Copper(i) ionic complexes based on imidazo[4,5-f][1,10]phenanthrolin diimine chelating ligands: crystal structures, and photo- and electroluminescence properties
Rozhkov, Anton V.; Eliseeva, Svetlana N.; Baykov, Sergey V.; Zelenkov, Lev E.; Goriachiy, Dmitry O.; Taydakov, Ilya V.; New Journal of Chemistry 44 (2020) 110–120; doi:10.1039/C9NJ05109K

data_7059141
_publ_section_title
;
 Copper(i) ionic complexes based on imidazo[4,5-f][1,10]phenanthrolin
 diimine chelating ligands: crystal structures, and photo- and
 electroluminescence properties
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              110
_journal_page_last               120
_journal_paper_doi               10.1039/C9NJ05109K
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C55 H39 Br Cu N4 O2 P2, B F4'
_chemical_formula_sum            'C55 H39 B Br Cu F4 N4 O2 P2'
_chemical_formula_weight         1080.10
_chemical_properties_physical    Moisture-sensitive
_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             2019-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-14 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                100.1100(10)
_cell_angle_beta                 103.415(2)
_cell_angle_gamma                111.011(2)
_cell_formula_units_Z            2
_cell_length_a                   13.1619(3)
_cell_length_b                   14.2651(2)
_cell_length_c                   14.9940(3)
_cell_measurement_reflns_used    17061
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      70.2910
_cell_measurement_theta_min      3.1580
_cell_volume                     2450.37(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_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    -51.00 -26.00   0.50    1.50    --  -38.95 123.00  74.00   50
  2  \w    -83.00 -56.00   0.50    1.50    --  -38.95 148.00-121.00   54
  3  \w     18.00  94.00   0.50    1.50    --   38.95-148.00-170.00  152
  4  \w      1.00  48.00   0.50    1.50    --   38.95-123.00  -5.00   94
  5  \w     60.00  85.00   0.50    8.00    --  100.00-148.00-170.00   50
  6  \w     92.00 125.00   0.50    8.00    --  100.00 123.00  74.00   66
  7  \w     86.00 111.00   0.50    8.00    --  100.00 148.00-121.00   50
  8  \w     70.00  96.00   0.50    8.00    --  100.00-123.00  -5.00   52
  9  \w   -100.00 -72.00   0.50    1.50    --  -38.95 -77.00 -60.00   56
 10  \w    -91.00 -18.00   0.50    1.50    --  -38.95 138.00 150.00  146
 11  \w     -6.00  25.00   0.50    1.50    --  -38.95  77.00  60.00   62
 12  \w    -33.00  29.00   0.50    1.50    --  -38.95  32.00-150.00  124
 13  \w   -102.00 -45.00   0.50    1.50    --  -38.95 -54.00 150.00  114
 14  \w    -56.00 -19.00   0.50    1.50    --  -38.95 -77.00 -60.00   74
 15  \w    -64.00 -12.00   0.50    1.50    --  -38.95  77.00  60.00  104
 16  \w    -98.00 -16.00   0.50    1.50    --  -38.95 -65.00-180.00  164
 17  \w    -14.00  12.00   0.50    1.50    --   38.95 -43.00 -30.00   52
 18  \w     41.00  66.00   0.50    1.50    --   38.95  65.00-150.00   50
 19  \w     24.00  54.00   0.50    1.50    --   38.95 -43.00 -30.00   60
 20  \w     24.00  94.00   0.50    1.50    --   38.95  54.00 -90.00  140
 21  \w     73.00 101.00   0.50    1.50    --   38.95  32.00 -30.00   56
 22  \w     31.00  56.00   0.50    1.50    --   38.95 -43.00-180.00   50
 23  \w     26.00 105.00   0.50    1.50    --   38.95  32.00 120.00  158
 24  \w     53.00  82.00   0.50    1.50    --   38.95-138.00  60.00   58
 25  \w     16.00 102.00   0.50    1.50    --   38.95  65.00 120.00  172
 26  \w     72.00 103.00   0.50    1.50    --   38.95  65.00-150.00   62
 27  \w     41.00  67.00   0.50    1.50    --   38.95  32.00 -30.00   52
 28  \w     26.00  83.00   0.50    1.50    --   38.95  32.00  60.00  114
 29  \w     11.00  46.00   0.50    1.50    --   38.95-138.00  60.00   70
 30  \w     51.00  77.00   0.50    1.50    --   38.95-138.00-150.00   52
 31  \w    -23.00   3.00   0.50    1.50    --   38.95 -43.00-180.00   52
 32  \w     70.00 105.00   0.50    8.00    --  100.00  15.00   0.00   70
 33  \w     83.00 108.00   0.50    8.00    --  100.00  45.00 -30.00   50
 34  \w    118.00 151.00   0.50    8.00    --  100.00  93.00-120.00   66
 35  \w     99.00 124.00   0.50    8.00    --  100.00 -77.00 150.00   50
 36  \w     52.00 122.00   0.50    8.00    --  100.00-133.00 120.00  140
 37  \w     54.00 118.00   0.50    8.00    --  100.00 -45.00 -60.00  128
 38  \w    111.00 156.00   0.50    8.00    --  100.00  15.00   0.00   90
 39  \w     31.00 101.00   0.50    8.00    --  100.00-111.00-120.00  140
 40  \w     34.00 106.00   0.50    8.00    --  100.00 -37.00  90.00  144
 41  \w     72.00  97.00   0.50    8.00    --  100.00-111.00-180.00   50
 42  \w     56.00  94.00   0.50    8.00    --  100.00 -93.00 120.00   76
 43  \w    131.00 156.00   0.50    8.00    --  100.00 133.00   0.00   50
 44  \w     81.00 132.00   0.50    8.00    --  100.00  53.00 -90.00  102
 45  \w     43.00  78.00   0.50    8.00    --  100.00 -77.00 150.00   70
 46  \w     34.00  60.00   0.50    8.00    --  100.00 -69.00 -30.00   52
 47  \w     46.00 118.00   0.50    8.00    --  100.00-133.00  90.00  144
 48  \w     32.00 109.00   0.50    8.00    --  100.00-111.00 120.00  154
 49  \w     35.00  61.00   0.50    8.00    --  100.00 -61.00-150.00   52
 50  \w     85.00 110.00   0.50    8.00    --  100.00 -61.00  90.00   50
 51  \w     35.00  77.00   0.50    8.00    --  100.00 -61.00  90.00   84
 52  \w    107.00 141.00   0.50    8.00    --  100.00  53.00  60.00   68
 53  \w     81.00 130.00   0.50    8.00    --  100.00  93.00 -60.00   98
 54  \w     69.00 124.00   0.50    8.00    --  100.00 133.00   0.00  110
 55  \w     36.00 123.00   0.50    8.00    --  100.00-133.00 -30.00  174
 56  \w     34.00 105.00   0.50    8.00    --  100.00-111.00 -30.00  142
 57  \w     34.00  83.00   0.50    8.00    --  100.00 -69.00 -60.00   98
 58  \w     87.00 142.00   0.50    8.00    --  100.00  37.00   0.00  110
 59  \w     83.00 108.00   0.50    8.00    --  100.00 -93.00-150.00   50
 60  \w     74.00 156.00   0.50    8.00    --  100.00  77.00   0.00  164
 61  \w    103.00 141.00   0.50    8.00    --  100.00 111.00   0.00   76
 62  \w    108.00 157.00   0.50    8.00    --  100.00  30.00 -90.00   98
 63  \w     65.00  90.00   0.50    8.00    --  100.00 -45.00 -30.00   50
 64  \w    112.00 156.00   0.50    8.00    --  100.00  45.00 -30.00   88
 65  \w     81.00 148.00   0.50    8.00    --  100.00  22.00 150.00  134
 66  \w     96.00 121.00   0.50    8.00    --  100.00  69.00-180.00   50
 67  \w     59.00  84.00   0.50    8.00    --  100.00 -86.00 -60.00   50
 68  \w     59.00  84.00   0.50    8.00    --  100.00 -30.00 -60.00   50
 69  \w     89.00 122.00   0.50    8.00    --  100.00 -61.00 150.00   66
 70  \w     85.00 123.00   0.50    8.00    --  100.00-133.00-120.00   76
 71  \w     63.00 114.00   0.50    8.00    --  100.00 -30.00-120.00  102
 72  \w     31.00  59.00   0.50    8.00    --  100.00 -30.00-120.00   56
 73  \w     99.00 125.00   0.50    8.00    --  100.00 -86.00 -90.00   52
 74  \w     76.00 126.00   0.50    8.00    --  100.00  77.00  60.00  100
 75  \w     79.00 106.00   0.50    8.00    --  100.00 -69.00 -30.00   54
 76  \w     85.00 110.00   0.50    8.00    --  100.00  93.00 -30.00   50
 77  \w     37.00  62.00   0.50    8.00    --  100.00 -15.00  60.00   50
 78  \w     66.00 127.00   0.50    8.00    --  100.00 -15.00  60.00  122
 79  \w     76.00 146.00   0.50    8.00    --  100.00  69.00  30.00  140
 80  \w     35.00  60.00   0.50    1.50    --   38.95  77.00-180.00   50
 81  \w    -43.00 -18.00   0.50    1.50    --    8.00 126.00  27.48   50
 82  \w    -39.00  -7.00   0.50    1.50    --    8.00 124.00 156.21   64
 83  \w    -10.00  15.00   0.50    1.50    --   28.00 104.00 139.06   50
 84  \w     -7.00  18.00   0.50    1.50    --   28.00  99.00   4.22   50
 85  \w     -9.00  16.00   0.50    1.50    --   28.00 102.00 -93.27   50
 86  \w      5.00  30.00   0.50    1.50    --   36.00  89.00  29.70   50
 87  \w      6.00  31.00   0.50    1.50    --   36.00  87.00 -76.91   50
 88  \w      4.00  29.00   0.50    1.50    --   36.00  90.00 154.41   50
 89  \w      5.00  30.00   0.50    1.50    --   36.00  88.00 -28.57   50
 90  \w      6.00  31.00   0.50    1.50    --   36.00  86.00 139.06   50
 91  \w      6.00  31.00   0.50    1.50    --   36.00  86.00-141.96   50
 92  \w      5.00  30.00   0.50    1.50    --   36.00  89.00  82.77   50
 93  \w     10.00  35.00   0.50    1.50    --   38.95  84.00-161.62   50
 94  \w     11.00  36.00   0.50    1.50    --   40.00  84.00 -97.08   50
 95  \w     17.00  42.00   0.50    1.50    --   44.00  79.00 149.10   50
 96  \w     16.00  41.00   0.50    1.50    --   44.00  81.00   5.17   50
 97  \w     16.00  41.00   0.50    1.50    --   44.00  82.00 178.11   50
 98  \w     16.00  41.00   0.50    1.50    --   44.00  82.00 -33.96   50
 99  \w     16.00  41.00   0.50    1.50    --   44.00  81.00  40.31   50
100  \w     16.00  41.00   0.50    1.50    --   44.00  81.00 111.58   50
101  \w     16.00  41.00   0.50    1.50    --   44.00  80.00 -68.84   50
102  \w     16.00  41.00   0.50    1.50    --   44.00  81.00-144.37   50
103  \w     16.00  41.00   0.50    1.50    --   44.00  80.00  87.14   50
104  \w     27.00  53.00   0.50    1.50    --   52.00  76.00  45.89   52
105  \w     26.00  52.00   0.50    1.50    --   52.00  75.00  -0.50   52
106  \w     29.00  55.00   0.50    1.50    --   52.00  76.00 -35.77   52
107  \w     29.00  55.00   0.50    1.50    --   56.00  77.00 163.27   52
108  \w     29.00  55.00   0.50    1.50    --   56.00  77.00-121.41   52
109  \w     30.00  56.00   0.50    1.50    --   56.00  75.00 120.60   52
110  \w     32.00  59.00   0.50    1.50    --   56.00  69.00  80.43   54
111  \w     34.00  59.00   0.50    1.50    --   60.00  75.00  16.21   50
112  \w     35.00  61.00   0.50    1.50    --   60.00  70.00-164.14   52
113  \w     35.00  61.00   0.50    1.50    --   60.00  74.00-112.39   52
114  \w     79.00 105.00   0.50    1.50    --   64.00  77.00 136.02   52
115  \w     37.00  63.00   0.50    1.50    --   64.00  77.00 136.02   52
116  \w     39.00  65.00   0.50    1.50    --   64.00  71.00  88.57   52
117  \w     39.00  65.00   0.50    1.50    --   64.00  73.00-152.19   52
118  \w     37.00  63.00   0.50    1.50    --   64.00  77.00 -79.61   52
119  \w     43.00  93.00   0.50    1.50    --   68.00  76.00 -97.95  100
120  \w     46.00  72.00   0.50    1.50    --   68.00  75.00  23.73   52
121  \w     88.00 122.00   0.50    1.50    --   68.00  75.00  23.73   68
122  \w     47.00  73.00   0.50    8.00    --   72.00  77.00  90.16   52
123  \w    106.00 132.00   0.50    8.00    --   72.00  72.00-128.97   52
124  \w     46.00  72.00   0.50    8.00    --   72.00  75.00 -64.64   52
125  \w     47.00  73.00   0.50    8.00    --   72.00  72.00-128.97   52
126  \w     47.00  73.00   0.50    8.00    --   72.00  74.00 -27.71   52
127  \w    113.00 139.00   0.50    8.00    --   72.00  76.00 -49.75   52
128  \w     46.00  72.00   0.50    8.00    --   72.00  76.00 -49.75   52
129  \w     46.00  72.00   0.50    8.00    --   72.00  74.00 149.84   52
130  \w     45.00  71.00   0.50    8.00    --   72.00  77.00   5.86   52
131  \w     57.00  83.00   0.50    8.00    --   80.00  65.00-109.85   52
132  \w    108.00 144.00   0.50    8.00    --   80.00  70.00-171.07   72
133  \w     55.00  96.00   0.50    8.00    --   80.00  70.00-171.07   82
134  \w     56.00  82.00   0.50    8.00    --   80.00  68.00  60.07   52
135  \w     57.00  82.00   0.50    8.00    --   80.00  66.00 175.02   50
136  \w     58.00  89.00   0.50    8.00    --   84.00  74.00  56.75   62
137  \w     96.00 108.50   0.50    8.00    --   84.00  72.00  74.43   25
;
_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      0.0922859000
_diffrn_orient_matrix_UB_12      0.0822026000
_diffrn_orient_matrix_UB_13      0.0915022000
_diffrn_orient_matrix_UB_21      -0.0494404000
_diffrn_orient_matrix_UB_22      -0.0699015000
_diffrn_orient_matrix_UB_23      0.0606759000
_diffrn_orient_matrix_UB_31      0.0810262000
_diffrn_orient_matrix_UB_32      -0.0540595000
_diffrn_orient_matrix_UB_33      -0.0094125000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            40971
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.577
_diffrn_reflns_theta_min         3.161
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.721
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.50a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       prism
_exptl_crystal_F_000             1096
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.906
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     632
_refine_ls_number_reflns         9295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0662P)^2^+2.1085P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1255
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8064
_reflns_number_total             9295
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj05109k2.cif
_cod_data_source_block           13072_rav-303
_cod_depositor_comments
;Adding full bibliography for 7059140--7059142.cif.

 Adding full bibliography for 7059140--7059142.cif.
;
_cod_original_cell_volume        2450.37(9)
_cod_database_code               7059141
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C55 H39 B1 Br1 Cu1 F4 N4 O2 P2'
_reflns_odcompleteness_completeness 95.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C15(H15), C1(H1), C39(H39), C2(H2A), C9(H9), C8(H8), C7(H7), C31(H31),
  C42(H42), C18(H18), C17(H17), C40(H40), C51(H51), C41(H41), C29(H29), C3(H3A),
  C30(H30), C49(H49), C45(H45), C47(H47), C28(H28), C21(H21), C46(H46),
 C56(H56), C33(H33), C48(H48), C22(H22), C52(H52), C37(H37), C34(H34), C53(H53),
  C25(H25), C35(H35), C54(H54), C36(H36), C23(H23), C24(H24)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              39940
_shelx_fab_checksum              62199
_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 2.295
_oxdiff_exptl_absorpt_empirical_full_min 0.701