# 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_a086
_database_code_depnum_ccdc_archive 'CCDC 1541442'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        (pthpy)2Iracac
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H23 Ir N2 O2 S2'
_chemical_formula_sum            'C31 H23 Ir N2 O2 S2'
_chemical_formula_weight         711.85

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'
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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   10.4155(5)
_cell_length_b                   17.9067(8)
_cell_length_c                   14.6999(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.6850(10)
_cell_angle_gamma                90.00
_cell_volume                     2581.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    186(2)
_cell_measurement_reflns_used    7431
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.38
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    5.367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3472
_exptl_absorpt_correction_T_max  0.5897
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      186(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12948
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.35
_reflns_number_total             4721
_reflns_number_gt                4244
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0325P)²+0.2985P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4721
_refine_ls_number_parameters     345
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0578
_refine_ls_wR_factor_gt          0.0561
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.444353(12) 0.220159(7) 0.116414(8) 0.02457(6) Uani 1 1 d . . .
S1 S 0.95561(10) 0.14027(7) 0.50209(7) 0.0493(3) Uani 1 1 d . . .
S2 S -0.05736(15) 0.23509(8) -0.28903(9) 0.0775(5) Uani 1 1 d U . .
O1 O 0.3461(2) 0.30230(14) 0.17739(16) 0.0304(5) Uani 1 1 d . . .
O2 O 0.5627(2) 0.30984(14) 0.08832(17) 0.0333(6) Uani 1 1 d . . .
N1 N 0.5991(3) 0.19649(16) 0.24116(19) 0.0279(6) Uani 1 1 d . . .
N2 N 0.2877(3) 0.23322(15) -0.0099(2) 0.0273(6) Uani 1 1 d . . .
C1 C 0.5458(3) 0.14615(19) 0.0674(2) 0.0269(7) Uani 1 1 d . . .
C2 C 0.6677(3) 0.11814(18) 0.1368(2) 0.0272(7) Uani 1 1 d . . .
C3 C 0.7452(4) 0.0651(2) 0.1094(3) 0.0363(9) Uani 1 1 d . . .
H3 H 0.8178 0.0470 0.1526 0.044 Uiso 1 1 calc R . .
C4 C 0.7097(4) 0.0406(2) 0.0154(3) 0.0410(9) Uani 1 1 d . . .
H4 H 0.7646 0.0048 -0.0021 0.049 Uiso 1 1 calc R . .
C5 C 0.5931(4) 0.0685(2) -0.0533(3) 0.0394(9) Uani 1 1 d . . .
H5 H 0.5684 0.0523 -0.1184 0.047 Uiso 1 1 calc R . .
C6 C 0.5128(4) 0.1196(2) -0.0275(2) 0.0343(8) Uani 1 1 d . . .
H6 H 0.4326 0.1375 -0.0756 0.041 Uiso 1 1 calc R . .
C7 C 0.6962(3) 0.14768(18) 0.2347(2) 0.0262(7) Uani 1 1 d . . .
C8 C 0.8087(3) 0.13237(19) 0.3197(2) 0.0291(7) Uani 1 1 d . . .
C9 C 0.9304(3) 0.0887(2) 0.3339(3) 0.0359(8) Uani 1 1 d . . .
H9 H 0.9477 0.0651 0.2876 0.043 Uiso 1 1 calc R . .
C10 C 1.0143(4) 0.0883(2) 0.4262(3) 0.0433(9) Uani 1 1 d . . .
H10 H 1.0982 0.0617 0.4475 0.052 Uiso 1 1 calc R . .
C11 C 0.8109(4) 0.1645(2) 0.4068(2) 0.0361(8) Uani 1 1 d . . .
C12 C 0.7073(4) 0.2123(2) 0.4115(3) 0.0456(10) Uani 1 1 d . . .
H12 H 0.7081 0.2336 0.4709 0.055 Uiso 1 1 calc R . .
C13 C 0.6052(4) 0.2271(2) 0.3271(3) 0.0369(9) Uani 1 1 d . . .
H13 H 0.5348 0.2603 0.3283 0.044 Uiso 1 1 calc R . .
C14 C 0.3193(3) 0.14176(19) 0.1322(2) 0.0305(8) Uani 1 1 d . . .
C15 C 0.1865(4) 0.14384(19) 0.0627(3) 0.0326(8) Uani 1 1 d . . .
C16 C 0.0852(4) 0.0968(2) 0.0729(3) 0.0436(9) Uani 1 1 d . . .
H16 H 0.0024 0.1004 0.0324 0.052 Uiso 1 1 calc R . .
C17 C 0.1143(5) 0.0454(2) 0.1453(3) 0.0515(11) Uani 1 1 d . . .
H17 H 0.0440 0.0140 0.1514 0.062 Uiso 1 1 calc R . .
C18 C 0.2457(4) 0.0386(2) 0.2102(3) 0.0488(10) Uani 1 1 d . . .
H18 H 0.2667 0.0010 0.2586 0.059 Uiso 1 1 calc R . .
C19 C 0.3464(4) 0.0871(2) 0.2040(3) 0.0387(9) Uani 1 1 d . . .
H19 H 0.4359 0.0829 0.2496 0.046 Uiso 1 1 calc R . .
C20 C 0.1726(3) 0.1929(2) -0.0206(3) 0.0305(8) Uani 1 1 d . . .
C21 C 0.0633(4) 0.1963(2) -0.1095(3) 0.0413(10) Uani 1 1 d . . .
C22 C -0.0691(4) 0.1619(2) -0.1419(3) 0.0623(14) Uani 1 1 d . . .
H22 H -0.0995 0.1337 -0.1054 0.075 Uiso 1 1 calc R . .
C23 C -0.1401(5) 0.1777(3) -0.2333(4) 0.0850(16) Uani 1 1 d U . .
H23 H -0.2292 0.1588 -0.2651 0.102 Uiso 1 1 calc R . .
C24 C 0.0824(4) 0.2394(3) -0.1841(3) 0.0491(12) Uani 1 1 d . . .
C25 C 0.2012(4) 0.2795(2) -0.1721(3) 0.0462(11) Uani 1 1 d . . .
H25 H 0.2132 0.3079 -0.2232 0.055 Uiso 1 1 calc R . .
C26 C 0.2996(4) 0.27600(19) -0.0834(3) 0.0373(9) Uani 1 1 d . . .
H26 H 0.3802 0.3046 -0.0723 0.045 Uiso 1 1 calc R . .
C27 C 0.3570(4) 0.3720(2) 0.1716(2) 0.0323(8) Uani 1 1 d . . .
C28 C 0.4445(4) 0.4106(2) 0.1319(3) 0.0411(9) Uani 1 1 d . . .
H28 H 0.4382 0.4636 0.1304 0.049 Uiso 1 1 calc R . .
C29 C 0.5395(4) 0.3789(2) 0.0947(2) 0.0355(8) Uani 1 1 d . . .
C30 C 0.2681(4) 0.4184(2) 0.2116(3) 0.0404(9) Uani 1 1 d . . .
H30A H 0.2125 0.4523 0.1614 0.061 Uiso 1 1 calc R . .
H30B H 0.3255 0.4476 0.2667 0.061 Uiso 1 1 calc R . .
H30C H 0.2084 0.3855 0.2328 0.061 Uiso 1 1 calc R . .
C31 C 0.6257(4) 0.4302(2) 0.0569(3) 0.0478(10) Uani 1 1 d . . .
H31A H 0.7225 0.4197 0.0908 0.072 Uiso 1 1 calc R . .
H31B H 0.6061 0.4822 0.0680 0.072 Uiso 1 1 calc R . .
H31C H 0.6044 0.4217 -0.0125 0.072 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 C1 1.976(3) . ?
Ir1 C14 1.982(4) . ?
Ir1 N2 2.030(3) . ?
Ir1 N1 2.037(3) . ?
Ir1 O2 2.147(2) . ?
Ir1 O1 2.152(2) . ?
S1 C10 1.716(4) . ?
S1 C11 1.732(3) . ?
S2 C23 1.717(7) . ?
S2 C24 1.729(4) . ?
O1 C27 1.259(4) . ?
O2 C29 1.270(4) . ?
N1 C13 1.358(5) . ?
N1 C7 1.364(4) . ?
N2 C20 1.362(4) . ?
N2 C26 1.365(4) . ?
C1 C6 1.403(5) . ?
C1 C2 1.425(4) . ?
C2 C3 1.391(5) . ?
C2 C7 1.467(4) . ?
C3 C4 1.376(5) . ?
C3 H3 0.8700 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.422(4) . ?
C8 C11 1.397(5) . ?
C8 C9 1.444(5) . ?
C9 C10 1.344(5) . ?
C9 H9 0.8700 . ?
C10 H10 0.9500 . ?
C11 C12 1.397(5) . ?
C12 C13 1.361(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.397(5) . ?
C14 C15 1.416(5) . ?
C15 C16 1.397(5) . ?
C15 C20 1.475(5) . ?
C16 C17 1.363(6) . ?
C16 H16 0.8700 . ?
C17 C18 1.385(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.416(5) . ?
C21 C24 1.408(6) . ?
C21 C22 1.437(5) . ?
C22 C23 1.327(7) . ?
C22 H22 0.8700 . ?
C23 H23 0.9500 . ?
C24 C25 1.390(6) . ?
C25 C26 1.361(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.417(5) . ?
C27 C30 1.504(5) . ?
C28 C29 1.402(5) . ?
C28 H28 0.9500 . ?
C29 C31 1.514(5) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ir1 C14 91.22(14) . . ?
C1 Ir1 N2 96.19(12) . . ?
C14 Ir1 N2 80.28(13) . . ?
C1 Ir1 N1 80.25(12) . . ?
C14 Ir1 N1 95.69(13) . . ?
N2 Ir1 N1 174.60(11) . . ?
C1 Ir1 O2 91.11(12) . . ?
C14 Ir1 O2 174.28(11) . . ?
N2 Ir1 O2 94.28(10) . . ?
N1 Ir1 O2 89.86(10) . . ?
C1 Ir1 O1 176.25(11) . . ?
C14 Ir1 O1 90.67(12) . . ?
N2 Ir1 O1 87.33(10) . . ?
N1 Ir1 O1 96.34(10) . . ?
O2 Ir1 O1 87.32(10) . . ?
C10 S1 C11 90.79(18) . . ?
C23 S2 C24 90.4(2) . . ?
C27 O1 Ir1 125.7(2) . . ?
C29 O2 Ir1 125.4(2) . . ?
C13 N1 C7 121.3(3) . . ?
C13 N1 Ir1 121.9(2) . . ?
C7 N1 Ir1 116.8(2) . . ?
C20 N2 C26 121.1(3) . . ?
C20 N2 Ir1 116.8(2) . . ?
C26 N2 Ir1 122.0(2) . . ?
C6 C1 C2 117.0(3) . . ?
C6 C1 Ir1 127.4(3) . . ?
C2 C1 Ir1 115.6(2) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 C7 125.8(3) . . ?
C1 C2 C7 114.4(3) . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 122.1(3) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
N1 C7 C8 118.3(3) . . ?
N1 C7 C2 112.9(3) . . ?
C8 C7 C2 128.8(3) . . ?
C11 C8 C7 118.7(3) . . ?
C11 C8 C9 110.4(3) . . ?
C7 C8 C9 130.9(3) . . ?
C10 C9 C8 112.9(3) . . ?
C10 C9 H9 123.5 . . ?
C8 C9 H9 123.5 . . ?
C9 C10 S1 113.6(3) . . ?
C9 C10 H10 123.2 . . ?
S1 C10 H10 123.2 . . ?
C8 C11 C12 121.5(3) . . ?
C8 C11 S1 112.3(3) . . ?
C12 C11 S1 126.1(3) . . ?
C13 C12 C11 116.9(3) . . ?
C13 C12 H12 121.5 . . ?
C11 C12 H12 121.5 . . ?
N1 C13 C12 123.2(3) . . ?
N1 C13 H13 118.4 . . ?
C12 C13 H13 118.4 . . ?
C19 C14 C15 117.6(3) . . ?
C19 C14 Ir1 127.7(3) . . ?
C15 C14 Ir1 114.7(3) . . ?
C16 C15 C14 119.7(4) . . ?
C16 C15 C20 125.6(3) . . ?
C14 C15 C20 114.4(3) . . ?
C17 C16 C15 120.9(4) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 120.4(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C19 119.5(4) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C14 121.5(4) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
N2 C20 C21 119.2(4) . . ?
N2 C20 C15 112.5(3) . . ?
C21 C20 C15 128.0(3) . . ?
C24 C21 C20 117.5(4) . . ?
C24 C21 C22 110.4(4) . . ?
C20 C21 C22 132.1(4) . . ?
C23 C22 C21 112.9(5) . . ?
C23 C22 H22 123.5 . . ?
C21 C22 H22 123.5 . . ?
C22 C23 S2 114.4(4) . . ?
C22 C23 H23 122.8 . . ?
S2 C23 H23 122.8 . . ?
C25 C24 C21 122.5(3) . . ?
C25 C24 S2 125.6(4) . . ?
C21 C24 S2 111.9(4) . . ?
C26 C25 C24 116.7(4) . . ?
C26 C25 H25 121.7 . . ?
C24 C25 H25 121.7 . . ?
C25 C26 N2 123.0(4) . . ?
C25 C26 H26 118.5 . . ?
N2 C26 H26 118.5 . . ?
O1 C27 C28 126.7(3) . . ?
O1 C27 C30 116.1(3) . . ?
C28 C27 C30 117.2(3) . . ?
C29 C28 C27 126.8(4) . . ?
C29 C28 H28 116.6 . . ?
C27 C28 H28 116.6 . . ?
O2 C29 C28 126.9(3) . . ?
O2 C29 C31 114.3(3) . . ?
C28 C29 C31 118.8(4) . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 Ir1 O1 C27 -164.2(3) . . . . ?
N2 Ir1 O1 C27 -83.9(3) . . . . ?
N1 Ir1 O1 C27 100.0(3) . . . . ?
O2 Ir1 O1 C27 10.5(3) . . . . ?
C1 Ir1 O2 C29 171.9(3) . . . . ?
N2 Ir1 O2 C29 75.6(3) . . . . ?
N1 Ir1 O2 C29 -107.9(3) . . . . ?
O1 Ir1 O2 C29 -11.5(3) . . . . ?
C1 Ir1 N1 C13 -176.9(3) . . . . ?
C14 Ir1 N1 C13 -86.7(3) . . . . ?
O2 Ir1 N1 C13 91.9(3) . . . . ?
O1 Ir1 N1 C13 4.6(3) . . . . ?
C1 Ir1 N1 C7 2.4(2) . . . . ?
C14 Ir1 N1 C7 92.7(3) . . . . ?
O2 Ir1 N1 C7 -88.7(2) . . . . ?
O1 Ir1 N1 C7 -176.0(2) . . . . ?
C1 Ir1 N2 C20 97.2(2) . . . . ?
C14 Ir1 N2 C20 7.1(2) . . . . ?
O2 Ir1 N2 C20 -171.2(2) . . . . ?
O1 Ir1 N2 C20 -84.1(2) . . . . ?
C1 Ir1 N2 C26 -78.2(3) . . . . ?
C14 Ir1 N2 C26 -168.4(3) . . . . ?
O2 Ir1 N2 C26 13.4(3) . . . . ?
O1 Ir1 N2 C26 100.5(3) . . . . ?
C14 Ir1 C1 C6 83.8(3) . . . . ?
N2 Ir1 C1 C6 3.4(3) . . . . ?
N1 Ir1 C1 C6 179.3(3) . . . . ?
O2 Ir1 C1 C6 -91.0(3) . . . . ?
C14 Ir1 C1 C2 -97.6(3) . . . . ?
N2 Ir1 C1 C2 -178.0(3) . . . . ?
N1 Ir1 C1 C2 -2.1(2) . . . . ?
O2 Ir1 C1 C2 87.6(3) . . . . ?
C6 C1 C2 C3 -2.0(5) . . . . ?
Ir1 C1 C2 C3 179.2(3) . . . . ?
C6 C1 C2 C7 -179.7(3) . . . . ?
Ir1 C1 C2 C7 1.5(4) . . . . ?
C1 C2 C3 C4 2.3(5) . . . . ?
C7 C2 C3 C4 179.7(3) . . . . ?
C2 C3 C4 C5 -0.9(6) . . . . ?
C3 C4 C5 C6 -0.7(6) . . . . ?
C4 C5 C6 C1 0.9(6) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
Ir1 C1 C6 C5 179.1(3) . . . . ?
C13 N1 C7 C8 -3.2(5) . . . . ?
Ir1 N1 C7 C8 177.4(2) . . . . ?
C13 N1 C7 C2 177.1(3) . . . . ?
Ir1 N1 C7 C2 -2.3(4) . . . . ?
C3 C2 C7 N1 -177.1(3) . . . . ?
C1 C2 C7 N1 0.5(4) . . . . ?
C3 C2 C7 C8 3.3(6) . . . . ?
C1 C2 C7 C8 -179.1(3) . . . . ?
N1 C7 C8 C11 3.6(5) . . . . ?
C2 C7 C8 C11 -176.9(3) . . . . ?
N1 C7 C8 C9 -174.6(3) . . . . ?
C2 C7 C8 C9 5.0(6) . . . . ?
C11 C8 C9 C10 1.1(5) . . . . ?
C7 C8 C9 C10 179.4(4) . . . . ?
C8 C9 C10 S1 -0.6(4) . . . . ?
C11 S1 C10 C9 0.0(3) . . . . ?
C7 C8 C11 C12 -1.5(5) . . . . ?
C9 C8 C11 C12 177.1(3) . . . . ?
C7 C8 C11 S1 -179.6(3) . . . . ?
C9 C8 C11 S1 -1.1(4) . . . . ?
C10 S1 C11 C8 0.7(3) . . . . ?
C10 S1 C11 C12 -177.4(4) . . . . ?
C8 C11 C12 C13 -1.0(6) . . . . ?
S1 C11 C12 C13 176.9(3) . . . . ?
C7 N1 C13 C12 0.7(6) . . . . ?
Ir1 N1 C13 C12 -179.9(3) . . . . ?
C11 C12 C13 N1 1.4(6) . . . . ?
C1 Ir1 C14 C19 75.0(3) . . . . ?
N2 Ir1 C14 C19 171.1(3) . . . . ?
N1 Ir1 C14 C19 -5.3(3) . . . . ?
O1 Ir1 C14 C19 -101.8(3) . . . . ?
C1 Ir1 C14 C15 -106.5(3) . . . . ?
N2 Ir1 C14 C15 -10.4(2) . . . . ?
N1 Ir1 C14 C15 173.2(2) . . . . ?
O1 Ir1 C14 C15 76.8(2) . . . . ?
C19 C14 C15 C16 5.8(5) . . . . ?
Ir1 C14 C15 C16 -172.8(3) . . . . ?
C19 C14 C15 C20 -169.0(3) . . . . ?
Ir1 C14 C15 C20 12.4(4) . . . . ?
C14 C15 C16 C17 -4.3(5) . . . . ?
C20 C15 C16 C17 169.9(4) . . . . ?
C15 C16 C17 C18 -0.3(6) . . . . ?
C16 C17 C18 C19 3.2(6) . . . . ?
C17 C18 C19 C14 -1.5(6) . . . . ?
C15 C14 C19 C18 -3.0(5) . . . . ?
Ir1 C14 C19 C18 175.5(3) . . . . ?
C26 N2 C20 C21 -0.6(5) . . . . ?
Ir1 N2 C20 C21 -176.1(3) . . . . ?
C26 N2 C20 C15 173.2(3) . . . . ?
Ir1 N2 C20 C15 -2.3(4) . . . . ?
C16 C15 C20 N2 179.1(3) . . . . ?
C14 C15 C20 N2 -6.4(4) . . . . ?
C16 C15 C20 C21 -7.8(6) . . . . ?
C14 C15 C20 C21 166.7(3) . . . . ?
N2 C20 C21 C24 2.5(5) . . . . ?
C15 C20 C21 C24 -170.2(3) . . . . ?
N2 C20 C21 C22 -178.9(4) . . . . ?
C15 C20 C21 C22 8.4(7) . . . . ?
C24 C21 C22 C23 1.0(5) . . . . ?
C20 C21 C22 C23 -177.7(4) . . . . ?
C21 C22 C23 S2 -0.4(5) . . . . ?
C24 S2 C23 C22 -0.2(4) . . . . ?
C20 C21 C24 C25 -1.9(6) . . . . ?
C22 C21 C24 C25 179.3(4) . . . . ?
C20 C21 C24 S2 177.8(3) . . . . ?
C22 C21 C24 S2 -1.1(4) . . . . ?
C23 S2 C24 C25 -179.6(4) . . . . ?
C23 S2 C24 C21 0.7(3) . . . . ?
C21 C24 C25 C26 -0.7(6) . . . . ?
S2 C24 C25 C26 179.7(3) . . . . ?
C24 C25 C26 N2 2.8(5) . . . . ?
C20 N2 C26 C25 -2.2(5) . . . . ?
Ir1 N2 C26 C25 173.0(3) . . . . ?
Ir1 O1 C27 C28 -6.1(5) . . . . ?
Ir1 O1 C27 C30 174.3(2) . . . . ?
O1 C27 C28 C29 -2.5(6) . . . . ?
C30 C27 C28 C29 177.1(3) . . . . ?
Ir1 O2 C29 C28 8.3(5) . . . . ?
Ir1 O2 C29 C31 -171.5(2) . . . . ?
C27 C28 C29 O2 1.2(6) . . . . ?
C27 C28 C29 C31 -178.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.206
_refine_diff_density_min         -0.791
_refine_diff_density_rms         0.100
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and methol'
####################################################################### 
# 
# 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_A123
_database_code_depnum_ccdc_archive 'CCDC 1541443'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        (pfupy)2Iracac
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H23 Ir N2 O4, C H2 Cl2 '
_chemical_formula_sum            'C32 H25 Cl2 Ir N2 O4'
_chemical_formula_weight         764.66

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'
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   15.8143(10)
_cell_length_b                   17.4936(11)
_cell_length_c                   10.0825(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.1900(10)
_cell_angle_gamma                90
_cell_volume                     2753.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6994
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      26.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    5.086
_shelx_estimated_absorpt_T_min   0.461
_shelx_estimated_absorpt_T_max   0.605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.527
_exptl_absorpt_correction_T_max  0.670
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17710
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.748
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5031
_reflns_number_gt                4395
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'SMART (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0634P)²+7.9230P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5031
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.22491(2) 0.03413(2) 0.48246(2) 0.02517(11) Uani 1 1 d . . . . .
O1 O 0.0669(3) -0.2623(3) 0.6447(6) 0.0532(14) Uani 1 1 d . . . . .
O2 O 0.3957(3) 0.3334(3) 0.3653(5) 0.0394(11) Uani 1 1 d . . . . .
O3 O 0.2631(3) -0.0298(2) 0.3177(5) 0.0371(11) Uani 1 1 d . . . . .
O4 O 0.1171(3) 0.0741(2) 0.3422(4) 0.0303(9) Uani 1 1 d . . . . .
N1 N 0.1640(3) -0.0612(3) 0.5372(5) 0.0266(11) Uani 1 1 d . . . . .
N2 N 0.2890(3) 0.1306(3) 0.4434(5) 0.0271(11) Uani 1 1 d . . . . .
C1 C 0.3179(4) -0.0086(4) 0.6169(6) 0.0307(14) Uani 1 1 d . . . . .
C2 C 0.4010(4) 0.0202(4) 0.6582(7) 0.0391(16) Uani 1 1 d . . . . .
H2 H 0.4173 0.0646 0.6183 0.047 Uiso 1 1 calc R U . . .
C3 C 0.4588(5) -0.0148(5) 0.7555(8) 0.0466(19) Uani 1 1 d . . . . .
H3 H 0.5134 0.0056 0.7787 0.056 Uiso 1 1 calc R U . . .
C4 C 0.4370(5) -0.0797(5) 0.8188(7) 0.0488(19) Uani 1 1 d . . . . .
H4 H 0.4757 -0.1023 0.8865 0.059 Uiso 1 1 calc R U . . .
C5 C 0.3557(5) -0.1110(4) 0.7801(7) 0.0447(17) Uani 1 1 d . . . . .
H5 H 0.3401 -0.1552 0.8215 0.054 Uiso 1 1 calc R U . . .
C6 C 0.2983(4) -0.0765(4) 0.6799(6) 0.0329(14) Uani 1 1 d . . . . .
C7 C 0.2120(4) -0.1066(4) 0.6301(6) 0.0293(13) Uani 1 1 d . . . . .
C8 C 0.0836(4) -0.0792(3) 0.4862(6) 0.0312(14) Uani 1 1 d . . . . .
H8 H 0.0528 -0.0451 0.4261 0.037 Uiso 1 1 calc R U . . .
C9 C 0.0431(4) -0.1451(4) 0.5169(7) 0.0352(15) Uani 1 1 d . . . . .
H9 H -0.0133 -0.1562 0.4802 0.042 Uiso 1 1 calc R U . . .
C10 C 0.0919(5) -0.1931(4) 0.6055(7) 0.0401(17) Uani 1 1 d . . . . .
C11 C 0.1749(4) -0.1766(4) 0.6644(7) 0.0384(16) Uani 1 1 d . . . . .
C12 C 0.2023(6) -0.2409(5) 0.7502(9) 0.064(2) Uani 1 1 d . . . . .
H12 H 0.2546 -0.2473 0.8061 0.077 Uiso 1 1 calc R U . . .
C13 C 0.1361(6) -0.2891(5) 0.7321(11) 0.072(3) Uani 1 1 d . . . . .
H13 H 0.1367 -0.3364 0.7745 0.086 Uiso 1 1 calc R U . . .
C14 C 0.1868(4) 0.1039(3) 0.6158(5) 0.0260(12) Uani 1 1 d . . . . .
C15 C 0.1360(4) 0.0871(3) 0.7145(6) 0.0278(13) Uani 1 1 d . . . . .
H15 H 0.1237 0.0364 0.7315 0.033 Uiso 1 1 calc R U . . .
C16 C 0.1042(4) 0.1443(4) 0.7867(6) 0.0326(14) Uani 1 1 d . . . . .
H16 H 0.0704 0.1315 0.8508 0.039 Uiso 1 1 calc R U . . .
C17 C 0.1218(4) 0.2207(4) 0.7652(6) 0.0323(14) Uani 1 1 d . . . . .
H17 H 0.0983 0.2589 0.8122 0.039 Uiso 1 1 calc R U . . .
C18 C 0.1746(4) 0.2393(4) 0.6731(6) 0.0320(14) Uani 1 1 d . . . . .
H18 H 0.1881 0.2902 0.6600 0.038 Uiso 1 1 calc R U . . .
C19 C 0.2079(4) 0.1818(3) 0.5995(5) 0.0254(12) Uani 1 1 d . . . . .
C20 C 0.2679(4) 0.1952(3) 0.5047(5) 0.0254(13) Uani 1 1 d . . . . .
C21 C 0.3482(4) 0.1318(4) 0.3598(6) 0.0332(14) Uani 1 1 d . . . . .
H21 H 0.3609 0.0859 0.3208 0.040 Uiso 1 1 calc R U . . .
C22 C 0.3903(4) 0.1954(4) 0.3293(6) 0.0366(15) Uani 1 1 d . . . . .
H22 H 0.4319 0.1941 0.2737 0.044 Uiso 1 1 calc R U . . .
C23 C 0.3666(4) 0.2627(4) 0.3877(6) 0.0312(14) Uani 1 1 d . . . . .
C24 C 0.3064(4) 0.2643(3) 0.4748(6) 0.0277(13) Uani 1 1 d . . . . .
C25 C 0.2990(4) 0.3442(4) 0.5064(6) 0.0335(14) Uani 1 1 d . . . . .
H25 H 0.2642 0.3656 0.5626 0.040 Uiso 1 1 calc R U . . .
C26 C 0.3530(5) 0.3815(4) 0.4375(6) 0.0383(15) Uani 1 1 d . . . . .
H26 H 0.3602 0.4343 0.4393 0.046 Uiso 1 1 calc R U . . .
C27 C 0.2713(6) -0.0695(5) 0.0972(8) 0.056(2) Uani 1 1 d . . . . .
H27A H 0.3306 -0.0550 0.1087 0.085 Uiso 1 1 calc R U . . .
H27B H 0.2445 -0.0579 0.0072 0.085 Uiso 1 1 calc R U . . .
H27C H 0.2670 -0.1234 0.1131 0.085 Uiso 1 1 calc R U . . .
C28 C 0.2267(5) -0.0256(4) 0.1963(7) 0.0375(16) Uani 1 1 d . . . . .
C29 C 0.1527(5) 0.0142(4) 0.1460(7) 0.0392(16) Uani 1 1 d . . . . .
H29 H 0.1348 0.0112 0.0537 0.047 Uiso 1 1 calc R U . . .
C30 C 0.1014(4) 0.0585(4) 0.2186(6) 0.0310(14) Uani 1 1 d . . . . .
C31 C 0.0187(5) 0.0922(4) 0.1447(6) 0.0415(16) Uani 1 1 d . . . . .
H31A H -0.0260 0.0859 0.1979 0.062 Uiso 1 1 calc R U . . .
H31B H 0.0031 0.0665 0.0602 0.062 Uiso 1 1 calc R U . . .
H31C H 0.0268 0.1457 0.1291 0.062 Uiso 1 1 calc R U . . .
Cl1 Cl 0.5430(2) 0.3190(2) 0.1724(4) 0.1126(12) Uani 1 1 d . . . . .
Cl2 Cl 0.6165(2) 0.2576(2) -0.0472(4) 0.1098(11) Uani 1 1 d . . . . .
C32 C 0.5900(7) 0.3382(6) 0.0417(10) 0.078(3) Uani 1 1 d . . . . .
H32A H 0.6419 0.3669 0.0723 0.093 Uiso 1 1 calc R U . . .
H32B H 0.5523 0.3707 -0.0194 0.093 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C14 1.980(6) . ?
Ir1 C1 1.980(6) . ?
Ir1 N2 2.038(5) . ?
Ir1 N1 2.045(5) . ?
Ir1 O4 2.150(4) . ?
Ir1 O3 2.166(4) . ?
O1 C10 1.352(8) . ?
O1 C13 1.372(11) . ?
O2 C23 1.351(7) . ?
O2 C26 1.361(8) . ?
O3 C28 1.269(9) . ?
O4 C30 1.261(7) . ?
N1 C8 1.330(8) . ?
N1 C7 1.364(8) . ?
N2 C20 1.355(7) . ?
N2 C21 1.357(8) . ?
C1 C6 1.405(9) . ?
C1 C2 1.407(9) . ?
C2 C3 1.373(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.474(9) . ?
C7 C11 1.424(9) . ?
C8 C9 1.378(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(10) . ?
C11 C12 1.442(10) . ?
C12 C13 1.335(13) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.405(8) . ?
C14 C19 1.419(8) . ?
C15 C16 1.378(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.402(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.468(8) . ?
C20 C24 1.408(8) . ?
C21 C22 1.356(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.395(9) . ?
C22 H22 0.9300 . ?
C23 C24 1.395(8) . ?
C24 C25 1.442(9) . ?
C25 C26 1.352(9) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.520(9) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.386(10) . ?
C29 C30 1.409(10) . ?
C29 H29 0.9300 . ?
C30 C31 1.517(10) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
Cl1 C32 1.647(10) . ?
Cl2 C32 1.758(11) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 Ir1 C1 92.4(2) . . ?
C14 Ir1 N2 80.5(2) . . ?
C1 Ir1 N2 96.1(2) . . ?
C14 Ir1 N1 96.4(2) . . ?
C1 Ir1 N1 80.7(2) . . ?
N2 Ir1 N1 175.52(18) . . ?
C14 Ir1 O4 87.19(19) . . ?
C1 Ir1 O4 175.4(2) . . ?
N2 Ir1 O4 88.31(18) . . ?
N1 Ir1 O4 94.82(18) . . ?
C14 Ir1 O3 172.4(2) . . ?
C1 Ir1 O3 93.6(2) . . ?
N2 Ir1 O3 94.08(18) . . ?
N1 Ir1 O3 89.27(17) . . ?
O4 Ir1 O3 87.25(17) . . ?
C10 O1 C13 104.7(6) . . ?
C23 O2 C26 105.4(5) . . ?
C28 O3 Ir1 124.8(4) . . ?
C30 O4 Ir1 126.2(4) . . ?
C8 N1 C7 121.3(5) . . ?
C8 N1 Ir1 123.5(4) . . ?
C7 N1 Ir1 115.2(4) . . ?
C20 N2 C21 121.0(5) . . ?
C20 N2 Ir1 115.9(4) . . ?
C21 N2 Ir1 123.2(4) . . ?
C6 C1 C2 115.6(6) . . ?
C6 C1 Ir1 115.8(5) . . ?
C2 C1 Ir1 128.6(5) . . ?
C3 C2 C1 122.4(7) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C4 C3 C2 120.9(7) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.9(7) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.0(7) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 122.2(6) . . ?
C5 C6 C7 123.8(6) . . ?
C1 C6 C7 114.0(5) . . ?
N1 C7 C11 117.5(6) . . ?
N1 C7 C6 114.2(5) . . ?
C11 C7 C6 128.3(6) . . ?
N1 C8 C9 124.1(6) . . ?
N1 C8 H8 117.9 . . ?
C9 C8 H8 117.9 . . ?
C10 C9 C8 115.2(6) . . ?
C10 C9 H9 122.4 . . ?
C8 C9 H9 122.4 . . ?
O1 C10 C9 125.4(7) . . ?
O1 C10 C11 111.3(6) . . ?
C9 C10 C11 123.3(6) . . ?
C10 C11 C7 118.4(6) . . ?
C10 C11 C12 105.5(7) . . ?
C7 C11 C12 136.1(7) . . ?
C13 C12 C11 104.9(8) . . ?
C13 C12 H12 127.5 . . ?
C11 C12 H12 127.5 . . ?
C12 C13 O1 113.5(7) . . ?
C12 C13 H13 123.2 . . ?
O1 C13 H13 123.2 . . ?
C15 C14 C19 117.1(5) . . ?
C15 C14 Ir1 128.5(5) . . ?
C19 C14 Ir1 114.2(4) . . ?
C16 C15 C14 121.3(6) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 121.1(6) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 119.2(6) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 120.3(6) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.8(5) . . ?
C18 C19 C20 124.5(6) . . ?
C14 C19 C20 114.7(5) . . ?
N2 C20 C24 118.2(5) . . ?
N2 C20 C19 113.3(5) . . ?
C24 C20 C19 128.5(5) . . ?
C22 C21 N2 124.5(6) . . ?
C22 C21 H21 117.7 . . ?
N2 C21 H21 117.7 . . ?
C21 C22 C23 115.0(6) . . ?
C21 C22 H22 122.5 . . ?
C23 C22 H22 122.5 . . ?
O2 C23 C24 111.8(6) . . ?
O2 C23 C22 125.5(6) . . ?
C24 C23 C22 122.6(6) . . ?
C23 C24 C20 118.6(5) . . ?
C23 C24 C25 104.2(5) . . ?
C20 C24 C25 137.1(6) . . ?
C26 C25 C24 106.0(6) . . ?
C26 C25 H25 127.0 . . ?
C24 C25 H25 127.0 . . ?
C25 C26 O2 112.6(6) . . ?
C25 C26 H26 123.7 . . ?
O2 C26 H26 123.7 . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C28 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O3 C28 C29 127.4(6) . . ?
O3 C28 C27 114.7(7) . . ?
C29 C28 C27 117.8(7) . . ?
C28 C29 C30 127.5(6) . . ?
C28 C29 H29 116.2 . . ?
C30 C29 H29 116.2 . . ?
O4 C30 C29 126.4(6) . . ?
O4 C30 C31 114.9(6) . . ?
C29 C30 C31 118.8(6) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
Cl1 C32 Cl2 114.8(6) . . ?
Cl1 C32 H32A 108.6 . . ?
Cl2 C32 H32A 108.6 . . ?
Cl1 C32 H32B 108.6 . . ?
Cl2 C32 H32B 108.6 . . ?
H32A C32 H32B 107.5 . . ?

_refine_diff_density_max         1.816
_refine_diff_density_min         -1.421
_refine_diff_density_rms         0.150



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and methol'
