# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_5
# Added during the CSD deposition process: Monday 19 December 2016 03:40 PM
# end Validation Reply Form


_database_code_depnum_ccdc_archive 'CCDC 1521969'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-06-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_CHEMW03_5                   
;
PROBLEM: WARNING: The ratio of given/expected molecular weight as
RESPONSE: The difference is due to masked solvent (hexane)
;
_vrf_PLAT201_5                   
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          1 Report
RESPONSE: disorder between two close positions
;

_audit_creation_date             2016-12-18
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        
'Tetrakis[2-phenyl-4-(2,4,6-trimethylphenyl)pyridine-C2,N?]-bis(?-oxamidato-N,N?,O,O?)diiridium(III) '
_chemical_formula_moiety         'C82 H74 Ir2 N6 O2,C6 H14'
_chemical_formula_sum            'C88 H88 Ir2 N6 O2'
_chemical_formula_weight         1646.04
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0100 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4830 7.6260 '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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   15.122(3)
_cell_length_b                   24.292(4)
_cell_length_c                   19.265(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.237(2)
_cell_angle_gamma                90
_cell_volume                     7071(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9392
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.51
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.845
_exptl_absorpt_coefficient_mu    3.481
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1052 before and 0.0523 after correction.
The Ratio of minimum to maximum transmission is 0.7388.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3312
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 Over a hemisphere of the reciprocal space was covered by 3 runs of 
narrow-frame omega scans.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            42109
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         29.559
_diffrn_reflns_theta_min         1.538
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 0.0350
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device       'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Kappa Rigaku Saturn724+'
_diffrn_measurement_method       'thick-slice ω scans'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  'double crystal silicon'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7944
_reflns_number_total             10354
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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_data_collection       'Rigaku CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'Rigaku CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        
;
Rigaku CrystalClear (Rigaku Inc., 2008), then transformed to Bruker format 
using APEX2 
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
'ShelXL 2014/7 multi-CPU version (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max         1.703
_refine_diff_density_min         -1.868
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       0.00021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         10354
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+13.9850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0830
_refine_special_details          
;The mesityl group at C(9) is partly disordered: C(24), C(25), C(26) 
& C(30) with attached hydrogens, occupy positions A and B with 
the probabilities of 0.727(9) and 0.273(9), respectively. 
Within any single dimeric molecule, both ligands cannot have 
conformation B simultaneously, as this would result in impossibly 
short non-bonding contact of 2.97 Å between C(30B) and its equivalent    
via the twofold axis. 
The bridging ligand is disordered: O atoms and NH groups are statistically 
mixed, hence its stereochemistry is not unequivocal. The the best fit to the 
observed electron density is the overlap of two trans configurations: 
O(1) and N(1)H(1) with occupancies 0.64(3), or N(2)H(2) and O(2) with 
occupancies 0.36(3).  
Methyl groups were refined as rigid bodies rotating around C---C bonds, 
with a common refined U for three H atoms, except C(40)H₃ which was 
treated as ideally disordered (AFIX 123), C(30A)H₃ and C(30B)H₃ which 
were not allowed to rotate (AFIX 33). Other H atoms: riding model at 
idealised C---H and N---H distances. The disordered hydrogen atoms of the 
bridging ligand were located in the difference Fourier map. 
The unit cell contains four (symmetrically related) enclosed voids, each 
probably occupied by a single disordered hexane molecule. The contribution 
of the latter to the structure factors, was accounted for using PLATON 
SQUEEZE solvent-masking program (Speck, 2003, 2009)., SQUEEZE
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C26A-C27 \\sim C26B-C27
 with sigma of 0.02
 C26A-C25A \\sim C26B-C25B
 with sigma of 0.02
 C9-C24A \\sim C9-C24B
 with sigma of 0.02
 C25A-C24A \\sim C25B-C24B
 with sigma of 0.02
 C29-C24B \\sim C29-C24A
 with sigma of 0.02
 C30B-C25B \\sim C25A-C30A
 with sigma of 0.02
 Ir_$1-O2 \\sim Ir-O1
 with sigma of 0.02
 O1-C23 \\sim O2-C23
 with sigma of 0.02
 N1-C23 \\sim N2-C23
 with sigma of 0.02
 Ir_$1-N2 \\sim Ir-N1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C30A) = Uanis(C30B)
Uanis(C25A) = Uanis(C25B)
Uanis(C26A) = Uanis(C26B)
Uiso(C24B) = Uiso(C24B)
Uanis(N1) = Uanis(O1)
Uanis(O2) = Uanis(N2)
4. Others
 Uiso(H31A)=Uiso(H31B)=Uiso(H31C)=FVAR(1)
 Uiso(H32A)=Uiso(H32B)=Uiso(H32C)=FVAR(2)
 Uiso(H39A)=Uiso(H39B)=Uiso(H39C)=FVAR(3)
 Uiso(H41A)=Uiso(H41B)=Uiso(H41C)=FVAR(4)
 Sof(C24B)=Sof(C25B)=Sof(C26B)=Sof(H26B)=Sof(C30B)=Sof(H30D)=Sof(H30E)=
 Sof(H30F)=1-FVAR(5)
 Sof(C24A)=Sof(C25A)=Sof(C26A)=Sof(H26A)=Sof(C30A)=Sof(H30A)=Sof(H30B)=
 Sof(H30C)=FVAR(5)
 Sof(O2)=Sof(N1)=Sof(H1N)=1-FVAR(6)
 Sof(O1)=Sof(N2)=Sof(H2N)=FVAR(6)
 Fixed Sof: H40D(0.5) H40E(0.5) H40F(0.5) H40A(0.5) H40B(0.5) H40C(0.5)
5.a Riding coordinates:
 N2(H2N), N1(H1N), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11),
 C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C21(H21), C22(H22), C28(H28),
  C35(H35), C37(H37), C40(H40D,H40E,H40F,H40A,H40B,H40C), C26A(H26A), C30A(H30A,
 H30B,H30C), C26B(H26B), C30B(H30D,H30E,H30F)
5.b Rotating group:
 C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C39(H39A,H39B,H39C), C41(H41A,H41B,
 H41C)
;
_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
Ir Ir 0.38497(2) 0.57740(2) 0.60701(2) 0.02261(5) Uani 1 1 d D . . . .
O1 O 0.2420(8) 0.5643(6) 0.5913(7) 0.0214(18) Uani 0.64(3) 1 d D . P A 1
N2 N 0.1333(13) 0.5737(11) 0.5033(10) 0.021(2) Uani 0.64(3) 1 d D . P A 1
H2N H 0.0876 0.5726 0.5303 0.026 Uiso 0.64(3) 1 d R . P A 1
O2 O 0.1341(19) 0.5668(18) 0.5054(14) 0.021(2) Uani 0.36(3) 1 d D . P A 2
N1 N 0.2448(19) 0.5738(12) 0.5914(16) 0.0214(18) Uani 0.36(3) 1 d D . P A 2
H1N H 0.2111 0.5683 0.6270 0.026 Uiso 0.36(3) 1 d R . P A 2
N3 N 0.3773(2) 0.66127(10) 0.60277(15) 0.0262(6) Uani 1 1 d . . . . .
N4 N 0.40211(19) 0.49512(11) 0.62082(15) 0.0242(6) Uani 1 1 d . . . . .
C1 C 0.5138(2) 0.59514(13) 0.61192(18) 0.0253(7) Uani 1 1 d . . . . .
C2 C 0.5870(2) 0.55932(14) 0.61480(19) 0.0295(8) Uani 1 1 d . . . . .
H2 H 0.5770 0.5208 0.6180 0.035 Uiso 1 1 d R . . . .
C3 C 0.6737(3) 0.57875(16) 0.6134(2) 0.0351(8) Uani 1 1 d . . . . .
H3 H 0.7218 0.5536 0.6151 0.042 Uiso 1 1 d R . . . .
C4 C 0.6898(3) 0.63493(17) 0.6091(2) 0.0401(9) Uani 1 1 d . . . . .
H4 H 0.7489 0.6480 0.6073 0.048 Uiso 1 1 d R . . . .
C5 C 0.6203(3) 0.67189(15) 0.6077(2) 0.0343(8) Uani 1 1 d . . . . .
H5 H 0.6315 0.7103 0.6048 0.041 Uiso 1 1 d R . . . .
C6 C 0.5331(2) 0.65221(13) 0.61046(19) 0.0280(7) Uani 1 1 d . . . . .
C7 C 0.4560(3) 0.68811(13) 0.61064(18) 0.0273(7) Uani 1 1 d . . . . .
C8 C 0.4575(3) 0.74556(13) 0.6196(2) 0.0310(8) Uani 1 1 d . . . . .
H8 H 0.5126 0.7640 0.6263 0.037 Uiso 1 1 d R . . . .
C9 C 0.3795(3) 0.77556(14) 0.61874(19) 0.0354(9) Uani 1 1 d D . . . .
C10 C 0.3005(3) 0.74687(14) 0.6067(2) 0.0340(9) Uani 1 1 d . . . . .
H10 H 0.2458 0.7662 0.6037 0.041 Uiso 1 1 d R . . . .
C11 C 0.3017(3) 0.69016(13) 0.59919(19) 0.0303(8) Uani 1 1 d . . . . .
H11 H 0.2474 0.6712 0.5912 0.036 Uiso 1 1 d R . . . .
C12 C 0.3868(2) 0.57473(13) 0.71151(18) 0.0239(7) Uani 1 1 d . . . . .
C13 C 0.3687(3) 0.61645(15) 0.7579(2) 0.0324(8) Uani 1 1 d . . . . .
H13 H 0.3586 0.6528 0.7411 0.039 Uiso 1 1 d R . . . .
C14 C 0.3650(3) 0.60626(15) 0.8285(2) 0.0345(8) Uani 1 1 d . . . . .
H14 H 0.3506 0.6354 0.8590 0.041 Uiso 1 1 d R . . . .
C15 C 0.3819(3) 0.55394(16) 0.8555(2) 0.0372(9) Uani 1 1 d . . . . .
H15 H 0.3797 0.5473 0.9040 0.045 Uiso 1 1 d R . . . .
C16 C 0.4020(3) 0.51184(15) 0.8105(2) 0.0368(9) Uani 1 1 d . . . . .
H16 H 0.4149 0.4761 0.8281 0.044 Uiso 1 1 d R . . . .
C17 C 0.4036(2) 0.52162(13) 0.73916(19) 0.0285(8) Uani 1 1 d . . . . .
C18 C 0.4150(2) 0.47817(13) 0.68778(18) 0.0259(7) Uani 1 1 d . . . . .
C19 C 0.4324(2) 0.42274(13) 0.7026(2) 0.0272(7) Uani 1 1 d . . . . .
H19 H 0.4474 0.4121 0.7490 0.033 Uiso 1 1 d R . . . .
C20 C 0.4279(2) 0.38287(13) 0.65057(19) 0.0257(7) Uani 1 1 d . . . . .
C21 C 0.4134(2) 0.40228(14) 0.5824(2) 0.0280(7) Uani 1 1 d . . . . .
H21 H 0.4106 0.3770 0.5447 0.034 Uiso 1 1 d R . . . .
C22 C 0.4035(2) 0.45753(13) 0.56990(19) 0.0269(7) Uani 1 1 d . . . . .
H22 H 0.3971 0.4697 0.5231 0.032 Uiso 1 1 d R . . . .
C23 C 0.2149(2) 0.56902(11) 0.52740(18) 0.0244(7) Uani 1 1 d D . . . .
C27 C 0.3686(3) 0.94843(16) 0.6625(3) 0.0487(12) Uani 1 1 d D . . . .
C28 C 0.3578(3) 0.91003(16) 0.7136(2) 0.0400(10) Uani 1 1 d . . . . .
H28 H 0.3471 0.9221 0.7595 0.048 Uiso 1 1 d R . . . .
C29 C 0.3618(3) 0.85392(14) 0.7002(2) 0.0322(8) Uani 1 1 d D . . . .
C31 C 0.3600(4) 1.00930(16) 0.6786(3) 0.0680(17) Uani 1 1 d . . . . .
H31A H 0.2971 1.0193 0.6799 0.126(16) Uiso 1 1 d GR . . . .
H31B H 0.3879 1.0312 0.6425 0.126(16) Uiso 1 1 d GR . . . .
H31C H 0.3893 1.0175 0.7239 0.126(16) Uiso 1 1 d GR . . . .
C32 C 0.3466(4) 0.81323(19) 0.7574(2) 0.0500(12) Uani 1 1 d . . . . .
H32A H 0.2895 0.7949 0.7489 0.059(9) Uiso 1 1 d GR . . . .
H32B H 0.3464 0.8325 0.8022 0.059(9) Uiso 1 1 d GR . . . .
H32C H 0.3941 0.7858 0.7586 0.059(9) Uiso 1 1 d GR . . . .
C33 C 0.4315(2) 0.32280(13) 0.66700(19) 0.0275(7) Uani 1 1 d . . . . .
C34 C 0.4791(3) 0.28619(13) 0.6257(2) 0.0309(8) Uani 1 1 d . . . . .
C35 C 0.4729(3) 0.22996(14) 0.6378(2) 0.0327(8) Uani 1 1 d . . . . .
H35 H 0.5058 0.2055 0.6102 0.039 Uiso 1 1 d R . . . .
C36 C 0.4206(3) 0.20807(13) 0.6886(2) 0.0317(8) Uani 1 1 d . . . . .
C37 C 0.3771(3) 0.24451(13) 0.7301(2) 0.0304(8) Uani 1 1 d . . . . .
H37 H 0.3425 0.2304 0.7662 0.037 Uiso 1 1 d R . . . .
C38 C 0.3818(2) 0.30164(13) 0.72088(19) 0.0283(8) Uani 1 1 d . . . . .
C39 C 0.5406(3) 0.30519(15) 0.5708(2) 0.0393(10) Uani 1 1 d . . . . .
H39A H 0.5865 0.2774 0.5647 0.050(8) Uiso 1 1 d GR . . . .
H39B H 0.5682 0.3400 0.5852 0.050(8) Uiso 1 1 d GR . . . .
H39C H 0.5069 0.3105 0.5268 0.050(8) Uiso 1 1 d GR . . . .
C40 C 0.4094(3) 0.14647(14) 0.6974(2) 0.0379(9) Uani 1 1 d . . . . .
H40D H 0.3834 0.1307 0.6545 0.057 Uiso 0.5 1 d R . P B 2
H40E H 0.4672 0.1296 0.7078 0.057 Uiso 0.5 1 d R . P B 2
H40F H 0.3702 0.1394 0.7358 0.057 Uiso 0.5 1 d R . P B 2
H40A H 0.3466 0.1369 0.6909 0.057 Uiso 0.5 1 d R . P C 1
H40B H 0.4437 0.1271 0.6629 0.057 Uiso 0.5 1 d R . P C 1
H40C H 0.4305 0.1357 0.7442 0.057 Uiso 0.5 1 d R . P C 1
C41 C 0.3304(3) 0.33629(14) 0.7707(2) 0.0357(9) Uani 1 1 d . . . . .
H41A H 0.3714 0.3524 0.8057 0.054(8) Uiso 1 1 d GR . . . .
H41B H 0.2873 0.3131 0.7937 0.054(8) Uiso 1 1 d GR . . . .
H41C H 0.2993 0.3659 0.7451 0.054(8) Uiso 1 1 d GR . . . .
C24A C 0.3853(4) 0.8358(2) 0.6351(3) 0.0274(13) Uiso 0.727(9) 1 d D . P D 1
C25A C 0.4044(6) 0.8739(2) 0.5834(3) 0.0447(19) Uani 0.727(9) 1 d D . P D 1
C26A C 0.3985(6) 0.9298(2) 0.5990(4) 0.054(2) Uani 0.727(9) 1 d D . P D 1
H26A H 0.4175 0.9562 0.5663 0.065 Uiso 0.727(9) 1 d R . P D 1
C30A C 0.4280(8) 0.8540(3) 0.5116(4) 0.074(3) Uani 0.727(9) 1 d D . P D 1
H30A H 0.4748 0.8263 0.5171 0.112 Uiso 0.727(9) 1 d R . P D 1
H30B H 0.4495 0.8851 0.4847 0.112 Uiso 0.727(9) 1 d R . P D 1
H30C H 0.3762 0.8377 0.4873 0.112 Uiso 0.727(9) 1 d R . P D 1
C24B C 0.3602(10) 0.8357(4) 0.6316(5) 0.017(3) Uiso 0.273(9) 1 d D . P D 2
C25B C 0.3592(16) 0.8750(6) 0.5779(8) 0.0447(19) Uani 0.273(9) 1 d D . P D 2
C26B C 0.3522(18) 0.9313(7) 0.5933(9) 0.054(2) Uani 0.273(9) 1 d D . P D 2
H26B H 0.3436 0.9571 0.5565 0.065 Uiso 0.273(9) 1 d R . P D 2
C30B C 0.348(2) 0.8567(7) 0.5017(9) 0.074(3) Uani 0.273(9) 1 d D . P D 2
H30D H 0.4081 0.8562 0.4838 0.112 Uiso 0.273(9) 1 d R . P D 2
H30E H 0.3112 0.8823 0.4742 0.112 Uiso 0.273(9) 1 d R . P D 2
H30F H 0.3227 0.8196 0.4985 0.112 Uiso 0.273(9) 1 d R . P D 2


_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
Ir O1 2.194(13) . ?
Ir N2 2.135(18) 2_556 ?
Ir O2 2.19(2) 2_556 ?
Ir N1 2.13(3) . ?
Ir N3 2.042(3) . ?
Ir N4 2.032(3) . ?
Ir C1 1.993(4) . ?
Ir C12 2.013(3) . ?
O1 C23 1.286(14) . ?
N2 Ir 2.135(18) 2_556 ?
N2 C23 1.307(19) . ?
O2 Ir 2.19(2) 2_556 ?
O2 C23 1.28(3) . ?
N1 C23 1.30(3) . ?
N3 C7 1.360(5) . ?
N3 C11 1.340(5) . ?
N4 C18 1.361(4) . ?
N4 C22 1.341(4) . ?
C1 C2 1.408(5) . ?
C1 C6 1.417(4) . ?
C2 C3 1.394(5) . ?
C3 C4 1.389(5) . ?
C4 C5 1.382(6) . ?
C5 C6 1.407(5) . ?
C6 C7 1.456(5) . ?
C7 C8 1.406(4) . ?
C8 C9 1.386(6) . ?
C9 C10 1.395(6) . ?
C9 C24A 1.499(6) . ?
C9 C24B 1.512(10) . ?
C10 C11 1.385(5) . ?
C12 C13 1.386(5) . ?
C12 C17 1.415(5) . ?
C13 C14 1.385(5) . ?
C14 C15 1.393(5) . ?
C15 C16 1.383(5) . ?
C16 C17 1.395(5) . ?
C17 C18 1.462(5) . ?
C18 C19 1.399(4) . ?
C19 C20 1.393(5) . ?
C20 C21 1.404(5) . ?
C20 C33 1.494(4) . ?
C21 C22 1.371(5) . ?
C23 C23 1.526(7) 2_556 ?
C27 C28 1.372(7) . ?
C27 C31 1.518(5) . ?
C27 C26A 1.396(8) . ?
C27 C26B 1.410(15) . ?
C28 C29 1.389(5) . ?
C29 C32 1.505(6) . ?
C29 C24A 1.388(7) . ?
C29 C24B 1.394(11) . ?
C33 C34 1.410(5) . ?
C33 C38 1.403(5) . ?
C34 C35 1.390(5) . ?
C34 C39 1.507(6) . ?
C35 C36 1.387(6) . ?
C36 C37 1.378(5) . ?
C36 C40 1.516(5) . ?
C37 C38 1.401(4) . ?
C38 C41 1.514(5) . ?
C24A C25A 1.398(7) . ?
C25A C26A 1.395(7) . ?
C25A C30A 1.520(9) . ?
C24B C25B 1.407(14) . ?
C25B C26B 1.403(15) . ?
C25B C30B 1.537(16) . ?

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
N2 Ir O1 76.6(4) 2_556 . ?
N1 Ir O2 76.3(6) . 2_556 ?
N3 Ir O1 94.9(4) . . ?
N3 Ir N2 89.8(7) . 2_556 ?
N3 Ir O2 94.2(12) . 2_556 ?
N3 Ir N1 88.9(8) . . ?
N4 Ir O1 89.8(4) . . ?
N4 Ir N2 95.7(7) . 2_556 ?
N4 Ir O2 91.4(11) . 2_556 ?
N4 Ir N1 95.7(8) . . ?
N4 Ir N3 173.47(11) . . ?
C1 Ir O1 173.4(4) . . ?
C1 Ir N2 98.3(6) . 2_556 ?
C1 Ir O2 99.4(8) . 2_556 ?
C1 Ir N1 168.6(8) . . ?
C1 Ir N3 80.80(13) . . ?
C1 Ir N4 94.99(13) . . ?
C1 Ir C12 89.10(14) . . ?
C12 Ir O1 96.2(4) . . ?
C12 Ir N2 172.1(7) . 2_556 ?
C12 Ir O2 169.0(11) . 2_556 ?
C12 Ir N1 96.6(9) . . ?
C12 Ir N3 94.05(12) . . ?
C12 Ir N4 80.83(12) . . ?
C23 O1 Ir 113.2(9) . . ?
C23 N2 Ir 116.1(13) . 2_556 ?
C23 O2 Ir 114.2(18) . 2_556 ?
C23 N1 Ir 116(2) . . ?
C7 N3 Ir 115.2(2) . . ?
C11 N3 Ir 124.9(2) . . ?
C11 N3 C7 119.6(3) . . ?
C18 N4 Ir 115.8(2) . . ?
C22 N4 Ir 125.4(2) . . ?
C22 N4 C18 118.8(3) . . ?
C2 C1 Ir 129.3(3) . . ?
C2 C1 C6 116.3(3) . . ?
C6 C1 Ir 114.3(3) . . ?
C3 C2 C1 121.9(3) . . ?
C4 C3 C2 120.1(4) . . ?
C5 C4 C3 120.3(4) . . ?
C4 C5 C6 119.5(3) . . ?
C1 C6 C7 114.8(3) . . ?
C5 C6 C1 121.8(3) . . ?
C5 C6 C7 123.3(3) . . ?
N3 C7 C6 114.2(3) . . ?
N3 C7 C8 120.0(3) . . ?
C8 C7 C6 125.8(3) . . ?
C9 C8 C7 120.7(4) . . ?
C8 C9 C10 117.5(3) . . ?
C8 C9 C24A 117.9(4) . . ?
C8 C9 C24B 132.5(7) . . ?
C10 C9 C24A 124.4(4) . . ?
C10 C9 C24B 109.9(7) . . ?
C11 C10 C9 119.9(4) . . ?
N3 C11 C10 122.0(4) . . ?
C13 C12 Ir 128.8(3) . . ?
C13 C12 C17 117.4(3) . . ?
C17 C12 Ir 113.6(2) . . ?
C14 C13 C12 121.3(3) . . ?
C13 C14 C15 121.0(4) . . ?
C16 C15 C14 118.9(4) . . ?
C15 C16 C17 120.3(3) . . ?
C12 C17 C18 115.3(3) . . ?
C16 C17 C12 121.1(3) . . ?
C16 C17 C18 123.4(3) . . ?
N4 C18 C17 114.0(3) . . ?
N4 C18 C19 120.2(3) . . ?
C19 C18 C17 125.7(3) . . ?
C20 C19 C18 121.3(3) . . ?
C19 C20 C21 116.1(3) . . ?
C19 C20 C33 121.8(3) . . ?
C21 C20 C33 121.9(3) . . ?
C22 C21 C20 120.3(3) . . ?
N4 C22 C21 122.9(3) . . ?
O1 C23 N2 127.4(7) . . ?
O1 C23 C23 117.3(7) . 2_556 ?
N2 C23 C23 115.3(9) . 2_556 ?
O2 C23 N1 127.6(11) . . ?
O2 C23 C23 116.8(14) . 2_556 ?
N1 C23 C23 115.5(15) . 2_556 ?
C28 C27 C31 120.1(5) . . ?
C28 C27 C26A 117.5(4) . . ?
C28 C27 C26B 117.2(8) . . ?
C26A C27 C31 121.9(5) . . ?
C26B C27 C31 117.9(8) . . ?
C27 C28 C29 121.8(4) . . ?
C28 C29 C32 119.9(4) . . ?
C28 C29 C24B 119.3(5) . . ?
C24A C29 C28 119.6(4) . . ?
C24A C29 C32 120.4(4) . . ?
C24B C29 C32 119.3(5) . . ?
C34 C33 C20 120.8(3) . . ?
C38 C33 C20 119.9(3) . . ?
C38 C33 C34 119.1(3) . . ?
C33 C34 C39 123.1(3) . . ?
C35 C34 C33 119.1(4) . . ?
C35 C34 C39 117.8(3) . . ?
C36 C35 C34 122.7(4) . . ?
C35 C36 C40 121.8(3) . . ?
C37 C36 C35 117.5(3) . . ?
C37 C36 C40 120.7(4) . . ?
C36 C37 C38 122.4(4) . . ?
C33 C38 C41 124.7(3) . . ?
C37 C38 C33 119.2(3) . . ?
C37 C38 C41 116.1(3) . . ?
C29 C24A C9 119.0(4) . . ?
C29 C24A C25A 120.1(5) . . ?
C25A C24A C9 120.6(5) . . ?
C24A C25A C30A 120.0(5) . . ?
C26A C25A C24A 118.4(6) . . ?
C26A C25A C30A 121.6(6) . . ?
C25A C26A C27 121.9(6) . . ?
C29 C24B C9 117.8(7) . . ?
C29 C24B C25B 118.7(10) . . ?
C25B C24B C9 122.2(10) . . ?
C24B C25B C30B 120.2(13) . . ?
C26B C25B C24B 120.4(15) . . ?
C26B C25B C30B 118.5(13) . . ?
C25B C26B C27 118.4(14) . . ?

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

#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1521970'
_audit_update_record             
;
2016-12-10 deposited with the CCDC.
2017-06-21 downloaded from the CCDC.
;
_audit_creation_date             2016-12-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C102 H98 Ir2 N6 O2, C5 H12, C6 H5 Cl'
_chemical_formula_sum            'C113 H115 Cl Ir2 N6 O2'
_chemical_formula_weight         2008.95
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.0305(6)
_cell_length_b                   12.8786(6)
_cell_length_c                   16.9004(8)
_cell_angle_alpha                73.0878(16)
_cell_angle_beta                 70.7745(17)
_cell_angle_gamma                78.2922(17)
_cell_volume                     2348.8(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.15
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.798
_exptl_absorpt_coefficient_mu    2.913
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.7820
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0921 before and 0.0526 after correction.
The Ratio of minimum to maximum transmission is 0.9072.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1022
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.003
0.00 0.00 1.00 0.035
-1.00 1.00 0.00 0.029
-1.00 2.00 1.00 0.024
1.00 -2.00 -1.00 0.017
-1.00 2.00 -2.00 0.021
2.00 2.00 1.00 0.025
-2.00 -2.00 -1.00 0.022

_exptl_crystal_size_max          0.081
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.051
_exptl_special_details           
;
 Data were collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 4 runs of 340 narrow-frame ω-scans (scan 
width 0.5°, 45 s exposure), every run at a different φ angle.
Two runs of 358 φ-scans (scan width 1°, 3s exposure) were used for 
scaling overflowing intensities. Crystal to detector distance 3.50 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0573
_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       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            37364
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.149
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7606
_reflns_number_total             9580
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3 v.2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 multi-CPU (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max         1.361
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     619
_refine_ls_number_reflns         9580
_refine_ls_number_restraints     577
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.025
_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)+(0.0420P)²+1.6250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0859
_refine_special_details          
;
 The disoredred solvent was refined as a superposition of PhCl and 
n-pentane, both with occupancies of 0.5. 
Methyl groups were refined as rigid bodies rotating around C---C 
 bonds, with a common refined U for three H atoms. Other H atoms: 
 riding model.
;
_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
 C60-C61 = C59-C60 = C61-C62
 1.53 with sigma of 0.02
 C59-C58
 1.5 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Uiso(H41A)=Uiso(H41B)=Uiso(H41C)=FVAR(1)
 Uiso(H40A)=Uiso(H40B)=Uiso(H40C)=FVAR(2)
 Uiso(H39A)=Uiso(H39B)=Uiso(H39C)=FVAR(3)
 Uiso(H49A)=Uiso(H49B)=Uiso(H49C)=FVAR(4)
 Uiso(H51A)=Uiso(H51B)=Uiso(H51C)=FVAR(5)
 Uiso(H32A)=Uiso(H32B)=Uiso(H32C)=FVAR(6)
 Uiso(H30A)=Uiso(H30B)=Uiso(H30C)=FVAR(7)
 Uiso(H50A)=Uiso(H50B)=Uiso(H50C)=FVAR(8)
 Uiso(H31A)=Uiso(H31B)=Uiso(H31C)=FVAR(9)
 Fixed Sof: C58(0.5) H58A(0.5) H58B(0.5) H58C(0.5) C59(0.5) H59A(0.5)
 H59B(0.5) C60(0.5) H60A(0.5) H60B(0.5) C61(0.5) H61A(0.5) H61B(0.5) C62(0.5)
 H62A(0.5) H62B(0.5) H62C(0.5) Cl21(0.5) C52(0.5) C57(0.5) H57(0.5) C56(0.5)
 H56(0.5) C55(0.5) H55(0.5) C54(0.5) H54(0.5) C53(0.5) H53(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C59(H59A,H59B), C60(H60A,H60B), C61(H61A,H61B)
5.b Me refined with riding coordinates:
 C58(H58A,H58B,H58C), C62(H62A,H62B,H62C)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16), C19(H19), C21(H21), C22(H22), C26(H26), C28(H28),
  C35(H35), C37(H37), C43(H43), C44(H44), C46(H46), C47(H47), C57(H57),
 C56(H56), C55(H55), C54(H54), C53(H53)
5.d Fitted hexagon refined as free rotating group:
 C52(C57,C56,C55,C54,C53)
5.e Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C39(H39A,H39B,
 H39C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C49(H49A,H49B,H49C), C50(H50A,
 H50B,H50C), C51(H51A,H51B,H51C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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
Ir Ir 0.30050(2) 0.59257(2) 0.61740(2) 0.03043(7) Uani 1 1 d . U . . .
O1 O 0.3903(3) 0.4361(2) 0.59010(19) 0.0339(7) Uani 1 1 d . U . . .
N2 N 0.4424(3) 0.6359(3) 0.5016(2) 0.0302(8) Uani 1 1 d . U . . .
N3 N 0.1946(3) 0.6305(3) 0.5391(2) 0.0303(8) Uani 1 1 d . U . . .
N4 N 0.3974(3) 0.5513(3) 0.7033(2) 0.0301(8) Uani 1 1 d . U . . .
C1 C 0.2327(4) 0.7428(3) 0.6294(3) 0.0342(10) Uani 1 1 d . U . . .
C2 C 0.2585(5) 0.8019(4) 0.6775(3) 0.0439(12) Uani 1 1 d . U . . .
H2 H 0.3067 0.7664 0.7146 0.053 Uiso 1 1 calc R . . . .
C3 C 0.2157(6) 0.9097(4) 0.6721(4) 0.0686(19) Uani 1 1 d . U . . .
H3 H 0.2355 0.9481 0.7049 0.082 Uiso 1 1 calc R . . . .
C4 C 0.1442(7) 0.9635(5) 0.6200(5) 0.088(3) Uani 1 1 d . U . . .
H4 H 0.1142 1.0382 0.6172 0.105 Uiso 1 1 calc R . . . .
C5 C 0.1167(6) 0.9077(4) 0.5720(4) 0.072(2) Uani 1 1 d . U . . .
H5 H 0.0682 0.9443 0.5354 0.086 Uiso 1 1 calc R . . . .
C6 C 0.1592(5) 0.7991(4) 0.5768(3) 0.0426(12) Uani 1 1 d . U . . .
C7 C 0.1364(4) 0.7328(3) 0.5276(3) 0.0372(11) Uani 1 1 d . U . . .
C8 C 0.0647(4) 0.7653(4) 0.4728(3) 0.0393(11) Uani 1 1 d . U . . .
H8 H 0.0254 0.8378 0.4642 0.047 Uiso 1 1 calc R . . . .
C9 C 0.0492(4) 0.6944(4) 0.4304(3) 0.0358(10) Uani 1 1 d . U . . .
C10 C 0.1105(4) 0.5898(4) 0.4444(3) 0.0391(11) Uani 1 1 d . U . . .
H10 H 0.1034 0.5386 0.4161 0.047 Uiso 1 1 calc R . . . .
C11 C 0.1805(4) 0.5603(4) 0.4984(3) 0.0355(10) Uani 1 1 d . U . . .
H11 H 0.2205 0.4882 0.5076 0.043 Uiso 1 1 calc R . . . .
C12 C 0.1749(4) 0.5334(3) 0.7257(3) 0.0346(10) Uani 1 1 d . U . . .
C13 C 0.0559(4) 0.5285(4) 0.7367(3) 0.0449(12) Uani 1 1 d . U . . .
H13 H 0.0251 0.5566 0.6886 0.054 Uiso 1 1 calc R . . . .
C14 C -0.0175(5) 0.4836(5) 0.8160(4) 0.0574(15) Uani 1 1 d . U . . .
H14 H -0.0977 0.4792 0.8213 0.069 Uiso 1 1 calc R . . . .
C15 C 0.0236(5) 0.4442(5) 0.8889(4) 0.0589(15) Uani 1 1 d . U . . .
H15 H -0.0286 0.4150 0.9437 0.071 Uiso 1 1 calc R . . . .
C16 C 0.1388(5) 0.4482(4) 0.8805(3) 0.0515(14) Uani 1 1 d . U . . .
H16 H 0.1676 0.4214 0.9297 0.062 Uiso 1 1 calc R . . . .
C17 C 0.2162(4) 0.4921(4) 0.7993(3) 0.0367(11) Uani 1 1 d . U . . .
C18 C 0.3411(4) 0.4977(3) 0.7859(3) 0.0350(10) Uani 1 1 d . U . . .
C19 C 0.4033(4) 0.4535(4) 0.8456(3) 0.0379(11) Uani 1 1 d . U . . .
H19 H 0.3628 0.4167 0.9023 0.045 Uiso 1 1 calc R . . . .
C20 C 0.5230(4) 0.4610(4) 0.8258(3) 0.0383(11) Uani 1 1 d . U . . .
C21 C 0.5784(4) 0.5172(4) 0.7418(3) 0.0364(11) Uani 1 1 d . U . . .
H21 H 0.6602 0.5256 0.7250 0.044 Uiso 1 1 calc R . . . .
C22 C 0.5130(4) 0.5605(4) 0.6836(3) 0.0336(10) Uani 1 1 d . U . . .
H22 H 0.5518 0.5986 0.6268 0.040 Uiso 1 1 calc R . . . .
C23 C 0.4832(4) 0.4440(3) 0.5263(3) 0.0291(10) Uani 1 1 d . U . . .
C24 C -0.0291(4) 0.7284(4) 0.3722(3) 0.0382(11) Uani 1 1 d . U . . .
C25 C 0.0204(5) 0.7435(5) 0.2836(4) 0.0577(15) Uani 1 1 d . U . . .
C26 C -0.0548(6) 0.7720(6) 0.2323(4) 0.0748(19) Uani 1 1 d . U . . .
H26 H -0.0213 0.7841 0.1715 0.090 Uiso 1 1 calc R . . . .
C27 C -0.1754(6) 0.7834(5) 0.2652(5) 0.0696(17) Uani 1 1 d . U . . .
C28 C -0.2224(5) 0.7685(4) 0.3523(4) 0.0555(14) Uani 1 1 d . U . . .
H28 H -0.3062 0.7768 0.3759 0.067 Uiso 1 1 calc R . . . .
C29 C -0.1527(4) 0.7418(4) 0.4075(4) 0.0466(12) Uani 1 1 d . U . . .
C30 C 0.1538(5) 0.7316(7) 0.2441(4) 0.095(3) Uani 1 1 d . U . . .
H30A H 0.1880 0.6594 0.2709 0.128(17) Uiso 1 1 calc GR . . . .
H30B H 0.1871 0.7884 0.2541 0.128(17) Uiso 1 1 calc GR . . . .
H30C H 0.1724 0.7392 0.1819 0.128(17) Uiso 1 1 calc GR . . . .
C31 C -0.2552(7) 0.8112(7) 0.2062(6) 0.115(3) Uani 1 1 d . U . . .
H31A H -0.3235 0.7697 0.2340 0.16(2) Uiso 1 1 calc GR . . . .
H31B H -0.2104 0.7923 0.1513 0.16(2) Uiso 1 1 calc GR . . . .
H31C H -0.2829 0.8896 0.1954 0.16(2) Uiso 1 1 calc GR . . . .
C32 C -0.2095(5) 0.7292(5) 0.5021(4) 0.0683(17) Uani 1 1 d . U . . .
H32A H -0.2010 0.7934 0.5187 0.096(13) Uiso 1 1 calc GR . . . .
H32B H -0.1711 0.6635 0.5340 0.096(13) Uiso 1 1 calc GR . . . .
H32C H -0.2939 0.7224 0.5159 0.096(13) Uiso 1 1 calc GR . . . .
C33 C 0.5884(4) 0.4090(4) 0.8908(3) 0.0379(11) Uani 1 1 d . U . . .
C34 C 0.5956(5) 0.2960(4) 0.9250(3) 0.0461(12) Uani 1 1 d . U . . .
C35 C 0.6567(5) 0.2491(4) 0.9864(3) 0.0482(12) Uani 1 1 d . U . . .
H35 H 0.6618 0.1722 1.0094 0.058 Uiso 1 1 calc R . . . .
C36 C 0.7094(4) 0.3098(4) 1.0147(3) 0.0443(12) Uani 1 1 d . U . . .
C37 C 0.7017(4) 0.4217(4) 0.9804(3) 0.0439(12) Uani 1 1 d . U . . .
H37 H 0.7386 0.4645 0.9994 0.053 Uiso 1 1 calc R . . . .
C38 C 0.6418(4) 0.4735(4) 0.9190(3) 0.0396(11) Uani 1 1 d . U . . .
C39 C 0.5429(6) 0.2223(5) 0.8951(4) 0.0677(17) Uani 1 1 d . U . . .
H39A H 0.5541 0.2487 0.8327 0.080(11) Uiso 1 1 calc GR . . . .
H39B H 0.4580 0.2230 0.9255 0.080(11) Uiso 1 1 calc GR . . . .
H39C H 0.5825 0.1476 0.9077 0.080(11) Uiso 1 1 calc GR . . . .
C40 C 0.7754(6) 0.2576(5) 1.0812(4) 0.0688(18) Uani 1 1 d . U . . .
H40A H 0.7926 0.3145 1.1019 0.110(15) Uiso 1 1 calc GR . . . .
H40B H 0.8499 0.2166 1.0551 0.110(15) Uiso 1 1 calc GR . . . .
H40C H 0.7266 0.2078 1.1299 0.110(15) Uiso 1 1 calc GR . . . .
C41 C 0.6309(5) 0.5961(4) 0.8884(3) 0.0477(13) Uani 1 1 d . U . . .
H41A H 0.6868 0.6172 0.8309 0.069(10) Uiso 1 1 calc GR . . . .
H41B H 0.6489 0.6270 0.9287 0.069(10) Uiso 1 1 calc GR . . . .
H41C H 0.5499 0.6241 0.8855 0.069(10) Uiso 1 1 calc GR . . . .
C42 C 0.4439(4) 0.7442(3) 0.4456(3) 0.0307(10) Uani 1 1 d . U . . .
C43 C 0.4560(4) 0.8322(3) 0.4711(3) 0.0370(11) Uani 1 1 d . U . . .
H43 H 0.4722 0.8214 0.5245 0.044 Uiso 1 1 calc R . . . .
C44 C 0.4444(4) 0.9374(3) 0.4191(3) 0.0391(11) Uani 1 1 d . U . . .
H44 H 0.4534 0.9973 0.4376 0.047 Uiso 1 1 calc R . . . .
C45 C 0.4202(4) 0.9569(3) 0.3411(3) 0.0353(10) Uani 1 1 d . U . . .
C46 C 0.4091(5) 0.8671(3) 0.3163(3) 0.0405(12) Uani 1 1 d . U . . .
H46 H 0.3924 0.8776 0.2631 0.049 Uiso 1 1 calc R . . . .
C47 C 0.4217(4) 0.7624(3) 0.3671(3) 0.0378(11) Uani 1 1 d . U . . .
H47 H 0.4150 0.7022 0.3479 0.045 Uiso 1 1 calc R . . . .
C48 C 0.3987(5) 1.0735(4) 0.2854(3) 0.0468(12) Uani 1 1 d . U . . .
C49 C 0.2653(6) 1.1079(5) 0.3059(5) 0.0768(19) Uani 1 1 d . U . . .
H49A H 0.2320 1.1050 0.3677 0.067(10) Uiso 1 1 calc GR . . . .
H49B H 0.2283 1.0582 0.2907 0.067(10) Uiso 1 1 calc GR . . . .
H49C H 0.2500 1.1826 0.2724 0.067(10) Uiso 1 1 calc GR . . . .
C50 C 0.4523(8) 1.0763(5) 0.1907(4) 0.105(3) Uani 1 1 d . U . . .
H50A H 0.4075 1.0356 0.1734 0.108(15) Uiso 1 1 calc GR . . . .
H50B H 0.5350 1.0429 0.1804 0.108(15) Uiso 1 1 calc GR . . . .
H50C H 0.4493 1.1523 0.1568 0.108(15) Uiso 1 1 calc GR . . . .
C51 C 0.4519(6) 1.1554(4) 0.3070(4) 0.0729(19) Uani 1 1 d . U . . .
H51A H 0.5369 1.1325 0.2991 0.106(14) Uiso 1 1 calc GR . . . .
H51B H 0.4127 1.1589 0.3672 0.106(14) Uiso 1 1 calc GR . . . .
H51C H 0.4404 1.2277 0.2688 0.106(14) Uiso 1 1 calc GR . . . .
C58 C -0.071(2) 1.0000(16) 0.9920(13) 0.158(9) Uani 0.5 1 d D U P A -2
H58A H -0.0906 1.0783 0.9898 0.237 Uiso 0.5 1 calc R . P A -2
H58B H -0.0772 0.9588 1.0517 0.237 Uiso 0.5 1 calc R . P A -2
H58C H 0.0101 0.9863 0.9555 0.237 Uiso 0.5 1 calc R . P A -2
C59 C -0.152(3) 0.966(2) 0.961(2) 0.223(12) Uani 0.5 1 d D U P A -2
H59A H -0.1462 1.0136 0.9024 0.268 Uiso 0.5 1 calc R . P A -2
H59B H -0.2325 0.9864 0.9975 0.268 Uiso 0.5 1 calc R . P A -2
C60 C -0.154(2) 0.850(2) 0.9534(14) 0.185(10) Uani 0.5 1 d D U P A -2
H60A H -0.1278 0.7956 1.0006 0.222 Uiso 0.5 1 calc R . P A -2
H60B H -0.2356 0.8397 0.9589 0.222 Uiso 0.5 1 calc R . P A -2
C61 C -0.076(2) 0.8350(18) 0.8708(14) 0.156(7) Uani 0.5 1 d D U P A -2
H61A H 0.0037 0.8556 0.8605 0.188 Uiso 0.5 1 calc R . P A -2
H61B H -0.1086 0.8792 0.8232 0.188 Uiso 0.5 1 calc R . P A -2
C62 C -0.0691(12) 0.7059(16) 0.8789(11) 0.111(6) Uani 0.5 1 d D U P A -2
H62A H -0.0172 0.6881 0.8250 0.167 Uiso 0.5 1 calc R . P A -2
H62B H -0.0373 0.6639 0.9268 0.167 Uiso 0.5 1 calc R . P A -2
H62C H -0.1488 0.6874 0.8898 0.167 Uiso 0.5 1 calc R . P A -2
Cl21 Cl -0.3417(4) 0.9550(4) 1.0140(3) 0.1173(16) Uani 0.5 1 d . U P B 1
C52 C -0.2233(7) 0.9050(8) 0.9404(6) 0.074(4) Uani 0.5 1 d . U P B 1
C57 C -0.2091(8) 0.7962(7) 0.9373(6) 0.078(4) Uani 0.5 1 d G U P B 1
H57 H -0.2647 0.7488 0.9771 0.094 Uiso 0.5 1 calc R . P B 1
C56 C -0.1136(9) 0.7569(7) 0.8762(7) 0.074(4) Uani 0.5 1 d G U P B 1
H56 H -0.1040 0.6826 0.8741 0.089 Uiso 0.5 1 calc R . P B 1
C55 C -0.0323(7) 0.8263(10) 0.8180(7) 0.101(5) Uani 0.5 1 d G U P B 1
H55 H 0.0330 0.7994 0.7762 0.121 Uiso 0.5 1 calc R . P B 1
C54 C -0.0465(8) 0.9350(9) 0.8211(6) 0.100(5) Uani 0.5 1 d G U P B 1
H54 H 0.0091 0.9824 0.7814 0.119 Uiso 0.5 1 calc R . P B 1
C53 C -0.1419(9) 0.9744(6) 0.8823(7) 0.107(5) Uani 0.5 1 d G U P B 1
H53 H -0.1516 1.0487 0.8843 0.128 Uiso 0.5 1 calc R . P B 1


_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
Ir O1 2.184(3) . ?
Ir N2 2.147(3) . ?
Ir N3 2.023(4) . ?
Ir N4 2.040(4) . ?
Ir C1 1.982(4) . ?
Ir C12 2.013(4) . ?
O1 C23 1.269(5) . ?
N2 C23 1.309(5) 2_666 ?
N2 C42 1.439(5) . ?
N3 C7 1.353(5) . ?
N3 C11 1.351(5) . ?
N4 C18 1.374(5) . ?
N4 C22 1.341(6) . ?
C1 C2 1.401(6) . ?
C1 C6 1.406(6) . ?
C2 C3 1.367(7) . ?
C3 C4 1.378(8) . ?
C4 C5 1.377(8) . ?
C5 C6 1.377(6) . ?
C6 C7 1.469(6) . ?
C7 C8 1.389(6) . ?
C8 C9 1.386(6) . ?
C9 C10 1.393(6) . ?
C9 C24 1.497(7) . ?
C10 C11 1.364(6) . ?
C12 C13 1.394(7) . ?
C12 C17 1.412(6) . ?
C13 C14 1.373(7) . ?
C14 C15 1.399(8) . ?
C15 C16 1.357(7) . ?
C16 C17 1.411(6) . ?
C17 C18 1.457(6) . ?
C18 C19 1.376(6) . ?
C19 C20 1.383(6) . ?
C20 C21 1.400(6) . ?
C20 C33 1.484(6) . ?
C21 C22 1.382(6) . ?
C23 N2 1.309(5) 2_666 ?
C23 C23 1.514(8) 2_666 ?
C24 C25 1.386(7) . ?
C24 C29 1.402(7) . ?
C25 C26 1.380(8) . ?
C25 C30 1.516(8) . ?
C26 C27 1.366(8) . ?
C27 C28 1.362(9) . ?
C27 C31 1.524(8) . ?
C28 C29 1.381(8) . ?
C29 C32 1.492(8) . ?
C33 C34 1.397(7) . ?
C33 C38 1.407(7) . ?
C34 C35 1.393(7) . ?
C34 C39 1.515(8) . ?
C35 C36 1.363(7) . ?
C36 C37 1.384(7) . ?
C36 C40 1.510(7) . ?
C37 C38 1.391(7) . ?
C38 C41 1.505(7) . ?
C42 C43 1.373(6) . ?
C42 C47 1.383(6) . ?
C43 C44 1.392(6) . ?
C44 C45 1.385(6) . ?
C45 C46 1.383(6) . ?
C45 C48 1.545(6) . ?
C46 C47 1.381(6) . ?
C48 C49 1.525(8) . ?
C48 C50 1.508(8) . ?
C48 C51 1.520(8) . ?
C58 C59 1.441(18) . ?
C59 C60 1.532(18) . ?
C60 C61 1.446(17) . ?
C61 C62 1.616(17) . ?
Cl21 C52 1.708(9) . ?
C52 C57 1.3900 . ?
C52 C53 1.3900 . ?
C57 C56 1.3900 . ?
C56 C55 1.3900 . ?
C55 C54 1.3900 . ?
C54 C53 1.3900 . ?

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
N2 Ir O1 75.64(12) . . ?
N3 Ir O1 98.97(12) . . ?
N3 Ir N2 86.07(14) . . ?
N3 Ir N4 176.07(14) . . ?
N4 Ir O1 81.92(12) . . ?
N4 Ir N2 97.86(14) . . ?
C1 Ir O1 173.20(15) . . ?
C1 Ir N2 97.56(16) . . ?
C1 Ir N3 80.06(16) . . ?
C1 Ir N4 99.50(16) . . ?
C1 Ir C12 89.20(18) . . ?
C12 Ir O1 97.59(14) . . ?
C12 Ir N2 173.23(14) . . ?
C12 Ir N3 95.34(17) . . ?
C12 Ir N4 80.74(17) . . ?
C23 O1 Ir 114.0(2) . . ?
C23 N2 Ir 117.3(3) 2_666 . ?
C23 N2 C42 119.0(4) 2_666 . ?
C42 N2 Ir 122.4(3) . . ?
C7 N3 Ir 116.9(3) . . ?
C11 N3 Ir 123.7(3) . . ?
C11 N3 C7 119.4(4) . . ?
C18 N4 Ir 115.8(3) . . ?
C22 N4 Ir 125.5(3) . . ?
C22 N4 C18 118.2(4) . . ?
C2 C1 Ir 127.4(3) . . ?
C2 C1 C6 116.8(4) . . ?
C6 C1 Ir 115.5(3) . . ?
C3 C2 C1 121.2(5) . . ?
C2 C3 C4 121.1(5) . . ?
C5 C4 C3 119.2(5) . . ?
C6 C5 C4 120.3(5) . . ?
C1 C6 C7 114.1(4) . . ?
C5 C6 C1 121.3(4) . . ?
C5 C6 C7 124.5(4) . . ?
N3 C7 C6 113.2(4) . . ?
N3 C7 C8 119.9(4) . . ?
C8 C7 C6 126.9(4) . . ?
C9 C8 C7 121.4(4) . . ?
C8 C9 C10 116.7(4) . . ?
C8 C9 C24 121.7(4) . . ?
C10 C9 C24 121.5(4) . . ?
C11 C10 C9 120.5(4) . . ?
N3 C11 C10 122.0(4) . . ?
C13 C12 Ir 128.9(4) . . ?
C13 C12 C17 117.4(4) . . ?
C17 C12 Ir 113.6(3) . . ?
C14 C13 C12 121.1(5) . . ?
C13 C14 C15 121.2(5) . . ?
C16 C15 C14 119.2(5) . . ?
C15 C16 C17 120.4(5) . . ?
C12 C17 C18 116.3(4) . . ?
C16 C17 C12 120.6(5) . . ?
C16 C17 C18 123.1(4) . . ?
N4 C18 C17 113.2(4) . . ?
N4 C18 C19 120.3(4) . . ?
C19 C18 C17 126.5(4) . . ?
C18 C19 C20 122.1(4) . . ?
C19 C20 C21 116.8(4) . . ?
C19 C20 C33 120.8(4) . . ?
C21 C20 C33 122.4(4) . . ?
C22 C21 C20 119.4(4) . . ?
N4 C22 C21 123.2(4) . . ?
O1 C23 N2 127.3(4) . 2_666 ?
O1 C23 C23 119.4(5) . 2_666 ?
N2 C23 C23 113.3(5) 2_666 2_666 ?
C25 C24 C9 119.9(4) . . ?
C25 C24 C29 120.1(5) . . ?
C29 C24 C9 119.9(5) . . ?
C24 C25 C30 120.9(5) . . ?
C26 C25 C24 118.2(5) . . ?
C26 C25 C30 120.9(5) . . ?
C27 C26 C25 122.8(6) . . ?
C26 C27 C31 121.0(7) . . ?
C28 C27 C26 118.1(6) . . ?
C28 C27 C31 120.9(6) . . ?
C27 C28 C29 122.3(5) . . ?
C24 C29 C32 121.9(5) . . ?
C28 C29 C24 118.4(5) . . ?
C28 C29 C32 119.7(5) . . ?
C34 C33 C20 120.0(5) . . ?
C34 C33 C38 119.8(4) . . ?
C38 C33 C20 120.1(4) . . ?
C33 C34 C39 122.0(5) . . ?
C35 C34 C33 119.1(5) . . ?
C35 C34 C39 118.8(5) . . ?
C36 C35 C34 122.2(5) . . ?
C35 C36 C37 118.3(5) . . ?
C35 C36 C40 121.5(5) . . ?
C37 C36 C40 120.2(5) . . ?
C36 C37 C38 122.2(5) . . ?
C33 C38 C41 122.2(4) . . ?
C37 C38 C33 118.4(5) . . ?
C37 C38 C41 119.4(5) . . ?
C43 C42 N2 121.8(4) . . ?
C43 C42 C47 118.6(4) . . ?
C47 C42 N2 119.3(4) . . ?
C42 C43 C44 120.2(4) . . ?
C45 C44 C43 121.7(4) . . ?
C44 C45 C48 122.5(4) . . ?
C46 C45 C44 117.1(4) . . ?
C46 C45 C48 120.3(4) . . ?
C47 C46 C45 121.4(4) . . ?
C46 C47 C42 120.9(4) . . ?
C49 C48 C45 108.3(4) . . ?
C50 C48 C45 110.5(4) . . ?
C50 C48 C49 110.6(6) . . ?
C50 C48 C51 108.8(5) . . ?
C51 C48 C45 111.4(4) . . ?
C51 C48 C49 107.2(5) . . ?
C58 C59 C60 127(3) . . ?
C61 C60 C59 110(2) . . ?
C60 C61 C62 104.0(18) . . ?
C57 C52 Cl21 120.5(6) . . ?
C57 C52 C53 120.0 . . ?
C53 C52 Cl21 119.5(6) . . ?
C52 C57 C56 120.0 . . ?
C57 C56 C55 120.0 . . ?
C54 C55 C56 120.0 . . ?
C55 C54 C53 120.0 . . ?
C54 C53 C52 120.0 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'

#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chlorobenzene, pentane'
_exptl_crystal_preparation       ', Luminescent'
