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_7247580
_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 H14 N O3, Br, H2 O'
_chemical_formula_sum            'C15 H16 Br N O4'
_chemical_formula_weight         354.20
_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   mixed
_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                 92.616(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.72040(10)
_cell_length_b                   21.1550(5)
_cell_length_c                   15.1364(3)
_cell_measurement_reflns_used    14065
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.7200
_cell_measurement_theta_min      3.5850
_cell_volume                     1509.95(6)
_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 1.000
_diffrn_measured_fraction_theta_max 0.968
_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    -61.00  26.00   0.50    4.55    --  -49.71  19.00   0.00  174
  2  \w     27.00 115.00   0.50    4.55    --   49.71  77.00 -60.00  176
  3  \w     98.00 178.00   0.50   16.07    --  107.75  38.00  30.00  160
  4  \w     85.00 173.00   0.50   16.07    --  107.75  77.00-180.00  176
  5  \w     39.00 110.00   0.50   16.07    --  107.75 -99.00  30.00  142
  6  \w     33.00  71.00   0.50   16.07    --  107.75 -38.00 -60.00   76
  7  \w     33.00  71.00   0.50   16.07    --  107.75 -38.00 -90.00   76
  8  \w     39.00 110.00   0.50   16.07    --  107.75 -99.00 -30.00  142
  9  \w     33.00  71.00   0.50   16.07    --  107.75 -38.00-180.00   76
 10  \w     38.00 117.00   0.50   16.07    --  107.75-125.00 -60.00  158
 11  \w     33.00  71.00   0.50   16.07    --  107.75 -38.00  60.00   76
 12  \w     33.00  71.00   0.50   16.07    --  107.75 -38.00  30.00   76
 13  \w     37.00  96.00   0.50   16.07    --  107.75 -57.00 120.00  118
 14  \w     39.00 110.00   0.50   16.07    --  107.75 -99.00 150.00  142
 15  \w     37.00  96.00   0.50   16.07    --  107.75 -57.00 150.00  118
 16  \w     35.00 121.00   0.50    4.55    --   49.71  57.00 150.00  172
 17  \w     59.00 120.00   0.50    4.55    --   49.71 178.00 150.00  122
 18  \w     27.00 115.00   0.50    4.55    --   49.71  77.00  30.00  176
 19  \w     27.00 115.00   0.50    4.55    --   49.71  77.00-150.00  176
 20  \w     35.00 121.00   0.50    4.55    --   49.71  57.00-150.00  172
 21  \w     27.00 115.00   0.50    4.55    --   49.71  77.00-120.00  176
 22  \w     27.00 115.00   0.50    4.55    --   49.71  77.00  60.00  176
 23  \w    -92.00 -16.00   0.50   16.07    --  -86.25 125.00  60.00  152
 24  \w    -97.00 -11.00   0.50   16.07    --  -86.25  19.00-120.00  172
 25  \w   -124.00 -39.00   0.50    4.55    --  -49.71 -38.00  30.00  170
 26  \w   -120.00 -38.00   0.50    4.55    --  -49.71-178.00  30.00  164
 27  \w   -155.00 -82.00   0.50   16.07    --  -86.25 -99.00 150.00  146
 28  \w   -151.00 -64.00   0.50   16.07    --  -86.25 -77.00  90.00  174
 29  \w   -151.00 -64.00   0.50   16.07    --  -86.25 -77.00  30.00  174
 30  \w   -157.00 -85.50   0.50   16.07    --  -86.25 -57.00-150.00  143
;
_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      -0.1307539000
_diffrn_orient_matrix_UB_12      -0.0666901000
_diffrn_orient_matrix_UB_13      -0.0054233000
_diffrn_orient_matrix_UB_21      -0.1478950000
_diffrn_orient_matrix_UB_22      0.0167720000
_diffrn_orient_matrix_UB_23      -0.0898027000
_diffrn_orient_matrix_UB_31      0.2603704000
_diffrn_orient_matrix_UB_32      -0.0239355000
_diffrn_orient_matrix_UB_33      -0.0478263000
_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  0.0516
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22483
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.882
_diffrn_reflns_theta_min         4.180
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.854
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.466
_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    1.558
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.034
_refine_diff_density_max         1.271
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0443P)^2^+4.7773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2808
_reflns_number_total             3130
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00758h2.cif
_cod_data_source_block           ps010-5
_cod_depositor_comments
'Adding full bibliography for 7247579--7247585.cif.'
_cod_database_code               7247580
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H16 Br1 N1 O4'
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.332
_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, All O(H,H) groups
2.a Riding coordinates:
 O4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C7(H7), C6(H6), C14(H14), C11(H11), C8(H8), C4(H4), C13(H13), C3(H3),
  C10(H10)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              97351
_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 1.993
_oxdiff_exptl_absorpt_empirical_full_min 0.432