Charge-transfer mediated J-aggregation in red emitting ultra-small-single-benzenic <i>meta</i>-fluorophore crystals.
Mandal, Mrinal; Mardanya, Sukumar; Saha, Arijit; Singh, Manjeev; Ghosh, Swarnali; Chatterjee, Tanmay; Patra, Ramen; Bhunia, Surojit; Mandal, Saptarshi; Mukherjee, Soumen; Debnath, Rahul; Reddy, C. Malla; Das, Mousumi; Mandal, Prasun K.; Chemical science 16 (2025) 901–909; doi:10.1039/d4sc06851c

data_1573309
_publ_section_title
;
 Charge-transfer mediated J-aggregation in red emitting
 ultra-small-single-benzenic <i>meta</i>-fluorophore crystals.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              901
_journal_page_last               909
_journal_paper_doi               10.1039/d4sc06851c
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C14 H15 N3'
_chemical_formula_sum            'C14 H15 N3'
_chemical_formula_weight         225.29
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-04-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-10-01 deposited with the CCDC.	2024-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                63.309(8)
_cell_angle_beta                 64.432(7)
_cell_angle_gamma                72.772(7)
_cell_formula_units_Z            2
_cell_length_a                   8.7161(6)
_cell_length_b                   9.2511(7)
_cell_length_c                   9.8844(7)
_cell_measurement_reflns_used    5436
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.7690
_cell_measurement_theta_min      5.3460
_cell_volume                     637.16(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -50.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311  -57.0000   30.0000 114

  2 omega   55.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311 -178.0000   60.0000 66

  3 omega  -50.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311  -57.0000  120.0000 114

  4 omega  -12.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   57.0000 -120.0000 114

  5 omega  -12.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   57.0000 -180.0000 114

  6 omega   -4.00  109.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656  -94.0000 -150.0000 113

  7 omega  100.00  153.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656  111.0000 -150.0000 53

  8 omega   30.00  144.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   61.0000  -60.0000 114

  9 omega  100.00  153.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656  111.0000 -120.0000 53

 10 omega   30.00  144.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   61.0000 -120.0000 114

 11 omega   30.00  144.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   61.0000   60.0000 114

 12 omega   57.00  150.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656  178.0000 -120.0000 93

 13 omega   30.00  144.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   61.0000 -180.0000 114

 14 omega   30.00  144.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   61.0000    0.0000 114

 15 omega  100.00  153.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656  111.0000  150.0000 53

 16 omega  101.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  -30.0000 77

 17 omega   29.00  145.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -65.0000 -180.0000 116

 18 omega   21.00  113.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  150.0000 92

 19 omega   36.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   32.0000   30.0000 142

 20 omega   69.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000   60.0000 109

 21 omega   71.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   65.0000   90.0000 107

 22 omega   21.00  113.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  -60.0000 92

 23 omega   21.00  113.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000   30.0000 92

 24 omega   86.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  138.0000    0.0000 92

 25 omega   19.00  158.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -89.0000  -60.0000 139

 26 omega   23.00  151.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 128

 27 omega  101.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000   90.0000 77

 28 omega   25.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   21.0000  -30.0000 153

 29 omega   31.00  147.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -54.0000    0.0000 116

 30 omega   21.00  113.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000 -180.0000 92

 31 omega   29.00  145.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -65.0000    0.0000 116

 32 omega   69.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000    0.0000 109

 33 omega  101.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  -60.0000 77

 34 omega  -17.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   77.0000   60.0000 128

 35 omega  -50.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311  -57.0000  -60.0000 114

 36 omega  -17.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   77.0000  120.0000 128

 37 omega  -12.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   57.0000 -150.0000 114

 38 omega  -12.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   57.0000  -30.0000 114

 39 omega  100.00  153.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656  111.0000   30.0000 53

 40 omega   24.00  152.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   77.0000  -90.0000 128

 41 omega   24.00  152.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   77.0000   60.0000 128

 42 omega   24.00  152.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   77.0000 -150.0000 128

 43 omega   25.00  152.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   76.0000  -13.8545 127

 44 omega   24.00  152.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   77.0000  120.0000 128

 45 omega   30.00  144.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   61.0000  120.0000 114

 46 omega   24.00  152.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   77.0000   30.0000 128

 47 omega   24.00  152.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   77.0000  150.0000 128

 48 omega  100.00  153.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656  111.0000   90.0000 53

 49 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 113

 50 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 113

 51 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 113

 52 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 113

 53 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 113

 54 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 113

 55 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 113

 56 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 113

 57 omega   58.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   43.0000 -120.0000 120

 58 omega   58.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   43.0000 -180.0000 120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9819
_diffrn_reflns_theta_full        66.25
_diffrn_reflns_theta_max         66.25
_diffrn_reflns_theta_min         5.35
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.022(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0782
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1021P)^2^+0.3208P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2270
_refine_ls_wR_factor_ref         0.2367
_reflns_number_gt                1757
_reflns_number_total             2213
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4sc06851c2.cif
_cod_data_source_block           deabcn2
_cod_depositor_comments
'Adding full bibliography for 1573309--1573310.cif.'
_cod_original_cell_volume        637.16(8)
_cod_database_code               1573309
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C7(H7), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'