# Electronic Supplementary Material (ESI) for ChemComm.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1059389'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H34 Cl Ir N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         686.27
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.9592(12)
_cell_length_b                   11.0891(12)
_cell_length_c                   22.818(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2773.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3007
_cell_measurement_theta_min      2.5614
_cell_measurement_theta_max      22.8895
_cell_measurement_temperature    173

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360

_exptl_absorpt_coefficient_mu    4.936
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16350
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0883
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         28.773
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             6583
_reflns_number_gt                5376
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0938
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_number_reflns         6583
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.335
_refine_diff_density_min         -1.008
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0032(2)
_refine_ls_abs_structure_details 
;
Flack x determined using 2005 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(8)

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'
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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5795(8) 0.5874(9) 0.6862(4) 0.021(2) Uani d . . . 1 . .
C C2 0.3968(9) 0.5484(9) 0.6425(5) 0.027(3) Uani d . . . 1 . .
H H2 0.3388 0.5277 0.6132 0.032 Uiso calc U . R 1 . .
C C3 0.3736(7) 0.5747(8) 0.6992(5) 0.024(2) Uani d . . . 1 . .
C C4 0.2754(8) 0.5904(10) 0.7442(4) 0.028(2) Uani d . . . 1 . .
H H4A 0.214 0.5252 0.7416 0.034 Uiso calc U . R 1 . .
H H4B 0.2341 0.6693 0.7399 0.034 Uiso calc U . R 1 . .
C C5 0.3482(8) 0.5834(9) 0.8025(5) 0.029(2) Uani d . . . 1 . .
H H5A 0.309 0.6335 0.8331 0.035 Uiso calc U . R 1 . .
H H5B 0.353 0.4991 0.8166 0.035 Uiso calc U . R 1 . .
C C6 0.4758(8) 0.6319(9) 0.7876(4) 0.023(2) Uani d . . . 1 . .
H H6 0.4751 0.7218 0.7913 0.028 Uiso calc U . R 1 . .
C C7 0.5772(9) 0.5822(11) 0.8248(4) 0.026(2) Uani d . . . 1 . .
C C8 0.6221(10) 0.4652(11) 0.8171(5) 0.039(3) Uani d . . . 1 . .
H H8 0.5867 0.4148 0.788 0.047 Uiso calc U . R 1 . .
C C9 0.7158(11) 0.4222(14) 0.8505(6) 0.059(4) Uani d . . . 1 . .
H H9 0.7471 0.3434 0.8441 0.07 Uiso calc U . R 1 . .
C C10 0.7643(15) 0.4950(18) 0.8937(7) 0.081(6) Uani d . . . 1 . .
H H10 0.8283 0.4645 0.9175 0.098 Uiso calc U . R 1 . .
C C11 0.7238(12) 0.6075(14) 0.9030(6) 0.057(4) Uani d . . . 1 . .
H H11 0.7598 0.6559 0.9327 0.069 Uiso calc U . R 1 . .
C C12 0.6276(11) 0.6540(12) 0.8685(5) 0.040(3) Uani d . . . 1 . .
H H12 0.5977 0.7332 0.8752 0.048 Uiso calc U . R 1 . .
C C13 0.5884(10) 0.5530(9) 0.5787(5) 0.024(2) Uani d . . . 1 . .
H H13 0.6737 0.5276 0.5881 0.029 Uiso calc U . R 1 . .
C C14 0.5977(9) 0.6761(10) 0.5508(5) 0.024(2) Uani d . . . 1 . .
C C15 0.5187(11) 0.7706(10) 0.5637(5) 0.032(3) Uani d . . . 1 . .
H H15 0.4574 0.7602 0.5927 0.038 Uiso calc U . R 1 . .
C C16 0.5286(10) 0.8807(10) 0.5344(6) 0.038(3) Uani d . . . 1 . .
H H16 0.4741 0.9446 0.5434 0.045 Uiso calc U . R 1 . .
C C17 0.6176(11) 0.8968(12) 0.4923(5) 0.045(3) Uani d . . . 1 . .
H H17 0.6239 0.9711 0.4719 0.054 Uiso calc U . R 1 . .
C C18 0.6970(12) 0.8041(10) 0.4804(5) 0.045(3) Uani d . . . 1 . .
H H18 0.7587 0.815 0.4517 0.054 Uiso calc U . R 1 . .
C C19 0.6882(10) 0.6951(10) 0.5095(5) 0.032(3) Uani d . . . 1 . .
H H19 0.7449 0.6326 0.5011 0.039 Uiso calc U . R 1 . .
C C20 0.5363(10) 0.4564(10) 0.5381(5) 0.027(3) Uani d . . . 1 . .
C C21 0.4519(12) 0.4824(12) 0.4952(6) 0.047(3) Uani d . . . 1 . .
H H21 0.4242 0.5629 0.4904 0.056 Uiso calc U . R 1 . .
C C22 0.4065(13) 0.3918(14) 0.4588(6) 0.056(4) Uani d . . . 1 . .
H H22 0.3466 0.4101 0.43 0.068 Uiso calc U . R 1 . .
C C23 0.4485(16) 0.2773(16) 0.4648(7) 0.065(5) Uani d . . . 1 . .
H H23 0.4191 0.2154 0.4397 0.078 Uiso calc U . R 1 . .
C C24 0.5322(16) 0.2512(15) 0.5066(9) 0.064(5) Uani d . . . 1 . .
H H24 0.5609 0.1707 0.5104 0.076 Uiso calc U . R 1 . .
C C25 0.5767(13) 0.3384(11) 0.5435(6) 0.048(4) Uani d . . . 1 . .
H H25 0.635 0.318 0.5726 0.057 Uiso calc U . R 1 . .
C C26 0.7613(10) 0.7656(7) 0.7393(4) 0.026(2) Uani d . . . 1 . .
H H26 0.6799 0.7897 0.7552 0.031 Uiso calc U . R 1 . .
C C27 0.7725(11) 0.7786(8) 0.6771(5) 0.030(2) Uani d . . . 1 . .
H H27 0.7008 0.7665 0.6544 0.037 Uiso calc U . R 1 . .
C C28 0.8856(11) 0.8093(11) 0.6448(6) 0.043(3) Uani d . . . 1 . .
H H28A 0.9039 0.8959 0.6506 0.052 Uiso calc U . R 1 . .
H H28B 0.8719 0.7961 0.6024 0.052 Uiso calc U . R 1 . .
C C29 0.9966(11) 0.7344(12) 0.6644(6) 0.043(3) Uani d . . . 1 . .
H H29A 1.0538 0.7258 0.6311 0.052 Uiso calc U . R 1 . .
H H29B 1.0396 0.7776 0.6963 0.052 Uiso calc U . R 1 . .
C C30 0.9598(8) 0.6111(11) 0.6857(5) 0.032(3) Uani d . . . 1 . .
H H30 0.9504 0.5483 0.6577 0.038 Uiso calc U . R 1 . .
C C31 0.9393(8) 0.5851(12) 0.7438(5) 0.032(3) Uani d . . . 1 . .
H H31 0.9202 0.504 0.7536 0.039 Uiso calc U . R 1 . .
C C32 0.9448(9) 0.6756(10) 0.7934(6) 0.034(3) Uani d . . . 1 . .
H H32A 1.0306 0.7 0.7997 0.041 Uiso calc U . R 1 . .
H H32B 0.9153 0.6368 0.8299 0.041 Uiso calc U . R 1 . .
C C33 0.8674(10) 0.7886(10) 0.7811(5) 0.031(3) Uani d . . . 1 . .
H H33A 0.8347 0.8195 0.8187 0.038 Uiso calc U . R 1 . .
H H33B 0.9206 0.8518 0.7643 0.038 Uiso calc U . R 1 . .
Cl Cl1 0.7715(3) 0.3837(2) 0.68101(12) 0.0369(6) Uani d . . . 1 . .
Ir Ir1 0.76354(3) 0.59476(3) 0.69949(2) 0.02211(13) Uani d . . . 1 . .
N N1 0.4871(7) 0.5992(8) 0.7247(4) 0.0219(18) Uani d . . . 1 . .
N N2 0.5220(7) 0.5577(7) 0.6355(4) 0.023(2) Uani d . . . 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.346(11) ?
C1 N2 . 1.359(13) ?
C1 Ir1 . 2.042(9) ?
C2 C3 . 1.352(15) ?
C2 N2 . 1.385(13) ?
C2 H2 . 0.95 ?
C3 N1 . 1.399(11) ?
C3 C4 . 1.497(13) ?
C4 C5 . 1.553(14) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.537(12) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 N1 . 1.487(12) ?
C6 C7 . 1.503(14) ?
C6 H6 . 1.0 ?
C7 C12 . 1.391(16) ?
C7 C8 . 1.398(16) ?
C8 C9 . 1.365(16) ?
C8 H8 . 0.95 ?
C9 C10 . 1.38(2) ?
C9 H9 . 0.95 ?
C10 C11 . 1.34(2) ?
C10 H10 . 0.95 ?
C11 C12 . 1.412(17) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?
C13 N2 . 1.486(13) ?
C13 C14 . 1.510(14) ?
C13 C20 . 1.527(15) ?
C13 H13 . 1.0 ?
C14 C19 . 1.384(14) ?
C14 C15 . 1.391(15) ?
C15 C16 . 1.396(15) ?
C15 H15 . 0.95 ?
C16 C17 . 1.379(16) ?
C16 H16 . 0.95 ?
C17 C18 . 1.374(16) ?
C17 H17 . 0.95 ?
C18 C19 . 1.383(15) ?
C18 H18 . 0.95 ?
C19 H19 . 0.95 ?
C20 C21 . 1.377(17) ?
C20 C25 . 1.387(16) ?
C21 C22 . 1.395(17) ?
C21 H21 . 0.95 ?
C22 C23 . 1.36(2) ?
C22 H22 . 0.95 ?
C23 C24 . 1.35(2) ?
C23 H23 . 0.95 ?
C24 C25 . 1.37(2) ?
C24 H24 . 0.95 ?
C25 H25 . 0.95 ?
C26 C27 . 1.432(14) ?
C26 C33 . 1.526(14) ?
C26 Ir1 . 2.101(8) ?
C26 H26 . 1.0 ?
C27 C28 . 1.481(16) ?
C27 Ir1 . 2.104(9) ?
C27 H27 . 0.95 ?
C28 C29 . 1.538(17) ?
C28 H28A . 0.99 ?
C28 H28B . 0.99 ?
C29 C30 . 1.506(17) ?
C29 H29A . 0.99 ?
C29 H29B . 0.99 ?
C30 C31 . 1.376(16) ?
C30 Ir1 . 2.182(9) ?
C30 H30 . 0.95 ?
C31 C32 . 1.514(16) ?
C31 Ir1 . 2.178(10) ?
C31 H31 . 0.95 ?
C32 C33 . 1.538(15) ?
C32 H32A . 0.99 ?
C32 H32B . 0.99 ?
C33 H33A . 0.99 ?
C33 H33B . 0.99 ?
Cl1 Ir1 . 2.379(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 N2 . . 103.3(8) ?
N1 C1 Ir1 . . 130.0(7) ?
N2 C1 Ir1 . . 126.5(7) ?
C3 C2 N2 . . 106.3(9) ?
C3 C2 H2 . . 126.8 ?
N2 C2 H2 . . 126.8 ?
C2 C3 N1 . . 105.8(8) ?
C2 C3 C4 . . 144.8(9) ?
N1 C3 C4 . . 109.4(9) ?
C3 C4 C5 . . 102.3(7) ?
C3 C4 H4A . . 111.3 ?
C5 C4 H4A . . 111.3 ?
C3 C4 H4B . . 111.3 ?
C5 C4 H4B . . 111.3 ?
H4A C4 H4B . . 109.2 ?
C6 C5 C4 . . 105.1(8) ?
C6 C5 H5A . . 110.7 ?
C4 C5 H5A . . 110.7 ?
C6 C5 H5B . . 110.7 ?
C4 C5 H5B . . 110.7 ?
H5A C5 H5B . . 108.8 ?
N1 C6 C7 . . 113.2(8) ?
N1 C6 C5 . . 101.8(8) ?
C7 C6 C5 . . 114.8(9) ?
N1 C6 H6 . . 108.9 ?
C7 C6 H6 . . 108.9 ?
C5 C6 H6 . . 108.9 ?
C12 C7 C8 . . 118.8(11) ?
C12 C7 C6 . . 119.3(11) ?
C8 C7 C6 . . 122.0(10) ?
C9 C8 C7 . . 121.3(13) ?
C9 C8 H8 . . 119.4 ?
C7 C8 H8 . . 119.4 ?
C8 C9 C10 . . 118.9(15) ?
C8 C9 H9 . . 120.5 ?
C10 C9 H9 . . 120.5 ?
C11 C10 C9 . . 122.0(14) ?
C11 C10 H10 . . 119.0 ?
C9 C10 H10 . . 119.0 ?
C10 C11 C12 . . 119.9(13) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
C7 C12 C11 . . 119.1(13) ?
C7 C12 H12 . . 120.4 ?
C11 C12 H12 . . 120.4 ?
N2 C13 C14 . . 111.7(8) ?
N2 C13 C20 . . 111.7(8) ?
C14 C13 C20 . . 113.8(9) ?
N2 C13 H13 . . 106.4 ?
C14 C13 H13 . . 106.4 ?
C20 C13 H13 . . 106.4 ?
C19 C14 C15 . . 118.4(10) ?
C19 C14 C13 . . 118.3(10) ?
C15 C14 C13 . . 123.3(9) ?
C14 C15 C16 . . 120.6(10) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
C17 C16 C15 . . 120.1(11) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C18 C17 C16 . . 119.3(11) ?
C18 C17 H17 . . 120.4 ?
C16 C17 H17 . . 120.4 ?
C17 C18 C19 . . 121.0(11) ?
C17 C18 H18 . . 119.5 ?
C19 C18 H18 . . 119.5 ?
C18 C19 C14 . . 120.6(11) ?
C18 C19 H19 . . 119.7 ?
C14 C19 H19 . . 119.7 ?
C21 C20 C25 . . 118.3(12) ?
C21 C20 C13 . . 122.4(11) ?
C25 C20 C13 . . 119.3(11) ?
C20 C21 C22 . . 120.8(13) ?
C20 C21 H21 . . 119.6 ?
C22 C21 H21 . . 119.6 ?
C23 C22 C21 . . 119.5(15) ?
C23 C22 H22 . . 120.2 ?
C21 C22 H22 . . 120.2 ?
C24 C23 C22 . . 120.0(15) ?
C24 C23 H23 . . 120.0 ?
C22 C23 H23 . . 120.0 ?
C23 C24 C25 . . 121.4(16) ?
C23 C24 H24 . . 119.3 ?
C25 C24 H24 . . 119.3 ?
C24 C25 C20 . . 119.9(15) ?
C24 C25 H25 . . 120.1 ?
C20 C25 H25 . . 120.1 ?
C27 C26 C33 . . 122.6(11) ?
C27 C26 Ir1 . . 70.2(5) ?
C33 C26 Ir1 . . 114.3(7) ?
C27 C26 H26 . . 114.1 ?
C33 C26 H26 . . 114.1 ?
Ir1 C26 H26 . . 114.1 ?
C26 C27 C28 . . 126.0(11) ?
C26 C27 Ir1 . . 69.9(5) ?
C28 C27 Ir1 . . 112.5(8) ?
C26 C27 H27 . . 117.0 ?
C28 C27 H27 . . 117.0 ?
Ir1 C27 H27 . . 87.5 ?
C27 C28 C29 . . 113.1(10) ?
C27 C28 H28A . . 109.0 ?
C29 C28 H28A . . 109.0 ?
C27 C28 H28B . . 109.0 ?
C29 C28 H28B . . 109.0 ?
H28A C28 H28B . . 107.8 ?
C30 C29 C28 . . 111.9(9) ?
C30 C29 H29A . . 109.2 ?
C28 C29 H29A . . 109.2 ?
C30 C29 H29B . . 109.2 ?
C28 C29 H29B . . 109.2 ?
H29A C29 H29B . . 107.9 ?
C31 C30 C29 . . 123.0(11) ?
C31 C30 Ir1 . . 71.5(6) ?
C29 C30 Ir1 . . 112.7(8) ?
C31 C30 H30 . . 118.5 ?
C29 C30 H30 . . 118.5 ?
Ir1 C30 H30 . . 85.9 ?
C30 C31 C32 . . 125.2(12) ?
C30 C31 Ir1 . . 71.7(6) ?
C32 C31 Ir1 . . 110.5(7) ?
C30 C31 H31 . . 117.4 ?
C32 C31 H31 . . 117.4 ?
Ir1 C31 H31 . . 87.7 ?
C31 C32 C33 . . 112.4(10) ?
C31 C32 H32A . . 109.1 ?
C33 C32 H32A . . 109.1 ?
C31 C32 H32B . . 109.1 ?
C33 C32 H32B . . 109.1 ?
H32A C32 H32B . . 107.8 ?
C26 C33 C32 . . 113.4(9) ?
C26 C33 H33A . . 108.9 ?
C32 C33 H33A . . 108.9 ?
C26 C33 H33B . . 108.9 ?
C32 C33 H33B . . 108.9 ?
H33A C33 H33B . . 107.7 ?
C1 Ir1 C26 . . 95.1(4) ?
C1 Ir1 C27 . . 92.8(4) ?
C26 Ir1 C27 . . 39.8(4) ?
C1 Ir1 C31 . . 160.2(4) ?
C26 Ir1 C31 . . 81.6(5) ?
C27 Ir1 C31 . . 96.8(5) ?
C1 Ir1 C30 . . 163.0(4) ?
C26 Ir1 C30 . . 89.9(4) ?
C27 Ir1 C30 . . 80.7(5) ?
C31 Ir1 C30 . . 36.8(4) ?
C1 Ir1 Cl1 . . 88.3(3) ?
C26 Ir1 Cl1 . . 164.5(3) ?
C27 Ir1 Cl1 . . 155.2(3) ?
C31 Ir1 Cl1 . . 90.1(4) ?
C30 Ir1 Cl1 . . 91.1(3) ?
C1 N1 C3 . . 112.3(8) ?
C1 N1 C6 . . 135.7(8) ?
C3 N1 C6 . . 112.0(8) ?
C1 N2 C2 . . 112.3(8) ?
C1 N2 C13 . . 121.6(8) ?
C2 N2 C13 . . 125.7(9) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N2 C2 C3 N1 . . . . 0.0(11) ?
N2 C2 C3 C4 . . . . 177.8(13) ?
C2 C3 C4 C5 . . . . 163.4(14) ?
N1 C3 C4 C5 . . . . -18.8(10) ?
C3 C4 C5 C6 . . . . 29.6(10) ?
C4 C5 C6 N1 . . . . -29.1(10) ?
C4 C5 C6 C7 . . . . -151.8(9) ?
N1 C6 C7 C12 . . . . 139.2(10) ?
C5 C6 C7 C12 . . . . -104.5(11) ?
N1 C6 C7 C8 . . . . -41.3(14) ?
C5 C6 C7 C8 . . . . 75.0(13) ?
C12 C7 C8 C9 . . . . -1.8(16) ?
C6 C7 C8 C9 . . . . 178.8(10) ?
C7 C8 C9 C10 . . . . 1.8(18) ?
C8 C9 C10 C11 . . . . -1.(2) ?
C9 C10 C11 C12 . . . . 1.(2) ?
C8 C7 C12 C11 . . . . 1.2(16) ?
C6 C7 C12 C11 . . . . -179.3(9) ?
C10 C11 C12 C7 . . . . -0.8(18) ?
N2 C13 C14 C19 . . . . 158.9(9) ?
C20 C13 C14 C19 . . . . -73.5(13) ?
N2 C13 C14 C15 . . . . -22.2(15) ?
C20 C13 C14 C15 . . . . 105.4(12) ?
C19 C14 C15 C16 . . . . 1.8(17) ?
C13 C14 C15 C16 . . . . -177.1(11) ?
C14 C15 C16 C17 . . . . -0.2(19) ?
C15 C16 C17 C18 . . . . -1.0(19) ?
C16 C17 C18 C19 . . . . 0.5(19) ?
C17 C18 C19 C14 . . . . 1.2(18) ?
C15 C14 C19 C18 . . . . -2.3(17) ?
C13 C14 C19 C18 . . . . 176.7(10) ?
N2 C13 C20 C21 . . . . 96.2(13) ?
C14 C13 C20 C21 . . . . -31.4(15) ?
N2 C13 C20 C25 . . . . -85.2(13) ?
C14 C13 C20 C25 . . . . 147.2(10) ?
C25 C20 C21 C22 . . . . 1.2(19) ?
C13 C20 C21 C22 . . . . 179.8(11) ?
C20 C21 C22 C23 . . . . -2.(2) ?
C21 C22 C23 C24 . . . . 1.(2) ?
C22 C23 C24 C25 . . . . 0.(3) ?
C23 C24 C25 C20 . . . . 0.(2) ?
C21 C20 C25 C24 . . . . 0.(2) ?
C13 C20 C25 C24 . . . . -178.8(12) ?
C33 C26 C27 C28 . . . . 3.1(16) ?
Ir1 C26 C27 C28 . . . . -103.8(10) ?
C33 C26 C27 Ir1 . . . . 106.9(9) ?
C26 C27 C28 C29 . . . . 47.2(15) ?
Ir1 C27 C28 C29 . . . . -33.7(13) ?
C27 C28 C29 C30 . . . . 30.1(15) ?
C28 C29 C30 C31 . . . . -94.5(13) ?
C28 C29 C30 Ir1 . . . . -12.5(13) ?
C29 C30 C31 C32 . . . . 2.9(16) ?
Ir1 C30 C31 C32 . . . . -102.6(10) ?
C29 C30 C31 Ir1 . . . . 105.5(10) ?
C30 C31 C32 C33 . . . . 51.0(14) ?
Ir1 C31 C32 C33 . . . . -30.6(11) ?
C27 C26 C33 C32 . . . . -90.1(12) ?
Ir1 C26 C33 C32 . . . . -8.9(11) ?
C31 C32 C33 C26 . . . . 26.3(13) ?
N2 C1 N1 C3 . . . . 1.4(11) ?
Ir1 C1 N1 C3 . . . . -173.2(7) ?
N2 C1 N1 C6 . . . . -178.6(11) ?
Ir1 C1 N1 C6 . . . . 6.7(18) ?
C2 C3 N1 C1 . . . . -1.0(12) ?
C4 C3 N1 C1 . . . . -179.6(8) ?
C2 C3 N1 C6 . . . . 179.1(8) ?
C4 C3 N1 C6 . . . . 0.4(11) ?
C7 C6 N1 C1 . . . . -37.8(16) ?
C5 C6 N1 C1 . . . . -161.6(11) ?
C7 C6 N1 C3 . . . . 142.1(9) ?
C5 C6 N1 C3 . . . . 18.3(11) ?
N1 C1 N2 C2 . . . . -1.4(11) ?
Ir1 C1 N2 C2 . . . . 173.5(7) ?
N1 C1 N2 C13 . . . . 171.1(8) ?
Ir1 C1 N2 C13 . . . . -14.0(14) ?
C3 C2 N2 C1 . . . . 0.9(12) ?
C3 C2 N2 C13 . . . . -171.3(9) ?
C14 C13 N2 C1 . . . . -83.9(12) ?
C20 C13 N2 C1 . . . . 147.4(10) ?
C14 C13 N2 C2 . . . . 87.5(12) ?
C20 C13 N2 C2 . . . . -41.2(14) ?

####################################################################### 
# 
# 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_yoshida33_p212121
_database_code_depnum_ccdc_archive 'CCDC 1059390'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H48 Cl3 Ir N2'
_chemical_formula_weight         855.35
_chemical_absolute_configuration ad

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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.0761(4)
_cell_length_b                   15.8222(8)
_cell_length_c                   28.1212(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3593.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    9223
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      28.05
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1720
_exptl_absorpt_coefficient_mu    3.970
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2996
_exptl_absorpt_correction_T_max  0.6923
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_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 APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            20564
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         28.57
_reflns_number_total             8211
_reflns_number_gt                7709
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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)+(0.0330P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(7)
_refine_ls_number_reflns         8211
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0513
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
C1 C 1.0392(6) 0.0151(3) 0.87583(16) 0.0176(9) Uani 1 1 d . . .
C2 C 1.2035(6) -0.0885(3) 0.84435(15) 0.0200(10) Uani 1 1 d . . .
H2 H 1.2494 -0.1427 0.8383 0.024 Uiso 1 1 calc R . .
C3 C 1.2512(6) -0.0150(3) 0.82515(16) 0.0181(10) Uani 1 1 d . . .
C4 C 1.3784(7) 0.0224(3) 0.79296(16) 0.0270(10) Uani 1 1 d . . .
H4A H 1.3715 -0.0026 0.7608 0.032 Uiso 1 1 calc R . .
H4B H 1.4913 0.0134 0.8057 0.032 Uiso 1 1 calc R . .
C5 C 1.3345(6) 0.1175(3) 0.79186(17) 0.0246(11) Uani 1 1 d . . .
H5A H 1.2966 0.1338 0.7597 0.029 Uiso 1 1 calc R . .
H5B H 1.4332 0.1517 0.7999 0.029 Uiso 1 1 calc R . .
C6 C 1.1945(6) 0.1332(3) 0.82884(16) 0.0200(10) Uani 1 1 d . . .
H6 H 1.2440 0.1629 0.8568 0.024 Uiso 1 1 calc R . .
C7 C 1.0493(6) 0.1865(3) 0.81064(16) 0.0213(10) Uani 1 1 d . . .
C8 C 0.9576(6) 0.1613(3) 0.77027(16) 0.0216(10) Uani 1 1 d . . .
C9 C 0.8372(6) 0.2154(3) 0.75275(17) 0.0294(11) Uani 1 1 d . . .
H9 H 0.7758 0.1992 0.7254 0.035 Uiso 1 1 calc R . .
C10 C 0.8041(7) 0.2921(4) 0.77407(19) 0.0347(12) Uani 1 1 d . . .
H10 H 0.7224 0.3287 0.7612 0.042 Uiso 1 1 calc R . .
C11 C 0.8914(8) 0.3152(3) 0.81444(19) 0.0335(12) Uani 1 1 d . . .
H11 H 0.8677 0.3679 0.8292 0.040 Uiso 1 1 calc R . .
C12 C 1.0124(6) 0.2634(3) 0.83385(18) 0.0264(11) Uani 1 1 d . . .
C13 C 0.9782(6) 0.0770(3) 0.74529(15) 0.0235(10) Uani 1 1 d . . .
H13 H 1.0751 0.0475 0.7599 0.028 Uiso 1 1 calc R . .
C14 C 0.8263(7) 0.0213(4) 0.75250(19) 0.0350(13) Uani 1 1 d . . .
H14A H 0.8095 0.0114 0.7866 0.053 Uiso 1 1 calc R . .
H14B H 0.8430 -0.0330 0.7363 0.053 Uiso 1 1 calc R . .
H14C H 0.7287 0.0495 0.7392 0.053 Uiso 1 1 calc R . .
C15 C 1.0140(8) 0.0875(4) 0.69178(18) 0.0371(14) Uani 1 1 d . . .
H15A H 1.0406 0.0324 0.6779 0.056 Uiso 1 1 calc R . .
H15B H 1.1079 0.1260 0.6875 0.056 Uiso 1 1 calc R . .
H15C H 0.9161 0.1110 0.6760 0.056 Uiso 1 1 calc R . .
C16 C 1.1007(7) 0.2921(3) 0.87949(18) 0.0331(11) Uani 1 1 d . . .
H16 H 1.1347 0.2404 0.8975 0.040 Uiso 1 1 calc R . .
C17 C 1.2573(8) 0.3411(4) 0.8666(3) 0.0501(17) Uani 1 1 d . . .
H17A H 1.2267 0.3958 0.8527 0.075 Uiso 1 1 calc R . .
H17B H 1.3222 0.3086 0.8436 0.075 Uiso 1 1 calc R . .
H17C H 1.3235 0.3505 0.8954 0.075 Uiso 1 1 calc R . .
C18 C 0.9903(9) 0.3460(5) 0.9124(2) 0.0524(18) Uani 1 1 d . . .
H18A H 0.9589 0.3982 0.8960 0.079 Uiso 1 1 calc R . .
H18B H 1.0514 0.3599 0.9415 0.079 Uiso 1 1 calc R . .
H18C H 0.8904 0.3140 0.9206 0.079 Uiso 1 1 calc R . .
C19 C 0.9759(6) -0.1331(3) 0.90105(16) 0.0203(10) Uani 1 1 d . . .
H19 H 0.9195 -0.1031 0.9278 0.024 Uiso 1 1 calc R . .
C20 C 1.0928(5) -0.1969(3) 0.92336(16) 0.0199(8) Uani 1 1 d . . .
C21 C 1.0881(6) -0.2813(3) 0.91201(15) 0.0231(10) Uani 1 1 d . . .
H21 H 1.0092 -0.3014 0.8896 0.028 Uiso 1 1 calc R . .
C22 C 1.1992(7) -0.3378(3) 0.93331(18) 0.0300(12) Uani 1 1 d . . .
H22 H 1.1961 -0.3960 0.9251 0.036 Uiso 1 1 calc R . .
C23 C 1.3126(7) -0.3092(3) 0.96601(19) 0.0337(13) Uani 1 1 d . . .
H23 H 1.3876 -0.3477 0.9804 0.040 Uiso 1 1 calc R . .
C24 C 1.3180(7) -0.2250(3) 0.97792(17) 0.0312(12) Uani 1 1 d . . .
H24 H 1.3961 -0.2054 1.0006 0.037 Uiso 1 1 calc R . .
C25 C 1.2088(7) -0.1685(3) 0.95663(17) 0.0275(12) Uani 1 1 d . . .
H25 H 1.2131 -0.1103 0.9647 0.033 Uiso 1 1 calc R . .
C26 C 0.8401(6) -0.1703(3) 0.87007(17) 0.0209(10) Uani 1 1 d . . .
C27 C 0.8480(6) -0.1705(3) 0.82106(18) 0.0249(11) Uani 1 1 d . . .
H27 H 0.9429 -0.1478 0.8057 0.030 Uiso 1 1 calc R . .
C28 C 0.7196(7) -0.2030(4) 0.79387(19) 0.0337(12) Uani 1 1 d . . .
H28 H 0.7264 -0.2023 0.7601 0.040 Uiso 1 1 calc R . .
C29 C 0.5827(7) -0.2365(3) 0.8160(2) 0.0353(13) Uani 1 1 d . . .
H29 H 0.4948 -0.2593 0.7975 0.042 Uiso 1 1 calc R . .
C30 C 0.5729(7) -0.2368(3) 0.8648(2) 0.0347(13) Uani 1 1 d . . .
H30 H 0.4775 -0.2595 0.8799 0.042 Uiso 1 1 calc R . .
C31 C 0.6994(6) -0.2049(3) 0.89191(19) 0.0282(11) Uani 1 1 d . . .
H31 H 0.6918 -0.2062 0.9256 0.034 Uiso 1 1 calc R . .
C32 C 0.7290(6) 0.0632(4) 0.98678(16) 0.0280(11) Uani 1 1 d . . .
H32 H 0.8210 0.0397 1.0032 0.034 Uiso 1 1 calc R . .
C33 C 0.7398(6) 0.1478(3) 0.97404(16) 0.0249(11) Uani 1 1 d . . .
H33 H 0.8386 0.1779 0.9810 0.030 Uiso 1 1 calc R . .
C34 C 0.5993(7) 0.1935(3) 0.94942(18) 0.0303(11) Uani 1 1 d . . .
H34A H 0.5980 0.2532 0.9599 0.036 Uiso 1 1 calc R . .
H34B H 0.4929 0.1675 0.9590 0.036 Uiso 1 1 calc R . .
C35 C 0.6148(8) 0.1905(3) 0.89467(18) 0.0295(11) Uani 1 1 d . . .
H35A H 0.5026 0.1918 0.8805 0.035 Uiso 1 1 calc R . .
H35B H 0.6746 0.2416 0.8837 0.035 Uiso 1 1 calc R . .
C36 C 0.7050(6) 0.1129(3) 0.87694(18) 0.0237(11) Uani 1 1 d . . .
H36 H 0.7934 0.1209 0.8551 0.028 Uiso 1 1 calc R . .
C37 C 0.6662(6) 0.0286(3) 0.89081(17) 0.0216(10) Uani 1 1 d . . .
H37 H 0.7300 -0.0165 0.8781 0.026 Uiso 1 1 calc R . .
C38 C 0.5268(6) 0.0079(3) 0.92521(19) 0.0285(10) Uani 1 1 d . . .
H38A H 0.4786 -0.0476 0.9167 0.034 Uiso 1 1 calc R . .
H38B H 0.4387 0.0510 0.9220 0.034 Uiso 1 1 calc R . .
C39 C 0.5857(7) 0.0052(4) 0.97708(18) 0.0317(12) Uani 1 1 d . . .
H39A H 0.4923 0.0210 0.9981 0.038 Uiso 1 1 calc R . .
H39B H 0.6185 -0.0534 0.9851 0.038 Uiso 1 1 calc R . .
C40 C 0.6010(10) 0.5011(5) 0.9068(2) 0.0608(19) Uani 1 1 d . . .
H40A H 0.6306 0.4419 0.9144 0.073 Uiso 1 1 calc R . .
H40B H 0.5019 0.5160 0.9257 0.073 Uiso 1 1 calc R . .
Cl1 Cl 1.12283(15) 0.08167(9) 0.97489(4) 0.0336(3) Uani 1 1 d . . .
Cl2 Cl 0.5518(3) 0.50763(19) 0.84722(8) 0.0973(9) Uani 1 1 d . . .
Cl3 Cl 0.7632(2) 0.56647(11) 0.92345(6) 0.0570(4) Uani 1 1 d . . .
Ir1 Ir 0.887605(19) 0.070835(11) 0.925208(6) 0.01757(5) Uani 1 1 d . . .
N1 N 1.0724(4) -0.0691(3) 0.87511(12) 0.0178(7) Uani 1 1 d . . .
N2 N 1.1491(4) 0.0464(2) 0.84382(12) 0.0159(8) 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
C1 N2 1.358(6) . ?
C1 N1 1.360(6) . ?
C1 Ir1 2.051(5) . ?
C2 C3 1.338(6) . ?
C2 N1 1.401(5) . ?
C2 H2 0.9500 . ?
C3 N2 1.378(6) . ?
C3 C4 1.492(7) . ?
C4 C5 1.545(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.556(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N2 1.483(6) . ?
C6 C7 1.532(7) . ?
C6 H6 1.0000 . ?
C7 C12 1.413(7) . ?
C7 C8 1.413(7) . ?
C8 C9 1.385(7) . ?
C8 C13 1.518(7) . ?
C9 C10 1.380(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(7) . ?
C11 H11 0.9500 . ?
C12 C16 1.537(7) . ?
C13 C14 1.524(7) . ?
C13 C15 1.541(6) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.527(8) . ?
C16 C18 1.542(8) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 N1 1.471(6) . ?
C19 C20 1.518(6) . ?
C19 C26 1.519(6) . ?
C19 H19 1.0000 . ?
C20 C21 1.373(6) . ?
C20 C25 1.398(7) . ?
C21 C22 1.401(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.375(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.374(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.391(7) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.380(7) . ?
C26 C31 1.403(7) . ?
C27 C28 1.387(7) . ?
C27 H27 0.9500 . ?
C28 C29 1.375(8) . ?
C28 H28 0.9500 . ?
C29 C30 1.376(8) . ?
C29 H29 0.9500 . ?
C30 C31 1.371(7) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.388(8) . ?
C32 C39 1.502(7) . ?
C32 Ir1 2.157(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.514(7) . ?
C33 Ir1 2.189(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.546(7) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.513(7) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.425(7) . ?
C36 Ir1 2.112(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.520(7) . ?
C37 Ir1 2.140(5) . ?
C37 H37 0.9500 . ?
C38 C39 1.535(7) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 Cl2 1.724(7) . ?
C40 Cl3 1.733(7) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
Cl1 Ir1 2.3644(12) . ?

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 C1 N1 102.7(4) . . ?
N2 C1 Ir1 133.0(3) . . ?
N1 C1 Ir1 123.3(3) . . ?
C3 C2 N1 106.1(4) . . ?
C3 C2 H2 127.0 . . ?
N1 C2 H2 127.0 . . ?
C2 C3 N2 106.7(4) . . ?
C2 C3 C4 142.0(5) . . ?
N2 C3 C4 111.3(4) . . ?
C3 C4 C5 103.9(4) . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4B 111.0 . . ?
C5 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C4 C5 C6 108.0(4) . . ?
C4 C5 H5A 110.1 . . ?
C6 C5 H5A 110.1 . . ?
C4 C5 H5B 110.1 . . ?
C6 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
N2 C6 C7 114.5(4) . . ?
N2 C6 C5 102.8(4) . . ?
C7 C6 C5 114.9(4) . . ?
N2 C6 H6 108.1 . . ?
C7 C6 H6 108.1 . . ?
C5 C6 H6 108.1 . . ?
C12 C7 C8 120.2(5) . . ?
C12 C7 C6 118.8(4) . . ?
C8 C7 C6 121.0(4) . . ?
C9 C8 C7 118.7(5) . . ?
C9 C8 C13 117.1(4) . . ?
C7 C8 C13 124.2(4) . . ?
C10 C9 C8 121.6(5) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 119.3(5) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 121.6(5) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C7 118.4(5) . . ?
C11 C12 C16 118.7(5) . . ?
C7 C12 C16 122.9(5) . . ?
C8 C13 C14 111.0(4) . . ?
C8 C13 C15 112.1(4) . . ?
C14 C13 C15 110.1(4) . . ?
C8 C13 H13 107.8 . . ?
C14 C13 H13 107.8 . . ?
C15 C13 H13 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C12 109.7(5) . . ?
C17 C16 C18 109.9(5) . . ?
C12 C16 C18 113.3(5) . . ?
C17 C16 H16 107.9 . . ?
C12 C16 H16 107.9 . . ?
C18 C16 H16 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 109.4(4) . . ?
N1 C19 C26 111.4(4) . . ?
C20 C19 C26 115.3(4) . . ?
N1 C19 H19 106.7 . . ?
C20 C19 H19 106.7 . . ?
C26 C19 H19 106.7 . . ?
C21 C20 C25 119.1(4) . . ?
C21 C20 C19 122.2(4) . . ?
C25 C20 C19 118.6(4) . . ?
C20 C21 C22 120.2(5) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 120.1(5) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.2(5) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.9(5) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C20 120.4(5) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
C27 C26 C31 118.3(5) . . ?
C27 C26 C19 122.7(4) . . ?
C31 C26 C19 119.0(4) . . ?
C26 C27 C28 121.1(5) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
C29 C28 C27 119.7(5) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C28 C29 C30 120.0(5) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C31 C30 C29 120.7(5) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C26 120.3(5) . . ?
C30 C31 H31 119.9 . . ?
C26 C31 H31 119.9 . . ?
C33 C32 C39 126.2(5) . . ?
C33 C32 Ir1 72.6(3) . . ?
C39 C32 Ir1 110.3(3) . . ?
C33 C32 H32 116.9 . . ?
C39 C32 H32 116.9 . . ?
Ir1 C32 H32 87.0 . . ?
C32 C33 C34 122.1(5) . . ?
C32 C33 Ir1 70.1(3) . . ?
C34 C33 Ir1 112.8(3) . . ?
C32 C33 H33 118.9 . . ?
C34 C33 H33 118.9 . . ?
Ir1 C33 H33 87.2 . . ?
C33 C34 C35 112.3(5) . . ?
C33 C34 H34A 109.1 . . ?
C35 C34 H34A 109.1 . . ?
C33 C34 H34B 109.1 . . ?
C35 C34 H34B 109.1 . . ?
H34A C34 H34B 107.9 . . ?
C36 C35 C34 113.1(4) . . ?
C36 C35 H35A 109.0 . . ?
C34 C35 H35A 109.0 . . ?
C36 C35 H35B 109.0 . . ?
C34 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C37 C36 C35 124.4(4) . . ?
C37 C36 Ir1 71.5(3) . . ?
C35 C36 Ir1 112.3(3) . . ?
C37 C36 H36 117.8 . . ?
C35 C36 H36 117.8 . . ?
Ir1 C36 H36 86.1 . . ?
C36 C37 C38 122.6(4) . . ?
C36 C37 Ir1 69.4(3) . . ?
C38 C37 Ir1 113.5(3) . . ?
C36 C37 H37 118.7 . . ?
C38 C37 H37 118.7 . . ?
Ir1 C37 H37 87.3 . . ?
C37 C38 C39 112.4(4) . . ?
C37 C38 H38A 109.1 . . ?
C39 C38 H38A 109.1 . . ?
C37 C38 H38B 109.1 . . ?
C39 C38 H38B 109.1 . . ?
H38A C38 H38B 107.8 . . ?
C32 C39 C38 113.2(4) . . ?
C32 C39 H39A 108.9 . . ?
C38 C39 H39A 108.9 . . ?
C32 C39 H39B 108.9 . . ?
C38 C39 H39B 108.9 . . ?
H39A C39 H39B 107.8 . . ?
Cl2 C40 Cl3 113.7(4) . . ?
Cl2 C40 H40A 108.8 . . ?
Cl3 C40 H40A 108.8 . . ?
Cl2 C40 H40B 108.8 . . ?
Cl3 C40 H40B 108.8 . . ?
H40A C40 H40B 107.7 . . ?
C1 Ir1 C36 96.73(19) . . ?
C1 Ir1 C37 93.35(19) . . ?
C36 Ir1 C37 39.16(18) . . ?
C1 Ir1 C32 150.92(19) . . ?
C36 Ir1 C32 96.83(19) . . ?
C37 Ir1 C32 81.3(2) . . ?
C1 Ir1 C33 171.7(2) . . ?
C36 Ir1 C33 81.22(18) . . ?
C37 Ir1 C33 90.11(18) . . ?
C32 Ir1 C33 37.3(2) . . ?
C1 Ir1 Cl1 87.22(13) . . ?
C36 Ir1 Cl1 156.64(14) . . ?
C37 Ir1 Cl1 163.95(13) . . ?
C32 Ir1 Cl1 90.39(14) . . ?
C33 Ir1 Cl1 91.55(13) . . ?
C1 N1 C2 111.8(4) . . ?
C1 N1 C19 124.2(4) . . ?
C2 N1 C19 123.8(4) . . ?
C1 N2 C3 112.7(4) . . ?
C1 N2 C6 133.5(4) . . ?
C3 N2 C6 113.4(4) . . ?

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
N1 C2 C3 N2 -0.6(5) . . . . ?
N1 C2 C3 C4 175.7(6) . . . . ?
C2 C3 C4 C5 -179.3(6) . . . . ?
N2 C3 C4 C5 -3.1(5) . . . . ?
C3 C4 C5 C6 6.8(5) . . . . ?
C4 C5 C6 N2 -7.8(5) . . . . ?
C4 C5 C6 C7 -132.9(4) . . . . ?
N2 C6 C7 C12 121.3(5) . . . . ?
C5 C6 C7 C12 -120.0(5) . . . . ?
N2 C6 C7 C8 -61.2(6) . . . . ?
C5 C6 C7 C8 57.5(6) . . . . ?
C12 C7 C8 C9 3.1(7) . . . . ?
C6 C7 C8 C9 -174.3(4) . . . . ?
C12 C7 C8 C13 -174.9(4) . . . . ?
C6 C7 C8 C13 7.7(7) . . . . ?
C7 C8 C9 C10 -0.7(8) . . . . ?
C13 C8 C9 C10 177.4(5) . . . . ?
C8 C9 C10 C11 -1.1(8) . . . . ?
C9 C10 C11 C12 0.5(9) . . . . ?
C10 C11 C12 C7 1.9(8) . . . . ?
C10 C11 C12 C16 -178.3(5) . . . . ?
C8 C7 C12 C11 -3.7(7) . . . . ?
C6 C7 C12 C11 173.8(4) . . . . ?
C8 C7 C12 C16 176.5(5) . . . . ?
C6 C7 C12 C16 -6.0(7) . . . . ?
C9 C8 C13 C14 -67.0(6) . . . . ?
C7 C8 C13 C14 111.0(5) . . . . ?
C9 C8 C13 C15 56.6(6) . . . . ?
C7 C8 C13 C15 -125.4(5) . . . . ?
C11 C12 C16 C17 -92.0(6) . . . . ?
C7 C12 C16 C17 87.8(6) . . . . ?
C11 C12 C16 C18 31.3(7) . . . . ?
C7 C12 C16 C18 -148.9(5) . . . . ?
N1 C19 C20 C21 -119.3(5) . . . . ?
C26 C19 C20 C21 7.2(6) . . . . ?
N1 C19 C20 C25 60.8(5) . . . . ?
C26 C19 C20 C25 -172.7(4) . . . . ?
C25 C20 C21 C22 -0.5(7) . . . . ?
C19 C20 C21 C22 179.6(4) . . . . ?
C20 C21 C22 C23 0.5(7) . . . . ?
C21 C22 C23 C24 -0.1(8) . . . . ?
C22 C23 C24 C25 -0.3(8) . . . . ?
C23 C24 C25 C20 0.4(8) . . . . ?
C21 C20 C25 C24 0.0(7) . . . . ?
C19 C20 C25 C24 179.9(4) . . . . ?
N1 C19 C26 C27 24.0(6) . . . . ?
C20 C19 C26 C27 -101.5(5) . . . . ?
N1 C19 C26 C31 -155.0(4) . . . . ?
C20 C19 C26 C31 79.5(5) . . . . ?
C31 C26 C27 C28 0.7(7) . . . . ?
C19 C26 C27 C28 -178.3(5) . . . . ?
C26 C27 C28 C29 -0.5(8) . . . . ?
C27 C28 C29 C30 0.5(8) . . . . ?
C28 C29 C30 C31 -0.6(8) . . . . ?
C29 C30 C31 C26 0.8(8) . . . . ?
C27 C26 C31 C30 -0.8(7) . . . . ?
C19 C26 C31 C30 178.2(5) . . . . ?
C39 C32 C33 C34 2.3(7) . . . . ?
Ir1 C32 C33 C34 105.1(4) . . . . ?
C39 C32 C33 Ir1 -102.7(5) . . . . ?
C32 C33 C34 C35 -92.2(6) . . . . ?
Ir1 C33 C34 C35 -12.1(6) . . . . ?
C33 C34 C35 C36 28.5(7) . . . . ?
C34 C35 C36 C37 50.5(7) . . . . ?
C34 C35 C36 Ir1 -31.8(6) . . . . ?
C35 C36 C37 C38 0.5(8) . . . . ?
Ir1 C36 C37 C38 105.3(4) . . . . ?
C35 C36 C37 Ir1 -104.9(5) . . . . ?
C36 C37 C38 C39 -91.0(6) . . . . ?
Ir1 C37 C38 C39 -11.3(5) . . . . ?
C33 C32 C39 C38 49.1(7) . . . . ?
Ir1 C32 C39 C38 -33.7(5) . . . . ?
C37 C38 C39 C32 29.8(6) . . . . ?
N2 C1 Ir1 C36 76.9(4) . . . . ?
N1 C1 Ir1 C36 -116.7(4) . . . . ?
N2 C1 Ir1 C37 116.0(4) . . . . ?
N1 C1 Ir1 C37 -77.5(4) . . . . ?
N2 C1 Ir1 C32 -165.8(4) . . . . ?
N1 C1 Ir1 C32 0.7(6) . . . . ?
N2 C1 Ir1 C33 1.6(15) . . . . ?
N1 C1 Ir1 C33 168.1(11) . . . . ?
N2 C1 Ir1 Cl1 -80.0(4) . . . . ?
N1 C1 Ir1 Cl1 86.4(4) . . . . ?
C37 C36 Ir1 C1 87.0(3) . . . . ?
C35 C36 Ir1 C1 -152.6(4) . . . . ?
C35 C36 Ir1 C37 120.4(5) . . . . ?
C37 C36 Ir1 C32 -67.2(3) . . . . ?
C35 C36 Ir1 C32 53.2(4) . . . . ?
C37 C36 Ir1 C33 -101.1(3) . . . . ?
C35 C36 Ir1 C33 19.3(4) . . . . ?
C37 C36 Ir1 Cl1 -174.3(3) . . . . ?
C35 C36 Ir1 Cl1 -53.9(6) . . . . ?
C36 C37 Ir1 C1 -96.6(3) . . . . ?
C38 C37 Ir1 C1 145.8(4) . . . . ?
C38 C37 Ir1 C36 -117.6(5) . . . . ?
C36 C37 Ir1 C32 112.2(3) . . . . ?
C38 C37 Ir1 C32 -5.4(4) . . . . ?
C36 C37 Ir1 C33 75.9(3) . . . . ?
C38 C37 Ir1 C33 -41.7(4) . . . . ?
C36 C37 Ir1 Cl1 171.9(4) . . . . ?
C38 C37 Ir1 Cl1 54.3(7) . . . . ?
C33 C32 Ir1 C1 177.0(3) . . . . ?
C39 C32 Ir1 C1 -60.0(5) . . . . ?
C33 C32 Ir1 C36 -65.7(3) . . . . ?
C39 C32 Ir1 C36 57.3(4) . . . . ?
C33 C32 Ir1 C37 -101.8(3) . . . . ?
C39 C32 Ir1 C37 21.2(4) . . . . ?
C39 C32 Ir1 C33 123.0(5) . . . . ?
C33 C32 Ir1 Cl1 92.0(3) . . . . ?
C39 C32 Ir1 Cl1 -145.0(4) . . . . ?
C32 C33 Ir1 C1 -169.9(12) . . . . ?
C34 C33 Ir1 C1 72.6(14) . . . . ?
C32 C33 Ir1 C36 113.7(3) . . . . ?
C34 C33 Ir1 C36 -3.8(4) . . . . ?
C32 C33 Ir1 C37 75.4(3) . . . . ?
C34 C33 Ir1 C37 -42.1(4) . . . . ?
C34 C33 Ir1 C32 -117.5(5) . . . . ?
C32 C33 Ir1 Cl1 -88.6(3) . . . . ?
C34 C33 Ir1 Cl1 153.9(4) . . . . ?
N2 C1 N1 C2 1.8(5) . . . . ?
Ir1 C1 N1 C2 -168.1(3) . . . . ?
N2 C1 N1 C19 -174.5(4) . . . . ?
Ir1 C1 N1 C19 15.6(6) . . . . ?
C3 C2 N1 C1 -0.8(5) . . . . ?
C3 C2 N1 C19 175.5(4) . . . . ?
C20 C19 N1 C1 -138.2(4) . . . . ?
C26 C19 N1 C1 93.1(5) . . . . ?
C20 C19 N1 C2 45.9(5) . . . . ?
C26 C19 N1 C2 -82.9(5) . . . . ?
N1 C1 N2 C3 -2.3(5) . . . . ?
Ir1 C1 N2 C3 166.2(3) . . . . ?
N1 C1 N2 C6 -174.2(4) . . . . ?
Ir1 C1 N2 C6 -5.7(7) . . . . ?
C2 C3 N2 C1 1.9(5) . . . . ?
C4 C3 N2 C1 -175.7(4) . . . . ?
C2 C3 N2 C6 175.5(4) . . . . ?
C4 C3 N2 C6 -2.1(5) . . . . ?
C7 C6 N2 C1 -56.6(6) . . . . ?
C5 C6 N2 C1 178.1(4) . . . . ?
C7 C6 N2 C3 131.5(4) . . . . ?
C5 C6 N2 C3 6.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.927
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.171
