# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

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#                                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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data_md_5b


_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H36 Ir N O3 P, C24 H20 B, C H2 Cl2'
_chemical_formula_sum            'C54 H58 B Cl2 Ir N O3 P'
_chemical_formula_weight         1073.89

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'
B B 0.0013 0.0007 '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'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   18.696(2)
_cell_length_b                   11.6073(14)
_cell_length_c                   24.032(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.526(2)
_cell_angle_gamma                90
_cell_volume                     4817.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9672
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.82

_exptl_crystal_description       irregular
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_F_000             2176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    2.960
_shelx_estimated_absorpt_T_min   0.481
_shelx_estimated_absorpt_T_max   0.603

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3395
_exptl_absorpt_correction_T_max  0.4309
_exptl_absorpt_process_details   'SADABS v.2008/1; (Sheldrick 1996)'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            82883
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.359
_diffrn_reflns_theta_max         28.086
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11700
_reflns_number_gt                9026
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
 There is no evidence of twining structure, althoug the residual 
 peak and deepest hole are very large:
 Highest peak    5.26  at  0.2793  0.3247  0.0372  [  0.73 A from IR ]
 Deepest hole   -3.51  at  0.2200  0.4008  0.0051  [  0.67 A from IR ]
 The highest peak is situated almost in the plane Ir P1 C15, at 0.73 A
 from IR, 1.6 from C15 and 1.8 from P1.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+26.1479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11700
_refine_ls_number_parameters     577
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir Ir 0.24949(2) 0.36625(2) 0.02054(2) 0.01545(4) Uani 1 1 d . . . . .
C1 C 0.2590(3) 0.5403(4) -0.0214(2) 0.0219(9) Uani 1 1 d . . . . .
C2 C 0.1870(3) 0.4862(4) -0.05476(18) 0.0221(9) Uani 1 1 d . . . . .
C3 C 0.1435(2) 0.4811(4) -0.0160(2) 0.0219(9) Uani 1 1 d . . . . .
C4 C 0.1914(2) 0.5245(4) 0.0414(2) 0.0217(9) Uani 1 1 d . . . . .
C5 C 0.2647(2) 0.5599(4) 0.03862(19) 0.0205(9) Uani 1 1 d . . . . .
C6 C 0.3177(3) 0.5731(4) -0.0467(2) 0.0320(11) Uani 1 1 d . . . . .
H6A H 0.3182 0.5153 -0.0762 0.048 Uiso 1 1 calc R U . . .
H6B H 0.3690 0.5769 -0.0140 0.048 Uiso 1 1 calc R U . . .
H6C H 0.3045 0.6485 -0.0663 0.048 Uiso 1 1 calc R U . . .
C7 C 0.1554(3) 0.4594(5) -0.1206(2) 0.0345(12) Uani 1 1 d . . . . .
H7A H 0.1320 0.5288 -0.1435 0.052 Uiso 1 1 calc R U . . .
H7B H 0.1161 0.3988 -0.1292 0.052 Uiso 1 1 calc R U . . .
H7C H 0.1975 0.4329 -0.1322 0.052 Uiso 1 1 calc R U . . .
C8 C 0.0605(3) 0.4445(4) -0.0361(2) 0.0317(11) Uani 1 1 d . . . . .
H8A H 0.0511 0.4124 -0.0018 0.047 Uiso 1 1 calc R U . . .
H8B H 0.0494 0.3859 -0.0677 0.047 Uiso 1 1 calc R U . . .
H8C H 0.0268 0.5113 -0.0520 0.047 Uiso 1 1 calc R U . . .
C9 C 0.1682(3) 0.5426(4) 0.0935(2) 0.0280(10) Uani 1 1 d . . . . .
H9A H 0.1477 0.6208 0.0919 0.042 Uiso 1 1 calc R U . . .
H9B H 0.2134 0.5325 0.1312 0.042 Uiso 1 1 calc R U . . .
H9C H 0.1282 0.4865 0.0918 0.042 Uiso 1 1 calc R U . . .
C10 C 0.3278(3) 0.6255(4) 0.0865(2) 0.0280(10) Uani 1 1 d . . . . .
H10A H 0.3176 0.7083 0.0805 0.042 Uiso 1 1 calc R U . . .
H10B H 0.3777 0.6079 0.0839 0.042 Uiso 1 1 calc R U . . .
H10C H 0.3294 0.6031 0.1262 0.042 Uiso 1 1 calc R U . . .
O1 O 0.13307(16) 0.2011(2) -0.00752(13) 0.0179(6) Uani 1 1 d . . . . .
C11 C 0.1976(2) 0.2224(3) -0.01653(17) 0.0159(8) Uani 1 1 d . . . . .
C12 C 0.2190(2) 0.1462(4) -0.05332(17) 0.0175(8) Uani 1 1 d . . . . .
H12 H 0.1818 0.0911 -0.0762 0.021 Uiso 1 1 calc R U . . .
C13 C 0.2897(2) 0.1457(4) -0.05843(17) 0.0169(8) Uani 1 1 d . . . . .
C14 C 0.3544(2) 0.2216(4) -0.02614(18) 0.0178(8) Uani 1 1 d . . . . .
C15 C 0.3486(2) 0.3087(4) 0.01340(18) 0.0195(9) Uani 1 1 d . . . . .
C16 C 0.4174(2) 0.3681(4) 0.0471(2) 0.0246(9) Uani 1 1 d . . . . .
H16 H 0.4168 0.4216 0.0768 0.030 Uiso 1 1 calc R U . . .
C17 C 0.4858(2) 0.3515(4) 0.0386(2) 0.0263(10) Uani 1 1 d . . . . .
H17 H 0.5309 0.3936 0.0621 0.032 Uiso 1 1 calc R U . . .
C18 C 0.4887(2) 0.2732(4) -0.0043(2) 0.0255(10) Uani 1 1 d . . . . .
H18 H 0.5346 0.2649 -0.0119 0.031 Uiso 1 1 calc R U . . .
C19 C 0.4244(2) 0.2079(4) -0.03547(19) 0.0208(9) Uani 1 1 d . . . . .
H19 H 0.4269 0.1526 -0.0638 0.025 Uiso 1 1 calc R U . . .
C110 C 0.0877(2) 0.0957(4) -0.02883(19) 0.0196(8) Uani 1 1 d . . . . .
H11A H 0.0633 0.0970 -0.0729 0.029 Uiso 1 1 calc R U . . .
H11B H 0.0476 0.0911 -0.0120 0.029 Uiso 1 1 calc R U . . .
H11C H 0.1219 0.0286 -0.0158 0.029 Uiso 1 1 calc R U . . .
C111 C 0.2997(2) 0.0549(4) -0.09913(18) 0.0183(8) Uani 1 1 d . . . . .
C112 C 0.2534(2) 0.0574(4) -0.16050(18) 0.0195(8) Uani 1 1 d . . . . .
H112 H 0.2155 0.1160 -0.1760 0.023 Uiso 1 1 calc R U . . .
C113 C 0.2624(2) -0.0253(4) -0.19907(19) 0.0222(9) Uani 1 1 d . . . . .
H113 H 0.2320 -0.0229 -0.2410 0.027 Uiso 1 1 calc R U . . .
C114 C 0.3165(2) -0.1107(4) -0.1750(2) 0.0238(9) Uani 1 1 d . . . . .
C115 C 0.3615(3) -0.1179(4) -0.1143(2) 0.0275(10) Uani 1 1 d . . . . .
H115 H 0.3974 -0.1791 -0.0988 0.033 Uiso 1 1 calc R U . . .
C116 C 0.3532(3) -0.0336(4) -0.07654(19) 0.0232(9) Uani 1 1 d . . . . .
H116 H 0.3843 -0.0363 -0.0347 0.028 Uiso 1 1 calc R U . . .
O3 O 0.3099(2) -0.1725(3) -0.26845(16) 0.0405(9) Uani 1 1 d . . . . .
O2 O 0.3579(2) -0.2899(4) -0.1932(2) 0.0530(11) Uani 1 1 d . . . . .
N1 N 0.3289(2) -0.1976(4) -0.2154(2) 0.0340(10) Uani 1 1 d . . . . .
P1 P 0.28479(7) 0.27612(10) 0.11122(5) 0.0219(2) Uani 1 1 d . . . . .
C31 C 0.3299(4) 0.1388(5) 0.1147(3) 0.0489(15) Uani 1 1 d . . . . .
H31A H 0.3789 0.1491 0.1094 0.073 Uiso 1 1 calc R U . . .
H31B H 0.2956 0.0890 0.0826 0.073 Uiso 1 1 calc R U . . .
H31C H 0.3399 0.1031 0.1539 0.073 Uiso 1 1 calc R U . . .
C32 C 0.3519(3) 0.3533(6) 0.1746(2) 0.0503(16) Uani 1 1 d . . . . .
H32A H 0.3622 0.3086 0.2115 0.075 Uiso 1 1 calc R U . . .
H32B H 0.3297 0.4281 0.1782 0.075 Uiso 1 1 calc R U . . .
H32C H 0.4005 0.3652 0.1688 0.075 Uiso 1 1 calc R U . . .
C33 C 0.2056(3) 0.2407(4) 0.1339(2) 0.0310(11) Uani 1 1 d . . . . .
H33A H 0.2258 0.2005 0.1727 0.047 Uiso 1 1 calc R U . . .
H33B H 0.1686 0.1909 0.1034 0.047 Uiso 1 1 calc R U . . .
H33C H 0.1795 0.3117 0.1378 0.047 Uiso 1 1 calc R U . . .
B1 B 0.0132(3) 0.8554(4) -0.1826(2) 0.0181(9) Uani 1 1 d . . . . .
C11B C 0.0572(2) 0.8357(4) -0.22882(19) 0.0195(9) Uani 1 1 d . . . . .
C12B C 0.1141(2) 0.7516(4) -0.2196(2) 0.0225(9) Uani 1 1 d . . . . .
H12B H 0.1305 0.7080 -0.1834 0.027 Uiso 1 1 calc R U . . .
C13B C 0.1478(3) 0.7286(4) -0.2609(2) 0.0296(11) Uani 1 1 d . . . . .
H13B H 0.1865 0.6707 -0.2525 0.035 Uiso 1 1 calc R U . . .
C14B C 0.1254(3) 0.7892(5) -0.3139(2) 0.0316(11) Uani 1 1 d . . . . .
H14B H 0.1487 0.7741 -0.3420 0.038 Uiso 1 1 calc R U . . .
C15B C 0.0686(3) 0.8727(5) -0.3259(2) 0.0309(10) Uani 1 1 d . . . . .
H15B H 0.0525 0.9152 -0.3624 0.037 Uiso 1 1 calc R U . . .
C16B C 0.0351(3) 0.8942(4) -0.28414(19) 0.0242(9) Uani 1 1 d . . . . .
H16B H -0.0044 0.9509 -0.2935 0.029 Uiso 1 1 calc R U . . .
C21B C 0.0693(2) 0.8281(3) -0.11187(18) 0.0179(8) Uani 1 1 d . . . . .
C22B C 0.1953(3) 0.8366(4) -0.0280(2) 0.0228(9) Uani 1 1 d . . . . .
H22B H 0.2495 0.8498 -0.0144 0.027 Uiso 1 1 calc R U . . .
C23B C 0.1495(2) 0.8471(3) -0.08861(18) 0.0194(9) Uani 1 1 d . . . . .
H23B H 0.1734 0.8679 -0.1156 0.023 Uiso 1 1 calc R U . . .
C24B C 0.1626(2) 0.8069(4) 0.01295(19) 0.0216(9) Uani 1 1 d . . . . .
H24B H 0.1938 0.8005 0.0547 0.026 Uiso 1 1 calc R U . . .
C25B C 0.0831(2) 0.7867(4) -0.00818(19) 0.0218(9) Uani 1 1 d . . . . .
H25B H 0.0597 0.7659 0.0192 0.026 Uiso 1 1 calc R U . . .
C26B C 0.0381(2) 0.7969(4) -0.06926(19) 0.0212(9) Uani 1 1 d . . . . .
H26B H -0.0159 0.7822 -0.0828 0.025 Uiso 1 1 calc R U . . .
C31B C -0.0138(2) 0.9896(4) -0.18129(17) 0.0176(8) Uani 1 1 d . . . . .
C32B C 0.0262(3) 1.0834(4) -0.19230(19) 0.0221(9) Uani 1 1 d . . . . .
H32D H 0.0675 1.0689 -0.2051 0.027 Uiso 1 1 calc R U . . .
C33B C 0.0075(3) 1.1970(4) -0.1851(2) 0.0295(11) Uani 1 1 d . . . . .
H33D H 0.0358 1.2582 -0.1932 0.035 Uiso 1 1 calc R U . . .
C34B C -0.0521(3) 1.2214(4) -0.1663(2) 0.0327(12) Uani 1 1 d . . . . .
H34B H -0.0649 1.2990 -0.1615 0.039 Uiso 1 1 calc R U . . .
C35B C -0.0927(3) 1.1317(4) -0.15448(19) 0.0285(10) Uani 1 1 d . . . . .
H35B H -0.1335 1.1473 -0.1412 0.034 Uiso 1 1 calc R U . . .
C36B C -0.0738(2) 1.0181(4) -0.16208(19) 0.0214(9) Uani 1 1 d . . . . .
H36B H -0.1026 0.9575 -0.1540 0.026 Uiso 1 1 calc R U . . .
C41B C -0.0616(2) 0.7666(4) -0.20762(18) 0.0182(8) Uani 1 1 d . . . . .
C42B C -0.0554(2) 0.6499(4) -0.19180(19) 0.0222(9) Uani 1 1 d . . . . .
H42B H -0.0080 0.6230 -0.1624 0.027 Uiso 1 1 calc R U . . .
C43B C -0.1150(3) 0.5717(4) -0.2170(2) 0.0252(10) Uani 1 1 d . . . . .
H43B H -0.1079 0.4934 -0.2046 0.030 Uiso 1 1 calc R U . . .
C44B C -0.1853(3) 0.6076(4) -0.26027(19) 0.0251(10) Uani 1 1 d . . . . .
H44B H -0.2267 0.5546 -0.2776 0.030 Uiso 1 1 calc R U . . .
C45B C -0.1936(3) 0.7223(4) -0.27765(19) 0.0245(9) Uani 1 1 d . . . . .
H45B H -0.2409 0.7485 -0.3074 0.029 Uiso 1 1 calc R U . . .
C46B C -0.1329(2) 0.7992(4) -0.25170(18) 0.0202(9) Uani 1 1 d . . . . .
H46B H -0.1401 0.8773 -0.2644 0.024 Uiso 1 1 calc R U . . .
Cl1S Cl 0.43846(8) 0.91380(12) 0.09396(5) 0.0395(3) Uani 1 1 d . . . . .
Cl2S Cl 0.51851(8) 1.02721(12) 0.20947(6) 0.0405(3) Uani 1 1 d . . . . .
C1S C 0.4662(3) 0.9044(4) 0.1728(2) 0.0266(10) Uani 1 1 d . . . . .
H1S1 H 0.4194 0.8963 0.1823 0.032 Uiso 1 1 calc R U . . .
H1S2 H 0.4986 0.8349 0.1879 0.032 Uiso 1 1 calc R U . . .


_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 1.965(4) . ?
Ir C15 2.037(4) . ?
Ir C2 2.226(4) . ?
Ir C3 2.267(4) . ?
Ir P1 2.2754(11) . ?
Ir C4 2.285(4) . ?
Ir C5 2.287(4) . ?
Ir C1 2.295(4) . ?
C1 C2 1.423(6) . ?
C1 C5 1.424(6) . ?
C1 C6 1.493(6) . ?
C2 C3 1.454(6) . ?
C2 C7 1.494(6) . ?
C3 C4 1.418(6) . ?
C3 C8 1.499(6) . ?
C4 C5 1.456(6) . ?
C4 C9 1.490(6) . ?
C5 C10 1.502(6) . ?
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 . ?
O1 C11 1.327(5) . ?
O1 C110 1.464(5) . ?
C11 C12 1.414(6) . ?
C12 C13 1.373(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.457(6) . ?
C13 C111 1.498(6) . ?
C14 C19 1.418(6) . ?
C14 C15 1.421(6) . ?
C15 C16 1.410(6) . ?
C16 C17 1.384(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.375(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C110 H11A 0.9800 . ?
C110 H11B 0.9800 . ?
C110 H11C 0.9800 . ?
C111 C116 1.391(6) . ?
C111 C112 1.395(5) . ?
C112 C113 1.388(6) . ?
C112 H112 0.9500 . ?
C113 C114 1.376(6) . ?
C113 H113 0.9500 . ?
C114 C115 1.379(6) . ?
C114 N1 1.479(6) . ?
C115 C116 1.383(6) . ?
C115 H115 0.9500 . ?
C116 H116 0.9500 . ?
O3 N1 1.221(5) . ?
O2 N1 1.227(6) . ?
P1 C31 1.790(6) . ?
P1 C32 1.798(5) . ?
P1 C33 1.809(5) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
B1 C11B 1.631(6) . ?
B1 C31B 1.641(6) . ?
B1 C21B 1.651(6) . ?
B1 C41B 1.653(6) . ?
C11B C12B 1.398(6) . ?
C11B C16B 1.407(6) . ?
C12B C13B 1.391(6) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.372(7) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.384(7) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.394(6) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
C21B C23B 1.404(6) . ?
C21B C26B 1.406(6) . ?
C22B C23B 1.383(6) . ?
C22B C24B 1.387(6) . ?
C22B H22B 0.9500 . ?
C23B H23B 0.9500 . ?
C24B C25B 1.393(6) . ?
C24B H24B 0.9500 . ?
C25B C26B 1.390(6) . ?
C25B H25B 0.9500 . ?
C26B H26B 0.9500 . ?
C31B C32B 1.401(6) . ?
C31B C36B 1.406(6) . ?
C32B C33B 1.392(6) . ?
C32B H32D 0.9500 . ?
C33B C34B 1.382(7) . ?
C33B H33D 0.9500 . ?
C34B C35B 1.381(7) . ?
C34B H34B 0.9500 . ?
C35B C36B 1.396(6) . ?
C35B H35B 0.9500 . ?
C36B H36B 0.9500 . ?
C41B C42B 1.400(6) . ?
C41B C46B 1.400(6) . ?
C42B C43B 1.383(6) . ?
C42B H42B 0.9500 . ?
C43B C44B 1.391(6) . ?
C43B H43B 0.9500 . ?
C44B C45B 1.387(6) . ?
C44B H44B 0.9500 . ?
C45B C46B 1.389(6) . ?
C45B H45B 0.9500 . ?
C46B H46B 0.9500 . ?
Cl1S C1S 1.765(5) . ?
Cl2S C1S 1.762(5) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 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 C15 89.47(16) . . ?
C11 Ir C2 98.53(16) . . ?
C15 Ir C2 110.34(16) . . ?
C11 Ir C3 96.74(16) . . ?
C15 Ir C3 148.01(16) . . ?
C2 Ir C3 37.74(16) . . ?
C11 Ir P1 87.43(12) . . ?
C15 Ir P1 89.46(12) . . ?
C2 Ir P1 159.26(12) . . ?
C3 Ir P1 122.05(12) . . ?
C11 Ir C4 126.07(16) . . ?
C15 Ir C4 143.67(16) . . ?
C2 Ir C4 61.98(16) . . ?
C3 Ir C4 36.30(15) . . ?
P1 Ir C4 98.47(11) . . ?
C11 Ir C5 157.72(15) . . ?
C15 Ir C5 106.70(16) . . ?
C2 Ir C5 61.85(15) . . ?
C3 Ir C5 61.45(15) . . ?
P1 Ir C5 107.50(11) . . ?
C4 Ir C5 37.13(15) . . ?
C11 Ir C1 131.07(16) . . ?
C15 Ir C1 91.45(16) . . ?
C2 Ir C1 36.65(15) . . ?
C3 Ir C1 61.05(15) . . ?
P1 Ir C1 141.50(12) . . ?
C4 Ir C1 60.79(15) . . ?
C5 Ir C1 36.21(15) . . ?
C2 C1 C5 109.2(4) . . ?
C2 C1 C6 124.6(4) . . ?
C5 C1 C6 126.2(4) . . ?
C2 C1 Ir 69.1(2) . . ?
C5 C1 Ir 71.6(2) . . ?
C6 C1 Ir 126.6(3) . . ?
C1 C2 C3 107.3(4) . . ?
C1 C2 C7 126.4(4) . . ?
C3 C2 C7 125.4(4) . . ?
C1 C2 Ir 74.3(2) . . ?
C3 C2 Ir 72.7(2) . . ?
C7 C2 Ir 127.0(3) . . ?
C4 C3 C2 108.0(4) . . ?
C4 C3 C8 127.2(4) . . ?
C2 C3 C8 124.6(4) . . ?
C4 C3 Ir 72.5(2) . . ?
C2 C3 Ir 69.6(2) . . ?
C8 C3 Ir 127.0(3) . . ?
C3 C4 C5 108.1(4) . . ?
C3 C4 C9 126.0(4) . . ?
C5 C4 C9 125.6(4) . . ?
C3 C4 Ir 71.2(2) . . ?
C5 C4 Ir 71.5(2) . . ?
C9 C4 Ir 127.9(3) . . ?
C1 C5 C4 107.2(4) . . ?
C1 C5 C10 126.0(4) . . ?
C4 C5 C10 125.8(4) . . ?
C1 C5 Ir 72.2(2) . . ?
C4 C5 Ir 71.4(2) . . ?
C10 C5 Ir 130.4(3) . . ?
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 . . ?
C11 O1 C110 122.6(3) . . ?
O1 C11 C12 118.6(4) . . ?
O1 C11 Ir 114.0(3) . . ?
C12 C11 Ir 127.3(3) . . ?
C13 C12 C11 124.9(4) . . ?
C13 C12 H12 117.6 . . ?
C11 C12 H12 117.6 . . ?
C12 C13 C14 125.6(4) . . ?
C12 C13 C111 115.2(4) . . ?
C14 C13 C111 119.1(3) . . ?
C19 C14 C15 119.8(4) . . ?
C19 C14 C13 118.5(4) . . ?
C15 C14 C13 121.7(4) . . ?
C16 C15 C14 116.4(4) . . ?
C16 C15 Ir 116.8(3) . . ?
C14 C15 Ir 126.5(3) . . ?
C17 C16 C15 122.6(4) . . ?
C17 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
C16 C17 C18 120.0(4) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 119.4(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C14 121.2(4) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?
O1 C110 H11A 109.5 . . ?
O1 C110 H11B 109.5 . . ?
H11A C110 H11B 109.5 . . ?
O1 C110 H11C 109.5 . . ?
H11A C110 H11C 109.5 . . ?
H11B C110 H11C 109.5 . . ?
C116 C111 C112 119.3(4) . . ?
C116 C111 C13 121.1(4) . . ?
C112 C111 C13 119.6(4) . . ?
C113 C112 C111 120.5(4) . . ?
C113 C112 H112 119.8 . . ?
C111 C112 H112 119.8 . . ?
C114 C113 C112 118.3(4) . . ?
C114 C113 H113 120.8 . . ?
C112 C113 H113 120.8 . . ?
C113 C114 C115 122.8(4) . . ?
C113 C114 N1 119.3(4) . . ?
C115 C114 N1 117.8(4) . . ?
C114 C115 C116 118.3(4) . . ?
C114 C115 H115 120.8 . . ?
C116 C115 H115 120.8 . . ?
C115 C116 C111 120.8(4) . . ?
C115 C116 H116 119.6 . . ?
C111 C116 H116 119.6 . . ?
O3 N1 O2 124.5(4) . . ?
O3 N1 C114 117.9(4) . . ?
O2 N1 C114 117.6(4) . . ?
C31 P1 C32 103.9(3) . . ?
C31 P1 C33 102.1(3) . . ?
C32 P1 C33 104.1(3) . . ?
C31 P1 Ir 114.34(19) . . ?
C32 P1 Ir 115.8(2) . . ?
C33 P1 Ir 114.96(16) . . ?
P1 C31 H31A 109.5 . . ?
P1 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
P1 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
P1 C32 H32A 109.5 . . ?
P1 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
P1 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
P1 C33 H33A 109.5 . . ?
P1 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
P1 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C11B B1 C31B 112.7(4) . . ?
C11B B1 C21B 112.8(3) . . ?
C31B B1 C21B 103.9(3) . . ?
C11B B1 C41B 104.0(3) . . ?
C31B B1 C41B 112.1(3) . . ?
C21B B1 C41B 111.7(3) . . ?
C12B C11B C16B 114.7(4) . . ?
C12B C11B B1 122.8(4) . . ?
C16B C11B B1 122.2(4) . . ?
C13B C12B C11B 123.1(4) . . ?
C13B C12B H12B 118.4 . . ?
C11B C12B H12B 118.4 . . ?
C14B C13B C12B 120.2(5) . . ?
C14B C13B H13B 119.9 . . ?
C12B C13B H13B 119.9 . . ?
C13B C14B C15B 119.3(4) . . ?
C13B C14B H14B 120.3 . . ?
C15B C14B H14B 120.3 . . ?
C14B C15B C16B 119.7(5) . . ?
C14B C15B H15B 120.1 . . ?
C16B C15B H15B 120.1 . . ?
C15B C16B C11B 122.9(4) . . ?
C15B C16B H16B 118.5 . . ?
C11B C16B H16B 118.5 . . ?
C23B C21B C26B 115.4(4) . . ?
C23B C21B B1 122.7(4) . . ?
C26B C21B B1 121.5(4) . . ?
C23B C22B C24B 120.4(4) . . ?
C23B C22B H22B 119.8 . . ?
C24B C22B H22B 119.8 . . ?
C22B C23B C21B 122.8(4) . . ?
C22B C23B H23B 118.6 . . ?
C21B C23B H23B 118.6 . . ?
C22B C24B C25B 118.8(4) . . ?
C22B C24B H24B 120.6 . . ?
C25B C24B H24B 120.6 . . ?
C26B C25B C24B 120.0(4) . . ?
C26B C25B H25B 120.0 . . ?
C24B C25B H25B 120.0 . . ?
C25B C26B C21B 122.7(4) . . ?
C25B C26B H26B 118.7 . . ?
C21B C26B H26B 118.7 . . ?
C32B C31B C36B 115.4(4) . . ?
C32B C31B B1 123.0(4) . . ?
C36B C31B B1 121.3(4) . . ?
C33B C32B C31B 122.4(4) . . ?
C33B C32B H32D 118.8 . . ?
C31B C32B H32D 118.8 . . ?
C34B C33B C32B 120.4(5) . . ?
C34B C33B H33D 119.8 . . ?
C32B C33B H33D 119.8 . . ?
C35B C34B C33B 119.2(4) . . ?
C35B C34B H34B 120.4 . . ?
C33B C34B H34B 120.4 . . ?
C34B C35B C36B 119.9(4) . . ?
C34B C35B H35B 120.1 . . ?
C36B C35B H35B 120.1 . . ?
C35B C36B C31B 122.7(4) . . ?
C35B C36B H36B 118.7 . . ?
C31B C36B H36B 118.7 . . ?
C42B C41B C46B 115.0(4) . . ?
C42B C41B B1 122.3(4) . . ?
C46B C41B B1 122.3(4) . . ?
C43B C42B C41B 123.2(4) . . ?
C43B C42B H42B 118.4 . . ?
C41B C42B H42B 118.4 . . ?
C42B C43B C44B 120.2(4) . . ?
C42B C43B H43B 119.9 . . ?
C44B C43B H43B 119.9 . . ?
C45B C44B C43B 118.5(4) . . ?
C45B C44B H44B 120.8 . . ?
C43B C44B H44B 120.8 . . ?
C44B C45B C46B 120.3(4) . . ?
C44B C45B H45B 119.9 . . ?
C46B C45B H45B 119.9 . . ?
C45B C46B C41B 122.9(4) . . ?
C45B C46B H46B 118.5 . . ?
C41B C46B H46B 118.5 . . ?
Cl2S C1S Cl1S 111.5(3) . . ?
Cl2S C1S H1S1 109.3 . . ?
Cl1S C1S H1S1 109.3 . . ?
Cl2S C1S H1S2 109.3 . . ?
Cl1S C1S H1S2 109.3 . . ?
H1S1 C1S H1S2 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
C5 C1 C2 C3 5.1(5) . . . . ?
C6 C1 C2 C3 -173.6(4) . . . . ?
Ir C1 C2 C3 65.7(3) . . . . ?
C5 C1 C2 C7 174.7(4) . . . . ?
C6 C1 C2 C7 -4.0(7) . . . . ?
Ir C1 C2 C7 -124.7(5) . . . . ?
C5 C1 C2 Ir -60.6(3) . . . . ?
C6 C1 C2 Ir 120.7(4) . . . . ?
C1 C2 C3 C4 -4.0(5) . . . . ?
C7 C2 C3 C4 -173.8(4) . . . . ?
Ir C2 C3 C4 62.8(3) . . . . ?
C1 C2 C3 C8 171.7(4) . . . . ?
C7 C2 C3 C8 1.9(7) . . . . ?
Ir C2 C3 C8 -121.5(4) . . . . ?
C1 C2 C3 Ir -66.8(3) . . . . ?
C7 C2 C3 Ir 123.5(5) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C8 C3 C4 C5 -174.1(4) . . . . ?
Ir C3 C4 C5 62.3(3) . . . . ?
C2 C3 C4 C9 175.4(4) . . . . ?
C8 C3 C4 C9 -0.1(7) . . . . ?
Ir C3 C4 C9 -123.7(4) . . . . ?
C2 C3 C4 Ir -60.9(3) . . . . ?
C8 C3 C4 Ir 123.5(4) . . . . ?
C2 C1 C5 C4 -4.2(5) . . . . ?
C6 C1 C5 C4 174.4(4) . . . . ?
Ir C1 C5 C4 -63.2(3) . . . . ?
C2 C1 C5 C10 -173.5(4) . . . . ?
C6 C1 C5 C10 5.1(7) . . . . ?
Ir C1 C5 C10 127.4(4) . . . . ?
C2 C1 C5 Ir 59.0(3) . . . . ?
C6 C1 C5 Ir -122.3(5) . . . . ?
C3 C4 C5 C1 1.7(5) . . . . ?
C9 C4 C5 C1 -172.4(4) . . . . ?
Ir C4 C5 C1 63.8(3) . . . . ?
C3 C4 C5 C10 171.0(4) . . . . ?
C9 C4 C5 C10 -3.0(7) . . . . ?
Ir C4 C5 C10 -126.9(4) . . . . ?
C3 C4 C5 Ir -62.1(3) . . . . ?
C9 C4 C5 Ir 123.8(4) . . . . ?
C110 O1 C11 C12 6.6(5) . . . . ?
C110 O1 C11 Ir -176.9(3) . . . . ?
O1 C11 C12 C13 -168.4(4) . . . . ?
Ir C11 C12 C13 15.6(6) . . . . ?
C11 C12 C13 C14 1.4(7) . . . . ?
C11 C12 C13 C111 178.6(4) . . . . ?
C12 C13 C14 C19 178.4(4) . . . . ?
C111 C13 C14 C19 1.2(6) . . . . ?
C12 C13 C14 C15 -2.4(6) . . . . ?
C111 C13 C14 C15 -179.6(4) . . . . ?
C19 C14 C15 C16 -7.6(6) . . . . ?
C13 C14 C15 C16 173.2(4) . . . . ?
C19 C14 C15 Ir 166.4(3) . . . . ?
C13 C14 C15 Ir -12.8(6) . . . . ?
C14 C15 C16 C17 6.1(7) . . . . ?
Ir C15 C16 C17 -168.5(4) . . . . ?
C15 C16 C17 C18 -0.4(7) . . . . ?
C16 C17 C18 C19 -3.8(7) . . . . ?
C17 C18 C19 C14 2.1(7) . . . . ?
C15 C14 C19 C18 3.8(6) . . . . ?
C13 C14 C19 C18 -177.0(4) . . . . ?
C12 C13 C111 C116 -114.4(4) . . . . ?
C14 C13 C111 C116 63.1(5) . . . . ?
C12 C13 C111 C112 64.0(5) . . . . ?
C14 C13 C111 C112 -118.5(4) . . . . ?
C116 C111 C112 C113 -2.3(6) . . . . ?
C13 C111 C112 C113 179.3(4) . . . . ?
C111 C112 C113 C114 1.7(6) . . . . ?
C112 C113 C114 C115 0.3(7) . . . . ?
C112 C113 C114 N1 -178.0(4) . . . . ?
C113 C114 C115 C116 -1.7(7) . . . . ?
N1 C114 C115 C116 176.7(4) . . . . ?
C114 C115 C116 C111 1.0(7) . . . . ?
C112 C111 C116 C115 0.9(7) . . . . ?
C13 C111 C116 C115 179.3(4) . . . . ?
C113 C114 N1 O3 22.1(6) . . . . ?
C115 C114 N1 O3 -156.3(4) . . . . ?
C113 C114 N1 O2 -158.1(4) . . . . ?
C115 C114 N1 O2 23.4(6) . . . . ?
C31B B1 C11B C12B 150.0(4) . . . . ?
C21B B1 C11B C12B 32.8(6) . . . . ?
C41B B1 C11B C12B -88.4(4) . . . . ?
C31B B1 C11B C16B -36.7(5) . . . . ?
C21B B1 C11B C16B -153.9(4) . . . . ?
C41B B1 C11B C16B 85.0(5) . . . . ?
C16B C11B C12B C13B 1.3(6) . . . . ?
B1 C11B C12B C13B 175.1(4) . . . . ?
C11B C12B C13B C14B -0.3(7) . . . . ?
C12B C13B C14B C15B -0.5(7) . . . . ?
C13B C14B C15B C16B 0.1(7) . . . . ?
C14B C15B C16B C11B 1.0(7) . . . . ?
C12B C11B C16B C15B -1.7(6) . . . . ?
B1 C11B C16B C15B -175.6(4) . . . . ?
C11B B1 C21B C23B 32.1(6) . . . . ?
C31B B1 C21B C23B -90.2(4) . . . . ?
C41B B1 C21B C23B 148.8(4) . . . . ?
C11B B1 C21B C26B -155.4(4) . . . . ?
C31B B1 C21B C26B 82.3(5) . . . . ?
C41B B1 C21B C26B -38.7(5) . . . . ?
C24B C22B C23B C21B -0.4(6) . . . . ?
C26B C21B C23B C22B -0.4(6) . . . . ?
B1 C21B C23B C22B 172.6(4) . . . . ?
C23B C22B C24B C25B 0.7(6) . . . . ?
C22B C24B C25B C26B -0.3(7) . . . . ?
C24B C25B C26B C21B -0.4(7) . . . . ?
C23B C21B C26B C25B 0.8(6) . . . . ?
B1 C21B C26B C25B -172.2(4) . . . . ?
C11B B1 C31B C32B -29.6(5) . . . . ?
C21B B1 C31B C32B 92.7(4) . . . . ?
C41B B1 C31B C32B -146.5(4) . . . . ?
C11B B1 C31B C36B 157.8(4) . . . . ?
C21B B1 C31B C36B -79.9(4) . . . . ?
C41B B1 C31B C36B 40.9(5) . . . . ?
C36B C31B C32B C33B -0.4(6) . . . . ?
B1 C31B C32B C33B -173.4(4) . . . . ?
C31B C32B C33B C34B 0.3(7) . . . . ?
C32B C33B C34B C35B 0.2(7) . . . . ?
C33B C34B C35B C36B -0.5(6) . . . . ?
C34B C35B C36B C31B 0.3(6) . . . . ?
C32B C31B C36B C35B 0.1(6) . . . . ?
B1 C31B C36B C35B 173.2(4) . . . . ?
C11B B1 C41B C42B 83.6(5) . . . . ?
C31B B1 C41B C42B -154.4(4) . . . . ?
C21B B1 C41B C42B -38.2(5) . . . . ?
C11B B1 C41B C46B -88.4(5) . . . . ?
C31B B1 C41B C46B 33.6(5) . . . . ?
C21B B1 C41B C46B 149.7(4) . . . . ?
C46B C41B C42B C43B -0.6(6) . . . . ?
B1 C41B C42B C43B -173.2(4) . . . . ?
C41B C42B C43B C44B 0.1(7) . . . . ?
C42B C43B C44B C45B 0.5(7) . . . . ?
C43B C44B C45B C46B -0.6(7) . . . . ?
C44B C45B C46B C41B 0.0(7) . . . . ?
C42B C41B C46B C45B 0.5(6) . . . . ?
B1 C41B C46B C45B 173.1(4) . . . . ?

_refine_diff_density_max         5.259
_refine_diff_density_min         -3.510
_refine_diff_density_rms         0.139



_database_code_depnum_ccdc_archive 'CCDC 1010426'
