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_7249796
_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         'C18 H21 N3 O2'
_chemical_formula_sum            'C18 H21 N3 O2'
_chemical_formula_weight         311.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.97860(10)
_cell_length_b                   7.24420(10)
_cell_length_c                   36.2940(5)
_cell_measurement_reflns_used    18920
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      79.5090
_cell_measurement_theta_min      4.8510
_cell_volume                     1571.90(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_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      99.9(6)
_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 0.993
_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   -114.00 -25.00   0.50    4.00    --  -48.87 -77.00-150.00  178
  2  \w    -26.00  27.00   0.50    4.00    --  -48.87  19.00 -60.00  106
  3  \w   -124.00 -35.00   0.50    4.00    --  -48.87 -38.00 120.00  178
  4  \w    -27.00  26.00   0.50    4.00    --   48.87 -19.00  30.00  106
  5  \w    -23.00 121.00   0.50    4.00    --   48.87   0.00  60.00  288
  6  \w     60.00 122.00   0.50    4.00    --   48.87-178.00   0.00  124
  7  \w     60.00 122.00   0.50    4.00    --   48.87-178.00  60.00  124
  8  \w    -43.00 -13.00   0.50   16.00    --  -88.50  38.00   0.00   60
  9  \w    -43.00 -13.00   0.50   16.00    --  -88.50  38.00 -30.00   60
 10  \w    -66.00 -17.00   0.50   16.00    --  -88.50  57.00 -60.00   98
 11  \w   -164.00 -75.00   0.50   16.00    --  -88.50 -19.00 150.00  178
 12  \w    -43.00 -13.00   0.50   16.00    --  -88.50  38.00-180.00   60
 13  \w    -66.00 -17.00   0.50   16.00    --  -88.50  57.00-120.00   98
 14  \w   -105.00 -22.00   0.50   16.00    --  -88.50  77.00 120.00  166
 15  \w   -164.00 -75.00   0.50   16.00    --  -88.50 -19.00  60.00  178
 16  \w    -43.00 -13.00   0.50   16.00    --  -88.50  38.00 -60.00   60
 17  \w    -43.00 -13.00   0.50   16.00    --  -88.50  38.00  30.00   60
 18  \w    -43.00 -13.00   0.50   16.00    --  -88.50  38.00 -90.00   60
 19  \w     38.00  66.00   0.50   16.00    --  110.00 -57.00 120.00   56
 20  \w     41.00 113.00   0.50   16.00    --  110.00-125.00  90.00  144
 21  \w     41.00 113.00   0.50   16.00    --  110.00-125.00 -60.00  144
 22  \w     45.00 105.00   0.50   16.00    --  110.00 -77.00-150.00  120
 23  \w     38.00  66.00   0.50   16.00    --  110.00 -57.00 -90.00   56
 24  \w     38.00  66.00   0.50   16.00    --  110.00 -57.00 -30.00   56
 25  \w     41.00 106.00   0.50   16.00    --  110.00 -99.00 120.00  130
 26  \w     94.00 178.00   0.50   16.00    --  110.00  57.00-180.00  168
 27  \w     41.00 113.00   0.50   16.00    --  110.00-125.00-150.00  144
 28  \w     41.00 113.00   0.50   16.00    --  110.00-125.00  30.00  144
 29  \w     38.00  66.00   0.50   16.00    --  110.00 -57.00   0.00   56
 30  \w     97.00 178.00   0.50   16.00    --  110.00  19.00 150.00  162
 31  \w     41.00 106.00   0.50   16.00    --  110.00 -99.00 -30.00  130
 32  \w     97.00 178.00   0.50   16.00    --  110.00  19.00  90.00  162
 33  \w     38.00  66.00   0.50   16.00    --  110.00 -57.00 -60.00   56
 34  \w     38.00  66.00   0.50   16.00    --  110.00 -57.00  30.00   56
 35  \w   -114.00 -25.00   0.50    4.00    --  -48.87 -77.00  90.00  178
 36  \w   -114.00 -25.00   0.50    4.00    --  -48.87 -77.00 150.00  178
 37  \w   -114.00 -25.00   0.50    4.00    --  -48.87 -77.00  60.00  178
 38  \w   -114.00 -25.00   0.50    4.00    --  -48.87 -77.00 -30.00  178
 39  \w   -120.00 -33.00   0.50    4.00    --  -48.87 -57.00 -90.00  174
 40  \w   -114.00 -25.00   0.50    4.00    --  -48.87 -77.00-120.00  178
 41  \w     33.00 121.00   0.50    4.00    --   48.87  57.00  60.00  176
 42  \w     33.00 121.00   0.50    4.00    --   48.87  57.00 -30.00  176
 43  \w     97.00 166.00   0.50   16.00    --  110.00  19.00 -90.00  138
;
_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      -0.0572934000
_diffrn_orient_matrix_UB_12      0.0812140000
_diffrn_orient_matrix_UB_13      0.0380756000
_diffrn_orient_matrix_UB_21      -0.0122393000
_diffrn_orient_matrix_UB_22      0.1945718000
_diffrn_orient_matrix_UB_23      -0.0170276000
_diffrn_orient_matrix_UB_31      -0.2508998000
_diffrn_orient_matrix_UB_32      -0.0280171000
_diffrn_orient_matrix_UB_33      -0.0078655000
_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  0.0644
_diffrn_reflns_av_unetI/netI     0.0847
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            29983
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.557
_diffrn_reflns_theta_min         4.874
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
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    1.316
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1179 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3310
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.194
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0598
_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^)+(0.0310P)^2^+0.8071P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.647
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                3120
_reflns_number_total             3310
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra07856j2.cif
_cod_data_source_block           ps_dok64
_cod_database_code               7249796
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H21 N3 O2'
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.851
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C16(H16A,H16B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C11(H11), C10(H10), C4(H4), C6(H6), C8(H8), C7(H7), C3(H3)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              12260
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.005
_oxdiff_exptl_absorpt_empirical_full_min 0.614