# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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 retrieval see:
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_3a

_audit_creation_method           'SHELXL-97 (Sheldrick, 2008)'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H44 Cl Ir N2 O'
_chemical_formula_sum            'C33 H44 Cl Ir N2 O'
_chemical_formula_weight         712.35

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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

_cell_length_a                   17.1507(5)
_cell_length_b                   7.7780(2)
_cell_length_c                   24.0381(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.298(3)
_cell_angle_gamma                90.00
_cell_volume                     3077.78(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5074
_cell_measurement_theta_min      3.5310
_cell_measurement_theta_max      26.5230

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.285
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.071
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1432
_exptl_absorpt_coefficient_mu    4.452
_exptl_absorpt_correction_T_min  0.321
_exptl_absorpt_correction_T_max  0.729
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_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  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1333
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14245
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         26.37
_reflns_number_total             6286
_reflns_number_gt                4492
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0300P)²+4.9942P] where P=(Fo²+2Fc²)/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         6286
_refine_ls_number_parameters     337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.157897(13) 0.95991(3) 0.190117(11) 0.05203(10) Uani 1 1 d . . .
O1 O 0.4074(3) 1.0606(4) 0.2073(2) 0.0587(11) Uani 1 1 d . . .
H1 H 0.3586 1.0815 0.1988 0.088 Uiso 1 1 calc R . .
N1 N 0.2481(3) 0.9404(6) 0.3186(2) 0.0458(12) Uani 1 1 d . . .
C1 C 0.2494(3) 0.9100(7) 0.2627(3) 0.0444(14) Uani 1 1 d . . .
Cl1 Cl 0.22304(10) 1.2117(2) 0.17150(8) 0.0669(5) Uani 1 1 d . . .
C2 C 0.3669(3) 0.8169(6) 0.3244(2) 0.0381(13) Uani 1 1 d . . .
N2 N 0.3220(3) 0.8355(5) 0.26647(19) 0.0389(11) Uani 1 1 d . . .
C4 C 0.3457(3) 0.8790(7) 0.4178(3) 0.0483(14) Uani 1 1 d . . .
H4 H 0.3131 0.9211 0.4397 0.058 Uiso 1 1 calc R . .
C5 C 0.4213(4) 0.8117(7) 0.4439(2) 0.0465(14) Uani 1 1 d . . .
C7 C 0.4443(3) 0.7529(6) 0.3511(2) 0.0416(13) Uani 1 1 d . . .
H7 H 0.4768 0.7108 0.3291 0.050 Uiso 1 1 calc R . .
C6 C 0.4717(3) 0.7532(6) 0.4111(3) 0.0421(14) Uani 1 1 d . . .
C9 C 0.4496(4) 0.8043(8) 0.5095(3) 0.0628(18) Uani 1 1 d . . .
H9A H 0.4630 0.6879 0.5217 0.094 Uiso 1 1 calc R . .
H9B H 0.4070 0.8448 0.5249 0.094 Uiso 1 1 calc R . .
H9C H 0.4967 0.8757 0.5235 0.094 Uiso 1 1 calc R . .
C20 C 0.4193(3) 0.8810(7) 0.2089(2) 0.0438(13) Uani 1 1 d . . .
H20 H 0.4653 0.8555 0.2427 0.053 Uiso 1 1 calc R . .
C10 C 0.1784(4) 1.0203(8) 0.3331(3) 0.0614(18) Uani 1 1 d . . .
H10A H 0.1449 0.9301 0.3421 0.074 Uiso 1 1 calc R . .
H10B H 0.1459 1.0807 0.2991 0.074 Uiso 1 1 calc R . .
C11 C 0.0824(4) 0.7805(10) 0.2148(4) 0.086(3) Uani 1 1 d . . .
H11 H 0.1004 0.7481 0.2559 0.104 Uiso 1 1 calc R . .
C12 C 0.1247(5) 0.7002(10) 0.1807(4) 0.084(3) Uani 1 1 d . . .
H12 H 0.1674 0.6225 0.2025 0.101 Uiso 1 1 calc R . .
C13 C 0.0917(6) 0.6524(11) 0.1167(4) 0.110(2) Uani 1 1 d . . .
H13A H 0.1367 0.6132 0.1029 0.132 Uiso 1 1 calc R . .
H13B H 0.0545 0.5566 0.1135 0.132 Uiso 1 1 calc R . .
C31 C 0.2469(5) 1.5166(10) 0.5229(3) 0.090(3) Uani 1 1 d . . .
H31A H 0.1975 1.5782 0.5204 0.134 Uiso 1 1 calc R . .
H31B H 0.2881 1.5958 0.5193 0.134 Uiso 1 1 calc R . .
H31C H 0.2645 1.4594 0.5597 0.134 Uiso 1 1 calc R . .
C14 C 0.0499(5) 0.7899(11) 0.0787(4) 0.110(2) Uani 1 1 d . . .
H14A H -0.0082 0.7777 0.0730 0.132 Uiso 1 1 calc R . .
H14B H 0.0600 0.7773 0.0412 0.132 Uiso 1 1 calc R . .
C16 C 0.0413(4) 1.0560(10) 0.1381(3) 0.073(2) Uani 1 1 d . . .
H16 H 0.0398 1.1808 0.1322 0.087 Uiso 1 1 calc R . .
C19 C 0.3471(3) 0.7796(7) 0.2155(2) 0.0429(13) Uani 1 1 d . . .
H19 H 0.3017 0.8060 0.1815 0.052 Uiso 1 1 calc R . .
C18 C -0.0075(5) 0.8277(13) 0.1931(4) 0.111(2) Uani 1 1 d . . .
H18A H -0.0358 0.7354 0.1684 0.133 Uiso 1 1 calc R . .
H18B H -0.0292 0.8343 0.2262 0.133 Uiso 1 1 calc R . .
C17 C -0.0258(5) 0.9885(13) 0.1609(5) 0.111(2) Uani 1 1 d . . .
H17A H -0.0388 1.0750 0.1860 0.133 Uiso 1 1 calc R . .
H17B H -0.0738 0.9718 0.1286 0.133 Uiso 1 1 calc R . .
C23 C 0.3839(4) 0.5303(8) 0.1622(3) 0.0628(18) Uani 1 1 d . . .
H23A H 0.3951 0.4079 0.1642 0.075 Uiso 1 1 calc R . .
H23B H 0.3394 0.5518 0.1277 0.075 Uiso 1 1 calc R . .
C21 C 0.4416(4) 0.8198(7) 0.1555(3) 0.0544(16) Uani 1 1 d . . .
H21A H 0.4896 0.8808 0.1525 0.065 Uiso 1 1 calc R . .
H21B H 0.3975 0.8460 0.1213 0.065 Uiso 1 1 calc R . .
C30 C 0.2407(4) 1.2973(8) 0.3799(3) 0.0558(16) Uani 1 1 d . . .
C29 C 0.2560(4) 1.4136(9) 0.4256(3) 0.0627(18) Uani 1 1 d . . .
H29 H 0.2834 1.5149 0.4229 0.075 Uiso 1 1 calc R . .
C28 C 0.2320(4) 1.3845(10) 0.4746(3) 0.0608(17) Uani 1 1 d . . .
C27 C 0.1936(4) 1.2320(10) 0.4783(3) 0.0659(19) Uani 1 1 d . . .
H27 H 0.1779 1.2088 0.5115 0.079 Uiso 1 1 calc R . .
C26 C 0.1771(4) 1.1102(9) 0.4336(3) 0.0613(18) Uani 1 1 d . . .
C25 C 0.2010(3) 1.1454(8) 0.3835(3) 0.0530(16) Uani 1 1 d . . .
C24 C 0.3589(4) 0.5853(7) 0.2158(3) 0.0540(16) Uani 1 1 d . . .
H24A H 0.3086 0.5283 0.2160 0.065 Uiso 1 1 calc R . .
H24B H 0.4005 0.5515 0.2505 0.065 Uiso 1 1 calc R . .
C22 C 0.4581(4) 0.6268(8) 0.1579(3) 0.0632(18) Uani 1 1 d . . .
H22A H 0.4722 0.5914 0.1232 0.076 Uiso 1 1 calc R . .
H22B H 0.5036 0.6004 0.1912 0.076 Uiso 1 1 calc R . .
C32 C 0.1348(5) 0.9450(10) 0.4422(4) 0.093(3) Uani 1 1 d . . .
H32A H 0.0819 0.9405 0.4148 0.139 Uiso 1 1 calc R . .
H32B H 0.1293 0.9418 0.4809 0.139 Uiso 1 1 calc R . .
H32C H 0.1663 0.8482 0.4364 0.139 Uiso 1 1 calc R . .
C33 C 0.2672(5) 1.3417(10) 0.3268(3) 0.088(2) Uani 1 1 d . . .
H33A H 0.3120 1.2695 0.3253 0.132 Uiso 1 1 calc R . .
H33B H 0.2838 1.4600 0.3288 0.132 Uiso 1 1 calc R . .
H33C H 0.2228 1.3239 0.2927 0.132 Uiso 1 1 calc R . .
C8 C 0.5575(3) 0.6959(8) 0.4404(3) 0.0569(17) Uani 1 1 d . . .
H8A H 0.5563 0.5990 0.4649 0.085 Uiso 1 1 calc R . .
H8B H 0.5869 0.7884 0.4634 0.085 Uiso 1 1 calc R . .
H8C H 0.5838 0.6637 0.4116 0.085 Uiso 1 1 calc R . .
C3 C 0.3197(3) 0.8821(7) 0.3575(2) 0.0422(13) Uani 1 1 d . . .
C15 C 0.0753(4) 0.9671(10) 0.1015(3) 0.072(2) Uani 1 1 d . . .
H15 H 0.0942 1.0401 0.0747 0.087 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C1 2.030(6) . ?
Ir1 C12 2.093(7) . ?
Ir1 C11 2.100(7) . ?
Ir1 C16 2.172(6) . ?
Ir1 C15 2.203(6) . ?
Ir1 Cl1 2.3591(16) . ?
O1 C20 1.410(6) . ?
O1 H1 0.8200 . ?
N1 C1 1.371(7) . ?
N1 C3 1.395(7) . ?
N1 C10 1.472(7) . ?
C1 N2 1.354(7) . ?
C2 C3 1.381(7) . ?
C2 C7 1.394(7) . ?
C2 N2 1.397(7) . ?
N2 C19 1.473(7) . ?
C4 C5 1.375(8) . ?
C4 C3 1.391(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(8) . ?
C5 C9 1.517(8) . ?
C7 C6 1.386(7) . ?
C7 H7 0.9300 . ?
C6 C8 1.509(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C20 C19 1.514(7) . ?
C20 C21 1.515(8) . ?
C20 H20 0.9800 . ?
C10 C25 1.518(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.387(11) . ?
C11 C18 1.528(10) . ?
C11 H11 0.9800 . ?
C12 C13 1.529(11) . ?
C12 H12 0.9800 . ?
C13 C14 1.458(11) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C31 C28 1.519(9) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C14 C15 1.501(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 C15 1.370(10) . ?
C16 C17 1.503(11) . ?
C16 H16 0.9800 . ?
C19 C24 1.524(7) . ?
C19 H19 0.9800 . ?
C18 C17 1.457(12) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C23 C22 1.507(9) . ?
C23 C24 1.529(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C21 C22 1.526(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C30 C25 1.379(8) . ?
C30 C29 1.391(9) . ?
C30 C33 1.509(9) . ?
C29 C28 1.369(9) . ?
C29 H29 0.9300 . ?
C28 C27 1.372(9) . ?
C27 C26 1.399(9) . ?
C27 H27 0.9300 . ?
C26 C25 1.405(9) . ?
C26 C32 1.518(9) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C15 H15 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ir1 C12 91.7(3) . . ?
C1 Ir1 C11 91.1(3) . . ?
C12 Ir1 C11 38.6(3) . . ?
C1 Ir1 C16 157.7(3) . . ?
C12 Ir1 C16 95.2(3) . . ?
C11 Ir1 C16 81.4(3) . . ?
C1 Ir1 C15 165.5(3) . . ?
C12 Ir1 C15 80.7(3) . . ?
C11 Ir1 C15 90.6(3) . . ?
C16 Ir1 C15 36.5(2) . . ?
C1 Ir1 Cl1 91.65(15) . . ?
C12 Ir1 Cl1 155.4(3) . . ?
C11 Ir1 Cl1 165.5(3) . . ?
C16 Ir1 Cl1 90.8(2) . . ?
C15 Ir1 Cl1 90.3(2) . . ?
C20 O1 H1 109.5 . . ?
C1 N1 C3 110.3(5) . . ?
C1 N1 C10 122.8(5) . . ?
C3 N1 C10 126.9(5) . . ?
N2 C1 N1 106.0(5) . . ?
N2 C1 Ir1 127.9(4) . . ?
N1 C1 Ir1 126.0(4) . . ?
C3 C2 C7 120.1(5) . . ?
C3 C2 N2 106.8(5) . . ?
C7 C2 N2 133.1(5) . . ?
C1 N2 C2 110.5(5) . . ?
C1 N2 C19 123.3(5) . . ?
C2 N2 C19 126.2(4) . . ?
C5 C4 C3 117.8(6) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C4 C5 C6 121.3(5) . . ?
C4 C5 C9 118.3(6) . . ?
C6 C5 C9 120.4(5) . . ?
C6 C7 C2 118.7(5) . . ?
C6 C7 H7 120.7 . . ?
C2 C7 H7 120.7 . . ?
C7 C6 C5 120.2(5) . . ?
C7 C6 C8 119.2(5) . . ?
C5 C6 C8 120.5(5) . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C20 C19 113.8(5) . . ?
O1 C20 C21 110.9(5) . . ?
C19 C20 C21 109.5(5) . . ?
O1 C20 H20 107.5 . . ?
C19 C20 H20 107.5 . . ?
C21 C20 H20 107.5 . . ?
N1 C10 C25 114.6(5) . . ?
N1 C10 H10A 108.6 . . ?
C25 C10 H10A 108.6 . . ?
N1 C10 H10B 108.6 . . ?
C25 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C18 123.4(8) . . ?
C12 C11 Ir1 70.4(5) . . ?
C18 C11 Ir1 112.7(6) . . ?
C12 C11 H11 114.2 . . ?
C18 C11 H11 114.2 . . ?
Ir1 C11 H11 114.2 . . ?
C11 C12 C13 126.7(8) . . ?
C11 C12 Ir1 71.0(4) . . ?
C13 C12 Ir1 110.9(6) . . ?
C11 C12 H12 113.4 . . ?
C13 C12 H12 113.4 . . ?
Ir1 C12 H12 113.4 . . ?
C14 C13 C12 115.4(8) . . ?
C14 C13 H13A 108.4 . . ?
C12 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C12 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C13 C14 C15 113.8(7) . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C15 C16 C17 124.4(8) . . ?
C15 C16 Ir1 73.0(4) . . ?
C17 C16 Ir1 110.2(5) . . ?
C15 C16 H16 114.0 . . ?
C17 C16 H16 114.0 . . ?
Ir1 C16 H16 114.0 . . ?
N2 C19 C20 111.8(4) . . ?
N2 C19 C24 111.0(5) . . ?
C20 C19 C24 114.0(5) . . ?
N2 C19 H19 106.5 . . ?
C20 C19 H19 106.5 . . ?
C24 C19 H19 106.5 . . ?
C17 C18 C11 115.7(7) . . ?
C17 C18 H18A 108.3 . . ?
C11 C18 H18A 108.3 . . ?
C17 C18 H18B 108.3 . . ?
C11 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C18 C17 C16 114.9(8) . . ?
C18 C17 H17A 108.5 . . ?
C16 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
C16 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C22 C23 C24 111.2(5) . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
C24 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C20 C21 C22 111.5(5) . . ?
C20 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
C20 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C25 C30 C29 119.6(6) . . ?
C25 C30 C33 121.4(6) . . ?
C29 C30 C33 119.0(6) . . ?
C28 C29 C30 122.4(7) . . ?
C28 C29 H29 118.8 . . ?
C30 C29 H29 118.8 . . ?
C29 C28 C27 117.7(7) . . ?
C29 C28 C31 121.3(7) . . ?
C27 C28 C31 121.1(7) . . ?
C28 C27 C26 122.2(7) . . ?
C28 C27 H27 118.9 . . ?
C26 C27 H27 118.9 . . ?
C27 C26 C25 118.7(6) . . ?
C27 C26 C32 118.1(7) . . ?
C25 C26 C32 123.2(7) . . ?
C30 C25 C26 119.3(6) . . ?
C30 C25 C10 121.2(6) . . ?
C26 C25 C10 119.3(6) . . ?
C19 C24 C23 110.0(5) . . ?
C19 C24 H24A 109.7 . . ?
C23 C24 H24A 109.7 . . ?
C19 C24 H24B 109.7 . . ?
C23 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
C23 C22 C21 109.9(5) . . ?
C23 C22 H22A 109.7 . . ?
C21 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C26 C32 H32A 109.5 . . ?
C26 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C26 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C3 C4 121.7(5) . . ?
C2 C3 N1 106.3(5) . . ?
C4 C3 N1 131.9(5) . . ?
C16 C15 C14 124.4(8) . . ?
C16 C15 Ir1 70.5(4) . . ?
C14 C15 Ir1 111.8(5) . . ?
C16 C15 H15 114.1 . . ?
C14 C15 H15 114.1 . . ?
Ir1 C15 H15 114.1 . . ?

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
C3 N1 C1 N2 -0.9(6) . . . . ?
C10 N1 C1 N2 -179.7(5) . . . . ?
C3 N1 C1 Ir1 176.9(4) . . . . ?
C10 N1 C1 Ir1 -1.9(7) . . . . ?
C12 Ir1 C1 N2 74.8(5) . . . . ?
C11 Ir1 C1 N2 113.4(5) . . . . ?
C16 Ir1 C1 N2 -176.9(6) . . . . ?
C15 Ir1 C1 N2 16.9(13) . . . . ?
Cl1 Ir1 C1 N2 -80.9(4) . . . . ?
C12 Ir1 C1 N1 -102.6(5) . . . . ?
C11 Ir1 C1 N1 -63.9(5) . . . . ?
C16 Ir1 C1 N1 5.7(9) . . . . ?
C15 Ir1 C1 N1 -160.4(9) . . . . ?
Cl1 Ir1 C1 N1 101.8(4) . . . . ?
N1 C1 N2 C2 0.4(6) . . . . ?
Ir1 C1 N2 C2 -177.4(4) . . . . ?
N1 C1 N2 C19 179.0(4) . . . . ?
Ir1 C1 N2 C19 1.2(7) . . . . ?
C3 C2 N2 C1 0.3(6) . . . . ?
C7 C2 N2 C1 -178.3(5) . . . . ?
C3 C2 N2 C19 -178.3(5) . . . . ?
C7 C2 N2 C19 3.1(9) . . . . ?
C3 C4 C5 C6 2.0(8) . . . . ?
C3 C4 C5 C9 -178.8(5) . . . . ?
C3 C2 C7 C6 1.2(8) . . . . ?
N2 C2 C7 C6 179.7(5) . . . . ?
C2 C7 C6 C5 2.1(8) . . . . ?
C2 C7 C6 C8 -175.8(5) . . . . ?
C4 C5 C6 C7 -3.8(8) . . . . ?
C9 C5 C6 C7 177.1(5) . . . . ?
C4 C5 C6 C8 174.0(5) . . . . ?
C9 C5 C6 C8 -5.1(8) . . . . ?
C1 N1 C10 C25 -141.4(6) . . . . ?
C3 N1 C10 C25 40.0(8) . . . . ?
C1 Ir1 C11 C12 -91.4(5) . . . . ?
C16 Ir1 C11 C12 109.7(5) . . . . ?
C15 Ir1 C11 C12 74.2(5) . . . . ?
Cl1 Ir1 C11 C12 167.8(7) . . . . ?
C1 Ir1 C11 C18 149.6(7) . . . . ?
C12 Ir1 C11 C18 -119.0(9) . . . . ?
C16 Ir1 C11 C18 -9.3(7) . . . . ?
C15 Ir1 C11 C18 -44.8(7) . . . . ?
Cl1 Ir1 C11 C18 48.8(14) . . . . ?
C18 C11 C12 C13 2.6(13) . . . . ?
Ir1 C11 C12 C13 -102.3(8) . . . . ?
C18 C11 C12 Ir1 104.9(8) . . . . ?
C1 Ir1 C12 C11 89.6(5) . . . . ?
C16 Ir1 C12 C11 -69.2(5) . . . . ?
C15 Ir1 C12 C11 -102.8(5) . . . . ?
Cl1 Ir1 C12 C11 -172.7(4) . . . . ?
C1 Ir1 C12 C13 -147.3(7) . . . . ?
C11 Ir1 C12 C13 123.1(9) . . . . ?
C16 Ir1 C12 C13 53.8(7) . . . . ?
C15 Ir1 C12 C13 20.3(6) . . . . ?
Cl1 Ir1 C12 C13 -49.6(9) . . . . ?
C11 C12 C13 C14 50.1(13) . . . . ?
Ir1 C12 C13 C14 -31.2(11) . . . . ?
C12 C13 C14 C15 24.6(13) . . . . ?
C1 Ir1 C16 C15 -174.2(5) . . . . ?
C12 Ir1 C16 C15 -66.6(5) . . . . ?
C11 Ir1 C16 C15 -102.8(5) . . . . ?
Cl1 Ir1 C16 C15 89.6(5) . . . . ?
C1 Ir1 C16 C17 -53.1(10) . . . . ?
C12 Ir1 C16 C17 54.6(7) . . . . ?
C11 Ir1 C16 C17 18.4(6) . . . . ?
C15 Ir1 C16 C17 121.2(8) . . . . ?
Cl1 Ir1 C16 C17 -149.3(6) . . . . ?
C1 N2 C19 C20 115.2(5) . . . . ?
C2 N2 C19 C20 -66.5(6) . . . . ?
C1 N2 C19 C24 -116.3(5) . . . . ?
C2 N2 C19 C24 62.0(6) . . . . ?
O1 C20 C19 N2 -54.6(6) . . . . ?
C21 C20 C19 N2 -179.2(4) . . . . ?
O1 C20 C19 C24 178.5(5) . . . . ?
C21 C20 C19 C24 53.9(6) . . . . ?
C12 C11 C18 C17 -82.6(11) . . . . ?
Ir1 C11 C18 C17 -1.7(12) . . . . ?
C11 C18 C17 C16 18.1(13) . . . . ?
C15 C16 C17 C18 57.8(12) . . . . ?
Ir1 C16 C17 C18 -24.9(10) . . . . ?
O1 C20 C21 C22 177.6(5) . . . . ?
C19 C20 C21 C22 -56.1(7) . . . . ?
C25 C30 C29 C28 -0.9(10) . . . . ?
C33 C30 C29 C28 178.4(6) . . . . ?
C30 C29 C28 C27 1.8(10) . . . . ?
C30 C29 C28 C31 -177.8(6) . . . . ?
C29 C28 C27 C26 -1.4(9) . . . . ?
C31 C28 C27 C26 178.2(6) . . . . ?
C28 C27 C26 C25 0.2(9) . . . . ?
C28 C27 C26 C32 179.6(6) . . . . ?
C29 C30 C25 C26 -0.4(9) . . . . ?
C33 C30 C25 C26 -179.7(6) . . . . ?
C29 C30 C25 C10 176.1(5) . . . . ?
C33 C30 C25 C10 -3.2(9) . . . . ?
C27 C26 C25 C30 0.7(9) . . . . ?
C32 C26 C25 C30 -178.6(6) . . . . ?
C27 C26 C25 C10 -175.8(5) . . . . ?
C32 C26 C25 C10 4.8(9) . . . . ?
N1 C10 C25 C30 65.9(8) . . . . ?
N1 C10 C25 C26 -117.6(6) . . . . ?
N2 C19 C24 C23 179.3(5) . . . . ?
C20 C19 C24 C23 -53.3(7) . . . . ?
C22 C23 C24 C19 54.9(7) . . . . ?
C24 C23 C22 C21 -58.3(7) . . . . ?
C20 C21 C22 C23 59.4(7) . . . . ?
C7 C2 C3 C4 -3.0(8) . . . . ?
N2 C2 C3 C4 178.2(5) . . . . ?
C7 C2 C3 N1 178.0(5) . . . . ?
N2 C2 C3 N1 -0.8(6) . . . . ?
C5 C4 C3 C2 1.3(8) . . . . ?
C5 C4 C3 N1 -180.0(5) . . . . ?
C1 N1 C3 C2 1.1(6) . . . . ?
C10 N1 C3 C2 179.8(5) . . . . ?
C1 N1 C3 C4 -177.7(6) . . . . ?
C10 N1 C3 C4 1.0(10) . . . . ?
C17 C16 C15 C14 0.5(11) . . . . ?
Ir1 C16 C15 C14 103.6(7) . . . . ?
C17 C16 C15 Ir1 -103.1(7) . . . . ?
C13 C14 C15 C16 -87.3(10) . . . . ?
C13 C14 C15 Ir1 -6.6(11) . . . . ?
C1 Ir1 C15 C16 171.2(8) . . . . ?
C12 Ir1 C15 C16 112.2(5) . . . . ?
C11 Ir1 C15 C16 74.7(5) . . . . ?
Cl1 Ir1 C15 C16 -90.8(5) . . . . ?
C1 Ir1 C15 C14 50.9(13) . . . . ?
C12 Ir1 C15 C14 -8.1(6) . . . . ?
C11 Ir1 C15 C14 -45.6(7) . . . . ?
C16 Ir1 C15 C14 -120.3(8) . . . . ?
Cl1 Ir1 C15 C14 148.9(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.002
_refine_diff_density_min         -1.464
_refine_diff_density_rms         0.100
_database_code_depnum_ccdc_archive 'CCDC 985402'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3c

_audit_creation_method           'SHELXL-97 (Sheldrick, 2008)'
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H50 Cl Ir N2 O2'
_chemical_formula_sum            'C37 H50 Cl Ir N2 O2'
_chemical_formula_weight         782.44

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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

_cell_length_a                   15.8455(5)
_cell_length_b                   12.8111(4)
_cell_length_c                   18.1170(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.400(3)
_cell_angle_gamma                90.00
_cell_volume                     3447.06(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4821
_cell_measurement_theta_min      3.3940
_cell_measurement_theta_max      28.2830

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.113
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1584
_exptl_absorpt_coefficient_mu    3.985
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_T_max  0.637
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_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  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16266
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         26.37
_reflns_number_total             7045
_reflns_number_gt                5293
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0389P)²+0.8078P] where P=(Fo²+2Fc²)/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         7045
_refine_ls_number_parameters     395
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0729
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.981
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.001

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 0.334095(11) 0.475245(16) 0.152677(9) 0.03870(7) Uani 1 1 d . . .
O1 O 0.25222(18) 0.7445(3) -0.00247(19) 0.0507(9) Uani 1 1 d . . .
N1 N 0.2542(2) 0.4075(3) -0.01719(18) 0.0328(8) Uani 1 1 d . . .
C1 C 0.3011(3) 0.4830(4) 0.0344(2) 0.0330(9) Uani 1 1 d . . .
Cl1 Cl 0.44162(8) 0.34925(13) 0.14933(7) 0.0655(4) Uani 1 1 d . . .
C2 C 0.3102(3) 0.5148(3) -0.0855(2) 0.0334(10) Uani 1 1 d . . .
O2 O 0.1867(2) 0.8273(4) -0.1154(2) 0.0877(14) Uani 1 1 d . . .
N2 N 0.3323(2) 0.5504(3) -0.00765(18) 0.0349(9) Uani 1 1 d . . .
C5 C 0.2529(3) 0.4035(4) -0.2244(2) 0.0391(11) Uani 1 1 d . . .
C6 C 0.3050(3) 0.4935(4) -0.2177(2) 0.0399(12) Uani 1 1 d . . .
C15 C 0.4067(4) 0.5055(6) 0.2757(3) 0.081(2) Uani 1 1 d U . .
H15 H 0.4694 0.4817 0.2930 0.097 Uiso 1 1 calc R . .
C7 C 0.3329(3) 0.5507(4) -0.1483(2) 0.0367(11) Uani 1 1 d . . .
H7 H 0.3661 0.6117 -0.1440 0.044 Uiso 1 1 calc R . .
C8 C 0.3323(4) 0.5296(4) -0.2858(3) 0.0572(14) Uani 1 1 d . . .
H8A H 0.3585 0.4722 -0.3044 0.086 Uiso 1 1 calc R . .
H8B H 0.3755 0.5850 -0.2685 0.086 Uiso 1 1 calc R . .
H8C H 0.2802 0.5543 -0.3277 0.086 Uiso 1 1 calc R . .
C9 C 0.2227(3) 0.3408(4) -0.3002(2) 0.0609(15) Uani 1 1 d . . .
H9A H 0.1939 0.3864 -0.3438 0.091 Uiso 1 1 calc R . .
H9B H 0.1809 0.2879 -0.2975 0.091 Uiso 1 1 calc R . .
H9C H 0.2740 0.3085 -0.3072 0.091 Uiso 1 1 calc R . .
C10 C 0.2175(3) 0.3173(4) 0.0109(2) 0.0428(11) Uani 1 1 d . . .
H10A H 0.1950 0.3406 0.0516 0.051 Uiso 1 1 calc R . .
H10B H 0.2660 0.2684 0.0350 0.051 Uiso 1 1 calc R . .
C3 C 0.2606(2) 0.4241(4) -0.0915(2) 0.0314(9) Uani 1 1 d . . .
C12 C 0.2683(4) 0.6125(5) 0.1663(3) 0.0687(16) Uani 1 1 d U . .
H12 H 0.2549 0.6611 0.1220 0.082 Uiso 1 1 calc R . .
C11 C 0.2097(3) 0.5279(4) 0.1529(3) 0.0543(13) Uani 1 1 d . . .
H11 H 0.1624 0.5282 0.1007 0.065 Uiso 1 1 calc R . .
C30 C 0.1555(3) 0.1571(4) -0.0682(2) 0.0415(11) Uani 1 1 d . . .
C16 C 0.3463(3) 0.4255(5) 0.2714(2) 0.0560(14) Uani 1 1 d . . .
H16 H 0.3735 0.3565 0.2869 0.067 Uiso 1 1 calc R . .
C21 C 0.5336(3) 0.7330(4) 0.0722(3) 0.0547(13) Uani 1 1 d . . .
H21A H 0.5360 0.7350 0.1265 0.066 Uiso 1 1 calc R . .
H21B H 0.5949 0.7292 0.0726 0.066 Uiso 1 1 calc R . .
C19 C 0.3842(3) 0.6429(3) 0.0274(2) 0.0347(10) Uani 1 1 d . . .
H19 H 0.3856 0.6461 0.0818 0.042 Uiso 1 1 calc R . .
C18 C 0.1825(4) 0.4741(5) 0.2159(3) 0.0717(17) Uani 1 1 d . . .
H18A H 0.1433 0.5203 0.2316 0.086 Uiso 1 1 calc R . .
H18B H 0.1485 0.4118 0.1936 0.086 Uiso 1 1 calc R . .
C17 C 0.2607(4) 0.4443(5) 0.2875(3) 0.0652(16) Uani 1 1 d . . .
H17A H 0.2710 0.4994 0.3263 0.078 Uiso 1 1 calc R . .
H17B H 0.2454 0.3815 0.3099 0.078 Uiso 1 1 calc R . .
C20 C 0.4818(2) 0.6367(4) 0.0318(3) 0.0441(11) Uani 1 1 d . . .
H20A H 0.4839 0.6312 -0.0209 0.053 Uiso 1 1 calc R . .
H20B H 0.5097 0.5747 0.0609 0.053 Uiso 1 1 calc R . .
C22 C 0.4899(3) 0.8309(4) 0.0309(3) 0.0547(13) Uani 1 1 d . . .
H22A H 0.4919 0.8317 -0.0220 0.066 Uiso 1 1 calc R . .
H22B H 0.5228 0.8911 0.0588 0.066 Uiso 1 1 calc R . .
C34 C 0.1830(3) 0.7868(5) -0.0574(3) 0.0566(14) Uani 1 1 d U . .
C25 C 0.1433(3) 0.2609(4) -0.0510(2) 0.0352(10) Uani 1 1 d . . .
C24 C 0.3394(2) 0.7426(4) -0.0122(2) 0.0384(11) Uani 1 1 d . . .
H24 H 0.3317 0.7414 -0.0683 0.046 Uiso 1 1 calc R . .
C23 C 0.3927(3) 0.8374(4) 0.0268(3) 0.0498(12) Uani 1 1 d . . .
H23A H 0.3912 0.8438 0.0797 0.060 Uiso 1 1 calc R . .
H23B H 0.3650 0.8993 -0.0024 0.060 Uiso 1 1 calc R . .
C4 C 0.2307(2) 0.3687(4) -0.1613(2) 0.0373(10) Uani 1 1 d . . .
H4 H 0.1962 0.3087 -0.1657 0.045 Uiso 1 1 calc R . .
C27 C -0.0042(3) 0.2576(5) -0.1500(3) 0.0619(16) Uani 1 1 d . . .
H27 H -0.0581 0.2913 -0.1771 0.074 Uiso 1 1 calc R . .
C26 C 0.0625(3) 0.3126(4) -0.0918(3) 0.0479(12) Uani 1 1 d . . .
C33 C 0.2404(3) 0.0977(4) -0.0257(3) 0.0601(14) Uani 1 1 d . . .
H33A H 0.2912 0.1352 -0.0296 0.090 Uiso 1 1 calc R . .
H33B H 0.2374 0.0299 -0.0490 0.090 Uiso 1 1 calc R . .
H33C H 0.2469 0.0902 0.0288 0.090 Uiso 1 1 calc R . .
C32 C 0.0466(3) 0.4235(5) -0.0735(4) 0.0765(17) Uani 1 1 d . . .
H32A H 0.0724 0.4349 -0.0177 0.115 Uiso 1 1 calc R . .
H32B H -0.0170 0.4368 -0.0910 0.115 Uiso 1 1 calc R . .
H32C H 0.0741 0.4698 -0.1001 0.115 Uiso 1 1 calc R . .
C13 C 0.3089(6) 0.6631(6) 0.2459(4) 0.117(3) Uani 1 1 d U . .
H13A H 0.2673 0.6561 0.2742 0.140 Uiso 1 1 calc R . .
H13B H 0.3169 0.7370 0.2388 0.140 Uiso 1 1 calc R . .
C35 C 0.0985(3) 0.7806(6) -0.0351(4) 0.081(2) Uani 1 1 d U . .
H35 H 0.1096 0.7215 0.0014 0.097 Uiso 1 1 calc R . .
C14 C 0.3980(6) 0.6169(8) 0.2949(4) 0.128(4) Uani 1 1 d U . .
H14A H 0.4459 0.6568 0.2865 0.153 Uiso 1 1 calc R . .
H14B H 0.4050 0.6227 0.3501 0.153 Uiso 1 1 calc R . .
C37 C 0.0218(5) 0.7537(10) -0.0963(6) 0.203(6) Uani 1 1 d U . .
H37A H 0.0068 0.8080 -0.1353 0.304 Uiso 1 1 calc R . .
H37B H -0.0269 0.7445 -0.0769 0.304 Uiso 1 1 calc R . .
H37C H 0.0318 0.6897 -0.1195 0.304 Uiso 1 1 calc R . .
C29 C 0.0870(3) 0.1074(5) -0.1271(3) 0.0579(14) Uani 1 1 d . . .
H29A H 0.0951 0.0385 -0.1393 0.069 Uiso 1 1 calc R . .
C28 C 0.0064(4) 0.1570(5) -0.1687(3) 0.0625(16) Uani 1 1 d . . .
C31 C -0.0691(4) 0.0993(7) -0.2311(4) 0.112(3) Uani 1 1 d . . .
H31A H -0.1254 0.1150 -0.2249 0.169 Uiso 1 1 calc R . .
H31B H -0.0582 0.0255 -0.2255 0.169 Uiso 1 1 calc R . .
H31C H -0.0712 0.1211 -0.2825 0.169 Uiso 1 1 calc R . .
C36 C 0.0955(5) 0.8715(7) 0.0128(5) 0.129(3) Uani 1 1 d . . .
H36A H 0.1558 0.8945 0.0414 0.194 Uiso 1 1 calc R . .
H36B H 0.0663 0.8528 0.0493 0.194 Uiso 1 1 calc R . .
H36C H 0.0627 0.9268 -0.0207 0.194 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C1 2.024(4) . ?
Ir1 C11 2.084(5) . ?
Ir1 C12 2.102(6) . ?
Ir1 C15 2.157(5) . ?
Ir1 C16 2.186(4) . ?
Ir1 Cl1 2.3630(13) . ?
O1 C34 1.313(6) . ?
O1 C24 1.453(5) . ?
N1 C1 1.369(5) . ?
N1 C3 1.401(4) . ?
N1 C10 1.463(5) . ?
C1 N2 1.354(5) . ?
C2 C7 1.386(5) . ?
C2 C3 1.386(6) . ?
C2 N2 1.406(5) . ?
O2 C34 1.192(6) . ?
N2 C19 1.456(5) . ?
C5 C4 1.381(6) . ?
C5 C6 1.399(6) . ?
C5 C9 1.518(6) . ?
C6 C7 1.388(6) . ?
C6 C8 1.516(6) . ?
C15 C16 1.386(8) . ?
C15 C14 1.487(10) . ?
C15 H15 0.9800 . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C25 1.497(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C3 C4 1.382(5) . ?
C12 C11 1.393(7) . ?
C12 C13 1.505(8) . ?
C12 H12 0.9800 . ?
C11 C18 1.519(7) . ?
C11 H11 0.9800 . ?
C30 C29 1.384(6) . ?
C30 C25 1.395(6) . ?
C30 C33 1.504(6) . ?
C16 C17 1.503(7) . ?
C16 H16 0.9800 . ?
C21 C22 1.500(7) . ?
C21 C20 1.522(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C19 C24 1.515(6) . ?
C19 C20 1.522(5) . ?
C19 H19 0.9800 . ?
C18 C17 1.497(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C22 C23 1.519(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C34 C35 1.528(7) . ?
C25 C26 1.402(6) . ?
C24 C23 1.506(6) . ?
C24 H24 0.9800 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C4 H4 0.9300 . ?
C27 C28 1.359(8) . ?
C27 C26 1.396(7) . ?
C27 H27 0.9300 . ?
C26 C32 1.500(8) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C13 C14 1.501(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C35 C37 1.374(9) . ?
C35 C36 1.463(9) . ?
C35 H35 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C29 C28 1.390(7) . ?
C29 H29A 0.9300 . ?
C28 C31 1.520(7) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ir1 C11 95.20(17) . . ?
C1 Ir1 C12 97.37(19) . . ?
C11 Ir1 C12 38.9(2) . . ?
C1 Ir1 C15 159.0(2) . . ?
C11 Ir1 C15 96.0(2) . . ?
C12 Ir1 C15 80.5(3) . . ?
C1 Ir1 C16 163.3(2) . . ?
C11 Ir1 C16 81.49(19) . . ?
C12 Ir1 C16 90.3(2) . . ?
C15 Ir1 C16 37.2(2) . . ?
C1 Ir1 Cl1 85.90(12) . . ?
C11 Ir1 Cl1 155.74(17) . . ?
C12 Ir1 Cl1 164.99(18) . . ?
C15 Ir1 Cl1 91.1(2) . . ?
C16 Ir1 Cl1 90.50(15) . . ?
C34 O1 C24 119.6(4) . . ?
C1 N1 C3 110.2(3) . . ?
C1 N1 C10 120.5(3) . . ?
C3 N1 C10 128.7(4) . . ?
N2 C1 N1 106.5(3) . . ?
N2 C1 Ir1 128.1(3) . . ?
N1 C1 Ir1 124.5(3) . . ?
C7 C2 C3 121.2(4) . . ?
C7 C2 N2 132.1(4) . . ?
C3 C2 N2 106.7(3) . . ?
C1 N2 C2 110.2(4) . . ?
C1 N2 C19 122.4(3) . . ?
C2 N2 C19 127.4(3) . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 C9 119.2(4) . . ?
C6 C5 C9 120.3(4) . . ?
C7 C6 C5 120.4(4) . . ?
C7 C6 C8 119.0(4) . . ?
C5 C6 C8 120.5(4) . . ?
C16 C15 C14 127.2(7) . . ?
C16 C15 Ir1 72.5(3) . . ?
C14 C15 Ir1 110.8(5) . . ?
C16 C15 H15 113.0 . . ?
C14 C15 H15 113.0 . . ?
Ir1 C15 H15 113.0 . . ?
C6 C7 C2 118.4(4) . . ?
C6 C7 H7 120.8 . . ?
C2 C7 H7 120.8 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C25 115.1(3) . . ?
N1 C10 H10A 108.5 . . ?
C25 C10 H10A 108.5 . . ?
N1 C10 H10B 108.5 . . ?
C25 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 N1 133.3(4) . . ?
C2 C3 N1 106.3(3) . . ?
C11 C12 C13 122.6(5) . . ?
C11 C12 Ir1 69.9(3) . . ?
C13 C12 Ir1 114.1(5) . . ?
C11 C12 H12 114.2 . . ?
C13 C12 H12 114.2 . . ?
Ir1 C12 H12 114.2 . . ?
C12 C11 C18 124.6(5) . . ?
C12 C11 Ir1 71.3(3) . . ?
C18 C11 Ir1 111.8(3) . . ?
C12 C11 H11 113.9 . . ?
C18 C11 H11 113.9 . . ?
Ir1 C11 H11 113.9 . . ?
C29 C30 C25 118.6(4) . . ?
C29 C30 C33 119.0(5) . . ?
C25 C30 C33 122.4(4) . . ?
C15 C16 C17 121.5(6) . . ?
C15 C16 Ir1 70.3(3) . . ?
C17 C16 Ir1 111.6(3) . . ?
C15 C16 H16 115.1 . . ?
C17 C16 H16 115.1 . . ?
Ir1 C16 H16 115.1 . . ?
C22 C21 C20 111.1(4) . . ?
C22 C21 H21A 109.4 . . ?
C20 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
N2 C19 C24 112.3(3) . . ?
N2 C19 C20 112.9(4) . . ?
C24 C19 C20 111.7(4) . . ?
N2 C19 H19 106.5 . . ?
C24 C19 H19 106.5 . . ?
C20 C19 H19 106.5 . . ?
C17 C18 C11 113.6(5) . . ?
C17 C18 H18A 108.8 . . ?
C11 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C11 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C16 C17 C18 113.8(4) . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C20 C21 110.5(4) . . ?
C19 C20 H20A 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C21 C22 C23 110.7(4) . . ?
C21 C22 H22A 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
O2 C34 O1 124.2(4) . . ?
O2 C34 C35 124.9(5) . . ?
O1 C34 C35 110.9(5) . . ?
C30 C25 C26 120.3(4) . . ?
C30 C25 C10 119.6(4) . . ?
C26 C25 C10 120.1(4) . . ?
O1 C24 C23 109.3(4) . . ?
O1 C24 C19 105.4(3) . . ?
C23 C24 C19 111.3(3) . . ?
O1 C24 H24 110.3 . . ?
C23 C24 H24 110.3 . . ?
C19 C24 H24 110.3 . . ?
C24 C23 C22 111.8(4) . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 107.9 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C28 C27 C26 122.7(5) . . ?
C28 C27 H27 118.6 . . ?
C26 C27 H27 118.6 . . ?
C27 C26 C25 118.2(5) . . ?
C27 C26 C32 120.2(5) . . ?
C25 C26 C32 121.6(4) . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C26 C32 H32A 109.5 . . ?
C26 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C26 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C12 C13 C14 113.4(6) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C37 C35 C36 118.5(7) . . ?
C37 C35 C34 114.2(6) . . ?
C36 C35 C34 109.2(5) . . ?
C37 C35 H35 104.5 . . ?
C36 C35 H35 104.5 . . ?
C34 C35 H35 104.5 . . ?
C15 C14 C13 112.6(6) . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C30 C29 C28 122.3(5) . . ?
C30 C29 H29A 118.8 . . ?
C28 C29 H29A 118.8 . . ?
C27 C28 C29 117.9(5) . . ?
C27 C28 C31 120.9(6) . . ?
C29 C28 C31 121.2(6) . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 N2 3.7(4) . . . . ?
C10 N1 C1 N2 175.1(3) . . . . ?
C3 N1 C1 Ir1 -166.2(3) . . . . ?
C10 N1 C1 Ir1 5.2(5) . . . . ?
C11 Ir1 C1 N2 110.1(4) . . . . ?
C12 Ir1 C1 N2 71.0(4) . . . . ?
C15 Ir1 C1 N2 -11.8(9) . . . . ?
C16 Ir1 C1 N2 -172.3(5) . . . . ?
Cl1 Ir1 C1 N2 -94.3(4) . . . . ?
C11 Ir1 C1 N1 -82.2(4) . . . . ?
C12 Ir1 C1 N1 -121.3(4) . . . . ?
C15 Ir1 C1 N1 155.9(6) . . . . ?
C16 Ir1 C1 N1 -4.6(8) . . . . ?
Cl1 Ir1 C1 N1 73.4(3) . . . . ?
N1 C1 N2 C2 -3.7(4) . . . . ?
Ir1 C1 N2 C2 165.7(3) . . . . ?
N1 C1 N2 C19 178.7(3) . . . . ?
Ir1 C1 N2 C19 -11.8(6) . . . . ?
C7 C2 N2 C1 -173.9(4) . . . . ?
C3 C2 N2 C1 2.3(4) . . . . ?
C7 C2 N2 C19 3.6(7) . . . . ?
C3 C2 N2 C19 179.8(4) . . . . ?
C4 C5 C6 C7 -1.9(6) . . . . ?
C9 C5 C6 C7 -179.8(4) . . . . ?
C4 C5 C6 C8 177.7(4) . . . . ?
C9 C5 C6 C8 -0.2(6) . . . . ?
C1 Ir1 C15 C16 -170.8(5) . . . . ?
C11 Ir1 C15 C16 67.4(4) . . . . ?
C12 Ir1 C15 C16 103.2(4) . . . . ?
Cl1 Ir1 C15 C16 -89.3(4) . . . . ?
C1 Ir1 C15 C14 65.2(9) . . . . ?
C11 Ir1 C15 C14 -56.5(5) . . . . ?
C12 Ir1 C15 C14 -20.7(5) . . . . ?
C16 Ir1 C15 C14 -123.9(7) . . . . ?
Cl1 Ir1 C15 C14 146.7(5) . . . . ?
C5 C6 C7 C2 1.8(6) . . . . ?
C8 C6 C7 C2 -177.7(4) . . . . ?
C3 C2 C7 C6 -0.1(6) . . . . ?
N2 C2 C7 C6 175.7(4) . . . . ?
C1 N1 C10 C25 160.2(4) . . . . ?
C3 N1 C10 C25 -30.2(6) . . . . ?
C7 C2 C3 C4 -1.6(6) . . . . ?
N2 C2 C3 C4 -178.3(3) . . . . ?
C7 C2 C3 N1 176.7(3) . . . . ?
N2 C2 C3 N1 0.0(4) . . . . ?
C1 N1 C3 C4 175.7(4) . . . . ?
C10 N1 C3 C4 5.2(7) . . . . ?
C1 N1 C3 C2 -2.3(4) . . . . ?
C10 N1 C3 C2 -172.8(4) . . . . ?
C1 Ir1 C12 C11 89.2(3) . . . . ?
C15 Ir1 C12 C11 -112.0(3) . . . . ?
C16 Ir1 C12 C11 -76.0(3) . . . . ?
Cl1 Ir1 C12 C11 -169.1(4) . . . . ?
C1 Ir1 C12 C13 -153.1(5) . . . . ?
C11 Ir1 C12 C13 117.7(6) . . . . ?
C15 Ir1 C12 C13 5.7(5) . . . . ?
C16 Ir1 C12 C13 41.8(5) . . . . ?
Cl1 Ir1 C12 C13 -51.4(8) . . . . ?
C13 C12 C11 C18 -2.4(9) . . . . ?
Ir1 C12 C11 C18 104.0(5) . . . . ?
C13 C12 C11 Ir1 -106.4(6) . . . . ?
C1 Ir1 C11 C12 -95.3(3) . . . . ?
C15 Ir1 C11 C12 66.8(3) . . . . ?
C16 Ir1 C11 C12 101.2(3) . . . . ?
Cl1 Ir1 C11 C12 173.1(3) . . . . ?
C1 Ir1 C11 C18 144.0(4) . . . . ?
C12 Ir1 C11 C18 -120.7(5) . . . . ?
C15 Ir1 C11 C18 -53.8(5) . . . . ?
C16 Ir1 C11 C18 -19.4(4) . . . . ?
Cl1 Ir1 C11 C18 52.5(6) . . . . ?
C14 C15 C16 C17 -0.7(8) . . . . ?
Ir1 C15 C16 C17 -103.8(4) . . . . ?
C14 C15 C16 Ir1 103.1(6) . . . . ?
C1 Ir1 C16 C15 168.5(6) . . . . ?
C11 Ir1 C16 C15 -111.8(4) . . . . ?
C12 Ir1 C16 C15 -73.8(4) . . . . ?
Cl1 Ir1 C16 C15 91.2(4) . . . . ?
C1 Ir1 C16 C17 -74.4(8) . . . . ?
C11 Ir1 C16 C17 5.3(4) . . . . ?
C12 Ir1 C16 C17 43.3(4) . . . . ?
C15 Ir1 C16 C17 117.1(6) . . . . ?
Cl1 Ir1 C16 C17 -151.7(4) . . . . ?
C1 N2 C19 C24 -120.7(4) . . . . ?
C2 N2 C19 C24 62.2(5) . . . . ?
C1 N2 C19 C20 112.0(4) . . . . ?
C2 N2 C19 C20 -65.2(5) . . . . ?
C12 C11 C18 C17 -50.4(8) . . . . ?
Ir1 C11 C18 C17 31.3(6) . . . . ?
C15 C16 C17 C18 89.7(6) . . . . ?
Ir1 C16 C17 C18 10.3(7) . . . . ?
C11 C18 C17 C16 -27.1(8) . . . . ?
N2 C19 C20 C21 -177.4(4) . . . . ?
C24 C19 C20 C21 54.9(5) . . . . ?
C22 C21 C20 C19 -56.7(5) . . . . ?
C20 C21 C22 C23 57.1(6) . . . . ?
C24 O1 C34 O2 -2.1(8) . . . . ?
C24 O1 C34 C35 -179.8(4) . . . . ?
C29 C30 C25 C26 1.2(6) . . . . ?
C33 C30 C25 C26 -179.3(4) . . . . ?
C29 C30 C25 C10 -178.3(4) . . . . ?
C33 C30 C25 C10 1.1(6) . . . . ?
N1 C10 C25 C30 117.5(4) . . . . ?
N1 C10 C25 C26 -62.0(5) . . . . ?
C34 O1 C24 C23 93.1(5) . . . . ?
C34 O1 C24 C19 -147.2(4) . . . . ?
N2 C19 C24 O1 59.6(4) . . . . ?
C20 C19 C24 O1 -172.3(3) . . . . ?
N2 C19 C24 C23 178.0(3) . . . . ?
C20 C19 C24 C23 -54.0(5) . . . . ?
O1 C24 C23 C22 170.3(4) . . . . ?
C19 C24 C23 C22 54.3(5) . . . . ?
C21 C22 C23 C24 -56.1(5) . . . . ?
C2 C3 C4 C5 1.6(6) . . . . ?
N1 C3 C4 C5 -176.2(4) . . . . ?
C6 C5 C4 C3 0.1(6) . . . . ?
C9 C5 C4 C3 178.1(4) . . . . ?
C28 C27 C26 C25 -0.3(7) . . . . ?
C28 C27 C26 C32 -179.7(5) . . . . ?
C30 C25 C26 C27 -0.6(6) . . . . ?
C10 C25 C26 C27 178.9(4) . . . . ?
C30 C25 C26 C32 178.7(4) . . . . ?
C10 C25 C26 C32 -1.8(7) . . . . ?
C11 C12 C13 C14 91.1(8) . . . . ?
Ir1 C12 C13 C14 10.4(8) . . . . ?
O2 C34 C35 C37 44.4(11) . . . . ?
O1 C34 C35 C37 -137.9(8) . . . . ?
O2 C34 C35 C36 -90.8(8) . . . . ?
O1 C34 C35 C36 86.9(7) . . . . ?
C16 C15 C14 C13 -51.0(9) . . . . ?
Ir1 C15 C14 C13 32.4(8) . . . . ?
C12 C13 C14 C15 -28.3(9) . . . . ?
C25 C30 C29 C28 -0.9(7) . . . . ?
C33 C30 C29 C28 179.7(4) . . . . ?
C26 C27 C28 C29 0.7(8) . . . . ?
C26 C27 C28 C31 178.4(5) . . . . ?
C30 C29 C28 C27 0.0(7) . . . . ?
C30 C29 C28 C31 -177.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.249
_refine_diff_density_min         -0.966
_refine_diff_density_rms         0.094
_database_code_depnum_ccdc_archive 'CCDC 985403'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3d

_audit_creation_method           'SHELXL-97 (Sheldrick, 2008)'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H52 Cl Ir N2 O2'
_chemical_formula_sum            'C38 H52 Cl Ir N2 O2'
_chemical_formula_weight         796.47

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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

_cell_length_a                   15.8134(6)
_cell_length_b                   13.3320(4)
_cell_length_c                   18.0822(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.855(4)
_cell_angle_gamma                90.00
_cell_volume                     3538.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      26.37

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.102
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    3.884
_exptl_absorpt_correction_T_min  0.428
_exptl_absorpt_correction_T_max  0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1333
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20108
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         26.37
_reflns_number_total             7221
_reflns_number_gt                5873
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0205P)²+0.9325P] where P=(Fo²+2Fc²)/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         7221
_refine_ls_number_parameters     405
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0549
_refine_ls_wR_factor_gt          0.0504
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.164987(8) 0.478963(10) 0.349307(7) 0.03457(5) Uani 1 1 d . . .
N1 N 0.24189(15) 0.40843(18) 0.52019(14) 0.0314(6) Uani 1 1 d . . .
O1 O 0.25935(13) 0.73839(16) 0.51756(13) 0.0418(5) Uani 1 1 d . . .
C1 C 0.20059(19) 0.4837(2) 0.46946(18) 0.0314(7) Uani 1 1 d . . .
Cl1 Cl 0.05285(6) 0.36190(8) 0.34969(5) 0.0570(2) Uani 1 1 d . . .
C3 C 0.23545(18) 0.4237(2) 0.59428(16) 0.0299(7) Uani 1 1 d . . .
C2 C 0.19209(18) 0.5152(2) 0.58932(17) 0.0298(6) Uani 1 1 d . . .
N2 N 0.17263(15) 0.55161(19) 0.51182(14) 0.0312(6) Uani 1 1 d . . .
O2 O 0.30928(16) 0.8383(2) 0.62351(16) 0.0713(8) Uani 1 1 d . . .
C4 C 0.25995(19) 0.3662(2) 0.66261(17) 0.0355(7) Uani 1 1 d . . .
H4 H 0.2907 0.3058 0.6663 0.043 Uiso 1 1 calc R . .
C5 C 0.23767(19) 0.4004(3) 0.72587(17) 0.0366(7) Uani 1 1 d . . .
C6 C 0.19429(19) 0.4932(3) 0.72057(18) 0.0366(8) Uani 1 1 d . . .
C26 C 0.3405(2) 0.1636(2) 0.56987(19) 0.0414(8) Uani 1 1 d . . .
C7 C 0.17135(19) 0.5512(2) 0.65282(17) 0.0352(7) Uani 1 1 d . . .
H7 H 0.1427 0.6128 0.6496 0.042 Uiso 1 1 calc R . .
C12 C 0.2370(2) 0.6082(3) 0.3397(2) 0.0538(10) Uani 1 1 d . . .
H12 H 0.2550 0.6522 0.3865 0.065 Uiso 1 1 calc R . .
C13 C 0.1956(4) 0.6625(3) 0.2616(3) 0.0890(15) Uani 1 1 d . . .
H13A H 0.1886 0.7327 0.2721 0.107 Uiso 1 1 calc R . .
H13B H 0.2370 0.6585 0.2334 0.107 Uiso 1 1 calc R . .
C34 C 0.3233(2) 0.7927(3) 0.5726(2) 0.0442(8) Uani 1 1 d . . .
C14 C 0.1050(4) 0.6218(4) 0.2092(3) 0.1036(19) Uani 1 1 d . . .
H14A H 0.0995 0.6276 0.1541 0.124 Uiso 1 1 calc R . .
H14B H 0.0575 0.6626 0.2158 0.124 Uiso 1 1 calc R . .
C16 C 0.1472(2) 0.4347(3) 0.22846(19) 0.0544(10) Uani 1 1 d . . .
H16 H 0.1166 0.3701 0.2114 0.065 Uiso 1 1 calc R . .
C15 C 0.0896(3) 0.5140(4) 0.2257(2) 0.0681(12) Uani 1 1 d . . .
H15 H 0.0251 0.4951 0.2072 0.082 Uiso 1 1 calc R . .
C18 C 0.3150(3) 0.4730(3) 0.2850(2) 0.0655(12) Uani 1 1 d . . .
H18A H 0.3547 0.5169 0.2698 0.079 Uiso 1 1 calc R . .
H18B H 0.3484 0.4118 0.3061 0.079 Uiso 1 1 calc R . .
C20 C 0.02285(19) 0.6372(3) 0.46684(19) 0.0428(8) Uani 1 1 d . . .
H20A H -0.0053 0.5783 0.4360 0.051 Uiso 1 1 calc R . .
H20B H 0.0189 0.6313 0.5189 0.051 Uiso 1 1 calc R . .
C33 C 0.4479(2) 0.4219(3) 0.5813(2) 0.0578(10) Uani 1 1 d . . .
H33A H 0.4258 0.4344 0.5249 0.087 Uiso 1 1 calc R . .
H33B H 0.5118 0.4371 0.6043 0.087 Uiso 1 1 calc R . .
H33C H 0.4155 0.4636 0.6052 0.087 Uiso 1 1 calc R . .
C25 C 0.3515(2) 0.2643(2) 0.55435(18) 0.0348(7) Uani 1 1 d . . .
C24 C 0.16797(19) 0.7368(2) 0.51876(18) 0.0365(7) Uani 1 1 d . . .
H24 H 0.1713 0.7355 0.5740 0.044 Uiso 1 1 calc R . .
C23 C 0.1164(2) 0.8290(2) 0.4769(2) 0.0498(9) Uani 1 1 d . . .
H23A H 0.1196 0.8342 0.4245 0.060 Uiso 1 1 calc R . .
H23B H 0.1445 0.8884 0.5070 0.060 Uiso 1 1 calc R . .
C21 C -0.0277(2) 0.7304(3) 0.4254(2) 0.0530(9) Uani 1 1 d . . .
H21A H -0.0293 0.7323 0.3712 0.064 Uiso 1 1 calc R . .
H21B H -0.0900 0.7276 0.4228 0.064 Uiso 1 1 calc R . .
C30 C 0.4331(2) 0.3138(3) 0.5959(2) 0.0431(8) Uani 1 1 d . . .
C28 C 0.4932(3) 0.1622(3) 0.6709(2) 0.0592(10) Uani 1 1 d . . .
C29 C 0.5025(2) 0.2610(3) 0.6532(2) 0.0555(10) Uani 1 1 d . . .
H29 H 0.5572 0.2936 0.6806 0.067 Uiso 1 1 calc R . .
C27 C 0.4118(3) 0.1152(3) 0.6286(2) 0.0532(9) Uani 1 1 d . . .
H27 H 0.4045 0.0484 0.6399 0.064 Uiso 1 1 calc R . .
C36 C 0.4003(3) 0.8589(4) 0.4877(3) 0.0911(16) Uani 1 1 d . . .
H36A H 0.3541 0.8305 0.4414 0.137 Uiso 1 1 calc R . .
H36B H 0.4566 0.8630 0.4793 0.137 Uiso 1 1 calc R . .
H36C H 0.3820 0.9248 0.4971 0.137 Uiso 1 1 calc R . .
C35 C 0.4130(2) 0.7927(3) 0.5597(2) 0.0501(9) Uani 1 1 d . . .
C22 C 0.0171(2) 0.8239(3) 0.4684(2) 0.0576(10) Uani 1 1 d . . .
H22A H 0.0137 0.8251 0.5209 0.069 Uiso 1 1 calc R . .
H22B H -0.0150 0.8822 0.4393 0.069 Uiso 1 1 calc R . .
C32 C 0.2550(2) 0.1052(3) 0.5253(2) 0.0580(10) Uani 1 1 d . . .
H32A H 0.2038 0.1372 0.5319 0.087 Uiso 1 1 calc R . .
H32B H 0.2610 0.0381 0.5458 0.087 Uiso 1 1 calc R . .
H32C H 0.2455 0.1032 0.4697 0.087 Uiso 1 1 calc R . .
C9 C 0.2582(2) 0.3347(3) 0.79859(19) 0.0561(10) Uani 1 1 d . . .
H9A H 0.2922 0.3724 0.8455 0.084 Uiso 1 1 calc R . .
H9B H 0.2933 0.2778 0.7944 0.084 Uiso 1 1 calc R . .
H9C H 0.2021 0.3122 0.8021 0.084 Uiso 1 1 calc R . .
C8 C 0.1713(3) 0.5309(3) 0.7897(2) 0.0549(10) Uani 1 1 d . . .
H8A H 0.1352 0.4817 0.8033 0.082 Uiso 1 1 calc R . .
H8B H 0.1376 0.5924 0.7750 0.082 Uiso 1 1 calc R . .
H8C H 0.2265 0.5426 0.8348 0.082 Uiso 1 1 calc R . .
C17 C 0.2333(3) 0.4478(3) 0.2121(2) 0.0651(11) Uani 1 1 d . . .
H17A H 0.2454 0.3864 0.1891 0.078 Uiso 1 1 calc R . .
H17B H 0.2240 0.5009 0.1732 0.078 Uiso 1 1 calc R . .
C11 C 0.2917(2) 0.5230(3) 0.3496(2) 0.0453(8) Uani 1 1 d . . .
H11 H 0.3406 0.5189 0.4023 0.054 Uiso 1 1 calc R . .
C10 C 0.2747(2) 0.3187(2) 0.49198(18) 0.0408(8) Uani 1 1 d . . .
H10A H 0.2945 0.3383 0.4493 0.049 Uiso 1 1 calc R . .
H10B H 0.2241 0.2726 0.4697 0.049 Uiso 1 1 calc R . .
C19 C 0.12243(19) 0.6422(2) 0.47613(17) 0.0335(7) Uani 1 1 d . . .
H19 H 0.1228 0.6463 0.4221 0.040 Uiso 1 1 calc R . .
C38 C 0.4400(3) 0.6874(3) 0.5455(3) 0.0734(13) Uani 1 1 d . . .
H38A H 0.4469 0.6462 0.5909 0.110 Uiso 1 1 calc R . .
H38B H 0.4966 0.6896 0.5374 0.110 Uiso 1 1 calc R . .
H38C H 0.3935 0.6596 0.4991 0.110 Uiso 1 1 calc R . .
C37 C 0.4867(3) 0.8348(4) 0.6331(3) 0.0884(16) Uani 1 1 d . . .
H37A H 0.4665 0.8972 0.6474 0.133 Uiso 1 1 calc R . .
H37B H 0.5410 0.8458 0.6223 0.133 Uiso 1 1 calc R . .
H37C H 0.4993 0.7880 0.6763 0.133 Uiso 1 1 calc R . .
C31 C 0.5718(3) 0.1069(4) 0.7332(3) 0.0967(16) Uani 1 1 d . . .
H31A H 0.6073 0.0733 0.7077 0.145 Uiso 1 1 calc R . .
H31B H 0.5481 0.0585 0.7598 0.145 Uiso 1 1 calc R . .
H31C H 0.6095 0.1540 0.7715 0.145 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C1 2.032(3) . ?
Ir1 C11 2.086(3) . ?
Ir1 C12 2.109(3) . ?
Ir1 C15 2.156(4) . ?
Ir1 C16 2.178(3) . ?
Ir1 Cl1 2.3642(8) . ?
N1 C1 1.353(4) . ?
N1 C3 1.396(3) . ?
N1 C10 1.468(4) . ?
O1 C34 1.337(4) . ?
O1 C24 1.453(3) . ?
C1 N2 1.361(4) . ?
C3 C4 1.381(4) . ?
C3 C2 1.386(4) . ?
C2 C7 1.392(4) . ?
C2 N2 1.405(3) . ?
N2 C19 1.458(4) . ?
O2 C34 1.191(4) . ?
C4 C5 1.393(4) . ?
C5 C6 1.401(4) . ?
C5 C9 1.511(4) . ?
C6 C7 1.378(4) . ?
C6 C8 1.513(4) . ?
C26 C27 1.388(5) . ?
C26 C25 1.396(4) . ?
C26 C32 1.507(5) . ?
C12 C11 1.398(5) . ?
C12 C13 1.502(5) . ?
C13 C14 1.494(6) . ?
C34 C35 1.522(4) . ?
C14 C15 1.506(6) . ?
C16 C15 1.385(6) . ?
C16 C17 1.506(5) . ?
C18 C17 1.500(5) . ?
C18 C11 1.505(5) . ?
C20 C21 1.516(4) . ?
C20 C19 1.522(4) . ?
C33 C30 1.500(5) . ?
C25 C30 1.394(4) . ?
C25 C10 1.501(4) . ?
C24 C19 1.513(4) . ?
C24 C23 1.513(4) . ?
C23 C22 1.521(4) . ?
C21 C22 1.502(5) . ?
C30 C29 1.388(5) . ?
C28 C29 1.377(5) . ?
C28 C27 1.378(5) . ?
C28 C31 1.521(5) . ?
C36 C35 1.521(5) . ?
C35 C37 1.511(5) . ?
C35 C38 1.517(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ir1 C11 96.02(12) . . ?
C1 Ir1 C12 96.87(13) . . ?
C11 Ir1 C12 38.93(13) . . ?
C1 Ir1 C15 158.01(15) . . ?
C11 Ir1 C15 95.85(15) . . ?
C12 Ir1 C15 81.08(16) . . ?
C1 Ir1 C16 164.11(14) . . ?
C11 Ir1 C16 81.02(13) . . ?
C12 Ir1 C16 90.60(14) . . ?
C15 Ir1 C16 37.26(15) . . ?
C1 Ir1 Cl1 85.82(8) . . ?
C11 Ir1 Cl1 155.03(10) . . ?
C12 Ir1 Cl1 165.63(11) . . ?
C15 Ir1 Cl1 91.14(13) . . ?
C16 Ir1 Cl1 90.42(11) . . ?
C1 N1 C3 110.7(2) . . ?
C1 N1 C10 120.8(2) . . ?
C3 N1 C10 127.8(2) . . ?
C34 O1 C24 118.5(2) . . ?
N1 C1 N2 106.7(2) . . ?
N1 C1 Ir1 125.0(2) . . ?
N2 C1 Ir1 127.1(2) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 N1 133.0(3) . . ?
C2 C3 N1 106.1(2) . . ?
C3 C2 C7 120.9(3) . . ?
C3 C2 N2 106.8(2) . . ?
C7 C2 N2 132.2(3) . . ?
C1 N2 C2 109.6(2) . . ?
C1 N2 C19 122.6(2) . . ?
C2 N2 C19 127.5(2) . . ?
C3 C4 C5 118.7(3) . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 C9 119.1(3) . . ?
C6 C5 C9 120.8(3) . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 C8 118.9(3) . . ?
C5 C6 C8 120.0(3) . . ?
C27 C26 C25 118.3(3) . . ?
C27 C26 C32 118.8(3) . . ?
C25 C26 C32 122.9(3) . . ?
C6 C7 C2 118.4(3) . . ?
C11 C12 C13 123.0(3) . . ?
C11 C12 Ir1 69.67(19) . . ?
C13 C12 Ir1 114.2(3) . . ?
C14 C13 C12 113.7(4) . . ?
O2 C34 O1 123.0(3) . . ?
O2 C34 C35 124.8(3) . . ?
O1 C34 C35 112.1(3) . . ?
C13 C14 C15 114.1(4) . . ?
C15 C16 C17 122.4(4) . . ?
C15 C16 Ir1 70.5(2) . . ?
C17 C16 Ir1 112.1(2) . . ?
C16 C15 C14 125.6(4) . . ?
C16 C15 Ir1 72.2(2) . . ?
C14 C15 Ir1 110.1(3) . . ?
C17 C18 C11 113.7(3) . . ?
C21 C20 C19 110.6(3) . . ?
C30 C25 C26 120.4(3) . . ?
C30 C25 C10 120.3(3) . . ?
C26 C25 C10 119.3(3) . . ?
O1 C24 C19 107.0(2) . . ?
O1 C24 C23 109.5(3) . . ?
C19 C24 C23 110.9(2) . . ?
C24 C23 C22 111.0(3) . . ?
C22 C21 C20 111.3(3) . . ?
C29 C30 C25 118.6(3) . . ?
C29 C30 C33 119.2(3) . . ?
C25 C30 C33 122.2(3) . . ?
C29 C28 C27 117.7(3) . . ?
C29 C28 C31 120.5(4) . . ?
C27 C28 C31 121.8(4) . . ?
C28 C29 C30 122.4(4) . . ?
C28 C27 C26 122.6(4) . . ?
C37 C35 C38 108.6(3) . . ?
C37 C35 C36 110.5(4) . . ?
C38 C35 C36 110.4(3) . . ?
C37 C35 C34 108.8(3) . . ?
C38 C35 C34 111.3(3) . . ?
C36 C35 C34 107.2(3) . . ?
C21 C22 C23 111.0(3) . . ?
C18 C17 C16 113.5(3) . . ?
C12 C11 C18 125.4(3) . . ?
C12 C11 Ir1 71.40(19) . . ?
C18 C11 Ir1 112.7(2) . . ?
N1 C10 C25 115.1(2) . . ?
N2 C19 C24 112.8(2) . . ?
N2 C19 C20 112.5(2) . . ?
C24 C19 C20 111.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 N2 4.1(3) . . . . ?
C10 N1 C1 N2 175.7(2) . . . . ?
C3 N1 C1 Ir1 -164.3(2) . . . . ?
C10 N1 C1 Ir1 7.3(4) . . . . ?
C11 Ir1 C1 N1 -84.8(3) . . . . ?
C12 Ir1 C1 N1 -124.0(2) . . . . ?
C15 Ir1 C1 N1 152.9(4) . . . . ?
C16 Ir1 C1 N1 -6.5(6) . . . . ?
Cl1 Ir1 C1 N1 70.2(2) . . . . ?
C11 Ir1 C1 N2 109.2(3) . . . . ?
C12 Ir1 C1 N2 70.0(3) . . . . ?
C15 Ir1 C1 N2 -13.1(5) . . . . ?
C16 Ir1 C1 N2 -172.5(4) . . . . ?
Cl1 Ir1 C1 N2 -95.8(2) . . . . ?
C1 N1 C3 C4 174.4(3) . . . . ?
C10 N1 C3 C4 3.5(5) . . . . ?
C1 N1 C3 C2 -3.0(3) . . . . ?
C10 N1 C3 C2 -173.9(3) . . . . ?
C4 C3 C2 C7 -0.6(4) . . . . ?
N1 C3 C2 C7 177.3(2) . . . . ?
C4 C3 C2 N2 -177.1(2) . . . . ?
N1 C3 C2 N2 0.8(3) . . . . ?
N1 C1 N2 C2 -3.5(3) . . . . ?
Ir1 C1 N2 C2 164.5(2) . . . . ?
N1 C1 N2 C19 -178.0(2) . . . . ?
Ir1 C1 N2 C19 -10.0(4) . . . . ?
C3 C2 N2 C1 1.7(3) . . . . ?
C7 C2 N2 C1 -174.2(3) . . . . ?
C3 C2 N2 C19 175.9(2) . . . . ?
C7 C2 N2 C19 -0.1(5) . . . . ?
C2 C3 C4 C5 2.0(4) . . . . ?
N1 C3 C4 C5 -175.2(3) . . . . ?
C3 C4 C5 C6 -2.3(4) . . . . ?
C3 C4 C5 C9 175.7(3) . . . . ?
C4 C5 C6 C7 1.3(4) . . . . ?
C9 C5 C6 C7 -176.8(3) . . . . ?
C4 C5 C6 C8 -179.2(3) . . . . ?
C9 C5 C6 C8 2.8(4) . . . . ?
C5 C6 C7 C2 0.2(4) . . . . ?
C8 C6 C7 C2 -179.4(3) . . . . ?
C3 C2 C7 C6 -0.5(4) . . . . ?
N2 C2 C7 C6 174.9(3) . . . . ?
C1 Ir1 C12 C11 91.1(2) . . . . ?
C15 Ir1 C12 C11 -111.0(2) . . . . ?
C16 Ir1 C12 C11 -74.9(2) . . . . ?
Cl1 Ir1 C12 C11 -168.9(3) . . . . ?
C1 Ir1 C12 C13 -150.9(3) . . . . ?
C11 Ir1 C12 C13 118.0(4) . . . . ?
C15 Ir1 C12 C13 7.0(3) . . . . ?
C16 Ir1 C12 C13 43.2(3) . . . . ?
Cl1 Ir1 C12 C13 -50.8(6) . . . . ?
C11 C12 C13 C14 87.6(5) . . . . ?
Ir1 C12 C13 C14 7.0(5) . . . . ?
C24 O1 C34 O2 1.5(5) . . . . ?
C24 O1 C34 C35 -175.9(3) . . . . ?
C12 C13 C14 C15 -24.0(6) . . . . ?
C1 Ir1 C16 C15 167.4(4) . . . . ?
C11 Ir1 C16 C15 -112.2(3) . . . . ?
C12 Ir1 C16 C15 -74.3(3) . . . . ?
Cl1 Ir1 C16 C15 91.3(3) . . . . ?
C1 Ir1 C16 C17 -74.6(6) . . . . ?
C11 Ir1 C16 C17 5.7(3) . . . . ?
C12 Ir1 C16 C17 43.6(3) . . . . ?
C15 Ir1 C16 C17 118.0(4) . . . . ?
Cl1 Ir1 C16 C17 -150.7(3) . . . . ?
C17 C16 C15 C14 -2.0(6) . . . . ?
Ir1 C16 C15 C14 102.4(4) . . . . ?
C17 C16 C15 Ir1 -104.4(3) . . . . ?
C13 C14 C15 C16 -53.1(6) . . . . ?
C13 C14 C15 Ir1 29.0(5) . . . . ?
C1 Ir1 C15 C16 -170.8(3) . . . . ?
C11 Ir1 C15 C16 66.8(3) . . . . ?
C12 Ir1 C15 C16 102.9(3) . . . . ?
Cl1 Ir1 C15 C16 -89.2(2) . . . . ?
C1 Ir1 C15 C14 66.9(5) . . . . ?
C11 Ir1 C15 C14 -55.4(3) . . . . ?
C12 Ir1 C15 C14 -19.3(3) . . . . ?
C16 Ir1 C15 C14 -122.2(4) . . . . ?
Cl1 Ir1 C15 C14 148.6(3) . . . . ?
C27 C26 C25 C30 1.5(4) . . . . ?
C32 C26 C25 C30 -178.1(3) . . . . ?
C27 C26 C25 C10 -179.0(3) . . . . ?
C32 C26 C25 C10 1.4(4) . . . . ?
C34 O1 C24 C19 -157.4(3) . . . . ?
C34 O1 C24 C23 82.4(3) . . . . ?
O1 C24 C23 C22 173.4(3) . . . . ?
C19 C24 C23 C22 55.6(4) . . . . ?
C19 C20 C21 C22 -55.7(4) . . . . ?
C26 C25 C30 C29 -0.6(5) . . . . ?
C10 C25 C30 C29 179.9(3) . . . . ?
C26 C25 C30 C33 -179.9(3) . . . . ?
C10 C25 C30 C33 0.6(5) . . . . ?
C27 C28 C29 C30 0.9(6) . . . . ?
C31 C28 C29 C30 178.9(3) . . . . ?
C25 C30 C29 C28 -0.6(5) . . . . ?
C33 C30 C29 C28 178.7(3) . . . . ?
C29 C28 C27 C26 0.0(6) . . . . ?
C31 C28 C27 C26 -177.9(3) . . . . ?
C25 C26 C27 C28 -1.2(5) . . . . ?
C32 C26 C27 C28 178.4(3) . . . . ?
O2 C34 C35 C37 15.4(5) . . . . ?
O1 C34 C35 C37 -167.3(3) . . . . ?
O2 C34 C35 C38 135.0(4) . . . . ?
O1 C34 C35 C38 -47.7(4) . . . . ?
O2 C34 C35 C36 -104.2(4) . . . . ?
O1 C34 C35 C36 73.1(4) . . . . ?
C20 C21 C22 C23 56.6(4) . . . . ?
C24 C23 C22 C21 -56.5(4) . . . . ?
C11 C18 C17 C16 -25.1(5) . . . . ?
C15 C16 C17 C18 89.1(5) . . . . ?
Ir1 C16 C17 C18 8.8(5) . . . . ?
C13 C12 C11 C18 -1.3(6) . . . . ?
Ir1 C12 C11 C18 105.1(3) . . . . ?
C13 C12 C11 Ir1 -106.3(4) . . . . ?
C17 C18 C11 C12 -52.7(5) . . . . ?
C17 C18 C11 Ir1 30.0(4) . . . . ?
C1 Ir1 C11 C12 -93.5(2) . . . . ?
C15 Ir1 C11 C12 68.0(2) . . . . ?
C16 Ir1 C11 C12 102.3(2) . . . . ?
Cl1 Ir1 C11 C12 173.49(18) . . . . ?
C1 Ir1 C11 C18 145.1(3) . . . . ?
C12 Ir1 C11 C18 -121.4(4) . . . . ?
C15 Ir1 C11 C18 -53.4(3) . . . . ?
C16 Ir1 C11 C18 -19.1(3) . . . . ?
Cl1 Ir1 C11 C18 52.1(4) . . . . ?
C1 N1 C10 C25 154.5(3) . . . . ?
C3 N1 C10 C25 -35.4(4) . . . . ?
C30 C25 C10 N1 -58.4(4) . . . . ?
C26 C25 C10 N1 122.1(3) . . . . ?
C1 N2 C19 C24 -124.4(3) . . . . ?
C2 N2 C19 C24 62.1(4) . . . . ?
C1 N2 C19 C20 108.1(3) . . . . ?
C2 N2 C19 C20 -65.4(4) . . . . ?
O1 C24 C19 N2 57.4(3) . . . . ?
C23 C24 C19 N2 176.8(2) . . . . ?
O1 C24 C19 C20 -174.7(2) . . . . ?
C23 C24 C19 C20 -55.3(3) . . . . ?
C21 C20 C19 N2 -176.8(3) . . . . ?
C21 C20 C19 C24 55.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.918
_refine_diff_density_rms         0.076
_database_code_depnum_ccdc_archive 'CCDC 985404'
