#------------------------------------------------------------------------------
#$Date: 2020-10-24 00:24:39 +0300 (Sat, 24 Oct 2020) $
#$Revision: 258583 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/81/4518175.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_4518175
loop_
_publ_author_name
'Dodge, Henry M.'
'Kita, Matthew R.'
'Chen, Chun-Hsing'
'Miller, Alexander J. M.'
_publ_section_title
;
 Identifying and Evading Olefin Isomerization Catalyst Deactivation
 Pathways Resulting from Ion-Tunable Hemilability
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              13019
_journal_page_last               13030
_journal_paper_doi               10.1021/acscatal.0c03784
_journal_year                    2020
_chemical_formula_moiety         'C24 H42.00 Cl1 Ir1 N1 O6 P1'
_chemical_formula_sum            'C24 H42 Cl Ir N O6 P'
_chemical_formula_weight         699.25
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2019-06-14
_audit_creation_method           CRYSTALS_ver_14.61_build_6236
_cell_angle_alpha                108.591(4)
_cell_angle_beta                 95.505(5)
_cell_angle_gamma                94.138(4)
_cell_formula_units_Z            2
_cell_length_a                   7.9554(9)
_cell_length_b                   13.3409(14)
_cell_length_c                   13.5830(14)
_cell_measurement_reflns_used    9654
_cell_measurement_temperature    273
_cell_measurement_theta_max      72
_cell_measurement_theta_min      3
_cell_volume                     1352.0(3)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      273
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24983
_diffrn_reflns_theta_full        25.360
_diffrn_reflns_theta_max         72.458
_diffrn_reflns_theta_min         3.460
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    11.347
_exptl_absorpt_correction_T_max  0.57
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'block fragment'
_exptl_crystal_F_000             700.000
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.80
_refine_diff_density_min         -0.84
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0692
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5180
_refine_ls_number_restraints     46
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0197
_refine_ls_shift/su_max          0.0248336
_refine_ls_shift/su_mean         0.0008194
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.02P)² + 2.05P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0495
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0495
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              15
_reflns_limit_k_min              -16
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                5065
_reflns_number_total             5204
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0205
_oxford_refine_ls_scale          0.13217(3)
_oxford_reflns_number_all        5180
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title '19041_0m in P1'
_cod_data_source_file            cs0c03784_si_002.cif
_cod_data_source_block           19041
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C24 H42.00 Cl1 Ir1 N1 O6 P1'
_cod_database_code               4518175
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Ir1 Ir 0.392327(15) 0.781236(9) 0.273390(9) 0.0237 1.0000 Uani . . . . . .
Cl1 Cl 0.52680(11) 0.75437(6) 0.11339(6) 0.0413 1.0000 Uani . . . . . .
P1 P 0.43105(10) 0.63683(6) 0.31197(6) 0.0314 1.0000 Uani . . . . . .
O1 O 0.3340(4) 0.64731(18) 0.41759(19) 0.0465 1.0000 Uani . . . . . .
O2 O 0.1302(11) 0.6978(8) 0.5954(9) 0.0508 0.292(7) Uani D U P 1 1 .
O3 O 0.1133(3) 0.73572(17) 0.18647(17) 0.0369 1.0000 Uani . . . . . .
O4 O 0.0743(3) 0.74717(19) -0.02800(18) 0.0425 1.0000 Uani . . . . . .
O5 O 0.2419(3) 0.94281(19) -0.02345(18) 0.0396 1.0000 Uani . . . . . .
O6 O 0.2758(3) 1.11880(18) 0.16732(18) 0.0380 1.0000 Uani . . . . . .
O21 O 0.2128(6) 0.7102(3) 0.6199(2) 0.0521 0.708(7) Uani D U P 1 2 .
N1 N 0.3137(3) 0.94048(19) 0.27999(19) 0.0275 1.0000 Uani . . . . . .
C1 C 0.2939(4) 0.8189(2) 0.4068(2) 0.0268 1.0000 Uani . . . . . .
C2 C 0.2763(4) 0.7461(2) 0.4604(2) 0.0335 1.0000 Uani . . . . . .
C3 C 0.2053(5) 0.7727(3) 0.5539(3) 0.0444 1.0000 Uani D U . . . .
C4 C 0.1525(5) 0.8733(3) 0.5928(2) 0.0431 1.0000 Uani . . . . . .
C5 C 0.1741(4) 0.9474(3) 0.5422(2) 0.0363 1.0000 Uani . . . . . .
C6 C 0.2467(4) 0.9210(2) 0.4495(2) 0.0301 1.0000 Uani . . . . . .
C7 C 0.2906(4) 0.9973(2) 0.3928(2) 0.0330 1.0000 Uani . . . . . .
C8 C 0.2342(18) 0.6206(10) 0.6020(13) 0.0589 0.292(7) Uani D U P 1 1 .
C9 C 0.6446(5) 0.6151(3) 0.3593(3) 0.0450 1.0000 Uani . . . . . .
C10 C 0.7099(8) 0.7022(5) 0.4626(4) 0.0913 1.0000 Uani . . . . . .
C11 C 0.7655(6) 0.6082(5) 0.2782(5) 0.0754 1.0000 Uani . . . . . .
C12 C 0.3249(5) 0.5070(3) 0.2273(3) 0.0467 1.0000 Uani . . . . . .
C13 C 0.3270(8) 0.4191(3) 0.2775(4) 0.0790 1.0000 Uani . . . . . .
C14 C 0.3878(7) 0.4722(3) 0.1201(3) 0.0677 1.0000 Uani . . . . . .
C15 C 0.1503(4) 0.9218(2) 0.2096(2) 0.0313 1.0000 Uani . . . . . .
C16 C 0.0319(4) 0.8321(3) 0.2163(3) 0.0343 1.0000 Uani . . . . . .
C17 C 0.0338(5) 0.6540(3) 0.0928(3) 0.0488 1.0000 Uani . . . . . .
C18 C 0.1091(5) 0.6550(3) -0.0037(3) 0.0464 1.0000 Uani . . . . . .
C19 C 0.1682(5) 0.7589(3) -0.1082(3) 0.0465 1.0000 Uani . . . . . .
C20 C 0.1560(4) 0.8671(3) -0.1162(3) 0.0426 1.0000 Uani . . . . . .
C21 C 0.2343(5) 1.0494(3) -0.0209(3) 0.0411 1.0000 Uani . . . . . .
C22 C 0.3447(5) 1.1205(3) 0.0746(3) 0.0436 1.0000 Uani . . . . . .
C23 C 0.3971(5) 1.1175(3) 0.2505(3) 0.0406 1.0000 Uani . . . . . .
C24 C 0.4407(4) 1.0062(2) 0.2451(3) 0.0356 1.0000 Uani . . . . . .
C81 C 0.1265(9) 0.6081(5) 0.5733(5) 0.0659 0.708(7) Uani D U P 1 2 .
H1 H 0.560(4) 0.826(3) 0.329(3) 0.0336 1.0000 Uiso . . . . . .
H41 H 0.0994 0.8913 0.6550 0.0520 1.0000 Uiso R . . . . .
H51 H 0.1394 1.0164 0.5709 0.0435 1.0000 Uiso R . . . . .
H71 H 0.3933 1.0400 0.4275 0.0396 1.0000 Uiso R . . . . .
H72 H 0.2017 1.0414 0.3942 0.0396 1.0000 Uiso R . . . . .
H81 H 0.1716 0.5751 0.6301 0.0730 0.292(7) Uiso R . P 1 1 .
H82 H 0.3373 0.6506 0.6466 0.0730 0.292(7) Uiso R . P 1 1 .
H83 H 0.2590 0.5808 0.5344 0.0730 0.292(7) Uiso R . P 1 1 .
H91 H 0.6363 0.5491 0.3722 0.0541 1.0000 Uiso R . . . . .
H101 H 0.8205 0.6906 0.4868 0.1099 1.0000 Uiso R . . . . .
H102 H 0.7143 0.7696 0.4525 0.1099 1.0000 Uiso R . . . . .
H103 H 0.6357 0.7008 0.5130 0.1099 1.0000 Uiso R . . . . .
H111 H 0.8746 0.5969 0.3051 0.0904 1.0000 Uiso R . . . . .
H112 H 0.7733 0.6726 0.2624 0.0904 1.0000 Uiso R . . . . .
H113 H 0.7242 0.5506 0.2164 0.0904 1.0000 Uiso R . . . . .
H121 H 0.2087 0.5170 0.2148 0.0561 1.0000 Uiso R . . . . .
H131 H 0.2699 0.3548 0.2291 0.0947 1.0000 Uiso R . . . . .
H132 H 0.2712 0.4392 0.3386 0.0947 1.0000 Uiso R . . . . .
H133 H 0.4413 0.4090 0.2960 0.0947 1.0000 Uiso R . . . . .
H141 H 0.3300 0.4049 0.0787 0.0812 1.0000 Uiso R . . . . .
H142 H 0.3661 0.5231 0.0862 0.0812 1.0000 Uiso R . . . . .
H143 H 0.5064 0.4670 0.1285 0.0812 1.0000 Uiso R . . . . .
H151 H 0.0955 0.9849 0.2285 0.0375 1.0000 Uiso R . . . . .
H152 H 0.1748 0.9056 0.1395 0.0375 1.0000 Uiso R . . . . .
H161 H 0.0058 0.8472 0.2860 0.0412 1.0000 Uiso R . . . . .
H162 H -0.0698 0.8237 0.1703 0.0412 1.0000 Uiso R . . . . .
H171 H -0.0832 0.6634 0.0834 0.0584 1.0000 Uiso R . . . . .
H172 H 0.0450 0.5868 0.1015 0.0584 1.0000 Uiso R . . . . .
H181 H 0.2285 0.6541 0.0077 0.0555 1.0000 Uiso R . . . . .
H182 H 0.0614 0.5939 -0.0605 0.0555 1.0000 Uiso R . . . . .
H191 H 0.2838 0.7502 -0.0918 0.0560 1.0000 Uiso R . . . . .
H192 H 0.1229 0.7067 -0.1730 0.0560 1.0000 Uiso R . . . . .
H201 H 0.2074 0.8726 -0.1749 0.0510 1.0000 Uiso R . . . . .
H202 H 0.0401 0.8793 -0.1242 0.0510 1.0000 Uiso R . . . . .
H211 H 0.2738 1.0583 -0.0817 0.0493 1.0000 Uiso R . . . . .
H212 H 0.1205 1.0664 -0.0181 0.0493 1.0000 Uiso R . . . . .
H221 H 0.3533 1.1912 0.0725 0.0523 1.0000 Uiso R . . . . .
H222 H 0.4544 1.0968 0.0756 0.0523 1.0000 Uiso R . . . . .
H231 H 0.4985 1.1589 0.2490 0.0487 1.0000 Uiso R . . . . .
H232 H 0.3531 1.1485 0.3146 0.0487 1.0000 Uiso R . . . . .
H241 H 0.5457 1.0140 0.2880 0.0427 1.0000 Uiso R . . . . .
H242 H 0.4534 0.9684 0.1745 0.0427 1.0000 Uiso R . . . . .
H811 H 0.1383 0.5724 0.6235 0.0819 0.708(7) Uiso R . P 1 2 .
H812 H 0.0094 0.6119 0.5548 0.0819 0.708(7) Uiso R . P 1 2 .
H813 H 0.1744 0.5702 0.5126 0.0819 0.708(7) Uiso R . P 1 2 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Ir -4.7710 6.5667 27.3049 1.5928 16.7296 8.8655 15.6115 0.4179 5.8338 45.0011
11.4722 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl1 . Ir1 . P1 . 103.24(3) yes
Cl1 . Ir1 . O3 . 94.96(6) yes
P1 . Ir1 . O3 . 100.13(6) yes
Cl1 . Ir1 . N1 . 94.86(6) yes
P1 . Ir1 . N1 . 161.90(6) yes
O3 . Ir1 . N1 . 78.24(8) yes
Cl1 . Ir1 . C1 . 173.90(9) yes
P1 . Ir1 . C1 . 81.56(8) yes
O3 . Ir1 . C1 . 87.81(10) yes
N1 . Ir1 . C1 . 80.36(10) yes
Cl1 . Ir1 . H1 . 86.1(13) no
P1 . Ir1 . H1 . 87.8(13) no
O3 . Ir1 . H1 . 171.5(14) no
N1 . Ir1 . H1 . 93.3(14) no
C1 . Ir1 . H1 . 90.4(13) no
Ir1 . P1 . O1 . 105.75(8) yes
Ir1 . P1 . C9 . 119.91(12) yes
O1 . P1 . C9 . 100.28(15) yes
Ir1 . P1 . C12 . 120.81(13) yes
O1 . P1 . C12 . 98.53(15) yes
C9 . P1 . C12 . 107.09(17) yes
P1 . O1 . C2 . 113.62(19) yes
C3 . O2 . C8 . 113.16(10) yes
Ir1 . O3 . C16 . 105.96(17) yes
Ir1 . O3 . C17 . 134.4(2) yes
C16 . O3 . C17 . 115.5(3) yes
C18 . O4 . C19 . 111.1(3) yes
C20 . O5 . C21 . 113.4(3) yes
C22 . O6 . C23 . 114.9(3) yes
C3 . O21 . C81 . 113.18(10) yes
Ir1 . N1 . C7 . 106.46(16) yes
Ir1 . N1 . C15 . 107.33(17) yes
C7 . N1 . C15 . 111.3(2) yes
Ir1 . N1 . C24 . 113.42(17) yes
C7 . N1 . C24 . 109.6(2) yes
C15 . N1 . C24 . 108.7(2) yes
Ir1 . C1 . C2 . 120.9(2) yes
Ir1 . C1 . C6 . 119.4(2) yes
C2 . C1 . C6 . 119.7(3) yes
C1 . C2 . O1 . 117.5(3) yes
C1 . C2 . C3 . 120.8(3) yes
O1 . C2 . C3 . 121.7(3) yes
O2 . C3 . C2 . 124.5(5) yes
O2 . C3 . C4 . 113.5(5) yes
C2 . C3 . C4 . 118.6(3) yes
O21 . C3 . C2 . 122.5(3) yes
O21 . C3 . C4 . 117.9(3) yes
C2 . C3 . C4 . 118.6(3) yes
C3 . C4 . C5 . 121.3(3) yes
C3 . C4 . H41 . 119.4 no
C5 . C4 . H41 . 119.3 no
C4 . C5 . C6 . 119.9(3) yes
C4 . C5 . H51 . 120.0 no
C6 . C5 . H51 . 120.0 no
C1 . C6 . C5 . 119.7(3) yes
C1 . C6 . C7 . 115.5(3) yes
C5 . C6 . C7 . 124.7(3) yes
N1 . C7 . C6 . 112.1(2) yes
N1 . C7 . H71 . 108.8 no
C6 . C7 . H71 . 108.8 no
N1 . C7 . H72 . 108.8 no
C6 . C7 . H72 . 108.8 no
H71 . C7 . H72 . 109.5 no
O2 . C8 . H81 . 106.0 no
O2 . C8 . H82 . 111.9 no
H81 . C8 . H82 . 109.5 no
O2 . C8 . H83 . 110.4 no
H81 . C8 . H83 . 109.5 no
H82 . C8 . H83 . 109.5 no
P1 . C9 . C10 . 109.8(3) yes
P1 . C9 . C11 . 111.6(3) yes
C10 . C9 . C11 . 111.8(4) yes
P1 . C9 . H91 . 107.8 no
C10 . C9 . H91 . 107.9 no
C11 . C9 . H91 . 107.8 no
C9 . C10 . H101 . 109.4 no
C9 . C10 . H102 . 109.5 no
H101 . C10 . H102 . 109.5 no
C9 . C10 . H103 . 109.5 no
H101 . C10 . H103 . 109.5 no
H102 . C10 . H103 . 109.5 no
C9 . C11 . H111 . 109.5 no
C9 . C11 . H112 . 109.5 no
H111 . C11 . H112 . 109.5 no
C9 . C11 . H113 . 109.5 no
H111 . C11 . H113 . 109.5 no
H112 . C11 . H113 . 109.5 no
P1 . C12 . C13 . 114.5(3) yes
P1 . C12 . C14 . 112.1(3) yes
C13 . C12 . C14 . 111.9(4) yes
P1 . C12 . H121 . 105.9 no
C13 . C12 . H121 . 105.9 no
C14 . C12 . H121 . 105.9 no
C12 . C13 . H131 . 109.4 no
C12 . C13 . H132 . 109.5 no
H131 . C13 . H132 . 109.5 no
C12 . C13 . H133 . 109.4 no
H131 . C13 . H133 . 109.5 no
H132 . C13 . H133 . 109.5 no
C12 . C14 . H141 . 109.5 no
C12 . C14 . H142 . 109.5 no
H141 . C14 . H142 . 109.5 no
C12 . C14 . H143 . 109.4 no
H141 . C14 . H143 . 109.5 no
H142 . C14 . H143 . 109.5 no
N1 . C15 . C16 . 113.0(2) yes
N1 . C15 . H151 . 108.6 no
C16 . C15 . H151 . 108.6 no
N1 . C15 . H152 . 108.6 no
C16 . C15 . H152 . 108.6 no
H151 . C15 . H152 . 109.5 no
C15 . C16 . O3 . 108.9(2) yes
C15 . C16 . H161 . 109.6 no
O3 . C16 . H161 . 109.6 no
C15 . C16 . H162 . 109.6 no
O3 . C16 . H162 . 109.6 no
H161 . C16 . H162 . 109.5 no
O3 . C17 . C18 . 113.7(3) yes
O3 . C17 . H171 . 108.4 no
C18 . C17 . H171 . 108.5 no
O3 . C17 . H172 . 108.4 no
C18 . C17 . H172 . 108.4 no
H171 . C17 . H172 . 109.5 no
C17 . C18 . O4 . 110.3(3) yes
C17 . C18 . H181 . 109.3 no
O4 . C18 . H181 . 109.3 no
C17 . C18 . H182 . 109.2 no
O4 . C18 . H182 . 109.2 no
H181 . C18 . H182 . 109.5 no
O4 . C19 . C20 . 109.3(3) yes
O4 . C19 . H191 . 109.5 no
C20 . C19 . H191 . 109.5 no
O4 . C19 . H192 . 109.5 no
C20 . C19 . H192 . 109.5 no
H191 . C19 . H192 . 109.5 no
C19 . C20 . O5 . 108.4(3) yes
C19 . C20 . H201 . 109.7 no
O5 . C20 . H201 . 109.7 no
C19 . C20 . H202 . 109.8 no
O5 . C20 . H202 . 109.8 no
H201 . C20 . H202 . 109.5 no
O5 . C21 . C22 . 108.2(3) yes
O5 . C21 . H211 . 109.8 no
C22 . C21 . H211 . 109.8 no
O5 . C21 . H212 . 109.8 no
C22 . C21 . H212 . 109.8 no
H211 . C21 . H212 . 109.5 no
C21 . C22 . O6 . 110.9(3) yes
C21 . C22 . H221 . 109.1 no
O6 . C22 . H221 . 109.2 no
C21 . C22 . H222 . 109.1 no
O6 . C22 . H222 . 109.1 no
H221 . C22 . H222 . 109.5 no
O6 . C23 . C24 . 114.1(3) yes
O6 . C23 . H231 . 108.3 no
C24 . C23 . H231 . 108.3 no
O6 . C23 . H232 . 108.3 no
C24 . C23 . H232 . 108.3 no
H231 . C23 . H232 . 109.5 no
C23 . C24 . N1 . 116.2(3) yes
C23 . C24 . H241 . 107.8 no
N1 . C24 . H241 . 107.8 no
C23 . C24 . H242 . 107.8 no
N1 . C24 . H242 . 107.8 no
H241 . C24 . H242 . 109.5 no
O21 . C81 . H811 . 107.0 no
O21 . C81 . H812 . 110.7 no
H811 . C81 . H812 . 109.5 no
O21 . C81 . H813 . 110.7 no
H811 . C81 . H813 . 109.5 no
H812 . C81 . H813 . 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ir1 . Cl1 . 2.4496(8) yes
Ir1 . P1 . 2.1861(7) yes
Ir1 . O3 . 2.352(2) yes
Ir1 . N1 . 2.235(2) yes
Ir1 . C1 . 1.974(3) yes
Ir1 . H1 . 1.45(3) no
P1 . O1 . 1.665(2) yes
P1 . C9 . 1.834(4) yes
P1 . C12 . 1.835(4) yes
O1 . C2 . 1.392(4) yes
O2 . C3 . 1.417(7) yes
O2 . C8 . 1.386(8) yes
O3 . C16 . 1.441(4) yes
O3 . C17 . 1.439(4) yes
O4 . C18 . 1.409(4) yes
O4 . C19 . 1.420(4) yes
O5 . C20 . 1.414(4) yes
O5 . C21 . 1.418(4) yes
O6 . C22 . 1.427(4) yes
O6 . C23 . 1.419(4) yes
O21 . C3 . 1.405(4) yes
O21 . C81 . 1.399(6) yes
N1 . C7 . 1.513(4) yes
N1 . C15 . 1.492(4) yes
N1 . C24 . 1.498(4) yes
C1 . C2 . 1.395(4) yes
C1 . C6 . 1.394(4) yes
C2 . C3 . 1.392(4) yes
C3 . C4 . 1.389(5) yes
C3 . C4 . 1.389(5) yes
C4 . C5 . 1.383(5) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.390(4) yes
C5 . H51 . 0.950 no
C6 . C7 . 1.500(4) yes
C7 . H71 . 0.950 no
C7 . H72 . 0.950 no
C8 . H81 . 0.950 no
C8 . H82 . 0.950 no
C8 . H83 . 0.950 no
C9 . C10 . 1.524(6) yes
C9 . C11 . 1.515(6) yes
C9 . H91 . 0.950 no
C10 . H101 . 0.950 no
C10 . H102 . 0.950 no
C10 . H103 . 0.950 no
C11 . H111 . 0.950 no
C11 . H112 . 0.950 no
C11 . H113 . 0.950 no
C12 . C13 . 1.533(5) yes
C12 . C14 . 1.527(6) yes
C12 . H121 . 0.950 no
C13 . H131 . 0.950 no
C13 . H132 . 0.950 no
C13 . H133 . 0.950 no
C14 . H141 . 0.950 no
C14 . H142 . 0.950 no
C14 . H143 . 0.950 no
C15 . C16 . 1.500(4) yes
C15 . H151 . 0.950 no
C15 . H152 . 0.950 no
C16 . H161 . 0.950 no
C16 . H162 . 0.950 no
C17 . C18 . 1.495(5) yes
C17 . H171 . 0.950 no
C17 . H172 . 0.950 no
C18 . H181 . 0.950 no
C18 . H182 . 0.950 no
C19 . C20 . 1.490(5) yes
C19 . H191 . 0.950 no
C19 . H192 . 0.950 no
C20 . H201 . 0.950 no
C20 . H202 . 0.950 no
C21 . C22 . 1.493(5) yes
C21 . H211 . 0.950 no
C21 . H212 . 0.950 no
C22 . H221 . 0.950 no
C22 . H222 . 0.950 no
C23 . C24 . 1.530(4) yes
C23 . H231 . 0.950 no
C23 . H232 . 0.950 no
C24 . H241 . 0.950 no
C24 . H242 . 0.950 no
C81 . H811 . 0.950 no
C81 . H812 . 0.950 no
C81 . H813 . 0.950 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C8 . H83 . O1 . 125 0.95 2.16 2.817(6) yes
C15 . H152 . O4 . 133 0.95 2.57 3.292(6) yes
C15 . H152 . O5 . 157 0.95 2.51 3.408(6) yes
C20 . H202 . O6 2_575 170 0.95 2.53 3.469(6) yes
C81 . H813 . O1 . 125 0.95 2.30 2.953(6) yes
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
Cl1 Ir1 P1 O1 -177.38(11) . . . . no
Cl1 Ir1 P1 C9 70.51(15) . . . . no
Cl1 Ir1 P1 C12 -67.04(15) . . . . no
O3 Ir1 P1 O1 -79.77(12) . . . . no
O3 Ir1 P1 C9 168.12(15) . . . . no
O3 Ir1 P1 C12 30.57(16) . . . . no
C1 Ir1 P1 O1 6.46(14) . . . . no
C1 Ir1 P1 C9 -105.65(17) . . . . no
C1 Ir1 P1 C12 116.80(17) . . . . no
Cl1 Ir1 O3 C16 -112.72(19) . . . . no
Cl1 Ir1 O3 C17 42.2(3) . . . . no
P1 Ir1 O3 C16 142.85(19) . . . . no
P1 Ir1 O3 C17 -62.2(3) . . . . no
N1 Ir1 O3 C16 -18.8(2) . . . . no
N1 Ir1 O3 C17 136.2(3) . . . . no
C1 Ir1 O3 C16 61.9(2) . . . . no
C1 Ir1 O3 C17 -143.2(3) . . . . no
Cl1 Ir1 N1 C7 -157.32(17) . . . . no
Cl1 Ir1 N1 C15 83.40(16) . . . . no
Cl1 Ir1 N1 C24 -36.6(2) . . . . no
O3 Ir1 N1 C7 108.60(18) . . . . no
O3 Ir1 N1 C15 -10.67(16) . . . . no
O3 Ir1 N1 C24 -130.7(2) . . . . no
C1 Ir1 N1 C7 18.85(19) . . . . no
C1 Ir1 N1 C15 -100.43(19) . . . . no
C1 Ir1 N1 C24 139.5(2) . . . . no
P1 Ir1 C1 C2 -5.1(2) . . . . no
P1 Ir1 C1 C6 172.8(3) . . . . no
O3 Ir1 C1 C2 95.5(3) . . . . no
O3 Ir1 C1 C6 -86.6(2) . . . . no
N1 Ir1 C1 C2 174.0(3) . . . . no
N1 Ir1 C1 C6 -8.2(2) . . . . no
Ir1 P1 O1 C2 -7.9(2) . . . . no
C9 P1 O1 C2 117.4(3) . . . . no
C12 P1 O1 C2 -133.4(2) . . . . no
Ir1 P1 C9 C10 62.4(4) . . . . no
Ir1 P1 C9 C11 -62.1(4) . . . . no
O1 P1 C9 C10 -52.6(4) . . . . no
O1 P1 C9 C11 -177.1(4) . . . . no
C12 P1 C9 C10 -155.0(3) . . . . no
C12 P1 C9 C11 80.6(4) . . . . no
Ir1 P1 C12 C13 -165.1(3) . . . . no
Ir1 P1 C12 C14 66.1(3) . . . . no
O1 P1 C12 C13 -51.0(4) . . . . no
O1 P1 C12 C14 -179.8(3) . . . . no
C9 P1 C12 C13 52.6(4) . . . . no
C9 P1 C12 C14 -76.2(3) . . . . no
P1 O1 C2 C1 4.9(4) . . . . no
P1 O1 C2 C3 -174.4(3) . . . . no
Ir1 O3 C16 C15 45.0(3) . . . . no
C17 O3 C16 C15 -115.4(3) . . . . no
Ir1 O3 C17 C18 -58.3(4) . . . . no
C16 O3 C17 C18 94.9(4) . . . . no
C19 O4 C18 C17 170.1(3) . . . . no
C18 O4 C19 C20 -168.4(3) . . . . no
C21 O5 C20 C19 -178.2(3) . . . . no
C20 O5 C21 C22 -173.9(3) . . . . no
C23 O6 C22 C21 139.4(3) . . . . no
C22 O6 C23 C24 -85.8(4) . . . . no
C81 O21 C3 C2 -63.4(6) . . . . no
C81 O21 C3 C4 128.4(5) . . . . no
Ir1 N1 C7 C6 -26.4(3) . . . . no
C15 N1 C7 C6 90.3(3) . . . . no
C24 N1 C7 C6 -149.5(3) . . . . no
Ir1 N1 C15 C16 40.0(3) . . . . no
C7 N1 C15 C16 -76.2(3) . . . . no
C24 N1 C15 C16 163.0(3) . . . . no
Ir1 N1 C24 C23 -178.4(2) . . . . no
C7 N1 C24 C23 -59.5(4) . . . . no
C15 N1 C24 C23 62.3(4) . . . . no
Ir1 C1 C2 O1 1.4(4) . . . . no
Ir1 C1 C2 C3 -179.4(3) . . . . no
C6 C1 C2 O1 -176.5(3) . . . . no
C6 C1 C2 C3 2.8(5) . . . . no
Ir1 C1 C6 C5 178.7(2) . . . . no
Ir1 C1 C6 C7 -5.2(4) . . . . no
C2 C1 C6 C5 -3.5(5) . . . . no
C2 C1 C6 C7 172.7(3) . . . . no
O1 C2 C3 O21 11.0(6) . . . . no
O1 C2 C3 C4 179.1(3) . . . . no
C1 C2 C3 O21 -168.2(4) . . . . no
C1 C2 C3 C4 -0.1(5) . . . . no
O21 C3 C4 C5 166.7(4) . . . . no
C2 C3 C4 C5 -2.0(6) . . . . no
C3 C4 C5 C6 1.3(5) . . . . no
C4 C5 C6 C1 1.4(5) . . . . no
C4 C5 C6 C7 -174.3(3) . . . . no
C1 C6 C7 N1 22.5(4) . . . . no
C5 C6 C7 N1 -161.6(3) . . . . no
N1 C15 C16 O3 -60.2(3) . . . . no
O3 C17 C18 O4 -67.6(4) . . . . no
O4 C19 C20 O5 66.9(4) . . . . no
O5 C21 C22 O6 -67.5(4) . . . . no
O6 C23 C24 N1 -78.0(4) . . . . no
