#------------------------------------------------------------------------------
#$Date: 2024-09-06 03:59:12 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294587 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/68/7716809.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_7716809
loop_
_publ_author_name
'Masternak, Joanna'
'Okła, Karol'
'Kubas, Adam'
'Voller, Jiří'
'Kozlanská, Karolína'
'Zienkiewicz-Machnik, Małgorzata'
'Gilewska, Agnieszka'
'Sitkowski, Jerzy'
'Kamecka, Anna'
'Kazimierczuk, Katarzyna'
'Barszcz, Barbara'
_publ_section_title
;
 Synthesis, photophysical characterisation, quantum-chemical study and
 in vitro antiproliferative activity of cyclometalated Ir(III)
 complexes based on 3,5-dimethyl-1-phenyl-1H-pyrazole and N,N-donor
 ligands.
;
_journal_issue                   34
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14438
_journal_page_last               14450
_journal_paper_doi               10.1039/d4dt01796j
_journal_volume                  53
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         '2(C33 H30 Ir N6 O), 2(F6P), C H2 Cl2'
_chemical_formula_sum            'C67 H62 Cl2 F12 Ir2 N12 O2 P2'
_chemical_formula_weight         1812.52
_chemical_name_systematic
;
[(di(2-pyridyl)ketone-κ²N,N')-bis(3,5-dimethyl-1-phenyl-1H-pyrazole-κ²N,\
C)iridium(III)] hexafluorophosphate dichloromethane hemisolvate
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2021-05-11
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-01-03 deposited with the CCDC.	2024-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.374(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4234(5)
_cell_length_b                   20.1866(7)
_cell_length_c                   17.6610(8)
_cell_measurement_reflns_used    98285
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.75
_cell_measurement_theta_min      2.26
_cell_volume                     3583.1(3)
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_unetI/netI     0.014
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            53401
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.188
_diffrn_reflns_theta_min         2.264
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.913
_exptl_absorpt_correction_T_max  0.6541
_exptl_absorpt_correction_T_min  0.5659
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
        Numerical  absorption  correction was  performed
        after the  optimization of  the  crystal-shape
        description due to Herrendorf?s method
        [Herrendorf, 1994]
        Herrendorf,  W. (1994).HABITUS, a program for the
        optimization  of  the  crystal description for
 the numerical absorption correction by means of
        suitable, psi scanned reflections;dissertation
        1994,Karlsruhe;extension 1998,Gießen
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.68
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1780
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.895
_refine_diff_density_min         -1.758
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     464
_refine_ls_number_reflns         9644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0421P)²+8.1903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0
_reflns_number_gt                9049
_reflns_number_total             9644
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt01796j2.cif
_cod_data_source_block           b2c_2020
_cod_depositor_comments
'Adding full bibliography for 7716806--7716809.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7716809
_shelx_shelxl_version_number     2018/3
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'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3108(3) 0.81219(18) 0.45321(19) 0.0312(6) Uani 1 1 d . . . . .
H1 H 0.26279 0.808485 0.491852 0.037 Uiso 1 1 calc R U . . .
C4 C 0.4469(4) 0.82487(19) 0.3428(2) 0.0363(7) Uani 1 1 d . . . . .
H4 H 0.497593 0.828844 0.305578 0.044 Uiso 1 1 calc R U . . .
C5 C 0.4889(3) 0.78341(16) 0.4069(2) 0.0282(6) Uani 1 1 d . . . . .
C6 C 0.6164(3) 0.74643(18) 0.4130(2) 0.0319(6) Uani 1 1 d . . . . .
C7 C 0.6330(3) 0.67503(17) 0.43538(18) 0.0283(6) Uani 1 1 d . . . . .
C8 C 0.7009(3) 0.63609(19) 0.3932(2) 0.0343(7) Uani 1 1 d . . . . .
H8 H 0.733523 0.655316 0.352894 0.041 Uiso 1 1 calc R U . . .
C9 C 0.7202(4) 0.56962(19) 0.4104(2) 0.0387(8) Uani 1 1 d . . . . .
H9 H 0.763777 0.542 0.381451 0.046 Uiso 1 1 calc R U . . .
C10 C 0.6742(4) 0.54436(18) 0.4713(2) 0.0385(8) Uani 1 1 d . . . . .
H10 H 0.688018 0.499063 0.485706 0.046 Uiso 1 1 calc R U . . .
C11 C 0.6081(3) 0.58558(16) 0.5107(2) 0.0321(6) Uani 1 1 d . . . . .
H11 H 0.577643 0.567455 0.552484 0.038 Uiso 1 1 calc R U . . .
C12 C 0.7280(3) 0.80704(17) 0.6193(2) 0.0294(6) Uani 1 1 d . . . . .
C13 C 0.8406(3) 0.80747(17) 0.6832(2) 0.0310(6) Uani 1 1 d . . . . .
H13 H 0.904217 0.84211 0.696882 0.037 Uiso 1 1 calc R U . . .
C14 C 0.8426(3) 0.74869(17) 0.72297(19) 0.0294(6) Uani 1 1 d . . . . .
C15 C 0.6783(4) 0.86198(17) 0.5626(2) 0.0381(7) Uani 1 1 d . . . . .
H15A H 0.701902 0.853014 0.513433 0.057 Uiso 1 1 calc R U . . .
H15B H 0.719067 0.903799 0.585009 0.057 Uiso 1 1 calc R U . . .
H15C H 0.581393 0.865222 0.552136 0.057 Uiso 1 1 calc R U . . .
C16 C 0.9411(3) 0.7266(2) 0.7960(2) 0.0360(7) Uani 1 1 d . . . . .
H16A H 0.894674 0.715094 0.835703 0.054 Uiso 1 1 calc R U . . .
H16B H 1.004474 0.762476 0.815822 0.054 Uiso 1 1 calc R U . . .
H16C H 0.989046 0.687727 0.784528 0.054 Uiso 1 1 calc R U . . .
C17 C 0.6705(3) 0.65460(15) 0.69919(18) 0.0257(5) Uani 1 1 d . . . . .
C18 C 0.7316(3) 0.60909(18) 0.7561(2) 0.0345(7) Uani 1 1 d . . . . .
H18 H 0.821606 0.614891 0.785215 0.041 Uiso 1 1 calc R U . . .
C19 C 0.6586(4) 0.55467(19) 0.7700(2) 0.0385(7) Uani 1 1 d . . . . .
H19 H 0.698993 0.523036 0.808867 0.046 Uiso 1 1 calc R U . . .
C20 C 0.5272(3) 0.54660(16) 0.7272(2) 0.0329(7) Uani 1 1 d . . . . .
H20 H 0.477222 0.509978 0.737601 0.039 Uiso 1 1 calc R U . . .
C21 C 0.4684(3) 0.59185(15) 0.66909(18) 0.0272(6) Uani 1 1 d . . . . .
H21 H 0.378307 0.585824 0.640265 0.033 Uiso 1 1 calc R U . . .
C22 C 0.5397(3) 0.64618(15) 0.65232(17) 0.0239(5) Uani 1 1 d . . . . .
C23 C 0.2298(3) 0.63008(16) 0.46932(17) 0.0268(6) Uani 1 1 d . . . . .
C24 C 0.1041(3) 0.61874(17) 0.48011(19) 0.0300(6) Uani 1 1 d . . . . .
H24 H 0.037659 0.590363 0.449412 0.036 Uiso 1 1 calc R U . . .
C25 C 0.0936(3) 0.65617(16) 0.54337(18) 0.0269(6) Uani 1 1 d . . . . .
C26 C 0.2870(4) 0.60441(18) 0.40587(19) 0.0331(7) Uani 1 1 d . . . . .
H26A H 0.327242 0.641041 0.383862 0.05 Uiso 1 1 calc R U . . .
H26B H 0.216164 0.584269 0.364378 0.05 Uiso 1 1 calc R U . . .
H26C H 0.355075 0.571069 0.427758 0.05 Uiso 1 1 calc R U . . .
C27 C -0.0224(3) 0.66160(19) 0.5785(2) 0.0335(7) Uani 1 1 d . . . . .
H27A H 0.007725 0.653266 0.635083 0.05 Uiso 1 1 calc R U . . .
H27B H -0.090164 0.628882 0.553956 0.05 Uiso 1 1 calc R U . . .
H27C H -0.06046 0.706209 0.569248 0.05 Uiso 1 1 calc R U . . .
C28 C 0.2593(3) 0.73984(15) 0.62566(17) 0.0255(5) Uani 1 1 d . . . . .
C29 C 0.1805(3) 0.7692(2) 0.6687(2) 0.0393(8) Uani 1 1 d . . . . .
H29 H 0.092552 0.753884 0.66389 0.047 Uiso 1 1 calc R U . . .
C30 C 0.2324(4) 0.8211(2) 0.7186(2) 0.0450(9) Uani 1 1 d . . . . .
H30 H 0.179579 0.841895 0.74808 0.054 Uiso 1 1 calc R U . . .
C31 C 0.3613(4) 0.84291(19) 0.7258(2) 0.0361(7) Uani 1 1 d . . . . .
H31 H 0.396947 0.878236 0.760531 0.043 Uiso 1 1 calc R U . . .
C32 C 0.4385(3) 0.81301(17) 0.68203(19) 0.0296(6) Uani 1 1 d . . . . .
H32 H 0.526562 0.828464 0.687483 0.036 Uiso 1 1 calc R U . . .
C33 C 0.3900(3) 0.76096(14) 0.63038(16) 0.0226(5) Uani 1 1 d . . . . .
C35 C 0.2622(3) 0.85451(18) 0.3905(2) 0.0351(7) Uani 1 1 d . . . . .
H35 H 0.183151 0.879152 0.386772 0.042 Uiso 1 1 calc R U . . .
C36 C 0.3303(4) 0.86053(19) 0.3333(2) 0.0378(7) Uani 1 1 d . . . . .
H36 H 0.297971 0.888301 0.288955 0.045 Uiso 1 1 calc R U . . .
C37 C 0.9374(19) 0.4174(8) 0.9357(8) 0.100(5) Uani 0.5 1 d . . P . .
H37A H 1.006122 0.448105 0.926903 0.12 Uiso 0.5 1 calc R U P . .
H37B H 0.89428 0.395826 0.885034 0.12 Uiso 0.5 1 calc R U P . .
Cl1 Cl 1.0139(3) 0.35673(18) 1.00405(18) 0.0777(8) Uani 0.5 1 d . . P . .
Cl2 Cl 0.8187(5) 0.4625(2) 0.9673(3) 0.1148(15) Uani 0.5 1 d . . P . .
F1 F 0.9238(3) 0.56969(11) 0.30655(14) 0.0450(5) Uani 1 1 d . . . . .
F2 F 1.0463(3) 0.53398(14) 0.22770(17) 0.0603(7) Uani 1 1 d . . . . .
F3 F 1.0642(3) 0.48386(12) 0.34383(15) 0.0538(6) Uani 1 1 d . . . . .
F4 F 0.9658(2) 0.42967(12) 0.23177(15) 0.0469(6) Uani 1 1 d . . . . .
F5 F 0.8429(3) 0.46525(12) 0.31031(16) 0.0494(6) Uani 1 1 d . . . . .
F6 F 0.8248(3) 0.51517(14) 0.19450(16) 0.0617(7) Uani 1 1 d . . . . .
Ir1 Ir 0.48286(2) 0.71041(2) 0.56237(2) 0.02174(4) Uani 1 1 d . . . . .
N1 N 0.4221(3) 0.77603(13) 0.46239(15) 0.0252(5) Uani 1 1 d . . . . .
N2 N 0.5846(3) 0.65019(13) 0.49313(15) 0.0256(5) Uani 1 1 d . . . . .
N3 N 0.6637(2) 0.74927(13) 0.61806(15) 0.0248(5) Uani 1 1 d . . . . .
N4 N 0.7345(3) 0.71310(12) 0.68212(16) 0.0252(5) Uani 1 1 d . . . . .
N5 N 0.2964(2) 0.67188(13) 0.52444(14) 0.0237(5) Uani 1 1 d . . . . .
N6 N 0.2116(2) 0.68877(13) 0.56963(14) 0.0238(5) Uani 1 1 d . . . . .
O1 O 0.7055(3) 0.77423(15) 0.39269(19) 0.0456(7) Uani 1 1 d . . . . .
P1 P 0.94527(9) 0.49973(4) 0.26872(5) 0.03045(16) Uani 1 1 d . . . . .
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 0 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 1 0 0.0760
2 -1 0 0.0620
0 0 -1 0.0780
0 0 1 0.0870
0 1 0 0.0760
0 -1 0 0.0610
1 0 -2 0.0830
-1 0 2 0.1060
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C35 123.6(3) . . ?
N1 C1 H1 118.2 . . ?
C35 C1 H1 118.2 . . ?
C5 C4 C36 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C36 C4 H4 120.3 . . ?
N1 C5 C4 123.2(3) . . ?
N1 C5 C6 120.5(3) . . ?
C4 C5 C6 116.3(3) . . ?
O1 C6 C7 118.6(3) . . ?
O1 C6 C5 118.6(3) . . ?
C7 C6 C5 122.5(3) . . ?
N2 C7 C8 122.5(3) . . ?
N2 C7 C6 121.2(3) . . ?
C8 C7 C6 116.3(3) . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 118.0(3) . . ?
C8 C9 H9 121 . . ?
C10 C9 H9 121 . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N2 C11 C10 123.4(3) . . ?
N2 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
N3 C12 C13 109.1(3) . . ?
N3 C12 C15 123.5(3) . . ?
C13 C12 C15 127.3(3) . . ?
C14 C13 C12 107.7(3) . . ?
C14 C13 H13 126.2 . . ?
C12 C13 H13 126.2 . . ?
N4 C14 C13 106.5(3) . . ?
N4 C14 C16 125.6(3) . . ?
C13 C14 C16 127.9(3) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 122.3(3) . . ?
C18 C17 N4 123.4(3) . . ?
C22 C17 N4 114.2(3) . . ?
C17 C18 C19 118.9(3) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C22 121.1(3) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C21 C22 C17 117.2(3) . . ?
C21 C22 Ir1 127.6(2) . . ?
C17 C22 Ir1 115.0(2) . . ?
N5 C23 C24 109.3(3) . . ?
N5 C23 C26 122.2(3) . . ?
C24 C23 C26 128.5(3) . . ?
C25 C24 C23 107.5(3) . . ?
C25 C24 H24 126.2 . . ?
C23 C24 H24 126.2 . . ?
N6 C25 C24 106.4(3) . . ?
N6 C25 C27 125.2(3) . . ?
C24 C25 C27 128.4(3) . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C33 122.7(3) . . ?
C29 C28 N6 122.7(3) . . ?
C33 C28 N6 114.5(2) . . ?
C30 C29 C28 118.9(3) . . ?
C30 C29 H29 120.6 . . ?
C28 C29 H29 120.6 . . ?
C29 C30 C31 120.3(3) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C30 C31 C32 120.0(3) . . ?
C30 C31 H31 120 . . ?
C32 C31 H31 120 . . ?
C31 C32 C33 121.8(3) . . ?
C31 C32 H32 119.1 . . ?
C33 C32 H32 119.1 . . ?
C32 C33 C28 116.3(3) . . ?
C32 C33 Ir1 128.7(2) . . ?
C28 C33 Ir1 115.0(2) . . ?
C1 C35 C36 119.2(3) . . ?
C1 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
C4 C36 C35 118.0(3) . . ?
C4 C36 H36 121 . . ?
C35 C36 H36 121 . . ?
Cl2 C37 Cl1 112.1(8) . . ?
Cl2 C37 H37A 109.2 . . ?
Cl1 C37 H37A 109.2 . . ?
Cl2 C37 H37B 109.2 . . ?
Cl1 C37 H37B 109.2 . . ?
H37A C37 H37B 107.9 . . ?
C33 Ir1 C22 86.73(11) . . ?
C33 Ir1 N5 79.72(11) . . ?
C22 Ir1 N5 93.95(11) . . ?
C33 Ir1 N3 92.67(11) . . ?
C22 Ir1 N3 79.99(11) . . ?
N5 Ir1 N3 170.59(10) . . ?
C33 Ir1 N1 95.39(11) . . ?
C22 Ir1 N1 177.59(11) . . ?
N5 Ir1 N1 85.31(10) . . ?
N3 Ir1 N1 101.02(10) . . ?
C33 Ir1 N2 176.50(11) . . ?
C22 Ir1 N2 89.91(10) . . ?
N5 Ir1 N2 99.55(10) . . ?
N3 Ir1 N2 87.71(10) . . ?
N1 Ir1 N2 87.95(10) . . ?
C1 N1 C5 116.5(3) . . ?
C1 N1 Ir1 119.2(2) . . ?
C5 N1 Ir1 124.3(2) . . ?
C11 N2 C7 116.9(3) . . ?
C11 N2 Ir1 119.6(2) . . ?
C7 N2 Ir1 123.4(2) . . ?
C12 N3 N4 106.8(3) . . ?
C12 N3 Ir1 137.4(2) . . ?
N4 N3 Ir1 114.59(18) . . ?
C14 N4 N3 109.9(3) . . ?
C14 N4 C17 133.5(3) . . ?
N3 N4 C17 115.5(2) . . ?
C23 N5 N6 106.8(2) . . ?
C23 N5 Ir1 138.4(2) . . ?
N6 N5 Ir1 114.65(18) . . ?
C25 N6 N5 110.0(2) . . ?
C25 N6 C28 134.7(3) . . ?
N5 N6 C28 114.9(2) . . ?
F2 P1 F6 90.72(18) . . ?
F2 P1 F3 90.21(16) . . ?
F6 P1 F3 179.06(18) . . ?
F2 P1 F4 91.28(14) . . ?
F6 P1 F4 89.94(14) . . ?
F3 P1 F4 90.18(14) . . ?
F2 P1 F1 89.39(14) . . ?
F6 P1 F1 90.22(14) . . ?
F3 P1 F1 89.65(14) . . ?
F4 P1 F1 179.31(14) . . ?
F2 P1 F5 179.84(15) . . ?
F6 P1 F5 89.26(16) . . ?
F3 P1 F5 89.80(15) . . ?
F4 P1 F5 88.88(13) . . ?
F1 P1 F5 90.45(13) . . ?
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
C1 N1 1.344(4) . ?
C1 C35 1.383(5) . ?
C1 H1 0.95 . ?
C4 C5 1.382(5) . ?
C4 C36 1.384(5) . ?
C4 H4 0.95 . ?
C5 N1 1.352(4) . ?
C5 C6 1.502(4) . ?
C6 O1 1.219(4) . ?
C6 C7 1.492(5) . ?
C7 N2 1.349(4) . ?
C7 C8 1.397(4) . ?
C8 C9 1.379(5) . ?
C8 H8 0.95 . ?
C9 C10 1.384(5) . ?
C9 H9 0.95 . ?
C10 C11 1.381(4) . ?
C10 H10 0.95 . ?
C11 N2 1.348(4) . ?
C11 H11 0.95 . ?
C12 N3 1.342(4) . ?
C12 C13 1.396(5) . ?
C12 C15 1.492(5) . ?
C13 C14 1.376(5) . ?
C13 H13 0.95 . ?
C14 N4 1.369(4) . ?
C14 C16 1.488(5) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 C18 1.386(4) . ?
C17 C22 1.405(4) . ?
C17 N4 1.428(4) . ?
C18 C19 1.394(5) . ?
C18 H18 0.95 . ?
C19 C20 1.388(5) . ?
C19 H19 0.95 . ?
C20 C21 1.389(4) . ?
C20 H20 0.95 . ?
C21 C22 1.400(4) . ?
C21 H21 0.95 . ?
C22 Ir1 2.014(3) . ?
C23 N5 1.335(4) . ?
C23 C24 1.392(4) . ?
C23 C26 1.495(4) . ?
C24 C25 1.377(4) . ?
C24 H24 0.95 . ?
C25 N6 1.364(4) . ?
C25 C27 1.502(4) . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?
C27 H27A 0.98 . ?
C27 H27B 0.98 . ?
C27 H27C 0.98 . ?
C28 C29 1.391(4) . ?
C28 C33 1.409(4) . ?
C28 N6 1.424(4) . ?
C29 C30 1.384(5) . ?
C29 H29 0.95 . ?
C30 C31 1.388(5) . ?
C30 H30 0.95 . ?
C31 C32 1.392(4) . ?
C31 H31 0.95 . ?
C32 C33 1.395(4) . ?
C32 H32 0.95 . ?
C33 Ir1 2.009(3) . ?
C35 C36 1.385(5) . ?
C35 H35 0.95 . ?
C36 H36 0.95 . ?
C37 Cl2 1.743(17) . ?
C37 Cl1 1.756(15) . ?
C37 H37A 0.99 . ?
C37 H37B 0.99 . ?
F1 P1 1.603(2) . ?
F2 P1 1.586(2) . ?
F3 P1 1.590(3) . ?
F4 P1 1.595(2) . ?
F5 P1 1.605(2) . ?
F6 P1 1.587(3) . ?
Ir1 N5 2.035(2) . ?
Ir1 N3 2.038(2) . ?
Ir1 N1 2.163(3) . ?
Ir1 N2 2.188(2) . ?
N3 N4 1.384(4) . ?
N5 N6 1.381(3) . ?
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
C36 C4 C5 N1 -0.7(6) . . . . ?
C36 C4 C5 C6 -180.0(3) . . . . ?
N1 C5 C6 O1 -142.6(4) . . . . ?
C4 C5 C6 O1 36.7(5) . . . . ?
N1 C5 C6 C7 43.7(5) . . . . ?
C4 C5 C6 C7 -137.0(3) . . . . ?
O1 C6 C7 N2 144.8(4) . . . . ?
C5 C6 C7 N2 -41.5(5) . . . . ?
O1 C6 C7 C8 -35.3(5) . . . . ?
C5 C6 C7 C8 138.5(3) . . . . ?
N2 C7 C8 C9 0.0(5) . . . . ?
C6 C7 C8 C9 -180.0(3) . . . . ?
C7 C8 C9 C10 -1.9(6) . . . . ?
C8 C9 C10 C11 1.8(6) . . . . ?
C9 C10 C11 N2 0.3(6) . . . . ?
N3 C12 C13 C14 -1.4(4) . . . . ?
C15 C12 C13 C14 175.2(3) . . . . ?
C12 C13 C14 N4 1.4(4) . . . . ?
C12 C13 C14 C16 -178.5(3) . . . . ?
C22 C17 C18 C19 -3.1(5) . . . . ?
N4 C17 C18 C19 177.9(3) . . . . ?
C17 C18 C19 C20 0.1(5) . . . . ?
C18 C19 C20 C21 1.4(5) . . . . ?
C19 C20 C21 C22 0.1(5) . . . . ?
C20 C21 C22 C17 -3.0(4) . . . . ?
C20 C21 C22 Ir1 171.3(2) . . . . ?
C18 C17 C22 C21 4.6(4) . . . . ?
N4 C17 C22 C21 -176.4(3) . . . . ?
C18 C17 C22 Ir1 -170.5(2) . . . . ?
N4 C17 C22 Ir1 8.6(3) . . . . ?
N5 C23 C24 C25 1.1(4) . . . . ?
C26 C23 C24 C25 -176.1(3) . . . . ?
C23 C24 C25 N6 -0.3(4) . . . . ?
C23 C24 C25 C27 179.7(3) . . . . ?
C33 C28 C29 C30 -0.4(6) . . . . ?
N6 C28 C29 C30 -176.3(4) . . . . ?
C28 C29 C30 C31 -0.5(7) . . . . ?
C29 C30 C31 C32 0.7(7) . . . . ?
C30 C31 C32 C33 -0.1(6) . . . . ?
C31 C32 C33 C28 -0.7(5) . . . . ?
C31 C32 C33 Ir1 -179.6(3) . . . . ?
C29 C28 C33 C32 0.9(5) . . . . ?
N6 C28 C33 C32 177.2(3) . . . . ?
C29 C28 C33 Ir1 180.0(3) . . . . ?
N6 C28 C33 Ir1 -3.8(3) . . . . ?
N1 C1 C35 C36 0.2(6) . . . . ?
C5 C4 C36 C35 1.9(6) . . . . ?
C1 C35 C36 C4 -1.7(6) . . . . ?
C35 C1 N1 C5 1.0(5) . . . . ?
C35 C1 N1 Ir1 -178.7(3) . . . . ?
C4 C5 N1 C1 -0.8(5) . . . . ?
C6 C5 N1 C1 178.5(3) . . . . ?
C4 C5 N1 Ir1 178.9(3) . . . . ?
C6 C5 N1 Ir1 -1.8(4) . . . . ?
C10 C11 N2 C7 -2.2(5) . . . . ?
C10 C11 N2 Ir1 -178.5(3) . . . . ?
C8 C7 N2 C11 2.0(5) . . . . ?
C6 C7 N2 C11 -178.0(3) . . . . ?
C8 C7 N2 Ir1 178.2(2) . . . . ?
C6 C7 N2 Ir1 -1.8(4) . . . . ?
C13 C12 N3 N4 0.8(3) . . . . ?
C15 C12 N3 N4 -175.9(3) . . . . ?
C13 C12 N3 Ir1 167.0(2) . . . . ?
C15 C12 N3 Ir1 -9.7(5) . . . . ?
C13 C14 N4 N3 -0.9(3) . . . . ?
C16 C14 N4 N3 179.0(3) . . . . ?
C13 C14 N4 C17 -168.1(3) . . . . ?
C16 C14 N4 C17 11.9(5) . . . . ?
C12 N3 N4 C14 0.1(3) . . . . ?
Ir1 N3 N4 C14 -169.70(19) . . . . ?
C12 N3 N4 C17 169.8(3) . . . . ?
Ir1 N3 N4 C17 0.0(3) . . . . ?
C18 C17 N4 C14 -19.9(5) . . . . ?
C22 C17 N4 C14 161.0(3) . . . . ?
C18 C17 N4 N3 173.5(3) . . . . ?
C22 C17 N4 N3 -5.6(4) . . . . ?
C24 C23 N5 N6 -1.5(3) . . . . ?
C26 C23 N5 N6 175.9(3) . . . . ?
C24 C23 N5 Ir1 173.4(2) . . . . ?
C26 C23 N5 Ir1 -9.2(5) . . . . ?
C24 C25 N6 N5 -0.6(4) . . . . ?
C27 C25 N6 N5 179.4(3) . . . . ?
C24 C25 N6 C28 171.3(3) . . . . ?
C27 C25 N6 C28 -8.7(6) . . . . ?
C23 N5 N6 C25 1.4(3) . . . . ?
Ir1 N5 N6 C25 -174.9(2) . . . . ?
C23 N5 N6 C28 -172.3(3) . . . . ?
Ir1 N5 N6 C28 11.4(3) . . . . ?
C29 C28 N6 C25 -0.4(6) . . . . ?
C33 C28 N6 C25 -176.7(3) . . . . ?
C29 C28 N6 N5 171.2(3) . . . . ?
C33 C28 N6 N5 -5.1(4) . . . . ?
