Proton-induced fluorescence in modified quino[7,8-h]quinolines: dual sensing for protons and π-donors.
Pozharskii, Alexander F.; Ozeryanskii, Valery A.; Mikshiev, Vladimir Y.; Chernyshev, Anatoly V.; Metelitsa, Anatoly V.; Antonov, Alexander S.; Organic & biomolecular chemistry 17 (2019) 8221–8233; doi:10.1039/c9ob01391a

data_7157044
_publ_section_title
;
 Proton-induced fluorescence in modified quino[7,8-h]quinolines: dual
 sensing for protons and \p-donors.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8221
_journal_page_last               8233
_journal_paper_doi               10.1039/c9ob01391a
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'Cl O4, C38 H25 N4'
_chemical_formula_sum            'C38 H25 Cl N4 O4'
_chemical_formula_weight         637.07
_chemical_melting_point          'Decomp. above 250 deg.C'
_chemical_name_systematic
'2,4,9,11-Tetraphenylquinazolino[7,8-h]quinazolinium perchlorate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-01-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-31 deposited with the CCDC.    2019-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.50014(11)
_cell_length_b                   16.7058(2)
_cell_length_c                   22.9329(3)
_cell_measurement_reflns_used    19081
_cell_measurement_temperature    100.03(10)
_cell_measurement_theta_max      75.9770
_cell_measurement_theta_min      3.8360
_cell_volume                     2873.40(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega -115.00  -15.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000 -120.0000 100

  2 omega  -44.00  -19.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -150.0000 25

  3 omega   -8.00   19.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -120.0000 27

  4 omega   91.00  125.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000 -180.0000 34

  5 omega   89.00  120.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 31

  6 omega   35.00   61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 26

  7 omega   77.00  103.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 26

  8 omega   75.00  115.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 40

  9 omega   41.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 30

 10 omega   81.00  143.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -90.0000 62

 11 omega   69.00  107.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 38

 12 omega   31.00   66.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 35

 13 omega  111.00  176.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   60.0000 65

 14 omega   80.00  143.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  -30.0000 63

 15 omega -115.00  -90.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -131.0000  175.0000 25

 16 omega -103.00  -77.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -133.0000  -93.0000 26

 17 omega   58.00  122.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  150.0000 64

 18 omega   48.00   75.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 27

 19 omega   49.00   80.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 31

 20 omega   48.00   74.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 26

 21 omega   61.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 27

 22 omega   52.00   78.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 26

 23 omega   89.00  115.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 26

 24 omega   91.00  146.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 55

 25 omega   80.00  105.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -60.0000 25

 26 omega   47.00   90.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 43

 27 omega  105.00  131.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -180.0000 26

 28 omega   62.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 27

 29 omega   81.00  128.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   30.0000 47

 30 omega -113.00  -13.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   90.0000 100

 31 omega  -44.00  -11.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000 -180.0000 33

 32 omega -113.00  -11.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000    0.0000 102

 33 omega -129.00  -40.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  178.0000   30.0000 89

 34 omega  -94.00  -50.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000 -180.0000 44

 35 omega   57.00  130.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000   60.0000 73

 36 omega    4.00   29.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   86.0000   52.8512 25

 37 omega    1.00   26.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   93.0000  -85.4236 25

 38 omega    7.00   32.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   88.0000 -178.6407 25

 39 omega   22.00   47.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000 -125.6501 25

 40 omega   26.00   52.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   77.0000  -82.3753 26

 41 omega   26.00   52.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   77.0000  -30.0270 26

 42 omega  101.00  127.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000 -169.1533 26

 43 omega  106.00  143.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000  -12.0284 37

 44 omega   31.00   57.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000 -169.1533 26

 45 omega   30.00   56.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000  101.9631 26

 46 omega   31.00   57.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000  143.3234 26

 47 omega   97.00  123.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000   71.1952 26

 48 omega   31.00   57.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000   71.1952 26

 49 omega   31.00   57.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000  -12.0284 26

 50 omega   30.00   57.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000   26.9756 27

 51 omega   41.00   66.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   70.0000 -136.2288 25

 52 omega   41.00   77.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   62.0000    7.4926 36

 53 omega   82.00  122.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   74.0000  132.9034 40

 54 omega   44.00   79.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   74.0000  132.9034 35

 55 omega   42.00   67.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   77.0000 -116.1905 25

 56 omega   43.00   69.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   72.0000  104.7457 26

 57 omega   47.00   73.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   74.0000  -85.9555 26

 58 omega   50.00   81.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   66.0000  -53.8640 31

 59 omega   51.00   77.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   75.0000  177.6134 26

 60 omega   53.00   80.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   65.0000   75.2261 27

 61 omega   55.00   84.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   72.0000 -159.9117 29

 62 omega   66.00   92.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   61.0000 -121.8366 26

 63 omega   63.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   76.0000   49.4733 26

 64 omega  138.00  165.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   77.0000    8.9710 27

 65 omega   62.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   77.0000    8.9710 26

 66 omega   66.00   93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   60.0000  -28.0969 27

 67 omega   66.00  119.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   60.0000   52.3654 53

 68 omega   72.00  112.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0000   70.0000  153.6152 40

 69 omega   76.00  101.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   74.0000  172.7644 25

 70 omega   85.00  114.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 29

 71 omega   79.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 30

 72 omega   82.00  141.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   64.0000  -31.5459 59

 73 omega  147.00  173.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 26

 74 omega   79.00  114.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 35

 75 omega   79.00  105.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 26

 76 omega   79.00  130.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 51

 77 omega  122.00  136.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 14
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0032612000
_diffrn_orient_matrix_UB_12      -0.0798895000
_diffrn_orient_matrix_UB_13      0.0335283000
_diffrn_orient_matrix_UB_21      -0.0047265000
_diffrn_orient_matrix_UB_22      -0.0460385000
_diffrn_orient_matrix_UB_23      -0.0582096000
_diffrn_orient_matrix_UB_31      0.2052724000
_diffrn_orient_matrix_UB_32      -0.0023658000
_diffrn_orient_matrix_UB_33      -0.0008156000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            39372
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.218
_diffrn_reflns_theta_min         3.273
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       prism
_exptl_crystal_F_000             1320
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.404(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         5985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0666P)^2^+0.3027P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5619
_reflns_number_total             5985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01391a2.cif
_cod_data_source_block           yufu_spbu-1
_cod_depositor_comments
'Adding full bibliography for 7157043--7157048.cif.'
_cod_database_code               7157044
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C38 H25 Cl O4 N4'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.596(16)
 0.404(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3. Others
 Sof(O1)=Sof(O1AA)=Sof(O2AA)=Sof(O0AA)=1-FVAR(1)
 Sof(O2)=Sof(O3)=Sof(O4)=Sof(O20)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), N10(H10), C13(H13), C14(H14), C16(H16), C19(H19),
 C1H(H1H), C1I(H1I), C1J(H1J), C1K(H1K), C1M(H1M), C1O(H1O), C1P(H1P), C1Q(H1Q),
  C1R(H1R), C1U(H1U), C1V(H1V), C1W(H1W), C1A(H1A), C1S(H1S), C1X(H1X),
 C1Y(H1Y), C1Z(H1Z)
;
_shelx_res_checksum              71536
_olex2_date_sample_data_collection 1492071513.02
_olex2_submission_special_instructions 'No special instructions were received'