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_7249801
_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         'C16 H19 N3 O'
_chemical_formula_sum            'C16 H19 N3 O'
_chemical_formula_weight         269.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-19
_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                 97.8960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.95080(10)
_cell_length_b                   7.29470(10)
_cell_length_c                   16.1641(2)
_cell_measurement_reflns_used    16751
_cell_measurement_temperature    100.01(13)
_cell_measurement_theta_max      79.1190
_cell_measurement_theta_min      2.7560
_cell_volume                     1395.79(3)
_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      100.01(13)
_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 0.977
_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   -121.00 -75.00   0.50    4.00    --  -49.12   0.00-180.00   92
  2  \w   -121.00 -75.00   0.50    4.00    --  -49.12   0.00 120.00   92
  3  \w    -41.00  26.00   0.50    4.00    --  -49.12  38.00  90.00  134
  4  \w    -19.00  27.00   0.50    4.00    --  -49.12  19.00 -30.00   92
  5  \w   -121.00 -75.00   0.50    4.00    --  -49.12   0.00-120.00   92
  6  \w   -121.00 -75.00   0.50    4.00    --  -49.12   0.00 150.00   92
  7  \w     62.00 120.00   0.50    4.00    --   49.12 178.00-150.00  116
  8  \w    -27.00  19.00   0.50    4.00    --   49.12 -19.00-120.00   92
  9  \w     60.00 122.00   0.50    4.00    --   49.12-178.00  30.00  124
 10  \w    -41.00 -13.00   0.50   20.00    --  -88.50  38.00 120.00   56
 11  \w   -112.00 -22.00   0.50   20.00    --  -88.50  77.00   0.00  180
 12  \w   -164.00 -75.00   0.50   20.00    --  -88.50 -19.00 120.00  178
 13  \w    -41.00 -13.00   0.50   20.00    --  -88.50  38.00 -60.00   56
 14  \w   -112.00 -22.00   0.50   20.00    --  -88.50  77.00  90.00  180
 15  \w    -41.00 -13.00   0.50   20.00    --  -88.50  38.00   0.00   56
 16  \w   -157.00 -69.00   0.50   20.00    --  -88.50 -67.00 -63.57  176
 17  \w   -160.00 -75.00   0.50   20.00    --  -88.50   0.00-180.00  170
 18  \w    -66.00 -17.00   0.50   20.00    --  -88.50  57.00  90.00   98
 19  \w   -112.00 -22.00   0.50   20.00    --  -88.50  77.00 -90.00  180
 20  \w   -157.00 -69.00   0.50   20.00    --  -88.50 -67.00 -63.57  176
 21  \w     38.00  66.00   0.50   20.00    --  110.00 -57.00-180.00   56
 22  \w     38.00  66.00   0.50   20.00    --  110.00 -57.00 120.00   56
 23  \w    105.00 178.00   0.50   20.00    --  110.00   0.00-180.00  146
 24  \w     41.00 113.00   0.50   20.00    --  110.00-125.00-180.00  144
 25  \w     41.00 113.00   0.50   20.00    --  110.00-125.00-180.00  144
 26  \w     38.00  66.00   0.50   20.00    --  110.00 -57.00 -60.00   56
 27  \w     38.00  66.00   0.50   20.00    --  110.00 -57.00   0.00   56
 28  \w     38.00  66.00   0.50   20.00    --  110.00 -57.00 -90.00   56
 29  \w     41.00 113.00   0.50   20.00    --  110.00-125.00 -30.00  144
 30  \w     41.00  77.00   0.50   20.00    --  110.00 -99.00 -90.00   72
 31  \w     38.00  66.00   0.50   20.00    --  110.00 -57.00 150.00   56
 32  \w     41.00 113.00   0.50   20.00    --  110.00-125.00 150.00  144
 33  \w     41.00 113.00   0.50   20.00    --  110.00-125.00  60.00  144
 34  \w     41.00 113.00   0.50   20.00    --  110.00-125.00  60.00  144
 35  \w     38.00  66.00   0.50   20.00    --  110.00 -57.00-120.00   56
 36  \w     97.00 178.00   0.50   20.00    --  110.00  19.00-120.00  162
 37  \w     41.00 106.00   0.50   20.00    --  110.00 -99.00-180.00  130
 38  \w     38.00  66.00   0.50   20.00    --  110.00 -57.00-150.00   56
 39  \w     86.00 176.00   0.50   20.00    --  110.00  77.00-180.00  180
 40  \w     86.00 176.00   0.50   20.00    --  110.00  77.00-180.00  180
 41  \w   -121.00 -75.00   0.50    4.00    --  -49.12   0.00 -60.00   92
 42  \w   -114.00 -41.00   0.50    4.00    --  -49.12 -77.00  60.00  146
 43  \w     26.00 114.00   0.50    4.00    --   49.12  77.00   0.00  176
;
_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      0.0575727000
_diffrn_orient_matrix_UB_12      0.0647449000
_diffrn_orient_matrix_UB_13      -0.0745037000
_diffrn_orient_matrix_UB_21      -0.1162595000
_diffrn_orient_matrix_UB_22      0.0142460000
_diffrn_orient_matrix_UB_23      -0.0541228000
_diffrn_orient_matrix_UB_31      -0.0103689000
_diffrn_orient_matrix_UB_32      0.2004747000
_diffrn_orient_matrix_UB_33      0.0279187000
_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  0.0377
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27539
_diffrn_reflns_point_group_measured_fraction_full 0.868
_diffrn_reflns_point_group_measured_fraction_max 0.805
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.440
_diffrn_reflns_theta_min         2.760
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.917
_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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1500 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         4881
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0561P)^2^+0.3238P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.524
_reflns_Friedel_fraction_full    0.710
_reflns_Friedel_fraction_max     0.602
_reflns_number_gt                4628
_reflns_number_total             4881
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra07856j2.cif
_cod_data_source_block           ps_dok57a
_cod_database_code               7249801
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H19 N3 O'
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.854
_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:
 C7(H7), C11(H11), C8(H8), C24(H24), C3(H3), C10(H10), C13(H13), C14(H14),
 C26(H26), C30(H30), C31(H31), C4(H4), C34(H34), C6(H6), C23(H23), C28(H28),
 C27(H27), C33(H33)
2.b Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C1(H1a,H1b,H1c), C36(H36a,H36b,
 H36c), C35(H35a,H35b,H35c), C21(H21a,H21b,H21c)
;
_shelx_res_checksum              56748
_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 1.304
_oxdiff_exptl_absorpt_empirical_full_min 0.590