#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:00:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180367 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/36/7203692.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_7203692
loop_
_publ_author_name
'Wu, Fang-Iy'
'Su, Huei-Jen'
'Shu, Ching-Fong'
'Luo, Liyang'
'Diau, Wei-Guang'
'Cheng, Chien-Hong'
'Duan, Jiun-Pey'
'Lee, Gene-Hsiang'
_publ_section_title
;
 Tuning the emission and morphology of cyclometalated iridium complexes
 and their applications to organic light-emitting diodes
;
_journal_issue                   10
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              1035
_journal_paper_doi               10.1039/b415754k
_journal_volume                  15
_journal_year                    2005
_chemical_formula_sum            'C47 H35 Ir N2 O2'
_chemical_formula_weight         851.97
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.876(1)
_cell_angle_beta                 91.234(1)
_cell_angle_gamma                100.583(1)
_cell_formula_units_Z            2
_cell_length_a                   11.2451(5)
_cell_length_b                   11.7178(5)
_cell_length_c                   14.2394(6)
_cell_measurement_reflns_used    4102
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20.88
_cell_measurement_theta_min      2.47
_cell_volume                     1759.35(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'BRUKER SMART APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23504
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    3.839
_exptl_absorpt_correction_T_max  0.8312
_exptl_absorpt_correction_T_min  0.5140
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.259
_refine_diff_density_min         -0.745
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         8059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0240P)²+1.4088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0787
_reflns_number_gt                7269
_reflns_number_total             8059
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b415754k.txt
_cod_data_source_block           ic10619
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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-1
_cod_database_code               7203692
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_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
Ir Ir 0.751548(14) 0.985302(14) 0.743403(12) 0.02686(6) Uani 1 1 d . . .
O1 O 0.8708(3) 1.0669(3) 0.8780(2) 0.0402(8) Uani 1 1 d . . .
O2 O 0.6318(3) 0.9018(3) 0.8329(2) 0.0405(8) Uani 1 1 d . . .
N1 N 0.8740(3) 0.8699(3) 0.7089(3) 0.0305(8) Uani 1 1 d . . .
N2 N 0.6312(3) 1.1024(3) 0.7637(3) 0.0291(8) Uani 1 1 d . . .
C1 C 0.8637(4) 1.0711(4) 0.6711(3) 0.0286(9) Uani 1 1 d . . .
C2 C 0.8500(4) 1.1711(4) 0.6387(3) 0.0357(10) Uani 1 1 d . . .
H2A H 0.7776 1.1991 0.6468 0.043 Uiso 1 1 calc R . .
C3 C 0.9411(5) 1.2282(4) 0.5954(4) 0.0420(11) Uani 1 1 d . . .
H3A H 0.9293 1.2937 0.5744 0.050 Uiso 1 1 calc R . .
C4 C 1.0506(5) 1.1891(4) 0.5828(4) 0.0425(11) Uani 1 1 d . . .
H4A H 1.1125 1.2297 0.5553 0.051 Uiso 1 1 calc R . .
C5 C 1.0672(4) 1.0907(4) 0.6111(3) 0.0353(10) Uani 1 1 d . . .
H5A H 1.1399 1.0634 0.6015 0.042 Uiso 1 1 calc R . .
C6 C 0.9749(4) 1.0313(4) 0.6543(3) 0.0292(9) Uani 1 1 d . . .
C7 C 0.9777(4) 0.9185(4) 0.6777(3) 0.0296(9) Uani 1 1 d . . .
C8 C 1.0763(4) 0.8592(4) 0.6638(3) 0.0343(10) Uani 1 1 d . . .
H8A H 1.1489 0.8991 0.6479 0.041 Uiso 1 1 calc R . .
C9 C 1.0704(4) 0.7462(4) 0.6726(3) 0.0355(10) Uani 1 1 d . . .
C10 C 0.9578(4) 0.6868(4) 0.6979(3) 0.0335(10) Uani 1 1 d . . .
C11 C 0.9394(5) 0.5689(4) 0.7085(4) 0.0460(12) Uani 1 1 d . . .
H11A H 1.0032 0.5273 0.7008 0.055 Uiso 1 1 calc R . .
C12 C 0.8298(5) 0.5151(5) 0.7297(5) 0.0568(15) Uani 1 1 d . . .
H12A H 0.8184 0.4371 0.7358 0.068 Uiso 1 1 calc R . .
C13 C 0.7347(5) 0.5781(5) 0.7421(4) 0.0562(15) Uani 1 1 d . . .
H13A H 0.6592 0.5401 0.7547 0.067 Uiso 1 1 calc R . .
C14 C 0.7489(4) 0.6923(4) 0.7364(4) 0.0466(12) Uani 1 1 d . . .
H14A H 0.6840 0.7324 0.7463 0.056 Uiso 1 1 calc R . .
C15 C 0.8611(4) 0.7515(4) 0.7157(3) 0.0334(10) Uani 1 1 d . . .
C16 C 1.1776(4) 0.6863(4) 0.6542(4) 0.0388(11) Uani 1 1 d . . .
C17 C 1.2853(4) 0.7405(5) 0.7133(4) 0.0458(12) Uani 1 1 d . . .
H17A H 1.2884 0.8108 0.7655 0.055 Uiso 1 1 calc R . .
C18 C 1.3876(5) 0.6903(5) 0.6946(5) 0.0550(15) Uani 1 1 d . . .
H18A H 1.4592 0.7266 0.7345 0.066 Uiso 1 1 calc R . .
C19 C 1.3838(5) 0.5869(5) 0.6172(5) 0.0565(15) Uani 1 1 d . . .
H19A H 1.4528 0.5534 0.6048 0.068 Uiso 1 1 calc R . .
C20 C 1.2782(5) 0.5327(5) 0.5580(5) 0.0594(15) Uani 1 1 d . . .
H20A H 1.2760 0.4632 0.5052 0.071 Uiso 1 1 calc R . .
C21 C 1.1750(5) 0.5822(5) 0.5775(4) 0.0496(13) Uani 1 1 d . . .
H21A H 1.1033 0.5447 0.5381 0.059 Uiso 1 1 calc R . .
C22 C 0.6370(4) 0.9016(4) 0.6264(3) 0.0302(9) Uani 1 1 d . . .
C23 C 0.6489(4) 0.8018(4) 0.5462(3) 0.0371(10) Uani 1 1 d . . .
H23A H 0.7205 0.7721 0.5426 0.045 Uiso 1 1 calc R . .
C24 C 0.5567(5) 0.7472(4) 0.4731(4) 0.0454(12) Uani 1 1 d . . .
H24A H 0.5669 0.6816 0.4206 0.054 Uiso 1 1 calc R . .
C25 C 0.4484(5) 0.7891(4) 0.4766(4) 0.0445(12) Uani 1 1 d . . .
H25A H 0.3859 0.7505 0.4276 0.053 Uiso 1 1 calc R . .
C26 C 0.4341(4) 0.8876(4) 0.5526(3) 0.0391(11) Uani 1 1 d . . .
H26A H 0.3626 0.9171 0.5544 0.047 Uiso 1 1 calc R . .
C27 C 0.5271(4) 0.9435(4) 0.6274(3) 0.0306(9) Uani 1 1 d . . .
C28 C 0.5254(4) 1.0539(4) 0.7068(3) 0.0301(9) Uani 1 1 d . . .
C29 C 0.4266(4) 1.1135(4) 0.7216(3) 0.0359(10) Uani 1 1 d . . .
H29A H 0.3533 1.0749 0.6850 0.043 Uiso 1 1 calc R . .
C30 C 0.4344(4) 1.2257(4) 0.7877(3) 0.0330(10) Uani 1 1 d . . .
C31 C 0.5498(4) 1.2848(4) 0.8405(3) 0.0315(9) Uani 1 1 d . . .
C32 C 0.5716(4) 1.4032(4) 0.9059(3) 0.0406(11) Uani 1 1 d . . .
H32A H 0.5085 1.4457 0.9170 0.049 Uiso 1 1 calc R . .
C33 C 0.6829(5) 1.4573(5) 0.9533(4) 0.0484(13) Uani 1 1 d . . .
H33A H 0.6959 1.5363 0.9958 0.058 Uiso 1 1 calc R . .
C34 C 0.7777(4) 1.3934(5) 0.9377(4) 0.0482(13) Uani 1 1 d . . .
H34A H 0.8540 1.4307 0.9697 0.058 Uiso 1 1 calc R . .
C35 C 0.7602(4) 1.2783(4) 0.8767(3) 0.0409(11) Uani 1 1 d . . .
H35A H 0.8246 1.2374 0.8675 0.049 Uiso 1 1 calc R . .
C36 C 0.6462(4) 1.2197(4) 0.8269(3) 0.0303(9) Uani 1 1 d . . .
C37 C 0.3260(4) 1.2832(4) 0.8025(3) 0.0337(10) Uani 1 1 d . . .
C38 C 0.2241(4) 1.2270(4) 0.8362(4) 0.0412(11) Uani 1 1 d . . .
H38A H 0.2246 1.1548 0.8510 0.049 Uiso 1 1 calc R . .
C39 C 0.1201(4) 1.2779(5) 0.8485(4) 0.0479(13) Uani 1 1 d . . .
H39A H 0.0519 1.2398 0.8715 0.057 Uiso 1 1 calc R . .
C40 C 0.1188(5) 1.3834(5) 0.8265(4) 0.0496(13) Uani 1 1 d . . .
H40A H 0.0493 1.4166 0.8339 0.060 Uiso 1 1 calc R . .
C41 C 0.2199(5) 1.4408(5) 0.7936(4) 0.0495(13) Uani 1 1 d . . .
H41A H 0.2186 1.5132 0.7794 0.059 Uiso 1 1 calc R . .
C42 C 0.3234(4) 1.3918(4) 0.7814(4) 0.0426(11) Uani 1 1 d . . .
H42A H 0.3913 1.4313 0.7591 0.051 Uiso 1 1 calc R . .
C43 C 0.9411(6) 1.1412(7) 1.0454(4) 0.077(2) Uani 1 1 d . . .
H43A H 1.0203 1.1444 1.0212 0.115 Uiso 1 1 calc R . .
H43B H 0.9380 1.1070 1.0991 0.115 Uiso 1 1 calc R . .
H43C H 0.9249 1.2220 1.0677 0.115 Uiso 1 1 calc R . .
C44 C 0.8465(5) 1.0626(5) 0.9633(4) 0.0502(13) Uani 1 1 d . . .
C45 C 0.7436(6) 0.9954(6) 0.9882(4) 0.0640(17) Uani 1 1 d . . .
H45A H 0.7396 1.0019 1.0546 0.077 Uiso 1 1 calc R . .
C46 C 0.6468(5) 0.9200(5) 0.9257(4) 0.0545(14) Uani 1 1 d . . .
C47 C 0.5475(6) 0.8476(7) 0.9671(5) 0.088(2) Uani 1 1 d . . .
H47A H 0.4699 0.8491 0.9385 0.132 Uiso 1 1 calc R . .
H47B H 0.5511 0.8826 1.0373 0.132 Uiso 1 1 calc R . .
H47C H 0.5583 0.7649 0.9519 0.132 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'
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'
Ir Ir -1.4442 7.9887 '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
_geom_angle_publ_flag
C1 Ir C22 93.26(17) . . ?
C1 Ir N2 95.73(15) . . ?
C22 Ir N2 80.08(15) . . ?
C1 Ir N1 79.75(15) . . ?
C22 Ir N1 96.43(15) . . ?
N2 Ir N1 174.18(13) . . ?
C1 Ir O2 175.80(14) . . ?
C22 Ir O2 90.36(15) . . ?
N2 Ir O2 82.79(13) . . ?
N1 Ir O2 101.98(13) . . ?
C1 Ir O1 91.15(15) . . ?
C22 Ir O1 175.38(14) . . ?
N2 Ir O1 100.85(13) . . ?
N1 Ir O1 82.99(13) . . ?
O2 Ir O1 85.28(12) . . ?
C44 O1 Ir 126.6(3) . . ?
C46 O2 Ir 126.8(3) . . ?
C7 N1 C15 118.2(3) . . ?
C7 N1 Ir 113.9(3) . . ?
C15 N1 Ir 127.9(3) . . ?
C28 N2 C36 118.5(3) . . ?
C28 N2 Ir 113.3(3) . . ?
C36 N2 Ir 128.1(3) . . ?
C2 C1 C6 116.2(4) . . ?
C2 C1 Ir 128.1(3) . . ?
C6 C1 Ir 115.5(3) . . ?
C3 C2 C1 121.6(4) . . ?
C2 C3 C4 120.6(4) . . ?
C5 C4 C3 119.9(4) . . ?
C4 C5 C6 119.9(4) . . ?
C5 C6 C1 121.7(4) . . ?
C5 C6 C7 124.5(4) . . ?
C1 C6 C7 113.6(4) . . ?
N1 C7 C8 121.2(4) . . ?
N1 C7 C6 114.7(4) . . ?
C8 C7 C6 124.0(4) . . ?
C9 C8 C7 122.8(4) . . ?
C8 C9 C10 117.6(4) . . ?
C8 C9 C16 120.3(4) . . ?
C10 C9 C16 122.0(4) . . ?
C11 C10 C15 118.5(4) . . ?
C11 C10 C9 123.3(4) . . ?
C15 C10 C9 118.2(4) . . ?
C12 C11 C10 121.0(4) . . ?
C11 C12 C13 119.4(5) . . ?
C14 C13 C12 121.9(5) . . ?
C13 C14 C15 120.5(5) . . ?
N1 C15 C14 119.8(4) . . ?
N1 C15 C10 121.6(4) . . ?
C14 C15 C10 118.6(4) . . ?
C21 C16 C17 118.9(4) . . ?
C21 C16 C9 121.8(4) . . ?
C17 C16 C9 119.2(4) . . ?
C18 C17 C16 120.3(5) . . ?
C19 C18 C17 120.1(5) . . ?
C18 C19 C20 120.2(5) . . ?
C19 C20 C21 119.7(5) . . ?
C16 C21 C20 120.8(5) . . ?
C23 C22 C27 116.9(4) . . ?
C23 C22 Ir 128.0(3) . . ?
C27 C22 Ir 115.0(3) . . ?
C24 C23 C22 121.2(4) . . ?
C23 C24 C25 120.7(4) . . ?
C26 C25 C24 119.8(4) . . ?
C25 C26 C27 119.9(4) . . ?
C26 C27 C22 121.4(4) . . ?
C26 C27 C28 124.3(4) . . ?
C22 C27 C28 114.0(4) . . ?
N2 C28 C29 120.8(4) . . ?
N2 C28 C27 114.9(4) . . ?
C29 C28 C27 124.2(4) . . ?
C30 C29 C28 122.5(4) . . ?
C29 C30 C31 117.5(4) . . ?
C29 C30 C37 120.3(4) . . ?
C31 C30 C37 122.2(4) . . ?
C32 C31 C36 118.5(4) . . ?
C32 C31 C30 123.1(4) . . ?
C36 C31 C30 118.5(4) . . ?
C33 C32 C31 121.5(4) . . ?
C32 C33 C34 119.5(4) . . ?
C35 C34 C33 121.1(5) . . ?
C34 C35 C36 120.8(4) . . ?
N2 C36 C35 119.7(4) . . ?
N2 C36 C31 121.6(4) . . ?
C35 C36 C31 118.6(4) . . ?
C38 C37 C42 118.7(4) . . ?
C38 C37 C30 119.6(4) . . ?
C42 C37 C30 121.8(4) . . ?
C37 C38 C39 120.6(5) . . ?
C40 C39 C38 119.9(5) . . ?
C39 C40 C41 120.2(5) . . ?
C40 C41 C42 120.5(5) . . ?
C41 C42 C37 120.1(5) . . ?
O1 C44 C45 126.8(5) . . ?
O1 C44 C43 115.0(5) . . ?
C45 C44 C43 118.3(5) . . ?
C46 C45 C44 127.6(5) . . ?
O2 C46 C45 126.4(5) . . ?
O2 C46 C47 114.4(5) . . ?
C45 C46 C47 119.1(5) . . ?
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
Ir C1 1.963(4) . ?
Ir C22 1.973(4) . ?
Ir N2 2.066(3) . ?
Ir N1 2.072(3) . ?
Ir O2 2.170(3) . ?
Ir O1 2.177(3) . ?
O1 C44 1.264(6) . ?
O2 C46 1.279(6) . ?
N1 C7 1.345(5) . ?
N1 C15 1.399(5) . ?
N2 C28 1.355(5) . ?
N2 C36 1.385(5) . ?
C1 C2 1.409(6) . ?
C1 C6 1.414(5) . ?
C2 C3 1.376(6) . ?
C3 C4 1.388(7) . ?
C4 C5 1.367(6) . ?
C5 C6 1.397(6) . ?
C6 C7 1.459(6) . ?
C7 C8 1.402(5) . ?
C8 C9 1.356(6) . ?
C9 C10 1.435(6) . ?
C9 C16 1.494(6) . ?
C10 C11 1.412(6) . ?
C10 C15 1.423(6) . ?
C11 C12 1.359(7) . ?
C12 C13 1.394(7) . ?
C13 C14 1.344(7) . ?
C14 C15 1.405(6) . ?
C16 C21 1.376(7) . ?
C16 C17 1.392(7) . ?
C17 C18 1.383(6) . ?
C18 C19 1.374(8) . ?
C19 C20 1.376(8) . ?
C20 C21 1.389(7) . ?
C22 C23 1.406(6) . ?
C22 C27 1.411(6) . ?
C23 C24 1.375(7) . ?
C24 C25 1.391(7) . ?
C25 C26 1.370(6) . ?
C26 C27 1.397(6) . ?
C27 C28 1.454(6) . ?
C28 C29 1.405(6) . ?
C29 C30 1.363(6) . ?
C30 C31 1.433(6) . ?
C30 C37 1.487(6) . ?
C31 C32 1.403(6) . ?
C31 C36 1.422(6) . ?
C32 C33 1.360(7) . ?
C33 C34 1.397(6) . ?
C34 C35 1.352(6) . ?
C35 C36 1.404(6) . ?
C37 C38 1.381(6) . ?
C37 C42 1.396(6) . ?
C38 C39 1.399(6) . ?
C39 C40 1.362(7) . ?
C40 C41 1.375(7) . ?
C41 C42 1.382(6) . ?
C43 C44 1.520(8) . ?
C44 C45 1.389(8) . ?
C45 C46 1.381(8) . ?
C46 C47 1.512(8) . ?
