#------------------------------------------------------------------------------
#$Date: 2016-03-23 02:57:22 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179221 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/45/4314504.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_4314504
loop_
_publ_author_name
'Daniel Schneidenbach'
'Sven Ammermann'
'Marc Debeaux'
'Andreas Freund'
'Mike Zöllner'
'Constantin Daniliuc'
'Peter G. Jones'
'Wolfgang Kowalsky'
'Hans-Hermann Johannes'
_publ_section_title
;
 Efficient and Long-Time Stable Red Iridium(III) Complexes for Organic
 Light-Emitting Diodes Based on Quinoxaline Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              397
_journal_page_last               406
_journal_paper_doi               10.1021/ic9009898
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C38 H30 Cl2 F2 Ir N5 O3'
_chemical_formula_weight         905.77
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.325(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4887(6)
_cell_length_b                   8.2755(3)
_cell_length_c                   39.004(2)
_cell_measurement_reflns_used    30782
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.1493
_cell_measurement_theta_min      2.4565
_cell_volume                     3375.9(3)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_collection
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1057
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur S'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            73795
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    4.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1784
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.089
_refine_diff_density_min         -2.141
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    'OH free, rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         7750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0292
_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)+(0.0173P)²+4.2224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0509
_reflns_number_gt                6583
_reflns_number_total             7750
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic9009898_si_001_2.cif
_cod_data_source_block           amir
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4314504
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
Ir Ir 0.695067(12) 0.340143(14) 0.111942(3) 0.00862(4) Uani 1 1 d . . .
N1 N 0.8071(3) 0.2032(3) 0.14656(7) 0.0107(6) Uani 1 1 d . . .
N2 N 1.0034(3) 0.0905(3) 0.19303(7) 0.0172(6) Uani 1 1 d . . .
N3 N 0.5896(2) 0.4626(3) 0.07366(6) 0.0089(5) Uani 1 1 d . . .
N4 N 0.4130(3) 0.6229(3) 0.02833(6) 0.0105(6) Uani 1 1 d . . .
N5 N 0.5849(3) 0.4763(3) 0.14695(6) 0.0112(6) Uani 1 1 d . . .
O1 O 0.8242(2) 0.5275(3) 0.13113(5) 0.0129(5) Uani 1 1 d . . .
O2 O 0.8383(2) 0.7572(3) 0.16083(6) 0.0228(6) Uani 1 1 d . . .
F1 F 0.90966(19) 0.2078(2) -0.00648(5) 0.0183(4) Uani 1 1 d . . .
F2 F 0.46133(18) -0.2412(2) 0.10807(5) 0.0145(4) Uani 1 1 d . . .
C1 C 0.9233(3) 0.1691(4) 0.13599(8) 0.0126(6) Uani 1 1 d . . .
C2 C 1.0255(3) 0.1249(4) 0.16131(9) 0.0150(7) Uani 1 1 d . . .
C3 C 0.8800(3) 0.0950(4) 0.20197(8) 0.0142(7) Uani 1 1 d . . .
C4 C 0.8522(4) 0.0403(4) 0.23462(9) 0.0224(8) Uani 1 1 d . . .
H4 H 0.9192 -0.0004 0.2500 0.027 Uiso 1 1 calc R . .
C5 C 0.7306(4) 0.0448(4) 0.24462(9) 0.0229(8) Uani 1 1 d . . .
H5 H 0.7128 0.0075 0.2668 0.027 Uiso 1 1 calc R . .
C6 C 0.6311(4) 0.1055(4) 0.22176(8) 0.0175(8) Uani 1 1 d . . .
H6 H 0.5460 0.1069 0.2285 0.021 Uiso 1 1 calc R . .
C7 C 0.6555(3) 0.1622(4) 0.19002(8) 0.0157(7) Uani 1 1 d . . .
H7 H 0.5879 0.2046 0.1751 0.019 Uiso 1 1 calc R . .
C8 C 0.7805(3) 0.1580(4) 0.17935(8) 0.0137(6) Uani 1 1 d . . .
C9 C 0.9307(3) 0.1829(4) 0.09882(8) 0.0110(6) Uani 1 1 d . . .
C10 C 0.8205(3) 0.2520(3) 0.08121(8) 0.0086(6) Uani 1 1 d . . .
C11 C 0.8163(3) 0.2622(4) 0.04531(8) 0.0110(7) Uani 1 1 d . . .
H11 H 0.7456 0.3114 0.0327 0.013 Uiso 1 1 calc R . .
C12 C 0.9155(3) 0.2002(4) 0.02866(8) 0.0130(7) Uani 1 1 d . . .
C13 C 1.0212(3) 0.1256(4) 0.04524(9) 0.0137(7) Uani 1 1 d . . .
H13 H 1.0870 0.0818 0.0326 0.016 Uiso 1 1 calc R . .
C14 C 1.0282(3) 0.1168(4) 0.08054(9) 0.0139(7) Uani 1 1 d . . .
H14 H 1.0993 0.0657 0.0926 0.017 Uiso 1 1 calc R . .
C15 C 1.1644(3) 0.1298(4) 0.15371(9) 0.0215(8) Uani 1 1 d . . .
H15A H 1.2175 0.1502 0.1750 0.032 Uiso 1 1 calc R . .
H15B H 1.1774 0.2164 0.1372 0.032 Uiso 1 1 calc R . .
H15C H 1.1884 0.0260 0.1440 0.032 Uiso 1 1 calc R . .
C16 C 0.4737(3) 0.3970(4) 0.06464(8) 0.0096(6) Uani 1 1 d . . .
C17 C 0.3812(3) 0.4893(4) 0.04320(8) 0.0105(7) Uani 1 1 d . . .
C18 C 0.5358(3) 0.6774(4) 0.03376(7) 0.0109(6) Uani 1 1 d . . .
C19 C 0.5704(3) 0.8179(4) 0.01649(8) 0.0135(7) Uani 1 1 d . . .
H19 H 0.5106 0.8678 0.0003 0.016 Uiso 1 1 calc R . .
C20 C 0.6897(3) 0.8832(4) 0.02287(8) 0.0156(7) Uani 1 1 d . . .
H20 H 0.7123 0.9794 0.0115 0.019 Uiso 1 1 calc R . .
C21 C 0.7788(3) 0.8072(4) 0.04638(8) 0.0161(7) Uani 1 1 d . . .
H21 H 0.8615 0.8531 0.0507 0.019 Uiso 1 1 calc R . .
C22 C 0.7492(3) 0.6688(4) 0.06322(8) 0.0134(6) Uani 1 1 d . . .
H22 H 0.8113 0.6179 0.0786 0.016 Uiso 1 1 calc R . .
C23 C 0.6252(3) 0.6022(4) 0.05750(8) 0.0101(6) Uani 1 1 d . . .
C24 C 0.4588(3) 0.2319(4) 0.07720(8) 0.0093(6) Uani 1 1 d . . .
C25 C 0.5653(3) 0.1752(4) 0.09845(7) 0.0091(6) Uani 1 1 d . . .
C26 C 0.5636(3) 0.0125(4) 0.10857(8) 0.0112(7) Uani 1 1 d . . .
H26 H 0.6330 -0.0312 0.1227 0.013 Uiso 1 1 calc R . .
C27 C 0.4612(3) -0.0832(4) 0.09806(8) 0.0109(7) Uani 1 1 d . . .
C28 C 0.3574(3) -0.0305(4) 0.07747(8) 0.0122(7) Uani 1 1 d . . .
H28 H 0.2885 -0.1009 0.0707 0.015 Uiso 1 1 calc R . .
C29 C 0.3573(3) 0.1285(4) 0.06704(8) 0.0118(7) Uani 1 1 d . . .
H29 H 0.2871 0.1687 0.0527 0.014 Uiso 1 1 calc R . .
C30 C 0.2420(3) 0.4459(4) 0.03791(9) 0.0147(7) Uani 1 1 d . . .
H30A H 0.1925 0.5421 0.0307 0.022 Uiso 1 1 calc R . .
H30B H 0.2123 0.4047 0.0595 0.022 Uiso 1 1 calc R . .
H30C H 0.2303 0.3626 0.0201 0.022 Uiso 1 1 calc R . .
C31 C 0.6468(3) 0.6056(4) 0.16113(8) 0.0132(7) Uani 1 1 d . . .
C32 C 0.5897(4) 0.7101(4) 0.18318(8) 0.0188(8) Uani 1 1 d . . .
H32 H 0.6358 0.7998 0.1930 0.023 Uiso 1 1 calc R . .
C33 C 0.4650(4) 0.6824(4) 0.19077(9) 0.0224(8) Uani 1 1 d . . .
H33 H 0.4246 0.7511 0.2062 0.027 Uiso 1 1 calc R . .
C34 C 0.3997(4) 0.5517(4) 0.17536(9) 0.0224(8) Uani 1 1 d . . .
H34 H 0.3131 0.5314 0.1796 0.027 Uiso 1 1 calc R . .
C35 C 0.4626(3) 0.4521(4) 0.15387(8) 0.0167(7) Uani 1 1 d . . .
H35 H 0.4178 0.3627 0.1435 0.020 Uiso 1 1 calc R . .
C36 C 0.7806(3) 0.6341(4) 0.15062(8) 0.0138(7) Uani 1 1 d . . .
C99 C 0.0815(4) 0.7036(4) 0.21056(9) 0.0264(9) Uani 1 1 d . . .
H99A H 0.1150 0.7475 0.1894 0.032 Uiso 1 1 calc R . .
H99B H -0.0025 0.7546 0.2133 0.032 Uiso 1 1 calc R . .
Cl2 Cl 0.06124(9) 0.49175(11) 0.20620(2) 0.0290(2) Uani 1 1 d . . .
Cl1 Cl 0.18781(10) 0.75293(14) 0.24631(3) 0.0376(3) Uani 1 1 d . . .
C98 C 1.1037(4) 0.6445(5) 0.10690(10) 0.0345(10) Uani 1 1 d . . .
H98A H 1.1963 0.6403 0.1052 0.052 Uiso 1 1 calc R . .
H98B H 1.0608 0.6657 0.0842 0.052 Uiso 1 1 calc R . .
H98C H 1.0742 0.5408 0.1155 0.052 Uiso 1 1 calc R . .
O99 O 1.0747(3) 0.7680(4) 0.12951(7) 0.0346(7) Uani 1 1 d . . .
H99 H 0.999(6) 0.750(8) 0.1386(16) 0.11(2) Uiso 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'
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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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
C25 Ir C10 93.45(12) . . ?
C25 Ir N3 79.90(11) . . ?
C10 Ir N3 95.01(11) . . ?
C25 Ir N1 98.18(11) . . ?
C10 Ir N1 79.76(11) . . ?
N3 Ir N1 174.35(10) . . ?
C25 Ir O1 173.77(10) . . ?
C10 Ir O1 92.66(10) . . ?
N3 Ir O1 100.78(9) . . ?
N1 Ir O1 81.72(9) . . ?
C25 Ir N5 97.92(11) . . ?
C10 Ir N5 168.50(11) . . ?
N3 Ir N5 85.31(9) . . ?
N1 Ir N5 100.25(10) . . ?
O1 Ir N5 76.01(9) . . ?
C1 N1 C8 118.6(3) . . ?
C1 N1 Ir 113.5(2) . . ?
C8 N1 Ir 127.6(2) . . ?
C2 N2 C3 118.3(3) . . ?
C16 N3 C23 119.0(3) . . ?
C16 N3 Ir 114.5(2) . . ?
C23 N3 Ir 126.5(2) . . ?
C17 N4 C18 118.7(3) . . ?
C35 N5 C31 118.2(3) . . ?
C35 N5 Ir 127.6(2) . . ?
C31 N5 Ir 114.0(2) . . ?
C36 O1 Ir 117.5(2) . . ?
N1 C1 C2 119.0(3) . . ?
N1 C1 C9 113.9(3) . . ?
C2 C1 C9 127.2(3) . . ?
N2 C2 C1 121.7(3) . . ?
N2 C2 C15 115.7(3) . . ?
C1 C2 C15 122.3(3) . . ?
N2 C3 C4 119.3(3) . . ?
N2 C3 C8 121.3(3) . . ?
C4 C3 C8 119.4(3) . . ?
C5 C4 C3 120.9(3) . . ?
C4 C5 C6 119.5(3) . . ?
C7 C6 C5 121.0(3) . . ?
C6 C7 C8 120.2(3) . . ?
N1 C8 C7 121.7(3) . . ?
N1 C8 C3 119.1(3) . . ?
C7 C8 C3 119.0(3) . . ?
C14 C9 C10 120.7(3) . . ?
C14 C9 C1 124.7(3) . . ?
C10 C9 C1 114.2(3) . . ?
C11 C10 C9 118.1(3) . . ?
C11 C10 Ir 127.5(2) . . ?
C9 C10 Ir 114.1(2) . . ?
C12 C11 C10 119.0(3) . . ?
C11 C12 F1 118.7(3) . . ?
C11 C12 C13 123.8(3) . . ?
F1 C12 C13 117.5(3) . . ?
C14 C13 C12 118.1(3) . . ?
C13 C14 C9 120.2(3) . . ?
N3 C16 C17 119.2(3) . . ?
N3 C16 C24 113.8(3) . . ?
C17 C16 C24 127.0(3) . . ?
N4 C17 C16 121.4(3) . . ?
N4 C17 C30 114.8(3) . . ?
C16 C17 C30 123.7(3) . . ?
N4 C18 C19 118.2(3) . . ?
N4 C18 C23 121.9(3) . . ?
C19 C18 C23 119.8(3) . . ?
C20 C19 C18 120.3(3) . . ?
C19 C20 C21 119.7(3) . . ?
C22 C21 C20 121.6(3) . . ?
C21 C22 C23 119.3(3) . . ?
N3 C23 C18 118.7(3) . . ?
N3 C23 C22 122.1(3) . . ?
C18 C23 C22 119.2(3) . . ?
C29 C24 C25 120.8(3) . . ?
C29 C24 C16 125.0(3) . . ?
C25 C24 C16 113.9(3) . . ?
C26 C25 C24 117.1(3) . . ?
C26 C25 Ir 127.8(2) . . ?
C24 C25 Ir 115.1(2) . . ?
C27 C26 C25 119.7(3) . . ?
F2 C27 C26 119.0(3) . . ?
F2 C27 C28 117.1(3) . . ?
C26 C27 C28 124.0(3) . . ?
C27 C28 C29 117.3(3) . . ?
C28 C29 C24 121.1(3) . . ?
N5 C31 C32 122.1(3) . . ?
N5 C31 C36 116.2(3) . . ?
C32 C31 C36 121.7(3) . . ?
C33 C32 C31 119.3(3) . . ?
C32 C33 C34 118.6(3) . . ?
C35 C34 C33 119.0(3) . . ?
N5 C35 C34 122.6(3) . . ?
O2 C36 O1 125.1(3) . . ?
O2 C36 C31 118.9(3) . . ?
O1 C36 C31 116.0(3) . . ?
Cl1 C99 Cl2 111.6(2) . . ?
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 C25 1.971(3) . ?
Ir C10 1.985(3) . ?
Ir N3 2.057(2) . ?
Ir N1 2.062(3) . ?
Ir O1 2.156(2) . ?
Ir N5 2.170(3) . ?
N1 C1 1.345(4) . ?
N1 C8 1.381(4) . ?
N2 C2 1.307(4) . ?
N2 C3 1.366(4) . ?
N3 C16 1.353(4) . ?
N3 C23 1.381(4) . ?
N4 C17 1.304(4) . ?
N4 C18 1.366(4) . ?
N5 C35 1.345(4) . ?
N5 C31 1.348(4) . ?
O1 C36 1.271(4) . ?
O2 C36 1.236(4) . ?
F1 C12 1.369(3) . ?
F2 C27 1.364(3) . ?
C1 C2 1.448(4) . ?
C1 C9 1.462(4) . ?
C2 C15 1.509(5) . ?
C3 C4 1.402(5) . ?
C3 C8 1.414(4) . ?
C4 C5 1.363(5) . ?
C5 C6 1.413(5) . ?
C6 C7 1.366(4) . ?
C7 C8 1.406(5) . ?
C9 C14 1.401(5) . ?
C9 C10 1.419(4) . ?
C10 C11 1.400(4) . ?
C11 C12 1.368(5) . ?
C12 C13 1.386(5) . ?
C13 C14 1.375(5) . ?
C16 C17 1.449(4) . ?
C16 C24 1.464(4) . ?
C17 C30 1.503(4) . ?
C18 C19 1.405(4) . ?
C18 C23 1.412(4) . ?
C19 C20 1.369(5) . ?
C20 C21 1.408(5) . ?
C21 C22 1.367(4) . ?
C22 C23 1.415(4) . ?
C24 C29 1.400(4) . ?
C24 C25 1.419(4) . ?
C25 C26 1.404(4) . ?
C26 C27 1.372(4) . ?
C27 C28 1.374(4) . ?
C28 C29 1.378(4) . ?
C31 C32 1.387(5) . ?
C31 C36 1.510(5) . ?
C32 C33 1.382(5) . ?
C33 C34 1.392(5) . ?
C34 C35 1.379(5) . ?
C99 Cl1 1.766(4) . ?
C99 Cl2 1.773(4) . ?
C98 O99 1.398(5) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O99 H99 O2 0.90(7) 1.96(7) 2.846(4) 168(6) .
