# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2013


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# 
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#  This CIF contains data from an original supplementary publication 
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#  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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data_nd062712_0m
_database_code_depnum_ccdc_archive 'CCDC 907877'
#TrackingRef '14964_web_deposit_cif_file_0_NihalDeligonul_1351197435.nd062712_0m.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H22 Cl2 F4 Ir N2 O'
_chemical_formula_sum            
'C31 H22 Cl2 F4 Ir N2 O'
_chemical_formula_weight         777.61
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   10.3467(12)
_cell_length_b                   11.3394(13)
_cell_length_c                   23.950(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.0790(10)
_cell_angle_gamma                90.00
_cell_volume                     2808.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    9967
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      28.04
_exptl_crystal_description       Needles
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1508
_exptl_absorpt_coefficient_mu    5.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2510
_exptl_absorpt_correction_T_max  0.4647
_exptl_absorpt_process_details   'AXscale in APEX 2(Bruker, 2004)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      160(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 AXS APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            34275
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         28.08
_reflns_number_total             6786
_reflns_number_gt                6457
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0115P)^2^+4.0451P] where P=(Fo^2^+2Fc^2^)/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         6786
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0183
_refine_ls_wR_factor_ref         0.0420
_refine_ls_wR_factor_gt          0.0414
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_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 0.099315(7) 0.832340(7) 0.166765(3) 0.01311(3) Uani 1 1 d . . .
C1 C -0.0549(2) 0.9849(2) 0.24314(10) 0.0238(5) Uani 1 1 d . . .
H1 H -0.0481 0.9192 0.2677 0.029 Uiso 1 1 calc R . .
C2 C -0.1212(3) 1.0834(2) 0.26035(11) 0.0291(5) Uani 1 1 d . . .
H2 H -0.1594 1.0851 0.2958 0.035 Uiso 1 1 calc R . .
C3 C -0.1309(3) 1.1796(2) 0.22481(12) 0.0313(6) Uani 1 1 d . . .
H3 H -0.1755 1.2487 0.2356 0.038 Uiso 1 1 calc R . .
C4 C -0.0744(3) 1.1736(2) 0.17332(11) 0.0261(5) Uani 1 1 d . . .
H4 H -0.0800 1.2392 0.1487 0.031 Uiso 1 1 calc R . .
C5 C -0.0092(2) 1.07173(19) 0.15720(9) 0.0172(4) Uani 1 1 d . . .
C6 C 0.0544(2) 1.05258(19) 0.10419(9) 0.0158(4) Uani 1 1 d . . .
C7 C 0.0610(2) 1.1342(2) 0.06083(10) 0.0205(4) Uani 1 1 d . . .
C8 C 0.1277(2) 1.1149(2) 0.01316(10) 0.0249(5) Uani 1 1 d . . .
H8 H 0.1311 1.1723 -0.0157 0.030 Uiso 1 1 calc R . .
C9 C 0.1894(2) 1.0076(2) 0.00951(10) 0.0249(5) Uani 1 1 d . . .
C10 C 0.1855(2) 0.9215(2) 0.05005(10) 0.0208(4) Uani 1 1 d . . .
H10 H 0.2290 0.8486 0.0451 0.025 Uiso 1 1 calc R . .
C11 C 0.1171(2) 0.94199(18) 0.09851(9) 0.0153(4) Uani 1 1 d . . .
C12 C 0.3182(2) 0.6720(2) 0.13900(10) 0.0223(5) Uani 1 1 d . . .
H12 H 0.3709 0.7280 0.1586 0.027 Uiso 1 1 calc R . .
C13 C 0.3759(2) 0.5740(2) 0.11663(11) 0.0261(5) Uani 1 1 d . . .
H13 H 0.4668 0.5630 0.1206 0.031 Uiso 1 1 calc R . .
C14 C 0.2994(2) 0.4918(2) 0.08823(11) 0.0278(5) Uani 1 1 d . . .
H14 H 0.3372 0.4234 0.0727 0.033 Uiso 1 1 calc R . .
C15 C 0.1674(2) 0.5103(2) 0.08267(10) 0.0240(5) Uani 1 1 d . . .
H15 H 0.1140 0.4547 0.0632 0.029 Uiso 1 1 calc R . .
C16 C 0.1129(2) 0.61118(19) 0.10576(9) 0.0165(4) Uani 1 1 d . . .
C17 C -0.0236(2) 0.64549(19) 0.10359(9) 0.0168(4) Uani 1 1 d . . .
C18 C -0.1245(2) 0.5843(2) 0.07662(10) 0.0212(5) Uani 1 1 d . . .
C19 C -0.2507(2) 0.6226(2) 0.07461(10) 0.0227(5) Uani 1 1 d . . .
H19 H -0.3175 0.5804 0.0550 0.027 Uiso 1 1 calc R . .
C20 C -0.2746(2) 0.7263(2) 0.10282(10) 0.0213(5) Uani 1 1 d . . .
C21 C -0.1809(2) 0.7914(2) 0.13085(10) 0.0185(4) Uani 1 1 d . . .
H21 H -0.2032 0.8619 0.1497 0.022 Uiso 1 1 calc R . .
C22 C -0.0515(2) 0.75279(19) 0.13142(9) 0.0153(4) Uani 1 1 d . . .
C23 C 0.0979(2) 0.74510(19) 0.24352(9) 0.0160(4) Uani 1 1 d . . .
C24 C 0.0177(2) 0.65238(19) 0.25985(10) 0.0195(4) Uani 1 1 d . . .
H24 H -0.0459 0.6236 0.2337 0.023 Uiso 1 1 calc R . .
C25 C 0.0271(2) 0.6005(2) 0.31274(10) 0.0225(5) Uani 1 1 d . . .
C26 C 0.1240(2) 0.6391(2) 0.35040(10) 0.0252(5) Uani 1 1 d . . .
H26 H 0.1336 0.6037 0.3863 0.030 Uiso 1 1 calc R . .
C27 C 0.2067(2) 0.7296(2) 0.33538(10) 0.0235(5) Uani 1 1 d . . .
H27 H 0.2733 0.7550 0.3609 0.028 Uiso 1 1 calc R . .
C28 C 0.1926(2) 0.7831(2) 0.28341(10) 0.0189(4) Uani 1 1 d . . .
C29 C 0.2763(3) 0.8873(2) 0.26976(10) 0.0250(5) Uani 1 1 d . . .
C30 C -0.0656(3) 0.5045(3) 0.32884(13) 0.0356(6) Uani 1 1 d . . .
H30A H -0.1515 0.5386 0.3337 0.053 Uiso 1 1 calc R . .
H30B H -0.0348 0.4680 0.3639 0.053 Uiso 1 1 calc R . .
H30 H -0.0707 0.4446 0.2993 0.053 Uiso 1 1 calc R . .
F1 F 0.25625(19) 0.98622(15) -0.03744(7) 0.0415(4) Uani 1 1 d . . .
F2 F -0.00047(16) 1.24020(13) 0.06419(7) 0.0331(4) Uani 1 1 d . . .
F3 F -0.39892(14) 0.76513(14) 0.10202(7) 0.0349(4) Uani 1 1 d . . .
F4 F -0.10072(15) 0.48057(13) 0.05056(7) 0.0337(4) Uani 1 1 d . . .
N1 N 0.00058(17) 0.97774(16) 0.19310(8) 0.0160(4) Uani 1 1 d . . .
N2 N 0.18950(18) 0.69106(16) 0.13406(8) 0.0165(4) Uani 1 1 d . . .
O1 O 0.27780(15) 0.90005(14) 0.20968(7) 0.0209(3) Uani 1 1 d . . .
C32 C 0.3379(4) 0.7360(4) 0.92810(18) 0.0539(10) Uani 1 1 d . . .
Cl2 Cl 0.35369(9) 0.64708(7) 0.86949(3) 0.04513(18) Uani 1 1 d . . .
Cl1 Cl 0.4210(4) 0.6744(5) 0.9823(2) 0.0695(8) Uani 0.40 1 d P . .
Cl1A Cl 0.4588(3) 0.7239(3) 0.98191(13) 0.0695(8) Uani 0.60 1 d P . .
H33A H 0.374(7) 0.823(6) 0.916(3) 0.16(3) Uiso 1 1 d . . .
H32A H 0.266(6) 0.733(5) 0.938(2) 0.10(2) Uiso 1 1 d . . .
H29 H 0.243(3) 0.966(3) 0.2844(13) 0.033(8) Uiso 1 1 d . . .
H29B H 0.366(3) 0.876(3) 0.2833(13) 0.034(8) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ir1 0.01468(4) 0.01179(4) 0.01291(4) 0.00066(3) 0.00097(3) 0.00035(3)
C1 0.0285(12) 0.0252(12) 0.0178(11) -0.0011(9) 0.0033(9) 0.0048(10)
C2 0.0346(14) 0.0327(14) 0.0204(12) -0.0052(10) 0.0051(10) 0.0095(11)
C3 0.0361(14) 0.0262(13) 0.0317(14) -0.0074(11) 0.0031(11) 0.0123(11)
C4 0.0321(13) 0.0188(11) 0.0275(13) -0.0003(9) 0.0006(10) 0.0061(10)
C5 0.0179(10) 0.0152(10) 0.0182(10) -0.0013(8) -0.0024(8) -0.0002(8)
C6 0.0174(10) 0.0134(9) 0.0162(10) -0.0004(8) -0.0022(8) -0.0018(8)
C7 0.0253(11) 0.0134(10) 0.0226(11) 0.0016(8) -0.0027(9) 0.0004(9)
C8 0.0337(13) 0.0219(11) 0.0192(11) 0.0075(9) 0.0005(10) -0.0035(10)
C9 0.0334(13) 0.0267(12) 0.0150(11) -0.0006(9) 0.0072(9) -0.0020(10)
C10 0.0260(11) 0.0181(10) 0.0183(11) -0.0005(9) 0.0024(9) 0.0010(9)
C11 0.0169(10) 0.0137(9) 0.0152(10) 0.0002(8) -0.0021(8) -0.0012(8)
C12 0.0176(10) 0.0221(11) 0.0273(12) 0.0002(9) 0.0025(9) 0.0005(9)
C13 0.0177(11) 0.0259(12) 0.0350(14) 0.0023(10) 0.0051(10) 0.0058(9)
C14 0.0302(13) 0.0223(12) 0.0314(13) -0.0024(10) 0.0084(10) 0.0089(10)
C15 0.0276(12) 0.0179(11) 0.0267(12) -0.0042(9) 0.0026(9) 0.0051(9)
C16 0.0200(10) 0.0142(10) 0.0155(10) 0.0003(8) 0.0017(8) 0.0023(8)
C17 0.0198(10) 0.0145(10) 0.0160(10) 0.0001(8) 0.0004(8) 0.0010(8)
C18 0.0259(11) 0.0163(10) 0.0214(11) -0.0031(9) -0.0001(9) -0.0006(9)
C19 0.0215(11) 0.0220(11) 0.0245(12) -0.0016(9) -0.0025(9) -0.0056(9)
C20 0.0149(10) 0.0226(11) 0.0265(12) 0.0029(9) 0.0016(9) 0.0007(9)
C21 0.0184(10) 0.0162(10) 0.0210(11) -0.0004(8) 0.0023(8) 0.0002(8)
C22 0.0184(10) 0.0149(9) 0.0125(10) 0.0025(8) 0.0012(8) 0.0001(8)
C23 0.0171(10) 0.0146(9) 0.0166(10) 0.0010(8) 0.0013(8) 0.0026(8)
C24 0.0195(10) 0.0169(10) 0.0222(11) 0.0012(8) 0.0038(8) 0.0014(8)
C25 0.0245(11) 0.0177(11) 0.0259(12) 0.0066(9) 0.0098(9) 0.0049(9)
C26 0.0322(13) 0.0218(11) 0.0218(12) 0.0074(9) 0.0036(10) 0.0097(10)
C27 0.0273(12) 0.0228(12) 0.0198(11) 0.0020(9) -0.0045(9) 0.0055(9)
C28 0.0197(10) 0.0180(10) 0.0191(11) 0.0008(9) 0.0006(8) 0.0021(8)
C29 0.0298(13) 0.0237(12) 0.0210(12) 0.0030(10) -0.0062(10) -0.0069(10)
C30 0.0344(14) 0.0301(14) 0.0430(16) 0.0142(12) 0.0119(12) -0.0023(12)
F1 0.0646(12) 0.0382(9) 0.0233(8) 0.0060(7) 0.0224(8) 0.0082(8)
F2 0.0465(9) 0.0180(7) 0.0352(9) 0.0083(6) 0.0057(7) 0.0105(6)
F3 0.0142(7) 0.0348(9) 0.0553(11) -0.0109(8) -0.0030(7) 0.0024(6)
F4 0.0321(8) 0.0238(8) 0.0448(9) -0.0184(7) -0.0040(7) 0.0014(6)
N1 0.0177(8) 0.0150(9) 0.0154(9) -0.0018(7) 0.0000(7) 0.0007(7)
N2 0.0179(9) 0.0148(8) 0.0171(9) 0.0021(7) 0.0032(7) 0.0014(7)
O1 0.0210(8) 0.0211(8) 0.0205(8) 0.0014(6) -0.0013(6) -0.0051(6)
C32 0.051(2) 0.055(2) 0.056(2) -0.0190(18) -0.0068(18) 0.0198(18)
Cl2 0.0593(5) 0.0336(4) 0.0436(4) 0.0015(3) 0.0165(4) 0.0125(3)
Cl1 0.0573(17) 0.113(3) 0.0375(5) -0.0044(15) -0.0067(10) 0.0308(13)
Cl1A 0.0573(17) 0.113(3) 0.0375(5) -0.0044(15) -0.0067(10) 0.0308(13)
_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 C22 1.967(2) . ?
Ir1 N2 2.0257(18) . ?
Ir1 N1 2.0510(18) . ?
Ir1 C11 2.067(2) . ?
Ir1 C23 2.088(2) . ?
Ir1 O1 2.2177(16) . ?
C1 N1 1.350(3) . ?
C1 C2 1.381(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.371(3) . ?
C5 C6 1.467(3) . ?
C6 C7 1.394(3) . ?
C6 C11 1.421(3) . ?
C7 F2 1.364(3) . ?
C7 C8 1.373(3) . ?
C8 C9 1.379(4) . ?
C8 H8 0.9500 . ?
C9 F1 1.363(3) . ?
C9 C10 1.379(3) . ?
C10 C11 1.401(3) . ?
C10 H10 0.9500 . ?
C12 N2 1.350(3) . ?
C12 C13 1.379(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(3) . ?
C15 H15 0.9500 . ?
C16 N2 1.367(3) . ?
C16 C17 1.464(3) . ?
C17 C18 1.393(3) . ?
C17 C22 1.422(3) . ?
C18 F4 1.358(3) . ?
C18 C19 1.375(3) . ?
C19 C20 1.383(3) . ?
C19 H19 0.9500 . ?
C20 F3 1.359(3) . ?
C20 C21 1.375(3) . ?
C21 C22 1.408(3) . ?
C21 H21 0.9500 . ?
C23 C24 1.404(3) . ?
C23 C28 1.411(3) . ?
C24 C25 1.397(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.395(4) . ?
C25 C30 1.510(3) . ?
C26 C27 1.391(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.387(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.508(3) . ?
C29 O1 1.447(3) . ?
C29 H29 1.02(3) . ?
C29 H29B 0.98(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30 0.9800 . ?
C32 Cl1 1.683(7) . ?
C32 Cl2 1.741(4) . ?
C32 Cl1A 1.768(5) . ?
C32 H33A 1.10(7) . ?
C32 H32A 0.79(6) . ?
Cl1 Cl1A 0.684(5) . ?
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
C22 Ir1 N2 80.81(8) . . ?
C22 Ir1 N1 96.01(8) . . ?
N2 Ir1 N1 175.00(7) . . ?
C22 Ir1 C11 91.57(8) . . ?
N2 Ir1 C11 96.57(8) . . ?
N1 Ir1 C11 79.59(8) . . ?
C22 Ir1 C23 97.51(8) . . ?
N2 Ir1 C23 89.07(8) . . ?
N1 Ir1 C23 95.19(8) . . ?
C11 Ir1 C23 169.99(8) . . ?
C22 Ir1 O1 172.94(7) . . ?
N2 Ir1 O1 93.75(7) . . ?
N1 Ir1 O1 89.71(7) . . ?
C11 Ir1 O1 93.54(7) . . ?
C23 Ir1 O1 77.79(7) . . ?
N1 C1 C2 123.1(2) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 118.6(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 119.0(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C4 119.6(2) . . ?
N1 C5 C6 113.74(19) . . ?
C4 C5 C6 126.7(2) . . ?
C7 C6 C11 118.7(2) . . ?
C7 C6 C5 125.6(2) . . ?
C11 C6 C5 115.73(19) . . ?
F2 C7 C8 116.0(2) . . ?
F2 C7 C6 120.4(2) . . ?
C8 C7 C6 123.6(2) . . ?
C7 C8 C9 116.2(2) . . ?
C7 C8 H8 121.9 . . ?
C9 C8 H8 121.9 . . ?
F1 C9 C8 117.4(2) . . ?
F1 C9 C10 118.9(2) . . ?
C8 C9 C10 123.7(2) . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C6 118.2(2) . . ?
C10 C11 Ir1 128.12(16) . . ?
C6 C11 Ir1 113.65(15) . . ?
N2 C12 C13 122.3(2) . . ?
N2 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C12 C13 C14 119.0(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
N2 C16 C15 120.2(2) . . ?
N2 C16 C17 112.50(18) . . ?
C15 C16 C17 127.3(2) . . ?
C18 C17 C22 118.8(2) . . ?
C18 C17 C16 126.2(2) . . ?
C22 C17 C16 115.01(19) . . ?
F4 C18 C19 116.4(2) . . ?
F4 C18 C17 119.9(2) . . ?
C19 C18 C17 123.6(2) . . ?
C18 C19 C20 116.0(2) . . ?
C18 C19 H19 122.0 . . ?
C20 C19 H19 122.0 . . ?
F3 C20 C21 118.9(2) . . ?
F3 C20 C19 117.0(2) . . ?
C21 C20 C19 124.1(2) . . ?
C20 C21 C22 119.4(2) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C21 C22 C17 118.1(2) . . ?
C21 C22 Ir1 126.91(16) . . ?
C17 C22 Ir1 115.00(15) . . ?
C24 C23 C28 116.3(2) . . ?
C24 C23 Ir1 128.56(17) . . ?
C28 C23 Ir1 115.12(16) . . ?
C25 C24 C23 123.1(2) . . ?
C25 C24 H24 118.5 . . ?
C23 C24 H24 118.5 . . ?
C26 C25 C24 118.6(2) . . ?
C26 C25 C30 120.6(2) . . ?
C24 C25 C30 120.8(2) . . ?
C27 C26 C25 119.9(2) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C28 C27 C26 120.6(2) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C23 121.5(2) . . ?
C27 C28 C29 119.7(2) . . ?
C23 C28 C29 118.8(2) . . ?
O1 C29 C28 108.70(19) . . ?
O1 C29 H29 105.7(17) . . ?
C28 C29 H29 113.7(17) . . ?
O1 C29 H29B 107.4(18) . . ?
C28 C29 H29B 111.5(19) . . ?
H29 C29 H29B 109(3) . . ?
C25 C30 H30A 109.5 . . ?
C25 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C25 C30 H30 109.5 . . ?
H30A C30 H30 109.5 . . ?
H30B C30 H30 109.5 . . ?
C1 N1 C5 119.06(19) . . ?
C1 N1 Ir1 123.67(16) . . ?
C5 N1 Ir1 117.27(14) . . ?
C12 N2 C16 119.30(19) . . ?
C12 N2 Ir1 124.03(16) . . ?
C16 N2 Ir1 116.66(14) . . ?
C29 O1 Ir1 112.80(13) . . ?
Cl1 C32 Cl2 108.8(3) . . ?
Cl1 C32 Cl1A 22.68(19) . . ?
Cl2 C32 Cl1A 117.3(2) . . ?
Cl1 C32 H33A 114(4) . . ?
Cl2 C32 H33A 106(4) . . ?
Cl1A C32 H33A 91(4) . . ?
Cl1 C32 H32A 102(4) . . ?
Cl2 C32 H32A 109(4) . . ?
Cl1A C32 H32A 115(4) . . ?
H33A C32 H32A 117(6) . . ?
Cl1A Cl1 C32 85.7(7) . . ?
Cl1 Cl1A C32 71.7(7) . . ?
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.08
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.066
_refine_diff_density_min         -1.144
_refine_diff_density_rms         0.086


data_nd072312_0m
_database_code_depnum_ccdc_archive 'CCDC 907878'
#TrackingRef '14965_web_deposit_cif_file_1_NihalDeligonul_1351197435.nd072312_0m.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H19 F4 Ir N2 O'
_chemical_formula_sum            
'C30 H19 F4 Ir N2 O'
_chemical_formula_weight         691.67
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   9.7368(6)
_cell_length_b                   16.1179(10)
_cell_length_c                   15.8357(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.2750(10)
_cell_angle_gamma                90.00
_cell_volume                     2484.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    9867
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.00
_exptl_crystal_description       irregular
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336
_exptl_absorpt_coefficient_mu    5.431
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.2398
_exptl_absorpt_correction_T_max  0.5814
_exptl_absorpt_process_details   'AXscale in APEX 2 (Bruker, 2004)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      160(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 AXS APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            29949
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5714
_reflns_number_gt                5330
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0140P)^2^+1.3444P] where P=(Fo^2^+2Fc^2^)/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         5714
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0157
_refine_ls_R_factor_gt           0.0137
_refine_ls_wR_factor_ref         0.0337
_refine_ls_wR_factor_gt          0.0330
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.007
_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 0.294535(6) 0.216572(4) 0.589544(4) 0.01784(3) Uani 1 1 d . . .
C2 C -0.00737(18) 0.21914(11) 0.57604(12) 0.0217(4) Uani 1 1 d . . .
C1 C 0.10299(18) 0.27096(11) 0.60224(12) 0.0210(4) Uani 1 1 d . . .
C3 C 0.03124(19) 0.13833(12) 0.54768(12) 0.0251(4) Uani 1 1 d . . .
C5 C -0.1754(2) 0.32226(14) 0.60826(15) 0.0341(5) Uani 1 1 d . . .
C4 C -0.1457(2) 0.24463(14) 0.57857(13) 0.0278(4) Uani 1 1 d . . .
C7 C 0.0665(2) 0.34978(13) 0.63141(13) 0.0285(4) Uani 1 1 d . . .
C6 C -0.0698(2) 0.37584(13) 0.63465(15) 0.0347(5) Uani 1 1 d . . .
C12 C 0.4211(2) 0.21298(11) 0.42272(13) 0.0275(4) Uani 1 1 d . . .
C18 C 0.46818(17) 0.14959(11) 0.56033(12) 0.0230(4) Uani 1 1 d . . .
C13 C 0.50264(18) 0.15479(12) 0.47448(12) 0.0251(4) Uani 1 1 d . . .
C14 C 0.6065(2) 0.10358(13) 0.44441(14) 0.0330(5) Uani 1 1 d . . .
C16 C 0.6480(2) 0.04889(13) 0.57885(16) 0.0356(5) Uani 1 1 d . . .
C15 C 0.6802(2) 0.05008(13) 0.49526(16) 0.0368(5) Uani 1 1 d . . .
C17 C 0.5453(2) 0.09690(12) 0.61275(14) 0.0288(4) Uani 1 1 d . . .
C9 C 0.2506(3) 0.32481(15) 0.34042(14) 0.0432(6) Uani 1 1 d . . .
C8 C 0.2329(2) 0.30313(14) 0.42367(13) 0.0317(4) Uani 1 1 d . . .
C10 C 0.3598(4) 0.29090(16) 0.29857(16) 0.0533(7) Uani 1 1 d . . .
C11 C 0.4443(3) 0.23513(16) 0.33930(15) 0.0451(6) Uani 1 1 d . . .
C19 C 0.39777(17) 0.31149(11) 0.63796(11) 0.0208(3) Uani 1 1 d . . .
C20 C 0.44923(19) 0.38001(12) 0.59421(13) 0.0254(4) Uani 1 1 d . . .
C22 C 0.5269(2) 0.44449(14) 0.72567(15) 0.0345(5) Uani 1 1 d . . .
C24 C 0.41246(19) 0.31023(13) 0.72723(12) 0.0258(4) Uani 1 1 d . . .
C21 C 0.5116(2) 0.44339(12) 0.63897(14) 0.0311(4) Uani 1 1 d . . .
C23 C 0.4765(2) 0.37728(14) 0.76780(13) 0.0338(5) Uani 1 1 d . . .
N1 N 0.31526(16) 0.24907(10) 0.46506(9) 0.0221(3) Uani 1 1 d . . .
F2 F 0.72201(15) -0.00209(9) 0.63074(11) 0.0574(4) Uani 1 1 d . . .
F4 F 0.56100(14) 0.50933(8) 0.59595(9) 0.0466(3) Uani 1 1 d . . .
F3 F 0.49040(17) 0.37810(10) 0.85336(8) 0.0557(4) Uani 1 1 d . . .
F1 F 0.63768(15) 0.10337(9) 0.36096(9) 0.0508(4) Uani 1 1 d . . .
C25 C 0.3575(2) 0.23681(13) 0.76857(12) 0.0282(4) Uani 1 1 d . . .
C26 C 0.3626(3) 0.21705(17) 0.85447(15) 0.0442(6) Uani 1 1 d . . .
N2 N 0.29694(15) 0.18266(10) 0.71264(10) 0.0238(3) Uani 1 1 d . . .
O1 O 0.15398(13) 0.11630(8) 0.54675(8) 0.0253(3) Uani 1 1 d . . .
C29 C 0.2469(2) 0.11008(14) 0.74079(14) 0.0327(4) Uani 1 1 d . . .
C28 C 0.2527(3) 0.08818(17) 0.82464(15) 0.0444(6) Uani 1 1 d . . .
C27 C 0.3101(3) 0.14267(19) 0.88204(16) 0.0520(7) Uani 1 1 d . . .
C30 C -0.1028(3) 0.4610(2) 0.6671(3) 0.0659(10) Uani 1 1 d . . .
H4 H 0.138(2) 0.3868(13) 0.6487(13) 0.026(5) Uiso 1 1 d . . .
H2 H -0.216(2) 0.2086(13) 0.5622(15) 0.025(6) Uiso 1 1 d . . .
H17 H 0.207(2) 0.0746(14) 0.6979(14) 0.031(6) Uiso 1 1 d . . .
H12 H 0.443(2) 0.3826(13) 0.5354(14) 0.027(6) Uiso 1 1 d . . .
H1 H -0.037(2) 0.1022(14) 0.5296(14) 0.028(6) Uiso 1 1 d . . .
H6 H 0.160(3) 0.3249(15) 0.4537(16) 0.040(7) Uiso 1 1 d . . .
H16 H 0.213(3) 0.0382(17) 0.8435(17) 0.050(7) Uiso 1 1 d . . .
H11 H 0.527(2) 0.0893(13) 0.6683(14) 0.022(5) Uiso 1 1 d . . .
H13 H 0.567(3) 0.4885(17) 0.7519(17) 0.049(7) Uiso 1 1 d . . .
H7 H 0.190(3) 0.3596(17) 0.3145(16) 0.045(7) Uiso 1 1 d . . .
H10 H 0.748(3) 0.0147(17) 0.4727(17) 0.053(7) Uiso 1 1 d . . .
H3 H -0.267(3) 0.3383(16) 0.6138(16) 0.048(7) Uiso 1 1 d . . .
H14 H 0.402(3) 0.2538(18) 0.8916(18) 0.050(7) Uiso 1 1 d . . .
H8 H 0.385(3) 0.3067(19) 0.244(2) 0.062(9) Uiso 1 1 d . . .
H5 H -0.029(4) 0.493(2) 0.670(2) 0.084(11) Uiso 1 1 d . . .
H15 H 0.311(3) 0.1300(18) 0.9420(19) 0.060(8) Uiso 1 1 d . . .
H9 H 0.519(3) 0.2102(17) 0.312(2) 0.061(9) Uiso 1 1 d . . .
H5B H -0.169(4) 0.484(3) 0.639(3) 0.109(15) Uiso 1 1 d . . .
H5A H -0.142(5) 0.457(3) 0.724(3) 0.15(2) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ir1 0.01583(4) 0.01884(4) 0.01883(4) -0.00205(2) -0.00004(2) 0.00208(2)
C2 0.0200(8) 0.0243(9) 0.0209(9) -0.0018(7) 0.0004(7) 0.0015(7)
C1 0.0190(8) 0.0241(9) 0.0201(9) -0.0028(7) 0.0015(7) 0.0017(7)
C3 0.0235(9) 0.0254(9) 0.0264(9) -0.0046(8) -0.0019(7) -0.0016(8)
C5 0.0200(9) 0.0365(12) 0.0459(12) -0.0055(10) 0.0011(9) 0.0075(8)
C4 0.0193(9) 0.0328(10) 0.0313(10) -0.0023(9) -0.0015(7) 0.0005(8)
C7 0.0230(9) 0.0268(10) 0.0357(11) -0.0095(8) 0.0008(8) 0.0009(8)
C6 0.0264(10) 0.0297(11) 0.0482(13) -0.0121(9) 0.0026(9) 0.0068(8)
C12 0.0336(10) 0.0224(9) 0.0266(10) -0.0064(7) 0.0058(8) -0.0008(8)
C18 0.0172(8) 0.0184(8) 0.0333(10) -0.0048(7) 0.0010(7) -0.0008(7)
C13 0.0221(8) 0.0207(9) 0.0327(10) -0.0069(8) 0.0047(7) -0.0011(7)
C14 0.0274(10) 0.0297(11) 0.0423(12) -0.0146(9) 0.0089(9) -0.0027(8)
C16 0.0221(9) 0.0232(10) 0.0611(15) -0.0020(9) -0.0089(9) 0.0042(8)
C15 0.0205(9) 0.0266(10) 0.0635(15) -0.0179(10) 0.0018(9) 0.0025(8)
C17 0.0229(9) 0.0253(10) 0.0379(12) 0.0005(8) -0.0033(8) 0.0017(8)
C9 0.0694(17) 0.0332(12) 0.0267(11) 0.0034(9) -0.0070(11) 0.0093(12)
C8 0.0386(11) 0.0292(10) 0.0270(10) -0.0014(8) -0.0046(9) 0.0060(9)
C10 0.093(2) 0.0439(14) 0.0234(12) 0.0041(10) 0.0108(13) 0.0061(14)
C11 0.0627(16) 0.0427(13) 0.0308(12) -0.0043(10) 0.0179(11) 0.0072(12)
C19 0.0145(8) 0.0225(8) 0.0254(9) -0.0033(7) 0.0005(7) 0.0044(7)
C20 0.0211(9) 0.0257(9) 0.0296(10) -0.0008(8) -0.0002(7) 0.0015(7)
C22 0.0277(10) 0.0309(11) 0.0446(13) -0.0117(9) -0.0063(9) -0.0049(8)
C24 0.0212(9) 0.0309(10) 0.0252(9) -0.0025(8) -0.0023(7) -0.0013(8)
C21 0.0234(9) 0.0245(10) 0.0452(12) 0.0011(9) 0.0003(8) -0.0004(8)
C23 0.0318(10) 0.0420(12) 0.0274(10) -0.0086(9) -0.0052(8) -0.0036(9)
N1 0.0250(8) 0.0203(7) 0.0209(8) -0.0024(6) 0.0004(6) 0.0012(6)
F2 0.0434(8) 0.0495(9) 0.0786(11) 0.0033(8) -0.0152(7) 0.0265(7)
F4 0.0500(8) 0.0308(7) 0.0588(9) 0.0064(6) -0.0052(7) -0.0150(6)
F3 0.0707(10) 0.0659(10) 0.0299(7) -0.0130(7) -0.0093(7) -0.0244(8)
F1 0.0500(8) 0.0553(9) 0.0481(8) -0.0174(7) 0.0210(7) 0.0102(7)
C25 0.0244(9) 0.0372(11) 0.0229(9) -0.0001(8) -0.0028(7) -0.0011(8)
C26 0.0507(15) 0.0561(16) 0.0254(11) 0.0012(10) -0.0066(10) -0.0119(12)
N2 0.0197(7) 0.0287(8) 0.0232(8) 0.0010(7) 0.0011(6) 0.0003(6)
O1 0.0233(6) 0.0222(6) 0.0304(7) -0.0059(5) -0.0014(5) 0.0020(5)
C29 0.0295(10) 0.0352(11) 0.0333(11) 0.0046(9) -0.0006(8) -0.0064(9)
C28 0.0442(13) 0.0505(15) 0.0384(13) 0.0167(11) 0.0008(10) -0.0113(11)
C27 0.0589(16) 0.0704(18) 0.0266(12) 0.0147(12) -0.0029(11) -0.0148(14)
C30 0.0356(14) 0.0429(16) 0.119(3) -0.0410(18) -0.0001(17) 0.0093(13)
_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 C19 1.9760(18) . ?
Ir1 N2 2.0241(16) . ?
Ir1 N1 2.0539(15) . ?
Ir1 C18 2.0672(18) . ?
Ir1 C1 2.0746(18) . ?
Ir1 O1 2.2143(13) . ?
C2 C4 1.409(3) . ?
C2 C1 1.416(2) . ?
C2 C3 1.431(3) . ?
C1 C7 1.400(3) . ?
C3 O1 1.247(2) . ?
C3 H1 0.92(2) . ?
C5 C4 1.370(3) . ?
C5 C6 1.399(3) . ?
C5 H3 0.93(3) . ?
C4 H2 0.93(2) . ?
C7 C6 1.394(3) . ?
C7 H4 0.96(2) . ?
C6 C30 1.503(3) . ?
C12 N1 1.372(2) . ?
C12 C11 1.392(3) . ?
C12 C13 1.467(3) . ?
C18 C17 1.395(3) . ?
C18 C13 1.410(3) . ?
C13 C14 1.397(3) . ?
C14 F1 1.362(3) . ?
C14 C15 1.372(3) . ?
C16 F2 1.358(2) . ?
C16 C15 1.367(3) . ?
C16 C17 1.382(3) . ?
C15 H10 0.95(3) . ?
C17 H11 0.91(2) . ?
C9 C10 1.378(4) . ?
C9 C8 1.378(3) . ?
C9 H7 0.90(3) . ?
C8 N1 1.345(3) . ?
C8 H6 0.94(3) . ?
C10 C11 1.370(4) . ?
C10 H8 0.94(3) . ?
C11 H9 0.94(3) . ?
C19 C20 1.402(3) . ?
C19 C24 1.418(3) . ?
C20 C21 1.377(3) . ?
C20 H12 0.93(2) . ?
C22 C23 1.369(3) . ?
C22 C21 1.378(3) . ?
C22 H13 0.90(3) . ?
C24 C23 1.397(3) . ?
C24 C25 1.460(3) . ?
C21 F4 1.356(2) . ?
C23 F3 1.359(2) . ?
C25 N2 1.368(3) . ?
C25 C26 1.397(3) . ?
C26 C27 1.378(4) . ?
C26 H14 0.91(3) . ?
N2 C29 1.347(3) . ?
C29 C28 1.374(3) . ?
C29 H17 0.96(2) . ?
C28 C27 1.374(4) . ?
C28 H16 0.95(3) . ?
C27 H15 0.97(3) . ?
C30 H5 0.89(4) . ?
C30 H5B 0.85(4) . ?
C30 H5A 0.99(5) . ?
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
C19 Ir1 N2 80.83(7) . . ?
C19 Ir1 N1 96.60(7) . . ?
N2 Ir1 N1 173.65(6) . . ?
C19 Ir1 C18 94.57(7) . . ?
N2 Ir1 C18 94.73(7) . . ?
N1 Ir1 C18 79.63(7) . . ?
C19 Ir1 C1 94.93(7) . . ?
N2 Ir1 C1 90.68(7) . . ?
N1 Ir1 C1 95.34(7) . . ?
C18 Ir1 C1 169.71(7) . . ?
C19 Ir1 O1 171.68(6) . . ?
N2 Ir1 O1 95.25(6) . . ?
N1 Ir1 O1 88.03(6) . . ?
C18 Ir1 O1 93.06(6) . . ?
C1 Ir1 O1 77.72(6) . . ?
C4 C2 C1 122.62(17) . . ?
C4 C2 C3 122.16(17) . . ?
C1 C2 C3 115.21(16) . . ?
C7 C1 C2 115.80(16) . . ?
C7 C1 Ir1 130.59(14) . . ?
C2 C1 Ir1 113.60(12) . . ?
O1 C3 C2 121.44(17) . . ?
O1 C3 H1 119.8(13) . . ?
C2 C3 H1 118.8(13) . . ?
C4 C5 C6 120.48(18) . . ?
C4 C5 H3 119.6(16) . . ?
C6 C5 H3 119.8(16) . . ?
C5 C4 C2 119.03(18) . . ?
C5 C4 H2 120.4(13) . . ?
C2 C4 H2 120.5(13) . . ?
C6 C7 C1 122.30(18) . . ?
C6 C7 H4 119.6(13) . . ?
C1 C7 H4 118.1(13) . . ?
C7 C6 C5 119.77(18) . . ?
C7 C6 C30 119.9(2) . . ?
C5 C6 C30 120.3(2) . . ?
N1 C12 C11 119.6(2) . . ?
N1 C12 C13 113.64(17) . . ?
C11 C12 C13 126.7(2) . . ?
C17 C18 C13 118.26(17) . . ?
C17 C18 Ir1 128.08(15) . . ?
C13 C18 Ir1 113.46(13) . . ?
C14 C13 C18 118.88(18) . . ?
C14 C13 C12 125.02(19) . . ?
C18 C13 C12 116.06(16) . . ?
F1 C14 C15 116.29(18) . . ?
F1 C14 C13 120.7(2) . . ?
C15 C14 C13 123.0(2) . . ?
F2 C16 C15 117.65(19) . . ?
F2 C16 C17 118.9(2) . . ?
C15 C16 C17 123.5(2) . . ?
C16 C15 C14 116.67(19) . . ?
C16 C15 H10 122.2(17) . . ?
C14 C15 H10 121.1(17) . . ?
C16 C17 C18 119.6(2) . . ?
C16 C17 H11 117.5(13) . . ?
C18 C17 H11 122.7(13) . . ?
C10 C9 C8 118.3(2) . . ?
C10 C9 H7 121.9(17) . . ?
C8 C9 H7 119.8(17) . . ?
N1 C8 C9 123.0(2) . . ?
N1 C8 H6 116.6(15) . . ?
C9 C8 H6 120.4(15) . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H8 116.5(19) . . ?
C9 C10 H8 123.7(19) . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H9 121.9(19) . . ?
C12 C11 H9 117.6(19) . . ?
C20 C19 C24 118.34(17) . . ?
C20 C19 Ir1 127.04(14) . . ?
C24 C19 Ir1 114.51(14) . . ?
C21 C20 C19 119.23(19) . . ?
C21 C20 H12 119.9(14) . . ?
C19 C20 H12 120.9(14) . . ?
C23 C22 C21 116.32(19) . . ?
C23 C22 H13 123.4(17) . . ?
C21 C22 H13 120.3(17) . . ?
C23 C24 C19 118.78(19) . . ?
C23 C24 C25 125.82(18) . . ?
C19 C24 C25 115.40(17) . . ?
F4 C21 C20 118.69(19) . . ?
F4 C21 C22 117.29(18) . . ?
C20 C21 C22 124.0(2) . . ?
F3 C23 C22 116.71(19) . . ?
F3 C23 C24 119.97(19) . . ?
C22 C23 C24 123.32(19) . . ?
C8 N1 C12 118.88(17) . . ?
C8 N1 Ir1 124.25(14) . . ?
C12 N1 Ir1 116.88(13) . . ?
N2 C25 C26 119.4(2) . . ?
N2 C25 C24 112.59(17) . . ?
C26 C25 C24 128.0(2) . . ?
C27 C26 C25 120.1(2) . . ?
C27 C26 H14 120.9(18) . . ?
C25 C26 H14 119.0(18) . . ?
C29 N2 C25 119.60(17) . . ?
C29 N2 Ir1 123.82(14) . . ?
C25 N2 Ir1 116.54(13) . . ?
C3 O1 Ir1 111.99(12) . . ?
N2 C29 C28 122.4(2) . . ?
N2 C29 H17 115.2(13) . . ?
C28 C29 H17 122.5(13) . . ?
C27 C28 C29 118.9(2) . . ?
C27 C28 H16 120.0(16) . . ?
C29 C28 H16 121.0(16) . . ?
C28 C27 C26 119.7(2) . . ?
C28 C27 H15 120.6(17) . . ?
C26 C27 H15 119.7(17) . . ?
C6 C30 H5 112(2) . . ?
C6 C30 H5B 112(3) . . ?
H5 C30 H5B 112(4) . . ?
C6 C30 H5A 110(3) . . ?
H5 C30 H5A 109(4) . . ?
H5B C30 H5A 101(4) . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.061