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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  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_hthozs
#TrackingRef 'Hthozs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H24 Ir N3 O S'
_chemical_formula_weight         678.79

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'
S S 0.1246 0.1234 '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/n

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

_cell_length_a                   12.1220(10)
_cell_length_b                   9.7920(8)
_cell_length_c                   21.8210(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.5210(10)
_cell_angle_gamma                90.00
_cell_volume                     2578.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    164
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      23.55

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    5.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4494
_exptl_absorpt_correction_T_max  0.5246
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14885
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         27.16
_reflns_number_total             5681
_reflns_number_gt                4251
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0223P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5681
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0566
_refine_ls_wR_factor_gt          0.0512
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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 0.754454(12) 0.215049(17) 0.068940(7) 0.04242(6) Uani 1 1 d . . .
S1 S 0.48990(10) 0.37836(14) -0.08479(6) 0.0744(4) Uani 1 1 d . . .
C11 C 0.6571(3) 0.1377(5) 0.12921(17) 0.0481(10) Uani 1 1 d . . .
C22 C 0.8885(3) 0.1415(5) 0.12041(19) 0.0531(11) Uani 1 1 d . . .
O1 O 0.8572(2) 0.3170(3) 0.00952(12) 0.0525(7) Uani 1 1 d . . .
N2 N 0.7796(3) 0.0405(3) 0.02052(15) 0.0494(9) Uani 1 1 d . . .
N3 N 0.6171(2) 0.2826(3) 0.00740(14) 0.0431(7) Uani 1 1 d . . .
C26 C 0.7183(3) 0.3935(4) -0.07078(17) 0.0494(11) Uani 1 1 d . . .
C18 C 1.0210(4) -0.0473(6) 0.1297(3) 0.0836(17) Uani 1 1 d . . .
H18 H 1.0459 -0.1301 0.1153 0.100 Uiso 1 1 calc R . .
C8 C 0.5019(4) 0.0697(7) 0.2122(2) 0.0918(19) Uani 1 1 d . . .
H8 H 0.4490 0.0470 0.2386 0.110 Uiso 1 1 calc R . .
C30 C 0.9144(3) 0.4343(4) -0.07360(19) 0.0537(11) Uani 1 1 d . . .
H30 H 0.9866 0.4279 -0.0551 0.064 Uiso 1 1 calc R . .
C14 C 0.8372(5) -0.1860(5) -0.0444(3) 0.0863(18) Uani 1 1 d . . .
H14 H 0.8571 -0.2622 -0.0662 0.104 Uiso 1 1 calc R . .
N1 N 0.7387(3) 0.3828(3) 0.12231(13) 0.0460(8) Uani 1 1 d . . .
C28 C 0.7898(5) 0.5123(6) -0.1569(2) 0.0949(19) Uani 1 1 d . . .
H28 H 0.7770 0.5554 -0.1949 0.114 Uiso 1 1 calc R . .
C19 C 1.0754(4) 0.0111(7) 0.1812(3) 0.098(2) Uani 1 1 d . . .
H19 H 1.1369 -0.0314 0.2017 0.118 Uiso 1 1 calc R . .
C5 C 0.6745(3) 0.3671(5) 0.16996(18) 0.0530(11) Uani 1 1 d . . .
C6 C 0.6232(3) 0.2328(5) 0.17227(18) 0.0539(11) Uani 1 1 d . . .
C29 C 0.8972(4) 0.4981(5) -0.1292(2) 0.0701(14) Uani 1 1 d . . .
H29 H 0.9568 0.5318 -0.1484 0.084 Uiso 1 1 calc R . .
C17 C 0.9280(3) 0.0168(5) 0.0983(2) 0.0593(12) Uani 1 1 d . . .
C15 C 0.8986(4) -0.1490(5) 0.0086(3) 0.0766(15) Uani 1 1 d . . .
H15 H 0.9606 -0.2001 0.0227 0.092 Uiso 1 1 calc R . .
C16 C 0.8696(4) -0.0355(5) 0.0421(2) 0.0593(12) Uani 1 1 d . . .
C21 C 0.9452(4) 0.1984(5) 0.1731(2) 0.0655(13) Uani 1 1 d . . .
H21 H 0.9208 0.2802 0.1887 0.079 Uiso 1 1 calc R . .
C31 C 0.8277(3) 0.3772(4) -0.04263(17) 0.0439(9) Uani 1 1 d . . .
C20 C 1.0376(4) 0.1335(7) 0.2022(2) 0.0823(17) Uani 1 1 d . . .
H20 H 1.0750 0.1737 0.2368 0.099 Uiso 1 1 calc R . .
C3 C 0.7192(4) 0.5940(6) 0.2029(2) 0.0783(16) Uani 1 1 d . . .
H3 H 0.7132 0.6652 0.2306 0.094 Uiso 1 1 calc R . .
C13 C 0.7461(4) -0.1105(5) -0.0654(2) 0.0745(15) Uani 1 1 d . . .
H13 H 0.7026 -0.1350 -0.1011 0.089 Uiso 1 1 calc R . .
C12 C 0.7205(4) 0.0036(4) -0.0317(2) 0.0574(11) Uani 1 1 d . . .
H12 H 0.6598 0.0565 -0.0461 0.069 Uiso 1 1 calc R . .
C10 C 0.6153(4) 0.0065(5) 0.13244(19) 0.0652(13) Uani 1 1 d . . .
H10 H 0.6396 -0.0609 0.1069 0.078 Uiso 1 1 calc R . .
C27 C 0.7034(4) 0.4629(6) -0.1280(2) 0.0853(17) Uani 1 1 d . . .
H27 H 0.6318 0.4751 -0.1466 0.102 Uiso 1 1 calc R . .
C4 C 0.6659(4) 0.4745(6) 0.2111(2) 0.0685(14) Uani 1 1 d . . .
H4 H 0.6237 0.4642 0.2442 0.082 Uiso 1 1 calc R . .
C9 C 0.5381(5) -0.0267(6) 0.1729(2) 0.0861(17) Uani 1 1 d . . .
H9 H 0.5105 -0.1152 0.1735 0.103 Uiso 1 1 calc R . .
C2 C 0.7821(4) 0.6114(5) 0.1540(2) 0.0736(14) Uani 1 1 d . . .
H2 H 0.8175 0.6938 0.1477 0.088 Uiso 1 1 calc R . .
C1 C 0.7905(3) 0.5027(5) 0.1150(2) 0.0582(12) Uani 1 1 d . . .
H1 H 0.8337 0.5121 0.0823 0.070 Uiso 1 1 calc R . .
C7 C 0.5443(4) 0.1989(6) 0.21221(19) 0.0720(15) Uani 1 1 d . . .
H7 H 0.5206 0.2643 0.2389 0.086 Uiso 1 1 calc R . .
C25 C 0.6205(3) 0.3467(4) -0.04390(18) 0.0448(9) Uani 1 1 d . . .
C23 C 0.5046(3) 0.2428(5) 0.0209(2) 0.0633(13) Uani 1 1 d . . .
H23A H 0.4940 0.2666 0.0630 0.076 Uiso 1 1 calc R . .
H23B H 0.4958 0.1448 0.0163 0.076 Uiso 1 1 calc R . .
C24 C 0.4187(3) 0.3147(4) -0.02244(19) 0.0596(12) Uani 1 1 d . . .
H24A H 0.3853 0.3893 -0.0015 0.072 Uiso 1 1 calc R . .
H24B H 0.3607 0.2515 -0.0376 0.072 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 0.03711(9) 0.04511(11) 0.04616(10) 0.00629(8) 0.00978(6) 0.00565(8)
S1 0.0502(7) 0.0930(11) 0.0765(8) 0.0243(8) -0.0115(6) 0.0003(7)
C11 0.042(2) 0.053(3) 0.049(2) 0.010(2) 0.0032(19) 0.000(2)
C22 0.041(2) 0.062(3) 0.058(3) 0.017(2) 0.010(2) 0.002(2)
O1 0.0374(15) 0.060(2) 0.0608(17) 0.0169(15) 0.0095(13) 0.0067(13)
N2 0.045(2) 0.044(2) 0.062(2) 0.0065(18) 0.0197(18) 0.0054(16)
N3 0.0345(17) 0.047(2) 0.0477(18) -0.0013(17) 0.0061(14) 0.0020(16)
C26 0.045(3) 0.054(3) 0.049(2) 0.001(2) 0.004(2) -0.0026(19)
C18 0.054(3) 0.083(4) 0.117(5) 0.043(4) 0.028(3) 0.026(3)
C8 0.081(4) 0.134(6) 0.064(3) 0.021(4) 0.026(3) -0.021(4)
C30 0.051(3) 0.049(3) 0.064(3) 0.004(2) 0.019(2) 0.004(2)
C14 0.101(5) 0.056(4) 0.112(5) -0.013(3) 0.060(4) 0.012(3)
N1 0.0394(18) 0.054(2) 0.0440(19) -0.0012(17) 0.0001(15) 0.0049(16)
C28 0.093(4) 0.138(6) 0.054(3) 0.033(3) 0.006(3) -0.015(4)
C19 0.054(3) 0.121(6) 0.117(5) 0.065(5) -0.006(3) 0.009(4)
C5 0.044(2) 0.070(3) 0.043(2) -0.002(2) -0.0021(19) 0.016(2)
C6 0.046(2) 0.075(3) 0.041(2) 0.006(2) 0.0051(19) 0.007(2)
C29 0.075(4) 0.082(4) 0.057(3) 0.010(3) 0.027(3) -0.013(3)
C17 0.040(2) 0.065(3) 0.076(3) 0.025(3) 0.021(2) 0.015(2)
C15 0.074(4) 0.051(3) 0.110(4) 0.010(3) 0.035(3) 0.024(3)
C16 0.049(3) 0.051(3) 0.082(3) 0.019(3) 0.029(3) 0.014(2)
C21 0.051(3) 0.074(4) 0.071(3) 0.031(3) 0.003(2) -0.003(2)
C31 0.046(2) 0.041(2) 0.047(2) -0.0023(19) 0.0132(19) 0.0049(19)
C20 0.060(3) 0.102(5) 0.082(4) 0.046(4) -0.011(3) -0.006(3)
C3 0.076(4) 0.086(4) 0.070(3) -0.030(3) -0.013(3) 0.012(3)
C13 0.085(4) 0.060(4) 0.085(4) -0.015(3) 0.038(3) -0.006(3)
C12 0.061(3) 0.050(3) 0.065(3) -0.001(2) 0.024(2) 0.001(2)
C10 0.071(3) 0.066(3) 0.061(3) 0.010(2) 0.017(2) -0.006(3)
C27 0.066(3) 0.138(5) 0.051(3) 0.027(3) -0.001(2) -0.016(3)
C4 0.066(3) 0.088(4) 0.050(3) -0.013(3) -0.001(2) 0.012(3)
C9 0.095(4) 0.094(5) 0.071(3) 0.025(3) 0.020(3) -0.027(3)
C2 0.065(3) 0.066(4) 0.085(4) -0.018(3) -0.016(3) -0.010(3)
C1 0.049(3) 0.061(3) 0.063(3) 0.001(3) -0.007(2) -0.003(2)
C7 0.065(3) 0.109(5) 0.045(3) 0.006(3) 0.017(2) 0.002(3)
C25 0.041(2) 0.046(2) 0.047(2) -0.004(2) 0.0014(18) 0.0057(19)
C23 0.036(2) 0.077(4) 0.077(3) 0.018(3) 0.005(2) 0.000(2)
C24 0.045(2) 0.063(3) 0.070(3) 0.000(2) 0.000(2) 0.002(2)

_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 C11 1.999(4) . ?
Ir1 C22 2.017(4) . ?
Ir1 N1 2.033(3) . ?
Ir1 N2 2.048(3) . ?
Ir1 O1 2.131(3) . ?
Ir1 N3 2.140(3) . ?
S1 C25 1.769(4) . ?
S1 C24 1.792(4) . ?
C11 C10 1.386(6) . ?
C11 C6 1.412(5) . ?
C22 C21 1.397(6) . ?
C22 C17 1.414(6) . ?
O1 C31 1.300(4) . ?
N2 C12 1.336(5) . ?
N2 C16 1.365(5) . ?
N3 C25 1.288(5) . ?
N3 C23 1.475(5) . ?
C26 C31 1.416(5) . ?
C26 C27 1.418(5) . ?
C26 C25 1.446(5) . ?
C18 C19 1.372(7) . ?
C18 C17 1.410(6) . ?
C18 H18 0.9300 . ?
C8 C7 1.365(7) . ?
C8 C9 1.375(7) . ?
C8 H8 0.9300 . ?
C30 C29 1.363(5) . ?
C30 C31 1.418(5) . ?
C30 H30 0.9300 . ?
C14 C15 1.362(7) . ?
C14 C13 1.370(7) . ?
C14 H14 0.9300 . ?
N1 C1 1.349(5) . ?
N1 C5 1.366(5) . ?
C28 C27 1.362(6) . ?
C28 C29 1.388(6) . ?
C28 H28 0.9300 . ?
C19 C20 1.376(8) . ?
C19 H19 0.9300 . ?
C5 C4 1.393(6) . ?
C5 C6 1.458(6) . ?
C6 C7 1.394(6) . ?
C29 H29 0.9300 . ?
C17 C16 1.449(6) . ?
C15 C16 1.393(6) . ?
C15 H15 0.9300 . ?
C21 C20 1.388(6) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?
C3 C4 1.357(7) . ?
C3 C2 1.380(6) . ?
C3 H3 0.9300 . ?
C13 C12 1.388(6) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C10 C9 1.385(6) . ?
C10 H10 0.9300 . ?
C27 H27 0.9300 . ?
C4 H4 0.9300 . ?
C9 H9 0.9300 . ?
C2 C1 1.373(6) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C7 H7 0.9300 . ?
C23 C24 1.511(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 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
C11 Ir1 C22 89.63(15) . . ?
C11 Ir1 N1 80.51(16) . . ?
C22 Ir1 N1 94.85(16) . . ?
C11 Ir1 N2 98.63(15) . . ?
C22 Ir1 N2 80.64(17) . . ?
N1 Ir1 N2 175.43(12) . . ?
C11 Ir1 O1 174.09(15) . . ?
C22 Ir1 O1 91.11(13) . . ?
N1 Ir1 O1 93.59(12) . . ?
N2 Ir1 O1 87.27(11) . . ?
C11 Ir1 N3 93.27(13) . . ?
C22 Ir1 N3 174.73(15) . . ?
N1 Ir1 N3 89.97(11) . . ?
N2 Ir1 N3 94.57(13) . . ?
O1 Ir1 N3 86.45(11) . . ?
C25 S1 C24 91.70(19) . . ?
C10 C11 C6 116.5(4) . . ?
C10 C11 Ir1 128.8(3) . . ?
C6 C11 Ir1 114.6(3) . . ?
C21 C22 C17 118.0(4) . . ?
C21 C22 Ir1 128.4(4) . . ?
C17 C22 Ir1 113.5(3) . . ?
C31 O1 Ir1 128.1(2) . . ?
C12 N2 C16 119.4(4) . . ?
C12 N2 Ir1 124.9(3) . . ?
C16 N2 Ir1 115.5(3) . . ?
C25 N3 C23 114.1(3) . . ?
C25 N3 Ir1 127.4(3) . . ?
C23 N3 Ir1 118.2(2) . . ?
C31 C26 C27 118.1(4) . . ?
C31 C26 C25 123.9(4) . . ?
C27 C26 C25 118.0(4) . . ?
C19 C18 C17 120.7(5) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C7 C8 C9 119.5(5) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C29 C30 C31 123.2(4) . . ?
C29 C30 H30 118.4 . . ?
C31 C30 H30 118.4 . . ?
C15 C14 C13 119.8(5) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C1 N1 C5 119.6(4) . . ?
C1 N1 Ir1 124.4(3) . . ?
C5 N1 Ir1 115.9(3) . . ?
C27 C28 C29 119.6(5) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C18 C19 C20 119.1(5) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
N1 C5 C4 119.3(4) . . ?
N1 C5 C6 113.8(4) . . ?
C4 C5 C6 126.8(4) . . ?
C7 C6 C11 121.3(5) . . ?
C7 C6 C5 123.9(4) . . ?
C11 C6 C5 114.8(4) . . ?
C30 C29 C28 119.4(4) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C18 C17 C22 120.0(5) . . ?
C18 C17 C16 123.9(5) . . ?
C22 C17 C16 116.1(4) . . ?
C14 C15 C16 120.8(5) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
N2 C16 C15 119.2(5) . . ?
N2 C16 C17 114.1(4) . . ?
C15 C16 C17 126.7(4) . . ?
C20 C21 C22 120.3(5) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
O1 C31 C26 126.7(3) . . ?
O1 C31 C30 116.2(4) . . ?
C26 C31 C30 117.0(4) . . ?
C19 C20 C21 121.8(6) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C4 C3 C2 120.9(5) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C14 C13 C12 118.1(5) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
N2 C12 C13 122.7(4) . . ?
N2 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C9 C10 C11 121.5(5) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C28 C27 C26 122.6(5) . . ?
C28 C27 H27 118.7 . . ?
C26 C27 H27 118.7 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C8 C9 C10 120.8(5) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C1 C2 C3 117.6(5) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
N1 C1 C2 122.6(4) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C8 C7 C6 120.1(5) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
N3 C25 C26 127.1(3) . . ?
N3 C25 S1 115.0(3) . . ?
C26 C25 S1 117.9(3) . . ?
N3 C23 C24 110.4(3) . . ?
N3 C23 H23A 109.6 . . ?
C24 C23 H23A 109.6 . . ?
N3 C23 H23B 109.6 . . ?
C24 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
C23 C24 S1 106.4(3) . . ?
C23 C24 H24A 110.4 . . ?
S1 C24 H24A 110.4 . . ?
C23 C24 H24B 110.4 . . ?
S1 C24 H24B 110.4 . . ?
H24A C24 H24B 108.6 . . ?

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
C22 Ir1 C11 C10 -84.4(4) . . . . ?
N1 Ir1 C11 C10 -179.4(4) . . . . ?
N2 Ir1 C11 C10 -3.9(4) . . . . ?
O1 Ir1 C11 C10 178.4(10) . . . . ?
N3 Ir1 C11 C10 91.2(4) . . . . ?
C22 Ir1 C11 C6 98.7(3) . . . . ?
N1 Ir1 C11 C6 3.8(3) . . . . ?
N2 Ir1 C11 C6 179.2(3) . . . . ?
O1 Ir1 C11 C6 1.5(14) . . . . ?
N3 Ir1 C11 C6 -85.7(3) . . . . ?
C11 Ir1 C22 C21 -81.8(4) . . . . ?
N1 Ir1 C22 C21 -1.4(4) . . . . ?
N2 Ir1 C22 C21 179.4(4) . . . . ?
O1 Ir1 C22 C21 92.3(4) . . . . ?
N3 Ir1 C22 C21 154.8(14) . . . . ?
C11 Ir1 C22 C17 98.8(3) . . . . ?
N1 Ir1 C22 C17 179.3(3) . . . . ?
N2 Ir1 C22 C17 0.0(3) . . . . ?
O1 Ir1 C22 C17 -87.0(3) . . . . ?
N3 Ir1 C22 C17 -24.6(17) . . . . ?
C11 Ir1 O1 C31 -92.4(12) . . . . ?
C22 Ir1 O1 C31 170.4(3) . . . . ?
N1 Ir1 O1 C31 -94.7(3) . . . . ?
N2 Ir1 O1 C31 89.8(3) . . . . ?
N3 Ir1 O1 C31 -4.9(3) . . . . ?
C11 Ir1 N2 C12 95.0(3) . . . . ?
C22 Ir1 N2 C12 -176.8(3) . . . . ?
N1 Ir1 N2 C12 173.8(14) . . . . ?
O1 Ir1 N2 C12 -85.2(3) . . . . ?
N3 Ir1 N2 C12 1.0(3) . . . . ?
C11 Ir1 N2 C16 -90.3(3) . . . . ?
C22 Ir1 N2 C16 -2.1(3) . . . . ?
N1 Ir1 N2 C16 -11.6(17) . . . . ?
O1 Ir1 N2 C16 89.4(3) . . . . ?
N3 Ir1 N2 C16 175.7(3) . . . . ?
C11 Ir1 N3 C25 179.0(4) . . . . ?
C22 Ir1 N3 C25 -57.8(16) . . . . ?
N1 Ir1 N3 C25 98.5(3) . . . . ?
N2 Ir1 N3 C25 -82.1(3) . . . . ?
O1 Ir1 N3 C25 4.9(3) . . . . ?
C11 Ir1 N3 C23 -6.9(3) . . . . ?
C22 Ir1 N3 C23 116.4(15) . . . . ?
N1 Ir1 N3 C23 -87.4(3) . . . . ?
N2 Ir1 N3 C23 92.1(3) . . . . ?
O1 Ir1 N3 C23 179.0(3) . . . . ?
C11 Ir1 N1 C1 176.7(3) . . . . ?
C22 Ir1 N1 C1 87.8(3) . . . . ?
N2 Ir1 N1 C1 97.2(15) . . . . ?
O1 Ir1 N1 C1 -3.6(3) . . . . ?
N3 Ir1 N1 C1 -90.0(3) . . . . ?
C11 Ir1 N1 C5 -0.3(3) . . . . ?
C22 Ir1 N1 C5 -89.1(3) . . . . ?
N2 Ir1 N1 C5 -79.8(16) . . . . ?
O1 Ir1 N1 C5 179.4(3) . . . . ?
N3 Ir1 N1 C5 93.0(3) . . . . ?
C17 C18 C19 C20 0.2(8) . . . . ?
C1 N1 C5 C4 -1.5(5) . . . . ?
Ir1 N1 C5 C4 175.6(3) . . . . ?
C1 N1 C5 C6 179.8(3) . . . . ?
Ir1 N1 C5 C6 -3.1(4) . . . . ?
C10 C11 C6 C7 -5.4(6) . . . . ?
Ir1 C11 C6 C7 171.9(3) . . . . ?
C10 C11 C6 C5 176.2(4) . . . . ?
Ir1 C11 C6 C5 -6.5(4) . . . . ?
N1 C5 C6 C7 -172.2(4) . . . . ?
C4 C5 C6 C7 9.3(7) . . . . ?
N1 C5 C6 C11 6.2(5) . . . . ?
C4 C5 C6 C11 -172.3(4) . . . . ?
C31 C30 C29 C28 1.9(7) . . . . ?
C27 C28 C29 C30 0.2(8) . . . . ?
C19 C18 C17 C22 -1.0(7) . . . . ?
C19 C18 C17 C16 177.1(4) . . . . ?
C21 C22 C17 C18 0.8(6) . . . . ?
Ir1 C22 C17 C18 -179.8(3) . . . . ?
C21 C22 C17 C16 -177.5(4) . . . . ?
Ir1 C22 C17 C16 2.0(5) . . . . ?
C13 C14 C15 C16 0.3(8) . . . . ?
C12 N2 C16 C15 0.8(6) . . . . ?
Ir1 N2 C16 C15 -174.2(3) . . . . ?
C12 N2 C16 C17 178.7(3) . . . . ?
Ir1 N2 C16 C17 3.8(4) . . . . ?
C14 C15 C16 N2 -1.2(7) . . . . ?
C14 C15 C16 C17 -178.9(4) . . . . ?
C18 C17 C16 N2 178.1(4) . . . . ?
C22 C17 C16 N2 -3.8(5) . . . . ?
C18 C17 C16 C15 -4.2(7) . . . . ?
C22 C17 C16 C15 174.0(4) . . . . ?
C17 C22 C21 C20 0.3(6) . . . . ?
Ir1 C22 C21 C20 -179.1(3) . . . . ?
Ir1 O1 C31 C26 2.9(6) . . . . ?
Ir1 O1 C31 C30 -178.4(3) . . . . ?
C27 C26 C31 O1 179.9(4) . . . . ?
C25 C26 C31 O1 1.4(6) . . . . ?
C27 C26 C31 C30 1.2(6) . . . . ?
C25 C26 C31 C30 -177.2(4) . . . . ?
C29 C30 C31 O1 178.6(4) . . . . ?
C29 C30 C31 C26 -2.6(6) . . . . ?
C18 C19 C20 C21 0.9(8) . . . . ?
C22 C21 C20 C19 -1.1(7) . . . . ?
C15 C14 C13 C12 0.9(7) . . . . ?
C16 N2 C12 C13 0.5(6) . . . . ?
Ir1 N2 C12 C13 175.0(3) . . . . ?
C14 C13 C12 N2 -1.4(7) . . . . ?
C6 C11 C10 C9 4.5(6) . . . . ?
Ir1 C11 C10 C9 -172.4(3) . . . . ?
C29 C28 C27 C26 -1.5(9) . . . . ?
C31 C26 C27 C28 0.7(8) . . . . ?
C25 C26 C27 C28 179.3(5) . . . . ?
C2 C3 C4 C5 0.1(7) . . . . ?
N1 C5 C4 C3 1.3(6) . . . . ?
C6 C5 C4 C3 179.8(4) . . . . ?
C7 C8 C9 C10 -1.4(8) . . . . ?
C11 C10 C9 C8 -1.2(8) . . . . ?
C4 C3 C2 C1 -1.3(7) . . . . ?
C5 N1 C1 C2 0.3(6) . . . . ?
Ir1 N1 C1 C2 -176.6(3) . . . . ?
C3 C2 C1 N1 1.2(7) . . . . ?
C9 C8 C7 C6 0.5(8) . . . . ?
C11 C6 C7 C8 3.0(7) . . . . ?
C5 C6 C7 C8 -178.7(4) . . . . ?
C23 N3 C25 C26 -177.3(4) . . . . ?
Ir1 N3 C25 C26 -2.9(6) . . . . ?
C23 N3 C25 S1 2.4(5) . . . . ?
Ir1 N3 C25 S1 176.77(17) . . . . ?
C31 C26 C25 N3 -1.4(7) . . . . ?
C27 C26 C25 N3 -179.9(4) . . . . ?
C31 C26 C25 S1 178.9(3) . . . . ?
C27 C26 C25 S1 0.5(6) . . . . ?
C24 S1 C25 N3 6.6(3) . . . . ?
C24 S1 C25 C26 -173.7(3) . . . . ?
C25 N3 C23 C24 -12.5(5) . . . . ?
Ir1 N3 C23 C24 172.6(3) . . . . ?
N3 C23 C24 S1 16.1(5) . . . . ?
C25 S1 C24 C23 -12.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.090

# Attachment 'thozo.cif'

#===================================================================
# 1
_contact_author_name             'Dong-Xia zhu'
_contact_author_address          
;
Institute of Functional Material Chemistry,
Department of Chemistry,
Northeast Normal University,
Changchun 130024, P. R. China
;
_contact_author_email            zhudx047@nenu.edu.cn
_contact_author_phone            +86-431-85099544
_requested_journal               'Journal of Material Chemistry'
_database_code_depnum_ccdc_archive 'CCDC 835019'
#######################################################################
#
#                 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_htozo
#TrackingRef 'thozo.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H24 Ir N3 O2'
_chemical_formula_weight         662.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   p21/n

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

_cell_length_a                   11.734(2)
_cell_length_b                   9.6222(19)
_cell_length_c                   22.223(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.82(3)
_cell_angle_gamma                90.00
_cell_volume                     2491.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    164
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      23.55

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    5.394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3971
_exptl_absorpt_correction_T_max  0.4790
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22661
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.47
_reflns_number_total             5608
_reflns_number_gt                4155
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0000P)^2^+2.0993P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5608
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0567
_refine_ls_wR_factor_gt          0.0489
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
C23 C -0.0092(5) 0.7403(6) 0.0262(3) 0.0686(15) Uani 1 1 d . . .
H23A H -0.0241 0.8391 0.0291 0.082 Uiso 1 1 calc R . .
H23B H -0.0243 0.6955 0.0636 0.082 Uiso 1 1 calc R . .
C24 C -0.0811(4) 0.6768(5) -0.0279(2) 0.0605(13) Uani 1 1 d . . .
H24A H -0.1285 0.6022 -0.0153 0.073 Uiso 1 1 calc R . .
H24B H -0.1304 0.7463 -0.0492 0.073 Uiso 1 1 calc R . .
C25 C 0.1066(4) 0.6523(4) -0.0372(2) 0.0470(11) Uani 1 1 d . . .
C26 C 0.2035(4) 0.6046(4) -0.0666(2) 0.0503(12) Uani 1 1 d . . .
C31 C 0.3181(4) 0.6166(4) -0.0396(2) 0.0426(11) Uani 1 1 d . . .
C30 C 0.4042(4) 0.5610(4) -0.0729(2) 0.0503(12) Uani 1 1 d . . .
H30 H 0.4804 0.5648 -0.0559 0.060 Uiso 1 1 calc R . .
C29 C 0.3794(6) 0.5025(6) -0.1287(3) 0.0720(16) Uani 1 1 d . . .
H29 H 0.4380 0.4694 -0.1495 0.086 Uiso 1 1 calc R . .
C28 C 0.2663(7) 0.4926(7) -0.1540(3) 0.096(2) Uani 1 1 d . . .
H28 H 0.2488 0.4514 -0.1918 0.115 Uiso 1 1 calc R . .
C27 C 0.1796(6) 0.5431(6) -0.1239(2) 0.0811(18) Uani 1 1 d . . .
H27 H 0.1039 0.5363 -0.1416 0.097 Uiso 1 1 calc R . .
C1 C 0.2908(4) 0.4903(5) 0.1203(2) 0.0524(12) Uani 1 1 d . . .
H1 H 0.3382 0.4811 0.0898 0.063 Uiso 1 1 calc R . .
C2 C 0.2789(5) 0.3787(5) 0.1584(3) 0.0672(15) Uani 1 1 d . . .
H2 H 0.3185 0.2963 0.1542 0.081 Uiso 1 1 calc R . .
C3 C 0.2066(5) 0.3928(6) 0.2031(3) 0.0742(17) Uani 1 1 d . . .
H3 H 0.1952 0.3187 0.2286 0.089 Uiso 1 1 calc R . .
C4 C 0.1525(5) 0.5167(6) 0.2091(2) 0.0670(15) Uani 1 1 d . . .
H4 H 0.1060 0.5272 0.2399 0.080 Uiso 1 1 calc R . .
C5 C 0.1654(4) 0.6268(5) 0.1706(2) 0.0508(12) Uani 1 1 d . . .
C6 C 0.1158(4) 0.7656(5) 0.1716(2) 0.0503(11) Uani 1 1 d . . .
C7 C 0.0341(5) 0.8033(6) 0.2096(2) 0.0711(16) Uani 1 1 d . . .
H7 H 0.0073 0.7380 0.2354 0.085 Uiso 1 1 calc R . .
C8 C -0.0064(5) 0.9376(7) 0.2085(3) 0.0819(18) Uani 1 1 d . . .
H8 H -0.0611 0.9629 0.2335 0.098 Uiso 1 1 calc R . .
C9 C 0.0332(5) 1.0343(6) 0.1710(3) 0.0795(18) Uani 1 1 d . . .
H9 H 0.0059 1.1250 0.1708 0.095 Uiso 1 1 calc R . .
C10 C 0.1137(5) 0.9973(5) 0.1332(2) 0.0624(14) Uani 1 1 d . . .
H10 H 0.1408 1.0650 0.1086 0.075 Uiso 1 1 calc R . .
C11 C 0.1558(4) 0.8617(5) 0.1307(2) 0.0465(11) Uani 1 1 d . . .
C12 C 0.2214(5) 0.9934(5) -0.0279(2) 0.0558(13) Uani 1 1 d . . .
H12 H 0.1581 0.9402 -0.0429 0.067 Uiso 1 1 calc R . .
C13 C 0.2495(5) 1.1072(5) -0.0605(3) 0.0690(16) Uani 1 1 d . . .
H13 H 0.2055 1.1306 -0.0967 0.083 Uiso 1 1 calc R . .
C14 C 0.3426(6) 1.1854(6) -0.0393(3) 0.081(2) Uani 1 1 d . . .
H14 H 0.3630 1.2624 -0.0609 0.098 Uiso 1 1 calc R . .
C15 C 0.4054(5) 1.1492(5) 0.0140(3) 0.0767(18) Uani 1 1 d . . .
H15 H 0.4693 1.2015 0.0288 0.092 Uiso 1 1 calc R . .
C16 C 0.3740(5) 1.0339(5) 0.0464(2) 0.0563(13) Uani 1 1 d . . .
C17 C 0.4365(4) 0.9808(5) 0.1024(2) 0.0556(13) Uani 1 1 d . . .
C18 C 0.5334(5) 1.0450(6) 0.1329(3) 0.0743(17) Uani 1 1 d . . .
H18 H 0.5586 1.1292 0.1188 0.089 Uiso 1 1 calc R . .
C19 C 0.5912(5) 0.9858(7) 0.1828(3) 0.086(2) Uani 1 1 d . . .
H19 H 0.6555 1.0295 0.2027 0.103 Uiso 1 1 calc R . .
C20 C 0.5547(5) 0.8607(7) 0.2041(3) 0.0793(18) Uani 1 1 d . . .
H20 H 0.5958 0.8193 0.2378 0.095 Uiso 1 1 calc R . .
C21 C 0.4565(5) 0.7960(5) 0.1754(2) 0.0622(13) Uani 1 1 d . . .
H21 H 0.4314 0.7132 0.1911 0.075 Uiso 1 1 calc R . .
C22 C 0.3948(4) 0.8538(5) 0.1234(2) 0.0509(12) Uani 1 1 d . . .
Ir1 Ir 0.254571(15) 0.780244(16) 0.073012(8) 0.03989(6) Uani 1 1 d . . .
N3 N 0.1093(3) 0.7145(4) 0.01365(16) 0.0440(8) Uani 1 1 d . . .
N1 N 0.2362(3) 0.6110(3) 0.12591(16) 0.0452(9) Uani 1 1 d . . .
N2 N 0.2816(3) 0.9561(3) 0.02491(18) 0.0475(10) Uani 1 1 d . . .
O1 O 0.3530(3) 0.6698(3) 0.01303(14) 0.0499(8) Uani 1 1 d . . .
O2 O 0.0007(3) 0.6243(4) -0.06589(16) 0.0690(10) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C23 0.042(3) 0.089(4) 0.074(4) -0.013(3) 0.004(3) -0.001(2)
C24 0.045(3) 0.062(3) 0.073(4) 0.009(3) -0.001(3) -0.002(2)
C25 0.044(3) 0.045(2) 0.050(3) 0.005(2) -0.004(2) -0.001(2)
C26 0.058(3) 0.053(3) 0.040(3) 0.002(2) 0.005(2) 0.000(2)
C31 0.051(3) 0.037(2) 0.041(3) 0.0068(18) 0.012(2) -0.0031(18)
C30 0.046(3) 0.053(3) 0.054(3) -0.001(2) 0.016(2) 0.000(2)
C29 0.083(5) 0.084(4) 0.052(4) -0.008(3) 0.025(3) 0.012(3)
C28 0.111(7) 0.126(6) 0.050(4) -0.028(3) 0.006(4) 0.013(4)
C27 0.080(5) 0.114(5) 0.046(3) -0.017(3) -0.004(3) 0.009(4)
C1 0.048(3) 0.054(3) 0.054(3) 0.001(2) 0.002(2) 0.001(2)
C2 0.066(4) 0.060(3) 0.071(4) 0.011(3) -0.011(3) 0.006(3)
C3 0.079(5) 0.073(4) 0.067(4) 0.026(3) -0.003(3) -0.012(3)
C4 0.073(4) 0.080(4) 0.049(3) 0.017(3) 0.012(3) -0.010(3)
C5 0.048(3) 0.065(3) 0.038(3) 0.003(2) 0.003(2) -0.009(2)
C6 0.049(3) 0.066(3) 0.037(2) -0.008(2) 0.007(2) -0.003(2)
C7 0.065(4) 0.103(4) 0.049(3) -0.009(3) 0.022(3) -0.004(3)
C8 0.070(5) 0.114(5) 0.066(4) -0.024(3) 0.024(3) 0.015(4)
C9 0.077(5) 0.080(4) 0.084(5) -0.018(3) 0.020(4) 0.018(3)
C10 0.058(4) 0.068(3) 0.064(4) -0.008(3) 0.017(3) 0.005(2)
C11 0.040(3) 0.057(3) 0.044(3) -0.009(2) 0.008(2) -0.001(2)
C12 0.057(4) 0.056(3) 0.058(3) 0.003(2) 0.020(3) 0.003(2)
C13 0.082(5) 0.058(3) 0.073(4) 0.019(3) 0.036(3) 0.012(3)
C14 0.096(6) 0.057(4) 0.101(5) 0.014(3) 0.052(4) -0.009(3)
C15 0.075(5) 0.060(3) 0.102(5) -0.009(3) 0.040(4) -0.025(3)
C16 0.057(4) 0.050(3) 0.068(4) -0.015(2) 0.030(3) -0.009(2)
C17 0.038(3) 0.062(3) 0.069(4) -0.024(3) 0.017(3) -0.012(2)
C18 0.053(4) 0.082(4) 0.089(5) -0.032(3) 0.013(3) -0.023(3)
C19 0.056(4) 0.110(5) 0.091(5) -0.048(4) 0.005(4) -0.019(4)
C20 0.059(4) 0.109(5) 0.067(4) -0.036(4) -0.008(3) 0.005(3)
C21 0.057(4) 0.072(3) 0.057(3) -0.025(3) 0.006(3) 0.001(3)
C22 0.035(3) 0.063(3) 0.056(3) -0.023(2) 0.011(2) -0.004(2)
Ir1 0.03771(10) 0.04198(9) 0.04114(9) -0.00379(8) 0.00952(7) -0.00380(8)
N3 0.033(2) 0.051(2) 0.048(2) -0.0021(18) 0.0050(16) -0.0036(17)
N1 0.042(2) 0.048(2) 0.044(2) -0.0014(16) 0.0017(18) -0.0041(16)
N2 0.049(3) 0.037(2) 0.060(3) -0.0052(17) 0.020(2) -0.0029(16)
O1 0.038(2) 0.0626(19) 0.0499(19) -0.0113(15) 0.0098(15) -0.0014(14)
O2 0.046(2) 0.091(3) 0.066(2) -0.0179(19) -0.0083(19) -0.0019(18)

_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
C23 N3 1.472(6) . ?
C23 C24 1.514(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 O2 1.443(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 N3 1.276(5) . ?
C25 O2 1.355(5) . ?
C25 C26 1.452(6) . ?
C26 C27 1.401(7) . ?
C26 C31 1.410(6) . ?
C31 O1 1.298(5) . ?
C31 C30 1.426(6) . ?
C30 C29 1.360(7) . ?
C30 H30 0.9300 . ?
C29 C28 1.382(8) . ?
C29 H29 0.9300 . ?
C28 C27 1.372(8) . ?
C28 H28 0.9300 . ?
C27 H27 0.9300 . ?
C1 N1 1.340(5) . ?
C1 C2 1.385(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(6) . ?
C4 H4 0.9300 . ?
C5 N1 1.376(5) . ?
C5 C6 1.458(6) . ?
C6 C7 1.399(6) . ?
C6 C11 1.416(6) . ?
C7 C8 1.377(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.366(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.399(6) . ?
C10 H10 0.9300 . ?
C11 Ir1 1.987(4) . ?
C12 N2 1.344(6) . ?
C12 C13 1.375(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.363(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.396(7) . ?
C15 H15 0.9300 . ?
C16 N2 1.356(6) . ?
C16 C17 1.461(7) . ?
C17 C18 1.396(7) . ?
C17 C22 1.416(6) . ?
C18 C19 1.354(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.396(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.405(7) . ?
C21 H21 0.9300 . ?
C22 Ir1 2.006(5) . ?
Ir1 N1 2.035(3) . ?
Ir1 N2 2.046(3) . ?
Ir1 N3 2.124(4) . ?
Ir1 O1 2.146(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C23 C24 103.3(4) . . ?
N3 C23 H23A 111.1 . . ?
C24 C23 H23A 111.1 . . ?
N3 C23 H23B 111.1 . . ?
C24 C23 H23B 111.1 . . ?
H23A C23 H23B 109.1 . . ?
O2 C24 C23 105.0(4) . . ?
O2 C24 H24A 110.7 . . ?
C23 C24 H24A 110.7 . . ?
O2 C24 H24B 110.7 . . ?
C23 C24 H24B 110.7 . . ?
H24A C24 H24B 108.8 . . ?
N3 C25 O2 115.7(4) . . ?
N3 C25 C26 127.5(4) . . ?
O2 C25 C26 116.7(4) . . ?
C27 C26 C31 120.0(5) . . ?
C27 C26 C25 117.3(5) . . ?
C31 C26 C25 122.7(4) . . ?
O1 C31 C26 126.8(4) . . ?
O1 C31 C30 116.7(4) . . ?
C26 C31 C30 116.5(4) . . ?
C29 C30 C31 122.7(5) . . ?
C29 C30 H30 118.7 . . ?
C31 C30 H30 118.7 . . ?
C30 C29 C28 119.4(5) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C27 C28 C29 120.6(6) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C28 C27 C26 120.8(6) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
N1 C1 C2 122.0(5) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C1 C2 C3 118.5(5) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 119.1(5) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.5(5) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
N1 C5 C4 118.8(5) . . ?
N1 C5 C6 112.8(4) . . ?
C4 C5 C6 128.3(5) . . ?
C7 C6 C11 121.5(5) . . ?
C7 C6 C5 123.3(4) . . ?
C11 C6 C5 115.2(4) . . ?
C8 C7 C6 119.5(5) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C7 120.6(5) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.1(5) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 122.3(5) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C10 C11 C6 115.9(4) . . ?
C10 C11 Ir1 129.0(4) . . ?
C6 C11 Ir1 114.8(3) . . ?
N2 C12 C13 122.5(5) . . ?
N2 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C14 C13 C12 119.4(6) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 119.2(5) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C16 120.1(6) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
N2 C16 C15 120.4(6) . . ?
N2 C16 C17 114.0(4) . . ?
C15 C16 C17 125.5(5) . . ?
C18 C17 C22 121.0(6) . . ?
C18 C17 C16 123.9(5) . . ?
C22 C17 C16 115.1(4) . . ?
C19 C18 C17 120.7(6) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 120.2(6) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 120.3(6) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C22 121.1(5) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C17 116.7(5) . . ?
C21 C22 Ir1 128.9(4) . . ?
C17 C22 Ir1 114.5(4) . . ?
C11 Ir1 C22 90.20(18) . . ?
C11 Ir1 N1 80.41(16) . . ?
C22 Ir1 N1 95.55(18) . . ?
C11 Ir1 N2 98.58(16) . . ?
C22 Ir1 N2 80.31(19) . . ?
N1 Ir1 N2 175.75(15) . . ?
C11 Ir1 N3 91.80(16) . . ?
C22 Ir1 N3 175.00(17) . . ?
N1 Ir1 N3 89.31(14) . . ?
N2 Ir1 N3 94.86(15) . . ?
C11 Ir1 O1 173.48(15) . . ?
C22 Ir1 O1 93.16(15) . . ?
N1 Ir1 O1 93.69(13) . . ?
N2 Ir1 O1 87.51(12) . . ?
N3 Ir1 O1 85.31(12) . . ?
C25 N3 C23 108.9(4) . . ?
C25 N3 Ir1 128.5(3) . . ?
C23 N3 Ir1 122.6(3) . . ?
C1 N1 C5 120.0(4) . . ?
C1 N1 Ir1 123.7(3) . . ?
C5 N1 Ir1 116.3(3) . . ?
C12 N2 C16 118.3(4) . . ?
C12 N2 Ir1 125.3(3) . . ?
C16 N2 Ir1 116.1(4) . . ?
C31 O1 Ir1 128.3(3) . . ?
C25 O2 C24 107.0(4) . . ?

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
N3 C23 C24 O2 -1.0(5) . . . . ?
N3 C25 C26 C27 -177.7(5) . . . . ?
O2 C25 C26 C27 4.5(6) . . . . ?
N3 C25 C26 C31 3.0(7) . . . . ?
O2 C25 C26 C31 -174.8(4) . . . . ?
C27 C26 C31 O1 -179.4(4) . . . . ?
C25 C26 C31 O1 -0.2(7) . . . . ?
C27 C26 C31 C30 -1.3(6) . . . . ?
C25 C26 C31 C30 178.0(4) . . . . ?
O1 C31 C30 C29 -179.9(4) . . . . ?
C26 C31 C30 C29 1.8(6) . . . . ?
C31 C30 C29 C28 -1.7(8) . . . . ?
C30 C29 C28 C27 1.0(10) . . . . ?
C29 C28 C27 C26 -0.5(10) . . . . ?
C31 C26 C27 C28 0.7(8) . . . . ?
C25 C26 C27 C28 -178.6(5) . . . . ?
N1 C1 C2 C3 1.0(8) . . . . ?
C1 C2 C3 C4 -1.9(9) . . . . ?
C2 C3 C4 C5 2.0(9) . . . . ?
C3 C4 C5 N1 -1.2(8) . . . . ?
C3 C4 C5 C6 -178.7(5) . . . . ?
N1 C5 C6 C7 174.6(5) . . . . ?
C4 C5 C6 C7 -7.8(8) . . . . ?
N1 C5 C6 C11 -5.0(6) . . . . ?
C4 C5 C6 C11 172.6(5) . . . . ?
C11 C6 C7 C8 -1.8(8) . . . . ?
C5 C6 C7 C8 178.7(5) . . . . ?
C6 C7 C8 C9 -0.4(9) . . . . ?
C7 C8 C9 C10 0.7(10) . . . . ?
C8 C9 C10 C11 1.4(10) . . . . ?
C9 C10 C11 C6 -3.4(8) . . . . ?
C9 C10 C11 Ir1 171.1(4) . . . . ?
C7 C6 C11 C10 3.6(7) . . . . ?
C5 C6 C11 C10 -176.8(4) . . . . ?
C7 C6 C11 Ir1 -171.7(4) . . . . ?
C5 C6 C11 Ir1 7.9(5) . . . . ?
N2 C12 C13 C14 0.6(8) . . . . ?
C12 C13 C14 C15 -0.3(8) . . . . ?
C13 C14 C15 C16 -0.3(9) . . . . ?
C14 C15 C16 N2 0.6(8) . . . . ?
C14 C15 C16 C17 177.2(5) . . . . ?
N2 C16 C17 C18 -179.3(4) . . . . ?
C15 C16 C17 C18 4.0(8) . . . . ?
N2 C16 C17 C22 3.2(6) . . . . ?
C15 C16 C17 C22 -173.5(4) . . . . ?
C22 C17 C18 C19 1.2(8) . . . . ?
C16 C17 C18 C19 -176.2(5) . . . . ?
C17 C18 C19 C20 0.0(9) . . . . ?
C18 C19 C20 C21 -1.7(9) . . . . ?
C19 C20 C21 C22 2.1(8) . . . . ?
C20 C21 C22 C17 -0.8(7) . . . . ?
C20 C21 C22 Ir1 178.4(4) . . . . ?
C18 C17 C22 C21 -0.8(7) . . . . ?
C16 C17 C22 C21 176.8(4) . . . . ?
C18 C17 C22 Ir1 179.8(4) . . . . ?
C16 C17 C22 Ir1 -2.6(5) . . . . ?
C10 C11 Ir1 C22 83.8(5) . . . . ?
C6 C11 Ir1 C22 -101.6(4) . . . . ?
C10 C11 Ir1 N1 179.4(5) . . . . ?
C6 C11 Ir1 N1 -6.0(3) . . . . ?
C10 C11 Ir1 N2 3.6(5) . . . . ?
C6 C11 Ir1 N2 178.1(4) . . . . ?
C10 C11 Ir1 N3 -91.6(5) . . . . ?
C6 C11 Ir1 N3 83.0(4) . . . . ?
C10 C11 Ir1 O1 -155.2(12) . . . . ?
C6 C11 Ir1 O1 19.4(16) . . . . ?
C21 C22 Ir1 C11 83.1(4) . . . . ?
C17 C22 Ir1 C11 -97.7(3) . . . . ?
C21 C22 Ir1 N1 2.7(4) . . . . ?
C17 C22 Ir1 N1 -178.0(3) . . . . ?
C21 C22 Ir1 N2 -178.3(4) . . . . ?
C17 C22 Ir1 N2 1.0(3) . . . . ?
C21 C22 Ir1 N3 -163.3(15) . . . . ?
C17 C22 Ir1 N3 15.9(19) . . . . ?
C21 C22 Ir1 O1 -91.3(4) . . . . ?
C17 C22 Ir1 O1 87.9(3) . . . . ?
O2 C25 N3 C23 -0.8(5) . . . . ?
C26 C25 N3 C23 -178.7(4) . . . . ?
O2 C25 N3 Ir1 -179.2(3) . . . . ?
C26 C25 N3 Ir1 3.0(7) . . . . ?
C24 C23 N3 C25 1.1(5) . . . . ?
C24 C23 N3 Ir1 179.6(3) . . . . ?
C11 Ir1 N3 C25 178.5(4) . . . . ?
C22 Ir1 N3 C25 65.0(18) . . . . ?
N1 Ir1 N3 C25 -101.1(4) . . . . ?
N2 Ir1 N3 C25 79.7(4) . . . . ?
O1 Ir1 N3 C25 -7.4(4) . . . . ?
C11 Ir1 N3 C23 0.4(4) . . . . ?
C22 Ir1 N3 C23 -113.2(17) . . . . ?
N1 Ir1 N3 C23 80.7(4) . . . . ?
N2 Ir1 N3 C23 -98.4(4) . . . . ?
O1 Ir1 N3 C23 174.5(4) . . . . ?
C2 C1 N1 C5 -0.1(7) . . . . ?
C2 C1 N1 Ir1 177.9(4) . . . . ?
C4 C5 N1 C1 0.2(7) . . . . ?
C6 C5 N1 C1 178.1(4) . . . . ?
C4 C5 N1 Ir1 -178.0(4) . . . . ?
C6 C5 N1 Ir1 -0.1(5) . . . . ?
C11 Ir1 N1 C1 -174.7(4) . . . . ?
C22 Ir1 N1 C1 -85.5(4) . . . . ?
N2 Ir1 N1 C1 -98.1(18) . . . . ?
N3 Ir1 N1 C1 93.3(4) . . . . ?
O1 Ir1 N1 C1 8.1(4) . . . . ?
C11 Ir1 N1 C5 3.4(3) . . . . ?
C22 Ir1 N1 C5 92.6(3) . . . . ?
N2 Ir1 N1 C5 79.9(19) . . . . ?
N3 Ir1 N1 C5 -88.6(3) . . . . ?
O1 Ir1 N1 C5 -173.8(3) . . . . ?
C13 C12 N2 C16 -0.3(7) . . . . ?
C13 C12 N2 Ir1 -174.7(3) . . . . ?
C15 C16 N2 C12 -0.3(6) . . . . ?
C17 C16 N2 C12 -177.3(4) . . . . ?
C15 C16 N2 Ir1 174.6(4) . . . . ?
C17 C16 N2 Ir1 -2.4(5) . . . . ?
C11 Ir1 N2 C12 -96.0(4) . . . . ?
C22 Ir1 N2 C12 175.3(4) . . . . ?
N1 Ir1 N2 C12 -171.9(17) . . . . ?
N3 Ir1 N2 C12 -3.4(4) . . . . ?
O1 Ir1 N2 C12 81.7(4) . . . . ?
C11 Ir1 N2 C16 89.5(3) . . . . ?
C22 Ir1 N2 C16 0.8(3) . . . . ?
N1 Ir1 N2 C16 14(2) . . . . ?
N3 Ir1 N2 C16 -177.9(3) . . . . ?
O1 Ir1 N2 C16 -92.8(3) . . . . ?
C26 C31 O1 Ir1 -8.3(6) . . . . ?
C30 C31 O1 Ir1 173.6(3) . . . . ?
C11 Ir1 O1 C31 73.8(14) . . . . ?
C22 Ir1 O1 C31 -165.3(3) . . . . ?
N1 Ir1 O1 C31 98.9(3) . . . . ?
N2 Ir1 O1 C31 -85.2(3) . . . . ?
N3 Ir1 O1 C31 9.9(3) . . . . ?
N3 C25 O2 C24 0.1(5) . . . . ?
C26 C25 O2 C24 178.2(4) . . . . ?
C23 C24 O2 C25 0.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.111


_database_code_depnum_ccdc_archive 'CCDC 835020'