#------------------------------------------------------------------------------
#$Date: 2019-12-16 12:02:30 +0200 (Mon, 16 Dec 2019) $
#$Revision: 245210 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/65/1556590.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_1556590
loop_
_publ_author_name
'Grotjahn, D.B.'
'Martin, J.K.'
'Tom, T.N.'
'Rheingold, A.L.'
_publ_section_title
;
 Cationic Protic Imidazolylidene NHC Complexes of Cp*IrCl+ and Cp*RhCl+
 with a Pyridyl Tether Formed at Ambient Temperature
;
_journal_name_full               Inorganics
_journal_page_first              27
_journal_paper_doi               10.3390/inorganics6010027
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C23 H32 Cl Ir N3, F6 P, 1.5(C4 H8 O)'
_chemical_formula_sum            'C29 H44 Cl F6 Ir N3 O1.5 P'
_chemical_formula_weight         831.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.9277(7)
_cell_length_b                   19.2100(11)
_cell_length_c                   28.2172(16)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.24
_cell_volume                     6465.4(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.899
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.899
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            54283
_diffrn_reflns_point_group_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.551
_diffrn_reflns_theta_min         2.010
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.326
_exptl_absorpt_correction_T_max  0.6476
_exptl_absorpt_correction_T_min  0.4110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3312
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.198
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         7090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0287
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0114P)²+11.8459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0502
_refine_ls_wR_factor_ref         0.0563
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5367
_reflns_number_total             7090
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            9bIr_Fig2_Grot304.cif
_cod_data_source_block           grot304
_cod_original_formula_sum        'C29 H44 Cl F6 Ir N3 O1.50 P'
_cod_database_code               1556590
_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_max   0.648
_shelx_estimated_absorpt_t_min   0.411
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F4) = Uanis(F4B)
Uanis(F2) = Uanis(F2B)
3. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C1S(H1SA,H1SB), C2S(H2SA,H2SB), C3S(H3SA,H3SB), C4S(H4SA,H4SB),
 C5S(H5SA,H5SB), C6S(H6SA,H6SB)
4.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3A), C6(H6), C7(H7), C8(H8), C9(H9)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,
 H23B,H23C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, 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
Ir1 Ir 0.53833(2) 0.24355(2) 0.36214(2) 0.01359(4) Uani 1 1 d . . . . .
Cl1 Cl 0.64529(7) 0.24069(4) 0.28953(4) 0.0202(2) Uani 1 1 d . . . . .
P1 P 0.01847(9) 0.12167(5) 0.43657(5) 0.0264(3) Uani 1 1 d . . . . .
F1 F -0.0054(4) 0.0520(2) 0.4681(2) 0.0473(14) Uani 0.740(5) 1 d . . . A 1
F2 F -0.0555(3) 0.0879(3) 0.39604(16) 0.0485(12) Uani 0.740(5) 1 d . . . A 1
F3 F 0.0490(5) 0.1860(2) 0.4062(2) 0.0362(13) Uani 0.740(5) 1 d . . . A 1
F4 F 0.0996(4) 0.1481(2) 0.47911(17) 0.0416(11) Uani 0.740(5) 1 d . . . A 1
F1B F -0.0571(11) 0.0592(6) 0.4430(7) 0.048(5) Uani 0.260(5) 1 d . . . A 2
F2B F -0.0582(9) 0.1399(7) 0.3864(4) 0.0485(12) Uani 0.260(5) 1 d . . . A 2
F3B F 0.0707(13) 0.2025(7) 0.4259(6) 0.033(4) Uani 0.260(5) 1 d . . . A 2
F4B F 0.0759(12) 0.1194(7) 0.4810(6) 0.0416(11) Uani 0.260(5) 1 d . . . A 2
F5 F 0.1225(2) 0.08206(12) 0.41221(10) 0.0428(7) Uani 1 1 d . . . . .
F6 F -0.0855(2) 0.16140(13) 0.46062(10) 0.0444(8) Uani 1 1 d . . . . .
N1 N 0.6644(2) 0.30986(13) 0.38868(12) 0.0161(7) Uani 1 1 d . . . . .
N2 N 0.4670(2) 0.39180(13) 0.36539(12) 0.0146(7) Uani 1 1 d . . . . .
N3 N 0.4014(2) 0.34729(13) 0.30167(12) 0.0158(7) Uani 1 1 d . . . . .
H3 H 0.3860 0.3174 0.2789 0.019 Uiso 1 1 calc R . . . .
C1 C 0.4642(3) 0.33208(16) 0.34002(14) 0.0148(8) Uani 1 1 d . . . . .
C2 C 0.3635(3) 0.41618(17) 0.30229(15) 0.0154(8) Uani 1 1 d . . . . .
C3 C 0.4055(3) 0.44357(17) 0.34228(15) 0.0188(9) Uani 1 1 d . . . . .
H3A H 0.3951 0.4900 0.3530 0.023 Uiso 1 1 calc R . . . .
C4 C 0.5235(3) 0.39728(17) 0.41059(15) 0.0179(9) Uani 1 1 d . . . . .
H4A H 0.4818 0.3696 0.4344 0.021 Uiso 1 1 calc R . . . .
H4B H 0.5223 0.4465 0.4210 0.021 Uiso 1 1 calc R . . . .
C5 C 0.6433(3) 0.37242(16) 0.40913(15) 0.0181(9) Uani 1 1 d . . . . .
C6 C 0.7278(3) 0.41162(18) 0.42928(15) 0.0220(9) Uani 1 1 d . . . . .
H6 H 0.7114 0.4557 0.4429 0.026 Uiso 1 1 calc R . . . .
C7 C 0.8365(3) 0.38631(19) 0.42952(16) 0.0264(10) Uani 1 1 d . . . . .
H7 H 0.8951 0.4121 0.4441 0.032 Uiso 1 1 calc R . . . .
C8 C 0.8585(3) 0.32308(19) 0.40831(16) 0.0275(11) Uani 1 1 d . . . . .
H8 H 0.9326 0.3050 0.4077 0.033 Uiso 1 1 calc R . . . .
C9 C 0.7716(3) 0.28670(18) 0.38811(15) 0.0226(10) Uani 1 1 d . . . . .
H9 H 0.7873 0.2435 0.3731 0.027 Uiso 1 1 calc R . . . .
C10 C 0.2860(3) 0.44608(17) 0.26570(15) 0.0193(9) Uani 1 1 d . . . . .
C11 C 0.3348(3) 0.4389(2) 0.21624(15) 0.0295(11) Uani 1 1 d . . . . .
H11A H 0.4057 0.4646 0.2144 0.044 Uiso 1 1 calc GR . . . .
H11B H 0.2819 0.4579 0.1930 0.044 Uiso 1 1 calc GR . . . .
H11C H 0.3483 0.3896 0.2093 0.044 Uiso 1 1 calc GR . . . .
C12 C 0.1726(3) 0.4077(2) 0.26822(18) 0.0363(12) Uani 1 1 d . . . . .
H12A H 0.1836 0.3585 0.2604 0.055 Uiso 1 1 calc GR . . . .
H12B H 0.1202 0.4286 0.2456 0.055 Uiso 1 1 calc GR . . . .
H12C H 0.1419 0.4117 0.3003 0.055 Uiso 1 1 calc GR . . . .
C13 C 0.2696(4) 0.52344(18) 0.27681(16) 0.0302(11) Uani 1 1 d . . . . .
H13A H 0.2369 0.5285 0.3085 0.045 Uiso 1 1 calc GR . . . .
H13B H 0.2191 0.5441 0.2533 0.045 Uiso 1 1 calc GR . . . .
H13C H 0.3422 0.5472 0.2758 0.045 Uiso 1 1 calc GR . . . .
C14 C 0.4144(3) 0.20752(16) 0.41259(15) 0.0166(9) Uani 1 1 d . . . . .
C15 C 0.5229(3) 0.18281(16) 0.42755(14) 0.0151(8) Uani 1 1 d . . . . .
C16 C 0.5673(3) 0.13826(16) 0.39141(15) 0.0176(9) Uani 1 1 d . . . . .
C17 C 0.4862(3) 0.13503(16) 0.35386(15) 0.0178(9) Uani 1 1 d . . . . .
C18 C 0.3914(3) 0.17771(16) 0.36656(15) 0.0165(8) Uani 1 1 d . . . . .
C19 C 0.3321(3) 0.24790(18) 0.44161(16) 0.0279(10) Uani 1 1 d . . . . .
H19A H 0.2777 0.2159 0.4558 0.042 Uiso 1 1 calc GR . . . .
H19B H 0.2928 0.2813 0.4213 0.042 Uiso 1 1 calc GR . . . .
H19C H 0.3720 0.2730 0.4667 0.042 Uiso 1 1 calc GR . . . .
C20 C 0.5775(3) 0.1991(2) 0.47334(16) 0.0285(10) Uani 1 1 d . . . . .
H20A H 0.5623 0.1616 0.4960 0.043 Uiso 1 1 calc GR . . . .
H20B H 0.5478 0.2430 0.4857 0.043 Uiso 1 1 calc GR . . . .
H20C H 0.6586 0.2033 0.4686 0.043 Uiso 1 1 calc GR . . . .
C21 C 0.6751(3) 0.09760(18) 0.39355(17) 0.0291(11) Uani 1 1 d . . . . .
H21A H 0.7284 0.1217 0.4143 0.044 Uiso 1 1 calc GR . . . .
H21B H 0.7070 0.0937 0.3616 0.044 Uiso 1 1 calc GR . . . .
H21C H 0.6602 0.0510 0.4061 0.044 Uiso 1 1 calc GR . . . .
C22 C 0.4993(3) 0.09388(19) 0.30976(16) 0.0281(11) Uani 1 1 d . . . . .
H22A H 0.4791 0.0453 0.3159 0.042 Uiso 1 1 calc GR . . . .
H22B H 0.5774 0.0963 0.2991 0.042 Uiso 1 1 calc GR . . . .
H22C H 0.4501 0.1129 0.2851 0.042 Uiso 1 1 calc GR . . . .
C23 C 0.2845(3) 0.18616(19) 0.33877(16) 0.0253(10) Uani 1 1 d . . . . .
H23A H 0.2997 0.1787 0.3050 0.038 Uiso 1 1 calc GR . . . .
H23B H 0.2550 0.2333 0.3435 0.038 Uiso 1 1 calc GR . . . .
H23C H 0.2292 0.1520 0.3497 0.038 Uiso 1 1 calc GR . . . .
O1S O 0.1559(2) 0.48205(13) 0.49350(11) 0.0289(7) Uani 1 1 d . . . . .
O2S O 0.0000 0.1183(3) 0.2500 0.076(2) Uani 1 2 d S T P . .
C1S C 0.1130(4) 0.5286(2) 0.45806(16) 0.0306(11) Uani 1 1 d . . . . .
H1SA H 0.1581 0.5718 0.4571 0.037 Uiso 1 1 calc R . . . .
H1SB H 0.0342 0.5409 0.4651 0.037 Uiso 1 1 calc R . . . .
C2S C 0.1206(3) 0.4905(2) 0.41080(17) 0.0309(11) Uani 1 1 d . . . . .
H2SA H 0.1642 0.5179 0.3875 0.037 Uiso 1 1 calc R . . . .
H2SB H 0.0451 0.4812 0.3977 0.037 Uiso 1 1 calc R . . . .
C3S C 0.1811(3) 0.4222(2) 0.42327(17) 0.0310(11) Uani 1 1 d . . . . .
H3SA H 0.1273 0.3835 0.4274 0.037 Uiso 1 1 calc R . . . .
H3SB H 0.2366 0.4094 0.3987 0.037 Uiso 1 1 calc R . . . .
C4S C 0.2377(3) 0.44046(19) 0.46939(16) 0.0268(10) Uani 1 1 d . . . . .
H4SA H 0.2558 0.3980 0.4878 0.032 Uiso 1 1 calc R . . . .
H4SB H 0.3074 0.4671 0.4638 0.032 Uiso 1 1 calc R . . . .
C5S C 0.0484(5) 0.1616(3) 0.2152(2) 0.0653(18) Uani 1 1 d . . . . .
H5SA H 0.0245 0.1462 0.1833 0.078 Uiso 1 1 calc R . . . .
H5SB H 0.1311 0.1585 0.2169 0.078 Uiso 1 1 calc R . . . .
C6S C 0.0125(5) 0.2344(3) 0.2232(2) 0.0629(18) Uani 1 1 d . . . . .
H6SA H -0.0552 0.2458 0.2045 0.076 Uiso 1 1 calc R . . . .
H6SB H 0.0730 0.2677 0.2152 0.076 Uiso 1 1 calc R . . . .
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'
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 0.0060 '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_
_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 Ir1 Cl1 86.46(9) . .
N1 Ir1 C14 116.52(14) . .
N1 Ir1 C15 94.73(12) . .
N1 Ir1 C16 107.98(12) . .
N1 Ir1 C17 144.71(12) . .
N1 Ir1 C18 155.50(14) . .
C1 Ir1 Cl1 89.32(11) . .
C1 Ir1 N1 85.01(12) . .
C1 Ir1 C14 100.00(13) . .
C1 Ir1 C15 132.31(14) . .
C1 Ir1 C16 162.85(13) . .
C1 Ir1 C17 130.26(14) . .
C1 Ir1 C18 98.96(13) . .
C14 Ir1 Cl1 155.67(10) . .
C14 Ir1 C15 38.64(13) . .
C14 Ir1 C16 64.47(13) . .
C14 Ir1 C17 64.65(13) . .
C15 Ir1 Cl1 138.34(9) . .
C15 Ir1 C16 37.98(13) . .
C16 Ir1 Cl1 102.33(11) . .
C17 Ir1 Cl1 92.16(11) . .
C17 Ir1 C15 63.82(14) . .
C17 Ir1 C16 38.08(13) . .
C18 Ir1 Cl1 117.60(11) . .
C18 Ir1 C14 39.00(14) . .
C18 Ir1 C15 64.68(14) . .
C18 Ir1 C16 64.56(12) . .
C18 Ir1 C17 38.69(12) . .
F2 P1 F1 87.8(2) . .
F2 P1 F4 174.0(2) . .
F2 P1 F5 85.84(18) . .
F2 P1 F6 93.98(18) . .
F3 P1 F1 176.3(3) . .
F3 P1 F2 93.4(3) . .
F3 P1 F4 91.1(2) . .
F3 P1 F5 87.7(2) . .
F3 P1 F6 92.1(2) . .
F4 P1 F1 87.5(2) . .
F1B P1 F2B 86.8(7) . .
F1B P1 F3B 164.8(8) . .
F1B P1 F5 97.8(5) . .
F1B P1 F6 82.3(5) . .
F3B P1 F2B 82.2(7) . .
F4B P1 F1B 98.9(8) . .
F4B P1 F2B 169.2(7) . .
F4B P1 F3B 90.4(7) . .
F4B P1 F5 89.5(6) . .
F4B P1 F6 90.8(6) . .
F5 P1 F1 88.9(2) . .
F5 P1 F4 90.2(2) . .
F5 P1 F2B 98.9(4) . .
F5 P1 F3B 94.2(5) . .
F6 P1 F1 91.4(2) . .
F6 P1 F4 90.0(2) . .
F6 P1 F2B 80.8(4) . .
F6 P1 F3B 85.6(5) . .
F6 P1 F5 179.70(19) . .
C5 N1 Ir1 123.7(2) . .
C9 N1 Ir1 118.1(2) . .
C9 N1 C5 118.1(3) . .
C1 N2 C3 110.1(3) . .
C1 N2 C4 122.7(3) . .
C3 N2 C4 127.2(3) . .
C1 N3 H3 124.0 . .
C1 N3 C2 112.0(3) . .
C2 N3 H3 124.0 . .
N2 C1 Ir1 122.8(3) . .
N3 C1 Ir1 132.5(3) . .
N3 C1 N2 104.7(3) . .
N3 C2 C10 123.6(3) . .
C3 C2 N3 105.1(3) . .
C3 C2 C10 131.2(3) . .
N2 C3 H3A 126.0 . .
C2 C3 N2 108.0(3) . .
C2 C3 H3A 126.0 . .
N2 C4 H4A 108.9 . .
N2 C4 H4B 108.9 . .
N2 C4 C5 113.2(3) . .
H4A C4 H4B 107.7 . .
C5 C4 H4A 108.9 . .
C5 C4 H4B 108.9 . .
N1 C5 C4 117.9(3) . .
N1 C5 C6 121.6(3) . .
C6 C5 C4 120.5(3) . .
C5 C6 H6 120.2 . .
C5 C6 C7 119.6(3) . .
C7 C6 H6 120.2 . .
C6 C7 H7 120.5 . .
C8 C7 C6 119.0(4) . .
C8 C7 H7 120.5 . .
C7 C8 H8 120.5 . .
C9 C8 C7 119.0(4) . .
C9 C8 H8 120.5 . .
N1 C9 C8 122.7(3) . .
N1 C9 H9 118.6 . .
C8 C9 H9 118.6 . .
C2 C10 C11 111.2(3) . .
C2 C10 C12 109.0(3) . .
C2 C10 C13 108.0(3) . .
C11 C10 C12 109.6(4) . .
C11 C10 C13 109.0(3) . .
C13 C10 C12 110.0(3) . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C10 C13 H13A 109.5 . .
C10 C13 H13B 109.5 . .
C10 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 C14 Ir1 71.6(2) . .
C15 C14 C18 107.6(3) . .
C15 C14 C19 126.8(4) . .
C18 C14 Ir1 70.4(2) . .
C18 C14 C19 125.0(3) . .
C19 C14 Ir1 129.9(2) . .
C14 C15 Ir1 69.7(2) . .
C14 C15 C20 125.5(3) . .
C16 C15 Ir1 71.8(2) . .
C16 C15 C14 108.7(3) . .
C16 C15 C20 125.8(3) . .
C20 C15 Ir1 125.8(2) . .
C15 C16 Ir1 70.24(19) . .
C15 C16 C17 107.6(3) . .
C15 C16 C21 126.6(4) . .
C17 C16 Ir1 70.05(19) . .
C17 C16 C21 125.6(4) . .
C21 C16 Ir1 128.5(2) . .
C16 C17 Ir1 71.87(19) . .
C16 C17 C18 108.7(3) . .
C16 C17 C22 124.9(3) . .
C18 C17 Ir1 69.78(18) . .
C18 C17 C22 126.5(4) . .
C22 C17 Ir1 124.6(3) . .
C14 C18 Ir1 70.56(19) . .
C14 C18 C23 125.8(3) . .
C17 C18 Ir1 71.53(18) . .
C17 C18 C14 107.5(3) . .
C17 C18 C23 126.6(4) . .
C23 C18 Ir1 126.3(2) . .
C14 C19 H19A 109.5 . .
C14 C19 H19B 109.5 . .
C14 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C15 C20 H20A 109.5 . .
C15 C20 H20B 109.5 . .
C15 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C16 C21 H21A 109.5 . .
C16 C21 H21B 109.5 . .
C16 C21 H21C 109.5 . .
H21A C21 H21B 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C17 C22 H22A 109.5 . .
C17 C22 H22B 109.5 . .
C17 C22 H22C 109.5 . .
H22A C22 H22B 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C18 C23 H23A 109.5 . .
C18 C23 H23B 109.5 . .
C18 C23 H23C 109.5 . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C4S O1S C1S 105.0(3) . .
C5S O2S C5S 107.6(6) . 3
O1S C1S H1SA 110.3 . .
O1S C1S H1SB 110.3 . .
O1S C1S C2S 106.9(3) . .
H1SA C1S H1SB 108.6 . .
C2S C1S H1SA 110.3 . .
C2S C1S H1SB 110.3 . .
C1S C2S H2SA 111.0 . .
C1S C2S H2SB 111.0 . .
C1S C2S C3S 103.7(3) . .
H2SA C2S H2SB 109.0 . .
C3S C2S H2SA 111.0 . .
C3S C2S H2SB 111.0 . .
C2S C3S H3SA 111.4 . .
C2S C3S H3SB 111.4 . .
H3SA C3S H3SB 109.2 . .
C4S C3S C2S 102.1(3) . .
C4S C3S H3SA 111.4 . .
C4S C3S H3SB 111.4 . .
O1S C4S C3S 103.6(3) . .
O1S C4S H4SA 111.0 . .
O1S C4S H4SB 111.0 . .
C3S C4S H4SA 111.0 . .
C3S C4S H4SB 111.0 . .
H4SA C4S H4SB 109.0 . .
O2S C5S H5SA 109.8 . .
O2S C5S H5SB 109.8 . .
O2S C5S C6S 109.5(5) . .
H5SA C5S H5SB 108.2 . .
C6S C5S H5SA 109.8 . .
C6S C5S H5SB 109.8 . .
C5S C6S C6S 101.8(4) . 3
C5S C6S H6SA 111.4 . .
C5S C6S H6SB 111.4 . .
C6S C6S H6SA 111.4 3 .
C6S C6S H6SB 111.4 3 .
H6SA C6S H6SB 109.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir1 Cl1 2.4143(10) .
Ir1 N1 2.108(3) .
Ir1 C1 2.016(3) .
Ir1 C14 2.166(4) .
Ir1 C15 2.191(4) .
Ir1 C16 2.212(3) .
Ir1 C17 2.188(3) .
Ir1 C18 2.164(3) .
P1 F1 1.632(5) .
P1 F2 1.583(4) .
P1 F3 1.547(6) .
P1 F4 1.624(4) .
P1 F1B 1.512(11) .
P1 F2B 1.720(12) .
P1 F3B 1.699(14) .
P1 F4B 1.429(15) .
P1 F5 1.609(3) .
P1 F6 1.607(3) .
N1 C5 1.357(4) .
N1 C9 1.354(4) .
N2 C1 1.353(4) .
N2 C3 1.397(4) .
N2 C4 1.446(5) .
N3 H3 0.8800 .
N3 C1 1.348(5) .
N3 C2 1.398(4) .
C2 C3 1.342(5) .
C2 C10 1.500(5) .
C3 H3A 0.9500 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C4 C5 1.508(5) .
C5 C6 1.380(5) .
C6 H6 0.9500 .
C6 C7 1.385(5) .
C7 H7 0.9500 .
C7 C8 1.379(5) .
C8 H8 0.9500 .
C8 C9 1.374(5) .
C9 H9 0.9500 .
C10 C11 1.518(6) .
C10 C12 1.542(5) .
C10 C13 1.531(5) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 C15 1.442(5) .
C14 C18 1.446(5) .
C14 C19 1.495(5) .
C15 C16 1.433(5) .
C15 C20 1.480(5) .
C16 C17 1.435(5) .
C16 C21 1.506(5) .
C17 C18 1.442(5) .
C17 C22 1.482(5) .
C18 C23 1.506(5) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
O1S C1S 1.435(4) .
O1S C4S 1.432(4) .
O2S C5S 1.410(6) 3
O2S C5S 1.410(6) .
C1S H1SA 0.9900 .
C1S H1SB 0.9900 .
C1S C2S 1.523(6) .
C2S H2SA 0.9900 .
C2S H2SB 0.9900 .
C2S C3S 1.538(5) .
C3S H3SA 0.9900 .
C3S H3SB 0.9900 .
C3S C4S 1.507(6) .
C4S H4SA 0.9900 .
C4S H4SB 0.9900 .
C5S H5SA 0.9900 .
C5S H5SB 0.9900 .
C5S C6S 1.479(7) .
C6S C6S 1.543(12) 3
C6S H6SA 0.9900 .
C6S H6SB 0.9900 .
