Unraveling the structure–property relationships in fluorescent phenylhydrazones: the role of substituents and molecular interactions
Sobczak, Paulina; Sierański, Tomasz; Świątkowski, Marcin; Trzęsowska-Kruszyńska, Agata; Kolińska, Jolanta; RSC Advances 15 (2025) 1514–1526; doi:10.1039/D4RA07856J

data_7249800
_publ_section_title
;
 Unraveling the structure--property relationships in fluorescent
 phenylhydrazones: the role of substituents and molecular interactions
;
_journal_issue                   3
_journal_name_full               'RSC Advances'
_journal_page_first              1514
_journal_page_last               1526
_journal_paper_doi               10.1039/D4RA07856J
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C12 H11 N3 O3 S'
_chemical_formula_sum            'C12 H11 N3 O3 S'
_chemical_formula_weight         277.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-07
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-04-23 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.8050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.92380(10)
_cell_length_b                   23.4635(3)
_cell_length_c                   11.4920(2)
_cell_measurement_reflns_used    16933
_cell_measurement_temperature    105(7)
_cell_measurement_theta_max      79.6300
_cell_measurement_theta_min      3.7510
_cell_volume                     2574.72(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      105(7)
_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 0.957
_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    -72.00  17.00   0.50    1.00    --  -48.87  77.00 -90.00  178
  2  \w    -72.00  17.00   0.50    1.00    --  -48.87  77.00-150.00  178
  3  \w    -72.00  17.00   0.50    1.00    --  -48.87  77.00  90.00  178
  4  \w     25.00 114.00   0.50    1.00    --   48.87  77.00 150.00  178
  5  \w   -112.00 -22.00   0.50    2.00    --  -88.50  77.00  90.00  180
  6  \w   -112.00 -22.00   0.50    2.00    --  -88.50  77.00  60.00  180
  7  \w   -112.00 -22.00   0.50    2.00    --  -88.50  77.00 120.00  180
  8  \w     86.00 176.00   0.50    2.00    --  110.00  77.00  30.00  180
  9  \w     86.00 176.00   0.50    2.00    --  110.00  77.00  60.00  180
 10  \w     86.00 176.00   0.50    2.00    --  110.00  77.00 120.00  180
 11  \w     86.00 176.00   0.50    2.00    --  110.00  77.00   0.00  180
 12  \w     86.00 176.00   0.50    2.00    --  110.00  77.00  90.00  180
 13  \w   -124.00 -89.00   0.50    1.00    --  -48.87 -38.00 -60.00   70
 14  \w     25.00 114.00   0.50    1.00    --   48.87  77.00-150.00  178
 15  \w     33.00 121.00   0.50    1.00    --   48.87  57.00  60.00  176
 16  \w     25.00 114.00   0.50    1.00    --   48.87  77.00 -60.00  178
;
_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      -0.1374841000
_diffrn_orient_matrix_UB_12      -0.0274805000
_diffrn_orient_matrix_UB_13      -0.0742562000
_diffrn_orient_matrix_UB_21      0.0301166000
_diffrn_orient_matrix_UB_22      -0.0527717000
_diffrn_orient_matrix_UB_23      0.0828180000
_diffrn_orient_matrix_UB_31      -0.0787452000
_diffrn_orient_matrix_UB_32      0.0277591000
_diffrn_orient_matrix_UB_33      0.0839181000
_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  0.0231
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26227
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.321
_diffrn_reflns_theta_min         3.768
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.326
_exptl_absorpt_correction_T_max  0.896
_exptl_absorpt_correction_T_min  0.797
_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            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0478P)^2^+0.7416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0890
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4808
_reflns_number_total             5353
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra07856j2.cif
_cod_data_source_block           ps_dok68
_cod_original_cell_volume        2574.71(6)
_cod_database_code               7249800
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H11 N3 O3 S1'
_shelx_estimated_absorpt_t_max   0.854
_shelx_estimated_absorpt_t_min   0.707
_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
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C28(H28), C24(H24), C32(H32), C11(H11), C31(H31), C23(H23),
 C3(H3), C26(H26), C4(H4), C27(H27), C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              70297
_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 1.321
_oxdiff_exptl_absorpt_empirical_full_min 0.759