(3) 0.050(2) 0.043(2) 0.0134(18) 0.014(2) -0.0021(19)
C12 0.064(3) 0.050(2) 0.050(3) 0.0150(19) 0.006(2) 0.007(2)
C13 0.047(2) 0.0395(19) 0.039(2) 0.0016(15) 0.0017(17) -0.0095(15)
C14 0.055(3) 0.054(2) 0.046(3) 0.0128(18) 0.009(2) -0.0069(19)
C15 0.052(3) 0.068(3) 0.043(3) 0.000(2) 0.006(2) -0.013(2)
C16 0.045(2) 0.055(2) 0.049(3) 0.0004(18) 0.0058(19) -0.0070(17)
C17 0.053(2) 0.042(2) 0.043(2) 0.0029(16) -0.0022(19) -0.0076(16)
C18 0.055(3) 0.098(4) 0.079(4) 0.021(3) 0.008(3) 0.013(3)
C19 0.085(4) 0.061(3) 0.057(3) -0.001(2) 0.011(3) -0.003(2)
C20 0.125(5) 0.057(3) 0.067(4) -0.006(3) 0.035(4) 0.003(3)
C21 0.125(5) 0.078(4) 0.047(3) -0.013(3) 0.016(3) -0.034(4)
C22 0.102(5) 0.093(4) 0.054(3) 0.007(3) -0.006(3) -0.023(3)
C23 0.090(4) 0.063(3) 0.065(3) 0.002(2) 0.001(3) -0.001(3)
C24 0.077(3) 0.048(2) 0.054(3) -0.006(2) 0.013(2) -0.013(2)
C25 0.062(3) 0.048(2) 0.049(3) -0.0067(18) 0.004(2) -0.0067(19)
C26 0.052(2) 0.051(2) 0.049(3) 0.0007(18) 0.002(2) -0.0106(18)
C27 0.042(2) 0.0386(19) 0.033(2) 0.0071(15) -0.0071(17) -0.0064(15)
C28 0.043(2) 0.0353(18) 0.042(2) 0.0093(15) -0.0046(18) -0.0048(15)
C29 0.050(2) 0.045(2) 0.050(3) 0.0038(17) -0.002(2) -0.0132(17)
C30 0.064(3) 0.040(2) 0.059(3) -0.0074(18) -0.003(2) -0.0134(18)
C31 0.039(2) 0.0348(18) 0.041(2) 0.0119(15) -0.0047(17) -0.0030(14)
C32 0.045(2) 0.047(2) 0.056(3) 0.0116(18) -0.001(2) -0.0090(17)
C33 0.048(2) 0.058(3) 0.054(3) 0.016(2) 0.003(2) -0.0107(19)
C34 0.055(3) 0.053(2) 0.046(3) 0.0099(18) 0.008(2) 0.0035(18)
C35 0.055(2) 0.041(2) 0.046(2) 0.0070(17) 0.006(2) -0.0065(17)
C36 0.082(3) 0.066(3) 0.070(3) 0.004(2) 0.029(3) 0.001(2)
C37 0.088(4) 0.066(3) 0.061(3) -0.016(2) -0.002(3) -0.020(3)
C38 0.054(3) 0.054(2) 0.044(3) -0.0065(19) 0.008(2) -0.0163(19)
C39 0.064(3) 0.069(3) 0.051(3) -0.003(2) -0.010(2) -0.013(2)
C40 0.048(2) 0.061(3) 0.040(2) 0.0101(19) 0.0046(19) -0.0102(19)
C41 0.064(3) 0.076(3) 0.067(3) 0.022(3) -0.009(3) 0.005(2)
Ir1 0.04454(9) 0.03318(8) 0.03732(9) 0.00419(6) 0.00147(6) -0.00873(6)
N1 0.0417(17) 0.0348(15) 0.0365(17) -0.0003(12) 0.0000(14) -0.0097(13)
N2 0.0401(17) 0.0367(15) 0.0392(18) 0.0081(13) 0.0021(14) -0.0043(12)
O1 0.0532(19) 0.090(2) 0.102(3) 0.049(2) 0.0193(19) 0.0148(16)
O2 0.075(2) 0.080(2) 0.083(3) -0.0402(19) 0.0242(19) -0.0238(17)
O3 0.0564(17) 0.0435(15) 0.0432(17) -0.0013(12) 0.0006(14) -0.0107(12)
O4 0.0504(16) 0.0461(15) 0.0475(17) 0.0094(12) -0.0012(14) -0.0034(12)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.358(7) . ?
C1 C2 1.386(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.327(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.362(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.370(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.347(7) . ?
C5 H5A 0.9300 . ?
C6 O1 1.394(5) . ?
C7 C12 1.376(5) . ?
C7 C8 1.380(5) . ?
C7 O1 1.391(5) . ?
C8 C9 1.384(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.426(5) . ?
C9 Ir1 1.992(4) . ?
C10 C11 1.393(5) . ?
C10 C13 1.463(5) . ?
C11 C12 1.374(6) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 N1 1.359(4) . ?
C13 C14 1.387(5) . ?
C14 C15 1.363(6) . ?
C14 H14A 0.9300 . ?
C15 C16 1.379(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.373(6) . ?
C16 C18 1.504(6) . ?
C17 N1 1.333(5) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C24 1.365(6) . ?
C19 C20 1.392(7) . ?
C19 H19A 0.9300 . ?
C20 C21 1.358(7) . ?
C20 H20A 0.9300 . ?
C21 C22 1.355(8) . ?
C21 H21A 0.9300 . ?
C22 C23 1.393(7) . ?
C22 H22A 0.9300 . ?
C23 C24 1.363(6) . ?
C23 H23A 0.9300 . ?
C24 O2 1.382(5) . ?
C25 C30 1.369(6) . ?
C25 C26 1.379(5) . ?
C25 O2 1.393(5) . ?
C26 C27 1.388(5) . ?
C26 H26A 0.9300 . ?
C27 C28 1.419(5) . ?
C27 Ir1 1.992(4) . ?
C28 C29 1.391(5) . ?
C28 C31 1.459(5) . ?
C29 C30 1.374(5) . ?
C29 H29A 0.9300 . ?
C30 H30A 0.9300 . ?
C31 N2 1.350(4) . ?
C31 C32 1.385(5) . ?
C32 C33 1.377(6) . ?
C32 H32A 0.9300 . ?
C33 C34 1.389(5) . ?
C33 H33A 0.9300 . ?
C34 C35 1.375(6) . ?
C34 C36 1.509(6) . ?
C35 N2 1.350(5) . ?
C35 H35A 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C38 1.512(5) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 O3 1.258(5) . ?
C38 C39 1.385(6) . ?
C39 C40 1.394(6) . ?
C39 H39A 0.9300 . ?
C40 O4 1.266(5) . ?
C40 C41 1.497(6) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
Ir1 N1 2.034(3) . ?
Ir1 N2 2.042(3) . ?
Ir1 O3 2.142(3) . ?
Ir1 O4 2.163(3) . ?

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
C6 C1 C2 117.9(6) . . ?
C6 C1 H1A 121.0 . . ?
C2 C1 H1A 121.0 . . ?
C3 C2 C1 121.1(6) . . ?
C3 C2 H2A 119.4 . . ?
C1 C2 H2A 119.4 . . ?
C2 C3 C4 120.7(6) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C3 C4 C5 118.9(6) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
C6 C5 C4 120.4(6) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C1 121.0(5) . . ?
C5 C6 O1 120.9(5) . . ?
C1 C6 O1 117.9(5) . . ?
C12 C7 C8 122.1(4) . . ?
C12 C7 O1 123.2(4) . . ?
C8 C7 O1 114.8(3) . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 H8A 119.4 . . ?
C9 C8 H8A 119.4 . . ?
C8 C9 C10 116.7(3) . . ?
C8 C9 Ir1 129.8(3) . . ?
C10 C9 Ir1 113.3(3) . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 C13 123.7(3) . . ?
C9 C10 C13 115.5(3) . . ?
C12 C11 C10 120.9(4) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C11 C12 C7 118.3(4) . . ?
C11 C12 H12A 120.8 . . ?
C7 C12 H12A 120.8 . . ?
N1 C13 C14 119.4(3) . . ?
N1 C13 C10 113.7(3) . . ?
C14 C13 C10 126.8(3) . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C14 C15 C16 120.9(4) . . ?
C14 C15 H15A 119.5 . . ?
C16 C15 H15A 119.5 . . ?
C17 C16 C15 116.5(4) . . ?
C17 C16 C18 120.7(4) . . ?
C15 C16 C18 122.8(4) . . ?
N1 C17 C16 123.9(4) . . ?
N1 C17 H17A 118.0 . . ?
C16 C17 H17A 118.0 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 119.1(6) . . ?
C24 C19 H19A 120.4 . . ?
C20 C19 H19A 120.4 . . ?
C21 C20 C19 120.1(5) . . ?
C21 C20 H20A 119.9 . . ?
C19 C20 H20A 119.9 . . ?
C22 C21 C20 120.6(5) . . ?
C22 C21 H21A 119.7 . . ?
C20 C21 H21A 119.7 . . ?
C21 C22 C23 120.1(6) . . ?
C21 C22 H22A 120.0 . . ?
C23 C22 H22A 120.0 . . ?
C24 C23 C22 119.2(5) . . ?
C24 C23 H23A 120.4 . . ?
C22 C23 H23A 120.4 . . ?
C23 C24 C19 120.9(5) . . ?
C23 C24 O2 123.0(4) . . ?
C19 C24 O2 115.8(5) . . ?
C30 C25 C26 121.4(4) . . ?
C30 C25 O2 124.0(4) . . ?
C26 C25 O2 114.5(4) . . ?
C25 C26 C27 121.1(4) . . ?
C25 C26 H26A 119.4 . . ?
C27 C26 H26A 119.4 . . ?
C26 C27 C28 117.3(3) . . ?
C26 C27 Ir1 128.9(3) . . ?
C28 C27 Ir1 113.8(3) . . ?
C29 C28 C27 120.3(4) . . ?
C29 C28 C31 124.6(3) . . ?
C27 C28 C31 115.1(3) . . ?
C30 C29 C28 120.8(4) . . ?
C30 C29 H29A 119.6 . . ?
C28 C29 H29A 119.6 . . ?
C25 C30 C29 119.1(4) . . ?
C25 C30 H30A 120.4 . . ?
C29 C30 H30A 120.4 . . ?
N2 C31 C32 119.7(4) . . ?
N2 C31 C28 114.5(3) . . ?
C32 C31 C28 125.9(3) . . ?
C33 C32 C31 120.0(4) . . ?
C33 C32 H32A 120.0 . . ?
C31 C32 H32A 120.0 . . ?
C32 C33 C34 120.7(4) . . ?
C32 C33 H33A 119.6 . . ?
C34 C33 H33A 119.6 . . ?
C35 C34 C33 116.2(4) . . ?
C35 C34 C36 121.2(4) . . ?
C33 C34 C36 122.6(4) . . ?
N2 C35 C34 123.8(4) . . ?
N2 C35 H35A 118.1 . . ?
C34 C35 H35A 118.1 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 H37A 109.5 . . ?
C38 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C38 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O3 C38 C39 126.7(4) . . ?
O3 C38 C37 114.8(4) . . ?
C39 C38 C37 118.4(4) . . ?
C38 C39 C40 129.1(4) . . ?
C38 C39 H39A 115.4 . . ?
C40 C39 H39A 115.4 . . ?
O4 C40 C39 125.7(4) . . ?
O4 C40 C41 116.1(4) . . ?
C39 C40 C41 118.2(4) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C27 Ir1 C9 93.66(15) . . ?
C27 Ir1 N1 94.02(13) . . ?
C9 Ir1 N1 81.35(14) . . ?
C27 Ir1 N2 81.07(14) . . ?
C9 Ir1 N2 96.41(14) . . ?
N1 Ir1 N2 174.49(11) . . ?
C27 Ir1 O3 175.75(12) . . ?
C9 Ir1 O3 88.67(12) . . ?
N1 Ir1 O3 89.85(11) . . ?
N2 Ir1 O3 95.14(11) . . ?
C27 Ir1 O4 90.25(12) . . ?
C9 Ir1 O4 174.38(12) . . ?
N1 Ir1 O4 94.37(11) . . ?
N2 Ir1 O4 88.17(11) . . ?
O3 Ir1 O4 87.69(10) . . ?
C17 N1 C13 119.2(3) . . ?
C17 N1 Ir1 124.8(3) . . ?
C13 N1 Ir1 115.7(2) . . ?
C35 N2 C31 119.5(3) . . ?
C35 N2 Ir1 125.4(2) . . ?
C31 N2 Ir1 115.1(2) . . ?
C7 O1 C6 119.2(3) . . ?
C24 O2 C25 122.5(3) . . ?
C38 O3 Ir1 125.3(2) . . ?
C40 O4 Ir1 125.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.896
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.091