#------------------------------------------------------------------------------
#$Date: 2016-06-15 12:57:50 +0300 (Wed, 15 Jun 2016) $
#$Revision: 183471 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/65/4086527.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_4086527
loop_
_publ_author_name
'Laviska, David A.'
'Zhou, Tian'
'Kumar, Akshai'
'Emge, Thomas J.'
'Krogh-Jespersen, Karsten'
'Goldman, Alan S.'
_publ_section_title
;
 Single and Double C--H Activation of Biphenyl or Phenanthrene. An Example
 of C--H Addition to Ir(III) More Facile than Addition to Ir(I)
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              1613
_journal_paper_doi               10.1021/acs.organomet.6b00055
_journal_volume                  35
_journal_year                    2016
_chemical_formula_sum            'C39 H51 Ir O P2'
_chemical_formula_weight         789.94
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.274(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5438(17)
_cell_length_b                   18.322(3)
_cell_length_c                   16.267(2)
_cell_measurement_reflns_used    7600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.51
_cell_measurement_theta_min      2.27
_cell_volume                     3361.9(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            40659
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    4.097
_exptl_absorpt_correction_T_max  0.7911
_exptl_absorpt_correction_T_min  0.4156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_refine_diff_density_max         3.027
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         10701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0339
_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)+(0.0400P)²+8.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0815
_reflns_number_gt                9135
_reflns_number_total             10701
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om6b00055_si.cif
_cod_data_source_block           phen_co
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 4624 2016-04-14 12:54:50Z antanas 
;
_cod_original_cell_volume        3362.0(9)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4086527
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
Ir1 Ir 0.337505(10) 0.126870(6) 0.312293(7) 0.01183(4) Uani 1 1 d . . .
P1 P 0.34915(7) 0.06353(4) 0.18511(5) 0.01349(14) Uani 1 1 d . . .
P2 P 0.24283(7) 0.17790(4) 0.41537(5) 0.01349(14) Uani 1 1 d . . .
C1 C 0.1563(3) 0.11088(18) 0.25923(19) 0.0154(6) Uani 1 1 d . . .
C2 C 0.1203(3) 0.05228(17) 0.2029(2) 0.0147(6) Uani 1 1 d . . .
C3 C 0.0004(3) 0.03800(19) 0.1726(2) 0.0199(6) Uani 1 1 d . . .
H3 H -0.0231 -0.0023 0.1362 0.024 Uiso 1 1 calc R . .
C4 C -0.0853(3) 0.0826(2) 0.1955(2) 0.0218(7) Uani 1 1 d . . .
H4 H -0.1670 0.0725 0.1744 0.026 Uiso 1 1 calc R . .
C5 C -0.0523(3) 0.1414(2) 0.2488(2) 0.0204(7) Uani 1 1 d . . .
H5 H -0.1111 0.1721 0.2634 0.024 Uiso 1 1 calc R . .
C6 C 0.0676(3) 0.15541(18) 0.2810(2) 0.0151(6) Uani 1 1 d . . .
C7 C 0.2158(3) 0.00634(18) 0.1777(2) 0.0166(6) Uani 1 1 d . . .
H7A H 0.1885 -0.0116 0.1194 0.020 Uiso 1 1 calc R . .
H7B H 0.2342 -0.0363 0.2155 0.020 Uiso 1 1 calc R . .
C8 C 0.1089(3) 0.21455(18) 0.3462(2) 0.0165(6) Uani 1 1 d . . .
H8A H 0.0471 0.2249 0.3785 0.020 Uiso 1 1 calc R . .
H8B H 0.1270 0.2602 0.3188 0.020 Uiso 1 1 calc R . .
C9 C 0.4750(3) -0.00381(18) 0.1865(2) 0.0170(6) Uani 1 1 d . . .
C10 C 0.5843(3) 0.0358(2) 0.1684(2) 0.0223(7) Uani 1 1 d . . .
H10A H 0.6512 0.0018 0.1759 0.033 Uiso 1 1 calc R . .
H10B H 0.6047 0.0769 0.2074 0.033 Uiso 1 1 calc R . .
H10C H 0.5665 0.0540 0.1104 0.033 Uiso 1 1 calc R . .
C11 C 0.4405(3) -0.06923(19) 0.1270(2) 0.0219(7) Uani 1 1 d . . .
H11A H 0.4149 -0.0516 0.0691 0.033 Uiso 1 1 calc R . .
H11B H 0.3755 -0.0962 0.1433 0.033 Uiso 1 1 calc R . .
H11C H 0.5091 -0.1015 0.1308 0.033 Uiso 1 1 calc R . .
C12 C 0.5132(3) -0.0370(2) 0.2750(2) 0.0232(7) Uani 1 1 d . . .
H12A H 0.4453 -0.0614 0.2904 0.035 Uiso 1 1 calc R . .
H12B H 0.5419 0.0019 0.3157 0.035 Uiso 1 1 calc R . .
H12C H 0.5768 -0.0725 0.2754 0.035 Uiso 1 1 calc R . .
C13 C 0.3208(3) 0.11201(19) 0.0792(2) 0.0178(6) Uani 1 1 d . . .
C14 C 0.4093(3) 0.17565(19) 0.0792(2) 0.0206(6) Uani 1 1 d . . .
H14A H 0.4093 0.1897 0.0211 0.031 Uiso 1 1 calc R . .
H14B H 0.4890 0.1600 0.1073 0.031 Uiso 1 1 calc R . .
H14C H 0.3854 0.2175 0.1092 0.031 Uiso 1 1 calc R . .
C15 C 0.3277(3) 0.0604(2) 0.0057(2) 0.0230(7) Uani 1 1 d . . .
H15A H 0.2776 0.0176 0.0080 0.035 Uiso 1 1 calc R . .
H15B H 0.4100 0.0447 0.0101 0.035 Uiso 1 1 calc R . .
H15C H 0.3001 0.0861 -0.0477 0.035 Uiso 1 1 calc R . .
C16 C 0.1933(3) 0.1423(2) 0.0592(2) 0.0214(7) Uani 1 1 d . . .
H16A H 0.1833 0.1749 0.0105 0.032 Uiso 1 1 calc R . .
H16B H 0.1786 0.1694 0.1079 0.032 Uiso 1 1 calc R . .
H16C H 0.1369 0.1017 0.0465 0.032 Uiso 1 1 calc R . .
C17 C 0.1753(3) 0.11001(18) 0.4816(2) 0.0167(6) Uani 1 1 d . . .
C18 C 0.2674(3) 0.0863(2) 0.5596(2) 0.0244(7) Uani 1 1 d . . .
H18A H 0.2391 0.0425 0.5838 0.037 Uiso 1 1 calc R . .
H18B H 0.2791 0.1257 0.6013 0.037 Uiso 1 1 calc R . .
H18C H 0.3427 0.0755 0.5434 0.037 Uiso 1 1 calc R . .
C19 C 0.0668(4) 0.1426(2) 0.5106(3) 0.0287(8) Uani 1 1 d . . .
H19A H 0.0020 0.1502 0.4616 0.043 Uiso 1 1 calc R . .
H19B H 0.0889 0.1894 0.5388 0.043 Uiso 1 1 calc R . .
H19C H 0.0409 0.1088 0.5498 0.043 Uiso 1 1 calc R . .
C20 C 0.1265(3) 0.0411(2) 0.4321(2) 0.0221(7) Uani 1 1 d . . .
H20A H 0.1901 0.0171 0.4108 0.033 Uiso 1 1 calc R . .
H20B H 0.0625 0.0548 0.3846 0.033 Uiso 1 1 calc R . .
H20C H 0.0956 0.0076 0.4692 0.033 Uiso 1 1 calc R . .
C21 C 0.3166(3) 0.2544(2) 0.4860(2) 0.0203(6) Uani 1 1 d . . .
C22 C 0.4325(3) 0.2279(2) 0.5432(2) 0.0279(8) Uani 1 1 d . . .
H22A H 0.4815 0.2036 0.5091 0.042 Uiso 1 1 calc R . .
H22B H 0.4141 0.1934 0.5847 0.042 Uiso 1 1 calc R . .
H22C H 0.4757 0.2697 0.5723 0.042 Uiso 1 1 calc R . .
C23 C 0.2362(4) 0.2878(2) 0.5400(3) 0.0326(9) Uani 1 1 d . . .
H23A H 0.2753 0.3304 0.5702 0.049 Uiso 1 1 calc R . .
H23B H 0.2208 0.2515 0.5806 0.049 Uiso 1 1 calc R . .
H23C H 0.1610 0.3029 0.5037 0.049 Uiso 1 1 calc R . .
C24 C 0.3508(3) 0.3145(2) 0.4303(2) 0.0243(7) Uani 1 1 d . . .
H24A H 0.3762 0.3580 0.4644 0.036 Uiso 1 1 calc R . .
H24B H 0.2822 0.3266 0.3856 0.036 Uiso 1 1 calc R . .
H24C H 0.4159 0.2973 0.4052 0.036 Uiso 1 1 calc R . .
C25 C 0.5192(3) 0.15554(18) 0.3535(2) 0.0155(6) Uani 1 1 d . . .
C26 C 0.5506(3) 0.22135(17) 0.3174(2) 0.0154(6) Uani 1 1 d . . .
C27 C 0.4557(3) 0.26100(17) 0.2652(2) 0.0151(6) Uani 1 1 d . . .
C28 C 0.3395(3) 0.22991(17) 0.2538(2) 0.0150(6) Uani 1 1 d . . .
C29 C 0.2485(3) 0.27173(18) 0.2060(2) 0.0182(6) Uani 1 1 d . . .
H29 H 0.1694 0.2542 0.1976 0.022 Uiso 1 1 calc R . .
C30 C 0.2694(3) 0.33854(19) 0.1699(2) 0.0217(7) Uani 1 1 d . . .
H30 H 0.2049 0.3648 0.1371 0.026 Uiso 1 1 calc R . .
C31 C 0.3829(4) 0.36683(18) 0.1815(2) 0.0232(7) Uani 1 1 d . . .
H31 H 0.3961 0.4119 0.1562 0.028 Uiso 1 1 calc R . .
C32 C 0.4783(3) 0.32871(18) 0.2306(2) 0.0189(6) Uani 1 1 d . . .
C33 C 0.5984(4) 0.3552(2) 0.2466(2) 0.0242(7) Uani 1 1 d . . .
H33 H 0.6152 0.4001 0.2223 0.029 Uiso 1 1 calc R . .
C34 C 0.6879(3) 0.3174(2) 0.2955(2) 0.0235(7) Uani 1 1 d . . .
H34 H 0.7662 0.3362 0.3046 0.028 Uiso 1 1 calc R . .
C35 C 0.6672(3) 0.24946(19) 0.3340(2) 0.0179(6) Uani 1 1 d . . .
C36 C 0.7561(3) 0.2106(2) 0.3896(2) 0.0220(7) Uani 1 1 d . . .
H36 H 0.8355 0.2278 0.4012 0.026 Uiso 1 1 calc R . .
C37 C 0.7276(3) 0.1480(2) 0.4268(2) 0.0201(6) Uani 1 1 d . . .
H37 H 0.7877 0.1227 0.4653 0.024 Uiso 1 1 calc R . .
C38 C 0.6107(3) 0.12029(18) 0.4090(2) 0.0179(6) Uani 1 1 d . . .
H38 H 0.5940 0.0765 0.4356 0.021 Uiso 1 1 calc R . .
O1 O 0.3989(2) -0.00635(14) 0.42357(17) 0.0249(5) Uani 1 1 d . . .
C39 C 0.3688(3) 0.04120(18) 0.3776(2) 0.0165(6) Uani 1 1 d . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
C39 Ir1 C1 99.76(13) . .
C39 Ir1 C28 167.47(13) . .
C1 Ir1 C28 92.56(12) . .
C39 Ir1 C25 88.30(13) . .
C1 Ir1 C25 171.82(12) . .
C28 Ir1 C25 79.46(12) . .
C39 Ir1 P2 89.53(10) . .
C1 Ir1 P2 77.20(9) . .
C28 Ir1 P2 90.96(8) . .
C25 Ir1 P2 104.52(9) . .
C39 Ir1 P1 92.52(10) . .
C1 Ir1 P1 79.19(9) . .
C28 Ir1 P1 92.06(9) . .
C25 Ir1 P1 99.14(9) . .
P2 Ir1 P1 156.31(3) . .
C7 P1 C9 104.88(15) . .
C7 P1 C13 103.01(15) . .
C9 P1 C13 107.33(15) . .
C7 P1 Ir1 97.60(11) . .
C9 P1 Ir1 119.04(11) . .
C13 P1 Ir1 121.59(11) . .
C8 P2 C21 108.21(16) . .
C8 P2 C17 101.06(15) . .
C21 P2 C17 108.89(15) . .
C8 P2 Ir1 99.50(10) . .
C21 P2 Ir1 120.19(11) . .
C17 P2 Ir1 116.34(10) . .
C6 C1 C2 118.1(3) . .
C6 C1 Ir1 121.8(2) . .
C2 C1 Ir1 120.0(2) . .
C3 C2 C1 120.3(3) . .
C3 C2 C7 121.8(3) . .
C1 C2 C7 117.9(3) . .
C2 C3 C4 120.3(3) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
C5 C4 C3 120.5(3) . .
C5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
C4 C5 C6 119.8(3) . .
C4 C5 H5 120.1 . .
C6 C5 H5 120.1 . .
C5 C6 C1 120.9(3) . .
C5 C6 C8 122.1(3) . .
C1 C6 C8 116.7(3) . .
C2 C7 P1 108.2(2) . .
C2 C7 H7A 110.1 . .
P1 C7 H7A 110.1 . .
C2 C7 H7B 110.1 . .
P1 C7 H7B 110.1 . .
H7A C7 H7B 108.4 . .
C6 C8 P2 105.4(2) . .
C6 C8 H8A 110.7 . .
P2 C8 H8A 110.7 . .
C6 C8 H8B 110.7 . .
P2 C8 H8B 110.7 . .
H8A C8 H8B 108.8 . .
C10 C9 C11 111.1(3) . .
C10 C9 C12 106.4(3) . .
C11 C9 C12 105.4(3) . .
C10 C9 P1 110.3(2) . .
C11 C9 P1 113.7(2) . .
C12 C9 P1 109.5(2) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C15 C13 C16 105.2(3) . .
C15 C13 C14 108.6(3) . .
C16 C13 C14 109.2(3) . .
C15 C13 P1 112.9(2) . .
C16 C13 P1 109.4(2) . .
C14 C13 P1 111.4(2) . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C13 C16 H16A 109.5 . .
C13 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C13 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C18 C17 C20 108.2(3) . .
C18 C17 C19 108.6(3) . .
C20 C17 C19 104.2(3) . .
C18 C17 P2 110.8(2) . .
C20 C17 P2 112.7(2) . .
C19 C17 P2 111.9(2) . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C17 C19 H19A 109.5 . .
C17 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C17 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C17 C20 H20A 109.5 . .
C17 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C17 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C24 C21 C23 108.4(3) . .
C24 C21 C22 106.6(3) . .
C23 C21 C22 109.5(3) . .
C24 C21 P2 108.2(2) . .
C23 C21 P2 113.1(2) . .
C22 C21 P2 110.8(3) . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C21 C23 H23A 109.5 . .
C21 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C21 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C21 C24 H24A 109.5 . .
C21 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C21 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C38 C25 C26 115.8(3) . .
C38 C25 Ir1 130.6(2) . .
C26 C25 Ir1 113.6(2) . .
C35 C26 C25 123.2(3) . .
C35 C26 C27 120.4(3) . .
C25 C26 C27 116.4(3) . .
C32 C27 C28 123.1(3) . .
C32 C27 C26 120.0(3) . .
C28 C27 C26 116.9(3) . .
C29 C28 C27 115.3(3) . .
C29 C28 Ir1 131.4(2) . .
C27 C28 Ir1 113.3(2) . .
C28 C29 C30 122.5(3) . .
C28 C29 H29 118.8 . .
C30 C29 H29 118.8 . .
C31 C30 C29 120.9(3) . .
C31 C30 H30 119.6 . .
C29 C30 H30 119.6 . .
C30 C31 C32 119.8(3) . .
C30 C31 H31 120.1 . .
C32 C31 H31 120.1 . .
C31 C32 C27 118.5(3) . .
C31 C32 C33 123.0(3) . .
C27 C32 C33 118.5(3) . .
C34 C33 C32 121.2(3) . .
C34 C33 H33 119.4 . .
C32 C33 H33 119.4 . .
C33 C34 C35 121.6(3) . .
C33 C34 H34 119.2 . .
C35 C34 H34 119.2 . .
C36 C35 C26 118.2(3) . .
C36 C35 C34 123.5(3) . .
C26 C35 C34 118.2(3) . .
C37 C36 C35 119.8(3) . .
C37 C36 H36 120.1 . .
C35 C36 H36 120.1 . .
C36 C37 C38 121.2(3) . .
C36 C37 H37 119.4 . .
C38 C37 H37 119.4 . .
C25 C38 C37 121.7(3) . .
C25 C38 H38 119.1 . .
C37 C38 H38 119.1 . .
O1 C39 Ir1 171.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir1 C39 1.887(3) .
Ir1 C1 2.107(3) .
Ir1 C28 2.116(3) .
Ir1 C25 2.127(3) .
Ir1 P2 2.3790(8) .
Ir1 P1 2.4008(9) .
P1 C7 1.844(3) .
P1 C9 1.902(3) .
P1 C13 1.903(3) .
P2 C8 1.836(3) .
P2 C21 1.896(3) .
P2 C17 1.916(3) .
C1 C6 1.412(4) .
C1 C2 1.416(4) .
C2 C3 1.392(4) .
C2 C7 1.512(4) .
C3 C4 1.393(5) .
C3 H3 0.9500 .
C4 C5 1.385(5) .
C4 H4 0.9500 .
C5 C6 1.396(5) .
C5 H5 0.9500 .
C6 C8 1.521(5) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.537(5) .
C9 C11 1.539(5) .
C9 C12 1.538(5) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C15 1.539(5) .
C13 C16 1.541(5) .
C13 C14 1.550(5) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 C18 1.535(5) .
C17 C20 1.539(5) .
C17 C19 1.550(5) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 C24 1.529(5) .
C21 C23 1.535(5) .
C21 C22 1.537(5) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C25 C38 1.394(5) .
C25 C26 1.422(4) .
C26 C35 1.412(4) .
C26 C27 1.433(4) .
C27 C32 1.409(4) .
C27 C28 1.432(4) .
C28 C29 1.396(4) .
C29 C30 1.400(5) .
C29 H29 0.9500 .
C30 C31 1.384(5) .
C30 H30 0.9500 .
C31 C32 1.402(5) .
C31 H31 0.9500 .
C32 C33 1.441(5) .
C33 C34 1.353(6) .
C33 H33 0.9500 .
C34 C35 1.436(5) .
C34 H34 0.9500 .
C35 C36 1.408(5) .
C36 C37 1.369(5) .
C36 H36 0.9500 .
C37 C38 1.414(5) .
C37 H37 0.9500 .
C38 H38 0.9500 .
O1 C39 1.153(4) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C39 Ir1 P1 C7 67.15(15) . . . .
C1 Ir1 P1 C7 -32.30(14) . . . .
C28 Ir1 P1 C7 -124.51(14) . . . .
C25 Ir1 P1 C7 155.83(14) . . . .
P2 Ir1 P1 C7 -27.41(14) . . . .
C39 Ir1 P1 C9 -44.59(16) . . . .
C1 Ir1 P1 C9 -144.04(15) . . . .
C28 Ir1 P1 C9 123.74(15) . . . .
C25 Ir1 P1 C9 44.09(15) . . . .
P2 Ir1 P1 C9 -139.15(13) . . . .
C39 Ir1 P1 C13 177.56(16) . . . .
C1 Ir1 P1 C13 78.11(15) . . . .
C28 Ir1 P1 C13 -14.10(15) . . . .
C25 Ir1 P1 C13 -93.76(16) . . . .
P2 Ir1 P1 C13 83.00(15) . . . .
C39 Ir1 P2 C8 -134.10(15) . . . .
C1 Ir1 P2 C8 -33.98(14) . . . .
C28 Ir1 P2 C8 58.42(14) . . . .
C25 Ir1 P2 C8 137.78(14) . . . .
P1 Ir1 P2 C8 -38.91(14) . . . .
C39 Ir1 P2 C21 108.26(17) . . . .
C1 Ir1 P2 C21 -151.62(16) . . . .
C28 Ir1 P2 C21 -59.22(16) . . . .
C25 Ir1 P2 C21 20.14(16) . . . .
P1 Ir1 P2 C21 -156.55(14) . . . .
C39 Ir1 P2 C17 -26.65(15) . . . .
C1 Ir1 P2 C17 73.46(15) . . . .
C28 Ir1 P2 C17 165.87(15) . . . .
C25 Ir1 P2 C17 -114.77(15) . . . .
P1 Ir1 P2 C17 68.54(14) . . . .
C39 Ir1 C1 C6 111.9(3) . . . .
C28 Ir1 C1 C6 -65.8(3) . . . .
C25 Ir1 C1 C6 -78.5(9) . . . .
P2 Ir1 C1 C6 24.7(2) . . . .
P1 Ir1 C1 C6 -157.4(3) . . . .
C39 Ir1 C1 C2 -65.3(3) . . . .
C28 Ir1 C1 C2 117.0(2) . . . .
C25 Ir1 C1 C2 104.3(8) . . . .
P2 Ir1 C1 C2 -152.6(3) . . . .
P1 Ir1 C1 C2 25.4(2) . . . .
C6 C1 C2 C3 -2.3(5) . . . .
Ir1 C1 C2 C3 175.1(2) . . . .
C6 C1 C2 C7 178.0(3) . . . .
Ir1 C1 C2 C7 -4.7(4) . . . .
C1 C2 C3 C4 1.9(5) . . . .
C7 C2 C3 C4 -178.3(3) . . . .
C2 C3 C4 C5 -0.2(5) . . . .
C3 C4 C5 C6 -1.1(5) . . . .
C4 C5 C6 C1 0.7(5) . . . .
C4 C5 C6 C8 -174.0(3) . . . .
C2 C1 C6 C5 0.9(5) . . . .
Ir1 C1 C6 C5 -176.3(2) . . . .
C2 C1 C6 C8 175.9(3) . . . .
Ir1 C1 C6 C8 -1.4(4) . . . .
C3 C2 C7 P1 152.9(3) . . . .
C1 C2 C7 P1 -27.4(3) . . . .
C9 P1 C7 C2 162.8(2) . . . .
C13 P1 C7 C2 -85.1(2) . . . .
Ir1 P1 C7 C2 39.9(2) . . . .
C5 C6 C8 P2 144.0(3) . . . .
C1 C6 C8 P2 -30.9(3) . . . .
C21 P2 C8 C6 169.5(2) . . . .
C17 P2 C8 C6 -76.2(2) . . . .
Ir1 P2 C8 C6 43.2(2) . . . .
C7 P1 C9 C10 164.6(2) . . . .
C13 P1 C9 C10 55.5(3) . . . .
Ir1 P1 C9 C10 -87.7(2) . . . .
C7 P1 C9 C11 39.0(3) . . . .
C13 P1 C9 C11 -70.1(3) . . . .
Ir1 P1 C9 C11 146.7(2) . . . .
C7 P1 C9 C12 -78.6(3) . . . .
C13 P1 C9 C12 172.3(2) . . . .
Ir1 P1 C9 C12 29.1(3) . . . .
C7 P1 C13 C15 -70.0(3) . . . .
C9 P1 C13 C15 40.4(3) . . . .
Ir1 P1 C13 C15 -177.6(2) . . . .
C7 P1 C13 C16 46.7(3) . . . .
C9 P1 C13 C16 157.1(2) . . . .
Ir1 P1 C13 C16 -60.8(3) . . . .
C7 P1 C13 C14 167.5(2) . . . .
C9 P1 C13 C14 -82.1(3) . . . .
Ir1 P1 C13 C14 60.0(3) . . . .
C8 P2 C17 C18 -165.4(2) . . . .
C21 P2 C17 C18 -51.6(3) . . . .
Ir1 P2 C17 C18 88.1(2) . . . .
C8 P2 C17 C20 73.2(3) . . . .
C21 P2 C17 C20 -173.0(2) . . . .
Ir1 P2 C17 C20 -33.4(3) . . . .
C8 P2 C17 C19 -43.9(3) . . . .
C21 P2 C17 C19 69.9(3) . . . .
Ir1 P2 C17 C19 -150.4(2) . . . .
C8 P2 C21 C24 -61.2(3) . . . .
C17 P2 C21 C24 -170.3(2) . . . .
Ir1 P2 C21 C24 51.9(3) . . . .
C8 P2 C21 C23 58.9(3) . . . .
C17 P2 C21 C23 -50.1(3) . . . .
Ir1 P2 C21 C23 172.0(2) . . . .
C8 P2 C21 C22 -177.7(2) . . . .
C17 P2 C21 C22 73.2(3) . . . .
Ir1 P2 C21 C22 -64.6(3) . . . .
C39 Ir1 C25 C38 -2.1(3) . . . .
C1 Ir1 C25 C38 -171.9(7) . . . .
C28 Ir1 C25 C38 175.2(3) . . . .
P2 Ir1 C25 C38 86.9(3) . . . .
P1 Ir1 C25 C38 -94.4(3) . . . .
C39 Ir1 C25 C26 177.5(2) . . . .
C1 Ir1 C25 C26 7.7(10) . . . .
C28 Ir1 C25 C26 -5.2(2) . . . .
P2 Ir1 C25 C26 -93.4(2) . . . .
P1 Ir1 C25 C26 85.2(2) . . . .
C38 C25 C26 C35 1.6(5) . . . .
Ir1 C25 C26 C35 -178.1(2) . . . .
C38 C25 C26 C27 -175.5(3) . . . .
Ir1 C25 C26 C27 4.9(4) . . . .
C35 C26 C27 C32 -0.5(5) . . . .
C25 C26 C27 C32 176.7(3) . . . .
C35 C26 C27 C28 -177.9(3) . . . .
C25 C26 C27 C28 -0.8(4) . . . .
C32 C27 C28 C29 -0.4(5) . . . .
C26 C27 C28 C29 177.0(3) . . . .
C32 C27 C28 Ir1 178.9(2) . . . .
C26 C27 C28 Ir1 -3.6(4) . . . .
C39 Ir1 C28 C29 -163.7(5) . . . .
C1 Ir1 C28 C29 5.7(3) . . . .
C25 Ir1 C28 C29 -176.1(3) . . . .
P2 Ir1 C28 C29 -71.5(3) . . . .
P1 Ir1 C28 C29 85.0(3) . . . .
C39 Ir1 C28 C27 17.2(7) . . . .
C1 Ir1 C28 C27 -173.5(2) . . . .
C25 Ir1 C28 C27 4.7(2) . . . .
P2 Ir1 C28 C27 109.3(2) . . . .
P1 Ir1 C28 C27 -94.2(2) . . . .
C27 C28 C29 C30 1.5(5) . . . .
Ir1 C28 C29 C30 -177.7(3) . . . .
C28 C29 C30 C31 -1.0(5) . . . .
C29 C30 C31 C32 -0.7(5) . . . .
C30 C31 C32 C27 1.7(5) . . . .
C30 C31 C32 C33 -179.0(3) . . . .
C28 C27 C32 C31 -1.2(5) . . . .
C26 C27 C32 C31 -178.5(3) . . . .
C28 C27 C32 C33 179.5(3) . . . .
C26 C27 C32 C33 2.1(5) . . . .
C31 C32 C33 C34 178.9(3) . . . .
C27 C32 C33 C34 -1.8(5) . . . .
C32 C33 C34 C35 -0.3(5) . . . .
C25 C26 C35 C36 -0.5(5) . . . .
C27 C26 C35 C36 176.4(3) . . . .
C25 C26 C35 C34 -178.5(3) . . . .
C27 C26 C35 C34 -1.6(5) . . . .
C33 C34 C35 C36 -175.8(3) . . . .
C33 C34 C35 C26 2.0(5) . . . .
C26 C35 C36 C37 -1.1(5) . . . .
C34 C35 C36 C37 176.8(3) . . . .
C35 C36 C37 C38 1.6(5) . . . .
C26 C25 C38 C37 -1.1(5) . . . .
Ir1 C25 C38 C37 178.5(3) . . . .
C36 C37 C38 C25 -0.5(5) . . . .
C1 Ir1 C39 O1 -154.2(19) . . . .
C28 Ir1 C39 O1 15(2) . . . .
C25 Ir1 C39 O1 27(2) . . . .
P2 Ir1 C39 O1 -77(2) . . . .
P1 Ir1 C39 O1 126(2) . . . .
