# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_sauvageot2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 {Bis-(2-phenylpyridine)}{4,4-dimethyl-2,2-dipyridylamine} 
iridium hexafluorophosphate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H29 F6 Ir N5 P'
_chemical_formula_sum            'C34 H29 F6 Ir N5 P'
_chemical_formula_weight         844.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   13.828(3)
_cell_length_b                   16.821(4)
_cell_length_c                   15.516(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.367(13)
_cell_angle_gamma                90.00
_cell_volume                     3609.2(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      29.26

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1656
_exptl_absorpt_coefficient_mu    3.804
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0700
_exptl_absorpt_correction_T_max  0.6437
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            58333
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         29.57
_reflns_number_total             10078
_reflns_number_gt                6709
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0354P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10078
_refine_ls_number_parameters     426
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0701
_refine_ls_wR_factor_gt          0.0649
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.663585(7) 0.252039(6) 0.516815(6) 0.01848(4) Uani 1 1 d . . .
P3 P 0.10389(7) 0.08037(5) 0.12781(5) 0.0357(2) Uani 1 1 d . . .
N3 N 0.79463(18) 0.26122(13) 0.44263(15) 0.0235(5) Uani 1 1 d . . .
N5 N 0.72735(16) 0.34022(13) 0.60131(14) 0.0193(5) Uani 1 1 d . . .
C29 C 0.7904(2) 0.39505(17) 0.57550(18) 0.0234(6) Uani 1 1 d . . .
N1 N 0.72249(17) 0.15425(14) 0.57409(14) 0.0224(5) Uani 1 1 d . . .
N2 N 0.59026(18) 0.34343(14) 0.45888(14) 0.0241(5) Uani 1 1 d . . .
N4 N 0.83570(18) 0.38896(15) 0.49637(15) 0.0312(6) Uani 1 1 d . . .
H4 H 0.8561 0.4345 0.4753 0.037 Uiso 1 1 calc R . .
C23 C 0.8545(2) 0.32399(17) 0.44485(17) 0.0245(6) Uani 1 1 d . . .
C24 C 0.9350(2) 0.32969(19) 0.3919(2) 0.0361(8) Uani 1 1 d . . .
H24 H 0.9751 0.3755 0.3948 0.043 Uiso 1 1 calc R . .
C7 C 0.6927(2) 0.08237(17) 0.54232(17) 0.0241(6) Uani 1 1 d . . .
C11 C 0.7856(2) 0.15604(18) 0.64104(18) 0.0292(7) Uani 1 1 d . . .
H11 H 0.8068 0.2060 0.6624 0.035 Uiso 1 1 calc R . .
C1 C 0.6243(2) 0.08893(17) 0.47064(17) 0.0226(6) Uani 1 1 d . . .
C12 C 0.5405(2) 0.24871(16) 0.58476(18) 0.0221(5) Uani 1 1 d . . .
C18 C 0.4995(2) 0.35753(18) 0.48983(18) 0.0287(7) Uani 1 1 d . . .
C6 C 0.5825(2) 0.02277(18) 0.43029(17) 0.0270(7) Uani 1 1 d . . .
H6 H 0.5994 -0.0293 0.4486 0.032 Uiso 1 1 calc R . .
C17 C 0.5167(2) 0.19676(18) 0.65135(18) 0.0282(7) Uani 1 1 d . . .
H17 H 0.5614 0.1566 0.6680 0.034 Uiso 1 1 calc R . .
C13 C 0.4720(2) 0.30675(18) 0.56160(18) 0.0282(7) Uani 1 1 d . . .
C3 C 0.5355(2) 0.17551(18) 0.37650(17) 0.0265(6) Uani 1 1 d . . .
H3 H 0.5191 0.2273 0.3568 0.032 Uiso 1 1 calc R . .
C22 C 0.6228(2) 0.38779(19) 0.39233(18) 0.0323(7) Uani 1 1 d . . .
H22 H 0.6856 0.3773 0.3705 0.039 Uiso 1 1 calc R . .
C8 C 0.7269(2) 0.01289(18) 0.57880(18) 0.0326(7) Uani 1 1 d . . .
H8 H 0.7064 -0.0369 0.5562 0.039 Uiso 1 1 calc R . .
C16 C 0.4290(3) 0.2025(2) 0.6938(2) 0.0389(8) Uani 1 1 d . . .
H16 H 0.4142 0.1663 0.7389 0.047 Uiso 1 1 calc R . .
C21 C 0.5695(3) 0.4466(2) 0.3555(2) 0.0424(9) Uani 1 1 d . . .
H21 H 0.5952 0.4774 0.3097 0.051 Uiso 1 1 calc R . .
C9 C 0.7901(3) 0.0150(2) 0.6473(2) 0.0440(9) Uani 1 1 d . . .
H9 H 0.8133 -0.0328 0.6726 0.053 Uiso 1 1 calc R . .
C2 C 0.6014(2) 0.16674(16) 0.44416(17) 0.0213(6) Uani 1 1 d . . .
C10 C 0.8195(3) 0.0883(2) 0.6788(2) 0.0393(8) Uani 1 1 d . . .
H10 H 0.8630 0.0913 0.7263 0.047 Uiso 1 1 calc R . .
C4 C 0.4935(2) 0.1096(2) 0.33737(19) 0.0321(7) Uani 1 1 d . . .
H4A H 0.4482 0.1170 0.2918 0.039 Uiso 1 1 calc R . .
C19 C 0.4425(3) 0.4164(2) 0.4518(2) 0.0393(8) Uani 1 1 d . . .
H19 H 0.3789 0.4257 0.4722 0.047 Uiso 1 1 calc R . .
C5 C 0.5169(2) 0.0333(2) 0.36402(19) 0.0324(8) Uani 1 1 d . . .
H5 H 0.4879 -0.0114 0.3368 0.039 Uiso 1 1 calc R . .
C15 C 0.3631(3) 0.2605(2) 0.6710(2) 0.0429(9) Uani 1 1 d . . .
H15 H 0.3033 0.2642 0.7004 0.052 Uiso 1 1 calc R . .
C20 C 0.4779(3) 0.4610(2) 0.3853(2) 0.0458(9) Uani 1 1 d . . .
H20 H 0.4394 0.5016 0.3600 0.055 Uiso 1 1 calc R . .
C14 C 0.3837(2) 0.3132(2) 0.6054(2) 0.0396(8) Uani 1 1 d . . .
H14 H 0.3386 0.3534 0.5900 0.048 Uiso 1 1 calc R . .
C32 C 0.7113(2) 0.41281(17) 0.73406(18) 0.0265(6) Uani 1 1 d . . .
H32 H 0.6829 0.4162 0.7895 0.032 Uiso 1 1 calc R . .
C26 C 0.8966(3) 0.2025(2) 0.3356(2) 0.0364(8) Uani 1 1 d . . .
H26 H 0.9090 0.1588 0.2985 0.044 Uiso 1 1 calc R . .
C33 C 0.6913(2) 0.35000(17) 0.68152(17) 0.0244(6) Uani 1 1 d . . .
H33 H 0.6490 0.3102 0.7027 0.029 Uiso 1 1 calc R . .
C27 C 0.8200(2) 0.20074(19) 0.38967(19) 0.0327(7) Uani 1 1 d . . .
H27 H 0.7815 0.1540 0.3905 0.039 Uiso 1 1 calc R . .
C25 C 0.9573(3) 0.2687(2) 0.3346(2) 0.0376(8) Uani 1 1 d . . .
C31 C 0.7736(2) 0.47183(18) 0.7058(2) 0.0335(8) Uani 1 1 d . . .
C30 C 0.8131(2) 0.46201(19) 0.6249(2) 0.0341(8) Uani 1 1 d . . .
H30 H 0.8560 0.5010 0.6028 0.041 Uiso 1 1 calc R . .
F2 F 0.03970(15) 0.01848(12) 0.07511(14) 0.0565(6) Uani 1 1 d . . .
F1 F 0.02853(19) 0.14757(12) 0.10424(14) 0.0688(7) Uani 1 1 d . . .
F4 F 0.16998(17) 0.14168(15) 0.17722(17) 0.0840(9) Uani 1 1 d . . .
F3 F 0.17831(16) 0.01077(13) 0.14954(13) 0.0583(6) Uani 1 1 d . . .
F6 F 0.16313(19) 0.09582(15) 0.04134(14) 0.0731(8) Uani 1 1 d . . .
F5 F 0.04644(16) 0.06208(15) 0.21217(12) 0.0664(7) Uani 1 1 d . . .
C34 C 0.7986(3) 0.5416(2) 0.7620(3) 0.0681(14) Uani 1 1 d . . .
H34A H 0.8668 0.5382 0.7794 0.102 Uiso 1 1 calc R . .
H34B H 0.7578 0.5410 0.8134 0.102 Uiso 1 1 calc R . .
H34C H 0.7877 0.5910 0.7299 0.102 Uiso 1 1 calc R . .
C28 C 1.0413(3) 0.2745(3) 0.2760(3) 0.0668(14) Uani 1 1 d . . .
H28A H 1.0194 0.2679 0.2162 0.100 Uiso 1 1 calc R . .
H28B H 1.0882 0.2327 0.2903 0.100 Uiso 1 1 calc R . .
H28C H 1.0720 0.3267 0.2827 0.100 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C12 2.008(3) . ?
Ir1 C2 2.014(3) . ?
Ir1 N1 2.037(2) . ?
Ir1 N2 2.046(2) . ?
Ir1 N3 2.159(2) . ?
Ir1 N5 2.164(2) . ?
P3 F5 1.566(2) . ?
P3 F4 1.574(2) . ?
P3 F1 1.579(2) . ?
P3 F2 1.591(2) . ?
P3 F3 1.593(2) . ?
P3 F6 1.598(2) . ?
N3 C23 1.342(3) . ?
N3 C27 1.355(4) . ?
N5 C29 1.332(3) . ?
N5 C33 1.354(3) . ?
C29 N4 1.386(3) . ?
C29 C30 1.397(4) . ?
N1 C11 1.352(4) . ?
N1 C7 1.368(4) . ?
N2 C22 1.354(4) . ?
N2 C18 1.368(4) . ?
N4 C23 1.380(3) . ?
N4 H4 0.8800 . ?
C23 C24 1.391(4) . ?
C24 C25 1.393(4) . ?
C24 H24 0.9500 . ?
C7 C8 1.381(4) . ?
C7 C1 1.459(4) . ?
C11 C10 1.362(4) . ?
C11 H11 0.9500 . ?
C1 C6 1.400(4) . ?
C1 C2 1.407(4) . ?
C12 C17 1.395(4) . ?
C12 C13 1.406(4) . ?
C18 C19 1.394(4) . ?
C18 C13 1.456(4) . ?
C6 C5 1.378(4) . ?
C6 H6 0.9500 . ?
C17 C16 1.387(4) . ?
C17 H17 0.9500 . ?
C13 C14 1.405(4) . ?
C3 C4 1.389(4) . ?
C3 C2 1.394(4) . ?
C3 H3 0.9500 . ?
C22 C21 1.358(4) . ?
C22 H22 0.9500 . ?
C8 C9 1.372(5) . ?
C8 H8 0.9500 . ?
C16 C15 1.380(5) . ?
C16 H16 0.9500 . ?
C21 C20 1.373(5) . ?
C21 H21 0.9500 . ?
C9 C10 1.387(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C4 C5 1.387(4) . ?
C4 H4A 0.9500 . ?
C19 C20 1.368(5) . ?
C19 H19 0.9500 . ?
C5 H5 0.9500 . ?
C15 C14 1.380(5) . ?
C15 H15 0.9500 . ?
C20 H20 0.9500 . ?
C14 H14 0.9500 . ?
C32 C33 1.362(4) . ?
C32 C31 1.387(4) . ?
C32 H32 0.9500 . ?
C26 C27 1.357(4) . ?
C26 C25 1.393(5) . ?
C26 H26 0.9500 . ?
C33 H33 0.9500 . ?
C27 H27 0.9500 . ?
C25 C28 1.484(5) . ?
C31 C30 1.381(4) . ?
C31 C34 1.501(4) . ?
C30 H30 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 Ir1 C2 85.07(11) . . ?
C12 Ir1 N1 94.95(10) . . ?
C2 Ir1 N1 80.62(11) . . ?
C12 Ir1 N2 80.35(11) . . ?
C2 Ir1 N2 94.64(11) . . ?
N1 Ir1 N2 173.64(9) . . ?
C12 Ir1 N3 177.41(10) . . ?
C2 Ir1 N3 96.27(10) . . ?
N1 Ir1 N3 87.46(9) . . ?
N2 Ir1 N3 97.31(9) . . ?
C12 Ir1 N5 92.54(9) . . ?
C2 Ir1 N5 176.74(9) . . ?
N1 Ir1 N5 97.41(10) . . ?
N2 Ir1 N5 87.13(9) . . ?
N3 Ir1 N5 86.21(9) . . ?
F5 P3 F4 91.01(14) . . ?
F5 P3 F1 89.81(13) . . ?
F4 P3 F1 91.37(14) . . ?
F5 P3 F2 90.96(13) . . ?
F4 P3 F2 177.98(13) . . ?
F1 P3 F2 89.10(13) . . ?
F5 P3 F3 90.53(12) . . ?
F4 P3 F3 90.35(14) . . ?
F1 P3 F3 178.23(14) . . ?
F2 P3 F3 89.17(12) . . ?
F5 P3 F6 178.03(14) . . ?
F4 P3 F6 90.19(14) . . ?
F1 P3 F6 91.73(14) . . ?
F2 P3 F6 87.83(13) . . ?
F3 P3 F6 87.89(12) . . ?
C23 N3 C27 116.4(3) . . ?
C23 N3 Ir1 124.22(18) . . ?
C27 N3 Ir1 119.4(2) . . ?
C29 N5 C33 116.0(2) . . ?
C29 N5 Ir1 123.86(18) . . ?
C33 N5 Ir1 119.30(18) . . ?
N5 C29 N4 121.0(3) . . ?
N5 C29 C30 122.6(3) . . ?
N4 C29 C30 116.4(3) . . ?
C11 N1 C7 119.2(2) . . ?
C11 N1 Ir1 124.8(2) . . ?
C7 N1 Ir1 115.94(19) . . ?
C22 N2 C18 118.9(3) . . ?
C22 N2 Ir1 125.6(2) . . ?
C18 N2 Ir1 115.43(19) . . ?
C23 N4 C29 131.3(2) . . ?
C23 N4 H4 114.4 . . ?
C29 N4 H4 114.4 . . ?
N3 C23 N4 121.3(2) . . ?
N3 C23 C24 122.3(3) . . ?
N4 C23 C24 116.2(3) . . ?
C23 C24 C25 120.5(3) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
N1 C7 C8 119.9(3) . . ?
N1 C7 C1 113.6(2) . . ?
C8 C7 C1 126.5(3) . . ?
N1 C11 C10 122.0(3) . . ?
N1 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C6 C1 C2 121.2(3) . . ?
C6 C1 C7 123.0(3) . . ?
C2 C1 C7 115.9(2) . . ?
C17 C12 C13 117.5(3) . . ?
C17 C12 Ir1 127.7(2) . . ?
C13 C12 Ir1 114.7(2) . . ?
N2 C18 C19 119.5(3) . . ?
N2 C18 C13 114.3(3) . . ?
C19 C18 C13 126.2(3) . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C16 C17 C12 121.4(3) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 C18 123.8(3) . . ?
C12 C13 C18 115.1(3) . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
N2 C22 C21 122.7(3) . . ?
N2 C22 H22 118.7 . . ?
C21 C22 H22 118.7 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C15 C16 C17 120.3(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C22 C21 C20 119.1(3) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C8 C9 C10 118.6(3) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 Ir1 128.4(2) . . ?
C1 C2 Ir1 113.9(2) . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C19 C20 C21 119.5(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C15 C14 C13 119.5(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C33 C32 C31 119.4(3) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C27 C26 C25 119.8(3) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
N5 C33 C32 124.7(3) . . ?
N5 C33 H33 117.6 . . ?
C32 C33 H33 117.6 . . ?
N3 C27 C26 124.4(3) . . ?
N3 C27 H27 117.8 . . ?
C26 C27 H27 117.8 . . ?
C26 C25 C24 116.5(3) . . ?
C26 C25 C28 122.2(3) . . ?
C24 C25 C28 121.3(3) . . ?
C30 C31 C32 116.8(3) . . ?
C30 C31 C34 122.0(3) . . ?
C32 C31 C34 121.1(3) . . ?
C31 C30 C29 120.4(3) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
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 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.57
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.023
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.104

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 0.000 327 104 ' '
2 0.000 0.000 0.500 327 104 ' '
_platon_squeeze_details          
;
;
_database_code_depnum_ccdc_archive 'CCDC 988580'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sauvageot1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 {Bis-(1-phenylpyrazole)}{4,4-dimethyl-2,2-dipyridylamine}
 iridium hexafluorophosphate 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H27 F6 Ir N7 P'
_chemical_formula_sum            'C30 H27 F6 Ir N7 P'
_chemical_formula_weight         821.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.3281(6)
_cell_length_b                   15.4516(10)
_cell_length_c                   23.6282(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.742(3)
_cell_angle_gamma                90.00
_cell_volume                     3401.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9948
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      26.94

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1604
_exptl_absorpt_coefficient_mu    4.035
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.635
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            61905
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0341
_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         2.17
_diffrn_reflns_theta_max         27.14
_reflns_number_total             7497
_reflns_number_gt                6347
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0239P)²+7.5997P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7497
_refine_ls_number_parameters     412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0691
_refine_ls_wR_factor_gt          0.0665
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.717365(15) 0.566033(9) 0.696282(6) 0.02075(5) Uani 1 1 d . . .
P1 P 0.92343(18) 0.26978(11) 0.99413(7) 0.0595(4) Uani 1 1 d . . .
F1 F 0.8827(5) 0.2685(4) 1.05769(18) 0.1188(18) Uani 1 1 d . . .
F2 F 0.9647(7) 0.2683(4) 0.9322(2) 0.154(2) Uani 1 1 d . . .
F3 F 0.8465(5) 0.1775(2) 0.98894(18) 0.0941(13) Uani 1 1 d . . .
F4 F 0.7771(5) 0.3132(3) 0.9752(3) 0.127(2) Uani 1 1 d . . .
F5 F 0.9911(6) 0.3621(3) 1.0035(3) 0.134(2) Uani 1 1 d . . .
F6 F 1.0691(4) 0.2249(3) 1.0135(2) 0.1171(18) Uani 1 1 d . . .
N7 N 0.9096(3) 0.51677(19) 0.66084(14) 0.0230(7) Uani 1 1 d . . .
N6 N 0.7773(4) 0.4347(2) 0.59190(16) 0.0307(8) Uani 1 1 d . . .
N5 N 0.6207(3) 0.44688(19) 0.66704(14) 0.0244(7) Uani 1 1 d . . .
N4 N 0.5346(4) 0.6774(2) 0.62708(16) 0.0343(8) Uani 1 1 d . . .
N3 N 0.6574(3) 0.6296(2) 0.62391(15) 0.0280(7) Uani 1 1 d . . .
N2 N 0.8429(4) 0.5797(2) 0.80935(15) 0.0334(8) Uani 1 1 d . . .
N1 N 0.7771(4) 0.5199(2) 0.77409(14) 0.0278(7) Uani 1 1 d . . .
C29 C 1.0397(4) 0.5436(3) 0.68090(19) 0.0301(9) Uani 1 1 d . . .
H29 H 1.0461 0.5726 0.7164 0.036 Uiso 1 1 calc R . .
C28 C 1.1631(4) 0.5313(3) 0.6529(2) 0.0333(10) Uani 1 1 d . . .
H28 H 1.2529 0.5492 0.6697 0.040 Uiso 1 1 calc R . .
C27 C 1.1567(4) 0.4927(3) 0.59998(18) 0.0279(9) Uani 1 1 d . . .
C26 C 1.0259(4) 0.4614(3) 0.58050(18) 0.0269(9) Uani 1 1 d . . .
H26 H 1.0175 0.4326 0.5450 0.032 Uiso 1 1 calc R . .
C25 C 0.9054(4) 0.4714(2) 0.61249(17) 0.0232(8) Uani 1 1 d . . .
C19 C 0.6625(4) 0.4034(3) 0.62187(17) 0.0234(8) Uani 1 1 d . . .
C23 C 0.5088(4) 0.4123(3) 0.69478(19) 0.0304(9) Uani 1 1 d . . .
H23 H 0.4790 0.4408 0.7278 0.036 Uiso 1 1 calc R . .
C22 C 0.4377(5) 0.3390(3) 0.67756(19) 0.0347(10) Uani 1 1 d . . .
H22 H 0.3610 0.3175 0.6985 0.042 Uiso 1 1 calc R . .
C21 C 0.4782(4) 0.2958(3) 0.62899(19) 0.0325(9) Uani 1 1 d . . .
C20 C 0.5932(4) 0.3288(3) 0.60142(18) 0.0275(9) Uani 1 1 d . . .
H20 H 0.6252 0.3007 0.5685 0.033 Uiso 1 1 calc R . .
C24 C 0.3998(6) 0.2167(3) 0.6070(2) 0.0462(12) Uani 1 1 d . . .
H24B H 0.3090 0.2340 0.5877 0.069 Uiso 1 1 calc R . .
H24C H 0.3802 0.1783 0.6387 0.069 Uiso 1 1 calc R . .
H24A H 0.4591 0.1862 0.5803 0.069 Uiso 1 1 calc R . .
C30 C 1.2880(5) 0.4858(3) 0.5652(2) 0.0433(12) Uani 1 1 d . . .
H30B H 1.2693 0.4449 0.5341 0.065 Uiso 1 1 calc R . .
H30A H 1.3695 0.4653 0.5894 0.065 Uiso 1 1 calc R . .
H30C H 1.3106 0.5428 0.5498 0.065 Uiso 1 1 calc R . .
C10 C 0.5305(4) 0.6184(3) 0.71973(18) 0.0271(9) Uani 1 1 d . . .
C15 C 0.4600(5) 0.6101(3) 0.7699(2) 0.0396(11) Uani 1 1 d . . .
H15 H 0.4991 0.5741 0.7993 0.048 Uiso 1 1 calc R . .
C14 C 0.3312(5) 0.6548(3) 0.7774(2) 0.0478(13) Uani 1 1 d . . .
H14 H 0.2841 0.6480 0.8119 0.057 Uiso 1 1 calc R . .
C13 C 0.2723(5) 0.7076(3) 0.7363(3) 0.0524(15) Uani 1 1 d . . .
H13 H 0.1859 0.7379 0.7425 0.063 Uiso 1 1 calc R . .
C12 C 0.3376(5) 0.7170(3) 0.6860(2) 0.0463(13) Uani 1 1 d . . .
H12 H 0.2971 0.7532 0.6570 0.056 Uiso 1 1 calc R . .
C11 C 0.4643(4) 0.6724(3) 0.6786(2) 0.0345(10) Uani 1 1 d . . .
C16 C 0.7117(6) 0.6476(3) 0.5750(2) 0.0436(12) Uani 1 1 d . . .
H16 H 0.7977 0.6238 0.5618 0.052 Uiso 1 1 calc R . .
C17 C 0.6233(7) 0.7075(4) 0.5454(3) 0.0668(17) Uani 1 1 d . . .
H17 H 0.6376 0.7314 0.5090 0.080 Uiso 1 1 calc R . .
C18 C 0.5135(6) 0.7242(4) 0.5793(2) 0.0563(15) Uani 1 1 d . . .
H18 H 0.4353 0.7622 0.5708 0.068 Uiso 1 1 calc R . .
C1 C 0.8137(4) 0.6725(2) 0.73004(17) 0.0243(8) Uani 1 1 d . . .
C2 C 0.8650(4) 0.6635(3) 0.78608(18) 0.0283(9) Uani 1 1 d . . .
C7 C 0.7699(6) 0.4478(3) 0.8033(2) 0.0426(12) Uani 1 1 d . . .
H7 H 0.7303 0.3951 0.7889 0.051 Uiso 1 1 calc R . .
C8 C 0.8282(7) 0.4592(4) 0.8581(2) 0.0582(15) Uani 1 1 d . . .
H8 H 0.8351 0.4174 0.8876 0.070 Uiso 1 1 calc R . .
C9 C 0.8737(6) 0.5435(4) 0.8604(2) 0.0519(14) Uani 1 1 d . . .
H9 H 0.9189 0.5715 0.8923 0.062 Uiso 1 1 calc R . .
C3 C 0.9333(5) 0.7282(3) 0.8174(2) 0.0422(12) Uani 1 1 d . . .
H3 H 0.9671 0.7184 0.8554 0.051 Uiso 1 1 calc R . .
C4 C 0.9508(5) 0.8066(3) 0.7919(3) 0.0503(14) Uani 1 1 d . . .
H4 H 0.9973 0.8523 0.8125 0.060 Uiso 1 1 calc R . .
C5 C 0.9015(5) 0.8200(3) 0.7368(2) 0.0450(13) Uani 1 1 d . . .
H5 H 0.9135 0.8751 0.7198 0.054 Uiso 1 1 calc R . .
C6 C 0.8343(5) 0.7537(3) 0.7056(2) 0.0355(10) Uani 1 1 d . . .
H6 H 0.8021 0.7637 0.6675 0.043 Uiso 1 1 calc R . .
H1 H 0.787(5) 0.411(3) 0.565(2) 0.029(14) 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 C1 2.020(4) . ?
Ir1 C10 2.023(4) . ?
Ir1 N1 2.025(3) . ?
Ir1 N3 2.027(3) . ?
Ir1 N5 2.150(3) . ?
Ir1 N7 2.154(3) . ?
P1 F2 1.531(5) . ?
P1 F1 1.567(5) . ?
P1 F4 1.567(4) . ?
P1 F5 1.572(4) . ?
P1 F6 1.574(4) . ?
P1 F3 1.598(4) . ?
N7 C25 1.339(5) . ?
N7 C29 1.348(5) . ?
N6 C25 1.390(5) . ?
N6 C19 1.397(5) . ?
N6 H1 0.74(5) . ?
N5 C19 1.335(5) . ?
N5 C23 1.367(5) . ?
N4 C18 1.347(6) . ?
N4 N3 1.369(5) . ?
N4 C11 1.411(6) . ?
N3 C16 1.313(6) . ?
N2 C9 1.348(6) . ?
N2 N1 1.369(5) . ?
N2 C2 1.425(5) . ?
N1 C7 1.314(5) . ?
C29 C28 1.368(6) . ?
C29 H29 0.9500 . ?
C28 C27 1.384(6) . ?
C28 H28 0.9500 . ?
C27 C26 1.372(6) . ?
C27 C30 1.511(6) . ?
C26 C25 1.393(5) . ?
C26 H26 0.9500 . ?
C19 C20 1.398(5) . ?
C23 C22 1.364(6) . ?
C23 H23 0.9500 . ?
C22 C21 1.395(6) . ?
C22 H22 0.9500 . ?
C21 C20 1.379(6) . ?
C21 C24 1.504(6) . ?
C20 H20 0.9500 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 H24A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30C 0.9800 . ?
C10 C15 1.388(6) . ?
C10 C11 1.403(6) . ?
C15 C14 1.404(6) . ?
C15 H15 0.9500 . ?
C14 C13 1.365(8) . ?
C14 H14 0.9500 . ?
C13 C12 1.367(8) . ?
C13 H13 0.9500 . ?
C12 C11 1.387(6) . ?
C12 H12 0.9500 . ?
C16 C17 1.404(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.356(8) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C1 C2 1.393(6) . ?
C1 C6 1.397(6) . ?
C2 C3 1.381(6) . ?
C7 C8 1.391(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.371(8) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C3 C4 1.366(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ir1 C10 86.51(15) . . ?
C1 Ir1 N1 80.23(15) . . ?
C10 Ir1 N1 95.46(15) . . ?
C1 Ir1 N3 92.20(15) . . ?
C10 Ir1 N3 80.25(15) . . ?
N1 Ir1 N3 171.56(13) . . ?
C1 Ir1 N5 175.00(15) . . ?
C10 Ir1 N5 94.39(14) . . ?
N1 Ir1 N5 94.78(13) . . ?
N3 Ir1 N5 92.81(13) . . ?
C1 Ir1 N7 94.51(13) . . ?
C10 Ir1 N7 172.77(15) . . ?
N1 Ir1 N7 91.76(13) . . ?
N3 Ir1 N7 92.55(13) . . ?
N5 Ir1 N7 85.21(12) . . ?
F2 P1 F1 178.3(4) . . ?
F2 P1 F4 89.4(3) . . ?
F1 P1 F4 91.8(3) . . ?
F2 P1 F5 91.8(4) . . ?
F1 P1 F5 89.5(3) . . ?
F4 P1 F5 89.4(3) . . ?
F2 P1 F6 91.0(3) . . ?
F1 P1 F6 87.8(3) . . ?
F4 P1 F6 179.1(3) . . ?
F5 P1 F6 91.4(3) . . ?
F2 P1 F3 92.6(3) . . ?
F1 P1 F3 86.2(3) . . ?
F4 P1 F3 88.8(2) . . ?
F5 P1 F3 175.2(3) . . ?
F6 P1 F3 90.4(3) . . ?
C25 N7 C29 116.7(3) . . ?
C25 N7 Ir1 121.7(3) . . ?
C29 N7 Ir1 120.5(3) . . ?
C25 N6 C19 129.1(4) . . ?
C25 N6 H1 111(4) . . ?
C19 N6 H1 113(4) . . ?
C19 N5 C23 116.5(3) . . ?
C19 N5 Ir1 123.6(3) . . ?
C23 N5 Ir1 119.9(3) . . ?
C18 N4 N3 109.5(4) . . ?
C18 N4 C11 134.2(4) . . ?
N3 N4 C11 116.2(3) . . ?
C16 N3 N4 107.0(4) . . ?
C16 N3 Ir1 137.9(3) . . ?
N4 N3 Ir1 114.4(3) . . ?
C9 N2 N1 109.6(4) . . ?
C9 N2 C2 133.9(4) . . ?
N1 N2 C2 116.6(3) . . ?
C7 N1 N2 106.6(4) . . ?
C7 N1 Ir1 139.1(3) . . ?
N2 N1 Ir1 114.3(3) . . ?
N7 C29 C28 123.5(4) . . ?
N7 C29 H29 118.2 . . ?
C28 C29 H29 118.2 . . ?
C29 C28 C27 119.7(4) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C26 C27 C28 117.1(4) . . ?
C26 C27 C30 121.6(4) . . ?
C28 C27 C30 121.3(4) . . ?
C27 C26 C25 120.4(4) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
N7 C25 N6 120.1(3) . . ?
N7 C25 C26 122.0(4) . . ?
N6 C25 C26 117.9(4) . . ?
N5 C19 N6 119.5(4) . . ?
N5 C19 C20 122.9(4) . . ?
N6 C19 C20 117.6(4) . . ?
C22 C23 N5 123.6(4) . . ?
C22 C23 H23 118.2 . . ?
N5 C23 H23 118.2 . . ?
C23 C22 C21 119.7(4) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C20 C21 C22 117.3(4) . . ?
C20 C21 C24 120.9(4) . . ?
C22 C21 C24 121.8(4) . . ?
C21 C20 C19 119.9(4) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
H24B C24 H24A 109.5 . . ?
H24C C24 H24A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30A 109.5 . . ?
H30B C30 H30A 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
C15 C10 C11 115.8(4) . . ?
C15 C10 Ir1 130.3(4) . . ?
C11 C10 Ir1 113.9(3) . . ?
C10 C15 C14 120.4(5) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C13 C14 C15 121.4(5) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C13 C12 120.1(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C12 C11 118.4(5) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C12 C11 C10 123.9(4) . . ?
C12 C11 N4 121.1(4) . . ?
C10 C11 N4 115.0(3) . . ?
N3 C16 C17 109.7(5) . . ?
N3 C16 H16 125.1 . . ?
C17 C16 H16 125.1 . . ?
C18 C17 C16 105.8(5) . . ?
C18 C17 H17 127.1 . . ?
C16 C17 H17 127.1 . . ?
N4 C18 C17 108.0(5) . . ?
N4 C18 H18 126.0 . . ?
C17 C18 H18 126.0 . . ?
C2 C1 C6 115.7(4) . . ?
C2 C1 Ir1 114.8(3) . . ?
C6 C1 Ir1 129.4(3) . . ?
C3 C2 C1 124.4(4) . . ?
C3 C2 N2 121.5(4) . . ?
C1 C2 N2 114.1(3) . . ?
N1 C7 C8 110.7(5) . . ?
N1 C7 H7 124.6 . . ?
C8 C7 H7 124.6 . . ?
C9 C8 C7 105.3(5) . . ?
C9 C8 H8 127.4 . . ?
C7 C8 H8 127.4 . . ?
N2 C9 C8 107.8(5) . . ?
N2 C9 H9 126.1 . . ?
C8 C9 H9 126.1 . . ?
C4 C3 C2 117.9(5) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 120.6(5) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.7(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.6(5) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?

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 Ir1 N7 C25 -147.6(3) . . . . ?
C10 Ir1 N7 C25 -49.8(12) . . . . ?
N1 Ir1 N7 C25 132.1(3) . . . . ?
N3 Ir1 N7 C25 -55.2(3) . . . . ?
N5 Ir1 N7 C25 37.4(3) . . . . ?
C1 Ir1 N7 C29 20.3(3) . . . . ?
C10 Ir1 N7 C29 118.2(11) . . . . ?
N1 Ir1 N7 C29 -60.0(3) . . . . ?
N3 Ir1 N7 C29 112.7(3) . . . . ?
N5 Ir1 N7 C29 -154.6(3) . . . . ?
C1 Ir1 N5 C19 -116.5(14) . . . . ?
C10 Ir1 N5 C19 143.4(3) . . . . ?
N1 Ir1 N5 C19 -120.8(3) . . . . ?
N3 Ir1 N5 C19 62.9(3) . . . . ?
N7 Ir1 N5 C19 -29.4(3) . . . . ?
C1 Ir1 N5 C23 64.3(15) . . . . ?
C10 Ir1 N5 C23 -35.8(3) . . . . ?
N1 Ir1 N5 C23 60.0(3) . . . . ?
N3 Ir1 N5 C23 -116.2(3) . . . . ?
N7 Ir1 N5 C23 151.4(3) . . . . ?
C18 N4 N3 C16 0.7(5) . . . . ?
C11 N4 N3 C16 -175.5(4) . . . . ?
C18 N4 N3 Ir1 173.2(3) . . . . ?
C11 N4 N3 Ir1 -3.0(4) . . . . ?
C1 Ir1 N3 C16 86.8(5) . . . . ?
C10 Ir1 N3 C16 172.9(5) . . . . ?
N1 Ir1 N3 C16 112.8(9) . . . . ?
N5 Ir1 N3 C16 -93.2(5) . . . . ?
N7 Ir1 N3 C16 -7.8(5) . . . . ?
C1 Ir1 N3 N4 -82.4(3) . . . . ?
C10 Ir1 N3 N4 3.7(3) . . . . ?
N1 Ir1 N3 N4 -56.4(10) . . . . ?
N5 Ir1 N3 N4 97.6(3) . . . . ?
N7 Ir1 N3 N4 -177.0(3) . . . . ?
C9 N2 N1 C7 -0.9(5) . . . . ?
C2 N2 N1 C7 178.8(4) . . . . ?
C9 N2 N1 Ir1 177.9(3) . . . . ?
C2 N2 N1 Ir1 -2.4(4) . . . . ?
C1 Ir1 N1 C7 -179.5(5) . . . . ?
C10 Ir1 N1 C7 95.0(5) . . . . ?
N3 Ir1 N1 C7 154.1(8) . . . . ?
N5 Ir1 N1 C7 0.1(5) . . . . ?
N7 Ir1 N1 C7 -85.2(5) . . . . ?
C1 Ir1 N1 N2 2.3(3) . . . . ?
C10 Ir1 N1 N2 -83.2(3) . . . . ?
N3 Ir1 N1 N2 -24.1(10) . . . . ?
N5 Ir1 N1 N2 -178.0(3) . . . . ?
N7 Ir1 N1 N2 96.6(3) . . . . ?
C25 N7 C29 C28 4.1(6) . . . . ?
Ir1 N7 C29 C28 -164.5(3) . . . . ?
N7 C29 C28 C27 2.8(7) . . . . ?
C29 C28 C27 C26 -5.8(6) . . . . ?
C29 C28 C27 C30 174.0(4) . . . . ?
C28 C27 C26 C25 2.1(6) . . . . ?
C30 C27 C26 C25 -177.7(4) . . . . ?
C29 N7 C25 N6 174.1(4) . . . . ?
Ir1 N7 C25 N6 -17.6(5) . . . . ?
C29 N7 C25 C26 -7.9(6) . . . . ?
Ir1 N7 C25 C26 160.5(3) . . . . ?
C19 N6 C25 N7 -31.0(6) . . . . ?
C19 N6 C25 C26 150.9(4) . . . . ?
C27 C26 C25 N7 4.9(6) . . . . ?
C27 C26 C25 N6 -177.0(4) . . . . ?
C23 N5 C19 N6 -179.3(4) . . . . ?
Ir1 N5 C19 N6 1.5(5) . . . . ?
C23 N5 C19 C20 3.1(6) . . . . ?
Ir1 N5 C19 C20 -176.1(3) . . . . ?
C25 N6 C19 N5 40.3(6) . . . . ?
C25 N6 C19 C20 -142.0(4) . . . . ?
C19 N5 C23 C22 -2.1(6) . . . . ?
Ir1 N5 C23 C22 177.1(3) . . . . ?
N5 C23 C22 C21 -0.4(7) . . . . ?
C23 C22 C21 C20 2.0(7) . . . . ?
C23 C22 C21 C24 -177.7(4) . . . . ?
C22 C21 C20 C19 -1.0(6) . . . . ?
C24 C21 C20 C19 178.6(4) . . . . ?
N5 C19 C20 C21 -1.6(6) . . . . ?
N6 C19 C20 C21 -179.2(4) . . . . ?
C1 Ir1 C10 C15 -89.8(4) . . . . ?
N1 Ir1 C10 C15 -9.9(4) . . . . ?
N3 Ir1 C10 C15 177.4(4) . . . . ?
N5 Ir1 C10 C15 85.3(4) . . . . ?
N7 Ir1 C10 C15 171.9(9) . . . . ?
C1 Ir1 C10 C11 89.1(3) . . . . ?
N1 Ir1 C10 C11 168.9(3) . . . . ?
N3 Ir1 C10 C11 -3.7(3) . . . . ?
N5 Ir1 C10 C11 -95.8(3) . . . . ?
N7 Ir1 C10 C11 -9.2(12) . . . . ?
C11 C10 C15 C14 -0.5(6) . . . . ?
Ir1 C10 C15 C14 178.4(3) . . . . ?
C10 C15 C14 C13 -0.5(7) . . . . ?
C15 C14 C13 C12 1.0(8) . . . . ?
C14 C13 C12 C11 -0.6(7) . . . . ?
C13 C12 C11 C10 -0.4(7) . . . . ?
C13 C12 C11 N4 178.1(4) . . . . ?
C15 C10 C11 C12 0.9(6) . . . . ?
Ir1 C10 C11 C12 -178.2(4) . . . . ?
C15 C10 C11 N4 -177.7(4) . . . . ?
Ir1 C10 C11 N4 3.3(5) . . . . ?
C18 N4 C11 C12 6.2(8) . . . . ?
N3 N4 C11 C12 -178.8(4) . . . . ?
C18 N4 C11 C10 -175.2(5) . . . . ?
N3 N4 C11 C10 -0.2(5) . . . . ?
N4 N3 C16 C17 -0.5(6) . . . . ?
Ir1 N3 C16 C17 -170.2(4) . . . . ?
N3 C16 C17 C18 0.1(7) . . . . ?
N3 N4 C18 C17 -0.7(6) . . . . ?
C11 N4 C18 C17 174.5(5) . . . . ?
C16 C17 C18 N4 0.4(7) . . . . ?
C10 Ir1 C1 C2 94.2(3) . . . . ?
N1 Ir1 C1 C2 -1.9(3) . . . . ?
N3 Ir1 C1 C2 174.3(3) . . . . ?
N5 Ir1 C1 C2 -6.3(16) . . . . ?
N7 Ir1 C1 C2 -92.9(3) . . . . ?
C10 Ir1 C1 C6 -84.8(4) . . . . ?
N1 Ir1 C1 C6 179.0(4) . . . . ?
N3 Ir1 C1 C6 -4.7(4) . . . . ?
N5 Ir1 C1 C6 174.7(13) . . . . ?
N7 Ir1 C1 C6 88.0(4) . . . . ?
C6 C1 C2 C3 -0.3(6) . . . . ?
Ir1 C1 C2 C3 -179.5(3) . . . . ?
C6 C1 C2 N2 -179.6(3) . . . . ?
Ir1 C1 C2 N2 1.2(4) . . . . ?
C9 N2 C2 C3 1.1(7) . . . . ?
N1 N2 C2 C3 -178.5(4) . . . . ?
C9 N2 C2 C1 -179.6(5) . . . . ?
N1 N2 C2 C1 0.8(5) . . . . ?
N2 N1 C7 C8 1.0(5) . . . . ?
Ir1 N1 C7 C8 -177.3(4) . . . . ?
N1 C7 C8 C9 -0.7(6) . . . . ?
N1 N2 C9 C8 0.4(6) . . . . ?
C2 N2 C9 C8 -179.2(5) . . . . ?
C7 C8 C9 N2 0.2(6) . . . . ?
C1 C2 C3 C4 0.6(6) . . . . ?
N2 C2 C3 C4 179.8(4) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 -0.7(7) . . . . ?
C4 C5 C6 C1 0.9(7) . . . . ?
C2 C1 C6 C5 -0.4(6) . . . . ?
Ir1 C1 C6 C5 178.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.14
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.046
_refine_diff_density_min         -2.006
_refine_diff_density_rms         0.106

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.500 279 121 ' '
2 0.500 0.500 1.000 280 121 ' '
_platon_squeeze_details          
;
;
_database_code_depnum_ccdc_archive 'CCDC 988579'
