Synthesis of naphthalene-fused imidazo[1,2-<i>a</i>]pyridinium salts showing green luminescence with high quantum yields and large Stokes shift.
Abe, Sota; Katayama, Tetsuro; Furube, Akihiro; Tabata, Atsushi; Yoshida, Yasushi; Ueta, Shoko; Arakawa, Yukihiro; Minagawa, Keiji; Imada, Yasushi; Yagishita, Fumitoshi; Organic & biomolecular chemistry 23 (2025) 4355–4359; doi:10.1039/d5ob00447k

data_7160496
_publ_section_title
;
 Synthesis of naphthalene-fused imidazo[1,2-<i>a</i>]pyridinium salts
 showing green luminescence with high quantum yields and large Stokes
 shift.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4355
_journal_page_last               4359
_journal_paper_doi               10.1039/d5ob00447k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H17 I N2 O2'
_chemical_formula_sum            'C23 H17 I N2 O2'
_chemical_formula_weight         480.28
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-03-05 deposited with the CCDC.	2025-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.365(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.82330(10)
_cell_length_b                   13.6419(3)
_cell_length_c                   21.6469(4)
_cell_measurement_reflns_used    20953
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      68.47
_cell_measurement_theta_min      3.24
_cell_volume                     2014.91(6)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'Image Plate'
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22533
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         3.830
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    12.652
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR(Rigaku,1995)
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_description       needle
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.471
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0378P)^2^+5.1790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1132
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3246
_reflns_number_total             3684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00447k2.cif
_cod_data_source_block           shelx_trans
_cod_depositor_comments          'Adding full bibliography for 7160496.cif.'
_cod_database_code               7160496
_shelx_shelxl_version_number     2018/3
_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:
 C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00P(H00P), C00R(H00R), C00S(H00S), C00T(H00T)
2.b Idealised Me refined as rotating group:
 C00B(H00A,H00B,H00C), C00Q(H00D,H00E,H00F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'