# 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).
# 
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# 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. 
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data_rph330
_database_code_depnum_ccdc_archive 'CCDC 1406693'
_audit_update_record             
;
2015-06-13 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;
_audit_creation_date             2015-06-02
_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         'C15 H24 F4 Ir P'
_chemical_formula_sum            'C15 H24 F4 Ir P'
_chemical_formula_weight         503.51
_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'
H H 0.0000 0.0000 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.6958(17)
_cell_length_b                   17.033(2)
_cell_length_c                   17.415(2)
_cell_angle_alpha                109.330(2)
_cell_angle_beta                 100.572(2)
_cell_angle_gamma                90.329(2)
_cell_volume                     3484.2(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9330
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      0.000
_cell_measurement_theta_min      0.000
_shelx_estimated_absorpt_T_max   0.697
_shelx_estimated_absorpt_T_min   0.510
_exptl_absorpt_coefficient_mu    7.784
_exptl_absorpt_correction_T_max  0.663
_exptl_absorpt_correction_T_min  0.577253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.1020 before and 0.0381 after correction.
The Ratio of minimum to maximum transmission is 0.5773.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.920
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.1042
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29848
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         1.264
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.938
_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                9897
_reflns_number_total             15068
_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       'SAINT v7.06A (Bruker, 2003)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.06A (Bruker, 2003)'
_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         2.343
_refine_diff_density_min         -2.398
_refine_diff_density_rms         0.223
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     789
_refine_ls_number_reflns         15068
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0503P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1156
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C),
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,
 H30B,H30C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C),
 C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C43(H43A,H43B,H43C), C44(H44A,H44B,
 H44C), C45(H45A,H45B,H45C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C53(H53A,
 H53B,H53C), C54(H54A,H54B,H54C), C55(H55A,H55B,H55C), C58(H58A,H58B,H58C),
 C59(H59A,H59B,H59C), C60(H60A,H60B,H60C)
;
_atom_sites_solution_hydrogens   geom
_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 0.11803(3) 0.88393(2) 0.21642(2) 0.02377(10) Uani 1 1 d . . . . .
Ir2 Ir 0.66504(3) 1.06486(2) 0.26966(2) 0.02342(10) Uani 1 1 d . . . . .
Ir3 Ir 0.71459(3) 1.58903(2) 0.29518(2) 0.02430(10) Uani 1 1 d . . . . .
Ir4 Ir 1.25609(3) 1.37570(2) 0.21774(2) 0.02521(10) Uani 1 1 d . . . . .
P1 P 0.1589(2) 0.82672(19) 0.31667(17) 0.0329(6) Uani 1 1 d . . . . .
P2 P 0.5338(2) 0.97291(17) 0.17871(17) 0.0283(6) Uani 1 1 d . . . . .
P3 P 0.7850(2) 1.48952(17) 0.20122(17) 0.0321(6) Uani 1 1 d . . . . .
P4 P 1.3119(2) 1.41880(18) 0.12168(17) 0.0329(6) Uani 1 1 d . . . . .
F1 F 0.2648(5) 0.9920(4) 0.3682(4) 0.0468(17) Uani 1 1 d . . . . .
F2 F 0.2941(5) 1.0961(4) 0.2851(5) 0.066(2) Uani 1 1 d . . . . .
F3 F 0.1766(5) 1.1238(4) 0.3619(4) 0.059(2) Uani 1 1 d . . . . .
F4 F 0.1262(5) 1.0787(4) 0.2296(4) 0.0490(17) Uani 1 1 d . . . . .
F5 F 0.6331(5) 1.0655(4) 0.0974(4) 0.0453(16) Uani 1 1 d . . . . .
F6 F 0.8155(6) 1.2081(5) 0.2502(4) 0.067(2) Uani 1 1 d . . . . .
F7 F 0.8166(6) 1.1427(4) 0.1221(5) 0.060(2) Uani 1 1 d . . . . .
F8 F 0.6927(6) 1.2243(5) 0.1528(6) 0.072(2) Uani 1 1 d . . . . .
F9 F 0.6866(5) 1.6060(4) 0.1279(4) 0.0419(16) Uani 1 1 d . . . . .
F10 F 0.5344(5) 1.7165(4) 0.2677(4) 0.0437(16) Uani 1 1 d . . . . .
F11 F 0.6473(5) 1.7704(4) 0.2181(5) 0.066(2) Uani 1 1 d . . . . .
F12 F 0.5201(5) 1.6824(4) 0.1359(4) 0.0557(19) Uani 1 1 d . . . . .
F13 F 1.2188(5) 1.5520(4) 0.2342(4) 0.0446(16) Uani 1 1 d . . . . .
F14 F 1.2106(6) 1.4821(4) 0.3987(4) 0.0505(18) Uani 1 1 d . . . . .
F15 F 1.0902(5) 1.5477(4) 0.3433(4) 0.0528(19) Uani 1 1 d . . . . .
F16 F 1.2511(5) 1.6021(4) 0.3907(4) 0.0468(17) Uani 1 1 d . . . . .
C1 C 0.0529(7) 0.7672(5) 0.1031(6) 0.023(2) Uani 1 1 d . . . . .
C2 C -0.0348(7) 0.8138(6) 0.1304(6) 0.025(2) Uani 1 1 d . . . . .
C3 C -0.0221(7) 0.8955(6) 0.1228(6) 0.026(2) Uani 1 1 d . . . . .
C4 C 0.0730(7) 0.8985(6) 0.0913(6) 0.024(2) Uani 1 1 d . . . . .
C5 C 0.1198(8) 0.8198(6) 0.0809(5) 0.025(2) Uani 1 1 d . . . . .
C6 C 0.0669(9) 0.6774(6) 0.0899(7) 0.040(3) Uani 1 1 d . . . . .
H6A H 0.0489 0.6455 0.0303 0.060 Uiso 1 1 calc GR . . . .
H6B H 0.0192 0.6571 0.1187 0.060 Uiso 1 1 calc GR . . . .
H6C H 0.1416 0.6703 0.1118 0.060 Uiso 1 1 calc GR . . . .
C7 C -0.1328(8) 0.7824(7) 0.1530(7) 0.037(3) Uani 1 1 d . . . . .
H7A H -0.1842 0.7515 0.1022 0.055 Uiso 1 1 calc GR . . . .
H7B H -0.1666 0.8299 0.1863 0.055 Uiso 1 1 calc GR . . . .
H7C H -0.1111 0.7455 0.1850 0.055 Uiso 1 1 calc GR . . . .
C8 C -0.1018(8) 0.9596(6) 0.1356(6) 0.033(2) Uani 1 1 d . . . . .
H8A H -0.0653 1.0148 0.1498 0.049 Uiso 1 1 calc GR . . . .
H8B H -0.1368 0.9582 0.1809 0.049 Uiso 1 1 calc GR . . . .
H8C H -0.1559 0.9480 0.0845 0.049 Uiso 1 1 calc GR . . . .
C9 C 0.1101(7) 0.9639(6) 0.0623(6) 0.032(2) Uani 1 1 d . . . . .
H9A H 0.0633 1.0102 0.0740 0.047 Uiso 1 1 calc GR . . . .
H9B H 0.1077 0.9408 0.0024 0.047 Uiso 1 1 calc GR . . . .
H9C H 0.1840 0.9842 0.0912 0.047 Uiso 1 1 calc GR . . . .
C10 C 0.2152(7) 0.7922(6) 0.0420(6) 0.031(2) Uani 1 1 d . . . . .
H10A H 0.2566 0.7576 0.0700 0.047 Uiso 1 1 calc GR . . . .
H10B H 0.2607 0.8412 0.0475 0.047 Uiso 1 1 calc GR . . . .
H10C H 0.1909 0.7597 -0.0169 0.047 Uiso 1 1 calc GR . . . .
C11 C 0.1894(8) 0.9826(6) 0.2906(7) 0.036(3) Uani 1 1 d . . . . .
C12 C 0.1972(10) 1.0677(7) 0.2909(7) 0.049(3) Uani 1 1 d . . . . .
C13 C 0.0897(10) 0.7276(7) 0.2974(7) 0.051(3) Uani 1 1 d . . . . .
H13A H 0.1173 0.7064 0.3425 0.077 Uiso 1 1 calc GR . . . .
H13B H 0.1015 0.6880 0.2447 0.077 Uiso 1 1 calc GR . . . .
H13C H 0.0126 0.7344 0.2944 0.077 Uiso 1 1 calc GR . . . .
C14 C 0.1272(10) 0.8841(8) 0.4166(7) 0.053(4) Uani 1 1 d . . . . .
H14A H 0.0492 0.8872 0.4108 0.080 Uiso 1 1 calc GR . . . .
H14B H 0.1621 0.9406 0.4368 0.080 Uiso 1 1 calc GR . . . .
H14C H 0.1531 0.8555 0.4561 0.080 Uiso 1 1 calc GR . . . .
C15 C 0.2981(8) 0.8046(8) 0.3419(8) 0.049(3) Uani 1 1 d . . . . .
H15A H 0.3106 0.7931 0.3942 0.073 Uiso 1 1 calc GR . . . .
H15B H 0.3450 0.8529 0.3476 0.073 Uiso 1 1 calc GR . . . .
H15C H 0.3137 0.7558 0.2974 0.073 Uiso 1 1 calc GR . . . .
C16 C 0.6598(8) 1.0362(7) 0.3899(6) 0.034(3) Uani 1 1 d . . . . .
C17 C 0.6404(10) 1.1214(8) 0.4023(6) 0.045(3) Uani 1 1 d . . . . .
C18 C 0.7336(11) 1.1617(6) 0.3932(7) 0.044(3) Uani 1 1 d . . . . .
C19 C 0.8094(8) 1.1014(7) 0.3721(6) 0.029(2) Uani 1 1 d . . . . .
C20 C 0.7639(8) 1.0234(6) 0.3698(6) 0.027(2) Uani 1 1 d . . . . .
C21 C 0.5936(10) 0.9750(10) 0.4083(8) 0.070(4) Uani 1 1 d . . . . .
H21A H 0.5986 0.9189 0.3697 0.105 Uiso 1 1 calc GR . . . .
H21B H 0.5185 0.9892 0.4019 0.105 Uiso 1 1 calc GR . . . .
H21C H 0.6198 0.9766 0.4654 0.105 Uiso 1 1 calc GR . . . .
C22 C 0.5398(12) 1.1615(10) 0.4280(8) 0.086(6) Uani 1 1 d . . . . .
H22A H 0.5425 1.1699 0.4868 0.130 Uiso 1 1 calc GR . . . .
H22B H 0.4762 1.1249 0.3945 0.130 Uiso 1 1 calc GR . . . .
H22C H 0.5358 1.2154 0.4192 0.130 Uiso 1 1 calc GR . . . .
C23 C 0.7519(16) 1.2527(8) 0.4130(8) 0.101(7) Uani 1 1 d . . . . .
H23A H 0.7458 1.2817 0.4707 0.152 Uiso 1 1 calc GR . . . .
H23B H 0.6980 1.2714 0.3760 0.152 Uiso 1 1 calc GR . . . .
H23C H 0.8239 1.2654 0.4054 0.152 Uiso 1 1 calc GR . . . .
C24 C 0.9236(9) 1.1151(8) 0.3667(7) 0.054(4) Uani 1 1 d . . . . .
H24A H 0.9338 1.1687 0.3585 0.081 Uiso 1 1 calc GR . . . .
H24B H 0.9412 1.0700 0.3198 0.081 Uiso 1 1 calc GR . . . .
H24C H 0.9708 1.1157 0.4182 0.081 Uiso 1 1 calc GR . . . .
C25 C 0.8207(10) 0.9444(7) 0.3601(7) 0.049(3) Uani 1 1 d . . . . .
H25A H 0.8538 0.9428 0.4150 0.073 Uiso 1 1 calc GR . . . .
H25B H 0.8765 0.9428 0.3276 0.073 Uiso 1 1 calc GR . . . .
H25C H 0.7689 0.8961 0.3314 0.073 Uiso 1 1 calc GR . . . .
C26 C 0.6854(8) 1.1015(7) 0.1853(7) 0.034(3) Uani 1 1 d . . . . .
C27 C 0.7517(9) 1.1679(7) 0.1782(7) 0.041(3) Uani 1 1 d . . . . .
C28 C 0.4252(8) 1.0152(7) 0.1221(7) 0.041(3) Uani 1 1 d . . . . .
H28A H 0.3741 0.9695 0.0842 0.061 Uiso 1 1 calc GR . . . .
H28B H 0.4555 1.0443 0.0902 0.061 Uiso 1 1 calc GR . . . .
H28C H 0.3881 1.0544 0.1616 0.061 Uiso 1 1 calc GR . . . .
C29 C 0.4565(9) 0.9126(8) 0.2203(8) 0.054(3) Uani 1 1 d . . . . .
H29A H 0.4013 0.8760 0.1756 0.081 Uiso 1 1 calc GR . . . .
H29B H 0.4221 0.9505 0.2628 0.081 Uiso 1 1 calc GR . . . .
H29C H 0.5043 0.8788 0.2451 0.081 Uiso 1 1 calc GR . . . .
C30 C 0.5746(9) 0.8920(7) 0.0937(7) 0.043(3) Uani 1 1 d . . . . .
H30A H 0.6278 0.8597 0.1160 0.065 Uiso 1 1 calc GR . . . .
H30B H 0.6062 0.9177 0.0597 0.065 Uiso 1 1 calc GR . . . .
H30C H 0.5118 0.8550 0.0595 0.065 Uiso 1 1 calc GR . . . .
C31 C 0.6770(7) 1.5420(6) 0.3957(6) 0.027(2) Uani 1 1 d . . . . .
C32 C 0.7900(7) 1.5686(6) 0.4171(6) 0.027(2) Uani 1 1 d . . . . .
C33 C 0.8003(8) 1.6520(6) 0.4252(6) 0.030(2) Uani 1 1 d . . . . .
C34 C 0.6969(8) 1.6832(6) 0.4159(6) 0.030(2) Uani 1 1 d . . . . .
C35 C 0.6197(8) 1.6138(6) 0.3971(6) 0.025(2) Uani 1 1 d . . . . .
C36 C 0.6298(10) 1.4592(7) 0.3863(7) 0.044(3) Uani 1 1 d . . . . .
H36A H 0.6140 1.4598 0.4395 0.067 Uiso 1 1 calc GR . . . .
H36B H 0.6807 1.4170 0.3688 0.067 Uiso 1 1 calc GR . . . .
H36C H 0.5632 1.4458 0.3444 0.067 Uiso 1 1 calc GR . . . .
C37 C 0.8806(9) 1.5154(8) 0.4339(7) 0.047(3) Uani 1 1 d . . . . .
H37A H 0.9432 1.5300 0.4144 0.071 Uiso 1 1 calc GR . . . .
H37B H 0.8574 1.4564 0.4045 0.071 Uiso 1 1 calc GR . . . .
H37C H 0.8999 1.5254 0.4936 0.071 Uiso 1 1 calc GR . . . .
C38 C 0.9043(9) 1.7074(8) 0.4528(7) 0.052(3) Uani 1 1 d . . . . .
H38A H 0.9201 1.7322 0.5135 0.078 Uiso 1 1 calc GR . . . .
H38B H 0.8965 1.7518 0.4284 0.078 Uiso 1 1 calc GR . . . .
H38C H 0.9632 1.6739 0.4344 0.078 Uiso 1 1 calc GR . . . .
C39 C 0.6730(9) 1.7718(7) 0.4357(7) 0.043(3) Uani 1 1 d . . . . .
H39A H 0.6948 1.8008 0.4956 0.065 Uiso 1 1 calc GR . . . .
H39B H 0.5958 1.7754 0.4184 0.065 Uiso 1 1 calc GR . . . .
H39C H 0.7127 1.7978 0.4060 0.065 Uiso 1 1 calc GR . . . .
C40 C 0.5014(8) 1.6157(7) 0.3909(6) 0.035(3) Uani 1 1 d . . . . .
H40A H 0.4668 1.5605 0.3564 0.052 Uiso 1 1 calc GR . . . .
H40B H 0.4747 1.6572 0.3657 0.052 Uiso 1 1 calc GR . . . .
H40C H 0.4846 1.6305 0.4465 0.052 Uiso 1 1 calc GR . . . .
C41 C 0.6632(8) 1.6318(6) 0.2115(6) 0.033(2) Uani 1 1 d . . . . .
C42 C 0.5934(9) 1.6998(7) 0.2088(7) 0.039(3) Uani 1 1 d . . . . .
C43 C 0.8483(10) 1.4085(7) 0.2351(7) 0.050(3) Uani 1 1 d . . . . .
H43A H 0.8771 1.3697 0.1896 0.075 Uiso 1 1 calc GR . . . .
H43B H 0.7951 1.3783 0.2512 0.075 Uiso 1 1 calc GR . . . .
H43C H 0.9069 1.4337 0.2827 0.075 Uiso 1 1 calc GR . . . .
C44 C 0.6902(9) 1.4256(7) 0.1091(7) 0.051(3) Uani 1 1 d . . . . .
H44A H 0.7296 1.3888 0.0696 0.077 Uiso 1 1 calc GR . . . .
H44B H 0.6488 1.4618 0.0831 0.077 Uiso 1 1 calc GR . . . .
H44C H 0.6411 1.3918 0.1249 0.077 Uiso 1 1 calc GR . . . .
C45 C 0.8931(8) 1.5223(7) 0.1607(7) 0.043(3) Uani 1 1 d . . . . .
H45A H 0.9539 1.5480 0.2064 0.064 Uiso 1 1 calc GR . . . .
H45B H 0.8677 1.5628 0.1338 0.064 Uiso 1 1 calc GR . . . .
H45C H 0.9159 1.4736 0.1201 0.064 Uiso 1 1 calc GR . . . .
C46 C 1.2587(8) 1.2341(6) 0.1584(6) 0.030(2) Uani 1 1 d . . . . .
C47 C 1.1618(8) 1.2551(6) 0.1878(7) 0.031(2) Uani 1 1 d . . . . .
C48 C 1.1868(8) 1.2935(6) 0.2747(6) 0.030(2) Uani 1 1 d . . . . .
C49 C 1.2992(8) 1.2995(6) 0.3010(6) 0.031(2) Uani 1 1 d . . . . .
C50 C 1.3466(7) 1.2642(6) 0.2298(6) 0.024(2) Uani 1 1 d . . . . .
C51 C 1.2674(8) 1.1814(6) 0.0731(6) 0.034(3) Uani 1 1 d . . . . .
H51A H 1.2497 1.1228 0.0652 0.051 Uiso 1 1 calc GR . . . .
H51B H 1.3410 1.1880 0.0652 0.051 Uiso 1 1 calc GR . . . .
H51C H 1.2174 1.1987 0.0327 0.051 Uiso 1 1 calc GR . . . .
C52 C 1.0515(8) 1.2280(7) 0.1353(7) 0.036(3) Uani 1 1 d . . . . .
H52A H 1.0343 1.1693 0.1271 0.055 Uiso 1 1 calc GR . . . .
H52B H 1.0494 1.2349 0.0814 0.055 Uiso 1 1 calc GR . . . .
H52C H 0.9988 1.2623 0.1632 0.055 Uiso 1 1 calc GR . . . .
C53 C 1.1026(9) 1.3097(7) 0.3285(7) 0.044(3) Uani 1 1 d . . . . .
H53A H 1.0522 1.3477 0.3129 0.066 Uiso 1 1 calc GR . . . .
H53B H 1.1377 1.3350 0.3869 0.066 Uiso 1 1 calc GR . . . .
H53C H 1.0635 1.2569 0.3205 0.066 Uiso 1 1 calc GR . . . .
C54 C 1.3606(9) 1.3303(7) 0.3902(6) 0.039(3) Uani 1 1 d . . . . .
H54A H 1.3203 1.3718 0.4247 0.058 Uiso 1 1 calc GR . . . .
H54B H 1.4312 1.3557 0.3926 0.058 Uiso 1 1 calc GR . . . .
H54C H 1.3701 1.2832 0.4107 0.058 Uiso 1 1 calc GR . . . .
C55 C 1.4628(8) 1.2502(7) 0.2306(7) 0.037(3) Uani 1 1 d . . . . .
H55A H 1.5064 1.3018 0.2648 0.056 Uiso 1 1 calc GR . . . .
H55B H 1.4756 1.2338 0.1738 0.056 Uiso 1 1 calc GR . . . .
H55C H 1.4826 1.2059 0.2536 0.056 Uiso 1 1 calc GR . . . .
C56 C 1.2237(9) 1.4836(7) 0.2683(7) 0.043(3) Uani 1 1 d . . . . .
C57 C 1.1950(9) 1.5280(7) 0.3497(7) 0.044(3) Uani 1 1 d . . . . .
C58 C 1.4107(9) 1.5076(7) 0.1566(7) 0.046(3) Uani 1 1 d . . . . .
H58A H 1.4759 1.4953 0.1892 0.069 Uiso 1 1 calc GR . . . .
H58B H 1.3810 1.5570 0.1910 0.069 Uiso 1 1 calc GR . . . .
H58C H 1.4283 1.5183 0.1083 0.069 Uiso 1 1 calc GR . . . .
C59 C 1.2077(9) 1.4442(7) 0.0495(7) 0.044(3) Uani 1 1 d . . . . .
H59A H 1.2405 1.4688 0.0153 0.066 Uiso 1 1 calc GR . . . .
H59B H 1.1623 1.4841 0.0804 0.066 Uiso 1 1 calc GR . . . .
H59C H 1.1637 1.3933 0.0138 0.066 Uiso 1 1 calc GR . . . .
C60 C 1.3836(8) 1.3448(7) 0.0526(7) 0.039(3) Uani 1 1 d . . . . .
H60A H 1.3335 1.2985 0.0145 0.059 Uiso 1 1 calc GR . . . .
H60B H 1.4400 1.3234 0.0852 0.059 Uiso 1 1 calc GR . . . .
H60C H 1.4161 1.3726 0.0206 0.059 Uiso 1 1 calc GR . . . .


_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 P1 2.251(3) . ?
Ir1 C1 2.306(9) . ?
Ir1 C2 2.271(9) . ?
Ir1 C3 2.239(9) . ?
Ir1 C4 2.246(9) . ?
Ir1 C5 2.253(8) . ?
Ir1 C11 1.853(10) . ?
Ir2 P2 2.258(3) . ?
Ir2 C16 2.313(10) . ?
Ir2 C17 2.271(10) . ?
Ir2 C18 2.248(10) . ?
Ir2 C19 2.232(9) . ?
Ir2 C20 2.267(9) . ?
Ir2 C26 1.832(10) . ?
Ir3 P3 2.251(3) . ?
Ir3 C31 2.273(9) . ?
Ir3 C32 2.300(9) . ?
Ir3 C33 2.222(9) . ?
Ir3 C34 2.234(9) . ?
Ir3 C35 2.253(9) . ?
Ir3 C41 1.854(10) . ?
Ir4 P4 2.254(3) . ?
Ir4 C46 2.291(9) . ?
Ir4 C47 2.227(10) . ?
Ir4 C48 2.224(10) . ?
Ir4 C49 2.248(11) . ?
Ir4 C50 2.275(9) . ?
Ir4 C56 1.841(11) . ?
P1 C13 1.798(12) . ?
P1 C14 1.811(10) . ?
P1 C15 1.814(10) . ?
P2 C28 1.837(10) . ?
P2 C29 1.813(12) . ?
P2 C30 1.816(11) . ?
P3 C43 1.810(11) . ?
P3 C44 1.825(11) . ?
P3 C45 1.816(11) . ?
P4 C58 1.822(11) . ?
P4 C59 1.809(11) . ?
P4 C60 1.810(11) . ?
F1 C11 1.465(12) . ?
F2 C12 1.352(13) . ?
F3 C12 1.360(12) . ?
F4 C12 1.331(14) . ?
F5 C26 1.471(12) . ?
F6 C27 1.323(13) . ?
F7 C27 1.356(12) . ?
F8 C27 1.359(12) . ?
F9 C41 1.462(11) . ?
F10 C42 1.337(12) . ?
F11 C42 1.327(12) . ?
F12 C42 1.371(12) . ?
F13 C56 1.469(13) . ?
F14 C57 1.327(14) . ?
F15 C57 1.367(12) . ?
F16 C57 1.347(12) . ?
C1 C2 1.431(12) . ?
C1 C5 1.420(13) . ?
C1 C6 1.486(13) . ?
C2 C3 1.452(13) . ?
C2 C7 1.517(13) . ?
C3 C4 1.423(13) . ?
C3 C8 1.483(13) . ?
C4 C5 1.439(13) . ?
C4 C9 1.473(13) . ?
C5 C10 1.498(12) . ?
C11 C12 1.449(16) . ?
C16 C17 1.424(15) . ?
C16 C20 1.428(13) . ?
C16 C21 1.486(15) . ?
C17 C18 1.423(17) . ?
C17 C22 1.522(16) . ?
C18 C19 1.417(15) . ?
C18 C23 1.479(16) . ?
C19 C20 1.431(14) . ?
C19 C24 1.493(14) . ?
C20 C25 1.505(13) . ?
C26 C27 1.458(15) . ?
C31 C32 1.444(13) . ?
C31 C35 1.424(13) . ?
C31 C36 1.475(13) . ?
C32 C33 1.383(13) . ?
C32 C37 1.515(13) . ?
C33 C34 1.421(14) . ?
C33 C38 1.522(13) . ?
C34 C35 1.440(13) . ?
C34 C39 1.479(14) . ?
C35 C40 1.487(13) . ?
C41 C42 1.470(14) . ?
C46 C47 1.421(13) . ?
C46 C50 1.455(13) . ?
C46 C51 1.484(13) . ?
C47 C48 1.408(14) . ?
C47 C52 1.501(13) . ?
C48 C49 1.410(13) . ?
C48 C53 1.515(14) . ?
C49 C50 1.430(13) . ?
C49 C54 1.518(13) . ?
C50 C55 1.493(13) . ?
C56 C57 1.482(15) . ?

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
P1 Ir1 C1 100.8(2) . . ?
P1 Ir1 C2 107.0(3) . . ?
P1 Ir1 C5 125.6(3) . . ?
C2 Ir1 C1 36.4(3) . . ?
C3 Ir1 P1 140.4(3) . . ?
C3 Ir1 C1 61.8(3) . . ?
C3 Ir1 C2 37.5(3) . . ?
C3 Ir1 C4 37.0(3) . . ?
C3 Ir1 C5 61.8(3) . . ?
C4 Ir1 P1 161.9(2) . . ?
C4 Ir1 C1 61.6(3) . . ?
C4 Ir1 C2 61.9(3) . . ?
C4 Ir1 C5 37.3(3) . . ?
C5 Ir1 C1 36.3(3) . . ?
C5 Ir1 C2 61.0(3) . . ?
C11 Ir1 P1 88.3(4) . . ?
C11 Ir1 C1 166.4(4) . . ?
C11 Ir1 C2 149.5(4) . . ?
C11 Ir1 C3 116.6(4) . . ?
C11 Ir1 C4 108.3(4) . . ?
C11 Ir1 C5 130.2(4) . . ?
P2 Ir2 C16 101.0(3) . . ?
P2 Ir2 C17 116.9(3) . . ?
P2 Ir2 C20 116.9(3) . . ?
C17 Ir2 C16 36.2(4) . . ?
C18 Ir2 P2 153.1(4) . . ?
C18 Ir2 C16 60.8(4) . . ?
C18 Ir2 C17 36.7(4) . . ?
C18 Ir2 C20 61.3(4) . . ?
C19 Ir2 P2 153.3(3) . . ?
C19 Ir2 C16 61.2(3) . . ?
C19 Ir2 C17 61.5(4) . . ?
C19 Ir2 C18 36.9(4) . . ?
C19 Ir2 C20 37.1(3) . . ?
C20 Ir2 C16 36.3(3) . . ?
C20 Ir2 C17 60.9(4) . . ?
C26 Ir2 P2 88.4(4) . . ?
C26 Ir2 C16 170.6(4) . . ?
C26 Ir2 C17 137.7(5) . . ?
C26 Ir2 C18 110.2(5) . . ?
C26 Ir2 C19 110.4(4) . . ?
C26 Ir2 C20 138.9(4) . . ?
P3 Ir3 C31 110.8(3) . . ?
P3 Ir3 C32 102.0(3) . . ?
P3 Ir3 C35 144.7(3) . . ?
C31 Ir3 C32 36.8(3) . . ?
C33 Ir3 P3 123.2(3) . . ?
C33 Ir3 C31 61.3(4) . . ?
C33 Ir3 C32 35.6(3) . . ?
C33 Ir3 C34 37.2(4) . . ?
C33 Ir3 C35 61.8(4) . . ?
C34 Ir3 P3 160.3(3) . . ?
C34 Ir3 C31 61.9(4) . . ?
C34 Ir3 C32 60.7(4) . . ?
C34 Ir3 C35 37.4(3) . . ?
C35 Ir3 C31 36.7(3) . . ?
C35 Ir3 C32 60.8(3) . . ?
C41 Ir3 P3 87.6(3) . . ?
C41 Ir3 C31 147.4(4) . . ?
C41 Ir3 C32 166.4(4) . . ?
C41 Ir3 C33 130.9(4) . . ?
C41 Ir3 C34 108.1(4) . . ?
C41 Ir3 C35 115.8(4) . . ?
P4 Ir4 C46 100.6(3) . . ?
P4 Ir4 C50 109.4(3) . . ?
C47 Ir4 P4 123.7(3) . . ?
C47 Ir4 C46 36.6(3) . . ?
C47 Ir4 C49 61.5(4) . . ?
C47 Ir4 C50 61.9(3) . . ?
C48 Ir4 P4 160.2(3) . . ?
C48 Ir4 C46 61.2(4) . . ?
C48 Ir4 C47 36.9(4) . . ?
C48 Ir4 C49 36.7(3) . . ?
C48 Ir4 C50 61.6(3) . . ?
C49 Ir4 P4 143.6(3) . . ?
C49 Ir4 C46 61.4(3) . . ?
C49 Ir4 C50 36.9(3) . . ?
C50 Ir4 C46 37.2(3) . . ?
C56 Ir4 P4 88.1(4) . . ?
C56 Ir4 C46 167.1(4) . . ?
C56 Ir4 C47 130.5(5) . . ?
C56 Ir4 C48 108.7(5) . . ?
C56 Ir4 C49 116.1(4) . . ?
C56 Ir4 C50 147.6(4) . . ?
C13 P1 Ir1 116.1(4) . . ?
C13 P1 C14 99.6(6) . . ?
C13 P1 C15 101.7(6) . . ?
C14 P1 Ir1 116.7(4) . . ?
C14 P1 C15 103.8(6) . . ?
C15 P1 Ir1 116.4(4) . . ?
C28 P2 Ir2 117.1(4) . . ?
C29 P2 Ir2 116.9(4) . . ?
C29 P2 C28 100.5(5) . . ?
C29 P2 C30 101.9(6) . . ?
C30 P2 Ir2 116.7(4) . . ?
C30 P2 C28 101.0(5) . . ?
C43 P3 Ir3 116.8(4) . . ?
C43 P3 C44 99.9(6) . . ?
C43 P3 C45 99.6(6) . . ?
C44 P3 Ir3 116.0(4) . . ?
C45 P3 Ir3 117.4(4) . . ?
C45 P3 C44 104.4(5) . . ?
C58 P4 Ir4 118.6(4) . . ?
C59 P4 Ir4 116.0(4) . . ?
C59 P4 C58 103.7(6) . . ?
C59 P4 C60 102.0(5) . . ?
C60 P4 Ir4 115.6(4) . . ?
C60 P4 C58 98.1(5) . . ?
C2 C1 Ir1 70.5(5) . . ?
C2 C1 C6 127.4(9) . . ?
C5 C1 Ir1 69.8(5) . . ?
C5 C1 C2 107.4(8) . . ?
C5 C1 C6 124.8(9) . . ?
C6 C1 Ir1 130.4(7) . . ?
C1 C2 Ir1 73.1(5) . . ?
C1 C2 C3 108.1(8) . . ?
C1 C2 C7 127.5(9) . . ?
C3 C2 Ir1 70.0(5) . . ?
C3 C2 C7 124.0(9) . . ?
C7 C2 Ir1 128.3(7) . . ?
C2 C3 Ir1 72.4(5) . . ?
C2 C3 C8 125.4(9) . . ?
C4 C3 Ir1 71.8(5) . . ?
C4 C3 C2 107.8(8) . . ?
C4 C3 C8 126.4(9) . . ?
C8 C3 Ir1 127.2(7) . . ?
C3 C4 Ir1 71.3(6) . . ?
C3 C4 C5 107.5(9) . . ?
C3 C4 C9 127.2(8) . . ?
C5 C4 Ir1 71.6(5) . . ?
C5 C4 C9 124.8(9) . . ?
C9 C4 Ir1 129.2(7) . . ?
C1 C5 Ir1 73.9(5) . . ?
C1 C5 C4 109.2(8) . . ?
C1 C5 C10 124.3(8) . . ?
C4 C5 Ir1 71.1(5) . . ?
C4 C5 C10 126.0(9) . . ?
C10 C5 Ir1 127.7(7) . . ?
F1 C11 Ir1 126.1(7) . . ?
C12 C11 Ir1 134.3(9) . . ?
C12 C11 F1 99.5(9) . . ?
F2 C12 F3 103.8(10) . . ?
F2 C12 C11 116.1(10) . . ?
F3 C12 C11 112.4(10) . . ?
F4 C12 F2 106.4(10) . . ?
F4 C12 F3 105.5(9) . . ?
F4 C12 C11 111.9(10) . . ?
C17 C16 Ir2 70.3(6) . . ?
C17 C16 C20 107.6(9) . . ?
C17 C16 C21 126.6(11) . . ?
C20 C16 Ir2 70.1(5) . . ?
C20 C16 C21 125.1(11) . . ?
C21 C16 Ir2 132.8(8) . . ?
C16 C17 Ir2 73.5(6) . . ?
C16 C17 C22 124.3(12) . . ?
C18 C17 Ir2 70.8(6) . . ?
C18 C17 C16 108.2(9) . . ?
C18 C17 C22 127.3(12) . . ?
C22 C17 Ir2 125.4(8) . . ?
C17 C18 Ir2 72.5(6) . . ?
C17 C18 C23 125.0(13) . . ?
C19 C18 Ir2 71.0(6) . . ?
C19 C18 C17 108.3(9) . . ?
C19 C18 C23 126.3(13) . . ?
C23 C18 Ir2 128.1(8) . . ?
C18 C19 Ir2 72.2(6) . . ?
C18 C19 C20 107.8(9) . . ?
C18 C19 C24 128.2(11) . . ?
C20 C19 Ir2 72.8(5) . . ?
C20 C19 C24 123.2(10) . . ?
C24 C19 Ir2 128.3(7) . . ?
C16 C20 Ir2 73.6(5) . . ?
C16 C20 C19 108.1(8) . . ?
C16 C20 C25 125.1(10) . . ?
C19 C20 Ir2 70.1(5) . . ?
C19 C20 C25 126.3(10) . . ?
C25 C20 Ir2 128.4(7) . . ?
F5 C26 Ir2 126.7(7) . . ?
C27 C26 Ir2 135.7(9) . . ?
C27 C26 F5 97.6(8) . . ?
F6 C27 F7 106.1(9) . . ?
F6 C27 F8 108.4(10) . . ?
F6 C27 C26 110.5(10) . . ?
F7 C27 F8 103.3(9) . . ?
F7 C27 C26 115.2(10) . . ?
F8 C27 C26 112.9(9) . . ?
C32 C31 Ir3 72.6(5) . . ?
C32 C31 C36 126.5(9) . . ?
C35 C31 Ir3 70.9(5) . . ?
C35 C31 C32 106.9(8) . . ?
C35 C31 C36 126.1(9) . . ?
C36 C31 Ir3 128.2(7) . . ?
C31 C32 Ir3 70.6(5) . . ?
C31 C32 C37 125.3(9) . . ?
C33 C32 Ir3 69.1(5) . . ?
C33 C32 C31 108.4(8) . . ?
C33 C32 C37 126.1(9) . . ?
C37 C32 Ir3 129.5(7) . . ?
C32 C33 Ir3 75.3(6) . . ?
C32 C33 C34 109.6(8) . . ?
C32 C33 C38 126.6(10) . . ?
C34 C33 Ir3 71.8(5) . . ?
C34 C33 C38 123.2(10) . . ?
C38 C33 Ir3 126.3(7) . . ?
C33 C34 Ir3 71.0(5) . . ?
C33 C34 C35 106.9(8) . . ?
C33 C34 C39 126.5(9) . . ?
C35 C34 Ir3 72.0(5) . . ?
C35 C34 C39 125.9(9) . . ?
C39 C34 Ir3 129.8(7) . . ?
C31 C35 Ir3 72.5(5) . . ?
C31 C35 C34 108.0(8) . . ?
C31 C35 C40 123.7(9) . . ?
C34 C35 Ir3 70.6(5) . . ?
C34 C35 C40 127.8(9) . . ?
C40 C35 Ir3 128.8(7) . . ?
F9 C41 Ir3 127.5(7) . . ?
F9 C41 C42 100.4(8) . . ?
C42 C41 Ir3 132.0(8) . . ?
F10 C42 F12 104.8(9) . . ?
F10 C42 C41 111.6(9) . . ?
F11 C42 F10 107.4(9) . . ?
F11 C42 F12 105.4(9) . . ?
F11 C42 C41 113.2(9) . . ?
F12 C42 C41 113.9(9) . . ?
C47 C46 Ir4 69.2(5) . . ?
C47 C46 C50 107.2(9) . . ?
C47 C46 C51 126.1(9) . . ?
C50 C46 Ir4 70.8(5) . . ?
C50 C46 C51 126.3(9) . . ?
C51 C46 Ir4 131.2(8) . . ?
C46 C47 Ir4 74.2(6) . . ?
C46 C47 C52 124.3(9) . . ?
C48 C47 Ir4 71.4(6) . . ?
C48 C47 C46 108.8(9) . . ?
C48 C47 C52 126.3(9) . . ?
C52 C47 Ir4 127.7(7) . . ?
C47 C48 Ir4 71.7(6) . . ?
C47 C48 C49 108.6(8) . . ?
C47 C48 C53 123.1(9) . . ?
C49 C48 Ir4 72.6(6) . . ?
C49 C48 C53 127.4(9) . . ?
C53 C48 Ir4 130.0(7) . . ?
C48 C49 Ir4 70.7(6) . . ?
C48 C49 C50 108.5(8) . . ?
C48 C49 C54 126.4(9) . . ?
C50 C49 Ir4 72.6(6) . . ?
C50 C49 C54 124.8(9) . . ?
C54 C49 Ir4 127.0(7) . . ?
C46 C50 Ir4 72.0(5) . . ?
C46 C50 C55 126.5(9) . . ?
C49 C50 Ir4 70.5(6) . . ?
C49 C50 C46 106.8(8) . . ?
C49 C50 C55 126.1(9) . . ?
C55 C50 Ir4 128.9(7) . . ?
F13 C56 Ir4 127.1(8) . . ?
F13 C56 C57 99.4(9) . . ?
C57 C56 Ir4 133.5(10) . . ?
F14 C57 F15 107.2(9) . . ?
F14 C57 F16 107.7(9) . . ?
F14 C57 C56 110.9(10) . . ?
F15 C57 C56 113.2(10) . . ?
F16 C57 F15 103.8(8) . . ?
F16 C57 C56 113.6(10) . . ?

_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_rph342
_database_code_depnum_ccdc_archive 'CCDC 1406694'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;
_audit_creation_date             2015-07-13
_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         'C16 H24 F6 Ir P'
_chemical_formula_sum            'C16 H24 F6 Ir P'
_chemical_formula_weight         553.52
_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'
H H 0.0000 0.0000 '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'
P P 0.1023 0.0942 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.379(5)
_cell_length_b                   13.834(7)
_cell_length_c                   17.073(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.450(8)
_cell_angle_gamma                90
_cell_volume                     1946.2(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9411
_cell_measurement_temperature    218.15
_cell_measurement_theta_max      27.875
_cell_measurement_theta_min      2.426
_shelx_estimated_absorpt_T_max   0.542
_shelx_estimated_absorpt_T_min   0.193
_exptl_absorpt_coefficient_mu    6.992
_exptl_absorpt_correction_T_max  0.6552
_exptl_absorpt_correction_T_min  0.525861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.1324 before and 0.0385 after correction.
The Ratio of minimum to maximum transmission is 0.5259.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.889
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13762
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.134
_diffrn_reflns_theta_min         2.426
_diffrn_ambient_temperature      218.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.908
_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                3812
_reflns_number_total             4323
_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       'SAINT v7.06A (Bruker, 2003)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.06A (Bruker, 2003)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.802
_refine_diff_density_min         -1.561
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4323
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+4.5862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0829
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-F2 = C12-F2A = C12-F3 = C12-F3A
 1.4 with sigma of 0.02
 C13-F4 = C13-F4A = C13-F5 = C13-F5A = C13-F6 = C13-F6A
 1.35 with sigma of 0.02
3. Others
 Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
4.a Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.90462(2) 0.32953(2) 0.86698(2) 0.03825(8) Uani 1 1 d . . . . .
P1 P 0.66645(18) 0.37656(13) 0.79464(10) 0.0601(4) Uani 1 1 d . . . . .
F1 F 0.6063(5) 0.2749(4) 0.9268(3) 0.0903(14) Uani 1 1 d . . . . .
F2 F 0.751(3) 0.2503(10) 1.0641(8) 0.154(7) Uani 0.74(3) 1 d D . P A 1
F3 F 0.9821(11) 0.2118(10) 1.0308(7) 0.088(3) Uani 0.74(3) 1 d D . P A 1
F4 F 0.5933(17) 0.0967(13) 0.9847(15) 0.207(10) Uani 0.74(3) 1 d D . P A 1
F5 F 0.799(2) 0.0659(12) 1.0677(8) 0.101(5) Uani 0.74(3) 1 d D . P A 1
F6 F 0.818(3) 0.0627(6) 0.9461(8) 0.160(8) Uani 0.74(3) 1 d D . P A 1
F2A F 0.793(5) 0.249(2) 1.0735(9) 0.093(11) Uani 0.26(3) 1 d D . P A 2
F3A F 0.971(2) 0.170(3) 1.005(2) 0.082(10) Uani 0.26(3) 1 d D . P A 2
F4A F 0.595(2) 0.128(2) 1.0241(15) 0.097(10) Uani 0.26(3) 1 d D . P A 2
F5A F 0.816(7) 0.053(2) 1.061(2) 0.102(17) Uani 0.26(3) 1 d D . P A 2
F6A F 0.673(6) 0.078(2) 0.9316(13) 0.115(15) Uani 0.26(3) 1 d D . P A 2
C1 C 1.1490(7) 0.2622(4) 0.8689(4) 0.0576(15) Uani 1 1 d . . . . .
C2 C 1.1678(7) 0.3423(5) 0.9226(3) 0.0583(15) Uani 1 1 d . . . . .
C3 C 1.1240(7) 0.4263(4) 0.8756(4) 0.0586(16) Uani 1 1 d . . . . .
C4 C 1.0838(7) 0.3968(5) 0.7958(4) 0.0629(17) Uani 1 1 d . . . . .
C5 C 1.0934(7) 0.2964(5) 0.7925(4) 0.0587(15) Uani 1 1 d . . . . .
C6 C 1.1953(11) 0.1603(5) 0.8906(8) 0.118(4) Uani 1 1 d . . . . .
H6A H 1.3061 0.1490 0.8835 0.176 Uiso 1 1 calc GR . . . .
H6B H 1.1230 0.1167 0.8565 0.176 Uiso 1 1 calc GR . . . .
H6C H 1.1869 0.1489 0.9457 0.176 Uiso 1 1 calc GR . . . .
C7 C 1.2445(10) 0.3412(9) 1.0087(5) 0.123(5) Uani 1 1 d . . . . .
H7A H 1.3577 0.3596 1.0144 0.185 Uiso 1 1 calc GR . . . .
H7B H 1.2370 0.2767 1.0301 0.185 Uiso 1 1 calc GR . . . .
H7C H 1.1886 0.3865 1.0377 0.185 Uiso 1 1 calc GR . . . .
C8 C 1.1441(10) 0.5276(6) 0.9054(8) 0.130(5) Uani 1 1 d . . . . .
H8A H 1.2523 0.5502 0.9023 0.195 Uiso 1 1 calc GR . . . .
H8B H 1.1286 0.5298 0.9603 0.195 Uiso 1 1 calc GR . . . .
H8C H 1.0644 0.5687 0.8730 0.195 Uiso 1 1 calc GR . . . .
C9 C 1.0598(11) 0.4640(9) 0.7249(7) 0.143(5) Uani 1 1 d . . . . .
H9A H 1.1647 0.4836 0.7139 0.215 Uiso 1 1 calc GR . . . .
H9B H 1.0000 0.5207 0.7365 0.215 Uiso 1 1 calc GR . . . .
H9C H 0.9992 0.4309 0.6789 0.215 Uiso 1 1 calc GR . . . .
C10 C 1.0671(11) 0.2360(9) 0.7170(6) 0.119(4) Uani 1 1 d . . . . .
H10A H 1.1712 0.2149 0.7059 0.178 Uiso 1 1 calc GR . . . .
H10B H 1.0116 0.2744 0.6728 0.178 Uiso 1 1 calc GR . . . .
H10C H 1.0017 0.1799 0.7241 0.178 Uiso 1 1 calc GR . . . .
C11 C 0.7808(8) 0.2715(4) 0.9342(4) 0.0587(14) Uani 1 1 d . . . . .
C12 C 0.8187(8) 0.2097(5) 1.0040(4) 0.0673(17) Uani 1 1 d D . . . .
C13 C 0.7448(12) 0.1095(5) 1.0017(4) 0.090(3) Uani 1 1 d D . . . .
C14 C 0.6739(10) 0.4439(9) 0.7034(6) 0.133(5) Uani 1 1 d . . . . .
H14A H 0.5656 0.4484 0.6718 0.199 Uiso 1 1 calc GR . . . .
H14B H 0.7446 0.4108 0.6731 0.199 Uiso 1 1 calc GR . . . .
H14C H 0.7155 0.5084 0.7169 0.199 Uiso 1 1 calc GR . . . .
C15 C 0.5297(10) 0.2799(8) 0.7522(6) 0.103(3) Uani 1 1 d . . . . .
H15A H 0.4273 0.3075 0.7262 0.155 Uiso 1 1 calc GR . . . .
H15B H 0.5109 0.2366 0.7943 0.155 Uiso 1 1 calc GR . . . .
H15C H 0.5782 0.2442 0.7136 0.155 Uiso 1 1 calc GR . . . .
C16 C 0.5355(9) 0.4546(7) 0.8403(6) 0.101(3) Uani 1 1 d . . . . .
H16A H 0.4310 0.4603 0.8053 0.152 Uiso 1 1 calc GR . . . .
H16B H 0.5847 0.5180 0.8492 0.152 Uiso 1 1 calc GR . . . .
H16C H 0.5208 0.4271 0.8907 0.152 Uiso 1 1 calc GR . . . .


_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 P1 2.2443(18) . ?
Ir1 C1 2.244(5) . ?
Ir1 C2 2.244(6) . ?
Ir1 C3 2.257(5) . ?
Ir1 C4 2.294(5) . ?
Ir1 C5 2.250(5) . ?
Ir1 C11 1.863(6) . ?
P1 C14 1.826(8) . ?
P1 C15 1.823(8) . ?
P1 C16 1.813(8) . ?
F1 C11 1.445(7) . ?
F2 C12 1.380(11) . ?
F3 C12 1.363(10) . ?
F4 C13 1.262(13) . ?
F5 C13 1.287(11) . ?
F6 C13 1.382(12) . ?
F2A C12 1.359(17) . ?
F3A C12 1.391(17) . ?
F4A C13 1.397(17) . ?
F5A C13 1.322(19) . ?
F6A C13 1.312(17) . ?
C1 C2 1.429(9) . ?
C1 C5 1.387(9) . ?
C1 C6 1.491(8) . ?
C2 C3 1.422(9) . ?
C2 C7 1.494(10) . ?
C3 C4 1.403(10) . ?
C3 C8 1.491(9) . ?
C4 C5 1.393(10) . ?
C4 C9 1.509(10) . ?
C5 C10 1.518(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 C12 1.455(9) . ?
C12 C13 1.517(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?

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
P1 Ir1 C1 147.79(19) . . ?
P1 Ir1 C3 119.75(18) . . ?
P1 Ir1 C4 101.11(16) . . ?
P1 Ir1 C5 113.21(19) . . ?
C1 Ir1 C3 61.0(2) . . ?
C1 Ir1 C4 59.5(2) . . ?
C1 Ir1 C5 35.9(2) . . ?
C2 Ir1 P1 156.56(18) . . ?
C2 Ir1 C1 37.1(2) . . ?
C2 Ir1 C3 36.8(2) . . ?
C2 Ir1 C4 60.3(2) . . ?
C2 Ir1 C5 61.2(2) . . ?
C3 Ir1 C4 35.9(2) . . ?
C5 Ir1 C3 60.6(2) . . ?
C5 Ir1 C4 35.7(2) . . ?
C11 Ir1 P1 85.7(2) . . ?
C11 Ir1 C1 114.9(3) . . ?
C11 Ir1 C2 112.8(3) . . ?
C11 Ir1 C3 138.9(3) . . ?
C11 Ir1 C4 173.1(3) . . ?
C11 Ir1 C5 142.0(3) . . ?
C14 P1 Ir1 116.9(3) . . ?
C15 P1 Ir1 116.0(3) . . ?
C15 P1 C14 98.7(5) . . ?
C16 P1 Ir1 118.9(3) . . ?
C16 P1 C14 100.4(5) . . ?
C16 P1 C15 102.8(4) . . ?
C2 C1 Ir1 71.4(3) . . ?
C2 C1 C6 125.5(8) . . ?
C5 C1 Ir1 72.2(3) . . ?
C5 C1 C2 108.6(5) . . ?
C5 C1 C6 125.7(8) . . ?
C6 C1 Ir1 126.3(5) . . ?
C1 C2 Ir1 71.4(3) . . ?
C1 C2 C7 127.0(8) . . ?
C3 C2 Ir1 72.1(3) . . ?
C3 C2 C1 106.5(5) . . ?
C3 C2 C7 125.8(7) . . ?
C7 C2 Ir1 129.0(5) . . ?
C2 C3 Ir1 71.1(3) . . ?
C2 C3 C8 125.0(8) . . ?
C4 C3 Ir1 73.5(3) . . ?
C4 C3 C2 107.6(5) . . ?
C4 C3 C8 126.7(8) . . ?
C8 C3 Ir1 128.3(4) . . ?
C3 C4 Ir1 70.6(3) . . ?
C3 C4 C9 124.9(8) . . ?
C5 C4 Ir1 70.4(3) . . ?
C5 C4 C3 108.9(5) . . ?
C5 C4 C9 125.6(8) . . ?
C9 C4 Ir1 132.0(5) . . ?
C1 C5 Ir1 71.8(3) . . ?
C1 C5 C4 108.3(5) . . ?
C1 C5 C10 125.6(8) . . ?
C4 C5 Ir1 73.9(3) . . ?
C4 C5 C10 125.7(8) . . ?
C10 C5 Ir1 125.7(5) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F1 C11 Ir1 126.9(4) . . ?
F1 C11 C12 99.0(5) . . ?
C12 C11 Ir1 134.0(5) . . ?
F2 C12 C11 108.1(8) . . ?
F2 C12 C13 99.8(8) . . ?
F3 C12 F2 105.5(10) . . ?
F3 C12 C11 108.6(7) . . ?
F3 C12 C13 114.1(8) . . ?
F2A C12 F3A 116(2) . . ?
F2A C12 C11 115.7(12) . . ?
F2A C12 C13 105.2(16) . . ?
F3A C12 C11 107.7(12) . . ?
F3A C12 C13 90.4(16) . . ?
C11 C12 C13 119.3(6) . . ?
F4 C13 F5 108.5(13) . . ?
F4 C13 F6 109.4(12) . . ?
F4 C13 C12 121.5(11) . . ?
F5 C13 F6 104.5(12) . . ?
F5 C13 C12 109.1(10) . . ?
F6 C13 C12 102.5(8) . . ?
F4A C13 C12 102.1(13) . . ?
F5A C13 F4A 101(3) . . ?
F5A C13 C12 113(2) . . ?
F6A C13 F4A 91(2) . . ?
F6A C13 F5A 125(2) . . ?
F6A C13 C12 116.2(12) . . ?
P1 C14 H14A 109.5 . . ?
P1 C14 H14B 109.5 . . ?
P1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
P1 C15 H15A 109.5 . . ?
P1 C15 H15B 109.5 . . ?
P1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
P1 C16 H16A 109.5 . . ?
P1 C16 H16B 109.5 . . ?
P1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_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_rph377
_database_code_depnum_ccdc_archive 'CCDC 1406695'
_audit_update_record             
;
2015-06-13 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Cl F6 Ir O'
_chemical_formula_weight         541.92

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   9.3707(9)
_cell_length_b                   8.5612(8)
_cell_length_c                   20.956(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.0900(10)
_cell_angle_gamma                90.00
_cell_volume                     1664.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9398
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      28.01

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.163
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    8.241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1606
_exptl_absorpt_correction_T_max  0.6834
_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_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12291
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3274
_reflns_number_gt                3011
_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+4.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3274
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.012
_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 0.28687(2) 0.40577(2) 0.344457(9) 0.01942(10) Uani 1 1 d . . .
Cl1 Cl 0.30573(15) 0.18615(15) 0.27535(7) 0.0276(3) Uani 1 1 d . . .
F1 F 0.1078(4) 0.1711(4) 0.39522(17) 0.0401(9) Uani 1 1 d . . .
F2 F 0.1667(5) 0.3866(5) 0.4910(2) 0.0500(11) Uani 1 1 d . . .
F3 F 0.3964(4) 0.3352(5) 0.49895(18) 0.0463(10) Uani 1 1 d . . .
O1 O 0.6017(5) 0.4027(5) 0.3964(3) 0.0421(12) Uani 1 1 d . . .
C11 C 0.2486(6) 0.2322(7) 0.4104(3) 0.0298(13) Uani 1 1 d . . .
H11A H 0.3177 0.1450 0.4062 0.036 Uiso 1 1 calc R . .
F4 F 0.3469(6) 0.0354(5) 0.5254(2) 0.0638(13) Uani 1 1 d . . .
F5 F 0.1215(6) 0.0755(6) 0.5180(2) 0.0727(16) Uani 1 1 d . . .
C5 C 0.1002(6) 0.4990(6) 0.2760(3) 0.0226(11) Uani 1 1 d . . .
C10 C 0.0071(7) 0.4055(6) 0.2260(3) 0.0313(14) Uani 1 1 d . . .
H10A H -0.0687 0.4726 0.2036 0.047 Uiso 1 1 calc R . .
H10B H -0.0370 0.3190 0.2468 0.047 Uiso 1 1 calc R . .
H10C H 0.0660 0.3638 0.1948 0.047 Uiso 1 1 calc R . .
C4 C 0.2319(6) 0.5771(6) 0.2650(3) 0.0230(11) Uani 1 1 d . . .
C3 C 0.2841(5) 0.6600(7) 0.3226(3) 0.0245(11) Uani 1 1 d . . .
C14 C 0.4842(7) 0.4001(6) 0.3780(3) 0.0321(14) Uani 1 1 d . . .
C2 C 0.1893(6) 0.6271(6) 0.3696(3) 0.0243(11) Uani 1 1 d . . .
C1 C 0.0732(6) 0.5310(7) 0.3386(3) 0.0262(12) Uani 1 1 d . . .
C9 C 0.2920(7) 0.5766(7) 0.2024(3) 0.0334(14) Uani 1 1 d . . .
H9A H 0.2524 0.6652 0.1760 0.050 Uiso 1 1 calc R . .
H9B H 0.2656 0.4789 0.1794 0.050 Uiso 1 1 calc R . .
H9C H 0.3972 0.5855 0.2109 0.050 Uiso 1 1 calc R . .
C12 C 0.2629(7) 0.2754(8) 0.4797(3) 0.0362(14) Uani 1 1 d . . .
C13 C 0.2483(7) 0.1436(9) 0.5283(3) 0.0380(15) Uani 1 1 d . . .
C8 C 0.4082(6) 0.7682(7) 0.3320(3) 0.0368(15) Uani 1 1 d . . .
H8A H 0.3756 0.8740 0.3195 0.055 Uiso 1 1 calc R . .
H8B H 0.4804 0.7345 0.3054 0.055 Uiso 1 1 calc R . .
H8C H 0.4509 0.7678 0.3775 0.055 Uiso 1 1 calc R . .
C7 C 0.1942(8) 0.7107(8) 0.4328(3) 0.0396(15) Uani 1 1 d . . .
H7A H 0.1380 0.8074 0.4264 0.059 Uiso 1 1 calc R . .
H7B H 0.2944 0.7359 0.4497 0.059 Uiso 1 1 calc R . .
H7C H 0.1534 0.6436 0.4635 0.059 Uiso 1 1 calc R . .
C6 C -0.0597(6) 0.4857(8) 0.3663(3) 0.0375(15) Uani 1 1 d . . .
H6A H -0.1340 0.5658 0.3556 0.056 Uiso 1 1 calc R . .
H6B H -0.0368 0.4766 0.4132 0.056 Uiso 1 1 calc R . .
H6C H -0.0952 0.3852 0.3481 0.056 Uiso 1 1 calc R . .
F6 F 0.2648(4) 0.1996(5) 0.58787(17) 0.0452(9) 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 C14 1.884(7) . ?
Ir1 C11 2.093(6) . ?
Ir1 C2 2.199(5) . ?
Ir1 C3 2.224(6) . ?
Ir1 C4 2.224(5) . ?
Ir1 C5 2.247(5) . ?
Ir1 C1 2.259(5) . ?
Ir1 Cl1 2.3949(13) . ?
F1 C11 1.413(6) . ?
F2 C12 1.355(7) . ?
F3 C12 1.359(7) . ?
O1 C14 1.115(8) . ?
C11 C12 1.486(8) . ?
F4 C13 1.316(9) . ?
F5 C13 1.314(8) . ?
C5 C1 1.398(8) . ?
C5 C4 1.450(8) . ?
C5 C10 1.497(8) . ?
C4 C3 1.426(8) . ?
C4 C9 1.498(8) . ?
C3 C2 1.444(8) . ?
C3 C8 1.478(8) . ?
C2 C1 1.443(8) . ?
C2 C7 1.500(8) . ?
C1 C6 1.497(8) . ?
C12 C13 1.540(9) . ?
C13 F6 1.325(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
C14 Ir1 C11 89.2(3) . . ?
C14 Ir1 C2 110.6(2) . . ?
C11 Ir1 C2 109.7(2) . . ?
C14 Ir1 C3 94.8(2) . . ?
C11 Ir1 C3 146.3(2) . . ?
C2 Ir1 C3 38.1(2) . . ?
C14 Ir1 C4 114.1(2) . . ?
C11 Ir1 C4 156.7(2) . . ?
C2 Ir1 C4 63.3(2) . . ?
C3 Ir1 C4 37.4(2) . . ?
C14 Ir1 C5 151.9(2) . . ?
C11 Ir1 C5 118.9(2) . . ?
C2 Ir1 C5 62.3(2) . . ?
C3 Ir1 C5 62.32(19) . . ?
C4 Ir1 C5 37.8(2) . . ?
C14 Ir1 C1 148.0(2) . . ?
C11 Ir1 C1 98.1(2) . . ?
C2 Ir1 C1 37.7(2) . . ?
C3 Ir1 C1 62.6(2) . . ?
C4 Ir1 C1 62.4(2) . . ?
C5 Ir1 C1 36.2(2) . . ?
C14 Ir1 Cl1 93.07(18) . . ?
C11 Ir1 Cl1 82.87(17) . . ?
C2 Ir1 Cl1 152.82(15) . . ?
C3 Ir1 Cl1 130.07(16) . . ?
C4 Ir1 Cl1 95.40(15) . . ?
C5 Ir1 Cl1 90.55(14) . . ?
C1 Ir1 Cl1 118.68(15) . . ?
F1 C11 C12 105.3(5) . . ?
F1 C11 Ir1 110.8(4) . . ?
C12 C11 Ir1 117.9(4) . . ?
C1 C5 C4 109.2(5) . . ?
C1 C5 C10 126.6(5) . . ?
C4 C5 C10 124.2(5) . . ?
C1 C5 Ir1 72.4(3) . . ?
C4 C5 Ir1 70.2(3) . . ?
C10 C5 Ir1 125.6(4) . . ?
C3 C4 C5 107.1(5) . . ?
C3 C4 C9 128.0(5) . . ?
C5 C4 C9 124.7(5) . . ?
C3 C4 Ir1 71.3(3) . . ?
C5 C4 Ir1 72.0(3) . . ?
C9 C4 Ir1 125.3(4) . . ?
C4 C3 C2 108.0(5) . . ?
C4 C3 C8 126.5(6) . . ?
C2 C3 C8 125.4(6) . . ?
C4 C3 Ir1 71.3(3) . . ?
C2 C3 Ir1 70.0(3) . . ?
C8 C3 Ir1 126.9(4) . . ?
O1 C14 Ir1 176.9(6) . . ?
C1 C2 C3 107.6(5) . . ?
C1 C2 C7 126.6(5) . . ?
C3 C2 C7 124.3(5) . . ?
C1 C2 Ir1 73.4(3) . . ?
C3 C2 Ir1 71.9(3) . . ?
C7 C2 Ir1 131.3(4) . . ?
C5 C1 C2 108.0(5) . . ?
C5 C1 C6 125.7(5) . . ?
C2 C1 C6 126.1(5) . . ?
C5 C1 Ir1 71.4(3) . . ?
C2 C1 Ir1 68.9(3) . . ?
C6 C1 Ir1 129.4(4) . . ?
F2 C12 F3 106.9(5) . . ?
F2 C12 C11 112.0(5) . . ?
F3 C12 C11 109.7(5) . . ?
F2 C12 C13 105.9(5) . . ?
F3 C12 C13 104.1(5) . . ?
C11 C12 C13 117.5(6) . . ?
F5 C13 F4 107.7(7) . . ?
F5 C13 F6 107.4(6) . . ?
F4 C13 F6 108.0(5) . . ?
F5 C13 C12 112.3(6) . . ?
F4 C13 C12 110.8(5) . . ?
F6 C13 C12 110.5(6) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         2.295
_refine_diff_density_min         -1.080
_refine_diff_density_rms         0.166
####################################################################### 
# 
# 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_rph383
_database_code_depnum_ccdc_archive 'CCDC 1406696'
_audit_update_record             
;
2015-06-13 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 Cl F4 Ir O'
_chemical_formula_sum            'C13 H16 Cl F4 Ir O'
_chemical_formula_weight         491.91

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   I2/a
_symmetry_space_group_name_Hall  '-I 2ya'

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

_cell_length_a                   14.360(5)
_cell_length_b                   7.631(3)
_cell_length_c                   27.696(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.863(6)
_cell_angle_gamma                90.00
_cell_volume                     3013.4(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    208(2)
_cell_measurement_reflns_used    6165
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      28.22

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1856
_exptl_absorpt_coefficient_mu    9.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.422
_exptl_absorpt_correction_T_max  0.483
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      208(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_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10240
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         28.24
_reflns_number_total             3522
_reflns_number_gt                3175
_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)+(0.0362P)²+10.7034P] 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         3522
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0769
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.930719(11) -0.00730(2) 0.392833(6) 0.02712(8) Uani 1 1 d . . .
Cl1 Cl 1.07047(8) 0.09822(18) 0.43990(5) 0.0433(3) Uani 1 1 d . . .
O1 O 0.8024(3) 0.1870(6) 0.45205(14) 0.0558(10) Uani 1 1 d . . .
F1 F 1.0064(2) 0.1734(5) 0.31465(12) 0.0604(9) Uani 1 1 d . . .
F2 F 0.8100(2) 0.3736(4) 0.35387(13) 0.0583(9) Uani 1 1 d . . .
F3 F 0.8046(2) 0.1835(4) 0.29677(12) 0.0601(9) Uani 1 1 d . . .
F4 F 0.8834(3) 0.4196(5) 0.29138(13) 0.0667(10) Uani 1 1 d . . .
C1 C 0.9120(3) -0.1990(6) 0.33055(16) 0.0324(10) Uani 1 1 d . . .
C2 C 0.8359(3) -0.2111(6) 0.36027(15) 0.0274(9) Uani 1 1 d . . .
C3 C 0.8734(3) -0.2738(6) 0.40791(15) 0.0291(9) Uani 1 1 d . . .
C4 C 0.9713(3) -0.2872(6) 0.40867(17) 0.0318(9) Uani 1 1 d . . .
C5 C 0.9961(3) -0.2370(6) 0.36138(17) 0.0338(10) Uani 1 1 d . . .
C6 C 0.9034(4) -0.1649(7) 0.27740(16) 0.0445(12) Uani 1 1 d . . .
H6A H 0.9031 -0.2754 0.2601 0.067 Uiso 1 1 calc R . .
H6B H 0.9562 -0.0947 0.2700 0.067 Uiso 1 1 calc R . .
H6C H 0.8455 -0.1024 0.2675 0.067 Uiso 1 1 calc R . .
C7 C 0.7335(3) -0.1971(7) 0.34177(18) 0.0379(11) Uani 1 1 d . . .
H7A H 0.7105 -0.3103 0.3297 0.057 Uiso 1 1 calc R . .
H7B H 0.7250 -0.1118 0.3157 0.057 Uiso 1 1 calc R . .
H7C H 0.6989 -0.1601 0.3680 0.057 Uiso 1 1 calc R . .
C8 C 0.8161(4) -0.3209(7) 0.44770(17) 0.0399(11) Uani 1 1 d . . .
H8A H 0.7969 -0.4425 0.4443 0.060 Uiso 1 1 calc R . .
H8B H 0.7610 -0.2465 0.4456 0.060 Uiso 1 1 calc R . .
H8C H 0.8533 -0.3040 0.4790 0.060 Uiso 1 1 calc R . .
C9 C 1.0403(4) -0.3480(7) 0.45053(19) 0.0440(12) Uani 1 1 d . . .
H9A H 1.0508 -0.4729 0.4476 0.066 Uiso 1 1 calc R . .
H9B H 1.0155 -0.3241 0.4809 0.066 Uiso 1 1 calc R . .
H9C H 1.0992 -0.2860 0.4500 0.066 Uiso 1 1 calc R . .
C10 C 1.0925(4) -0.2488(8) 0.3459(2) 0.0495(14) Uani 1 1 d . . .
H10A H 1.1051 -0.3689 0.3372 0.074 Uiso 1 1 calc R . .
H10B H 1.1384 -0.2116 0.3724 0.074 Uiso 1 1 calc R . .
H10C H 1.0962 -0.1734 0.3180 0.074 Uiso 1 1 calc R . .
C11 C 0.9475(3) 0.2131(7) 0.34983(19) 0.0392(11) Uani 1 1 d . . .
H11A H 0.9791 0.3043 0.3713 0.047 Uiso 1 1 calc R . .
C12 C 0.8621(4) 0.2947(7) 0.32255(19) 0.0466(13) Uani 1 1 d . . .
C13 C 0.8524(3) 0.1206(6) 0.42980(16) 0.0336(10) 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 C13 1.882(5) . ?
Ir1 C11 2.091(5) . ?
Ir1 C2 2.189(4) . ?
Ir1 C5 2.216(5) . ?
Ir1 C4 2.243(5) . ?
Ir1 C3 2.252(4) . ?
Ir1 C1 2.253(4) . ?
Ir1 Cl1 2.3979(13) . ?
O1 C13 1.121(6) . ?
F1 C11 1.397(6) . ?
F2 C12 1.353(6) . ?
F3 C12 1.331(6) . ?
F4 C12 1.346(6) . ?
C1 C5 1.424(6) . ?
C1 C2 1.447(6) . ?
C1 C6 1.485(6) . ?
C2 C3 1.446(6) . ?
C2 C7 1.502(6) . ?
C3 C4 1.406(6) . ?
C3 C8 1.496(6) . ?
C4 C5 1.450(6) . ?
C4 C9 1.506(6) . ?
C5 C10 1.499(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 C12 1.497(7) . ?
C11 H11A 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 Ir1 C11 90.6(2) . . ?
C13 Ir1 C2 102.10(18) . . ?
C11 Ir1 C2 116.43(18) . . ?
C13 Ir1 C5 158.94(19) . . ?
C11 Ir1 C5 109.2(2) . . ?
C2 Ir1 C5 63.14(16) . . ?
C13 Ir1 C4 123.05(19) . . ?
C11 Ir1 C4 146.31(18) . . ?
C2 Ir1 C4 62.50(15) . . ?
C5 Ir1 C4 37.94(17) . . ?
C13 Ir1 C3 96.44(18) . . ?
C11 Ir1 C3 154.37(18) . . ?
C2 Ir1 C3 37.97(15) . . ?
C5 Ir1 C3 62.60(17) . . ?
C4 Ir1 C3 36.45(16) . . ?
C13 Ir1 C1 136.77(18) . . ?
C11 Ir1 C1 95.60(19) . . ?
C2 Ir1 C1 37.99(16) . . ?
C5 Ir1 C1 37.15(17) . . ?
C4 Ir1 C1 62.35(17) . . ?
C3 Ir1 C1 62.78(16) . . ?
C13 Ir1 Cl1 92.64(15) . . ?
C11 Ir1 Cl1 83.89(14) . . ?
C2 Ir1 Cl1 154.35(12) . . ?
C5 Ir1 Cl1 96.47(13) . . ?
C4 Ir1 Cl1 91.87(12) . . ?
C3 Ir1 Cl1 120.20(11) . . ?
C1 Ir1 Cl1 130.54(12) . . ?
C5 C1 C2 106.9(4) . . ?
C5 C1 C6 126.4(4) . . ?
C2 C1 C6 126.6(4) . . ?
C5 C1 Ir1 70.0(3) . . ?
C2 C1 Ir1 68.6(2) . . ?
C6 C1 Ir1 129.3(4) . . ?
C3 C2 C1 108.4(4) . . ?
C3 C2 C7 125.3(4) . . ?
C1 C2 C7 125.2(4) . . ?
C3 C2 Ir1 73.4(2) . . ?
C1 C2 Ir1 73.4(3) . . ?
C7 C2 Ir1 128.7(3) . . ?
C4 C3 C2 107.5(4) . . ?
C4 C3 C8 127.5(4) . . ?
C2 C3 C8 125.0(4) . . ?
C4 C3 Ir1 71.4(3) . . ?
C2 C3 Ir1 68.7(2) . . ?
C8 C3 Ir1 126.8(3) . . ?
C3 C4 C5 108.7(4) . . ?
C3 C4 C9 126.8(4) . . ?
C5 C4 C9 124.5(4) . . ?
C3 C4 Ir1 72.1(3) . . ?
C5 C4 Ir1 70.0(3) . . ?
C9 C4 Ir1 125.1(3) . . ?
C1 C5 C4 108.2(4) . . ?
C1 C5 C10 125.9(4) . . ?
C4 C5 C10 125.3(4) . . ?
C1 C5 Ir1 72.9(3) . . ?
C4 C5 Ir1 72.1(3) . . ?
C10 C5 Ir1 127.5(4) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F1 C11 C12 105.4(4) . . ?
F1 C11 Ir1 110.1(3) . . ?
C12 C11 Ir1 118.6(3) . . ?
F1 C11 H11A 107.4 . . ?
C12 C11 H11A 107.4 . . ?
Ir1 C11 H11A 107.4 . . ?
F3 C12 F4 106.3(4) . . ?
F3 C12 F2 105.8(5) . . ?
F4 C12 F2 106.3(5) . . ?
F3 C12 C11 115.1(5) . . ?
F4 C12 C11 112.6(5) . . ?
F2 C12 C11 110.1(4) . . ?
O1 C13 Ir1 175.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.944
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.613
_refine_diff_density_min         -0.931
_refine_diff_density_rms         0.129
####################################################################### 
# 
# 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_rph396
_database_code_depnum_ccdc_archive 'CCDC 1406697'
_audit_update_record             
;
2015-06-13 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 F4 Ir O'
_chemical_formula_weight         455.45

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                   8.418(2)
_cell_length_b                   12.121(3)
_cell_length_c                   14.427(4)
_cell_angle_alpha                103.242(3)
_cell_angle_beta                 97.509(3)
_cell_angle_gamma                95.759(3)
_cell_volume                     1407.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4630
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.15

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    9.519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1624
_exptl_absorpt_correction_T_max  0.5555
_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            10817
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5418
_reflns_number_gt                3814
_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)+(0.0600P)²+0.7000P] 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         5418
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1150
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.033
_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 1.17939(4) 0.18494(3) 0.23180(3) 0.02504(13) Uani 1 1 d . . .
Ir1' Ir -0.82501(4) 0.68613(3) 0.22171(3) 0.02301(13) Uani 1 1 d . . .
F1' F -0.9285(7) 0.7354(5) 0.4054(4) 0.0404(15) Uani 1 1 d . . .
F1 F 1.3776(7) 0.2308(5) 0.4156(4) 0.0435(16) Uani 1 1 d . . .
F2' F -1.2279(6) 0.6637(5) 0.2037(4) 0.0414(15) Uani 1 1 d . . .
F2 F 1.6333(7) 0.1583(6) 0.3522(5) 0.0516(17) Uani 1 1 d . . .
F3 F 1.5731(7) 0.2028(5) 0.2153(4) 0.0459(16) Uani 1 1 d . . .
F3' F -1.2143(7) 0.6092(5) 0.3374(5) 0.0466(16) Uani 1 1 d . . .
F4 F 1.6224(7) 0.3340(5) 0.3495(5) 0.0496(17) Uani 1 1 d . . .
F4' F -1.2097(7) 0.7869(5) 0.3411(5) 0.0490(17) Uani 1 1 d . . .
O1 O 1.3235(9) 0.1667(7) 0.0503(5) 0.047(2) Uani 1 1 d . . .
O1' O -1.0616(9) 0.6239(7) 0.0376(5) 0.046(2) Uani 1 1 d . . .
C1 C 0.9961(11) 0.2547(9) 0.3213(7) 0.029(2) Uani 1 1 d . . .
C1' C -0.6000(10) 0.6538(8) 0.3071(7) 0.026(2) Uani 1 1 d . . .
C2' C -0.5904(11) 0.7750(8) 0.3112(7) 0.028(2) Uani 1 1 d . . .
C2 C 0.9954(11) 0.1335(9) 0.3178(7) 0.030(2) Uani 1 1 d . . .
C3 C 0.9459(11) 0.0706(8) 0.2177(7) 0.027(2) Uani 1 1 d . . .
C3' C -0.5906(10) 0.7894(8) 0.2154(7) 0.027(2) Uani 1 1 d . . .
C4 C 0.9163(11) 0.1528(8) 0.1601(7) 0.028(2) Uani 1 1 d . . .
C4' C -0.5990(11) 0.6777(8) 0.1521(7) 0.026(2) Uani 1 1 d . . .
C5 C 0.9510(10) 0.2649(7) 0.2242(7) 0.024(2) Uani 1 1 d . . .
C5' C -0.6067(10) 0.5957(7) 0.2092(6) 0.022(2) Uani 1 1 d . . .
C6' C -0.5964(12) 0.6025(9) 0.3908(7) 0.033(2) Uani 1 1 d . . .
H6'A H -0.4839 0.6034 0.4193 0.049 Uiso 1 1 calc R . .
H6'B H -0.6502 0.5234 0.3697 0.049 Uiso 1 1 calc R . .
H6'C H -0.6527 0.6468 0.4390 0.049 Uiso 1 1 calc R . .
C6 C 1.0318(12) 0.3505(9) 0.4096(7) 0.038(3) Uani 1 1 d . . .
H6A H 0.9338 0.3592 0.4391 0.058 Uiso 1 1 calc R . .
H6B H 1.0680 0.4215 0.3924 0.058 Uiso 1 1 calc R . .
H6C H 1.1170 0.3339 0.4556 0.058 Uiso 1 1 calc R . .
C7' C -0.5727(12) 0.8700(9) 0.4008(7) 0.038(3) Uani 1 1 d . . .
H7'A H -0.4576 0.8962 0.4251 0.057 Uiso 1 1 calc R . .
H7'B H -0.6233 0.8421 0.4500 0.057 Uiso 1 1 calc R . .
H7'C H -0.6254 0.9337 0.3858 0.057 Uiso 1 1 calc R . .
C7 C 1.0236(12) 0.0815(9) 0.4008(7) 0.037(3) Uani 1 1 d . . .
H7A H 0.9217 0.0682 0.4250 0.056 Uiso 1 1 calc R . .
H7B H 1.1028 0.1332 0.4521 0.056 Uiso 1 1 calc R . .
H7C H 1.0650 0.0085 0.3803 0.056 Uiso 1 1 calc R . .
C8 C 0.9149(11) -0.0565(7) 0.1812(8) 0.031(2) Uani 1 1 d . . .
H8A H 0.8172 -0.0862 0.2027 0.047 Uiso 1 1 calc R . .
H8B H 1.0074 -0.0901 0.2064 0.047 Uiso 1 1 calc R . .
H8C H 0.9000 -0.0767 0.1106 0.047 Uiso 1 1 calc R . .
C8' C -0.5700(12) 0.9018(8) 0.1862(8) 0.039(3) Uani 1 1 d . . .
H8'A H -0.4590 0.9398 0.2096 0.059 Uiso 1 1 calc R . .
H8'B H -0.6457 0.9511 0.2144 0.059 Uiso 1 1 calc R . .
H8'C H -0.5922 0.8872 0.1158 0.059 Uiso 1 1 calc R . .
C9' C -0.5897(11) 0.6520(8) 0.0464(6) 0.029(2) Uani 1 1 d . . .
H9'A H -0.4765 0.6510 0.0371 0.043 Uiso 1 1 calc R . .
H9'B H -0.6345 0.7110 0.0187 0.043 Uiso 1 1 calc R . .
H9'C H -0.6519 0.5772 0.0142 0.043 Uiso 1 1 calc R . .
C9 C 0.8528(12) 0.1241(8) 0.0558(7) 0.033(2) Uani 1 1 d . . .
H9A H 0.7344 0.1124 0.0462 0.049 Uiso 1 1 calc R . .
H9B H 0.8919 0.0540 0.0238 0.049 Uiso 1 1 calc R . .
H9C H 0.8901 0.1870 0.0282 0.049 Uiso 1 1 calc R . .
C10' C -0.6041(11) 0.4693(7) 0.1728(7) 0.027(2) Uani 1 1 d . . .
H10A H -0.4919 0.4540 0.1729 0.040 Uiso 1 1 calc R . .
H10B H -0.6639 0.4432 0.1070 0.040 Uiso 1 1 calc R . .
H10C H -0.6547 0.4283 0.2149 0.040 Uiso 1 1 calc R . .
C10 C 0.9240(12) 0.3751(8) 0.1973(7) 0.034(2) Uani 1 1 d . . .
H10D H 0.8174 0.3943 0.2101 0.051 Uiso 1 1 calc R . .
H10E H 0.9295 0.3664 0.1286 0.051 Uiso 1 1 calc R . .
H10F H 1.0078 0.4365 0.2356 0.051 Uiso 1 1 calc R . .
C11 C 1.2746(11) 0.1757(8) 0.1228(8) 0.032(2) Uani 1 1 d . . .
C11' C -0.9783(11) 0.6462(8) 0.1103(7) 0.028(2) Uani 1 1 d . . .
C12' C -0.9736(12) 0.7050(8) 0.3061(7) 0.031(2) Uani 1 1 d . . .
C12 C 1.3752(12) 0.2123(9) 0.3172(8) 0.033(2) Uani 1 1 d . . .
C13' C -1.1582(12) 0.6913(9) 0.2954(8) 0.036(3) Uani 1 1 d . . .
C13 C 1.5506(13) 0.2253(10) 0.3081(8) 0.040(3) 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 1.843(11) . ?
Ir1 C12 1.875(10) . ?
Ir1 C2 2.233(9) . ?
Ir1 C5 2.240(9) . ?
Ir1 C3 2.246(9) . ?
Ir1 C1 2.246(9) . ?
Ir1 C4 2.273(9) . ?
Ir1' C12' 1.852(10) . ?
Ir1' C11' 1.860(10) . ?
Ir1' C2' 2.235(10) . ?
Ir1' C5' 2.239(8) . ?
Ir1' C1' 2.240(8) . ?
Ir1' C3' 2.252(9) . ?
Ir1' C4' 2.265(9) . ?
F1' C12' 1.385(11) . ?
F1 C12 1.383(12) . ?
F2' C13' 1.328(12) . ?
F2 C13 1.335(11) . ?
F3 C13 1.347(12) . ?
F3' C13' 1.355(11) . ?
F4 C13 1.358(12) . ?
F4' C13' 1.338(11) . ?
O1 C11 1.159(12) . ?
O1' C11' 1.142(11) . ?
C1 C5 1.439(13) . ?
C1 C2 1.458(13) . ?
C1 C6 1.488(13) . ?
C1' C5' 1.417(13) . ?
C1' C2' 1.450(13) . ?
C1' C6' 1.478(12) . ?
C2' C3' 1.433(13) . ?
C2' C7' 1.501(12) . ?
C2 C3 1.453(13) . ?
C2 C7 1.481(12) . ?
C3 C4 1.456(12) . ?
C3 C8 1.494(12) . ?
C3' C4' 1.439(13) . ?
C3' C8' 1.515(13) . ?
C4 C5 1.435(12) . ?
C4 C9 1.479(13) . ?
C4' C5' 1.430(12) . ?
C4' C9' 1.500(12) . ?
C5 C10 1.505(12) . ?
C5' C10' 1.506(12) . ?
C12' C13' 1.529(14) . ?
C12 C13 1.495(14) . ?

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 C12 95.0(4) . . ?
C11 Ir1 C2 155.0(4) . . ?
C12 Ir1 C2 104.0(4) . . ?
C11 Ir1 C5 113.0(4) . . ?
C12 Ir1 C5 135.8(4) . . ?
C2 Ir1 C5 63.0(3) . . ?
C11 Ir1 C3 117.3(4) . . ?
C12 Ir1 C3 133.3(4) . . ?
C2 Ir1 C3 37.9(3) . . ?
C5 Ir1 C3 62.6(3) . . ?
C11 Ir1 C1 149.4(4) . . ?
C12 Ir1 C1 105.5(4) . . ?
C2 Ir1 C1 38.0(3) . . ?
C5 Ir1 C1 37.4(3) . . ?
C3 Ir1 C1 63.0(4) . . ?
C11 Ir1 C4 98.4(4) . . ?
C12 Ir1 C4 166.6(4) . . ?
C2 Ir1 C4 63.0(3) . . ?
C5 Ir1 C4 37.1(3) . . ?
C3 Ir1 C4 37.6(3) . . ?
C1 Ir1 C4 62.5(3) . . ?
C12' Ir1' C11' 95.4(4) . . ?
C12' Ir1' C2' 104.5(4) . . ?
C11' Ir1' C2' 154.0(4) . . ?
C12' Ir1' C5' 135.5(4) . . ?
C11' Ir1' C5' 113.7(4) . . ?
C2' Ir1' C5' 62.1(3) . . ?
C12' Ir1' C1' 105.5(4) . . ?
C11' Ir1' C1' 149.6(4) . . ?
C2' Ir1' C1' 37.8(3) . . ?
C5' Ir1' C1' 36.9(3) . . ?
C12' Ir1' C3' 133.2(4) . . ?
C11' Ir1' C3' 116.9(4) . . ?
C2' Ir1' C3' 37.2(3) . . ?
C5' Ir1' C3' 62.2(3) . . ?
C1' Ir1' C3' 62.7(3) . . ?
C12' Ir1' C4' 166.0(4) . . ?
C11' Ir1' C4' 98.6(4) . . ?
C2' Ir1' C4' 61.9(3) . . ?
C5' Ir1' C4' 37.0(3) . . ?
C1' Ir1' C4' 62.0(3) . . ?
C3' Ir1' C4' 37.2(3) . . ?
C5 C1 C2 107.7(9) . . ?
C5 C1 C6 126.1(9) . . ?
C2 C1 C6 126.2(9) . . ?
C5 C1 Ir1 71.0(5) . . ?
C2 C1 Ir1 70.5(5) . . ?
C6 C1 Ir1 125.4(7) . . ?
C5' C1' C2' 107.2(8) . . ?
C5' C1' C6' 127.0(9) . . ?
C2' C1' C6' 125.7(9) . . ?
C5' C1' Ir1' 71.5(5) . . ?
C2' C1' Ir1' 70.9(5) . . ?
C6' C1' Ir1' 124.8(6) . . ?
C3' C2' C1' 108.3(8) . . ?
C3' C2' C7' 125.5(9) . . ?
C1' C2' C7' 126.1(9) . . ?
C3' C2' Ir1' 72.0(5) . . ?
C1' C2' Ir1' 71.3(5) . . ?
C7' C2' Ir1' 125.4(7) . . ?
C3 C2 C1 107.5(8) . . ?
C3 C2 C7 125.3(9) . . ?
C1 C2 C7 127.0(9) . . ?
C3 C2 Ir1 71.6(5) . . ?
C1 C2 Ir1 71.5(5) . . ?
C7 C2 Ir1 126.8(7) . . ?
C2 C3 C4 108.1(8) . . ?
C2 C3 C8 126.1(8) . . ?
C4 C3 C8 125.5(9) . . ?
C2 C3 Ir1 70.6(5) . . ?
C4 C3 Ir1 72.2(5) . . ?
C8 C3 Ir1 127.3(6) . . ?
C2' C3' C4' 107.5(8) . . ?
C2' C3' C8' 126.7(9) . . ?
C4' C3' C8' 125.6(9) . . ?
C2' C3' Ir1' 70.7(5) . . ?
C4' C3' Ir1' 71.9(5) . . ?
C8' C3' Ir1' 127.0(6) . . ?
C5 C4 C3 107.5(8) . . ?
C5 C4 C9 126.8(9) . . ?
C3 C4 C9 125.6(9) . . ?
C5 C4 Ir1 70.2(5) . . ?
C3 C4 Ir1 70.2(5) . . ?
C9 C4 Ir1 127.7(7) . . ?
C5' C4' C3' 107.8(8) . . ?
C5' C4' C9' 125.9(9) . . ?
C3' C4' C9' 126.2(8) . . ?
C5' C4' Ir1' 70.5(5) . . ?
C3' C4' Ir1' 71.0(5) . . ?
C9' C4' Ir1' 127.3(6) . . ?
C1 C5 C4 109.3(8) . . ?
C1 C5 C10 124.5(9) . . ?
C4 C5 C10 125.8(9) . . ?
C1 C5 Ir1 71.5(5) . . ?
C4 C5 Ir1 72.7(5) . . ?
C10 C5 Ir1 127.9(6) . . ?
C1' C5' C4' 109.1(8) . . ?
C1' C5' C10' 125.3(8) . . ?
C4' C5' C10' 125.3(8) . . ?
C1' C5' Ir1' 71.6(5) . . ?
C4' C5' Ir1' 72.5(5) . . ?
C10' C5' Ir1' 127.1(6) . . ?
O1 C11 Ir1 175.0(9) . . ?
O1' C11' Ir1' 173.9(9) . . ?
F1' C12' C13' 102.1(8) . . ?
F1' C12' Ir1' 122.7(7) . . ?
C13' C12' Ir1' 135.2(8) . . ?
F1 C12 C13 103.2(8) . . ?
F1 C12 Ir1 121.1(7) . . ?
C13 C12 Ir1 135.7(8) . . ?
F2' C13' F4' 108.8(8) . . ?
F2' C13' F3' 108.1(9) . . ?
F4' C13' F3' 105.2(8) . . ?
F2' C13' C12' 112.2(8) . . ?
F4' C13' C12' 111.3(9) . . ?
F3' C13' C12' 111.1(8) . . ?
F2 C13 F3 108.4(9) . . ?
F2 C13 F4 105.9(8) . . ?
F3 C13 F4 106.5(9) . . ?
F2 C13 C12 112.6(9) . . ?
F3 C13 C12 111.9(9) . . ?
F4 C13 C12 111.1(9) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         4.327
_refine_diff_density_min         -1.523
_refine_diff_density_rms         0.217
####################################################################### 
# 
# 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_rph409
_database_code_depnum_ccdc_archive 'CCDC 1406698'
_audit_update_record             
;
2015-06-13 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Cl F6 Ir O'
_chemical_formula_weight         589.96

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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.5574(18)
_cell_length_b                   10.840(2)
_cell_length_c                   17.604(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1823.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9766
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.14

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    7.531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2110
_exptl_absorpt_correction_T_max  0.3143
_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            15503
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         28.14
_reflns_number_total             4184
_reflns_number_gt                3997
_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          
; 
 The molecule contains two chiral centers.  The crystal contains all four 
 possible forms.  The relative stereochemistry shown is present 89%.  Only
 the second position of the Ir atom is located and refined.  The inverted 
 forms are obtained by refining as racemic twin (BASF = approx. 0.5).
 All non-Ir atoms have an occupancy of 0.89, but since the 0.11 fraction
 was not available for refinement, this discrepancy was ignored.	     

 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)+(0.0500P)²+7.5000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.515(14)
_refine_ls_number_reflns         4184
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.003

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 0.44096(3) 0.50765(2) 0.886594(14) 0.01940(9) Uani 0.89 1 d P . .
Ir1' Ir 0.5509(4) 0.5099(2) 0.89171(15) 0.0481(8) Uani 0.11 1 d P A 1
Cl1 Cl 0.3135(3) 0.5189(2) 1.00166(13) 0.0549(6) Uani 1 1 d . A .
F1 F 0.6868(6) 0.3494(5) 0.8861(4) 0.0584(16) Uani 1 1 d . . .
F2 F 0.5251(7) 0.1560(5) 0.9324(3) 0.0538(16) Uani 1 1 d . . .
F3 F 0.4705(6) 0.0207(4) 1.0558(3) 0.0504(13) Uani 1 1 d . A .
F4 F 0.4773(6) 0.1215(5) 1.1959(3) 0.0452(13) Uani 1 1 d . . .
F5 F 0.5462(6) 0.3638(5) 1.2122(3) 0.0480(13) Uani 1 1 d . A .
F6 F 0.6136(6) 0.5031(5) 1.0904(3) 0.0500(12) Uani 1 1 d . . .
O1 O 0.3341(11) 0.2822(10) 0.8302(6) 0.081(3) Uani 1 1 d . . .
C1 C 0.5866(8) 0.6572(7) 0.8421(4) 0.0287(16) Uani 1 1 d . A .
C2 C 0.5334(9) 0.5779(6) 0.7821(4) 0.0295(17) Uani 1 1 d . A .
C3 C 0.3849(9) 0.5948(7) 0.7752(4) 0.0302(16) Uani 1 1 d . A .
C4 C 0.3443(9) 0.6767(6) 0.8355(5) 0.0252(17) Uani 1 1 d . A .
C5 C 0.4674(9) 0.7115(6) 0.8770(4) 0.0268(16) Uani 1 1 d . A .
C6 C 0.7338(8) 0.6753(9) 0.8618(5) 0.0341(19) Uani 1 1 d . . .
H6A H 0.7706 0.7466 0.8340 0.051 Uiso 1 1 calc R A 1
H6B H 0.7872 0.6014 0.8480 0.051 Uiso 1 1 calc R A 1
H6C H 0.7422 0.6899 0.9165 0.051 Uiso 1 1 calc R A 1
C7 C 0.6239(8) 0.5039(8) 0.7284(4) 0.0339(15) Uani 1 1 d . . .
H7A H 0.6531 0.5562 0.6859 0.051 Uiso 1 1 calc R A .
H7B H 0.5704 0.4335 0.7090 0.051 Uiso 1 1 calc R . .
H7C H 0.7068 0.4739 0.7555 0.051 Uiso 1 1 calc R . .
C8 C 0.2936(9) 0.5426(8) 0.7164(4) 0.0367(18) Uani 1 1 d . . .
H8A H 0.2867 0.6004 0.6738 0.055 Uiso 1 1 calc R A .
H8B H 0.2002 0.5282 0.7377 0.055 Uiso 1 1 calc R . .
H8C H 0.3328 0.4643 0.6985 0.055 Uiso 1 1 calc R . .
C9 C 0.1961(9) 0.7212(8) 0.8500(5) 0.0354(17) Uani 1 1 d . . .
H9A H 0.1791 0.7969 0.8211 0.053 Uiso 1 1 calc R A .
H9B H 0.1840 0.7377 0.9044 0.053 Uiso 1 1 calc R . .
H9C H 0.1296 0.6575 0.8340 0.053 Uiso 1 1 calc R . .
C10 C 0.4704(12) 0.8020(7) 0.9404(4) 0.042(2) Uani 1 1 d . . .
H10A H 0.4313 0.8807 0.9231 0.064 Uiso 1 1 calc R A .
H10B H 0.5672 0.8144 0.9570 0.064 Uiso 1 1 calc R . .
H10C H 0.4146 0.7705 0.9829 0.064 Uiso 1 1 calc R . .
C11 C 0.3683(12) 0.3386(10) 0.8549(6) 0.032(2) Uani 1 1 d . A .
C12 C 0.6072(9) 0.4201(8) 0.9413(5) 0.040(2) Uani 1 1 d . A .
H12A H 0.6844 0.4691 0.9649 0.048 Uiso 1 1 calc R B 1
C13 C 0.5725(9) 0.3347(7) 1.0066(4) 0.0306(16) Uani 1 1 d . . .
C14 C 0.5368(10) 0.2116(7) 1.0010(4) 0.0376(19) Uani 1 1 d . A .
C15 C 0.5025(9) 0.1401(7) 1.0631(5) 0.0321(16) Uani 1 1 d . . .
C16 C 0.5038(8) 0.1898(8) 1.1348(4) 0.0282(16) Uani 1 1 d . A .
C17 C 0.5388(9) 0.3134(7) 1.1428(4) 0.0331(17) Uani 1 1 d . . .
C18 C 0.5714(10) 0.3823(7) 1.0805(5) 0.0409(19) Uani 1 1 d . A .


_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 Ir1' 1.055(4) . ?
Ir1 C11 2.038(10) . ?
Ir1 C12 2.086(9) . ?
Ir1 C2 2.177(7) . ?
Ir1 C5 2.231(6) . ?
Ir1 C3 2.241(8) . ?
Ir1 C4 2.241(8) . ?
Ir1 C1 2.276(8) . ?
Ir1 Cl1 2.367(2) . ?
Ir1' C12 1.414(8) . ?
Ir1' C1 1.851(8) . ?
Ir1' C2 2.072(7) . ?
Ir1' F1 2.173(6) . ?
Ir1' C5 2.341(7) . ?
Ir1' C6 2.558(9) . ?
F1 C12 1.452(11) . ?
F2 C14 1.354(9) . ?
F3 C15 1.337(9) . ?
F4 C16 1.330(9) . ?
F5 C17 1.340(8) . ?
F6 C18 1.382(9) . ?
O1 C11 0.818(13) . ?
C1 C5 1.422(11) . ?
C1 C2 1.454(10) . ?
C1 C6 1.462(11) . ?
C2 C3 1.436(12) . ?
C2 C7 1.513(10) . ?
C3 C4 1.437(11) . ?
C3 C8 1.468(11) . ?
C4 C5 1.435(11) . ?
C4 C9 1.517(12) . ?
C5 C10 1.485(9) . ?
C12 C13 1.512(10) . ?
C13 C14 1.381(11) . ?
C13 C18 1.399(11) . ?
C14 C15 1.380(11) . ?
C15 C16 1.372(11) . ?
C16 C17 1.388(11) . ?
C17 C18 1.363(12) . ?

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
Ir1' Ir1 C11 112.6(4) . . ?
Ir1' Ir1 C12 38.1(3) . . ?
C11 Ir1 C12 88.7(4) . . ?
Ir1' Ir1 C2 70.1(3) . . ?
C11 Ir1 C2 102.8(4) . . ?
C12 Ir1 C2 103.9(3) . . ?
Ir1' Ir1 C5 82.6(3) . . ?
C11 Ir1 C5 155.3(4) . . ?
C12 Ir1 C5 113.5(3) . . ?
C2 Ir1 C5 62.9(3) . . ?
Ir1' Ir1 C3 107.6(3) . . ?
C11 Ir1 C3 93.3(4) . . ?
C12 Ir1 C3 141.0(3) . . ?
C2 Ir1 C3 37.9(3) . . ?
C5 Ir1 C3 62.8(3) . . ?
Ir1' Ir1 C4 115.2(2) . . ?
C11 Ir1 C4 119.0(4) . . ?
C12 Ir1 C4 150.6(3) . . ?
C2 Ir1 C4 62.8(3) . . ?
C5 Ir1 C4 37.4(3) . . ?
C3 Ir1 C4 37.4(3) . . ?
Ir1' Ir1 C1 53.4(2) . . ?
C11 Ir1 C1 139.0(4) . . ?
C12 Ir1 C1 91.0(3) . . ?
C2 Ir1 C1 38.0(3) . . ?
C5 Ir1 C1 36.8(3) . . ?
C3 Ir1 C1 62.9(3) . . ?
C4 Ir1 C1 62.1(3) . . ?
Ir1' Ir1 Cl1 116.01(16) . . ?
C11 Ir1 Cl1 96.1(3) . . ?
C12 Ir1 Cl1 91.2(3) . . ?
C2 Ir1 Cl1 156.0(2) . . ?
C5 Ir1 Cl1 94.1(2) . . ?
C3 Ir1 Cl1 127.1(2) . . ?
C4 Ir1 Cl1 95.1(2) . . ?
C1 Ir1 Cl1 124.9(2) . . ?
Ir1 Ir1' C12 114.5(4) . . ?
Ir1 Ir1' C1 99.4(3) . . ?
C12 Ir1' C1 144.6(5) . . ?
Ir1 Ir1' C2 81.3(3) . . ?
C12 Ir1' C2 148.3(5) . . ?
C1 Ir1' C2 43.1(3) . . ?
Ir1 Ir1' F1 124.9(3) . . ?
C12 Ir1' F1 41.4(4) . . ?
C1 Ir1' F1 124.0(3) . . ?
C2 Ir1' F1 106.9(3) . . ?
Ir1 Ir1' C5 70.9(3) . . ?
C12 Ir1' C5 147.2(5) . . ?
C1 Ir1' C5 37.4(3) . . ?
C2 Ir1' C5 62.5(3) . . ?
F1 Ir1' C5 161.1(3) . . ?
Ir1 Ir1' C6 132.8(3) . . ?
C12 Ir1' C6 110.5(5) . . ?
C1 Ir1' C6 34.2(3) . . ?
C2 Ir1' C6 67.3(3) . . ?
F1 Ir1' C6 98.3(3) . . ?
C5 Ir1' C6 63.7(3) . . ?
C12 F1 Ir1' 40.0(4) . . ?
C5 C1 C2 106.2(7) . . ?
C5 C1 C6 127.8(7) . . ?
C2 C1 C6 126.0(7) . . ?
C5 C1 Ir1' 90.3(5) . . ?
C2 C1 Ir1' 76.6(4) . . ?
C6 C1 Ir1' 100.4(5) . . ?
C5 C1 Ir1 69.9(4) . . ?
C2 C1 Ir1 67.3(4) . . ?
C6 C1 Ir1 127.1(5) . . ?
Ir1' C1 Ir1 27.22(16) . . ?
C3 C2 C1 109.4(7) . . ?
C3 C2 C7 125.4(7) . . ?
C1 C2 C7 124.6(7) . . ?
C3 C2 Ir1' 101.8(5) . . ?
C1 C2 Ir1' 60.4(4) . . ?
C7 C2 Ir1' 110.3(5) . . ?
C3 C2 Ir1 73.5(4) . . ?
C1 C2 Ir1 74.6(4) . . ?
C7 C2 Ir1 125.1(5) . . ?
Ir1' C2 Ir1 28.62(14) . . ?
C2 C3 C4 106.5(7) . . ?
C2 C3 C8 126.7(8) . . ?
C4 C3 C8 126.7(8) . . ?
C2 C3 Ir1 68.7(4) . . ?
C4 C3 Ir1 71.3(4) . . ?
C8 C3 Ir1 126.6(5) . . ?
C5 C4 C3 108.4(7) . . ?
C5 C4 C9 126.6(7) . . ?
C3 C4 C9 125.0(8) . . ?
C5 C4 Ir1 70.9(4) . . ?
C3 C4 Ir1 71.3(4) . . ?
C9 C4 Ir1 125.2(5) . . ?
C1 C5 C4 109.2(6) . . ?
C1 C5 C10 125.6(8) . . ?
C4 C5 C10 124.8(8) . . ?
C1 C5 Ir1 73.3(4) . . ?
C4 C5 Ir1 71.7(4) . . ?
C10 C5 Ir1 126.8(5) . . ?
C1 C5 Ir1' 52.3(4) . . ?
C4 C5 Ir1' 95.2(4) . . ?
C10 C5 Ir1' 121.8(5) . . ?
Ir1 C5 Ir1' 26.55(12) . . ?
C1 C6 Ir1' 45.4(4) . . ?
O1 C11 Ir1 162.5(15) . . ?
Ir1' C12 F1 98.6(6) . . ?
Ir1' C12 C13 143.9(7) . . ?
F1 C12 C13 107.5(6) . . ?
Ir1' C12 Ir1 27.4(2) . . ?
F1 C12 Ir1 109.3(6) . . ?
C13 C12 Ir1 117.6(6) . . ?
C14 C13 C18 114.9(7) . . ?
C14 C13 C12 126.2(7) . . ?
C18 C13 C12 118.9(7) . . ?
F2 C14 C15 116.0(7) . . ?
F2 C14 C13 121.0(7) . . ?
C15 C14 C13 122.9(7) . . ?
F3 C15 C16 118.1(7) . . ?
F3 C15 C14 121.4(7) . . ?
C16 C15 C14 120.5(7) . . ?
F4 C16 C15 121.6(7) . . ?
F4 C16 C17 120.0(7) . . ?
C15 C16 C17 118.3(7) . . ?
F5 C17 C18 119.9(7) . . ?
F5 C17 C16 120.0(7) . . ?
C18 C17 C16 120.1(7) . . ?
C17 C18 F6 119.0(7) . . ?
C17 C18 C13 123.3(7) . . ?
F6 C18 C13 117.6(8) . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.552
_refine_diff_density_min         -1.436
_refine_diff_density_rms         0.184
####################################################################### 
# 
# 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_rph412a
_database_code_depnum_ccdc_archive 'CCDC 1406699'
_audit_update_record             
;
2015-06-13 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;
_audit_creation_date             2015-06-02
_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         'C18 H15 F6 Ir O'
_chemical_formula_sum            'C18 H15 F6 Ir O'
_chemical_formula_weight         553.50
_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'
H H 0.0000 0.0000 '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                   18.596(6)
_cell_length_b                   10.887(3)
_cell_length_c                   8.594(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1739.8(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6172
_cell_measurement_temperature    208.15
_cell_measurement_theta_max      28.10
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   0.613
_shelx_estimated_absorpt_T_min   0.307
_exptl_absorpt_coefficient_mu    7.738
_exptl_absorpt_correction_T_max  0.293
_exptl_absorpt_correction_T_min  0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.113
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       blade
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8271
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.097
_diffrn_reflns_theta_min         2.190
_diffrn_ambient_temperature      208.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.935
_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                1928
_reflns_number_total             2094
_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         1.570
_refine_diff_density_min         -2.064
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2094
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0215
_refine_ls_restrained_S_all      1.070
_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)+(0.0361P)²+0.4113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0573
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.29291(2) 0.2500 -0.35500(2) 0.02620(8) Uani 1 2 d S T P . .
F1 F 0.24366(14) 0.2500 -0.0374(3) 0.0512(7) Uani 1 2 d S T P . .
F2 F 0.37126(11) 0.03363(18) -0.0298(3) 0.0565(5) Uani 1 1 d . . . . .
F3 F 0.48563(14) 0.0344(2) 0.1593(2) 0.0648(7) Uani 1 1 d . . . . .
F4 F 0.54471(14) 0.2500 0.2527(3) 0.0665(10) Uani 1 2 d S T P . .
O1 O 0.1307(2) 0.2500 -0.3387(4) 0.0630(13) Uani 1 2 d S T P . .
C1 C 0.4045(2) 0.2500 -0.4470(5) 0.0302(8) Uani 1 2 d S T P . .
C2 C 0.36907(14) 0.1428(3) -0.5085(3) 0.0315(6) Uani 1 1 d . . . . .
C3 C 0.31081(16) 0.1839(3) -0.6039(3) 0.0308(6) Uani 1 1 d . . . . .
C4 C 0.4746(3) 0.2500 -0.3572(6) 0.0444(12) Uani 1 2 d S T P . .
H4A H 0.515(3) 0.2500 -0.425(7) 0.067 Uiso 1 2 d RS T P . .
H4B H 0.479(2) 0.180(4) -0.300(5) 0.067 Uiso 1 1 d R . . . .
C5 C 0.39102(18) 0.0119(3) -0.4838(4) 0.0443(8) Uani 1 1 d . . . . .
H5A H 0.4284 -0.0097 -0.5575 0.066 Uiso 1 1 calc GR . . . .
H5B H 0.3498 -0.0413 -0.4993 0.066 Uiso 1 1 calc GR . . . .
H5C H 0.4090 0.0019 -0.3787 0.066 Uiso 1 1 calc GR . . . .
C6 C 0.26040(18) 0.1032(3) -0.6935(4) 0.0440(8) Uani 1 1 d . . . . .
H6A H 0.2807 0.0860 -0.7951 0.066 Uiso 1 1 calc GR . . . .
H6B H 0.2146 0.1446 -0.7058 0.066 Uiso 1 1 calc GR . . . .
H6C H 0.2533 0.0268 -0.6375 0.066 Uiso 1 1 calc GR . . . .
C7 C 0.1938(3) 0.2500 -0.3376(6) 0.0437(12) Uani 1 2 d S T P . .
C8 C 0.3015(2) 0.2500 -0.1397(5) 0.0328(10) Uani 1 2 d S T P . .
C9 C 0.3674(2) 0.2500 -0.0384(5) 0.0334(9) Uani 1 2 d S T P . .
C10 C 0.39855(16) 0.1422(3) 0.0132(4) 0.0389(7) Uani 1 1 d . . . . .
C11 C 0.45774(18) 0.1410(3) 0.1102(4) 0.0443(8) Uani 1 1 d . . . . .
C12 C 0.4877(3) 0.2500 0.1577(5) 0.0460(12) 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 2.221(4) . ?
Ir1 C2 2.260(3) 7_565 ?
Ir1 C2 2.260(3) . ?
Ir1 C3 2.281(3) 7_565 ?
Ir1 C3 2.281(3) . ?
Ir1 C7 1.850(5) . ?
Ir1 C8 1.857(4) . ?
F1 C8 1.390(5) . ?
F2 C10 1.338(4) . ?
F3 C11 1.340(4) . ?
F4 C12 1.338(5) . ?
O1 C7 1.172(6) . ?
C1 C2 1.441(4) 7_565 ?
C1 C2 1.441(4) . ?
C1 C4 1.515(6) . ?
C2 C3 1.430(4) . ?
C2 C5 1.498(4) . ?
C3 C3 1.440(6) 7_565 ?
C3 C6 1.498(4) . ?
C8 C9 1.503(6) . ?
C9 C10 1.382(4) . ?
C9 C10 1.382(4) 7_565 ?
C10 C11 1.381(4) . ?
C11 C12 1.373(4) . ?
C12 C11 1.373(4) 7_565 ?

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 C2 37.50(9) . . ?
C1 Ir1 C2 37.50(9) . 7_565 ?
C1 Ir1 C3 61.96(12) . . ?
C1 Ir1 C3 61.96(12) . 7_565 ?
C2 Ir1 C2 62.16(14) . 7_565 ?
C2 Ir1 C3 36.70(11) . . ?
C2 Ir1 C3 36.70(11) 7_565 7_565 ?
C2 Ir1 C3 61.59(10) 7_565 . ?
C2 Ir1 C3 61.59(10) . 7_565 ?
C3 Ir1 C3 36.80(16) 7_565 . ?
C7 Ir1 C1 163.80(18) . . ?
C7 Ir1 C2 132.21(13) . 7_565 ?
C7 Ir1 C2 132.21(13) . . ?
C7 Ir1 C3 102.79(16) . . ?
C7 Ir1 C3 102.79(16) . 7_565 ?
C7 Ir1 C8 90.3(2) . . ?
C8 Ir1 C1 105.90(17) . . ?
C8 Ir1 C2 121.84(13) . 7_565 ?
C8 Ir1 C2 121.84(13) . . ?
C8 Ir1 C3 157.15(11) . . ?
C8 Ir1 C3 157.15(11) . 7_565 ?
C2 C1 Ir1 72.72(18) . . ?
C2 C1 Ir1 72.72(18) 7_565 . ?
C2 C1 C2 108.2(3) 7_565 . ?
C2 C1 C4 125.51(17) 7_565 . ?
C2 C1 C4 125.51(17) . . ?
C4 C1 Ir1 128.5(3) . . ?
C1 C2 Ir1 69.78(18) . . ?
C1 C2 C5 126.4(3) . . ?
C3 C2 Ir1 72.45(16) . . ?
C3 C2 C1 107.7(3) . . ?
C3 C2 C5 125.8(3) . . ?
C5 C2 Ir1 125.4(2) . . ?
C2 C3 Ir1 70.85(16) . . ?
C2 C3 C3 108.21(17) . 7_565 ?
C2 C3 C6 125.9(3) . . ?
C3 C3 Ir1 71.60(8) 7_565 . ?
C3 C3 C6 125.89(19) 7_565 . ?
C6 C3 Ir1 125.2(2) . . ?
O1 C7 Ir1 174.9(4) . . ?
F1 C8 Ir1 124.3(3) . . ?
F1 C8 C9 105.4(3) . . ?
C9 C8 Ir1 130.3(3) . . ?
C10 C9 C8 121.83(19) . . ?
C10 C9 C8 121.83(19) 7_565 . ?
C10 C9 C10 116.3(4) . 7_565 ?
F2 C10 C9 120.2(3) . . ?
F2 C10 C11 117.5(3) . . ?
C11 C10 C9 122.4(3) . . ?
F3 C11 C10 120.4(3) . . ?
F3 C11 C12 119.9(3) . . ?
C12 C11 C10 119.7(3) . . ?
F4 C12 C11 120.2(2) . . ?
F4 C12 C11 120.2(2) . 7_565 ?
C11 C12 C11 119.6(4) . 7_565 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
