Supplementary Material (ESI) for Dalton Transactions
This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222

_publ_contact_author_name        'Frank Glorius'
_publ_contact_author_email       GLORIUS@UNI-MUENSTER.DE

_publ_section_title              
;
Investigation of the properties of
4,5-dialkylated N-heterocyclic carbenes
;
loop_
_publ_author_name
'Frank Glorius'
'Roland Frohlich'
'Matyas Tursky'
'Slawomir Urban'

# Attachment 'glo5061.cif'

data_glo5061
_database_code_depnum_ccdc_archive 'CCDC 730784'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H35 Cl Ir N2 O2'
_chemical_formula_weight         695.26

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   P21/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                   7.9293(1)
_cell_length_b                   19.9537(3)
_cell_length_c                   18.4870(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.594(1)
_cell_angle_gamma                90.00
_cell_volume                     2915.59(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    6265
_cell_measurement_theta_min      0.41
_cell_measurement_theta_max      27.88

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1380
_exptl_absorpt_coefficient_mu    4.700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2550
_exptl_absorpt_correction_T_max  0.6507
_exptl_absorpt_process_details   
'Denzo (otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode NOnius FR591'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\w and \ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20121
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         28.26
_reflns_number_total             7105
_reflns_number_gt                6043
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0359P)^2^+1.8061P] 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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7105
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0673
_refine_ls_wR_factor_gt          0.0627
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.476405(13) 0.683574(5) 0.720999(6) 0.02561(5) Uani 1 1 d . . .
Cl2 Cl 0.25979(11) 0.71606(6) 0.63383(5) 0.0507(2) Uani 1 1 d . . .
C3 C 0.3143(5) 0.68360(17) 0.7904(2) 0.0392(8) Uani 1 1 d . . .
O4 O 0.2168(4) 0.68299(15) 0.83162(16) 0.0635(9) Uani 1 1 d . . .
C5 C 0.6443(5) 0.65669(18) 0.7909(2) 0.0392(8) Uani 1 1 d . . .
O6 O 0.7378(4) 0.64128(16) 0.83137(16) 0.0617(8) Uani 1 1 d . . .
N7 N 0.7013(3) 0.73330(12) 0.60130(12) 0.0248(5) Uani 1 1 d . . .
C8 C 0.6456(4) 0.68169(13) 0.64075(16) 0.0241(6) Uani 1 1 d . . .
N9 N 0.7217(3) 0.62697(12) 0.61543(12) 0.0248(5) Uani 1 1 d . . .
C10 C 0.8248(3) 0.64358(15) 0.55988(15) 0.0270(6) Uani 1 1 d . . .
C11 C 0.8125(4) 0.71082(15) 0.55127(15) 0.0278(6) Uani 1 1 d . . .
C12 C 0.9296(4) 0.59217(16) 0.52565(18) 0.0368(7) Uani 1 1 d . . .
H12A H 0.8762 0.5483 0.5305 0.044 Uiso 1 1 calc R . .
H12B H 1.0409 0.5905 0.5528 0.044 Uiso 1 1 calc R . .
C13 C 0.9553(5) 0.60359(19) 0.44604(19) 0.0451(9) Uani 1 1 d . . .
H13A H 0.8445 0.6022 0.4185 0.054 Uiso 1 1 calc R . .
H13B H 1.0226 0.5664 0.4291 0.054 Uiso 1 1 calc R . .
C14 C 1.0417(5) 0.6689(2) 0.4286(2) 0.0480(9) Uani 1 1 d . . .
H14A H 1.1398 0.6753 0.4637 0.058 Uiso 1 1 calc R . .
H14B H 1.0839 0.6650 0.3804 0.058 Uiso 1 1 calc R . .
C15 C 0.9302(5) 0.73075(19) 0.42972(18) 0.0441(8) Uani 1 1 d . . .
H15A H 0.8198 0.7201 0.4047 0.053 Uiso 1 1 calc R . .
H15B H 0.9811 0.7663 0.4020 0.053 Uiso 1 1 calc R . .
C16 C 0.9022(4) 0.75780(17) 0.50480(17) 0.0358(7) Uani 1 1 d . . .
H16A H 1.0123 0.7689 0.5298 0.043 Uiso 1 1 calc R . .
H16B H 0.8367 0.7994 0.4993 0.043 Uiso 1 1 calc R . .
C17 C 0.7010(4) 0.55991(14) 0.64258(16) 0.0283(6) Uani 1 1 d . . .
C18 C 0.8264(4) 0.53274(16) 0.69028(17) 0.0333(7) Uani 1 1 d . . .
C19 C 0.8026(5) 0.46811(17) 0.71553(19) 0.0415(8) Uani 1 1 d . . .
H19 H 0.8866 0.4490 0.7479 0.050 Uiso 1 1 calc R . .
C20 C 0.6605(5) 0.43106(17) 0.6949(2) 0.0456(9) Uani 1 1 d . . .
C21 C 0.5384(4) 0.45999(17) 0.6468(2) 0.0438(9) Uani 1 1 d . . .
H21 H 0.4409 0.4352 0.6322 0.053 Uiso 1 1 calc R . .
C22 C 0.5550(4) 0.52455(16) 0.61935(18) 0.0334(7) Uani 1 1 d . . .
C23 C 0.9862(4) 0.5703(2) 0.71472(19) 0.0465(9) Uani 1 1 d . . .
H23A H 1.0776 0.5554 0.6867 0.070 Uiso 1 1 calc R . .
H23B H 1.0157 0.5616 0.7658 0.070 Uiso 1 1 calc R . .
H23C H 0.9681 0.6180 0.7073 0.070 Uiso 1 1 calc R . .
C24 C 0.6380(6) 0.3607(2) 0.7236(3) 0.0721(14) Uani 1 1 d . . .
H24A H 0.7327 0.3330 0.7117 0.108 Uiso 1 1 calc R . .
H24B H 0.5336 0.3418 0.7014 0.108 Uiso 1 1 calc R . .
H24C H 0.6335 0.3622 0.7758 0.108 Uiso 1 1 calc R . .
C25 C 0.4217(4) 0.55461(19) 0.5667(2) 0.0494(9) Uani 1 1 d . . .
H25A H 0.3604 0.5889 0.5910 0.074 Uiso 1 1 calc R . .
H25B H 0.3437 0.5199 0.5487 0.074 Uiso 1 1 calc R . .
H25C H 0.4750 0.5745 0.5264 0.074 Uiso 1 1 calc R . .
C26 C 0.6631(4) 0.80306(14) 0.61151(16) 0.0278(6) Uani 1 1 d . . .
C27 C 0.5488(4) 0.83551(18) 0.56215(18) 0.0373(7) Uani 1 1 d . . .
C28 C 0.5210(5) 0.90345(18) 0.5736(2) 0.0496(9) Uani 1 1 d . . .
H28 H 0.4438 0.9265 0.5413 0.060 Uiso 1 1 calc R . .
C29 C 0.6031(5) 0.93830(18) 0.6310(2) 0.0510(10) Uani 1 1 d . . .
C30 C 0.7158(5) 0.90425(17) 0.6780(2) 0.0444(8) Uani 1 1 d . . .
H30 H 0.7719 0.9276 0.7170 0.053 Uiso 1 1 calc R . .
C31 C 0.7494(4) 0.83680(16) 0.66959(17) 0.0332(7) Uani 1 1 d . . .
C32 C 0.4615(5) 0.7998(2) 0.4983(2) 0.0519(10) Uani 1 1 d . . .
H32A H 0.5320 0.8014 0.4578 0.078 Uiso 1 1 calc R . .
H32B H 0.3541 0.8214 0.4847 0.078 Uiso 1 1 calc R . .
H32C H 0.4419 0.7535 0.5112 0.078 Uiso 1 1 calc R . .
C34 C 0.8773(5) 0.8018(2) 0.7211(2) 0.0464(9) Uani 1 1 d . . .
H34A H 0.9364 0.8346 0.7525 0.070 Uiso 1 1 calc R . .
H34B H 0.9581 0.7782 0.6936 0.070 Uiso 1 1 calc R . .
H34C H 0.8200 0.7700 0.7503 0.070 Uiso 1 1 calc R . .
C33 C 0.5698(7) 1.0124(2) 0.6412(3) 0.0849(17) Uani 1 1 d . . .
H33A H 0.6603 1.0382 0.6225 0.127 Uiso 1 1 calc R . .
H33B H 0.5651 1.0219 0.6925 0.127 Uiso 1 1 calc R . .
H33C H 0.4629 1.0244 0.6153 0.127 Uiso 1 1 calc R . .
C41 C 1.0457(8) 0.5569(3) 1.0370(3) 0.0914(18) Uani 1 1 d . . .
H41 H 1.0742 0.5962 1.0632 0.110 Uiso 1 1 calc R . .
C42 C 0.9919(8) 0.5602(3) 0.9664(3) 0.0900(18) Uani 1 1 d . . .
H42 H 0.9893 0.6017 0.9423 0.108 Uiso 1 1 calc R . .
C43 C 0.9414(9) 0.5040(3) 0.9297(3) 0.097(2) Uani 1 1 d . . .
H43 H 0.8974 0.5070 0.8810 0.116 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ir1 0.02891(7) 0.02223(7) 0.02655(7) -0.00179(4) 0.00756(4) -0.00012(4)
Cl2 0.0389(4) 0.0634(6) 0.0501(5) 0.0010(4) 0.0038(4) 0.0113(4)
C3 0.0433(19) 0.038(2) 0.0382(19) -0.0058(14) 0.0136(15) -0.0001(14)
O4 0.0607(19) 0.082(2) 0.0531(17) -0.0088(14) 0.0354(15) -0.0001(14)
C5 0.049(2) 0.0277(17) 0.043(2) 0.0031(15) 0.0164(16) -0.0049(16)
O6 0.0621(18) 0.066(2) 0.0556(17) 0.0042(15) -0.0064(14) -0.0064(15)
N7 0.0294(12) 0.0201(12) 0.0257(12) 0.0018(9) 0.0065(9) 0.0016(10)
C8 0.0243(14) 0.0225(14) 0.0256(14) 0.0006(11) 0.0031(11) -0.0009(11)
N9 0.0273(12) 0.0182(12) 0.0296(12) 0.0010(9) 0.0061(9) 0.0018(9)
C10 0.0256(14) 0.0270(15) 0.0295(14) 0.0004(12) 0.0081(11) -0.0004(11)
C11 0.0291(14) 0.0272(15) 0.0277(14) 0.0018(12) 0.0061(11) 0.0024(12)
C12 0.0409(18) 0.0279(17) 0.0436(18) -0.0012(14) 0.0149(14) 0.0090(14)
C13 0.049(2) 0.043(2) 0.046(2) -0.0103(16) 0.0179(16) 0.0043(17)
C14 0.050(2) 0.053(2) 0.044(2) 0.0030(17) 0.0243(17) 0.0070(18)
C15 0.051(2) 0.047(2) 0.0366(18) 0.0097(15) 0.0189(15) 0.0033(17)
C16 0.0368(17) 0.0319(17) 0.0405(17) 0.0072(14) 0.0136(13) -0.0008(14)
C17 0.0306(15) 0.0206(14) 0.0348(15) -0.0010(12) 0.0097(11) 0.0006(11)
C18 0.0345(16) 0.0273(16) 0.0390(17) 0.0034(13) 0.0078(13) 0.0034(13)
C19 0.0453(19) 0.0304(18) 0.051(2) 0.0126(15) 0.0155(15) 0.0129(15)
C20 0.047(2) 0.0243(17) 0.070(2) 0.0044(17) 0.0338(18) 0.0025(15)
C21 0.0386(18) 0.0281(18) 0.068(2) -0.0074(16) 0.0224(16) -0.0092(14)
C22 0.0299(15) 0.0259(16) 0.0456(18) -0.0095(13) 0.0107(13) -0.0025(12)
C23 0.0374(19) 0.047(2) 0.054(2) 0.0114(16) -0.0049(15) -0.0008(15)
C24 0.072(3) 0.029(2) 0.122(4) 0.021(2) 0.049(3) 0.004(2)
C25 0.0358(18) 0.044(2) 0.066(2) -0.0173(18) -0.0073(16) -0.0004(16)
C26 0.0318(15) 0.0187(14) 0.0338(16) 0.0031(11) 0.0089(12) 0.0011(11)
C27 0.0401(18) 0.0369(18) 0.0355(17) 0.0098(14) 0.0063(13) 0.0057(14)
C28 0.054(2) 0.0319(19) 0.064(2) 0.0175(17) 0.0123(18) 0.0156(17)
C29 0.059(2) 0.0267(19) 0.070(3) -0.0004(18) 0.025(2) 0.0051(17)
C30 0.052(2) 0.0267(18) 0.056(2) -0.0091(16) 0.0147(17) -0.0078(15)
C31 0.0351(16) 0.0281(16) 0.0375(17) -0.0017(13) 0.0100(13) -0.0062(13)
C32 0.058(2) 0.058(2) 0.039(2) 0.0094(18) -0.0059(17) 0.0090(19)
C34 0.043(2) 0.049(2) 0.046(2) -0.0027(17) -0.0061(15) -0.0079(17)
C33 0.108(4) 0.021(2) 0.129(5) -0.003(2) 0.031(4) 0.011(2)
C41 0.124(5) 0.069(4) 0.079(4) -0.012(3) -0.003(3) 0.017(3)
C42 0.135(5) 0.063(4) 0.074(4) 0.020(3) 0.019(3) 0.024(3)
C43 0.145(6) 0.089(4) 0.054(3) 0.003(3) -0.006(3) 0.040(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C5 1.859(4) . ?
Ir1 C3 1.887(4) . ?
Ir1 C8 2.079(3) . ?
Ir1 Cl2 2.3502(9) . ?
C3 O4 1.128(4) . ?
C5 O6 1.055(4) . ?
N7 C8 1.356(4) . ?
N7 C11 1.402(4) . ?
N7 C26 1.440(4) . ?
C8 N9 1.350(4) . ?
N9 C10 1.402(3) . ?
N9 C17 1.443(4) . ?
C10 C11 1.354(4) . ?
C10 C12 1.493(4) . ?
C11 C16 1.490(4) . ?
C12 C13 1.519(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C14 1.519(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.519(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C16 1.522(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 C18 1.386(4) . ?
C17 C22 1.394(4) . ?
C18 C19 1.389(4) . ?
C18 C23 1.510(5) . ?
C19 C20 1.375(5) . ?
C19 H19 0.9400 . ?
C20 C21 1.387(6) . ?
C20 C24 1.516(5) . ?
C21 C22 1.395(5) . ?
C21 H21 0.9400 . ?
C22 C25 1.503(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
C26 C27 1.393(4) . ?
C26 C31 1.399(4) . ?
C27 C28 1.392(5) . ?
C27 C32 1.500(5) . ?
C28 C29 1.387(6) . ?
C28 H28 0.9400 . ?
C29 C30 1.374(6) . ?
C29 C33 1.516(5) . ?
C30 C31 1.383(5) . ?
C30 H30 0.9400 . ?
C31 C34 1.506(5) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 H32C 0.9700 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 H34C 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 H33C 0.9700 . ?
C41 C42 1.341(7) . ?
C41 C43 1.363(8) 3_767 ?
C41 H41 0.9400 . ?
C42 C43 1.355(8) . ?
C42 H42 0.9400 . ?
C43 C41 1.363(8) 3_767 ?
C43 H43 0.9400 . ?

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
C5 Ir1 C3 90.95(15) . . ?
C5 Ir1 C8 91.37(13) . . ?
C3 Ir1 C8 177.09(13) . . ?
C5 Ir1 Cl2 178.73(10) . . ?
C3 Ir1 Cl2 88.03(12) . . ?
C8 Ir1 Cl2 89.63(8) . . ?
O4 C3 Ir1 179.3(3) . . ?
O6 C5 Ir1 178.9(3) . . ?
C8 N7 C11 111.2(2) . . ?
C8 N7 C26 125.6(2) . . ?
C11 N7 C26 123.1(2) . . ?
N9 C8 N7 104.7(2) . . ?
N9 C8 Ir1 126.5(2) . . ?
N7 C8 Ir1 128.8(2) . . ?
C8 N9 C10 111.5(2) . . ?
C8 N9 C17 124.3(2) . . ?
C10 N9 C17 124.3(2) . . ?
C11 C10 N9 106.3(2) . . ?
C11 C10 C12 132.0(3) . . ?
N9 C10 C12 121.7(3) . . ?
C10 C11 N7 106.4(2) . . ?
C10 C11 C16 131.2(3) . . ?
N7 C11 C16 122.3(3) . . ?
C10 C12 C13 115.5(3) . . ?
C10 C12 H12A 108.4 . . ?
C13 C12 H12A 108.4 . . ?
C10 C12 H12B 108.4 . . ?
C13 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C12 C13 C14 115.6(3) . . ?
C12 C13 H13A 108.4 . . ?
C14 C13 H13A 108.4 . . ?
C12 C13 H13B 108.4 . . ?
C14 C13 H13B 108.4 . . ?
H13A C13 H13B 107.4 . . ?
C15 C14 C13 114.9(3) . . ?
C15 C14 H14A 108.5 . . ?
C13 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C13 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C14 C15 C16 115.4(3) . . ?
C14 C15 H15A 108.4 . . ?
C16 C15 H15A 108.4 . . ?
C14 C15 H15B 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.5 . . ?
C11 C16 C15 114.5(3) . . ?
C11 C16 H16A 108.6 . . ?
C15 C16 H16A 108.6 . . ?
C11 C16 H16B 108.6 . . ?
C15 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C22 122.3(3) . . ?
C18 C17 N9 119.2(3) . . ?
C22 C17 N9 118.5(3) . . ?
C17 C18 C19 117.8(3) . . ?
C17 C18 C23 122.6(3) . . ?
C19 C18 C23 119.6(3) . . ?
C20 C19 C18 122.4(3) . . ?
C20 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
C19 C20 C21 117.9(3) . . ?
C19 C20 C24 121.2(4) . . ?
C21 C20 C24 120.9(4) . . ?
C20 C21 C22 122.5(3) . . ?
C20 C21 H21 118.8 . . ?
C22 C21 H21 118.8 . . ?
C17 C22 C21 117.1(3) . . ?
C17 C22 C25 121.4(3) . . ?
C21 C22 C25 121.5(3) . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
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 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C31 122.1(3) . . ?
C27 C26 N7 119.7(3) . . ?
C31 C26 N7 118.1(3) . . ?
C28 C27 C26 117.1(3) . . ?
C28 C27 C32 120.9(3) . . ?
C26 C27 C32 122.0(3) . . ?
C29 C28 C27 122.3(3) . . ?
C29 C28 H28 118.9 . . ?
C27 C28 H28 118.9 . . ?
C30 C29 C28 118.5(3) . . ?
C30 C29 C33 120.9(4) . . ?
C28 C29 C33 120.6(4) . . ?
C29 C30 C31 122.1(3) . . ?
C29 C30 H30 118.9 . . ?
C31 C30 H30 118.9 . . ?
C30 C31 C26 117.9(3) . . ?
C30 C31 C34 120.4(3) . . ?
C26 C31 C34 121.7(3) . . ?
C27 C32 H32A 109.5 . . ?
C27 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C27 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C29 C33 H33A 109.5 . . ?
C29 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C29 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C42 C41 C43 119.3(6) . 3_767 ?
C42 C41 H41 120.3 . . ?
C43 C41 H41 120.3 3_767 . ?
C41 C42 C43 120.4(6) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C42 C43 C41 120.2(5) . 3_767 ?
C42 C43 H43 119.9 . . ?
C41 C43 H43 119.9 3_767 . ?

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
C5 Ir1 C3 O4 -96(36) . . . . ?
C8 Ir1 C3 O4 46(37) . . . . ?
Cl2 Ir1 C3 O4 83(36) . . . . ?
C3 Ir1 C5 O6 9(19) . . . . ?
C8 Ir1 C5 O6 -170(100) . . . . ?
Cl2 Ir1 C5 O6 -28(23) . . . . ?
C11 N7 C8 N9 0.0(3) . . . . ?
C26 N7 C8 N9 -176.0(3) . . . . ?
C11 N7 C8 Ir1 -178.7(2) . . . . ?
C26 N7 C8 Ir1 5.4(4) . . . . ?
C5 Ir1 C8 N9 66.4(3) . . . . ?
C3 Ir1 C8 N9 -76(3) . . . . ?
Cl2 Ir1 C8 N9 -112.8(3) . . . . ?
C5 Ir1 C8 N7 -115.2(3) . . . . ?
C3 Ir1 C8 N7 102(3) . . . . ?
Cl2 Ir1 C8 N7 65.5(3) . . . . ?
N7 C8 N9 C10 -0.3(3) . . . . ?
Ir1 C8 N9 C10 178.4(2) . . . . ?
N7 C8 N9 C17 179.1(2) . . . . ?
Ir1 C8 N9 C17 -2.2(4) . . . . ?
C8 N9 C10 C11 0.5(3) . . . . ?
C17 N9 C10 C11 -178.9(3) . . . . ?
C8 N9 C10 C12 176.8(3) . . . . ?
C17 N9 C10 C12 -2.7(4) . . . . ?
N9 C10 C11 N7 -0.5(3) . . . . ?
C12 C10 C11 N7 -176.2(3) . . . . ?
N9 C10 C11 C16 174.7(3) . . . . ?
C12 C10 C11 C16 -1.0(6) . . . . ?
C8 N7 C11 C10 0.4(3) . . . . ?
C26 N7 C11 C10 176.4(3) . . . . ?
C8 N7 C11 C16 -175.4(3) . . . . ?
C26 N7 C11 C16 0.6(4) . . . . ?
C11 C10 C12 C13 -37.0(5) . . . . ?
N9 C10 C12 C13 147.8(3) . . . . ?
C10 C12 C13 C14 59.8(4) . . . . ?
C12 C13 C14 C15 -76.1(4) . . . . ?
C13 C14 C15 C16 78.0(4) . . . . ?
C10 C11 C16 C15 39.2(5) . . . . ?
N7 C11 C16 C15 -146.2(3) . . . . ?
C14 C15 C16 C11 -62.9(4) . . . . ?
C8 N9 C17 C18 -101.1(3) . . . . ?
C10 N9 C17 C18 78.2(4) . . . . ?
C8 N9 C17 C22 79.3(4) . . . . ?
C10 N9 C17 C22 -101.4(3) . . . . ?
C22 C17 C18 C19 -0.5(4) . . . . ?
N9 C17 C18 C19 179.9(3) . . . . ?
C22 C17 C18 C23 178.9(3) . . . . ?
N9 C17 C18 C23 -0.7(4) . . . . ?
C17 C18 C19 C20 -0.1(5) . . . . ?
C23 C18 C19 C20 -179.5(3) . . . . ?
C18 C19 C20 C21 0.4(5) . . . . ?
C18 C19 C20 C24 -179.9(3) . . . . ?
C19 C20 C21 C22 -0.2(5) . . . . ?
C24 C20 C21 C22 -179.9(3) . . . . ?
C18 C17 C22 C21 0.7(4) . . . . ?
N9 C17 C22 C21 -179.7(3) . . . . ?
C18 C17 C22 C25 -179.1(3) . . . . ?
N9 C17 C22 C25 0.5(4) . . . . ?
C20 C21 C22 C17 -0.3(5) . . . . ?
C20 C21 C22 C25 179.4(3) . . . . ?
C8 N7 C26 C27 -105.9(3) . . . . ?
C11 N7 C26 C27 78.6(4) . . . . ?
C8 N7 C26 C31 77.0(4) . . . . ?
C11 N7 C26 C31 -98.5(3) . . . . ?
C31 C26 C27 C28 -1.1(5) . . . . ?
N7 C26 C27 C28 -178.1(3) . . . . ?
C31 C26 C27 C32 177.7(3) . . . . ?
N7 C26 C27 C32 0.7(5) . . . . ?
C26 C27 C28 C29 0.4(5) . . . . ?
C32 C27 C28 C29 -178.3(4) . . . . ?
C27 C28 C29 C30 0.1(6) . . . . ?
C27 C28 C29 C33 179.6(4) . . . . ?
C28 C29 C30 C31 0.0(6) . . . . ?
C33 C29 C30 C31 -179.5(4) . . . . ?
C29 C30 C31 C26 -0.6(5) . . . . ?
C29 C30 C31 C34 178.3(3) . . . . ?
C27 C26 C31 C30 1.2(5) . . . . ?
N7 C26 C31 C30 178.2(3) . . . . ?
C27 C26 C31 C34 -177.8(3) . . . . ?
N7 C26 C31 C34 -0.7(4) . . . . ?
C43 C41 C42 C43 3.9(11) 3_767 . . . ?
C41 C42 C43 C41 -3.9(11) . . . 3_767 ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        28.26
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.122
_refine_diff_density_min         -1.109
_refine_diff_density_rms         0.095

# Attachment 'glo5065.cif'

data_glo5065
_database_code_depnum_ccdc_archive 'CCDC 730785'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H42 Cl Ir N2 O2'
_chemical_formula_weight         726.34

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           orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   19.4679(3)
_cell_length_b                   17.5361(2)
_cell_length_c                   9.5159(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3248.64(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4339
_cell_measurement_theta_min      0.41
_cell_measurement_theta_max      27.88

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    4.222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4856
_exptl_absorpt_correction_T_max  0.8167
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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            22070
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         28.28
_reflns_number_total             4104
_reflns_number_gt                3408
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SNM (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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.
Group C10-C11 refined with split positions, due to symmetry restrictions
the occupancy is set to 0.5.
;

_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^)+(0.0295P)^2^+7.2020P] 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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4104
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.962413(11) 0.2500 0.10506(2) 0.03380(8) Uani 1 2 d S . .
Cl2 Cl 1.05161(8) 0.2500 -0.0558(2) 0.0553(4) Uani 1 2 d S . .
C3 C 1.0292(4) 0.2500 0.2493(8) 0.069(2) Uani 1 2 d S . .
O4 O 1.0688(4) 0.2500 0.3343(7) 0.118(3) Uani 1 2 d S . .
C5 C 0.8932(4) 0.2500 0.2348(6) 0.0499(15) Uani 1 2 d S . .
O6 O 0.8514(3) 0.2500 0.3183(5) 0.0760(16) Uani 1 2 d S . .
N7 N 0.86329(15) 0.18885(15) -0.1235(3) 0.0271(6) Uani 1 1 d . . .
C8 C 0.8922(2) 0.2500 -0.0619(5) 0.0250(9) Uani 1 2 d S . .
C9 C 0.81450(18) 0.21181(18) -0.2224(3) 0.0293(7) Uani 1 1 d . . .
C10A C 0.7621(14) 0.1676(16) -0.296(3) 0.032(4) Uani 0.50 1 d P . 1
H10A H 0.7252 0.1536 -0.2311 0.039 Uiso 0.50 1 calc PR . 1
H10B H 0.7823 0.1206 -0.3336 0.039 Uiso 0.50 1 calc PR . 1
C11A C 0.7335(7) 0.2147(9) -0.4145(16) 0.041(3) Uani 0.50 1 d P . 1
H11A H 0.7579 0.1988 -0.4997 0.049 Uiso 0.50 1 calc PR . 1
H11B H 0.6856 0.1988 -0.4265 0.049 Uiso 0.50 1 calc PR . 1
C10B C 0.7753(14) 0.1583(16) -0.321(3) 0.033(4) Uani 0.50 1 d P . 2
H10C H 0.7601 0.1123 -0.2718 0.040 Uiso 0.50 1 calc PR . 2
H10D H 0.8039 0.1433 -0.4014 0.040 Uiso 0.50 1 calc PR . 2
C11B C 0.7130(7) 0.2064(10) -0.3704(19) 0.053(5) Uani 0.50 1 d P . 2
H11C H 0.7028 0.1905 -0.4668 0.064 Uiso 0.50 1 calc PR . 2
H11D H 0.6738 0.1905 -0.3128 0.064 Uiso 0.50 1 calc PR . 2
C12 C 0.8810(2) 0.10936(18) -0.1041(4) 0.0312(7) Uani 1 1 d . . .
C13 C 0.9298(2) 0.0776(2) -0.1933(4) 0.0388(9) Uani 1 1 d . . .
C14 C 0.9427(3) -0.0008(2) -0.1789(5) 0.0546(12) Uani 1 1 d . . .
H14 H 0.9758 -0.0242 -0.2363 0.065 Uiso 1 1 calc R . .
C15 C 0.9074(3) -0.0438(2) -0.0818(5) 0.0637(14) Uani 1 1 d . . .
H15 H 0.9164 -0.0963 -0.0741 0.076 Uiso 1 1 calc R . .
C16 C 0.8598(3) -0.0109(2) 0.0028(5) 0.0569(12) Uani 1 1 d . . .
H16 H 0.8362 -0.0414 0.0681 0.068 Uiso 1 1 calc R . .
C17 C 0.8447(2) 0.0668(2) -0.0043(4) 0.0396(9) Uani 1 1 d . . .
C18 C 0.9682(2) 0.1224(2) -0.3060(5) 0.0469(10) Uani 1 1 d . . .
H18 H 0.9620 0.1773 -0.2851 0.056 Uiso 1 1 calc R . .
C19 C 0.9376(3) 0.1076(4) -0.4513(5) 0.088(2) Uani 1 1 d . . .
H19A H 0.9390 0.0534 -0.4712 0.133 Uiso 1 1 calc R . .
H19B H 0.9641 0.1349 -0.5215 0.133 Uiso 1 1 calc R . .
H19C H 0.8904 0.1252 -0.4533 0.133 Uiso 1 1 calc R . .
C20 C 1.0454(3) 0.1064(3) -0.3081(6) 0.0676(14) Uani 1 1 d . . .
H20A H 1.0640 0.1133 -0.2144 0.101 Uiso 1 1 calc R . .
H20B H 1.0678 0.1414 -0.3725 0.101 Uiso 1 1 calc R . .
H20C H 1.0533 0.0544 -0.3386 0.101 Uiso 1 1 calc R . .
C21 C 0.7914(3) 0.1006(3) 0.0931(4) 0.0510(11) Uani 1 1 d . . .
H21 H 0.7947 0.1568 0.0864 0.061 Uiso 1 1 calc R . .
C22 C 0.8047(3) 0.0782(3) 0.2470(5) 0.0777(17) Uani 1 1 d . . .
H22A H 0.7960 0.0241 0.2591 0.117 Uiso 1 1 calc R . .
H22B H 0.7744 0.1071 0.3079 0.117 Uiso 1 1 calc R . .
H22C H 0.8521 0.0892 0.2709 0.117 Uiso 1 1 calc R . .
C23 C 0.7179(3) 0.0776(4) 0.0524(7) 0.0861(18) Uani 1 1 d . . .
H23A H 0.7069 0.0983 -0.0395 0.129 Uiso 1 1 calc R . .
H23B H 0.6858 0.0975 0.1213 0.129 Uiso 1 1 calc R . .
H23C H 0.7144 0.0224 0.0496 0.129 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ir1 0.03586(12) 0.02984(11) 0.03570(12) 0.000 -0.01033(9) 0.000
Cl2 0.0327(8) 0.0577(10) 0.0755(11) 0.000 0.0046(7) 0.000
C3 0.069(5) 0.077(5) 0.061(4) 0.000 -0.025(4) 0.000
O4 0.097(5) 0.165(7) 0.092(5) 0.000 -0.067(4) 0.000
C5 0.064(4) 0.050(4) 0.036(3) 0.000 -0.011(3) 0.000
O6 0.085(4) 0.097(4) 0.046(3) 0.000 0.023(3) 0.000
N7 0.0315(15) 0.0187(13) 0.0312(15) 0.0004(11) -0.0075(11) -0.0005(11)
C8 0.024(2) 0.023(2) 0.027(2) 0.000 -0.0006(18) 0.000
C9 0.0325(18) 0.0220(16) 0.0334(18) 0.0011(13) -0.0069(14) -0.0013(14)
C10A 0.034(9) 0.020(8) 0.042(9) -0.013(6) -0.005(5) 0.002(6)
C11A 0.039(8) 0.034(6) 0.050(8) -0.006(5) -0.020(5) -0.003(5)
C10B 0.037(10) 0.017(6) 0.046(10) -0.012(6) -0.011(6) 0.008(6)
C11B 0.035(8) 0.029(5) 0.096(14) 0.012(7) -0.033(7) -0.010(5)
C12 0.043(2) 0.0172(14) 0.0335(18) -0.0007(13) -0.0120(15) 0.0020(14)
C13 0.051(2) 0.0258(18) 0.039(2) -0.0024(15) -0.0110(18) 0.0058(16)
C14 0.076(3) 0.031(2) 0.057(3) -0.0072(19) -0.009(2) 0.017(2)
C15 0.095(4) 0.0220(19) 0.074(3) 0.005(2) -0.008(3) 0.013(2)
C16 0.083(4) 0.027(2) 0.061(3) 0.0146(19) -0.009(3) -0.004(2)
C17 0.052(2) 0.0265(18) 0.040(2) 0.0044(15) -0.0104(18) -0.0036(16)
C18 0.053(3) 0.040(2) 0.047(2) -0.0003(18) 0.0024(19) 0.0118(19)
C19 0.092(4) 0.130(6) 0.043(3) 0.017(3) -0.008(3) 0.002(4)
C20 0.060(3) 0.074(4) 0.069(3) -0.009(3) 0.006(3) 0.016(3)
C21 0.066(3) 0.041(2) 0.046(2) 0.0044(18) 0.002(2) -0.009(2)
C22 0.120(5) 0.067(3) 0.046(3) 0.011(2) 0.008(3) -0.011(3)
C23 0.064(4) 0.105(5) 0.090(4) -0.011(4) 0.000(3) -0.014(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C5 1.828(7) . ?
Ir1 C3 1.890(7) . ?
Ir1 C8 2.096(5) . ?
Ir1 Cl2 2.3147(17) . ?
C3 O4 1.119(8) . ?
C5 O6 1.138(8) . ?
N7 C8 1.346(4) . ?
N7 C9 1.396(4) . ?
N7 C12 1.448(4) . ?
C8 N7 1.346(4) 7_565 ?
C9 C9 1.339(6) 7_565 ?
C9 C10A 1.46(3) . ?
C9 C10B 1.53(3) . ?
C10A C11A 1.50(4) . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C11A C11A 1.24(3) 7_565 ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C10B C11B 1.55(3) . ?
C10B H10C 0.9800 . ?
C10B H10D 0.9800 . ?
C11B C11B 1.53(3) 7_565 ?
C11B H11C 0.9800 . ?
C11B H11D 0.9800 . ?
C12 C13 1.391(5) . ?
C12 C17 1.399(5) . ?
C13 C14 1.404(5) . ?
C13 C18 1.526(6) . ?
C14 C15 1.375(7) . ?
C14 H14 0.9400 . ?
C15 C16 1.357(7) . ?
C15 H15 0.9400 . ?
C16 C17 1.396(5) . ?
C16 H16 0.9400 . ?
C17 C21 1.513(6) . ?
C18 C19 1.527(7) . ?
C18 C20 1.529(6) . ?
C18 H18 0.9900 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C23 1.537(7) . ?
C21 C22 1.538(6) . ?
C21 H21 0.9900 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?

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
C5 Ir1 C3 90.9(3) . . ?
C5 Ir1 C8 91.8(2) . . ?
C3 Ir1 C8 177.3(3) . . ?
C5 Ir1 Cl2 178.90(19) . . ?
C3 Ir1 Cl2 88.0(3) . . ?
C8 Ir1 Cl2 89.32(14) . . ?
O4 C3 Ir1 179.8(9) . . ?
O6 C5 Ir1 178.2(6) . . ?
C8 N7 C9 110.4(3) . . ?
C8 N7 C12 127.8(3) . . ?
C9 N7 C12 121.7(3) . . ?
N7 C8 N7 105.7(4) . 7_565 ?
N7 C8 Ir1 127.10(19) . . ?
N7 C8 Ir1 127.10(19) 7_565 . ?
C9 C9 N7 106.76(17) 7_565 . ?
C9 C9 C10A 122.0(11) 7_565 . ?
N7 C9 C10A 130.2(12) . . ?
C9 C9 C10B 127.7(11) 7_565 . ?
N7 C9 C10B 125.2(11) . . ?
C10A C9 C10B 14.6(12) . . ?
C9 C10A C11A 109(2) . . ?
C9 C10A H10A 109.9 . . ?
C11A C10A H10A 109.9 . . ?
C9 C10A H10B 109.9 . . ?
C11A C10A H10B 109.9 . . ?
H10A C10A H10B 108.3 . . ?
C11A C11A C10A 123.4(12) 7_565 . ?
C11A C11A H11A 106.5 7_565 . ?
C10A C11A H11A 106.5 . . ?
C11A C11A H11B 106.5 7_565 . ?
C10A C11A H11B 106.5 . . ?
H11A C11A H11B 106.5 . . ?
C9 C10B C11B 104.0(16) . . ?
C9 C10B H10C 111.0 . . ?
C11B C10B H10C 111.0 . . ?
C9 C10B H10D 111.0 . . ?
C11B C10B H10D 111.0 . . ?
H10C C10B H10D 109.0 . . ?
C11B C11B C10B 123.0(13) 7_565 . ?
C11B C11B H11C 106.6 7_565 . ?
C10B C11B H11C 106.6 . . ?
C11B C11B H11D 106.6 7_565 . ?
C10B C11B H11D 106.6 . . ?
H11C C11B H11D 106.5 . . ?
C13 C12 C17 123.1(3) . . ?
C13 C12 N7 118.1(3) . . ?
C17 C12 N7 118.6(3) . . ?
C12 C13 C14 117.1(4) . . ?
C12 C13 C18 123.8(3) . . ?
C14 C13 C18 119.1(4) . . ?
C15 C14 C13 120.9(4) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 122.0(4) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C16 C17 C12 116.5(4) . . ?
C16 C17 C21 119.8(4) . . ?
C12 C17 C21 123.6(3) . . ?
C13 C18 C19 111.0(4) . . ?
C13 C18 C20 113.3(4) . . ?
C19 C18 C20 109.9(4) . . ?
C13 C18 H18 107.5 . . ?
C19 C18 H18 107.5 . . ?
C20 C18 H18 107.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 C23 112.4(4) . . ?
C17 C21 C22 111.6(4) . . ?
C23 C21 C22 109.3(4) . . ?
C17 C21 H21 107.8 . . ?
C23 C21 H21 107.8 . . ?
C22 C21 H21 107.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C5 Ir1 C3 O4 180(100) . . . . ?
C8 Ir1 C3 O4 0(100) . . . . ?
Cl2 Ir1 C3 O4 0(100) . . . . ?
C3 Ir1 C5 O6 0.000(12) . . . . ?
C8 Ir1 C5 O6 180.000(12) . . . . ?
Cl2 Ir1 C5 O6 -0.001(17) . . . . ?
C9 N7 C8 N7 -1.5(5) . . . 7_565 ?
C12 N7 C8 N7 173.9(2) . . . 7_565 ?
C9 N7 C8 Ir1 174.6(3) . . . . ?
C12 N7 C8 Ir1 -10.0(6) . . . . ?
C5 Ir1 C8 N7 -87.6(4) . . . . ?
C3 Ir1 C8 N7 92.4(4) . . . . ?
Cl2 Ir1 C8 N7 92.4(4) . . . . ?
C5 Ir1 C8 N7 87.6(4) . . . 7_565 ?
C3 Ir1 C8 N7 -92.4(4) . . . 7_565 ?
Cl2 Ir1 C8 N7 -92.4(4) . . . 7_565 ?
C8 N7 C9 C9 0.9(3) . . . 7_565 ?
C12 N7 C9 C9 -174.8(3) . . . 7_565 ?
C8 N7 C9 C10A -167.8(10) . . . . ?
C12 N7 C9 C10A 16.5(11) . . . . ?
C8 N7 C9 C10B 174.9(11) . . . . ?
C12 N7 C9 C10B -0.8(12) . . . . ?
C9 C9 C10A C11A 25.4(15) 7_565 . . . ?
N7 C9 C10A C11A -167.3(8) . . . . ?
C10B C9 C10A C11A -92(10) . . . . ?
C9 C10A C11A C11A -25.9(16) . . . 7_565 ?
C9 C9 C10B C11B -25.5(19) 7_565 . . . ?
N7 C9 C10B C11B 161.8(9) . . . . ?
C10A C9 C10B C11B 46(8) . . . . ?
C9 C10B C11B C11B 24.0(19) . . . 7_565 ?
C8 N7 C12 C13 -90.9(5) . . . . ?
C9 N7 C12 C13 84.0(4) . . . . ?
C8 N7 C12 C17 93.9(5) . . . . ?
C9 N7 C12 C17 -91.2(4) . . . . ?
C17 C12 C13 C14 -0.7(6) . . . . ?
N7 C12 C13 C14 -175.7(3) . . . . ?
C17 C12 C13 C18 177.9(4) . . . . ?
N7 C12 C13 C18 2.9(5) . . . . ?
C12 C13 C14 C15 0.9(7) . . . . ?
C18 C13 C14 C15 -177.7(4) . . . . ?
C13 C14 C15 C16 -0.5(8) . . . . ?
C14 C15 C16 C17 -0.2(8) . . . . ?
C15 C16 C17 C12 0.4(7) . . . . ?
C15 C16 C17 C21 -179.6(4) . . . . ?
C13 C12 C17 C16 0.1(6) . . . . ?
N7 C12 C17 C16 175.1(3) . . . . ?
C13 C12 C17 C21 -179.9(4) . . . . ?
N7 C12 C17 C21 -4.9(5) . . . . ?
C12 C13 C18 C19 -101.5(5) . . . . ?
C14 C13 C18 C19 77.1(5) . . . . ?
C12 C13 C18 C20 134.3(4) . . . . ?
C14 C13 C18 C20 -47.1(6) . . . . ?
C16 C17 C21 C23 -72.8(6) . . . . ?
C12 C17 C21 C23 107.2(5) . . . . ?
C16 C17 C21 C22 50.4(6) . . . . ?
C12 C17 C21 C22 -129.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         1.877
_refine_diff_density_min         -2.281
_refine_diff_density_rms         0.111