Dual emission of ESIPT-capable 2-(2-hydroxyphenyl)-4-(1H-pyrazol-1-yl)pyrimidines: interplay of fluorescence and phosphorescence
Shekhovtsov, Nikita A.; Nikolaenkova, Elena B.; Ryadun, Alexey A.; Vorobyeva, Sofia N.; Krivopalov, Viktor P.; Bushuev, Mark B.; New Journal of Chemistry 47 (2023) 6361–6377; doi:10.1039/D3NJ00570D

data_7062354
_publ_section_title
;
 Dual emission of ESIPT-capable
 2-(2-hydroxyphenyl)-4-(1H-pyrazol-1-yl)pyrimidines: interplay of
 fluorescence and phosphorescence
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6361
_journal_page_last               6377
_journal_paper_doi               10.1039/D3NJ00570D
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C26 H20 N4 O'
_chemical_formula_sum            'C26 H20 N4 O'
_chemical_formula_weight         404.46
_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     iterative
_audit_creation_date             2023-01-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-01-27 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                94.126(3)
_cell_angle_beta                 113.697(3)
_cell_angle_gamma                109.740(3)
_cell_formula_units_Z            2
_cell_length_a                   10.0306(9)
_cell_length_b                   10.1285(9)
_cell_length_c                   12.2622(10)
_cell_measurement_reflns_used    4864
_cell_measurement_temperature    250.0
_cell_measurement_theta_max      25.45
_cell_measurement_theta_min      2.20
_cell_volume                     1042.06(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      250.0
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20705
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.404
_diffrn_reflns_theta_min         1.869
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0561 before and 0.0471 after correction.
The Ratio of minimum to maximum transmission is 0.9333.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0704P)^2^+0.0829P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1327
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2924
_reflns_number_total             4276
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj00570d2.cif
_cod_data_source_block           bch_l60
_cod_depositor_comments
'Adding full bibliography for 7062353--7062354.cif.'
_cod_database_code               7062354
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.994
_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), C14(H14), C19(H19), C6(H6), C22(H22), C18(H18), C15(H15), C16(H16),
 C17(H17), C5(H5), C3(H3), C23(H23), C4(H4), C26(H26), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              36426
_shelx_hkl_checksum              25305
_olex2_submission_special_instructions 'No special instructions were received'