#------------------------------------------------------------------------------
#$Date: 2018-08-16 18:56:10 +0300 (Thu, 16 Aug 2018) $
#$Revision: 209813 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/09/4060962.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_4060962
loop_
_publ_author_name
'Ionkin, Alex S.'
'Marshall, William J.'
'Fish, Brian M.'
_publ_section_title
;
 Synthesis and Structural Characterization of a Series of Novel
 Polyaromatic Ligands Containing Pyrene and Related Biscyclometalated
 Iridium(III) Complexes
;
_journal_coden_ASTM              ORGND7
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1461
_journal_page_last               1471
_journal_paper_doi               10.1021/om0510775
_journal_volume                  25
_journal_year                    2006
_chemical_formula_sum            'C66 H50 F6 Ir N2 O3 P'
_chemical_formula_weight         1256.25
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 113.766(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.579(3)
_cell_length_b                   12.2266(19)
_cell_length_c                   22.819(4)
_cell_measurement_temperature    293(2)
_cell_volume                     5254.6(14)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_meas      hemisphere
_cod_duplicate_entry             4074987
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               4060962
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.202129(8) 0.289455(13) 0.464576(7) 0.02034(6) Uani 1 1 d . . .
P1 P 0.20311(6) 0.15467(10) 0.53905(5) 0.0231(2) Uani 1 1 d . . .
F1 F -0.00457(14) 0.3190(2) 0.48213(14) 0.0376(7) Uani 1 1 d . . .
F2 F -0.03824(13) 0.1537(3) 0.48356(13) 0.0414(7) Uani 1 1 d . . .
F3 F -0.06141(14) 0.2348(3) 0.39376(13) 0.0402(7) Uani 1 1 d . . .
F4 F 0.10378(15) 0.0285(2) 0.41650(13) 0.0398(7) Uani 1 1 d . . .
F5 F -0.00076(16) 0.0138(2) 0.41408(15) 0.0462(8) Uani 1 1 d . . .
F6 F 0.01797(16) 0.1149(2) 0.34580(13) 0.0449(7) Uani 1 1 d . . .
O1 O 0.08849(15) 0.2692(2) 0.43227(14) 0.0240(7) Uani 1 1 d . . .
N17 N 0.19591(18) 0.1985(3) 0.38637(16) 0.0228(8) Uani 1 1 d . . .
N40 N 0.20903(17) 0.4014(3) 0.53274(15) 0.0201(7) Uani 1 1 d . . .
C1 C 0.1078(2) 0.1459(4) 0.5232(2) 0.0265(10) Uani 1 1 d . . .
H1A H 0.0959 0.0711 0.5291 0.032 Uiso 1 1 calc R . .
H1B H 0.0981 0.1918 0.5534 0.032 Uiso 1 1 calc R . .
C2 C 0.0611(2) 0.1835(4) 0.4537(2) 0.0243(9) Uani 1 1 d . . .
C3 C -0.0107(2) 0.2220(4) 0.4532(2) 0.0298(10) Uani 1 1 d . . .
C4 C 0.0449(2) 0.0855(4) 0.4072(2) 0.0314(10) Uani 1 1 d . . .
C5 C 0.2472(2) 0.1967(4) 0.6232(2) 0.0272(10) Uani 1 1 d . . .
C6 C 0.2129(3) 0.2364(4) 0.6602(2) 0.0331(11) Uani 1 1 d . . .
H6A H 0.1636 0.2380 0.6433 0.040 Uiso 1 1 calc R . .
C7 C 0.2515(3) 0.2738(5) 0.7221(3) 0.0446(14) Uani 1 1 d . . .
H7A H 0.2277 0.3003 0.7463 0.053 Uiso 1 1 calc R . .
C8 C 0.3245(3) 0.2720(5) 0.7480(2) 0.0440(14) Uani 1 1 d . . .
H8A H 0.3501 0.2959 0.7897 0.053 Uiso 1 1 calc R . .
C9 C 0.3593(3) 0.2343(5) 0.7114(3) 0.0502(15) Uani 1 1 d . . .
H9A H 0.4087 0.2340 0.7283 0.060 Uiso 1 1 calc R . .
C10 C 0.3212(3) 0.1972(5) 0.6499(2) 0.0436(14) Uani 1 1 d . . .
H10A H 0.3454 0.1719 0.6259 0.052 Uiso 1 1 calc R . .
C11 C 0.2367(2) 0.0146(4) 0.5427(2) 0.0265(10) Uani 1 1 d . . .
C12 C 0.2004(3) -0.0780(4) 0.5482(2) 0.0373(12) Uani 1 1 d . . .
H12A H 0.1566 -0.0705 0.5508 0.045 Uiso 1 1 calc R . .
C13 C 0.2284(3) -0.1807(4) 0.5499(3) 0.0489(15) Uani 1 1 d . . .
H13A H 0.2023 -0.2418 0.5516 0.059 Uiso 1 1 calc R . .
C14 C 0.2941(3) -0.1942(5) 0.5491(3) 0.0541(16) Uani 1 1 d . . .
H14A H 0.3132 -0.2639 0.5519 0.065 Uiso 1 1 calc R . .
C15 C 0.3318(3) -0.1039(5) 0.5443(3) 0.0478(14) Uani 1 1 d . . .
H15A H 0.3764 -0.1126 0.5437 0.057 Uiso 1 1 calc R . .
C16 C 0.3032(2) -0.0008(4) 0.5405(2) 0.0351(11) Uani 1 1 d . . .
H16A H 0.3285 0.0597 0.5364 0.042 Uiso 1 1 calc R . .
C18 C 0.2214(2) 0.0977(4) 0.3875(2) 0.0284(10) Uani 1 1 d . . .
H18A H 0.2414 0.0619 0.4268 0.034 Uiso 1 1 calc R . .
C19 C 0.2197(3) 0.0436(4) 0.3342(2) 0.0350(11) Uani 1 1 d . . .
H19A H 0.2383 -0.0267 0.3378 0.042 Uiso 1 1 calc R . .
C20 C 0.1903(3) 0.0941(4) 0.2750(2) 0.0328(11) Uani 1 1 d . . .
C21 C 0.1633(2) 0.1981(4) 0.2732(2) 0.0276(10) Uani 1 1 d . . .
H21A H 0.1429 0.2340 0.2341 0.033 Uiso 1 1 calc R . .
C22 C 0.1656(2) 0.2514(4) 0.3286(2) 0.0236(9) Uani 1 1 d . . .
C23 C 0.1883(3) 0.0403(5) 0.2150(3) 0.0471(14) Uani 1 1 d . . .
H23A H 0.1481 0.0670 0.1788 0.071 Uiso 1 1 calc R . .
H23B H 0.1843 -0.0375 0.2183 0.071 Uiso 1 1 calc R . .
H23C H 0.2311 0.0571 0.2096 0.071 Uiso 1 1 calc R . .
C24 C 0.1482(2) 0.3661(4) 0.3332(2) 0.0226(9) Uani 1 1 d . . .
C25 C 0.1776(2) 0.4080(3) 0.39650(19) 0.0209(9) Uani 1 1 d . . .
C26 C 0.1802(2) 0.5201(4) 0.4048(2) 0.0249(9) Uani 1 1 d . . .
H26A H 0.2004 0.5482 0.4461 0.030 Uiso 1 1 calc R . .
C27 C 0.1533(2) 0.5930(4) 0.3531(2) 0.0245(9) Uani 1 1 d . . .
C28 C 0.1154(2) 0.5503(4) 0.2907(2) 0.0253(9) Uani 1 1 d . . .
C29 C 0.1105(2) 0.4350(4) 0.2806(2) 0.0231(9) Uani 1 1 d . . .
C30 C 0.1590(3) 0.7100(4) 0.3609(2) 0.0315(10) Uani 1 1 d . . .
H30A H 0.1853 0.7390 0.4013 0.038 Uiso 1 1 calc R . .
C31 C 0.1273(3) 0.7783(4) 0.3114(3) 0.0355(11) Uani 1 1 d . . .
H31A H 0.1322 0.8534 0.3182 0.043 Uiso 1 1 calc R . .
C32 C 0.0865(3) 0.7380(4) 0.2487(2) 0.0330(11) Uani 1 1 d . . .
C33 C 0.0802(2) 0.6231(4) 0.2385(2) 0.0275(10) Uani 1 1 d . . .
C34 C 0.0501(3) 0.8069(4) 0.1956(3) 0.0417(13) Uani 1 1 d . . .
H34A H 0.0538 0.8823 0.2011 0.050 Uiso 1 1 calc R . .
C35 C 0.0099(3) 0.7654(5) 0.1369(3) 0.0436(14) Uani 1 1 d . . .
H35A H -0.0131 0.8129 0.1030 0.052 Uiso 1 1 calc R . .
C36 C 0.0027(3) 0.6530(5) 0.1266(2) 0.0389(12) Uani 1 1 d . . .
H36A H -0.0253 0.6259 0.0861 0.047 Uiso 1 1 calc R . .
C37 C 0.0374(2) 0.5811(4) 0.1770(2) 0.0315(11) Uani 1 1 d . . .
C38 C 0.0271(2) 0.4648(4) 0.1696(2) 0.0313(11) Uani 1 1 d . . .
H38A H -0.0039 0.4363 0.1305 0.038 Uiso 1 1 calc R . .
C39 C 0.0619(2) 0.3964(4) 0.2189(2) 0.0291(10) Uani 1 1 d . . .
H39A H 0.0542 0.3215 0.2128 0.035 Uiso 1 1 calc R . .
C41 C 0.1516(2) 0.4385(4) 0.5403(2) 0.0258(10) Uani 1 1 d . . .
H41A H 0.1071 0.4133 0.5126 0.031 Uiso 1 1 calc R . .
C42 C 0.1557(2) 0.5121(4) 0.5871(2) 0.0299(10) Uani 1 1 d . . .
H42A H 0.1148 0.5358 0.5913 0.036 Uiso 1 1 calc R . .
C43 C 0.2221(3) 0.5505(4) 0.6281(2) 0.0353(11) Uani 1 1 d . . .
C44 C 0.2807(2) 0.5144(4) 0.6180(2) 0.0334(11) Uani 1 1 d . . .
H44A H 0.3252 0.5420 0.6438 0.040 Uiso 1 1 calc R . .
C45 C 0.2757(2) 0.4392(4) 0.57124(19) 0.0226(9) Uani 1 1 d . . .
C46 C 0.2294(3) 0.6303(6) 0.6806(3) 0.0629(19) Uani 1 1 d . . .
H46A H 0.2778 0.6542 0.7010 0.094 Uiso 1 1 calc R . .
H46B H 0.2157 0.5953 0.7116 0.094 Uiso 1 1 calc R . .
H46C H 0.1992 0.6922 0.6627 0.094 Uiso 1 1 calc R . .
C47 C 0.3312(2) 0.3959(4) 0.5530(2) 0.0278(10) Uani 1 1 d . . .
C48 C 0.3057(2) 0.3247(4) 0.4988(2) 0.0238(9) Uani 1 1 d . . .
C49 C 0.3540(2) 0.2895(4) 0.4735(2) 0.0285(10) Uani 1 1 d . . .
H49A H 0.3380 0.2431 0.4382 0.034 Uiso 1 1 calc R . .
C50 C 0.4253(2) 0.3218(4) 0.4995(2) 0.0310(11) Uani 1 1 d . . .
C51 C 0.4516(2) 0.3876(4) 0.5552(2) 0.0294(10) Uani 1 1 d . . .
C52 C 0.4047(2) 0.4219(5) 0.5838(2) 0.0429(14) Uani 1 1 d . . .
C53 C 0.4723(3) 0.2910(5) 0.4698(3) 0.0539(17) Uani 1 1 d . . .
H53A H 0.4554 0.2482 0.4330 0.065 Uiso 1 1 calc R . .
C54 C 0.5408(3) 0.3238(5) 0.4948(3) 0.0596(18) Uani 1 1 d . . .
H54A H 0.5700 0.3038 0.4743 0.072 Uiso 1 1 calc R . .
C55 C 0.5697(2) 0.3882(4) 0.5516(3) 0.0385(12) Uani 1 1 d . . .
C56 C 0.5243(2) 0.4194(4) 0.5819(2) 0.0332(11) Uani 1 1 d . . .
C57 C 0.6409(3) 0.4227(5) 0.5785(3) 0.0461(14) Uani 1 1 d . . .
H57A H 0.6713 0.4007 0.5597 0.055 Uiso 1 1 calc R . .
C58 C 0.6668(3) 0.4884(5) 0.6322(3) 0.0466(14) Uani 1 1 d . . .
H58A H 0.7133 0.5138 0.6479 0.056 Uiso 1 1 calc R . .
C59 C 0.6237(3) 0.5154(6) 0.6618(3) 0.0604(18) Uani 1 1 d . . .
H59A H 0.6415 0.5576 0.6988 0.072 Uiso 1 1 calc R . .
C60 C 0.5526(3) 0.4810(6) 0.6378(3) 0.0565(18) Uani 1 1 d . . .
C61 C 0.5082(3) 0.4991(9) 0.6697(4) 0.111(4) Uani 1 1 d . . .
H61A H 0.5269 0.5335 0.7094 0.134 Uiso 1 1 calc R . .
C62 C 0.4390(3) 0.4684(8) 0.6452(3) 0.096(3) Uani 1 1 d . . .
H62A H 0.4130 0.4786 0.6700 0.116 Uiso 1 1 calc R . .
O82 O 0.5015(5) 0.1208(9) 0.6280(5) 0.185(4) Uani 1 1 d . . .
C81 C 0.5294(8) 0.0415(13) 0.5959(10) 0.189(7) Uani 1 1 d . . .
C83 C 0.5969(8) 0.0592(15) 0.5917(9) 0.216(8) Uani 1 1 d . . .
C85 C 0.4969(13) -0.035(2) 0.577(2) 0.60(4) Uani 1 1 d . . .
C70 C 0.462(3) 0.805(2) 0.727(3) 1.08(9) Uani 1 1 d . . .
C71 C 0.3805(10) 0.8979(18) 0.7285(11) 0.287(12) Uani 1 1 d . . .
O72 O 0.4073(7) 0.7210(12) 0.7227(6) 0.245(6) Uani 1 1 d . . .
C74 C 0.529(3) 0.995(3) 0.6775(17) 0.74(5) Uani 1 1 d . . .
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
Ir1 C48 1.999(4) . ?
Ir1 C25 2.034(4) . ?
Ir1 N40 2.034(3) . ?
Ir1 N17 2.062(3) . ?
Ir1 O1 2.164(3) . ?
Ir1 P1 2.3615(12) . ?
P1 C5 1.836(4) . ?
P1 C11 1.836(5) . ?
P1 C1 1.848(4) . ?
F1 C3 1.340(5) . ?
F2 C3 1.348(5) . ?
F3 C3 1.346(5) . ?
F4 C4 1.339(5) . ?
F5 C4 1.339(5) . ?
F6 C4 1.333(5) . ?
O1 C2 1.371(5) . ?
N17 C18 1.336(6) . ?
N17 C22 1.372(6) . ?
N40 C41 1.340(5) . ?
N40 C45 1.377(5) . ?
C1 C2 1.555(6) . ?
C2 C3 1.544(6) . ?
C2 C4 1.545(7) . ?
C5 C6 1.387(6) . ?
C5 C10 1.395(6) . ?
C6 C7 1.391(7) . ?
C7 C8 1.375(8) . ?
C8 C9 1.381(8) . ?
C9 C10 1.379(7) . ?
C11 C12 1.391(6) . ?
C11 C16 1.402(6) . ?
C12 C13 1.375(7) . ?
C13 C14 1.368(8) . ?
C14 C15 1.379(8) . ?
C15 C16 1.380(7) . ?
C18 C19 1.374(6) . ?
C19 C20 1.383(7) . ?
C20 C21 1.381(6) . ?
C20 C23 1.504(6) . ?
C21 C22 1.406(6) . ?
C22 C24 1.461(6) . ?
C24 C29 1.416(6) . ?
C24 C25 1.418(6) . ?
C25 C26 1.382(6) . ?
C26 C27 1.403(6) . ?
C27 C28 1.418(6) . ?
C27 C30 1.441(6) . ?
C28 C29 1.426(6) . ?
C28 C33 1.429(6) . ?
C29 C39 1.438(6) . ?
C30 C31 1.343(7) . ?
C31 C32 1.424(7) . ?
C32 C34 1.416(7) . ?
C32 C33 1.422(7) . ?
C33 C37 1.418(7) . ?
C34 C35 1.358(8) . ?
C35 C36 1.392(8) . ?
C36 C37 1.394(7) . ?
C37 C38 1.437(7) . ?
C38 C39 1.353(6) . ?
C41 C42 1.373(6) . ?
C42 C43 1.391(7) . ?
C43 C44 1.387(6) . ?
C43 C46 1.505(7) . ?
C44 C45 1.380(6) . ?
C45 C47 1.464(6) . ?
C47 C52 1.423(6) . ?
C47 C48 1.427(6) . ?
C48 C49 1.403(6) . ?
C49 C50 1.401(6) . ?
C50 C51 1.415(7) . ?
C50 C53 1.437(7) . ?
C51 C56 1.424(6) . ?
C51 C52 1.428(6) . ?
C52 C62 1.411(8) . ?
C53 C54 1.350(8) . ?
C54 C55 1.426(8) . ?
C55 C57 1.406(7) . ?
C55 C56 1.419(7) . ?
C56 C60 1.390(7) . ?
C57 C58 1.379(8) . ?
C58 C59 1.355(7) . ?
C59 C60 1.403(7) . ?
C60 C61 1.398(8) . ?
C61 C62 1.357(8) . ?
O82 C81 1.463(15) . ?
O82 C74 1.85(3) 1_545 ?
C81 C85 1.134(17) . ?
C81 C83 1.448(17) . ?
C81 C74 1.95(4) 1_545 ?
C70 O72 1.50(5) . ?
C70 C70 1.48(7) 2_656 ?
C70 C71 2.04(8) . ?
C74 O82 1.85(3) 1_565 ?
C74 C81 1.95(4) 1_565 ?
