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_7059140
_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 H40 Cu N4 O2 P2, C2 H6 O S, B F4'
_chemical_formula_sum            'C57 H46 B Cu F4 N4 O3 P2 S'
_chemical_formula_weight         1079.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-20 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.9260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.63140(10)
_cell_length_b                   16.24840(10)
_cell_length_c                   17.9278(2)
_cell_measurement_reflns_used    32935
_cell_measurement_temperature    130.0(2)
_cell_measurement_theta_max      73.8570
_cell_measurement_theta_min      3.4620
_cell_volume                     5135.32(7)
_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      130.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_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    -98.00 -21.00   0.50    0.83    --  -38.82 -64.00-166.00  154
  2  \w     31.00  57.00   0.50    0.83    --   38.82 -64.00-166.00   52
  3  \w     23.00 104.00   0.50    0.83    --   38.82  64.00 -29.00  162
  4  \w    129.00 157.00   0.50    3.31    --  107.00  64.00 -29.00   56
  5  \w     43.00 130.00   0.50    3.31    --  107.00 -64.00-166.00  174
  6  \w     84.00 111.00   0.50    3.31    --  107.00  64.00 -29.00   54
  7  \w    -88.00 -62.00   0.50    0.83    --  -38.82 -77.00  60.00   52
  8  \w    -42.00  -2.00   0.50    0.83    --  -38.82 -11.00-150.00   80
  9  \w    -38.00 -12.00   0.50    0.83    --  -38.82 -77.00  60.00   52
 10  \w   -115.00 -47.00   0.50    0.83    --  -38.82 -11.00-150.00  136
 11  \w   -107.00 -44.00   0.50    0.83    --  -38.82 -32.00 120.00  126
 12  \w    -14.00  11.00   0.50    0.83    --  -38.82  64.00 -29.00   50
 13  \w    -60.00 -28.00   0.50    0.83    --  -38.82  64.00 -29.00   64
 14  \w     27.00  59.00   0.50    0.83    --   38.82  43.00 -30.00   64
 15  \w     29.00 105.00   0.50    0.83    --   38.82  43.00 -90.00  152
 16  \w     66.00  92.00   0.50    0.83    --   38.82  43.00 -30.00   52
 17  \w    -25.00  25.00   0.50    0.83    --   38.82 -43.00  60.00  100
 18  \w     30.00  55.00   0.50    0.83    --   38.82  32.00 -90.00   50
 19  \w     29.00  62.00   0.50    0.83    --   38.82  32.00-180.00   66
 20  \w     46.00  74.00   0.50    0.83    --   38.82-104.00  60.00   56
 21  \w     80.00 105.00   0.50    0.83    --   38.82  32.00-150.00   50
 22  \w     58.00  84.00   0.50    0.83    --   38.82  32.00 -90.00   52
 23  \w    -15.00  23.00   0.50    0.83    --   38.82-104.00  60.00   76
 24  \w     75.00 101.00   0.50    0.83    --   38.82  32.00-180.00   52
 25  \w     29.00  54.00   0.50    0.83    --   38.82 -43.00  60.00   50
 26  \w     63.00  89.00   0.50    3.31    --  107.00 -53.00 -60.00   52
 27  \w     38.00  71.00   0.50    3.31    --  107.00 -30.00 150.00   66
 28  \w     90.00 143.00   0.50    3.31    --  107.00 111.00  30.00  106
 29  \w     71.00 124.00   0.50    3.31    --  107.00 -45.00  60.00  106
 30  \w     38.00 110.00   0.50    3.31    --  107.00-111.00  60.00  144
 31  \w     90.00 116.00   0.50    3.31    --  107.00  45.00 -60.00   52
 32  \w     88.00 117.00   0.50    3.31    --  107.00  22.00 -90.00   58
 33  \w    104.00 157.00   0.50    3.31    --  107.00  61.00 -60.00  106
 34  \w     88.00 135.00   0.50    3.31    --  107.00 -86.00  90.00   94
 35  \w     88.00 119.00   0.50    3.31    --  107.00  53.00 -60.00   62
 36  \w     37.00  63.00   0.50    3.31    --  107.00 -86.00  90.00   52
 37  \w     43.00 134.00   0.50    3.31    --  107.00 -77.00  30.00  182
 38  \w    131.00 156.00   0.50    3.31    --  107.00  69.00 -90.00   50
 39  \w     86.00 117.00   0.50    3.31    --  107.00  69.00-180.00   62
 40  \w    107.00 137.00   0.50    3.31    --  107.00 -93.00 120.00   60
 41  \w     83.00 108.00   0.50    3.31    --  107.00  69.00 -90.00   50
 42  \w     93.00 157.00   0.50    3.31    --  107.00  30.00  30.00  128
 43  \w    132.00 157.00   0.50    3.31    --  107.00  69.00-180.00   50
 44  \w     33.00  73.00   0.50    3.31    --  107.00 -93.00 120.00   80
 45  \w    102.00 148.00   0.50    3.31    --  107.00  30.00   0.00   92
 46  \w    118.00 146.00   0.50    3.31    --  107.00  53.00 -90.00   56
 47  \w     76.00 113.00   0.50    3.31    --  107.00 -30.00 150.00   74
 48  \w    121.00 147.00   0.50    3.31    --  107.00  22.00 -90.00   52
 49  \w     96.00 121.00   0.50    3.31    --  107.00  64.00 -29.00   50
 50  \w    -13.00  21.00   0.50    0.83    --  -38.82  54.00 150.00   68
 51  \w    -51.00 -20.00   0.50    0.83    --  -38.82  54.00 150.00   62
 52  \w    -80.00 -21.00   0.50    0.83    --  -38.82 -21.00  30.00  118
 53  \w    -50.00   5.00   0.50    0.83    --  -38.82  32.00 -30.00  110
 54  \w     40.00  93.00   0.50    0.83    --   38.82  32.00  90.00  106
 55  \w     27.00  55.00   0.50    0.83    --   38.82  54.00 120.00   56
 56  \w    -32.00  44.00   0.50    0.83    --   38.82 -21.00-150.00  152
 57  \w     78.00 103.00   0.50    0.83    --   38.82  54.00 120.00   50
 58  \w     27.00  52.00   0.50    0.83    --   38.82  43.00 150.00   50
 59  \w    -14.00  24.00   0.50    0.83    --   38.82 -32.00-180.00   76
 60  \w     50.00  84.00   0.50    0.83    --   38.82  65.00 120.00   68
 61  \w     83.00 108.00   0.50    3.31    --  107.00  69.00  90.00   50
 62  \w     43.00  93.00   0.50    3.31    --  107.00-133.00 -30.00  100
 63  \w     44.00  70.00   0.50    3.31    --  107.00 -37.00-180.00   52
 64  \w    120.00 146.00   0.50    3.31    --  107.00  77.00  60.00   52
 65  \w     80.00 106.00   0.50    3.31    --  107.00  77.00  60.00   52
 66  \w    123.00 156.00   0.50    3.31    --  107.00  61.00  30.00   66
 67  \w     87.00 125.00   0.50    3.31    --  107.00  53.00  60.00   76
 68  \w     81.00 107.00   0.50    3.31    --  107.00  77.00  30.00   52
 69  \w    123.00 149.00   0.50    3.31    --  107.00  30.00-120.00   52
 70  \w    119.00 157.00   0.50    3.31    --  107.00  77.00   0.00   76
 71  \w    126.00 151.00   0.50    3.31    --  107.00  77.00  30.00   50
 72  \w     44.00 109.00   0.50    3.31    --  107.00-111.00-120.00  130
 73  \w     85.00 110.00   0.50    3.31    --  107.00  61.00  90.00   50
 74  \w     85.00 110.00   0.50    3.31    --  107.00  61.00  60.00   50
 75  \w     80.00 105.00   0.50    3.31    --  107.00  77.00   0.00   50
 76  \w     93.00 120.00   0.50    3.31    --  107.00  30.00-120.00   54
 77  \w     83.00 135.00   0.50    3.31    --  107.00  69.00 120.00  104
 78  \w     87.00 113.00   0.50    3.31    --  107.00  53.00 120.00   52
 79  \w     32.00  58.00   0.50    3.31    --  107.00 -15.00 -90.00   52
 80  \w     86.00 115.00   0.50    3.31    --  107.00  61.00  30.00   58
 81  \w    120.00 149.00   0.50    3.31    --  107.00  93.00 -60.00   58
 82  \w     87.00 113.00   0.50    3.31    --  107.00-111.00  90.00   52
 83  \w     80.00 157.00   0.50    3.31    --  107.00  77.00  90.00  154
 84  \w     83.00 108.00   0.50    3.31    --  107.00  69.00  60.00   50
 85  \w     90.00 135.00   0.50    3.31    --  107.00 -15.00 -90.00   90
 86  \w     55.00  81.00   0.50    3.31    --  107.00 -53.00-150.00   52
 87  \w     91.00 126.00   0.50    3.31    --  107.00 -53.00-150.00   70
 88  \w     82.00 108.00   0.50    3.31    --  107.00  70.00  73.43   52
 89  \w     87.00 112.00   0.50    3.31    --  107.00  53.00  30.00   50
 90  \w     58.00  84.00   0.50    3.31    --  107.00-133.00   0.00   52
 91  \w     93.00 121.00   0.50    3.31    --  107.00 -37.00-180.00   56
 92  \w     83.00 109.00   0.50    3.31    --  107.00  69.00  30.00   52
 93  \w     95.00 121.00   0.50    3.31    --  107.00  30.00-150.00   52
 94  \w    132.00 157.00   0.50    3.31    --  107.00  53.00  60.00   50
 95  \w     90.00 116.00   0.50    3.31    --  107.00  45.00  30.00   52
 96  \w     91.00 134.00   0.50    3.31    --  107.00  45.00  60.00   86
 97  \w     89.00 117.00   0.50    3.31    --  107.00  45.00  90.00   56
 98  \w    123.00 156.00   0.50    3.31    --  107.00  45.00  90.00   66
 99  \w     92.00 118.00   0.50    3.31    --  107.00  45.00 120.00   52
100  \w     85.00 132.00   0.50    3.31    --  107.00  61.00 120.00   94
101  \w     87.00 157.00   0.50    3.31    --  107.00  53.00  90.00  140
;
_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      -0.0851660000
_diffrn_orient_matrix_UB_12      0.0096290000
_diffrn_orient_matrix_UB_13      -0.0184654000
_diffrn_orient_matrix_UB_21      -0.0053411000
_diffrn_orient_matrix_UB_22      0.0695104000
_diffrn_orient_matrix_UB_23      0.0581123000
_diffrn_orient_matrix_UB_31      0.0187302000
_diffrn_orient_matrix_UB_32      0.0637574000
_diffrn_orient_matrix_UB_33      -0.0605985000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            65708
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.024
_diffrn_reflns_theta_min         3.488
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
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    1.396
_exptl_crystal_description       prism
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.236
_refine_diff_density_min         -1.227
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     661
_refine_ls_number_reflns         10330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0567
_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^)+(0.0881P)^2^+7.8022P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.1594
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9393
_reflns_number_total             10330
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj05109k2.cif
_cod_data_source_block           8344-12023_rav-279
_cod_depositor_comments
;Adding full bibliography for 7059140--7059142.cif.

 Adding full bibliography for 7059140--7059142.cif.
;
_cod_database_code               7059140
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C55 B Cu F4 N4 O2 P2'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C27(H27), C3(H3A), C39(H39), C33(H33), C51(H51), C9(H9), C7(H7),
 C31(H31), C42(H42), C1(H1), C40(H40), C52(H52), C36(H36), C49(H49), C53(H53),
 C8(H8), C34(H34), C2(H2A), C21(H21), C45(H45), C35(H35), C41(H41), C23(H23),
 C22(H22), C25(H25), C28(H28), C30(H30), C29(H29), C15(H15), C55(H55), C48(H48),
  C46(H46), C54(H54), C24(H24), C16(H16), C47(H47), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,H2SC)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              17187
_shelx_fab_checksum              67145
_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 1.298
_oxdiff_exptl_absorpt_empirical_full_min 0.787