# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_final3
_database_code_depnum_ccdc_archive 'CCDC 988733'
_audit_update_record             
;
2015-03-19 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '[Ir(C2H4)(POCOP)] (6)'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H43 Ir O2 P2'
_chemical_formula_weight         617.72

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'
Ir Ir -1.4442 7.9887 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.5336(10)
_cell_length_b                   11.7835(14)
_cell_length_c                   13.3762(15)
_cell_angle_alpha                100.381(2)
_cell_angle_beta                 95.958(2)
_cell_angle_gamma                103.944(2)
_cell_volume                     1268.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6865
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      29.55

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    5.405
_shelx_estimated_absorpt_T_min   0.703
_shelx_estimated_absorpt_T_max   0.855
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7035
_exptl_absorpt_correction_T_max  0.8546
_exptl_absorpt_process_details   SADABS-2004/1

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19459
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.566
_diffrn_reflns_theta_max         31.153
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             7478
_reflns_number_gt                6577
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0179P)²] 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         7478
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0496
_refine_ls_wR_factor_gt          0.0473
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Ir1 Ir 0.96253(2) 0.77859(2) 0.22414(2) 0.00921(3) Uani 1 1 d . . . . .
P1 P 1.17006(9) 0.94933(6) 0.25277(5) 0.01032(14) Uani 1 1 d . . . . .
P2 P 0.80944(9) 0.60515(6) 0.25508(5) 0.01049(14) Uani 1 1 d . . . . .
O2 O 0.9095(2) 0.58017(17) 0.35839(15) 0.0135(4) Uani 1 1 d . . . . .
O1 O 1.2906(2) 0.94985(17) 0.35849(14) 0.0126(4) Uani 1 1 d . . . . .
C1 C 1.0965(3) 0.7654(2) 0.3543(2) 0.0116(5) Uani 1 1 d . . . . .
C2 C 1.2391(3) 0.8529(2) 0.4036(2) 0.0109(5) Uani 1 1 d . . . . .
C3 C 1.3316(3) 0.8468(3) 0.4926(2) 0.0131(5) Uani 1 1 d . . . . .
H3A H 1.4269 0.9089 0.5238 0.016 Uiso 1 1 calc R U . . .
C4 C 1.2817(3) 0.7476(3) 0.5353(2) 0.0144(6) Uani 1 1 d . . . . .
H4A H 1.3446 0.7414 0.5961 0.017 Uiso 1 1 calc R U . . .
C5 C 1.1411(4) 0.6568(3) 0.4908(2) 0.0147(6) Uani 1 1 d . . . . .
H5A H 1.1073 0.5889 0.5202 0.018 Uiso 1 1 calc R U . . .
C6 C 1.0522(3) 0.6686(2) 0.4025(2) 0.0121(5) Uani 1 1 d . . . . .
C7 C 1.3280(3) 0.9666(2) 0.1645(2) 0.0122(5) Uani 1 1 d . . . . .
C8 C 1.3329(4) 0.8385(3) 0.1190(2) 0.0202(7) Uani 1 1 d . . . . .
H8A H 1.4134 0.8406 0.0717 0.030 Uiso 1 1 calc R U . . .
H8B H 1.2248 0.7925 0.0816 0.030 Uiso 1 1 calc R U . . .
H8C H 1.3635 0.8004 0.1747 0.030 Uiso 1 1 calc R U . . .
C9 C 1.4999(4) 1.0365(3) 0.2218(2) 0.0181(6) Uani 1 1 d . . . . .
H9A H 1.5773 1.0430 0.1726 0.027 Uiso 1 1 calc R U . . .
H9B H 1.5341 0.9941 0.2733 0.027 Uiso 1 1 calc R U . . .
H9C H 1.4975 1.1167 0.2561 0.027 Uiso 1 1 calc R U . . .
C10 C 1.2847(4) 1.0274(3) 0.0771(2) 0.0193(6) Uani 1 1 d . . . . .
H10A H 1.3708 1.0341 0.0337 0.029 Uiso 1 1 calc R U . . .
H10B H 1.2752 1.1075 0.1064 0.029 Uiso 1 1 calc R U . . .
H10C H 1.1805 0.9796 0.0356 0.029 Uiso 1 1 calc R U . . .
C11 C 1.1118(4) 1.0912(3) 0.2958(2) 0.0145(6) Uani 1 1 d . . . . .
C12 C 1.2580(4) 1.2022(3) 0.3306(2) 0.0194(6) Uani 1 1 d . . . . .
H12A H 1.2186 1.2730 0.3520 0.029 Uiso 1 1 calc R U . . .
H12B H 1.3194 1.2127 0.2734 0.029 Uiso 1 1 calc R U . . .
H12C H 1.3293 1.1916 0.3886 0.029 Uiso 1 1 calc R U . . .
C13 C 0.9912(4) 1.1113(3) 0.2119(3) 0.0216(7) Uani 1 1 d . . . . .
H13A H 0.9624 1.1861 0.2362 0.032 Uiso 1 1 calc R U . . .
H13B H 0.8923 1.0444 0.1962 0.032 Uiso 1 1 calc R U . . .
H13C H 1.0417 1.1161 0.1498 0.032 Uiso 1 1 calc R U . . .
C14 C 1.0241(4) 1.0715(3) 0.3885(2) 0.0215(7) Uani 1 1 d . . . . .
H14A H 0.9895 1.1431 0.4156 0.032 Uiso 1 1 calc R U . . .
H14B H 1.0988 1.0564 0.4423 0.032 Uiso 1 1 calc R U . . .
H14C H 0.9280 1.0026 0.3669 0.032 Uiso 1 1 calc R U . . .
C15 C 0.8026(4) 0.4650(3) 0.1618(2) 0.0153(6) Uani 1 1 d . . . . .
C16 C 0.9830(4) 0.4666(3) 0.1574(3) 0.0239(7) Uani 1 1 d . . . . .
H16A H 0.9884 0.3948 0.1093 0.036 Uiso 1 1 calc R U . . .
H16B H 1.0373 0.4680 0.2260 0.036 Uiso 1 1 calc R U . . .
H16C H 1.0379 0.5379 0.1339 0.036 Uiso 1 1 calc R U . . .
C17 C 0.7168(4) 0.3500(3) 0.1935(2) 0.0207(6) Uani 1 1 d . . . . .
H17A H 0.7180 0.2806 0.1410 0.031 Uiso 1 1 calc R U . . .
H17B H 0.6035 0.3500 0.2001 0.031 Uiso 1 1 calc R U . . .
H17C H 0.7739 0.3459 0.2596 0.031 Uiso 1 1 calc R U . . .
C18 C 0.7222(4) 0.4681(3) 0.0548(2) 0.0234(7) Uani 1 1 d . . . . .
H18A H 0.7191 0.3942 0.0063 0.035 Uiso 1 1 calc R U . . .
H18B H 0.7855 0.5369 0.0316 0.035 Uiso 1 1 calc R U . . .
H18C H 0.6105 0.4750 0.0579 0.035 Uiso 1 1 calc R U . . .
C19 C 0.6081(3) 0.6014(3) 0.3013(2) 0.0158(6) Uani 1 1 d . . . . .
C20 C 0.5723(4) 0.5196(3) 0.3784(3) 0.0243(7) Uani 1 1 d . . . . .
H20A H 0.4663 0.5209 0.3999 0.036 Uiso 1 1 calc R U . . .
H20B H 0.6581 0.5481 0.4386 0.036 Uiso 1 1 calc R U . . .
H20C H 0.5696 0.4376 0.3456 0.036 Uiso 1 1 calc R U . . .
C21 C 0.4627(4) 0.5651(3) 0.2136(2) 0.0226(7) Uani 1 1 d . . . . .
H21A H 0.3617 0.5648 0.2425 0.034 Uiso 1 1 calc R U . . .
H21B H 0.4549 0.4849 0.1740 0.034 Uiso 1 1 calc R U . . .
H21C H 0.4787 0.6224 0.1684 0.034 Uiso 1 1 calc R U . . .
C22 C 0.6267(4) 0.7308(3) 0.3583(3) 0.0244(7) Uani 1 1 d . . . . .
H22A H 0.5254 0.7362 0.3850 0.037 Uiso 1 1 calc R U . . .
H22B H 0.6490 0.7848 0.3106 0.037 Uiso 1 1 calc R U . . .
H22C H 0.7174 0.7537 0.4155 0.037 Uiso 1 1 calc R U . . .
C23 C 0.8978(4) 0.8022(3) 0.0688(2) 0.0199(6) Uani 1 1 d . . . . .
H23A H 0.9394 0.8836 0.0562 0.024 Uiso 1 1 calc R U . . .
H23B H 0.9042 0.7378 0.0118 0.024 Uiso 1 1 calc R U . . .
C24 C 0.7569(4) 0.7822(3) 0.1140(2) 0.0192(6) Uani 1 1 d . . . . .
H24A H 0.6741 0.7050 0.0858 0.023 Uiso 1 1 calc R U . . .
H24B H 0.7093 0.8508 0.1302 0.023 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
Ir1 C1 2.032(3) . ?
Ir1 C23 2.178(3) . ?
Ir1 C24 2.185(3) . ?
Ir1 P2 2.2771(7) . ?
Ir1 P1 2.2793(7) . ?
P1 O1 1.658(2) . ?
P1 C11 1.867(3) . ?
P1 C7 1.881(3) . ?
P2 O2 1.658(2) . ?
P2 C15 1.866(3) . ?
P2 C19 1.879(3) . ?
O2 C6 1.391(3) . ?
O1 C2 1.387(3) . ?
C1 C2 1.401(4) . ?
C1 C6 1.403(4) . ?
C2 C3 1.383(4) . ?
C3 C4 1.388(4) . ?
C4 C5 1.394(4) . ?
C5 C6 1.384(4) . ?
C7 C10 1.534(4) . ?
C7 C8 1.535(4) . ?
C7 C9 1.541(4) . ?
C11 C13 1.531(4) . ?
C11 C12 1.535(4) . ?
C11 C14 1.539(4) . ?
C15 C17 1.531(4) . ?
C15 C18 1.533(4) . ?
C15 C16 1.543(4) . ?
C19 C21 1.536(4) . ?
C19 C20 1.539(4) . ?
C19 C22 1.539(4) . ?
C23 C24 1.390(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
C1 Ir1 C23 161.07(11) . . ?
C1 Ir1 C24 161.77(11) . . ?
C23 Ir1 C24 37.16(11) . . ?
C1 Ir1 P2 78.82(8) . . ?
C23 Ir1 P2 112.98(9) . . ?
C24 Ir1 P2 89.14(8) . . ?
C1 Ir1 P1 78.72(8) . . ?
C23 Ir1 P1 89.15(9) . . ?
C24 Ir1 P1 112.21(8) . . ?
P2 Ir1 P1 157.48(3) . . ?
O1 P1 C11 99.60(12) . . ?
O1 P1 C7 98.44(11) . . ?
C11 P1 C7 112.33(13) . . ?
O1 P1 Ir1 106.29(7) . . ?
C11 P1 Ir1 115.33(9) . . ?
C7 P1 Ir1 120.58(9) . . ?
O2 P2 C15 99.07(12) . . ?
O2 P2 C19 98.82(12) . . ?
C15 P2 C19 112.25(14) . . ?
O2 P2 Ir1 106.42(7) . . ?
C15 P2 Ir1 116.30(10) . . ?
C19 P2 Ir1 119.68(10) . . ?
C6 O2 P2 114.76(17) . . ?
C2 O1 P1 114.90(17) . . ?
C2 C1 C6 114.7(2) . . ?
C2 C1 Ir1 122.7(2) . . ?
C6 C1 Ir1 122.6(2) . . ?
C3 C2 O1 118.7(2) . . ?
C3 C2 C1 123.9(3) . . ?
O1 C2 C1 117.4(2) . . ?
C2 C3 C4 118.2(3) . . ?
C3 C4 C5 121.3(3) . . ?
C6 C5 C4 117.9(3) . . ?
C5 C6 O2 118.7(2) . . ?
C5 C6 C1 124.0(3) . . ?
O2 C6 C1 117.4(2) . . ?
C10 C7 C8 109.5(2) . . ?
C10 C7 C9 108.4(2) . . ?
C8 C7 C9 108.1(2) . . ?
C10 C7 P1 113.0(2) . . ?
C8 C7 P1 104.99(19) . . ?
C9 C7 P1 112.69(19) . . ?
C13 C11 C12 110.0(2) . . ?
C13 C11 C14 108.4(2) . . ?
C12 C11 C14 108.5(2) . . ?
C13 C11 P1 110.9(2) . . ?
C12 C11 P1 113.9(2) . . ?
C14 C11 P1 104.7(2) . . ?
C17 C15 C18 109.9(2) . . ?
C17 C15 C16 108.8(2) . . ?
C18 C15 C16 108.5(3) . . ?
C17 C15 P2 114.2(2) . . ?
C18 C15 P2 110.0(2) . . ?
C16 C15 P2 105.2(2) . . ?
C21 C19 C20 108.9(2) . . ?
C21 C19 C22 109.1(3) . . ?
C20 C19 C22 107.9(2) . . ?
C21 C19 P2 113.4(2) . . ?
C20 C19 P2 112.8(2) . . ?
C22 C19 P2 104.6(2) . . ?
C24 C23 Ir1 71.66(17) . . ?
C23 C24 Ir1 71.18(17) . . ?

_refine_diff_density_max         1.308
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.147

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_final2
_database_code_depnum_ccdc_archive 'CCDC 988734'
_audit_update_record             
;
2015-03-19 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '[Ir(C3H6)(POCOP)] (7)'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H45 Ir O2 P2'
_chemical_formula_weight         631.75

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.2181(9)
_cell_length_b                   10.7350(6)
_cell_length_c                   15.8712(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.894(2)
_cell_angle_gamma                90
_cell_volume                     2629.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      38.21

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.437
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.227
_exptl_absorpt_coefficient_mu    5.218
_shelx_estimated_absorpt_T_min   0.209
_shelx_estimated_absorpt_T_max   0.384
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2089
_exptl_absorpt_correction_T_max  0.3838
_exptl_absorpt_process_details   SADABS-2004/1

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46673
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.311
_diffrn_reflns_theta_max         36.319
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             12703
_reflns_number_gt                10319
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+6.5195P] 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         12703
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_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
Ir1 Ir 0.27191(2) 0.56731(2) 0.31070(2) 0.01809(4) Uani 1 1 d . . . . .
P1 P 0.17392(5) 0.42066(7) 0.23864(5) 0.02040(13) Uani 1 1 d . . . . .
P2 P 0.33223(5) 0.76092(7) 0.33790(5) 0.02100(13) Uani 1 1 d . . . . .
O1 O 0.10405(14) 0.4914(2) 0.15376(16) 0.0248(4) Uani 1 1 d . . . . .
O2 O 0.27976(15) 0.8491(2) 0.25284(16) 0.0258(4) Uani 1 1 d . . . . .
C1 C 0.19572(16) 0.6660(2) 0.20655(18) 0.0177(4) Uani 1 1 d . . . . .
C2 C 0.12438(17) 0.6140(3) 0.14265(19) 0.0205(5) Uani 1 1 d . . . . .
C3 C 0.07354(19) 0.6767(3) 0.0683(2) 0.0242(5) Uani 1 1 d . . . . .
H3A H 0.0267 0.6362 0.0261 0.029 Uiso 1 1 calc R U . . .
C4 C 0.0934(2) 0.8008(3) 0.0575(2) 0.0255(5) Uani 1 1 d . . . . .
H4A H 0.0596 0.8461 0.0073 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1620(2) 0.8586(3) 0.1196(2) 0.0234(5) Uani 1 1 d . . . . .
H5A H 0.1750 0.9436 0.1128 0.028 Uiso 1 1 calc R U . . .
C6 C 0.21120(19) 0.7908(3) 0.19147(19) 0.0209(5) Uani 1 1 d . . . . .
C7 C 0.2099(2) 0.2978(3) 0.1729(2) 0.0264(5) Uani 1 1 d . . . . .
C8 C 0.2502(3) 0.3721(4) 0.1127(3) 0.0356(7) Uani 1 1 d . . . . .
H8A H 0.2707 0.3144 0.0756 0.053 Uiso 1 1 calc R U . . .
H8B H 0.2990 0.4213 0.1491 0.053 Uiso 1 1 calc R U . . .
H8C H 0.2065 0.4279 0.0748 0.053 Uiso 1 1 calc R U . . .
C9 C 0.1353(3) 0.2187(4) 0.1157(3) 0.0398(8) Uani 1 1 d . . . . .
H9A H 0.1580 0.1567 0.0832 0.060 Uiso 1 1 calc R U . . .
H9B H 0.0935 0.2724 0.0736 0.060 Uiso 1 1 calc R U . . .
H9C H 0.1066 0.1762 0.1537 0.060 Uiso 1 1 calc R U . . .
C10 C 0.2781(4) 0.2109(5) 0.2311(3) 0.0517(12) Uani 1 1 d . . . . .
H10A H 0.2945 0.1487 0.1940 0.078 Uiso 1 1 calc R U . . .
H10B H 0.2544 0.1687 0.2734 0.078 Uiso 1 1 calc R U . . .
H10C H 0.3293 0.2592 0.2635 0.078 Uiso 1 1 calc R U . . .
C11 C 0.0950(2) 0.3579(3) 0.2930(3) 0.0307(6) Uani 1 1 d . . . . .
C12 C 0.0074(3) 0.3224(5) 0.2273(4) 0.0531(12) Uani 1 1 d . . . . .
H12A H -0.0307 0.2904 0.2597 0.080 Uiso 1 1 calc R U . . .
H12B H 0.0159 0.2580 0.1870 0.080 Uiso 1 1 calc R U . . .
H12C H -0.0190 0.3961 0.1931 0.080 Uiso 1 1 calc R U . . .
C13 C 0.1321(3) 0.2470(4) 0.3530(3) 0.0470(10) Uani 1 1 d . . . . .
H13A H 0.0891 0.2169 0.3800 0.070 Uiso 1 1 calc R U . . .
H13B H 0.1846 0.2729 0.3995 0.070 Uiso 1 1 calc R U . . .
H13C H 0.1465 0.1802 0.3178 0.070 Uiso 1 1 calc R U . . .
C14 C 0.0786(3) 0.4657(4) 0.3492(4) 0.0460(10) Uani 1 1 d . . . . .
H14A H 0.0375 0.4391 0.3797 0.069 Uiso 1 1 calc R U . . .
H14B H 0.0546 0.5368 0.3108 0.069 Uiso 1 1 calc R U . . .
H14C H 0.1334 0.4902 0.3930 0.069 Uiso 1 1 calc R U . . .
C15 C 0.4440(2) 0.7877(3) 0.3315(3) 0.0320(7) Uani 1 1 d . . . . .
C16 C 0.4370(7) 0.7294(10) 0.2364(8) 0.048(2) Uani 0.554(8) 1 d . . P A 1
H16A H 0.4928 0.7380 0.2250 0.072 Uiso 0.554(8) 1 calc R U P A 1
H16B H 0.3921 0.7735 0.1904 0.072 Uiso 0.554(8) 1 calc R U P A 1
H16C H 0.4218 0.6409 0.2357 0.072 Uiso 0.554(8) 1 calc R U P A 1
C17 C 0.4658(15) 0.9243(19) 0.3267(11) 0.044(4) Uani 0.554(8) 1 d . . P A 1
H17A H 0.5249 0.9322 0.3234 0.066 Uiso 0.554(8) 1 calc R U P A 1
H17B H 0.4616 0.9673 0.3797 0.066 Uiso 0.554(8) 1 calc R U P A 1
H17C H 0.4250 0.9618 0.2739 0.066 Uiso 0.554(8) 1 calc R U P A 1
C18 C 0.5117(6) 0.7103(16) 0.3967(11) 0.077(5) Uani 0.554(8) 1 d . . P A 1
H18A H 0.5687 0.7281 0.3903 0.116 Uiso 0.554(8) 1 calc R U P A 1
H18B H 0.4982 0.6218 0.3852 0.116 Uiso 0.554(8) 1 calc R U P A 1
H18C H 0.5121 0.7307 0.4570 0.116 Uiso 0.554(8) 1 calc R U P A 1
C16A C 0.4623(7) 0.6999(11) 0.2715(7) 0.034(2) Uani 0.446(8) 1 d . . P A 2
H16D H 0.5209 0.7143 0.2682 0.051 Uiso 0.446(8) 1 calc R U P A 2
H16E H 0.4202 0.7104 0.2126 0.051 Uiso 0.446(8) 1 calc R U P A 2
H16F H 0.4582 0.6151 0.2927 0.051 Uiso 0.446(8) 1 calc R U P A 2
C17A C 0.4630(16) 0.9195(19) 0.3043(18) 0.050(5) Uani 0.446(8) 1 d . . P A 2
H17D H 0.5228 0.9235 0.3026 0.075 Uiso 0.446(8) 1 calc R U P A 2
H17E H 0.4551 0.9800 0.3474 0.075 Uiso 0.446(8) 1 calc R U P A 2
H17F H 0.4232 0.9389 0.2455 0.075 Uiso 0.446(8) 1 calc R U P A 2
C18A C 0.5110(6) 0.7691(10) 0.4280(7) 0.036(2) Uani 0.446(8) 1 d . . P A 2
H18D H 0.5701 0.7828 0.4260 0.054 Uiso 0.446(8) 1 calc R U P A 2
H18E H 0.5060 0.6841 0.4485 0.054 Uiso 0.446(8) 1 calc R U P A 2
H18F H 0.4982 0.8289 0.4689 0.054 Uiso 0.446(8) 1 calc R U P A 2
C19 C 0.3098(3) 0.8549(4) 0.4281(3) 0.0383(8) Uani 1 1 d . . . . .
C20 C 0.3213(9) 0.9960(10) 0.4208(9) 0.044(3) Uani 0.554(8) 1 d . . P A 1
H20A H 0.3086 1.0381 0.4702 0.066 Uiso 0.554(8) 1 calc R U P A 1
H20B H 0.2816 1.0262 0.3647 0.066 Uiso 0.554(8) 1 calc R U P A 1
H20C H 0.3812 1.0140 0.4228 0.066 Uiso 0.554(8) 1 calc R U P A 1
C21 C 0.3794(11) 0.8216(10) 0.5200(6) 0.065(4) Uani 0.554(8) 1 d . . P A 1
H21A H 0.3679 0.8706 0.5672 0.097 Uiso 0.554(8) 1 calc R U P A 1
H21B H 0.4376 0.8410 0.5172 0.097 Uiso 0.554(8) 1 calc R U P A 1
H21C H 0.3758 0.7327 0.5323 0.097 Uiso 0.554(8) 1 calc R U P A 1
C22 C 0.2227(9) 0.8234(12) 0.4299(10) 0.061(3) Uani 0.554(8) 1 d . . P A 1
H22A H 0.2093 0.8714 0.4766 0.091 Uiso 0.554(8) 1 calc R U P A 1
H22B H 0.2198 0.7342 0.4417 0.091 Uiso 0.554(8) 1 calc R U P A 1
H22C H 0.1806 0.8437 0.3725 0.091 Uiso 0.554(8) 1 calc R U P A 1
C20A C 0.3443(9) 0.9821(19) 0.4381(14) 0.063(6) Uani 0.446(8) 1 d . . P A 2
H20D H 0.3296 1.0238 0.4865 0.095 Uiso 0.446(8) 1 calc R U P A 2
H20E H 0.3188 1.0283 0.3829 0.095 Uiso 0.446(8) 1 calc R U P A 2
H20F H 0.4074 0.9794 0.4514 0.095 Uiso 0.446(8) 1 calc R U P A 2
C21A C 0.3304(9) 0.7784(17) 0.5135(7) 0.059(4) Uani 0.446(8) 1 d . . P A 2
H21D H 0.3185 0.8284 0.5601 0.089 Uiso 0.446(8) 1 calc R U P A 2
H21E H 0.3917 0.7544 0.5321 0.089 Uiso 0.446(8) 1 calc R U P A 2
H21F H 0.2943 0.7033 0.5029 0.089 Uiso 0.446(8) 1 calc R U P A 2
C22A C 0.2051(7) 0.8647(12) 0.3940(7) 0.036(2) Uani 0.446(8) 1 d . . P A 2
H22D H 0.1855 0.9128 0.4368 0.054 Uiso 0.446(8) 1 calc R U P A 2
H22E H 0.1801 0.7808 0.3884 0.054 Uiso 0.446(8) 1 calc R U P A 2
H22F H 0.1865 0.9063 0.3363 0.054 Uiso 0.446(8) 1 calc R U P A 2
C23 C 0.3627(4) 0.4223(6) 0.3862(4) 0.0268(13) Uani 0.554(8) 1 d . . P A 1
H23A H 0.3370 0.3397 0.3906 0.032 Uiso 0.554(8) 1 calc R U P A 1
H23B H 0.4194 0.4170 0.3751 0.032 Uiso 0.554(8) 1 calc R U P A 1
C24 C 0.3555(5) 0.5121(6) 0.4474(4) 0.0328(14) Uani 0.554(8) 1 d . . P A 1
H24A H 0.4084 0.5647 0.4715 0.039 Uiso 0.554(8) 1 calc R U P A 1
C25 C 0.3086(5) 0.4833(7) 0.5129(4) 0.0383(17) Uani 0.554(8) 1 d . . P A 1
H25A H 0.3506 0.4606 0.5698 0.058 Uiso 0.554(8) 1 calc R U P A 1
H25B H 0.2686 0.4138 0.4911 0.058 Uiso 0.554(8) 1 calc R U P A 1
H25C H 0.2759 0.5568 0.5208 0.058 Uiso 0.554(8) 1 calc R U P A 1
C23A C 0.3151(6) 0.4345(7) 0.4194(5) 0.0303(17) Uani 0.446(8) 1 d . . P A 2
H23C H 0.3024 0.4559 0.4748 0.036 Uiso 0.446(8) 1 calc R U P A 2
H23D H 0.3066 0.3451 0.4036 0.036 Uiso 0.446(8) 1 calc R U P A 2
C24A C 0.3865(5) 0.4912(9) 0.4061(6) 0.034(2) Uani 0.446(8) 1 d . . P A 2
H24B H 0.4179 0.5503 0.4539 0.041 Uiso 0.446(8) 1 calc R U P A 2
C25A C 0.4422(10) 0.4165(14) 0.3698(10) 0.063(4) Uani 0.446(8) 1 d . . P A 2
H25D H 0.4920 0.3869 0.4181 0.094 Uiso 0.446(8) 1 calc R U P A 2
H25E H 0.4625 0.4672 0.3288 0.094 Uiso 0.446(8) 1 calc R U P A 2
H25F H 0.4095 0.3449 0.3381 0.094 Uiso 0.446(8) 1 calc R U P A 2


_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
Ir1 C1 2.031(3) . ?
Ir1 C24A 2.165(7) . ?
Ir1 C23A 2.182(7) . ?
Ir1 C23 2.223(5) . ?
Ir1 C24 2.256(6) . ?
Ir1 P1 2.2793(8) . ?
Ir1 P2 2.2811(8) . ?
P1 O1 1.655(2) . ?
P1 C11 1.875(3) . ?
P1 C7 1.882(3) . ?
P2 O2 1.654(2) . ?
P2 C15 1.869(3) . ?
P2 C19 1.876(4) . ?
O1 C2 1.381(4) . ?
O2 C6 1.383(4) . ?
C1 C6 1.397(4) . ?
C1 C2 1.399(4) . ?
C2 C3 1.388(4) . ?
C3 C4 1.394(4) . ?
C4 C5 1.385(5) . ?
C5 C6 1.383(4) . ?
C7 C10 1.524(5) . ?
C7 C9 1.528(5) . ?
C7 C8 1.536(5) . ?
C11 C13 1.527(6) . ?
C11 C12 1.530(6) . ?
C11 C14 1.534(6) . ?
C15 C16A 1.434(12) . ?
C15 C18 1.505(11) . ?
C15 C17 1.52(2) . ?
C15 C17A 1.54(2) . ?
C15 C18A 1.595(11) . ?
C15 C16 1.606(11) . ?
C19 C22 1.461(12) . ?
C19 C20A 1.47(2) . ?
C19 C21A 1.531(14) . ?
C19 C20 1.535(12) . ?
C19 C21 1.586(11) . ?
C19 C22A 1.619(12) . ?
C23 C24 1.399(10) . ?
C24 C25 1.498(9) . ?
C23A C24A 1.381(13) . ?
C24A C25A 1.452(17) . ?

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
C1 Ir1 C24A 160.5(3) . . ?
C1 Ir1 C23A 162.1(2) . . ?
C24A Ir1 C23A 37.1(3) . . ?
C1 Ir1 C23 160.08(18) . . ?
C1 Ir1 C24 162.8(2) . . ?
C23 Ir1 C24 36.4(2) . . ?
C1 Ir1 P1 78.22(8) . . ?
C24A Ir1 P1 114.0(3) . . ?
C23A Ir1 P1 87.2(2) . . ?
C23 Ir1 P1 91.76(18) . . ?
C24 Ir1 P1 114.93(18) . . ?
C1 Ir1 P2 78.30(8) . . ?
C24A Ir1 P2 89.2(3) . . ?
C23A Ir1 P2 115.5(2) . . ?
C23 Ir1 P2 111.21(18) . . ?
C24 Ir1 P2 87.78(18) . . ?
P1 Ir1 P2 156.44(3) . . ?
O1 P1 C11 98.41(15) . . ?
O1 P1 C7 96.99(14) . . ?
C11 P1 C7 112.02(16) . . ?
O1 P1 Ir1 106.79(9) . . ?
C11 P1 Ir1 119.12(12) . . ?
C7 P1 Ir1 118.37(11) . . ?
O2 P2 C15 97.58(15) . . ?
O2 P2 C19 98.26(16) . . ?
C15 P2 C19 112.2(2) . . ?
O2 P2 Ir1 106.48(9) . . ?
C15 P2 Ir1 119.78(12) . . ?
C19 P2 Ir1 117.52(15) . . ?
C2 O1 P1 114.26(18) . . ?
C6 O2 P2 114.62(19) . . ?
C6 C1 C2 114.2(2) . . ?
C6 C1 Ir1 122.9(2) . . ?
C2 C1 Ir1 122.9(2) . . ?
O1 C2 C3 117.9(3) . . ?
O1 C2 C1 117.6(2) . . ?
C3 C2 C1 124.5(3) . . ?
C2 C3 C4 117.9(3) . . ?
C5 C4 C3 120.4(3) . . ?
C6 C5 C4 119.0(3) . . ?
O2 C6 C5 118.6(3) . . ?
O2 C6 C1 117.5(2) . . ?
C5 C6 C1 123.9(3) . . ?
C10 C7 C9 108.3(3) . . ?
C10 C7 C8 109.1(3) . . ?
C9 C7 C8 109.2(3) . . ?
C10 C7 P1 112.6(3) . . ?
C9 C7 P1 113.3(3) . . ?
C8 C7 P1 104.2(2) . . ?
C13 C11 C12 109.7(4) . . ?
C13 C11 C14 109.4(4) . . ?
C12 C11 C14 107.1(4) . . ?
C13 C11 P1 111.9(3) . . ?
C12 C11 P1 113.4(3) . . ?
C14 C11 P1 105.1(2) . . ?
C18 C15 C17 115.9(11) . . ?
C16A C15 C17A 108.5(11) . . ?
C16A C15 C18A 109.7(6) . . ?
C17A C15 C18A 104.4(11) . . ?
C18 C15 C16 104.9(9) . . ?
C17 C15 C16 106.3(7) . . ?
C16A C15 P2 109.7(5) . . ?
C18 C15 P2 113.1(5) . . ?
C17 C15 P2 113.4(9) . . ?
C17A C15 P2 116.0(9) . . ?
C18A C15 P2 108.3(5) . . ?
C16 C15 P2 101.6(4) . . ?
C20A C19 C21A 115.6(10) . . ?
C22 C19 C20 111.7(7) . . ?
C22 C19 C21 110.5(9) . . ?
C20 C19 C21 102.9(7) . . ?
C20A C19 C22A 107.5(7) . . ?
C21A C19 C22A 104.6(7) . . ?
C22 C19 P2 107.8(5) . . ?
C20A C19 P2 115.3(9) . . ?
C21A C19 P2 110.2(6) . . ?
C20 C19 P2 114.6(5) . . ?
C21 C19 P2 109.3(5) . . ?
C22A C19 P2 102.0(4) . . ?
C24 C23 Ir1 73.1(3) . . ?
C23 C24 C25 120.6(7) . . ?
C23 C24 Ir1 70.5(3) . . ?
C25 C24 Ir1 116.0(5) . . ?
C24A C23A Ir1 70.8(4) . . ?
C23A C24A C25A 118.0(11) . . ?
C23A C24A Ir1 72.1(4) . . ?
C25A C24A Ir1 115.9(8) . . ?

_refine_diff_density_max         3.971
_refine_diff_density_min         -2.802
_refine_diff_density_rms         0.193

_shelxl_version_number           2013-4

