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_7249798
_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_absolute_configuration rmad
_chemical_formula_moiety         'C15 H15 Br N2 O'
_chemical_formula_sum            'C15 H15 Br N2 O'
_chemical_formula_weight         319.20
_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             2024-01-10
_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                   5.30400(10)
_cell_length_b                   8.79880(10)
_cell_length_c                   29.2208(3)
_cell_measurement_reflns_used    10212
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      78.4780
_cell_measurement_theta_min      2.9970
_cell_volume                     1363.70(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      100.02(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 0.976
_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   -120.00 -33.00   0.50    1.00    --  -48.87 -57.00 -60.00  174
  2  \w    -20.00  27.00   0.50    1.00    --  -48.87  19.00-150.00   94
  3  \w    -41.00  27.00   0.50    1.00    --  -48.87  38.00-120.00  136
  4  \w    -27.00  20.00   0.50    1.00    --   48.87 -19.00  30.00   94
  5  \w    -27.00  20.00   0.50    1.00    --   48.87 -19.00 -30.00   94
  6  \w   -164.00 -75.00   0.50    2.00    --  -88.50 -38.00  30.00  178
  7  \w    -66.00 -17.00   0.50    2.00    --  -88.50  57.00 -90.00   98
  8  \w    -66.00 -17.00   0.50    2.00    --  -88.50  57.00  30.00   98
  9  \w    -41.00 -13.00   0.50    2.00    --  -88.50  38.00  90.00   56
 10  \w    -66.00 -17.00   0.50    2.00    --  -88.50  57.00 -30.00   98
 11  \w    -41.00 -13.00   0.50    2.00    --  -88.50  38.00   0.00   56
 12  \w     45.00 134.00   0.50    2.00    --  110.00 -77.00  30.00  178
 13  \w     41.00 106.00   0.50    2.00    --  110.00 -99.00   0.00  130
 14  \w     38.00  66.00   0.50    2.00    --  110.00 -57.00  90.00   56
 15  \w     38.00  66.00   0.50    2.00    --  110.00 -57.00  60.00   56
 16  \w     38.00  66.00   0.50    2.00    --  110.00 -57.00 120.00   56
 17  \w     38.00  66.00   0.50    2.00    --  110.00 -57.00 150.00   56
 18  \w     38.00  66.00   0.50    2.00    --  110.00 -57.00 -30.00   56
 19  \w     38.00 178.00   0.50    2.00    --  110.00   0.00 -60.00  280
 20  \w     97.00 178.00   0.50    2.00    --  110.00  19.00-180.00  162
 21  \w   -114.00 -25.00   0.50    1.00    --  -48.87 -77.00-180.00  178
 22  \w   -120.00 -33.00   0.50    1.00    --  -48.87 -57.00  90.00  174
 23  \w     25.00 114.00   0.50    1.00    --   48.87  77.00-120.00  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      -0.1149456000
_diffrn_orient_matrix_UB_12      0.0737386000
_diffrn_orient_matrix_UB_13      0.0430365000
_diffrn_orient_matrix_UB_21      0.0610416000
_diffrn_orient_matrix_UB_22      0.1587141000
_diffrn_orient_matrix_UB_23      -0.0192766000
_diffrn_orient_matrix_UB_31      -0.2596571000
_diffrn_orient_matrix_UB_32      0.0047538000
_diffrn_orient_matrix_UB_33      -0.0235890000
_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  0.0285
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            13843
_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         79.672
_diffrn_reflns_theta_min         3.025
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.050
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1075 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0209
_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^)+(0.0205P)^2^+0.9103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0507
_refine_ls_wR_factor_ref         0.0511
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                2770
_reflns_number_total             2847
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra07856j2.cif
_cod_data_source_block           ps_dok98_1b
_cod_database_code               7249798
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H15 Br N2 O1'
_shelx_estimated_absorpt_t_max   0.895
_shelx_estimated_absorpt_t_min   0.488
_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:
 C3(H3), C7(H7), C10(H10), C6(H6), C13(H13), C11(H11), C4(H4), C14(H14)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              41703
_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 1.618
_oxdiff_exptl_absorpt_empirical_full_min 0.742