#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:35:21 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178717 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/28/4082828.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_4082828
loop_
_publ_author_name
'Casarrubios, Luis'
'Esteruelas, Miguel A.'
'Larramona, Carmen'
'Muntaner, Jaime G.'
'Oliván, Montserrat'
'Oñate, Enrique'
'Sierra, Miguel A.'
_publ_section_title
;
 Chelated Assisted Metal-Mediated N--H Bond Activation of β-Lactams:
 Preparation of Irida-, Rhoda-, Osma-, and Ruthenatrinems
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              1820
_journal_paper_doi               10.1021/om500162m
_journal_volume                  33
_journal_year                    2014
_chemical_formula_sum            'C27 H29 Cl Ir N2 O2'
_chemical_formula_weight         641.17
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.514(4)
_cell_angle_beta                 108.068(3)
_cell_angle_gamma                105.722(4)
_cell_formula_units_Z            2
_cell_length_a                   10.853(2)
_cell_length_b                   10.896(2)
_cell_length_c                   12.009(3)
_cell_measurement_reflns_used    2192
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      20.24
_cell_measurement_theta_min      2.23
_cell_volume                     1257.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1015
_diffrn_reflns_av_sigmaI/netI    0.1337
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9523
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    5.443
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Absorption correction performed with SADABS program. This is based on the
method of Blessing: Blessing, R. H., Acta Crystallogr., Sect. A 1995, 51, 33.

SADABS: Area-Detector Absorption Correction. Bruker-AXS 
within SAINT+ package, v. 6.1 (2000).
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             630
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         2.032
_refine_diff_density_min         -1.143
_refine_diff_density_rms         0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0370P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                2936
_reflns_number_total             4298
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om500162m_si_002.cif
_cod_data_source_block           jm-p64
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4082828.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4082828
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.2411(9) 0.0892(8) 0.1360(8) 0.0336(17) Uani 1 1 d .
C1 C 0.1706(12) 0.0018(12) 0.0177(12) 0.047(3) Uani 1 1 d .
C2 C 0.1012(12) -0.1167(10) 0.0663(10) 0.043(3) Uani 1 1 d .
H2 H 0.0025 -0.1346 0.0476 0.051 Uiso 1 1 calc R
C3 C 0.1927(11) -0.0210(9) 0.1904(9) 0.0336(17) Uani 1 1 d .
H3 H 0.1396 -0.0012 0.2391 0.040 Uiso 1 1 calc R
C4 C 0.3171(13) -0.0476(10) 0.2616(9) 0.043(3) Uani 1 1 d .
C5 C 0.3129(15) -0.1553(11) 0.3094(11) 0.061(4) Uani 1 1 d .
H5 H 0.2279 -0.2165 0.2962 0.073 Uiso 1 1 calc R
C6 C 0.4303(17) -0.1744(13) 0.3757(12) 0.063(4) Uani 1 1 d .
H6 H 0.4262 -0.2484 0.4061 0.076 Uiso 1 1 calc R
C7 C 0.5527(16) -0.0830(14) 0.3959(11) 0.059(4) Uani 1 1 d .
H7 H 0.6343 -0.0940 0.4400 0.071 Uiso 1 1 calc R
C8 C 0.5560(13) 0.0271(12) 0.3507(11) 0.050(3) Uani 1 1 d .
H8 H 0.6402 0.0919 0.3683 0.060 Uiso 1 1 calc R
C9 C 0.0632(11) -0.3253(11) -0.0582(11) 0.039(3) Uani 1 1 d .
C10 C -0.0412(12) -0.3205(12) -0.1552(11) 0.052(3) Uani 1 1 d .
H10 H -0.0718 -0.2487 -0.1493 0.063 Uiso 1 1 calc R
C11 C -0.1010(12) -0.4172(12) -0.2592(11) 0.049(3) Uani 1 1 d .
H11 H -0.1741 -0.4133 -0.3228 0.059 Uiso 1 1 calc R
C12 C -0.0529(14) -0.5215(13) -0.2704(13) 0.068(4) Uani 1 1 d .
H12 H -0.0917 -0.5871 -0.3424 0.082 Uiso 1 1 calc R
C13 C 0.0526(15) -0.5284(13) -0.1749(13) 0.065(4) Uani 1 1 d .
H13 H 0.0857 -0.5982 -0.1827 0.078 Uiso 1 1 calc R
C14 C 0.1087(13) -0.4333(13) -0.0689(12) 0.058(4) Uani 1 1 d .
H14 H 0.1775 -0.4401 -0.0034 0.070 Uiso 1 1 calc R
C15 C 0.6314(12) 0.2903(13) 0.2116(12) 0.050(3) Uani 1 1 d .
C16 C 0.6132(12) 0.3731(13) 0.2748(12) 0.050(3) Uani 1 1 d .
C17 C 0.5055(12) 0.4189(10) 0.2130(10) 0.045(2) Uani 1 1 d .
C18 C 0.4491(12) 0.3353(11) 0.0887(10) 0.045(2) Uani 1 1 d .
C19 C 0.5259(14) 0.2494(11) 0.0826(11) 0.051(3) Uani 1 1 d .
C20 C 0.7448(12) 0.2254(13) 0.2357(13) 0.070(4) Uani 1 1 d .
H20A H 0.8107 0.2649 0.3168 0.105 Uiso 1 1 calc R
H20B H 0.7904 0.2383 0.1793 0.105 Uiso 1 1 calc R
H20C H 0.7036 0.1327 0.2260 0.105 Uiso 1 1 calc R
C21 C 0.7097(16) 0.4533(14) 0.4090(13) 0.092(5) Uani 1 1 d .
H21A H 0.7124 0.3943 0.4609 0.139 Uiso 1 1 calc R
H21B H 0.6744 0.5191 0.4358 0.139 Uiso 1 1 calc R
H21C H 0.8010 0.4952 0.4116 0.139 Uiso 1 1 calc R
C22 C 0.4599(15) 0.5286(11) 0.2541(13) 0.074(4) Uani 1 1 d .
H22A H 0.5030 0.6057 0.2323 0.110 Uiso 1 1 calc R
H22B H 0.4854 0.5475 0.3404 0.110 Uiso 1 1 calc R
H22C H 0.3617 0.5034 0.2161 0.110 Uiso 1 1 calc R
C23 C 0.3303(13) 0.3416(13) -0.0125(12) 0.072(4) Uani 1 1 d .
H23A H 0.2588 0.3487 0.0165 0.108 Uiso 1 1 calc R
H23B H 0.2954 0.2630 -0.0770 0.108 Uiso 1 1 calc R
H23C H 0.3604 0.4171 -0.0421 0.108 Uiso 1 1 calc R
C24 C 0.5155(15) 0.1633(12) -0.0300(12) 0.070(4) Uani 1 1 d .
H24A H 0.4234 0.1019 -0.0697 0.105 Uiso 1 1 calc R
H24B H 0.5788 0.1159 -0.0104 0.105 Uiso 1 1 calc R
H24C H 0.5377 0.2163 -0.0828 0.105 Uiso 1 1 calc R
Cl1 Cl 0.3579(3) 0.2702(3) 0.3814(3) 0.0515(8) Uani 1 1 d .
Ir1 Ir 0.43246(5) 0.21605(5) 0.21471(4) 0.03515(18) Uani 1 1 d .
N2 N 0.4383(10) 0.0423(8) 0.2811(8) 0.039(2) Uani 1 1 d .
O1 O 0.1613(9) 0.0066(8) -0.0855(8) 0.059(2) Uani 1 1 d .
O2 O 0.1370(8) -0.2317(8) 0.0481(7) 0.048(2) Uani 1 1 d .
C25 C -0.005(2) -0.074(3) 0.581(2) 0.147(8) Uiso 1 1 d .
H25 H -0.0066 -0.1259 0.6356 0.176 Uiso 1 1 calc R
C26 C 0.067(3) 0.052(3) 0.620(2) 0.163(9) Uiso 1 1 d .
H26 H 0.1097 0.0877 0.7030 0.195 Uiso 1 1 calc R
C27 C 0.081(3) 0.132(3) 0.546(3) 0.196(11) Uiso 1 1 d .
H27 H 0.1377 0.2203 0.5761 0.235 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1 N1 C3 90.1(8) . .
C1 N1 Ir1 131.0(7) . .
C3 N1 Ir1 120.0(6) . .
O1 C1 N1 136.7(11) . .
O1 C1 C2 130.0(11) . .
N1 C1 C2 93.3(9) . .
O2 C2 C3 112.2(9) . .
O2 C2 C1 116.9(9) . .
C3 C2 C1 82.9(8) . .
O2 C2 H2 113.8 . .
C3 C2 H2 113.8 . .
C1 C2 H2 113.8 . .
C4 C3 N1 106.8(8) . .
C4 C3 C2 117.6(9) . .
N1 C3 C2 93.1(8) . .
C4 C3 H3 112.6 . .
N1 C3 H3 112.6 . .
C2 C3 H3 112.6 . .
N2 C4 C5 119.9(11) . .
N2 C4 C3 116.1(9) . .
C5 C4 C3 123.9(12) . .
C6 C5 C4 121.6(13) . .
C6 C5 H5 119.2 . .
C4 C5 H5 119.2 . .
C5 C6 C7 118.4(11) . .
C5 C6 H6 120.8 . .
C7 C6 H6 120.8 . .
C6 C7 C8 119.7(12) . .
C6 C7 H7 120.2 . .
C8 C7 H7 120.2 . .
N2 C8 C7 121.3(13) . .
N2 C8 H8 119.4 . .
C7 C8 H8 119.4 . .
O2 C9 C10 127.6(10) . .
O2 C9 C14 113.9(10) . .
C10 C9 C14 118.3(12) . .
C9 C10 C11 121.8(11) . .
C9 C10 H10 119.1 . .
C11 C10 H10 119.1 . .
C12 C11 C10 119.5(12) . .
C12 C11 H11 120.2 . .
C10 C11 H11 120.2 . .
C11 C12 C13 119.9(13) . .
C11 C12 H12 120.0 . .
C13 C12 H12 120.0 . .
C14 C13 C12 120.2(12) . .
C14 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
C13 C14 C9 120.1(11) . .
C13 C14 H14 119.9 . .
C9 C14 H14 119.9 . .
C16 C15 C20 131.8(13) . .
C16 C15 C19 111.4(11) . .
C20 C15 C19 116.7(12) . .
C16 C15 Ir1 71.2(9) . .
C20 C15 Ir1 127.7(8) . .
C19 C15 Ir1 70.8(6) . .
C15 C16 C17 114.4(13) . .
C15 C16 C21 127.0(12) . .
C17 C16 C21 117.5(12) . .
C15 C16 Ir1 75.6(9) . .
C17 C16 Ir1 73.3(6) . .
C21 C16 Ir1 129.0(9) . .
C18 C17 C16 103.5(10) . .
C18 C17 C22 124.8(11) . .
C16 C17 C22 131.5(12) . .
C18 C17 Ir1 70.4(6) . .
C16 C17 Ir1 66.9(6) . .
C22 C17 Ir1 128.8(8) . .
C17 C18 C19 108.3(10) . .
C17 C18 C23 124.9(11) . .
C19 C18 C23 126.8(11) . .
C17 C18 Ir1 69.6(6) . .
C19 C18 Ir1 70.8(6) . .
C23 C18 Ir1 125.2(8) . .
C18 C19 C24 125.3(12) . .
C18 C19 C15 102.3(9) . .
C24 C19 C15 131.5(12) . .
C18 C19 Ir1 70.7(6) . .
C24 C19 Ir1 133.1(8) . .
C15 C19 Ir1 67.3(6) . .
C15 C20 H20A 109.5 . .
C15 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C15 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C16 C21 H21A 109.5 . .
C16 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C16 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C17 C22 H22A 109.5 . .
C17 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C17 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C18 C23 H23A 109.5 . .
C18 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C18 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C19 C24 H24A 109.5 . .
C19 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C19 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
N1 Ir1 C16 167.5(3) . .
N1 Ir1 C15 149.0(5) . .
C16 Ir1 C15 33.2(4) . .
N1 Ir1 C17 127.9(4) . .
C16 Ir1 C17 39.8(4) . .
C15 Ir1 C17 62.7(4) . .
N1 Ir1 C18 103.4(4) . .
C16 Ir1 C18 65.5(4) . .
C15 Ir1 C18 65.2(4) . .
C17 Ir1 C18 40.0(4) . .
N1 Ir1 C19 110.8(4) . .
C16 Ir1 C19 64.6(5) . .
C15 Ir1 C19 42.0(5) . .
C17 Ir1 C19 66.1(4) . .
C18 Ir1 C19 38.5(4) . .
N1 Ir1 N2 75.0(3) . .
C16 Ir1 N2 117.5(4) . .
C15 Ir1 N2 102.3(4) . .
C17 Ir1 N2 156.0(4) . .
C18 Ir1 N2 153.4(4) . .
C19 Ir1 N2 116.5(4) . .
N1 Ir1 Cl1 83.5(3) . .
C16 Ir1 Cl1 97.8(4) . .
C15 Ir1 Cl1 127.2(4) . .
C17 Ir1 Cl1 91.9(3) . .
C18 Ir1 Cl1 123.6(3) . .
C19 Ir1 Cl1 157.9(3) . .
N2 Ir1 Cl1 82.9(2) . .
C4 N2 C8 119.0(9) . .
C4 N2 Ir1 116.8(7) . .
C8 N2 Ir1 123.8(8) . .
C9 O2 C2 118.2(8) . .
C26 C25 C27 120(3) . 2_556
C26 C25 H25 119.9 . .
C27 C25 H25 119.9 2_556 .
C25 C26 C27 124(3) . .
C25 C26 H26 118.1 . .
C27 C26 H26 118.1 . .
C26 C27 C25 116(3) . 2_556
C26 C27 H27 122.0 . .
C25 C27 H27 122.1 2_556 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.428(14) .
N1 C3 1.500(11) .
N1 Ir1 1.989(9) .
C1 O1 1.222(13) .
C1 C2 1.595(15) .
C2 O2 1.417(12) .
C2 C3 1.534(15) .
C2 H2 0.9800 .
C3 C4 1.485(14) .
C3 H3 0.9800 .
C4 N2 1.337(14) .
C4 C5 1.376(15) .
C5 C6 1.366(17) .
C5 H5 0.9300 .
C6 C7 1.351(18) .
C6 H6 0.9300 .
C7 C8 1.384(16) .
C7 H7 0.9300 .
C8 N2 1.361(13) .
C8 H8 0.9300 .
C9 O2 1.359(12) .
C9 C10 1.369(15) .
C9 C14 1.398(15) .
C10 C11 1.352(15) .
C10 H10 0.9300 .
C11 C12 1.380(16) .
C11 H11 0.9300 .
C12 C13 1.374(16) .
C12 H12 0.9300 .
C13 C14 1.360(16) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C15 C16 1.191(16) .
C15 C20 1.553(15) .
C15 C19 1.526(17) .
C15 Ir1 2.105(11) .
C16 C17 1.432(15) .
C16 C21 1.580(18) .
C16 Ir1 2.058(12) .
C17 C18 1.470(15) .
C17 C22 1.489(14) .
C17 Ir1 2.142(10) .
C18 C19 1.420(15) .
C18 C23 1.498(15) .
C18 Ir1 2.154(10) .
C19 C24 1.481(15) .
C19 Ir1 2.155(11) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
Cl1 Ir1 2.434(3) .
Ir1 N2 2.168(8) .
C25 C26 1.31(3) .
C25 C27 1.44(3) 2_556
C25 H25 0.9300 .
C26 C27 1.35(3) .
C26 H26 0.9300 .
C27 C25 1.44(3) 2_556
C27 H27 0.9300 .
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_4
C3 N1 C1 O1 -173.9(14) . .
Ir1 N1 C1 O1 -42.3(18) . .
C3 N1 C1 C2 5.8(8) . .
Ir1 N1 C1 C2 137.4(7) . .
O1 C1 C2 O2 62.6(16) . .
N1 C1 C2 O2 -117.1(10) . .
O1 C1 C2 C3 174.0(12) . .
N1 C1 C2 C3 -5.7(8) . .
C1 N1 C3 C4 113.9(9) . .
Ir1 N1 C3 C4 -25.3(11) . .
C1 N1 C3 C2 -6.1(8) . .
Ir1 N1 C3 C2 -145.3(7) . .
O2 C2 C3 C4 11.0(14) . .
C1 C2 C3 C4 -105.2(10) . .
O2 C2 C3 N1 121.7(9) . .
C1 C2 C3 N1 5.5(7) . .
N1 C3 C4 N2 12.3(13) . .
C2 C3 C4 N2 115.0(11) . .
N1 C3 C4 C5 -169.4(10) . .
C2 C3 C4 C5 -66.7(15) . .
N2 C4 C5 C6 -0.9(18) . .
C3 C4 C5 C6 -179.1(11) . .
C4 C5 C6 C7 1(2) . .
C5 C6 C7 C8 0.7(19) . .
C6 C7 C8 N2 -3.2(19) . .
O2 C9 C10 C11 175.8(12) . .
C14 C9 C10 C11 0.5(18) . .
C9 C10 C11 C12 -2(2) . .
C10 C11 C12 C13 2(2) . .
C11 C12 C13 C14 1(2) . .
C12 C13 C14 C9 -3(2) . .
O2 C9 C14 C13 -173.9(12) . .
C10 C9 C14 C13 2.0(19) . .
C20 C15 C16 C17 172.0(11) . .
C19 C15 C16 C17 -4.2(15) . .
Ir1 C15 C16 C17 -63.7(9) . .
C20 C15 C16 C21 4(2) . .
C19 C15 C16 C21 -172.1(11) . .
Ir1 C15 C16 C21 128.3(13) . .
C20 C15 C16 Ir1 -124.3(13) . .
C19 C15 C16 Ir1 59.6(8) . .
C15 C16 C17 C18 3.6(14) . .
C21 C16 C17 C18 172.8(10) . .
Ir1 C16 C17 C18 -61.5(7) . .
C15 C16 C17 C22 -172.8(12) . .
C21 C16 C17 C22 -3.6(18) . .
Ir1 C16 C17 C22 122.1(12) . .
C15 C16 C17 Ir1 65.1(11) . .
C21 C16 C17 Ir1 -125.7(11) . .
C16 C17 C18 C19 -1.4(12) . .
C22 C17 C18 C19 175.3(10) . .
Ir1 C17 C18 C19 -60.5(7) . .
C16 C17 C18 C23 178.4(10) . .
C22 C17 C18 C23 -4.9(18) . .
Ir1 C17 C18 C23 119.3(11) . .
C16 C17 C18 Ir1 59.1(7) . .
C22 C17 C18 Ir1 -124.2(11) . .
C17 C18 C19 C24 -170.6(11) . .
C23 C18 C19 C24 9.6(18) . .
Ir1 C18 C19 C24 129.7(12) . .
C17 C18 C19 C15 -0.6(11) . .
C23 C18 C19 C15 179.6(11) . .
Ir1 C18 C19 C15 -60.3(7) . .
C17 C18 C19 Ir1 59.7(7) . .
C23 C18 C19 Ir1 -120.1(11) . .
C16 C15 C19 C18 2.9(14) . .
C20 C15 C19 C18 -173.9(9) . .
Ir1 C15 C19 C18 62.7(7) . .
C16 C15 C19 C24 172.0(12) . .
C20 C15 C19 C24 -4.8(17) . .
Ir1 C15 C19 C24 -128.2(13) . .
C16 C15 C19 Ir1 -59.8(10) . .
C20 C15 C19 Ir1 123.4(9) . .
C1 N1 Ir1 C16 80(2) . .
C3 N1 Ir1 C16 -159.7(19) . .
C1 N1 Ir1 C15 -10.0(12) . .
C3 N1 Ir1 C15 110.2(9) . .
C1 N1 Ir1 C17 89.5(9) . .
C3 N1 Ir1 C17 -150.3(7) . .
C1 N1 Ir1 C18 53.8(9) . .
C3 N1 Ir1 C18 174.0(7) . .
C1 N1 Ir1 C19 14.2(9) . .
C3 N1 Ir1 C19 134.4(7) . .
C1 N1 Ir1 N2 -98.9(8) . .
C3 N1 Ir1 N2 21.4(7) . .
C1 N1 Ir1 Cl1 176.8(8) . .
C3 N1 Ir1 Cl1 -62.9(7) . .
C15 C16 Ir1 N1 -110(2) . .
C17 C16 Ir1 N1 12(2) . .
C21 C16 Ir1 N1 123.9(19) . .
C17 C16 Ir1 C15 121.5(11) . .
C21 C16 Ir1 C15 -126.3(14) . .
C15 C16 Ir1 C17 -121.5(11) . .
C21 C16 Ir1 C17 112.2(15) . .
C15 C16 Ir1 C18 -81.6(8) . .
C17 C16 Ir1 C18 39.9(7) . .
C21 C16 Ir1 C18 152.1(13) . .
C15 C16 Ir1 C19 -39.0(8) . .
C17 C16 Ir1 C19 82.5(7) . .
C21 C16 Ir1 C19 -165.3(13) . .
C15 C16 Ir1 N2 69.0(9) . .
C17 C16 Ir1 N2 -169.6(6) . .
C21 C16 Ir1 N2 -57.4(13) . .
C15 C16 Ir1 Cl1 154.9(7) . .
C17 C16 Ir1 Cl1 -83.6(7) . .
C21 C16 Ir1 Cl1 28.6(11) . .
C16 C15 Ir1 N1 156.7(7) . .
C20 C15 Ir1 N1 -74.4(13) . .
C19 C15 Ir1 N1 35.0(10) . .
C20 C15 Ir1 C16 128.9(16) . .
C19 C15 Ir1 C16 -121.8(10) . .
C16 C15 Ir1 C17 37.9(7) . .
C20 C15 Ir1 C17 166.8(14) . .
C19 C15 Ir1 C17 -83.8(6) . .
C16 C15 Ir1 C18 82.6(8) . .
C20 C15 Ir1 C18 -148.5(14) . .
C19 C15 Ir1 C18 -39.1(6) . .
C16 C15 Ir1 C19 121.8(10) . .
C20 C15 Ir1 C19 -109.4(15) . .
C16 C15 Ir1 N2 -122.1(7) . .
C20 C15 Ir1 N2 6.7(13) . .
C19 C15 Ir1 N2 116.1(6) . .
C16 C15 Ir1 Cl1 -31.8(9) . .
C20 C15 Ir1 Cl1 97.1(12) . .
C19 C15 Ir1 Cl1 -153.6(5) . .
C18 C17 Ir1 N1 -61.9(8) . .
C16 C17 Ir1 N1 -176.8(7) . .
C22 C17 Ir1 N1 57.6(13) . .
C18 C17 Ir1 C16 114.9(10) . .
C22 C17 Ir1 C16 -125.6(15) . .
C18 C17 Ir1 C15 83.2(7) . .
C16 C17 Ir1 C15 -31.7(7) . .
C22 C17 Ir1 C15 -157.3(13) . .
C16 C17 Ir1 C18 -114.9(10) . .
C22 C17 Ir1 C18 119.5(14) . .
C18 C17 Ir1 C19 36.6(7) . .
C16 C17 Ir1 C19 -78.4(8) . .
C22 C17 Ir1 C19 156.0(13) . .
C18 C17 Ir1 N2 138.2(9) . .
C16 C17 Ir1 N2 23.3(13) . .
C22 C17 Ir1 N2 -102.3(13) . .
C18 C17 Ir1 Cl1 -145.2(6) . .
C16 C17 Ir1 Cl1 99.9(7) . .
C22 C17 Ir1 Cl1 -25.7(11) . .
C17 C18 Ir1 N1 134.3(6) . .
C19 C18 Ir1 N1 -106.7(7) . .
C23 C18 Ir1 N1 15.4(11) . .
C17 C18 Ir1 C16 -39.7(7) . .
C19 C18 Ir1 C16 79.3(8) . .
C23 C18 Ir1 C16 -158.6(12) . .
C17 C18 Ir1 C15 -76.3(8) . .
C19 C18 Ir1 C15 42.7(7) . .
C23 C18 Ir1 C15 164.8(12) . .
C19 C18 Ir1 C17 119.0(10) . .
C23 C18 Ir1 C17 -118.9(13) . .
C17 C18 Ir1 C19 -119.0(10) . .
C23 C18 Ir1 C19 122.1(14) . .
C17 C18 Ir1 N2 -142.7(8) . .
C19 C18 Ir1 N2 -23.7(13) . .
C23 C18 Ir1 N2 98.4(13) . .
C17 C18 Ir1 Cl1 43.3(8) . .
C19 C18 Ir1 Cl1 162.2(6) . .
C23 C18 Ir1 Cl1 -75.7(11) . .
C18 C19 Ir1 N1 85.4(7) . .
C24 C19 Ir1 N1 -35.3(14) . .
C15 C19 Ir1 N1 -161.6(6) . .
C18 C19 Ir1 C16 -82.0(7) . .
C24 C19 Ir1 C16 157.3(14) . .
C15 C19 Ir1 C16 31.0(6) . .
C18 C19 Ir1 C15 -113.0(9) . .
C24 C19 Ir1 C15 126.2(16) . .
C18 C19 Ir1 C17 -38.0(7) . .
C24 C19 Ir1 C17 -158.7(14) . .
C15 C19 Ir1 C17 75.0(7) . .
C24 C19 Ir1 C18 -120.7(16) . .
C15 C19 Ir1 C18 113.0(9) . .
C18 C19 Ir1 N2 168.4(6) . .
C24 C19 Ir1 N2 47.7(14) . .
C15 C19 Ir1 N2 -78.5(7) . .
C18 C19 Ir1 Cl1 -42.6(13) . .
C24 C19 Ir1 Cl1 -163.3(8) . .
C15 C19 Ir1 Cl1 70.5(12) . .
C5 C4 N2 C8 -1.6(16) . .
C3 C4 N2 C8 176.8(10) . .
C5 C4 N2 Ir1 -174.9(8) . .
C3 C4 N2 Ir1 3.4(12) . .
C7 C8 N2 C4 3.6(16) . .
C7 C8 N2 Ir1 176.5(8) . .
N1 Ir1 N2 C4 -13.4(8) . .
C16 Ir1 N2 C4 166.9(8) . .
C15 Ir1 N2 C4 -161.6(8) . .
C17 Ir1 N2 C4 150.3(9) . .
C18 Ir1 N2 C4 -103.3(11) . .
C19 Ir1 N2 C4 -119.5(8) . .
Cl1 Ir1 N2 C4 71.8(7) . .
N1 Ir1 N2 C8 173.6(9) . .
C16 Ir1 N2 C8 -6.2(10) . .
C15 Ir1 N2 C8 25.4(10) . .
C17 Ir1 N2 C8 -22.7(14) . .
C18 Ir1 N2 C8 83.7(13) . .
C19 Ir1 N2 C8 67.5(10) . .
Cl1 Ir1 N2 C8 -101.3(9) . .
C10 C9 O2 C2 3.0(17) . .
C14 C9 O2 C2 178.4(10) . .
C3 C2 O2 C9 179.6(9) . .
C1 C2 O2 C9 -87.1(12) . .
C27 C25 C26 C27 -4(5) 2_556 .
C25 C26 C27 C25 4(5) . 2_556
