# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2012


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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. 
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#  fide research purposes only. It may contain copyright material 
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#  Bona fide researchers may freely download Mercury and enCIFer
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data_glc41
_database_code_depnum_ccdc_archive 'CCDC 898188'
#TrackingRef '15468_web_deposit_cif_file_0_AytacGurhanGOKCE_1353065607.CCDC_898188_2a.cif'


_audit_creation_method           'SHELXL-97 (Sheldrick, 2008)'
_chemical_name_systematic        
;(1,3-Diisopropylbenzimidazol-2-ylidene)
chloro(\m^4^-1,5-cyclooctadiene)iridium^I^
;
_chemical_name_common            
;
(1,3-Diisopropylbenzimidazol-2-ylidene) chloro(mu$4!-1,5-
cyclooctadiene)iridium$I!
;
_chemical_formula_moiety         'C21 H30 Cl Ir N2'
_chemical_formula_sum            'C21 H30 Cl Ir N2'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         538.12

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'
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 21/n'
_symmetry_int_tables_number      14

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                   9.7923(2)
_cell_length_b                   15.4117(3)
_cell_length_c                   13.5711(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.422(2)
_cell_angle_gamma                90.00
_cell_volume                     2030.94(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4461
_cell_measurement_theta_min      3.0369
_cell_measurement_theta_max      29.1588

_exptl_crystal_size_max          0.3075
_exptl_crystal_size_mid          0.2469
_exptl_crystal_size_min          0.1595
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    6.712
_exptl_absorpt_correction_T_min  0.55391
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w 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            9821
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         29.22
_reflns_number_total             4641
_reflns_number_gt                3814
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11
;
_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 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^)+(0.0214P)^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         4641
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0580
_refine_ls_wR_factor_gt          0.0537
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
C22 C 0.2760(4) 0.2170(3) 0.5729(3) 0.0346(10) Uani 1 1 d . . .
H22 H 0.2797 0.2801 0.5820 0.041 Uiso 1 1 calc R . .
C25 C 0.3386(4) 0.0832(3) 0.4479(3) 0.0394(11) Uani 1 1 d . . .
H25 H 0.3666 0.0657 0.3840 0.047 Uiso 1 1 calc R . .
C26 C 0.2248(4) 0.0400(3) 0.4717(3) 0.0378(10) Uani 1 1 d . . .
H26 H 0.1861 -0.0016 0.4211 0.045 Uiso 1 1 calc R . .
C23 C 0.4125(5) 0.1704(3) 0.6021(4) 0.0551(14) Uani 1 1 d . . .
H23A H 0.4834 0.2132 0.6215 0.066 Uiso 1 1 calc R . .
H23B H 0.4046 0.1340 0.6594 0.066 Uiso 1 1 calc R . .
C27 C 0.1991(5) 0.0169(3) 0.5762(3) 0.0515(13) Uani 1 1 d . . .
H27A H 0.2865 0.0041 0.6158 0.062 Uiso 1 1 calc R . .
H27B H 0.1430 -0.0351 0.5738 0.062 Uiso 1 1 calc R . .
C28 C 0.1275(6) 0.0889(3) 0.6262(3) 0.0547(14) Uani 1 1 d . . .
H28A H 0.0296 0.0763 0.6193 0.066 Uiso 1 1 calc R . .
H28B H 0.1614 0.0887 0.6966 0.066 Uiso 1 1 calc R . .
C92 C -0.2539(5) 0.2370(3) 0.3413(3) 0.0491(12) Uani 1 1 d . . .
H92A H -0.2024 0.2195 0.2891 0.074 Uiso 1 1 calc R . .
H92B H -0.3047 0.2889 0.3217 0.074 Uiso 1 1 calc R . .
H92C H -0.3168 0.1917 0.3536 0.074 Uiso 1 1 calc R . .
C91 C -0.2258(4) 0.2812(3) 0.5232(3) 0.0469(12) Uani 1 1 d . . .
H91A H -0.1580 0.2905 0.5799 0.070 Uiso 1 1 calc R . .
H91B H -0.2880 0.2362 0.5378 0.070 Uiso 1 1 calc R . .
H91C H -0.2764 0.3339 0.5077 0.070 Uiso 1 1 calc R . .
C24 C 0.4556(4) 0.1159(4) 0.5216(4) 0.0622(16) Uani 1 1 d . . .
H24A H 0.5068 0.0665 0.5512 0.075 Uiso 1 1 calc R . .
H24B H 0.5176 0.1494 0.4862 0.075 Uiso 1 1 calc R . .
C81 C 0.3825(5) 0.4293(3) 0.4250(4) 0.0597(14) Uani 1 1 d . . .
H81A H 0.3750 0.4203 0.4941 0.089 Uiso 1 1 calc R . .
H81B H 0.3516 0.4867 0.4059 0.089 Uiso 1 1 calc R . .
H81C H 0.4768 0.4226 0.4140 0.089 Uiso 1 1 calc R . .
C82 C 0.3007(5) 0.3700(4) 0.2522(3) 0.0689(17) Uani 1 1 d . . .
H82A H 0.2443 0.3257 0.2178 0.103 Uiso 1 1 calc R . .
H82B H 0.3943 0.3628 0.2396 0.103 Uiso 1 1 calc R . .
H82C H 0.2678 0.4260 0.2291 0.103 Uiso 1 1 calc R . .
C21 C 0.1471(4) 0.1783(3) 0.5855(3) 0.0359(10) Uani 1 1 d . . .
H21 H 0.0779 0.2202 0.6013 0.043 Uiso 1 1 calc R . .
Ir1 Ir 0.172006(15) 0.175546(10) 0.434806(10) 0.02656(6) Uani 1 1 d . . .
Cl1 Cl 0.11473(15) 0.14118(9) 0.26464(8) 0.0602(4) Uani 1 1 d . . .
N2 N -0.0484(3) 0.3174(2) 0.4151(2) 0.0241(7) Uani 1 1 d . . .
N1 N 0.1494(3) 0.3657(2) 0.3823(2) 0.0256(7) Uani 1 1 d . . .
C1 C 0.0829(4) 0.2931(3) 0.4102(3) 0.0250(8) Uani 1 1 d . . .
C2 C 0.0575(4) 0.4346(3) 0.3661(3) 0.0269(9) Uani 1 1 d . . .
C4 C -0.1841(4) 0.4576(3) 0.3793(3) 0.0360(10) Uani 1 1 d . . .
H4 H -0.2686 0.4378 0.3944 0.043 Uiso 1 1 calc R . .
C3 C -0.0678(4) 0.4044(3) 0.3885(3) 0.0264(9) Uani 1 1 d . . .
C8 C 0.2937(4) 0.3628(3) 0.3629(3) 0.0377(10) Uani 1 1 d . . .
H8 H 0.3294 0.3053 0.3836 0.045 Uiso 1 1 calc R . .
C7 C 0.0731(5) 0.5189(3) 0.3341(3) 0.0380(10) Uani 1 1 d . . .
H7 H 0.1576 0.5394 0.3196 0.046 Uiso 1 1 calc R . .
C9 C -0.1554(4) 0.2546(3) 0.4357(3) 0.0309(9) Uani 1 1 d . . .
H9 H -0.1079 0.1998 0.4538 0.037 Uiso 1 1 calc R . .
C6 C -0.0429(5) 0.5715(3) 0.3247(3) 0.0436(12) Uani 1 1 d . . .
H6 H -0.0363 0.6285 0.3031 0.052 Uiso 1 1 calc R . .
C5 C -0.1669(5) 0.5411(3) 0.3466(3) 0.0464(12) Uani 1 1 d . . .
H5 H -0.2424 0.5782 0.3391 0.056 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
C22 0.039(2) 0.030(2) 0.033(2) -0.0087(19) -0.0018(18) 0.001(2)
C25 0.037(2) 0.032(2) 0.050(3) -0.009(2) 0.006(2) 0.012(2)
C26 0.045(3) 0.019(2) 0.048(3) -0.0083(19) -0.001(2) 0.008(2)
C23 0.035(3) 0.061(4) 0.064(3) -0.012(3) -0.014(2) 0.002(3)
C27 0.064(3) 0.032(3) 0.059(3) 0.011(2) 0.008(2) 0.002(3)
C28 0.070(3) 0.054(3) 0.042(3) 0.004(3) 0.013(2) -0.010(3)
C92 0.054(3) 0.046(3) 0.044(3) 0.000(2) -0.005(2) -0.018(3)
C91 0.038(3) 0.059(3) 0.045(3) -0.002(2) 0.011(2) -0.006(3)
C24 0.028(2) 0.054(4) 0.101(4) -0.018(3) -0.003(3) 0.013(3)
C81 0.038(3) 0.066(4) 0.074(3) -0.006(3) 0.004(2) -0.013(3)
C82 0.067(4) 0.096(5) 0.051(3) -0.004(3) 0.035(3) -0.008(4)
C21 0.040(2) 0.038(3) 0.030(2) -0.001(2) 0.0064(18) 0.009(2)
Ir1 0.02919(9) 0.02241(9) 0.02822(10) -0.00184(7) 0.00418(6) 0.00526(7)
Cl1 0.0899(10) 0.0554(8) 0.0330(6) -0.0107(6) -0.0010(6) 0.0256(8)
N2 0.0214(15) 0.0218(17) 0.0298(17) 0.0012(14) 0.0057(13) 0.0013(14)
N1 0.0253(16) 0.0236(17) 0.0284(17) 0.0020(14) 0.0053(13) -0.0005(15)
C1 0.028(2) 0.026(2) 0.0220(19) 0.0004(16) 0.0055(15) 0.0033(18)
C2 0.030(2) 0.026(2) 0.0234(19) 0.0015(17) -0.0017(16) 0.0001(18)
C4 0.034(2) 0.033(2) 0.041(2) -0.001(2) 0.0024(18) 0.008(2)
C3 0.026(2) 0.026(2) 0.027(2) -0.0018(17) 0.0012(16) 0.0019(18)
C8 0.031(2) 0.039(3) 0.046(3) 0.004(2) 0.0150(19) 0.001(2)
C7 0.046(3) 0.031(2) 0.037(2) 0.003(2) 0.0020(19) -0.005(2)
C9 0.029(2) 0.027(2) 0.037(2) 0.0064(18) 0.0037(17) -0.0034(19)
C6 0.061(3) 0.018(2) 0.048(3) 0.002(2) -0.007(2) 0.001(2)
C5 0.058(3) 0.029(3) 0.050(3) -0.005(2) -0.004(2) 0.018(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
C22 C21 1.426(6) . ?
C22 C23 1.524(6) . ?
C22 Ir1 2.112(4) . ?
C22 H22 0.9800 . ?
C25 C26 1.372(6) . ?
C25 C24 1.507(6) . ?
C25 Ir1 2.155(4) . ?
C25 H25 0.9800 . ?
C26 C27 1.515(6) . ?
C26 Ir1 2.194(4) . ?
C26 H26 0.9800 . ?
C23 C24 1.482(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C27 C28 1.519(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C21 1.506(6) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C92 C9 1.525(5) . ?
C92 H92A 0.9600 . ?
C92 H92B 0.9600 . ?
C92 H92C 0.9600 . ?
C91 C9 1.506(5) . ?
C91 H91A 0.9600 . ?
C91 H91B 0.9600 . ?
C91 H91C 0.9600 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C81 C8 1.525(6) . ?
C81 H81A 0.9600 . ?
C81 H81B 0.9600 . ?
C81 H81C 0.9600 . ?
C82 C8 1.516(5) . ?
C82 H82A 0.9600 . ?
C82 H82B 0.9600 . ?
C82 H82C 0.9600 . ?
C21 Ir1 2.092(4) . ?
C21 H21 0.9800 . ?
Ir1 C1 2.020(4) . ?
Ir1 Cl1 2.3650(11) . ?
N2 C1 1.349(5) . ?
N2 C3 1.396(5) . ?
N2 C9 1.479(5) . ?
N1 C1 1.372(5) . ?
N1 C2 1.392(5) . ?
N1 C8 1.471(5) . ?
C2 C3 1.383(5) . ?
C2 C7 1.385(5) . ?
C4 C5 1.378(6) . ?
C4 C3 1.395(5) . ?
C4 H4 0.9300 . ?
C8 H8 0.9800 . ?
C7 C6 1.388(6) . ?
C7 H7 0.9300 . ?
C9 H9 0.9800 . ?
C6 C5 1.369(6) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?

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
C21 C22 C23 122.1(4) . . ?
C21 C22 Ir1 69.4(2) . . ?
C23 C22 Ir1 113.2(3) . . ?
C21 C22 H22 114.7 . . ?
C23 C22 H22 114.7 . . ?
Ir1 C22 H22 114.7 . . ?
C26 C25 C24 125.3(4) . . ?
C26 C25 Ir1 73.1(2) . . ?
C24 C25 Ir1 109.6(3) . . ?
C26 C25 H25 113.8 . . ?
C24 C25 H25 113.8 . . ?
Ir1 C25 H25 113.8 . . ?
C25 C26 C27 125.0(4) . . ?
C25 C26 Ir1 70.1(2) . . ?
C27 C26 Ir1 112.1(3) . . ?
C25 C26 H26 113.9 . . ?
C27 C26 H26 113.9 . . ?
Ir1 C26 H26 113.9 . . ?
C24 C23 C22 113.5(4) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C26 C27 C28 112.8(4) . . ?
C26 C27 H27A 109.0 . . ?
C28 C27 H27A 109.0 . . ?
C26 C27 H27B 109.0 . . ?
C28 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
C21 C28 C27 114.7(4) . . ?
C21 C28 H28A 108.6 . . ?
C27 C28 H28A 108.6 . . ?
C21 C28 H28B 108.6 . . ?
C27 C28 H28B 108.6 . . ?
H28A C28 H28B 107.6 . . ?
C9 C92 H92A 109.5 . . ?
C9 C92 H92B 109.5 . . ?
H92A C92 H92B 109.5 . . ?
C9 C92 H92C 109.5 . . ?
H92A C92 H92C 109.5 . . ?
H92B C92 H92C 109.5 . . ?
C9 C91 H91A 109.5 . . ?
C9 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
C9 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?
C23 C24 C25 114.4(4) . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24B 108.7 . . ?
C25 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C8 C81 H81A 109.5 . . ?
C8 C81 H81B 109.5 . . ?
H81A C81 H81B 109.5 . . ?
C8 C81 H81C 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
C8 C82 H82A 109.5 . . ?
C8 C82 H82B 109.5 . . ?
H82A C82 H82B 109.5 . . ?
C8 C82 H82C 109.5 . . ?
H82A C82 H82C 109.5 . . ?
H82B C82 H82C 109.5 . . ?
C22 C21 C28 125.7(4) . . ?
C22 C21 Ir1 71.0(2) . . ?
C28 C21 Ir1 112.1(3) . . ?
C22 C21 H21 113.5 . . ?
C28 C21 H21 113.5 . . ?
Ir1 C21 H21 113.5 . . ?
C1 Ir1 C21 92.36(15) . . ?
C1 Ir1 C22 91.38(15) . . ?
C21 Ir1 C22 39.65(16) . . ?
C1 Ir1 C25 155.83(17) . . ?
C21 Ir1 C25 96.64(16) . . ?
C22 Ir1 C25 81.58(16) . . ?
C1 Ir1 C26 167.33(16) . . ?
C21 Ir1 C26 81.38(16) . . ?
C22 Ir1 C26 90.75(16) . . ?
C25 Ir1 C26 36.76(15) . . ?
C1 Ir1 Cl1 89.79(10) . . ?
C21 Ir1 Cl1 156.44(13) . . ?
C22 Ir1 Cl1 163.76(13) . . ?
C25 Ir1 Cl1 90.81(11) . . ?
C26 Ir1 Cl1 91.65(11) . . ?
C1 N2 C3 110.6(3) . . ?
C1 N2 C9 122.1(3) . . ?
C3 N2 C9 127.0(3) . . ?
C1 N1 C2 110.2(3) . . ?
C1 N1 C8 121.8(3) . . ?
C2 N1 C8 127.7(3) . . ?
N2 C1 N1 106.1(3) . . ?
N2 C1 Ir1 129.4(3) . . ?
N1 C1 Ir1 124.5(3) . . ?
C3 C2 C7 121.5(4) . . ?
C3 C2 N1 106.4(3) . . ?
C7 C2 N1 132.1(4) . . ?
C5 C4 C3 116.5(4) . . ?
C5 C4 H4 121.8 . . ?
C3 C4 H4 121.8 . . ?
C2 C3 C4 121.3(4) . . ?
C2 C3 N2 106.6(3) . . ?
C4 C3 N2 132.1(4) . . ?
N1 C8 C82 110.0(3) . . ?
N1 C8 C81 111.9(4) . . ?
C82 C8 C81 113.8(4) . . ?
N1 C8 H8 106.9 . . ?
C82 C8 H8 106.9 . . ?
C81 C8 H8 106.9 . . ?
C2 C7 C6 117.0(4) . . ?
C2 C7 H7 121.5 . . ?
C6 C7 H7 121.5 . . ?
N2 C9 C91 112.3(3) . . ?
N2 C9 C92 110.1(3) . . ?
C91 C9 C92 114.0(4) . . ?
N2 C9 H9 106.7 . . ?
C91 C9 H9 106.7 . . ?
C92 C9 H9 106.7 . . ?
C5 C6 C7 121.2(4) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C5 C4 122.5(4) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?

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
C24 C25 C26 C27 -1.1(7) . . . . ?
Ir1 C25 C26 C27 -103.5(4) . . . . ?
C24 C25 C26 Ir1 102.5(4) . . . . ?
C21 C22 C23 C24 88.6(6) . . . . ?
Ir1 C22 C23 C24 9.2(6) . . . . ?
C25 C26 C27 C28 87.4(5) . . . . ?
Ir1 C26 C27 C28 6.8(5) . . . . ?
C26 C27 C28 C21 -24.1(6) . . . . ?
C22 C23 C24 C25 -26.6(7) . . . . ?
C26 C25 C24 C23 -52.2(7) . . . . ?
Ir1 C25 C24 C23 30.7(6) . . . . ?
C23 C22 C21 C28 -1.2(6) . . . . ?
Ir1 C22 C21 C28 104.0(4) . . . . ?
C23 C22 C21 Ir1 -105.2(4) . . . . ?
C27 C28 C21 C22 -51.5(6) . . . . ?
C27 C28 C21 Ir1 30.3(5) . . . . ?
C22 C21 Ir1 C1 -89.3(3) . . . . ?
C28 C21 Ir1 C1 148.9(3) . . . . ?
C28 C21 Ir1 C22 -121.7(4) . . . . ?
C22 C21 Ir1 C25 68.2(3) . . . . ?
C28 C21 Ir1 C25 -53.5(4) . . . . ?
C22 C21 Ir1 C26 101.7(3) . . . . ?
C28 C21 Ir1 C26 -20.0(3) . . . . ?
C22 C21 Ir1 Cl1 175.8(2) . . . . ?
C28 C21 Ir1 Cl1 54.1(5) . . . . ?
C21 C22 Ir1 C1 92.0(3) . . . . ?
C23 C22 Ir1 C1 -150.8(4) . . . . ?
C23 C22 Ir1 C21 117.2(4) . . . . ?
C21 C22 Ir1 C25 -111.2(3) . . . . ?
C23 C22 Ir1 C25 6.0(4) . . . . ?
C21 C22 Ir1 C26 -75.5(3) . . . . ?
C23 C22 Ir1 C26 41.7(4) . . . . ?
C21 C22 Ir1 Cl1 -174.0(3) . . . . ?
C23 C22 Ir1 Cl1 -56.8(6) . . . . ?
C26 C25 Ir1 C1 177.0(3) . . . . ?
C24 C25 Ir1 C1 54.9(5) . . . . ?
C26 C25 Ir1 C21 65.9(3) . . . . ?
C24 C25 Ir1 C21 -56.2(4) . . . . ?
C26 C25 Ir1 C22 102.7(3) . . . . ?
C24 C25 Ir1 C22 -19.4(3) . . . . ?
C24 C25 Ir1 C26 -122.2(5) . . . . ?
C26 C25 Ir1 Cl1 -91.7(2) . . . . ?
C24 C25 Ir1 Cl1 146.2(3) . . . . ?
C25 C26 Ir1 C1 -174.5(6) . . . . ?
C27 C26 Ir1 C1 -53.8(8) . . . . ?
C25 C26 Ir1 C21 -113.5(3) . . . . ?
C27 C26 Ir1 C21 7.2(3) . . . . ?
C25 C26 Ir1 C22 -74.8(3) . . . . ?
C27 C26 Ir1 C22 45.9(3) . . . . ?
C27 C26 Ir1 C25 120.7(4) . . . . ?
C25 C26 Ir1 Cl1 89.1(2) . . . . ?
C27 C26 Ir1 Cl1 -150.1(3) . . . . ?
C3 N2 C1 N1 1.3(4) . . . . ?
C9 N2 C1 N1 175.3(3) . . . . ?
C3 N2 C1 Ir1 -177.7(3) . . . . ?
C9 N2 C1 Ir1 -3.7(5) . . . . ?
C2 N1 C1 N2 -2.3(4) . . . . ?
C8 N1 C1 N2 -175.9(3) . . . . ?
C2 N1 C1 Ir1 176.7(2) . . . . ?
C8 N1 C1 Ir1 3.1(5) . . . . ?
C21 Ir1 C1 N2 -66.1(3) . . . . ?
C22 Ir1 C1 N2 -105.8(3) . . . . ?
C25 Ir1 C1 N2 -178.1(3) . . . . ?
C26 Ir1 C1 N2 -6.2(9) . . . . ?
Cl1 Ir1 C1 N2 90.4(3) . . . . ?
C21 Ir1 C1 N1 115.1(3) . . . . ?
C22 Ir1 C1 N1 75.4(3) . . . . ?
C25 Ir1 C1 N1 3.1(6) . . . . ?
C26 Ir1 C1 N1 175.0(5) . . . . ?
Cl1 Ir1 C1 N1 -88.4(3) . . . . ?
C1 N1 C2 C3 2.4(4) . . . . ?
C8 N1 C2 C3 175.6(3) . . . . ?
C1 N1 C2 C7 -177.4(4) . . . . ?
C8 N1 C2 C7 -4.2(7) . . . . ?
C7 C2 C3 C4 0.3(6) . . . . ?
N1 C2 C3 C4 -179.5(3) . . . . ?
C7 C2 C3 N2 178.3(3) . . . . ?
N1 C2 C3 N2 -1.5(4) . . . . ?
C5 C4 C3 C2 0.2(6) . . . . ?
C5 C4 C3 N2 -177.1(4) . . . . ?
C1 N2 C3 C2 0.2(4) . . . . ?
C9 N2 C3 C2 -173.5(3) . . . . ?
C1 N2 C3 C4 177.8(4) . . . . ?
C9 N2 C3 C4 4.1(6) . . . . ?
C1 N1 C8 C82 107.2(4) . . . . ?
C2 N1 C8 C82 -65.3(5) . . . . ?
C1 N1 C8 C81 -125.3(4) . . . . ?
C2 N1 C8 C81 62.2(5) . . . . ?
C3 C2 C7 C6 -0.6(6) . . . . ?
N1 C2 C7 C6 179.2(4) . . . . ?
C1 N2 C9 C91 125.0(4) . . . . ?
C3 N2 C9 C91 -62.0(5) . . . . ?
C1 N2 C9 C92 -106.8(4) . . . . ?
C3 N2 C9 C92 66.1(5) . . . . ?
C2 C7 C6 C5 0.3(6) . . . . ?
C7 C6 C5 C4 0.3(7) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.840
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.573
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.121


data_glc39
_database_code_depnum_ccdc_archive 'CCDC 898189'
#TrackingRef '15469_web_deposit_cif_file_1_AytacGurhanGOKCE_1353065607.CCDC_898189_2b.cif'


_audit_creation_method           'SHELXL-97 (Sheldrick, 2008)'
_chemical_name_systematic        
;(1,3-Diisopropyl-(5,6-dimethyl)benzimidazol-2-ylidene)
chloro(\m^4^-1,5-cyclooctadiene)iridium^I^
;
_chemical_name_common            
;
(1,3-Diisopropyl-(5,6-dimethyl)benzimidazol-2-ylidene)
chloro(mu$4!-1,5-cyclooctadiene)iridium$I!
;
_chemical_formula_moiety         'C23 H34 Cl Ir N2'
_chemical_formula_sum            'C23 H34 Cl Ir N2'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         566.17

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'
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   'C 2/m'
_symmetry_int_tables_number      12

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

_cell_length_a                   17.1618(16)
_cell_length_b                   14.1773(7)
_cell_length_c                   12.8587(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 133.312(16)
_cell_angle_gamma                90.00
_cell_volume                     2276.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5439
_cell_measurement_theta_min      3.2562
_cell_measurement_theta_max      29.3167
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.193
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    5.992
_exptl_absorpt_correction_T_min  0.42928
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w 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            12104
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         29.38
_reflns_number_total             2843
_reflns_number_gt                2567
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11
;
_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 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^)+(0.0589P)^2^+2.5671P] 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         2843
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.005
_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
C2 C 0.1971(3) -0.0492(3) 0.7469(5) 0.0302(10) Uani 1 1 d . . .
C3 C 0.1482(4) -0.0985(4) 0.7822(5) 0.0376(11) Uani 1 1 d . . .
H3 H 0.1473 -0.1641 0.7809 0.045 Uiso 1 1 calc R . .
C1 C 0.2893(5) 0.0000 0.6918(7) 0.0319(14) Uani 1 2 d S . .
C81 C 0.3209(5) -0.2389(4) 0.8067(7) 0.0525(14) Uani 1 1 d . . .
H81A H 0.3866 -0.2106 0.8899 0.079 Uiso 1 1 calc R . .
H81B H 0.3363 -0.2975 0.7864 0.079 Uiso 1 1 calc R . .
H81C H 0.2755 -0.2505 0.8239 0.079 Uiso 1 1 calc R . .
C21 C 0.4752(4) 0.0492(4) 0.6016(5) 0.0379(11) Uani 1 1 d . . .
H21 H 0.4327 0.0774 0.5066 0.045 Uiso 1 1 calc R . .
C4 C 0.1008(4) -0.0494(4) 0.8192(6) 0.0405(12) Uani 1 1 d . . .
C24 C 0.5144(4) -0.0503(4) 0.8494(5) 0.0470(14) Uani 1 1 d . . .
H24 H 0.4974 -0.0789 0.9013 0.056 Uiso 1 1 calc R . .
C8 C 0.2652(4) -0.1734(4) 0.6813(6) 0.0386(11) Uani 1 1 d . . .
H8 H 0.3114 -0.1690 0.6621 0.046 Uiso 1 1 calc R . .
C82 C 0.1597(5) -0.2091(5) 0.5471(7) 0.0613(17) Uani 1 1 d . . .
H82A H 0.1113 -0.2147 0.5605 0.092 Uiso 1 1 calc R . .
H82B H 0.1692 -0.2697 0.5239 0.092 Uiso 1 1 calc R . .
H82C H 0.1307 -0.1658 0.4706 0.092 Uiso 1 1 calc R . .
C22 C 0.5674(5) 0.1083(6) 0.7206(7) 0.0647(19) Uani 1 1 d . . .
H22A H 0.6311 0.0869 0.7429 0.078 Uiso 1 1 calc R . .
H22B H 0.5542 0.1729 0.6873 0.078 Uiso 1 1 calc R . .
C23 C 0.5889(7) 0.1074(7) 0.8514(7) 0.084(3) Uani 1 1 d . . .
H23A H 0.5873 0.1720 0.8748 0.101 Uiso 1 1 calc R . .
H23B H 0.6610 0.0839 0.9280 0.101 Uiso 1 1 calc R . .
C5 C 0.0531(5) -0.1028(5) 0.8649(7) 0.0549(16) Uani 1 1 d . . .
H5A H -0.0225 -0.0910 0.7986 0.082 Uiso 1 1 calc R . .
H5B H 0.0859 -0.0825 0.9586 0.082 Uiso 1 1 calc R . .
H5C H 0.0654 -0.1691 0.8668 0.082 Uiso 1 1 calc R . .
N1 N 0.2554(3) -0.0767(3) 0.7137(4) 0.0316(8) Uani 1 1 d . . .
Cl1 Cl 0.22679(16) 0.0000 0.4002(2) 0.0571(6) Uani 1 2 d S . .
Ir1 Ir 0.381178(17) 0.0000 0.64590(2) 0.02766(11) Uani 1 2 d S . .

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
C2 0.028(2) 0.037(3) 0.036(2) 0.0006(19) 0.0262(19) -0.0005(18)
C3 0.037(2) 0.036(3) 0.047(3) 0.004(2) 0.031(2) 0.001(2)
C1 0.032(3) 0.032(4) 0.034(3) 0.000 0.023(3) 0.000
C81 0.062(4) 0.037(3) 0.069(4) 0.007(3) 0.049(3) 0.008(3)
C21 0.046(3) 0.048(3) 0.040(2) -0.001(2) 0.037(2) -0.006(2)
C4 0.032(2) 0.049(3) 0.045(2) 0.003(2) 0.029(2) -0.001(2)
C24 0.048(3) 0.061(4) 0.027(2) 0.014(2) 0.024(2) 0.009(3)
C8 0.053(3) 0.028(3) 0.057(3) -0.007(2) 0.046(3) -0.001(2)
C82 0.075(4) 0.051(4) 0.061(4) -0.017(3) 0.048(4) -0.014(3)
C22 0.062(4) 0.078(5) 0.069(4) -0.022(4) 0.051(4) -0.037(4)
C23 0.090(5) 0.105(7) 0.056(4) -0.033(4) 0.050(4) -0.061(5)
C5 0.060(4) 0.062(4) 0.074(4) 0.010(3) 0.059(3) 0.004(3)
N1 0.039(2) 0.028(2) 0.044(2) -0.0010(16) 0.0345(18) 0.0011(16)
Cl1 0.0388(10) 0.0802(16) 0.0335(8) 0.000 0.0175(8) 0.000
Ir1 0.02968(15) 0.03279(17) 0.02863(14) 0.000 0.02314(12) 0.000

_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
C2 N1 1.386(6) . ?
C2 C3 1.387(7) . ?
C2 C2 1.394(10) 6 ?
C3 C4 1.379(7) . ?
C3 H3 0.9300 . ?
C1 N1 1.351(6) . ?
C1 N1 1.351(6) 6 ?
C1 Ir1 2.028(7) . ?
C81 C8 1.504(8) . ?
C81 H81A 0.9600 . ?
C81 H81B 0.9600 . ?
C81 H81C 0.9600 . ?
C21 C21 1.395(11) 6 ?
C21 C22 1.492(8) . ?
C21 Ir1 2.162(5) . ?
C21 H21 0.9800 . ?
C4 C4 1.402(12) 6 ?
C4 C5 1.500(8) . ?
C24 C24 1.427(12) 6 ?
C24 C23 1.499(9) 6 ?
C24 Ir1 2.092(5) . ?
C24 H24 0.9800 . ?
C8 N1 1.476(6) . ?
C8 C82 1.491(8) . ?
C8 H8 0.9800 . ?
C82 H82A 0.9600 . ?
C82 H82B 0.9600 . ?
C82 H82C 0.9600 . ?
C22 C23 1.454(9) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.499(9) 6 ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
Cl1 Ir1 2.349(2) . ?
Ir1 C24 2.092(5) 6 ?
Ir1 C21 2.162(5) 6 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C2 C3 133.3(5) . . ?
N1 C2 C2 106.4(3) . 6 ?
C3 C2 C2 120.3(3) . 6 ?
C4 C3 C2 119.4(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
N1 C1 N1 107.3(6) . 6 ?
N1 C1 Ir1 126.3(3) . . ?
N1 C1 Ir1 126.3(3) 6 . ?
C8 C81 H81A 109.5 . . ?
C8 C81 H81B 109.5 . . ?
H81A C81 H81B 109.5 . . ?
C8 C81 H81C 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
C21 C21 C22 124.2(4) 6 . ?
C21 C21 Ir1 71.18(15) 6 . ?
C22 C21 Ir1 111.6(4) . . ?
C21 C21 H21 114.1 6 . ?
C22 C21 H21 114.1 . . ?
Ir1 C21 H21 114.1 . . ?
C3 C4 C4 120.3(3) . 6 ?
C3 C4 C5 119.4(6) . . ?
C4 C4 C5 120.3(4) 6 . ?
C24 C24 C23 122.7(5) 6 6 ?
C24 C24 Ir1 70.06(17) 6 . ?
C23 C24 Ir1 113.2(4) 6 . ?
C24 C24 H24 114.4 6 . ?
C23 C24 H24 114.4 6 . ?
Ir1 C24 H24 114.4 . . ?
N1 C8 C82 111.0(5) . . ?
N1 C8 C81 112.5(4) . . ?
C82 C8 C81 114.0(5) . . ?
N1 C8 H8 106.3 . . ?
C82 C8 H8 106.3 . . ?
C81 C8 H8 106.3 . . ?
C8 C82 H82A 109.5 . . ?
C8 C82 H82B 109.5 . . ?
H82A C82 H82B 109.5 . . ?
C8 C82 H82C 109.5 . . ?
H82A C82 H82C 109.5 . . ?
H82B C82 H82C 109.5 . . ?
C23 C22 C21 115.5(5) . . ?
C23 C22 H22A 108.4 . . ?
C21 C22 H22A 108.4 . . ?
C23 C22 H22B 108.4 . . ?
C21 C22 H22B 108.4 . . ?
H22A C22 H22B 107.5 . . ?
C22 C23 C24 116.6(5) . 6 ?
C22 C23 H23A 108.1 . . ?
C24 C23 H23A 108.1 6 . ?
C22 C23 H23B 108.1 . . ?
C24 C23 H23B 108.1 6 . ?
H23A C23 H23B 107.3 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 N1 C2 110.0(4) . . ?
C1 N1 C8 122.7(4) . . ?
C2 N1 C8 126.5(4) . . ?
C1 Ir1 C24 92.1(2) . 6 ?
C1 Ir1 C24 92.1(2) . . ?
C24 Ir1 C24 39.9(3) 6 . ?
C1 Ir1 C21 161.18(15) . 6 ?
C24 Ir1 C21 93.9(2) 6 6 ?
C24 Ir1 C21 81.2(2) . 6 ?
C1 Ir1 C21 161.18(15) . . ?
C24 Ir1 C21 81.2(2) 6 . ?
C24 Ir1 C21 93.9(2) . . ?
C21 Ir1 C21 37.6(3) 6 . ?
C1 Ir1 Cl1 90.37(19) . . ?
C24 Ir1 Cl1 159.90(17) 6 . ?
C24 Ir1 Cl1 159.90(17) . . ?
C21 Ir1 Cl1 90.15(15) 6 . ?
C21 Ir1 Cl1 90.15(15) . . ?

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
N1 C2 C3 C4 175.8(5) . . . . ?
C2 C2 C3 C4 -0.9(6) 6 . . . ?
C2 C3 C4 C4 0.9(6) . . . 6 ?
C2 C3 C4 C5 -176.7(5) . . . . ?
C21 C21 C22 C23 -70.4(8) 6 . . . ?
Ir1 C21 C22 C23 11.0(9) . . . . ?
C21 C22 C23 C24 -1.9(13) . . . 6 ?
N1 C1 N1 C2 1.3(7) 6 . . . ?
Ir1 C1 N1 C2 178.1(4) . . . . ?
N1 C1 N1 C8 171.8(3) 6 . . . ?
Ir1 C1 N1 C8 -11.4(8) . . . . ?
C3 C2 N1 C1 -177.9(5) . . . . ?
C2 C2 N1 C1 -0.8(4) 6 . . . ?
C3 C2 N1 C8 12.1(8) . . . . ?
C2 C2 N1 C8 -170.8(4) 6 . . . ?
C82 C8 N1 C1 -104.2(6) . . . . ?
C81 C8 N1 C1 126.8(6) . . . . ?
C82 C8 N1 C2 64.7(7) . . . . ?
C81 C8 N1 C2 -64.4(7) . . . . ?
N1 C1 Ir1 C24 -108.0(6) . . . 6 ?
N1 C1 Ir1 C24 68.1(6) 6 . . 6 ?
N1 C1 Ir1 C24 -68.1(6) . . . . ?
N1 C1 Ir1 C24 108.0(6) 6 . . . ?
N1 C1 Ir1 C21 0.4(11) . . . 6 ?
N1 C1 Ir1 C21 176.5(5) 6 . . 6 ?
N1 C1 Ir1 C21 -176.5(5) . . . . ?
N1 C1 Ir1 C21 -0.4(11) 6 . . . ?
N1 C1 Ir1 Cl1 91.9(5) . . . . ?
N1 C1 Ir1 Cl1 -91.9(5) 6 . . . ?
C24 C24 Ir1 C1 -90.76(9) 6 . . . ?
C23 C24 Ir1 C1 151.2(6) 6 . . . ?
C23 C24 Ir1 C24 -118.0(6) 6 . . 6 ?
C24 C24 Ir1 C21 106.92(16) 6 . . 6 ?
C23 C24 Ir1 C21 -11.1(6) 6 . . 6 ?
C24 C24 Ir1 C21 71.37(16) 6 . . . ?
C23 C24 Ir1 C21 -46.7(6) 6 . . . ?
C24 C24 Ir1 Cl1 172.4(5) 6 . . . ?
C23 C24 Ir1 Cl1 54.4(9) 6 . . . ?
C21 C21 Ir1 C1 178.4(7) 6 . . . ?
C22 C21 Ir1 C1 58.2(9) . . . . ?
C21 C21 Ir1 C24 108.18(18) 6 . . 6 ?
C22 C21 Ir1 C24 -12.0(5) . . . 6 ?
C21 C21 Ir1 C24 70.23(18) 6 . . . ?
C22 C21 Ir1 C24 -50.0(5) . . . . ?
C22 C21 Ir1 C21 -120.2(5) . . . 6 ?
C21 C21 Ir1 Cl1 -90.05(5) 6 . . . ?
C22 C21 Ir1 Cl1 149.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.871
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         3.440
_refine_diff_density_min         -2.277
_refine_diff_density_rms         0.160