#------------------------------------------------------------------------------
#$Date: 2020-04-03 02:16:36 +0300 (Fri, 03 Apr 2020) $
#$Revision: 249976 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557717.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_1557717
loop_
_publ_author_name
'Carrasco, Ana C.'
'Rodríguez-Fanjul, Vanessa'
'Habtemariam, Abraha'
'Pizarro, Ana M.'
_publ_section_title
;
 Structurally Strained Half-Sandwich Iridium(III) Complexes As Highly
 Potent Anticancer Agents.
;
_journal_name_full               'Journal of medicinal chemistry'
_journal_paper_doi               10.1021/acs.jmedchem.9b02000
_journal_year                    2020
_chemical_formula_sum            'C27.75 H28.75 Cl2.25 F6 Ir N2 P'
_chemical_formula_weight         807.21
_chemical_name_common            ACC_73_150K
_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
_cell_angle_alpha                81.1829(16)
_cell_angle_beta                 82.9683(14)
_cell_angle_gamma                87.8789(15)
_cell_formula_units_Z            2
_cell_length_a                   8.8214(2)
_cell_length_b                   12.8110(4)
_cell_length_c                   13.5282(4)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      25.6134
_cell_measurement_theta_min      2.6314
_cell_volume                     1499.15(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            51300
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    4.765
_exptl_absorpt_correction_T_max  0.61
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             787
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.116
_refine_diff_density_max         2.779
_refine_diff_density_min         -1.886
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         5499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0648P)²+12.4114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1227
_reflns_number_gt                5195
_reflns_number_total             5499
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jm9b02000_si_004.cif
_cod_data_source_block           02559AnaMPizarro
_cod_database_code               1557717
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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1521(9) 0.1028(6) 0.7854(6) 0.0254(17) Uani d . . . 1 . .
C C2 -0.0129(9) 0.0955(6) 0.7990(6) 0.0242(16) Uani d . . . 1 . .
C C3 -0.0654(9) 0.1191(5) 0.8992(5) 0.0215(15) Uani d . . . 1 . .
C C4 0.0678(9) 0.1413(6) 0.9451(6) 0.0225(15) Uani d . . . 1 . .
C C5 0.2055(9) 0.1274(6) 0.8747(6) 0.0232(16) Uani d . . . 1 . .
C C6 0.2473(11) 0.1051(7) 0.6841(6) 0.0336(19) Uani d . . . 1 . .
H H6A 0.2199 0.0448 0.6523 0.04 Uiso calc U . R 1 . .
H H6B 0.3567 0.0971 0.694 0.04 Uiso calc U . R 1 . .
C C7 0.2226(9) 0.2077(6) 0.6143(6) 0.0234(16) Uani d . . . 1 . .
C C8 0.2765(10) 0.2180(7) 0.5127(6) 0.0331(19) Uani d . . . 1 . .
H H8 0.3257 0.1599 0.4851 0.04 Uiso calc U . R 1 . .
C C9 0.2580(11) 0.3129(8) 0.4525(6) 0.040(2) Uani d . . . 1 . .
H H9 0.2947 0.3209 0.3828 0.048 Uiso calc U . R 1 . .
C C10 0.1862(11) 0.3965(7) 0.4932(6) 0.035(2) Uani d . . . 1 . .
H H10 0.1731 0.4626 0.4522 0.042 Uiso calc U . R 1 . .
C C11 0.1337(9) 0.3827(6) 0.5943(6) 0.0264(17) Uani d . . . 1 . .
H H11 0.0846 0.4403 0.6227 0.032 Uiso calc U . R 1 . .
C C12 -0.1087(11) 0.0584(7) 0.7273(7) 0.036(2) Uani d . . . 1 . .
H H12A -0.0986 -0.0185 0.7317 0.055 Uiso calc U . R 1 . .
H H12B -0.0741 0.0916 0.6584 0.055 Uiso calc U . R 1 . .
H H12C -0.2159 0.078 0.7449 0.055 Uiso calc U . R 1 . .
C C13 -0.2274(9) 0.1185(7) 0.9464(6) 0.0303(18) Uani d . . . 1 . .
H H13A -0.2892 0.1663 0.903 0.045 Uiso calc U . R 1 . .
H H13B -0.2327 0.1421 1.0123 0.045 Uiso calc U . R 1 . .
H H13C -0.2667 0.0467 0.955 0.045 Uiso calc U . R 1 . .
C C14 0.0695(10) 0.1664(6) 1.0486(6) 0.0281(17) Uani d . . . 1 . .
H H14A 0.1105 0.1056 1.091 0.042 Uiso calc U . R 1 . .
H H14B -0.0348 0.1826 1.0769 0.042 Uiso calc U . R 1 . .
H H14C 0.1339 0.2277 1.0461 0.042 Uiso calc U . R 1 . .
C C15 0.3679(10) 0.1338(7) 0.8946(7) 0.0340(19) Uani d . . . 1 . .
H H15A 0.4125 0.0625 0.9063 0.051 Uiso calc U . R 1 . .
H H15B 0.3713 0.1682 0.9542 0.051 Uiso calc U . R 1 . .
H H15C 0.4263 0.175 0.8362 0.051 Uiso calc U . R 1 . .
C C16 -0.1302(9) 0.3504(6) 0.7759(6) 0.0242(16) Uani d . . . 1 . .
C C17 -0.2533(9) 0.3262(7) 0.7308(6) 0.0313(18) Uani d . . . 1 . .
H H17 -0.2563 0.2589 0.7099 0.038 Uiso calc U . R 1 . .
C C18 -0.3742(10) 0.3980(8) 0.7149(7) 0.039(2) Uani d . . . 1 . .
C C19 -0.3668(12) 0.4961(7) 0.7485(7) 0.045(3) Uani d . . . 1 . .
H H19 -0.4497 0.545 0.7409 0.054 Uiso calc U . R 1 . .
C C20 -0.2476(11) 0.5232(7) 0.7908(7) 0.038(2) Uani d . . . 1 . .
H H20 -0.2467 0.5904 0.8121 0.046 Uiso calc U . R 1 . .
C C21 -0.1242(10) 0.4526(6) 0.8035(6) 0.0300(19) Uani d . . . 1 . .
C C22 0.0134(10) 0.4764(6) 0.8429(6) 0.0303(18) Uani d . . . 1 . .
C C23 0.0479(13) 0.5728(7) 0.8717(8) 0.049(3) Uani d . . . 1 . .
H H23 -0.0233 0.6302 0.8651 0.059 Uiso calc U . R 1 . .
C C24 0.1823(14) 0.5853(8) 0.9089(8) 0.053(3) Uani d . . . 1 . .
H H24 0.2047 0.6505 0.9288 0.063 Uiso calc U . R 1 . .
C C25 0.2832(13) 0.5023(8) 0.9170(7) 0.045(2) Uani d . . . 1 . .
H H25 0.3769 0.509 0.9432 0.054 Uiso calc U . R 1 . .
C C26 0.2494(10) 0.4090(7) 0.8872(6) 0.0321(19) Uani d . . . 1 . .
H H26 0.3215 0.3521 0.8928 0.039 Uiso calc U . R 1 . .
C C27 -0.5025(12) 0.3737(10) 0.6639(9) 0.056(3) Uani d . . . 1 . .
H H27A -0.5986 0.3845 0.7061 0.085 Uiso calc U . R 1 . .
H H27B -0.4939 0.2999 0.6523 0.085 Uiso calc U . R 1 . .
H H27C -0.5012 0.4203 0.5992 0.085 Uiso calc U . R 1 . .
C C28 0.2318(12) 0.7789(10) 0.6052(10) 0.037(3) Uani d . P . 0.75 . .
H H28 0.2947 0.785 0.6607 0.044 Uiso calc U P R 0.75 . .
Cl Cl1 0.2588(5) 0.6515(3) 0.5769(3) 0.0651(11) Uani d . P . 0.75 . .
Cl Cl2 0.0411(4) 0.8013(4) 0.6512(4) 0.0707(12) Uani d . P . 0.75 . .
Cl Cl3 0.2977(5) 0.8747(3) 0.5019(3) 0.0579(10) Uani d . P . 0.75 . .
F F1 0.4941(7) 0.7372(5) 0.7373(5) 0.0612(18) Uani d . . . 1 . .
F F2 0.7119(6) 0.7963(5) 0.7759(5) 0.0520(15) Uani d . . . 1 . .
F F3 0.5145(8) 0.7523(6) 0.8973(5) 0.0645(18) Uani d . . . 1 . .
F F4 0.5793(7) 0.9221(5) 0.8512(5) 0.0552(16) Uani d . . . 1 . .
F F5 0.3603(6) 0.8645(5) 0.8083(5) 0.0505(15) Uani d . . . 1 . .
F F6 0.5547(8) 0.9070(6) 0.6894(5) 0.0653(18) Uani d . . . 1 . .
Ir Ir1 0.05472(3) 0.25368(2) 0.80528(2) 0.01865(12) Uani d . . . 1 . .
N N1 0.1500(7) 0.2896(5) 0.6544(4) 0.0204(13) Uani d . . . 1 . .
N N2 0.1173(8) 0.3952(5) 0.8501(5) 0.0260(14) Uani d . . . 1 . .
P P1 0.5369(3) 0.83092(19) 0.79348(17) 0.0321(5) 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'
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 C1 C2 . . 110.4(7) ?
C5 C1 C6 . . 125.4(8) ?
C2 C1 C6 . . 123.2(7) ?
C5 C1 Ir1 . . 74.5(4) ?
C2 C1 Ir1 . . 71.1(4) ?
C6 C1 Ir1 . . 112.1(5) ?
C1 C2 C3 . . 107.1(7) ?
C1 C2 C12 . . 126.0(7) ?
C3 C2 C12 . . 126.6(7) ?
C1 C2 Ir1 . . 69.3(4) ?
C3 C2 Ir1 . . 72.4(4) ?
C12 C2 Ir1 . . 128.5(6) ?
C4 C3 C2 . . 107.7(6) ?
C4 C3 C13 . . 126.5(7) ?
C2 C3 C13 . . 125.8(7) ?
C4 C3 Ir1 . . 71.0(4) ?
C2 C3 Ir1 . . 68.7(4) ?
C13 C3 Ir1 . . 126.5(5) ?
C3 C4 C5 . . 108.7(6) ?
C3 C4 C14 . . 126.7(7) ?
C5 C4 C14 . . 124.4(7) ?
C3 C4 Ir1 . . 70.5(4) ?
C5 C4 Ir1 . . 71.2(4) ?
C14 C4 Ir1 . . 127.5(5) ?
C1 C5 C4 . . 105.9(7) ?
C1 C5 C15 . . 127.4(7) ?
C4 C5 C15 . . 126.7(7) ?
C1 C5 Ir1 . . 67.1(4) ?
C4 C5 Ir1 . . 70.0(4) ?
C15 C5 Ir1 . . 129.0(6) ?
C1 C6 C7 . . 111.6(6) ?
C1 C6 H6A . . 109.3 ?
C7 C6 H6A . . 109.3 ?
C1 C6 H6B . . 109.3 ?
C7 C6 H6B . . 109.3 ?
H6A C6 H6B . . 108.0 ?
N1 C7 C8 . . 120.9(7) ?
N1 C7 C6 . . 118.4(6) ?
C8 C7 C6 . . 120.6(7) ?
C9 C8 C7 . . 119.3(8) ?
C9 C8 H8 . . 120.4 ?
C7 C8 H8 . . 120.4 ?
C8 C9 C10 . . 119.9(8) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C11 C10 C9 . . 118.8(8) ?
C11 C10 H10 . . 120.6 ?
C9 C10 H10 . . 120.6 ?
N1 C11 C10 . . 121.9(7) ?
N1 C11 H11 . . 119.0 ?
C10 C11 H11 . . 119.0 ?
C2 C12 H12A . . 109.5 ?
C2 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C2 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C3 C13 H13A . . 109.5 ?
C3 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C3 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C4 C14 H14A . . 109.5 ?
C4 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C4 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C5 C15 H15A . . 109.5 ?
C5 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C5 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C17 C16 C21 . . 118.7(7) ?
C17 C16 Ir1 . . 126.4(6) ?
C21 C16 Ir1 . . 114.9(6) ?
C16 C17 C18 . . 121.7(9) ?
C16 C17 H17 . . 119.1 ?
C18 C17 H17 . . 119.1 ?
C17 C18 C19 . . 117.4(9) ?
C17 C18 C27 . . 121.7(10) ?
C19 C18 C27 . . 120.9(9) ?
C20 C19 C18 . . 122.5(8) ?
C20 C19 H19 . . 118.8 ?
C18 C19 H19 . . 118.8 ?
C19 C20 C21 . . 120.1(9) ?
C19 C20 H20 . . 120.0 ?
C21 C20 H20 . . 120.0 ?
C20 C21 C16 . . 119.5(9) ?
C20 C21 C22 . . 124.4(8) ?
C16 C21 C22 . . 116.2(7) ?
N2 C22 C23 . . 119.2(9) ?
N2 C22 C21 . . 114.2(7) ?
C23 C22 C21 . . 126.5(8) ?
C24 C23 C22 . . 121.1(10) ?
C24 C23 H23 . . 119.5 ?
C22 C23 H23 . . 119.5 ?
C25 C24 C23 . . 118.5(9) ?
C25 C24 H24 . . 120.7 ?
C23 C24 H24 . . 120.7 ?
C24 C25 C26 . . 119.9(10) ?
C24 C25 H25 . . 120.0 ?
C26 C25 H25 . . 120.0 ?
N2 C26 C25 . . 122.4(9) ?
N2 C26 H26 . . 118.8 ?
C25 C26 H26 . . 118.8 ?
C18 C27 H27A . . 109.5 ?
C18 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C18 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
Cl1 C28 Cl2 . . 110.8(7) ?
Cl1 C28 Cl3 . . 111.9(7) ?
Cl2 C28 Cl3 . . 112.4(7) ?
Cl1 C28 H28 . . 107.1 ?
Cl2 C28 H28 . . 107.1 ?
Cl3 C28 H28 . . 107.1 ?
C16 Ir1 N1 . . 90.4(3) ?
C16 Ir1 N2 . . 78.3(3) ?
N1 Ir1 N2 . . 96.1(2) ?
C16 Ir1 C1 . . 142.3(3) ?
N1 Ir1 C1 . . 81.2(3) ?
N2 Ir1 C1 . . 138.9(3) ?
C16 Ir1 C2 . . 106.5(3) ?
N1 Ir1 C2 . . 97.2(3) ?
N2 Ir1 C2 . . 165.8(3) ?
C1 Ir1 C2 . . 39.6(3) ?
C16 Ir1 C3 . . 99.1(3) ?
N1 Ir1 C3 . . 136.0(3) ?
N2 Ir1 C3 . . 127.8(3) ?
C1 Ir1 C3 . . 65.2(3) ?
C2 Ir1 C3 . . 38.9(3) ?
C16 Ir1 C4 . . 124.5(3) ?
N1 Ir1 C4 . . 143.4(3) ?
N2 Ir1 C4 . . 101.1(3) ?
C1 Ir1 C4 . . 64.6(3) ?
C2 Ir1 C4 . . 65.0(3) ?
C3 Ir1 C4 . . 38.4(3) ?
C16 Ir1 C5 . . 162.9(3) ?
N1 Ir1 C5 . . 105.3(3) ?
N2 Ir1 C5 . . 106.1(3) ?
C1 Ir1 C5 . . 38.3(3) ?
C2 Ir1 C5 . . 65.4(3) ?
C3 Ir1 C5 . . 65.0(3) ?
C4 Ir1 C5 . . 38.8(3) ?
C11 N1 C7 . . 119.1(6) ?
C11 N1 Ir1 . . 125.4(5) ?
C7 N1 Ir1 . . 115.2(5) ?
C26 N2 C22 . . 118.9(7) ?
C26 N2 Ir1 . . 124.8(6) ?
C22 N2 Ir1 . . 116.4(6) ?
F6 P1 F4 . . 91.5(4) ?
F6 P1 F2 . . 90.3(4) ?
F4 P1 F2 . . 90.6(3) ?
F6 P1 F1 . . 89.6(4) ?
F4 P1 F1 . . 178.8(4) ?
F2 P1 F1 . . 89.3(3) ?
F6 P1 F3 . . 178.1(4) ?
F4 P1 F3 . . 90.0(4) ?
F2 P1 F3 . . 90.8(4) ?
F1 P1 F3 . . 88.8(4) ?
F6 P1 F5 . . 88.9(4) ?
F4 P1 F5 . . 90.9(3) ?
F2 P1 F5 . . 178.4(3) ?
F1 P1 F5 . . 89.3(3) ?
F3 P1 F5 . . 90.0(4) ?
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
C1 C5 . 1.432(11) ?
C1 C2 . 1.449(11) ?
C1 C6 . 1.514(11) ?
C1 Ir1 . 2.127(7) ?
C2 C3 . 1.450(10) ?
C2 C12 . 1.501(11) ?
C2 Ir1 . 2.151(8) ?
C3 C4 . 1.451(11) ?
C3 C13 . 1.492(10) ?
C3 Ir1 . 2.201(7) ?
C4 C5 . 1.473(10) ?
C4 C14 . 1.485(10) ?
C4 Ir1 . 2.207(7) ?
C5 C15 . 1.497(12) ?
C5 Ir1 . 2.224(7) ?
C6 C7 . 1.522(11) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 N1 . 1.358(10) ?
C7 C8 . 1.386(11) ?
C8 C9 . 1.373(13) ?
C8 H8 . 0.95 ?
C9 C10 . 1.378(13) ?
C9 H9 . 0.95 ?
C10 C11 . 1.376(11) ?
C10 H10 . 0.95 ?
C11 N1 . 1.350(10) ?
C11 H11 . 0.95 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 C17 . 1.376(12) ?
C16 C21 . 1.420(11) ?
C16 Ir1 . 2.053(8) ?
C17 C18 . 1.398(12) ?
C17 H17 . 0.95 ?
C18 C19 . 1.407(15) ?
C18 C27 . 1.462(14) ?
C19 C20 . 1.337(15) ?
C19 H19 . 0.95 ?
C20 C21 . 1.399(12) ?
C20 H20 . 0.95 ?
C21 C22 . 1.444(13) ?
C22 N2 . 1.360(11) ?
C22 C23 . 1.405(13) ?
C23 C24 . 1.368(16) ?
C23 H23 . 0.95 ?
C24 C25 . 1.361(16) ?
C24 H24 . 0.95 ?
C25 C26 . 1.372(12) ?
C25 H25 . 0.95 ?
C26 N2 . 1.352(11) ?
C26 H26 . 0.95 ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 Cl1 . 1.734(12) ?
C28 Cl2 . 1.750(11) ?
C28 Cl3 . 1.769(15) ?
C28 H28 . 1.0 ?
F1 P1 . 1.595(6) ?
F2 P1 . 1.590(6) ?
F3 P1 . 1.594(7) ?
F4 P1 . 1.580(6) ?
F5 P1 . 1.597(6) ?
F6 P1 . 1.579(7) ?
Ir1 N1 . 2.099(6) ?
Ir1 N2 . 2.110(7) ?
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
C28 H28 F1 . 1.00 2.17 3.076(12) 149.6 ?
C28 H28 F5 . 1.00 2.51 3.436(12) 153.6 ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 C1 C2 C3 . . . . 1.6(8) ?
C6 C1 C2 C3 . . . . -167.5(7) ?
Ir1 C1 C2 C3 . . . . -63.0(5) ?
C5 C1 C2 C12 . . . . -172.2(7) ?
C6 C1 C2 C12 . . . . 18.7(12) ?
Ir1 C1 C2 C12 . . . . 123.2(8) ?
C5 C1 C2 Ir1 . . . . 64.6(5) ?
C6 C1 C2 Ir1 . . . . -104.5(7) ?
C1 C2 C3 C4 . . . . 0.4(8) ?
C12 C2 C3 C4 . . . . 174.1(7) ?
Ir1 C2 C3 C4 . . . . -60.6(5) ?
C1 C2 C3 C13 . . . . -178.6(7) ?
C12 C2 C3 C13 . . . . -4.9(12) ?
Ir1 C2 C3 C13 . . . . 120.4(7) ?
C1 C2 C3 Ir1 . . . . 61.0(5) ?
C12 C2 C3 Ir1 . . . . -125.3(8) ?
C2 C3 C4 C5 . . . . -2.2(8) ?
C13 C3 C4 C5 . . . . 176.8(7) ?
Ir1 C3 C4 C5 . . . . -61.3(5) ?
C2 C3 C4 C14 . . . . -178.1(7) ?
C13 C3 C4 C14 . . . . 0.9(12) ?
Ir1 C3 C4 C14 . . . . 122.8(8) ?
C2 C3 C4 Ir1 . . . . 59.1(5) ?
C13 C3 C4 Ir1 . . . . -121.9(7) ?
C2 C1 C5 C4 . . . . -2.9(8) ?
C6 C1 C5 C4 . . . . 165.9(7) ?
Ir1 C1 C5 C4 . . . . 59.6(5) ?
C2 C1 C5 C15 . . . . 175.0(7) ?
C6 C1 C5 C15 . . . . -16.2(12) ?
Ir1 C1 C5 C15 . . . . -122.6(8) ?
C2 C1 C5 Ir1 . . . . -62.5(5) ?
C6 C1 C5 Ir1 . . . . 106.3(7) ?
C3 C4 C5 C1 . . . . 3.1(8) ?
C14 C4 C5 C1 . . . . 179.2(7) ?
Ir1 C4 C5 C1 . . . . -57.7(5) ?
C3 C4 C5 C15 . . . . -174.8(7) ?
C14 C4 C5 C15 . . . . 1.3(12) ?
Ir1 C4 C5 C15 . . . . 124.4(8) ?
C3 C4 C5 Ir1 . . . . 60.9(5) ?
C14 C4 C5 Ir1 . . . . -123.1(7) ?
C5 C1 C6 C7 . . . . -98.1(9) ?
C2 C1 C6 C7 . . . . 69.3(10) ?
Ir1 C1 C6 C7 . . . . -11.9(9) ?
C1 C6 C7 N1 . . . . 13.6(11) ?
C1 C6 C7 C8 . . . . -168.1(8) ?
N1 C7 C8 C9 . . . . 1.0(13) ?
C6 C7 C8 C9 . . . . -177.3(9) ?
C7 C8 C9 C10 . . . . -0.1(15) ?
C8 C9 C10 C11 . . . . -0.2(15) ?
C9 C10 C11 N1 . . . . -0.3(14) ?
C21 C16 C17 C18 . . . . -2.2(12) ?
Ir1 C16 C17 C18 . . . . 179.6(6) ?
C16 C17 C18 C19 . . . . -1.1(12) ?
C16 C17 C18 C27 . . . . 177.9(8) ?
C17 C18 C19 C20 . . . . 2.5(13) ?
C27 C18 C19 C20 . . . . -176.5(9) ?
C18 C19 C20 C21 . . . . -0.4(14) ?
C19 C20 C21 C16 . . . . -3.1(12) ?
C19 C20 C21 C22 . . . . 176.3(8) ?
C17 C16 C21 C20 . . . . 4.3(11) ?
Ir1 C16 C21 C20 . . . . -177.2(6) ?
C17 C16 C21 C22 . . . . -175.1(7) ?
Ir1 C16 C21 C22 . . . . 3.3(9) ?
C20 C21 C22 N2 . . . . 179.1(7) ?
C16 C21 C22 N2 . . . . -1.5(10) ?
C20 C21 C22 C23 . . . . -1.9(13) ?
C16 C21 C22 C23 . . . . 177.5(8) ?
N2 C22 C23 C24 . . . . -1.6(14) ?
C21 C22 C23 C24 . . . . 179.4(9) ?
C22 C23 C24 C25 . . . . 0.5(16) ?
C23 C24 C25 C26 . . . . 0.5(16) ?
C24 C25 C26 N2 . . . . -0.5(15) ?
C10 C11 N1 C7 . . . . 1.2(12) ?
C10 C11 N1 Ir1 . . . . -173.0(6) ?
C8 C7 N1 C11 . . . . -1.5(12) ?
C6 C7 N1 C11 . . . . 176.8(7) ?
C8 C7 N1 Ir1 . . . . 173.3(6) ?
C6 C7 N1 Ir1 . . . . -8.4(9) ?
C25 C26 N2 C22 . . . . -0.7(12) ?
C25 C26 N2 Ir1 . . . . -178.8(7) ?
C23 C22 N2 C26 . . . . 1.7(11) ?
C21 C22 N2 C26 . . . . -179.3(7) ?
C23 C22 N2 Ir1 . . . . 179.9(6) ?
C21 C22 N2 Ir1 . . . . -1.0(8) ?
