New Schiff base salts as sources of blue and green light in the solid state: the role of the anion and protonation
Sobczak, Paulina; Sierański, Tomasz; Świątkowski, Marcin; Trzęsowska-Kruszyńska, Agata; CrystEngComm 25 (2023) 6185–6193; doi:10.1039/D3CE00758H

data_7247585
_publ_section_title
;
 New Schiff base salts as sources of blue and green light in the solid
 state: the role of the anion and protonation
;
_journal_issue                   44
_journal_name_full               CrystEngComm
_journal_page_first              6185
_journal_page_last               6193
_journal_paper_doi               10.1039/D3CE00758H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-06
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-07-28 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.4431(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.82566(3)
_cell_length_b                   15.07160(6)
_cell_length_c                   21.19950(9)
_cell_measurement_reflns_used    68442
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.7130
_cell_measurement_theta_min      3.5740
_cell_volume                     1221.227(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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    -25.00  26.00   0.50    0.10    --   49.71 -19.00-180.00  102
  2  \w    -43.00  24.00   0.50    0.10    --  -50.71  38.00 -60.00  134
  3  \w    -26.00  25.00   0.50    0.10    --  -50.71  19.00   0.00  102
  4  \w    -26.00  25.00   0.50    0.10    --  -50.71  19.00 150.00  102
  5  \w    -26.00  25.00   0.50    0.10    --  -50.71  19.00-120.00  102
  6  \w    -26.00  25.00   0.50    0.10    --  -50.71  19.00-150.00  102
  7  \w    -43.00 -11.00   0.50    0.22    --  -86.25  38.00 -60.00   64
  8  \w    -43.00 -11.00   0.50    0.22    --  -86.25  38.00  60.00   64
  9  \w    -43.00 -11.00   0.50    0.22    --  -86.25  38.00  90.00   64
 10  \w   -158.00 -73.00   0.50    0.22    --  -86.25-125.00  30.00  170
 11  \w    -43.00 -11.00   0.50    0.22    --  -86.25  38.00  30.00   64
 12  \w    -43.00 -11.00   0.50    0.22    --  -86.25  38.00 -30.00   64
 13  \w     39.00 107.00   0.50    0.22    --  107.75 -99.00 -60.00  136
 14  \w     39.00 107.00   0.50    0.22    --  107.75 -99.00 120.00  136
 15  \w     38.00 117.00   0.50    0.22    --  107.75-132.00 -55.00  158
 16  \w     37.00  66.00   0.50    0.22    --  107.75 -57.00 -60.00   58
 17  \w     43.00 105.00   0.50    0.22    --  107.75 -77.00 120.00  124
 18  \w     97.00 178.00   0.50    0.22    --  107.75  19.00-150.00  162
 19  \w     37.00  66.00   0.50    0.22    --  107.75 -57.00 -90.00   58
 20  \w     27.00 114.00   0.50    0.10    --   49.71  77.00 150.00  174
 21  \w     27.00 114.00   0.50    0.10    --   49.71  77.00 -60.00  174
 22  \w     60.00 121.00   0.50    0.10    --   49.71-178.00-180.00  122
 23  \w     27.00 114.00   0.50    0.10    --   49.71  77.00  30.00  174
 24  \w   -115.00 -28.00   0.50    0.10    --  -50.71 -77.00 -90.00  174
 25  \w   -157.00 -71.00   0.50    0.22    --  -86.25 -57.00 -30.00  172
 26  \w   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00 -60.00  174
 27  \w   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00 120.00  174
 28  \w   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00  30.00  174
 29  \w   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00-180.00  174
 30  \w   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00-120.00  174
 31  \w     97.00 178.00   0.50    0.22    --  107.75  38.00 -90.00  162
 32  \w     37.00 165.00   0.50    0.22    --  107.75   0.00 120.00  256
 33  \w     37.00  66.00   0.50    0.22    --  107.75 -57.00-180.00   58
 34  \w     39.00 107.00   0.50    0.22    --  107.75 -99.00  30.00  136
 35  \w     27.00 114.00   0.50    0.10    --   49.71  77.00 120.00  174
 36  \w     27.00 114.00   0.50    0.10    --   49.71  77.00-150.00  174
 37  \w     35.00 121.00   0.50    0.10    --   49.71  57.00 -60.00  172
 38  \w   -115.00 -28.00   0.50    0.10    --  -50.71 -77.00  30.00  174
 39  \w   -125.00 -40.00   0.50    0.10    --  -50.71 -38.00 150.00  170
 40  \w   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00  60.00  174
 41  \w   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00-150.00  174
 42  \w   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00   0.00  174
 43  \w    -43.00 -11.00   0.50    0.22    --  -86.25  38.00 120.00   64
 44  \w   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00  90.00  174
 45  \w   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00 150.00  174
 46  \w   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00 -90.00  174
 47  \w     43.00 105.00   0.50    0.22    --  107.75 -77.00   0.00  124
 48  \w     37.00  66.00   0.50    0.22    --  107.75 -57.00  30.00   58
 49  \w     37.00  66.00   0.50    0.22    --  107.75 -57.00 150.00   58
 50  \w     62.00 120.00   0.50    0.10    --   49.71 178.00  60.00  116
 51  \w   -125.00 -40.00   0.50    0.10    --  -50.71 -38.00 -90.00  170
 52  \w   -115.00 -28.00   0.50    0.10    --  -50.71 -77.00 120.00  174
 53  \w   -125.00 -40.00   0.50    0.10    --  -50.71 -38.00  60.00  170
 54  \w   -125.00 -40.00   0.50    0.10    --  -50.71 -38.00-180.00  170
 55  \w   -151.00 -64.00   0.50    0.22    --  -86.25 -77.00 -30.00  174
 56  \w     37.00  66.00   0.50    0.22    --  107.75 -57.00  90.00   58
 57  \w     85.00 172.00   0.50    0.22    --  107.75  77.00  60.00  174
 58  \w     94.00 178.00   0.50    0.22    --  107.75 125.00 -30.00  168
 59  \w     85.00 172.00   0.50    0.22    --  107.75  77.00 -30.00  174
 60  \w     37.00  66.00   0.50    0.22    --  107.75 -57.00 120.00   58
 61  \w     39.00 107.00   0.50    0.22    --  107.75 -99.00  60.00  136
 62  \w     85.00 172.00   0.50    0.22    --  107.75  77.00-150.00  174
 63  \w     85.00 172.00   0.50    0.22    --  107.75  77.00  30.00  174
 64  \w     85.00 172.00   0.50    0.22    --  107.75  77.00 120.00  174
 65  \w     35.00 121.00   0.50    0.10    --   49.71  57.00 120.00  172
 66  \w     35.00 121.00   0.50    0.10    --   49.71  57.00 -30.00  172
 67  \w     35.00 121.00   0.50    0.10    --   49.71  57.00  30.00  172
 68  \w     39.00 124.00   0.50    0.10    --   49.71  38.00 -60.00  170
 69  \w   -125.00 -40.00   0.50    0.10    --  -50.71 -38.00-120.00  170
 70  \w   -157.00 -71.00   0.50    0.22    --  -86.25 -57.00  30.00  172
 71  \w   -161.00 -76.00   0.50    0.22    --  -86.25 -38.00-150.00  170
 72  \w   -157.00 -71.00   0.50    0.22    --  -86.25 -57.00-180.00  172
 73  \w   -157.00 -71.00   0.50    0.22    --  -86.25 -57.00   0.00  172
 74  \w   -158.00 -73.00   0.50    0.22    --  -86.25-125.00-150.00  170
 75  \w   -161.00 -76.00   0.50    0.22    --  -86.25 -38.00 -90.00  170
 76  \w     43.00 105.00   0.50    0.22    --  107.75 -77.00 -60.00  124
 77  \w     93.00 178.00   0.50    0.22    --  107.75  57.00-180.00  170
 78  \w     37.00  66.00   0.50    0.22    --  107.75 -57.00-150.00   58
 79  \w     85.00 172.00   0.50    0.22    --  107.75  77.00  90.00  174
 80  \w     35.00 121.00   0.50    0.10    --   49.71  57.00-180.00  172
 81  \w    -25.00  26.00   0.50    0.10    --   49.71 -19.00 150.00  102
 82  \w   -125.00 -40.00   0.50    0.10    --  -50.71 -38.00  30.00  170
 83  \w   -115.00 -28.00   0.50    0.10    --  -50.71 -77.00 -30.00  174
 84  \w   -125.00 -40.00   0.50    0.10    --  -50.71 -38.00-150.00  170
 85  \w   -157.00 -71.00   0.50    0.22    --  -86.25 -57.00 120.00  172
 86  \w     93.00 178.00   0.50    0.22    --  107.75  57.00  60.00  170
 87  \w     37.00 165.00   0.50    0.22    --  107.75   0.00-180.00  256
 88  \w     93.00 178.00   0.50    0.22    --  107.75  57.00 -60.00  170
 89  \w     85.00 172.00   0.50    0.22    --  107.75  77.00   0.00  174
 90  \w     85.00 172.00   0.50    0.22    --  107.75  77.00 -90.00  174
 91  \w     37.00 165.00   0.50    0.22    --  107.75   0.00-150.00  256
 92  \w     37.00 165.00   0.50    0.22    --  107.75   0.00-120.00  256
 93  \w     37.00 165.00   0.50    0.22    --  107.75   0.00 -90.00  256
 94  \w     85.00 172.00   0.50    0.22    --  107.75  77.00-120.00  174
 95  \w   -122.00 -36.00   0.50    0.10    --  -50.71 -57.00  90.00  172
 96  \w   -126.00 -40.00   0.50    0.10    --  -50.71 -19.00  90.00  172
 97  \w   -126.00 -40.00   0.50    0.10    --  -50.71 -19.00 -90.00  172
 98  \w   -126.00 -40.00   0.50    0.10    --  -50.71 -19.00  30.00  172
 99  \w   -126.00 -40.00   0.50    0.10    --  -50.71 -19.00 -30.00  172
100  \w     37.00 165.00   0.50    0.22    --  107.75   0.00 -30.00  256
101  \w     37.00 165.00   0.50    0.22    --  107.75   0.00 150.00  256
102  \w     37.00 165.00   0.50    0.22    --  107.75   0.00 -60.00  256
103  \w     37.00 165.00   0.50    0.22    --  107.75   0.00  90.00  256
104  \w     37.00 165.00   0.50    0.22    --  107.75   0.00  60.00  256
105  \w     37.00 165.00   0.50    0.22    --  107.75   0.00  30.00  256
106  \w     37.00 165.00   0.50    0.22    --  107.75   0.00-180.00  256
107  \w     37.00 165.00   0.50    0.22    --  107.75   0.00-150.00  256
108  \w     37.00 165.00   0.50    0.22    --  107.75   0.00-120.00  256
109  \w     37.00 165.00   0.50    0.22    --  107.75   0.00   0.00  256
110  \w    -21.00 106.00   0.50    0.10    --   49.71   0.00-180.00  254
111  \w    -21.00 106.00   0.50    0.10    --   49.71   0.00 -60.00  254
112  \w   -115.00 -28.00   0.50    0.10    --  -50.71 -77.00  60.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0287775000
_diffrn_orient_matrix_UB_12      0.0350233000
_diffrn_orient_matrix_UB_13      -0.0682860000
_diffrn_orient_matrix_UB_21      -0.0556721000
_diffrn_orient_matrix_UB_22      0.0947184000
_diffrn_orient_matrix_UB_23      0.0249828000
_diffrn_orient_matrix_UB_31      0.3981935000
_diffrn_orient_matrix_UB_32      0.0157831000
_diffrn_orient_matrix_UB_33      0.0016933000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            85187
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.910
_diffrn_reflns_theta_min         3.599
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.68a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0432P)^2^+0.4861P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0893
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2533
_reflns_number_total             2622
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00758h2.cif
_cod_data_source_block           ps010-no3pl
_cod_depositor_comments
'Adding full bibliography for 7247579--7247585.cif.'
_cod_original_cell_volume        1221.225(11)
_cod_database_code               7247585
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H13 N1 O3'
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.843
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C7(H7), C6(H6), C4(H4), C14(H14), C13(H13), C3(H3), C8(H8)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              98530
_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 1.452
_oxdiff_exptl_absorpt_empirical_full_min 0.703