#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/45/1514505.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_1514505
loop_
_publ_author_name
'Schramm, York'
'Barrios-Landeros, Fabiola'
'Pfaltz, Andreas'
_publ_section_title
;
 Discovery of an iridacycle catalyst with improved reactivity and
 enantioselectivity in the hydrogenation of dialkyl ketimines
;
_journal_issue                   7
_journal_name_full               'Chemical Science'
_journal_page_first              2760
_journal_paper_doi               10.1039/c3sc50587a
_journal_volume                  4
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H44 Ir N2 O2 P, F6 P'
_chemical_formula_sum            'C42 H44 F6 Ir N2 O2 P2'
_chemical_formula_weight         976.98
_space_group_IT_number           173
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             07-11-09
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   19.4370(2)
_cell_length_b                   19.4370(2)
_cell_length_c                   18.1371(2)
_cell_measurement_reflns_used    23630
_cell_measurement_temperature    173
_cell_measurement_theta_max      28
_cell_measurement_theta_min      1
_cell_volume                     5934.13(11)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            47359
_diffrn_reflns_theta_full        27.863
_diffrn_reflns_theta_max         27.863
_diffrn_reflns_theta_min         1.210
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.523
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_description       plate
_exptl_crystal_F_000             2922
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.77
_refine_diff_density_min         -1.48
_refine_ls_abs_structure_details 'Flack (1983), 4563 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.012(5)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.7012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         5400
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0216
_refine_ls_shift/su_max          0.003822
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[σ²(F²) + ( 0.00P)² + 0.00P]
,where P=(max(Fo²,0) + 2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0234
_refine_ls_wR_factor_gt          0.0196
_refine_ls_wR_factor_ref         0.0196
_reflns_limit_h_max              0
_reflns_limit_h_min              -21
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              -23
_reflns_number_gt                5400
_reflns_number_total             9429
_reflns_threshold_expression     I>3.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          0.05380(3)
_oxford_structure_analysis_title '11091630 fab1-121_173k'
_cod_data_source_file            c3sc50587a.txt
_cod_data_source_block           fab1-121
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P 63 '
_cod_original_formula_sum        'C42 H44 F6 Ir1 N2 O2 P2'
_cod_database_code               1514505
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x-y,x,z+1/2
-y,x-y,z
-x,-y,z+1/2
-x+y,-x,z
y,-x+y,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Ir1 Ir 0.327810(9) 0.350321(9) 0.40278(4) 0.0270 1.0000 Uani . .
P1 P 0.30935(9) 0.33670(9) 0.52966(8) 0.0291 1.0000 Uani . .
P2 P 0.0000 0.0000 0.35910(13) 0.0333 1.0000 Uani S T
P3 P 0.6667 0.3333 0.37717(13) 0.0484 1.0000 Uani S T
P4 P 0.6667 0.3333 0.82362(17) 0.0665 1.0000 Uani S T
N1 N 0.4454(2) 0.4217(2) 0.42713(18) 0.0298 1.0000 Uani . .
N2 N 0.3512(2) 0.2540(2) 0.37279(19) 0.0311 1.0000 Uani . .
O1 O 0.5646(2) 0.4724(2) 0.47960(18) 0.0419 1.0000 Uani . .
O2 O 0.20680(19) 0.28120(19) 0.37045(16) 0.0358 1.0000 Uani . .
F1 F 0.0213(2) -0.0530(2) 0.4090(3) 0.0920 1.0000 Uani . .
F2 F 0.0742(2) 0.0215(2) 0.3091(2) 0.0852 1.0000 Uani . .
F3 F 0.6409(5) 0.2614(4) 0.3278(4) 0.2212 1.0000 Uani . .
F4 F 0.5938(3) 0.2832(3) 0.4237(4) 0.1734 1.0000 Uani . .
F5 F 0.5914(3) 0.3009(3) 0.8722(3) 0.1528 1.0000 Uani . .
F6 F 0.6367(3) 0.3793(3) 0.7721(2) 0.1154 1.0000 Uani . .
C1 C 0.4991(3) 0.4909(3) 0.3791(2) 0.0360 1.0000 Uani . .
C2 C 0.5804(2) 0.5101(3) 0.4066(5) 0.0456 1.0000 Uani . .
C3 C 0.4869(3) 0.4186(3) 0.4807(3) 0.0308 1.0000 Uani . .
C4 C 0.4637(3) 0.3624(3) 0.5428(3) 0.0319 1.0000 Uani . .
C5 C 0.5234(3) 0.3526(3) 0.5742(2) 0.0370 1.0000 Uani . .
C6 C 0.5069(3) 0.2998(3) 0.6321(3) 0.0431 1.0000 Uani . .
C7 C 0.4296(4) 0.2557(3) 0.6576(3) 0.0457 1.0000 Uani . .
C8 C 0.3706(3) 0.2658(3) 0.6274(2) 0.0402 1.0000 Uani . .
C9 C 0.3851(4) 0.3190(4) 0.5690(3) 0.0291 1.0000 Uani . .
C10 C 0.2172(3) 0.2633(3) 0.5740(2) 0.0301 1.0000 Uani . .
C11 C 0.1613(4) 0.1984(4) 0.5358(3) 0.0500 1.0000 Uani . .
C12 C 0.0921(4) 0.1407(4) 0.5696(3) 0.0579 1.0000 Uani . .
C13 C 0.0768(3) 0.1480(3) 0.6412(3) 0.0529 1.0000 Uani . .
C14 C 0.1331(4) 0.2111(4) 0.6827(3) 0.0559 1.0000 Uani . .
C15 C 0.2030(3) 0.2687(3) 0.6491(3) 0.0503 1.0000 Uani . .
C16 C 0.3286(3) 0.4276(4) 0.5774(3) 0.0290 1.0000 Uani . .
C17 C 0.2906(3) 0.4673(3) 0.5529(3) 0.0431 1.0000 Uani . .
C18 C 0.2981(3) 0.5321(3) 0.5900(3) 0.0474 1.0000 Uani . .
C19 C 0.3434(3) 0.5588(3) 0.6531(3) 0.0450 1.0000 Uani . .
C20 C 0.3821(3) 0.5206(3) 0.6778(3) 0.0403 1.0000 Uani . .
C21 C 0.3737(4) 0.4541(4) 0.6407(4) 0.0375 1.0000 Uani . .
C22 C 0.4829(3) 0.5598(3) 0.3818(3) 0.0394 1.0000 Uani . .
C23 C 0.5309(4) 0.6201(4) 0.3223(4) 0.0628 1.0000 Uani . .
C24 C 0.4971(4) 0.5989(4) 0.4581(3) 0.0512 1.0000 Uani . .
C25 C 0.3577(4) 0.3716(4) 0.2927(3) 0.0404 1.0000 Uani . .
C26 C 0.3540(4) 0.4294(4) 0.2487(3) 0.0421 1.0000 Uani . .
C27 C 0.3825(4) 0.4439(5) 0.1770(4) 0.0554 1.0000 Uani . .
C28 C 0.4123(3) 0.3990(5) 0.1486(3) 0.0634 1.0000 Uani . .
C29 C 0.4135(4) 0.3386(4) 0.1891(3) 0.0564 1.0000 Uani . .
C30 C 0.3855(4) 0.3257(4) 0.2619(3) 0.0377 1.0000 Uani . .
C31 C 0.3821(3) 0.2619(3) 0.3079(3) 0.0381 1.0000 Uani . .
C32 C 0.4117(4) 0.2084(4) 0.2802(3) 0.0578 1.0000 Uani . .
C33 C 0.3380(3) 0.1899(3) 0.4203(2) 0.0321 1.0000 Uani . .
C34 C 0.3992(3) 0.1905(3) 0.4586(3) 0.0412 1.0000 Uani . .
C35 C 0.3825(4) 0.1289(4) 0.5087(3) 0.0550 1.0000 Uani . .
C36 C 0.3074(5) 0.0689(4) 0.5198(3) 0.0600 1.0000 Uani . .
C37 C 0.2465(4) 0.0674(4) 0.4799(4) 0.0637 1.0000 Uani . .
C38 C 0.2618(4) 0.1283(3) 0.4299(3) 0.0531 1.0000 Uani . .
C39 C 0.1830(4) 0.2265(4) 0.3075(3) 0.0475 1.0000 Uani . .
C40 C 0.1262(4) 0.2400(4) 0.2634(3) 0.0647 1.0000 Uani . .
C41 C 0.0878(4) 0.2650(4) 0.3206(4) 0.0668 1.0000 Uani . .
C42 C 0.1572(3) 0.3170(4) 0.3718(3) 0.0582 1.0000 Uani . .
H11 H 0.4924 0.4717 0.3281 0.0411 1.0000 Uiso R .
H21 H 0.6043 0.4876 0.3747 0.0532 1.0000 Uiso R .
H22 H 0.6158 0.5672 0.4111 0.0531 1.0000 Uiso R .
H51 H 0.5752 0.3819 0.5561 0.0470 1.0000 Uiso R .
H61 H 0.5473 0.2942 0.6541 0.0592 1.0000 Uiso R .
H71 H 0.4173 0.2187 0.6956 0.0610 1.0000 Uiso R .
H81 H 0.3191 0.2365 0.6460 0.0541 1.0000 Uiso R .
H111 H 0.1703 0.1931 0.4859 0.0564 1.0000 Uiso R .
H121 H 0.0555 0.0962 0.5434 0.0632 1.0000 Uiso R .
H131 H 0.0289 0.1112 0.6633 0.0603 1.0000 Uiso R .
H141 H 0.1246 0.2148 0.7328 0.0621 1.0000 Uiso R .
H151 H 0.2407 0.3120 0.6772 0.0552 1.0000 Uiso R .
H171 H 0.2591 0.4486 0.5106 0.0572 1.0000 Uiso R .
H181 H 0.2719 0.5583 0.5723 0.0671 1.0000 Uiso R .
H191 H 0.3484 0.6029 0.6794 0.0542 1.0000 Uiso R .
H201 H 0.4138 0.5385 0.7201 0.0452 1.0000 Uiso R .
H211 H 0.3995 0.4279 0.6583 0.0485 1.0000 Uiso R .
H221 H 0.4269 0.5387 0.3705 0.0470 1.0000 Uiso R .
H231 H 0.5172 0.6614 0.3201 0.0861 1.0000 Uiso R .
H232 H 0.5204 0.5935 0.2751 0.0863 1.0000 Uiso R .
H233 H 0.5865 0.6435 0.3342 0.0861 1.0000 Uiso R .
H241 H 0.4804 0.6378 0.4583 0.0779 1.0000 Uiso R .
H242 H 0.4682 0.5586 0.4950 0.0780 1.0000 Uiso R .
H243 H 0.5531 0.6239 0.4672 0.0783 1.0000 Uiso R .
H261 H 0.3335 0.4596 0.2681 0.0474 1.0000 Uiso R .
H271 H 0.3795 0.4822 0.1481 0.0544 1.0000 Uiso R .
H281 H 0.4331 0.4100 0.1008 0.0602 1.0000 Uiso R .
H291 H 0.4331 0.3082 0.1679 0.0673 1.0000 Uiso R .
H321 H 0.4047 0.2027 0.2275 0.0929 1.0000 Uiso R .
H322 H 0.3825 0.1565 0.3025 0.0930 1.0000 Uiso R .
H323 H 0.4671 0.2318 0.2915 0.0932 1.0000 Uiso R .
H341 H 0.4513 0.2315 0.4511 0.0632 1.0000 Uiso R .
H351 H 0.4240 0.1292 0.5351 0.0800 1.0000 Uiso R .
H361 H 0.2982 0.0290 0.5537 0.0809 1.0000 Uiso R .
H371 H 0.1947 0.0260 0.4875 0.0772 1.0000 Uiso R .
H381 H 0.2200 0.1269 0.4022 0.0671 1.0000 Uiso R .
H391 H 0.1572 0.1717 0.3259 0.0642 1.0000 Uiso R .
H392 H 0.2297 0.2372 0.2779 0.0641 1.0000 Uiso R .
H401 H 0.0868 0.1918 0.2380 0.0810 1.0000 Uiso R .
H402 H 0.1551 0.2827 0.2275 0.0810 1.0000 Uiso R .
H411 H 0.0481 0.2191 0.3483 0.0901 1.0000 Uiso R .
H412 H 0.0637 0.2938 0.2992 0.0900 1.0000 Uiso R .
H421 H 0.1395 0.3166 0.4216 0.0813 1.0000 Uiso R .
H422 H 0.1864 0.3715 0.3540 0.0810 1.0000 Uiso R .
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 0.0033 0.0016 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'
Ir -1.4442 7.9887 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'
N 0.0061 0.0033 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 0.0106 0.0060 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 0.1023 0.0942 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'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 '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_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
P1 . Ir1 N1 . 85.41(10) yes
P1 . Ir1 N2 . 103.49(10) yes
N1 . Ir1 N2 . 89.68(14) yes
P1 . Ir1 O2 . 98.17(9) yes
N1 . Ir1 O2 . 175.80(13) yes
N2 . Ir1 O2 . 91.61(13) yes
P1 . Ir1 C25 . 173.43(19) yes
N1 . Ir1 C25 . 88.04(19) yes
N2 . Ir1 C25 . 77.0(2) yes
O2 . Ir1 C25 . 88.35(19) yes
Ir1 . P1 C9 . 108.5(2) yes
Ir1 . P1 C10 . 124.05(16) yes
C9 . P1 C10 . 104.5(3) yes
Ir1 . P1 C16 . 114.43(19) yes
C9 . P1 C16 . 101.7(3) yes
C10 . P1 C16 . 101.2(2) yes
F1 5_555 P2 F1 3_555 90.2(3) yes
F1 5_555 P2 F2 5_555 90.0(2) yes
F1 3_555 P2 F2 5_555 179.8(2) yes
F1 5_555 P2 F2 3_555 89.7(2) yes
F1 3_555 P2 F2 3_555 90.0(2) yes
F2 5_555 P2 F2 3_555 90.0(2) yes
F1 5_555 P2 F1 . 90.2(3) yes
F1 3_555 P2 F1 . 90.2(3) yes
F2 5_555 P2 F1 . 89.7(2) yes
F2 3_555 P2 F1 . 179.8(2) yes
F1 5_555 P2 F2 . 179.8(2) yes
F1 3_555 P2 F2 . 89.7(2) yes
F2 5_555 P2 F2 . 90.0(2) yes
F2 3_555 P2 F2 . 90.0(2) yes
F1 . P2 F2 . 90.0(2) yes
F3 3_655 P3 F3 5_665 88.8(5) yes
F3 3_655 P3 F4 3_655 88.0(4) yes
F3 5_665 P3 F4 3_655 176.8(4) yes
F3 3_655 P3 F4 5_665 91.4(4) yes
F3 5_665 P3 F4 5_665 88.0(4) yes
F4 3_655 P3 F4 5_665 91.8(4) yes
F3 3_655 P3 F3 . 88.8(5) yes
F3 5_665 P3 F3 . 88.8(5) yes
F4 3_655 P3 F3 . 91.4(4) yes
F4 5_665 P3 F3 . 176.8(4) yes
F3 3_655 P3 F4 . 176.8(4) yes
F3 5_665 P3 F4 . 91.4(4) yes
F4 3_655 P3 F4 . 91.8(4) yes
F4 5_665 P3 F4 . 91.8(4) yes
F3 . P3 F4 . 88.0(4) yes
F6 5_665 P4 F6 3_655 89.0(3) yes
F6 5_665 P4 F5 5_665 91.5(3) yes
F6 3_655 P4 F5 5_665 177.7(3) yes
F6 5_665 P4 F5 3_655 88.8(3) yes
F6 3_655 P4 F5 3_655 91.5(3) yes
F5 5_665 P4 F5 3_655 90.7(3) yes
F6 5_665 P4 F5 . 177.7(3) yes
F6 3_655 P4 F5 . 88.8(3) yes
F5 5_665 P4 F5 . 90.7(3) yes
F5 3_655 P4 F5 . 90.7(3) yes
F6 5_665 P4 F6 . 89.0(3) yes
F6 3_655 P4 F6 . 89.0(3) yes
F5 5_665 P4 F6 . 88.8(3) yes
F5 3_655 P4 F6 . 177.7(3) yes
F5 . P4 F6 . 91.5(3) yes
Ir1 . N1 C1 . 121.6(3) yes
Ir1 . N1 C3 . 130.3(3) yes
C1 . N1 C3 . 108.1(4) yes
Ir1 . N2 C31 . 113.8(4) yes
Ir1 . N2 C33 . 124.6(3) yes
C31 . N2 C33 . 121.5(4) yes
C2 . O1 C3 . 106.0(3) yes
Ir1 . O2 C39 . 121.3(3) yes
Ir1 . O2 C42 . 119.0(3) yes
C39 . O2 C42 . 108.6(4) yes
N1 . C1 C2 . 101.7(4) yes
N1 . C1 C22 . 114.3(4) yes
C2 . C1 C22 . 114.9(4) yes
N1 . C1 H11 . 107.9 no
C2 . C1 H11 . 109.2 no
C22 . C1 H11 . 108.5 no
C1 . C2 O1 . 104.0(4) yes
C1 . C2 H21 . 111.5 no
O1 . C2 H21 . 109.9 no
C1 . C2 H22 . 111.4 no
O1 . C2 H22 . 110.2 no
H21 . C2 H22 . 109.7 no
O1 . C3 N1 . 116.2(4) yes
O1 . C3 C4 . 113.4(4) yes
N1 . C3 C4 . 130.4(5) yes
C3 . C4 C5 . 116.6(5) yes
C3 . C4 C9 . 122.7(5) yes
C5 . C4 C9 . 120.7(5) yes
C4 . C5 C6 . 120.7(5) yes
C4 . C5 H51 . 119.6 no
C6 . C5 H51 . 119.7 no
C5 . C6 C7 . 119.2(5) yes
C5 . C6 H61 . 120.7 no
C7 . C6 H61 . 120.0 no
C6 . C7 C8 . 120.2(5) yes
C6 . C7 H71 . 120.2 no
C8 . C7 H71 . 119.5 no
C7 . C8 C9 . 122.1(6) yes
C7 . C8 H81 . 119.1 no
C9 . C8 H81 . 118.8 no
P1 . C9 C4 . 119.5(4) yes
P1 . C9 C8 . 123.5(5) yes
C4 . C9 C8 . 117.0(6) yes
P1 . C10 C11 . 120.9(4) yes
P1 . C10 C15 . 121.4(4) yes
C11 . C10 C15 . 117.6(5) yes
C10 . C11 C12 . 121.4(5) yes
C10 . C11 H111 . 118.9 no
C12 . C11 H111 . 119.7 no
C11 . C12 C13 . 120.8(6) yes
C11 . C12 H121 . 120.4 no
C13 . C12 H121 . 118.7 no
C12 . C13 C14 . 119.6(5) yes
C12 . C13 H131 . 121.1 no
C14 . C13 H131 . 119.2 no
C13 . C14 C15 . 119.5(5) yes
C13 . C14 H141 . 120.3 no
C15 . C14 H141 . 120.1 no
C10 . C15 C14 . 120.8(5) yes
C10 . C15 H151 . 119.8 no
C14 . C15 H151 . 119.3 no
P1 . C16 C17 . 118.6(4) yes
P1 . C16 C21 . 122.7(5) yes
C17 . C16 C21 . 118.5(6) yes
C16 . C17 C18 . 121.0(5) yes
C16 . C17 H171 . 118.5 no
C18 . C17 H171 . 120.5 no
C17 . C18 C19 . 120.5(5) yes
C17 . C18 H181 . 119.6 no
C19 . C18 H181 . 120.0 no
C18 . C19 C20 . 119.3(5) yes
C18 . C19 H191 . 121.1 no
C20 . C19 H191 . 119.5 no
C19 . C20 C21 . 120.2(5) yes
C19 . C20 H201 . 120.4 no
C21 . C20 H201 . 119.4 no
C20 . C21 C16 . 120.5(6) yes
C20 . C21 H211 . 119.7 no
C16 . C21 H211 . 119.8 no
C1 . C22 C23 . 109.7(5) yes
C1 . C22 C24 . 113.6(4) yes
C23 . C22 C24 . 111.6(5) yes
C1 . C22 H221 . 107.6 no
C23 . C22 H221 . 107.4 no
C24 . C22 H221 . 106.5 no
C22 . C23 H231 . 110.6 no
C22 . C23 H232 . 109.4 no
H231 . C23 H232 . 109.7 no
C22 . C23 H233 . 108.4 no
H231 . C23 H233 . 109.0 no
H232 . C23 H233 . 109.7 no
C22 . C24 H241 . 110.2 no
C22 . C24 H242 . 109.4 no
H241 . C24 H242 . 110.4 no
C22 . C24 H243 . 106.5 no
H241 . C24 H243 . 110.3 no
H242 . C24 H243 . 110.0 no
Ir1 . C25 C26 . 126.0(5) yes
Ir1 . C25 C30 . 115.2(5) yes
C26 . C25 C30 . 118.8(6) yes
C25 . C26 C27 . 121.3(7) yes
C25 . C26 H261 . 119.9 no
C27 . C26 H261 . 118.7 no
C26 . C27 C28 . 118.5(7) yes
C26 . C27 H271 . 120.7 no
C28 . C27 H271 . 120.7 no
C27 . C28 C29 . 122.0(6) yes
C27 . C28 H281 . 118.4 no
C29 . C28 H281 . 119.6 no
C28 . C29 C30 . 118.6(7) yes
C28 . C29 H291 . 120.1 no
C30 . C29 H291 . 121.3 no
C29 . C30 C25 . 120.6(7) yes
C29 . C30 C31 . 122.4(7) yes
C25 . C30 C31 . 116.9(5) yes
C30 . C31 N2 . 116.0(5) yes
C30 . C31 C32 . 121.6(5) yes
N2 . C31 C32 . 122.4(5) yes
C31 . C32 H321 . 109.2 no
C31 . C32 H322 . 110.9 no
H321 . C32 H322 . 108.6 no
C31 . C32 H323 . 109.1 no
H321 . C32 H323 . 109.0 no
H322 . C32 H323 . 109.9 no
N2 . C33 C34 . 121.4(5) yes
N2 . C33 C38 . 118.8(5) yes
C34 . C33 C38 . 119.8(5) yes
C33 . C34 C35 . 119.3(5) yes
C33 . C34 H341 . 120.0 no
C35 . C34 H341 . 120.7 no
C34 . C35 C36 . 121.5(6) yes
C34 . C35 H351 . 119.6 no
C36 . C35 H351 . 118.9 no
C35 . C36 C37 . 119.0(6) yes
C35 . C36 H361 . 119.4 no
C37 . C36 H361 . 121.6 no
C36 . C37 C38 . 120.4(6) yes
C36 . C37 H371 . 119.1 no
C38 . C37 H371 . 120.5 no
C37 . C38 C33 . 120.0(5) yes
C37 . C38 H381 . 120.3 no
C33 . C38 H381 . 119.7 no
O2 . C39 C40 . 106.3(5) yes
O2 . C39 H391 . 109.0 no
C40 . C39 H391 . 110.6 no
O2 . C39 H392 . 110.3 no
C40 . C39 H392 . 111.0 no
H391 . C39 H392 . 109.5 no
C39 . C40 C41 . 102.7(5) yes
C39 . C40 H401 . 112.2 no
C41 . C40 H401 . 111.1 no
C39 . C40 H402 . 110.2 no
C41 . C40 H402 . 110.7 no
H401 . C40 H402 . 109.9 no
C40 . C41 C42 . 102.5(5) yes
C40 . C41 H411 . 110.7 no
C42 . C41 H411 . 109.0 no
C40 . C41 H412 . 111.9 no
C42 . C41 H412 . 112.5 no
H411 . C41 H412 . 110.0 no
C41 . C42 O2 . 104.7(4) yes
C41 . C42 H421 . 111.7 no
O2 . C42 H421 . 109.5 no
C41 . C42 H422 . 111.0 no
O2 . C42 H422 . 110.7 no
H421 . C42 H422 . 109.2 no
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 P1 . 2.3237(13) yes
Ir1 N1 . 2.044(4) yes
Ir1 N2 . 2.205(4) yes
Ir1 O2 . 2.126(3) yes
Ir1 C25 . 2.063(5) yes
P1 C9 . 1.818(7) yes
P1 C10 . 1.827(5) yes
P1 C16 . 1.831(6) yes
P2 F1 5_555 1.574(4) yes
P2 F1 3_555 1.574(4) yes
P2 F2 5_555 1.573(3) yes
P2 F2 3_555 1.573(3) yes
P2 F1 . 1.574(4) yes
P2 F2 . 1.573(3) yes
P3 F3 3_655 1.519(6) yes
P3 F3 5_665 1.519(6) yes
P3 F4 3_655 1.513(5) yes
P3 F4 5_665 1.513(5) yes
P3 F3 . 1.519(6) yes
P3 F4 . 1.513(5) yes
P4 F6 5_665 1.591(4) yes
P4 F6 3_655 1.591(4) yes
P4 F5 5_665 1.547(5) yes
P4 F5 3_655 1.547(5) yes
P4 F5 . 1.547(5) yes
P4 F6 . 1.591(4) yes
N1 C1 . 1.500(5) yes
N1 C3 . 1.283(5) yes
N2 C31 . 1.295(5) yes
N2 C33 . 1.428(5) yes
O1 C2 . 1.469(8) yes
O1 C3 . 1.341(5) yes
O2 C39 . 1.470(6) yes
O2 C42 . 1.443(6) yes
C1 C2 . 1.514(7) yes
C1 C22 . 1.523(7) yes
C1 H11 . 0.982 no
C2 H21 . 0.973 no
C2 H22 . 0.974 no
C3 C4 . 1.474(7) yes
C4 C5 . 1.388(6) yes
C4 C9 . 1.408(8) yes
C5 C6 . 1.390(7) yes
C5 H51 . 0.934 no
C6 C7 . 1.385(7) yes
C6 H61 . 0.934 no
C7 C8 . 1.372(7) yes
C7 H71 . 0.936 no
C8 C9 . 1.405(7) yes
C8 H81 . 0.932 no
C10 C11 . 1.370(7) yes
C10 C15 . 1.404(7) yes
C11 C12 . 1.391(7) yes
C11 H111 . 0.936 no
C12 C13 . 1.356(7) yes
C12 H121 . 0.930 no
C13 C14 . 1.387(7) yes
C13 H131 . 0.934 no
C14 C15 . 1.396(7) yes
C14 H141 . 0.933 no
C15 H151 . 0.944 no
C16 C17 . 1.383(7) yes
C16 C21 . 1.377(8) yes
C17 C18 . 1.370(7) yes
C17 H171 . 0.934 no
C18 C19 . 1.378(7) yes
C18 H181 . 0.937 no
C19 C20 . 1.369(7) yes
C19 H191 . 0.943 no
C20 C21 . 1.394(8) yes
C20 H201 . 0.935 no
C21 H211 . 0.932 no
C22 C23 . 1.522(7) yes
C22 C24 . 1.536(7) yes
C22 H221 . 0.975 no
C23 H231 . 0.966 no
C23 H232 . 0.968 no
C23 H233 . 0.965 no
C24 H241 . 0.960 no
C24 H242 . 0.967 no
C24 H243 . 0.959 no
C25 C26 . 1.408(8) yes
C25 C30 . 1.373(9) yes
C26 C27 . 1.384(8) yes
C26 H261 . 0.928 no
C27 C28 . 1.368(10) yes
C27 H271 . 0.936 no
C28 C29 . 1.394(9) yes
C28 H281 . 0.936 no
C29 C30 . 1.402(8) yes
C29 H291 . 0.932 no
C30 C31 . 1.467(9) yes
C31 C32 . 1.504(7) yes
C32 H321 . 0.965 no
C32 H322 . 0.965 no
C32 H323 . 0.959 no
C33 C34 . 1.372(7) yes
C33 C38 . 1.372(7) yes
C34 C35 . 1.405(8) yes
C34 H341 . 0.933 no
C35 C36 . 1.353(8) yes
C35 H351 . 0.936 no
C36 C37 . 1.375(8) yes
C36 H361 . 0.934 no
C37 C38 . 1.401(7) yes
C37 H371 . 0.932 no
C38 H381 . 0.945 no
C39 C40 . 1.490(8) yes
C39 H391 . 0.980 no
C39 H392 . 0.982 no
C40 C41 . 1.494(8) yes
C40 H401 . 0.980 no
C40 H402 . 0.982 no
C41 C42 . 1.529(7) yes
C41 H411 . 0.977 no
C41 H412 . 0.973 no
C42 H421 . 0.965 no
C42 H422 . 0.973 no
