# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_0098abc14
_database_code_depnum_ccdc_archive 'CCDC 1520522'
_audit_update_record             
;
2016-12-02 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

#====================================================================
# [Ir(PCP)(CO)(H)(Ph)]
#--------------------------------------------------------------------
# Collected and solved by Adrian Chaplin
#--------------------------------------------------------------------  
# Start Validation Reply Form 

_vrf_DIFMX01_0098abc14           
; 
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75 
RESPONSE: 
The solution contains a large Fourier peak 0.79 A from Ir1 (6.18 eA-3) 
attributed to Fourier truncation errors. If this peak is excluded the
max/min residual density is 1.32/-1.84. 

This also addresses: DIFMX02, PLAT094, PLAT097
;

_vrf_PLAT041_0098abc14           
; 
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: 
The hydride ligand was not located.

This also addresses: PLAT043, PLAT068
;
#====================================================================

_audit_creation_date             2015-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            .
_chemical_name_systematic        .
_chemical_formula_moiety         'C31 H49 Ir O P2'
_chemical_formula_sum            'C31 H49 Ir O P2'
_chemical_formula_weight         691.84
_chemical_absolute_configuration .
_chemical_melting_point          'not measured'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.11917(16)
_cell_length_b                   10.6057(2)
_cell_length_c                   16.5557(3)
_cell_angle_alpha                80.6460(16)
_cell_angle_beta                 74.2931(16)
_cell_angle_gamma                81.3448(16)
_cell_volume                     1511.32(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    19837
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.4990
_cell_measurement_theta_min      3.4710
_shelx_estimated_absorpt_T_max   .
_shelx_estimated_absorpt_T_min   .
_exptl_absorpt_coefficient_mu    4.544
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   .
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             700
_exptl_crystal_recrystallization_method 'Crystals grown from heptane at 253 K'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_special_details           .
_exptl_transmission_factor_max   .
_exptl_transmission_factor_min   .
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30824
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        27.102
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         3.333
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   35.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1653  178.0000   30.0000 78

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1653   77.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1653  -99.0000 -120.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega -103.00   10.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.1028  -77.0000   60.0000 113

#__ type_ start__ end____ width___ exp.time_
  5 omega -113.00  -53.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.1028  178.0000   30.0000 60

#__ type_ start__ end____ width___ exp.time_
  6 omega -114.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.1028    0.0000 -180.0000 179

#__ type_ start__ end____ width___ exp.time_
  7 omega   -6.00   97.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1653   57.0000  -90.0000 103

#__ type_ start__ end____ width___ exp.time_
  8 omega -114.00  -57.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.1028 -178.0000  -90.0000 57

#__ type_ start__ end____ width___ exp.time_
  9 omega -100.00    2.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.1028  -38.0000  120.0000 102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction: Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0408692000
_diffrn_orient_matrix_UB_12      -0.0469890000
_diffrn_orient_matrix_UB_13      0.0238596000
_diffrn_orient_matrix_UB_21      -0.0218638000
_diffrn_orient_matrix_UB_22      -0.0493338000
_diffrn_orient_matrix_UB_23      -0.0170525000
_diffrn_orient_matrix_UB_31      0.0668067000
_diffrn_orient_matrix_UB_32      0.0032931000
_diffrn_orient_matrix_UB_33      -0.0339649000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6229
_reflns_number_total             6667
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         6.180
_refine_diff_density_min         -1.844
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         6667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.088
_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)+(0.0214P)²+7.4892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0764
_refine_special_details          .
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C30(H30A,
 H30B,H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C),
 C35(H35A,H35B,H35C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.20626(2) 0.31457(2) 0.26408(2) 0.01579(6) Uani 1 1 d . . . . .
P10 P 0.10138(13) 0.52495(11) 0.23018(7) 0.0168(2) Uani 1 1 d . . . . .
P11 P 0.37823(12) 0.15060(11) 0.31056(7) 0.0163(2) Uani 1 1 d . . . . .
O3 O -0.0945(4) 0.2311(4) 0.3805(2) 0.0310(8) Uani 1 1 d . . . . .
C2 C 0.0171(5) 0.2601(4) 0.3363(3) 0.0185(9) Uani 1 1 d . . . . .
C4 C 0.1866(5) 0.2331(4) 0.1568(3) 0.0174(9) Uani 1 1 d . . . . .
C5 C 0.0750(5) 0.1510(4) 0.1635(3) 0.0210(9) Uani 1 1 d . . . . .
H5 H 0.0046 0.1329 0.2168 0.025 Uiso 1 1 calc R . . . .
C6 C 0.0636(6) 0.0953(5) 0.0955(3) 0.0254(10) Uani 1 1 d . . . . .
H6 H -0.0143 0.0410 0.1031 0.031 Uiso 1 1 calc R . . . .
C7 C 0.1637(6) 0.1178(5) 0.0169(3) 0.0267(10) Uani 1 1 d . . . . .
H7 H 0.1572 0.0783 -0.0294 0.032 Uiso 1 1 calc R . . . .
C8 C 0.2732(6) 0.1991(5) 0.0074(3) 0.0253(10) Uani 1 1 d . . . . .
H8 H 0.3429 0.2165 -0.0462 0.030 Uiso 1 1 calc R . . . .
C9 C 0.2831(5) 0.2558(5) 0.0754(3) 0.0227(9) Uani 1 1 d . . . . .
H9 H 0.3588 0.3127 0.0663 0.027 Uiso 1 1 calc R . . . .
C12 C 0.2438(5) 0.4023(4) 0.3619(3) 0.0196(9) Uani 1 1 d . . . . .
C13 C 0.1566(5) 0.5173(4) 0.3852(3) 0.0182(9) Uani 1 1 d . . . . .
C14 C 0.1754(5) 0.5720(5) 0.4519(3) 0.0214(9) Uani 1 1 d . . . . .
H14 H 0.1145 0.6494 0.4675 0.026 Uiso 1 1 calc R . . . .
C15 C 0.2823(5) 0.5145(5) 0.4960(3) 0.0246(10) Uani 1 1 d . . . . .
H15 H 0.2932 0.5510 0.5425 0.029 Uiso 1 1 calc R . . . .
C16 C 0.3732(5) 0.4036(5) 0.4719(3) 0.0230(10) Uani 1 1 d . . . . .
H16 H 0.4479 0.3647 0.5014 0.028 Uiso 1 1 calc R . . . .
C17 C 0.3559(5) 0.3487(4) 0.4049(3) 0.0207(9) Uani 1 1 d . . . . .
C18 C 0.0446(5) 0.5816(4) 0.3346(3) 0.0203(9) Uani 1 1 d . . . . .
H18A H 0.0442 0.6761 0.3279 0.024 Uiso 1 1 calc R . . . .
H18B H -0.0601 0.5605 0.3646 0.024 Uiso 1 1 calc R . . . .
C19 C 0.4643(5) 0.2344(4) 0.3722(3) 0.0214(9) Uani 1 1 d . . . . .
H19A H 0.4879 0.1741 0.4205 0.026 Uiso 1 1 calc R . . . .
H19B H 0.5616 0.2643 0.3361 0.026 Uiso 1 1 calc R . . . .
C20 C -0.0798(6) 0.5559(5) 0.1924(3) 0.0261(10) Uani 1 1 d . . . . .
C21 C -0.1820(6) 0.4509(5) 0.2387(4) 0.0323(12) Uani 1 1 d . . . . .
H21A H -0.1291 0.3668 0.2245 0.048 Uiso 1 1 calc GR . . . .
H21B H -0.2783 0.4665 0.2213 0.048 Uiso 1 1 calc GR . . . .
H21C H -0.2038 0.4521 0.2998 0.048 Uiso 1 1 calc GR . . . .
C22 C -0.0428(7) 0.5470(6) 0.0974(3) 0.0372(13) Uani 1 1 d . . . . .
H22A H 0.0097 0.6208 0.0658 0.056 Uiso 1 1 calc GR . . . .
H22B H -0.1381 0.5472 0.0808 0.056 Uiso 1 1 calc GR . . . .
H22C H 0.0237 0.4672 0.0849 0.056 Uiso 1 1 calc GR . . . .
C23 C -0.1723(6) 0.6864(5) 0.2118(4) 0.0345(12) Uani 1 1 d . . . . .
H23A H -0.1981 0.6901 0.2729 0.052 Uiso 1 1 calc GR . . . .
H23B H -0.2668 0.6959 0.1929 0.052 Uiso 1 1 calc GR . . . .
H23C H -0.1108 0.7561 0.1821 0.052 Uiso 1 1 calc GR . . . .
C24 C 0.2462(6) 0.6353(5) 0.1643(3) 0.0274(11) Uani 1 1 d . . . . .
C25 C 0.3663(6) 0.6404(5) 0.2137(3) 0.0298(11) Uani 1 1 d . . . . .
H25A H 0.3169 0.6815 0.2647 0.045 Uiso 1 1 calc GR . . . .
H25B H 0.4479 0.6900 0.1779 0.045 Uiso 1 1 calc GR . . . .
H25C H 0.4102 0.5528 0.2299 0.045 Uiso 1 1 calc GR . . . .
C26 C 0.1757(7) 0.7736(5) 0.1445(4) 0.0380(13) Uani 1 1 d . . . . .
H26A H 0.1118 0.7758 0.1051 0.057 Uiso 1 1 calc GR . . . .
H26B H 0.2576 0.8287 0.1187 0.057 Uiso 1 1 calc GR . . . .
H26C H 0.1125 0.8047 0.1969 0.057 Uiso 1 1 calc GR . . . .
C27 C 0.3330(7) 0.5844(5) 0.0804(3) 0.0361(13) Uani 1 1 d . . . . .
H27A H 0.3906 0.5007 0.0923 0.054 Uiso 1 1 calc GR . . . .
H27B H 0.4042 0.6452 0.0469 0.054 Uiso 1 1 calc GR . . . .
H27C H 0.2597 0.5748 0.0488 0.054 Uiso 1 1 calc GR . . . .
C28 C 0.2891(5) 0.0162(5) 0.3896(3) 0.0234(10) Uani 1 1 d . . . . .
C29 C 0.1985(6) 0.0749(5) 0.4703(3) 0.0298(11) Uani 1 1 d . . . . .
H29A H 0.2702 0.0991 0.4983 0.045 Uiso 1 1 calc GR . . . .
H29B H 0.1360 0.0117 0.5087 0.045 Uiso 1 1 calc GR . . . .
H29C H 0.1317 0.1515 0.4551 0.045 Uiso 1 1 calc GR . . . .
C30 C 0.4040(6) -0.0941(5) 0.4163(4) 0.0332(12) Uani 1 1 d . . . . .
H30A H 0.4547 -0.1414 0.3682 0.050 Uiso 1 1 calc GR . . . .
H30B H 0.3493 -0.1526 0.4631 0.050 Uiso 1 1 calc GR . . . .
H30C H 0.4809 -0.0585 0.4347 0.050 Uiso 1 1 calc GR . . . .
C31 C 0.1789(6) -0.0428(5) 0.3539(3) 0.0267(10) Uani 1 1 d . . . . .
H31A H 0.1012 0.0247 0.3391 0.040 Uiso 1 1 calc GR . . . .
H31B H 0.1287 -0.1088 0.3967 0.040 Uiso 1 1 calc GR . . . .
H31C H 0.2370 -0.0819 0.3033 0.040 Uiso 1 1 calc GR . . . .
C32 C 0.5503(5) 0.0816(5) 0.2315(3) 0.0233(10) Uani 1 1 d . . . . .
C33 C 0.6116(6) 0.1913(5) 0.1636(3) 0.0305(11) Uani 1 1 d . . . . .
H33A H 0.5337 0.2277 0.1330 0.046 Uiso 1 1 calc GR . . . .
H33B H 0.7046 0.1579 0.1239 0.046 Uiso 1 1 calc GR . . . .
H33C H 0.6359 0.2584 0.1907 0.046 Uiso 1 1 calc GR . . . .
C34 C 0.5031(6) -0.0171(5) 0.1881(3) 0.0312(11) Uani 1 1 d . . . . .
H34A H 0.4810 -0.0947 0.2282 0.047 Uiso 1 1 calc GR . . . .
H34B H 0.5868 -0.0392 0.1394 0.047 Uiso 1 1 calc GR . . . .
H34C H 0.4114 0.0195 0.1687 0.047 Uiso 1 1 calc GR . . . .
C35 C 0.6829(6) 0.0201(5) 0.2715(4) 0.0318(12) Uani 1 1 d . . . . .
H35A H 0.7102 0.0831 0.3006 0.048 Uiso 1 1 calc GR . . . .
H35B H 0.7721 -0.0071 0.2270 0.048 Uiso 1 1 calc GR . . . .
H35C H 0.6507 -0.0548 0.3122 0.048 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 P10 2.3344(11) . ?
Ir1 P11 2.3394(11) . ?
Ir1 C2 1.923(4) . ?
Ir1 C4 2.156(4) . ?
Ir1 C12 2.119(4) . ?
P10 C18 1.838(4) . ?
P10 C20 1.887(5) . ?
P10 C24 1.891(5) . ?
P11 C19 1.840(5) . ?
P11 C28 1.890(5) . ?
P11 C32 1.888(5) . ?
O3 C2 1.133(5) . ?
C4 C5 1.407(6) . ?
C4 C9 1.401(6) . ?
C5 C6 1.389(6) . ?
C6 C7 1.380(7) . ?
C7 C8 1.377(7) . ?
C8 C9 1.389(6) . ?
C12 C13 1.401(6) . ?
C12 C17 1.401(6) . ?
C13 C14 1.388(6) . ?
C13 C18 1.509(6) . ?
C14 C15 1.384(7) . ?
C15 C16 1.381(7) . ?
C16 C17 1.389(6) . ?
C17 C19 1.518(6) . ?
C20 C21 1.531(7) . ?
C20 C22 1.531(7) . ?
C20 C23 1.542(7) . ?
C24 C25 1.546(7) . ?
C24 C26 1.531(7) . ?
C24 C27 1.537(7) . ?
C28 C29 1.540(7) . ?
C28 C30 1.541(7) . ?
C28 C31 1.543(7) . ?
C32 C33 1.536(7) . ?
C32 C34 1.531(7) . ?
C32 C35 1.544(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
P10 Ir1 P11 157.21(4) . . ?
C2 Ir1 P10 94.70(14) . . ?
C2 Ir1 P11 99.31(14) . . ?
C2 Ir1 C4 94.20(18) . . ?
C2 Ir1 C12 91.15(17) . . ?
C4 Ir1 P10 98.85(12) . . ?
C4 Ir1 P11 97.96(11) . . ?
C12 Ir1 P10 80.07(13) . . ?
C12 Ir1 P11 81.75(13) . . ?
C12 Ir1 C4 174.61(17) . . ?
C18 P10 Ir1 100.86(15) . . ?
C18 P10 C20 104.3(2) . . ?
C18 P10 C24 104.1(2) . . ?
C20 P10 Ir1 120.24(16) . . ?
C20 P10 C24 110.6(2) . . ?
C24 P10 Ir1 114.29(17) . . ?
C19 P11 Ir1 101.99(15) . . ?
C19 P11 C28 104.0(2) . . ?
C19 P11 C32 103.1(2) . . ?
C28 P11 Ir1 115.83(15) . . ?
C32 P11 Ir1 119.74(16) . . ?
C32 P11 C28 109.7(2) . . ?
O3 C2 Ir1 177.6(4) . . ?
C5 C4 Ir1 122.1(3) . . ?
C9 C4 Ir1 123.5(3) . . ?
C9 C4 C5 114.4(4) . . ?
C6 C5 C4 122.7(4) . . ?
C7 C6 C5 120.9(4) . . ?
C8 C7 C6 118.1(4) . . ?
C7 C8 C9 120.8(4) . . ?
C8 C9 C4 123.1(4) . . ?
C13 C12 Ir1 120.5(3) . . ?
C17 C12 Ir1 121.7(3) . . ?
C17 C12 C13 117.8(4) . . ?
C12 C13 C18 118.3(4) . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 C18 121.0(4) . . ?
C15 C14 C13 120.5(4) . . ?
C16 C15 C14 119.5(4) . . ?
C15 C16 C17 120.4(4) . . ?
C12 C17 C19 117.9(4) . . ?
C16 C17 C12 120.9(4) . . ?
C16 C17 C19 121.1(4) . . ?
C13 C18 P10 109.0(3) . . ?
C17 C19 P11 110.7(3) . . ?
C21 C20 P10 108.0(3) . . ?
C21 C20 C22 107.8(4) . . ?
C21 C20 C23 107.3(4) . . ?
C22 C20 P10 110.4(4) . . ?
C22 C20 C23 110.1(4) . . ?
C23 C20 P10 113.0(3) . . ?
C25 C24 P10 108.6(3) . . ?
C26 C24 P10 113.5(4) . . ?
C26 C24 C25 107.3(4) . . ?
C26 C24 C27 108.6(4) . . ?
C27 C24 P10 111.4(3) . . ?
C27 C24 C25 107.1(4) . . ?
C29 C28 P11 107.3(3) . . ?
C29 C28 C30 106.9(4) . . ?
C29 C28 C31 109.5(4) . . ?
C30 C28 P11 115.1(3) . . ?
C30 C28 C31 107.7(4) . . ?
C31 C28 P11 110.1(3) . . ?
C33 C32 P11 108.5(3) . . ?
C33 C32 C35 107.0(4) . . ?
C34 C32 P11 110.0(3) . . ?
C34 C32 C33 108.3(4) . . ?
C34 C32 C35 110.0(4) . . ?
C35 C32 P11 112.9(3) . . ?

_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_0101abc14
_database_code_depnum_ccdc_archive 'CCDC 1520525'
_audit_update_record             
;
2016-12-02 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

#====================================================================
# [Ir(PCP)(CO)(H)(2,4,6-C6H2F3)]
#--------------------------------------------------------------------
# Collected and solved by Adrian Chaplin
#--------------------------------------------------------------------  
# Start Validation Reply Form 

_vrf_PLAT041_0101abc14           
; 
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: 
The hydride ligand was not located.

This also addresses: PLAT043, PLAT068
;
#====================================================================

_audit_creation_date             2015-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            .
_chemical_name_systematic        .
_chemical_formula_moiety         'C31 H46 F3 Ir O P2'
_chemical_formula_sum            'C31 H46 F3 Ir O P2'
_chemical_formula_weight         745.82
_chemical_absolute_configuration .
_chemical_melting_point          'not measured'
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'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.9975(3)
_cell_length_b                   16.9033(3)
_cell_length_c                   19.9108(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6057.18(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13774
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.2460
_cell_measurement_theta_min      3.2890
_shelx_estimated_absorpt_T_max   .
_shelx_estimated_absorpt_T_min   .
_exptl_absorpt_coefficient_mu    4.556
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   .
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    .
_exptl_crystal_description       prism
_exptl_crystal_F_000             2992
_exptl_crystal_recrystallization_method 'Crystals grown from heptane at 253 K'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           .
_exptl_transmission_factor_max   .
_exptl_transmission_factor_min   .
_diffrn_reflns_av_R_equivalents  0.1137
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            80680
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        27.102
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         3.281
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -53.00   57.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       25.7882  -38.0000   30.0000 110

#__ type_ start__ end____ width___ exp.time_
  2 omega  -32.00  110.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       25.7882   19.0000 -150.0000 142

#__ type_ start__ end____ width___ exp.time_
  3 omega -119.00  -57.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.7257 -178.0000    0.0000 62

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00  110.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       25.7882   77.0000    0.0000 120

#__ type_ start__ end____ width___ exp.time_
  5 omega   -7.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       25.7882   57.0000  -60.0000 97

#__ type_ start__ end____ width___ exp.time_
  6 omega -119.00  -57.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.7257 -178.0000   90.0000 62

#__ type_ start__ end____ width___ exp.time_
  7 omega -119.00  -57.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.7257 -178.0000 -180.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction: Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0003575000
_diffrn_orient_matrix_UB_12      0.0365823000
_diffrn_orient_matrix_UB_13      0.0174579000
_diffrn_orient_matrix_UB_21      0.0367971000
_diffrn_orient_matrix_UB_22      0.0070412000
_diffrn_orient_matrix_UB_23      -0.0112527000
_diffrn_orient_matrix_UB_31      -0.0141060000
_diffrn_orient_matrix_UB_32      0.0193209000
_diffrn_orient_matrix_UB_33      -0.0289399000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4782
_reflns_number_total             6670
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         2.107
_refine_diff_density_min         -0.963
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         6670
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0803
_refine_special_details          .
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C30(H30A,
 H30B,H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C),
 C35(H35A,H35B,H35C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.62122(2) 0.69764(2) 0.37986(2) 0.01750(7) Uani 1 1 d . . . . .
P10 P 0.53754(7) 0.72233(8) 0.29125(6) 0.0200(3) Uani 1 1 d . . . . .
P11 P 0.69475(7) 0.62065(7) 0.45242(6) 0.0202(3) Uani 1 1 d . . . . .
F5 F 0.65839(16) 0.88414(16) 0.42244(14) 0.0329(7) Uani 1 1 d . . . . .
F7 F 0.49044(19) 0.94322(18) 0.59357(15) 0.0452(9) Uani 1 1 d . . . . .
F9 F 0.48621(15) 0.69211(16) 0.49956(14) 0.0312(7) Uani 1 1 d . . . . .
O3 O 0.7508(2) 0.7961(2) 0.32480(18) 0.0364(9) Uani 1 1 d . . . . .
C2 C 0.7016(3) 0.7650(3) 0.3485(3) 0.0270(11) Uani 1 1 d . . . . .
C4 C 0.5755(3) 0.7800(3) 0.4532(2) 0.0233(11) Uani 1 1 d . . . . .
C5 C 0.6007(3) 0.8567(3) 0.4619(2) 0.0246(11) Uani 1 1 d . . . . .
C6 C 0.5748(3) 0.9135(3) 0.5068(2) 0.0319(13) Uani 1 1 d . . . . .
H6 H 0.5954 0.9652 0.5084 0.038 Uiso 1 1 calc R . . . .
C7 C 0.5183(3) 0.8910(3) 0.5482(2) 0.0334(13) Uani 1 1 d . . . . .
C8 C 0.4894(3) 0.8168(3) 0.5454(2) 0.0307(13) Uani 1 1 d . . . . .
H8 H 0.4502 0.8010 0.5744 0.037 Uiso 1 1 calc R . . . .
C9 C 0.5190(3) 0.7649(3) 0.4987(2) 0.0231(11) Uani 1 1 d . . . . .
C12 C 0.6657(3) 0.6174(3) 0.3091(2) 0.0204(10) Uani 1 1 d . . . . .
C13 C 0.6387(3) 0.6147(3) 0.2425(2) 0.0244(11) Uani 1 1 d . . . . .
C14 C 0.6660(3) 0.5581(3) 0.1977(2) 0.0325(13) Uani 1 1 d . . . . .
H14 H 0.6477 0.5563 0.1530 0.039 Uiso 1 1 calc R . . . .
C15 C 0.7197(3) 0.5048(3) 0.2181(3) 0.0374(14) Uani 1 1 d . . . . .
H15 H 0.7353 0.4640 0.1885 0.045 Uiso 1 1 calc R . . . .
C16 C 0.7507(3) 0.5105(3) 0.2811(2) 0.0290(12) Uani 1 1 d . . . . .
H16 H 0.7897 0.4759 0.2940 0.035 Uiso 1 1 calc R . . . .
C17 C 0.7246(3) 0.5673(3) 0.3258(2) 0.0257(11) Uani 1 1 d . . . . .
C18 C 0.5857(3) 0.6779(3) 0.2189(2) 0.0272(12) Uani 1 1 d . . . . .
H18A H 0.5488 0.6546 0.1879 0.033 Uiso 1 1 calc R . . . .
H18B H 0.6134 0.7194 0.1943 0.033 Uiso 1 1 calc R . . . .
C19 C 0.7620(3) 0.5784(3) 0.3934(2) 0.0256(11) Uani 1 1 d . . . . .
H19A H 0.8051 0.6143 0.3887 0.031 Uiso 1 1 calc R . . . .
H19B H 0.7801 0.5269 0.4104 0.031 Uiso 1 1 calc R . . . .
C20 C 0.5177(3) 0.8263(3) 0.2629(3) 0.0277(12) Uani 1 1 d . . . . .
C21 C 0.5924(3) 0.8712(3) 0.2671(3) 0.0363(14) Uani 1 1 d . . . . .
H21A H 0.6086 0.8741 0.3140 0.054 Uiso 1 1 calc GR . . . .
H21B H 0.5861 0.9249 0.2494 0.054 Uiso 1 1 calc GR . . . .
H21C H 0.6300 0.8432 0.2405 0.054 Uiso 1 1 calc GR . . . .
C22 C 0.4623(3) 0.8670(3) 0.3102(3) 0.0335(13) Uani 1 1 d . . . . .
H22A H 0.4131 0.8430 0.3047 0.050 Uiso 1 1 calc GR . . . .
H22B H 0.4596 0.9235 0.2992 0.050 Uiso 1 1 calc GR . . . .
H22C H 0.4789 0.8606 0.3567 0.050 Uiso 1 1 calc GR . . . .
C23 C 0.4908(3) 0.8340(3) 0.1898(3) 0.0364(14) Uani 1 1 d . . . . .
H23A H 0.5236 0.8035 0.1603 0.055 Uiso 1 1 calc GR . . . .
H23B H 0.4916 0.8898 0.1764 0.055 Uiso 1 1 calc GR . . . .
H23C H 0.4400 0.8135 0.1861 0.055 Uiso 1 1 calc GR . . . .
C24 C 0.4473(3) 0.6649(3) 0.2949(2) 0.0245(11) Uani 1 1 d . . . . .
C25 C 0.4673(3) 0.5761(3) 0.2933(3) 0.0328(13) Uani 1 1 d . . . . .
H25A H 0.4879 0.5626 0.2492 0.049 Uiso 1 1 calc GR . . . .
H25B H 0.4224 0.5447 0.3014 0.049 Uiso 1 1 calc GR . . . .
H25C H 0.5041 0.5648 0.3282 0.049 Uiso 1 1 calc GR . . . .
C26 C 0.3956(3) 0.6806(3) 0.2360(3) 0.0354(13) Uani 1 1 d . . . . .
H26A H 0.3762 0.7347 0.2391 0.053 Uiso 1 1 calc GR . . . .
H26B H 0.3542 0.6430 0.2372 0.053 Uiso 1 1 calc GR . . . .
H26C H 0.4230 0.6744 0.1939 0.053 Uiso 1 1 calc GR . . . .
C27 C 0.4058(3) 0.6804(3) 0.3602(3) 0.0324(13) Uani 1 1 d . . . . .
H27A H 0.4370 0.6646 0.3983 0.049 Uiso 1 1 calc GR . . . .
H27B H 0.3596 0.6497 0.3607 0.049 Uiso 1 1 calc GR . . . .
H27C H 0.3942 0.7369 0.3637 0.049 Uiso 1 1 calc GR . . . .
C28 C 0.7539(3) 0.6714(3) 0.5182(2) 0.0268(11) Uani 1 1 d . . . . .
C29 C 0.7827(3) 0.7490(3) 0.4864(3) 0.0394(14) Uani 1 1 d . . . . .
H29A H 0.8084 0.7370 0.4442 0.059 Uiso 1 1 calc GR . . . .
H29B H 0.8172 0.7749 0.5175 0.059 Uiso 1 1 calc GR . . . .
H29C H 0.7406 0.7843 0.4773 0.059 Uiso 1 1 calc GR . . . .
C30 C 0.8226(3) 0.6228(3) 0.5387(3) 0.0347(13) Uani 1 1 d . . . . .
H30A H 0.8068 0.5754 0.5631 0.052 Uiso 1 1 calc GR . . . .
H30B H 0.8547 0.6549 0.5677 0.052 Uiso 1 1 calc GR . . . .
H30C H 0.8502 0.6072 0.4984 0.052 Uiso 1 1 calc GR . . . .
C31 C 0.7081(3) 0.6927(3) 0.5802(3) 0.0380(14) Uani 1 1 d . . . . .
H31A H 0.6637 0.7223 0.5665 0.057 Uiso 1 1 calc GR . . . .
H31B H 0.7381 0.7254 0.6105 0.057 Uiso 1 1 calc GR . . . .
H31C H 0.6930 0.6442 0.6035 0.057 Uiso 1 1 calc GR . . . .
C32 C 0.6505(3) 0.5290(3) 0.4891(2) 0.0218(10) Uani 1 1 d . . . . .
C33 C 0.6252(3) 0.4753(3) 0.4301(2) 0.0281(12) Uani 1 1 d . . . . .
H33A H 0.5925 0.5053 0.4001 0.042 Uiso 1 1 calc GR . . . .
H33B H 0.5983 0.4294 0.4479 0.042 Uiso 1 1 calc GR . . . .
H33C H 0.6688 0.4571 0.4050 0.042 Uiso 1 1 calc GR . . . .
C34 C 0.5823(3) 0.5492(3) 0.5317(3) 0.0310(12) Uani 1 1 d . . . . .
H34A H 0.5971 0.5840 0.5687 0.047 Uiso 1 1 calc GR . . . .
H34B H 0.5609 0.5004 0.5499 0.047 Uiso 1 1 calc GR . . . .
H34C H 0.5453 0.5761 0.5037 0.047 Uiso 1 1 calc GR . . . .
C35 C 0.7039(3) 0.4795(3) 0.5316(3) 0.0308(12) Uani 1 1 d . . . . .
H35A H 0.7503 0.4714 0.5068 0.046 Uiso 1 1 calc GR . . . .
H35B H 0.6811 0.4281 0.5415 0.046 Uiso 1 1 calc GR . . . .
H35C H 0.7145 0.5073 0.5737 0.046 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 P10 2.3569(12) . ?
Ir1 P11 2.3520(12) . ?
Ir1 C2 1.944(5) . ?
Ir1 C4 2.178(5) . ?
Ir1 C12 2.113(4) . ?
P10 C18 1.840(5) . ?
P10 C20 1.880(5) . ?
P10 C24 1.893(5) . ?
P11 C19 1.832(5) . ?
P11 C28 1.893(5) . ?
P11 C32 1.888(5) . ?
F5 C5 1.381(5) . ?
F7 C7 1.359(6) . ?
F9 C9 1.365(5) . ?
O3 C2 1.133(6) . ?
C4 C5 1.385(7) . ?
C4 C9 1.387(7) . ?
C5 C6 1.392(7) . ?
C6 C7 1.364(7) . ?
C7 C8 1.359(7) . ?
C8 C9 1.384(7) . ?
C12 C13 1.412(6) . ?
C12 C17 1.398(6) . ?
C13 C14 1.396(7) . ?
C13 C18 1.509(7) . ?
C14 C15 1.382(7) . ?
C15 C16 1.376(7) . ?
C16 C17 1.390(7) . ?
C17 C19 1.516(7) . ?
C20 C21 1.547(7) . ?
C20 C22 1.533(7) . ?
C20 C23 1.540(7) . ?
C24 C25 1.542(7) . ?
C24 C26 1.520(7) . ?
C24 C27 1.523(7) . ?
C28 C29 1.546(7) . ?
C28 C30 1.541(7) . ?
C28 C31 1.528(7) . ?
C32 C33 1.554(6) . ?
C32 C34 1.530(6) . ?
C32 C35 1.531(6) . ?

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
P11 Ir1 P10 156.54(4) . . ?
C2 Ir1 P10 97.57(15) . . ?
C2 Ir1 P11 95.86(15) . . ?
C2 Ir1 C4 97.0(2) . . ?
C2 Ir1 C12 83.1(2) . . ?
C4 Ir1 P10 98.48(12) . . ?
C4 Ir1 P11 98.87(12) . . ?
C12 Ir1 P10 81.73(13) . . ?
C12 Ir1 P11 80.89(13) . . ?
C12 Ir1 C4 179.75(18) . . ?
C18 P10 Ir1 102.30(16) . . ?
C18 P10 C20 103.6(2) . . ?
C18 P10 C24 103.0(2) . . ?
C20 P10 Ir1 120.78(16) . . ?
C20 P10 C24 109.1(2) . . ?
C24 P10 Ir1 115.37(15) . . ?
C19 P11 Ir1 101.13(15) . . ?
C19 P11 C28 104.4(2) . . ?
C19 P11 C32 102.0(2) . . ?
C28 P11 Ir1 119.38(16) . . ?
C32 P11 Ir1 116.98(15) . . ?
C32 P11 C28 110.0(2) . . ?
O3 C2 Ir1 170.9(5) . . ?
C5 C4 Ir1 124.0(4) . . ?
C5 C4 C9 109.3(4) . . ?
C9 C4 Ir1 126.7(4) . . ?
F5 C5 C4 119.3(4) . . ?
F5 C5 C6 112.7(4) . . ?
C4 C5 C6 128.1(5) . . ?
C7 C6 C5 116.5(5) . . ?
F7 C7 C6 119.7(5) . . ?
C8 C7 F7 119.1(5) . . ?
C8 C7 C6 121.2(5) . . ?
C7 C8 C9 117.8(5) . . ?
F9 C9 C4 119.4(4) . . ?
F9 C9 C8 113.4(4) . . ?
C8 C9 C4 127.2(5) . . ?
C13 C12 Ir1 121.1(3) . . ?
C17 C12 Ir1 121.1(3) . . ?
C17 C12 C13 117.7(4) . . ?
C12 C13 C18 119.1(4) . . ?
C14 C13 C12 120.1(5) . . ?
C14 C13 C18 120.6(4) . . ?
C15 C14 C13 120.3(5) . . ?
C16 C15 C14 120.4(5) . . ?
C15 C16 C17 119.7(5) . . ?
C12 C17 C19 118.2(4) . . ?
C16 C17 C12 121.5(5) . . ?
C16 C17 C19 120.3(4) . . ?
C13 C18 P10 110.1(3) . . ?
C17 C19 P11 109.0(3) . . ?
C21 C20 P10 106.1(3) . . ?
C22 C20 P10 111.0(3) . . ?
C22 C20 C21 108.1(4) . . ?
C22 C20 C23 109.8(4) . . ?
C23 C20 P10 115.0(4) . . ?
C23 C20 C21 106.4(4) . . ?
C25 C24 P10 107.4(3) . . ?
C26 C24 P10 113.9(3) . . ?
C26 C24 C25 107.3(4) . . ?
C26 C24 C27 109.1(4) . . ?
C27 C24 P10 111.4(3) . . ?
C27 C24 C25 107.4(4) . . ?
C29 C28 P11 106.8(3) . . ?
C30 C28 P11 113.2(3) . . ?
C30 C28 C29 107.0(4) . . ?
C31 C28 P11 111.3(3) . . ?
C31 C28 C29 108.1(4) . . ?
C31 C28 C30 110.2(4) . . ?
C33 C32 P11 108.1(3) . . ?
C34 C32 P11 111.7(3) . . ?
C34 C32 C33 108.3(4) . . ?
C34 C32 C35 108.6(4) . . ?
C35 C32 P11 113.4(3) . . ?
C35 C32 C33 106.4(4) . . ?

_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_0104abc14
_database_code_depnum_ccdc_archive 'CCDC 1520524'
_audit_update_record             
;
2016-12-02 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

#====================================================================
# [Ir(PCP)(CO)(H)(2,3-C6H3F2)]
#--------------------------------------------------------------------
# Collected and solved by Adrian Chaplin
#--------------------------------------------------------------------  
# Start Validation Reply Form 

_vrf_PLAT041_0104abc14           
; 
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: 
The hydride ligand was not located.

This also addresses: PLAT043, PLAT068
;
#====================================================================

_audit_creation_date             2015-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            .
_chemical_name_systematic        .
_chemical_formula_moiety         'C31 H47 F2 Ir O P2'
_chemical_formula_sum            'C31 H47 F2 Ir O P2'
_chemical_formula_weight         727.82
_chemical_absolute_configuration .
_chemical_melting_point          'not measured'
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'
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      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                   9.3553(3)
_cell_length_b                   10.5860(3)
_cell_length_c                   16.6571(5)
_cell_angle_alpha                79.927(2)
_cell_angle_beta                 74.522(3)
_cell_angle_gamma                81.288(2)
_cell_volume                     1555.74(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    34902
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.7610
_cell_measurement_theta_min      3.4420
_shelx_estimated_absorpt_T_max   .
_shelx_estimated_absorpt_T_min   .
_exptl_absorpt_coefficient_mu    4.428
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   .
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             732
_exptl_crystal_recrystallization_method 'Crystals grown from heptane at 253 K'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_exptl_special_details           .
_exptl_transmission_factor_max   .
_exptl_transmission_factor_min   .
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            55080
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        27.103
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         3.212
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -3.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3215   38.0000   30.0000 102

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3215   77.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
  3 omega  -66.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3215    0.0000  150.0000 179

#__ type_ start__ end____ width___ exp.time_
  4 omega  -25.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3215  -99.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
  5 omega -103.00    9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4153  -77.0000  -60.0000 112

#__ type_ start__ end____ width___ exp.time_
  6 omega -114.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4153 -178.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
  7 omega  -51.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4153   38.0000  -60.0000 102

#__ type_ start__ end____ width___ exp.time_
  8 omega -114.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4153 -178.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  9 omega   -3.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3215   38.0000 -150.0000 102

#__ type_ start__ end____ width___ exp.time_
 10 omega  -98.00    5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4153  -57.0000   30.0000 103

#__ type_ start__ end____ width___ exp.time_
 11 omega -101.00  -38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4153  155.0000 -129.0000 63

#__ type_ start__ end____ width___ exp.time_
 12 omega  -54.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4153   57.0000   30.0000 104

#__ type_ start__ end____ width___ exp.time_
 13 omega  -79.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4153  120.0000   73.0000 65

#__ type_ start__ end____ width___ exp.time_
 14 omega -103.00    9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4153  -77.0000 -180.0000 112

#__ type_ start__ end____ width___ exp.time_
 15 omega -113.00  -53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4153  178.0000  -90.0000 60

#__ type_ start__ end____ width___ exp.time_
 16 omega  -10.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3215   77.0000  150.0000 112

#__ type_ start__ end____ width___ exp.time_
 17 omega  -25.00    0.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3215  -99.0000 -120.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction: Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0568033000
_diffrn_orient_matrix_UB_12      0.0044545000
_diffrn_orient_matrix_UB_13      0.0376685000
_diffrn_orient_matrix_UB_21      0.0550698000
_diffrn_orient_matrix_UB_22      -0.0093595000
_diffrn_orient_matrix_UB_23      0.0232664000
_diffrn_orient_matrix_UB_31      0.0025106000
_diffrn_orient_matrix_UB_32      0.0676819000
_diffrn_orient_matrix_UB_33      -0.0056357000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6549
_reflns_number_total             6857
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.355
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         6857
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0169
_refine_ls_restrained_S_all      1.050
_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)+(0.0196P)²+0.8390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0408
_refine_ls_wR_factor_ref         0.0414
_refine_special_details          .
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C30(H30A,
 H30B,H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C),
 C35(H35A,H35B,H35C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.28942(2) 0.18522(2) 0.73450(2) 0.01353(3) Uani 1 1 d . . . . .
P10 P 0.12416(6) 0.35245(5) 0.68556(4) 0.01540(11) Uani 1 1 d . . . . .
P11 P 0.39064(7) -0.02706(5) 0.76923(4) 0.01694(12) Uani 1 1 d . . . . .
F5 F 0.51702(15) 0.37410(14) 0.76987(9) 0.0257(3) Uani 1 1 d . . . . .
F6 F 0.52770(16) 0.47133(14) 0.90175(9) 0.0287(3) Uani 1 1 d . . . . .
O3 O 0.58369(18) 0.25899(16) 0.61309(11) 0.0256(4) Uani 1 1 d . . . . .
C2 C 0.4751(3) 0.2357(2) 0.66113(14) 0.0177(4) Uani 1 1 d . . . . .
C4 C 0.3038(2) 0.2626(2) 0.84283(14) 0.0151(4) Uani 1 1 d . . . . .
C5 C 0.4102(2) 0.3423(2) 0.84191(14) 0.0175(4) Uani 1 1 d . . . . .
C6 C 0.4177(3) 0.3950(2) 0.91086(15) 0.0207(5) Uani 1 1 d . . . . .
C7 C 0.3182(3) 0.3727(2) 0.98769(15) 0.0242(5) Uani 1 1 d . . . . .
H7 H 0.3232 0.4096 1.0348 0.029 Uiso 1 1 calc R . . . .
C8 C 0.2098(3) 0.2933(2) 0.99272(15) 0.0253(5) Uani 1 1 d . . . . .
H8 H 0.1382 0.2750 1.0445 0.030 Uiso 1 1 calc R . . . .
C9 C 0.2046(3) 0.2402(2) 0.92328(14) 0.0202(5) Uani 1 1 d . . . . .
H9 H 0.1296 0.1852 0.9301 0.024 Uiso 1 1 calc R . . . .
C12 C 0.2547(3) 0.0995(2) 0.63693(14) 0.0169(4) Uani 1 1 d . . . . .
C13 C 0.1460(3) 0.1540(2) 0.59332(14) 0.0193(5) Uani 1 1 d . . . . .
C14 C 0.1280(3) 0.0993(2) 0.52692(15) 0.0234(5) Uani 1 1 d . . . . .
H14 H 0.0543 0.1381 0.4978 0.028 Uiso 1 1 calc R . . . .
C15 C 0.2182(3) -0.0122(2) 0.50312(15) 0.0246(5) Uani 1 1 d . . . . .
H15 H 0.2076 -0.0484 0.4570 0.029 Uiso 1 1 calc R . . . .
C16 C 0.3234(3) -0.0701(2) 0.54724(15) 0.0224(5) Uani 1 1 d . . . . .
H16 H 0.3832 -0.1473 0.5320 0.027 Uiso 1 1 calc R . . . .
C17 C 0.3415(3) -0.0155(2) 0.61379(14) 0.0186(5) Uani 1 1 d . . . . .
C18 C 0.0401(3) 0.2685(2) 0.62489(15) 0.0204(5) Uani 1 1 d . . . . .
H18A H -0.0545 0.2382 0.6609 0.025 Uiso 1 1 calc R . . . .
H18B H 0.0169 0.3291 0.5764 0.025 Uiso 1 1 calc R . . . .
C19 C 0.4504(3) -0.0809(2) 0.66451(15) 0.0208(5) Uani 1 1 d . . . . .
H19A H 0.5520 -0.0578 0.6357 0.025 Uiso 1 1 calc R . . . .
H19B H 0.4523 -0.1758 0.6705 0.025 Uiso 1 1 calc R . . . .
C20 C 0.2137(3) 0.4871(2) 0.60595(15) 0.0214(5) Uani 1 1 d . . . . .
C21 C 0.3005(3) 0.4275(2) 0.52604(15) 0.0269(5) Uani 1 1 d . . . . .
H21A H 0.3648 0.3501 0.5417 0.040 Uiso 1 1 calc GR . . . .
H21B H 0.3620 0.4905 0.4872 0.040 Uiso 1 1 calc GR . . . .
H21C H 0.2297 0.4041 0.4986 0.040 Uiso 1 1 calc GR . . . .
C22 C 0.3230(3) 0.5434(2) 0.64104(16) 0.0251(5) Uani 1 1 d . . . . .
H22A H 0.2684 0.5803 0.6921 0.038 Uiso 1 1 calc GR . . . .
H22B H 0.3709 0.6110 0.5988 0.038 Uiso 1 1 calc GR . . . .
H22C H 0.3993 0.4748 0.6546 0.038 Uiso 1 1 calc GR . . . .
C23 C 0.1039(3) 0.5991(2) 0.57799(18) 0.0317(6) Uani 1 1 d . . . . .
H23A H 0.0257 0.5643 0.5621 0.048 Uiso 1 1 calc GR . . . .
H23B H 0.1577 0.6551 0.5296 0.048 Uiso 1 1 calc GR . . . .
H23C H 0.0586 0.6492 0.6245 0.048 Uiso 1 1 calc GR . . . .
C24 C -0.0442(3) 0.4221(2) 0.76280(15) 0.0211(5) Uani 1 1 d . . . . .
C25 C -0.1099(3) 0.3109(2) 0.82942(16) 0.0284(6) Uani 1 1 d . . . . .
H25A H -0.1354 0.2466 0.8013 0.043 Uiso 1 1 calc GR . . . .
H25B H -0.1999 0.3454 0.8683 0.043 Uiso 1 1 calc GR . . . .
H25C H -0.0360 0.2704 0.8608 0.043 Uiso 1 1 calc GR . . . .
C26 C -0.1706(3) 0.4886(2) 0.72098(18) 0.0297(6) Uani 1 1 d . . . . .
H26A H -0.1387 0.5674 0.6841 0.044 Uiso 1 1 calc GR . . . .
H26B H -0.2602 0.5108 0.7646 0.044 Uiso 1 1 calc GR . . . .
H26C H -0.1931 0.4298 0.6878 0.044 Uiso 1 1 calc GR . . . .
C27 C 0.0022(3) 0.5179(2) 0.80784(17) 0.0302(6) Uani 1 1 d . . . . .
H27A H 0.0863 0.4769 0.8313 0.045 Uiso 1 1 calc GR . . . .
H27B H -0.0821 0.5437 0.8534 0.045 Uiso 1 1 calc GR . . . .
H27C H 0.0321 0.5943 0.7676 0.045 Uiso 1 1 calc GR . . . .
C28 C 0.5654(3) -0.0605(2) 0.80976(15) 0.0245(5) Uani 1 1 d . . . . .
C29 C 0.6668(3) 0.0453(2) 0.76551(18) 0.0304(6) Uani 1 1 d . . . . .
H29A H 0.6892 0.0466 0.7045 0.046 Uiso 1 1 calc GR . . . .
H29B H 0.7599 0.0276 0.7839 0.046 Uiso 1 1 calc GR . . . .
H29C H 0.6159 0.1293 0.7799 0.046 Uiso 1 1 calc GR . . . .
C30 C 0.6563(3) -0.1912(2) 0.79021(18) 0.0332(6) Uani 1 1 d . . . . .
H30A H 0.5969 -0.2618 0.8197 0.050 Uiso 1 1 calc GR . . . .
H30B H 0.7485 -0.2010 0.8091 0.050 Uiso 1 1 calc GR . . . .
H30C H 0.6809 -0.1936 0.7295 0.050 Uiso 1 1 calc GR . . . .
C31 C 0.5264(3) -0.0542(3) 0.90456(17) 0.0340(6) Uani 1 1 d . . . . .
H31A H 0.4617 0.0257 0.9165 0.051 Uiso 1 1 calc GR . . . .
H31B H 0.6182 -0.0556 0.9226 0.051 Uiso 1 1 calc GR . . . .
H31C H 0.4743 -0.1286 0.9351 0.051 Uiso 1 1 calc GR . . . .
C32 C 0.2470(3) -0.1387(2) 0.83303(16) 0.0257(5) Uani 1 1 d . . . . .
C33 C 0.1322(3) -0.1410(2) 0.78206(17) 0.0290(6) Uani 1 1 d . . . . .
H33A H 0.0894 -0.0526 0.7665 0.043 Uiso 1 1 calc GR . . . .
H33B H 0.0527 -0.1922 0.8163 0.043 Uiso 1 1 calc GR . . . .
H33C H 0.1818 -0.1797 0.7310 0.043 Uiso 1 1 calc GR . . . .
C34 C 0.1609(3) -0.0892(3) 0.91618(16) 0.0334(6) Uani 1 1 d . . . . .
H34A H 0.2318 -0.0755 0.9469 0.050 Uiso 1 1 calc GR . . . .
H34B H 0.0957 -0.1532 0.9505 0.050 Uiso 1 1 calc GR . . . .
H34C H 0.1003 -0.0076 0.9040 0.050 Uiso 1 1 calc GR . . . .
C35 C 0.3164(4) -0.2781(2) 0.85269(19) 0.0370(7) Uani 1 1 d . . . . .
H35A H 0.3799 -0.3072 0.8007 0.056 Uiso 1 1 calc GR . . . .
H35B H 0.2369 -0.3344 0.8767 0.056 Uiso 1 1 calc GR . . . .
H35C H 0.3766 -0.2817 0.8932 0.056 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 P10 2.3511(6) . ?
Ir1 P11 2.3397(6) . ?
Ir1 C2 1.928(2) . ?
Ir1 C4 2.150(2) . ?
Ir1 C12 2.111(2) . ?
P10 C18 1.838(2) . ?
P10 C20 1.897(2) . ?
P10 C24 1.892(2) . ?
P11 C19 1.847(2) . ?
P11 C28 1.893(3) . ?
P11 C32 1.900(2) . ?
F5 C5 1.369(3) . ?
F6 C6 1.364(3) . ?
O3 C2 1.143(3) . ?
C4 C5 1.395(3) . ?
C4 C9 1.416(3) . ?
C5 C6 1.384(3) . ?
C6 C7 1.373(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.386(3) . ?
C12 C13 1.401(3) . ?
C12 C17 1.410(3) . ?
C13 C14 1.393(3) . ?
C13 C18 1.520(3) . ?
C14 C15 1.395(3) . ?
C15 C16 1.389(4) . ?
C16 C17 1.395(3) . ?
C17 C19 1.508(3) . ?
C20 C21 1.547(3) . ?
C20 C22 1.539(3) . ?
C20 C23 1.540(3) . ?
C24 C25 1.547(3) . ?
C24 C26 1.548(3) . ?
C24 C27 1.534(3) . ?
C28 C29 1.535(4) . ?
C28 C30 1.548(3) . ?
C28 C31 1.534(3) . ?
C32 C33 1.541(4) . ?
C32 C34 1.540(3) . ?
C32 C35 1.537(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
P11 Ir1 P10 157.41(2) . . ?
C2 Ir1 P10 99.28(7) . . ?
C2 Ir1 P11 93.61(7) . . ?
C2 Ir1 C4 97.23(9) . . ?
C2 Ir1 C12 89.07(9) . . ?
C4 Ir1 P10 98.15(6) . . ?
C4 Ir1 P11 98.54(6) . . ?
C12 Ir1 P10 81.73(6) . . ?
C12 Ir1 P11 80.00(6) . . ?
C12 Ir1 C4 173.63(8) . . ?
C18 P10 Ir1 101.55(8) . . ?
C18 P10 C20 104.31(11) . . ?
C18 P10 C24 102.76(11) . . ?
C20 P10 Ir1 115.94(8) . . ?
C24 P10 Ir1 119.67(8) . . ?
C24 P10 C20 109.98(10) . . ?
C19 P11 Ir1 100.71(8) . . ?
C19 P11 C28 104.12(11) . . ?
C19 P11 C32 104.46(11) . . ?
C28 P11 Ir1 120.51(8) . . ?
C28 P11 C32 110.61(12) . . ?
C32 P11 Ir1 114.00(8) . . ?
O3 C2 Ir1 174.13(19) . . ?
C5 C4 Ir1 124.08(16) . . ?
C5 C4 C9 112.0(2) . . ?
C9 C4 Ir1 123.92(16) . . ?
F5 C5 C4 120.73(19) . . ?
F5 C5 C6 114.91(19) . . ?
C6 C5 C4 124.4(2) . . ?
F6 C6 C5 118.6(2) . . ?
F6 C6 C7 119.3(2) . . ?
C7 C6 C5 122.1(2) . . ?
C6 C7 C8 116.3(2) . . ?
C9 C8 C7 121.0(2) . . ?
C8 C9 C4 124.3(2) . . ?
C13 C12 Ir1 121.70(16) . . ?
C13 C12 C17 117.9(2) . . ?
C17 C12 Ir1 120.36(17) . . ?
C12 C13 C18 118.0(2) . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 C18 120.7(2) . . ?
C13 C14 C15 120.1(2) . . ?
C16 C15 C14 119.7(2) . . ?
C15 C16 C17 120.3(2) . . ?
C12 C17 C19 118.58(19) . . ?
C16 C17 C12 120.8(2) . . ?
C16 C17 C19 120.6(2) . . ?
C13 C18 P10 110.53(16) . . ?
C17 C19 P11 108.36(15) . . ?
C21 C20 P10 107.24(16) . . ?
C22 C20 P10 110.12(16) . . ?
C22 C20 C21 109.4(2) . . ?
C22 C20 C23 108.2(2) . . ?
C23 C20 P10 115.21(17) . . ?
C23 C20 C21 106.6(2) . . ?
C25 C24 P10 108.76(16) . . ?
C25 C24 C26 106.6(2) . . ?
C26 C24 P10 112.94(17) . . ?
C27 C24 P10 110.03(16) . . ?
C27 C24 C25 108.5(2) . . ?
C27 C24 C26 109.8(2) . . ?
C29 C28 P11 108.25(16) . . ?
C29 C28 C30 107.0(2) . . ?
C30 C28 P11 112.87(17) . . ?
C31 C28 P11 110.45(18) . . ?
C31 C28 C29 107.7(2) . . ?
C31 C28 C30 110.4(2) . . ?
C33 C32 P11 108.67(17) . . ?
C34 C32 P11 111.24(17) . . ?
C34 C32 C33 107.3(2) . . ?
C35 C32 P11 112.73(19) . . ?
C35 C32 C33 107.8(2) . . ?
C35 C32 C34 108.9(2) . . ?

_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_0100abc14
_database_code_depnum_ccdc_archive 'CCDC 1520523'
_audit_update_record             
;
2016-12-02 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

#====================================================================
# [Ir(PCP)(CO)(H)(2-C6H4F)]
#--------------------------------------------------------------------
# Collected and solved by Adrian Chaplin
#--------------------------------------------------------------------  
# Start Validation Reply Form 


_vrf_PLAT041_0100abc14           
; 
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: 
The hydride ligand was not located.

This also addresses: PLAT043, PLAT068
;

_vrf_PLAT301_0100abc14           
; 
PROBLEM: Main Residue  Disorder ............ Percentage =          3 Note   
RESPONSE: 
The structure contains a significant degree of disorder. 
See _publ_section_exptl_refinement.
;
#====================================================================

_audit_creation_date             2015-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            .
_chemical_name_systematic        .
_chemical_formula_moiety         'C31 H48 F Ir O P2'
_chemical_formula_sum            'C31 H48 F Ir O P2'
_chemical_formula_weight         709.83
_chemical_absolute_configuration .
_chemical_melting_point          'not measured'
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'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.0679(3)
_cell_length_b                   16.8659(3)
_cell_length_c                   19.8479(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6048.26(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12479
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.1760
_cell_measurement_theta_min      3.4840
_shelx_estimated_absorpt_T_max   .
_shelx_estimated_absorpt_T_min   .
_exptl_absorpt_coefficient_mu    4.549
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   .
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             2864
_exptl_crystal_recrystallization_method 'Crystals grown from heptane at 253 K'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           .
_exptl_transmission_factor_max   .
_exptl_transmission_factor_min   .
_diffrn_reflns_av_R_equivalents  0.1290
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            80924
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        27.103
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         3.280
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -6.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.6319   38.0000 -120.0000 111

#__ type_ start__ end____ width___ exp.time_
  2 omega  -58.00   62.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.6319  -77.0000  120.0000 120

#__ type_ start__ end____ width___ exp.time_
  3 omega   -7.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.6319   57.0000  -30.0000 111

#__ type_ start__ end____ width___ exp.time_
  4 omega -119.00  -57.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.5694 -178.0000  150.0000 62

#__ type_ start__ end____ width___ exp.time_
  5 omega   -7.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.6319   57.0000   90.0000 111

#__ type_ start__ end____ width___ exp.time_
  6 omega  -59.00   15.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       25.6319  -19.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
  7 omega -119.00  -57.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.5694 -178.0000  -90.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction: Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0083648000
_diffrn_orient_matrix_UB_12      0.0150092000
_diffrn_orient_matrix_UB_13      -0.0324995000
_diffrn_orient_matrix_UB_21      -0.0125903000
_diffrn_orient_matrix_UB_22      -0.0359048000
_diffrn_orient_matrix_UB_23      -0.0146718000
_diffrn_orient_matrix_UB_31      -0.0362276000
_diffrn_orient_matrix_UB_32      0.0159448000
_diffrn_orient_matrix_UB_33      -0.0024110000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4464
_reflns_number_total             6664
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.333
_refine_diff_density_min         -1.134
_refine_diff_density_rms         0.152
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         6664
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.000
_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)+(0.0362P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0938
_refine_special_details          .
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F5-C5 \\sim F9-C9
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F5 \\sim F9: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F9) \\sim Ueq, Uanis(F5) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(F5) = Uanis(F9)
4. Others
 Sof(F9)=Sof(H5)=1-FVAR(1)
 Sof(F5)=Sof(H9)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16)
5.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C30(H30A,
 H30B,H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C),
 C35(H35A,H35B,H35C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.37568(2) 0.20305(2) 0.87834(2) 0.01985(8) Uani 1 1 d . . . . .
P10 P 0.30421(8) 0.12593(9) 0.95159(7) 0.0224(3) Uani 1 1 d . . . . .
P11 P 0.45954(8) 0.22633(9) 0.79021(7) 0.0222(3) Uani 1 1 d . . . . .
F5 F 0.33975(19) 0.3901(2) 0.9236(2) 0.0404(11) Uani 0.947(6) 1 d D U P A 1
F9 F 0.517(3) 0.192(2) 1.001(4) 0.0404(11) Uani 0.053(6) 1 d D U P A 2
O3 O 0.2472(2) 0.3025(3) 0.8235(2) 0.0430(12) Uani 1 1 d . . . . .
C2 C 0.2963(3) 0.2700(4) 0.8467(3) 0.0303(14) Uani 1 1 d . . . . .
C4 C 0.4215(3) 0.2836(3) 0.9519(3) 0.0235(13) Uani 1 1 d . . . . .
C5 C 0.3986(3) 0.3616(4) 0.9618(3) 0.0309(14) Uani 1 1 d D . . . .
H5 H 0.3590 0.3796 0.9343 0.037 Uiso 0.053(6) 1 calc R . P A 2
C6 C 0.4269(4) 0.4152(4) 1.0069(3) 0.0409(17) Uani 1 1 d . . . . .
H6 H 0.4077 0.4675 1.0095 0.049 Uiso 1 1 calc R . . . .
C7 C 0.4838(4) 0.3912(4) 1.0482(3) 0.0416(17) Uani 1 1 d . . . . .
H7 H 0.5047 0.4269 1.0799 0.050 Uiso 1 1 calc R . . . .
C8 C 0.5097(3) 0.3154(4) 1.0432(3) 0.0357(16) Uani 1 1 d . . . . .
H8 H 0.5484 0.2980 1.0720 0.043 Uiso 1 1 calc R . . . .
C9 C 0.4795(3) 0.2637(4) 0.9961(3) 0.0300(14) Uani 1 1 d D . . . .
H9 H 0.4993 0.2115 0.9937 0.036 Uiso 0.947(6) 1 calc R . P A 1
C12 C 0.3324(3) 0.1212(3) 0.8079(3) 0.0225(12) Uani 1 1 d . . . . .
C13 C 0.2747(3) 0.0698(3) 0.8249(3) 0.0261(13) Uani 1 1 d . . . . .
C14 C 0.2499(3) 0.0124(4) 0.7806(3) 0.0366(16) Uani 1 1 d . . . . .
H14 H 0.2119 -0.0232 0.7940 0.044 Uiso 1 1 calc R . . . .
C15 C 0.2798(3) 0.0065(4) 0.7172(3) 0.0413(17) Uani 1 1 d . . . . .
H15 H 0.2647 -0.0349 0.6878 0.050 Uiso 1 1 calc R . . . .
C16 C 0.3325(3) 0.0617(4) 0.6962(3) 0.0350(15) Uani 1 1 d . . . . .
H16 H 0.3506 0.0605 0.6513 0.042 Uiso 1 1 calc R . . . .
C17 C 0.3585(3) 0.1183(4) 0.7413(3) 0.0298(14) Uani 1 1 d . . . . .
C18 C 0.2378(3) 0.0805(4) 0.8930(3) 0.0266(13) Uani 1 1 d . . . . .
H18A H 0.2215 0.0284 0.9107 0.032 Uiso 1 1 calc R . . . .
H18B H 0.1937 0.1149 0.8883 0.032 Uiso 1 1 calc R . . . .
C19 C 0.4117(3) 0.1823(3) 0.7177(3) 0.0292(14) Uani 1 1 d . . . . .
H19A H 0.3840 0.2239 0.6931 0.035 Uiso 1 1 calc R . . . .
H19B H 0.4484 0.1590 0.6864 0.035 Uiso 1 1 calc R . . . .
C20 C 0.2453(3) 0.1761(4) 1.0174(3) 0.0302(14) Uani 1 1 d . . . . .
C21 C 0.2151(3) 0.2537(4) 0.9856(3) 0.0395(17) Uani 1 1 d . . . . .
H21A H 0.2565 0.2891 0.9749 0.059 Uiso 1 1 calc GR . . . .
H21B H 0.1818 0.2800 1.0175 0.059 Uiso 1 1 calc GR . . . .
H21C H 0.1880 0.2411 0.9442 0.059 Uiso 1 1 calc GR . . . .
C22 C 0.2903(4) 0.1983(4) 1.0793(3) 0.0429(18) Uani 1 1 d . . . . .
H22A H 0.3037 0.1502 1.1041 0.064 Uiso 1 1 calc GR . . . .
H22B H 0.2609 0.2331 1.1085 0.064 Uiso 1 1 calc GR . . . .
H22C H 0.3354 0.2261 1.0654 0.064 Uiso 1 1 calc GR . . . .
C23 C 0.1778(3) 0.1259(4) 1.0389(3) 0.0334(15) Uani 1 1 d . . . . .
H23A H 0.1505 0.1090 0.9987 0.050 Uiso 1 1 calc GR . . . .
H23B H 0.1453 0.1578 1.0677 0.050 Uiso 1 1 calc GR . . . .
H23C H 0.1947 0.0792 1.0638 0.050 Uiso 1 1 calc GR . . . .
C24 C 0.3516(3) 0.0368(3) 0.9894(3) 0.0260(13) Uani 1 1 d . . . . .
C25 C 0.3753(3) -0.0184(3) 0.9315(3) 0.0284(13) Uani 1 1 d . . . . .
H25A H 0.3312 -0.0380 0.9080 0.043 Uiso 1 1 calc GR . . . .
H25B H 0.4032 -0.0633 0.9498 0.043 Uiso 1 1 calc GR . . . .
H25C H 0.4064 0.0110 0.8997 0.043 Uiso 1 1 calc GR . . . .
C26 C 0.3010(3) -0.0122(4) 1.0360(3) 0.0311(14) Uani 1 1 d . . . . .
H26A H 0.2909 0.0179 1.0772 0.047 Uiso 1 1 calc GR . . . .
H26B H 0.3257 -0.0621 1.0477 0.047 Uiso 1 1 calc GR . . . .
H26C H 0.2544 -0.0237 1.0128 0.047 Uiso 1 1 calc GR . . . .
C27 C 0.4212(3) 0.0613(4) 1.0291(3) 0.0341(15) Uani 1 1 d . . . . .
H27A H 0.4580 0.0831 0.9980 0.051 Uiso 1 1 calc GR . . . .
H27B H 0.4418 0.0148 1.0519 0.051 Uiso 1 1 calc GR . . . .
H27C H 0.4079 0.1016 1.0626 0.051 Uiso 1 1 calc GR . . . .
C28 C 0.4803(3) 0.3309(4) 0.7627(3) 0.0321(15) Uani 1 1 d . . . . .
C29 C 0.4071(3) 0.3763(4) 0.7666(4) 0.0418(17) Uani 1 1 d . . . . .
H29A H 0.3697 0.3491 0.7393 0.063 Uiso 1 1 calc GR . . . .
H29B H 0.4142 0.4303 0.7495 0.063 Uiso 1 1 calc GR . . . .
H29C H 0.3905 0.3787 0.8136 0.063 Uiso 1 1 calc GR . . . .
C30 C 0.5090(3) 0.3378(4) 0.6897(3) 0.0404(17) Uani 1 1 d . . . . .
H30A H 0.5577 0.3125 0.6862 0.061 Uiso 1 1 calc GR . . . .
H30B H 0.5132 0.3939 0.6773 0.061 Uiso 1 1 calc GR . . . .
H30C H 0.4744 0.3114 0.6590 0.061 Uiso 1 1 calc GR . . . .
C31 C 0.5365(3) 0.3701(4) 0.8102(3) 0.0347(15) Uani 1 1 d . . . . .
H31A H 0.5200 0.3637 0.8570 0.052 Uiso 1 1 calc GR . . . .
H31B H 0.5403 0.4267 0.7995 0.052 Uiso 1 1 calc GR . . . .
H31C H 0.5850 0.3449 0.8045 0.052 Uiso 1 1 calc GR . . . .
C32 C 0.5483(3) 0.1672(4) 0.7956(3) 0.0284(14) Uani 1 1 d . . . . .
C33 C 0.5281(3) 0.0788(3) 0.7924(3) 0.0346(15) Uani 1 1 d . . . . .
H33A H 0.4887 0.0675 0.8251 0.052 Uiso 1 1 calc GR . . . .
H33B H 0.5718 0.0468 0.8032 0.052 Uiso 1 1 calc GR . . . .
H33C H 0.5107 0.0656 0.7470 0.052 Uiso 1 1 calc GR . . . .
C34 C 0.5881(3) 0.1828(4) 0.8626(3) 0.0332(15) Uani 1 1 d . . . . .
H34A H 0.5963 0.2399 0.8680 0.050 Uiso 1 1 calc GR . . . .
H34B H 0.6359 0.1552 0.8627 0.050 Uiso 1 1 calc GR . . . .
H34C H 0.5576 0.1632 0.8999 0.050 Uiso 1 1 calc GR . . . .
C35 C 0.6026(3) 0.1834(4) 0.7377(3) 0.0384(16) Uani 1 1 d . . . . .
H35A H 0.5763 0.1800 0.6946 0.058 Uiso 1 1 calc GR . . . .
H35B H 0.6424 0.1440 0.7386 0.058 Uiso 1 1 calc GR . . . .
H35C H 0.6237 0.2366 0.7428 0.058 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 P10 2.3394(15) . ?
Ir1 P11 2.3474(15) . ?
Ir1 C2 1.931(6) . ?
Ir1 C4 2.159(5) . ?
Ir1 C12 2.115(5) . ?
P10 C18 1.838(5) . ?
P10 C20 1.886(6) . ?
P10 C24 1.885(6) . ?
P11 C19 1.836(6) . ?
P11 C28 1.884(6) . ?
P11 C32 1.892(6) . ?
F5 C5 1.392(7) . ?
F9 C9 1.391(12) . ?
O3 C2 1.140(7) . ?
C4 C5 1.393(8) . ?
C4 C9 1.409(8) . ?
C5 C6 1.371(8) . ?
C6 C7 1.376(9) . ?
C7 C8 1.364(9) . ?
C8 C9 1.390(8) . ?
C12 C13 1.397(7) . ?
C12 C17 1.405(8) . ?
C13 C14 1.383(8) . ?
C13 C18 1.518(8) . ?
C14 C15 1.372(9) . ?
C15 C16 1.395(8) . ?
C16 C17 1.390(8) . ?
C17 C19 1.519(8) . ?
C20 C21 1.552(8) . ?
C20 C22 1.521(8) . ?
C20 C23 1.545(7) . ?
C24 C25 1.540(8) . ?
C24 C26 1.542(7) . ?
C24 C27 1.539(7) . ?
C28 C29 1.532(8) . ?
C28 C30 1.544(8) . ?
C28 C31 1.535(8) . ?
C32 C33 1.537(8) . ?
C32 C34 1.535(8) . ?
C32 C35 1.536(8) . ?

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
P10 Ir1 P11 155.84(5) . . ?
C2 Ir1 P10 96.73(18) . . ?
C2 Ir1 P11 98.02(18) . . ?
C2 Ir1 C4 97.8(2) . . ?
C2 Ir1 C12 83.8(2) . . ?
C4 Ir1 P10 98.15(14) . . ?
C4 Ir1 P11 98.66(14) . . ?
C12 Ir1 P10 80.99(15) . . ?
C12 Ir1 P11 81.70(15) . . ?
C12 Ir1 C4 178.2(2) . . ?
C18 P10 Ir1 101.49(19) . . ?
C18 P10 C20 104.9(3) . . ?
C18 P10 C24 102.5(3) . . ?
C20 P10 Ir1 119.5(2) . . ?
C24 P10 Ir1 116.08(18) . . ?
C24 P10 C20 109.8(3) . . ?
C19 P11 Ir1 102.27(19) . . ?
C19 P11 C28 104.2(3) . . ?
C19 P11 C32 103.3(3) . . ?
C28 P11 Ir1 120.1(2) . . ?
C28 P11 C32 109.9(3) . . ?
C32 P11 Ir1 114.63(19) . . ?
O3 C2 Ir1 172.2(6) . . ?
C5 C4 Ir1 125.2(4) . . ?
C5 C4 C9 111.0(5) . . ?
C9 C4 Ir1 123.8(4) . . ?
F5 C5 C4 118.5(5) . . ?
C6 C5 F5 114.3(6) . . ?
C6 C5 C4 127.2(6) . . ?
C5 C6 C7 118.3(6) . . ?
C8 C7 C6 119.3(6) . . ?
C7 C8 C9 120.2(6) . . ?
F9 C9 C4 128(3) . . ?
C8 C9 F9 108(3) . . ?
C8 C9 C4 124.1(6) . . ?
C13 C12 Ir1 121.4(4) . . ?
C13 C12 C17 117.2(5) . . ?
C17 C12 Ir1 121.3(4) . . ?
C12 C13 C18 118.0(5) . . ?
C14 C13 C12 121.5(6) . . ?
C14 C13 C18 120.5(5) . . ?
C15 C14 C13 120.4(6) . . ?
C14 C15 C16 119.6(6) . . ?
C17 C16 C15 119.8(6) . . ?
C12 C17 C19 118.6(5) . . ?
C16 C17 C12 121.0(6) . . ?
C16 C17 C19 120.2(5) . . ?
C13 C18 P10 109.0(4) . . ?
C17 C19 P11 110.1(4) . . ?
C21 C20 P10 107.1(4) . . ?
C22 C20 P10 111.6(4) . . ?
C22 C20 C21 108.0(5) . . ?
C22 C20 C23 109.6(5) . . ?
C23 C20 P10 113.0(4) . . ?
C23 C20 C21 107.2(5) . . ?
C25 C24 P10 108.1(4) . . ?
C25 C24 C26 106.7(5) . . ?
C26 C24 P10 113.4(4) . . ?
C27 C24 P10 111.1(4) . . ?
C27 C24 C25 108.5(5) . . ?
C27 C24 C26 108.7(5) . . ?
C29 C28 P11 106.4(4) . . ?
C29 C28 C30 107.4(5) . . ?
C29 C28 C31 108.9(5) . . ?
C30 C28 P11 114.2(5) . . ?
C31 C28 P11 110.9(4) . . ?
C31 C28 C30 108.8(5) . . ?
C33 C32 P11 107.9(4) . . ?
C34 C32 P11 110.9(4) . . ?
C34 C32 C33 108.3(5) . . ?
C34 C32 C35 108.6(5) . . ?
C35 C32 P11 113.9(4) . . ?
C35 C32 C33 107.1(5) . . ?

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