# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

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

data_syhbzfa
_database_code_depnum_ccdc_archive 'CCDC 1055728'
_audit_update_record             
;
2015-05-23 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;
_audit_creation_date             2015-05-13
_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         'C43 H29 F2 Ir N2 O4'
_chemical_formula_sum            'C43 H29 F2 Ir N2 O4'
_chemical_formula_weight         867.88
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 O1 N1 F1 Ir1'
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'
N N 0.0061 0.0033 '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      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                   12.8015(6)
_cell_length_b                   21.5451(8)
_cell_length_c                   13.7718(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.598(6)
_cell_angle_gamma                90
_cell_volume                     3506.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5262
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7840
_cell_measurement_theta_min      2.6450
_shelx_estimated_absorpt_T_max   0.676
_shelx_estimated_absorpt_T_min   0.614
_exptl_absorpt_coefficient_mu    3.865
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15198
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         26.339
_diffrn_reflns_theta_min         2.475
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -84.00    0.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0184  -57.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega  -42.00   53.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0184   57.0000   30.0000 95
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0136009000
_diffrn_orient_matrix_UB_12      -0.0317268000
_diffrn_orient_matrix_UB_13      0.0022802000
_diffrn_orient_matrix_UB_21      0.0047332000
_diffrn_orient_matrix_UB_22      0.0041072000
_diffrn_orient_matrix_UB_23      0.0526510000
_diffrn_orient_matrix_UB_31      -0.0582765000
_diffrn_orient_matrix_UB_32      0.0077084000
_diffrn_orient_matrix_UB_33      -0.0183947000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5128
_reflns_number_total             7158
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    ?
_refine_diff_density_max         1.624
_refine_diff_density_min         -1.105
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         7158
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.039
_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)+(0.0496P)²+4.3102P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1186
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C33-C34 \\sim C38-C37
 with sigma of 0.02
 C31-C32 \\sim C33-C38
 with sigma of 0.02
 C5-C4 \\sim C37-C36
 with sigma of 0.02
 C38-C33 \\sim C34-C35
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C33) = Uanis(C38)
Uanis(C33) = Uanis(C38) = Uanis(C37) = Uanis(C36) = Uanis(C35) = Uanis(C34)
Uanis(C23) = Uanis(C33)
4.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C2(H2), C31(H31), C3(H3), C40(H40), C5(H5), C10(H10), C9(H9),
 C4(H4), C23(H23), C24(H24), C19(H19), C22(H22), C16(H16), C15(H15), C18(H18),
 C28(H28), C29(H29), C34(H34), C38(H38), C35(H35), C37(H37), C21(H21)
4.b Idealised Me refined as rotating group:
 C43(H43a,H43b,H43c), C42(H42a,H42b,H42c)
;
_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 0.72213(2) 0.60894(2) 0.31957(2) 0.04667(11) Uani 1 1 d . . . . .
O3 O 0.8184(4) 0.5328(2) 0.2992(4) 0.0535(12) Uani 1 1 d . . . . .
O1 O 0.4426(3) 0.5027(2) 0.1627(4) 0.0555(12) Uani 1 1 d . . . . .
O4 O 0.7714(4) 0.6621(2) 0.2121(4) 0.0667(14) Uani 1 1 d . . . . .
C33 C 0.3613(9) 0.7689(6) 0.2912(10) 0.1243(18) Uani 1 1 d D . . . .
N1 N 0.5821(4) 0.5729(2) 0.2060(4) 0.0446(13) Uani 1 1 d . . . . .
N2 N 0.8554(4) 0.6508(2) 0.4345(4) 0.0506(14) Uani 1 1 d . . . . .
C41 C 0.8794(6) 0.5341(4) 0.2463(6) 0.0571(19) Uani 1 1 d . . . . .
C12 C 0.7206(5) 0.5380(3) 0.5171(6) 0.0540(18) Uani 1 1 d . . . . .
H12 H 0.7785 0.5635 0.5602 0.065 Uiso 1 1 calc R . . . .
C2 C 0.5239(7) 0.6211(4) 0.0244(6) 0.068(2) Uani 1 1 d . . . . .
H2 H 0.5811 0.6506 0.0409 0.082 Uiso 1 1 calc R . . . .
C14 C 0.7396(6) 0.4767(4) 0.6816(6) 0.060(2) Uani 1 1 d . . . . .
C43 C 0.9470(6) 0.4756(4) 0.2512(7) 0.079(3) Uani 1 1 d . . . . .
H43A H 1.0149 0.4762 0.3137 0.119 Uiso 1 1 calc GR . . . .
H43B H 0.9664 0.4735 0.1905 0.119 Uiso 1 1 calc GR . . . .
H43C H 0.9026 0.4400 0.2525 0.119 Uiso 1 1 calc GR . . . .
C11 C 0.6854(5) 0.4897(4) 0.5627(6) 0.0574(19) Uani 1 1 d . . . . .
C31 C 0.5275(5) 0.6977(3) 0.3100(6) 0.064(2) Uani 1 1 d D . . . .
H31 H 0.4756 0.6690 0.2678 0.077 Uiso 1 1 calc R . . . .
C3 C 0.4418(7) 0.6151(4) -0.0773(6) 0.074(2) Uani 1 1 d . . . . .
H3 H 0.4443 0.6411 -0.1302 0.088 Uiso 1 1 calc R . . . .
C6 C 0.4299(6) 0.5380(4) 0.0731(6) 0.0561(18) Uani 1 1 d . . . . .
C32 C 0.6414(5) 0.6832(3) 0.3471(6) 0.0543(18) Uani 1 1 d D . . . .
C40 C 0.8902(7) 0.5825(5) 0.1867(7) 0.077(2) Uani 1 1 d . . . . .
H40 H 0.9385 0.5756 0.1518 0.092 Uiso 1 1 calc R . . . .
C20 C 0.9729(5) 0.6435(3) 0.4916(5) 0.0502(17) Uani 1 1 d . . . . .
C5 C 0.3481(6) 0.5314(4) -0.0280(6) 0.064(2) Uani 1 1 d D . . . .
H5 H 0.2913 0.5017 -0.0442 0.076 Uiso 1 1 calc R . . . .
C1 C 0.5155(5) 0.5811(3) 0.0987(6) 0.0495(16) Uani 1 1 d . . . . .
C10 C 0.5991(6) 0.4498(4) 0.4989(6) 0.064(2) Uani 1 1 d . . . . .
H10 H 0.5770 0.4162 0.5288 0.077 Uiso 1 1 calc R . . . .
C9 C 0.5473(6) 0.4604(4) 0.3924(6) 0.061(2) Uani 1 1 d . . . . .
H9 H 0.4892 0.4346 0.3506 0.073 Uiso 1 1 calc R . . . .
C4 C 0.3561(6) 0.5707(4) -0.1011(6) 0.070(2) Uani 1 1 d D . . . .
H4 H 0.3027 0.5681 -0.1696 0.084 Uiso 1 1 calc R . . . .
C7 C 0.5357(5) 0.5268(3) 0.2395(5) 0.0468(16) Uani 1 1 d . . . . .
C25 C 1.0111(6) 0.6977(3) 0.5489(7) 0.069(2) Uani 1 1 d . . . . .
C23 C 1.1936(9) 0.6582(6) 0.6205(10) 0.1243(18) Uani 1 1 d . . . . .
H23 H 1.2698 0.6623 0.6635 0.149 Uiso 1 1 calc R . . . .
C24 C 1.1222(6) 0.7069(4) 0.6165(7) 0.083(3) Uani 1 1 d . . . . .
H24 H 1.1466 0.7429 0.6560 0.100 Uiso 1 1 calc R . . . .
C30 C 0.4875(6) 0.7538(4) 0.3334(7) 0.073(2) Uani 1 1 d . . . . .
C8 C 0.5821(5) 0.5097(3) 0.3477(6) 0.0497(17) Uani 1 1 d . . . . .
C39 C 0.8388(7) 0.6409(5) 0.1708(7) 0.077(2) Uani 1 1 d . . . . .
C19 C 0.7713(6) 0.5265(5) 0.7477(7) 0.075(3) Uani 1 1 d . . . . .
H19 H 0.7588 0.5667 0.7214 0.090 Uiso 1 1 calc R . . . .
C13 C 0.6730(5) 0.5508(3) 0.4077(5) 0.0440(15) Uani 1 1 d . . . . .
C27 C 0.7160(6) 0.7289(3) 0.4132(7) 0.065(2) Uani 1 1 d . . . . .
C26 C 0.8314(6) 0.7071(3) 0.4590(7) 0.066(2) Uani 1 1 d . . . . .
C22 C 1.1586(6) 0.6037(4) 0.5646(7) 0.068(2) Uani 1 1 d . . . . .
H22 H 1.2108 0.5725 0.5707 0.081 Uiso 1 1 calc R . . . .
C16 C 0.8132(9) 0.4075(6) 0.8263(9) 0.099(3) Uani 1 1 d . . . . .
H16 H 0.8261 0.3669 0.8512 0.119 Uiso 1 1 calc R . . . .
C15 C 0.7613(8) 0.4201(6) 0.7177(8) 0.093(3) Uani 1 1 d . . . . .
H15 H 0.7421 0.3871 0.6705 0.111 Uiso 1 1 calc R . . . .
C42 C 0.8574(11) 0.6854(6) 0.0937(11) 0.140(5) Uani 1 1 d . . . . .
H42A H 0.7932 0.6841 0.0281 0.210 Uiso 1 1 calc GR . . . .
H42B H 0.9241 0.6735 0.0824 0.210 Uiso 1 1 calc GR . . . .
H42C H 0.8666 0.7267 0.1216 0.210 Uiso 1 1 calc GR . . . .
O2 O 0.9197(4) 0.7378(2) 0.5279(5) 0.0834(19) Uani 1 1 d . . . . .
F1 F 0.8960(5) 0.4461(4) 0.9975(4) 0.134(2) Uani 1 1 d . . . . .
C18 C 0.8243(7) 0.5154(6) 0.8584(8) 0.094(3) Uani 1 1 d . . . . .
H18 H 0.8452 0.5483 0.9057 0.112 Uiso 1 1 calc R . . . .
C17 C 0.8433(8) 0.4560(7) 0.8926(8) 0.094(3) Uani 1 1 d . . . . .
C28 C 0.6782(7) 0.7855(4) 0.4350(8) 0.097(3) Uani 1 1 d . . . . .
H28 H 0.7291 0.8145 0.4776 0.116 Uiso 1 1 calc R . . . .
C29 C 0.5639(7) 0.7980(4) 0.3927(8) 0.096(3) Uani 1 1 d . . . . .
H29 H 0.5378 0.8366 0.4041 0.116 Uiso 1 1 calc R . . . .
F2 F 0.0233(5) 0.8044(4) 0.1901(9) 0.212(5) Uani 1 1 d . . . . .
C36 C 0.1348(9) 0.7916(6) 0.2260(11) 0.1243(18) Uani 1 1 d D . . . .
C34 C 0.2980(8) 0.7448(6) 0.3458(11) 0.1243(18) Uani 1 1 d D . . . .
H34 H 0.3341 0.7206 0.4053 0.149 Uiso 1 1 calc R . . . .
C38 C 0.3127(8) 0.7933(6) 0.2072(10) 0.1243(18) Uani 1 1 d D . . . .
H38 H 0.3526 0.8038 0.1656 0.149 Uiso 1 1 calc R . . . .
C35 C 0.1837(8) 0.7559(6) 0.3139(10) 0.1243(18) Uani 1 1 d D . . . .
H35 H 0.1419 0.7398 0.3503 0.149 Uiso 1 1 calc R . . . .
C37 C 0.1894(8) 0.8068(6) 0.1692(11) 0.1243(18) Uani 1 1 d D . . . .
H37 H 0.1524 0.8261 0.1046 0.149 Uiso 1 1 calc R . . . .
C21 C 1.0458(6) 0.5955(3) 0.4992(6) 0.062(2) Uani 1 1 d . . . . .
H21 H 1.0207 0.5588 0.4619 0.074 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 O3 2.134(4) . ?
Ir1 O4 2.148(6) . ?
Ir1 N1 2.027(5) . ?
Ir1 N2 2.038(5) . ?
Ir1 C32 2.019(6) . ?
Ir1 C13 2.007(7) . ?
O3 C41 1.256(8) . ?
O1 C6 1.406(9) . ?
O1 C7 1.356(7) . ?
O4 C39 1.285(10) . ?
C33 C30 1.527(13) . ?
C33 C34 1.400(13) . ?
C33 C38 1.204(12) . ?
N1 C1 1.404(8) . ?
N1 C7 1.327(8) . ?
N2 C20 1.413(7) . ?
N2 C26 1.326(9) . ?
C41 C43 1.516(10) . ?
C41 C40 1.366(11) . ?
C12 H12 0.9300 . ?
C12 C11 1.377(10) . ?
C12 C13 1.419(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.397(10) . ?
C2 C1 1.375(10) . ?
C14 C11 1.539(10) . ?
C14 C19 1.364(11) . ?
C14 C15 1.306(13) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C11 C10 1.409(10) . ?
C31 H31 0.9300 . ?
C31 C32 1.382(8) . ?
C31 C30 1.398(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.397(11) . ?
C6 C5 1.391(9) . ?
C6 C1 1.374(9) . ?
C32 C27 1.429(9) . ?
C40 H40 0.9300 . ?
C40 C39 1.399(13) . ?
C20 C25 1.387(9) . ?
C20 C21 1.371(9) . ?
C5 H5 0.9300 . ?
C5 C4 1.348(10) . ?
C10 H10 0.9300 . ?
C10 C9 1.377(10) . ?
C9 H9 0.9300 . ?
C9 C8 1.384(10) . ?
C4 H4 0.9300 . ?
C7 C8 1.425(10) . ?
C25 C24 1.383(10) . ?
C25 O2 1.393(9) . ?
C23 H23 0.9300 . ?
C23 C24 1.379(13) . ?
C23 C22 1.380(14) . ?
C24 H24 0.9300 . ?
C30 C29 1.385(11) . ?
C8 C13 1.442(9) . ?
C39 C42 1.517(13) . ?
C19 H19 0.9300 . ?
C19 C18 1.430(12) . ?
C27 C26 1.443(9) . ?
C27 C28 1.387(10) . ?
C26 O2 1.338(8) . ?
C22 H22 0.9300 . ?
C22 C21 1.389(10) . ?
C16 H16 0.9300 . ?
C16 C15 1.410(13) . ?
C16 C17 1.342(15) . ?
C15 H15 0.9300 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
F1 C17 1.356(10) . ?
C18 H18 0.9300 . ?
C18 C17 1.354(15) . ?
C28 H28 0.9300 . ?
C28 C29 1.378(11) . ?
C29 H29 0.9300 . ?
F2 C36 1.348(12) . ?
C36 C35 1.367(16) . ?
C36 C37 1.275(13) . ?
C34 H34 0.9300 . ?
C34 C35 1.376(11) . ?
C38 H38 0.9300 . ?
C38 C37 1.489(12) . ?
C35 H35 0.9300 . ?
C37 H37 0.9300 . ?
C21 H21 0.9300 . ?

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
O3 Ir1 O4 88.9(2) . . ?
N1 Ir1 O3 89.35(18) . . ?
N1 Ir1 O4 94.6(2) . . ?
N1 Ir1 N2 175.56(19) . . ?
N2 Ir1 O3 95.09(19) . . ?
N2 Ir1 O4 85.4(2) . . ?
C32 Ir1 O3 175.8(2) . . ?
C32 Ir1 O4 90.8(3) . . ?
C32 Ir1 N1 94.8(2) . . ?
C32 Ir1 N2 80.8(2) . . ?
C13 Ir1 O3 86.0(2) . . ?
C13 Ir1 O4 173.1(2) . . ?
C13 Ir1 N1 80.6(2) . . ?
C13 Ir1 N2 99.8(2) . . ?
C13 Ir1 C32 94.5(3) . . ?
C41 O3 Ir1 125.4(5) . . ?
C7 O1 C6 104.3(5) . . ?
C39 O4 Ir1 122.7(5) . . ?
C34 C33 C30 117.6(10) . . ?
C38 C33 C30 122.6(11) . . ?
C38 C33 C34 119.1(12) . . ?
C1 N1 Ir1 139.7(5) . . ?
C7 N1 Ir1 113.6(4) . . ?
C7 N1 C1 106.7(5) . . ?
C20 N2 Ir1 141.0(4) . . ?
C26 N2 Ir1 113.3(4) . . ?
C26 N2 C20 105.1(5) . . ?
O3 C41 C43 115.3(7) . . ?
O3 C41 C40 126.5(7) . . ?
C40 C41 C43 118.2(8) . . ?
C11 C12 H12 118.4 . . ?
C11 C12 C13 123.2(6) . . ?
C13 C12 H12 118.4 . . ?
C3 C2 H2 121.8 . . ?
C1 C2 H2 121.8 . . ?
C1 C2 C3 116.4(7) . . ?
C19 C14 C11 117.6(8) . . ?
C15 C14 C11 121.3(8) . . ?
C15 C14 C19 121.0(9) . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C12 C11 C14 122.0(7) . . ?
C12 C11 C10 119.5(7) . . ?
C10 C11 C14 118.5(7) . . ?
C32 C31 H31 118.7 . . ?
C32 C31 C30 122.5(7) . . ?
C30 C31 H31 118.7 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(8) . . ?
C4 C3 H3 119.4 . . ?
C5 C6 O1 127.7(7) . . ?
C1 C6 O1 109.1(6) . . ?
C1 C6 C5 123.1(7) . . ?
C31 C32 Ir1 130.7(5) . . ?
C31 C32 C27 115.7(6) . . ?
C27 C32 Ir1 113.6(5) . . ?
C41 C40 H40 115.5 . . ?
C41 C40 C39 129.1(8) . . ?
C39 C40 H40 115.5 . . ?
C25 C20 N2 106.9(6) . . ?
C21 C20 N2 132.4(6) . . ?
C21 C20 C25 120.7(6) . . ?
C6 C5 H5 122.0 . . ?
C4 C5 C6 116.0(7) . . ?
C4 C5 H5 122.0 . . ?
C2 C1 N1 132.3(6) . . ?
C6 C1 N1 106.7(6) . . ?
C6 C1 C2 121.0(7) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 C11 120.3(7) . . ?
C9 C10 H10 119.8 . . ?
C10 C9 H9 120.2 . . ?
C10 C9 C8 119.7(7) . . ?
C8 C9 H9 120.2 . . ?
C3 C4 H4 118.9 . . ?
C5 C4 C3 122.2(7) . . ?
C5 C4 H4 118.9 . . ?
O1 C7 C8 127.2(6) . . ?
N1 C7 O1 113.1(6) . . ?
N1 C7 C8 119.6(6) . . ?
C20 C25 O2 108.6(6) . . ?
C24 C25 C20 123.4(7) . . ?
C24 C25 O2 127.9(7) . . ?
C24 C23 H23 118.1 . . ?
C24 C23 C22 123.8(9) . . ?
C22 C23 H23 118.1 . . ?
C25 C24 H24 122.8 . . ?
C23 C24 C25 114.3(8) . . ?
C23 C24 H24 122.8 . . ?
C31 C30 C33 121.6(8) . . ?
C29 C30 C33 118.8(8) . . ?
C29 C30 C31 119.5(7) . . ?
C9 C8 C7 125.9(6) . . ?
C9 C8 C13 122.9(7) . . ?
C7 C8 C13 111.2(6) . . ?
O4 C39 C40 127.3(8) . . ?
O4 C39 C42 113.5(9) . . ?
C40 C39 C42 119.2(9) . . ?
C14 C19 H19 120.7 . . ?
C14 C19 C18 118.6(10) . . ?
C18 C19 H19 120.7 . . ?
C12 C13 Ir1 131.0(5) . . ?
C12 C13 C8 114.4(6) . . ?
C8 C13 Ir1 114.1(5) . . ?
C32 C27 C26 112.1(6) . . ?
C28 C27 C32 122.6(6) . . ?
C28 C27 C26 125.1(7) . . ?
N2 C26 C27 119.0(6) . . ?
N2 C26 O2 114.6(6) . . ?
O2 C26 C27 126.4(7) . . ?
C23 C22 H22 119.9 . . ?
C23 C22 C21 120.3(8) . . ?
C21 C22 H22 119.9 . . ?
C15 C16 H16 121.1 . . ?
C17 C16 H16 121.1 . . ?
C17 C16 C15 117.8(11) . . ?
C14 C15 C16 121.9(11) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C26 O2 C25 104.7(5) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 C19 118.4(10) . . ?
C17 C18 H18 120.8 . . ?
C16 C17 F1 119.9(12) . . ?
C16 C17 C18 122.2(10) . . ?
C18 C17 F1 117.9(12) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 C27 118.9(8) . . ?
C29 C28 H28 120.5 . . ?
C30 C29 H29 119.7 . . ?
C28 C29 C30 120.6(7) . . ?
C28 C29 H29 119.7 . . ?
F2 C36 C35 120.1(13) . . ?
C37 C36 F2 118.3(13) . . ?
C37 C36 C35 121.0(11) . . ?
C33 C34 H34 119.1 . . ?
C35 C34 C33 121.9(13) . . ?
C35 C34 H34 119.1 . . ?
C33 C38 H38 119.7 . . ?
C33 C38 C37 120.6(13) . . ?
C37 C38 H38 119.7 . . ?
C36 C35 C34 116.7(13) . . ?
C36 C35 H35 121.7 . . ?
C34 C35 H35 121.7 . . ?
C36 C37 C38 119.4(12) . . ?
C36 C37 H37 120.3 . . ?
C38 C37 H37 120.3 . . ?
C20 C21 C22 117.5(7) . . ?
C20 C21 H21 121.3 . . ?
C22 C21 H21 121.3 . . ?

_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_syh4
_database_code_depnum_ccdc_archive 'CCDC 1055767'
_audit_update_record             
;
2015-05-23 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;
_audit_creation_date             2015-03-23
_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         'C45 H35 Ir N2 O4'
_chemical_formula_sum            'C45 H35 Ir N2 O4'
_chemical_formula_weight         859.95
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 O1 Ir1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 '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'

_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                   11.2055(3)
_cell_length_b                   12.7447(5)
_cell_length_c                   14.5575(5)
_cell_angle_alpha                65.313(4)
_cell_angle_beta                 87.690(2)
_cell_angle_gamma                77.970(3)
_cell_volume                     1844.90(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12902
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.1180
_cell_measurement_theta_min      3.3270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.375
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22203
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.183
_diffrn_reflns_theta_max         67.183
_diffrn_reflns_theta_min         3.346
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -3.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0339  -99.0000    0.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega  -35.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0339  -38.0000   90.0000 100

#__ type_ start__ end____ width___ exp.time_
  3 omega   15.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0339   38.0000  -90.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega -120.00  -95.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  125.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega   53.00   98.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -83.0000  144.1369 45

#__ type_ start__ end____ width___ exp.time_
  6 omega   14.00   40.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -84.0000 -149.2421 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   60.00  131.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  122.5876 71

#__ type_ start__ end____ width___ exp.time_
  8 omega   62.00   93.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
  9 omega   74.00  130.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000  -74.8272 56

#__ type_ start__ end____ width___ exp.time_
 10 omega   25.00   77.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 11 omega  134.00  159.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   71.00   96.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega  126.00  168.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  120.0000 42

#__ type_ start__ end____ width___ exp.time_
 14 omega   65.00  119.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000   30.0000 54

#__ type_ start__ end____ width___ exp.time_
 15 omega   22.00   75.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 16 omega   80.00  106.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -71.0000  -24.8238 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   37.00   63.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   21.00   76.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
 19 omega   48.00   73.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega   38.00   82.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
 21 omega  127.00  152.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega   67.00  111.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
 23 omega   17.00   52.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   60.0000 35

#__ type_ start__ end____ width___ exp.time_
 24 omega   20.00   53.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  -30.0000 33

#__ type_ start__ end____ width___ exp.time_
 25 omega   16.00   66.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
 26 omega   33.00   74.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
 27 omega   99.00  124.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 28 omega   92.00  125.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 29 omega  138.00  171.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 30 omega   63.00   89.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega  111.00  170.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000    0.0000 59

#__ type_ start__ end____ width___ exp.time_
 32 omega   57.00  109.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -84.0000 -149.2421 52

#__ type_ start__ end____ width___ exp.time_
 33 omega  102.00  127.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 34 omega   61.00   96.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
 35 omega   17.00   43.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000  -74.8272 26

#__ type_ start__ end____ width___ exp.time_
 36 omega   97.00  122.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 37 omega   16.00   64.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -150.0000 48

#__ type_ start__ end____ width___ exp.time_
 38 omega   19.00   45.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 39 omega   71.00   96.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 40 omega   21.00   46.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000    0.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 41 omega   80.00  106.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000    0.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 42 omega  127.00  152.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000    0.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 43 omega   81.00  106.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000 -153.6625 25

#__ type_ start__ end____ width___ exp.time_
 44 omega   73.00  110.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
 45 omega   18.00   43.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 46 omega   70.00  118.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000    1.4773 48
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0240231000
_diffrn_orient_matrix_UB_12      0.0855179000
_diffrn_orient_matrix_UB_13      0.0434819000
_diffrn_orient_matrix_UB_21      -0.0179735000
_diffrn_orient_matrix_UB_22      0.1012078000
_diffrn_orient_matrix_UB_23      -0.1071350000
_diffrn_orient_matrix_UB_31      -0.1375306000
_diffrn_orient_matrix_UB_32      0.0311098000
_diffrn_orient_matrix_UB_33      0.0153163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6005
_reflns_number_total             6581
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6581
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0245
_refine_ls_restrained_S_all      1.077
_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)+(0.0308P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0606
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C12(H12), C22(H22), C33(H33), C2(H2), C30(H30), C5(H5), C10(H10),
 C32(H32), C35(H35), C25(H25), C3(H3), C42(H42), C4(H4), C9(H9), C18(H18),
 C24(H24), C15(H15), C23(H23), C39(H39), C16(H16), C36(H36), C38(H38)
2.b Idealised Me refined as rotating group:
 C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C40(H40A,H40B,H40C), C20(H20A,H20B,
 H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.20656(2) 0.25250(2) 0.33860(2) 0.03556(6) Uani 1 1 d . . . . .
N1 N 0.1317(2) 0.4055(2) 0.2188(2) 0.0392(6) Uani 1 1 d . . . . .
N2 N 0.2791(2) 0.1096(2) 0.4674(2) 0.0382(6) Uani 1 1 d . . . . .
O2 O 0.4217(2) 0.0295(2) 0.59387(18) 0.0477(6) Uani 1 1 d . . . . .
O3 O 0.0761(2) 0.1728(2) 0.30281(19) 0.0458(5) Uani 1 1 d . . . . .
O4 O 0.3360(2) 0.1820(2) 0.25579(18) 0.0484(6) Uani 1 1 d . . . . .
O1 O -0.0200(2) 0.56490(19) 0.15915(17) 0.0456(5) Uani 1 1 d . . . . .
C13 C 0.0771(3) 0.3231(3) 0.4089(2) 0.0365(7) Uani 1 1 d . . . . .
C19 C 0.0045(4) 0.2428(3) 0.7309(3) 0.0525(9) Uani 1 1 d . . . . .
H19 H 0.0858 0.2446 0.7161 0.063 Uiso 1 1 calc R . . . .
C29 C 0.3383(3) 0.3155(3) 0.3764(2) 0.0377(7) Uani 1 1 d . . . . .
C1 C 0.1482(3) 0.4678(3) 0.1157(3) 0.0429(8) Uani 1 1 d . . . . .
C27 C 0.3706(3) 0.1255(3) 0.5089(2) 0.0396(7) Uani 1 1 d . . . . .
C7 C 0.0340(3) 0.4662(3) 0.2402(3) 0.0385(7) Uani 1 1 d . . . . .
C44 C -0.0055(4) 0.0497(4) 0.2511(4) 0.0700(12) Uani 1 1 d . . . . .
H44A H -0.0148 -0.0123 0.3155 0.105 Uiso 1 1 calc GR . . . .
H44B H 0.0106 0.0178 0.2015 0.105 Uiso 1 1 calc GR . . . .
H44C H -0.0792 0.1096 0.2309 0.105 Uiso 1 1 calc GR . . . .
C26 C 0.2634(3) -0.0053(3) 0.5285(3) 0.0411(7) Uani 1 1 d . . . . .
C12 C 0.0492(3) 0.2809(3) 0.5103(3) 0.0395(7) Uani 1 1 d . . . . .
H12 H 0.1000 0.2133 0.5569 0.047 Uiso 1 1 calc R . . . .
C21 C 0.3520(3) -0.0535(3) 0.6063(3) 0.0432(8) Uani 1 1 d . . . . .
C22 C 0.3667(4) -0.1667(3) 0.6816(3) 0.0539(9) Uani 1 1 d . . . . .
H22 H 0.4277 -0.1977 0.7330 0.065 Uiso 1 1 calc R . . . .
C33 C 0.5114(3) 0.2595(3) 0.4980(3) 0.0488(8) Uani 1 1 d . . . . .
H33 H 0.5561 0.2052 0.5572 0.059 Uiso 1 1 calc R . . . .
C8 C -0.0034(3) 0.4279(3) 0.3418(3) 0.0386(7) Uani 1 1 d . . . . .
C28 C 0.4108(3) 0.2348(3) 0.4649(2) 0.0403(7) Uani 1 1 d . . . . .
C34 C 0.5227(3) 0.5572(3) 0.2881(3) 0.0432(8) Uani 1 1 d . . . . .
C2 C 0.2347(4) 0.4479(4) 0.0517(3) 0.0577(10) Uani 1 1 d . . . . .
H2 H 0.3000 0.3833 0.0749 0.069 Uiso 1 1 calc R . . . .
C11 C -0.0523(3) 0.3362(3) 0.5446(3) 0.0410(7) Uani 1 1 d . . . . .
C41 C 0.1001(3) 0.1030(3) 0.2595(3) 0.0498(9) Uani 1 1 d . . . . .
C30 C 0.3746(3) 0.4220(3) 0.3219(3) 0.0420(7) Uani 1 1 d . . . . .
H30 H 0.3286 0.4779 0.2640 0.050 Uiso 1 1 calc R . . . .
C5 C 0.0356(4) 0.6471(3) -0.0200(3) 0.0565(9) Uani 1 1 d . . . . .
H5 H -0.0296 0.7118 -0.0428 0.068 Uiso 1 1 calc R . . . .
C10 C -0.1293(3) 0.4380(3) 0.4753(3) 0.0471(8) Uani 1 1 d . . . . .
H10 H -0.1973 0.4750 0.4974 0.057 Uiso 1 1 calc R . . . .
C32 C 0.5441(3) 0.3662(3) 0.4415(3) 0.0494(8) Uani 1 1 d . . . . .
H32 H 0.6108 0.3844 0.4632 0.059 Uiso 1 1 calc R . . . .
C35 C 0.5196(4) 0.5973(4) 0.1830(3) 0.0577(10) Uani 1 1 d . . . . .
H35 H 0.4868 0.5574 0.1528 0.069 Uiso 1 1 calc R . . . .
C25 C 0.1812(3) -0.0701(3) 0.5232(3) 0.0507(9) Uani 1 1 d . . . . .
H25 H 0.1203 -0.0389 0.4716 0.061 Uiso 1 1 calc R . . . .
C3 C 0.2199(4) 0.5288(4) -0.0488(3) 0.0695(12) Uani 1 1 d . . . . .
H3 H 0.2768 0.5183 -0.0942 0.083 Uiso 1 1 calc R . . . .
C31 C 0.4776(3) 0.4470(3) 0.3519(3) 0.0438(8) Uani 1 1 d . . . . .
C42 C 0.2114(4) 0.0718(4) 0.2227(3) 0.0635(11) Uani 1 1 d . . . . .
H42 H 0.2142 0.0183 0.1942 0.076 Uiso 1 1 calc R . . . .
C4 C 0.1216(4) 0.6255(4) -0.0834(3) 0.0652(11) Uani 1 1 d . . . . .
H4 H 0.1141 0.6771 -0.1517 0.078 Uiso 1 1 calc R . . . .
C9 C -0.1047(3) 0.4836(3) 0.3746(3) 0.0466(8) Uani 1 1 d . . . . .
H9 H -0.1558 0.5514 0.3287 0.056 Uiso 1 1 calc R . . . .
C6 C 0.0528(3) 0.5659(3) 0.0801(3) 0.0442(8) Uani 1 1 d . . . . .
C18 C -0.0267(4) 0.1966(4) 0.8307(3) 0.0637(11) Uani 1 1 d . . . . .
H18 H 0.0343 0.1691 0.8818 0.076 Uiso 1 1 calc R . . . .
C14 C -0.0829(3) 0.2859(3) 0.6536(3) 0.0423(8) Uani 1 1 d . . . . .
C24 C 0.1936(3) -0.1834(3) 0.5981(3) 0.0563(10) Uani 1 1 d . . . . .
H24 H 0.1398 -0.2295 0.5970 0.068 Uiso 1 1 calc R . . . .
C15 C -0.2031(3) 0.2808(4) 0.6784(3) 0.0576(10) Uani 1 1 d . . . . .
H15 H -0.2642 0.3099 0.6272 0.069 Uiso 1 1 calc R . . . .
C23 C 0.2845(3) -0.2303(3) 0.6751(3) 0.0561(10) Uani 1 1 d . . . . .
H23 H 0.2900 -0.3072 0.7239 0.067 Uiso 1 1 calc R . . . .
C37 C 0.6139(3) 0.7578(4) 0.1667(3) 0.0598(10) Uani 1 1 d . . . . .
C39 C 0.5699(3) 0.6187(3) 0.3302(3) 0.0522(9) Uani 1 1 d . . . . .
H39 H 0.5722 0.5933 0.4001 0.063 Uiso 1 1 calc R . . . .
C45 C 0.4286(4) 0.0589(5) 0.1792(4) 0.0749(13) Uani 1 1 d . . . . .
H45A H 0.4709 0.1204 0.1405 0.112 Uiso 1 1 calc GR . . . .
H45B H 0.4027 0.0269 0.1361 0.112 Uiso 1 1 calc GR . . . .
H45C H 0.4823 -0.0025 0.2333 0.112 Uiso 1 1 calc GR . . . .
C16 C -0.2329(4) 0.2327(4) 0.7792(3) 0.0623(11) Uani 1 1 d . . . . .
H16 H -0.3139 0.2293 0.7944 0.075 Uiso 1 1 calc R . . . .
C36 C 0.5647(4) 0.6957(4) 0.1238(4) 0.0663(11) Uani 1 1 d . . . . .
H36 H 0.5624 0.7211 0.0539 0.080 Uiso 1 1 calc R . . . .
C43 C 0.3187(4) 0.1088(3) 0.2225(3) 0.0535(9) Uani 1 1 d . . . . .
C40 C 0.6675(5) 0.8640(4) 0.1023(4) 0.0865(16) Uani 1 1 d . . . . .
H40A H 0.7295 0.8421 0.0623 0.130 Uiso 1 1 calc GR . . . .
H40B H 0.7028 0.8907 0.1454 0.130 Uiso 1 1 calc GR . . . .
H40C H 0.6041 0.9264 0.0584 0.130 Uiso 1 1 calc GR . . . .
C38 C 0.6146(3) 0.7183(3) 0.2704(3) 0.0582(10) Uani 1 1 d . . . . .
H38 H 0.6455 0.7590 0.3009 0.070 Uiso 1 1 calc R . . . .
C17 C -0.1456(4) 0.1900(4) 0.8569(3) 0.0618(10) Uani 1 1 d . . . . .
C20 C -0.1803(6) 0.1383(5) 0.9656(4) 0.0944(17) Uani 1 1 d . . . . .
H20A H -0.1077 0.1042 1.0095 0.142 Uiso 1 1 calc GR . . . .
H20B H -0.2253 0.0783 0.9757 0.142 Uiso 1 1 calc GR . . . .
H20C H -0.2301 0.1995 0.9809 0.142 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 N1 2.035(3) . ?
Ir1 N2 2.036(3) . ?
Ir1 O3 2.136(2) . ?
Ir1 O4 2.141(2) . ?
Ir1 C13 2.017(3) . ?
Ir1 C29 2.013(3) . ?
N1 C1 1.400(4) . ?
N1 C7 1.310(4) . ?
N2 C27 1.303(4) . ?
N2 C26 1.405(4) . ?
O2 C27 1.362(4) . ?
O2 C21 1.391(4) . ?
O3 C41 1.271(4) . ?
O4 C43 1.265(5) . ?
O1 C7 1.357(4) . ?
O1 C6 1.380(4) . ?
C13 C12 1.390(5) . ?
C13 C8 1.425(4) . ?
C19 C18 1.382(6) . ?
C19 C14 1.370(5) . ?
C29 C28 1.416(5) . ?
C29 C30 1.394(5) . ?
C1 C2 1.375(5) . ?
C1 C6 1.386(5) . ?
C27 C28 1.431(5) . ?
C7 C8 1.425(5) . ?
C44 C41 1.514(5) . ?
C26 C21 1.379(5) . ?
C26 C25 1.384(5) . ?
C12 C11 1.399(5) . ?
C21 C22 1.379(5) . ?
C22 C23 1.378(6) . ?
C33 C28 1.385(5) . ?
C33 C32 1.381(5) . ?
C8 C9 1.388(5) . ?
C34 C35 1.395(5) . ?
C34 C31 1.504(5) . ?
C34 C39 1.367(5) . ?
C2 C3 1.385(6) . ?
C11 C10 1.399(5) . ?
C11 C14 1.498(5) . ?
C41 C42 1.385(6) . ?
C30 C31 1.391(5) . ?
C5 C4 1.374(6) . ?
C5 C6 1.383(5) . ?
C10 C9 1.372(5) . ?
C32 C31 1.397(5) . ?
C35 C36 1.377(6) . ?
C25 C24 1.381(5) . ?
C3 C4 1.396(6) . ?
C42 C43 1.380(6) . ?
C18 C17 1.382(6) . ?
C14 C15 1.387(5) . ?
C24 C23 1.389(6) . ?
C15 C16 1.392(6) . ?
C37 C36 1.394(6) . ?
C37 C40 1.519(6) . ?
C37 C38 1.377(6) . ?
C39 C38 1.388(5) . ?
C45 C43 1.505(6) . ?
C16 C17 1.373(6) . ?
C17 C20 1.509(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
N1 Ir1 N2 173.92(11) . . ?
N1 Ir1 O3 87.71(10) . . ?
N1 Ir1 O4 96.69(10) . . ?
N2 Ir1 O3 96.05(10) . . ?
N2 Ir1 O4 88.21(10) . . ?
O3 Ir1 O4 88.29(9) . . ?
C13 Ir1 N1 80.40(12) . . ?
C13 Ir1 N2 94.83(12) . . ?
C13 Ir1 O3 89.40(11) . . ?
C13 Ir1 O4 176.36(11) . . ?
C29 Ir1 N1 96.05(12) . . ?
C29 Ir1 N2 80.39(12) . . ?
C29 Ir1 O3 175.61(10) . . ?
C29 Ir1 O4 89.04(11) . . ?
C29 Ir1 C13 93.44(12) . . ?
C1 N1 Ir1 140.0(2) . . ?
C7 N1 Ir1 113.4(2) . . ?
C7 N1 C1 106.5(3) . . ?
C27 N2 Ir1 113.1(2) . . ?
C27 N2 C26 106.6(3) . . ?
C26 N2 Ir1 140.4(2) . . ?
C27 O2 C21 104.4(2) . . ?
C41 O3 Ir1 124.7(2) . . ?
C43 O4 Ir1 124.3(2) . . ?
C7 O1 C6 104.5(2) . . ?
C12 C13 Ir1 130.2(2) . . ?
C12 C13 C8 115.8(3) . . ?
C8 C13 Ir1 113.8(2) . . ?
C14 C19 C18 120.7(4) . . ?
C28 C29 Ir1 114.7(2) . . ?
C30 C29 Ir1 128.5(2) . . ?
C30 C29 C28 116.4(3) . . ?
C2 C1 N1 132.9(3) . . ?
C2 C1 C6 120.7(3) . . ?
C6 C1 N1 106.4(3) . . ?
N2 C27 O2 113.6(3) . . ?
N2 C27 C28 120.8(3) . . ?
O2 C27 C28 125.6(3) . . ?
N1 C7 O1 113.5(3) . . ?
N1 C7 C8 119.9(3) . . ?
O1 C7 C8 126.6(3) . . ?
C21 C26 N2 106.8(3) . . ?
C21 C26 C25 120.3(3) . . ?
C25 C26 N2 132.9(3) . . ?
C13 C12 C11 122.5(3) . . ?
C26 C21 O2 108.7(3) . . ?
C22 C21 O2 127.5(3) . . ?
C22 C21 C26 123.8(3) . . ?
C23 C22 C21 115.2(4) . . ?
C32 C33 C28 118.8(3) . . ?
C7 C8 C13 111.9(3) . . ?
C9 C8 C13 122.4(3) . . ?
C9 C8 C7 125.7(3) . . ?
C29 C28 C27 111.0(3) . . ?
C33 C28 C29 122.8(3) . . ?
C33 C28 C27 126.1(3) . . ?
C35 C34 C31 119.7(3) . . ?
C39 C34 C35 118.4(3) . . ?
C39 C34 C31 121.9(3) . . ?
C1 C2 C3 116.9(4) . . ?
C12 C11 C14 121.3(3) . . ?
C10 C11 C12 119.3(3) . . ?
C10 C11 C14 119.4(3) . . ?
O3 C41 C44 114.5(3) . . ?
O3 C41 C42 126.2(3) . . ?
C42 C41 C44 119.3(4) . . ?
C31 C30 C29 121.8(3) . . ?
C4 C5 C6 115.4(4) . . ?
C9 C10 C11 120.3(3) . . ?
C33 C32 C31 120.5(3) . . ?
C36 C35 C34 120.4(4) . . ?
C24 C25 C26 116.8(4) . . ?
C2 C3 C4 121.5(4) . . ?
C30 C31 C34 121.6(3) . . ?
C30 C31 C32 119.7(3) . . ?
C32 C31 C34 118.7(3) . . ?
C43 C42 C41 129.1(4) . . ?
C5 C4 C3 122.1(4) . . ?
C10 C9 C8 119.7(3) . . ?
O1 C6 C1 109.0(3) . . ?
O1 C6 C5 127.6(3) . . ?
C5 C6 C1 123.4(3) . . ?
C17 C18 C19 122.0(4) . . ?
C19 C14 C11 122.1(3) . . ?
C19 C14 C15 118.2(3) . . ?
C15 C14 C11 119.7(3) . . ?
C25 C24 C23 121.7(4) . . ?
C14 C15 C16 120.5(4) . . ?
C22 C23 C24 122.1(3) . . ?
C36 C37 C40 121.6(4) . . ?
C38 C37 C36 117.8(4) . . ?
C38 C37 C40 120.6(4) . . ?
C34 C39 C38 121.2(4) . . ?
C17 C16 C15 121.5(4) . . ?
C35 C36 C37 121.2(4) . . ?
O4 C43 C42 126.6(4) . . ?
O4 C43 C45 114.9(4) . . ?
C42 C43 C45 118.4(4) . . ?
C37 C38 C39 121.0(4) . . ?
C18 C17 C20 122.4(4) . . ?
C16 C17 C18 117.1(4) . . ?
C16 C17 C20 120.5(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_syh3-4
_database_code_depnum_ccdc_archive 'CCDC 1055769'
_audit_update_record             
;
2015-05-23 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;
_audit_creation_date             2015-03-23
_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         'C43 H31 Ir N2 O4'
_chemical_formula_sum            'C43 H31 Ir N2 O4'
_chemical_formula_weight         831.90
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 N1 O1 Ir1'
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'
N N 0.0061 0.0033 '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      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                   10.0973(3)
_cell_length_b                   24.0180(9)
_cell_length_c                   14.6736(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.473(3)
_cell_angle_gamma                90
_cell_volume                     3499.32(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7351
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.9790
_cell_measurement_theta_min      2.8120
_shelx_estimated_absorpt_T_max   0.614
_shelx_estimated_absorpt_T_min   0.484
_exptl_absorpt_coefficient_mu    3.862
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19343
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.206
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   54.00   95.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       11.4559 -178.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega   21.00   59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       11.4559   38.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   42.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       11.4559   38.0000  150.0000 57

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00   53.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       11.4559  -99.0000    0.0000 54

#__ type_ start__ end____ width___ exp.time_
  5 omega   16.00   62.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0184   38.0000 -150.0000 46
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0584667000
_diffrn_orient_matrix_UB_12      -0.0028709000
_diffrn_orient_matrix_UB_13      -0.0200580000
_diffrn_orient_matrix_UB_21      -0.0115041000
_diffrn_orient_matrix_UB_22      0.0267978000
_diffrn_orient_matrix_UB_23      -0.0201785000
_diffrn_orient_matrix_UB_31      0.0394186000
_diffrn_orient_matrix_UB_32      0.0120757000
_diffrn_orient_matrix_UB_33      0.0400805000
_diffrn_radiation_monochromator  graphite
_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                5461
_reflns_number_total             7170
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.886
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         7170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.065
_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)+(0.0273P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0765
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C31(H31), C28(H28), C9(H9), C27(H27), C8(H8), C18(H18), C17(H17),
 C24(H24), C1(H1), C34(H34), C16(H16), C2(H2), C41(H41), C23(H23), C15(H15),
 C5(H5), C20(H20), C4(H4), C3(H3), C37(H37), C21(H21), C22(H22), C36(H36),
 C35(H35)
2.b Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C39(H39A,H39B,H39C)
;
_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 0.24599(2) 0.30623(2) 0.94572(2) 0.04753(8) Uani 1 1 d . . . . .
O4 O 0.3891(3) 0.24097(18) 0.9755(2) 0.0656(10) Uani 1 1 d . . . . .
N1 N 0.1771(4) 0.30185(16) 1.0668(2) 0.0455(9) Uani 1 1 d . . . . .
O3 O 0.0978(3) 0.24572(16) 0.8931(2) 0.0611(9) Uani 1 1 d . . . . .
N2 N 0.3165(4) 0.31908(18) 0.8255(2) 0.0533(11) Uani 1 1 d . . . . .
C11 C 0.1071(4) 0.36660(19) 0.9238(3) 0.0448(11) Uani 1 1 d . . . . .
C30 C 0.3874(4) 0.3639(2) 0.9880(3) 0.0479(12) Uani 1 1 d . . . . .
O2 O 0.4622(3) 0.36292(16) 0.7540(2) 0.0674(10) Uani 1 1 d . . . . .
O1 O 0.0303(3) 0.33286(15) 1.1524(2) 0.0616(9) Uani 1 1 d . . . . .
C12 C 0.0691(4) 0.4016(2) 0.8472(3) 0.0508(12) Uani 1 1 d . . . . .
H12 H 0.1133 0.3982 0.7971 0.061 Uiso 1 1 calc R . . . .
C10 C 0.0342(4) 0.3743(2) 0.9968(3) 0.0458(11) Uani 1 1 d . . . . .
C29 C 0.4604(5) 0.3815(2) 0.9198(3) 0.0519(12) Uani 1 1 d . . . . .
C42 C 0.3628(7) 0.1902(3) 0.9614(4) 0.0738(17) Uani 1 1 d . . . . .
C26 C 0.5280(4) 0.4287(2) 1.0941(3) 0.0539(12) Uani 1 1 d . . . . .
C13 C 0.0794(4) 0.3362(2) 1.0722(3) 0.0472(11) Uani 1 1 d . . . . .
C40 C 0.1169(6) 0.1944(3) 0.8921(3) 0.0683(15) Uani 1 1 d . . . . .
C25 C 0.5610(5) 0.4561(2) 1.1859(3) 0.0580(13) Uani 1 1 d . . . . .
C38 C 0.2952(6) 0.2988(3) 0.7335(3) 0.0685(16) Uani 1 1 d . . . . .
C32 C 0.4137(5) 0.3550(2) 0.8328(3) 0.0543(13) Uani 1 1 d . . . . .
C31 C 0.4258(4) 0.3889(2) 1.0753(3) 0.0510(12) Uani 1 1 d . . . . .
H31 H 0.3812 0.3784 1.1227 0.061 Uiso 1 1 calc R . . . .
C28 C 0.5630(5) 0.4204(2) 0.9366(3) 0.0635(14) Uani 1 1 d . . . . .
H28 H 0.6086 0.4306 0.8895 0.076 Uiso 1 1 calc R . . . .
C9 C -0.0658(5) 0.4141(2) 0.9946(3) 0.0590(13) Uani 1 1 d . . . . .
H9 H -0.1110 0.4180 1.0441 0.071 Uiso 1 1 calc R . . . .
C7 C -0.0319(4) 0.4412(2) 0.8430(3) 0.0475(11) Uani 1 1 d . . . . .
C27 C 0.5977(5) 0.4441(2) 1.0235(3) 0.0630(14) Uani 1 1 d . . . . .
H27 H 0.6668 0.4702 1.0352 0.076 Uiso 1 1 calc R . . . .
C19 C 0.1981(5) 0.2717(2) 1.1512(3) 0.0496(12) Uani 1 1 d . . . . .
C8 C -0.0972(5) 0.4478(2) 0.9176(3) 0.0591(13) Uani 1 1 d . . . . .
H8 H -0.1628 0.4752 0.9157 0.071 Uiso 1 1 calc R . . . .
C14 C 0.1083(5) 0.2913(2) 1.2023(3) 0.0565(13) Uani 1 1 d . . . . .
C6 C -0.0727(4) 0.4755(2) 0.7580(3) 0.0529(12) Uani 1 1 d . . . . .
C18 C 0.2892(5) 0.2302(2) 1.1862(3) 0.0666(15) Uani 1 1 d . . . . .
H18 H 0.3537 0.2172 1.1536 0.080 Uiso 1 1 calc R . . . .
C33 C 0.3899(5) 0.3263(3) 0.6911(3) 0.0685(16) Uani 1 1 d . . . . .
C17 C 0.2779(7) 0.2095(3) 1.2728(4) 0.0785(18) Uani 1 1 d . . . . .
H17 H 0.3364 0.1815 1.2987 0.094 Uiso 1 1 calc R . . . .
C24 C 0.4595(5) 0.4719(2) 1.2322(3) 0.0629(14) Uani 1 1 d . . . . .
H24 H 0.3705 0.4644 1.2056 0.075 Uiso 1 1 calc R . . . .
C1 C -0.0953(5) 0.5318(2) 0.7628(3) 0.0686(15) Uani 1 1 d . . . . .
H1 H -0.0834 0.5489 0.8206 0.082 Uiso 1 1 calc R . . . .
C34 C 0.4085(7) 0.3159(3) 0.6019(4) 0.094(2) Uani 1 1 d . . . . .
H34 H 0.4708 0.3352 0.5745 0.112 Uiso 1 1 calc R . . . .
C16 C 0.1843(7) 0.2287(3) 1.3212(3) 0.0771(18) Uani 1 1 d . . . . .
H16 H 0.1803 0.2129 1.3785 0.093 Uiso 1 1 calc R . . . .
C2 C -0.1351(6) 0.5637(3) 0.6842(4) 0.0819(17) Uani 1 1 d . . . . .
H2 H -0.1478 0.6018 0.6894 0.098 Uiso 1 1 calc R . . . .
C41 C 0.2368(7) 0.1664(3) 0.9238(4) 0.0844(18) Uani 1 1 d . . . . .
H41 H 0.2337 0.1278 0.9200 0.101 Uiso 1 1 calc R . . . .
C23 C 0.4867(6) 0.4985(3) 1.3169(4) 0.0806(17) Uani 1 1 d . . . . .
H23 H 0.4167 0.5085 1.3470 0.097 Uiso 1 1 calc R . . . .
C15 C 0.0956(6) 0.2704(3) 1.2884(3) 0.0740(17) Uani 1 1 d . . . . .
H15 H 0.0317 0.2836 1.3214 0.089 Uiso 1 1 calc R . . . .
C5 C -0.0942(5) 0.4517(3) 0.6709(3) 0.0756(17) Uani 1 1 d . . . . .
H5 H -0.0807 0.4136 0.6650 0.091 Uiso 1 1 calc R . . . .
C20 C 0.6926(5) 0.4680(3) 1.2277(4) 0.0841(19) Uani 1 1 d . . . . .
H20 H 0.7631 0.4579 1.1982 0.101 Uiso 1 1 calc R . . . .
C4 C -0.1354(6) 0.4835(3) 0.5923(3) 0.0829(18) Uani 1 1 d . . . . .
H4 H -0.1493 0.4666 0.5343 0.100 Uiso 1 1 calc R . . . .
C3 C -0.1558(6) 0.5391(3) 0.5988(4) 0.0785(17) Uani 1 1 d . . . . .
H3 H -0.1835 0.5603 0.5456 0.094 Uiso 1 1 calc R . . . .
C37 C 0.2132(6) 0.2585(3) 0.6873(3) 0.087(2) Uani 1 1 d . . . . .
H37 H 0.1495 0.2400 0.7146 0.104 Uiso 1 1 calc R . . . .
C21 C 0.7203(7) 0.4946(3) 1.3124(5) 0.102(2) Uani 1 1 d . . . . .
H21 H 0.8090 0.5020 1.3397 0.122 Uiso 1 1 calc R . . . .
C22 C 0.6176(8) 0.5100(3) 1.3564(4) 0.097(2) Uani 1 1 d . . . . .
H22 H 0.6365 0.5283 1.4131 0.117 Uiso 1 1 calc R . . . .
C36 C 0.2308(7) 0.2466(4) 0.5965(4) 0.113(3) Uani 1 1 d . . . . .
H36 H 0.1771 0.2197 0.5624 0.136 Uiso 1 1 calc R . . . .
C43 C 0.4804(7) 0.1513(3) 0.9903(4) 0.110(2) Uani 1 1 d . . . . .
H43A H 0.5571 0.1649 0.9670 0.165 Uiso 1 1 calc GR . . . .
H43B H 0.4572 0.1148 0.9656 0.165 Uiso 1 1 calc GR . . . .
H43C H 0.5015 0.1494 1.0567 0.165 Uiso 1 1 calc GR . . . .
C35 C 0.3267(8) 0.2744(4) 0.5563(4) 0.112(3) Uani 1 1 d . . . . .
H35 H 0.3364 0.2647 0.4965 0.134 Uiso 1 1 calc R . . . .
C39 C -0.0076(7) 0.1595(3) 0.8529(4) 0.101(2) Uani 1 1 d . . . . .
H39A H -0.0820 0.1712 0.8808 0.152 Uiso 1 1 calc GR . . . .
H39B H 0.0111 0.1209 0.8663 0.152 Uiso 1 1 calc GR . . . .
H39C H -0.0299 0.1647 0.7870 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 O4 2.123(4) . ?
Ir1 N1 2.025(3) . ?
Ir1 O3 2.127(3) . ?
Ir1 N2 2.042(3) . ?
Ir1 C11 2.002(4) . ?
Ir1 C30 2.006(5) . ?
O4 C42 1.257(7) . ?
N1 C13 1.300(6) . ?
N1 C19 1.417(5) . ?
O3 C40 1.248(6) . ?
N2 C38 1.415(6) . ?
N2 C32 1.297(6) . ?
C11 C12 1.401(6) . ?
C11 C10 1.417(6) . ?
C30 C29 1.411(6) . ?
C30 C31 1.403(6) . ?
O2 C32 1.348(5) . ?
O2 C33 1.385(6) . ?
O1 C13 1.360(5) . ?
O1 C14 1.395(6) . ?
C12 H12 0.9300 . ?
C12 C7 1.388(6) . ?
C10 C13 1.444(6) . ?
C10 C9 1.386(6) . ?
C29 C32 1.428(6) . ?
C29 C28 1.383(7) . ?
C42 C41 1.413(9) . ?
C42 C43 1.510(8) . ?
C26 C25 1.482(6) . ?
C26 C31 1.397(6) . ?
C26 C27 1.403(6) . ?
C40 C41 1.389(8) . ?
C40 C39 1.533(8) . ?
C25 C24 1.382(7) . ?
C25 C20 1.388(6) . ?
C38 C33 1.397(7) . ?
C38 C37 1.371(8) . ?
C31 H31 0.9300 . ?
C28 H28 0.9300 . ?
C28 C27 1.383(7) . ?
C9 H9 0.9300 . ?
C9 C8 1.379(6) . ?
C7 C8 1.385(6) . ?
C7 C6 1.490(6) . ?
C27 H27 0.9300 . ?
C19 C14 1.361(6) . ?
C19 C18 1.389(7) . ?
C8 H8 0.9300 . ?
C14 C15 1.387(6) . ?
C6 C1 1.374(7) . ?
C6 C5 1.382(6) . ?
C18 H18 0.9300 . ?
C18 C17 1.389(7) . ?
C33 C34 1.378(7) . ?
C17 H17 0.9300 . ?
C17 C16 1.362(8) . ?
C24 H24 0.9300 . ?
C24 C23 1.379(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.382(7) . ?
C34 H34 0.9300 . ?
C34 C35 1.386(9) . ?
C16 H16 0.9300 . ?
C16 C15 1.371(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(7) . ?
C41 H41 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.371(8) . ?
C15 H15 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.383(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(8) . ?
C4 H4 0.9300 . ?
C4 C3 1.357(8) . ?
C3 H3 0.9300 . ?
C37 H37 0.9300 . ?
C37 C36 1.405(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.369(9) . ?
C22 H22 0.9300 . ?
C36 H36 0.9300 . ?
C36 C35 1.392(9) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C35 H35 0.9300 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Ir1 O3 88.73(15) . . ?
N1 Ir1 O4 96.34(14) . . ?
N1 Ir1 O3 87.23(13) . . ?
N1 Ir1 N2 174.26(16) . . ?
N2 Ir1 O4 87.63(13) . . ?
N2 Ir1 O3 97.04(15) . . ?
C11 Ir1 O4 176.86(15) . . ?
C11 Ir1 N1 80.55(16) . . ?
C11 Ir1 O3 90.61(16) . . ?
C11 Ir1 N2 95.51(16) . . ?
C11 Ir1 C30 89.30(17) . . ?
C30 Ir1 O4 91.54(17) . . ?
C30 Ir1 N1 95.94(15) . . ?
C30 Ir1 O3 176.78(14) . . ?
C30 Ir1 N2 79.77(17) . . ?
C42 O4 Ir1 124.5(4) . . ?
C13 N1 Ir1 114.0(3) . . ?
C13 N1 C19 105.4(4) . . ?
C19 N1 Ir1 140.6(3) . . ?
C40 O3 Ir1 125.4(4) . . ?
C38 N2 Ir1 139.2(4) . . ?
C32 N2 Ir1 114.0(3) . . ?
C32 N2 C38 106.8(4) . . ?
C12 C11 Ir1 130.1(3) . . ?
C12 C11 C10 115.1(4) . . ?
C10 C11 Ir1 114.7(3) . . ?
C29 C30 Ir1 114.9(3) . . ?
C31 C30 Ir1 129.8(3) . . ?
C31 C30 C29 115.3(4) . . ?
C32 O2 C33 104.6(4) . . ?
C13 O1 C14 103.7(4) . . ?
C11 C12 H12 118.7 . . ?
C7 C12 C11 122.5(4) . . ?
C7 C12 H12 118.7 . . ?
C11 C10 C13 111.1(4) . . ?
C9 C10 C11 123.3(4) . . ?
C9 C10 C13 125.6(4) . . ?
C30 C29 C32 111.7(4) . . ?
C28 C29 C30 123.1(4) . . ?
C28 C29 C32 125.1(4) . . ?
O4 C42 C41 127.2(6) . . ?
O4 C42 C43 115.0(6) . . ?
C41 C42 C43 117.8(7) . . ?
C31 C26 C25 121.3(4) . . ?
C31 C26 C27 119.1(4) . . ?
C27 C26 C25 119.5(5) . . ?
N1 C13 O1 114.5(4) . . ?
N1 C13 C10 119.6(4) . . ?
O1 C13 C10 125.9(4) . . ?
O3 C40 C41 126.9(6) . . ?
O3 C40 C39 115.2(5) . . ?
C41 C40 C39 117.8(6) . . ?
C24 C25 C26 120.3(4) . . ?
C24 C25 C20 117.5(5) . . ?
C20 C25 C26 122.1(5) . . ?
C33 C38 N2 105.4(5) . . ?
C37 C38 N2 133.4(5) . . ?
C37 C38 C33 121.0(5) . . ?
N2 C32 O2 114.3(4) . . ?
N2 C32 C29 119.5(4) . . ?
O2 C32 C29 126.2(5) . . ?
C30 C31 H31 118.5 . . ?
C26 C31 C30 122.9(4) . . ?
C26 C31 H31 118.5 . . ?
C29 C28 H28 120.1 . . ?
C29 C28 C27 119.9(4) . . ?
C27 C28 H28 120.1 . . ?
C10 C9 H9 120.6 . . ?
C8 C9 C10 118.8(4) . . ?
C8 C9 H9 120.6 . . ?
C12 C7 C6 120.3(4) . . ?
C8 C7 C12 119.7(4) . . ?
C8 C7 C6 120.0(4) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 C26 119.6(5) . . ?
C28 C27 H27 120.2 . . ?
C14 C19 N1 107.2(4) . . ?
C14 C19 C18 120.4(4) . . ?
C18 C19 N1 132.3(4) . . ?
C9 C8 C7 120.6(5) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C19 C14 O1 109.1(4) . . ?
C19 C14 C15 123.9(5) . . ?
C15 C14 O1 126.9(5) . . ?
C1 C6 C7 121.6(4) . . ?
C1 C6 C5 117.1(4) . . ?
C5 C6 C7 121.2(5) . . ?
C19 C18 H18 122.1 . . ?
C19 C18 C17 115.9(5) . . ?
C17 C18 H18 122.1 . . ?
O2 C33 C38 108.9(4) . . ?
C34 C33 O2 127.1(6) . . ?
C34 C33 C38 124.0(6) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 C18 122.4(6) . . ?
C16 C17 H17 118.8 . . ?
C25 C24 H24 119.1 . . ?
C23 C24 C25 121.8(5) . . ?
C23 C24 H24 119.1 . . ?
C6 C1 H1 119.1 . . ?
C6 C1 C2 121.9(5) . . ?
C2 C1 H1 119.1 . . ?
C33 C34 H34 122.7 . . ?
C33 C34 C35 114.6(6) . . ?
C35 C34 H34 122.7 . . ?
C17 C16 H16 118.8 . . ?
C17 C16 C15 122.3(5) . . ?
C15 C16 H16 118.8 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(6) . . ?
C3 C2 H2 120.0 . . ?
C42 C41 H41 116.4 . . ?
C40 C41 C42 127.2(6) . . ?
C40 C41 H41 116.4 . . ?
C24 C23 H23 120.2 . . ?
C22 C23 C24 119.5(6) . . ?
C22 C23 H23 120.2 . . ?
C14 C15 H15 122.5 . . ?
C16 C15 C14 114.9(5) . . ?
C16 C15 H15 122.5 . . ?
C6 C5 H5 119.5 . . ?
C6 C5 C4 121.0(6) . . ?
C4 C5 H5 119.5 . . ?
C25 C20 H20 119.5 . . ?
C21 C20 C25 120.9(6) . . ?
C21 C20 H20 119.5 . . ?
C5 C4 H4 119.6 . . ?
C3 C4 C5 120.8(5) . . ?
C3 C4 H4 119.6 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.3(5) . . ?
C4 C3 H3 120.3 . . ?
C38 C37 H37 121.9 . . ?
C38 C37 C36 116.2(6) . . ?
C36 C37 H37 121.9 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.2(6) . . ?
C22 C21 H21 119.9 . . ?
C23 C22 H22 120.0 . . ?
C21 C22 C23 120.1(6) . . ?
C21 C22 H22 120.0 . . ?
C37 C36 H36 119.2 . . ?
C35 C36 C37 121.5(7) . . ?
C35 C36 H36 119.2 . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C34 C35 C36 122.6(6) . . ?
C34 C35 H35 118.7 . . ?
C36 C35 H35 118.7 . . ?
C40 C39 H39A 109.5 . . ?
C40 C39 H39B 109.5 . . ?
C40 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 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_wpj-8c
_database_code_depnum_ccdc_archive 'CCDC 1055777'
_audit_update_record             
;
2015-05-23 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;
_audit_creation_date             2015-05-13
_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         '2(C43 H27 F4 Ir N2 O4), C Cl4'
_chemical_formula_sum            'C87 H54 Cl4 F8 Ir2 N4 O8'
_chemical_formula_weight         1961.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 N1 O1 Ir1 F1'
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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 '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      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x+1/2, z+1/2'
'-x+1/2, -y+1/2, z'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'y, -x-1/2, -z-1/2'
'x-1/2, y-1/2, -z'
'-y-1/2, x, -z-1/2'

_cell_length_a                   14.81340(16)
_cell_length_b                   14.81340(16)
_cell_length_c                   17.0733(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3746.50(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16132
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      28.9780
_cell_measurement_theta_min      2.7400
_shelx_estimated_absorpt_T_max   0.620
_shelx_estimated_absorpt_T_min   0.550
_exptl_absorpt_coefficient_mu    3.774
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1924
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            45792
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.187
_diffrn_reflns_theta_max         25.187
_diffrn_reflns_theta_min         2.281
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -76.00  -32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.4559  178.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
  2 omega  -75.00  -36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0184  132.0000 -147.6080 39

#__ type_ start__ end____ width___ exp.time_
  3 omega -102.00   49.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0184    0.0000    0.0000 151

#__ type_ start__ end____ width___ exp.time_
  4 omega  -81.00   17.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0184  -57.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
  5 omega  -72.00    2.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0184  127.0000  120.4353 74

#__ type_ start__ end____ width___ exp.time_
  6 omega  -95.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0184  -19.0000 -120.0000 128

#__ type_ start__ end____ width___ exp.time_
  7 omega  -92.00  -67.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.0184  157.0000  -40.1332 25
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0127203000
_diffrn_orient_matrix_UB_12      0.0305453000
_diffrn_orient_matrix_UB_13      0.0300206000
_diffrn_orient_matrix_UB_21      -0.0385244000
_diffrn_orient_matrix_UB_22      -0.0127810000
_diffrn_orient_matrix_UB_23      0.0220528000
_diffrn_orient_matrix_UB_31      0.0254856000
_diffrn_orient_matrix_UB_32      -0.0345687000
_diffrn_orient_matrix_UB_33      0.0183667000
_diffrn_radiation_monochromator  graphite
_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                2471
_reflns_number_total             3369
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    ?
_refine_diff_density_max         0.855
_refine_diff_density_min         -1.368
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3369
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²+18.4175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0901
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 Cl1, C23
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C2(H2), C9(H9), C12(H12), C19(H19), C5(H5), C15(H15), C3(H3),
 C4(H4), C17(H17), C21(H21)
4.b Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c)
;
_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
Ir3A Ir 0.2500 0.7500 0.22030(2) 0.02087(11) Uani 1 2 d S T P . .
C13 C 0.3201(3) 0.6851(3) 0.1371(3) 0.0267(11) Uani 1 1 d . . . . .
N1AA N 0.1773(3) 0.6343(3) 0.2121(3) 0.0280(10) Uani 1 1 d . . . . .
O1 O 0.1563(2) 0.5018(2) 0.1528(2) 0.0336(9) Uani 1 1 d . . . . .
C11 C 0.4368(4) 0.6647(4) 0.0364(3) 0.0283(12) Uani 1 1 d . . . . .
C10 C 0.4036(4) 0.5777(4) 0.0203(3) 0.0318(13) Uani 1 1 d . . . . .
H10 H 0.4313 0.5426 -0.0179 0.038 Uiso 1 1 calc R . . . .
C1 C 0.0959(4) 0.5991(4) 0.2407(3) 0.0303(12) Uani 1 1 d . . . . .
C2 C 0.0331(4) 0.6309(4) 0.2934(4) 0.0376(14) Uani 1 1 d . . . . .
H2 H 0.0402 0.6864 0.3182 0.045 Uiso 1 1 calc R . . . .
C14 C 0.5151(4) 0.7019(4) -0.0106(3) 0.0294(12) Uani 1 1 d . . . . .
C22 C 0.3830(4) 0.6479(4) 0.4332(4) 0.0388(14) Uani 1 1 d . . . . .
H22A H 0.3720 0.5843 0.4291 0.058 Uiso 1 1 calc GR . . . .
H22B H 0.3755 0.6665 0.4867 0.058 Uiso 1 1 calc GR . . . .
H22C H 0.4435 0.6610 0.4165 0.058 Uiso 1 1 calc GR . . . .
C9 C 0.3305(4) 0.5441(4) 0.0609(3) 0.0313(12) Uani 1 1 d . . . . .
H9 H 0.3089 0.4863 0.0505 0.038 Uiso 1 1 calc R . . . .
C8 C 0.2891(3) 0.5978(3) 0.1178(3) 0.0272(12) Uani 1 1 d . . . . .
C12 C 0.3949(3) 0.7159(3) 0.0948(3) 0.0257(11) Uani 1 1 d . . . . .
H12 H 0.4177 0.7730 0.1060 0.031 Uiso 1 1 calc R . . . .
C19 C 0.5709(4) 0.7672(4) 0.0259(4) 0.0411(15) Uani 1 1 d . . . . .
H19 H 0.5645 0.7815 0.0787 0.049 Uiso 1 1 calc R . . . .
C5 C 0.0114(4) 0.4604(4) 0.2176(4) 0.0457(17) Uani 1 1 d . . . . .
H5 H 0.0051 0.4047 0.1931 0.055 Uiso 1 1 calc R . . . .
C15 C 0.5227(4) 0.6856(4) -0.0872(4) 0.0451(16) Uani 1 1 d . . . . .
H15 H 0.4835 0.6453 -0.1115 0.054 Uiso 1 1 calc R . . . .
C3 C -0.0409(4) 0.5767(4) 0.3080(4) 0.0451(16) Uani 1 1 d . . . . .
H3 H -0.0847 0.5960 0.3432 0.054 Uiso 1 1 calc R . . . .
C6 C 0.0839(4) 0.5163(4) 0.2036(4) 0.0350(13) Uani 1 1 d . . . . .
C4 C -0.0511(5) 0.4926(5) 0.2704(4) 0.0501(18) Uani 1 1 d . . . . .
H4 H -0.1018 0.4578 0.2815 0.060 Uiso 1 1 calc R . . . .
C7 C 0.2089(4) 0.5758(3) 0.1617(3) 0.0272(11) Uani 1 1 d . . . . .
F2 F 0.6916(3) 0.8688(3) 0.0149(3) 0.0735(14) Uani 1 1 d . . . . .
F1 F 0.5979(4) 0.7121(3) -0.2075(2) 0.0794(15) Uani 1 1 d . . . . .
C17 C 0.6465(4) 0.7920(4) -0.0982(4) 0.0453(16) Uani 1 1 d . . . . .
H17 H 0.6902 0.8216 -0.1277 0.054 Uiso 1 1 calc R . . . .
C18 C 0.6348(4) 0.8084(4) -0.0201(4) 0.0468(17) Uani 1 1 d . . . . .
C16 C 0.5894(5) 0.7287(5) -0.1306(4) 0.0485(17) Uani 1 1 d . . . . .
O2 O 0.3297(2) 0.6885(2) 0.3088(2) 0.0287(8) Uani 1 1 d . . . . .
C21 C 0.2500 0.7500 0.4188(5) 0.0280(16) Uani 1 2 d S T P . .
H21 H 0.2500 0.7500 0.4733 0.034 Uiso 1 2 calc RS T P . .
C20 C 0.3171(4) 0.6982(4) 0.3822(3) 0.0298(12) Uani 1 1 d . . . . .
Cl1 Cl 0.6725(5) 0.7177(4) 0.3133(4) 0.249(3) Uani 1 1 d . U . . .
C23 C 0.7500 0.7500 0.2500 0.182(10) Uani 1 4 d S TU 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
Ir3A C13 2.005(5) . ?
Ir3A C13 2.005(5) 3_565 ?
Ir3A N1AA 2.029(4) 3_565 ?
Ir3A N1AA 2.029(4) . ?
Ir3A O2 2.123(4) 3_565 ?
Ir3A O2 2.123(4) . ?
C13 C8 1.411(7) . ?
C13 C12 1.400(7) . ?
N1AA C1 1.401(7) . ?
N1AA C7 1.309(7) . ?
O1 C6 1.396(7) . ?
O1 C7 1.353(6) . ?
C11 C10 1.406(8) . ?
C11 C14 1.514(7) . ?
C11 C12 1.398(8) . ?
C10 H10 0.9300 . ?
C10 C9 1.379(8) . ?
C1 C2 1.378(8) . ?
C1 C6 1.392(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(8) . ?
C14 C19 1.417(8) . ?
C14 C15 1.335(9) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 C20 1.505(8) . ?
C9 H9 0.9300 . ?
C9 C8 1.397(8) . ?
C8 C7 1.443(7) . ?
C12 H12 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.374(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(8) . ?
C5 C4 1.378(10) . ?
C15 H15 0.9300 . ?
C15 C16 1.391(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.409(10) . ?
C4 H4 0.9300 . ?
F2 C18 1.365(7) . ?
F1 C16 1.341(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.367(9) . ?
C17 C16 1.378(9) . ?
O2 C20 1.276(7) . ?
C21 H21 0.9300 . ?
C21 C20 1.403(7) . ?
C21 C20 1.403(7) 3_565 ?
Cl1 C23 1.649(6) . ?
C23 Cl1 1.649(6) 8_756 ?
C23 Cl1 1.649(6) 3_665 ?
C23 Cl1 1.649(6) 6_576 ?

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 Ir3A C13 89.7(3) . 3_565 ?
C13 Ir3A N1AA 79.70(19) . . ?
C13 Ir3A N1AA 94.66(19) . 3_565 ?
C13 Ir3A N1AA 94.67(19) 3_565 . ?
C13 Ir3A N1AA 79.70(19) 3_565 3_565 ?
C13 Ir3A O2 176.36(17) . 3_565 ?
C13 Ir3A O2 90.63(18) . . ?
C13 Ir3A O2 90.63(18) 3_565 3_565 ?
C13 Ir3A O2 176.36(17) 3_565 . ?
N1AA Ir3A N1AA 172.1(3) 3_565 . ?
N1AA Ir3A O2 88.96(16) 3_565 3_565 ?
N1AA Ir3A O2 96.67(16) . 3_565 ?
N1AA Ir3A O2 96.67(16) 3_565 . ?
N1AA Ir3A O2 88.96(16) . . ?
O2 Ir3A O2 89.2(2) 3_565 . ?
C8 C13 Ir3A 115.9(4) . . ?
C12 C13 Ir3A 128.3(4) . . ?
C12 C13 C8 115.8(5) . . ?
C1 N1AA Ir3A 138.4(4) . . ?
C7 N1AA Ir3A 114.5(3) . . ?
C7 N1AA C1 106.8(4) . . ?
C7 O1 C6 104.3(4) . . ?
C10 C11 C14 119.9(5) . . ?
C12 C11 C10 118.8(5) . . ?
C12 C11 C14 121.3(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 C11 120.5(5) . . ?
C9 C10 H10 119.7 . . ?
C2 C1 N1AA 133.0(5) . . ?
C2 C1 C6 120.8(5) . . ?
C6 C1 N1AA 106.2(5) . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.1(6) . . ?
C3 C2 H2 121.4 . . ?
C19 C14 C11 117.6(5) . . ?
C15 C14 C11 121.2(5) . . ?
C15 C14 C19 120.3(5) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
C10 C9 H9 120.4 . . ?
C10 C9 C8 119.2(5) . . ?
C8 C9 H9 120.4 . . ?
C13 C8 C7 110.7(5) . . ?
C9 C8 C13 122.8(5) . . ?
C9 C8 C7 126.4(5) . . ?
C13 C12 H12 118.6 . . ?
C11 C12 C13 122.8(5) . . ?
C11 C12 H12 118.6 . . ?
C14 C19 H19 121.5 . . ?
C18 C19 C14 117.0(6) . . ?
C18 C19 H19 121.5 . . ?
C6 C5 H5 122.3 . . ?
C6 C5 C4 115.4(6) . . ?
C4 C5 H5 122.3 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.0(6) . . ?
C16 C15 H15 120.0 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.1(6) . . ?
C4 C3 H3 119.4 . . ?
C1 C6 O1 108.7(5) . . ?
C5 C6 O1 127.9(5) . . ?
C5 C6 C1 123.4(6) . . ?
C5 C4 C3 122.1(6) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
N1AA C7 O1 113.9(5) . . ?
N1AA C7 C8 119.1(5) . . ?
O1 C7 C8 126.8(5) . . ?
C18 C17 H17 122.1 . . ?
C18 C17 C16 115.8(6) . . ?
C16 C17 H17 122.1 . . ?
F2 C18 C19 117.7(6) . . ?
F2 C18 C17 117.8(6) . . ?
C17 C18 C19 124.5(6) . . ?
F1 C16 C15 120.3(6) . . ?
F1 C16 C17 117.4(6) . . ?
C17 C16 C15 122.3(6) . . ?
C20 O2 Ir3A 124.8(3) . . ?
C20 C21 H21 116.4 3_565 . ?
C20 C21 H21 116.4 . . ?
C20 C21 C20 127.2(7) . 3_565 ?
O2 C20 C22 114.8(5) . . ?
O2 C20 C21 127.0(5) . . ?
C21 C20 C22 118.2(5) . . ?
Cl1 C23 Cl1 115.5(3) 8_756 3_665 ?
Cl1 C23 Cl1 115.5(3) 6_576 . ?
Cl1 C23 Cl1 115.5(3) 6_576 3_665 ?
Cl1 C23 Cl1 98.0(6) 3_665 . ?
Cl1 C23 Cl1 115.5(3) 8_756 . ?
Cl1 C23 Cl1 98.0(6) 8_756 6_576 ?

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