# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_ligand4
_database_code_depnum_ccdc_archive 'CCDC 1478500'
_audit_update_record             
;
2016-06-25 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
((4,6-bis(trifluoromethyl)-1,3-phenylene)bis(oxy))bis(di-tert-butylphosphine)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H38 F6 O2 P2'
_chemical_formula_sum            'C24 H38 F6 O2 P2'
_chemical_formula_weight         534.48

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'
F F 0.0171 0.0103 '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      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                   12.132(5)
_cell_length_b                   18.353(5)
_cell_length_c                   14.104(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.774(5)
_cell_angle_gamma                90
_cell_volume                     2955.2(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3874
_cell_measurement_theta_min      2.9290
_cell_measurement_theta_max      28.7738

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.202
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89637
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1367
_diffrn_reflns_number            33067
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.935
_diffrn_reflns_theta_max         28.838
_diffrn_reflns_theta_full        26.500
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7037
_reflns_number_gt                4044
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Crystal Maker 8.7'
_computing_publication_material  'WinGX -2014.1'
_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)+(0.0726P)²+0.9739P] 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         7037
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_ref         0.1841
_refine_ls_wR_factor_gt          0.1548
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
P1 P -0.08823(6) 0.13533(4) 0.49618(5) 0.0555(2) Uani 1 1 d . . . . .
P2 P 0.30687(6) 0.14287(4) 0.78405(5) 0.0521(2) Uani 1 1 d . . . . .
O2 O 0.29532(14) 0.23422(9) 0.76636(12) 0.0522(4) Uani 1 1 d . . . . .
O1 O -0.08684(14) 0.22665(9) 0.51270(12) 0.0529(4) Uani 1 1 d . . . . .
F1 F -0.19923(17) 0.36166(11) 0.52339(17) 0.0998(7) Uani 1 1 d . . . . .
F3 F -0.09113(19) 0.45060(10) 0.51584(18) 0.1140(8) Uani 1 1 d . . . . .
F6 F 0.3177(2) 0.37264(11) 0.86470(14) 0.1032(7) Uani 1 1 d . . . . .
F4 F 0.27722(18) 0.45793(10) 0.75527(16) 0.1009(7) Uani 1 1 d . . . . .
F5 F 0.39555(17) 0.37303(11) 0.74955(17) 0.0990(7) Uani 1 1 d . . . . .
F2 F -0.1228(2) 0.36469(12) 0.40871(15) 0.1170(8) Uani 1 1 d . . . . .
C5 C 0.1979(2) 0.26668(13) 0.70196(16) 0.0425(5) Uani 1 1 d . . . . .
C1 C 0.0078(2) 0.26304(13) 0.57463(16) 0.0433(5) Uani 1 1 d . . . . .
C4 C 0.1955(2) 0.34289(13) 0.70057(18) 0.0470(6) Uani 1 1 d . . . . .
C6 C 0.1045(2) 0.22759(13) 0.63939(16) 0.0450(5) Uani 1 1 d . . . . .
H6 H 0.1066 0.1769 0.6408 0.054 Uiso 1 1 calc R U . . .
C3 C 0.0978(2) 0.37773(13) 0.63575(18) 0.0526(6) Uani 1 1 d . . . . .
H3 H 0.0956 0.4284 0.6345 0.063 Uiso 1 1 calc R U . . .
C2 C 0.0035(2) 0.33926(13) 0.57296(18) 0.0486(6) Uani 1 1 d . . . . .
C8 C 0.2955(3) 0.38616(16) 0.7673(2) 0.0676(8) Uani 1 1 d . . . . .
C10 C -0.1290(3) 0.13595(18) 0.3559(2) 0.0709(8) Uani 1 1 d . . . . .
C12 C 0.4410(3) 0.13022(17) 0.7500(3) 0.0726(9) Uani 1 1 d . . . . .
C9 C -0.2159(3) 0.11555(18) 0.5377(2) 0.0781(9) Uani 1 1 d . . . . .
C11 C 0.3388(3) 0.1437(2) 0.9235(3) 0.0873(11) Uani 1 1 d . . . . .
C18 C -0.0272(4) 0.1766(3) 0.3382(3) 0.1185(15) Uani 1 1 d . . . . .
H18A H 0.0453 0.1532 0.3751 0.178 Uiso 1 1 calc R U . . .
H18B H -0.0376 0.1761 0.2676 0.178 Uiso 1 1 calc R U . . .
H18C H -0.0257 0.2261 0.3607 0.178 Uiso 1 1 calc R U . . .
C23 C 0.3920(4) 0.1351(2) 0.6329(3) 0.1159(15) Uani 1 1 d . . . . .
H23A H 0.3309 0.0996 0.6070 0.174 Uiso 1 1 calc R U . . .
H23B H 0.3610 0.1830 0.6130 0.174 Uiso 1 1 calc R U . . .
H23C H 0.4539 0.1255 0.6065 0.174 Uiso 1 1 calc R U . . .
C7 C -0.1014(3) 0.37839(16) 0.5052(3) 0.0714(9) Uani 1 1 d . . . . .
C16 C -0.1290(4) 0.0566(2) 0.3219(3) 0.1204(16) Uani 1 1 d . . . . .
H16A H -0.0566 0.0338 0.3607 0.181 Uiso 1 1 calc R U . . .
H16B H -0.1932 0.0310 0.3319 0.181 Uiso 1 1 calc R U . . .
H16C H -0.1372 0.0554 0.2518 0.181 Uiso 1 1 calc R U . . .
C14 C -0.1635(4) 0.1200(2) 0.6535(3) 0.1232(16) Uani 1 1 d . . . . .
H14A H -0.1390 0.1690 0.6733 0.185 Uiso 1 1 calc R U . . .
H14B H -0.2216 0.1057 0.6822 0.185 Uiso 1 1 calc R U . . .
H14C H -0.0973 0.0879 0.6772 0.185 Uiso 1 1 calc R U . . .
C17 C -0.2416(4) 0.1744(2) 0.2967(2) 0.1109(14) Uani 1 1 d . . . . .
H17A H -0.2390 0.2238 0.3196 0.166 Uiso 1 1 calc R U . . .
H17B H -0.2507 0.1740 0.2264 0.166 Uiso 1 1 calc R U . . .
H17C H -0.3067 0.1496 0.3065 0.166 Uiso 1 1 calc R U . . .
C15 C -0.2540(4) 0.0370(2) 0.5089(3) 0.1299(17) Uani 1 1 d . . . . .
H15A H -0.1871 0.0055 0.5323 0.195 Uiso 1 1 calc R U . . .
H15B H -0.3106 0.0229 0.5391 0.195 Uiso 1 1 calc R U . . .
H15C H -0.2881 0.0333 0.4369 0.195 Uiso 1 1 calc R U . . .
C24 C 0.4865(4) 0.0531(2) 0.7796(4) 0.1215(15) Uani 1 1 d . . . . .
H24A H 0.4230 0.0191 0.7549 0.182 Uiso 1 1 calc R U . . .
H24B H 0.5458 0.0421 0.7508 0.182 Uiso 1 1 calc R U . . .
H24C H 0.5192 0.0496 0.8517 0.182 Uiso 1 1 calc R U . . .
C21 C 0.3434(5) 0.0629(2) 0.9562(3) 0.1331(18) Uani 1 1 d . . . . .
H21A H 0.4094 0.0394 0.9463 0.200 Uiso 1 1 calc R U . . .
H21B H 0.3510 0.0604 1.0262 0.200 Uiso 1 1 calc R U . . .
H21C H 0.2726 0.0387 0.9165 0.200 Uiso 1 1 calc R U . . .
C22 C 0.5368(3) 0.1871(2) 0.7866(4) 0.1170(16) Uani 1 1 d . . . . .
H22A H 0.5042 0.2347 0.7663 0.175 Uiso 1 1 calc R U . . .
H22B H 0.5701 0.1852 0.8587 0.175 Uiso 1 1 calc R U . . .
H22C H 0.5967 0.1776 0.7579 0.175 Uiso 1 1 calc R U . . .
C13 C -0.3191(4) 0.1688(3) 0.5023(4) 0.1301(17) Uani 1 1 d . . . . .
H13A H -0.2917 0.2174 0.5218 0.195 Uiso 1 1 calc R U . . .
H13B H -0.3539 0.1663 0.4302 0.195 Uiso 1 1 calc R U . . .
H13C H -0.3765 0.1560 0.5325 0.195 Uiso 1 1 calc R U . . .
C20 C 0.4497(4) 0.1855(3) 0.9867(3) 0.1398(19) Uani 1 1 d . . . . .
H20A H 0.5175 0.1630 0.9790 0.210 Uiso 1 1 calc R U . . .
H20B H 0.4445 0.2352 0.9641 0.210 Uiso 1 1 calc R U . . .
H20C H 0.4560 0.1845 1.0564 0.210 Uiso 1 1 calc R U . . .
C19 C 0.2355(5) 0.1814(3) 0.9386(3) 0.1392(19) Uani 1 1 d . . . . .
H19A H 0.1647 0.1567 0.9002 0.209 Uiso 1 1 calc R U . . .
H19B H 0.2439 0.1803 1.0087 0.209 Uiso 1 1 calc R U . . .
H19C H 0.2323 0.2310 0.9164 0.209 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
P1 O1 1.6915(18) . ?
P1 C9 1.868(3) . ?
P1 C10 1.870(3) . ?
P2 O2 1.6937(18) . ?
P2 C12 1.860(3) . ?
P2 C11 1.872(3) . ?
O2 C5 1.360(3) . ?
O1 C1 1.359(3) . ?
F1 C7 1.332(4) . ?
F3 C7 1.335(3) . ?
F6 C8 1.331(3) . ?
F4 C8 1.337(3) . ?
F5 C8 1.341(4) . ?
F2 C7 1.320(4) . ?
C5 C6 1.379(3) . ?
C5 C4 1.399(3) . ?
C1 C6 1.382(3) . ?
C1 C2 1.400(3) . ?
C4 C3 1.384(3) . ?
C4 C8 1.489(4) . ?
C3 C2 1.380(3) . ?
C2 C7 1.492(4) . ?
C10 C17 1.514(5) . ?
C10 C16 1.533(5) . ?
C10 C18 1.534(5) . ?
C12 C22 1.517(5) . ?
C12 C24 1.525(5) . ?
C12 C23 1.557(5) . ?
C9 C15 1.526(5) . ?
C9 C13 1.533(5) . ?
C9 C14 1.541(5) . ?
C11 C19 1.507(5) . ?
C11 C20 1.544(6) . ?
C11 C21 1.549(5) . ?

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
O1 P1 C9 96.89(13) . . ?
O1 P1 C10 97.26(12) . . ?
C9 P1 C10 112.51(15) . . ?
O2 P2 C12 96.98(12) . . ?
O2 P2 C11 97.12(13) . . ?
C12 P2 C11 112.58(16) . . ?
C5 O2 P2 122.80(15) . . ?
C1 O1 P1 122.83(15) . . ?
O2 C5 C6 122.7(2) . . ?
O2 C5 C4 117.2(2) . . ?
C6 C5 C4 120.2(2) . . ?
O1 C1 C6 122.5(2) . . ?
O1 C1 C2 117.5(2) . . ?
C6 C1 C2 120.0(2) . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 C8 120.3(2) . . ?
C5 C4 C8 121.1(2) . . ?
C5 C6 C1 120.6(2) . . ?
C2 C3 C4 121.7(2) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 C7 120.5(2) . . ?
C1 C2 C7 120.7(2) . . ?
F6 C8 F4 106.4(2) . . ?
F6 C8 F5 106.3(3) . . ?
F4 C8 F5 106.0(2) . . ?
F6 C8 C4 112.9(2) . . ?
F4 C8 C4 112.4(3) . . ?
F5 C8 C4 112.4(2) . . ?
C17 C10 C16 111.4(3) . . ?
C17 C10 C18 108.0(3) . . ?
C16 C10 C18 109.1(3) . . ?
C17 C10 P1 116.9(2) . . ?
C16 C10 P1 107.3(2) . . ?
C18 C10 P1 103.7(2) . . ?
C22 C12 C24 112.4(3) . . ?
C22 C12 C23 107.2(3) . . ?
C24 C12 C23 108.4(3) . . ?
C22 C12 P2 117.6(2) . . ?
C24 C12 P2 108.2(2) . . ?
C23 C12 P2 102.3(2) . . ?
C15 C9 C13 112.0(4) . . ?
C15 C9 C14 108.1(3) . . ?
C13 C9 C14 108.1(4) . . ?
C15 C9 P1 107.9(3) . . ?
C13 C9 P1 116.5(2) . . ?
C14 C9 P1 103.5(3) . . ?
C19 C11 C20 107.1(4) . . ?
C19 C11 C21 110.2(4) . . ?
C20 C11 C21 111.6(3) . . ?
C19 C11 P2 105.4(3) . . ?
C20 C11 P2 116.2(3) . . ?
C21 C11 P2 106.2(3) . . ?
F2 C7 F1 106.1(3) . . ?
F2 C7 F3 106.5(3) . . ?
F1 C7 F3 105.2(3) . . ?
F2 C7 C2 113.3(3) . . ?
F1 C7 C2 112.8(2) . . ?
F3 C7 C2 112.3(3) . . ?

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_compl5
_database_code_depnum_ccdc_archive 'CCDC 1478501'
_audit_update_record             
;
2016-06-25 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H37 Cl F6 Ir O2 P2'
_chemical_formula_sum            'C24 H37 Cl F6 Ir O2 P2'
_chemical_formula_weight         761.12

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'
F F 0.0171 0.0103 '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/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                   8.318(5)
_cell_length_b                   31.333(5)
_cell_length_c                   12.075(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.444(5)
_cell_angle_gamma                90
_cell_volume                     2968(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6554
_cell_measurement_theta_min      2.8984
_cell_measurement_theta_max      28.6550

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_F_000             1500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    4.754
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74925
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1367
_diffrn_reflns_number            18421
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.904
_diffrn_reflns_theta_max         28.719
_diffrn_reflns_theta_full        26.500
_diffrn_measured_fraction_theta_max 0.862
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.862
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             6622
_reflns_number_gt                5496
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Crystal Maker 8.7'
_computing_publication_material  'WinGX -2014.1'
_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)+(0.0322P)²+7.3757P] 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         6622
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.34782(2) 0.15418(2) 0.83947(2) 0.03630(7) Uani 1 1 d . . . . .
P2 P 0.54908(17) 0.16804(4) 1.01845(12) 0.0381(3) Uani 1 1 d . . . . .
P1 P 0.19500(16) 0.11883(5) 0.67084(11) 0.0419(3) Uani 1 1 d . . . . .
O2 O 0.6674(4) 0.12426(12) 1.0471(3) 0.0456(9) Uani 1 1 d . . . . .
F6 F 0.8380(6) 0.05659(17) 1.1881(3) 0.0957(15) Uani 1 1 d . . . . .
O1 O 0.3018(5) 0.07348(13) 0.6794(3) 0.0520(10) Uani 1 1 d . . . . .
F5 F 0.9342(6) 0.01094(15) 1.0988(4) 0.1081(18) Uani 1 1 d . . . . .
F3 F 0.5896(9) -0.0364(2) 0.7268(6) 0.177(4) Uani 1 1 d . . . . .
F4 F 0.9927(5) 0.07578(19) 1.0924(4) 0.1106(18) Uani 1 1 d . . . . .
C4 C 0.6691(7) 0.02367(18) 0.8963(5) 0.0510(14) Uani 1 1 d . . . . .
H4 H 0.7314 -0.0015 0.9074 0.061 Uiso 1 1 calc R U . . .
F2 F 0.3342(8) -0.01722(19) 0.6688(6) 0.136(2) Uani 1 1 d . . . . .
C5 C 0.7150(7) 0.05525(18) 0.9823(5) 0.0436(12) Uani 1 1 d . . . . .
F1 F 0.4999(10) 0.0114(2) 0.6027(5) 0.151(3) Uani 1 1 d . . . . .
C7 C 0.4910(11) -0.0036(2) 0.7018(7) 0.077(2) Uani 1 1 d . . . . .
C11 C 0.7163(8) 0.2084(2) 1.0288(6) 0.0577(16) Uani 1 1 d . . . . .
C3 C 0.5318(7) 0.02941(19) 0.7945(5) 0.0496(13) Uani 1 1 d . . . . .
C8 C 0.8686(8) 0.0499(2) 1.0894(6) 0.0609(17) Uani 1 1 d . . . . .
C12 C 0.4693(7) 0.1677(2) 1.1452(5) 0.0541(15) Uani 1 1 d . . . . .
C10 C -0.0142(8) 0.0982(2) 0.6704(6) 0.0622(17) Uani 1 1 d . . . . .
C6 C 0.6209(6) 0.09266(16) 0.9636(4) 0.0382(11) Uani 1 1 d . . . . .
C9 C 0.1917(8) 0.1388(2) 0.5263(5) 0.0610(17) Uani 1 1 d . . . . .
C1 C 0.4808(6) 0.09990(17) 0.8626(4) 0.0374(11) Uani 1 1 d . . . . .
C2 C 0.4408(6) 0.06722(18) 0.7802(4) 0.0419(12) Uani 1 1 d . . . . .
C23 C 0.6037(10) 0.1551(3) 1.2607(6) 0.089(3) Uani 1 1 d . . . . .
H23A H 0.6929 0.1761 1.2818 0.133 Uiso 1 1 calc R U . . .
H23B H 0.5525 0.1535 1.3210 0.133 Uiso 1 1 calc R U . . .
H23C H 0.6506 0.1278 1.2522 0.133 Uiso 1 1 calc R U . . .
C20 C 0.8593(10) 0.2078(3) 1.1472(8) 0.106(3) Uani 1 1 d . . . . .
H20A H 0.9089 0.1798 1.1616 0.159 Uiso 1 1 calc R U . . .
H20B H 0.9452 0.2282 1.1464 0.159 Uiso 1 1 calc R U . . .
H20C H 0.8140 0.2151 1.2082 0.159 Uiso 1 1 calc R U . . .
C24 C 0.3271(11) 0.1340(3) 1.1120(8) 0.101(3) Uani 1 1 d . . . . .
H24A H 0.2419 0.1418 1.0390 0.152 Uiso 1 1 calc R U . . .
H24B H 0.3742 0.1067 1.1036 0.152 Uiso 1 1 calc R U . . .
H24C H 0.2762 0.1324 1.1725 0.152 Uiso 1 1 calc R U . . .
C22 C 0.3891(11) 0.2117(3) 1.1553(7) 0.097(3) Uani 1 1 d . . . . .
H22A H 0.3048 0.2188 1.0814 0.146 Uiso 1 1 calc R U . . .
H22B H 0.3363 0.2103 1.2149 0.146 Uiso 1 1 calc R U . . .
H22C H 0.4765 0.2331 1.1760 0.146 Uiso 1 1 calc R U . . .
C19 C 0.7915(11) 0.1975(3) 0.9340(8) 0.107(3) Uani 1 1 d . . . . .
H19A H 0.8428 0.1697 0.9489 0.161 Uiso 1 1 calc R U . . .
H19B H 0.7028 0.1976 0.8588 0.161 Uiso 1 1 calc R U . . .
H19C H 0.8764 0.2182 0.9342 0.161 Uiso 1 1 calc R U . . .
C21 C 0.6352(11) 0.2526(2) 1.0038(9) 0.103(3) Uani 1 1 d . . . . .
H21A H 0.5871 0.2599 1.0634 0.154 Uiso 1 1 calc R U . . .
H21B H 0.7205 0.2733 1.0038 0.154 Uiso 1 1 calc R U . . .
H21C H 0.5470 0.2526 0.9285 0.154 Uiso 1 1 calc R U . . .
C15 C 0.3815(10) 0.1434(4) 0.5360(8) 0.116(4) Uani 1 1 d . . . . .
H15A H 0.4380 0.1623 0.5996 0.174 Uiso 1 1 calc R U . . .
H15B H 0.4354 0.1159 0.5504 0.174 Uiso 1 1 calc R U . . .
H15C H 0.3885 0.1548 0.4640 0.174 Uiso 1 1 calc R U . . .
C13 C 0.1061(11) 0.1823(3) 0.5033(7) 0.093(3) Uani 1 1 d . . . . .
H13A H 0.1592 0.2009 0.5685 0.139 Uiso 1 1 calc R U . . .
H13B H 0.1178 0.1943 0.4331 0.139 Uiso 1 1 calc R U . . .
H13C H -0.0126 0.1793 0.4936 0.139 Uiso 1 1 calc R U . . .
C18 C 0.0128(11) 0.0880(3) 0.7990(8) 0.099(3) Uani 1 1 d . . . . .
H18A H 0.0487 0.1133 0.8454 0.148 Uiso 1 1 calc R U . . .
H18B H -0.0921 0.0779 0.8065 0.148 Uiso 1 1 calc R U . . .
H18C H 0.0988 0.0664 0.8260 0.148 Uiso 1 1 calc R U . . .
C17 C -0.0704(12) 0.0580(4) 0.5993(10) 0.137(5) Uani 1 1 d . . . . .
H17A H 0.0178 0.0368 0.6250 0.205 Uiso 1 1 calc R U . . .
H17B H -0.1726 0.0474 0.6099 0.205 Uiso 1 1 calc R U . . .
H17C H -0.0922 0.0641 0.5177 0.205 Uiso 1 1 calc R U . . .
C14 C 0.1104(12) 0.1086(3) 0.4244(6) 0.101(3) Uani 1 1 d . . . . .
H14A H 0.1662 0.0814 0.4406 0.151 Uiso 1 1 calc R U . . .
H14B H -0.0083 0.1052 0.4143 0.151 Uiso 1 1 calc R U . . .
H14C H 0.1221 0.1202 0.3539 0.151 Uiso 1 1 calc R U . . .
C16 C -0.1471(9) 0.1335(3) 0.6353(9) 0.115(4) Uani 1 1 d . . . . .
H16A H -0.1049 0.1582 0.6831 0.172 Uiso 1 1 calc R U . . .
H16B H -0.1699 0.1406 0.5542 0.172 Uiso 1 1 calc R U . . .
H16C H -0.2502 0.1239 0.6464 0.172 Uiso 1 1 calc R U . . .
Cl1 Cl 0.1746(2) 0.21609(6) 0.82237(15) 0.0691(5) Uani 1 1 d . . . . .


_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 1.997(5) . ?
Ir1 P2 2.2919(15) . ?
Ir1 P1 2.2946(15) . ?
Ir1 Cl1 2.3840(16) . ?
P2 O2 1.656(4) . ?
P2 C11 1.853(6) . ?
P2 C12 1.859(6) . ?
P1 O1 1.661(4) . ?
P1 C9 1.846(6) . ?
P1 C10 1.855(6) . ?
O2 C6 1.374(6) . ?
F6 C8 1.317(7) . ?
O1 C2 1.386(6) . ?
F5 C8 1.325(7) . ?
F3 C7 1.288(9) . ?
F4 C8 1.304(8) . ?
C4 C5 1.393(8) . ?
C4 C3 1.383(8) . ?
F2 C7 1.303(9) . ?
C5 C6 1.386(7) . ?
C5 C8 1.494(8) . ?
F1 C7 1.310(10) . ?
C7 C3 1.478(9) . ?
C11 C21 1.527(10) . ?
C11 C19 1.515(10) . ?
C11 C20 1.526(9) . ?
C3 C2 1.385(8) . ?
C12 C23 1.521(9) . ?
C12 C24 1.536(11) . ?
C12 C22 1.554(10) . ?
C10 C17 1.507(11) . ?
C10 C16 1.521(11) . ?
C10 C18 1.527(10) . ?
C6 C1 1.397(7) . ?
C9 C14 1.520(10) . ?
C9 C13 1.521(11) . ?
C9 C15 1.550(10) . ?
C1 C2 1.389(7) . ?

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 P2 80.37(14) . . ?
C1 Ir1 P1 80.24(14) . . ?
P2 Ir1 P1 160.59(5) . . ?
C1 Ir1 Cl1 174.67(15) . . ?
P2 Ir1 Cl1 99.10(6) . . ?
P1 Ir1 Cl1 100.11(6) . . ?
O2 P2 C11 99.8(3) . . ?
O2 P2 C12 100.0(3) . . ?
C11 P2 C12 114.4(3) . . ?
O2 P2 Ir1 103.70(13) . . ?
C11 P2 Ir1 119.3(2) . . ?
C12 P2 Ir1 115.2(2) . . ?
O1 P1 C9 100.8(3) . . ?
O1 P1 C10 100.6(3) . . ?
C9 P1 C10 113.4(3) . . ?
O1 P1 Ir1 103.36(14) . . ?
C9 P1 Ir1 120.3(2) . . ?
C10 P1 Ir1 114.4(2) . . ?
C6 O2 P2 116.2(3) . . ?
C2 O1 P1 116.6(3) . . ?
C5 C4 C3 120.7(5) . . ?
C4 C5 C6 118.6(5) . . ?
C4 C5 C8 120.6(5) . . ?
C6 C5 C8 120.7(5) . . ?
F2 C7 F3 107.7(8) . . ?
F2 C7 F1 101.1(8) . . ?
F3 C7 F1 105.9(8) . . ?
F2 C7 C3 114.5(6) . . ?
F3 C7 C3 114.4(7) . . ?
F1 C7 C3 112.0(7) . . ?
C21 C11 C19 108.8(7) . . ?
C21 C11 C20 110.5(7) . . ?
C19 C11 C20 108.4(7) . . ?
C21 C11 P2 109.5(5) . . ?
C19 C11 P2 106.5(5) . . ?
C20 C11 P2 112.9(5) . . ?
C4 C3 C2 118.5(5) . . ?
C4 C3 C7 119.7(6) . . ?
C2 C3 C7 121.7(6) . . ?
F4 C8 F6 105.3(6) . . ?
F4 C8 F5 105.8(6) . . ?
F6 C8 F5 105.5(6) . . ?
F4 C8 C5 113.3(6) . . ?
F6 C8 C5 113.5(5) . . ?
F5 C8 C5 112.8(6) . . ?
C23 C12 C24 109.2(7) . . ?
C23 C12 C22 111.2(6) . . ?
C24 C12 C22 108.4(6) . . ?
C23 C12 P2 113.7(4) . . ?
C24 C12 P2 104.1(4) . . ?
C22 C12 P2 109.9(5) . . ?
C17 C10 C16 113.0(7) . . ?
C17 C10 C18 108.5(8) . . ?
C16 C10 C18 106.4(7) . . ?
C17 C10 P1 114.0(5) . . ?
C16 C10 P1 109.9(5) . . ?
C18 C10 P1 104.4(5) . . ?
O2 C6 C5 118.9(4) . . ?
O2 C6 C1 118.2(4) . . ?
C5 C6 C1 122.8(5) . . ?
C14 C9 C13 110.8(6) . . ?
C14 C9 C15 106.6(7) . . ?
C13 C9 C15 109.5(7) . . ?
C14 C9 P1 114.6(5) . . ?
C13 C9 P1 109.6(5) . . ?
C15 C9 P1 105.4(5) . . ?
C2 C1 C6 115.9(5) . . ?
C2 C1 Ir1 122.6(4) . . ?
C6 C1 Ir1 121.5(4) . . ?
O1 C2 C3 119.5(5) . . ?
O1 C2 C1 117.1(5) . . ?
C3 C2 C1 123.4(5) . . ?

_refine_diff_density_max         0.903
_refine_diff_density_min         -1.800
_refine_diff_density_rms         0.096

####################################################################### 
# 
# 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_compl6
_database_code_depnum_ccdc_archive 'CCDC 1478502'
_audit_update_record             
;
2016-06-25 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H57 F6 Ir O2 P2'
_chemical_formula_sum            'C38 H57 F6 Ir O2 P2'
_chemical_formula_weight         913.97

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'
F F 0.0171 0.0103 '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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.709(5)
_cell_length_b                   22.841(5)
_cell_length_c                   10.007(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.394(5)
_cell_angle_gamma                90
_cell_volume                     1988.9(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4009
_cell_measurement_theta_min      2.9372
_cell_measurement_theta_max      28.7395

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    3.496
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68517
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1367
_diffrn_reflns_number            22511
_diffrn_reflns_av_unetI/netI     0.1159
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.943
_diffrn_reflns_theta_max         28.803
_diffrn_reflns_theta_full        26.500
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             9107
_reflns_number_gt                6766
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_max     0.831
_reflns_Friedel_fraction_full    0.986

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Crystal Maker 8.7'
_computing_publication_material  'WinGX -2014.1'
_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)+(0.0320P)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_abs_structure_details 
;
 Flack x determined using 2291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.420(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9107
_refine_ls_number_parameters     442
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
Ir1 Ir 0.69586(5) 0.40103(7) 0.33644(4) 0.03173(13) Uani 1 1 d . . . . .
P1 P 0.7013(6) 0.3039(2) 0.3915(5) 0.0377(12) Uani 1 1 d . . . . .
P2 P 0.6494(6) 0.5000(2) 0.3637(5) 0.0352(11) Uani 1 1 d . . . . .
O1 O 0.6042(15) 0.2985(6) 0.5322(12) 0.041(3) Uani 1 1 d . . . . .
C3 C 0.472(2) 0.3487(10) 0.696(2) 0.042(6) Uani 1 1 d . . . . .
F6 F 0.5101(15) 0.5481(5) 0.7680(13) 0.067(3) Uani 1 1 d . . . . .
F4 F 0.3276(16) 0.5028(6) 0.8580(13) 0.074(4) Uani 1 1 d . . . . .
C8 C 0.396(2) 0.5096(8) 0.7436(17) 0.037(4) Uani 1 1 d . . . . .
C4 C 0.4238(12) 0.3985(11) 0.7515(10) 0.037(3) Uani 1 1 d . . . . .
H4 H 0.3718 0.3970 0.8307 0.044 Uiso 1 1 calc R U . . .
C1 C 0.5837(11) 0.4000(12) 0.5105(9) 0.029(2) Uani 1 1 d . . . . .
C10 C 0.579(2) 0.2527(7) 0.2905(17) 0.050(5) Uani 1 1 d . . . . .
C12 C 0.8167(19) 0.5472(7) 0.4147(16) 0.044(4) Uani 1 1 d . . . . .
F5 F 0.2918(15) 0.5369(6) 0.6652(13) 0.082(5) Uani 1 1 d . . . . .
C16 C 0.646(2) 0.2417(8) 0.153(2) 0.073(6) Uani 1 1 d . . . . .
H16A H 0.6665 0.2785 0.1104 0.109 Uiso 1 1 calc R U . . .
H16B H 0.7406 0.2200 0.1638 0.109 Uiso 1 1 calc R U . . .
H16C H 0.5742 0.2197 0.0977 0.109 Uiso 1 1 calc R U . . .
C2 C 0.555(2) 0.3493(8) 0.5813(19) 0.028(4) Uani 1 1 d . . . . .
C11 C 0.497(2) 0.5409(7) 0.2627(16) 0.040(4) Uani 1 1 d . . . . .
C22 C 0.906(2) 0.5117(10) 0.524(2) 0.080(8) Uani 1 1 d . . . . .
H22A H 0.8403 0.5039 0.5965 0.121 Uiso 1 1 calc R U . . .
H22B H 0.9398 0.4753 0.4869 0.121 Uiso 1 1 calc R U . . .
H22C H 0.9938 0.5338 0.5564 0.121 Uiso 1 1 calc R U . . .
C9 C 0.881(2) 0.2676(8) 0.463(2) 0.052(5) Uani 1 1 d . . . . .
C6 C 0.525(2) 0.4515(9) 0.5671(18) 0.034(4) Uani 1 1 d . . . . .
C20 C 0.405(2) 0.5848(8) 0.3452(18) 0.077(6) Uani 1 1 d . . . . .
H20A H 0.4731 0.6144 0.3814 0.116 Uiso 1 1 calc R U . . .
H20B H 0.3269 0.6027 0.2886 0.116 Uiso 1 1 calc R U . . .
H20C H 0.3583 0.5645 0.4169 0.116 Uiso 1 1 calc R U . . .
C17 C 0.429(2) 0.2864(9) 0.269(2) 0.084(8) Uani 1 1 d . . . . .
H17A H 0.4488 0.3230 0.2258 0.126 Uiso 1 1 calc R U . . .
H17B H 0.3586 0.2638 0.2132 0.126 Uiso 1 1 calc R U . . .
H17C H 0.3847 0.2936 0.3535 0.126 Uiso 1 1 calc R U . . .
C14 C 0.992(2) 0.2470(10) 0.3522(19) 0.084(7) Uani 1 1 d . . . . .
H14A H 1.0090 0.2787 0.2916 0.125 Uiso 1 1 calc R U . . .
H14B H 1.0885 0.2351 0.3936 0.125 Uiso 1 1 calc R U . . .
H14C H 0.9467 0.2146 0.3038 0.125 Uiso 1 1 calc R U . . .
C5 C 0.451(2) 0.4537(10) 0.691(2) 0.040(5) Uani 1 1 d . . . . .
O2 O 0.5575(14) 0.5043(6) 0.5069(13) 0.042(3) Uani 1 1 d . . . . .
C15 C 0.856(2) 0.2177(9) 0.557(2) 0.100(8) Uani 1 1 d . . . . .
H15A H 0.8031 0.1866 0.5095 0.150 Uiso 1 1 calc R U . . .
H15B H 0.9534 0.2037 0.5920 0.150 Uiso 1 1 calc R U . . .
H15C H 0.7953 0.2309 0.6287 0.150 Uiso 1 1 calc R U . . .
C23 C 0.767(2) 0.6064(7) 0.478(2) 0.074(6) Uani 1 1 d . . . . .
H23A H 0.7019 0.5989 0.5504 0.111 Uiso 1 1 calc R U . . .
H23B H 0.8572 0.6273 0.5100 0.111 Uiso 1 1 calc R U . . .
H23C H 0.7131 0.6296 0.4110 0.111 Uiso 1 1 calc R U . . .
C18 C 0.547(3) 0.1950(7) 0.3581(18) 0.092(7) Uani 1 1 d . . . . .
H18A H 0.6417 0.1736 0.3720 0.137 Uiso 1 1 calc R U . . .
H18B H 0.5030 0.2022 0.4428 0.137 Uiso 1 1 calc R U . . .
H18C H 0.4770 0.1724 0.3026 0.137 Uiso 1 1 calc R U . . .
F3 F 0.3807(17) 0.2996(6) 0.8874(13) 0.082(4) Uani 1 1 d . . . . .
F1 F 0.5800(17) 0.2638(6) 0.8018(14) 0.089(5) Uani 1 1 d . . . . .
F2 F 0.362(2) 0.2540(6) 0.6959(16) 0.093(4) Uani 1 1 d . . . . .
C7 C 0.452(3) 0.2911(9) 0.773(2) 0.052(6) Uani 1 1 d . . . . .
C19 C 0.562(2) 0.5763(8) 0.1439(18) 0.069(6) Uani 1 1 d . . . . .
H19A H 0.6336 0.6052 0.1782 0.104 Uiso 1 1 calc R U . . .
H19B H 0.6140 0.5501 0.0857 0.104 Uiso 1 1 calc R U . . .
H19C H 0.4794 0.5953 0.0948 0.104 Uiso 1 1 calc R U . . .
C24 C 0.921(2) 0.5597(8) 0.2993(18) 0.063(5) Uani 1 1 d . . . . .
H24A H 0.8648 0.5817 0.2317 0.094 Uiso 1 1 calc R U . . .
H24B H 1.0083 0.5818 0.3316 0.094 Uiso 1 1 calc R U . . .
H24C H 0.9543 0.5234 0.2621 0.094 Uiso 1 1 calc R U . . .
C21 C 0.3852(17) 0.4955(8) 0.2084(17) 0.057(5) Uani 1 1 d . . . . .
H21A H 0.4388 0.4674 0.1563 0.085 Uiso 1 1 calc R U . . .
H21B H 0.3385 0.4760 0.2813 0.085 Uiso 1 1 calc R U . . .
H21C H 0.3071 0.5142 0.1530 0.085 Uiso 1 1 calc R U . . .
C13 C 0.966(3) 0.3166(10) 0.541(2) 0.104(9) Uani 1 1 d . . . . .
H13A H 0.9838 0.3490 0.4827 0.157 Uiso 1 1 calc R U . . .
H13B H 0.9052 0.3293 0.6134 0.157 Uiso 1 1 calc R U . . .
H13C H 1.0632 0.3021 0.5767 0.157 Uiso 1 1 calc R U . . .
C25 C 0.7331(17) 0.4015(12) 0.1114(13) 0.061(4) Uani 1 1 d . . . . .
H25 H 0.6684 0.3714 0.0678 0.073 Uiso 1 1 calc R U . . .
C26 C 0.8562(19) 0.3752(6) 0.1787(14) 0.059(5) Uani 1 1 d . . . . .
H26 H 0.8557 0.3327 0.1647 0.070 Uiso 1 1 calc R U . . .
C27 C 1.0155(14) 0.3991(14) 0.1801(12) 0.065(4) Uani 1 1 d . . . . .
H27A H 1.0661 0.3916 0.2666 0.078 Uiso 1 1 calc R U . . .
H27B H 1.0112 0.4412 0.1670 0.078 Uiso 1 1 calc R U . . .
C30 C 0.965(2) 0.4282(8) -0.1200(18) 0.056(5) Uani 1 1 d . . . . .
H30A H 1.0173 0.4590 -0.0690 0.067 Uiso 1 1 calc R U . . .
H30B H 0.9916 0.4333 -0.2124 0.067 Uiso 1 1 calc R U . . .
C29 C 1.033(2) 0.3703(8) -0.0725(18) 0.059(5) Uani 1 1 d . . . . .
H29A H 1.1078 0.3578 -0.1360 0.070 Uiso 1 1 calc R U . . .
H29B H 0.9518 0.3413 -0.0739 0.070 Uiso 1 1 calc R U . . .
C32 C 0.7406(19) 0.4519(7) 0.0244(14) 0.065(5) Uani 1 1 d . . . . .
H32A H 0.8083 0.4808 0.0669 0.078 Uiso 1 1 calc R U . . .
H32B H 0.6390 0.4692 0.0150 0.078 Uiso 1 1 calc R U . . .
C28 C 1.1116(17) 0.3706(6) 0.0672(14) 0.051(4) Uani 1 1 d . . . . .
H28A H 1.2083 0.3914 0.0629 0.061 Uiso 1 1 calc R U . . .
H28B H 1.1352 0.3305 0.0925 0.061 Uiso 1 1 calc R U . . .
C31 C 0.797(2) 0.4392(7) -0.1135(13) 0.059(4) Uani 1 1 d . . . . .
H31A H 0.7422 0.4051 -0.1488 0.071 Uiso 1 1 calc R U . . .
H31B H 0.7698 0.4720 -0.1713 0.071 Uiso 1 1 calc R U . . .
C36 C 1.167(4) 0.1784(17) 0.016(4) 0.102(11) Uani 1 1 d . . . . .
H36 H 1.2592 0.1988 0.0122 0.122 Uiso 1 1 calc R U . . .
C33 C 0.896(4) 0.1201(15) 0.027(4) 0.093(11) Uani 1 1 d . . . . .
H33 H 0.8028 0.1008 0.0329 0.112 Uiso 1 1 calc R U . . .
C34 C 1.017(6) 0.1037(14) 0.099(4) 0.107(13) Uani 1 1 d . . . . .
H34 H 1.0112 0.0708 0.1536 0.129 Uiso 1 1 calc R U . . .
C38 C 0.912(4) 0.1671(15) -0.059(3) 0.098(10) Uani 1 1 d . . . . .
H38 H 0.8288 0.1792 -0.1128 0.117 Uiso 1 1 calc R U . . .
C35 C 1.155(4) 0.1343(17) 0.097(3) 0.100(10) Uani 1 1 d . . . . .
H35 H 1.2384 0.1233 0.1525 0.120 Uiso 1 1 calc R U . . .
C37 C 1.043(5) 0.1945(13) -0.064(4) 0.108(14) Uani 1 1 d . . . . .
H37 H 1.0517 0.2256 -0.1229 0.129 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(9) . ?
Ir1 C26 2.230(12) . ?
Ir1 P1 2.285(5) . ?
Ir1 C25 2.289(12) . ?
Ir1 P2 2.315(5) . ?
P1 O1 1.677(14) . ?
P1 C10 1.852(19) . ?
P1 C9 1.887(18) . ?
P2 O2 1.673(14) . ?
P2 C12 1.866(17) . ?
P2 C11 1.881(18) . ?
O1 C2 1.34(2) . ?
C3 C4 1.34(3) . ?
C3 C2 1.38(3) . ?
C3 C7 1.54(3) . ?
F6 C8 1.34(2) . ?
F4 C8 1.32(2) . ?
C8 F5 1.33(2) . ?
C8 C5 1.47(3) . ?
C4 C5 1.42(3) . ?
C1 C2 1.39(3) . ?
C1 C6 1.41(3) . ?
C10 C18 1.51(2) . ?
C10 C17 1.53(2) . ?
C10 C16 1.54(3) . ?
C12 C24 1.52(2) . ?
C12 C22 1.55(2) . ?
C12 C23 1.56(2) . ?
C11 C21 1.51(2) . ?
C11 C20 1.54(2) . ?
C11 C19 1.56(2) . ?
C9 C15 1.50(2) . ?
C9 C13 1.54(3) . ?
C9 C14 1.57(3) . ?
C6 O2 1.38(2) . ?
C6 C5 1.42(3) . ?
F3 C7 1.34(2) . ?
F1 C7 1.30(2) . ?
F2 C7 1.37(3) . ?
C25 C26 1.380(18) . ?
C25 C32 1.45(2) . ?
C26 C27 1.49(2) . ?
C27 C28 1.58(2) . ?
C30 C31 1.49(2) . ?
C30 C29 1.520(18) . ?
C29 C28 1.53(2) . ?
C32 C31 1.511(19) . ?
C36 C35 1.30(4) . ?
C36 C37 1.37(5) . ?
C33 C34 1.31(4) . ?
C33 C38 1.38(4) . ?
C34 C35 1.39(5) . ?
C38 C37 1.30(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 C26 160.2(7) . . ?
C1 Ir1 P1 77.8(8) . . ?
C26 Ir1 P1 84.6(4) . . ?
C1 Ir1 C25 159.4(5) . . ?
C26 Ir1 C25 35.5(5) . . ?
P1 Ir1 C25 103.9(7) . . ?
C1 Ir1 P2 79.5(8) . . ?
C26 Ir1 P2 117.4(4) . . ?
P1 Ir1 P2 157.15(10) . . ?
C25 Ir1 P2 98.3(7) . . ?
O1 P1 C10 96.5(8) . . ?
O1 P1 C9 95.2(8) . . ?
C10 P1 C9 112.1(8) . . ?
O1 P1 Ir1 105.5(5) . . ?
C10 P1 Ir1 118.4(5) . . ?
C9 P1 Ir1 121.7(7) . . ?
O2 P2 C12 97.3(7) . . ?
O2 P2 C11 94.6(7) . . ?
C12 P2 C11 112.6(8) . . ?
O2 P2 Ir1 104.5(5) . . ?
C12 P2 Ir1 117.3(6) . . ?
C11 P2 Ir1 123.0(5) . . ?
C2 O1 P1 115.2(13) . . ?
C4 C3 C2 121.3(19) . . ?
C4 C3 C7 118(2) . . ?
C2 C3 C7 120(2) . . ?
F4 C8 F5 104.3(16) . . ?
F4 C8 F6 106.0(14) . . ?
F5 C8 F6 106.4(16) . . ?
F4 C8 C5 112.0(17) . . ?
F5 C8 C5 114.9(15) . . ?
F6 C8 C5 112.5(17) . . ?
C3 C4 C5 121.0(10) . . ?
C2 C1 C6 114.5(9) . . ?
C2 C1 Ir1 123.5(16) . . ?
C6 C1 Ir1 122.0(16) . . ?
C18 C10 C17 109.2(18) . . ?
C18 C10 C16 110.0(15) . . ?
C17 C10 C16 108.0(16) . . ?
C18 C10 P1 114.8(13) . . ?
C17 C10 P1 103.2(12) . . ?
C16 C10 P1 111.2(13) . . ?
C24 C12 C22 109.7(17) . . ?
C24 C12 C23 109.0(14) . . ?
C22 C12 C23 108.0(16) . . ?
C24 C12 P2 112.5(11) . . ?
C22 C12 P2 104.8(13) . . ?
C23 C12 P2 112.8(12) . . ?
O1 C2 C3 118.9(18) . . ?
O1 C2 C1 117.9(18) . . ?
C3 C2 C1 123.1(18) . . ?
C21 C11 C20 107.2(16) . . ?
C21 C11 C19 109.3(14) . . ?
C20 C11 C19 106.5(14) . . ?
C21 C11 P2 106.4(11) . . ?
C20 C11 P2 113.9(12) . . ?
C19 C11 P2 113.3(13) . . ?
C15 C9 C13 108.2(18) . . ?
C15 C9 C14 109.0(16) . . ?
C13 C9 C14 106.4(18) . . ?
C15 C9 P1 115.4(14) . . ?
C13 C9 P1 104.3(14) . . ?
C14 C9 P1 113.1(13) . . ?
O2 C6 C1 117.8(17) . . ?
O2 C6 C5 117.2(18) . . ?
C1 C6 C5 124.5(18) . . ?
C6 C5 C4 115.4(18) . . ?
C6 C5 C8 120.8(19) . . ?
C4 C5 C8 123.7(18) . . ?
C6 O2 P2 115.9(13) . . ?
F1 C7 F3 107.9(16) . . ?
F1 C7 F2 106.9(19) . . ?
F3 C7 F2 107.5(18) . . ?
F1 C7 C3 113.8(18) . . ?
F3 C7 C3 111.9(19) . . ?
F2 C7 C3 108.6(17) . . ?
C26 C25 C32 125.9(18) . . ?
C26 C25 Ir1 69.9(7) . . ?
C32 C25 Ir1 127.4(16) . . ?
C25 C26 C27 123.3(17) . . ?
C25 C26 Ir1 74.5(8) . . ?
C27 C26 Ir1 120.4(13) . . ?
C26 C27 C28 111.3(17) . . ?
C31 C30 C29 120.3(16) . . ?
C30 C29 C28 115.9(14) . . ?
C25 C32 C31 114.9(15) . . ?
C29 C28 C27 115.3(12) . . ?
C30 C31 C32 115.4(13) . . ?
C35 C36 C37 119(3) . . ?
C34 C33 C38 118(3) . . ?
C33 C34 C35 121(4) . . ?
C37 C38 C33 120(3) . . ?
C36 C35 C34 120(3) . . ?
C38 C37 C36 121(4) . . ?

_refine_diff_density_max         1.338
_refine_diff_density_min         -0.916
_refine_diff_density_rms         0.137

####################################################################### 
# 
# 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_compl6
_database_code_depnum_ccdc_archive 'CCDC 1478503'
_audit_update_record             
;
2016-06-25 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(n2,n2-Cycloocta-1,5-diene)-chloro-(di-tert-butylphosphinous acid)-iridium'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H31 Cl Ir O P'
_chemical_formula_sum            'C16 H31 Cl Ir O P'
_chemical_formula_weight         498.03

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'
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                   7.96730(10)
_cell_length_b                   15.3786(2)
_cell_length_c                   14.8875(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.120(2)
_cell_angle_gamma                90
_cell_volume                     1805.82(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5904
_cell_measurement_theta_min      2.8966
_cell_measurement_theta_max      28.8056

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    7.625
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76280
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1367
_diffrn_reflns_number            19901
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.902
_diffrn_reflns_theta_max         28.869
_diffrn_reflns_theta_full        26.500
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4335
_reflns_number_gt                3315
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Crystal Maker 8.7'
_computing_publication_material  'WinGX -2014.1'
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0229P)²+0.4700P] 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         4335
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0589
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
P1 P 0.08281(15) 0.76539(9) 0.46041(9) 0.0327(3) Uani 1 1 d . . . . .
Cl1 Cl 0.26095(19) 0.73037(9) 0.26855(10) 0.0521(4) Uani 1 1 d . . . . .
C2 C 0.0098(7) 0.9521(3) 0.3798(4) 0.0461(14) Uani 1 1 d . . . . .
H2 H -0.0741 0.9345 0.4185 0.055 Uiso 1 1 calc R U . . .
C1 C 0.1742(7) 0.9641(3) 0.4282(4) 0.0433(13) Uani 1 1 d . . . . .
H1 H 0.1816 0.9536 0.4935 0.052 Uiso 1 1 calc R U . . .
C6 C 0.3372(7) 0.9299(4) 0.2775(4) 0.0484(15) Uani 1 1 d . . . . .
H6 H 0.4200 0.8966 0.2487 0.058 Uiso 1 1 calc R U . . .
C5 C 0.1747(7) 0.9322(4) 0.2274(4) 0.0453(14) Uani 1 1 d . . . . .
H5 H 0.1647 0.8998 0.1702 0.054 Uiso 1 1 calc R U . . .
C8 C 0.2951(8) 1.0331(4) 0.4035(4) 0.0580(16) Uani 1 1 d . . . . .
H8A H 0.2300 1.0814 0.3749 0.070 Uiso 1 1 calc R U . . .
H8B H 0.3615 1.0546 0.4587 0.070 Uiso 1 1 calc R U . . .
C4 C 0.0558(8) 1.0085(4) 0.2255(4) 0.0596(17) Uani 1 1 d . . . . .
H4A H -0.0104 1.0126 0.1657 0.072 Uiso 1 1 calc R U . . .
H4B H 0.1216 1.0615 0.2361 0.072 Uiso 1 1 calc R U . . .
C7 C 0.4140(8) 1.0005(4) 0.3405(4) 0.0634(18) Uani 1 1 d . . . . .
H7A H 0.4462 1.0488 0.3046 0.076 Uiso 1 1 calc R U . . .
H7B H 0.5162 0.9783 0.3764 0.076 Uiso 1 1 calc R U . . .
C3 C -0.0650(8) 1.0011(4) 0.2970(4) 0.0591(17) Uani 1 1 d . . . . .
H3A H -0.0954 1.0591 0.3147 0.071 Uiso 1 1 calc R U . . .
H3B H -0.1682 0.9721 0.2700 0.071 Uiso 1 1 calc R U . . .
C9 C 0.2552(6) 0.7108(4) 0.5372(4) 0.0412(13) Uani 1 1 d . . . . .
C10 C -0.1069(7) 0.6952(4) 0.4272(4) 0.0503(15) Uani 1 1 d . . . . .
C13 C 0.3957(7) 0.7797(4) 0.5549(5) 0.071(2) Uani 1 1 d . . . . .
H13A H 0.3535 0.8295 0.5836 0.107 Uiso 1 1 calc R U . . .
H13B H 0.4909 0.7558 0.5938 0.107 Uiso 1 1 calc R U . . .
H13C H 0.4305 0.7970 0.4983 0.107 Uiso 1 1 calc R U . . .
C11 C 0.3216(8) 0.6313(4) 0.4914(4) 0.0675(19) Uani 1 1 d . . . . .
H11A H 0.3532 0.6481 0.4340 0.101 Uiso 1 1 calc R U . . .
H11B H 0.4188 0.6082 0.5294 0.101 Uiso 1 1 calc R U . . .
H11C H 0.2346 0.5878 0.4821 0.101 Uiso 1 1 calc R U . . .
C12 C 0.2043(8) 0.6849(5) 0.6291(4) 0.073(2) Uani 1 1 d . . . . .
H12A H 0.1628 0.7351 0.6574 0.110 Uiso 1 1 calc R U . . .
H12B H 0.1170 0.6414 0.6200 0.110 Uiso 1 1 calc R U . . .
H12C H 0.3012 0.6619 0.6674 0.110 Uiso 1 1 calc R U . . .
C14 C -0.1671(8) 0.6489(5) 0.5075(5) 0.081(2) Uani 1 1 d . . . . .
H14A H -0.0811 0.6092 0.5341 0.121 Uiso 1 1 calc R U . . .
H14B H -0.1888 0.6911 0.5520 0.121 Uiso 1 1 calc R U . . .
H14C H -0.2693 0.6174 0.4871 0.121 Uiso 1 1 calc R U . . .
C16 C -0.2457(7) 0.7584(5) 0.3856(5) 0.086(3) Uani 1 1 d . . . . .
H16A H -0.2090 0.7878 0.3349 0.130 Uiso 1 1 calc R U . . .
H16B H -0.3477 0.7265 0.3654 0.130 Uiso 1 1 calc R U . . .
H16C H -0.2673 0.8003 0.4304 0.130 Uiso 1 1 calc R U . . .
C15 C -0.0727(9) 0.6287(5) 0.3547(5) 0.096(3) Uani 1 1 d . . . . .
H15A H -0.0349 0.6585 0.3045 0.144 Uiso 1 1 calc R U . . .
H15B H 0.0132 0.5886 0.3804 0.144 Uiso 1 1 calc R U . . .
H15C H -0.1751 0.5974 0.3338 0.144 Uiso 1 1 calc R U . . .
O1 O 0.0099(4) 0.8244(2) 0.5339(2) 0.0309(8) Uani 1 1 d . . . . .
H1A H -0.0227 0.7933 0.5727 0.046 Uiso 1 1 calc R U . . .
Ir1 Ir 0.16808(2) 0.84880(2) 0.34920(2) 0.03028(7) Uani 1 1 d . . . . .


_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
P1 O1 1.593(3) . ?
P1 C9 1.859(5) . ?
P1 C10 1.866(6) . ?
P1 Ir1 2.2729(13) . ?
Cl1 Ir1 2.3574(13) . ?
C2 C1 1.414(7) . ?
C2 C3 1.496(8) . ?
C2 Ir1 2.117(5) . ?
C1 C8 1.513(7) . ?
C1 Ir1 2.124(5) . ?
C6 C5 1.400(8) . ?
C6 C7 1.506(8) . ?
C6 Ir1 2.217(5) . ?
C5 C4 1.506(8) . ?
C5 Ir1 2.227(5) . ?
C8 C7 1.510(8) . ?
C4 C3 1.537(8) . ?
C9 C11 1.530(8) . ?
C9 C12 1.534(7) . ?
C9 C13 1.537(7) . ?
C10 C14 1.526(8) . ?
C10 C16 1.536(9) . ?
C10 C15 1.540(9) . ?

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
O1 P1 C9 98.3(2) . . ?
O1 P1 C10 98.7(2) . . ?
C9 P1 C10 113.7(3) . . ?
O1 P1 Ir1 110.75(13) . . ?
C9 P1 Ir1 115.59(17) . . ?
C10 P1 Ir1 116.60(19) . . ?
C1 C2 C3 125.9(5) . . ?
C1 C2 Ir1 70.8(3) . . ?
C3 C2 Ir1 112.4(4) . . ?
C2 C1 C8 123.0(5) . . ?
C2 C1 Ir1 70.2(3) . . ?
C8 C1 Ir1 114.6(4) . . ?
C5 C6 C7 125.3(6) . . ?
C5 C6 Ir1 72.0(3) . . ?
C7 C6 Ir1 109.1(4) . . ?
C6 C5 C4 124.2(5) . . ?
C6 C5 Ir1 71.2(3) . . ?
C4 C5 Ir1 112.1(4) . . ?
C7 C8 C1 113.2(5) . . ?
C5 C4 C3 112.5(5) . . ?
C6 C7 C8 113.0(5) . . ?
C2 C3 C4 113.1(5) . . ?
C11 C9 C12 110.0(5) . . ?
C11 C9 C13 109.8(5) . . ?
C12 C9 C13 107.7(5) . . ?
C11 C9 P1 111.0(4) . . ?
C12 C9 P1 113.6(4) . . ?
C13 C9 P1 104.5(4) . . ?
C14 C10 C16 108.8(5) . . ?
C14 C10 C15 110.3(6) . . ?
C16 C10 C15 109.0(6) . . ?
C14 C10 P1 113.3(4) . . ?
C16 C10 P1 104.5(4) . . ?
C15 C10 P1 110.7(4) . . ?
C2 Ir1 C1 39.0(2) . . ?
C2 Ir1 C6 95.9(2) . . ?
C1 Ir1 C6 80.1(2) . . ?
C2 Ir1 C5 80.0(2) . . ?
C1 Ir1 C5 88.2(2) . . ?
C6 Ir1 C5 36.7(2) . . ?
C2 Ir1 P1 91.04(16) . . ?
C1 Ir1 P1 93.09(15) . . ?
C6 Ir1 P1 158.84(16) . . ?
C5 Ir1 P1 164.10(15) . . ?
C2 Ir1 Cl1 158.21(16) . . ?
C1 Ir1 Cl1 160.47(15) . . ?
C6 Ir1 Cl1 86.20(16) . . ?
C5 Ir1 Cl1 89.14(15) . . ?
P1 Ir1 Cl1 94.74(5) . . ?

_refine_diff_density_max         0.726
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.160

