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_1573310
_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         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-10-31
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-10-01 deposited with the CCDC.	2024-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.614(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.292(4)
_cell_length_b                   10.450(3)
_cell_length_c                   6.872(2)
_cell_measurement_reflns_used    2119
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      3.32
_cell_volume                     1088.5(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      301.05
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1244
_diffrn_reflns_av_unetI/netI     0.0987
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8292
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.367
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4157
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1464 before and 0.0925 after correction.
The Ratio of minimum to maximum transmission is 0.5576.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.027(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1509
_refine_ls_R_factor_gt           0.1058
_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^)+(0.0961P)^2^+1.4564P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2431
_refine_ls_wR_factor_ref         0.2667
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1260
_reflns_number_total             1908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06851c2.cif
_cod_data_source_block           test5_a
_cod_depositor_comments
'Adding full bibliography for 1573309--1573310.cif.'
_cod_database_code               1573310
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.956
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C003(H003), C005(H005), C009(H009), C00C(H00C), C00D(H00D)
2.b Idealised Me refined as rotating group:
 C00E(H00A,H00B,H00E), C00F(H00F,H00G,H00H)
;
_shelx_res_checksum              58311
_shelx_hkl_checksum              20790
_olex2_submission_special_instructions 'No special instructions were received'