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_7247584
_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      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
_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                109.0366(8)
_cell_angle_beta                 94.0110(8)
_cell_angle_gamma                90.8565(8)
_cell_formula_units_Z            2
_cell_length_a                   3.89223(4)
_cell_length_b                   10.76523(10)
_cell_length_c                   15.40737(14)
_cell_measurement_reflns_used    24606
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.5470
_cell_measurement_theta_min      4.3220
_cell_volume                     608.291(11)
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_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    -60.00  25.00   0.50    0.31    --  -49.71  38.00   0.00  170
  2  \w    -72.00  15.00   0.50    0.31    --  -49.71  77.00   0.00  174
  3  \w    -71.00 -11.00   0.50    0.44    --  -86.25  38.00-120.00  120
  4  \w    -92.00 -16.00   0.50    0.44    --  -86.25 125.00 -60.00  152
  5  \w    -97.00 -11.00   0.50    0.44    --  -86.25  19.00-180.00  172
  6  \w    -96.00 -15.00   0.50    0.44    --  -86.25  57.00 -60.00  162
  7  \w   -121.00 -35.00   0.50    0.31    --  -49.71 -57.00-150.00  172
  8  \w     59.00 120.00   0.50    0.31    --   49.71 178.00-120.00  122
  9  \w     85.00 173.00   0.50    0.44    --  107.75  77.00 -90.00  176
 10  \w     98.00 178.00   0.50    0.44    --  107.75  38.00  30.00  160
 11  \w     98.00 178.00   0.50    0.44    --  107.75  38.00 -30.00  160
 12  \w     98.00 178.00   0.50    0.44    --  107.75  38.00 -90.00  160
 13  \w     85.00 173.00   0.50    0.44    --  107.75  77.00  60.00  176
 14  \w     91.00 178.00   0.50    0.44    --  107.75 125.00 150.00  174
 15  \w     98.00 178.00   0.50    0.44    --  107.75  38.00 150.00  160
 16  \w     93.00 178.00   0.50    0.44    --  107.75  57.00  90.00  170
 17  \w     85.00 173.00   0.50    0.44    --  107.75  77.00 -60.00  176
 18  \w     93.00 178.00   0.50    0.44    --  107.75  57.00-180.00  170
 19  \w     85.00 173.00   0.50    0.44    --  107.75  77.00-180.00  176
 20  \w     85.00 173.00   0.50    0.44    --  107.75  77.00-150.00  176
 21  \w     85.00 173.00   0.50    0.44    --  107.75  77.00   0.00  176
 22  \w     39.00 110.00   0.50    0.44    --  107.75 -99.00-150.00  142
 23  \w     33.00  71.00   0.50    0.44    --  107.75 -38.00 -30.00   76
 24  \w     37.00  96.00   0.50    0.44    --  107.75 -57.00  30.00  118
 25  \w     39.00 110.00   0.50    0.44    --  107.75 -99.00  60.00  142
 26  \w     38.00 117.00   0.50    0.44    --  107.75-125.00 120.00  158
 27  \w     39.00 110.00   0.50    0.44    --  107.75 -99.00 150.00  142
 28  \w     37.00 165.00   0.50    0.44    --  107.75   0.00  60.00  256
 29  \w     33.00  71.00   0.50    0.44    --  107.75 -38.00 -60.00   76
 30  \w     33.00  71.00   0.50    0.44    --  107.75 -38.00 -90.00   76
 31  \w     39.00 110.00   0.50    0.44    --  107.75 -99.00 -60.00  142
 32  \w     38.00 117.00   0.50    0.44    --  107.75-125.00-150.00  158
 33  \w     37.00  96.00   0.50    0.44    --  107.75 -57.00 -60.00  118
 34  \w     33.00  71.00   0.50    0.44    --  107.75 -38.00-120.00   76
 35  \w     37.00 165.00   0.50    0.44    --  107.75   0.00 -60.00  256
 36  \w     37.00 165.00   0.50    0.44    --  107.75   0.00  30.00  256
 37  \w     37.00 165.00   0.50    0.44    --  107.75   0.00 -30.00  256
 38  \w     37.00 165.00   0.50    0.44    --  107.75   0.00 -90.00  256
 39  \w     37.00 165.00   0.50    0.44    --  107.75   0.00-120.00  256
 40  \w     37.00 165.00   0.50    0.44    --  107.75   0.00-150.00  256
 41  \w     37.00 165.00   0.50    0.44    --  107.75   0.00   0.00  256
 42  \w     37.00 165.00   0.50    0.44    --  107.75   0.00-180.00  256
 43  \w     40.00 124.00   0.50    0.31    --   49.71  38.00 -90.00  168
 44  \w     37.00 165.00   0.50    0.44    --  107.75   0.00  90.00  256
 45  \w     37.00 165.00   0.50    0.44    --  107.75   0.00 120.00  256
 46  \w     27.00 115.00   0.50    0.31    --   49.71  77.00-120.00  176
 47  \w     27.00 115.00   0.50    0.31    --   49.71  77.00  60.00  176
 48  \w     27.00 115.00   0.50    0.31    --   49.71  77.00 150.00  176
 49  \w     27.00 115.00   0.50    0.31    --   49.71  77.00 -30.00  176
 50  \w     27.00 115.00   0.50    0.31    --   49.71  77.00  30.00  176
 51  \w     27.00 115.00   0.50    0.31    --   49.71  77.00 120.00  176
 52  \w   -120.00 -70.00   0.50    0.31    --  -49.71-125.00 -61.00  100
 53  \w   -121.00 -35.00   0.50    0.31    --  -49.71 -57.00 -30.00  172
 54  \w   -124.00 -39.00   0.50    0.31    --  -49.71 -38.00  60.00  170
 55  \w   -121.00 -35.00   0.50    0.31    --  -49.71 -57.00 150.00  172
 56  \w   -124.00 -39.00   0.50    0.31    --  -49.71 -38.00   0.00  170
 57  \w   -121.00 -35.00   0.50    0.31    --  -49.71 -57.00 -90.00  172
 58  \w   -121.00 -35.00   0.50    0.31    --  -49.71 -57.00 -60.00  172
 59  \w   -125.00 -38.00   0.50    0.31    --  -49.71 -19.00-180.00  174
 60  \w   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00-180.00  174
 61  \w   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00   0.00  174
 62  \w   -124.00 -39.00   0.50    0.31    --  -49.71 -38.00 150.00  170
 63  \w   -157.00 -71.00   0.50    0.44    --  -86.25 -57.00  90.00  172
 64  \w   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00  60.00  174
 65  \w   -157.00 -71.00   0.50    0.44    --  -86.25 -57.00 120.00  172
 66  \w   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00  30.00  174
 67  \w   -157.00 -71.00   0.50    0.44    --  -86.25 -57.00  30.00  172
 68  \w   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00 -90.00  174
 69  \w   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00-150.00  174
 70  \w   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00 -30.00  174
 71  \w   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00 -60.00  174
 72  \w   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00 120.00  174
 73  \w   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00 150.00  174
 74  \w   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00  90.00  174
 75  \w   -157.00 -71.00   0.50    0.44    --  -86.25 -57.00 150.00  172
 76  \w   -161.00 -75.00   0.50    0.44    --  -86.25 -19.00 120.00  172
 77  \w   -161.00 -76.00   0.50    0.44    --  -86.25 -38.00 120.00  170
 78  \w   -157.00 -71.00   0.50    0.44    --  -86.25 -57.00 -90.00  172
 79  \w   -151.00 -64.00   0.50    0.44    --  -86.25 -77.00-120.00  174
 80  \w   -157.00 -71.00   0.50    0.44    --  -86.25 -57.00-180.00  172
 81  \w   -161.00 -75.00   0.50    0.44    --  -86.25 -19.00-120.00  172
 82  \w   -161.00 -75.00   0.50    0.44    --  -86.25 -19.00-150.00  172
;
_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      -0.0636443000
_diffrn_orient_matrix_UB_12      0.0070630000
_diffrn_orient_matrix_UB_13      -0.0980682000
_diffrn_orient_matrix_UB_21      -0.1503870000
_diffrn_orient_matrix_UB_22      0.1367979000
_diffrn_orient_matrix_UB_23      0.0396238000
_diffrn_orient_matrix_UB_31      0.3619629000
_diffrn_orient_matrix_UB_32      0.0647345000
_diffrn_orient_matrix_UB_33      0.0084342000
_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  0.0391
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33767
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.744
_diffrn_reflns_theta_min         4.348
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.880
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       prism
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0484P)^2^+0.1845P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2383
_reflns_number_total             2543
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00758h2.cif
_cod_data_source_block           ps010
_cod_depositor_comments
'Adding full bibliography for 7247579--7247585.cif.'
_cod_database_code               7247584
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H13 N1 O3'
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.837
_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:
 C3(H3), C7(H7), C6(H6), C13(H13), C4(H4), C11(H11), C8(H8), C14(H14), C10(H10)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              95589
_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 1.440
_oxdiff_exptl_absorpt_empirical_full_min 0.697