# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_rph345a
_database_code_depnum_ccdc_archive 'CCDC 1403906'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-07-03 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        ?

_chemical_name_common            ?

_chemical_formula_moiety         'C15 H15 F6 Ir O'

_chemical_formula_sum            'C15 H15 F6 Ir O'

_chemical_melting_point          ?



_exptl_crystal_description       block

_exptl_crystal_colour            colorless



_diffrn_ambient_temperature      273(2)

_chemical_formula_weight         517.47



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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           monoclinic

_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

_symmetry_space_group_name_Hall  '-P 2ybc'



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   13.8295(15)

_cell_length_b                   8.5770(9)

_cell_length_c                   13.4797(14)

_cell_angle_alpha                90.00

_cell_angle_beta                 94.3780(10)

_cell_angle_gamma                90.00

_cell_volume                     1594.2(3)

_cell_formula_units_Z            4

_cell_measurement_temperature    273(2)

_cell_measurement_reflns_used    ?

_cell_measurement_theta_min      ?

_cell_measurement_theta_max      ?

_exptl_crystal_size_max          .3

_exptl_crystal_size_mid          .3

_exptl_crystal_size_min          .2

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.156

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             976

_exptl_absorpt_coefficient_mu    8.436

_exptl_absorpt_correction_type   empirical

_exptl_absorpt_correction_T_min  0.245

_exptl_absorpt_correction_T_max  0.390

_exptl_absorpt_process_details   SADABS



_exptl_special_details           
; 

 ? 

;
_diffrn_radiation_probe          ?

_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            12911

_diffrn_reflns_av_R_equivalents  0.0386

_diffrn_reflns_av_sigmaI/netI    0.0361

_diffrn_reflns_limit_h_min       -17

_diffrn_reflns_limit_h_max       17

_diffrn_reflns_limit_k_min       -10

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -17

_diffrn_reflns_limit_l_max       17

_diffrn_reflns_theta_min         1.48

_diffrn_reflns_theta_max         27.55

_reflns_number_total             3566

_reflns_number_gt                3272

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
; 

 Refinement of F² against ALL reflections.  The weighted R-factor wR and 

 goodness of fit S are based on F², conventional R-factors R are based 

 on F, with F set to zero for negative F². The threshold expression of 

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 

 not relevant to the choice of reflections for refinement.  R-factors based 

 on F² are statistically about twice as large as those based on F, and R- 

 factors based on ALL data will be even larger. 

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0434P)²+21.1758P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         3566

_refine_ls_number_parameters     213

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0472

_refine_ls_R_factor_gt           0.0439

_refine_ls_wR_factor_ref         0.1061

_refine_ls_wR_factor_gt          0.1045

_refine_ls_goodness_of_fit_ref   1.082

_refine_ls_restrained_S_all      1.082

_refine_ls_shift/su_max          0.037

_refine_ls_shift/su_mean         0.002



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group







Ir1 Ir 0.781795(19) 0.01934(3) 0.40745(2) 0.01851(11) Uani 1 1 d . . .
F5 F 0.8479(4) 0.0521(7) 0.6265(4) 0.0399(13) Uani 1 1 d . . .
C8 C 0.7834(5) 0.0305(8) 0.2395(5) 0.0204(14) Uani 1 1 d . . .
F4 F 0.7449(4) 0.2329(6) 0.5759(4) 0.0381(12) Uani 1 1 d . . .
F2 F 0.6299(4) -0.3006(6) 0.3692(4) 0.0452(14) Uani 1 1 d . . .
F1 F 0.5911(4) -0.3267(7) 0.5189(5) 0.0508(16) Uani 1 1 d . . .
C12 C 0.6745(5) -0.0984(9) 0.4801(6) 0.0233(15) Uani 1 1 d . . .
C15 C 0.8749(5) -0.1304(9) 0.4460(6) 0.0235(15) Uani 1 1 d . . .
F3 F 0.5158(4) -0.1616(7) 0.4208(5) 0.0448(14) Uani 1 1 d . . .
C5 C 0.5962(5) 0.0160(10) 0.2262(7) 0.0276(17) Uani 1 1 d . . .
H5A H 0.5753 0.0651 0.1642 0.041 Uiso 1 1 calc R . .
H5B H 0.5490 0.0341 0.2736 0.041 Uiso 1 1 calc R . .
H5C H 0.6029 -0.0942 0.2160 0.041 Uiso 1 1 calc R . .
C14 C 0.7701(6) 0.0799(10) 0.5571(6) 0.0285(18) Uani 1 1 d . . .
C10 C 0.8556(5) 0.1367(9) 0.2853(6) 0.0212(15) Uani 1 1 d . . .
C4 C 0.7046(5) 0.2155(8) 0.3288(6) 0.0214(15) Uani 1 1 d . . .
C9 C 0.9615(5) 0.1342(11) 0.2695(7) 0.0326(19) Uani 1 1 d . . .
H9A H 0.9723 0.1874 0.2087 0.049 Uiso 1 1 calc R . .
H9B H 0.9831 0.0282 0.2656 0.049 Uiso 1 1 calc R . .
H9C H 0.9970 0.1855 0.3242 0.049 Uiso 1 1 calc R . .
C7 C 0.8028(6) -0.0986(9) 0.1697(6) 0.0256(16) Uani 1 1 d . . .
H7A H 0.7912 -0.0627 0.1024 0.038 Uiso 1 1 calc R . .
H7B H 0.7606 -0.1847 0.1807 0.038 Uiso 1 1 calc R . .
H7C H 0.8691 -0.1315 0.1810 0.038 Uiso 1 1 calc R . .
O1 O 0.9334(5) -0.2207(8) 0.4675(5) 0.0378(15) Uani 1 1 d . . .
C11 C 0.6046(6) -0.2203(10) 0.4474(7) 0.0323(18) Uani 1 1 d . . .
C6 C 0.6915(5) 0.0825(9) 0.2646(5) 0.0197(14) Uani 1 1 d . . .
F6 F 0.6453(4) -0.0545(7) 0.6526(4) 0.0414(13) Uani 1 1 d . . .
C2 C 0.8068(6) 0.2514(9) 0.3391(6) 0.0245(16) Uani 1 1 d . . .
C13 C 0.6897(6) -0.0308(10) 0.5669(6) 0.0305(18) Uani 1 1 d . . .
C3 C 0.6235(6) 0.3126(10) 0.3659(7) 0.0319(19) Uani 1 1 d . . .
H3A H 0.5975 0.3800 0.3136 0.048 Uiso 1 1 calc R . .
H3B H 0.6482 0.3744 0.4216 0.048 Uiso 1 1 calc R . .
H3C H 0.5732 0.2451 0.3862 0.048 Uiso 1 1 calc R . .
C1 C 0.8499(7) 0.3925(10) 0.3902(7) 0.036(2) Uani 1 1 d . . .
H1A H 0.8534 0.4755 0.3428 0.053 Uiso 1 1 calc R . .
H1B H 0.9139 0.3685 0.4187 0.053 Uiso 1 1 calc R . .
H1C H 0.8101 0.4242 0.4419 0.053 Uiso 1 1 calc R . .






_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 C15 1.864(8) . ?
Ir1 C12 2.098(8) . ?
Ir1 C14 2.101(8) . ?
Ir1 C4 2.219(7) . ?
Ir1 C2 2.231(8) . ?
Ir1 C10 2.242(7) . ?
Ir1 C8 2.267(7) . ?
Ir1 C6 2.279(7) . ?
Ir1 C13 2.617(9) . ?
F5 C14 1.391(9) . ?
C8 C6 1.413(10) . ?
C8 C10 1.453(10) . ?
C8 C7 1.491(10) . ?
F4 C14 1.387(9) . ?
F2 C11 1.328(11) . ?
F1 C11 1.351(10) . ?
C12 C13 1.308(12) . ?
C12 C11 1.469(11) . ?
C15 O1 1.141(10) . ?
F3 C11 1.349(10) . ?
C5 C6 1.493(10) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C14 C13 1.476(13) . ?
C10 C2 1.422(11) . ?
C10 C9 1.495(10) . ?
C4 C6 1.435(10) . ?
C4 C2 1.444(11) . ?
C4 C3 1.513(10) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
F6 C13 1.364(10) . ?
C2 C1 1.494(11) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?



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


C15 Ir1 C12 92.1(3) . . ?
C15 Ir1 C14 90.3(3) . . ?
C12 Ir1 C14 64.0(3) . . ?
C15 Ir1 C4 162.3(3) . . ?
C12 Ir1 C4 104.9(3) . . ?
C14 Ir1 C4 101.7(3) . . ?
C15 Ir1 C2 127.2(3) . . ?
C12 Ir1 C2 139.4(3) . . ?
C14 Ir1 C2 101.6(3) . . ?
C4 Ir1 C2 37.9(3) . . ?
C15 Ir1 C10 99.8(3) . . ?
C12 Ir1 C10 159.6(3) . . ?
C14 Ir1 C10 131.8(3) . . ?
C4 Ir1 C10 62.5(3) . . ?
C2 Ir1 C10 37.1(3) . . ?
C15 Ir1 C8 104.4(3) . . ?
C12 Ir1 C8 123.2(3) . . ?
C14 Ir1 C8 162.8(3) . . ?
C4 Ir1 C8 62.1(3) . . ?
C2 Ir1 C8 62.4(3) . . ?
C10 Ir1 C8 37.6(3) . . ?
C15 Ir1 C6 136.2(3) . . ?
C12 Ir1 C6 98.5(3) . . ?
C14 Ir1 C6 132.5(3) . . ?
C4 Ir1 C6 37.2(3) . . ?
C2 Ir1 C6 62.1(3) . . ?
C10 Ir1 C6 61.6(3) . . ?
C8 Ir1 C6 36.2(3) . . ?
C15 Ir1 C13 91.5(3) . . ?
C12 Ir1 C13 29.7(3) . . ?
C14 Ir1 C13 34.3(3) . . ?
C4 Ir1 C13 105.7(3) . . ?
C2 Ir1 C13 125.9(3) . . ?
C10 Ir1 C13 162.7(3) . . ?
C8 Ir1 C13 150.4(3) . . ?
C6 Ir1 C13 117.6(3) . . ?
C6 C8 C10 107.6(6) . . ?
C6 C8 C7 126.4(7) . . ?
C10 C8 C7 125.6(7) . . ?
C6 C8 Ir1 72.3(4) . . ?
C10 C8 Ir1 70.2(4) . . ?
C7 C8 Ir1 127.9(5) . . ?
C13 C12 C11 129.8(8) . . ?
C13 C12 Ir1 97.7(6) . . ?
C11 C12 Ir1 132.5(6) . . ?
O1 C15 Ir1 178.1(7) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
F4 C14 F5 103.4(6) . . ?
F4 C14 C13 113.0(7) . . ?
F5 C14 C13 112.3(7) . . ?
F4 C14 Ir1 116.6(5) . . ?
F5 C14 Ir1 119.4(5) . . ?
C13 C14 Ir1 92.3(5) . . ?
C2 C10 C8 108.2(6) . . ?
C2 C10 C9 126.2(7) . . ?
C8 C10 C9 125.4(7) . . ?
C2 C10 Ir1 71.1(4) . . ?
C8 C10 Ir1 72.2(4) . . ?
C9 C10 Ir1 127.1(5) . . ?
C6 C4 C2 107.8(6) . . ?
C6 C4 C3 125.1(7) . . ?
C2 C4 C3 126.6(7) . . ?
C6 C4 Ir1 73.7(4) . . ?
C2 C4 Ir1 71.5(4) . . ?
C3 C4 Ir1 127.0(5) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
F2 C11 F3 105.8(7) . . ?
F2 C11 F1 106.0(7) . . ?
F3 C11 F1 105.7(7) . . ?
F2 C11 C12 113.5(7) . . ?
F3 C11 C12 112.3(7) . . ?
F1 C11 C12 112.9(7) . . ?
C8 C6 C4 108.7(6) . . ?
C8 C6 C5 125.7(7) . . ?
C4 C6 C5 125.5(7) . . ?
C8 C6 Ir1 71.5(4) . . ?
C4 C6 Ir1 69.1(4) . . ?
C5 C6 Ir1 128.0(5) . . ?
C10 C2 C4 107.6(7) . . ?
C10 C2 C1 127.4(7) . . ?
C4 C2 C1 124.8(7) . . ?
C10 C2 Ir1 71.9(4) . . ?
C4 C2 Ir1 70.6(4) . . ?
C1 C2 Ir1 127.0(6) . . ?
C12 C13 F6 129.8(9) . . ?
C12 C13 C14 105.9(7) . . ?
F6 C13 C14 124.3(8) . . ?
C12 C13 Ir1 52.6(5) . . ?
F6 C13 Ir1 177.4(7) . . ?
C14 C13 Ir1 53.3(4) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?



_diffrn_measured_fraction_theta_max 0.970

_diffrn_reflns_theta_full        27.55

_diffrn_measured_fraction_theta_full 0.970

_refine_diff_density_max         7.744

_refine_diff_density_min         -2.329

_refine_diff_density_rms         0.232

####################################################################### 
# 
# 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_rph416a
_database_code_depnum_ccdc_archive 'CCDC 1403907'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-07-03 downloaded from the CCDC.
;
_audit_creation_date             2015-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C28 F12 Ir2 O2)'
_chemical_formula_sum            'C14 F6 Ir O'
_chemical_formula_weight         490.34
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.2475(9)
_cell_length_b                   14.3291(8)
_cell_length_c                   7.6320(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1667.46(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6696
_cell_measurement_temperature    198.15
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.325
_shelx_estimated_absorpt_T_min   0.248
_exptl_absorpt_coefficient_mu    8.061
_exptl_absorpt_correction_T_max  0.288
_exptl_absorpt_correction_T_min  0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.953
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8721
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.166
_diffrn_reflns_theta_min         2.843
_diffrn_ambient_temperature      198.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1892
_reflns_number_total             2058
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.869
_refine_diff_density_min         -2.402
_refine_diff_density_rms         0.198
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2058
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.172
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0379P)²+17.3122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1116
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: F1(0.5) F2(0.5) F3(0.5) F4(0.5) F5(0.5) F6(0.5) C1(0.5) C2(0.5)
 C3(0.5) C4(0.5) C5(0.5) C6(0.5) C7(0.5) C8(0.5) C9(0.5) C11(0.5) C13(0.5)
 C14(0.5) C15(0.5)
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.62307(2) 0.2500 0.10303(5) 0.03116(15) Uani 1 2 d S T P . .
O1 O 0.4741(7) 0.2500 -0.1499(15) 0.073(3) Uani 1 2 d S T P . .
F1 F 0.4568(7) 0.4244(9) 0.287(2) 0.074(4) Uani 0.5 1 d . . . . .
F2 F 0.5527(10) 0.5305(9) 0.280(2) 0.091(5) Uani 0.5 1 d . . . . .
F3 F 0.5608(11) 0.4174(16) 0.4652(17) 0.115(7) Uani 0.5 1 d . . . . .
F4 F 0.6768(11) 0.5400(9) -0.024(2) 0.095(5) Uani 0.5 1 d . . . . .
F5 F 0.7782(9) 0.4523(12) -0.026(3) 0.102(6) Uani 0.5 1 d . . . . .
F6 F 0.6849(15) 0.4442(15) -0.216(2) 0.130(8) Uani 0.5 1 d . . . . .
C1 C 0.6328(14) 0.3983(14) 0.200(4) 0.053(6) Uani 0.5 1 d . . . . .
C2 C 0.6473(10) 0.3374(13) 0.344(2) 0.044(4) Uani 0.5 1 d . . . . .
C3 C 0.7256(9) 0.2842(11) 0.307(2) 0.042(4) Uani 0.5 1 d . . . . .
C4 C 0.7580(10) 0.3144(11) 0.144(2) 0.041(3) Uani 0.5 1 d . . . . .
C5 C 0.7023(14) 0.3828(13) 0.075(3) 0.048(4) Uani 0.5 1 d . . . . .
C6 C 0.5627(16) 0.4741(16) 0.184(4) 0.073(7) Uani 0.5 1 d . . . . .
C7 C 0.5941(15) 0.334(2) 0.512(3) 0.078(8) Uani 0.5 1 d . . . . .
C8 C 0.7664(12) 0.2129(14) 0.426(3) 0.060(5) Uani 0.5 1 d . . . . .
C9 C 0.8437(11) 0.2828(15) 0.059(3) 0.072(7) Uani 0.5 1 d . . . . .
C11 C 0.5414(12) 0.4420(15) 0.298(3) 0.056(5) Uani 0.5 1 d . . . . .
C13 C 0.5931(13) 0.3827(13) 0.179(2) 0.037(4) Uani 0.5 1 d . . . . .
C14 C 0.6471(13) 0.3894(12) 0.048(3) 0.042(3) Uani 0.5 1 d . . . . .
C15 C 0.7019(10) 0.4492(9) -0.0697(18) 0.034(3) Uani 0.5 1 d . . . . .
C16 C 0.5306(8) 0.2500 -0.0534(17) 0.046(3) Uani 1 2 d S T P . .


_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 2.255(19) 7_565 ?
Ir1 C1 2.255(19) . ?
Ir1 C2 2.255(16) . ?
Ir1 C2 2.255(16) 7_565 ?
Ir1 C3 2.258(16) 7_565 ?
Ir1 C3 2.258(16) . ?
Ir1 C5 2.264(18) . ?
Ir1 C13 2.040(18) 7_565 ?
Ir1 C13 2.040(18) . ?
Ir1 C14 2.074(16) . ?
Ir1 C14 2.074(16) 7_565 ?
Ir1 C16 1.847(12) . ?
O1 C16 1.134(15) . ?
F1 C11 1.32(2) . ?
F2 C6 1.10(3) . ?
F2 C11 1.29(3) . ?
F3 C7 1.35(3) . ?
F3 C11 1.36(3) . ?
F4 C15 1.40(2) . ?
F5 C5 1.71(2) . ?
F5 C15 1.21(2) . ?
F6 C15 1.15(2) . ?
C1 C2 1.42(3) . ?
C1 C5 1.44(3) . ?
C1 C6 1.53(3) . ?
C1 C11 1.70(3) . ?
C1 C13 0.66(2) . ?
C1 C14 1.18(3) . ?
C2 C3 1.44(2) . ?
C2 C7 1.52(3) . ?
C2 C13 1.64(2) . ?
C3 C3 0.98(3) 7_565 ?
C3 C4 1.41(2) . ?
C3 C4 1.95(2) 7_565 ?
C3 C8 1.10(2) 7_565 ?
C3 C8 1.50(2) . ?
C4 C3 1.95(2) 7_565 ?
C4 C4 1.85(3) 7_565 ?
C4 C5 1.40(3) . ?
C4 C9 2.02(2) 7_565 ?
C4 C9 1.53(2) . ?
C5 C13 1.85(3) . ?
C5 C14 0.87(2) . ?
C5 C15 1.46(2) . ?
C6 C11 1.04(3) . ?
C6 C13 1.39(3) . ?
C8 C3 1.10(2) 7_565 ?
C8 C8 1.06(4) 7_565 ?
C9 C4 2.02(2) 7_565 ?
C9 C9 0.94(4) 7_565 ?
C11 C13 1.47(2) . ?
C13 C14 1.30(3) . ?
C14 C15 1.50(2) . ?

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 C1 141.0(13) 7_565 . ?
C1 Ir1 C2 104.3(8) . 7_565 ?
C1 Ir1 C2 36.8(8) 7_565 7_565 ?
C1 Ir1 C2 36.8(8) . . ?
C1 Ir1 C2 104.3(8) 7_565 . ?
C1 Ir1 C3 86.2(7) . 7_565 ?
C1 Ir1 C3 61.6(7) 7_565 7_565 ?
C1 Ir1 C3 61.6(7) . . ?
C1 Ir1 C3 86.2(7) 7_565 . ?
C1 Ir1 C5 37.2(8) . . ?
C1 Ir1 C5 142.0(8) 7_565 . ?
C2 Ir1 C2 67.5(10) . 7_565 ?
C2 Ir1 C3 56.4(6) 7_565 . ?
C2 Ir1 C3 37.3(6) 7_565 7_565 ?
C2 Ir1 C3 37.3(6) . . ?
C2 Ir1 C3 56.4(6) . 7_565 ?
C2 Ir1 C5 117.2(7) 7_565 . ?
C2 Ir1 C5 61.5(7) . . ?
C3 Ir1 C3 25.1(8) 7_565 . ?
C3 Ir1 C5 60.9(6) . . ?
C3 Ir1 C5 83.0(7) 7_565 . ?
C13 Ir1 C1 143.1(7) 7_565 . ?
C13 Ir1 C1 16.8(6) 7_565 7_565 ?
C13 Ir1 C1 16.8(6) . . ?
C13 Ir1 C1 143.1(7) . 7_565 ?
C13 Ir1 C2 44.4(7) . . ?
C13 Ir1 C2 108.7(7) 7_565 . ?
C13 Ir1 C2 44.4(7) 7_565 7_565 ?
C13 Ir1 C2 108.7(7) . 7_565 ?
C13 Ir1 C3 75.9(7) 7_565 7_565 ?
C13 Ir1 C3 99.2(7) 7_565 . ?
C13 Ir1 C3 99.2(7) . 7_565 ?
C13 Ir1 C3 75.9(7) . . ?
C13 Ir1 C5 50.5(8) . . ?
C13 Ir1 C5 158.4(8) 7_565 . ?
C13 Ir1 C13 137.4(10) . 7_565 ?
C13 Ir1 C14 36.9(7) . . ?
C13 Ir1 C14 36.9(7) 7_565 7_565 ?
C13 Ir1 C14 174.2(7) 7_565 . ?
C13 Ir1 C14 174.2(7) . 7_565 ?
C14 Ir1 C1 164.3(8) . 7_565 ?
C14 Ir1 C1 31.4(8) . . ?
C14 Ir1 C1 164.3(8) 7_565 . ?
C14 Ir1 C1 31.4(8) 7_565 7_565 ?
C14 Ir1 C2 66.5(7) . . ?
C14 Ir1 C2 66.5(7) 7_565 7_565 ?
C14 Ir1 C2 132.1(7) . 7_565 ?
C14 Ir1 C2 132.1(7) 7_565 . ?
C14 Ir1 C3 103.0(7) 7_565 . ?
C14 Ir1 C3 78.9(7) 7_565 7_565 ?
C14 Ir1 C3 103.1(7) . 7_565 ?
C14 Ir1 C3 78.9(7) . . ?
C14 Ir1 C5 134.1(8) 7_565 . ?
C14 Ir1 C5 22.6(6) . . ?
C14 Ir1 C14 148.8(10) 7_565 . ?
C16 Ir1 C1 105.2(5) . . ?
C16 Ir1 C1 105.2(5) . 7_565 ?
C16 Ir1 C2 130.7(5) . 7_565 ?
C16 Ir1 C2 130.7(5) . . ?
C16 Ir1 C3 166.7(4) . . ?
C16 Ir1 C3 166.7(4) . 7_565 ?
C16 Ir1 C5 110.2(6) . . ?
C16 Ir1 C13 90.8(6) . 7_565 ?
C16 Ir1 C13 90.8(6) . . ?
C16 Ir1 C14 90.2(6) . . ?
C16 Ir1 C14 90.2(6) . 7_565 ?
C6 F2 C11 50.7(17) . . ?
C7 F3 C11 124.1(16) . . ?
C15 F5 C5 56.8(10) . . ?
C2 C1 Ir1 71.6(11) . . ?
C2 C1 C5 107.6(17) . . ?
C2 C1 C6 127(2) . . ?
C2 C1 C11 90.6(19) . . ?
C5 C1 Ir1 71.7(11) . . ?
C5 C1 C6 125(2) . . ?
C5 C1 C11 162(2) . . ?
C6 C1 Ir1 126.8(14) . . ?
C6 C1 C11 36.9(13) . . ?
C11 C1 Ir1 115.9(13) . . ?
C13 C1 Ir1 63(3) . . ?
C13 C1 C2 97(3) . . ?
C13 C1 C5 118(4) . . ?
C13 C1 C6 65(3) . . ?
C13 C1 C11 59(3) . . ?
C13 C1 C14 85(3) . . ?
C14 C1 Ir1 65.8(12) . . ?
C14 C1 C2 131(2) . . ?
C14 C1 C5 37.1(13) . . ?
C14 C1 C6 97(2) . . ?
C14 C1 C11 128(2) . . ?
C1 C2 Ir1 71.6(10) . . ?
C1 C2 C3 107.5(17) . . ?
C1 C2 C7 126(2) . . ?
C1 C2 C13 23.8(9) . . ?
C3 C2 Ir1 71.4(10) . . ?
C3 C2 C7 126.0(19) . . ?
C3 C2 C13 118.4(15) . . ?
C7 C2 Ir1 125.4(13) . . ?
C7 C2 C13 113.1(16) . . ?
C13 C2 Ir1 60.8(9) . . ?
C2 C3 Ir1 71.2(9) . . ?
C2 C3 C4 136.0(12) . 7_565 ?
C2 C3 C8 125.6(17) . . ?
C3 C3 Ir1 77.5(4) 7_565 . ?
C3 C3 C2 121.9(9) 7_565 . ?
C3 C3 C4 43.4(7) 7_565 7_565 ?
C3 C3 C4 107.9(9) 7_565 . ?
C3 C3 C8 92.2(13) 7_565 7_565 ?
C3 C3 C8 47.2(10) 7_565 . ?
C4 C3 Ir1 65.1(7) 7_565 . ?
C4 C3 Ir1 72.6(9) . . ?
C4 C3 C2 107.6(14) . . ?
C4 C3 C4 64.5(13) . 7_565 ?
C4 C3 C8 126.7(16) . . ?
C8 C3 Ir1 165.1(17) 7_565 . ?
C8 C3 Ir1 123.8(11) . . ?
C8 C3 C2 106.6(19) 7_565 . ?
C8 C3 C4 114.2(16) 7_565 7_565 ?
C8 C3 C4 121.2(17) 7_565 . ?
C8 C3 C4 77.7(12) . 7_565 ?
C8 C3 C8 45.0(19) 7_565 . ?
C3 C4 Ir1 64.1(6) 7_565 . ?
C3 C4 Ir1 71.2(8) . . ?
C3 C4 C3 28.6(10) . 7_565 ?
C3 C4 C4 72.1(9) . 7_565 ?
C3 C4 C9 82.4(10) 7_565 7_565 ?
C3 C4 C9 125.7(17) . . ?
C3 C4 C9 107.4(13) . 7_565 ?
C4 C4 Ir1 66.1(4) 7_565 . ?
C4 C4 C3 43.4(7) 7_565 7_565 ?
C4 C4 C9 46.3(7) 7_565 7_565 ?
C5 C4 Ir1 71.6(10) . . ?
C5 C4 C3 109.6(14) . . ?
C5 C4 C3 126.5(13) . 7_565 ?
C5 C4 C4 134.4(10) . 7_565 ?
C5 C4 C9 139.1(16) . 7_565 ?
C5 C4 C9 124.6(17) . . ?
C9 C4 Ir1 105.2(9) 7_565 . ?
C9 C4 Ir1 126.6(12) . . ?
C9 C4 C3 105.8(14) . 7_565 ?
C9 C4 C4 72.7(10) . 7_565 ?
C9 C4 C9 26.4(13) . 7_565 ?
F5 C5 Ir1 153.5(13) . . ?
F5 C5 C13 143.6(14) . . ?
C1 C5 Ir1 71.0(11) . . ?
C1 C5 F5 134.7(16) . . ?
C1 C5 C13 18.6(9) . . ?
C1 C5 C15 113.3(19) . . ?
C4 C5 Ir1 72.5(10) . . ?
C4 C5 F5 99.6(15) . . ?
C4 C5 C1 107.7(17) . . ?
C4 C5 C13 112.5(14) . . ?
C4 C5 C15 138.2(18) . . ?
C13 C5 Ir1 58.5(8) . . ?
C14 C5 Ir1 66.3(16) . . ?
C14 C5 F5 119(2) . . ?
C14 C5 C1 55.1(19) . . ?
C14 C5 C4 139(2) . . ?
C14 C5 C13 39.7(17) . . ?
C14 C5 C15 75.4(19) . . ?
C15 C5 Ir1 128.3(13) . . ?
C15 C5 F5 44.1(9) . . ?
C15 C5 C13 108.9(15) . . ?
F2 C6 C1 124(3) . . ?
F2 C6 C13 139(3) . . ?
C11 C6 F2 74(3) . . ?
C11 C6 C1 81(2) . . ?
C11 C6 C13 73.0(19) . . ?
C13 C6 C1 25.7(9) . . ?
F3 C7 C2 86.9(19) . . ?
C3 C8 C3 40.7(14) 7_565 . ?
C8 C8 C3 47.2(10) 7_565 . ?
C8 C8 C3 87.9(13) 7_565 7_565 ?
C4 C9 C4 60.9(12) . 7_565 ?
C9 C9 C4 46.3(7) 7_565 7_565 ?
C9 C9 C4 107.3(10) 7_565 . ?
F1 C11 F3 103(2) . . ?
F1 C11 C1 134.7(17) . . ?
F1 C11 C13 112.0(18) . . ?
F2 C11 F1 108.2(17) . . ?
F2 C11 F3 109(2) . . ?
F2 C11 C1 101.9(18) . . ?
F2 C11 C13 116(2) . . ?
F3 C11 C1 98.1(16) . . ?
F3 C11 C13 108.2(16) . . ?
C6 C11 F1 110(3) . . ?
C6 C11 F2 55(2) . . ?
C6 C11 F3 147(3) . . ?
C6 C11 C1 62.3(18) . . ?
C6 C11 C13 64.6(18) . . ?
C13 C11 C1 22.7(9) . . ?
C1 C13 Ir1 100(3) . . ?
C1 C13 C2 60(3) . . ?
C1 C13 C5 44(3) . . ?
C1 C13 C6 89(3) . . ?
C1 C13 C11 99(3) . . ?
C1 C13 C14 65(3) . . ?
C2 C13 Ir1 74.8(9) . . ?
C2 C13 C5 82.9(12) . . ?
C5 C13 Ir1 71.0(8) . . ?
C6 C13 Ir1 163.8(19) . . ?
C6 C13 C2 121(2) . . ?
C6 C13 C5 108.1(17) . . ?
C6 C13 C11 42.4(15) . . ?
C11 C13 Ir1 146.5(15) . . ?
C11 C13 C2 91.6(15) . . ?
C11 C13 C5 138.5(17) . . ?
C14 C13 Ir1 73.0(11) . . ?
C14 C13 C2 107.5(17) . . ?
C14 C13 C5 25.3(11) . . ?
C14 C13 C6 99.3(19) . . ?
C14 C13 C11 140.4(19) . . ?
C1 C14 Ir1 82.8(14) . . ?
C1 C14 C13 30.5(10) . . ?
C1 C14 C15 128.9(18) . . ?
C5 C14 Ir1 91.1(18) . . ?
C5 C14 C1 88(2) . . ?
C5 C14 C13 115(3) . . ?
C5 C14 C15 70.3(18) . . ?
C13 C14 Ir1 70.2(11) . . ?
C13 C14 C15 149.2(17) . . ?
C15 C14 Ir1 140.5(13) . . ?
F4 C15 C5 114.8(15) . . ?
F4 C15 C14 103.3(14) . . ?
F5 C15 F4 99.1(14) . . ?
F5 C15 C5 79.0(13) . . ?
F5 C15 C14 113.0(14) . . ?
F6 C15 F4 103.9(17) . . ?
F6 C15 F5 119(2) . . ?
F6 C15 C5 134.1(16) . . ?
F6 C15 C14 115.0(14) . . ?
C5 C15 C14 34.3(10) . . ?
O1 C16 Ir1 179.8(12) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_rph463
_database_code_depnum_ccdc_archive 'CCDC 1403908'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 F8 Ir O'
_chemical_formula_weight         555.47

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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.859(5)
_cell_length_b                   13.268(7)
_cell_length_c                   15.839(8)
_cell_angle_alpha                67.025(7)
_cell_angle_beta                 77.333(8)
_cell_angle_gamma                82.147(7)
_cell_volume                     1669.7(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    8.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2106
_exptl_absorpt_correction_T_max  0.4988
_exptl_absorpt_process_details   SADABS

_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_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            20486
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         25.40
_reflns_number_total             6070
_reflns_number_gt                5310
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0400P)²+11.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6070
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.34353(3) 0.16198(2) 0.117494(17) 0.01818(9) Uani 1 1 d . . .
Ir1' Ir -0.10039(3) -0.59088(2) 0.353070(17) 0.01932(9) Uani 1 1 d . . .
F1 F 0.1767(5) -0.0588(3) 0.1903(3) 0.0308(9) Uani 1 1 d . . .
F1' F 0.2547(5) -0.6184(4) 0.3550(3) 0.0399(11) Uani 1 1 d . . .
F2 F 0.0933(5) -0.0357(4) 0.3201(3) 0.0360(10) Uani 1 1 d . . .
F2' F 0.2989(5) -0.6052(4) 0.2120(4) 0.0431(12) Uani 1 1 d . . .
F3 F 0.2801(5) -0.1553(3) 0.3082(3) 0.0316(10) Uani 1 1 d . . .
F3' F 0.3310(5) -0.4684(4) 0.2460(3) 0.0355(10) Uani 1 1 d . . .
F4' F 0.1821(5) -0.3994(4) 0.1072(3) 0.0327(10) Uani 1 1 d . . .
F4 F 0.3536(5) -0.0457(3) 0.3964(3) 0.0297(9) Uani 1 1 d . . .
F5 F 0.4617(5) 0.1089(3) 0.3144(3) 0.0282(9) Uani 1 1 d . . .
F5' F -0.0664(5) -0.4081(3) 0.1375(3) 0.0283(9) Uani 1 1 d . . .
F6 F 0.6835(5) 0.0133(4) 0.2228(3) 0.0362(10) Uani 1 1 d . . .
F6' F 0.1381(5) -0.2932(4) 0.2378(3) 0.0336(10) Uani 1 1 d . . .
F7' F 0.0502(6) -0.2148(4) 0.1092(3) 0.0409(11) Uani 1 1 d . . .
F7 F 0.6556(5) -0.0689(4) 0.3725(3) 0.0374(11) Uani 1 1 d . . .
F8 F 0.5812(5) -0.1425(4) 0.2910(3) 0.0381(11) Uani 1 1 d . . .
F8' F -0.1064(5) -0.2877(4) 0.2387(3) 0.0359(10) Uani 1 1 d . . .
O1 O 0.6019(6) 0.2717(4) 0.1348(4) 0.0368(13) Uani 1 1 d . . .
O1' O -0.3597(6) -0.4394(5) 0.2740(4) 0.0443(15) Uani 1 1 d . . .
C1 C 0.1276(8) 0.1773(6) 0.0582(5) 0.0219(14) Uani 1 1 d . . .
C1' C -0.0201(8) -0.7647(6) 0.4413(5) 0.0236(15) Uani 1 1 d . . .
C2' C -0.0485(8) -0.7010(5) 0.4979(5) 0.0225(14) Uani 1 1 d . . .
C2 C 0.2530(8) 0.1419(6) 0.0006(5) 0.0221(14) Uani 1 1 d . . .
C3 C 0.3650(8) 0.2243(6) -0.0387(5) 0.0247(15) Uani 1 1 d . . .
C3' C -0.2083(8) -0.6609(6) 0.5041(5) 0.0260(16) Uani 1 1 d . . .
C4 C 0.3051(8) 0.3132(5) -0.0085(4) 0.0202(14) Uani 1 1 d . . .
C4' C -0.2796(8) -0.7041(6) 0.4546(5) 0.0270(16) Uani 1 1 d . . .
C5 C 0.1625(7) 0.2832(5) 0.0539(5) 0.0204(14) Uani 1 1 d . . .
C5' C -0.1636(8) -0.7642(6) 0.4120(5) 0.0218(14) Uani 1 1 d . . .
C6' C 0.1225(8) -0.8339(6) 0.4250(6) 0.0326(17) Uani 1 1 d . . .
H6'A H 0.1200 -0.9047 0.4774 0.049 Uiso 1 1 calc R . .
H6'B H 0.2143 -0.7966 0.4196 0.049 Uiso 1 1 calc R . .
H6'C H 0.1269 -0.8459 0.3672 0.049 Uiso 1 1 calc R . .
C6 C -0.0243(8) 0.1283(6) 0.1036(5) 0.0277(16) Uani 1 1 d . . .
H6A H -0.0931 0.1515 0.0578 0.042 Uiso 1 1 calc R . .
H6B H -0.0708 0.1530 0.1549 0.042 Uiso 1 1 calc R . .
H6C H -0.0094 0.0482 0.1281 0.042 Uiso 1 1 calc R . .
C7 C 0.2614(8) 0.0443(6) -0.0257(5) 0.0269(16) Uani 1 1 d . . .
H7A H 0.2110 0.0636 -0.0796 0.040 Uiso 1 1 calc R . .
H7B H 0.2087 -0.0158 0.0269 0.040 Uiso 1 1 calc R . .
H7C H 0.3702 0.0210 -0.0417 0.040 Uiso 1 1 calc R . .
C7' C 0.0626(10) -0.6873(7) 0.5515(5) 0.0356(18) Uani 1 1 d . . .
H7'A H 0.0571 -0.7491 0.6115 0.053 Uiso 1 1 calc R . .
H7'B H 0.0350 -0.6187 0.5622 0.053 Uiso 1 1 calc R . .
H7'C H 0.1682 -0.6853 0.5156 0.053 Uiso 1 1 calc R . .
C8 C 0.5114(8) 0.2225(6) -0.1077(5) 0.0301(17) Uani 1 1 d . . .
H8A H 0.4888 0.2548 -0.1711 0.045 Uiso 1 1 calc R . .
H8B H 0.5525 0.1466 -0.0948 0.045 Uiso 1 1 calc R . .
H8C H 0.5884 0.2650 -0.1021 0.045 Uiso 1 1 calc R . .
C8' C -0.2888(10) -0.5944(6) 0.5612(5) 0.039(2) Uani 1 1 d . . .
H8'A H -0.3257 -0.6438 0.6253 0.059 Uiso 1 1 calc R . .
H8'B H -0.3770 -0.5509 0.5340 0.059 Uiso 1 1 calc R . .
H8'C H -0.2159 -0.5453 0.5615 0.059 Uiso 1 1 calc R . .
C9 C 0.3781(9) 0.4208(6) -0.0387(5) 0.0301(17) Uani 1 1 d . . .
H9A H 0.3439 0.4727 -0.0957 0.045 Uiso 1 1 calc R . .
H9B H 0.4912 0.4092 -0.0506 0.045 Uiso 1 1 calc R . .
H9C H 0.3468 0.4505 0.0108 0.045 Uiso 1 1 calc R . .
C9' C -0.4482(9) -0.6901(7) 0.4489(7) 0.044(2) Uani 1 1 d . . .
H9'A H -0.5038 -0.7490 0.5012 0.066 Uiso 1 1 calc R . .
H9'B H -0.4608 -0.6929 0.3900 0.066 Uiso 1 1 calc R . .
H9'C H -0.4903 -0.6190 0.4520 0.066 Uiso 1 1 calc R . .
C10 C 0.0513(8) 0.3546(6) 0.0952(5) 0.0272(16) Uani 1 1 d . . .
H10A H -0.0151 0.3997 0.0506 0.041 Uiso 1 1 calc R . .
H10B H 0.1091 0.4021 0.1093 0.041 Uiso 1 1 calc R . .
H10C H -0.0130 0.3085 0.1527 0.041 Uiso 1 1 calc R . .
C10' C -0.1902(10) -0.8301(6) 0.3591(6) 0.0342(18) Uani 1 1 d . . .
H10D H -0.2165 -0.9042 0.4027 0.051 Uiso 1 1 calc R . .
H10E H -0.0959 -0.8342 0.3145 0.051 Uiso 1 1 calc R . .
H10F H -0.2756 -0.7949 0.3255 0.051 Uiso 1 1 calc R . .
C11' C -0.2526(8) -0.4916(6) 0.2971(5) 0.0309(17) Uani 1 1 d . . .
C11 C 0.5042(9) 0.2234(6) 0.1351(5) 0.0274(16) Uani 1 1 d . . .
C12 C 0.2233(9) -0.0521(6) 0.2624(5) 0.0280(16) Uani 1 1 d . . .
C12' C 0.2356(8) -0.5503(6) 0.2695(5) 0.0292(16) Uani 1 1 d . . .
C13' C 0.0682(7) -0.5115(6) 0.2632(5) 0.0211(14) Uani 1 1 d . . .
C13 C 0.3365(8) 0.0347(6) 0.2341(5) 0.0233(15) Uani 1 1 d . . .
C14 C 0.4306(8) 0.0142(6) 0.3086(5) 0.0258(15) Uani 1 1 d . . .
C14' C 0.0543(8) -0.4098(6) 0.1778(5) 0.0247(15) Uani 1 1 d . . .
C15' C 0.0352(9) -0.2996(6) 0.1917(5) 0.0279(16) Uani 1 1 d . . .
C15 C 0.5892(9) -0.0471(6) 0.2985(5) 0.0291(16) 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 C11 1.854(8) . ?
Ir1 C13 1.952(7) . ?
Ir1 C5 2.216(7) . ?
Ir1 C3 2.254(7) . ?
Ir1 C4 2.261(6) . ?
Ir1 C1 2.262(7) . ?
Ir1 C2 2.288(7) . ?
Ir1' C11' 1.862(8) . ?
Ir1' C13' 1.922(7) . ?
Ir1' C5' 2.218(7) . ?
Ir1' C3' 2.237(7) . ?
Ir1' C4' 2.238(7) . ?
Ir1' C2' 2.296(7) . ?
Ir1' C1' 2.291(7) . ?
F1 C12 1.333(8) . ?
F1' C12' 1.335(9) . ?
F2 C12 1.355(8) . ?
F2' C12' 1.363(8) . ?
F3 C12 1.360(8) . ?
F3' C12' 1.353(8) . ?
F4' C14' 1.385(8) . ?
F4 C14 1.379(8) . ?
F5 C14 1.363(8) . ?
F5' C14' 1.355(8) . ?
F6 C15 1.332(8) . ?
F6' C15' 1.317(9) . ?
F7' C15' 1.344(8) . ?
F7 C15 1.340(9) . ?
F8 C15 1.328(8) . ?
F8' C15' 1.335(8) . ?
O1 C11 1.144(9) . ?
O1' C11' 1.135(9) . ?
C1 C2 1.426(9) . ?
C1 C5 1.453(9) . ?
C1 C6 1.483(9) . ?
C1' C2' 1.419(9) . ?
C1' C5' 1.445(10) . ?
C1' C6' 1.495(9) . ?
C2' C3' 1.439(10) . ?
C2' C7' 1.501(10) . ?
C2 C3 1.436(10) . ?
C2 C7 1.496(9) . ?
C3 C4 1.435(9) . ?
C3 C8 1.506(9) . ?
C3' C4' 1.418(11) . ?
C3' C8' 1.508(10) . ?
C4 C5 1.419(9) . ?
C4 C9 1.506(9) . ?
C4' C5' 1.428(10) . ?
C4' C9' 1.498(10) . ?
C5 C10 1.497(9) . ?
C5' C10' 1.495(10) . ?
C12 C13 1.500(10) . ?
C12' C13' 1.513(10) . ?
C13' C14' 1.506(10) . ?
C13 C14 1.510(10) . ?
C14 C15 1.534(10) . ?
C14' C15' 1.543(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 Ir1 C13 94.9(3) . . ?
C11 Ir1 C5 114.1(3) . . ?
C13 Ir1 C5 132.7(3) . . ?
C11 Ir1 C3 104.1(3) . . ?
C13 Ir1 C3 147.0(3) . . ?
C5 Ir1 C3 62.2(2) . . ?
C11 Ir1 C4 91.6(3) . . ?
C13 Ir1 C4 169.6(3) . . ?
C5 Ir1 C4 36.9(2) . . ?
C3 Ir1 C4 37.1(2) . . ?
C11 Ir1 C1 151.4(3) . . ?
C13 Ir1 C1 110.1(3) . . ?
C5 Ir1 C1 37.9(2) . . ?
C3 Ir1 C1 61.7(2) . . ?
C4 Ir1 C1 61.8(2) . . ?
C11 Ir1 C2 140.2(3) . . ?
C13 Ir1 C2 116.7(3) . . ?
C5 Ir1 C2 62.1(2) . . ?
C3 Ir1 C2 36.9(2) . . ?
C4 Ir1 C2 61.5(2) . . ?
C1 Ir1 C2 36.5(2) . . ?
C11' Ir1' C13' 94.1(3) . . ?
C11' Ir1' C5' 113.8(3) . . ?
C13' Ir1' C5' 134.6(3) . . ?
C11' Ir1' C3' 104.3(3) . . ?
C13' Ir1' C3' 145.8(3) . . ?
C5' Ir1' C3' 62.4(3) . . ?
C11' Ir1' C4' 91.3(3) . . ?
C13' Ir1' C4' 172.0(3) . . ?
C5' Ir1' C4' 37.4(2) . . ?
C3' Ir1' C4' 36.9(3) . . ?
C11' Ir1' C2' 140.7(3) . . ?
C13' Ir1' C2' 116.8(3) . . ?
C5' Ir1' C2' 61.5(2) . . ?
C3' Ir1' C2' 37.0(2) . . ?
C4' Ir1' C2' 61.2(3) . . ?
C11' Ir1' C1' 150.6(3) . . ?
C13' Ir1' C1' 111.8(3) . . ?
C5' Ir1' C1' 37.3(2) . . ?
C3' Ir1' C1' 61.6(2) . . ?
C4' Ir1' C1' 61.7(2) . . ?
C2' Ir1' C1' 36.1(2) . . ?
C2 C1 C5 107.6(6) . . ?
C2 C1 C6 128.5(6) . . ?
C5 C1 C6 123.3(6) . . ?
C2 C1 Ir1 72.7(4) . . ?
C5 C1 Ir1 69.4(4) . . ?
C6 C1 Ir1 130.3(5) . . ?
C2' C1' C5' 107.4(6) . . ?
C2' C1' C6' 127.6(7) . . ?
C5' C1' C6' 124.5(6) . . ?
C2' C1' Ir1' 72.2(4) . . ?
C5' C1' Ir1' 68.6(4) . . ?
C6' C1' Ir1' 131.0(5) . . ?
C1' C2' C3' 108.4(6) . . ?
C1' C2' C7' 126.3(7) . . ?
C3' C2' C7' 124.9(6) . . ?
C1' C2' Ir1' 71.8(4) . . ?
C3' C2' Ir1' 69.3(4) . . ?
C7' C2' Ir1' 129.8(5) . . ?
C1 C2 C3 108.0(6) . . ?
C1 C2 C7 127.2(6) . . ?
C3 C2 C7 124.3(6) . . ?
C1 C2 Ir1 70.7(4) . . ?
C3 C2 Ir1 70.3(4) . . ?
C7 C2 Ir1 130.4(5) . . ?
C2 C3 C4 108.1(6) . . ?
C2 C3 C8 125.5(6) . . ?
C4 C3 C8 126.1(6) . . ?
C2 C3 Ir1 72.9(4) . . ?
C4 C3 Ir1 71.7(4) . . ?
C8 C3 Ir1 126.0(5) . . ?
C4' C3' C2' 107.8(6) . . ?
C4' C3' C8' 126.1(7) . . ?
C2' C3' C8' 125.8(7) . . ?
C4' C3' Ir1' 71.6(4) . . ?
C2' C3' Ir1' 73.8(4) . . ?
C8' C3' Ir1' 125.0(5) . . ?
C5 C4 C3 108.1(6) . . ?
C5 C4 C9 125.5(6) . . ?
C3 C4 C9 126.4(6) . . ?
C5 C4 Ir1 69.8(4) . . ?
C3 C4 Ir1 71.2(4) . . ?
C9 C4 Ir1 125.4(5) . . ?
C3' C4' C5' 108.3(6) . . ?
C3' C4' C9' 125.7(7) . . ?
C5' C4' C9' 125.9(7) . . ?
C3' C4' Ir1' 71.5(4) . . ?
C5' C4' Ir1' 70.6(4) . . ?
C9' C4' Ir1' 124.3(5) . . ?
C4 C5 C1 108.0(5) . . ?
C4 C5 C10 126.8(6) . . ?
C1 C5 C10 124.3(6) . . ?
C4 C5 Ir1 73.2(4) . . ?
C1 C5 Ir1 72.8(4) . . ?
C10 C5 Ir1 128.1(5) . . ?
C4' C5' C1' 107.9(6) . . ?
C4' C5' C10' 126.2(6) . . ?
C1' C5' C10' 125.3(6) . . ?
C4' C5' Ir1' 72.1(4) . . ?
C1' C5' Ir1' 74.1(4) . . ?
C10' C5' Ir1' 126.8(5) . . ?
O1' C11' Ir1' 170.2(7) . . ?
O1 C11 Ir1 171.1(7) . . ?
F1 C12 F2 106.4(6) . . ?
F1 C12 F3 104.4(5) . . ?
F2 C12 F3 105.5(6) . . ?
F1 C12 C13 113.3(6) . . ?
F2 C12 C13 112.5(6) . . ?
F3 C12 C13 114.0(6) . . ?
F1' C12' F3' 105.4(6) . . ?
F1' C12' F2' 105.9(6) . . ?
F3' C12' F2' 104.9(6) . . ?
F1' C12' C13' 113.1(6) . . ?
F3' C12' C13' 114.0(6) . . ?
F2' C12' C13' 112.8(6) . . ?
C12' C13' C14' 111.9(6) . . ?
C12' C13' Ir1' 121.9(5) . . ?
C14' C13' Ir1' 126.2(5) . . ?
C12 C13 C14 111.9(6) . . ?
C12 C13 Ir1 121.7(5) . . ?
C14 C13 Ir1 126.3(5) . . ?
F5 C14 F4 104.9(5) . . ?
F5 C14 C13 112.4(6) . . ?
F4 C14 C13 112.2(6) . . ?
F5 C14 C15 104.6(6) . . ?
F4 C14 C15 105.1(6) . . ?
C13 C14 C15 116.6(6) . . ?
F5' C14' F4' 103.9(5) . . ?
F5' C14' C13' 113.5(5) . . ?
F4' C14' C13' 112.5(6) . . ?
F5' C14' C15' 104.7(6) . . ?
F4' C14' C15' 104.7(5) . . ?
C13' C14' C15' 116.3(6) . . ?
F6' C15' F8' 108.6(6) . . ?
F6' C15' F7' 108.3(6) . . ?
F8' C15' F7' 107.0(6) . . ?
F6' C15' C14' 111.7(6) . . ?
F8' C15' C14' 110.0(6) . . ?
F7' C15' C14' 111.0(6) . . ?
F8 C15 F6 107.5(6) . . ?
F8 C15 F7 106.8(6) . . ?
F6 C15 F7 108.0(6) . . ?
F8 C15 C14 113.0(6) . . ?
F6 C15 C14 110.2(6) . . ?
F7 C15 C14 111.1(6) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         3.644
_refine_diff_density_min         -1.941
_refine_diff_density_rms         0.201
