Luminescent organic dyes containing a phenanthro[9,10-D]imidazole core and [Ir(N^C)(N^N)]<sup>+</sup> complexes based on the cyclometalating and diimine ligands of this type.
Solomatina, Anastasia I.; Kuznetsov, Kirill M.; Gurzhiy, Vladislav V.; Pavlovskiy, Vladimir V.; Porsev, Vitaly V.; Evarestov, Robert A.; Tunik, Sergey P.; Dalton transactions (Cambridge, England : 2003) 49 (2020) 6751–6763; doi:10.1039/d0dt00568a

data_7704078
_publ_section_title
;
 Luminescent organic dyes containing a phenanthro[9,10-D]imidazole core
 and [Ir(N^C)(N^N)]<sup>+</sup> complexes based on the cyclometalating and
 diimine ligands of this type.
;
_journal_issue                   20
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6751
_journal_page_last               6763
_journal_paper_doi               10.1039/d0dt00568a
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety
'C80 H51 Ir N7, F6 P, 0.13(C H Cl3), 0.25(C3 H6 O)'
_chemical_formula_sum            'C80.88 H52.62 Cl0.38 F6 Ir N7 O0.25 P'
_chemical_formula_weight         1476.89
_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
_audit_creation_date             2019-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-10 deposited with the CCDC.	2020-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                61.714(2)
_cell_angle_beta                 86.9580(10)
_cell_angle_gamma                82.3120(10)
_cell_formula_units_Z            4
_cell_length_a                   17.5554(2)
_cell_length_b                   20.8344(3)
_cell_length_c                   21.1839(4)
_cell_measurement_reflns_used    27574
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.6490
_cell_measurement_theta_min      2.3580
_cell_volume                     6761.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -45.00 -19.00   0.50    4.00    --  -38.20 137.00-170.00   52
  2  \w     54.00  80.00   0.50    4.00    --   38.20-137.00 126.00   52
  3  \w     18.00  44.00   0.50    4.00    --   38.20-137.00 126.00   52
  4  \w     77.00 122.00   0.50   16.00    --  104.92-137.00 126.00   90
  5  \w     88.00 113.00   0.50   16.00    --  104.92 137.00-170.00   50
  6  \w     98.00 124.00   0.50   16.00    --  104.92-132.00 -56.00   52
  7  \w    125.00 153.00   0.50   16.00    --  104.92 132.00  12.00   56
  8  \w     82.00 112.00   0.50   16.00    --  104.92 132.00  12.00   60
  9  \w   -104.00 -74.00   0.50    4.00    --  -38.20 -77.00  90.00   60
 10  \w    -91.00 -50.00   0.50    4.00    --  -38.20 132.00  12.00   82
 11  \w    -47.00 -15.00   0.50    4.00    --  -38.20 -77.00  90.00   64
 12  \w   -107.00 -54.00   0.50    4.00    --  -38.20 -32.00-180.00  106
 13  \w    -59.00  26.00   0.50    4.00    --  -38.20  65.00-150.00  170
 14  \w    -45.00  -7.00   0.50    4.00    --  -38.20 132.00  12.00   76
 15  \w    -76.00 -10.00   0.50    4.00    --  -38.20 104.00   0.00  132
 16  \w     -7.00  23.00   0.50    4.00    --  -38.20  54.00 -30.00   60
 17  \w   -107.00 -28.00   0.50    4.00    --  -38.20 -32.00-120.00  158
 18  \w    -22.00   4.00   0.50    4.00    --  -38.20  54.00-150.00   52
 19  \w    -76.00  13.00   0.50    4.00    --  -38.20 104.00-180.00  178
 20  \w    -57.00 -23.00   0.50    4.00    --  -38.20  54.00 -30.00   68
 21  \w    -75.00  35.00   0.50    4.00    --  -38.20  11.00 120.00  220
 22  \w    -90.00 -40.00   0.50    4.00    --  -38.20 -43.00 120.00  100
 23  \w     60.00  90.00   0.50    4.00    --   38.20  54.00 120.00   60
 24  \w    -20.00   5.00   0.50    4.00    --   38.20 -54.00 -90.00   50
 25  \w     20.00 108.00   0.50    4.00    --   38.20  21.00-180.00  176
 26  \w     12.00  82.00   0.50    4.00    --   38.20-132.00 -56.00  140
 27  \w    -26.00   6.00   0.50    4.00    --   38.20 -77.00   0.00   64
 28  \w     29.00  65.00   0.50    4.00    --   38.20 -77.00   0.00   72
 29  \w     22.00  57.00   0.50    4.00    --   38.20 -54.00 -90.00   70
 30  \w    -22.00  64.00   0.50    4.00    --   38.20 -77.00-120.00  172
 31  \w     18.00  57.00   0.50    4.00    --   38.20  54.00 120.00   78
 32  \w     21.00  46.00   0.50    4.00    --   38.20  65.00 -30.00   50
 33  \w     -3.00  46.00   0.50    4.00    --   38.20 -32.00 -30.00   98
 34  \w     60.00  87.00   0.50    4.00    --   38.20  65.00 -30.00   54
 35  \w     74.00  99.00   0.50    4.00    --   38.20  32.00 -60.00   50
 36  \w     12.00 102.00   0.50    4.00    --   38.20  77.00   0.00  180
 37  \w      2.00  58.00   0.50    4.00    --   38.20 -54.00  90.00  112
 38  \w     34.00 120.00   0.50   16.00    --  104.92 -22.00 -30.00  172
 39  \w     38.00  96.00   0.50   16.00    --  104.92-111.00 150.00  116
 40  \w     40.00 113.00   0.50   16.00    --  104.92-111.00 120.00  146
 41  \w    101.00 141.00   0.50   16.00    --  104.92  30.00-120.00   80
 42  \w     81.00 130.00   0.50   16.00    --  104.92  69.00  60.00   98
 43  \w     41.00 118.00   0.50   16.00    --  104.92 -45.00 -90.00  154
 44  \w     51.00 128.00   0.50   16.00    --  104.92 -69.00 -90.00  154
 45  \w     98.00 157.00   0.50   16.00    --  104.92  45.00 150.00  118
 46  \w     39.00 130.00   0.50   16.00    --  104.92 -77.00-180.00  182
 47  \w    104.00 131.00   0.50   16.00    --  104.92 111.00   0.00   54
 48  \w     39.00 109.00   0.50   16.00    --  104.92-111.00-180.00  140
 49  \w     79.00 116.00   0.50   16.00    --  104.92 -37.00  60.00   74
 50  \w     92.00 135.00   0.50   16.00    --  104.92  30.00 -90.00   86
 51  \w     49.00  75.00   0.50   16.00    --  104.92-111.00  60.00   52
 52  \w     90.00 140.00   0.50   16.00    --  104.92  22.00 150.00  100
 53  \w    116.00 149.00   0.50   16.00    --  104.92  93.00  60.00   66
 54  \w    113.00 139.00   0.50   16.00    --  104.92  37.00 -30.00   52
 55  \w     41.00 123.00   0.50   16.00    --  104.92 -45.00  90.00  164
 56  \w     95.00 131.00   0.50   16.00    --  104.92 -77.00 120.00   72
 57  \w     67.00 110.00   0.50   16.00    --  104.92-133.00 -90.00   86
 58  \w     95.00 153.00   0.50   16.00    --  104.92  15.00-150.00  116
 59  \w     46.00  72.00   0.50   16.00    --  104.92 -37.00  60.00   52
 60  \w     57.00  90.00   0.50   16.00    --  104.92 -77.00 120.00   66
 61  \w     40.00 108.00   0.50   16.00    --  104.92 -45.00   0.00  136
 62  \w     87.00 155.00   0.50   16.00    --  104.92  22.00 -60.00  136
 63  \w     41.00 122.00   0.50   16.00    --  104.92 -45.00-180.00  162
 64  \w     88.00 113.00   0.50   16.00    --  104.92-111.00   0.00   50
 65  \w     96.00 157.00   0.50   16.00    --  104.92  37.00-150.00  122
 66  \w     66.00 134.00   0.50   16.00    --  104.92 -86.00 -60.00  136
 67  \w     41.00 110.00   0.50   16.00    --  104.92-111.00 -60.00  138
 68  \w     63.00 114.00   0.50   16.00    --  104.92 -77.00  90.00  102
 69  \w     43.00 124.00   0.50   16.00    --  104.92 -22.00-120.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0323629000
_diffrn_orient_matrix_UB_12      -0.0368914000
_diffrn_orient_matrix_UB_13      0.0764023000
_diffrn_orient_matrix_UB_21      -0.0820432000
_diffrn_orient_matrix_UB_22      0.0186493000
_diffrn_orient_matrix_UB_23      -0.0313326000
_diffrn_orient_matrix_UB_31      0.0079842000
_diffrn_orient_matrix_UB_32      -0.0738332000
_diffrn_orient_matrix_UB_33      -0.0014443000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_number            25580
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.998
_diffrn_reflns_theta_min         2.369
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.745
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.206
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       lamina
_exptl_crystal_F_000             2965
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.023
_platon_squeeze_details
;
The unit cell contains disordered acetone
molecules which have been treated
as a diffuse contribution to the overall scattering
without specific atom positions by SQUEEZE/PLATON:
total Potential Solvent Accessible Void Vol is 444 Ang^3
and electron Count Voids / Cell =    98
that is approximately equal to 1 acetone molecule
per formula unit.
;
_refine_diff_density_max         3.292
_refine_diff_density_min         -2.832
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1712
_refine_ls_number_reflns         25580
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1123P)^2^+11.3540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.1687
_reflns_Friedel_coverage         0.000
_reflns_number_gt                21537
_reflns_number_total             25580
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt00568a2.cif
_cod_data_source_block           Compound_4_sai-ir6_sq
_cod_depositor_comments
'Adding full bibliography for 7704075--7704080.cif.'
_cod_database_code               7704078
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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. Restrained distances
 F2B-F5A = F1A-F6B
 2.1 with sigma of 0.02
 Cl1-C81 = Cl3-C81 = Cl2-C81
 1.75 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C8B) = Uanis(C9B) = Uanis(C10B) = Uanis(C11B) = Uanis(C12) = Uanis(C12B)
= Uanis(C13) = Uanis(C13B) = Uanis(C8) = Uanis(C9) = Uanis(C10) = Uanis(C11)
Uanis(F5A) = Uanis(P1A) = Uanis(F1A) = Uanis(F2A) = Uanis(F3A) = Uanis(F4A) =
Uanis(F6A) = Uanis(P1B) = Uanis(F2B) = Uanis(F3B) = Uanis(F4B) = Uanis(F6B)
Uanis(Cl2) = Uanis(C81) = Uanis(Cl3) = Uanis(Cl1)
4. Others
 Sof(C8B)=Sof(C13B)=Sof(H13B)=Sof(C12B)=Sof(H12B)=Sof(C11B)=Sof(H11B)=
 Sof(C10B)=Sof(H10B)=Sof(C9B)=Sof(H9B)=1-FVAR(1)
 Sof(C8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=
 Sof(C13)=Sof(H13)=FVAR(1)
 Sof(P1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=Sof(F6B)=1-FVAR(2)
 Sof(P1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F6A)=FVAR(2)
 Fixed Sof: Cl1(0.25) Cl2(0.25) Cl3(0.25) C81(0.25) H81(0.25) O1(0.5) C82(0.5)
 C83(0.5) H83A(0.5) H83B(0.5) H83C(0.5) C84(0.5) H84A(0.5) H84B(0.5) H84C(0.5)
5.a Ternary CH refined with riding coordinates:
 C81(H81)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C13B(H13B), C12B(H12B), C11B(H11B), C10B(H10B), C9B(H9B), C16(H16),
 C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), C29(H29),
  C30(H30), C31(H31), C32(H32), C36(H36), C37(H37), C38(H38), C39(H39),
 C40(H40), C43(H43), C44(H44), C45(H45), C46(H46), C49(H49), C50(H50), C51(H51),
  C52(H52), C55(H55), C56(H56), C57(H57), C58(H58), C62(H62), C63(H63),
 C64(H64), C65(H65), C66(H66), C69(H69), C70(H70), C71(H71), C72(H72), C75(H75),
  C76(H76), C77(H77), C78(H78), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A),
 C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A), C16A(H16A),
 C17A(H17A), C18A(H18A), C19A(H19A), C22A(H22A), C23A(H23A), C24A(H24A),
 C25A(H25A), C29A(H29A), C30A(H30A), C31A(H31A), C32A(H32A), C36A(H36A),
 C37A(H37A), C38A(H38A), C39A(H39A), C40A(H40A), C43A(H43A), C44A(H44A),
 C45A(H45A), C46A(H46A), C49A(H49A), C50A(H50A), C51A(H51A), C52A(H52A),
 C55A(H55A), C56A(H56A), C57A(H57A), C58A(H58A), C62A(H62A), C63A(H63A),
 C64A(H64A), C65A(H65A), C66A(H66A), C69A(H69A), C70A(H70A), C71A(H71A),
 C72A(H72A), C75A(H75A), C76A(H76A), C77A(H77A), C78A(H78A)
5.c Fitted hexagon refined as free rotating group:
 C8(C9,C10,C11,C12,C13), C8B(C13B,C12B,C11B,C10B,C9B)
5.d Idealised Me refined as rotating group:
 C83(H83A,H83B,H83C), C84(H84A,H84B,H84C)
;
_shelx_res_checksum              67028
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.843
_oxdiff_exptl_absorpt_empirical_full_min 0.661