#------------------------------------------------------------------------------
#$Date: 2019-12-25 22:55:48 +0200 (Wed, 25 Dec 2019) $
#$Revision: 245971 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/15/2311546.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2311546
loop_
_publ_author_name
'Kang, Youngjin'
'Park, Ki-Min'
'Kim, Jinho'
_publ_section_title
;
 Crystal structure of
 mer-tris-{2,6-di-fluoro-3-[5-(2-fluoro-phen-yl)pyridin-2-yl-κN]pyridin-4-yl-κC⁴}iridium(III)
 di-chloro-methane hemisolvate n-hexane hemisolvate.
;
_journal_issue                   'Pt 12'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1952
_journal_page_last               1955
_journal_paper_doi               10.1107/S2056989017016759
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac
'[Ir (C17 H11 F2 N2)3], 0.5C6 H14, 0.5C H2 Cl2'
_chemical_formula_moiety
'C51 H33 F6 Ir N6, 0.5(C6 H14), 0.5(C H2 Cl2)'
_chemical_formula_sum            'C54.5 H41 Cl F6 Ir N6'
_chemical_formula_weight         1121.58
_chemical_name_systematic
;mer-Tris{2,6-difluoro-3-[5-(2-fluorophenyl)pyridin-2-yl-κN]pyridin-4-yl-κC⁴}iridium(III) dichloromethane hemisolvate
n-hexane hemisolvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                117.0678(5)
_cell_angle_beta                 101.9336(6)
_cell_angle_gamma                97.2102(6)
_cell_formula_units_Z            2
_cell_length_a                   12.5753(2)
_cell_length_b                   14.4054(3)
_cell_length_c                   14.8668(3)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.32
_cell_volume                     2270.58(8)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2010)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            40374
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.247
_diffrn_reflns_theta_min         1.612
_exptl_absorpt_coefficient_mu    3.070
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_description       block
_exptl_crystal_F_000             1116
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_refine_diff_density_max         2.383
_refine_diff_density_min         -2.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     625
_refine_ls_number_reflns         11187
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0470P)²+1.7767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0801
_reflns_number_gt                10233
_reflns_number_total             11187
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hg5501sup1.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C54.50 H41 Cl F6 Ir N6'
_cod_database_code               2311546
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.359
_shelx_estimated_absorpt_t_max   0.565
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Ir Ir1 0.80627(2) 0.75047(2) 0.53831(2) 0.01827(4) Uani d 1
F F1 0.8673(2) 0.6415(2) 0.8511(2) 0.0543(7) Uani d 1
F F2 1.12093(19) 0.59363(19) 0.6739(2) 0.0429(6) Uani d 1
N N1 0.9274(2) 0.6888(2) 0.4727(2) 0.0208(5) Uani d 1
N N2 0.9932(3) 0.6203(2) 0.7616(3) 0.0340(7) Uani d 1
C C1 0.8725(2) 0.6929(2) 0.6358(3) 0.0212(6) Uani d 1
C C2 0.8363(3) 0.6866(3) 0.7161(3) 0.0276(7) Uani d 1
H H2 0.7702 0.7072 0.7304 0.033 Uiso calc 1
C C3 0.8993(3) 0.6498(3) 0.7734(3) 0.0341(8) Uani d 1
C C4 1.0248(3) 0.6251(3) 0.6851(3) 0.0298(7) Uani d 1
C C5 0.9706(3) 0.6581(2) 0.6176(3) 0.0232(6) Uani d 1
C C6 1.0025(2) 0.6582(2) 0.5291(3) 0.0229(6) Uani d 1
C C7 1.0955(3) 0.6311(3) 0.4960(3) 0.0303(7) Uani d 1
H H7 1.1495 0.6127 0.5356 0.036 Uiso calc 1
C C8 1.1101(3) 0.6307(3) 0.4064(3) 0.0330(8) Uani d 1
H H8 1.1749 0.6136 0.3859 0.040 Uiso calc 1
C C9 1.0306(3) 0.6551(3) 0.3459(3) 0.0300(7) Uani d 1
C C10 0.9416(3) 0.6851(2) 0.3839(3) 0.0252(7) Uani d 1
H H10 0.8873 0.7041 0.3450 0.030 Uiso calc 1
C C11 1.0395(3) 0.6562(3) 0.2480(3) 0.0339(8) Uani d 1
C C12 1.1385(4) 0.7141(4) 0.2506(4) 0.0489(11) Uani d 1
H H12 1.2007 0.7477 0.3130 0.059 Uiso calc 1
C C13 1.1479(5) 0.7235(4) 0.1634(5) 0.0611(14) Uani d 1
H H13 1.2159 0.7634 0.1662 0.073 Uiso calc 1
C C14 1.0573(5) 0.6742(4) 0.0724(4) 0.0597(14) Uani d 1
H H14 1.0625 0.6816 0.0131 0.072 Uiso calc 1
C C15 0.9605(5) 0.6148(4) 0.0677(4) 0.0510(11) Uani d 1
H H15 0.8996 0.5801 0.0042 0.061 Uiso calc 1
C C16 0.9490(4) 0.6041(3) 0.1545(3) 0.0388(9) Uani d 1
C C17 0.8413(4) 0.5336(4) 0.1405(4) 0.0510(11) Uani d 1
H H17A 0.8564 0.4994 0.1840 0.077 Uiso calc 1
H H17B 0.8090 0.4780 0.0659 0.077 Uiso calc 1
H H17C 0.7882 0.5775 0.1625 0.077 Uiso calc 1
F F3 0.5772(3) 0.7962(2) 0.2111(2) 0.0757(10) Uani d 1
F F4 0.8327(2) 1.08740(18) 0.4761(2) 0.0466(6) Uani d 1
N N3 0.9257(2) 0.9044(2) 0.6254(2) 0.0202(5) Uani d 1
N N4 0.7040(3) 0.9417(3) 0.3469(3) 0.0402(8) Uani d 1
C C18 0.7582(3) 0.8195(3) 0.4460(3) 0.0242(6) Uani d 1
C C19 0.6756(3) 0.7747(3) 0.3490(3) 0.0350(8) Uani d 1
H H19 0.6349 0.7013 0.3136 0.042 Uiso calc 1
C C20 0.6547(4) 0.8392(4) 0.3060(3) 0.0440(10) Uani d 1
C C21 0.7826(3) 0.9830(3) 0.4368(3) 0.0321(8) Uani d 1
C C22 0.8172(3) 0.9295(3) 0.4913(3) 0.0236(6) Uani d 1
C C23 0.9103(3) 0.9743(2) 0.5882(3) 0.0229(6) Uani d 1
C C24 0.9824(3) 1.0773(3) 0.6421(3) 0.0299(7) Uani d 1
H H24 0.9710 1.1270 0.6179 0.036 Uiso calc 1
C C25 1.0702(3) 1.1068(3) 0.7304(3) 0.0307(7) Uani d 1
H H25 1.1189 1.1771 0.7667 0.037 Uiso calc 1
C C26 1.0887(3) 1.0351(3) 0.7673(3) 0.0241(6) Uani d 1
C C27 1.0117(2) 0.9351(2) 0.7118(3) 0.0212(6) Uani d 1
H H27 1.0204 0.8854 0.7365 0.025 Uiso calc 1
C C28 1.1851(3) 1.0651(3) 0.8603(3) 0.0259(7) Uani d 1
C C29 1.2073(3) 1.1663(3) 0.9495(3) 0.0377(8) Uani d 1
H H29 1.1586 1.2118 0.9500 0.045 Uiso calc 1
C C30 1.2990(4) 1.2017(3) 1.0375(3) 0.0457(10) Uani d 1
H H30 1.3132 1.2709 1.0976 0.055 Uiso calc 1
C C31 1.3691(3) 1.1359(4) 1.0369(3) 0.0459(11) Uani d 1
H H31 1.4327 1.1599 1.0964 0.055 Uiso calc 1
C C32 1.3476(3) 1.0351(3) 0.9502(3) 0.0380(9) Uani d 1
H H32 1.3965 0.9903 0.9516 0.046 Uiso calc 1
C C33 1.2560(3) 0.9967(3) 0.8603(3) 0.0293(7) Uani d 1
C C34 1.2406(3) 0.8875(3) 0.7682(3) 0.0349(8) Uani d 1
H H34A 1.2296 0.8922 0.7033 0.052 Uiso calc 1
H H34B 1.1748 0.8377 0.7613 0.052 Uiso calc 1
H H34C 1.3075 0.8611 0.7796 0.052 Uiso calc 1
F F5 0.5676(2) 0.34823(18) 0.2318(2) 0.0532(7) Uani d 1
F F6 0.38409(17) 0.55554(19) 0.4386(2) 0.0466(6) Uani d 1
N N5 0.6894(2) 0.8035(2) 0.6117(2) 0.0210(5) Uani d 1
N N6 0.4774(3) 0.4534(3) 0.3367(3) 0.0386(8) Uani d 1
C C35 0.6786(3) 0.6197(3) 0.4518(3) 0.0232(6) Uani d 1
C C36 0.6739(3) 0.5210(3) 0.3648(3) 0.0298(7) Uani d 1
H H36 0.7383 0.5075 0.3418 0.036 Uiso calc 1
C C37 0.5732(3) 0.4448(3) 0.3142(3) 0.0356(8) Uani d 1
C C38 0.4829(3) 0.5465(3) 0.4172(3) 0.0324(8) Uani d 1
C C39 0.5777(3) 0.6319(3) 0.4795(3) 0.0255(7) Uani d 1
C C40 0.5854(3) 0.7342(3) 0.5712(3) 0.0246(6) Uani d 1
C C41 0.5035(3) 0.7659(3) 0.6217(3) 0.0325(8) Uani d 1
H H41 0.4299 0.7199 0.5929 0.039 Uiso calc 1
C C42 0.5293(3) 0.8633(3) 0.7127(3) 0.0339(8) Uani d 1
H H42 0.4734 0.8836 0.7469 0.041 Uiso calc 1
C C43 0.6366(3) 0.9335(3) 0.7561(3) 0.0256(7) Uani d 1
C C44 0.7122(3) 0.8998(3) 0.6997(3) 0.0243(6) Uani d 1
H H44 0.7842 0.9473 0.7245 0.029 Uiso calc 1
C C45 0.6669(3) 1.0390(3) 0.8546(3) 0.0288(7) Uani d 1
C C46 0.5870(3) 1.0993(3) 0.8704(3) 0.0356(8) Uani d 1
H H46 0.5167 1.0726 0.8173 0.043 Uiso calc 1
C C47 0.6081(4) 1.1971(3) 0.9618(3) 0.0428(9) Uani d 1
H H47 0.5525 1.2367 0.9713 0.051 Uiso calc 1
C C48 0.7093(4) 1.2364(3) 1.0383(3) 0.0456(10) Uani d 1
H H48 0.7247 1.3038 1.1009 0.055 Uiso calc 1
C C49 0.7893(3) 1.1773(3) 1.0239(3) 0.0385(9) Uani d 1
H H49 0.8592 1.2055 1.0778 0.046 Uiso calc 1
C C50 0.7712(3) 1.0787(3) 0.9339(3) 0.0311(7) Uani d 1
C C51 0.8620(3) 1.0185(4) 0.9291(3) 0.0417(9) Uani d 1
H H51A 0.8275 0.9409 0.8916 0.063 Uiso calc 1
H H51B 0.9071 1.0410 1.0011 0.063 Uiso calc 1
H H51C 0.9104 1.0347 0.8915 0.063 Uiso calc 1
C C52 0.3642(9) 0.5534(10) 0.1629(11) 0.164(5) Uani d 1
H H52A 0.3244 0.5125 0.1889 0.246 Uiso calc 1
H H52B 0.4233 0.6141 0.2223 0.246 Uiso calc 1
H H52C 0.3111 0.5806 0.1289 0.246 Uiso calc 1
C C53 0.4179(10) 0.4784(9) 0.0806(10) 0.143(4) Uani d 1
H H53A 0.4697 0.4498 0.1153 0.171 Uiso calc 1
H H53B 0.3576 0.4164 0.0220 0.171 Uiso calc 1
C C54 0.4771(10) 0.5289(7) 0.0381(9) 0.140(4) Uani d 1
H H54A 0.4255 0.5619 0.0091 0.168 Uiso calc 1
H H54C 0.5386 0.5887 0.0977 0.168 Uiso calc 1
C C55 0.4858(8) 1.0429(5) 0.4679(6) 0.070(3) Uani d 0.5
H H55A 0.5258 1.0535 0.4212 0.084 Uiso calc 0.5
H H55B 0.4281 1.0844 0.4747 0.084 Uiso calc 0.5
Cl Cl1 0.4193(4) 0.9067(4) 0.4086(4) 0.245(2) Uani d 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle
_geom_angle_publ_flag
C35 Ir1 N5 . 80.32(12) y
C35 Ir1 N1 . 98.62(12) y
N5 Ir1 N1 . 174.15(10) y
C35 Ir1 C1 . 92.12(12) y
N5 Ir1 C1 . 94.75(12) y
N1 Ir1 C1 . 79.51(12) y
C35 Ir1 C18 . 94.00(13) y
N5 Ir1 C18 . 88.72(11) y
N1 Ir1 C18 . 97.10(12) y
C1 Ir1 C18 . 173.39(11) y
C35 Ir1 N3 . 170.98(11) y
N5 Ir1 N3 . 94.39(10) y
N1 Ir1 N3 . 87.37(10) y
C1 Ir1 N3 . 95.61(11) y
C18 Ir1 N3 . 78.49(12) y
C10 N1 C6 . 119.6(3) ?
C10 N1 Ir1 . 123.6(2) ?
C6 N1 Ir1 . 116.6(2) ?
C4 N2 C3 . 114.9(3) ?
C2 C1 C5 . 117.7(3) ?
C2 C1 Ir1 . 129.4(2) ?
C5 C1 Ir1 . 112.8(2) ?
C3 C2 C1 . 117.8(3) ?
C3 C2 H2 . 121.1 ?
C1 C2 H2 . 121.1 ?
N2 C3 F1 . 113.6(3) ?
N2 C3 C2 . 126.4(4) ?
F1 C3 C2 . 120.0(4) ?
N2 C4 F2 . 113.9(3) ?
N2 C4 C5 . 126.7(3) ?
F2 C4 C5 . 119.4(3) ?
C4 C5 C1 . 116.4(3) ?
C4 C5 C6 . 126.8(3) ?
C1 C5 C6 . 116.8(3) ?
N1 C6 C7 . 118.6(3) ?
N1 C6 C5 . 112.9(3) ?
C7 C6 C5 . 128.5(3) ?
C8 C7 C6 . 120.9(3) ?
C8 C7 H7 . 119.6 ?
C6 C7 H7 . 119.6 ?
C7 C8 C9 . 120.5(3) ?
C7 C8 H8 . 119.8 ?
C9 C8 H8 . 119.8 ?
C10 C9 C8 . 116.5(3) ?
C10 C9 C11 . 119.3(3) ?
C8 C9 C11 . 124.1(3) ?
N1 C10 C9 . 123.8(3) ?
N1 C10 H10 . 118.1 ?
C9 C10 H10 . 118.1 ?
C12 C11 C16 . 119.2(4) ?
C12 C11 C9 . 119.0(4) ?
C16 C11 C9 . 121.7(3) ?
C13 C12 C11 . 121.1(5) ?
C13 C12 H12 . 119.5 ?
C11 C12 H12 . 119.5 ?
C14 C13 C12 . 119.4(4) ?
C14 C13 H13 . 120.3 ?
C12 C13 H13 . 120.3 ?
C15 C14 C13 . 120.3(5) ?
C15 C14 H14 . 119.9 ?
C13 C14 H14 . 119.9 ?
C14 C15 C16 . 121.4(5) ?
C14 C15 H15 . 119.3 ?
C16 C15 H15 . 119.3 ?
C15 C16 C11 . 118.7(4) ?
C15 C16 C17 . 117.6(4) ?
C11 C16 C17 . 123.6(4) ?
C16 C17 H17A . 109.5 ?
C16 C17 H17B . 109.5 ?
H17A C17 H17B . 109.5 ?
C16 C17 H17C . 109.5 ?
H17A C17 H17C . 109.5 ?
H17B C17 H17C . 109.5 ?
C27 N3 C23 . 119.4(3) ?
C27 N3 Ir1 . 124.7(2) ?
C23 N3 Ir1 . 115.9(2) ?
C21 N4 C20 . 114.6(3) ?
C19 C18 C22 . 116.7(3) ?
C19 C18 Ir1 . 129.1(3) ?
C22 C18 Ir1 . 114.1(2) ?
C20 C19 C18 . 118.2(3) ?
C20 C19 H19 . 120.9 ?
C18 C19 H19 . 120.9 ?
N4 C20 F3 . 114.1(3) ?
N4 C20 C19 . 127.1(4) ?
F3 C20 C19 . 118.8(4) ?
N4 C21 F4 . 113.4(3) ?
N4 C21 C22 . 126.5(3) ?
F4 C21 C22 . 120.1(3) ?
C21 C22 C18 . 116.9(3) ?
C21 C22 C23 . 126.1(3) ?
C18 C22 C23 . 117.0(3) ?
N3 C23 C24 . 119.5(3) ?
N3 C23 C22 . 114.0(3) ?
C24 C23 C22 . 126.4(3) ?
C25 C24 C23 . 119.9(3) ?
C25 C24 H24 . 120.0 ?
C23 C24 H24 . 120.0 ?
C24 C25 C26 . 121.1(3) ?
C24 C25 H25 . 119.5 ?
C26 C25 H25 . 119.5 ?
C27 C26 C25 . 115.9(3) ?
C27 C26 C28 . 122.8(3) ?
C25 C26 C28 . 121.4(3) ?
N3 C27 C26 . 124.1(3) ?
N3 C27 H27 . 117.9 ?
C26 C27 H27 . 117.9 ?
C29 C28 C33 . 119.4(3) ?
C29 C28 C26 . 118.1(3) ?
C33 C28 C26 . 122.4(3) ?
C30 C29 C28 . 121.3(4) ?
C30 C29 H29 . 119.4 ?
C28 C29 H29 . 119.4 ?
C31 C30 C29 . 119.3(4) ?
C31 C30 H30 . 120.3 ?
C29 C30 H30 . 120.3 ?
C30 C31 C32 . 120.2(4) ?
C30 C31 H31 . 119.9 ?
C32 C31 H31 . 119.9 ?
C31 C32 C33 . 122.0(4) ?
C31 C32 H32 . 119.0 ?
C33 C32 H32 . 119.0 ?
C32 C33 C28 . 117.7(3) ?
C32 C33 C34 . 118.6(3) ?
C28 C33 C34 . 123.6(3) ?
C33 C34 H34A . 109.5 ?
C33 C34 H34B . 109.5 ?
H34A C34 H34B . 109.5 ?
C33 C34 H34C . 109.5 ?
H34A C34 H34C . 109.5 ?
H34B C34 H34C . 109.5 ?
C44 N5 C40 . 120.0(3) ?
C44 N5 Ir1 . 122.9(2) ?
C40 N5 Ir1 . 117.0(2) ?
C38 N6 C37 . 114.1(3) ?
C36 C35 C39 . 116.7(3) ?
C36 C35 Ir1 . 128.7(2) ?
C39 C35 Ir1 . 114.4(2) ?
C37 C36 C35 . 117.6(3) ?
C37 C36 H36 . 121.2 ?
C35 C36 H36 . 121.2 ?
N6 C37 F5 . 113.9(3) ?
N6 C37 C36 . 127.4(4) ?
F5 C37 C36 . 118.6(3) ?
N6 C38 F6 . 113.8(3) ?
N6 C38 C39 . 126.6(3) ?
F6 C38 C39 . 119.5(3) ?
C38 C39 C35 . 117.4(3) ?
C38 C39 C40 . 127.0(3) ?
C35 C39 C40 . 115.6(3) ?
N5 C40 C41 . 118.9(3) ?
N5 C40 C39 . 112.5(3) ?
C41 C40 C39 . 128.6(3) ?
C42 C41 C40 . 120.1(3) ?
C42 C41 H41 . 120.0 ?
C40 C41 H41 . 120.0 ?
C41 C42 C43 . 121.2(3) ?
C41 C42 H42 . 119.4 ?
C43 C42 H42 . 119.4 ?
C44 C43 C42 . 115.9(3) ?
C44 C43 C45 . 121.8(3) ?
C42 C43 C45 . 122.3(3) ?
N5 C44 C43 . 123.7(3) ?
N5 C44 H44 . 118.1 ?
C43 C44 H44 . 118.1 ?
C46 C45 C50 . 119.1(3) ?
C46 C45 C43 . 118.1(3) ?
C50 C45 C43 . 122.7(3) ?
C47 C46 C45 . 121.4(4) ?
C47 C46 H46 . 119.3 ?
C45 C46 H46 . 119.3 ?
C48 C47 C46 . 119.7(4) ?
C48 C47 H47 . 120.2 ?
C46 C47 H47 . 120.2 ?
C47 C48 C49 . 119.6(4) ?
C47 C48 H48 . 120.2 ?
C49 C48 H48 . 120.2 ?
C48 C49 C50 . 122.5(4) ?
C48 C49 H49 . 118.8 ?
C50 C49 H49 . 118.8 ?
C49 C50 C45 . 117.7(3) ?
C49 C50 C51 . 118.0(3) ?
C45 C50 C51 . 124.3(3) ?
C50 C51 H51A . 109.5 ?
C50 C51 H51B . 109.5 ?
H51A C51 H51B . 109.5 ?
C50 C51 H51C . 109.5 ?
H51A C51 H51C . 109.5 ?
H51B C51 H51C . 109.5 ?
C53 C52 H52A . 109.5 ?
C53 C52 H52B . 109.5 ?
H52A C52 H52B . 109.5 ?
C53 C52 H52C . 109.5 ?
H52A C52 H52C . 109.5 ?
H52B C52 H52C . 109.5 ?
C54 C53 C52 . 114.3(9) ?
C54 C53 H53A . 108.7 ?
C52 C53 H53A . 108.7 ?
C54 C53 H53B . 108.7 ?
C52 C53 H53B . 108.7 ?
H53A C53 H53B . 107.6 ?
C54 C54 C53 2_665 120.0(12) ?
C54 C54 H54A 2_665 107.3 ?
C53 C54 H54A . 107.3 ?
C54 C54 H54C 2_665 107.3 ?
C53 C54 H54C . 107.3 ?
H54A C54 H54C . 106.9 ?
Cl1 C55 Cl1 2_676 113.6(6) ?
Cl1 C55 H55A 2_676 108.8 ?
Cl1 C55 H55A . 108.8 ?
Cl1 C55 H55B 2_676 108.8 ?
Cl1 C55 H55B . 108.8 ?
H55A C55 H55B . 107.7 ?
C55 Cl1 C55 2_676 66.4(6) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ir1 C35 . 1.991(3) y
Ir1 N5 . 2.030(3) y
Ir1 N1 . 2.056(3) y
Ir1 C1 . 2.061(3) y
Ir1 C18 . 2.070(3) y
Ir1 N3 . 2.143(3) y
F1 C3 . 1.349(4) ?
F2 C4 . 1.359(4) ?
N1 C10 . 1.346(4) ?
N1 C6 . 1.378(4) ?
N2 C4 . 1.307(5) ?
N2 C3 . 1.323(5) ?
C1 C2 . 1.397(5) ?
C1 C5 . 1.421(4) ?
C2 C3 . 1.369(5) ?
C2 H2 . 0.9500 ?
C4 C5 . 1.389(5) ?
C5 C6 . 1.453(5) ?
C6 C7 . 1.393(5) ?
C7 C8 . 1.378(5) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.392(5) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.386(5) ?
C9 C11 . 1.490(5) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.392(5) ?
C11 C16 . 1.404(6) ?
C12 C13 . 1.390(7) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.385(8) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.366(7) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.401(6) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.502(6) ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
F3 C20 . 1.345(5) ?
F4 C21 . 1.346(4) ?
N3 C27 . 1.343(4) ?
N3 C23 . 1.367(4) ?
N4 C21 . 1.305(5) ?
N4 C20 . 1.316(5) ?
C18 C19 . 1.392(5) ?
C18 C22 . 1.429(4) ?
C19 C20 . 1.369(5) ?
C19 H19 . 0.9500 ?
C21 C22 . 1.394(5) ?
C22 C23 . 1.460(5) ?
C23 C24 . 1.395(4) ?
C24 C25 . 1.377(5) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.396(5) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.389(4) ?
C26 C28 . 1.483(5) ?
C27 H27 . 0.9500 ?
C28 C29 . 1.395(5) ?
C28 C33 . 1.410(5) ?
C29 C30 . 1.387(6) ?
C29 H29 . 0.9500 ?
C30 C31 . 1.372(7) ?
C30 H30 . 0.9500 ?
C31 C32 . 1.378(6) ?
C31 H31 . 0.9500 ?
C32 C33 . 1.396(5) ?
C32 H32 . 0.9500 ?
C33 C34 . 1.496(5) ?
C34 H34A . 0.9800 ?
C34 H34B . 0.9800 ?
C34 H34C . 0.9800 ?
F5 C37 . 1.352(4) ?
F6 C38 . 1.352(4) ?
N5 C44 . 1.346(4) ?
N5 C40 . 1.367(4) ?
N6 C38 . 1.310(5) ?
N6 C37 . 1.322(5) ?
C35 C36 . 1.405(5) ?
C35 C39 . 1.420(4) ?
C36 C37 . 1.371(5) ?
C36 H36 . 0.9500 ?
C38 C39 . 1.389(5) ?
C39 C40 . 1.456(5) ?
C40 C41 . 1.400(5) ?
C41 C42 . 1.372(5) ?
C41 H41 . 0.9500 ?
C42 C43 . 1.401(5) ?
C42 H42 . 0.9500 ?
C43 C44 . 1.384(5) ?
C43 C45 . 1.483(5) ?
C44 H44 . 0.9500 ?
C45 C46 . 1.396(5) ?
C45 C50 . 1.413(5) ?
C46 C47 . 1.384(6) ?
C46 H46 . 0.9500 ?
C47 C48 . 1.367(6) ?
C47 H47 . 0.9500 ?
C48 C49 . 1.385(6) ?
C48 H48 . 0.9500 ?
C49 C50 . 1.386(5) ?
C49 H49 . 0.9500 ?
C50 C51 . 1.513(5) ?
C51 H51A . 0.9800 ?
C51 H51B . 0.9800 ?
C51 H51C . 0.9800 ?
C52 C53 . 1.562(14) ?
C52 H52A . 0.9800 ?
C52 H52B . 0.9800 ?
C52 H52C . 0.9800 ?
C53 C54 . 1.400(13) ?
C53 H53A . 0.9900 ?
C53 H53B . 0.9900 ?
C54 C54 2_665 1.358(18) ?
C54 H54A . 0.9900 ?
C54 H54C . 0.9900 ?
C55 Cl1 2_676 1.727(3) ?
C55 Cl1 . 1.741(3) ?
C55 H55A . 0.9900 ?
C55 H55B . 0.9900 ?
Cl1 C55 2_676 1.727(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C7 H7 F2 . 0.95 2.29 2.895(5) 121.3 y
C24 H24 F4 . 0.95 2.22 2.851(4) 122.9 y
C36 H36 F2 2_766 0.95 2.41 3.245(4) 146.1 y
C41 H41 F6 . 0.95 2.32 2.917(4) 120.5 y
C44 H44 N3 . 0.95 2.50 3.112(4) 122.2 y
C46 H46 F3 2_676 0.95 2.50 3.067(5) 118.7 y
C13 H13 <i>Cg</i>6 2_776 0.95 2.98 3.777(7) 142 y
C55 H55A <i>Cg</i>4 2_676 0.99 2.96 3.326(9) 103 y
C55 H55B <i>Cg</i>3 2_676 0.99 3.00 3.718(10) 131 y
C55 H55B <i>Cg</i>4 2_676 0.99 2.78 3.326(10) 116 y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C5 C1 C2 C3 . . 1.5(5)
Ir1 C1 C2 C3 . . -176.6(3)
C4 N2 C3 F1 . . 178.4(3)
C4 N2 C3 C2 . . -1.9(6)
C1 C2 C3 N2 . . 0.9(6)
C1 C2 C3 F1 . . -179.5(3)
C3 N2 C4 F2 . . -179.5(3)
C3 N2 C4 C5 . . 0.4(5)
N2 C4 C5 C1 . . 1.9(5)
F2 C4 C5 C1 . . -178.2(3)
N2 C4 C5 C6 . . -176.6(3)
F2 C4 C5 C6 . . 3.4(5)
C2 C1 C5 C4 . . -2.7(4)
Ir1 C1 C5 C4 . . 175.7(2)
C2 C1 C5 C6 . . 175.8(3)
Ir1 C1 C5 C6 . . -5.7(3)
C10 N1 C6 C7 . . 4.3(4)
Ir1 N1 C6 C7 . . -170.7(2)
C10 N1 C6 C5 . . -175.1(3)
Ir1 N1 C6 C5 . . 9.9(3)
C4 C5 C6 N1 . . 175.8(3)
C1 C5 C6 N1 . . -2.6(4)
C4 C5 C6 C7 . . -3.5(5)
C1 C5 C6 C7 . . 178.1(3)
N1 C6 C7 C8 . . -2.5(5)
C5 C6 C7 C8 . . 176.8(3)
C6 C7 C8 C9 . . -1.4(5)
C7 C8 C9 C10 . . 3.5(5)
C7 C8 C9 C11 . . -179.8(3)
C6 N1 C10 C9 . . -2.2(5)
Ir1 N1 C10 C9 . . 172.4(2)
C8 C9 C10 N1 . . -1.7(5)
C11 C9 C10 N1 . . -178.6(3)
C10 C9 C11 C12 . . 126.0(4)
C8 C9 C11 C12 . . -50.7(5)
C10 C9 C11 C16 . . -51.4(5)
C8 C9 C11 C16 . . 131.9(4)
C16 C11 C12 C13 . . 1.8(6)
C9 C11 C12 C13 . . -175.6(4)
C11 C12 C13 C14 . . -0.2(7)
C12 C13 C14 C15 . . -1.5(7)
C13 C14 C15 C16 . . 1.5(7)
C14 C15 C16 C11 . . 0.2(6)
C14 C15 C16 C17 . . -177.5(4)
C12 C11 C16 C15 . . -1.8(5)
C9 C11 C16 C15 . . 175.5(3)
C12 C11 C16 C17 . . 175.8(4)
C9 C11 C16 C17 . . -6.9(6)
C22 C18 C19 C20 . . -1.9(5)
Ir1 C18 C19 C20 . . 176.1(3)
C21 N4 C20 F3 . . -177.2(4)
C21 N4 C20 C19 . . 1.7(7)
C18 C19 C20 N4 . . -0.6(7)
C18 C19 C20 F3 . . 178.3(4)
C20 N4 C21 F4 . . 179.1(4)
C20 N4 C21 C22 . . -0.2(6)
N4 C21 C22 C18 . . -2.2(6)
F4 C21 C22 C18 . . 178.5(3)
N4 C21 C22 C23 . . 175.5(4)
F4 C21 C22 C23 . . -3.7(6)
C19 C18 C22 C21 . . 3.2(5)
Ir1 C18 C22 C21 . . -175.2(3)
C19 C18 C22 C23 . . -174.8(3)
Ir1 C18 C22 C23 . . 6.8(4)
C27 N3 C23 C24 . . -1.6(5)
Ir1 N3 C23 C24 . . 178.2(2)
C27 N3 C23 C22 . . 177.4(3)
Ir1 N3 C23 C22 . . -2.9(3)
C21 C22 C23 N3 . . 179.7(3)
C18 C22 C23 N3 . . -2.5(4)
C21 C22 C23 C24 . . -1.5(6)
C18 C22 C23 C24 . . 176.3(3)
N3 C23 C24 C25 . . 1.8(5)
C22 C23 C24 C25 . . -177.0(3)
C23 C24 C25 C26 . . 0.1(5)
C24 C25 C26 C27 . . -2.0(5)
C24 C25 C26 C28 . . 178.1(3)
C23 N3 C27 C26 . . -0.5(5)
Ir1 N3 C27 C26 . . 179.8(2)
C25 C26 C27 N3 . . 2.2(5)
C28 C26 C27 N3 . . -177.8(3)
C27 C26 C28 C29 . . -134.7(4)
C25 C26 C28 C29 . . 45.2(5)
C27 C26 C28 C33 . . 47.1(5)
C25 C26 C28 C33 . . -133.0(4)
C33 C28 C29 C30 . . 1.2(6)
C26 C28 C29 C30 . . -177.0(3)
C28 C29 C30 C31 . . -0.2(6)
C29 C30 C31 C32 . . -0.8(6)
C30 C31 C32 C33 . . 0.8(6)
C31 C32 C33 C28 . . 0.2(6)
C31 C32 C33 C34 . . 178.2(4)
C29 C28 C33 C32 . . -1.2(5)
C26 C28 C33 C32 . . 176.9(3)
C29 C28 C33 C34 . . -179.0(3)
C26 C28 C33 C34 . . -0.9(5)
C39 C35 C36 C37 . . -0.2(5)
Ir1 C35 C36 C37 . . -176.3(3)
C38 N6 C37 F5 . . 179.3(3)
C38 N6 C37 C36 . . -0.3(6)
C35 C36 C37 N6 . . 1.1(6)
C35 C36 C37 F5 . . -178.5(3)
C37 N6 C38 F6 . . 178.9(3)
C37 N6 C38 C39 . . -1.6(6)
N6 C38 C39 C35 . . 2.4(6)
F6 C38 C39 C35 . . -178.1(3)
N6 C38 C39 C40 . . -177.8(4)
F6 C38 C39 C40 . . 1.8(6)
C36 C35 C39 C38 . . -1.3(5)
Ir1 C35 C39 C38 . . 175.4(3)
C36 C35 C39 C40 . . 178.8(3)
Ir1 C35 C39 C40 . . -4.5(4)
C44 N5 C40 C41 . . 1.0(5)
Ir1 N5 C40 C41 . . 177.7(3)
C44 N5 C40 C39 . . -177.0(3)
Ir1 N5 C40 C39 . . -0.3(4)
C38 C39 C40 N5 . . -176.8(3)
C35 C39 C40 N5 . . 3.1(4)
C38 C39 C40 C41 . . 5.5(6)
C35 C39 C40 C41 . . -174.6(3)
N5 C40 C41 C42 . . -2.6(5)
C39 C40 C41 C42 . . 175.0(4)
C40 C41 C42 C43 . . 1.0(6)
C41 C42 C43 C44 . . 2.1(5)
C41 C42 C43 C45 . . -179.7(3)
C40 N5 C44 C43 . . 2.3(5)
Ir1 N5 C44 C43 . . -174.2(2)
C42 C43 C44 N5 . . -3.8(5)
C45 C43 C44 N5 . . 178.0(3)
C44 C43 C45 C46 . . 139.1(4)
C42 C43 C45 C46 . . -39.0(5)
C44 C43 C45 C50 . . -43.0(5)
C42 C43 C45 C50 . . 138.8(4)
C50 C45 C46 C47 . . 0.2(6)
C43 C45 C46 C47 . . 178.2(4)
C45 C46 C47 C48 . . 0.4(6)
C46 C47 C48 C49 . . -0.6(6)
C47 C48 C49 C50 . . 0.2(6)
C48 C49 C50 C45 . . 0.5(6)
C48 C49 C50 C51 . . -176.9(4)
C46 C45 C50 C49 . . -0.7(5)
C43 C45 C50 C49 . . -178.5(3)
C46 C45 C50 C51 . . 176.5(4)
C43 C45 C50 C51 . . -1.3(6)
C52 C53 C54 C54 . 2_665 -176.7(15)
Cl1 C55 Cl1 C55 2_676 2_676 0.0000(10)
