#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:21:43 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179106 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/68/4306827.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4306827
loop_
_publ_author_name
'Jan-Uwe Rohde'
'Matthew R. Kelley'
'Wei-Tsung Lee'
_publ_section_title
;
Synthesis, Characterization, and O2 Reactivity of Iridium(I) Complexes
Supported by Guanidinato Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11461
_journal_page_last               11463
_journal_paper_doi               10.1021/ic801867r
_journal_volume                  47
_journal_year                    2008
_chemical_formula_iupac          '[Ir (C17 H20 N3) (C8 H12)]'
_chemical_formula_moiety         'C25 H32 Ir N3'
_chemical_formula_structural     '(Ir (C17 H20 N3) (C8 H12))'
_chemical_formula_sum            'C25 H32 Ir N3'
_chemical_formula_weight         566.74
_chemical_name_systematic
; 
(η⁴-Cyclooctadiene)(N,N-diethyl-N',N''-
diphenylguanidinato-κ²N',N'')iridium(I)
;
_chemical_properties_physical    air-sensitive
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.034(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2528(11)
_cell_length_b                   17.8077(19)
_cell_length_c                   12.6997(14)
_cell_measurement_reflns_used    10100
_cell_measurement_temperature    209(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      3.03
_cell_volume                     2217.0(4)
_computing_cell_refinement       'HKL-2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL-2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Diamond 3.1 (Crystal Impact, 2008)'
_computing_publication_material  'SHELXTL v6.1 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXTL v6.1 (Bruker AXS, 2001)'
_computing_structure_solution    'SHELXTL v6.1 (Bruker AXS, 2001)'
_diffrn_ambient_temperature      209(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'area detector, φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed x-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19485
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         3.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.038
_exptl_absorpt_correction_T_max  0.8637
_exptl_absorpt_correction_T_min  0.4267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL-2000 (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             1120
_exptl_crystal_recrystallization_method 'n-pentane, -30 °C'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.922
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         5287
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0246
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0164P)²+0.7902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0472
_refine_ls_wR_factor_ref         0.0505
_reflns_number_gt                4310
_reflns_number_total             5287
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic801867r_si_001.cif
_cod_data_source_block           roh87
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4306827
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'
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 0.047169(11) 0.128092(6) 0.263813(9) 0.02912(5) Uani 1 1 d . . .
N1 N -0.0976(2) 0.04762(13) 0.2659(2) 0.0316(6) Uani 1 1 d . . .
N2 N 0.0954(2) 0.01765(13) 0.2354(2) 0.0323(6) Uani 1 1 d . . .
N3 N -0.0644(2) -0.08246(14) 0.2299(2) 0.0330(6) Uani 1 1 d . . .
C1 C -0.0235(3) -0.01035(17) 0.2433(2) 0.0305(7) Uani 1 1 d . . .
C2 C -0.1880(3) 0.04438(17) 0.3318(3) 0.0321(7) Uani 1 1 d . . .
C3 C -0.2880(3) 0.09944(19) 0.3137(3) 0.0416(8) Uani 1 1 d . . .
H3 H -0.2998 0.1332 0.2547 0.050 Uiso 1 1 calc R . .
C4 C -0.3709(4) 0.1048(2) 0.3829(3) 0.0521(10) Uani 1 1 d . . .
H4 H -0.4360 0.1433 0.3723 0.063 Uiso 1 1 calc R . .
C5 C -0.3578(4) 0.0542(2) 0.4662(3) 0.0583(11) Uani 1 1 d . . .
H5 H -0.4142 0.0578 0.5125 0.070 Uiso 1 1 calc R . .
C6 C -0.2622(4) -0.0018(2) 0.4821(3) 0.0533(10) Uani 1 1 d . . .
H6 H -0.2549 -0.0370 0.5387 0.064 Uiso 1 1 calc R . .
C7 C -0.1762(3) -0.00729(19) 0.4161(3) 0.0406(8) Uani 1 1 d . . .
H7 H -0.1105 -0.0457 0.4283 0.049 Uiso 1 1 calc R . .
C8 C 0.1793(3) -0.01037(16) 0.1732(3) 0.0316(7) Uani 1 1 d . . .
C9 C 0.3180(3) 0.00746(18) 0.2105(3) 0.0389(8) Uani 1 1 d . . .
H9 H 0.3534 0.0323 0.2782 0.047 Uiso 1 1 calc R . .
C10 C 0.4034(4) -0.01123(19) 0.1482(3) 0.0468(9) Uani 1 1 d . . .
H10 H 0.4962 0.0018 0.1733 0.056 Uiso 1 1 calc R . .
C11 C 0.3538(4) -0.04871(18) 0.0499(3) 0.0473(9) Uani 1 1 d . . .
H11 H 0.4123 -0.0610 0.0078 0.057 Uiso 1 1 calc R . .
C12 C 0.2183(4) -0.06812(18) 0.0136(3) 0.0405(8) Uani 1 1 d . . .
H12 H 0.1848 -0.0944 -0.0531 0.049 Uiso 1 1 calc R . .
C13 C 0.1299(3) -0.04937(16) 0.0744(2) 0.0328(7) Uani 1 1 d . . .
H13 H 0.0374 -0.0630 0.0489 0.039 Uiso 1 1 calc R . .
C14 C -0.2102(3) -0.10130(18) 0.1932(3) 0.0391(8) Uani 1 1 d . . .
H14A H -0.2637 -0.0548 0.1833 0.047 Uiso 1 1 calc R . .
H14B H -0.2328 -0.1310 0.2505 0.047 Uiso 1 1 calc R . .
C15 C -0.2496(4) -0.1452(2) 0.0865(3) 0.0527(10) Uani 1 1 d . . .
H15A H -0.2248 -0.1167 0.0301 0.079 Uiso 1 1 calc R . .
H15B H -0.3473 -0.1540 0.0636 0.079 Uiso 1 1 calc R . .
H15C H -0.2020 -0.1929 0.0974 0.079 Uiso 1 1 calc R . .
C16 C 0.0346(3) -0.14432(18) 0.2486(3) 0.0408(8) Uani 1 1 d . . .
H16A H 0.1272 -0.1236 0.2732 0.049 Uiso 1 1 calc R . .
H16B H 0.0243 -0.1708 0.1789 0.049 Uiso 1 1 calc R . .
C17 C 0.0161(4) -0.1998(2) 0.3340(3) 0.0633(12) Uani 1 1 d . . .
H17A H 0.0286 -0.1742 0.4036 0.095 Uiso 1 1 calc R . .
H17B H 0.0829 -0.2398 0.3434 0.095 Uiso 1 1 calc R . .
H17C H -0.0750 -0.2210 0.3094 0.095 Uiso 1 1 calc R . .
C18 C -0.0051(3) 0.21344(18) 0.3575(3) 0.0382(8) Uani 1 1 d D . .
H18 H -0.063(3) 0.1926(18) 0.394(3) 0.046 Uiso 1 1 d D . .
C19 C -0.0589(3) 0.23174(18) 0.2452(3) 0.0375(8) Uani 1 1 d D . .
H19 H -0.152(3) 0.2206(17) 0.210(3) 0.045 Uiso 1 1 d D . .
C20 C 0.0006(4) 0.29270(18) 0.1867(3) 0.0455(9) Uani 1 1 d . . .
H20A H -0.0736 0.3168 0.1301 0.055 Uiso 1 1 calc R . .
H20B H 0.0457 0.3312 0.2402 0.055 Uiso 1 1 calc R . .
C21 C 0.1032(3) 0.2594(2) 0.1334(3) 0.0450(9) Uani 1 1 d . . .
H21A H 0.0554 0.2453 0.0572 0.054 Uiso 1 1 calc R . .
H21B H 0.1710 0.2977 0.1314 0.054 Uiso 1 1 calc R . .
C22 C 0.1754(3) 0.19120(19) 0.1940(3) 0.0353(8) Uani 1 1 d D . .
H22 H 0.209(3) 0.1621(19) 0.149(3) 0.042 Uiso 1 1 d D . .
C23 C 0.2349(3) 0.18707(18) 0.3088(3) 0.0341(7) Uani 1 1 d D . .
H23 H 0.306(3) 0.1578(18) 0.336(3) 0.041 Uiso 1 1 d D . .
C24 C 0.2386(3) 0.25269(19) 0.3860(3) 0.0419(8) Uani 1 1 d . . .
H24A H 0.2312 0.2999 0.3451 0.050 Uiso 1 1 calc R . .
H24B H 0.3258 0.2528 0.4444 0.050 Uiso 1 1 calc R . .
C25 C 0.1209(3) 0.2468(2) 0.4372(3) 0.0448(9) Uani 1 1 d . . .
H25A H 0.1492 0.2153 0.5034 0.054 Uiso 1 1 calc R . .
H25B H 0.0994 0.2969 0.4595 0.054 Uiso 1 1 calc R . .
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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 Ir N2 63.68(9) . . ?
N1 Ir C18 101.03(11) . . ?
N2 Ir C18 153.63(12) . . ?
N1 Ir C22 155.68(12) . . ?
N2 Ir C22 102.75(11) . . ?
C18 Ir C22 98.44(13) . . ?
N1 Ir C23 159.76(12) . . ?
N2 Ir C23 105.74(11) . . ?
C18 Ir C23 81.39(13) . . ?
C22 Ir C23 38.87(12) . . ?
N1 Ir C19 104.94(12) . . ?
N2 Ir C19 160.38(12) . . ?
C18 Ir C19 39.04(13) . . ?
C22 Ir C19 81.50(13) . . ?
C23 Ir C19 89.67(13) . . ?
C1 N1 C2 126.5(3) . . ?
C1 N1 Ir 94.32(17) . . ?
C2 N1 Ir 129.09(19) . . ?
C1 N2 C8 128.4(3) . . ?
C1 N2 Ir 94.03(18) . . ?
C8 N2 Ir 129.93(19) . . ?
C1 N3 C14 120.5(3) . . ?
C1 N3 C16 121.3(3) . . ?
C14 N3 C16 118.1(2) . . ?
N3 C1 N2 126.8(3) . . ?
N3 C1 N1 125.3(3) . . ?
N2 C1 N1 108.0(3) . . ?
C3 C2 C7 119.2(3) . . ?
C3 C2 N1 116.9(3) . . ?
C7 C2 N1 123.8(3) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 121.1(4) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C2 119.4(3) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
C13 C8 C9 118.9(3) . . ?
C13 C8 N2 123.9(3) . . ?
C9 C8 N2 117.0(3) . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 119.7(3) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
N3 C14 C15 112.5(3) . . ?
N3 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
N3 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 112.2(3) . . ?
N3 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N3 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C25 126.3(3) . . ?
C19 C18 Ir 71.46(18) . . ?
C25 C18 Ir 110.8(2) . . ?
C19 C18 H18 119(2) . . ?
C25 C18 H18 112(2) . . ?
Ir C18 H18 107(2) . . ?
C18 C19 C20 124.0(3) . . ?
C18 C19 Ir 69.50(18) . . ?
C20 C19 Ir 113.9(2) . . ?
C18 C19 H19 118.4(19) . . ?
C20 C19 H19 113.7(19) . . ?
Ir C19 H19 106.3(19) . . ?
C21 C20 C19 111.2(3) . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 C20 112.6(3) . . ?
C22 C21 H21A 109.1 . . ?
C20 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C23 C22 C21 124.7(3) . . ?
C23 C22 Ir 70.81(17) . . ?
C21 C22 Ir 111.6(2) . . ?
C23 C22 H22 120(2) . . ?
C21 C22 H22 111(2) . . ?
Ir C22 H22 111(2) . . ?
C22 C23 C24 123.4(3) . . ?
C22 C23 Ir 70.32(18) . . ?
C24 C23 Ir 113.9(2) . . ?
C22 C23 H23 120(2) . . ?
C24 C23 H23 110(2) . . ?
Ir C23 H23 113(2) . . ?
C23 C24 C25 110.3(3) . . ?
C23 C24 H24A 109.6 . . ?
C25 C24 H24A 109.6 . . ?
C23 C24 H24B 109.6 . . ?
C25 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C18 C25 C24 111.6(3) . . ?
C18 C25 H25A 109.3 . . ?
C24 C25 H25A 109.3 . . ?
C18 C25 H25B 109.3 . . ?
C24 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
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 N1 2.069(2) . ?
Ir N2 2.085(2) . ?
Ir C18 2.095(3) . ?
Ir C22 2.112(3) . ?
Ir C23 2.119(3) . ?
Ir C19 2.120(3) . ?
N1 C1 1.361(4) . ?
N1 C2 1.420(4) . ?
N2 C1 1.348(4) . ?
N2 C8 1.417(4) . ?
N3 C1 1.346(4) . ?
N3 C14 1.469(4) . ?
N3 C16 1.470(4) . ?
C2 C3 1.388(4) . ?
C2 C7 1.390(4) . ?
C3 C4 1.393(5) . ?
C3 H3 0.9400 . ?
C4 C5 1.365(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.370(5) . ?
C5 H5 0.9400 . ?
C6 C7 1.387(4) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C8 C13 1.394(4) . ?
C8 C9 1.398(4) . ?
C9 C10 1.381(4) . ?
C9 H9 0.9400 . ?
C10 C11 1.375(5) . ?
C10 H10 0.9400 . ?
C11 C12 1.373(5) . ?
C11 H11 0.9400 . ?
C12 C13 1.392(4) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?
C14 C15 1.513(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 C17 1.520(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 C19 1.408(5) . ?
C18 C25 1.510(5) . ?
C18 H18 0.93(3) . ?
C19 C20 1.539(4) . ?
C19 H19 0.95(3) . ?
C20 C21 1.528(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C21 C22 1.510(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 C23 1.408(4) . ?
C22 H22 0.91(3) . ?
C23 C24 1.519(4) . ?
C23 H23 0.88(3) . ?
C24 C25 1.533(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
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
N2 Ir N1 C1 -0.76(17) . . . . ?
C18 Ir N1 C1 -157.98(19) . . . . ?
C22 Ir N1 C1 59.5(3) . . . . ?
C23 Ir N1 C1 -62.9(4) . . . . ?
C19 Ir N1 C1 162.11(18) . . . . ?
N2 Ir N1 C2 145.3(3) . . . . ?
C18 Ir N1 C2 -11.9(3) . . . . ?
C22 Ir N1 C2 -154.4(3) . . . . ?
C23 Ir N1 C2 83.1(4) . . . . ?
C19 Ir N1 C2 -51.8(3) . . . . ?
N1 Ir N2 C1 0.77(17) . . . . ?
C18 Ir N2 C1 59.6(3) . . . . ?
C22 Ir N2 C1 -157.72(19) . . . . ?
C23 Ir N2 C1 162.24(18) . . . . ?
C19 Ir N2 C1 -57.1(4) . . . . ?
N1 Ir N2 C8 151.2(3) . . . . ?
C18 Ir N2 C8 -149.9(3) . . . . ?
C22 Ir N2 C8 -7.3(3) . . . . ?
C23 Ir N2 C8 -47.3(3) . . . . ?
C19 Ir N2 C8 93.3(4) . . . . ?
C14 N3 C1 N2 -153.2(3) . . . . ?
C16 N3 C1 N2 25.1(5) . . . . ?
C14 N3 C1 N1 25.9(4) . . . . ?
C16 N3 C1 N1 -155.8(3) . . . . ?
C8 N2 C1 N3 26.9(5) . . . . ?
Ir N2 C1 N3 178.1(3) . . . . ?
C8 N2 C1 N1 -152.3(3) . . . . ?
Ir N2 C1 N1 -1.1(2) . . . . ?
C2 N1 C1 N3 34.5(5) . . . . ?
Ir N1 C1 N3 -178.1(3) . . . . ?
C2 N1 C1 N2 -146.3(3) . . . . ?
Ir N1 C1 N2 1.1(2) . . . . ?
C1 N1 C2 C3 -157.5(3) . . . . ?
Ir N1 C2 C3 66.3(4) . . . . ?
C1 N1 C2 C7 26.5(5) . . . . ?
Ir N1 C2 C7 -109.7(3) . . . . ?
C7 C2 C3 C4 3.1(5) . . . . ?
N1 C2 C3 C4 -173.1(3) . . . . ?
C2 C3 C4 C5 -2.5(5) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C4 C5 C6 C7 1.2(6) . . . . ?
C5 C6 C7 C2 -0.6(5) . . . . ?
C3 C2 C7 C6 -1.5(5) . . . . ?
N1 C2 C7 C6 174.3(3) . . . . ?
C1 N2 C8 C13 30.4(5) . . . . ?
Ir N2 C8 C13 -110.8(3) . . . . ?
C1 N2 C8 C9 -154.4(3) . . . . ?
Ir N2 C8 C9 64.4(4) . . . . ?
C13 C8 C9 C10 2.1(5) . . . . ?
N2 C8 C9 C10 -173.3(3) . . . . ?
C8 C9 C10 C11 -1.2(5) . . . . ?
C9 C10 C11 C12 -0.3(5) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
C11 C12 C13 C8 0.1(5) . . . . ?
C9 C8 C13 C12 -1.6(4) . . . . ?
N2 C8 C13 C12 173.6(3) . . . . ?
C1 N3 C14 C15 120.4(3) . . . . ?
C16 N3 C14 C15 -58.0(4) . . . . ?
C1 N3 C16 C17 123.3(3) . . . . ?
C14 N3 C16 C17 -58.4(4) . . . . ?
N1 Ir C18 C19 -100.2(2) . . . . ?
N2 Ir C18 C19 -151.6(2) . . . . ?
C22 Ir C18 C19 65.2(2) . . . . ?
C23 Ir C18 C19 100.2(2) . . . . ?
N1 Ir C18 C25 137.1(2) . . . . ?
N2 Ir C18 C25 85.7(3) . . . . ?
C22 Ir C18 C25 -57.6(3) . . . . ?
C23 Ir C18 C25 -22.5(2) . . . . ?
C19 Ir C18 C25 -122.8(3) . . . . ?
C25 C18 C19 C20 -3.0(5) . . . . ?
Ir C18 C19 C20 -105.6(3) . . . . ?
C25 C18 C19 Ir 102.6(3) . . . . ?
N1 Ir C19 C18 89.2(2) . . . . ?
N2 Ir C19 C18 141.0(3) . . . . ?
C22 Ir C19 C18 -114.8(2) . . . . ?
C23 Ir C19 C18 -76.7(2) . . . . ?
N1 Ir C19 C20 -151.7(2) . . . . ?
N2 Ir C19 C20 -99.9(4) . . . . ?
C18 Ir C19 C20 119.2(3) . . . . ?
C22 Ir C19 C20 4.3(2) . . . . ?
C23 Ir C19 C20 42.5(3) . . . . ?
C18 C19 C20 C21 93.0(4) . . . . ?
Ir C19 C20 C21 12.4(4) . . . . ?
C19 C20 C21 C22 -29.6(4) . . . . ?
C20 C21 C22 C23 -47.6(4) . . . . ?
C20 C21 C22 Ir 33.5(4) . . . . ?
N1 Ir C22 C23 -152.3(2) . . . . ?
N2 Ir C22 C23 -99.4(2) . . . . ?
C18 Ir C22 C23 64.8(2) . . . . ?
C19 Ir C22 C23 100.1(2) . . . . ?
N1 Ir C22 C21 87.1(4) . . . . ?
N2 Ir C22 C21 140.0(2) . . . . ?
C18 Ir C22 C21 -55.8(3) . . . . ?
C23 Ir C22 C21 -120.7(3) . . . . ?
C19 Ir C22 C21 -20.5(2) . . . . ?
C21 C22 C23 C24 -2.7(5) . . . . ?
Ir C22 C23 C24 -106.2(3) . . . . ?
C21 C22 C23 Ir 103.5(3) . . . . ?
N1 Ir C23 C22 146.3(3) . . . . ?
N2 Ir C23 C22 90.9(2) . . . . ?
C18 Ir C23 C22 -115.1(2) . . . . ?
C19 Ir C23 C22 -76.8(2) . . . . ?
N1 Ir C23 C24 -94.9(4) . . . . ?
N2 Ir C23 C24 -150.4(2) . . . . ?
C18 Ir C23 C24 3.6(2) . . . . ?
C22 Ir C23 C24 118.7(3) . . . . ?
C19 Ir C23 C24 41.9(3) . . . . ?
C22 C23 C24 C25 97.1(4) . . . . ?
Ir C23 C24 C25 15.7(4) . . . . ?
C19 C18 C25 C24 -43.9(5) . . . . ?
Ir C18 C25 C24 37.9(4) . . . . ?
C23 C24 C25 C18 -34.6(4) . . . . ?
