#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:55:39 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179906 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/02/7020257.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7020257
loop_
_publ_author_name
'Howarth, Ashlee J.'
'Davies, David L.'
'Lelj, Francesco'
'Wolf, Michael O.'
'Patrick, Brian O.'
_publ_section_title
;
 Atropisomerism in a thermally switchable, cyclometallated iridium
 complex.
;
_journal_issue                   34
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10150
_journal_page_last               10152
_journal_paper_doi               10.1039/c2dt31120h
_journal_volume                  41
_journal_year                    2012
_chemical_formula_sum            'C47 H44 F6 Ir N6 P'
_chemical_formula_weight         1030.05
_chemical_name_systematic
;
?
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.697(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.7310(17)
_cell_length_b                   23.624(2)
_cell_length_c                   21.5847(19)
_cell_measurement_reflns_used    9692
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      29.98
_cell_measurement_theta_min      2.61
_cell_volume                     8613.5(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            73975
_diffrn_reflns_theta_full        30.05
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    3.205
_exptl_absorpt_correction_T_max  0.638
_exptl_absorpt_correction_T_min  0.526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             4112
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_refine_diff_density_max         2.576
_refine_diff_density_min         -1.719
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         12853
_refine_ls_number_restraints     937
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0228P)²+51.4521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0786
_reflns_number_gt                10250
_reflns_number_total             12853
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2dt31120h.txt
_cod_data_source_block           mw162
_cod_original_cell_volume        8613.6(14)
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7020257
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.27489(19) 0.15117(14) 0.43431(17) 0.0264(7) Uani 1 1 d U . .
H1 H 0.2294 0.1628 0.4456 0.032 Uiso 1 1 calc R . .
C2 C 0.3258(2) 0.11229(16) 0.47368(19) 0.0337(8) Uani 1 1 d U . .
H2 H 0.3154 0.0974 0.5112 0.040 Uiso 1 1 calc R . .
C3 C 0.3920(2) 0.09546(16) 0.4575(2) 0.0372(9) Uani 1 1 d U . .
H3 H 0.4272 0.0681 0.4831 0.045 Uiso 1 1 calc R . .
C4 C 0.4065(2) 0.11900(15) 0.40322(19) 0.0323(8) Uani 1 1 d U . .
H4 H 0.4523 0.1085 0.3919 0.039 Uiso 1 1 calc R . .
C5 C 0.35346(18) 0.15799(13) 0.36580(16) 0.0222(6) Uani 1 1 d U . .
C6 C 0.36491(17) 0.18685(13) 0.30817(15) 0.0205(6) Uani 1 1 d U . .
C7 C 0.44088(18) 0.17706(15) 0.29323(17) 0.0267(7) Uani 1 1 d U . .
H7A H 0.4400 0.1394 0.2740 0.040 Uiso 1 1 calc R . .
H7B H 0.4853 0.1795 0.3334 0.040 Uiso 1 1 calc R . .
H7C H 0.4471 0.2059 0.2625 0.040 Uiso 1 1 calc R . .
C8 C 0.31881(19) 0.25280(15) 0.22262(16) 0.0241(6) Uani 1 1 d U . .
C9 C 0.3282(2) 0.31076(16) 0.23088(18) 0.0294(7) Uani 1 1 d U . .
H9 H 0.3231 0.3278 0.2693 0.035 Uiso 1 1 calc R . .
C10 C 0.3450(2) 0.34456(17) 0.1837(2) 0.0368(9) Uani 1 1 d U . .
H10 H 0.3510 0.3843 0.1900 0.044 Uiso 1 1 calc R . .
C11 C 0.3531(2) 0.32006(19) 0.12745(19) 0.0368(9) Uani 1 1 d U . .
C12 C 0.3391(2) 0.26163(18) 0.11654(17) 0.0325(8) Uani 1 1 d U . .
C13 C 0.32138(18) 0.22666(16) 0.16466(16) 0.0267(7) Uani 1 1 d U . .
C14 C 0.3088(2) 0.16760(17) 0.15210(18) 0.0315(8) Uani 1 1 d U . .
H14 H 0.2984 0.1439 0.1841 0.038 Uiso 1 1 calc R . .
C15 C 0.3114(2) 0.1446(2) 0.09482(19) 0.0387(9) Uani 1 1 d U . .
H15 H 0.3012 0.1053 0.0872 0.046 Uiso 1 1 calc R . .
C16 C 0.3291(2) 0.1783(2) 0.04606(18) 0.0394(9) Uani 1 1 d U . .
C17 C 0.3445(2) 0.2362(2) 0.05763(17) 0.0405(10) Uani 1 1 d U . .
C18 C 0.3653(2) 0.2709(2) 0.01042(19) 0.0454(11) Uani 1 1 d U . .
C19 C 0.3698(3) 0.2449(3) -0.0468(2) 0.0586(15) Uani 1 1 d U . .
H19 H 0.3850 0.2666 -0.0781 0.070 Uiso 1 1 calc R . .
C20 C 0.3527(3) 0.1886(3) -0.0581(2) 0.0594(14) Uani 1 1 d U . .
H20 H 0.3544 0.1724 -0.0979 0.071 Uiso 1 1 calc R . .
C21 C 0.3329(3) 0.1548(3) -0.0134(2) 0.0541(13) Uani 1 1 d U . .
H21 H 0.3219 0.1158 -0.0224 0.065 Uiso 1 1 calc R . .
C22 C 0.3816(3) 0.3290(2) 0.0248(2) 0.0519(12) Uani 1 1 d U . .
H22 H 0.3978 0.3517 -0.0052 0.062 Uiso 1 1 calc R . .
C23 C 0.3751(3) 0.3534(2) 0.0797(2) 0.0481(11) Uani 1 1 d U . .
H23 H 0.3850 0.3927 0.0868 0.058 Uiso 1 1 calc R . .
C24 C 0.30726(18) 0.31616(15) 0.41577(16) 0.0232(6) Uani 1 1 d U . .
H24 H 0.3402 0.2907 0.4463 0.028 Uiso 1 1 calc R . .
C25 C 0.3075(2) 0.37490(15) 0.42294(18) 0.0285(7) Uani 1 1 d U . .
H25 H 0.3400 0.3966 0.4581 0.034 Uiso 1 1 calc R . .
C26 C 0.2507(2) 0.39492(15) 0.36819(18) 0.0282(7) Uani 1 1 d U . .
H26 H 0.2366 0.4334 0.3584 0.034 Uiso 1 1 calc R . .
C27 C 0.15627(18) 0.34262(14) 0.27177(16) 0.0229(6) Uani 1 1 d U . .
C28 C 0.1151(2) 0.38908(16) 0.23805(18) 0.0311(7) Uani 1 1 d U . .
H28 H 0.1293 0.4266 0.2527 0.037 Uiso 1 1 calc R . .
C29 C 0.0526(2) 0.37849(17) 0.18220(18) 0.0346(8) Uani 1 1 d U . .
H29 H 0.0232 0.4091 0.1581 0.042 Uiso 1 1 calc R . .
C30 C 0.0332(2) 0.32334(17) 0.16161(17) 0.0327(8) Uani 1 1 d U . .
H30 H -0.0099 0.3165 0.1236 0.039 Uiso 1 1 calc R . .
C31 C 0.07608(19) 0.27771(15) 0.19608(16) 0.0262(7) Uani 1 1 d U . .
H31 H 0.0617 0.2402 0.1811 0.031 Uiso 1 1 calc R . .
C32 C 0.14005(18) 0.28630(14) 0.25250(15) 0.0220(6) Uani 1 1 d U . .
C33 C 0.1379(2) 0.12908(16) 0.2150(2) 0.0354(8) Uani 1 1 d U . .
H33 H 0.1728 0.1301 0.1893 0.042 Uiso 1 1 calc R . .
C34 C 0.0733(3) 0.09267(19) 0.2047(2) 0.0470(11) Uani 1 1 d U . .
H34 H 0.0563 0.0649 0.1715 0.056 Uiso 1 1 calc R . .
C35 C 0.0395(2) 0.10514(18) 0.2522(2) 0.0437(10) Uani 1 1 d U . .
H35 H -0.0058 0.0873 0.2582 0.052 Uiso 1 1 calc R . .
C36 C 0.07148(19) 0.18079(15) 0.34028(17) 0.0280(7) Uani 1 1 d U . .
C37 C 0.0131(2) 0.16887(18) 0.36935(19) 0.0363(9) Uani 1 1 d U . .
H37 H -0.0214 0.1375 0.3557 0.044 Uiso 1 1 calc R . .
C38 C 0.0069(2) 0.2041(2) 0.41879(19) 0.0381(9) Uani 1 1 d U . .
H38 H -0.0321 0.1967 0.4397 0.046 Uiso 1 1 calc R . .
C39 C 0.0569(2) 0.25003(18) 0.43795(17) 0.0317(8) Uani 1 1 d U . .
H39 H 0.0515 0.2743 0.4714 0.038 Uiso 1 1 calc R . .
C40 C 0.11523(19) 0.26098(15) 0.40844(16) 0.0259(7) Uani 1 1 d U . .
H40 H 0.1493 0.2926 0.4222 0.031 Uiso 1 1 calc R . .
C41 C 0.12439(17) 0.22612(14) 0.35877(15) 0.0215(6) Uani 1 1 d U . .
C42 C -0.1870(8) 0.0000 -0.0192(7) 0.124(5) Uani 1 2 d SU . .
H42A H -0.2358 0.0000 -0.0559 0.186 Uiso 1 2 calc SR . .
H42B H -0.1856 0.0339 0.0074 0.186 Uiso 0.50 1 calc PR . .
H42C H -0.1856 -0.0339 0.0074 0.186 Uiso 0.50 1 calc PR . .
C43 C -0.1135(6) 0.0000 -0.0454(6) 0.101(3) Uani 1 2 d SU . .
H43A H -0.1153 -0.0339 -0.0727 0.121 Uiso 0.50 1 calc PR . .
H43B H -0.1153 0.0339 -0.0727 0.121 Uiso 0.50 1 calc PR . .
C44 C -0.0348(7) 0.0000 0.0125(6) 0.110(4) Uani 1 2 d SU . .
H44A H -0.0329 0.0339 0.0399 0.132 Uiso 0.50 1 calc PR . .
H44B H -0.0329 -0.0339 0.0399 0.132 Uiso 0.50 1 calc PR . .
C45 C 0.3237(7) 0.0000 0.2119(6) 0.121(5) Uani 0.50 2 d SPU . .
H45A H 0.3689 0.0206 0.2058 0.181 Uiso 0.50 1 calc PR . .
H45B H 0.2767 0.0069 0.1747 0.181 Uiso 0.50 1 calc PR . .
H45C H 0.3354 -0.0406 0.2154 0.181 Uiso 0.50 1 calc PR . .
C46 C 0.3079(7) 0.0211(5) 0.2760(7) 0.099(5) Uani 0.50 1 d PU . .
H46A H 0.3571 0.0140 0.3120 0.119 Uiso 0.50 1 calc PR . .
H46B H 0.3015 0.0627 0.2722 0.119 Uiso 0.50 1 calc PR . .
C47 C 0.2433(6) 0.0000 0.2975(7) 0.113(4) Uani 0.50 2 d SPU . .
H47A H 0.1945 0.0075 0.2612 0.136 Uiso 0.25 1 calc PR . .
H47B H 0.2496 -0.0417 0.2999 0.136 Uiso 0.25 1 calc PR . .
C48 C 0.2258(7) 0.0159(4) 0.3543(7) 0.086(4) Uani 0.50 1 d PU . .
H48A H 0.2244 0.0578 0.3530 0.103 Uiso 0.50 1 calc PR . .
H48B H 0.2737 0.0057 0.3902 0.103 Uiso 0.50 1 calc PR . .
C49 C 0.1604(7) 0.0000 0.3777(8) 0.122(4) Uani 0.50 2 d SPU . .
H49A H 0.1156 0.0212 0.3481 0.147 Uiso 0.25 1 calc PR . .
H49B H 0.1511 -0.0399 0.3635 0.147 Uiso 0.25 1 calc PR . .
C50 C 0.1411(10) 0.0000 0.4368(7) 0.177(7) Uani 0.50 2 d SPU . .
H50A H 0.0877 -0.0153 0.4292 0.265 Uiso 0.50 1 calc PR . .
H50B H 0.1431 0.0388 0.4532 0.265 Uiso 0.50 1 calc PR . .
H50C H 0.1792 -0.0235 0.4689 0.265 Uiso 0.50 1 calc PR . .
C45B C 0.3237(7) 0.0000 0.2119(6) 0.121(5) Uani 0.50 2 d SPU . .
C47B C 0.2433(6) 0.0000 0.2975(7) 0.113(4) Uani 0.50 2 d SPU . .
H47C H 0.2496 0.0417 0.2999 0.136 Uiso 0.25 1 calc PR . .
H47D H 0.1945 -0.0075 0.2612 0.136 Uiso 0.25 1 calc PR . .
C49B C 0.1604(7) 0.0000 0.3777(8) 0.122(4) Uani 0.50 2 d SPU . .
H49C H 0.1511 0.0399 0.3635 0.147 Uiso 0.25 1 calc PR . .
H49D H 0.1156 -0.0212 0.3481 0.147 Uiso 0.25 1 calc PR . .
C50B C 0.1411(10) 0.0000 0.4368(7) 0.177(7) Uani 0.50 2 d SPU . .
N1 N 0.28716(15) 0.17317(11) 0.38080(13) 0.0219(5) Uani 1 1 d U . .
N2 N 0.30825(15) 0.22027(11) 0.27610(13) 0.0203(5) Uani 1 1 d U . .
N3 N 0.25403(15) 0.30092(11) 0.35991(12) 0.0201(5) Uani 1 1 d U . .
N4 N 0.21915(15) 0.35004(11) 0.33143(13) 0.0218(5) Uani 1 1 d U . .
N5 N 0.14346(16) 0.16222(12) 0.26619(15) 0.0261(6) Uani 1 1 d U . .
N6 N 0.08187(17) 0.14712(13) 0.28880(16) 0.0300(6) Uani 1 1 d U . .
F1 F 0.51260(18) 0.0000 0.42238(16) 0.0352(7) Uani 1 2 d SU . .
F2 F 0.49712(19) 0.0000 0.31434(16) 0.0462(8) Uani 1 2 d SU . .
F3 F 0.57113(12) 0.06791(8) 0.37873(11) 0.0313(4) Uani 1 1 d U . .
F4 F 0.62976(17) 0.0000 0.33474(15) 0.0312(6) Uani 1 2 d SU . .
F5 F 0.64528(16) 0.0000 0.44255(14) 0.0315(6) Uani 1 2 d SU . .
P1 P 0.57078(7) 0.0000 0.37787(6) 0.0199(2) Uani 1 2 d SU . .
F6 F -0.2181(2) 0.0000 0.2706(3) 0.0901(17) Uani 1 2 d SDU . .
F7 F -0.1392(3) 0.0000 0.3708(2) 0.0667(12) Uani 1 2 d SDU . .
F10 F -0.1225(3) -0.06619(12) 0.3017(2) 0.0918(13) Uani 1 1 d DU . .
F8 F -0.0322(3) 0.0000 0.3331(3) 0.118(2) Uani 1 2 d SU . .
F9 F -0.1120(3) 0.0000 0.2311(2) 0.0796(15) Uani 1 2 d SDU . .
P2 P -0.12612(10) 0.0000 0.30106(10) 0.0485(4) Uani 1 2 d SDU . .
Ir1 Ir 0.208381(7) 0.228849(5) 0.313923(6) 0.01833(4) Uani 1 1 d U . .
C53 C 0.3223(10) 0.0000 -0.1045(8) 0.211(9) Uiso 1 2 d SDU A 1
H53A H 0.3039 0.0000 -0.1521 0.317 Uiso 1 2 calc SR A 1
H53B H 0.3025 0.0339 -0.0883 0.317 Uiso 0.50 1 calc PR A 1
H53C H 0.3025 -0.0339 -0.0883 0.317 Uiso 0.50 1 calc PR A 1
C51 C 0.4564(9) 0.0000 -0.0099(11) 0.266(12) Uiso 1 2 d SDU . 1
H51A H 0.4396 0.0337 0.0098 0.319 Uiso 0.50 1 calc PR . 1
H51B H 0.4396 -0.0337 0.0098 0.319 Uiso 0.50 1 calc PR . 1
C52 C 0.4111(11) 0.0000 -0.0811(10) 0.273(12) Uiso 1 2 d SDU A 1
H52A H 0.4287 0.0336 -0.1004 0.328 Uiso 0.50 1 calc PR A 1
H52B H 0.4287 -0.0336 -0.1004 0.328 Uiso 0.50 1 calc PR A 1
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'
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
N1 C1 C2 122.6(3) . .
N1 C1 H1 118.7 . .
C2 C1 H1 118.7 . .
C3 C2 C1 118.8(3) . .
C3 C2 H2 120.6 . .
C1 C2 H2 120.6 . .
C2 C3 C4 119.2(3) . .
C2 C3 H3 120.4 . .
C4 C3 H3 120.4 . .
C5 C4 C3 119.3(3) . .
C5 C4 H4 120.3 . .
C3 C4 H4 120.3 . .
N1 C5 C4 121.3(3) . .
N1 C5 C6 115.3(3) . .
C4 C5 C6 123.4(3) . .
N2 C6 C5 116.4(3) . .
N2 C6 C7 125.5(3) . .
C5 C6 C7 118.1(3) . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C9 C8 C13 120.9(3) . .
C9 C8 N2 117.6(3) . .
C13 C8 N2 121.5(3) . .
C8 C9 C10 121.1(3) . .
C8 C9 H9 119.5 . .
C10 C9 H9 119.5 . .
C11 C10 C9 120.0(4) . .
C11 C10 H10 120.0 . .
C9 C10 H10 120.0 . .
C10 C11 C12 119.6(3) . .
C10 C11 C23 121.2(4) . .
C12 C11 C23 119.1(4) . .
C11 C12 C13 120.6(3) . .
C11 C12 C17 120.2(4) . .
C13 C12 C17 119.2(4) . .
C8 C13 C14 123.5(3) . .
C8 C13 C12 117.7(3) . .
C14 C13 C12 118.8(3) . .
C15 C14 C13 121.0(4) . .
C15 C14 H14 119.5 . .
C13 C14 H14 119.5 . .
C14 C15 C16 121.4(4) . .
C14 C15 H15 119.3 . .
C16 C15 H15 119.3 . .
C17 C16 C21 118.9(4) . .
C17 C16 C15 119.2(4) . .
C21 C16 C15 121.9(4) . .
C16 C17 C12 120.3(4) . .
C16 C17 C18 120.4(4) . .
C12 C17 C18 119.3(4) . .
C19 C18 C22 123.6(4) . .
C19 C18 C17 118.0(5) . .
C22 C18 C17 118.4(4) . .
C20 C19 C18 120.8(5) . .
C20 C19 H19 119.6 . .
C18 C19 H19 119.6 . .
C19 C20 C21 121.9(4) . .
C19 C20 H20 119.0 . .
C21 C20 H20 119.0 . .
C20 C21 C16 119.9(5) . .
C20 C21 H21 120.1 . .
C16 C21 H21 120.1 . .
C23 C22 C18 122.5(4) . .
C23 C22 H22 118.8 . .
C18 C22 H22 118.8 . .
C22 C23 C11 120.5(5) . .
C22 C23 H23 119.7 . .
C11 C23 H23 119.7 . .
N3 C24 C25 110.2(3) . .
N3 C24 H24 124.9 . .
C25 C24 H24 124.9 . .
C26 C25 C24 105.6(3) . .
C26 C25 H25 127.2 . .
C24 C25 H25 127.2 . .
N4 C26 C25 107.5(3) . .
N4 C26 H26 126.3 . .
C25 C26 H26 126.3 . .
C28 C27 C32 124.5(3) . .
C28 C27 N4 120.9(3) . .
C32 C27 N4 114.6(3) . .
C29 C28 C27 117.6(3) . .
C29 C28 H28 121.2 . .
C27 C28 H28 121.2 . .
C30 C29 C28 120.2(3) . .
C30 C29 H29 119.9 . .
C28 C29 H29 119.9 . .
C29 C30 C31 120.9(3) . .
C29 C30 H30 119.6 . .
C31 C30 H30 119.6 . .
C30 C31 C32 121.1(3) . .
C30 C31 H31 119.5 . .
C32 C31 H31 119.5 . .
C27 C32 C31 115.8(3) . .
C27 C32 Ir1 114.6(2) . .
C31 C32 Ir1 129.5(3) . .
N5 C33 C34 110.3(3) . .
N5 C33 H33 124.9 . .
C34 C33 H33 124.9 . .
C35 C34 C33 105.8(4) . .
C35 C34 H34 127.1 . .
C33 C34 H34 127.1 . .
N6 C35 C34 107.8(3) . .
N6 C35 H35 126.1 . .
C34 C35 H35 126.1 . .
C37 C36 C41 123.5(3) . .
C37 C36 N6 122.0(3) . .
C41 C36 N6 114.6(3) . .
C38 C37 C36 118.1(4) . .
C38 C37 H37 121.0 . .
C36 C37 H37 121.0 . .
C39 C38 C37 120.5(3) . .
C39 C38 H38 119.7 . .
C37 C38 H38 119.7 . .
C38 C39 C40 120.4(3) . .
C38 C39 H39 119.8 . .
C40 C39 H39 119.8 . .
C39 C40 C41 121.0(3) . .
C39 C40 H40 119.5 . .
C41 C40 H40 119.5 . .
C36 C41 C40 116.4(3) . .
C36 C41 Ir1 114.7(2) . .
C40 C41 Ir1 128.7(2) . .
C43 C42 H42A 109.5 . .
C43 C42 H42B 109.5 . .
H42A C42 H42B 109.5 . .
C43 C42 H42C 109.5 . .
H42A C42 H42C 109.5 . .
H42B C42 H42C 109.5 . .
C44 C43 C42 110.4(10) . .
C44 C43 H43A 109.6 . .
C42 C43 H43A 109.6 . .
C44 C43 H43B 109.6 . .
C42 C43 H43B 109.6 . .
H43A C43 H43B 108.1 . .
C44 C44 C43 110.3(13) 5 .
C44 C44 H44A 109.6 5 .
C43 C44 H44A 109.6 . .
C44 C44 H44B 109.6 5 .
C43 C44 H44B 109.6 . .
H44A C44 H44B 108.1 . .
C46 C45 H45A 109.5 . .
C46 C45 H45B 109.5 . .
H45A C45 H45B 109.5 . .
C46 C45 H45C 109.5 . .
H45A C45 H45C 109.5 . .
H45B C45 H45C 109.5 . .
C47 C46 C45 122.8(10) . .
C47 C46 H46A 106.6 . .
C45 C46 H46A 106.6 . .
C47 C46 H46B 106.6 . .
C45 C46 H46B 106.6 . .
H46A C46 H46B 106.6 . .
C48 C47 C46 126.4(9) . .
C48 C47 H47A 105.7 . .
C46 C47 H47A 105.7 . .
C48 C47 H47B 105.7 . .
C46 C47 H47B 105.7 . .
H47A C47 H47B 106.2 . .
C47 C48 C49 130.4(11) . .
C47 C48 H48A 104.7 . .
C49 C48 H48A 104.7 . .
C47 C48 H48B 104.7 . .
C49 C48 H48B 104.7 . .
H48A C48 H48B 105.7 . .
C50 C49 C48 138.7(12) . .
C50 C49 H49A 102.4 . .
C48 C49 H49A 102.4 . .
C50 C49 H49B 102.4 . .
C48 C49 H49B 102.4 . .
H49A C49 H49B 104.9 . .
C49 C50 H50A 109.5 . .
C49 C50 H50B 109.5 . .
H50A C50 H50B 109.5 . .
C49 C50 H50C 109.5 . .
H50A C50 H50C 109.5 . .
H50B C50 H50C 109.5 . .
C1 N1 C5 118.7(3) . .
C1 N1 Ir1 125.3(2) . .
C5 N1 Ir1 116.0(2) . .
C6 N2 C8 118.8(3) . .
C6 N2 Ir1 116.3(2) . .
C8 N2 Ir1 124.6(2) . .
C24 N3 N4 106.0(3) . .
C24 N3 Ir1 137.9(2) . .
N4 N3 Ir1 115.87(19) . .
C26 N4 N3 110.7(3) . .
C26 N4 C27 134.3(3) . .
N3 N4 C27 114.9(3) . .
C33 N5 N6 106.0(3) . .
C33 N5 Ir1 139.7(2) . .
N6 N5 Ir1 114.2(2) . .
C35 N6 N5 110.2(3) . .
C35 N6 C36 133.5(3) . .
N5 N6 C36 116.0(3) . .
F2 P1 F4 90.52(19) . .
F2 P1 F5 179.74(19) . .
F4 P1 F5 89.74(17) . .
F2 P1 F3 90.53(9) . 6
F4 P1 F3 90.33(8) . 6
F5 P1 F3 89.47(9) . 6
F2 P1 F3 90.53(9) . .
F4 P1 F3 90.33(8) . .
F5 P1 F3 89.47(9) . .
F3 P1 F3 178.74(18) 6 .
F2 P1 F1 90.43(19) . .
F4 P1 F1 179.06(19) . .
F5 P1 F1 89.32(17) . .
F3 P1 F1 89.66(8) 6 .
F3 P1 F1 89.66(8) . .
F6 P2 F10 92.23(18) . .
F6 P2 F10 92.23(18) . 6
F10 P2 F10 175.4(3) . 6
F6 P2 F7 87.9(3) . .
F10 P2 F7 90.54(14) . .
F10 P2 F7 90.54(14) 6 .
F6 P2 F8 179.3(3) . .
F10 P2 F8 87.77(18) . .
F10 P2 F8 87.77(18) 6 .
F7 P2 F8 91.3(3) . .
F6 P2 F9 92.6(3) . .
F10 P2 F9 89.44(14) . .
F10 P2 F9 89.44(14) 6 .
F7 P2 F9 179.4(3) . .
F8 P2 F9 88.1(3) . .
C41 Ir1 N3 92.03(12) . .
C41 Ir1 C32 87.32(12) . .
N3 Ir1 C32 80.01(12) . .
C41 Ir1 N5 80.28(12) . .
N3 Ir1 N5 169.93(10) . .
C32 Ir1 N5 93.05(13) . .
C41 Ir1 N1 94.77(11) . .
N3 Ir1 N1 96.06(10) . .
C32 Ir1 N1 175.63(12) . .
N5 Ir1 N1 91.09(11) . .
C41 Ir1 N2 170.46(11) . .
N3 Ir1 N2 90.73(10) . .
C32 Ir1 N2 102.15(11) . .
N5 Ir1 N2 97.91(10) . .
N1 Ir1 N2 75.86(10) . .
C52 C53 H53A 109.5 . .
C52 C53 H53B 109.5 . .
H53A C53 H53B 109.5 . .
C52 C53 H53C 109.5 . .
H53A C53 H53C 109.5 . .
H53B C53 H53C 109.5 . .
C51 C51 C52 119(3) 5_655 .
C51 C51 H51A 107.6 5_655 .
C52 C51 H51A 107.6 . .
C51 C51 H51B 107.6 5_655 .
C52 C51 H51B 107.6 . .
H51A C51 H51B 107.0 . .
C53 C52 C51 121.6(10) . .
C53 C52 H52A 106.9 . .
C51 C52 H52A 106.9 . .
C53 C52 H52B 106.9 . .
C51 C52 H52B 106.9 . .
H52A C52 H52B 106.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.343(4) .
C1 C2 1.384(5) .
C1 H1 0.9500 .
C2 C3 1.382(5) .
C2 H2 0.9500 .
C3 C4 1.389(5) .
C3 H3 0.9500 .
C4 C5 1.387(5) .
C4 H4 0.9500 .
C5 N1 1.359(4) .
C5 C6 1.486(4) .
C6 N2 1.300(4) .
C6 C7 1.495(4) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C9 1.384(5) .
C8 C13 1.408(5) .
C8 N2 1.446(4) .
C9 C10 1.396(5) .
C9 H9 0.9500 .
C10 C11 1.391(6) .
C10 H10 0.9500 .
C11 C12 1.409(6) .
C11 C23 1.441(5) .
C12 C13 1.435(5) .
C12 C17 1.435(5) .
C13 C14 1.426(5) .
C14 C15 1.364(5) .
C14 H14 0.9500 .
C15 C16 1.429(6) .
C15 H15 0.9500 .
C16 C17 1.401(6) .
C16 C21 1.419(6) .
C17 C18 1.440(6) .
C18 C19 1.403(6) .
C18 C22 1.418(7) .
C19 C20 1.369(8) .
C19 H19 0.9500 .
C20 C21 1.376(7) .
C20 H20 0.9500 .
C21 H21 0.9500 .
C22 C23 1.354(7) .
C22 H22 0.9500 .
C23 H23 0.9500 .
C24 N3 1.335(4) .
C24 C25 1.396(5) .
C24 H24 0.9500 .
C25 C26 1.383(5) .
C25 H25 0.9500 .
C26 N4 1.341(4) .
C26 H26 0.9500 .
C27 C28 1.394(5) .
C27 C32 1.398(5) .
C27 N4 1.435(4) .
C28 C29 1.390(5) .
C28 H28 0.9500 .
C29 C30 1.386(6) .
C29 H29 0.9500 .
C30 C31 1.396(5) .
C30 H30 0.9500 .
C31 C32 1.404(5) .
C31 H31 0.9500 .
C32 Ir1 2.023(3) .
C33 N5 1.332(5) .
C33 C34 1.394(5) .
C33 H33 0.9500 .
C34 C35 1.368(6) .
C34 H34 0.9500 .
C35 N6 1.346(5) .
C35 H35 0.9500 .
C36 C37 1.392(4) .
C36 C41 1.400(5) .
C36 N6 1.423(5) .
C37 C38 1.384(6) .
C37 H37 0.9500 .
C38 C39 1.383(6) .
C38 H38 0.9500 .
C39 C40 1.394(4) .
C39 H39 0.9500 .
C40 C41 1.400(5) .
C40 H40 0.9500 .
C41 Ir1 2.009(3) .
C42 C43 1.571(15) .
C42 H42A 0.9800 .
C42 H42B 0.9800 .
C42 H42C 0.9800 .
C43 C44 1.565(15) .
C43 H43A 0.9900 .
C43 H43B 0.9900 .
C44 C44 1.49(2) 5
C44 H44A 0.9900 .
C44 H44B 0.9900 .
C45 C46 1.573(17) .
C45 H45A 0.9800 .
C45 H45B 0.9800 .
C45 H45C 0.9800 .
C46 C47 1.448(18) .
C46 H46A 0.9900 .
C46 H46B 0.9900 .
C47 C48 1.404(18) .
C47 H47A 0.9900 .
C47 H47B 0.9900 .
C48 C49 1.448(18) .
C48 H48A 0.9900 .
C48 H48B 0.9900 .
C49 C50 1.42(2) .
C49 H49A 0.9900 .
C49 H49B 0.9900 .
C50 H50A 0.9800 .
C50 H50B 0.9800 .
C50 H50C 0.9800 .
N1 Ir1 2.131(3) .
N2 Ir1 2.173(2) .
N3 N4 1.370(4) .
N3 Ir1 2.013(3) .
N5 N6 1.372(4) .
N5 Ir1 2.035(3) .
F1 P1 1.609(3) .
F2 P1 1.580(3) .
F3 P1 1.6045(19) .
F4 P1 1.598(3) .
F5 P1 1.604(3) .
P1 F3 1.6045(19) 6
F6 P2 1.562(4) .
F7 P2 1.590(4) .
F10 P2 1.565(3) .
F8 P2 1.597(6) .
F9 P2 1.604(4) .
P2 F10 1.565(3) 6
C53 C52 1.501(9) .
C53 H53A 0.9800 .
C53 H53B 0.9800 .
C53 H53C 0.9800 .
C51 C51 1.47(3) 5_655
C51 C52 1.502(9) .
C51 H51A 0.9900 .
C51 H51B 0.9900 .
C52 H52A 0.9900 .
C52 H52B 0.9900 .
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_4
N1 C1 C2 C3 0.2(6) . .
C1 C2 C3 C4 1.5(6) . .
C2 C3 C4 C5 -1.3(6) . .
C3 C4 C5 N1 -0.7(6) . .
C3 C4 C5 C6 178.0(4) . .
N1 C5 C6 N2 -4.5(4) . .
C4 C5 C6 N2 176.8(3) . .
N1 C5 C6 C7 173.3(3) . .
C4 C5 C6 C7 -5.4(5) . .
C13 C8 C9 C10 -3.7(5) . .
N2 C8 C9 C10 174.8(3) . .
C8 C9 C10 C11 -0.4(6) . .
C9 C10 C11 C12 4.1(6) . .
C9 C10 C11 C23 -176.2(4) . .
C10 C11 C12 C13 -3.7(5) . .
C23 C11 C12 C13 176.6(3) . .
C10 C11 C12 C17 177.8(4) . .
C23 C11 C12 C17 -1.9(5) . .
C9 C8 C13 C14 -177.2(3) . .
N2 C8 C13 C14 4.3(5) . .
C9 C8 C13 C12 4.0(5) . .
N2 C8 C13 C12 -174.5(3) . .
C11 C12 C13 C8 -0.2(5) . .
C17 C12 C13 C8 178.2(3) . .
C11 C12 C13 C14 -179.1(3) . .
C17 C12 C13 C14 -0.6(5) . .
C8 C13 C14 C15 179.5(3) . .
C12 C13 C14 C15 -1.7(5) . .
C13 C14 C15 C16 1.8(6) . .
C14 C15 C16 C17 0.4(6) . .
C14 C15 C16 C21 179.2(4) . .
C21 C16 C17 C12 178.4(4) . .
C15 C16 C17 C12 -2.7(6) . .
C21 C16 C17 C18 -1.1(6) . .
C15 C16 C17 C18 177.8(4) . .
C11 C12 C17 C16 -178.7(4) . .
C13 C12 C17 C16 2.9(5) . .
C11 C12 C17 C18 0.8(5) . .
C13 C12 C17 C18 -177.7(3) . .
C16 C17 C18 C19 -0.3(6) . .
C12 C17 C18 C19 -179.8(4) . .
C16 C17 C18 C22 -179.0(4) . .
C12 C17 C18 C22 1.5(6) . .
C22 C18 C19 C20 -179.5(5) . .
C17 C18 C19 C20 1.9(7) . .
C18 C19 C20 C21 -2.2(7) . .
C19 C20 C21 C16 0.7(7) . .
C17 C16 C21 C20 0.9(6) . .
C15 C16 C21 C20 -177.9(4) . .
C19 C18 C22 C23 178.5(4) . .
C17 C18 C22 C23 -2.9(7) . .
C18 C22 C23 C11 1.9(7) . .
C10 C11 C23 C22 -179.1(4) . .
C12 C11 C23 C22 0.6(6) . .
N3 C24 C25 C26 0.4(4) . .
C24 C25 C26 N4 0.1(4) . .
C32 C27 C28 C29 1.4(5) . .
N4 C27 C28 C29 -177.2(3) . .
C27 C28 C29 C30 -0.2(5) . .
C28 C29 C30 C31 -0.5(5) . .
C29 C30 C31 C32 0.0(5) . .
C28 C27 C32 C31 -1.8(5) . .
N4 C27 C32 C31 176.8(3) . .
C28 C27 C32 Ir1 -178.0(3) . .
N4 C27 C32 Ir1 0.6(3) . .
C30 C31 C32 C27 1.1(4) . .
C30 C31 C32 Ir1 176.6(2) . .
N5 C33 C34 C35 0.0(5) . .
C33 C34 C35 N6 0.2(5) . .
C41 C36 C37 C38 0.6(6) . .
N6 C36 C37 C38 -179.5(3) . .
C36 C37 C38 C39 0.6(6) . .
C37 C38 C39 C40 -1.0(6) . .
C38 C39 C40 C41 0.3(5) . .
C37 C36 C41 C40 -1.3(5) . .
N6 C36 C41 C40 178.8(3) . .
C37 C36 C41 Ir1 174.7(3) . .
N6 C36 C41 Ir1 -5.2(4) . .
C39 C40 C41 C36 0.8(5) . .
C39 C40 C41 Ir1 -174.5(3) . .
C42 C43 C44 C44 180.0 . 5
C45 C46 C47 C48 179.0(9) . .
C46 C47 C48 C49 175.7(10) . .
C47 C48 C49 C50 161.5(8) . .
C2 C1 N1 C5 -2.1(5) . .
C2 C1 N1 Ir1 175.7(3) . .
C4 C5 N1 C1 2.3(5) . .
C6 C5 N1 C1 -176.5(3) . .
C4 C5 N1 Ir1 -175.6(3) . .
C6 C5 N1 Ir1 5.6(4) . .
C5 C6 N2 C8 175.3(3) . .
C7 C6 N2 C8 -2.3(5) . .
C5 C6 N2 Ir1 1.1(4) . .
C7 C6 N2 Ir1 -176.5(2) . .
C9 C8 N2 C6 -110.0(3) . .
C13 C8 N2 C6 68.5(4) . .
C9 C8 N2 Ir1 63.6(4) . .
C13 C8 N2 Ir1 -117.8(3) . .
C25 C24 N3 N4 -0.8(3) . .
C25 C24 N3 Ir1 -174.2(2) . .
C25 C26 N4 N3 -0.6(4) . .
C25 C26 N4 C27 176.3(3) . .
C24 N3 N4 C26 0.9(3) . .
Ir1 N3 N4 C26 176.0(2) . .
C24 N3 N4 C27 -176.7(2) . .
Ir1 N3 N4 C27 -1.6(3) . .
C28 C27 N4 C26 2.5(5) . .
C32 C27 N4 C26 -176.2(3) . .
C28 C27 N4 N3 179.3(3) . .
C32 C27 N4 N3 0.6(4) . .
C34 C33 N5 N6 -0.2(4) . .
C34 C33 N5 Ir1 -174.6(3) . .
C34 C35 N6 N5 -0.3(5) . .
C34 C35 N6 C36 173.1(4) . .
C33 N5 N6 C35 0.3(4) . .
Ir1 N5 N6 C35 176.4(3) . .
C33 N5 N6 C36 -174.4(3) . .
Ir1 N5 N6 C36 1.6(4) . .
C37 C36 N6 C35 9.2(6) . .
C41 C36 N6 C35 -170.9(4) . .
C37 C36 N6 N5 -177.6(3) . .
C41 C36 N6 N5 2.3(4) . .
C36 C41 Ir1 N3 178.1(2) . .
C40 C41 Ir1 N3 -6.5(3) . .
C36 C41 Ir1 C32 98.2(3) . .
C40 C41 Ir1 C32 -86.4(3) . .
C36 C41 Ir1 N5 4.7(2) . .
C40 C41 Ir1 N5 -179.9(3) . .
C36 C41 Ir1 N1 -85.6(2) . .
C40 C41 Ir1 N1 89.8(3) . .
C36 C41 Ir1 N2 -75.1(8) . .
C40 C41 Ir1 N2 100.3(7) . .
C24 N3 Ir1 C41 87.6(3) . .
N4 N3 Ir1 C41 -85.4(2) . .
C24 N3 Ir1 C32 174.5(3) . .
N4 N3 Ir1 C32 1.5(2) . .
C24 N3 Ir1 N5 127.5(6) . .
N4 N3 Ir1 N5 -45.5(7) . .
C24 N3 Ir1 N1 -7.5(3) . .
N4 N3 Ir1 N1 179.56(19) . .
C24 N3 Ir1 N2 -83.3(3) . .
N4 N3 Ir1 N2 103.7(2) . .
C27 C32 Ir1 C41 91.4(2) . .
C31 C32 Ir1 C41 -84.1(3) . .
C27 C32 Ir1 N3 -1.1(2) . .
C31 C32 Ir1 N3 -176.7(3) . .
C27 C32 Ir1 N5 171.5(2) . .
C31 C32 Ir1 N5 -4.0(3) . .
C27 C32 Ir1 N1 -27.3(15) . .
C31 C32 Ir1 N1 157.2(13) . .
C27 C32 Ir1 N2 -89.7(2) . .
C31 C32 Ir1 N2 94.7(3) . .
C33 N5 Ir1 C41 170.7(4) . .
N6 N5 Ir1 C41 -3.4(2) . .
C33 N5 Ir1 N3 130.1(6) . .
N6 N5 Ir1 N3 -44.0(7) . .
C33 N5 Ir1 C32 83.9(4) . .
N6 N5 Ir1 C32 -90.2(2) . .
C33 N5 Ir1 N1 -94.7(4) . .
N6 N5 Ir1 N1 91.2(2) . .
C33 N5 Ir1 N2 -18.8(4) . .
N6 N5 Ir1 N2 167.1(2) . .
C1 N1 Ir1 C41 -3.4(3) . .
C5 N1 Ir1 C41 174.4(2) . .
C1 N1 Ir1 N3 89.2(3) . .
C5 N1 Ir1 N3 -93.0(2) . .
C1 N1 Ir1 C32 115.0(14) . .
C5 N1 Ir1 C32 -67.2(15) . .
C1 N1 Ir1 N5 -83.7(3) . .
C5 N1 Ir1 N5 94.1(2) . .
C1 N1 Ir1 N2 178.4(3) . .
C5 N1 Ir1 N2 -3.8(2) . .
C6 N2 Ir1 C41 -9.4(8) . .
C8 N2 Ir1 C41 176.8(6) . .
C6 N2 Ir1 N3 97.4(2) . .
C8 N2 Ir1 N3 -76.4(3) . .
C6 N2 Ir1 C32 177.3(2) . .
C8 N2 Ir1 C32 3.6(3) . .
C6 N2 Ir1 N5 -87.8(2) . .
C8 N2 Ir1 N5 98.4(3) . .
C6 N2 Ir1 N1 1.3(2) . .
C8 N2 Ir1 N1 -172.5(3) . .
C51 C51 C52 C53 180.0 5_655 .
