# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cmpnd_1
_database_code_depnum_ccdc_archive 'CCDC 1812901'
loop_
_audit_author_name
_audit_author_address
'Pilar Garcia-Orduna'
'Instituto de S?ntesis Qu?mica y Cat?lisis Homog?nea (ISQCH, CSIC-Univ. Zaragoza)'
_audit_update_record             
;
2017-12-21 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H34 Cl Ir N6'
_chemical_formula_sum            'C24 H34 Cl Ir N6'
_chemical_formula_weight         634.22

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5778(3)
_cell_length_b                   10.4101(4)
_cell_length_c                   30.6151(12)
_cell_angle_alpha                90.5790(10)
_cell_angle_beta                 95.3880(10)
_cell_angle_gamma                90.4360(10)
_cell_volume                     2404.21(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      2.381
_cell_measurement_theta_max      29.467

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    5.689
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4000
_exptl_absorpt_correction_T_max  0.5371
_exptl_absorpt_process_details   
;
 SADABS: Area-Detector Absorption Correction. (1996) Bruker-AXS 
 within APEX2 package.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX DUO CCD system'
_diffrn_measurement_method       'narrow ω frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            25483
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         1.956
_diffrn_reflns_theta_max         29.625
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             12204
_reflns_number_gt                11060
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART in APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_cell_refinement       'SAINT+ in APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT+ in APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP program, SHELXTL v6.12, Bruker2000'
_computing_publication_material  'XCIF program, PLATON(Spek, 1998)'

_refine_special_details          
;
Hydrogen atoms of methyl and methylene groups have been included in the 
model in calculated positions and refined with a riding model. The rest
of the hydrogen atoms have been included in the model in observed positions
and freely refined. Isotropic atomic displacement parameters of some hydrogen
atoms have been constrained to be 1.2 times Ueq of their parent carbon
atoms.

Two reflections (0 0 1 and 0 0 2) have been found to be highly affected by 
the beamstop. They have beem omitted from the refinement.

At the end of the refinement nine residual density peaks of intensity bigger
than 1 eA^3 are found close to the metal atoms. They have no chemical sense.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0197P)²+3.8880P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12204
_refine_ls_number_parameters     649
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0563
_refine_ls_wR_factor_gt          0.0550
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.44604(2) 0.14915(2) 0.31525(2) 0.01247(3) Uani 1 1 d . . . . .
Cl1 Cl 0.63926(10) -0.01790(7) 0.33723(2) 0.01897(14) Uani 1 1 d . . . . .
N1 N 0.3558(3) 0.1539(2) 0.37853(8) 0.0141(5) Uani 1 1 d . . . . .
N2 N 0.4223(3) 0.2341(2) 0.41197(8) 0.0132(5) Uani 1 1 d . . . . .
N3 N 0.7715(3) 0.3643(2) 0.47793(8) 0.0169(5) Uani 1 1 d . . . . .
N4 N 0.7024(3) 0.2611(2) 0.45371(8) 0.0147(5) Uani 1 1 d . . . . .
N5 N 0.4863(3) 0.4965(2) 0.40607(8) 0.0173(5) Uani 1 1 d . . . . .
N6 N 0.6116(3) 0.4095(2) 0.39652(8) 0.0155(5) Uani 1 1 d . . . . .
C1 C 0.2042(4) 0.1052(3) 0.39102(10) 0.0152(6) Uani 1 1 d . . . . .
C2 C 0.1742(4) 0.1573(3) 0.43232(10) 0.0163(6) Uani 1 1 d . . . . .
C3 C 0.3139(4) 0.2381(3) 0.44505(9) 0.0147(6) Uani 1 1 d . . . . .
C4 C 0.0981(4) 0.0093(3) 0.36318(11) 0.0218(6) Uani 1 1 d . . . . .
H4A H -0.0088 0.0502 0.3494 0.033 Uiso 1 1 calc R U . . .
H4B H 0.0641 -0.0619 0.3814 0.033 Uiso 1 1 calc R U . . .
H4C H 0.1690 -0.0236 0.3404 0.033 Uiso 1 1 calc R U . . .
C5 C 0.3498(4) 0.3161(3) 0.48613(10) 0.0195(6) Uani 1 1 d . . . . .
H5A H 0.4487 0.2785 0.5045 0.029 Uiso 1 1 calc R U . . .
HB H 0.2438 0.3167 0.5022 0.029 Uiso 1 1 calc R U . . .
H5C H 0.3805 0.4043 0.4787 0.029 Uiso 1 1 calc R U . . .
C6 C 0.6042(4) 0.2796(3) 0.41107(9) 0.0139(5) Uani 1 1 d . . . . .
C7 C 0.8458(4) 0.3123(3) 0.51460(10) 0.0171(6) Uani 1 1 d . . . . .
C8 C 0.8235(4) 0.1780(3) 0.51431(10) 0.0179(6) Uani 1 1 d . . . . .
H8 H 0.861(5) 0.116(4) 0.5369(12) 0.021 Uiso 1 1 d . U . . .
C9 C 0.7311(4) 0.1468(3) 0.47480(10) 0.0157(6) Uani 1 1 d . . . . .
C10 C 0.9353(4) 0.3963(3) 0.55030(10) 0.0225(7) Uani 1 1 d . . . . .
H10A H 1.0191 0.4544 0.5378 0.034 Uiso 1 1 calc R U . . .
H10B H 0.9991 0.3426 0.5725 0.034 Uiso 1 1 calc R U . . .
H10C H 0.8460 0.4468 0.5639 0.034 Uiso 1 1 calc R U . . .
C11 C 0.6659(4) 0.0204(3) 0.45596(10) 0.0212(6) Uani 1 1 d . . . . .
H11A H 0.5364 0.0167 0.4550 0.032 Uiso 1 1 calc R U . . .
H11B H 0.7170 -0.0490 0.4743 0.032 Uiso 1 1 calc R U . . .
H11C H 0.7017 0.0107 0.4262 0.032 Uiso 1 1 calc R U . . .
C12 C 0.5350(4) 0.6043(3) 0.38739(10) 0.0188(6) Uani 1 1 d . . . . .
C13 C 0.6911(4) 0.5868(3) 0.36647(10) 0.0197(6) Uani 1 1 d . . . . .
C14 C 0.7385(4) 0.4609(3) 0.37308(10) 0.0173(6) Uani 1 1 d . . . . .
C15 C 0.4300(5) 0.7244(3) 0.39068(11) 0.0242(7) Uani 1 1 d . . . . .
H15A H 0.3088 0.7022 0.3968 0.036 Uiso 1 1 calc R U . . .
H15B H 0.4268 0.7708 0.3629 0.036 Uiso 1 1 calc R U . . .
H15C H 0.4854 0.7789 0.4145 0.036 Uiso 1 1 calc R U . . .
C16 C 0.8930(4) 0.3862(3) 0.36065(11) 0.0239(7) Uani 1 1 d . . . . .
H16A H 0.9700 0.3654 0.3871 0.036 Uiso 1 1 calc R U . . .
H16B H 0.9598 0.4374 0.3410 0.036 Uiso 1 1 calc R U . . .
H16C H 0.8511 0.3066 0.3456 0.036 Uiso 1 1 calc R U . . .
C17 C 0.2143(4) 0.2442(3) 0.29052(10) 0.0200(6) Uani 1 1 d . . . . .
C18 C 0.3505(4) 0.3360(3) 0.30113(10) 0.0197(6) Uani 1 1 d . . . . .
C19 C 0.4457(5) 0.4044(3) 0.26639(11) 0.0244(7) Uani 1 1 d . . . . .
H19A H 0.4798 0.4919 0.2771 0.029 Uiso 1 1 calc R U . . .
H19B H 0.3631 0.4131 0.2396 0.029 Uiso 1 1 calc R U . . .
C20 C 0.6115(5) 0.3340(3) 0.25470(11) 0.0254(7) Uani 1 1 d . . . . .
H20B H 0.6263 0.3473 0.2233 0.031 Uiso 1 1 calc R U . . .
H20A H 0.7165 0.3715 0.2721 0.031 Uiso 1 1 calc R U . . .
C21 C 0.6038(4) 0.1904(3) 0.26334(10) 0.0206(6) Uani 1 1 d . . . . .
C22 C 0.4630(4) 0.1103(3) 0.24731(10) 0.0184(6) Uani 1 1 d . . . . .
H22 H 0.485(5) 0.024(4) 0.2456(12) 0.022 Uiso 1 1 d . U . . .
C23 C 0.3055(5) 0.1601(3) 0.21800(10) 0.0231(7) Uani 1 1 d . . . . .
H23A H 0.2639 0.0923 0.1964 0.028 Uiso 1 1 calc R U . . .
H23B H 0.3437 0.2351 0.2015 0.028 Uiso 1 1 calc R U . . .
C24 C 0.1511(4) 0.1996(3) 0.24431(10) 0.0226(7) Uani 1 1 d . . . . .
H24B H 0.0846 0.2698 0.2288 0.027 Uiso 1 1 calc R U . . .
H24A H 0.0692 0.1256 0.2458 0.027 Uiso 1 1 calc R U . . .
Ir31 Ir 0.01689(2) 0.64807(2) 0.19075(2) 0.01349(3) Uani 1 1 d . . . . .
Cl31 Cl -0.10775(11) 0.45181(7) 0.16491(3) 0.02202(15) Uani 1 1 d . . . . .
N31 N 0.1288(3) 0.6694(2) 0.13039(8) 0.0158(5) Uani 1 1 d . . . . .
N32 N 0.0569(3) 0.7324(2) 0.09388(8) 0.0160(5) Uani 1 1 d . . . . .
N33 N -0.2922(4) 0.8543(3) 0.02693(9) 0.0206(5) Uani 1 1 d . . . . .
N34 N -0.2203(3) 0.7547(2) 0.05122(8) 0.0173(5) Uani 1 1 d . . . . .
N35 N 0.0175(4) 0.9919(3) 0.09518(9) 0.0209(5) Uani 1 1 d . . . . .
N36 N -0.1210(3) 0.9156(3) 0.10466(8) 0.0181(5) Uani 1 1 d . . . . .
C31 C 0.2889(4) 0.6299(3) 0.12070(10) 0.0196(6) Uani 1 1 d . . . . .
C32 C 0.3185(4) 0.6697(3) 0.07845(11) 0.0205(6) Uani 1 1 d . . . . .
C33 C 0.1702(4) 0.7352(3) 0.06181(10) 0.0180(6) Uani 1 1 d . . . . .
C34 C 0.4048(5) 0.5531(4) 0.15238(12) 0.0287(8) Uani 1 1 d . . . . .
H34A H 0.4153 0.5961 0.1811 0.043 Uiso 1 1 calc R U . . .
H34B H 0.5226 0.5453 0.1419 0.043 Uiso 1 1 calc R U . . .
H34C H 0.3528 0.4673 0.1549 0.043 Uiso 1 1 calc R U . . .
C35 C 0.1333(4) 0.8001(3) 0.01883(10) 0.0225(7) Uani 1 1 d . . . . .
H35A H 0.0419 0.7517 0.0006 0.034 Uiso 1 1 calc R U . . .
H35B H 0.2420 0.8038 0.0039 0.034 Uiso 1 1 calc R U . . .
H35C H 0.0916 0.8875 0.0237 0.034 Uiso 1 1 calc R U . . .
C36 C -0.1225(4) 0.7805(3) 0.09374(10) 0.0165(6) Uani 1 1 d . . . . .
C37 C -0.3667(4) 0.7978(3) -0.00953(10) 0.0218(6) Uani 1 1 d . . . . .
C38 C -0.3424(4) 0.6641(3) -0.00885(11) 0.0213(6) Uani 1 1 d . . . . .
C39 C -0.2475(4) 0.6384(3) 0.03069(10) 0.0188(6) Uani 1 1 d . . . . .
C40 C -0.4582(5) 0.8776(4) -0.04516(11) 0.0297(8) Uani 1 1 d . . . . .
H40C H -0.5459 0.9325 -0.0328 0.044 Uiso 1 1 calc R U . . .
H40B H -0.5179 0.8211 -0.0678 0.044 Uiso 1 1 calc R U . . .
H40A H -0.3707 0.9313 -0.0582 0.044 Uiso 1 1 calc R U . . .
C41 C -0.1792(5) 0.5142(3) 0.04923(12) 0.0265(7) Uani 1 1 d . . . . .
H41A H -0.0512 0.5094 0.0470 0.040 Uiso 1 1 calc R U . . .
H41B H -0.2389 0.4425 0.0327 0.040 Uiso 1 1 calc R U . . .
H41C H -0.2025 0.5091 0.0801 0.040 Uiso 1 1 calc R U . . .
C42 C -0.0219(5) 1.1072(3) 0.11075(10) 0.0227(7) Uani 1 1 d . . . . .
C43 C -0.1824(5) 1.1040(3) 0.13030(11) 0.0230(7) Uani 1 1 d . . . . .
C44 C -0.2454(4) 0.9806(3) 0.12582(10) 0.0214(6) Uani 1 1 d . . . . .
C45 C 0.1010(5) 1.2185(3) 0.10609(12) 0.0309(8) Uani 1 1 d . . . . .
H45A H 0.2238 1.1909 0.1129 0.046 Uiso 1 1 calc R U . . .
H45B H 0.0745 1.2875 0.1264 0.046 Uiso 1 1 calc R U . . .
H45C H 0.0852 1.2500 0.0759 0.046 Uiso 1 1 calc R U . . .
C46 C -0.4101(4) 0.9187(3) 0.13830(12) 0.0261(7) Uani 1 1 d . . . . .
H46A H -0.4856 0.8941 0.1117 0.039 Uiso 1 1 calc R U . . .
H46B H -0.4736 0.9791 0.1558 0.039 Uiso 1 1 calc R U . . .
H46C H -0.3798 0.8419 0.1556 0.039 Uiso 1 1 calc R U . . .
C47 C 0.1975(4) 0.7854(3) 0.22019(10) 0.0192(6) Uani 1 1 d . . . . .
H47 H 0.281(5) 0.791(4) 0.2032(13) 0.023 Uiso 1 1 d . U . . .
C48 C 0.0338(4) 0.8449(3) 0.20805(10) 0.0179(6) Uani 1 1 d . . . . .
H48 H 0.032(5) 0.896(4) 0.1847(12) 0.021 Uiso 1 1 d . U . . .
C49 C -0.0954(4) 0.8850(3) 0.24076(10) 0.0210(6) Uani 1 1 d . . . . .
H49A H -0.1588 0.9629 0.2299 0.025 Uiso 1 1 calc R U . . .
H49B H -0.0280 0.9072 0.2691 0.025 Uiso 1 1 calc R U . . .
C50 C -0.2316(4) 0.7796(3) 0.24816(11) 0.0208(6) Uani 1 1 d . . . . .
H50 H -0.2631 0.7853 0.2788 0.025 Uiso 1 1 calc R U . . .
H50B H -0.3407 0.7941 0.2285 0.025 Uiso 1 1 calc R U . . .
C51 C -0.1636(4) 0.6465(3) 0.23973(10) 0.0171(6) Uani 1 1 d . . . . .
C52 C -0.0001(4) 0.5992(3) 0.25753(10) 0.0176(6) Uani 1 1 d . . . . .
C53 C 0.1256(4) 0.6761(3) 0.28985(10) 0.0224(7) Uani 1 1 d . . . . .
H53A H 0.1864 0.6168 0.3113 0.027 Uiso 1 1 calc R U . . .
H53B H 0.0563 0.7373 0.3062 0.027 Uiso 1 1 calc R U . . .
C54 C 0.2653(4) 0.7509(3) 0.26666(11) 0.0220(6) Uani 1 1 d . . . . .
H54A H 0.2982 0.8305 0.2835 0.026 Uiso 1 1 calc R U . . .
H54B H 0.3731 0.6981 0.2660 0.026 Uiso 1 1 calc R U . . .
H2 H 0.085(5) 0.142(3) 0.4470(12) 0.019(9) Uiso 1 1 d . . . . .
H6 H 0.654(5) 0.220(3) 0.3900(12) 0.019(9) Uiso 1 1 d . . . . .
H13 H 0.753(5) 0.641(3) 0.3521(11) 0.015(8) Uiso 1 1 d . . . . .
H17 H 0.131(5) 0.238(3) 0.3110(11) 0.014(8) Uiso 1 1 d . . . . .
H18 H 0.339(5) 0.381(3) 0.3283(12) 0.020(9) Uiso 1 1 d . . . . .
H21 H 0.720(5) 0.150(3) 0.2700(12) 0.018(9) Uiso 1 1 d . . . . .
H32 H 0.421(5) 0.658(4) 0.0639(13) 0.027(10) Uiso 1 1 d . . . . .
H36 H -0.168(5) 0.734(4) 0.1169(12) 0.021(9) Uiso 1 1 d . . . . .
H38 H -0.377(5) 0.608(4) -0.0313(13) 0.027(10) Uiso 1 1 d . . . . .
H43 H -0.239(5) 1.168(4) 0.1425(13) 0.031(11) Uiso 1 1 d . . . . .
H51 H -0.248(5) 0.590(3) 0.2298(12) 0.016(9) Uiso 1 1 d . . . . .
H52 H 0.009(4) 0.511(3) 0.2593(11) 0.015(8) Uiso 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 C17 2.104(3) . ?
Ir1 N1 2.115(2) . ?
Ir1 C18 2.115(3) . ?
Ir1 C21 2.121(3) . ?
Ir1 C22 2.131(3) . ?
Ir1 Cl1 2.3449(7) . ?
N1 C1 1.341(4) . ?
N1 N2 1.371(3) . ?
N2 C3 1.363(4) . ?
N2 C6 1.457(4) . ?
N3 C7 1.330(4) . ?
N3 N4 1.371(3) . ?
N4 C9 1.369(4) . ?
N4 C6 1.456(4) . ?
N5 C12 1.330(4) . ?
N5 N6 1.366(4) . ?
N6 C14 1.362(4) . ?
N6 C6 1.430(4) . ?
C1 C2 1.410(4) . ?
C1 C4 1.487(4) . ?
C2 C3 1.372(4) . ?
C2 H2 0.86(4) . ?
C3 C5 1.492(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 HB 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 0.99(4) . ?
C7 C8 1.407(4) . ?
C7 C10 1.501(4) . ?
C8 C9 1.374(4) . ?
C8 H8 0.97(4) . ?
C9 C11 1.493(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.409(5) . ?
C12 C15 1.495(4) . ?
C13 C14 1.374(4) . ?
C13 H13 0.88(4) . ?
C14 C16 1.487(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.414(5) . ?
C17 C24 1.517(4) . ?
C17 H17 0.93(3) . ?
C18 C19 1.520(4) . ?
C18 H18 0.96(4) . ?
C19 C20 1.529(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.522(5) . ?
C20 H20B 0.9900 . ?
C20 H20A 0.9900 . ?
C21 C22 1.397(5) . ?
C21 H21 0.99(4) . ?
C22 C23 1.522(5) . ?
C22 H22 0.91(4) . ?
C23 C24 1.537(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24B 0.9900 . ?
C24 H24A 0.9900 . ?
Ir31 C47 2.108(3) . ?
Ir31 C48 2.112(3) . ?
Ir31 N31 2.117(3) . ?
Ir31 C51 2.123(3) . ?
Ir31 C52 2.127(3) . ?
Ir31 Cl31 2.3429(8) . ?
N31 C31 1.342(4) . ?
N31 N32 1.372(3) . ?
N32 C33 1.364(4) . ?
N32 C36 1.452(4) . ?
N33 C37 1.332(4) . ?
N33 N34 1.369(3) . ?
N34 C39 1.364(4) . ?
N34 C36 1.457(4) . ?
N35 C42 1.334(4) . ?
N35 N36 1.366(4) . ?
N36 C44 1.371(4) . ?
N36 C36 1.443(4) . ?
C31 C32 1.399(4) . ?
C31 C34 1.489(4) . ?
C32 C33 1.377(4) . ?
C32 H32 0.94(4) . ?
C33 C35 1.489(4) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36 0.95(4) . ?
C37 C38 1.406(5) . ?
C37 C40 1.498(4) . ?
C38 C39 1.378(4) . ?
C38 H38 0.92(4) . ?
C39 C41 1.494(4) . ?
C40 H40C 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40A 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 C43 1.406(5) . ?
C42 C45 1.497(5) . ?
C43 C44 1.369(5) . ?
C43 H43 0.89(4) . ?
C44 C46 1.484(5) . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 C48 1.411(4) . ?
C47 C54 1.514(4) . ?
C47 H47 0.86(4) . ?
C48 C49 1.522(4) . ?
C48 H48 0.89(4) . ?
C49 C50 1.534(4) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 C51 1.509(4) . ?
C50 H50 0.9900 . ?
C50 H50B 0.9900 . ?
C51 C52 1.401(4) . ?
C51 H51 0.90(4) . ?
C52 C53 1.524(4) . ?
C52 H52 0.93(4) . ?
C53 C54 1.539(5) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?

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
C17 Ir1 N1 89.48(11) . . ?
C17 Ir1 C18 39.17(13) . . ?
N1 Ir1 C18 92.18(11) . . ?
C17 Ir1 C21 98.15(13) . . ?
N1 Ir1 C21 159.45(11) . . ?
C18 Ir1 C21 82.13(13) . . ?
C17 Ir1 C22 81.97(12) . . ?
N1 Ir1 C22 162.11(11) . . ?
C18 Ir1 C22 91.04(12) . . ?
C21 Ir1 C22 38.37(12) . . ?
C17 Ir1 Cl1 160.12(9) . . ?
N1 Ir1 Cl1 89.80(7) . . ?
C18 Ir1 Cl1 160.68(9) . . ?
C21 Ir1 Cl1 89.34(9) . . ?
C22 Ir1 Cl1 92.96(9) . . ?
C1 N1 N2 106.0(2) . . ?
C1 N1 Ir1 127.9(2) . . ?
N2 N1 Ir1 124.48(18) . . ?
C3 N2 N1 111.5(2) . . ?
C3 N2 C6 130.0(2) . . ?
N1 N2 C6 117.3(2) . . ?
C7 N3 N4 104.0(2) . . ?
C9 N4 N3 112.8(2) . . ?
C9 N4 C6 126.5(2) . . ?
N3 N4 C6 120.6(2) . . ?
C12 N5 N6 104.2(2) . . ?
C14 N6 N5 113.0(2) . . ?
C14 N6 C6 125.9(3) . . ?
N5 N6 C6 121.1(2) . . ?
N1 C1 C2 109.2(3) . . ?
N1 C1 C4 121.0(3) . . ?
C2 C1 C4 129.7(3) . . ?
C3 C2 C1 107.3(3) . . ?
C3 C2 H2 126(2) . . ?
C1 C2 H2 127(2) . . ?
N2 C3 C2 106.0(3) . . ?
N2 C3 C5 124.5(3) . . ?
C2 C3 C5 129.6(3) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 HB 109.5 . . ?
H5A C5 HB 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
HB C5 H5C 109.5 . . ?
N6 C6 N4 112.6(2) . . ?
N6 C6 N2 111.8(2) . . ?
N4 C6 N2 110.0(2) . . ?
N6 C6 H6 111(2) . . ?
N4 C6 H6 108(2) . . ?
N2 C6 H6 104(2) . . ?
N3 C7 C8 111.7(3) . . ?
N3 C7 C10 120.1(3) . . ?
C8 C7 C10 128.2(3) . . ?
C9 C8 C7 106.2(3) . . ?
C9 C8 H8 125(2) . . ?
C7 C8 H8 129(2) . . ?
N4 C9 C8 105.4(3) . . ?
N4 C9 C11 123.5(3) . . ?
C8 C9 C11 131.1(3) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N5 C12 C13 111.3(3) . . ?
N5 C12 C15 120.7(3) . . ?
C13 C12 C15 128.0(3) . . ?
C14 C13 C12 106.1(3) . . ?
C14 C13 H13 123(2) . . ?
C12 C13 H13 131(2) . . ?
N6 C14 C13 105.4(3) . . ?
N6 C14 C16 122.7(3) . . ?
C13 C14 C16 131.9(3) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C24 124.7(3) . . ?
C18 C17 Ir1 70.83(18) . . ?
C24 C17 Ir1 112.0(2) . . ?
C18 C17 H17 115(2) . . ?
C24 C17 H17 116(2) . . ?
Ir1 C17 H17 109(2) . . ?
C17 C18 C19 122.6(3) . . ?
C17 C18 Ir1 70.00(18) . . ?
C19 C18 Ir1 113.8(2) . . ?
C17 C18 H18 113(2) . . ?
C19 C18 H18 118(2) . . ?
Ir1 C18 H18 109(2) . . ?
C18 C19 C20 113.0(3) . . ?
C18 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 112.9(3) . . ?
C21 C20 H20B 109.0 . . ?
C19 C20 H20B 109.0 . . ?
C21 C20 H20A 109.0 . . ?
C19 C20 H20A 109.0 . . ?
H20B C20 H20A 107.8 . . ?
C22 C21 C20 123.8(3) . . ?
C22 C21 Ir1 71.17(18) . . ?
C20 C21 Ir1 111.5(2) . . ?
C22 C21 H21 117(2) . . ?
C20 C21 H21 115(2) . . ?
Ir1 C21 H21 108(2) . . ?
C21 C22 C23 122.1(3) . . ?
C21 C22 Ir1 70.46(17) . . ?
C23 C22 Ir1 113.3(2) . . ?
C21 C22 H22 117(2) . . ?
C23 C22 H22 117(2) . . ?
Ir1 C22 H22 105(2) . . ?
C22 C23 C24 112.2(3) . . ?
C22 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
C22 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C17 C24 C23 112.3(3) . . ?
C17 C24 H24B 109.2 . . ?
C23 C24 H24B 109.2 . . ?
C17 C24 H24A 109.2 . . ?
C23 C24 H24A 109.2 . . ?
H24B C24 H24A 107.9 . . ?
C47 Ir31 C48 39.07(12) . . ?
C47 Ir31 N31 90.10(11) . . ?
C48 Ir31 N31 95.27(11) . . ?
C47 Ir31 C51 98.05(12) . . ?
C48 Ir31 C51 81.96(12) . . ?
N31 Ir31 C51 162.78(11) . . ?
C47 Ir31 C52 81.42(12) . . ?
C48 Ir31 C52 90.40(12) . . ?
N31 Ir31 C52 158.70(11) . . ?
C51 Ir31 C52 38.49(12) . . ?
C47 Ir31 Cl31 161.53(9) . . ?
C48 Ir31 Cl31 159.25(9) . . ?
N31 Ir31 Cl31 89.03(7) . . ?
C51 Ir31 Cl31 87.94(9) . . ?
C52 Ir31 Cl31 92.90(9) . . ?
C31 N31 N32 105.7(2) . . ?
C31 N31 Ir31 127.1(2) . . ?
N32 N31 Ir31 127.16(18) . . ?
C33 N32 N31 111.7(2) . . ?
C33 N32 C36 129.9(3) . . ?
N31 N32 C36 118.4(2) . . ?
C37 N33 N34 104.0(3) . . ?
C39 N34 N33 113.0(2) . . ?
C39 N34 C36 127.2(3) . . ?
N33 N34 C36 119.8(2) . . ?
C42 N35 N36 103.9(3) . . ?
N35 N36 C44 113.1(3) . . ?
N35 N36 C36 120.1(2) . . ?
C44 N36 C36 126.8(3) . . ?
N31 C31 C32 109.6(3) . . ?
N31 C31 C34 121.1(3) . . ?
C32 C31 C34 129.3(3) . . ?
C33 C32 C31 107.4(3) . . ?
C33 C32 H32 125(2) . . ?
C31 C32 H32 128(2) . . ?
N32 C33 C32 105.6(3) . . ?
N32 C33 C35 124.6(3) . . ?
C32 C33 C35 129.8(3) . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N36 C36 N32 110.8(2) . . ?
N36 C36 N34 111.5(2) . . ?
N32 C36 N34 109.8(2) . . ?
N36 C36 H36 109(2) . . ?
N32 C36 H36 103(2) . . ?
N34 C36 H36 113(2) . . ?
N33 C37 C38 111.7(3) . . ?
N33 C37 C40 119.9(3) . . ?
C38 C37 C40 128.5(3) . . ?
C39 C38 C37 106.0(3) . . ?
C39 C38 H38 128(2) . . ?
C37 C38 H38 125(2) . . ?
N34 C39 C38 105.4(3) . . ?
N34 C39 C41 124.2(3) . . ?
C38 C39 C41 130.4(3) . . ?
C37 C40 H40C 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40C C40 H40B 109.5 . . ?
C37 C40 H40A 109.5 . . ?
H40C C40 H40A 109.5 . . ?
H40B C40 H40A 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N35 C42 C43 111.4(3) . . ?
N35 C42 C45 119.7(3) . . ?
C43 C42 C45 128.9(3) . . ?
C44 C43 C42 106.5(3) . . ?
C44 C43 H43 124(3) . . ?
C42 C43 H43 129(3) . . ?
C43 C44 N36 105.1(3) . . ?
C43 C44 C46 132.1(3) . . ?
N36 C44 C46 122.8(3) . . ?
C42 C45 H45A 109.5 . . ?
C42 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C42 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C44 C46 H46A 109.5 . . ?
C44 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C44 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C48 C47 C54 124.9(3) . . ?
C48 C47 Ir31 70.61(18) . . ?
C54 C47 Ir31 112.6(2) . . ?
C48 C47 H47 119(3) . . ?
C54 C47 H47 112(3) . . ?
Ir31 C47 H47 106(3) . . ?
C47 C48 C49 123.5(3) . . ?
C47 C48 Ir31 70.32(18) . . ?
C49 C48 Ir31 113.6(2) . . ?
C47 C48 H48 115(2) . . ?
C49 C48 H48 114(2) . . ?
Ir31 C48 H48 113(2) . . ?
C48 C49 C50 112.7(3) . . ?
C48 C49 H49A 109.0 . . ?
C50 C49 H49A 109.0 . . ?
C48 C49 H49B 109.0 . . ?
C50 C49 H49B 109.0 . . ?
H49A C49 H49B 107.8 . . ?
C51 C50 C49 112.5(3) . . ?
C51 C50 H50 109.1 . . ?
C49 C50 H50 109.1 . . ?
C51 C50 H50B 109.1 . . ?
C49 C50 H50B 109.1 . . ?
H50 C50 H50B 107.8 . . ?
C52 C51 C50 124.7(3) . . ?
C52 C51 Ir31 70.93(17) . . ?
C50 C51 Ir31 111.4(2) . . ?
C52 C51 H51 118(2) . . ?
C50 C51 H51 114(2) . . ?
Ir31 C51 H51 105(2) . . ?
C51 C52 C53 122.9(3) . . ?
C51 C52 Ir31 70.58(17) . . ?
C53 C52 Ir31 113.9(2) . . ?
C51 C52 H52 116(2) . . ?
C53 C52 H52 116(2) . . ?
Ir31 C52 H52 107(2) . . ?
C52 C53 C54 112.0(3) . . ?
C52 C53 H53A 109.2 . . ?
C54 C53 H53A 109.2 . . ?
C52 C53 H53B 109.2 . . ?
C54 C53 H53B 109.2 . . ?
H53A C53 H53B 107.9 . . ?
C47 C54 C53 111.9(3) . . ?
C47 C54 H54A 109.2 . . ?
C53 C54 H54A 109.2 . . ?
C47 C54 H54B 109.2 . . ?
C53 C54 H54B 109.2 . . ?
H54A C54 H54B 107.9 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C3 -0.8(3) . . . . ?
Ir1 N1 N2 C3 165.69(19) . . . . ?
C1 N1 N2 C6 167.7(2) . . . . ?
Ir1 N1 N2 C6 -25.8(3) . . . . ?
C7 N3 N4 C9 0.5(3) . . . . ?
C7 N3 N4 C6 178.2(3) . . . . ?
C12 N5 N6 C14 1.1(3) . . . . ?
C12 N5 N6 C6 -179.7(3) . . . . ?
N2 N1 C1 C2 1.0(3) . . . . ?
Ir1 N1 C1 C2 -164.8(2) . . . . ?
N2 N1 C1 C4 -177.7(3) . . . . ?
Ir1 N1 C1 C4 16.5(4) . . . . ?
N1 C1 C2 C3 -0.9(3) . . . . ?
C4 C1 C2 C3 177.6(3) . . . . ?
N1 N2 C3 C2 0.2(3) . . . . ?
C6 N2 C3 C2 -166.4(3) . . . . ?
N1 N2 C3 C5 179.7(3) . . . . ?
C6 N2 C3 C5 13.1(5) . . . . ?
C1 C2 C3 N2 0.4(3) . . . . ?
C1 C2 C3 C5 -179.1(3) . . . . ?
C14 N6 C6 N4 88.2(3) . . . . ?
N5 N6 C6 N4 -90.9(3) . . . . ?
C14 N6 C6 N2 -147.3(3) . . . . ?
N5 N6 C6 N2 33.6(4) . . . . ?
C9 N4 C6 N6 -174.9(3) . . . . ?
N3 N4 C6 N6 7.8(4) . . . . ?
C9 N4 C6 N2 59.6(4) . . . . ?
N3 N4 C6 N2 -117.7(3) . . . . ?
C3 N2 C6 N6 -90.9(3) . . . . ?
N1 N2 C6 N6 103.1(3) . . . . ?
C3 N2 C6 N4 35.1(4) . . . . ?
N1 N2 C6 N4 -130.9(3) . . . . ?
N4 N3 C7 C8 -0.6(3) . . . . ?
N4 N3 C7 C10 -179.3(3) . . . . ?
N3 C7 C8 C9 0.5(4) . . . . ?
C10 C7 C8 C9 179.0(3) . . . . ?
N3 N4 C9 C8 -0.3(3) . . . . ?
C6 N4 C9 C8 -177.8(3) . . . . ?
N3 N4 C9 C11 178.6(3) . . . . ?
C6 N4 C9 C11 1.2(5) . . . . ?
C7 C8 C9 N4 -0.1(3) . . . . ?
C7 C8 C9 C11 -178.9(3) . . . . ?
N6 N5 C12 C13 -0.6(3) . . . . ?
N6 N5 C12 C15 -179.7(3) . . . . ?
N5 C12 C13 C14 0.0(4) . . . . ?
C15 C12 C13 C14 179.0(3) . . . . ?
N5 N6 C14 C13 -1.1(3) . . . . ?
C6 N6 C14 C13 179.7(3) . . . . ?
N5 N6 C14 C16 177.1(3) . . . . ?
C6 N6 C14 C16 -2.1(5) . . . . ?
C12 C13 C14 N6 0.7(3) . . . . ?
C12 C13 C14 C16 -177.3(3) . . . . ?
C24 C17 C18 C19 2.1(5) . . . . ?
Ir1 C17 C18 C19 106.0(3) . . . . ?
C24 C17 C18 Ir1 -103.9(3) . . . . ?
C17 C18 C19 C20 -90.8(4) . . . . ?
Ir1 C18 C19 C20 -10.1(4) . . . . ?
C18 C19 C20 C21 25.5(4) . . . . ?
C19 C20 C21 C22 52.4(4) . . . . ?
C19 C20 C21 Ir1 -28.8(3) . . . . ?
C20 C21 C22 C23 2.2(5) . . . . ?
Ir1 C21 C22 C23 105.9(3) . . . . ?
C20 C21 C22 Ir1 -103.7(3) . . . . ?
C21 C22 C23 C24 -93.7(4) . . . . ?
Ir1 C22 C23 C24 -12.9(3) . . . . ?
C18 C17 C24 C23 49.8(4) . . . . ?
Ir1 C17 C24 C23 -31.5(3) . . . . ?
C22 C23 C24 C17 28.8(4) . . . . ?
C31 N31 N32 C33 -1.2(3) . . . . ?
Ir31 N31 N32 C33 175.7(2) . . . . ?
C31 N31 N32 C36 176.7(3) . . . . ?
Ir31 N31 N32 C36 -6.4(4) . . . . ?
C37 N33 N34 C39 0.3(3) . . . . ?
C37 N33 N34 C36 178.7(3) . . . . ?
C42 N35 N36 C44 -0.2(3) . . . . ?
C42 N35 N36 C36 -178.1(3) . . . . ?
N32 N31 C31 C32 0.9(3) . . . . ?
Ir31 N31 C31 C32 -176.0(2) . . . . ?
N32 N31 C31 C34 -177.8(3) . . . . ?
Ir31 N31 C31 C34 5.3(4) . . . . ?
N31 C31 C32 C33 -0.4(4) . . . . ?
C34 C31 C32 C33 178.2(3) . . . . ?
N31 N32 C33 C32 0.9(3) . . . . ?
C36 N32 C33 C32 -176.6(3) . . . . ?
N31 N32 C33 C35 -177.9(3) . . . . ?
C36 N32 C33 C35 4.6(5) . . . . ?
C31 C32 C33 N32 -0.3(4) . . . . ?
C31 C32 C33 C35 178.4(3) . . . . ?
N35 N36 C36 N32 28.2(4) . . . . ?
C44 N36 C36 N32 -149.4(3) . . . . ?
N35 N36 C36 N34 -94.4(3) . . . . ?
C44 N36 C36 N34 88.0(4) . . . . ?
C33 N32 C36 N36 -83.9(4) . . . . ?
N31 N32 C36 N36 98.7(3) . . . . ?
C33 N32 C36 N34 39.7(4) . . . . ?
N31 N32 C36 N34 -137.7(3) . . . . ?
C39 N34 C36 N36 179.7(3) . . . . ?
N33 N34 C36 N36 1.6(4) . . . . ?
C39 N34 C36 N32 56.5(4) . . . . ?
N33 N34 C36 N32 -121.6(3) . . . . ?
N34 N33 C37 C38 -0.3(4) . . . . ?
N34 N33 C37 C40 -179.0(3) . . . . ?
N33 C37 C38 C39 0.2(4) . . . . ?
C40 C37 C38 C39 178.8(3) . . . . ?
N33 N34 C39 C38 -0.2(4) . . . . ?
C36 N34 C39 C38 -178.4(3) . . . . ?
N33 N34 C39 C41 178.3(3) . . . . ?
C36 N34 C39 C41 0.1(5) . . . . ?
C37 C38 C39 N34 0.0(3) . . . . ?
C37 C38 C39 C41 -178.4(3) . . . . ?
N36 N35 C42 C43 0.7(3) . . . . ?
N36 N35 C42 C45 -179.6(3) . . . . ?
N35 C42 C43 C44 -0.9(4) . . . . ?
C45 C42 C43 C44 179.4(3) . . . . ?
C42 C43 C44 N36 0.7(3) . . . . ?
C42 C43 C44 C46 -177.7(3) . . . . ?
N35 N36 C44 C43 -0.4(3) . . . . ?
C36 N36 C44 C43 177.4(3) . . . . ?
N35 N36 C44 C46 178.2(3) . . . . ?
C36 N36 C44 C46 -4.0(5) . . . . ?
C54 C47 C48 C49 1.3(5) . . . . ?
Ir31 C47 C48 C49 105.9(3) . . . . ?
C54 C47 C48 Ir31 -104.5(3) . . . . ?
C47 C48 C49 C50 -91.1(4) . . . . ?
Ir31 C48 C49 C50 -9.8(3) . . . . ?
C48 C49 C50 C51 26.6(4) . . . . ?
C49 C50 C51 C52 50.2(4) . . . . ?
C49 C50 C51 Ir31 -30.9(3) . . . . ?
C50 C51 C52 C53 3.2(5) . . . . ?
Ir31 C51 C52 C53 106.5(3) . . . . ?
C50 C51 C52 Ir31 -103.3(3) . . . . ?
C51 C52 C53 C54 -94.1(4) . . . . ?
Ir31 C52 C53 C54 -12.5(3) . . . . ?
C48 C47 C54 C53 49.9(4) . . . . ?
Ir31 C47 C54 C53 -31.5(3) . . . . ?
C52 C53 C54 C47 28.3(4) . . . . ?

_refine_diff_density_max         1.636
_refine_diff_density_min         -1.309
_refine_diff_density_rms         0.112

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene / deuterated benzene'
####################################################################### 
# 
# 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_cmpnd_3
_database_code_depnum_ccdc_archive 'CCDC 1812903'
loop_
_audit_author_name
_audit_author_address
'Pilar Garcia-Orduna'
'Instituto de S?ntesis Qu?mica y Cat?lisis Homog?nea (ISQCH, CSIC-Univ. Zaragoza)'
_audit_update_record             
;
2017-12-21 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H38 Ir N6, C F3 O3 S, C6 D6'
_chemical_formula_sum            'C31 H38 D6 F3 Ir N6 O3 S'
_chemical_formula_weight         836.02

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'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.4694(5)
_cell_length_b                   11.6677(5)
_cell_length_c                   13.9878(6)
_cell_angle_alpha                92.3850(10)
_cell_angle_beta                 103.8370(10)
_cell_angle_gamma                111.5710(10)
_cell_volume                     1672.77(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      2.251
_cell_measurement_theta_max      29.239

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.083
_exptl_absorpt_coefficient_mu    4.111
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4503
_exptl_absorpt_correction_T_max  0.6385
_exptl_absorpt_process_details   
;
 SADABS: Area-Detector Absorption Correction. (1996) Bruker-AXS 
 within APEX2 package.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX DUO CCD system'
_diffrn_measurement_method       'narrow ω frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_reflns_number            32584
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.515
_diffrn_reflns_theta_max         29.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8693
_reflns_number_gt                8200
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART in APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_cell_refinement       'SAINT+ in APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT+ in APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP program, SHELXTL v6.12, Bruker2000'
_computing_publication_material  'XCIF program, PLATON(Spek, 1998)'

_refine_special_details          
;
The asymmetric unit contains a Ir complex, a CF3SO3 counterion and a C6D6 
solvent molecule. This later has been found to be disordered. All the 
atoms of the disordered molecule have been included in two sets of
positions with complementary occupancy factors (0.59/0.41(1)) and 
isotropically refined, with a restraint leading to a regular
hexagon geometry.

Hydrogen atoms of phenyl groups and deuterium atoms of C6D6 have been 
included in the model in calculated positions and refined with a 
riding model. The rest of the hydrogen atoms (except hydrides) 
have been included in the model in observed positions and freely
refined. Hydride ligands have been located with potential minimization
calculus with HYDEX program and refined with a restraint in Ir-H
bond lenghts.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0196P)²+1.4510P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8693
_refine_ls_number_parameters     462
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0192
_refine_ls_wR_factor_ref         0.0457
_refine_ls_wR_factor_gt          0.0447
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir Ir 0.29238(2) 0.62367(2) 0.86489(2) 0.01303(3) Uani 1 1 d D . . . .
N1 N 0.29395(16) 0.48570(16) 0.95349(13) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.21363(16) 0.36413(16) 0.91401(13) 0.0142(3) Uani 1 1 d . . . . .
N3 N 0.27207(16) 0.48408(16) 0.74512(13) 0.0144(3) Uani 1 1 d . . . . .
N4 N 0.17758(17) 0.36795(16) 0.73891(13) 0.0145(3) Uani 1 1 d . . . . .
N5 N 0.08451(17) 0.52875(16) 0.84917(13) 0.0145(3) Uani 1 1 d . . . . .
N6 N 0.03019(16) 0.40125(16) 0.82158(13) 0.0145(3) Uani 1 1 d . . . . .
C1 C 0.3620(2) 0.4817(2) 1.04478(15) 0.0162(4) Uani 1 1 d . . . . .
C2 C 0.3234(2) 0.3579(2) 1.06377(16) 0.0182(4) Uani 1 1 d . . . . .
C3 C 0.2298(2) 0.2849(2) 0.98054(16) 0.0165(4) Uani 1 1 d . . . . .
C4 C 0.4611(2) 0.5971(2) 1.11060(16) 0.0199(4) Uani 1 1 d . . . . .
H4A H 0.5282 0.5767 1.1557 0.030 Uiso 1 1 calc R U . . .
H4B H 0.4187 0.6326 1.1496 0.030 Uiso 1 1 calc R U . . .
H4C H 0.5015 0.6577 1.0698 0.030 Uiso 1 1 calc R U . . .
C5 C 0.1551(2) 0.1474(2) 0.96008(17) 0.0226(4) Uani 1 1 d . . . . .
H5A H 0.0626 0.1289 0.9526 0.034 Uiso 1 1 calc R U . . .
H5B H 0.1882 0.1089 1.0155 0.034 Uiso 1 1 calc R U . . .
H5C H 0.1655 0.1140 0.8986 0.034 Uiso 1 1 calc R U . . .
C6 C 0.11652(19) 0.33769(19) 0.81886(15) 0.0148(4) Uani 1 1 d . . . . .
H6 H 0.067(2) 0.245(2) 0.8075(19) 0.018 Uiso 1 1 d . U . . .
C7 C 0.3175(2) 0.47807(19) 0.66647(16) 0.0163(4) Uani 1 1 d . . . . .
C8 C 0.2515(2) 0.3589(2) 0.61015(16) 0.0183(4) Uani 1 1 d . . . . .
C9 C 0.1627(2) 0.28989(19) 0.65754(16) 0.0168(4) Uani 1 1 d . . . . .
C10 C 0.4248(2) 0.5850(2) 0.64602(17) 0.0196(4) Uani 1 1 d . . . . .
H10A H 0.3894 0.6427 0.6138 0.029 Uiso 1 1 calc R U . . .
H10B H 0.4651 0.5542 0.6021 0.029 Uiso 1 1 calc R U . . .
H10C H 0.4905 0.6284 0.7088 0.029 Uiso 1 1 calc R U . . .
C11 C 0.0638(2) 0.1603(2) 0.63152(18) 0.0230(5) Uani 1 1 d . . . . .
H11A H 0.0777 0.1138 0.6869 0.034 Uiso 1 1 calc R U . . .
H11B H 0.0720 0.1202 0.5719 0.034 Uiso 1 1 calc R U . . .
H11C H -0.0236 0.1614 0.6185 0.034 Uiso 1 1 calc R U . . .
C12 C -0.0056(2) 0.5563(2) 0.87873(15) 0.0174(4) Uani 1 1 d . . . . .
C13 C -0.1169(2) 0.4472(2) 0.86945(17) 0.0207(4) Uani 1 1 d . . . . .
C14 C -0.0917(2) 0.3498(2) 0.83562(16) 0.0182(4) Uani 1 1 d . . . . .
C15 C 0.0139(2) 0.6841(2) 0.91908(17) 0.0209(4) Uani 1 1 d . . . . .
H15A H 0.1072 0.7369 0.9390 0.031 Uiso 1 1 calc R U . . .
H15B H -0.0207 0.6804 0.9770 0.031 Uiso 1 1 calc R U . . .
H15C H -0.0319 0.7192 0.8678 0.031 Uiso 1 1 calc R U . . .
C16 C -0.1721(2) 0.2137(2) 0.81504(18) 0.0239(5) Uani 1 1 d . . . . .
H16A H -0.1809 0.1820 0.7466 0.036 Uiso 1 1 calc R U . . .
H16B H -0.2586 0.1986 0.8236 0.036 Uiso 1 1 calc R U . . .
H16C H -0.1297 0.1709 0.8614 0.036 Uiso 1 1 calc R U . . .
C17 C 0.3830(2) 0.7939(2) 0.80286(17) 0.0191(4) Uani 1 1 d . . . . .
C18 C 0.2502(2) 0.73502(19) 0.75158(16) 0.0180(4) Uani 1 1 d . . . . .
C19 C 0.1546(2) 0.7950(2) 0.75139(18) 0.0210(4) Uani 1 1 d . . . . .
C20 C 0.1494(3) 0.8731(2) 0.6662(2) 0.0293(5) Uani 1 1 d . . . . .
C21 C 0.2811(3) 0.9688(2) 0.6623(2) 0.0313(6) Uani 1 1 d . . . . .
C22 C 0.3620(3) 1.0586(2) 0.7590(2) 0.0350(6) Uani 1 1 d . . . . .
C23 C 0.4764(3) 1.0304(2) 0.8216(2) 0.0326(6) Uani 1 1 d . . . . .
C24 C 0.4395(2) 0.9143(2) 0.87406(19) 0.0249(5) Uani 1 1 d . . . . .
C31A C 0.7075(5) 0.4678(3) 0.6353(2) 0.0291(12) Uiso 0.607(11) 1 d G . P A 1
D31A D 0.6881 0.5327 0.6620 0.035 Uiso 0.607(11) 1 calc R U P A 1
C32A C 0.6183(4) 0.3452(3) 0.6197(3) 0.0307(11) Uiso 0.607(11) 1 d G . P A 1
D32A D 0.5379 0.3263 0.6358 0.037 Uiso 0.607(11) 1 calc R U P A 1
C33A C 0.6466(4) 0.2503(2) 0.5806(4) 0.035(2) Uiso 0.607(11) 1 d G . P A 1
D33A D 0.5857 0.1665 0.5699 0.042 Uiso 0.607(11) 1 calc R U P A 1
C34A C 0.7642(4) 0.2780(3) 0.5570(4) 0.0330(15) Uiso 0.607(11) 1 d G . P A 1
D34A D 0.7835 0.2131 0.5302 0.040 Uiso 0.607(11) 1 calc R U P A 1
C35A C 0.8534(3) 0.4006(4) 0.5725(3) 0.0368(12) Uiso 0.607(11) 1 d G . P A 1
D35A D 0.9337 0.4195 0.5564 0.044 Uiso 0.607(11) 1 calc R U P A 1
C36A C 0.8250(4) 0.4955(2) 0.6117(3) 0.0280(11) Uiso 0.607(11) 1 d G . P A 1
D36A D 0.8860 0.5793 0.6223 0.034 Uiso 0.607(11) 1 calc R U P A 1
C31B C 0.7607(8) 0.4857(4) 0.6250(4) 0.0319(18) Uiso 0.393(11) 1 d G . P A 2
D31B D 0.7602 0.5617 0.6516 0.038 Uiso 0.393(11) 1 calc R U P A 2
C32B C 0.6554(7) 0.3744(6) 0.6178(5) 0.044(2) Uiso 0.393(11) 1 d G . P A 2
D32B D 0.5830 0.3743 0.6395 0.053 Uiso 0.393(11) 1 calc R U P A 2
C33B C 0.6561(6) 0.2632(5) 0.5788(7) 0.038(3) Uiso 0.393(11) 1 d G . P A 2
D33B D 0.5842 0.1871 0.5739 0.046 Uiso 0.393(11) 1 calc R U P A 2
C34B C 0.7621(7) 0.2632(4) 0.5471(7) 0.044(3) Uiso 0.393(11) 1 d G . P A 2
D34B D 0.7626 0.1872 0.5205 0.053 Uiso 0.393(11) 1 calc R U P A 2
C35B C 0.8674(5) 0.3745(6) 0.5543(5) 0.0381(19) Uiso 0.393(11) 1 d G . P A 2
D35B D 0.9398 0.3746 0.5326 0.046 Uiso 0.393(11) 1 calc R U P A 2
C36B C 0.8667(6) 0.4857(4) 0.5933(5) 0.0339(19) Uiso 0.393(11) 1 d G . P A 2
D36B D 0.9386 0.5618 0.5982 0.041 Uiso 0.393(11) 1 calc R U P A 2
C30 C 0.7359(2) 0.8866(2) 0.61565(17) 0.0235(5) Uani 1 1 d . . . . .
S1 S 0.79901(5) 0.87406(5) 0.74576(4) 0.02051(11) Uani 1 1 d . . . . .
O1 O 0.8129(2) 0.75719(18) 0.73987(16) 0.0414(5) Uani 1 1 d . . . . .
O2 O 0.91863(17) 0.98217(16) 0.77732(13) 0.0292(4) Uani 1 1 d . . . . .
O3 O 0.69819(18) 0.87627(19) 0.78949(14) 0.0356(4) Uani 1 1 d . . . . .
F1 F 0.82394(16) 0.89474(16) 0.56540(12) 0.0405(4) Uani 1 1 d . . . . .
F2 F 0.70828(19) 0.98704(15) 0.60567(12) 0.0439(4) Uani 1 1 d . . . . .
F3 F 0.62909(14) 0.78764(14) 0.56941(11) 0.0345(3) Uani 1 1 d . . . . .
H1 H 0.314(3) 0.724(2) 0.9584(17) 0.046(9) Uiso 1 1 d D . . . .
H2 H 0.4505(10) 0.675(3) 0.903(2) 0.046(9) Uiso 1 1 d D . . . .
H8 H 0.265(3) 0.332(3) 0.555(2) 0.030(7) Uiso 1 1 d . . . . .
H13 H -0.192(3) 0.442(3) 0.886(2) 0.030(7) Uiso 1 1 d . . . . .
H17 H 0.444(2) 0.779(2) 0.7719(18) 0.013(6) Uiso 1 1 d . . . . .
H18 H 0.230(3) 0.681(2) 0.691(2) 0.020(6) Uiso 1 1 d . . . . .
H19A H 0.068(3) 0.736(3) 0.744(2) 0.022(7) Uiso 1 1 d . . . . .
H19B H 0.181(3) 0.845(3) 0.813(2) 0.028(7) Uiso 1 1 d . . . . .
H20A H 0.112(3) 0.817(3) 0.598(2) 0.036(8) Uiso 1 1 d . . . . .
H20B H 0.094(3) 0.915(3) 0.673(2) 0.033(8) Uiso 1 1 d . . . . .
H21A H 0.341(3) 0.933(3) 0.645(2) 0.027(7) Uiso 1 1 d . . . . .
H21B H 0.265(3) 1.019(3) 0.608(2) 0.028(7) Uiso 1 1 d . . . . .
H22A H 0.400(3) 1.143(3) 0.739(2) 0.044(9) Uiso 1 1 d . . . . .
H22B H 0.305(3) 1.059(3) 0.798(2) 0.027(7) Uiso 1 1 d . . . . .
H23A H 0.527(3) 1.023(3) 0.783(2) 0.033(8) Uiso 1 1 d . . . . .
H23B H 0.532(3) 1.100(3) 0.875(2) 0.039(8) Uiso 1 1 d . . . . .
H24A H 0.515(3) 0.916(2) 0.922(2) 0.022(7) Uiso 1 1 d . . . . .
H24B H 0.380(3) 0.920(3) 0.912(2) 0.025(7) Uiso 1 1 d . . . . .
H222 H 0.350(2) 0.328(2) 1.1200(19) 0.011(6) Uiso 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
Ir N1 2.0747(18) . ?
Ir C18 2.168(2) . ?
Ir N5 2.1786(17) . ?
Ir N3 2.1957(17) . ?
Ir C17 2.199(2) . ?
Ir H1 1.629(10) . ?
Ir H2 1.626(10) . ?
N1 C1 1.340(3) . ?
N1 N2 1.377(2) . ?
N2 C3 1.367(3) . ?
N2 C6 1.453(3) . ?
N3 C7 1.334(3) . ?
N3 N4 1.372(2) . ?
N4 C9 1.364(3) . ?
N4 C6 1.446(2) . ?
N5 C12 1.334(3) . ?
N5 N6 1.380(2) . ?
N6 C14 1.370(3) . ?
N6 C6 1.445(3) . ?
C1 C2 1.404(3) . ?
C1 C4 1.491(3) . ?
C2 C3 1.372(3) . ?
C2 H222 0.90(3) . ?
C3 C5 1.491(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 1.01(3) . ?
C7 C8 1.406(3) . ?
C7 C10 1.491(3) . ?
C8 C9 1.375(3) . ?
C8 H8 0.89(3) . ?
C9 C11 1.483(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.407(3) . ?
C12 C15 1.488(3) . ?
C13 C14 1.365(3) . ?
C13 H13 0.93(3) . ?
C14 C16 1.487(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.405(3) . ?
C17 C24 1.514(3) . ?
C17 H17 0.97(2) . ?
C18 C19 1.501(3) . ?
C18 H18 0.96(3) . ?
C19 C20 1.534(3) . ?
C19 H19A 0.95(3) . ?
C19 H19B 0.94(3) . ?
C20 C21 1.529(4) . ?
C20 H20A 1.03(3) . ?
C20 H20B 0.96(3) . ?
C21 C22 1.535(4) . ?
C21 H21A 0.99(3) . ?
C21 H21B 1.00(3) . ?
C22 C23 1.546(4) . ?
C22 H22A 1.00(3) . ?
C22 H22B 0.95(3) . ?
C23 C24 1.537(3) . ?
C23 H23A 0.91(3) . ?
C23 H23B 0.99(3) . ?
C24 H24A 0.96(3) . ?
C24 H24B 0.98(3) . ?
C31A C32A 1.3900 . ?
C31A C36A 1.3900 . ?
C31A D31A 0.9500 . ?
C32A C33A 1.3900 . ?
C32A D32A 0.9500 . ?
C33A C34A 1.3900 . ?
C33A D33A 0.9500 . ?
C34A C35A 1.3900 . ?
C34A D34A 0.9500 . ?
C35A C36A 1.3900 . ?
C35A D35A 0.9500 . ?
C36A D36A 0.9500 . ?
C31B C32B 1.3900 . ?
C31B C36B 1.3900 . ?
C31B D31B 0.9500 . ?
C32B C33B 1.3900 . ?
C32B D32B 0.9500 . ?
C33B C34B 1.3900 . ?
C33B D33B 0.9500 . ?
C34B C35B 1.3900 . ?
C34B D34B 0.9500 . ?
C35B C36B 1.3900 . ?
C35B D35B 0.9500 . ?
C36B D36B 0.9500 . ?
C30 F2 1.326(3) . ?
C30 F3 1.330(3) . ?
C30 F1 1.341(3) . ?
C30 S1 1.824(2) . ?
S1 O1 1.4311(19) . ?
S1 O2 1.4351(17) . ?
S1 O3 1.4390(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir C18 166.96(8) . . ?
N1 Ir N5 79.63(7) . . ?
C18 Ir N5 89.82(7) . . ?
N1 Ir N3 84.17(6) . . ?
C18 Ir N3 87.90(7) . . ?
N5 Ir N3 88.26(6) . . ?
N1 Ir C17 154.47(8) . . ?
C18 Ir C17 37.53(8) . . ?
N5 Ir C17 125.55(7) . . ?
N3 Ir C17 99.33(7) . . ?
N1 Ir H1 93.0(12) . . ?
C18 Ir H1 95.3(12) . . ?
N5 Ir H1 93.4(11) . . ?
N3 Ir H1 176.4(12) . . ?
C17 Ir H1 82.3(12) . . ?
N1 Ir H2 85.5(12) . . ?
C18 Ir H2 105.5(12) . . ?
N5 Ir H2 164.4(12) . . ?
N3 Ir H2 95.1(12) . . ?
C17 Ir H2 69.0(12) . . ?
H1 Ir H2 82.5(16) . . ?
C1 N1 N2 105.98(17) . . ?
C1 N1 Ir 135.54(15) . . ?
N2 N1 Ir 118.39(13) . . ?
C3 N2 N1 110.96(17) . . ?
C3 N2 C6 128.96(18) . . ?
N1 N2 C6 119.57(16) . . ?
C7 N3 N4 105.16(16) . . ?
C7 N3 Ir 138.95(14) . . ?
N4 N3 Ir 115.57(12) . . ?
C9 N4 N3 112.09(16) . . ?
C9 N4 C6 127.75(17) . . ?
N3 N4 C6 119.85(16) . . ?
C12 N5 N6 105.40(16) . . ?
C12 N5 Ir 135.71(15) . . ?
N6 N5 Ir 117.23(12) . . ?
C14 N6 N5 111.37(16) . . ?
C14 N6 C6 125.98(18) . . ?
N5 N6 C6 118.25(16) . . ?
N1 C1 C2 109.59(19) . . ?
N1 C1 C4 121.51(19) . . ?
C2 C1 C4 128.9(2) . . ?
C3 C2 C1 107.27(19) . . ?
C3 C2 H222 123.9(16) . . ?
C1 C2 H222 128.8(16) . . ?
N2 C3 C2 106.19(18) . . ?
N2 C3 C5 123.68(19) . . ?
C2 C3 C5 130.1(2) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N6 C6 N4 111.74(17) . . ?
N6 C6 N2 110.97(16) . . ?
N4 C6 N2 111.02(16) . . ?
N6 C6 H6 110.3(14) . . ?
N4 C6 H6 107.1(14) . . ?
N2 C6 H6 105.4(15) . . ?
N3 C7 C8 110.29(18) . . ?
N3 C7 C10 122.78(19) . . ?
C8 C7 C10 126.92(19) . . ?
C9 C8 C7 106.94(18) . . ?
C9 C8 H8 125.6(19) . . ?
C7 C8 H8 127.5(19) . . ?
N4 C9 C8 105.52(18) . . ?
N4 C9 C11 122.98(18) . . ?
C8 C9 C11 131.46(19) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N5 C12 C13 109.96(19) . . ?
N5 C12 C15 123.86(19) . . ?
C13 C12 C15 126.14(19) . . ?
C14 C13 C12 107.42(19) . . ?
C14 C13 H13 126.0(18) . . ?
C12 C13 H13 126.6(18) . . ?
C13 C14 N6 105.80(19) . . ?
C13 C14 C16 130.88(19) . . ?
N6 C14 C16 123.32(19) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C24 123.4(2) . . ?
C18 C17 Ir 70.06(12) . . ?
C24 C17 Ir 115.72(15) . . ?
C18 C17 H17 116.8(15) . . ?
C24 C17 H17 114.6(15) . . ?
Ir C17 H17 106.3(14) . . ?
C17 C18 C19 122.7(2) . . ?
C17 C18 Ir 72.41(13) . . ?
C19 C18 Ir 121.94(15) . . ?
C17 C18 H18 116.0(16) . . ?
C19 C18 H18 113.4(16) . . ?
Ir C18 H18 102.7(16) . . ?
C18 C19 C20 110.62(19) . . ?
C18 C19 H19A 112.6(16) . . ?
C20 C19 H19A 107.8(17) . . ?
C18 C19 H19B 107.7(18) . . ?
C20 C19 H19B 110.8(18) . . ?
H19A C19 H19B 107(2) . . ?
C21 C20 C19 115.2(2) . . ?
C21 C20 H20A 105.0(17) . . ?
C19 C20 H20A 110.6(17) . . ?
C21 C20 H20B 109.0(18) . . ?
C19 C20 H20B 107.3(18) . . ?
H20A C20 H20B 110(3) . . ?
C20 C21 C22 115.2(2) . . ?
C20 C21 H21A 114.8(16) . . ?
C22 C21 H21A 104.5(17) . . ?
C20 C21 H21B 108.3(17) . . ?
C22 C21 H21B 108.6(17) . . ?
H21A C21 H21B 105(2) . . ?
C21 C22 C23 115.6(2) . . ?
C21 C22 H22A 106(2) . . ?
C23 C22 H22A 107(2) . . ?
C21 C22 H22B 108.0(18) . . ?
C23 C22 H22B 109.7(18) . . ?
H22A C22 H22B 110(2) . . ?
C24 C23 C22 116.3(2) . . ?
C24 C23 H23A 108.3(19) . . ?
C22 C23 H23A 110(2) . . ?
C24 C23 H23B 105.3(19) . . ?
C22 C23 H23B 109.8(18) . . ?
H23A C23 H23B 107(3) . . ?
C17 C24 C23 112.9(2) . . ?
C17 C24 H24A 108.2(16) . . ?
C23 C24 H24A 109.3(17) . . ?
C17 C24 H24B 112.3(17) . . ?
C23 C24 H24B 107.9(16) . . ?
H24A C24 H24B 106(2) . . ?
C32A C31A C36A 120.0 . . ?
C32A C31A D31A 120.0 . . ?
C36A C31A D31A 120.0 . . ?
C31A C32A C33A 120.0 . . ?
C31A C32A D32A 120.0 . . ?
C33A C32A D32A 120.0 . . ?
C34A C33A C32A 120.0 . . ?
C34A C33A D33A 120.0 . . ?
C32A C33A D33A 120.0 . . ?
C33A C34A C35A 120.0 . . ?
C33A C34A D34A 120.0 . . ?
C35A C34A D34A 120.0 . . ?
C34A C35A C36A 120.0 . . ?
C34A C35A D35A 120.0 . . ?
C36A C35A D35A 120.0 . . ?
C35A C36A C31A 120.0 . . ?
C35A C36A D36A 120.0 . . ?
C31A C36A D36A 120.0 . . ?
C32B C31B C36B 120.0 . . ?
C32B C31B D31B 120.0 . . ?
C36B C31B D31B 120.0 . . ?
C31B C32B C33B 120.0 . . ?
C31B C32B D32B 120.0 . . ?
C33B C32B D32B 120.0 . . ?
C34B C33B C32B 120.0 . . ?
C34B C33B D33B 120.0 . . ?
C32B C33B D33B 120.0 . . ?
C35B C34B C33B 120.0 . . ?
C35B C34B D34B 120.0 . . ?
C33B C34B D34B 120.0 . . ?
C36B C35B C34B 120.0 . . ?
C36B C35B D35B 120.0 . . ?
C34B C35B D35B 120.0 . . ?
C35B C36B C31B 120.0 . . ?
C35B C36B D36B 120.0 . . ?
C31B C36B D36B 120.0 . . ?
F2 C30 F3 108.1(2) . . ?
F2 C30 F1 107.0(2) . . ?
F3 C30 F1 106.32(19) . . ?
F2 C30 S1 112.14(16) . . ?
F3 C30 S1 112.41(16) . . ?
F1 C30 S1 110.63(17) . . ?
O1 S1 O2 115.51(12) . . ?
O1 S1 O3 114.75(13) . . ?
O2 S1 O3 114.97(12) . . ?
O1 S1 C30 102.93(12) . . ?
O2 S1 C30 102.89(11) . . ?
O3 S1 C30 103.25(11) . . ?

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
C1 N1 N2 C3 0.9(2) . . . . ?
Ir N1 N2 C3 177.90(12) . . . . ?
C1 N1 N2 C6 173.46(17) . . . . ?
Ir N1 N2 C6 -9.6(2) . . . . ?
C7 N3 N4 C9 -0.4(2) . . . . ?
Ir N3 N4 C9 174.34(13) . . . . ?
C7 N3 N4 C6 173.73(18) . . . . ?
Ir N3 N4 C6 -11.6(2) . . . . ?
C12 N5 N6 C14 -1.1(2) . . . . ?
Ir N5 N6 C14 166.51(14) . . . . ?
C12 N5 N6 C6 -158.99(18) . . . . ?
Ir N5 N6 C6 8.6(2) . . . . ?
N2 N1 C1 C2 -0.9(2) . . . . ?
Ir N1 C1 C2 -177.09(14) . . . . ?
N2 N1 C1 C4 179.42(17) . . . . ?
Ir N1 C1 C4 3.2(3) . . . . ?
N1 C1 C2 C3 0.6(2) . . . . ?
C4 C1 C2 C3 -179.8(2) . . . . ?
N1 N2 C3 C2 -0.6(2) . . . . ?
C6 N2 C3 C2 -172.23(19) . . . . ?
N1 N2 C3 C5 179.14(18) . . . . ?
C6 N2 C3 C5 7.5(3) . . . . ?
C1 C2 C3 N2 0.0(2) . . . . ?
C1 C2 C3 C5 -179.7(2) . . . . ?
C14 N6 C6 N4 136.5(2) . . . . ?
N5 N6 C6 N4 -69.1(2) . . . . ?
C14 N6 C6 N2 -99.0(2) . . . . ?
N5 N6 C6 N2 55.3(2) . . . . ?
C9 N4 C6 N6 -115.3(2) . . . . ?
N3 N4 C6 N6 71.6(2) . . . . ?
C9 N4 C6 N2 120.2(2) . . . . ?
N3 N4 C6 N2 -52.9(2) . . . . ?
C3 N2 C6 N6 114.0(2) . . . . ?
N1 N2 C6 N6 -57.0(2) . . . . ?
C3 N2 C6 N4 -121.1(2) . . . . ?
N1 N2 C6 N4 67.9(2) . . . . ?
N4 N3 C7 C8 0.4(2) . . . . ?
Ir N3 C7 C8 -172.34(16) . . . . ?
N4 N3 C7 C10 -178.59(19) . . . . ?
Ir N3 C7 C10 8.7(3) . . . . ?
N3 C7 C8 C9 -0.3(3) . . . . ?
C10 C7 C8 C9 178.6(2) . . . . ?
N3 N4 C9 C8 0.2(2) . . . . ?
C6 N4 C9 C8 -173.3(2) . . . . ?
N3 N4 C9 C11 -177.82(19) . . . . ?
C6 N4 C9 C11 8.7(3) . . . . ?
C7 C8 C9 N4 0.0(2) . . . . ?
C7 C8 C9 C11 177.8(2) . . . . ?
N6 N5 C12 C13 -0.4(2) . . . . ?
Ir N5 C12 C13 -164.52(16) . . . . ?
N6 N5 C12 C15 177.39(19) . . . . ?
Ir N5 C12 C15 13.2(3) . . . . ?
N5 C12 C13 C14 1.7(3) . . . . ?
C15 C12 C13 C14 -176.0(2) . . . . ?
C12 C13 C14 N6 -2.3(2) . . . . ?
C12 C13 C14 C16 178.1(2) . . . . ?
N5 N6 C14 C13 2.1(2) . . . . ?
C6 N6 C14 C13 157.9(2) . . . . ?
N5 N6 C14 C16 -178.20(19) . . . . ?
C6 N6 C14 C16 -22.4(3) . . . . ?
C24 C17 C18 C19 8.8(3) . . . . ?
Ir C17 C18 C19 117.1(2) . . . . ?
C24 C17 C18 Ir -108.3(2) . . . . ?
C17 C18 C19 C20 88.4(3) . . . . ?
Ir C18 C19 C20 177.11(17) . . . . ?
C18 C19 C20 C21 -53.0(3) . . . . ?
C19 C20 C21 C22 -53.6(3) . . . . ?
C20 C21 C22 C23 103.1(3) . . . . ?
C21 C22 C23 C24 -70.8(3) . . . . ?
C18 C17 C24 C23 -86.4(3) . . . . ?
Ir C17 C24 C23 -168.63(17) . . . . ?
C22 C23 C24 C17 72.6(3) . . . . ?
C36A C31A C32A C33A 0.0 . . . . ?
C31A C32A C33A C34A 0.0 . . . . ?
C32A C33A C34A C35A 0.0 . . . . ?
C33A C34A C35A C36A 0.0 . . . . ?
C34A C35A C36A C31A 0.0 . . . . ?
C32A C31A C36A C35A 0.0 . . . . ?
C36B C31B C32B C33B 0.0 . . . . ?
C31B C32B C33B C34B 0.0 . . . . ?
C32B C33B C34B C35B 0.0 . . . . ?
C33B C34B C35B C36B 0.0 . . . . ?
C34B C35B C36B C31B 0.0 . . . . ?
C32B C31B C36B C35B 0.0 . . . . ?
F2 C30 S1 O1 175.99(18) . . . . ?
F3 C30 S1 O1 54.0(2) . . . . ?
F1 C30 S1 O1 -64.70(19) . . . . ?
F2 C30 S1 O2 -63.6(2) . . . . ?
F3 C30 S1 O2 174.38(17) . . . . ?
F1 C30 S1 O2 55.69(18) . . . . ?
F2 C30 S1 O3 56.3(2) . . . . ?
F3 C30 S1 O3 -65.7(2) . . . . ?
F1 C30 S1 O3 175.61(16) . . . . ?

_refine_diff_density_max         1.057
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.088

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: deuterated benzene'
####################################################################### 
# 
# 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_cmpnd_2
_database_code_depnum_ccdc_archive 'CCDC 1812902'
loop_
_audit_author_name
_audit_author_address
'Pilar Garcia-Orduna'
'Instituto de S?ntesis Qu?mica y Cat?lisis Homog?nea (ISQCH, CSIC-Univ. Zaragoza)'
_audit_update_record             
;
2017-12-21 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H34 Ir N6, C F3 O3 S'
_chemical_formula_sum            'C25 H34 F3 Ir N6 O3 S'
_chemical_formula_weight         747.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.5533(3)
_cell_length_b                   13.9441(5)
_cell_length_c                   22.6818(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.3320(10)
_cell_angle_gamma                90
_cell_volume                     2688.71(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      2.465
_cell_measurement_theta_max      29.365

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_F_000             1480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.091
_exptl_absorpt_coefficient_mu    5.104
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5086
_exptl_absorpt_correction_T_max  0.6493
_exptl_absorpt_process_details   
;
 SADABS: Area-Detector Absorption Correction. (1996) Bruker-AXS 
 within APEX2 package.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX DUO CCD system'
_diffrn_measurement_method       'narrow ω frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_reflns_number            29413
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.717
_diffrn_reflns_theta_max         29.608
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7084
_reflns_number_gt                6414
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART in APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_cell_refinement       'SAINT+ in APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT+ in APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP program, SHELXTL v6.12, Bruker2000'
_computing_publication_material  'XCIF program, PLATON(Spek, 1998)'

_refine_special_details          
;
All hydrogen atoms have been observed in Fourier difference maps. 
In order to minimize the number of refined parameters, hydrogen
atoms of methyl groups have been included in the model in 
calculated positions and refined with a riding model. The rest of
hydrogen atoms have been included in observed positions and freely
refined. Isotropic atomic displacement parameters of H6 have been 
constrained to be 1.2 times Ueq of its parent carbon atom.

At the end of the refinement, when convergence is achieved the 
residual density peaks are observed close to iridum atom. They have 
no chemical sense.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0236P)²+1.5177P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7084
_refine_ls_number_parameters     421
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0188
_refine_ls_wR_factor_ref         0.0453
_refine_ls_wR_factor_gt          0.0441
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir Ir 0.65448(2) 0.82504(2) 0.77457(2) 0.01102(3) Uani 1 1 d . . . . .
N1 N 0.5351(2) 0.69828(13) 0.79485(8) 0.0124(3) Uani 1 1 d . . . . .
N2 N 0.5466(2) 0.66875(12) 0.85290(8) 0.0128(3) Uani 1 1 d . . . . .
N3 N 0.8420(2) 0.75950(12) 0.82809(7) 0.0122(3) Uani 1 1 d . . . . .
N4 N 0.80857(19) 0.71943(13) 0.88088(7) 0.0122(3) Uani 1 1 d . . . . .
N6 N 0.5892(2) 0.81442(12) 0.90497(8) 0.0125(3) Uani 1 1 d . . . . .
N5 N 0.4286(2) 0.82272(12) 0.89952(8) 0.0131(3) Uani 1 1 d . . . . .
C1 C 0.4447(2) 0.63219(15) 0.76447(9) 0.0144(4) Uani 1 1 d . . . . .
C2 C 0.3957(2) 0.56352(15) 0.80370(10) 0.0159(4) Uani 1 1 d D . . . .
C3 C 0.4612(2) 0.58842(15) 0.85953(10) 0.0145(4) Uani 1 1 d . . . . .
C4 C 0.4120(3) 0.63447(17) 0.69868(10) 0.0194(4) Uani 1 1 d . . . . .
H4A H 0.3097 0.6649 0.6875 0.029 Uiso 1 1 calc R U . . .
H4B H 0.4101 0.5688 0.6832 0.029 Uiso 1 1 calc R U . . .
H4C H 0.4944 0.6712 0.6820 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4487(3) 0.54480(16) 0.91907(10) 0.0188(4) Uani 1 1 d . . . . .
H5A H 0.5520 0.5209 0.9356 0.028 Uiso 1 1 calc R U . . .
H5B H 0.3735 0.4916 0.9149 0.028 Uiso 1 1 calc R U . . .
H5C H 0.4124 0.5934 0.9456 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6495(2) 0.71812(15) 0.89737(9) 0.0116(4) Uani 1 1 d . . . . .
H6 H 0.653(3) 0.6814(17) 0.9353(12) 0.014 Uiso 1 1 d . U . . .
C7 C 0.9978(2) 0.74716(15) 0.82753(9) 0.0141(4) Uani 1 1 d . . . . .
C8 C 1.0614(3) 0.70001(16) 0.87893(10) 0.0171(4) Uani 1 1 d . . . . .
C9 C 0.9394(3) 0.68210(15) 0.91206(10) 0.0155(4) Uani 1 1 d . . . . .
C10 C 1.0833(3) 0.77907(17) 0.77715(10) 0.0183(4) Uani 1 1 d . . . . .
H10A H 1.0297 0.7542 0.7399 0.027 Uiso 1 1 calc R U . . .
H10B H 1.1914 0.7547 0.7827 0.027 Uiso 1 1 calc R U . . .
H10C H 1.0850 0.8493 0.7758 0.027 Uiso 1 1 calc R U . . .
C11 C 0.9370(3) 0.63179(19) 0.97001(10) 0.0227(5) Uani 1 1 d . . . . .
H11A H 0.8918 0.6743 0.9981 0.034 Uiso 1 1 calc R U . . .
H11B H 1.0446 0.6145 0.9858 0.034 Uiso 1 1 calc R U . . .
H11C H 0.8730 0.5735 0.9642 0.034 Uiso 1 1 calc R U . . .
C12 C 0.4039(2) 0.91158(15) 0.91764(9) 0.0134(4) Uani 1 1 d . . . . .
C13 C 0.5460(3) 0.95924(16) 0.93570(9) 0.0156(4) Uani 1 1 d . . . . .
C14 C 0.6635(2) 0.89508(15) 0.92896(9) 0.0138(4) Uani 1 1 d . . . . .
C15 C 0.2398(2) 0.94834(16) 0.91741(10) 0.0173(4) Uani 1 1 d . . . . .
H15A H 0.1742 0.9230 0.8828 0.026 Uiso 1 1 calc R U . . .
H15B H 0.2405 1.0186 0.9156 0.026 Uiso 1 1 calc R U . . .
H15C H 0.1970 0.9276 0.9537 0.026 Uiso 1 1 calc R U . . .
C16 C 0.8375(3) 0.90578(17) 0.94427(11) 0.0213(5) Uani 1 1 d . . . . .
H16A H 0.8736 0.8615 0.9765 0.032 Uiso 1 1 calc R U . . .
H16B H 0.8616 0.9718 0.9570 0.032 Uiso 1 1 calc R U . . .
H16C H 0.8911 0.8911 0.9093 0.032 Uiso 1 1 calc R U . . .
C17 C 0.7814(3) 0.95650(15) 0.77916(10) 0.0161(4) Uani 1 1 d . . . . .
C18 C 0.7764(3) 0.91965(16) 0.72107(10) 0.0167(4) Uani 1 1 d . . . . .
C19 C 0.6716(3) 0.96448(17) 0.66946(10) 0.0198(4) Uani 1 1 d . . . . .
C20 C 0.5143(3) 0.91188(18) 0.65702(10) 0.0197(5) Uani 1 1 d . . . . .
C21 C 0.4613(2) 0.87057(16) 0.71327(9) 0.0151(4) Uani 1 1 d . . . . .
C22 C 0.4621(2) 0.92176(16) 0.76691(10) 0.0152(4) Uani 1 1 d . . . . .
C23 C 0.5079(3) 1.02725(17) 0.77504(10) 0.0186(4) Uani 1 1 d . . . . .
C24 C 0.6841(3) 1.04023(16) 0.79622(11) 0.0184(4) Uani 1 1 d . . . . .
S1 S 0.42574(7) 0.26811(4) 0.91562(2) 0.01786(11) Uani 1 1 d . . . . .
C25 C 0.6402(3) 0.26357(17) 0.92909(10) 0.0215(5) Uani 1 1 d . . . . .
O1 O 0.3838(2) 0.16911(13) 0.90579(10) 0.0368(5) Uani 1 1 d . . . . .
O2 O 0.3821(2) 0.30967(14) 0.96966(8) 0.0285(4) Uani 1 1 d . . . . .
O3 O 0.3988(2) 0.32894(12) 0.86446(8) 0.0257(4) Uani 1 1 d . . . . .
F1 F 0.69017(18) 0.20087(12) 0.97140(7) 0.0352(4) Uani 1 1 d . . . . .
F2 F 0.70057(17) 0.34919(11) 0.94625(7) 0.0299(3) Uani 1 1 d . . . . .
F3 F 0.70507(19) 0.23888(12) 0.88045(7) 0.0361(4) Uani 1 1 d . . . . .
H2 H 0.332(3) 0.5115(15) 0.7930(11) 0.022(7) Uiso 1 1 d D . . . .
H8 H 1.160(3) 0.6861(17) 0.8883(12) 0.017(7) Uiso 1 1 d . . . . .
H13 H 0.557(3) 1.0209(19) 0.9501(11) 0.019(6) Uiso 1 1 d . . . . .
H17 H 0.878(3) 0.9493(18) 0.8047(11) 0.015(6) Uiso 1 1 d . . . . .
H18 H 0.862(3) 0.8881(18) 0.7094(10) 0.010(6) Uiso 1 1 d . . . . .
H19A H 0.720(3) 0.967(2) 0.6361(13) 0.032(8) Uiso 1 1 d . . . . .
H19B H 0.657(3) 1.0321(18) 0.6790(10) 0.012(6) Uiso 1 1 d . . . . .
H20A H 0.522(3) 0.855(2) 0.6305(12) 0.021(7) Uiso 1 1 d . . . . .
H20B H 0.437(3) 0.9544(19) 0.6386(12) 0.020(7) Uiso 1 1 d . . . . .
H21 H 0.385(3) 0.8208(16) 0.7050(11) 0.008(6) Uiso 1 1 d . . . . .
H22 H 0.399(3) 0.8992(16) 0.7952(10) 0.009(6) Uiso 1 1 d . . . . .
H23A H 0.483(3) 1.063(2) 0.7365(13) 0.027(7) Uiso 1 1 d . . . . .
H23B H 0.446(3) 1.0542(19) 0.8043(12) 0.021(7) Uiso 1 1 d . . . . .
H24A H 0.724(3) 1.1007(18) 0.7799(10) 0.011(6) Uiso 1 1 d . . . . .
H24B H 0.703(3) 1.045(2) 0.8365(14) 0.032(8) Uiso 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
Ir N3 2.1101(17) . ?
Ir N1 2.1172(18) . ?
Ir C22 2.120(2) . ?
Ir C17 2.127(2) . ?
Ir C21 2.135(2) . ?
Ir C18 2.140(2) . ?
N1 C1 1.343(3) . ?
N1 N2 1.373(2) . ?
N2 C3 1.355(3) . ?
N2 C6 1.439(3) . ?
N3 C7 1.345(3) . ?
N3 N4 1.380(2) . ?
N4 C9 1.360(3) . ?
N4 C6 1.450(3) . ?
N6 N5 1.371(2) . ?
N6 C14 1.374(3) . ?
N6 C6 1.455(3) . ?
N5 C12 1.330(3) . ?
C1 C2 1.402(3) . ?
C1 C4 1.488(3) . ?
C2 C3 1.372(3) . ?
C2 H2 0.924(17) . ?
C3 C5 1.496(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 1.00(3) . ?
C7 C8 1.396(3) . ?
C7 C10 1.491(3) . ?
C8 C9 1.374(3) . ?
C8 H8 0.87(3) . ?
C9 C11 1.492(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.407(3) . ?
C12 C15 1.493(3) . ?
C13 C14 1.366(3) . ?
C13 H13 0.92(3) . ?
C14 C16 1.498(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.411(3) . ?
C17 C24 1.508(3) . ?
C17 H17 0.96(3) . ?
C18 C19 1.527(3) . ?
C18 H18 0.92(2) . ?
C19 C20 1.531(3) . ?
C19 H19A 0.90(3) . ?
C19 H19B 0.98(2) . ?
C20 C21 1.514(3) . ?
C20 H20A 1.00(3) . ?
C20 H20B 0.95(3) . ?
C21 C22 1.410(3) . ?
C21 H21 0.95(2) . ?
C22 C23 1.528(3) . ?
C22 H22 0.94(2) . ?
C23 C24 1.541(3) . ?
C23 H23A 1.01(3) . ?
C23 H23B 0.97(3) . ?
C24 H24A 0.99(2) . ?
C24 H24B 0.91(3) . ?
S1 O3 1.4352(17) . ?
S1 O1 1.4375(18) . ?
S1 O2 1.4420(18) . ?
S1 C25 1.827(2) . ?
C25 F1 1.333(3) . ?
C25 F3 1.333(3) . ?
C25 F2 1.341(3) . ?

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 Ir N1 82.40(7) . . ?
N3 Ir C22 148.95(7) . . ?
N1 Ir C22 99.23(8) . . ?
N3 Ir C17 89.63(8) . . ?
N1 Ir C17 164.71(8) . . ?
C22 Ir C17 80.97(8) . . ?
N3 Ir C21 171.09(8) . . ?
N1 Ir C21 91.87(8) . . ?
C22 Ir C21 38.70(8) . . ?
C17 Ir C21 97.45(8) . . ?
N3 Ir C18 101.89(8) . . ?
N1 Ir C18 156.18(8) . . ?
C22 Ir C18 89.07(8) . . ?
C17 Ir C18 38.61(9) . . ?
C21 Ir C18 80.68(8) . . ?
C1 N1 N2 105.23(17) . . ?
C1 N1 Ir 136.50(15) . . ?
N2 N1 Ir 118.26(13) . . ?
C3 N2 N1 111.83(17) . . ?
C3 N2 C6 127.84(18) . . ?
N1 N2 C6 120.18(16) . . ?
C7 N3 N4 104.88(16) . . ?
C7 N3 Ir 137.82(14) . . ?
N4 N3 Ir 117.22(12) . . ?
C9 N4 N3 111.64(17) . . ?
C9 N4 C6 127.07(18) . . ?
N3 N4 C6 121.28(16) . . ?
N5 N6 C14 112.43(16) . . ?
N5 N6 C6 115.58(16) . . ?
C14 N6 C6 130.38(18) . . ?
C12 N5 N6 104.05(17) . . ?
N1 C1 C2 109.78(19) . . ?
N1 C1 C4 122.27(19) . . ?
C2 C1 C4 127.9(2) . . ?
C3 C2 C1 107.01(19) . . ?
C3 C2 H2 127.7(17) . . ?
C1 C2 H2 125.3(17) . . ?
N2 C3 C2 106.10(19) . . ?
N2 C3 C5 121.98(19) . . ?
C2 C3 C5 131.9(2) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 N4 110.11(16) . . ?
N2 C6 N6 109.11(16) . . ?
N4 C6 N6 111.93(16) . . ?
N2 C6 H6 108.6(14) . . ?
N4 C6 H6 106.6(15) . . ?
N6 C6 H6 110.4(14) . . ?
N3 C7 C8 110.36(19) . . ?
N3 C7 C10 122.64(19) . . ?
C8 C7 C10 126.99(19) . . ?
C9 C8 C7 107.02(19) . . ?
C9 C8 H8 127.0(18) . . ?
C7 C8 H8 126.0(18) . . ?
N4 C9 C8 106.08(19) . . ?
N4 C9 C11 123.2(2) . . ?
C8 C9 C11 130.7(2) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N5 C12 C13 111.62(19) . . ?
N5 C12 C15 120.01(19) . . ?
C13 C12 C15 128.37(19) . . ?
C14 C13 C12 106.31(19) . . ?
C14 C13 H13 127.2(16) . . ?
C12 C13 H13 126.4(16) . . ?
C13 C14 N6 105.47(18) . . ?
C13 C14 C16 129.3(2) . . ?
N6 C14 C16 125.27(19) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C24 124.1(2) . . ?
C18 C17 Ir 71.19(12) . . ?
C24 C17 Ir 112.76(14) . . ?
C18 C17 H17 117.4(15) . . ?
C24 C17 H17 112.8(15) . . ?
Ir C17 H17 109.9(15) . . ?
C17 C18 C19 121.4(2) . . ?
C17 C18 Ir 70.20(12) . . ?
C19 C18 Ir 113.91(15) . . ?
C17 C18 H18 120.0(15) . . ?
C19 C18 H18 113.3(15) . . ?
Ir C18 H18 108.9(15) . . ?
C18 C19 C20 112.01(18) . . ?
C18 C19 H19A 111.9(19) . . ?
C20 C19 H19A 109.9(19) . . ?
C18 C19 H19B 107.7(14) . . ?
C20 C19 H19B 111.7(14) . . ?
H19A C19 H19B 103(2) . . ?
C21 C20 C19 111.42(18) . . ?
C21 C20 H20A 104.5(16) . . ?
C19 C20 H20A 111.8(16) . . ?
C21 C20 H20B 110.6(16) . . ?
C19 C20 H20B 109.6(16) . . ?
H20A C20 H20B 109(2) . . ?
C22 C21 C20 124.1(2) . . ?
C22 C21 Ir 70.06(12) . . ?
C20 C21 Ir 112.34(14) . . ?
C22 C21 H21 118.4(16) . . ?
C20 C21 H21 111.8(15) . . ?
Ir C21 H21 111.8(14) . . ?
C21 C22 C23 124.63(19) . . ?
C21 C22 Ir 71.24(12) . . ?
C23 C22 Ir 114.59(14) . . ?
C21 C22 H22 118.3(15) . . ?
C23 C22 H22 113.5(14) . . ?
Ir C22 H22 103.2(14) . . ?
C22 C23 C24 112.31(18) . . ?
C22 C23 H23A 110.1(16) . . ?
C24 C23 H23A 108.5(16) . . ?
C22 C23 H23B 107.8(16) . . ?
C24 C23 H23B 109.2(16) . . ?
H23A C23 H23B 109(2) . . ?
C17 C24 C23 112.14(19) . . ?
C17 C24 H24A 110.0(14) . . ?
C23 C24 H24A 110.1(14) . . ?
C17 C24 H24B 105.9(18) . . ?
C23 C24 H24B 112.4(18) . . ?
H24A C24 H24B 106(2) . . ?
O3 S1 O1 115.29(12) . . ?
O3 S1 O2 114.61(11) . . ?
O1 S1 O2 115.73(13) . . ?
O3 S1 C25 102.96(11) . . ?
O1 S1 C25 102.79(12) . . ?
O2 S1 C25 102.78(11) . . ?
F1 C25 F3 107.3(2) . . ?
F1 C25 F2 107.0(2) . . ?
F3 C25 F2 106.74(19) . . ?
F1 C25 S1 112.28(16) . . ?
F3 C25 S1 111.84(17) . . ?
F2 C25 S1 111.39(16) . . ?

_refine_diff_density_max         1.370
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.096

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: deuterated benzene'
####################################################################### 
# 
# 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_cmpnd_4
_database_code_depnum_ccdc_archive 'CCDC 1812904'
loop_
_audit_author_name
_audit_author_address
'Pilar Garcia-Orduna'
'Instituto de S?ntesis Qu?mica y Cat?lisis Homog?nea (ISQCH, CSIC-Univ. Zaragoza)'
_audit_update_record             
;
2017-12-21 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H38 Ir N6 O, C F3 O3 S'
_chemical_formula_sum            'C26 H38 F3 Ir N6 O4 S'
_chemical_formula_weight         779.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2713(3)
_cell_length_b                   9.7845(4)
_cell_length_c                   19.0733(7)
_cell_angle_alpha                75.6490(10)
_cell_angle_beta                 85.0880(10)
_cell_angle_gamma                79.8680(10)
_cell_volume                     1470.69(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9948
_cell_measurement_theta_min      2.664
_cell_measurement_theta_max      29.441

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    4.672
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4685
_exptl_absorpt_correction_T_max  0.6245
_exptl_absorpt_process_details   
;
 SADABS: Area-Detector Absorption Correction. (1996) Bruker-AXS 
 within APEX2 package.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX DUO CCD system'
_diffrn_measurement_method       'narrow ω frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_reflns_number            17642
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.177
_diffrn_reflns_theta_max         29.613
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7487
_reflns_number_gt                7264
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART in APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_cell_refinement       'SAINT+ in APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT+ in APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP program, SHELXTL v6.12, Bruker2000'
_computing_publication_material  'XCIF program, PLATON(Spek, 1998)'

_refine_special_details          
;
The asymmetric unit contains a Ir complex and a CF3SO3 counterion.

Hydrogen atoms have been observed in Fourier difference maps. 
In order to decrease the number of refined parameters, hydrogen
atoms of methyl groups have been included in the model in calculated
positions and refined with a riding model. The rest of hydrogen
atoms have been included in observed positions and freely refined.
A C-H bond length restraint has been included in the refinement
in the case of C2-H2 bond. 

Hydride has been freely refined, leading to a Ir-H 1.49(2) A 
bond length value. When including a restraint in 
Ir-H bond length in the refinement, the isotropic displacement
parameter of hydride value become too small. Therefore no restraint
has been applied for this atom.

Anisotropic atomic displacement parameter of fluorine atoms of CF3SO3
are high, probably due to a kinetic disorder. Attempts to model these 
atoms in two components lead to unrealistic geometrical parameters. 

At the end of the refinement residual density peaks are located close
to the metal atom. They have no chemical sense.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0216P)²+1.7063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7487
_refine_ls_number_parameters     456
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0190
_refine_ls_wR_factor_ref         0.0472
_refine_ls_wR_factor_gt          0.0468
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir Ir 0.82841(2) 0.58039(2) 0.65944(2) 0.01349(3) Uani 1 1 d . . . . .
N1 N 0.9127(2) 0.3647(2) 0.72441(10) 0.0166(4) Uani 1 1 d . . . . .
N2 N 0.8471(2) 0.3305(2) 0.79402(10) 0.0170(4) Uani 1 1 d . . . . .
N3 N 0.5945(2) 0.5230(2) 0.70552(10) 0.0162(4) Uani 1 1 d . . . . .
N4 N 0.5798(2) 0.4706(2) 0.77892(10) 0.0154(3) Uani 1 1 d . . . . .
N5 N 0.8723(2) 0.6282(2) 0.75677(11) 0.0172(4) Uani 1 1 d . . . . .
N6 N 0.7985(2) 0.5601(2) 0.81993(10) 0.0171(4) Uani 1 1 d . . . . .
C1 C 1.0275(3) 0.2535(2) 0.71798(12) 0.0187(4) Uani 1 1 d . . . . .
C2 C 1.0366(3) 0.1492(3) 0.78368(13) 0.0218(5) Uani 1 1 d D . . . .
C3 C 0.9224(3) 0.2006(2) 0.83152(13) 0.0197(4) Uani 1 1 d . . . . .
C4 C 1.1261(3) 0.2525(3) 0.64888(14) 0.0246(5) Uani 1 1 d . . . . .
H4A H 1.0863 0.3384 0.6120 0.037 Uiso 1 1 calc R U . . .
H4B H 1.1149 0.1674 0.6325 0.037 Uiso 1 1 calc R U . . .
H4C H 1.2420 0.2509 0.6568 0.037 Uiso 1 1 calc R U . . .
C5 C 0.8804(3) 0.1375(3) 0.90923(14) 0.0270(5) Uani 1 1 d . . . . .
H5A H 0.9100 0.1963 0.9394 0.040 Uiso 1 1 calc R U . . .
H5B H 0.9415 0.0403 0.9237 0.040 Uiso 1 1 calc R U . . .
H5C H 0.7621 0.1345 0.9156 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7258(3) 0.4357(2) 0.82038(12) 0.0163(4) Uani 1 1 d . . . . .
C7 C 0.4490(3) 0.5217(2) 0.68038(13) 0.0189(4) Uani 1 1 d . . . . .
C8 C 0.3420(3) 0.4694(3) 0.73770(13) 0.0211(5) Uani 1 1 d . . . . .
C9 C 0.4275(3) 0.4369(2) 0.79988(13) 0.0183(4) Uani 1 1 d . . . . .
C10 C 0.4156(3) 0.5677(3) 0.60147(13) 0.0254(5) Uani 1 1 d . . . . .
H10A H 0.4746 0.6469 0.5783 0.038 Uiso 1 1 calc R U . . .
H10B H 0.2973 0.5991 0.5955 0.038 Uiso 1 1 calc R U . . .
H10C H 0.4529 0.4874 0.5788 0.038 Uiso 1 1 calc R U . . .
C11 C 0.3737(3) 0.3848(3) 0.87681(14) 0.0254(5) Uani 1 1 d . . . . .
H11A H 0.4538 0.3033 0.9001 0.038 Uiso 1 1 calc R U . . .
H11B H 0.2659 0.3550 0.8790 0.038 Uiso 1 1 calc R U . . .
H11C H 0.3659 0.4617 0.9021 0.038 Uiso 1 1 calc R U . . .
C12 C 0.9677(3) 0.7091(3) 0.77599(14) 0.0210(5) Uani 1 1 d . . . . .
C13 C 0.9541(3) 0.6915(3) 0.85141(15) 0.0255(5) Uani 1 1 d . . . . .
C14 C 0.8492(3) 0.5960(3) 0.87837(13) 0.0222(5) Uani 1 1 d . . . . .
C15 C 1.0739(3) 0.7993(3) 0.72415(15) 0.0262(5) Uani 1 1 d . . . . .
H15A H 1.0954 0.7645 0.6798 0.039 Uiso 1 1 calc R U . . .
H15B H 1.1782 0.7943 0.7462 0.039 Uiso 1 1 calc R U . . .
H15C H 1.0179 0.8986 0.7124 0.039 Uiso 1 1 calc R U . . .
C16 C 0.7909(3) 0.5377(3) 0.95390(14) 0.0284(5) Uani 1 1 d . . . . .
H16A H 0.6705 0.5575 0.9574 0.043 Uiso 1 1 calc R U . . .
H16B H 0.8357 0.5829 0.9867 0.043 Uiso 1 1 calc R U . . .
H16C H 0.8278 0.4342 0.9674 0.043 Uiso 1 1 calc R U . . .
C17 C 0.7388(3) 0.8024(2) 0.62008(13) 0.0183(4) Uani 1 1 d . . . . .
C18 C 0.5750(3) 0.8431(3) 0.65824(15) 0.0253(5) Uani 1 1 d . . . . .
C19 C 0.5099(3) 1.0024(3) 0.65360(15) 0.0238(5) Uani 1 1 d . . . . .
C20 C 0.6332(4) 1.0927(3) 0.66628(16) 0.0322(6) Uani 1 1 d . . . . .
C21 C 0.7090(4) 1.1812(3) 0.59882(19) 0.0359(6) Uani 1 1 d . . . . .
C22 C 0.8141(4) 1.1064(3) 0.54543(17) 0.0320(6) Uani 1 1 d . . . . .
C23 C 0.7279(3) 1.0214(3) 0.50750(15) 0.0262(5) Uani 1 1 d . . . . .
C24 C 0.7499(3) 0.8572(3) 0.53780(14) 0.0248(5) Uani 1 1 d . . . . .
C25 C 0.8133(3) 0.5417(2) 0.57101(13) 0.0196(4) Uani 1 1 d . . . . .
O1 O 0.8097(2) 0.5174(2) 0.51535(10) 0.0284(4) Uani 1 1 d . . . . .
S S 0.36465(7) 0.79623(6) 0.91041(3) 0.02173(11) Uani 1 1 d . . . . .
O2 O 0.4290(3) 0.7223(3) 0.85581(14) 0.0457(6) Uani 1 1 d . . . . .
O3 O 0.1941(2) 0.8605(2) 0.90657(13) 0.0353(5) Uani 1 1 d . . . . .
O4 O 0.4130(3) 0.7233(2) 0.98234(12) 0.0424(5) Uani 1 1 d . . . . .
C26 C 0.4687(4) 0.9502(3) 0.88991(19) 0.0390(7) Uani 1 1 d . . . . .
F1 F 0.6292(3) 0.9117(3) 0.8941(2) 0.0919(11) Uani 1 1 d . . . . .
F2 F 0.4362(3) 1.0329(2) 0.82431(13) 0.0650(7) Uani 1 1 d . . . . .
F3 F 0.4188(3) 1.0332(2) 0.93598(14) 0.0650(7) Uani 1 1 d . . . . .
H H 0.997(3) 0.605(3) 0.6309(14) 0.012(6) Uiso 1 1 d . . . . .
H2 H 1.114(3) 0.066(3) 0.7948(19) 0.036(9) Uiso 1 1 d D . . . .
H6 H 0.693(3) 0.393(3) 0.8667(16) 0.013(6) Uiso 1 1 d . . . . .
H8 H 0.228(4) 0.463(4) 0.7348(19) 0.037(9) Uiso 1 1 d . . . . .
H13 H 1.005(4) 0.742(3) 0.8771(18) 0.030(8) Uiso 1 1 d . . . . .
H17 H 0.819(4) 0.846(4) 0.6375(18) 0.034(9) Uiso 1 1 d . . . . .
H18A H 0.483(4) 0.799(4) 0.6381(18) 0.035(9) Uiso 1 1 d . . . . .
H18B H 0.589(4) 0.802(3) 0.7118(18) 0.028(8) Uiso 1 1 d . . . . .
H19A H 0.461(3) 1.047(3) 0.6062(16) 0.018(7) Uiso 1 1 d . . . . .
H19B H 0.419(4) 1.005(3) 0.6889(17) 0.026(8) Uiso 1 1 d . . . . .
H20A H 0.725(5) 1.025(5) 0.699(2) 0.064(13) Uiso 1 1 d . . . . .
H20B H 0.569(4) 1.161(3) 0.6903(17) 0.026(8) Uiso 1 1 d . . . . .
H21A H 0.615(5) 1.250(4) 0.571(2) 0.043(10) Uiso 1 1 d . . . . .
H21B H 0.769(5) 1.239(4) 0.618(2) 0.047(10) Uiso 1 1 d . . . . .
H22A H 0.858(5) 1.176(4) 0.514(2) 0.053(11) Uiso 1 1 d . . . . .
H22B H 0.912(4) 1.040(4) 0.5741(19) 0.035(9) Uiso 1 1 d . . . . .
H23A H 0.605(4) 1.065(3) 0.5056(18) 0.030(8) Uiso 1 1 d . . . . .
H23B H 0.773(4) 1.040(4) 0.4589(19) 0.034(9) Uiso 1 1 d . . . . .
H24A H 0.663(4) 0.810(4) 0.5157(18) 0.036(9) Uiso 1 1 d . . . . .
H24B H 0.860(4) 0.821(3) 0.5209(16) 0.020(7) Uiso 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
Ir C25 1.837(2) . ?
Ir N5 2.098(2) . ?
Ir C17 2.133(2) . ?
Ir N3 2.1631(19) . ?
Ir N1 2.1935(19) . ?
Ir H 1.49(3) . ?
N1 C1 1.335(3) . ?
N1 N2 1.374(3) . ?
N2 C3 1.365(3) . ?
N2 C6 1.458(3) . ?
N3 C7 1.336(3) . ?
N3 N4 1.369(3) . ?
N4 C9 1.360(3) . ?
N4 C6 1.444(3) . ?
N5 C12 1.341(3) . ?
N5 N6 1.374(3) . ?
N6 C14 1.367(3) . ?
N6 C6 1.447(3) . ?
C1 C2 1.405(3) . ?
C1 C4 1.491(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.935(18) . ?
C3 C5 1.494(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 0.92(3) . ?
C7 C8 1.399(3) . ?
C7 C10 1.495(3) . ?
C8 C9 1.373(3) . ?
C8 H8 0.96(4) . ?
C9 C11 1.486(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.403(4) . ?
C12 C15 1.490(4) . ?
C13 C14 1.364(4) . ?
C13 H13 0.94(3) . ?
C14 C16 1.485(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.520(3) . ?
C17 C24 1.528(3) . ?
C17 H17 0.97(4) . ?
C18 C19 1.539(3) . ?
C18 H18A 1.08(3) . ?
C18 H18B 1.01(3) . ?
C19 C20 1.531(4) . ?
C19 H19A 0.99(3) . ?
C19 H19B 0.96(3) . ?
C20 C21 1.516(4) . ?
C20 H20A 1.05(4) . ?
C20 H20B 0.96(3) . ?
C21 C22 1.524(5) . ?
C21 H21A 1.02(4) . ?
C21 H21B 0.96(4) . ?
C22 C23 1.523(4) . ?
C22 H22A 0.90(4) . ?
C22 H22B 1.05(3) . ?
C23 C24 1.550(3) . ?
C23 H23A 1.03(3) . ?
C23 H23B 0.96(4) . ?
C24 H24A 1.08(4) . ?
C24 H24B 0.98(3) . ?
C25 O1 1.148(3) . ?
S O2 1.426(2) . ?
S O4 1.435(2) . ?
S O3 1.440(2) . ?
S C26 1.808(3) . ?
C26 F1 1.318(4) . ?
C26 F2 1.331(4) . ?
C26 F3 1.332(4) . ?

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
C25 Ir N5 173.68(9) . . ?
C25 Ir C17 92.69(10) . . ?
N5 Ir C17 87.40(8) . . ?
C25 Ir N3 96.71(9) . . ?
N5 Ir N3 89.56(7) . . ?
C17 Ir N3 95.80(8) . . ?
C25 Ir N1 100.39(9) . . ?
N5 Ir N1 79.86(7) . . ?
C17 Ir N1 166.70(8) . . ?
N3 Ir N1 80.42(7) . . ?
C25 Ir H 83.4(10) . . ?
N5 Ir H 90.2(10) . . ?
C17 Ir H 90.0(10) . . ?
N3 Ir H 174.2(10) . . ?
N1 Ir H 93.8(10) . . ?
C1 N1 N2 105.85(18) . . ?
C1 N1 Ir 137.05(16) . . ?
N2 N1 Ir 116.74(13) . . ?
C3 N2 N1 111.29(18) . . ?
C3 N2 C6 128.8(2) . . ?
N1 N2 C6 119.56(18) . . ?
C7 N3 N4 105.65(18) . . ?
C7 N3 Ir 136.32(16) . . ?
N4 N3 Ir 118.02(13) . . ?
C9 N4 N3 111.46(18) . . ?
C9 N4 C6 128.75(19) . . ?
N3 N4 C6 118.79(18) . . ?
C12 N5 N6 105.99(19) . . ?
C12 N5 Ir 135.21(17) . . ?
N6 N5 Ir 118.68(14) . . ?
C14 N6 N5 110.95(19) . . ?
C14 N6 C6 127.0(2) . . ?
N5 N6 C6 118.95(18) . . ?
N1 C1 C2 109.9(2) . . ?
N1 C1 C4 121.2(2) . . ?
C2 C1 C4 129.0(2) . . ?
C3 C2 C1 107.0(2) . . ?
C3 C2 H2 126(2) . . ?
C1 C2 H2 127(2) . . ?
N2 C3 C2 106.0(2) . . ?
N2 C3 C5 123.3(2) . . ?
C2 C3 C5 130.7(2) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 N6 112.65(18) . . ?
N4 C6 N2 110.68(18) . . ?
N6 C6 N2 109.84(18) . . ?
N4 C6 H6 105.7(17) . . ?
N6 C6 H6 110.6(17) . . ?
N2 C6 H6 107.2(17) . . ?
N3 C7 C8 110.0(2) . . ?
N3 C7 C10 122.4(2) . . ?
C8 C7 C10 127.5(2) . . ?
C9 C8 C7 106.9(2) . . ?
C9 C8 H8 126(2) . . ?
C7 C8 H8 127(2) . . ?
N4 C9 C8 106.0(2) . . ?
N4 C9 C11 123.3(2) . . ?
C8 C9 C11 130.6(2) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N5 C12 C13 109.3(2) . . ?
N5 C12 C15 124.2(2) . . ?
C13 C12 C15 126.5(2) . . ?
C14 C13 C12 107.5(2) . . ?
C14 C13 H13 128(2) . . ?
C12 C13 H13 125(2) . . ?
C13 C14 N6 106.2(2) . . ?
C13 C14 C16 130.8(2) . . ?
N6 C14 C16 123.0(2) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C24 116.7(2) . . ?
C18 C17 Ir 110.06(16) . . ?
C24 C17 Ir 115.23(16) . . ?
C18 C17 H17 107(2) . . ?
C24 C17 H17 105(2) . . ?
Ir C17 H17 102(2) . . ?
C17 C18 C19 118.8(2) . . ?
C17 C18 H18A 108.2(18) . . ?
C19 C18 H18A 107.9(18) . . ?
C17 C18 H18B 106.9(18) . . ?
C19 C18 H18B 103.3(18) . . ?
H18A C18 H18B 112(3) . . ?
C20 C19 C18 116.7(2) . . ?
C20 C19 H19A 108.8(17) . . ?
C18 C19 H19A 109.6(17) . . ?
C20 C19 H19B 109.8(19) . . ?
C18 C19 H19B 105.9(19) . . ?
H19A C19 H19B 106(2) . . ?
C21 C20 C19 116.0(3) . . ?
C21 C20 H20A 111(2) . . ?
C19 C20 H20A 108(2) . . ?
C21 C20 H20B 105.3(19) . . ?
C19 C20 H20B 104.2(19) . . ?
H20A C20 H20B 112(3) . . ?
C20 C21 C22 119.5(2) . . ?
C20 C21 H21A 107(2) . . ?
C22 C21 H21A 107(2) . . ?
C20 C21 H21B 103(2) . . ?
C22 C21 H21B 113(2) . . ?
H21A C21 H21B 107(3) . . ?
C23 C22 C21 116.6(2) . . ?
C23 C22 H22A 112(3) . . ?
C21 C22 H22A 105(3) . . ?
C23 C22 H22B 110.2(19) . . ?
C21 C22 H22B 106.6(19) . . ?
H22A C22 H22B 106(3) . . ?
C22 C23 C24 117.4(2) . . ?
C22 C23 H23A 108.1(18) . . ?
C24 C23 H23A 110.8(18) . . ?
C22 C23 H23B 105(2) . . ?
C24 C23 H23B 108(2) . . ?
H23A C23 H23B 107(3) . . ?
C17 C24 C23 117.1(2) . . ?
C17 C24 H24A 107.3(18) . . ?
C23 C24 H24A 111.6(18) . . ?
C17 C24 H24B 107.5(18) . . ?
C23 C24 H24B 105.4(18) . . ?
H24A C24 H24B 107(2) . . ?
O1 C25 Ir 177.6(2) . . ?
O2 S O4 114.62(15) . . ?
O2 S O3 116.53(15) . . ?
O4 S O3 113.78(14) . . ?
O2 S C26 103.61(16) . . ?
O4 S C26 103.36(16) . . ?
O3 S C26 102.49(14) . . ?
F1 C26 F2 108.8(3) . . ?
F1 C26 F3 107.7(3) . . ?
F2 C26 F3 105.7(3) . . ?
F1 C26 S 111.3(2) . . ?
F2 C26 S 112.0(2) . . ?
F3 C26 S 111.1(2) . . ?

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
C1 N1 N2 C3 1.4(3) . . . . ?
Ir N1 N2 C3 -172.94(15) . . . . ?
C1 N1 N2 C6 175.2(2) . . . . ?
Ir N1 N2 C6 0.9(2) . . . . ?
C7 N3 N4 C9 -0.1(2) . . . . ?
Ir N3 N4 C9 -178.91(14) . . . . ?
C7 N3 N4 C6 169.48(19) . . . . ?
Ir N3 N4 C6 -9.4(2) . . . . ?
C12 N5 N6 C14 -1.0(2) . . . . ?
Ir N5 N6 C14 175.71(15) . . . . ?
C12 N5 N6 C6 -162.44(19) . . . . ?
Ir N5 N6 C6 14.3(2) . . . . ?
N2 N1 C1 C2 -0.7(3) . . . . ?
Ir N1 C1 C2 171.82(17) . . . . ?
N2 N1 C1 C4 -179.9(2) . . . . ?
Ir N1 C1 C4 -7.4(4) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
C4 C1 C2 C3 179.0(2) . . . . ?
N1 N2 C3 C2 -1.5(3) . . . . ?
C6 N2 C3 C2 -174.6(2) . . . . ?
N1 N2 C3 C5 178.1(2) . . . . ?
C6 N2 C3 C5 4.9(4) . . . . ?
C1 C2 C3 N2 1.0(3) . . . . ?
C1 C2 C3 C5 -178.5(3) . . . . ?
C9 N4 C6 N6 -126.8(2) . . . . ?
N3 N4 C6 N6 65.7(3) . . . . ?
C9 N4 C6 N2 109.8(2) . . . . ?
N3 N4 C6 N2 -57.7(3) . . . . ?
C14 N6 C6 N4 132.3(2) . . . . ?
N5 N6 C6 N4 -69.6(2) . . . . ?
C14 N6 C6 N2 -103.8(2) . . . . ?
N5 N6 C6 N2 54.3(2) . . . . ?
C3 N2 C6 N4 -124.6(2) . . . . ?
N1 N2 C6 N4 62.8(3) . . . . ?
C3 N2 C6 N6 110.4(3) . . . . ?
N1 N2 C6 N6 -62.2(2) . . . . ?
N4 N3 C7 C8 0.3(3) . . . . ?
Ir N3 C7 C8 178.88(17) . . . . ?
N4 N3 C7 C10 -178.4(2) . . . . ?
Ir N3 C7 C10 0.2(4) . . . . ?
N3 C7 C8 C9 -0.5(3) . . . . ?
C10 C7 C8 C9 178.1(2) . . . . ?
N3 N4 C9 C8 -0.2(3) . . . . ?
C6 N4 C9 C8 -168.5(2) . . . . ?
N3 N4 C9 C11 -176.7(2) . . . . ?
C6 N4 C9 C11 15.0(4) . . . . ?
C7 C8 C9 N4 0.4(3) . . . . ?
C7 C8 C9 C11 176.6(2) . . . . ?
N6 N5 C12 C13 0.1(3) . . . . ?
Ir N5 C12 C13 -175.79(17) . . . . ?
N6 N5 C12 C15 178.6(2) . . . . ?
Ir N5 C12 C15 2.7(4) . . . . ?
N5 C12 C13 C14 0.8(3) . . . . ?
C15 C12 C13 C14 -177.6(2) . . . . ?
C12 C13 C14 N6 -1.4(3) . . . . ?
C12 C13 C14 C16 179.8(3) . . . . ?
N5 N6 C14 C13 1.5(3) . . . . ?
C6 N6 C14 C13 161.1(2) . . . . ?
N5 N6 C14 C16 -179.5(2) . . . . ?
C6 N6 C14 C16 -20.0(4) . . . . ?
C24 C17 C18 C19 -62.1(3) . . . . ?
Ir C17 C18 C19 164.14(19) . . . . ?
C17 C18 C19 C20 -45.6(3) . . . . ?
C18 C19 C20 C21 99.0(3) . . . . ?
C19 C20 C21 C22 -62.5(4) . . . . ?
C20 C21 C22 C23 63.7(4) . . . . ?
C21 C22 C23 C24 -99.7(3) . . . . ?
C18 C17 C24 C23 63.3(3) . . . . ?
Ir C17 C24 C23 -165.26(18) . . . . ?
C22 C23 C24 C17 42.9(3) . . . . ?
O2 S C26 F1 -61.2(3) . . . . ?
O4 S C26 F1 58.7(3) . . . . ?
O3 S C26 F1 177.2(3) . . . . ?
O2 S C26 F2 60.9(3) . . . . ?
O4 S C26 F2 -179.3(2) . . . . ?
O3 S C26 F2 -60.8(3) . . . . ?
O2 S C26 F3 178.7(2) . . . . ?
O4 S C26 F3 -61.4(3) . . . . ?
O3 S C26 F3 57.1(3) . . . . ?

_refine_diff_density_max         2.017
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.091

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane / pentane'
