# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# 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_HPZ128(LOW)
_database_code_depnum_ccdc_archive 'CCDC 1048812'
_audit_update_record             
;
2015-03-07 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H53 Ir N4'
_chemical_formula_weight         974.22

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4399(3)
_cell_length_b                   14.3879(4)
_cell_length_c                   16.0385(4)
_cell_angle_alpha                66.2380(10)
_cell_angle_beta                 78.2120(10)
_cell_angle_gamma                83.3700(10)
_cell_volume                     2156.91(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    252
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             988
_exptl_absorpt_coefficient_mu    3.139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5849
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33042
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         25.25
_reflns_number_total             7813
_reflns_number_gt                7412
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS 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)+(0.0358P)²+0.6553P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7813
_refine_ls_number_parameters     596
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.0597
_refine_ls_wR_factor_gt          0.0535
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.212
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.480294(9) 0.446804(7) 0.364756(6) 0.01827(5) Uani 1 1 d . . .
N1 N 0.3781(2) 0.45781(18) 0.48192(16) 0.0202(5) Uani 1 1 d . . .
N2 N 0.5335(2) 0.30115(18) 0.43880(17) 0.0211(5) Uani 1 1 d . . .
N3 N 0.5969(2) 0.44115(18) 0.24998(16) 0.0221(5) Uani 1 1 d . . .
N4 N 0.4161(2) 0.58875(17) 0.28965(16) 0.0207(5) Uani 1 1 d . . .
C1 C 0.3041(3) 0.5408(2) 0.4888(2) 0.0221(6) Uani 1 1 d . . .
C2 C 0.2697(3) 0.5253(2) 0.5847(2) 0.0258(6) Uani 1 1 d . . .
H2A H 0.2219 0.5722 0.6087 0.031 Uiso 1 1 calc R . .
C3 C 0.3168(3) 0.4331(2) 0.63454(19) 0.0243(6) Uani 1 1 d . . .
H3A H 0.3108 0.4037 0.6999 0.029 Uiso 1 1 calc R . .
C4 C 0.3781(3) 0.3866(2) 0.57132(19) 0.0215(6) Uani 1 1 d . . .
C5 C 0.4179(3) 0.2848(2) 0.5940(2) 0.0223(6) Uani 1 1 d . . .
C6 C 0.4824(3) 0.2444(2) 0.5299(2) 0.0229(6) Uani 1 1 d . . .
C7 C 0.5158(3) 0.1382(2) 0.5480(2) 0.0268(6) Uani 1 1 d . . .
H7A H 0.4890 0.0822 0.6041 0.032 Uiso 1 1 calc R . .
C8 C 0.5913(3) 0.1334(2) 0.4712(2) 0.0278(6) Uani 1 1 d . . .
H8A H 0.6290 0.0732 0.4638 0.033 Uiso 1 1 calc R . .
C9 C 0.6049(3) 0.2349(2) 0.4023(2) 0.0246(6) Uani 1 1 d . . .
C10 C 0.6820(3) 0.2643(2) 0.3143(2) 0.0250(6) Uani 1 1 d . . .
C11 C 0.6803(3) 0.3609(2) 0.2446(2) 0.0241(6) Uani 1 1 d . . .
C12 C 0.7542(3) 0.3902(2) 0.1521(2) 0.0306(7) Uani 1 1 d . . .
H12A H 0.8195 0.3498 0.1302 0.037 Uiso 1 1 calc R . .
C13 C 0.7138(3) 0.4855(2) 0.1022(2) 0.0309(7) Uani 1 1 d . . .
H13A H 0.7455 0.5242 0.0388 0.037 Uiso 1 1 calc R . .
C14 C 0.6139(3) 0.5181(2) 0.1623(2) 0.0244(6) Uani 1 1 d . . .
C15 C 0.5406(3) 0.6088(2) 0.1361(2) 0.0246(6) Uani 1 1 d . . .
C16 C 0.4447(3) 0.6394(2) 0.1951(2) 0.0237(6) Uani 1 1 d . . .
C17 C 0.3572(3) 0.7266(2) 0.1671(2) 0.0288(6) Uani 1 1 d . . .
H17A H 0.3564 0.7746 0.1056 0.035 Uiso 1 1 calc R . .
C18 C 0.2763(3) 0.7282(2) 0.2440(2) 0.0282(6) Uani 1 1 d . . .
H18A H 0.2072 0.7767 0.2463 0.034 Uiso 1 1 calc R . .
C19 C 0.3139(3) 0.6431(2) 0.3215(2) 0.0236(6) Uani 1 1 d . . .
C20 C 0.2631(3) 0.6224(2) 0.4141(2) 0.0232(6) Uani 1 1 d . . .
C21 C 0.3866(3) 0.2129(2) 0.6938(2) 0.0277(6) Uani 1 1 d . . .
C22 C 0.2602(3) 0.2076(2) 0.7441(2) 0.0339(7) Uani 1 1 d . . .
H22A H 0.1922 0.2511 0.7158 0.041 Uiso 1 1 calc R . .
C23 C 0.2329(4) 0.1386(3) 0.8359(2) 0.0450(9) Uani 1 1 d . . .
H23A H 0.1466 0.1370 0.8698 0.054 Uiso 1 1 calc R . .
C24 C 0.3284(5) 0.0729(3) 0.8781(2) 0.0521(11) Uani 1 1 d . . .
C25 C 0.4537(4) 0.0788(3) 0.8290(2) 0.0470(9) Uani 1 1 d . . .
H25A H 0.5210 0.0347 0.8577 0.056 Uiso 1 1 calc R . .
C26 C 0.4835(4) 0.1483(2) 0.7380(2) 0.0365(7) Uani 1 1 d . . .
H26A H 0.5710 0.1517 0.7057 0.044 Uiso 1 1 calc R . .
C27 C 0.2948(7) -0.0054(4) 0.9770(3) 0.0850(19) Uani 1 1 d . . .
H27A H 0.3746 -0.0437 0.9969 0.128 Uiso 1 1 calc R . .
H27B H 0.2316 -0.0522 0.9794 0.128 Uiso 1 1 calc R . .
H27C H 0.2566 0.0294 1.0183 0.128 Uiso 1 1 calc R . .
C31 C 0.7759(3) 0.1858(2) 0.2931(2) 0.0269(6) Uani 1 1 d . . .
C32 C 0.9037(4) 0.1811(3) 0.3007(3) 0.0561(12) Uani 1 1 d . . .
H32A H 0.9337 0.2272 0.3207 0.067 Uiso 1 1 calc R . .
C33 C 0.9912(4) 0.1103(4) 0.2798(4) 0.0654(14) Uani 1 1 d . . .
H33A H 1.0800 0.1092 0.2861 0.079 Uiso 1 1 calc R . .
C34 C 0.9548(3) 0.0425(3) 0.2508(2) 0.0385(8) Uani 1 1 d . . .
C35 C 0.8246(4) 0.0451(4) 0.2464(4) 0.0692(14) Uani 1 1 d . . .
H35A H 0.7939 -0.0026 0.2285 0.083 Uiso 1 1 calc R . .
C36 C 0.7372(4) 0.1153(4) 0.2673(4) 0.0674(15) Uani 1 1 d . . .
H36A H 0.6477 0.1146 0.2637 0.081 Uiso 1 1 calc R . .
C37 C 1.0507(4) -0.0343(3) 0.2269(3) 0.0509(10) Uani 1 1 d . . .
H37A H 1.1385 -0.0244 0.2341 0.076 Uiso 1 1 calc R . .
H37B H 1.0517 -0.0248 0.1628 0.076 Uiso 1 1 calc R . .
H37C H 1.0238 -0.1032 0.2684 0.076 Uiso 1 1 calc R . .
C41 C 0.5621(3) 0.6774(2) 0.0346(2) 0.0268(6) Uani 1 1 d . . .
C42 C 0.4994(4) 0.6614(4) -0.0250(2) 0.0599(13) Uani 1 1 d . . .
H42A H 0.4420 0.6066 -0.0024 0.072 Uiso 1 1 calc R . .
C43 C 0.5186(4) 0.7243(4) -0.1181(3) 0.0631(13) Uani 1 1 d . . .
H43A H 0.4725 0.7123 -0.1580 0.076 Uiso 1 1 calc R . .
C44 C 0.6018(3) 0.8030(3) -0.1542(2) 0.0368(8) Uani 1 1 d . . .
C45 C 0.6630(4) 0.8190(3) -0.0941(2) 0.0511(10) Uani 1 1 d . . .
H45A H 0.7213 0.8732 -0.1170 0.061 Uiso 1 1 calc R . .
C46 C 0.6422(4) 0.7575(3) 0.0004(2) 0.0471(9) Uani 1 1 d . . .
H46A H 0.6842 0.7717 0.0410 0.056 Uiso 1 1 calc R . .
C47 C 0.6247(4) 0.8701(4) -0.2563(2) 0.0546(11) Uani 1 1 d . . .
H47A H 0.5774 0.8443 -0.2888 0.082 Uiso 1 1 calc R . .
H47B H 0.7185 0.8700 -0.2812 0.082 Uiso 1 1 calc R . .
H47C H 0.5929 0.9397 -0.2648 0.082 Uiso 1 1 calc R . .
C51 C 0.1530(3) 0.6911(2) 0.4353(2) 0.0231(6) Uani 1 1 d . . .
C52 C 0.1745(3) 0.7723(3) 0.4546(3) 0.0357(8) Uani 1 1 d . . .
H52A H 0.2614 0.7861 0.4544 0.043 Uiso 1 1 calc R . .
C53 C 0.0708(3) 0.8346(3) 0.4742(3) 0.0416(8) Uani 1 1 d . . .
H53A H 0.0881 0.8899 0.4878 0.050 Uiso 1 1 calc R . .
C54 C -0.0571(3) 0.8174(2) 0.4742(2) 0.0323(7) Uani 1 1 d . . .
C55 C -0.0776(3) 0.7371(3) 0.4535(2) 0.0332(7) Uani 1 1 d . . .
H55A H -0.1643 0.7242 0.4523 0.040 Uiso 1 1 calc R . .
C56 C 0.0249(3) 0.6744(3) 0.4344(2) 0.0324(7) Uani 1 1 d . . .
H56A H 0.0074 0.6194 0.4204 0.039 Uiso 1 1 calc R . .
C57 C -0.1690(3) 0.8853(3) 0.4967(3) 0.0457(9) Uani 1 1 d . . .
H57A H -0.1342 0.9380 0.5090 0.069 Uiso 1 1 calc R . .
H57B H -0.2297 0.8445 0.5514 0.069 Uiso 1 1 calc R . .
H57C H -0.2154 0.9173 0.4441 0.069 Uiso 1 1 calc R . .
C61 C 0.3192(3) 0.3909(2) 0.3463(2) 0.0328(7) Uani 1 1 d D . .
H61A H 0.3269 0.3158 0.3751 0.039 Uiso 1 1 calc R . .
H61B H 0.2407 0.4121 0.3818 0.039 Uiso 1 1 calc R . .
C62 C 0.2942(5) 0.4190(5) 0.2529(3) 0.090(2) Uani 1 1 d D B .
H62A H 0.3700 0.3950 0.2174 0.108 Uiso 1 1 calc R . .
H62B H 0.2884 0.4941 0.2226 0.108 Uiso 1 1 calc R . .
C63 C 0.1696(4) 0.3768(3) 0.2470(3) 0.0628(12) Uani 1 1 d D . .
H63A H 0.1908 0.3073 0.2486 0.075 Uiso 1 1 calc R A 1
H63B H 0.1043 0.3709 0.3029 0.075 Uiso 1 1 calc R A 1
C64 C 0.1058(14) 0.4379(12) 0.1623(9) 0.159(11) Uani 0.449(7) 1 d PD B 1
H64A H 0.1734 0.4503 0.1061 0.191 Uiso 0.449(7) 1 calc PR B 1
H64B H 0.0386 0.3961 0.1601 0.191 Uiso 0.449(7) 1 calc PR B 1
C65 C 0.042(2) 0.5387(13) 0.1589(15) 0.182(15) Uani 0.449(7) 1 d PD B 1
H65A H -0.0019 0.5179 0.2241 0.218 Uiso 0.449(7) 1 calc PR B 1
H65B H 0.1206 0.5735 0.1557 0.218 Uiso 0.449(7) 1 calc PR B 1
C66 C -0.0434(11) 0.6302(10) 0.1152(9) 0.075(3) Uani 0.449(7) 1 d PDU B 1
H66A H -0.1292 0.6037 0.1200 0.090 Uiso 0.449(7) 1 calc PR B 1
H66B H -0.0581 0.6680 0.1562 0.090 Uiso 0.449(7) 1 calc PR B 1
C67 C -0.0117(13) 0.7080(14) 0.0185(10) 0.113(7) Uani 0.449(7) 1 d PD B 1
H67A H -0.0881 0.7547 0.0011 0.136 Uiso 0.449(7) 1 calc PR B 1
H67B H 0.0157 0.6752 -0.0264 0.136 Uiso 0.449(7) 1 calc PR B 1
C68 C 0.0987(16) 0.7636(14) 0.0219(16) 0.117(8) Uani 0.449(7) 1 d PD B 1
H68A H 0.1204 0.8210 -0.0374 0.175 Uiso 0.449(7) 1 calc PR B 1
H68B H 0.1755 0.7173 0.0339 0.175 Uiso 0.449(7) 1 calc PR B 1
H68C H 0.0724 0.7889 0.0715 0.175 Uiso 0.449(7) 1 calc PR B 1
C64' C 0.0510(6) 0.4326(6) 0.2636(6) 0.060(2) Uani 0.551(7) 1 d PD B 2
H64C H 0.0271 0.4113 0.3315 0.072 Uiso 0.551(7) 1 calc PR B 2
H64D H -0.0177 0.4079 0.2440 0.072 Uiso 0.551(7) 1 calc PR B 2
C65' C 0.0391(11) 0.5440(7) 0.2234(8) 0.102(4) Uani 0.551(7) 1 d PD B 2
H65C H 0.1078 0.5730 0.2392 0.122 Uiso 0.551(7) 1 calc PR B 2
H65D H -0.0475 0.5672 0.2485 0.122 Uiso 0.551(7) 1 calc PR B 2
C66' C 0.0544(13) 0.5794(9) 0.1187(8) 0.099(5) Uani 0.551(7) 1 d PDU B 2
H66C H -0.0084 0.5462 0.1019 0.119 Uiso 0.551(7) 1 calc PR B 2
H66D H 0.1445 0.5647 0.0916 0.119 Uiso 0.551(7) 1 calc PR B 2
C67' C 0.0243(17) 0.6961(9) 0.0857(10) 0.130(6) Uani 0.551(7) 1 d PD B 2
H67C H -0.0693 0.7035 0.1111 0.156 Uiso 0.551(7) 1 calc PR B 2
H67D H 0.0743 0.7197 0.1192 0.156 Uiso 0.551(7) 1 calc PR B 2
C68' C 0.0439(16) 0.7736(11) -0.0117(8) 0.106(5) Uani 0.551(7) 1 d PD B 2
H68D H 0.0397 0.8417 -0.0111 0.160 Uiso 0.551(7) 1 calc PR B 2
H68E H -0.0249 0.7685 -0.0429 0.160 Uiso 0.551(7) 1 calc PR B 2
H68F H 0.1297 0.7612 -0.0447 0.160 Uiso 0.551(7) 1 calc PR B 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
Ir1 N3 2.015(2) . ?
Ir1 N1 2.019(2) . ?
Ir1 N4 2.025(2) . ?
Ir1 N2 2.026(2) . ?
Ir1 C61 2.066(3) . ?
N1 C1 1.376(4) . ?
N1 C4 1.386(4) . ?
N2 C6 1.380(4) . ?
N2 C9 1.383(4) . ?
N3 C11 1.384(4) . ?
N3 C14 1.388(4) . ?
N4 C16 1.376(4) . ?
N4 C19 1.385(4) . ?
C1 C20 1.398(4) . ?
C1 C2 1.436(4) . ?
C2 C3 1.341(4) . ?
C3 C4 1.438(4) . ?
C4 C5 1.395(4) . ?
C5 C6 1.399(4) . ?
C5 C21 1.506(4) . ?
C6 C7 1.449(4) . ?
C7 C8 1.343(4) . ?
C8 C9 1.435(4) . ?
C9 C10 1.397(4) . ?
C10 C11 1.390(4) . ?
C10 C31 1.507(4) . ?
C11 C12 1.442(4) . ?
C12 C13 1.348(5) . ?
C13 C14 1.441(4) . ?
C14 C15 1.387(4) . ?
C15 C16 1.393(4) . ?
C15 C41 1.510(4) . ?
C16 C17 1.435(4) . ?
C17 C18 1.352(4) . ?
C18 C19 1.436(4) . ?
C19 C20 1.391(4) . ?
C20 C51 1.504(4) . ?
C21 C26 1.390(5) . ?
C21 C22 1.392(5) . ?
C22 C23 1.396(5) . ?
C23 C24 1.375(6) . ?
C24 C25 1.374(6) . ?
C24 C27 1.527(5) . ?
C25 C26 1.392(5) . ?
C31 C32 1.355(5) . ?
C31 C36 1.366(5) . ?
C32 C33 1.386(5) . ?
C33 C34 1.355(6) . ?
C34 C35 1.370(6) . ?
C34 C37 1.516(5) . ?
C35 C36 1.378(6) . ?
C41 C46 1.362(5) . ?
C41 C42 1.365(5) . ?
C42 C43 1.386(5) . ?
C43 C44 1.366(6) . ?
C44 C45 1.361(5) . ?
C44 C47 1.512(5) . ?
C45 C46 1.400(5) . ?
C51 C52 1.375(4) . ?
C51 C56 1.390(4) . ?
C52 C53 1.392(5) . ?
C53 C54 1.386(5) . ?
C54 C55 1.374(5) . ?
C54 C57 1.515(4) . ?
C55 C56 1.385(5) . ?
C61 C62 1.457(5) . ?
C62 C63 1.532(5) . ?
C63 C64' 1.433(7) . ?
C63 C64 1.528(9) . ?
C64 C65 1.509(10) . ?
C65 C66 1.503(10) . ?
C66 C67 1.499(10) . ?
C67 C68 1.499(9) . ?
C64' C65' 1.469(9) . ?
C65' C66' 1.524(9) . ?
C66' C67' 1.557(9) . ?
C67' C68' 1.498(9) . ?

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
N3 Ir1 N1 174.51(8) . . ?
N3 Ir1 N4 89.91(10) . . ?
N1 Ir1 N4 90.20(9) . . ?
N3 Ir1 N2 90.52(10) . . ?
N1 Ir1 N2 89.74(9) . . ?
N4 Ir1 N2 176.10(8) . . ?
N3 Ir1 C61 95.09(12) . . ?
N1 Ir1 C61 90.40(11) . . ?
N4 Ir1 C61 88.52(11) . . ?
N2 Ir1 C61 87.57(11) . . ?
C1 N1 C4 106.9(2) . . ?
C1 N1 Ir1 126.45(19) . . ?
C4 N1 Ir1 126.42(19) . . ?
C6 N2 C9 107.3(2) . . ?
C6 N2 Ir1 125.85(19) . . ?
C9 N2 Ir1 125.5(2) . . ?
C11 N3 C14 106.7(2) . . ?
C11 N3 Ir1 126.3(2) . . ?
C14 N3 Ir1 126.9(2) . . ?
C16 N4 C19 106.8(2) . . ?
C16 N4 Ir1 126.60(19) . . ?
C19 N4 Ir1 125.21(19) . . ?
N1 C1 C20 124.5(3) . . ?
N1 C1 C2 108.6(2) . . ?
C20 C1 C2 126.7(3) . . ?
C3 C2 C1 107.9(3) . . ?
C2 C3 C4 107.7(3) . . ?
N1 C4 C5 124.7(3) . . ?
N1 C4 C3 108.3(2) . . ?
C5 C4 C3 126.7(3) . . ?
C4 C5 C6 124.3(3) . . ?
C4 C5 C21 117.9(3) . . ?
C6 C5 C21 117.8(3) . . ?
N2 C6 C5 124.9(3) . . ?
N2 C6 C7 108.2(2) . . ?
C5 C6 C7 126.7(3) . . ?
C8 C7 C6 107.6(3) . . ?
C7 C8 C9 108.0(3) . . ?
N2 C9 C10 124.8(3) . . ?
N2 C9 C8 108.7(3) . . ?
C10 C9 C8 126.5(3) . . ?
C11 C10 C9 125.2(3) . . ?
C11 C10 C31 117.1(3) . . ?
C9 C10 C31 117.8(3) . . ?
N3 C11 C10 125.2(3) . . ?
N3 C11 C12 109.0(3) . . ?
C10 C11 C12 125.5(3) . . ?
C13 C12 C11 107.6(3) . . ?
C12 C13 C14 107.8(3) . . ?
C15 C14 N3 125.1(3) . . ?
C15 C14 C13 125.9(3) . . ?
N3 C14 C13 108.8(3) . . ?
C14 C15 C16 125.2(3) . . ?
C14 C15 C41 117.3(3) . . ?
C16 C15 C41 117.5(3) . . ?
N4 C16 C15 125.2(3) . . ?
N4 C16 C17 109.1(2) . . ?
C15 C16 C17 125.6(3) . . ?
C18 C17 C16 107.6(3) . . ?
C17 C18 C19 107.4(3) . . ?
N4 C19 C20 125.2(3) . . ?
N4 C19 C18 108.9(2) . . ?
C20 C19 C18 125.7(3) . . ?
C19 C20 C1 124.9(3) . . ?
C19 C20 C51 117.5(3) . . ?
C1 C20 C51 117.6(3) . . ?
C26 C21 C22 118.0(3) . . ?
C26 C21 C5 120.7(3) . . ?
C22 C21 C5 121.4(3) . . ?
C21 C22 C23 120.4(3) . . ?
C24 C23 C22 121.3(4) . . ?
C25 C24 C23 118.5(3) . . ?
C25 C24 C27 121.1(5) . . ?
C23 C24 C27 120.4(5) . . ?
C24 C25 C26 121.1(4) . . ?
C21 C26 C25 120.8(4) . . ?
C32 C31 C36 116.8(3) . . ?
C32 C31 C10 120.8(3) . . ?
C36 C31 C10 122.3(3) . . ?
C31 C32 C33 121.2(4) . . ?
C34 C33 C32 122.4(4) . . ?
C33 C34 C35 116.2(3) . . ?
C33 C34 C37 122.5(4) . . ?
C35 C34 C37 121.3(4) . . ?
C34 C35 C36 121.6(4) . . ?
C31 C36 C35 121.7(4) . . ?
C46 C41 C42 118.3(3) . . ?
C46 C41 C15 121.2(3) . . ?
C42 C41 C15 120.5(3) . . ?
C41 C42 C43 120.7(4) . . ?
C44 C43 C42 121.8(4) . . ?
C45 C44 C43 117.1(3) . . ?
C45 C44 C47 121.3(4) . . ?
C43 C44 C47 121.7(3) . . ?
C44 C45 C46 121.7(3) . . ?
C41 C46 C45 120.4(3) . . ?
C52 C51 C56 117.9(3) . . ?
C52 C51 C20 122.1(3) . . ?
C56 C51 C20 120.0(3) . . ?
C51 C52 C53 120.9(3) . . ?
C54 C53 C52 121.2(3) . . ?
C55 C54 C53 117.5(3) . . ?
C55 C54 C57 122.0(3) . . ?
C53 C54 C57 120.5(3) . . ?
C54 C55 C56 121.7(3) . . ?
C55 C56 C51 120.7(3) . . ?
C62 C61 Ir1 119.2(2) . . ?
C61 C62 C63 115.1(4) . . ?
C64' C63 C64 64.5(7) . . ?
C64' C63 C62 114.8(5) . . ?
C64 C63 C62 116.6(7) . . ?
C65 C64 C63 115.4(11) . . ?
C66 C65 C64 149.6(13) . . ?
C67 C66 C65 125.1(15) . . ?
C66 C67 C68 103.7(14) . . ?
C63 C64' C65' 123.0(7) . . ?
C64' C65' C66' 108.4(9) . . ?
C65' C66' C67' 103.5(10) . . ?
C68' C67' C66' 127.5(13) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.133
####################################################################### 
# 
# 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_ZPL1p
_database_code_depnum_ccdc_archive 'CCDC 1048813'
_audit_update_record             
;
2015-03-07 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'n-Pentyl (5,10,15,20-tetratolylporphyrinato) iridium(III)'
_chemical_name_common            Ir(ttp)-n-pentyl
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C53 H48 Ir N4'
_chemical_formula_weight         933.15

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   15.451(8)
_cell_length_b                   12.705(6)
_cell_length_c                   22.893(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.330(9)
_cell_angle_gamma                90.00
_cell_volume                     4421(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    611
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1884
_exptl_absorpt_coefficient_mu    3.059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5042
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33224
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         25.25
_reflns_number_total             7989
_reflns_number_gt                5530
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS 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)+(0.0386P)²+2.3533P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7989
_refine_ls_number_parameters     523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.654791(14) 0.919126(16) 0.550924(9) 0.03937(8) Uani 1 1 d . . .
N1 N 0.7268(3) 0.7886(3) 0.54529(19) 0.0438(11) Uani 1 1 d . . .
N2 N 0.5984(3) 0.8515(3) 0.61382(17) 0.0390(10) Uani 1 1 d . . .
N3 N 0.5758(3) 1.0445(3) 0.55170(19) 0.0408(11) Uani 1 1 d . . .
N4 N 0.7147(3) 0.9896(3) 0.49011(18) 0.0395(10) Uani 1 1 d . . .
C1 C 0.7892(4) 0.7743(4) 0.5104(3) 0.0490(14) Uani 1 1 d . . .
C2 C 0.8245(4) 0.6696(5) 0.5200(3) 0.0602(17) Uani 1 1 d . . .
H2A H 0.8681 0.6398 0.5020 0.072 Uiso 1 1 calc R . .
C3 C 0.7834(4) 0.6232(5) 0.5594(3) 0.0615(17) Uani 1 1 d . . .
H3A H 0.7932 0.5547 0.5734 0.074 Uiso 1 1 calc R . .
C4 C 0.7223(4) 0.6947(4) 0.5767(2) 0.0463(14) Uani 1 1 d . . .
C5 C 0.6713(3) 0.6785(4) 0.6191(2) 0.0404(13) Uani 1 1 d . . .
C6 C 0.6171(3) 0.7515(4) 0.6384(2) 0.0427(13) Uani 1 1 d . . .
C7 C 0.5740(4) 0.7411(5) 0.6881(2) 0.0500(14) Uani 1 1 d . . .
H7A H 0.5755 0.6819 0.7122 0.060 Uiso 1 1 calc R . .
C8 C 0.5313(4) 0.8301(4) 0.6943(2) 0.0477(14) Uani 1 1 d . . .
H8A H 0.4989 0.8448 0.7238 0.057 Uiso 1 1 calc R . .
C9 C 0.5442(4) 0.8993(4) 0.6471(2) 0.0425(13) Uani 1 1 d . . .
C10 C 0.5033(3) 0.9965(4) 0.6344(2) 0.0427(13) Uani 1 1 d . . .
C11 C 0.5133(4) 1.0580(4) 0.5866(2) 0.0427(13) Uani 1 1 d . . .
C12 C 0.4631(4) 1.1511(4) 0.5670(3) 0.0529(15) Uani 1 1 d . . .
H12A H 0.4149 1.1761 0.5820 0.064 Uiso 1 1 calc R . .
C13 C 0.4982(4) 1.1955(4) 0.5233(3) 0.0544(16) Uani 1 1 d . . .
H13A H 0.5167 1.2670 0.5338 0.065 Uiso 1 1 calc R . .
H13B H 0.4554 1.1972 0.4867 0.065 Uiso 1 1 calc R . .
C14 C 0.5733(4) 1.1319(4) 0.5157(2) 0.0435(13) Uani 1 1 d . . .
C15 C 0.6363(4) 1.1591(4) 0.4825(2) 0.0426(13) Uani 1 1 d . . .
C16 C 0.7034(3) 1.0937(4) 0.4720(2) 0.0415(13) Uani 1 1 d . . .
C17 C 0.7711(4) 1.1194(5) 0.4396(2) 0.0512(15) Uani 1 1 d . . .
H17A H 0.7804 1.1852 0.4241 0.061 Uiso 1 1 calc R . .
C18 C 0.8189(4) 1.0330(5) 0.4351(3) 0.0532(15) Uani 1 1 d . . .
H18A H 0.8658 1.0272 0.4149 0.064 Uiso 1 1 calc R . .
C19 C 0.7844(4) 0.9514(4) 0.4674(2) 0.0453(14) Uani 1 1 d . . .
C20 C 0.8181(4) 0.8493(5) 0.4747(2) 0.0475(14) Uani 1 1 d . . .
C21 C 0.6755(4) 0.5708(4) 0.6472(2) 0.0454(13) Uani 1 1 d . . .
C22 C 0.6067(4) 0.5035(5) 0.6332(3) 0.0613(17) Uani 1 1 d . . .
H22A H 0.5555 0.5258 0.6085 0.074 Uiso 1 1 calc R . .
C23 C 0.6122(5) 0.4011(5) 0.6555(3) 0.0674(19) Uani 1 1 d . . .
H23A H 0.5654 0.3551 0.6442 0.081 Uiso 1 1 calc R . .
C24 C 0.6852(5) 0.3673(5) 0.6937(3) 0.0599(17) Uani 1 1 d . . .
C25 C 0.7533(4) 0.4365(5) 0.7082(3) 0.0584(17) Uani 1 1 d . . .
H25A H 0.8037 0.4154 0.7340 0.070 Uiso 1 1 calc R . .
C26 C 0.7487(4) 0.5376(5) 0.6851(3) 0.0549(16) Uani 1 1 d . . .
H26A H 0.7960 0.5832 0.6956 0.066 Uiso 1 1 calc R . .
C27 C 0.6917(5) 0.2570(5) 0.7182(3) 0.093(2) Uani 1 1 d . . .
H27A H 0.7474 0.2480 0.7441 0.140 Uiso 1 1 calc R . .
H27B H 0.6868 0.2075 0.6861 0.140 Uiso 1 1 calc R . .
H27C H 0.6451 0.2453 0.7401 0.140 Uiso 1 1 calc R . .
C31 C 0.4513(4) 1.0391(5) 0.6780(3) 0.0582(16) Uani 1 1 d . . .
C32 C 0.3644(5) 1.0348(8) 0.6722(4) 0.111(3) Uani 1 1 d . . .
H32A H 0.3324 1.0020 0.6388 0.133 Uiso 1 1 calc R . .
C33 C 0.3198(7) 1.0766(11) 0.7133(5) 0.141(4) Uani 1 1 d . . .
H33A H 0.2591 1.0688 0.7082 0.170 Uiso 1 1 calc R . .
C34 C 0.3612(10) 1.1274(11) 0.7598(7) 0.177(6) Uani 1 1 d . . .
C35 C 0.4541(9) 1.1200(11) 0.7733(6) 0.208(8) Uani 1 1 d . . .
H35A H 0.4849 1.1435 0.8096 0.249 Uiso 1 1 calc R . .
C36 C 0.4981(7) 1.0770(8) 0.7310(5) 0.149(5) Uani 1 1 d . . .
H36A H 0.5593 1.0738 0.7384 0.178 Uiso 1 1 calc R . .
C37 C 0.3134(11) 1.1761(13) 0.8077(7) 0.311(12) Uani 1 1 d . . .
H37A H 0.2518 1.1827 0.7919 0.467 Uiso 1 1 calc R . .
H37B H 0.3376 1.2443 0.8188 0.467 Uiso 1 1 calc R . .
H37C H 0.3214 1.1313 0.8420 0.467 Uiso 1 1 calc R . .
C41 C 0.6346(4) 1.2689(4) 0.4584(2) 0.0461(13) Uani 1 1 d . . .
C42 C 0.6376(4) 1.3538(5) 0.4968(3) 0.0683(19) Uani 1 1 d . . .
H42A H 0.6392 1.3415 0.5370 0.082 Uiso 1 1 calc R . .
C43 C 0.6382(5) 1.4555(5) 0.4769(4) 0.082(2) Uani 1 1 d . . .
H43A H 0.6395 1.5109 0.5036 0.099 Uiso 1 1 calc R . .
C44 C 0.6369(4) 1.4761(5) 0.4182(4) 0.070(2) Uani 1 1 d . . .
C45 C 0.6317(4) 1.3928(5) 0.3801(3) 0.0684(19) Uani 1 1 d . . .
H45A H 0.6295 1.4053 0.3398 0.082 Uiso 1 1 calc R . .
C46 C 0.6295(4) 1.2903(4) 0.4000(3) 0.0560(16) Uani 1 1 d . . .
H46A H 0.6245 1.2352 0.3729 0.067 Uiso 1 1 calc R . .
C47 C 0.6400(6) 1.5892(5) 0.3960(4) 0.107(3) Uani 1 1 d . . .
H47A H 0.6389 1.5888 0.3540 0.161 Uiso 1 1 calc R . .
H47B H 0.6930 1.6225 0.4158 0.161 Uiso 1 1 calc R . .
H47C H 0.5900 1.6273 0.4044 0.161 Uiso 1 1 calc R . .
C51 C 0.8918(4) 0.8175(5) 0.4448(3) 0.0540(15) Uani 1 1 d . . .
C52 C 0.9771(4) 0.8367(6) 0.4697(3) 0.077(2) Uani 1 1 d . . .
H52A H 0.9893 0.8755 0.5047 0.092 Uiso 1 1 calc R . .
C53 C 1.0458(5) 0.7999(6) 0.4443(3) 0.084(2) Uani 1 1 d . . .
H53A H 1.1032 0.8171 0.4616 0.101 Uiso 1 1 calc R . .
C54 C 1.0317(5) 0.7394(6) 0.3948(3) 0.076(2) Uani 1 1 d . . .
C55 C 0.9460(6) 0.7212(7) 0.3690(3) 0.096(3) Uani 1 1 d . . .
H55A H 0.9343 0.6814 0.3344 0.115 Uiso 1 1 calc R . .
C56 C 0.8764(5) 0.7600(6) 0.3927(3) 0.083(2) Uani 1 1 d . . .
H56A H 0.8190 0.7475 0.3735 0.100 Uiso 1 1 calc R . .
C57 C 1.1069(6) 0.6931(8) 0.3684(4) 0.120(3) Uani 1 1 d . . .
H57A H 1.0834 0.6519 0.3340 0.180 Uiso 1 1 calc R . .
H57B H 1.1424 0.6490 0.3973 0.180 Uiso 1 1 calc R . .
H57C H 1.1423 0.7490 0.3571 0.180 Uiso 1 1 calc R . .
C61 C 0.7447(3) 0.9897(4) 0.6164(2) 0.0492(14) Uani 1 1 d . . .
H61A H 0.7521 1.0621 0.6048 0.059 Uiso 1 1 calc R . .
H61B H 0.7199 0.9913 0.6524 0.059 Uiso 1 1 calc R . .
C62 C 0.8338(4) 0.9400(6) 0.6306(3) 0.079(2) Uani 1 1 d . . .
H62A H 0.8580 0.9355 0.5945 0.095 Uiso 1 1 calc R . .
H62B H 0.8273 0.8688 0.6445 0.095 Uiso 1 1 calc R . .
C63 C 0.8980(5) 0.9974(6) 0.6766(3) 0.084(2) Uani 1 1 d . . .
H63A H 0.8767 0.9983 0.7139 0.101 Uiso 1 1 calc R . .
H63B H 0.9037 1.0697 0.6641 0.101 Uiso 1 1 calc R . .
C64 C 0.9891(7) 0.9419(10) 0.6851(6) 0.187(6) Uani 1 1 d . . .
H64A H 0.9832 0.8716 0.7005 0.225 Uiso 1 1 calc R . .
H64B H 1.0065 0.9347 0.6466 0.225 Uiso 1 1 calc R . .
C65 C 1.0538(8) 0.9930(13) 0.7221(7) 0.220(7) Uani 1 1 d . . .
H65A H 1.1076 0.9537 0.7257 0.330 Uiso 1 1 calc R . .
H65B H 1.0377 0.9999 0.7605 0.330 Uiso 1 1 calc R . .
H65C H 1.0620 1.0616 0.7064 0.330 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 N2 2.005(4) . ?
Ir1 N3 2.009(4) . ?
Ir1 N1 2.014(4) . ?
Ir1 N4 2.015(4) . ?
Ir1 C61 2.057(5) . ?
N1 C1 1.371(7) . ?
N1 C4 1.402(6) . ?
N2 C9 1.371(6) . ?
N2 C6 1.398(6) . ?
N3 C11 1.371(7) . ?
N3 C14 1.379(6) . ?
N4 C19 1.367(6) . ?
N4 C16 1.387(6) . ?
C1 C20 1.380(8) . ?
C1 C2 1.440(8) . ?
C2 C3 1.331(8) . ?
C3 C4 1.417(8) . ?
C4 C5 1.370(7) . ?
C5 C6 1.375(7) . ?
C5 C21 1.508(7) . ?
C6 C7 1.424(7) . ?
C7 C8 1.330(7) . ?
C8 C9 1.434(7) . ?
C9 C10 1.395(7) . ?
C10 C11 1.375(7) . ?
C10 C31 1.492(8) . ?
C11 C12 1.441(7) . ?
C12 C13 1.347(7) . ?
C13 C14 1.450(7) . ?
C14 C15 1.382(7) . ?
C15 C16 1.383(7) . ?
C15 C41 1.499(7) . ?
C16 C17 1.424(7) . ?
C17 C18 1.337(8) . ?
C18 C19 1.432(8) . ?
C19 C20 1.397(8) . ?
C20 C51 1.486(8) . ?
C21 C22 1.357(8) . ?
C21 C26 1.364(7) . ?
C22 C23 1.395(8) . ?
C23 C24 1.366(8) . ?
C24 C25 1.366(9) . ?
C24 C27 1.505(8) . ?
C25 C26 1.384(8) . ?
C31 C32 1.326(9) . ?
C31 C36 1.383(10) . ?
C32 C33 1.370(11) . ?
C33 C34 1.308(14) . ?
C34 C35 1.416(18) . ?
C34 C37 1.556(13) . ?
C35 C36 1.391(12) . ?
C41 C46 1.352(8) . ?
C41 C42 1.387(8) . ?
C42 C43 1.370(9) . ?
C43 C44 1.364(10) . ?
C44 C45 1.365(9) . ?
C44 C47 1.527(9) . ?
C45 C46 1.383(8) . ?
C51 C52 1.361(8) . ?
C51 C56 1.383(8) . ?
C52 C53 1.380(9) . ?
C53 C54 1.355(9) . ?
C54 C55 1.369(10) . ?
C54 C57 1.522(9) . ?
C55 C56 1.379(9) . ?
C61 C62 1.497(8) . ?
C62 C63 1.499(9) . ?
C63 C64 1.556(12) . ?
C64 C65 1.355(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ir1 N3 89.45(17) . . ?
N2 Ir1 N1 90.55(17) . . ?
N3 Ir1 N1 175.60(16) . . ?
N2 Ir1 N4 177.89(16) . . ?
N3 Ir1 N4 90.48(18) . . ?
N1 Ir1 N4 89.69(17) . . ?
N2 Ir1 C61 89.3(2) . . ?
N3 Ir1 C61 88.8(2) . . ?
N1 Ir1 C61 95.6(2) . . ?
N4 Ir1 C61 88.6(2) . . ?
C1 N1 C4 106.9(4) . . ?
C1 N1 Ir1 127.0(4) . . ?
C4 N1 Ir1 126.1(4) . . ?
C9 N2 C6 106.4(4) . . ?
C9 N2 Ir1 126.6(3) . . ?
C6 N2 Ir1 126.3(3) . . ?
C11 N3 C14 107.5(4) . . ?
C11 N3 Ir1 126.6(4) . . ?
C14 N3 Ir1 125.8(4) . . ?
C19 N4 C16 106.8(4) . . ?
C19 N4 Ir1 126.6(4) . . ?
C16 N4 Ir1 125.6(3) . . ?
N1 C1 C20 126.1(5) . . ?
N1 C1 C2 108.7(5) . . ?
C20 C1 C2 125.1(5) . . ?
C3 C2 C1 107.4(6) . . ?
C2 C3 C4 109.2(5) . . ?
C5 C4 N1 125.4(5) . . ?
C5 C4 C3 126.7(5) . . ?
N1 C4 C3 107.8(5) . . ?
C4 C5 C6 125.9(5) . . ?
C4 C5 C21 116.9(5) . . ?
C6 C5 C21 117.2(5) . . ?
C5 C6 N2 125.3(5) . . ?
C5 C6 C7 126.4(5) . . ?
N2 C6 C7 108.3(5) . . ?
C8 C7 C6 108.6(5) . . ?
C7 C8 C9 107.6(5) . . ?
N2 C9 C10 125.1(5) . . ?
N2 C9 C8 109.2(5) . . ?
C10 C9 C8 125.5(5) . . ?
C11 C10 C9 123.9(5) . . ?
C11 C10 C31 118.6(5) . . ?
C9 C10 C31 117.4(5) . . ?
N3 C11 C10 125.8(5) . . ?
N3 C11 C12 108.5(5) . . ?
C10 C11 C12 125.6(5) . . ?
C13 C12 C11 108.0(5) . . ?
C12 C13 C14 107.1(5) . . ?
N3 C14 C15 125.7(5) . . ?
N3 C14 C13 108.3(5) . . ?
C15 C14 C13 125.7(5) . . ?
C14 C15 C16 124.7(5) . . ?
C14 C15 C41 117.9(5) . . ?
C16 C15 C41 117.4(5) . . ?
C15 C16 N4 125.3(5) . . ?
C15 C16 C17 126.6(5) . . ?
N4 C16 C17 108.1(5) . . ?
C18 C17 C16 108.6(5) . . ?
C17 C18 C19 107.0(5) . . ?
N4 C19 C20 126.0(5) . . ?
N4 C19 C18 109.3(5) . . ?
C20 C19 C18 124.7(5) . . ?
C1 C20 C19 124.0(5) . . ?
C1 C20 C51 116.2(5) . . ?
C19 C20 C51 119.8(5) . . ?
C22 C21 C26 118.7(5) . . ?
C22 C21 C5 119.9(5) . . ?
C26 C21 C5 121.3(5) . . ?
C21 C22 C23 120.5(6) . . ?
C24 C23 C22 121.2(6) . . ?
C25 C24 C23 117.6(6) . . ?
C25 C24 C27 120.8(6) . . ?
C23 C24 C27 121.6(6) . . ?
C24 C25 C26 121.4(6) . . ?
C21 C26 C25 120.7(6) . . ?
C32 C31 C36 117.7(7) . . ?
C32 C31 C10 125.1(6) . . ?
C36 C31 C10 117.0(6) . . ?
C31 C32 C33 122.6(8) . . ?
C34 C33 C32 121.2(10) . . ?
C33 C34 C35 118.2(9) . . ?
C33 C34 C37 123.0(13) . . ?
C35 C34 C37 117.6(14) . . ?
C36 C35 C34 118.6(11) . . ?
C31 C36 C35 120.1(10) . . ?
C46 C41 C42 117.3(5) . . ?
C46 C41 C15 123.0(5) . . ?
C42 C41 C15 119.7(5) . . ?
C43 C42 C41 121.6(6) . . ?
C44 C43 C42 120.6(7) . . ?
C43 C44 C45 118.0(6) . . ?
C43 C44 C47 120.8(7) . . ?
C45 C44 C47 121.2(7) . . ?
C44 C45 C46 121.4(7) . . ?
C41 C46 C45 121.0(6) . . ?
C52 C51 C56 117.4(6) . . ?
C52 C51 C20 121.5(6) . . ?
C56 C51 C20 120.9(6) . . ?
C51 C52 C53 121.5(6) . . ?
C54 C53 C52 121.6(7) . . ?
C53 C54 C55 117.0(7) . . ?
C53 C54 C57 122.2(7) . . ?
C55 C54 C57 120.8(7) . . ?
C54 C55 C56 122.2(7) . . ?
C55 C56 C51 120.1(7) . . ?
C62 C61 Ir1 116.7(4) . . ?
C61 C62 C63 114.5(6) . . ?
C62 C63 C64 109.7(7) . . ?
C65 C64 C63 114.2(11) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.797
_refine_diff_density_rms         0.091
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/MeOH'
####################################################################### 
# 
# 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_HPZ2
_database_code_depnum_ccdc_archive 'CCDC 1048814'
_audit_update_record             
;
2015-02-11 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Adamantyl (5,10,15,20-tetratolylporphyri-nato) iridium(III) '
_chemical_name_common            Ir(ttp)-adamantyl
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C58 H51 Ir N4'
_chemical_formula_weight         996.23

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   11.0320(8)
_cell_length_b                   16.9785(12)
_cell_length_c                   25.1050(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.306(3)
_cell_angle_gamma                90.00
_cell_volume                     4682.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    211
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2016
_exptl_absorpt_coefficient_mu    2.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4657
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56597
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_sigmaI/netI    0.0938
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         25.25
_reflns_number_total             8462
_reflns_number_gt                4855
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS 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)+(0.0867P)²+10.4070P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8462
_refine_ls_number_parameters     568
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1375
_refine_ls_R_factor_gt           0.0778
_refine_ls_wR_factor_ref         0.1975
_refine_ls_wR_factor_gt          0.1743
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.008
_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 0.08234(4) 0.76284(3) 0.127004(15) 0.0597(2) Uani 1 1 d . . .
N1 N 0.0519(8) 0.7725(5) 0.2055(3) 0.057(2) Uani 1 1 d . . .
N2 N 0.2496(8) 0.7182(5) 0.1490(4) 0.065(2) Uani 1 1 d . . .
N3 N 0.1226(8) 0.7664(5) 0.0499(3) 0.055(2) Uani 1 1 d . . .
N4 N -0.0665(9) 0.8207(5) 0.1059(3) 0.076(3) Uani 1 1 d . . .
C1 C -0.0508(10) 0.8055(7) 0.2245(4) 0.061(3) Uani 1 1 d . . .
C2 C -0.0391(13) 0.7978(8) 0.2820(4) 0.083(4) Uani 1 1 d . . .
H2A H -0.0960 0.8133 0.3050 0.099 Uiso 1 1 calc R . .
C3 C 0.0695(12) 0.7642(6) 0.2960(4) 0.070(3) Uani 1 1 d . . .
H3A H 0.1019 0.7533 0.3308 0.085 Uiso 1 1 calc R . .
C4 C 0.1264(11) 0.7480(7) 0.2487(4) 0.067(3) Uani 1 1 d . . .
C5 C 0.2374(11) 0.7093(7) 0.2465(4) 0.068(3) Uani 1 1 d . . .
C6 C 0.2969(10) 0.6966(7) 0.1995(4) 0.064(3) Uani 1 1 d . . .
C7 C 0.4116(11) 0.6600(7) 0.1973(5) 0.072(3) Uani 1 1 d . . .
H7A H 0.4612 0.6401 0.2261 0.086 Uiso 1 1 calc R . .
C8 C 0.4355(10) 0.6594(7) 0.1453(4) 0.070(3) Uani 1 1 d . . .
H8A H 0.5058 0.6402 0.1322 0.084 Uiso 1 1 calc R . .
C9 C 0.3369(10) 0.6923(7) 0.1152(4) 0.065(3) Uani 1 1 d . . .
C10 C 0.3248(10) 0.7030(8) 0.0594(4) 0.069(3) Uani 1 1 d . . .
C11 C 0.2281(11) 0.7365(8) 0.0301(5) 0.085(4) Uani 1 1 d . . .
C12 C 0.2201(13) 0.7602(10) -0.0254(5) 0.107(6) Uani 1 1 d . . .
H12A H 0.2817 0.7534 -0.0479 0.128 Uiso 1 1 calc R . .
C13 C 0.1149(12) 0.7926(11) -0.0399(5) 0.110(5) Uani 1 1 d . . .
H13A H 0.0844 0.8067 -0.0744 0.132 Uiso 1 1 calc R . .
C14 C 0.0573(13) 0.8019(9) 0.0073(5) 0.089(4) Uani 1 1 d . . .
C15 C -0.0571(12) 0.8398(8) 0.0091(5) 0.082(4) Uani 1 1 d . . .
C16 C -0.1150(11) 0.8466(7) 0.0549(4) 0.073(3) Uani 1 1 d . . .
C17 C -0.2306(12) 0.8822(7) 0.0572(5) 0.081(4) Uani 1 1 d . . .
H17A H -0.2792 0.9029 0.0283 0.097 Uiso 1 1 calc R . .
C18 C -0.2584(11) 0.8809(7) 0.1089(4) 0.075(3) Uani 1 1 d . . .
H18A H -0.3282 0.9009 0.1221 0.090 Uiso 1 1 calc R . .
C19 C -0.1604(11) 0.8434(6) 0.1383(4) 0.065(3) Uani 1 1 d . . .
C20 C -0.1500(10) 0.8374(6) 0.1943(4) 0.063(3) Uani 1 1 d . . .
C21 C 0.2982(11) 0.6783(7) 0.2983(4) 0.066(3) Uani 1 1 d . . .
C22 C 0.3965(14) 0.7096(9) 0.3237(5) 0.107(5) Uani 1 1 d . . .
H22A H 0.4316 0.7536 0.3093 0.128 Uiso 1 1 calc R . .
C23 C 0.4501(14) 0.6775(12) 0.3727(6) 0.121(6) Uani 1 1 d . . .
H23A H 0.5187 0.7019 0.3896 0.145 Uiso 1 1 calc R . .
C24 C 0.4076(15) 0.6158(9) 0.3949(5) 0.093(4) Uani 1 1 d . . .
C25 C 0.2993(15) 0.5851(8) 0.3704(5) 0.099(5) Uani 1 1 d . . .
H25A H 0.2616 0.5434 0.3863 0.119 Uiso 1 1 calc R . .
C26 C 0.2476(13) 0.6157(8) 0.3230(5) 0.091(4) Uani 1 1 d . . .
H26A H 0.1762 0.5934 0.3072 0.109 Uiso 1 1 calc R . .
C27 C 0.4654(17) 0.5831(11) 0.4475(6) 0.147(7) Uani 1 1 d . . .
H27A H 0.5398 0.6108 0.4577 0.220 Uiso 1 1 calc R . .
H27B H 0.4825 0.5281 0.4435 0.220 Uiso 1 1 calc R . .
H27C H 0.4104 0.5898 0.4747 0.220 Uiso 1 1 calc R . .
C31 C 0.4296(10) 0.6757(7) 0.0295(4) 0.070(3) Uani 1 1 d . . .
C32 C 0.5327(11) 0.7186(8) 0.0282(5) 0.076(3) Uani 1 1 d . . .
H32A H 0.5435 0.7622 0.0506 0.091 Uiso 1 1 calc R . .
C33 C 0.6232(12) 0.7004(9) -0.0048(5) 0.090(4) Uani 1 1 d . . .
H33A H 0.6927 0.7315 -0.0042 0.108 Uiso 1 1 calc R . .
C34 C 0.6096(13) 0.6366(10) -0.0381(5) 0.092(4) Uani 1 1 d . . .
C35 C 0.5072(15) 0.5915(9) -0.0352(5) 0.102(5) Uani 1 1 d . . .
H35A H 0.4997 0.5450 -0.0549 0.123 Uiso 1 1 calc R . .
C36 C 0.4128(13) 0.6124(9) -0.0036(5) 0.101(5) Uani 1 1 d . . .
H36A H 0.3408 0.5837 -0.0053 0.121 Uiso 1 1 calc R . .
C37 C 0.7049(14) 0.6150(12) -0.0758(5) 0.140(7) Uani 1 1 d . . .
H37A H 0.7700 0.6527 -0.0721 0.210 Uiso 1 1 calc R . .
H37B H 0.6684 0.6151 -0.1120 0.210 Uiso 1 1 calc R . .
H37C H 0.7365 0.5634 -0.0669 0.210 Uiso 1 1 calc R . .
C41 C -0.1118(13) 0.8803(9) -0.0411(5) 0.104(5) Uani 1 1 d D . .
C42 C -0.1562(16) 0.8365(11) -0.0851(6) 0.141(7) Uani 1 1 d D . .
H42A H -0.1505 0.7819 -0.0832 0.170 Uiso 1 1 calc R . .
C43 C -0.209(2) 0.8703(15) -0.1318(7) 0.207(13) Uani 1 1 d D . .
H43A H -0.2396 0.8390 -0.1603 0.248 Uiso 1 1 calc R . .
C44 C -0.214(5) 0.9514(15) -0.1354(9) 0.34(3) Uani 1 1 d D . .
C45 C -0.185(3) 0.9965(13) -0.0903(8) 0.281(18) Uani 1 1 d D . .
H45A H -0.1994 1.0505 -0.0910 0.337 Uiso 1 1 calc R . .
C46 C -0.133(2) 0.9608(10) -0.0439(7) 0.194(11) Uani 1 1 d D . .
H46A H -0.1124 0.9917 -0.0138 0.233 Uiso 1 1 calc R . .
C47 C -0.267(3) 0.998(3) -0.1852(11) 0.49(4) Uani 1 1 d D . .
H47A H -0.2669 1.0530 -0.1770 0.737 Uiso 1 1 calc R . .
H47B H -0.3483 0.9806 -0.1955 0.737 Uiso 1 1 calc R . .
H47C H -0.2171 0.9887 -0.2141 0.737 Uiso 1 1 calc R . .
C51 C -0.2559(12) 0.8649(7) 0.2221(4) 0.072(3) Uani 1 1 d . . .
C52 C -0.3673(13) 0.8290(8) 0.2144(5) 0.091(4) Uani 1 1 d . . .
H52A H -0.3762 0.7858 0.1916 0.109 Uiso 1 1 calc R . .
C53 C -0.4679(13) 0.8549(8) 0.2394(6) 0.096(4) Uani 1 1 d . . .
H53A H -0.5432 0.8307 0.2318 0.115 Uiso 1 1 calc R . .
C54 C -0.4554(13) 0.9166(8) 0.2755(5) 0.082(4) Uani 1 1 d . . .
C55 C -0.3465(14) 0.9543(8) 0.2816(5) 0.085(4) Uani 1 1 d . . .
H55A H -0.3392 0.9989 0.3032 0.102 Uiso 1 1 calc R . .
C56 C -0.2454(12) 0.9291(7) 0.2571(4) 0.078(3) Uani 1 1 d . . .
H56A H -0.1712 0.9549 0.2638 0.093 Uiso 1 1 calc R . .
C57 C -0.5604(14) 0.9435(9) 0.3042(6) 0.125(6) Uani 1 1 d . . .
H57A H -0.5350 0.9863 0.3276 0.187 Uiso 1 1 calc R . .
H57B H -0.5887 0.9008 0.3247 0.187 Uiso 1 1 calc R . .
H57C H -0.6249 0.9610 0.2786 0.187 Uiso 1 1 calc R . .
C61 C -0.0037(10) 0.6473(6) 0.1208(4) 0.064(3) Uani 1 1 d . . .
C62 C -0.1100(14) 0.6453(8) 0.1585(5) 0.115(6) Uani 1 1 d . . .
H62A H -0.0776 0.6547 0.1952 0.138 Uiso 1 1 calc R . .
H62B H -0.1684 0.6866 0.1482 0.138 Uiso 1 1 calc R . .
C63 C -0.0637(13) 0.6353(9) 0.0644(5) 0.098(4) Uani 1 1 d . . .
H63A H -0.0028 0.6391 0.0390 0.118 Uiso 1 1 calc R . .
H63B H -0.1238 0.6763 0.0560 0.118 Uiso 1 1 calc R . .
C64 C 0.0835(12) 0.5822(9) 0.1363(5) 0.095(4) Uani 1 1 d . . .
H64A H 0.1187 0.5903 0.1727 0.114 Uiso 1 1 calc R . .
H64B H 0.1491 0.5830 0.1131 0.114 Uiso 1 1 calc R . .
C65 C -0.1746(13) 0.5636(8) 0.1543(5) 0.094(4) Uani 1 1 d . . .
H65A H -0.2398 0.5617 0.1783 0.113 Uiso 1 1 calc R . .
C66 C -0.2266(12) 0.5551(8) 0.0976(6) 0.097(4) Uani 1 1 d . . .
H66A H -0.2807 0.5990 0.0882 0.116 Uiso 1 1 calc R . .
H66B H -0.2740 0.5070 0.0938 0.116 Uiso 1 1 calc R . .
C67 C -0.1266(12) 0.5528(8) 0.0594(5) 0.085(4) Uani 1 1 d . . .
H67A H -0.1622 0.5442 0.0226 0.102 Uiso 1 1 calc R . .
C68 C -0.0344(13) 0.4922(8) 0.0745(5) 0.099(4) Uani 1 1 d . . .
H68A H 0.0305 0.4961 0.0511 0.119 Uiso 1 1 calc R . .
H68B H -0.0713 0.4405 0.0695 0.119 Uiso 1 1 calc R . .
C69 C 0.0192(12) 0.5000(8) 0.1320(5) 0.085(4) Uani 1 1 d . . .
H69A H 0.0773 0.4575 0.1415 0.101 Uiso 1 1 calc R . .
C70 C -0.0800(13) 0.5023(8) 0.1703(5) 0.097(4) Uani 1 1 d . . .
H70A H -0.1187 0.4511 0.1708 0.116 Uiso 1 1 calc R . .
H70B H -0.0436 0.5135 0.2061 0.116 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 N4 1.945(11) . ?
Ir1 N2 2.023(9) . ?
Ir1 N3 2.026(8) . ?
Ir1 N1 2.035(8) . ?
Ir1 C61 2.178(10) . ?
N1 C4 1.365(14) . ?
N1 C1 1.388(13) . ?
N2 C6 1.376(13) . ?
N2 C9 1.412(13) . ?
N3 C14 1.373(15) . ?
N3 C11 1.403(15) . ?
N4 C16 1.411(14) . ?
N4 C19 1.428(14) . ?
C1 C20 1.383(14) . ?
C1 C2 1.442(14) . ?
C2 C3 1.345(16) . ?
C3 C4 1.421(15) . ?
C4 C5 1.396(16) . ?
C5 C6 1.418(15) . ?
C5 C21 1.502(15) . ?
C6 C7 1.415(15) . ?
C7 C8 1.355(14) . ?
C8 C9 1.384(15) . ?
C9 C10 1.405(13) . ?
C10 C11 1.364(16) . ?
C10 C31 1.509(15) . ?
C11 C12 1.445(16) . ?
C12 C13 1.304(18) . ?
C13 C14 1.404(16) . ?
C14 C15 1.421(17) . ?
C15 C16 1.371(15) . ?
C15 C41 1.511(17) . ?
C16 C17 1.417(16) . ?
C17 C18 1.361(14) . ?
C18 C19 1.404(15) . ?
C19 C20 1.403(14) . ?
C20 C51 1.491(15) . ?
C21 C22 1.318(16) . ?
C21 C26 1.375(15) . ?
C22 C23 1.424(18) . ?
C23 C24 1.294(19) . ?
C24 C25 1.393(19) . ?
C24 C27 1.518(17) . ?
C25 C26 1.372(16) . ?
C31 C32 1.352(15) . ?
C31 C36 1.360(17) . ?
C32 C33 1.391(16) . ?
C33 C34 1.369(18) . ?
C34 C35 1.372(18) . ?
C34 C37 1.522(16) . ?
C35 C36 1.413(18) . ?
C41 C42 1.382(9) . ?
C41 C46 1.389(10) . ?
C42 C43 1.384(9) . ?
C43 C44 1.380(10) . ?
C44 C45 1.381(10) . ?
C44 C47 1.544(10) . ?
C45 C46 1.388(10) . ?
C51 C52 1.369(16) . ?
C51 C56 1.398(15) . ?
C52 C53 1.396(16) . ?
C53 C54 1.383(17) . ?
C54 C55 1.358(17) . ?
C54 C57 1.492(17) . ?
C55 C56 1.391(16) . ?
C61 C64 1.494(17) . ?
C61 C63 1.521(15) . ?
C61 C62 1.574(16) . ?
C62 C65 1.558(17) . ?
C63 C67 1.563(17) . ?
C64 C69 1.565(18) . ?
C65 C66 1.492(17) . ?
C65 C70 1.502(18) . ?
C66 C67 1.527(17) . ?
C67 C68 1.472(17) . ?
C68 C69 1.513(16) . ?
C69 C70 1.522(17) . ?

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
N4 Ir1 N2 171.5(3) . . ?
N4 Ir1 N3 88.8(3) . . ?
N2 Ir1 N3 89.8(4) . . ?
N4 Ir1 N1 90.7(3) . . ?
N2 Ir1 N1 89.7(4) . . ?
N3 Ir1 N1 172.9(3) . . ?
N4 Ir1 C61 94.8(4) . . ?
N2 Ir1 C61 93.6(4) . . ?
N3 Ir1 C61 95.2(3) . . ?
N1 Ir1 C61 91.8(3) . . ?
C4 N1 C1 107.4(8) . . ?
C4 N1 Ir1 127.1(7) . . ?
C1 N1 Ir1 125.4(7) . . ?
C6 N2 C9 104.4(9) . . ?
C6 N2 Ir1 127.6(8) . . ?
C9 N2 Ir1 127.5(7) . . ?
C14 N3 C11 105.9(9) . . ?
C14 N3 Ir1 127.7(8) . . ?
C11 N3 Ir1 126.2(7) . . ?
C16 N4 C19 101.5(10) . . ?
C16 N4 Ir1 130.1(8) . . ?
C19 N4 Ir1 128.3(7) . . ?
C20 C1 N1 126.7(9) . . ?
C20 C1 C2 125.3(11) . . ?
N1 C1 C2 108.0(10) . . ?
C3 C2 C1 107.2(10) . . ?
C2 C3 C4 108.3(10) . . ?
N1 C4 C5 125.3(10) . . ?
N1 C4 C3 109.0(10) . . ?
C5 C4 C3 125.5(11) . . ?
C4 C5 C6 125.4(10) . . ?
C4 C5 C21 117.0(10) . . ?
C6 C5 C21 117.6(11) . . ?
N2 C6 C7 110.2(9) . . ?
N2 C6 C5 124.1(11) . . ?
C7 C6 C5 125.7(10) . . ?
C8 C7 C6 107.1(10) . . ?
C7 C8 C9 108.1(10) . . ?
C8 C9 C10 126.5(11) . . ?
C8 C9 N2 110.0(9) . . ?
C10 C9 N2 123.4(10) . . ?
C11 C10 C9 126.1(11) . . ?
C11 C10 C31 117.1(10) . . ?
C9 C10 C31 116.8(10) . . ?
C10 C11 N3 126.3(10) . . ?
C10 C11 C12 127.8(12) . . ?
N3 C11 C12 105.2(11) . . ?
C13 C12 C11 111.1(12) . . ?
C12 C13 C14 105.8(12) . . ?
N3 C14 C13 111.3(13) . . ?
N3 C14 C15 125.3(10) . . ?
C13 C14 C15 123.4(12) . . ?
C16 C15 C14 123.3(11) . . ?
C16 C15 C41 118.7(12) . . ?
C14 C15 C41 117.8(11) . . ?
C15 C16 N4 124.6(11) . . ?
C15 C16 C17 124.1(11) . . ?
N4 C16 C17 111.3(10) . . ?
C18 C17 C16 108.3(11) . . ?
C17 C18 C19 106.2(11) . . ?
C20 C19 C18 123.2(11) . . ?
C20 C19 N4 123.7(10) . . ?
C18 C19 N4 112.7(10) . . ?
C1 C20 C19 124.4(10) . . ?
C1 C20 C51 118.7(10) . . ?
C19 C20 C51 116.8(10) . . ?
C22 C21 C26 116.3(11) . . ?
C22 C21 C5 124.0(11) . . ?
C26 C21 C5 119.6(11) . . ?
C21 C22 C23 121.4(13) . . ?
C24 C23 C22 122.9(14) . . ?
C23 C24 C25 116.3(13) . . ?
C23 C24 C27 122.0(15) . . ?
C25 C24 C27 121.4(14) . . ?
C26 C25 C24 120.8(13) . . ?
C25 C26 C21 122.0(13) . . ?
C32 C31 C36 118.6(11) . . ?
C32 C31 C10 122.1(11) . . ?
C36 C31 C10 118.6(11) . . ?
C31 C32 C33 123.1(13) . . ?
C34 C33 C32 119.7(13) . . ?
C33 C34 C35 117.0(12) . . ?
C33 C34 C37 121.8(15) . . ?
C35 C34 C37 121.2(14) . . ?
C34 C35 C36 122.9(13) . . ?
C31 C36 C35 118.4(12) . . ?
C42 C41 C46 116.3(15) . . ?
C42 C41 C15 120.5(13) . . ?
C46 C41 C15 122.8(13) . . ?
C41 C42 C43 123.0(18) . . ?
C44 C43 C42 119(2) . . ?
C43 C44 C45 119.6(19) . . ?
C43 C44 C47 125(3) . . ?
C45 C44 C47 115(2) . . ?
C44 C45 C46 119.6(18) . . ?
C45 C46 C41 121.8(17) . . ?
C52 C51 C56 117.3(12) . . ?
C52 C51 C20 121.7(11) . . ?
C56 C51 C20 121.0(12) . . ?
C51 C52 C53 122.4(13) . . ?
C54 C53 C52 119.8(13) . . ?
C55 C54 C53 117.8(12) . . ?
C55 C54 C57 121.2(14) . . ?
C53 C54 C57 120.9(15) . . ?
C54 C55 C56 122.8(12) . . ?
C55 C56 C51 119.6(12) . . ?
C64 C61 C63 110.9(11) . . ?
C64 C61 C62 109.0(10) . . ?
C63 C61 C62 105.8(10) . . ?
C64 C61 Ir1 112.5(8) . . ?
C63 C61 Ir1 109.7(8) . . ?
C62 C61 Ir1 108.7(7) . . ?
C65 C62 C61 109.9(10) . . ?
C61 C63 C67 110.3(11) . . ?
C61 C64 C69 111.4(10) . . ?
C66 C65 C70 112.6(11) . . ?
C66 C65 C62 106.5(12) . . ?
C70 C65 C62 107.3(13) . . ?
C65 C66 C67 111.5(11) . . ?
C68 C67 C66 112.2(12) . . ?
C68 C67 C63 108.4(11) . . ?
C66 C67 C63 105.5(11) . . ?
C67 C68 C69 112.6(11) . . ?
C68 C69 C70 111.3(11) . . ?
C68 C69 C64 106.2(11) . . ?
C70 C69 C64 106.4(11) . . ?
C65 C70 C69 111.8(11) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         3.405
_refine_diff_density_min         -1.679
_refine_diff_density_rms         0.131
# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.024 -0.008 0.173 15.6 0.2
2 0.024 0.008 0.827 15.5 0.8
3 0.024 0.492 0.327 15.6 0.6
4 -0.024 0.508 0.673 15.6 0.6
5 0.260 0.652 0.884 11.4 -0.2
6 0.260 0.848 0.384 11.4 -0.1
7 0.317 0.155 0.258 7.1 0.3
8 0.317 0.345 0.758 7.1 0.4
9 0.429 0.613 0.601 24.9 1.1
10 0.429 0.887 0.101 24.9 1.3
11 0.571 0.113 0.899 24.9 1.2
12 0.571 0.387 0.399 24.9 1.4
13 0.683 0.655 0.242 7.1 0.3
14 0.683 0.845 0.742 7.1 0.2
15 0.740 0.152 0.616 11.4 -0.1
16 0.740 0.348 0.116 11.4 -0.2
_platon_squeeze_details          
;
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_HPZ181(LOW)
_database_code_depnum_ccdc_archive 'CCDC 1059004'
_audit_update_record             
;
2015-04-11 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'c-Pentyl (5,10,15,20-tetratolylporphyri-nato) iridium(III) .CH2Cl2'
_chemical_name_common            'Ir(ttp)-c-pentyl. CH2Cl2'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H47 Cl2 Ir N4'
_chemical_formula_weight         1015.06

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'
Ir Ir -1.4442 7.9887 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   15.5148(6)
_cell_length_b                   18.2080(8)
_cell_length_c                   16.0602(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.5671(11)
_cell_angle_gamma                90.00
_cell_volume                     4325.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    1390
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2040
_exptl_absorpt_coefficient_mu    3.254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4297
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      172(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 D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            84813
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0118
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.25
_reflns_number_total             7831
_reflns_number_gt                7362
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0227P)²+13.6251P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7831
_refine_ls_number_parameters     550
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0590
_refine_ls_wR_factor_gt          0.0574
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.005
_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 0.398356(7) 0.398517(6) 0.557685(7) 0.01374(5) Uani 1 1 d . . .
N1 N 0.46760(17) 0.41950(14) 0.68433(16) 0.0167(5) Uani 1 1 d . . .
N2 N 0.51365(17) 0.41094(14) 0.52569(16) 0.0162(5) Uani 1 1 d . . .
N3 N 0.33035(16) 0.37439(14) 0.43204(16) 0.0158(5) Uani 1 1 d . . .
N4 N 0.28067(17) 0.39969(13) 0.58702(17) 0.0173(5) Uani 1 1 d . . .
C1 C 0.4318(2) 0.42173(17) 0.75309(19) 0.0181(6) Uani 1 1 d . . .
C2 C 0.5044(2) 0.42187(18) 0.8340(2) 0.0214(7) Uani 1 1 d . . .
H2A H 0.4984 0.4236 0.8911 0.026 Uiso 1 1 calc R . .
C3 C 0.5827(2) 0.41913(18) 0.8137(2) 0.0211(7) Uani 1 1 d . . .
H3A H 0.6418 0.4174 0.8540 0.025 Uiso 1 1 calc R . .
C4 C 0.5604(2) 0.41922(16) 0.71962(19) 0.0172(6) Uani 1 1 d . . .
C5 C 0.6219(2) 0.42602(16) 0.67256(19) 0.0169(6) Uani 1 1 d . . .
C6 C 0.5979(2) 0.42989(16) 0.58123(19) 0.0167(6) Uani 1 1 d . . .
C7 C 0.6575(2) 0.44392(18) 0.5296(2) 0.0199(6) Uani 1 1 d . . .
H7A H 0.7184 0.4604 0.5510 0.024 Uiso 1 1 calc R . .
C8 C 0.6117(2) 0.42952(18) 0.4452(2) 0.0213(7) Uani 1 1 d . . .
H8A H 0.6340 0.4343 0.3966 0.026 Uiso 1 1 calc R . .
C9 C 0.5225(2) 0.40551(16) 0.4431(2) 0.0166(6) Uani 1 1 d . . .
C10 C 0.4579(2) 0.37531(17) 0.37059(19) 0.0171(6) Uani 1 1 d . . .
C11 C 0.3689(2) 0.35954(16) 0.36705(19) 0.0166(6) Uani 1 1 d . . .
C12 C 0.3007(2) 0.32993(17) 0.2924(2) 0.0189(6) Uani 1 1 d . . .
H12A H 0.3098 0.3132 0.2396 0.023 Uiso 1 1 calc R . .
C13 C 0.2218(2) 0.33043(17) 0.3113(2) 0.0191(6) Uani 1 1 d . . .
H13A H 0.1647 0.3151 0.2737 0.023 Uiso 1 1 calc R . .
C14 C 0.2394(2) 0.35833(16) 0.39855(19) 0.0168(6) Uani 1 1 d . . .
C15 C 0.1752(2) 0.36972(16) 0.4421(2) 0.0181(6) Uani 1 1 d . . .
C16 C 0.1948(2) 0.39042(17) 0.5293(2) 0.0191(6) Uani 1 1 d . . .
C17 C 0.1294(2) 0.39982(18) 0.5755(2) 0.0240(7) Uani 1 1 d . . .
H17A H 0.0656 0.3971 0.5511 0.029 Uiso 1 1 calc R . .
C18 C 0.1751(2) 0.41321(19) 0.6597(2) 0.0240(7) Uani 1 1 d . . .
H18A H 0.1494 0.4216 0.7055 0.029 Uiso 1 1 calc R . .
C19 C 0.2702(2) 0.41255(17) 0.6679(2) 0.0193(6) Uani 1 1 d . . .
C20 C 0.3400(2) 0.42160(17) 0.7459(2) 0.0194(6) Uani 1 1 d . . .
C21 C 0.7204(2) 0.42641(17) 0.72334(19) 0.0172(6) Uani 1 1 d . . .
C22 C 0.7748(2) 0.48669(18) 0.7237(2) 0.0222(7) Uani 1 1 d . . .
H22A H 0.7491 0.5295 0.6921 0.027 Uiso 1 1 calc R . .
C23 C 0.8663(2) 0.4858(2) 0.7696(2) 0.0282(8) Uani 1 1 d . . .
H23A H 0.9020 0.5280 0.7689 0.034 Uiso 1 1 calc R . .
C24 C 0.9063(2) 0.4242(2) 0.8163(2) 0.0315(8) Uani 1 1 d . . .
C25 C 0.8514(2) 0.3639(2) 0.8171(2) 0.0307(8) Uani 1 1 d . . .
H25A H 0.8770 0.3215 0.8496 0.037 Uiso 1 1 calc R . .
C26 C 0.7600(2) 0.36461(18) 0.7715(2) 0.0240(7) Uani 1 1 d . . .
H26A H 0.7239 0.3228 0.7730 0.029 Uiso 1 1 calc R . .
C27 C 1.0063(3) 0.4230(3) 0.8652(3) 0.0605(14) Uani 1 1 d . . .
H27A H 1.0224 0.3755 0.8942 0.091 Uiso 1 1 calc R . .
H27B H 1.0204 0.4623 0.9089 0.091 Uiso 1 1 calc R . .
H27C H 1.0410 0.4306 0.8240 0.091 Uiso 1 1 calc R . .
C31 C 0.4861(2) 0.35730(17) 0.29199(19) 0.0179(6) Uani 1 1 d . . .
C32 C 0.5455(2) 0.29956(19) 0.2941(2) 0.0242(7) Uani 1 1 d . . .
H32A H 0.5699 0.2726 0.3466 0.029 Uiso 1 1 calc R . .
C33 C 0.5696(2) 0.2810(2) 0.2202(2) 0.0275(7) Uani 1 1 d . . .
H33A H 0.6094 0.2409 0.2226 0.033 Uiso 1 1 calc R . .
C34 C 0.5363(2) 0.32001(19) 0.1427(2) 0.0261(7) Uani 1 1 d . . .
C35 C 0.4772(3) 0.3776(2) 0.1409(2) 0.0289(8) Uani 1 1 d . . .
H35A H 0.4537 0.4050 0.0887 0.035 Uiso 1 1 calc R . .
C36 C 0.4518(2) 0.39578(18) 0.2144(2) 0.0243(7) Uani 1 1 d . . .
H36A H 0.4105 0.4349 0.2114 0.029 Uiso 1 1 calc R . .
C37 C 0.5635(3) 0.3009(2) 0.0626(3) 0.0413(10) Uani 1 1 d . . .
H37A H 0.6055 0.2592 0.0758 0.062 Uiso 1 1 calc R . .
H37B H 0.5931 0.3433 0.0455 0.062 Uiso 1 1 calc R . .
H37C H 0.5097 0.2877 0.0147 0.062 Uiso 1 1 calc R . .
C41 C 0.0778(2) 0.35769(17) 0.3919(2) 0.0186(6) Uani 1 1 d . . .
C42 C 0.0444(2) 0.28725(18) 0.36800(19) 0.0199(6) Uani 1 1 d . . .
H42A H 0.0842 0.2463 0.3818 0.024 Uiso 1 1 calc R . .
C43 C -0.0467(2) 0.27635(19) 0.3241(2) 0.0242(7) Uani 1 1 d . . .
H43A H -0.0685 0.2279 0.3089 0.029 Uiso 1 1 calc R . .
C44 C -0.1063(2) 0.3348(2) 0.3020(2) 0.0292(8) Uani 1 1 d . . .
C45 C -0.0724(2) 0.4050(2) 0.3251(3) 0.0349(9) Uani 1 1 d . . .
H45A H -0.1121 0.4459 0.3101 0.042 Uiso 1 1 calc R . .
C46 C 0.0180(2) 0.41680(19) 0.3696(2) 0.0290(8) Uani 1 1 d . . .
H46A H 0.0394 0.4653 0.3850 0.035 Uiso 1 1 calc R . .
C47 C -0.2055(2) 0.3227(3) 0.2569(3) 0.0458(11) Uani 1 1 d . . .
H47A H -0.2170 0.2702 0.2456 0.069 Uiso 1 1 calc R . .
H47B H -0.2235 0.3496 0.2015 0.069 Uiso 1 1 calc R . .
H47C H -0.2406 0.3406 0.2943 0.069 Uiso 1 1 calc R . .
C51 C 0.3133(2) 0.43045(19) 0.8277(2) 0.0215(7) Uani 1 1 d . . .
C52 C 0.2729(2) 0.3729(2) 0.8593(2) 0.0288(8) Uani 1 1 d . . .
H52A H 0.2652 0.3266 0.8307 0.035 Uiso 1 1 calc R . .
C53 C 0.2437(3) 0.3826(2) 0.9320(2) 0.0310(8) Uani 1 1 d . . .
H53A H 0.2163 0.3427 0.9525 0.037 Uiso 1 1 calc R . .
C54 C 0.2536(2) 0.4494(2) 0.9757(2) 0.0273(8) Uani 1 1 d . . .
C55 C 0.2952(2) 0.5060(2) 0.9451(2) 0.0297(8) Uani 1 1 d . . .
H55A H 0.3036 0.5520 0.9745 0.036 Uiso 1 1 calc R . .
C56 C 0.3251(2) 0.49716(19) 0.8721(2) 0.0268(7) Uani 1 1 d . . .
H56A H 0.3537 0.5369 0.8526 0.032 Uiso 1 1 calc R . .
C57 C 0.2185(3) 0.4590(2) 1.0534(2) 0.0369(9) Uani 1 1 d . . .
H57A H 0.2311 0.5091 1.0762 0.055 Uiso 1 1 calc R . .
H57B H 0.2486 0.4238 1.0991 0.055 Uiso 1 1 calc R . .
H57C H 0.1531 0.4503 1.0352 0.055 Uiso 1 1 calc R . .
C61 C 0.4165(2) 0.28746(17) 0.5897(2) 0.0209(6) Uani 1 1 d . . .
H61A H 0.4159 0.2833 0.6516 0.025 Uiso 1 1 calc R . .
C62 C 0.5042(3) 0.2535(2) 0.5868(3) 0.0409(10) Uani 1 1 d . . .
H62A H 0.5563 0.2747 0.6323 0.049 Uiso 1 1 calc R . .
H62B H 0.5132 0.2607 0.5288 0.049 Uiso 1 1 calc R . .
C63 C 0.4921(3) 0.1716(2) 0.6044(3) 0.0377(9) Uani 1 1 d . . .
H63A H 0.5276 0.1405 0.5762 0.045 Uiso 1 1 calc R . .
H63B H 0.5116 0.1614 0.6679 0.045 Uiso 1 1 calc R . .
C64 C 0.3905(3) 0.1572(2) 0.5645(2) 0.0341(9) Uani 1 1 d . . .
H64A H 0.3656 0.1337 0.6079 0.041 Uiso 1 1 calc R . .
H64B H 0.3793 0.1247 0.5130 0.041 Uiso 1 1 calc R . .
C65 C 0.3465(3) 0.23312(19) 0.5376(3) 0.0358(9) Uani 1 1 d . . .
H65A H 0.3338 0.2413 0.4741 0.043 Uiso 1 1 calc R . .
H65B H 0.2893 0.2375 0.5526 0.043 Uiso 1 1 calc R . .
C66 C 0.8435(5) 0.3101(6) 0.5980(5) 0.170(6) Uani 1 1 d . . .
H66A H 0.8486 0.3482 0.6432 0.204 Uiso 1 1 calc R . .
H66B H 0.8904 0.2727 0.6231 0.204 Uiso 1 1 calc R . .
Cl1 Cl 0.73812(13) 0.26834(8) 0.57737(9) 0.0798(5) Uani 1 1 d . . .
Cl2 Cl 0.86797(13) 0.3507(2) 0.50984(13) 0.1633(14) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 N2 2.017(3) . ?
Ir1 N4 2.019(3) . ?
Ir1 N3 2.023(2) . ?
Ir1 N1 2.029(2) . ?
Ir1 C61 2.085(3) . ?
N1 C1 1.379(4) . ?
N1 C4 1.379(4) . ?
N2 C9 1.378(4) . ?
N2 C6 1.386(4) . ?
N3 C11 1.377(4) . ?
N3 C14 1.382(4) . ?
N4 C19 1.377(4) . ?
N4 C16 1.384(4) . ?
C1 C20 1.394(4) . ?
C1 C2 1.440(4) . ?
C2 C3 1.350(5) . ?
C3 C4 1.445(4) . ?
C4 C5 1.391(4) . ?
C5 C6 1.402(4) . ?
C5 C21 1.499(4) . ?
C6 C7 1.440(4) . ?
C7 C8 1.352(4) . ?
C8 C9 1.441(4) . ?
C9 C10 1.400(4) . ?
C10 C11 1.394(4) . ?
C10 C31 1.493(4) . ?
C11 C12 1.443(4) . ?
C12 C13 1.348(4) . ?
C13 C14 1.437(4) . ?
C14 C15 1.393(4) . ?
C15 C16 1.392(4) . ?
C15 C41 1.499(4) . ?
C16 C17 1.437(4) . ?
C17 C18 1.346(5) . ?
C18 C19 1.440(4) . ?
C19 C20 1.397(4) . ?
C20 C51 1.500(4) . ?
C21 C22 1.383(4) . ?
C21 C26 1.399(4) . ?
C22 C23 1.387(5) . ?
C23 C24 1.388(5) . ?
C24 C25 1.393(5) . ?
C24 C27 1.512(5) . ?
C25 C26 1.385(5) . ?
C31 C36 1.388(5) . ?
C31 C32 1.392(5) . ?
C32 C33 1.389(5) . ?
C33 C34 1.391(5) . ?
C34 C35 1.387(5) . ?
C34 C37 1.510(5) . ?
C35 C36 1.392(5) . ?
C41 C42 1.393(4) . ?
C41 C46 1.395(5) . ?
C42 C43 1.390(4) . ?
C43 C44 1.383(5) . ?
C44 C45 1.391(5) . ?
C44 C47 1.506(5) . ?
C45 C46 1.385(5) . ?
C51 C56 1.393(5) . ?
C51 C52 1.393(5) . ?
C52 C53 1.386(5) . ?
C53 C54 1.389(5) . ?
C54 C55 1.383(5) . ?
C54 C57 1.513(5) . ?
C55 C56 1.393(5) . ?
C61 C62 1.509(5) . ?
C61 C65 1.520(5) . ?
C62 C63 1.539(5) . ?
C63 C64 1.534(5) . ?
C64 C65 1.544(5) . ?
C66 Cl2 1.738(7) . ?
C66 Cl1 1.741(11) . ?

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 Ir1 N4 172.84(10) . . ?
N2 Ir1 N3 90.33(10) . . ?
N4 Ir1 N3 89.94(10) . . ?
N2 Ir1 N1 89.56(10) . . ?
N4 Ir1 N1 90.38(10) . . ?
N3 Ir1 N1 178.29(10) . . ?
N2 Ir1 C61 96.19(11) . . ?
N4 Ir1 C61 90.96(11) . . ?
N3 Ir1 C61 91.51(11) . . ?
N1 Ir1 C61 86.80(11) . . ?
C1 N1 C4 107.1(2) . . ?
C1 N1 Ir1 126.1(2) . . ?
C4 N1 Ir1 125.6(2) . . ?
C9 N2 C6 106.8(2) . . ?
C9 N2 Ir1 126.2(2) . . ?
C6 N2 Ir1 126.9(2) . . ?
C11 N3 C14 106.8(2) . . ?
C11 N3 Ir1 125.7(2) . . ?
C14 N3 Ir1 126.7(2) . . ?
C19 N4 C16 106.8(3) . . ?
C19 N4 Ir1 126.5(2) . . ?
C16 N4 Ir1 126.7(2) . . ?
N1 C1 C20 125.6(3) . . ?
N1 C1 C2 109.1(3) . . ?
C20 C1 C2 125.2(3) . . ?
C3 C2 C1 107.4(3) . . ?
C2 C3 C4 107.6(3) . . ?
N1 C4 C5 125.4(3) . . ?
N1 C4 C3 108.7(3) . . ?
C5 C4 C3 125.5(3) . . ?
C4 C5 C6 124.3(3) . . ?
C4 C5 C21 117.3(3) . . ?
C6 C5 C21 118.3(3) . . ?
N2 C6 C5 124.2(3) . . ?
N2 C6 C7 108.6(3) . . ?
C5 C6 C7 126.7(3) . . ?
C8 C7 C6 107.9(3) . . ?
C7 C8 C9 107.1(3) . . ?
N2 C9 C10 125.0(3) . . ?
N2 C9 C8 109.2(3) . . ?
C10 C9 C8 125.5(3) . . ?
C11 C10 C9 124.6(3) . . ?
C11 C10 C31 117.4(3) . . ?
C9 C10 C31 118.0(3) . . ?
N3 C11 C10 125.4(3) . . ?
N3 C11 C12 109.0(3) . . ?
C10 C11 C12 125.4(3) . . ?
C13 C12 C11 107.4(3) . . ?
C12 C13 C14 107.7(3) . . ?
N3 C14 C15 125.0(3) . . ?
N3 C14 C13 109.0(3) . . ?
C15 C14 C13 126.0(3) . . ?
C16 C15 C14 124.9(3) . . ?
C16 C15 C41 117.3(3) . . ?
C14 C15 C41 117.8(3) . . ?
N4 C16 C15 125.5(3) . . ?
N4 C16 C17 109.0(3) . . ?
C15 C16 C17 125.3(3) . . ?
C18 C17 C16 107.5(3) . . ?
C17 C18 C19 107.8(3) . . ?
N4 C19 C20 125.9(3) . . ?
N4 C19 C18 108.9(3) . . ?
C20 C19 C18 125.2(3) . . ?
C1 C20 C19 124.8(3) . . ?
C1 C20 C51 118.2(3) . . ?
C19 C20 C51 117.0(3) . . ?
C22 C21 C26 118.1(3) . . ?
C22 C21 C5 121.8(3) . . ?
C26 C21 C5 120.2(3) . . ?
C21 C22 C23 121.2(3) . . ?
C22 C23 C24 121.0(3) . . ?
C23 C24 C25 117.8(3) . . ?
C23 C24 C27 120.9(4) . . ?
C25 C24 C27 121.3(4) . . ?
C26 C25 C24 121.3(3) . . ?
C25 C26 C21 120.6(3) . . ?
C36 C31 C32 118.4(3) . . ?
C36 C31 C10 121.1(3) . . ?
C32 C31 C10 120.5(3) . . ?
C33 C32 C31 120.7(3) . . ?
C32 C33 C34 121.1(3) . . ?
C35 C34 C33 118.0(3) . . ?
C35 C34 C37 120.7(3) . . ?
C33 C34 C37 121.3(3) . . ?
C34 C35 C36 121.2(3) . . ?
C31 C36 C35 120.7(3) . . ?
C42 C41 C46 118.5(3) . . ?
C42 C41 C15 120.9(3) . . ?
C46 C41 C15 120.6(3) . . ?
C43 C42 C41 120.5(3) . . ?
C44 C43 C42 121.2(3) . . ?
C43 C44 C45 118.0(3) . . ?
C43 C44 C47 121.2(3) . . ?
C45 C44 C47 120.8(3) . . ?
C46 C45 C44 121.5(3) . . ?
C45 C46 C41 120.3(3) . . ?
C56 C51 C52 118.2(3) . . ?
C56 C51 C20 121.0(3) . . ?
C52 C51 C20 120.8(3) . . ?
C53 C52 C51 120.6(3) . . ?
C52 C53 C54 121.6(3) . . ?
C55 C54 C53 117.7(3) . . ?
C55 C54 C57 122.0(3) . . ?
C53 C54 C57 120.3(3) . . ?
C54 C55 C56 121.5(3) . . ?
C51 C56 C55 120.4(3) . . ?
C62 C61 C65 102.5(3) . . ?
C62 C61 Ir1 116.5(2) . . ?
C65 C61 Ir1 118.4(2) . . ?
C61 C62 C63 103.2(3) . . ?
C64 C63 C62 104.9(3) . . ?
C63 C64 C65 106.0(3) . . ?
C61 C65 C64 104.3(3) . . ?
Cl2 C66 Cl1 117.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.427
_refine_diff_density_min         -1.681
_refine_diff_density_rms         0.089
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/MeOH'
