Highly phosphorescent iridium(iii) complexes based on 2-(biphenyl-4-yl)benzo[d]oxazole derivatives: synthesis, structures, properties and DFT calculations
Niu, Zhi-Gang; Zheng, Tao; Su, You-Hui; Wang, Peng-Jiang; Li, Xiao-Yan; Cui, Feng; Liang, Jiao; Li, Gao-Nan; New J. Chem. 39 (2015) 6025–; doi:10.1039/C5NJ00975H

data_7054881
_publ_section_title
;
 Highly phosphorescent iridium(iii) complexes based on
 2-(biphenyl-4-yl)benzo[d]oxazole derivatives: synthesis, structures,
 properties and DFT calculations
;
_journal_issue                   8
_journal_name_full               'New J. Chem.'
_journal_page_first              6025
_journal_paper_doi               10.1039/C5NJ00975H
_journal_volume                  39
_journal_year                    2015
_chemical_formula_moiety         'C45 H35 Ir N2 O4'
_chemical_formula_sum            'C45 H35 Ir N2 O4'
_chemical_formula_weight         859.95
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-05-23 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                65.313(4)
_cell_angle_beta                 87.690(2)
_cell_angle_gamma                77.970(3)
_cell_formula_units_Z            2
_cell_length_a                   11.2055(3)
_cell_length_b                   12.7447(5)
_cell_length_c                   14.5575(5)
_cell_measurement_reflns_used    12902
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.1180
_cell_measurement_theta_min      3.3270
_cell_volume                     1844.91(13)
_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      293(2)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega   -3.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0339  -99.0000    0.0000 79

  2 omega  -35.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0339  -38.0000   90.0000 100

  3 omega   15.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0339   38.0000  -90.0000 90

  4 omega -120.00  -95.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  125.0000 -180.0000 25

  5 omega   53.00   98.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -83.0000  144.1369 45

  6 omega   14.00   40.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -84.0000 -149.2421 26

  7 omega   60.00  131.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  122.5876 71

  8 omega   62.00   93.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 31

  9 omega   74.00  130.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000  -74.8272 56

 10 omega   25.00   77.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  150.0000 52

 11 omega  134.00  159.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -60.0000 25

 12 omega   71.00   96.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  120.0000 25

 13 omega  126.00  168.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  120.0000 42

 14 omega   65.00  119.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000   30.0000 54

 15 omega   22.00   75.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000    0.0000 53

 16 omega   80.00  106.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -71.0000  -24.8238 26

 17 omega   37.00   63.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -180.0000 26

 18 omega   21.00   76.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000 -150.0000 55

 19 omega   48.00   73.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   90.0000 25

 20 omega   38.00   82.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000  -90.0000 44

 21 omega  127.00  152.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000    0.0000 25

 22 omega   67.00  111.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -60.0000 44

 23 omega   17.00   52.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   60.0000 35

 24 omega   20.00   53.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  -30.0000 33

 25 omega   16.00   66.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   60.0000 50

 26 omega   33.00   74.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -30.0000 41

 27 omega   99.00  124.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -30.0000 25

 28 omega   92.00  125.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000 -180.0000 33

 29 omega  138.00  171.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000 -180.0000 33

 30 omega   63.00   89.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000    0.0000 26

 31 omega  111.00  170.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000    0.0000 59

 32 omega   57.00  109.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -84.0000 -149.2421 52

 33 omega  102.00  127.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   60.0000 25

 34 omega   61.00   96.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  150.0000 35

 35 omega   17.00   43.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000  -74.8272 26

 36 omega   97.00  122.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000   90.0000 25

 37 omega   16.00   64.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -150.0000 48

 38 omega   19.00   45.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  120.0000 26

 39 omega   71.00   96.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  120.0000 25

 40 omega   21.00   46.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000    0.0000 -120.0000 25

 41 omega   80.00  106.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000    0.0000 -120.0000 26

 42 omega  127.00  152.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000    0.0000 -120.0000 25

 43 omega   81.00  106.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000 -153.6625 25

 44 omega   73.00  110.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  -60.0000 37

 45 omega   18.00   43.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  120.0000 25

 46 omega   70.00  118.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000    1.4773 48
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0240231000
_diffrn_orient_matrix_UB_12      0.0855179000
_diffrn_orient_matrix_UB_13      0.0434819000
_diffrn_orient_matrix_UB_21      -0.0179735000
_diffrn_orient_matrix_UB_22      0.1012078000
_diffrn_orient_matrix_UB_23      -0.1071350000
_diffrn_orient_matrix_UB_31      -0.1375306000
_diffrn_orient_matrix_UB_32      0.0311098000
_diffrn_orient_matrix_UB_33      0.0153163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_laue_measured_fraction_full 0.994
_diffrn_reflns_laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22203
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.183
_diffrn_reflns_theta_max         67.183
_diffrn_reflns_theta_min         3.346
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.375
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47691
_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_colour            orange
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6581
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0308P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0606
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6005
_reflns_number_total             6581
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5nj00975h2.cif
_cod_data_source_block           syh4
_cod_depositor_comments
'Adding full bibliography for 7054880--7054883.cif.'
_cod_original_cell_volume        1844.90(12)
_cod_database_code               7054881
_chemical_oxdiff_formula         'C1 O1 Ir1 N1'
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C12(H12), C22(H22), C33(H33), C2(H2), C30(H30), C5(H5), C10(H10),
 C32(H32), C35(H35), C25(H25), C3(H3), C42(H42), C4(H4), C9(H9), C18(H18),
 C24(H24), C15(H15), C23(H23), C39(H39), C16(H16), C36(H36), C38(H38)
2.b Idealised Me refined as rotating group:
 C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C40(H40A,H40B,H40C), C20(H20A,H20B,
 H20C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'