#------------------------------------------------------------------------------
#$Date: 2019-10-18 12:28:40 +0300 (Fri, 18 Oct 2019) $
#$Revision: 219426 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/47/7234728.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_7234728
loop_
_publ_author_name
'Yan Jiao'
'Ming Li'
'Ning Wang'
'Tao Lu'
'Liang Zhou'
'Yan Huang'
'Zhiyun Lu'
'Daibing Luo'
'Xuemei Pu'
_publ_section_title
;
 A facile color-tuning strategy for constructing a library of Ir(iii)
 complexes with fine-tuned phosphorescence from bluish green to red using
 a synergetic substituent effect of -OCH3 and -CN at only the C-ring of
 C/Ν ligand
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              4269
_journal_page_last               4277
_journal_paper_doi               10.1039/C6TC00153J
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C47 H35 Ir N6 O4'
_chemical_formula_sum            'C47 H35 Ir N6 O4'
_chemical_formula_weight         940.01
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_cell_angle_alpha                107.588(4)
_cell_angle_beta                 97.441(3)
_cell_angle_gamma                110.780(4)
_cell_formula_units_Z            2
_cell_length_a                   12.9834(5)
_cell_length_b                   12.9966(6)
_cell_length_c                   17.3152(7)
_cell_measurement_reflns_used    11085
_cell_measurement_temperature    143.00(10)
_cell_measurement_theta_max      29.1100
_cell_measurement_theta_min      3.3050
_cell_volume                     2510.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      143.00(10)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00    3.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -77.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
  2 omega  -80.00  -53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -17.00   21.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -99.0000  -30.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega  -61.00  -35.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611 -178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   -2.00   86.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580   57.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega   10.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580   57.0000  150.0000 58

#__ type_ start__ end____ width___ exp.time_
  7 omega   -6.00   84.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580   38.0000    0.0000 90

#__ type_ start__ end____ width___ exp.time_
  8 omega  -53.00   45.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580  -38.0000 -180.0000 98
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0451702000
_diffrn_orient_matrix_UB_12      0.0547353000
_diffrn_orient_matrix_UB_13      0.0274122000
_diffrn_orient_matrix_UB_21      0.0147041000
_diffrn_orient_matrix_UB_22      -0.0286556000
_diffrn_orient_matrix_UB_23      0.0257719000
_diffrn_orient_matrix_UB_31      0.0376422000
_diffrn_orient_matrix_UB_32      -0.0122282000
_diffrn_orient_matrix_UB_33      -0.0238998000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22497
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.988
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         15.347
_refine_diff_density_min         -3.127
_refine_diff_density_rms         0.358
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         10246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.1010
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.1698P)²+55.1827P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2738
_refine_ls_wR_factor_ref         0.2790
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9045
_reflns_number_total             10246
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2016-4-4269.cif
_cod_data_source_block           131224_s3_lm
_cod_database_code               7234728
_chemical_oxdiff_formula         c12h12n1o5ir1
_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   0.614
_shelx_estimated_absorpt_t_min   0.498
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(N4)
Uanis(O1) = Uanis(O2)
Uanis(C9) = Uanis(C11) = Uanis(C12) = Uanis(C22) = Uanis(C27) = Uanis(C29) =
Uanis(C30) = Uanis(C32) = Uanis(C35) = Uanis(C24)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C13(H13), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C31(H31),
  C34(H34), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C44(H44)
3.b Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C42(H42a,H42b,H42c), C46(H46a,H46b,H46c), C47(H47a,H47b,
 H47c)
;
loop_
_space_group_symop_operation_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_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
C1 C 0.0599(10) 0.5342(11) 0.3952(8) 0.024(2) Uani 1 1 d . . . . .
C2 C -0.0552(10) 0.5046(11) 0.3647(8) 0.025(2) Uani 1 1 d . . . . .
H2 H -0.0995 0.4418 0.3124 0.030 Uiso 1 1 calc R . . . .
C3 C -0.1029(11) 0.5713(11) 0.4143(9) 0.029(3) Uani 1 1 d . . . . .
H3 H -0.1807 0.5561 0.3947 0.035 Uiso 1 1 calc R . . . .
C4 C -0.0381(12) 0.6598(13) 0.4920(9) 0.036(3) Uani 1 1 d . . . . .
H4 H -0.0745 0.7003 0.5257 0.044 Uiso 1 1 calc R . . . .
C5 C 0.0778(12) 0.6917(12) 0.5227(8) 0.029(3) Uani 1 1 d . . . . .
H5 H 0.1224 0.7538 0.5752 0.035 Uiso 1 1 calc R . . . .
C6 C 0.1230(10) 0.6260(10) 0.4707(7) 0.022(2) Uani 1 1 d . . . . .
C7 C 0.2360(10) 0.5496(10) 0.4125(7) 0.018(2) Uani 1 1 d . . . . .
C8 C 0.3287(10) 0.5260(10) 0.3856(7) 0.021(2) Uani 1 1 d . . . . .
C9 C 0.2923(10) 0.4421(10) 0.3032(8) 0.0217(7) Uani 1 1 d . . . . .
C10 C 0.3771(10) 0.4143(11) 0.2703(7) 0.023(2) Uani 1 1 d . . . . .
H10 H 0.3568 0.3574 0.2150 0.028 Uiso 1 1 calc R . . . .
C11 C 0.4909(10) 0.4697(10) 0.3184(8) 0.0217(7) Uani 1 1 d . . . . .
C12 C 0.5236(10) 0.5507(10) 0.4011(8) 0.0217(7) Uani 1 1 d . . . . .
C13 C 0.4422(10) 0.5793(10) 0.4351(8) 0.022(2) Uani 1 1 d . . . . .
H13 H 0.4627 0.6343 0.4912 0.026 Uiso 1 1 calc R . . . .
C14 C 0.3349(10) 0.7318(11) 0.5442(7) 0.022(2) Uani 1 1 d . . . . .
C15 C 0.4039(12) 0.8235(13) 0.5217(10) 0.039(3) Uani 1 1 d . . . . .
H15 H 0.3822 0.8259 0.4679 0.046 Uiso 1 1 calc R . . . .
C16 C 0.5055(15) 0.9112(14) 0.5812(12) 0.050(4) Uani 1 1 d . . . . .
H16 H 0.5573 0.9698 0.5660 0.061 Uiso 1 1 calc R . . . .
C17 C 0.5303(13) 0.9126(15) 0.6609(12) 0.054(5) Uani 1 1 d . . . . .
H17 H 0.5967 0.9751 0.7019 0.064 Uiso 1 1 calc R . . . .
C18 C 0.4578(14) 0.8217(16) 0.6826(10) 0.048(4) Uani 1 1 d . . . . .
H18 H 0.4764 0.8215 0.7374 0.058 Uiso 1 1 calc R . . . .
C19 C 0.3586(11) 0.7320(13) 0.6228(9) 0.036(3) Uani 1 1 d . . . . .
H19 H 0.3081 0.6716 0.6371 0.044 Uiso 1 1 calc R . . . .
C20 C 0.5774(11) 0.4439(11) 0.2810(8) 0.027(3) Uani 1 1 d . . . . .
C21 C 0.6720(11) 0.6829(13) 0.5262(9) 0.033(3) Uani 1 1 d . . . . .
H21A H 0.6549 0.7502 0.5252 0.050 Uiso 1 1 calc GR . . . .
H21B H 0.7544 0.7107 0.5488 0.050 Uiso 1 1 calc GR . . . .
H21C H 0.6311 0.6471 0.5618 0.050 Uiso 1 1 calc GR . . . .
C22 C 0.1422(10) 0.1621(10) 0.1006(8) 0.0217(7) Uani 1 1 d . . . . .
C23 C 0.1494(11) 0.0789(11) 0.1327(8) 0.027(3) Uani 1 1 d . . . . .
H23 H 0.1477 0.0888 0.1891 0.032 Uiso 1 1 calc R . . . .
C24 C 0.1592(10) -0.0195(10) 0.0799(7) 0.0217(7) Uani 1 1 d . . . . .
H24 H 0.1659 -0.0770 0.1011 0.026 Uiso 1 1 calc R . . . .
C25 C 0.1595(13) -0.0358(12) -0.0035(10) 0.036(3) Uani 1 1 d . . . . .
H25 H 0.1607 -0.1070 -0.0389 0.043 Uiso 1 1 calc R . . . .
C26 C 0.1582(13) 0.0481(11) -0.0358(9) 0.030(3) Uani 1 1 d . . . . .
H26 H 0.1632 0.0393 -0.0916 0.036 Uiso 1 1 calc R . . . .
C27 C 0.1492(10) 0.1472(10) 0.0178(8) 0.0217(7) Uani 1 1 d . . . . .
C28 C 0.1364(9) 0.3185(9) 0.0806(7) 0.017(2) Uani 1 1 d . . . . .
C29 C 0.1368(10) 0.4360(10) 0.1055(8) 0.0217(7) Uani 1 1 d . . . . .
C30 C 0.1404(10) 0.4807(10) 0.1912(8) 0.0217(7) Uani 1 1 d . . . . .
C31 C 0.1487(10) 0.5957(10) 0.2234(7) 0.021(2) Uani 1 1 d . . . . .
H31 H 0.1490 0.6290 0.2805 0.025 Uiso 1 1 calc R . . . .
C32 C 0.1568(10) 0.6641(10) 0.1732(8) 0.0217(7) Uani 1 1 d . . . . .
C33 C 0.1471(10) 0.6152(10) 0.0872(8) 0.024(2) Uani 1 1 d . . . . .
C34 C 0.1376(10) 0.4986(11) 0.0529(8) 0.023(2) Uani 1 1 d . . . . .
H34 H 0.1319 0.4631 -0.0051 0.028 Uiso 1 1 calc R . . . .
C35 C 0.1695(10) 0.2805(10) -0.0643(8) 0.0217(7) Uani 1 1 d . . . . .
C36 C 0.2749(14) 0.3666(14) -0.0557(9) 0.040(3) Uani 1 1 d . . . . .
H36 H 0.3345 0.3994 -0.0055 0.047 Uiso 1 1 calc R . . . .
C37 C 0.2921(15) 0.4045(15) -0.1227(10) 0.048(4) Uani 1 1 d . . . . .
H37 H 0.3626 0.4667 -0.1166 0.058 Uiso 1 1 calc R . . . .
C38 C 0.2085(16) 0.3530(15) -0.1964(11) 0.048(4) Uani 1 1 d . . . . .
H38 H 0.2207 0.3803 -0.2410 0.057 Uiso 1 1 calc R . . . .
C39 C 0.1069(15) 0.2617(14) -0.2062(9) 0.041(3) Uani 1 1 d . . . . .
H39 H 0.0502 0.2233 -0.2584 0.050 Uiso 1 1 calc R . . . .
C40 C 0.0868(12) 0.2251(12) -0.1390(8) 0.032(3) Uani 1 1 d . . . . .
H40 H 0.0164 0.1625 -0.1453 0.038 Uiso 1 1 calc R . . . .
C41 C 0.1748(11) 0.7858(11) 0.2115(8) 0.026(3) Uani 1 1 d . . . . .
C42 C 0.1541(13) 0.6403(13) -0.0430(8) 0.034(3) Uani 1 1 d . . . . .
H42A H 0.0903 0.5621 -0.0729 0.051 Uiso 1 1 calc GR . . . .
H42B H 0.2264 0.6330 -0.0450 0.051 Uiso 1 1 calc GR . . . .
H42C H 0.1477 0.6949 -0.0699 0.051 Uiso 1 1 calc GR . . . .
C43 C -0.1264(10) 0.2043(12) 0.2196(7) 0.029(3) Uani 1 1 d . . . . .
C44 C -0.0969(12) 0.1360(11) 0.2592(8) 0.032(3) Uani 1 1 d . . . . .
H44 H -0.1585 0.0707 0.2611 0.039 Uiso 1 1 calc R . . . .
C45 C 0.0123(12) 0.1529(11) 0.2964(7) 0.028(3) Uani 1 1 d . . . . .
C46 C -0.2511(12) 0.1753(15) 0.1884(9) 0.040(3) Uani 1 1 d . . . . .
H46A H -0.2628 0.2485 0.2057 0.060 Uiso 1 1 calc GR . . . .
H46B H -0.2966 0.1210 0.2122 0.060 Uiso 1 1 calc GR . . . .
H46C H -0.2750 0.1374 0.1269 0.060 Uiso 1 1 calc GR . . . .
C47 C 0.0234(14) 0.0626(12) 0.3327(9) 0.037(3) Uani 1 1 d . . . . .
H47A H 0.0957 0.0563 0.3288 0.056 Uiso 1 1 calc GR . . . .
H47B H -0.0404 -0.0150 0.3009 0.056 Uiso 1 1 calc GR . . . .
H47C H 0.0220 0.0886 0.3918 0.056 Uiso 1 1 calc GR . . . .
Ir1 Ir 0.12328(3) 0.36623(4) 0.24978(3) 0.01890(19) Uani 1 1 d . . . . .
N1 N 0.1329(8) 0.4824(9) 0.3596(6) 0.0205(15) Uani 1 1 d . . . . .
N2 N 0.2362(8) 0.6379(8) 0.4812(6) 0.0205(19) Uani 1 1 d . . . . .
N3 N 0.6412(10) 0.4203(13) 0.2489(8) 0.040(3) Uani 1 1 d . . . . .
N4 N 0.1335(8) 0.2670(9) 0.1366(6) 0.0205(15) Uani 1 1 d . . . . .
N5 N 0.1470(9) 0.2488(9) 0.0064(6) 0.025(2) Uani 1 1 d . . . . .
N6 N 0.1890(12) 0.8833(10) 0.2454(8) 0.042(3) Uani 1 1 d . . . . .
O1 O 0.6366(8) 0.5969(8) 0.4431(6) 0.0301(14) Uani 1 1 d . . . . .
O2 O 0.1513(8) 0.6853(8) 0.0428(6) 0.0301(14) Uani 1 1 d . . . . .
O3 O -0.0595(7) 0.2903(8) 0.2050(5) 0.0231(17) Uani 1 1 d . . . . .
O4 O 0.1062(8) 0.2350(7) 0.3039(5) 0.0245(18) Uani 1 1 d . . . . .
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'
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'
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
C2 C1 N1 130.2(11) . .
C6 C1 C2 120.8(11) . .
C6 C1 N1 109.0(10) . .
C1 C2 H2 121.5 . .
C1 C2 C3 116.9(12) . .
C3 C2 H2 121.5 . .
C2 C3 H3 119.6 . .
C4 C3 C2 120.8(12) . .
C4 C3 H3 119.6 . .
C3 C4 H4 118.6 . .
C3 C4 C5 122.8(12) . .
C5 C4 H4 118.6 . .
C4 C5 H5 122.6 . .
C6 C5 C4 114.8(12) . .
C6 C5 H5 122.6 . .
C1 C6 C5 123.8(12) . .
C1 C6 N2 107.0(10) . .
C5 C6 N2 129.2(11) . .
N1 C7 C8 115.9(10) . .
N1 C7 N2 112.8(10) . .
N2 C7 C8 131.0(10) . .
C9 C8 C7 111.8(10) . .
C9 C8 C13 123.3(11) . .
C13 C8 C7 124.9(11) . .
C8 C9 C10 116.3(11) . .
C8 C9 Ir1 115.8(8) . .
C10 C9 Ir1 127.7(9) . .
C9 C10 H10 119.7 . .
C11 C10 C9 120.7(11) . .
C11 C10 H10 119.7 . .
C10 C11 C20 119.3(11) . .
C12 C11 C10 121.5(11) . .
C12 C11 C20 119.2(11) . .
C13 C12 C11 119.1(11) . .
O1 C12 C11 116.5(10) . .
O1 C12 C13 124.4(11) . .
C8 C13 H13 120.4 . .
C12 C13 C8 119.1(11) . .
C12 C13 H13 120.4 . .
C15 C14 N2 117.6(11) . .
C19 C14 C15 122.1(12) . .
C19 C14 N2 120.3(11) . .
C14 C15 H15 121.0 . .
C16 C15 C14 118.0(15) . .
C16 C15 H15 121.0 . .
C15 C16 H16 119.9 . .
C17 C16 C15 120.2(16) . .
C17 C16 H16 119.9 . .
C16 C17 H17 119.8 . .
C16 C17 C18 120.4(14) . .
C18 C17 H17 119.8 . .
C17 C18 H18 120.2 . .
C19 C18 C17 119.5(16) . .
C19 C18 H18 120.2 . .
C14 C19 C18 119.5(15) . .
C14 C19 H19 120.2 . .
C18 C19 H19 120.2 . .
N3 C20 C11 177.1(15) . .
H21A C21 H21B 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
O1 C21 H21A 109.5 . .
O1 C21 H21B 109.5 . .
O1 C21 H21C 109.5 . .
C23 C22 C27 119.7(11) . .
N4 C22 C23 131.5(11) . .
N4 C22 C27 108.7(10) . .
C22 C23 H23 121.1 . .
C22 C23 C24 117.9(12) . .
C24 C23 H23 121.0 . .
C23 C24 H24 119.3 . .
C23 C24 C25 121.4(11) . .
C25 C24 H24 119.3 . .
C24 C25 H25 119.1 . .
C26 C25 C24 121.9(12) . .
C26 C25 H25 119.1 . .
C25 C26 H26 121.9 . .
C25 C26 C27 116.2(12) . .
C27 C26 H26 121.9 . .
C26 C27 C22 122.6(11) . .
C26 C27 N5 131.5(12) . .
N5 C27 C22 105.8(10) . .
N4 C28 C29 119.1(10) . .
N4 C28 N5 110.3(10) . .
N5 C28 C29 130.4(10) . .
C30 C29 C28 111.1(10) . .
C34 C29 C28 124.9(11) . .
C34 C29 C30 124.0(10) . .
C29 C30 Ir1 115.7(8) . .
C31 C30 C29 116.2(10) . .
C31 C30 Ir1 128.0(9) . .
C30 C31 H31 119.4 . .
C30 C31 C32 121.2(11) . .
C32 C31 H31 119.4 . .
C31 C32 C41 118.8(11) . .
C33 C32 C31 121.1(10) . .
C33 C32 C41 120.1(11) . .
C32 C33 C34 118.6(10) . .
O2 C33 C32 117.4(10) . .
O2 C33 C34 123.9(11) . .
C29 C34 C33 118.6(11) . .
C29 C34 H34 120.7 . .
C33 C34 H34 120.7 . .
C36 C35 N5 119.2(11) . .
C40 C35 C36 120.9(12) . .
C40 C35 N5 119.9(11) . .
C35 C36 H36 120.7 . .
C35 C36 C37 118.5(14) . .
C37 C36 H36 120.7 . .
C36 C37 H37 119.6 . .
C38 C37 C36 120.8(15) . .
C38 C37 H37 119.6 . .
C37 C38 H38 120.0 . .
C37 C38 C39 120.0(14) . .
C39 C38 H38 120.0 . .
C38 C39 H39 120.0 . .
C38 C39 C40 120.0(15) . .
C40 C39 H39 120.0 . .
C35 C40 C39 119.5(13) . .
C35 C40 H40 120.3 . .
C39 C40 H40 120.3 . .
N6 C41 C32 177.3(14) . .
H42A C42 H42B 109.5 . .
H42A C42 H42C 109.5 . .
H42B C42 H42C 109.5 . .
O2 C42 H42A 109.5 . .
O2 C42 H42B 109.5 . .
O2 C42 H42C 109.5 . .
C44 C43 C46 118.7(12) . .
O3 C43 C44 127.5(12) . .
O3 C43 C46 113.8(13) . .
C43 C44 H44 116.3 . .
C45 C44 C43 127.3(12) . .
C45 C44 H44 116.3 . .
C44 C45 C47 117.8(12) . .
O4 C45 C44 127.7(12) . .
O4 C45 C47 114.5(13) . .
C43 C46 H46A 109.5 . .
C43 C46 H46B 109.5 . .
C43 C46 H46C 109.5 . .
H46A C46 H46B 109.5 . .
H46A C46 H46C 109.5 . .
H46B C46 H46C 109.5 . .
C45 C47 H47A 109.5 . .
C45 C47 H47B 109.5 . .
C45 C47 H47C 109.5 . .
H47A C47 H47B 109.5 . .
H47A C47 H47C 109.5 . .
H47B C47 H47C 109.5 . .
C9 Ir1 N4 94.9(4) . .
C9 Ir1 O3 174.4(4) . .
C9 Ir1 O4 89.2(4) . .
C30 Ir1 C9 91.0(5) . .
C30 Ir1 N4 80.3(4) . .
C30 Ir1 O3 91.6(4) . .
C30 Ir1 O4 175.6(4) . .
N1 Ir1 C9 79.1(4) . .
N1 Ir1 C30 93.9(4) . .
N1 Ir1 N4 171.6(4) . .
N1 Ir1 O3 95.7(3) . .
N1 Ir1 O4 90.5(4) . .
N4 Ir1 O3 90.5(3) . .
N4 Ir1 O4 95.3(4) . .
O4 Ir1 O3 88.6(3) . .
C1 N1 Ir1 136.9(8) . .
C7 N1 C1 104.7(9) . .
C7 N1 Ir1 117.1(8) . .
C6 N2 C14 126.9(10) . .
C7 N2 C6 106.4(9) . .
C7 N2 C14 126.2(10) . .
C22 N4 Ir1 138.5(8) . .
C28 N4 C22 108.2(9) . .
C28 N4 Ir1 113.2(8) . .
C27 N5 C35 125.2(10) . .
C28 N5 C27 106.9(10) . .
C28 N5 C35 127.3(10) . .
C12 O1 C21 117.2(9) . .
C33 O2 C42 117.6(10) . .
C43 O3 Ir1 124.1(8) . .
C45 O4 Ir1 124.3(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.388(16) .
C1 C6 1.376(17) .
C1 N1 1.443(15) .
C2 H2 0.9500 .
C2 C3 1.393(17) .
C3 H3 0.9500 .
C3 C4 1.387(19) .
C4 H4 0.9500 .
C4 C5 1.392(19) .
C5 H5 0.9500 .
C5 C6 1.382(16) .
C6 N2 1.403(15) .
C7 C8 1.442(16) .
C7 N1 1.328(15) .
C7 N2 1.379(14) .
C8 C9 1.404(17) .
C8 C13 1.406(16) .
C9 C10 1.409(16) .
C9 Ir1 2.007(12) .
C10 H10 0.9500 .
C10 C11 1.399(16) .
C11 C12 1.398(17) .
C11 C20 1.456(17) .
C12 C13 1.382(16) .
C12 O1 1.369(15) .
C13 H13 0.9500 .
C14 C15 1.411(19) .
C14 C19 1.353(19) .
C14 N2 1.430(15) .
C15 H15 0.9500 .
C15 C16 1.40(2) .
C16 H16 0.9500 .
C16 C17 1.37(3) .
C17 H17 0.9500 .
C17 C18 1.41(3) .
C18 H18 0.9500 .
C18 C19 1.40(2) .
C19 H19 0.9500 .
C20 N3 1.133(17) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C21 O1 1.422(17) .
C22 C23 1.380(17) .
C22 C27 1.409(17) .
C22 N4 1.369(15) .
C23 H23 0.9500 .
C23 C24 1.388(16) .
C24 H24 0.9500 .
C24 C25 1.397(19) .
C25 H25 0.9500 .
C25 C26 1.372(18) .
C26 H26 0.9500 .
C26 C27 1.395(17) .
C27 N5 1.401(15) .
C28 C29 1.454(15) .
C28 N4 1.331(15) .
C28 N5 1.386(15) .
C29 C30 1.408(17) .
C29 C34 1.392(16) .
C30 C31 1.387(16) .
C30 Ir1 2.006(12) .
C31 H31 0.9500 .
C31 C32 1.409(16) .
C32 C33 1.399(17) .
C32 C41 1.434(16) .
C33 C34 1.404(16) .
C33 O2 1.350(15) .
C34 H34 0.9500 .
C35 C36 1.381(18) .
C35 C40 1.368(18) .
C35 N5 1.437(15) .
C36 H36 0.9500 .
C36 C37 1.40(2) .
C37 H37 0.9500 .
C37 C38 1.37(3) .
C38 H38 0.9500 .
C38 C39 1.37(2) .
C39 H39 0.9500 .
C39 C40 1.404(19) .
C40 H40 0.9500 .
C41 N6 1.158(17) .
C42 H42A 0.9800 .
C42 H42B 0.9800 .
C42 H42C 0.9800 .
C42 O2 1.435(16) .
C43 C44 1.39(2) .
C43 C46 1.508(18) .
C43 O3 1.267(16) .
C44 H44 0.9500 .
C44 C45 1.39(2) .
C45 C47 1.529(18) .
C45 O4 1.262(16) .
C46 H46A 0.9800 .
C46 H46B 0.9800 .
C46 H46C 0.9800 .
C47 H47A 0.9800 .
C47 H47B 0.9800 .
C47 H47C 0.9800 .
Ir1 N1 1.996(9) .
Ir1 N4 2.046(9) .
Ir1 O3 2.146(8) .
Ir1 O4 2.143(8) .
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
C1 C2 C3 C4 -2(2) . . . .
C1 C6 N2 C7 -2.0(13) . . . .
C1 C6 N2 C14 170.5(11) . . . .
C2 C1 C6 C5 2(2) . . . .
C2 C1 C6 N2 -176.5(11) . . . .
C2 C1 N1 C7 176.3(13) . . . .
C2 C1 N1 Ir1 11(2) . . . .
C2 C3 C4 C5 4(2) . . . .
C3 C4 C5 C6 -2(2) . . . .
C4 C5 C6 C1 -1(2) . . . .
C4 C5 C6 N2 177.4(13) . . . .
C5 C6 N2 C7 179.1(13) . . . .
C5 C6 N2 C14 -8(2) . . . .
C6 C1 C2 C3 -0.5(19) . . . .
C6 C1 N1 C7 -3.7(13) . . . .
C6 C1 N1 Ir1 -169.4(9) . . . .
C7 C8 C9 C10 178.9(10) . . . .
C7 C8 C9 Ir1 -6.0(13) . . . .
C7 C8 C13 C12 -178.6(11) . . . .
C8 C7 N1 C1 -172.2(10) . . . .
C8 C7 N1 Ir1 -3.1(13) . . . .
C8 C7 N2 C6 173.3(11) . . . .
C8 C7 N2 C14 0.7(19) . . . .
C8 C9 C10 C11 -0.6(17) . . . .
C9 C8 C13 C12 1.6(18) . . . .
C9 C10 C11 C12 2.3(18) . . . .
C9 C10 C11 C20 -176.6(11) . . . .
C10 C11 C12 C13 -2.0(18) . . . .
C10 C11 C12 O1 178.1(11) . . . .
C11 C12 C13 C8 0.1(17) . . . .
C11 C12 O1 C21 177.6(11) . . . .
C13 C8 C9 C10 -1.3(18) . . . .
C13 C8 C9 Ir1 173.9(9) . . . .
C13 C12 O1 C21 -2.3(17) . . . .
C14 C15 C16 C17 -6(2) . . . .
C15 C14 C19 C18 -4(2) . . . .
C15 C14 N2 C6 -98.8(15) . . . .
C15 C14 N2 C7 72.3(16) . . . .
C15 C16 C17 C18 4(3) . . . .
C16 C17 C18 C19 -2(3) . . . .
C17 C18 C19 C14 2(2) . . . .
C19 C14 C15 C16 6(2) . . . .
C19 C14 N2 C6 80.1(17) . . . .
C19 C14 N2 C7 -108.8(14) . . . .
C20 C11 C12 C13 176.9(11) . . . .
C20 C11 C12 O1 -3.0(16) . . . .
C22 C23 C24 C25 -1.3(19) . . . .
C22 C27 N5 C28 -1.2(13) . . . .
C22 C27 N5 C35 170.1(11) . . . .
C23 C22 C27 C26 3.0(19) . . . .
C23 C22 C27 N5 -176.1(11) . . . .
C23 C22 N4 C28 176.1(13) . . . .
C23 C22 N4 Ir1 -1(2) . . . .
C23 C24 C25 C26 5(2) . . . .
C24 C25 C26 C27 -4(2) . . . .
C25 C26 C27 C22 0(2) . . . .
C25 C26 C27 N5 179.0(13) . . . .
C26 C27 N5 C28 179.8(13) . . . .
C26 C27 N5 C35 -9(2) . . . .
C27 C22 C23 C24 -2.4(18) . . . .
C27 C22 N4 C28 -0.9(13) . . . .
C27 C22 N4 Ir1 -178.1(9) . . . .
C28 C29 C30 C31 175.8(10) . . . .
C28 C29 C30 Ir1 -7.7(13) . . . .
C28 C29 C34 C33 -175.0(11) . . . .
C29 C28 N4 C22 -175.7(10) . . . .
C29 C28 N4 Ir1 2.4(13) . . . .
C29 C28 N5 C27 175.9(11) . . . .
C29 C28 N5 C35 5(2) . . . .
C29 C30 C31 C32 -2.0(17) . . . .
C30 C29 C34 C33 2.6(18) . . . .
C30 C31 C32 C33 5.4(18) . . . .
C30 C31 C32 C41 -174.9(11) . . . .
C31 C32 C33 C34 -4.8(17) . . . .
C31 C32 C33 O2 177.4(11) . . . .
C32 C33 C34 C29 0.8(17) . . . .
C32 C33 O2 C42 173.2(11) . . . .
C34 C29 C30 C31 -2.1(18) . . . .
C34 C29 C30 Ir1 174.5(9) . . . .
C34 C33 O2 C42 -4.5(17) . . . .
C35 C36 C37 C38 -3(3) . . . .
C36 C35 C40 C39 -4(2) . . . .
C36 C35 N5 C27 -101.6(15) . . . .
C36 C35 N5 C28 68.0(17) . . . .
C36 C37 C38 C39 -1(3) . . . .
C37 C38 C39 C40 3(3) . . . .
C38 C39 C40 C35 -1(2) . . . .
C40 C35 C36 C37 6(2) . . . .
C40 C35 N5 C27 78.2(16) . . . .
C40 C35 N5 C28 -112.2(14) . . . .
C41 C32 C33 C34 175.6(11) . . . .
C41 C32 C33 O2 -2.2(17) . . . .
C43 C44 C45 C47 -177.3(12) . . . .
C43 C44 C45 O4 2(2) . . . .
C44 C43 O3 Ir1 -6.4(17) . . . .
C44 C45 O4 Ir1 -5.8(17) . . . .
C46 C43 C44 C45 -175.9(12) . . . .
C46 C43 O3 Ir1 174.3(8) . . . .
C47 C45 O4 Ir1 173.8(8) . . . .
Ir1 C9 C10 C11 -175.1(9) . . . .
Ir1 C30 C31 C32 -178.0(9) . . . .
N1 C1 C2 C3 179.5(12) . . . .
N1 C1 C6 C5 -177.5(12) . . . .
N1 C1 C6 N2 3.5(13) . . . .
N1 C7 C8 C9 5.8(15) . . . .
N1 C7 C8 C13 -174.0(11) . . . .
N1 C7 N2 C6 -0.3(13) . . . .
N1 C7 N2 C14 -172.9(11) . . . .
N2 C7 C8 C9 -167.6(11) . . . .
N2 C7 C8 C13 13(2) . . . .
N2 C7 N1 C1 2.4(13) . . . .
N2 C7 N1 Ir1 171.5(7) . . . .
N2 C14 C15 C16 -175.2(13) . . . .
N2 C14 C19 C18 177.3(13) . . . .
N4 C22 C23 C24 -179.0(12) . . . .
N4 C22 C27 C26 -179.6(12) . . . .
N4 C22 C27 N5 1.3(13) . . . .
N4 C28 C29 C30 3.4(15) . . . .
N4 C28 C29 C34 -178.8(11) . . . .
N4 C28 N5 C27 0.8(13) . . . .
N4 C28 N5 C35 -170.3(11) . . . .
N5 C28 C29 C30 -171.4(11) . . . .
N5 C28 C29 C34 6(2) . . . .
N5 C28 N4 C22 0.0(13) . . . .
N5 C28 N4 Ir1 178.1(7) . . . .
N5 C35 C36 C37 -174.2(13) . . . .
N5 C35 C40 C39 176.1(12) . . . .
O1 C12 C13 C8 180.0(11) . . . .
O2 C33 C34 C29 178.5(11) . . . .
O3 C43 C44 C45 5(2) . . . .
