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


data_global
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
A.Petronilho
M.Rahman
H.Al-Sayyed
J.A.Woods
H.Muller-Bunz
;
D.MacElroy
;
S.Bernhard
M.Albrecht
_publ_contact_author_name        'Prof. Dr. Martin Albrecht'
_publ_contact_author_email       martin.albrecht@ucd.ie

data_complex2
_database_code_depnum_ccdc_archive 'CCDC 867256'
#TrackingRef '- complex2.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 Cl2 Ir N3, C H2 Cl2'
_chemical_formula_sum            'C21 H28 Cl4 Ir N3'
_chemical_formula_weight         656.46

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.96981(5)
_cell_length_b                   9.18519(5)
_cell_length_c                   14.95269(7)
_cell_angle_alpha                86.2178(4)
_cell_angle_beta                 76.6774(4)
_cell_angle_gamma                77.1641(4)
_cell_volume                     1168.690(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    56442
_cell_measurement_theta_min      3.2465
_cell_measurement_theta_max      32.7084

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2450
_exptl_crystal_size_mid          0.1752
_exptl_crystal_size_min          0.1017
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    6.183
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.454
_exptl_absorpt_correction_T_max  0.712
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            75290
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.25
_diffrn_reflns_theta_max         32.78
_reflns_number_total             8215
_reflns_number_gt                7947
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0143P)^2^+1.0218P] 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         8215
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0153
_refine_ls_R_factor_gt           0.0142
_refine_ls_wR_factor_ref         0.0328
_refine_ls_wR_factor_gt          0.0323
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.004
_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
Ir Ir 0.716510(6) 0.717821(6) 0.701259(3) 0.01034(2) Uani 1 1 d . . .
Cl1 Cl 0.44431(4) 0.70021(4) 0.73504(2) 0.01477(6) Uani 1 1 d . . .
Cl2 Cl 0.75124(4) 0.52496(4) 0.58971(2) 0.01635(6) Uani 1 1 d . . .
C1 C 0.73867(17) 0.64362(17) 0.84364(10) 0.0149(2) Uani 1 1 d . . .
C2 C 0.86867(17) 0.56389(17) 0.78106(10) 0.0169(3) Uani 1 1 d . . .
C3 C 0.95002(17) 0.67072(19) 0.72470(10) 0.0179(3) Uani 1 1 d . . .
C4 C 0.86857(18) 0.81790(18) 0.75728(10) 0.0166(3) Uani 1 1 d . . .
C5 C 0.73291(17) 0.80296(17) 0.82812(10) 0.0148(2) Uani 1 1 d . . .
C6 C 0.62303(19) 0.5806(2) 0.91554(11) 0.0207(3) Uani 1 1 d . . .
H6A H 0.6414 0.4725 0.9077 0.031 Uiso 1 1 calc R . .
H6B H 0.5164 0.6271 0.9094 0.031 Uiso 1 1 calc R . .
H6C H 0.6356 0.6008 0.9766 0.031 Uiso 1 1 calc R . .
C7 C 0.9173(2) 0.39853(19) 0.77202(13) 0.0263(3) Uani 1 1 d . . .
H7A H 0.8367 0.3518 0.8112 0.039 Uiso 1 1 calc R . .
H7B H 1.0169 0.3632 0.7910 0.039 Uiso 1 1 calc R . .
H7C H 0.9302 0.3719 0.7079 0.039 Uiso 1 1 calc R . .
C8 C 1.10265(19) 0.6300(2) 0.65655(12) 0.0267(4) Uani 1 1 d . . .
H8A H 1.1252 0.7190 0.6209 0.040 Uiso 1 1 calc R . .
H8B H 1.0963 0.5545 0.6150 0.040 Uiso 1 1 calc R . .
H8C H 1.1866 0.5897 0.6890 0.040 Uiso 1 1 calc R . .
C9 C 0.9187(2) 0.9610(2) 0.72512(12) 0.0245(3) Uani 1 1 d . . .
H9A H 0.9867 0.9822 0.7632 0.037 Uiso 1 1 calc R . .
H9B H 0.8260 1.0426 0.7303 0.037 Uiso 1 1 calc R . .
H9C H 0.9763 0.9518 0.6608 0.037 Uiso 1 1 calc R . .
C10 C 0.6194(2) 0.92156(19) 0.88733(11) 0.0209(3) Uani 1 1 d . . .
H10A H 0.6450 0.9174 0.9479 0.031 Uiso 1 1 calc R . .
H10B H 0.5128 0.9055 0.8944 0.031 Uiso 1 1 calc R . .
H10C H 0.6258 1.0197 0.8586 0.031 Uiso 1 1 calc R . .
C11 C 0.68311(16) 0.88966(16) 0.60816(9) 0.0124(2) Uani 1 1 d . . .
C12 C 0.58652(16) 1.03386(15) 0.61778(9) 0.0126(2) Uani 1 1 d . . .
C13 C 0.47790(17) 1.11344(16) 0.69789(10) 0.0137(2) Uani 1 1 d . . .
C14 C 0.34296(17) 1.06507(16) 0.74318(10) 0.0159(3) Uani 1 1 d . . .
H14 H 0.3160 0.9822 0.7208 0.019 Uiso 1 1 calc R . .
C15 C 0.24786(18) 1.13873(18) 0.82126(11) 0.0199(3) Uani 1 1 d . . .
H15 H 0.1569 1.1047 0.8528 0.024 Uiso 1 1 calc R . .
C16 C 0.2850(2) 1.26180(18) 0.85338(11) 0.0224(3) Uani 1 1 d . . .
H16 H 0.2212 1.3098 0.9077 0.027 Uiso 1 1 calc R . .
C17 C 0.4156(2) 1.31459(18) 0.80598(12) 0.0229(3) Uani 1 1 d . . .
H17 H 0.4390 1.4010 0.8264 0.027 Uiso 1 1 calc R . .
C18 C 0.51196(19) 1.24026(17) 0.72856(11) 0.0185(3) Uani 1 1 d . . .
H18 H 0.6015 1.2759 0.6963 0.022 Uiso 1 1 calc R . .
N1 N 0.77030(15) 0.89742(14) 0.51971(8) 0.0149(2) Uani 1 1 d . . .
C19 C 0.9046(2) 0.78828(19) 0.47038(12) 0.0246(3) Uani 1 1 d . . .
H19A H 0.8962 0.7830 0.4065 0.037 Uiso 1 1 calc R . .
H19B H 0.9053 0.6899 0.5001 0.037 Uiso 1 1 calc R . .
H19C H 1.0020 0.8190 0.4715 0.037 Uiso 1 1 calc R . .
N2 N 0.73500(16) 1.02710(15) 0.47546(9) 0.0168(2) Uani 1 1 d . . .
N3 N 0.62282(15) 1.10821(14) 0.53647(8) 0.0142(2) Uani 1 1 d . . .
C20 C 0.55140(19) 1.26007(17) 0.50968(11) 0.0184(3) Uani 1 1 d . . .
H20A H 0.6026 1.3321 0.5296 0.028 Uiso 1 1 calc R . .
H20B H 0.4394 1.2827 0.5389 0.028 Uiso 1 1 calc R . .
H20C H 0.5647 1.2667 0.4427 0.028 Uiso 1 1 calc R . .
C21 C 0.1276(2) 0.8030(2) 0.92170(12) 0.0244(3) Uani 1 1 d . . .
H21A H 0.0341 0.8774 0.9119 0.029 Uiso 1 1 calc R . .
H21B H 0.2114 0.8011 0.8653 0.029 Uiso 1 1 calc R . .
Cl3 Cl 0.19096(5) 0.85737(5) 1.01557(3) 0.02841(8) Uani 1 1 d . . .
Cl4 Cl 0.08115(6) 0.62636(5) 0.94079(4) 0.03392(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
Ir 0.01050(2) 0.01112(3) 0.00977(2) 0.00042(2) -0.00183(2) -0.00367(2)
Cl1 0.01207(13) 0.01659(14) 0.01625(14) 0.00164(11) -0.00279(11) -0.00524(11)
Cl2 0.01944(15) 0.01438(14) 0.01532(14) -0.00314(11) -0.00262(11) -0.00424(12)
C1 0.0153(6) 0.0189(7) 0.0126(6) 0.0024(5) -0.0060(5) -0.0055(5)
C2 0.0161(6) 0.0183(7) 0.0171(6) 0.0017(5) -0.0071(5) -0.0028(5)
C3 0.0132(6) 0.0256(7) 0.0158(6) -0.0005(5) -0.0039(5) -0.0052(5)
C4 0.0176(6) 0.0208(7) 0.0147(6) 0.0012(5) -0.0054(5) -0.0091(5)
C5 0.0163(6) 0.0170(6) 0.0123(6) -0.0003(5) -0.0044(5) -0.0050(5)
C6 0.0224(7) 0.0267(8) 0.0149(6) 0.0066(6) -0.0043(5) -0.0107(6)
C7 0.0295(8) 0.0178(7) 0.0303(8) 0.0010(6) -0.0132(7) 0.0038(6)
C8 0.0126(6) 0.0425(10) 0.0233(8) -0.0038(7) -0.0008(6) -0.0044(6)
C9 0.0303(8) 0.0274(8) 0.0237(7) 0.0048(6) -0.0101(6) -0.0196(7)
C10 0.0249(7) 0.0218(7) 0.0157(6) -0.0046(5) -0.0054(5) -0.0026(6)
C11 0.0132(6) 0.0135(6) 0.0115(5) 0.0000(4) -0.0025(4) -0.0051(5)
C12 0.0142(6) 0.0127(6) 0.0123(5) 0.0016(4) -0.0036(4) -0.0056(5)
C13 0.0154(6) 0.0125(6) 0.0134(6) 0.0008(5) -0.0038(5) -0.0033(5)
C14 0.0153(6) 0.0123(6) 0.0190(6) 0.0002(5) -0.0023(5) -0.0027(5)
C15 0.0174(6) 0.0172(7) 0.0214(7) 0.0007(5) 0.0003(5) -0.0009(5)
C16 0.0249(8) 0.0179(7) 0.0199(7) -0.0041(6) -0.0018(6) 0.0027(6)
C17 0.0300(8) 0.0161(7) 0.0229(7) -0.0045(6) -0.0063(6) -0.0041(6)
C18 0.0227(7) 0.0155(6) 0.0188(7) -0.0007(5) -0.0045(5) -0.0073(5)
N1 0.0171(5) 0.0146(5) 0.0121(5) 0.0017(4) -0.0005(4) -0.0050(4)
C19 0.0255(8) 0.0211(7) 0.0193(7) 0.0001(6) 0.0071(6) -0.0014(6)
N2 0.0199(6) 0.0164(6) 0.0133(5) 0.0014(4) -0.0016(4) -0.0049(5)
N3 0.0162(5) 0.0146(5) 0.0128(5) 0.0017(4) -0.0036(4) -0.0055(4)
C20 0.0233(7) 0.0154(6) 0.0178(6) 0.0046(5) -0.0075(5) -0.0052(5)
C21 0.0286(8) 0.0231(8) 0.0197(7) 0.0003(6) -0.0031(6) -0.0042(6)
Cl3 0.0295(2) 0.0273(2) 0.0297(2) -0.00347(16) -0.00613(16) -0.00841(16)
Cl4 0.0409(2) 0.0264(2) 0.0396(2) -0.00154(18) -0.0146(2) -0.01166(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
Ir C11 2.0521(14) . ?
Ir C4 2.1430(14) . ?
Ir C5 2.1464(14) . ?
Ir C3 2.1478(15) . ?
Ir C2 2.2263(15) . ?
Ir C1 2.2315(14) . ?
Ir Cl1 2.4164(3) . ?
Ir Cl2 2.4335(3) . ?
C1 C2 1.407(2) . ?
C1 C5 1.458(2) . ?
C1 C6 1.496(2) . ?
C2 C3 1.460(2) . ?
C2 C7 1.490(2) . ?
C3 C4 1.443(2) . ?
C3 C8 1.494(2) . ?
C4 C5 1.443(2) . ?
C4 C9 1.497(2) . ?
C5 C10 1.492(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N1 1.3790(17) . ?
C11 C12 1.408(2) . ?
C12 N3 1.3629(18) . ?
C12 C13 1.476(2) . ?
C13 C14 1.394(2) . ?
C13 C18 1.398(2) . ?
C14 C15 1.392(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 N2 1.3349(18) . ?
N1 C19 1.467(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N2 N3 1.3165(17) . ?
N3 C20 1.4711(19) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 Cl4 1.7529(18) . ?
C21 Cl3 1.7689(18) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?

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 Ir C4 92.60(6) . . ?
C11 Ir C5 109.96(5) . . ?
C4 Ir C5 39.32(5) . . ?
C11 Ir C3 112.05(6) . . ?
C4 Ir C3 39.31(6) . . ?
C5 Ir C3 65.99(6) . . ?
C11 Ir C2 150.98(5) . . ?
C4 Ir C2 64.63(6) . . ?
C5 Ir C2 64.31(6) . . ?
C3 Ir C2 38.94(6) . . ?
C11 Ir C1 148.64(5) . . ?
C4 Ir C1 64.47(5) . . ?
C5 Ir C1 38.84(5) . . ?
C3 Ir C1 64.17(6) . . ?
C2 Ir C1 36.80(5) . . ?
C11 Ir Cl1 92.97(4) . . ?
C4 Ir Cl1 138.77(4) . . ?
C5 Ir Cl1 101.13(4) . . ?
C3 Ir Cl1 154.37(4) . . ?
C2 Ir Cl1 115.97(4) . . ?
C1 Ir Cl1 91.67(4) . . ?
C11 Ir Cl2 93.86(4) . . ?
C4 Ir Cl2 135.77(4) . . ?
C5 Ir Cl2 155.03(4) . . ?
C3 Ir Cl2 98.73(4) . . ?
C2 Ir Cl2 91.25(4) . . ?
C1 Ir Cl2 117.46(4) . . ?
Cl1 Ir Cl2 84.471(12) . . ?
C2 C1 C5 108.71(13) . . ?
C2 C1 C6 127.32(14) . . ?
C5 C1 C6 123.97(14) . . ?
C2 C1 Ir 71.40(8) . . ?
C5 C1 Ir 67.42(8) . . ?
C6 C1 Ir 127.23(10) . . ?
C1 C2 C3 108.52(13) . . ?
C1 C2 C7 126.69(15) . . ?
C3 C2 C7 124.79(14) . . ?
C1 C2 Ir 71.80(8) . . ?
C3 C2 Ir 67.62(8) . . ?
C7 C2 Ir 126.08(11) . . ?
C4 C3 C2 107.20(13) . . ?
C4 C3 C8 127.35(15) . . ?
C2 C3 C8 124.83(15) . . ?
C4 C3 Ir 70.17(8) . . ?
C2 C3 Ir 73.44(8) . . ?
C8 C3 Ir 128.68(11) . . ?
C5 C4 C3 108.22(13) . . ?
C5 C4 C9 125.85(15) . . ?
C3 C4 C9 125.90(14) . . ?
C5 C4 Ir 70.47(8) . . ?
C3 C4 Ir 70.53(8) . . ?
C9 C4 Ir 126.06(11) . . ?
C4 C5 C1 107.17(13) . . ?
C4 C5 C10 128.32(14) . . ?
C1 C5 C10 123.82(13) . . ?
C4 C5 Ir 70.21(8) . . ?
C1 C5 Ir 73.74(8) . . ?
C10 C5 Ir 128.81(11) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 101.35(12) . . ?
N1 C11 Ir 126.54(10) . . ?
C12 C11 Ir 131.61(10) . . ?
N3 C12 C11 107.14(12) . . ?
N3 C12 C13 120.17(12) . . ?
C11 C12 C13 132.23(12) . . ?
C14 C13 C18 119.59(13) . . ?
C14 C13 C12 121.55(13) . . ?
C18 C13 C12 118.87(13) . . ?
C15 C14 C13 119.73(14) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.47(15) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.98(15) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 119.69(15) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C13 120.44(15) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
N2 N1 C11 115.22(12) . . ?
N2 N1 C19 115.48(12) . . ?
C11 N1 C19 129.08(13) . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 N2 N1 103.49(11) . . ?
N2 N3 C12 112.79(12) . . ?
N2 N3 C20 118.46(12) . . ?
C12 N3 C20 128.72(13) . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Cl4 C21 Cl3 111.48(10) . . ?
Cl4 C21 H21A 109.3 . . ?
Cl3 C21 H21A 109.3 . . ?
Cl4 C21 H21B 109.3 . . ?
Cl3 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?

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
C11 Ir C1 C2 -127.72(11) . . . . ?
C4 Ir C1 C2 -81.12(10) . . . . ?
C5 Ir C1 C2 -120.43(12) . . . . ?
C3 Ir C1 C2 -37.30(9) . . . . ?
Cl1 Ir C1 C2 133.81(8) . . . . ?
Cl2 Ir C1 C2 49.17(9) . . . . ?
C11 Ir C1 C5 -7.29(14) . . . . ?
C4 Ir C1 C5 39.30(9) . . . . ?
C3 Ir C1 C5 83.13(9) . . . . ?
C2 Ir C1 C5 120.43(12) . . . . ?
Cl1 Ir C1 C5 -105.76(8) . . . . ?
Cl2 Ir C1 C5 169.60(7) . . . . ?
C11 Ir C1 C6 109.08(15) . . . . ?
C4 Ir C1 C6 155.67(15) . . . . ?
C5 Ir C1 C6 116.36(17) . . . . ?
C3 Ir C1 C6 -160.51(16) . . . . ?
C2 Ir C1 C6 -123.21(18) . . . . ?
Cl1 Ir C1 C6 10.60(14) . . . . ?
Cl2 Ir C1 C6 -74.04(14) . . . . ?
C5 C1 C2 C3 0.60(16) . . . . ?
C6 C1 C2 C3 -179.09(14) . . . . ?
Ir C1 C2 C3 57.81(10) . . . . ?
C5 C1 C2 C7 -179.09(15) . . . . ?
C6 C1 C2 C7 1.2(3) . . . . ?
Ir C1 C2 C7 -121.89(16) . . . . ?
C5 C1 C2 Ir -57.20(10) . . . . ?
C6 C1 C2 Ir 123.10(15) . . . . ?
C11 Ir C2 C1 121.93(12) . . . . ?
C4 Ir C2 C1 80.66(9) . . . . ?
C5 Ir C2 C1 36.88(8) . . . . ?
C3 Ir C2 C1 119.80(13) . . . . ?
Cl1 Ir C2 C1 -53.35(9) . . . . ?
Cl2 Ir C2 C1 -137.81(8) . . . . ?
C11 Ir C2 C3 2.13(16) . . . . ?
C4 Ir C2 C3 -39.14(9) . . . . ?
C5 Ir C2 C3 -82.92(9) . . . . ?
C1 Ir C2 C3 -119.80(13) . . . . ?
Cl1 Ir C2 C3 -173.15(7) . . . . ?
Cl2 Ir C2 C3 102.39(8) . . . . ?
C11 Ir C2 C7 -115.48(16) . . . . ?
C4 Ir C2 C7 -156.75(16) . . . . ?
C5 Ir C2 C7 159.47(16) . . . . ?
C3 Ir C2 C7 -117.61(18) . . . . ?
C1 Ir C2 C7 122.59(18) . . . . ?
Cl1 Ir C2 C7 69.24(15) . . . . ?
Cl2 Ir C2 C7 -15.22(14) . . . . ?
C1 C2 C3 C4 2.05(17) . . . . ?
C7 C2 C3 C4 -178.25(14) . . . . ?
Ir C2 C3 C4 62.44(10) . . . . ?
C1 C2 C3 C8 173.63(14) . . . . ?
C7 C2 C3 C8 -6.7(2) . . . . ?
Ir C2 C3 C8 -125.98(16) . . . . ?
C1 C2 C3 Ir -60.39(10) . . . . ?
C7 C2 C3 Ir 119.31(15) . . . . ?
C11 Ir C3 C4 65.31(9) . . . . ?
C5 Ir C3 C4 -37.56(8) . . . . ?
C2 Ir C3 C4 -115.80(12) . . . . ?
C1 Ir C3 C4 -80.53(9) . . . . ?
Cl1 Ir C3 C4 -101.46(12) . . . . ?
Cl2 Ir C3 C4 163.11(8) . . . . ?
C11 Ir C3 C2 -178.89(8) . . . . ?
C4 Ir C3 C2 115.80(12) . . . . ?
C5 Ir C3 C2 78.25(9) . . . . ?
C1 Ir C3 C2 35.27(8) . . . . ?
Cl1 Ir C3 C2 14.35(16) . . . . ?
Cl2 Ir C3 C2 -81.09(8) . . . . ?
C11 Ir C3 C8 -57.20(17) . . . . ?
C4 Ir C3 C8 -122.51(19) . . . . ?
C5 Ir C3 C8 -160.07(18) . . . . ?
C2 Ir C3 C8 121.7(2) . . . . ?
C1 Ir C3 C8 156.96(18) . . . . ?
Cl1 Ir C3 C8 136.03(13) . . . . ?
Cl2 Ir C3 C8 40.60(16) . . . . ?
C2 C3 C4 C5 -3.93(16) . . . . ?
C8 C3 C4 C5 -175.23(15) . . . . ?
Ir C3 C4 C5 60.67(10) . . . . ?
C2 C3 C4 C9 174.41(14) . . . . ?
C8 C3 C4 C9 3.1(3) . . . . ?
Ir C3 C4 C9 -120.99(15) . . . . ?
C2 C3 C4 Ir -64.60(10) . . . . ?
C8 C3 C4 Ir 124.09(16) . . . . ?
C11 Ir C4 C5 118.94(9) . . . . ?
C3 Ir C4 C5 -118.52(12) . . . . ?
C2 Ir C4 C5 -79.74(9) . . . . ?
C1 Ir C4 C5 -38.82(8) . . . . ?
Cl1 Ir C4 C5 21.45(12) . . . . ?
Cl2 Ir C4 C5 -142.83(7) . . . . ?
C11 Ir C4 C3 -122.55(9) . . . . ?
C5 Ir C4 C3 118.52(12) . . . . ?
C2 Ir C4 C3 38.78(9) . . . . ?
C1 Ir C4 C3 79.69(9) . . . . ?
Cl1 Ir C4 C3 139.97(7) . . . . ?
Cl2 Ir C4 C3 -24.31(11) . . . . ?
C11 Ir C4 C9 -1.76(15) . . . . ?
C5 Ir C4 C9 -120.70(18) . . . . ?
C3 Ir C4 C9 120.79(18) . . . . ?
C2 Ir C4 C9 159.56(16) . . . . ?
C1 Ir C4 C9 -159.52(16) . . . . ?
Cl1 Ir C4 C9 -99.25(14) . . . . ?
Cl2 Ir C4 C9 96.47(15) . . . . ?
C3 C4 C5 C1 4.29(16) . . . . ?
C9 C4 C5 C1 -174.05(14) . . . . ?
Ir C4 C5 C1 65.00(10) . . . . ?
C3 C4 C5 C10 174.92(14) . . . . ?
C9 C4 C5 C10 -3.4(2) . . . . ?
Ir C4 C5 C10 -124.37(16) . . . . ?
C3 C4 C5 Ir -60.71(10) . . . . ?
C9 C4 C5 Ir 120.95(15) . . . . ?
C2 C1 C5 C4 -3.03(16) . . . . ?
C6 C1 C5 C4 176.68(13) . . . . ?
Ir C1 C5 C4 -62.66(10) . . . . ?
C2 C1 C5 C10 -174.18(14) . . . . ?
C6 C1 C5 C10 5.5(2) . . . . ?
Ir C1 C5 C10 126.18(14) . . . . ?
C2 C1 C5 Ir 59.63(10) . . . . ?
C6 C1 C5 Ir -120.65(14) . . . . ?
C11 Ir C5 C4 -68.45(10) . . . . ?
C3 Ir C5 C4 37.54(9) . . . . ?
C2 Ir C5 C4 80.61(9) . . . . ?
C1 Ir C5 C4 115.58(12) . . . . ?
Cl1 Ir C5 C4 -165.78(8) . . . . ?
Cl2 Ir C5 C4 93.27(12) . . . . ?
C11 Ir C5 C1 175.97(8) . . . . ?
C4 Ir C5 C1 -115.58(12) . . . . ?
C3 Ir C5 C1 -78.03(9) . . . . ?
C2 Ir C5 C1 -34.97(8) . . . . ?
Cl1 Ir C5 C1 78.64(8) . . . . ?
Cl2 Ir C5 C1 -22.31(14) . . . . ?
C11 Ir C5 C10 55.35(15) . . . . ?
C4 Ir C5 C10 123.80(17) . . . . ?
C3 Ir C5 C10 161.35(15) . . . . ?
C2 Ir C5 C10 -155.59(15) . . . . ?
C1 Ir C5 C10 -120.62(17) . . . . ?
Cl1 Ir C5 C10 -41.98(14) . . . . ?
Cl2 Ir C5 C10 -142.93(11) . . . . ?
C4 Ir C11 N1 91.35(13) . . . . ?
C5 Ir C11 N1 127.50(12) . . . . ?
C3 Ir C11 N1 56.17(13) . . . . ?
C2 Ir C11 N1 54.72(18) . . . . ?
C1 Ir C11 N1 132.36(12) . . . . ?
Cl1 Ir C11 N1 -129.53(12) . . . . ?
Cl2 Ir C11 N1 -44.87(12) . . . . ?
C4 Ir C11 C12 -78.97(14) . . . . ?
C5 Ir C11 C12 -42.81(14) . . . . ?
C3 Ir C11 C12 -114.15(13) . . . . ?
C2 Ir C11 C12 -115.59(15) . . . . ?
C1 Ir C11 C12 -37.96(19) . . . . ?
Cl1 Ir C11 C12 60.16(13) . . . . ?
Cl2 Ir C11 C12 144.81(13) . . . . ?
N1 C11 C12 N3 1.20(14) . . . . ?
Ir C11 C12 N3 173.28(10) . . . . ?
N1 C11 C12 C13 -170.73(14) . . . . ?
Ir C11 C12 C13 1.3(2) . . . . ?
N3 C12 C13 C14 123.93(15) . . . . ?
C11 C12 C13 C14 -65.0(2) . . . . ?
N3 C12 C13 C18 -56.01(19) . . . . ?
C11 C12 C13 C18 115.06(18) . . . . ?
C18 C13 C14 C15 -3.3(2) . . . . ?
C12 C13 C14 C15 176.73(14) . . . . ?
C13 C14 C15 C16 1.2(2) . . . . ?
C14 C15 C16 C17 1.7(3) . . . . ?
C15 C16 C17 C18 -2.5(3) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
C14 C13 C18 C17 2.6(2) . . . . ?
C12 C13 C18 C17 -177.45(14) . . . . ?
C12 C11 N1 N2 -1.26(16) . . . . ?
Ir C11 N1 N2 -173.89(10) . . . . ?
C12 C11 N1 C19 173.03(15) . . . . ?
Ir C11 N1 C19 0.4(2) . . . . ?
C11 N1 N2 N3 0.77(16) . . . . ?
C19 N1 N2 N3 -174.32(13) . . . . ?
N1 N2 N3 C12 0.10(16) . . . . ?
N1 N2 N3 C20 -178.38(12) . . . . ?
C11 C12 N3 N2 -0.88(16) . . . . ?
C13 C12 N3 N2 172.22(13) . . . . ?
C11 C12 N3 C20 177.41(13) . . . . ?
C13 C12 N3 C20 -9.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.949
_diffrn_reflns_theta_full        32.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.953
_refine_diff_density_rms         0.091