Aggregation-induced emission active seminaphthofluoresceins: a new class of xanthene luminogens for bioimaging.
McKay, Laura; Zhang, Issan; Suh, Imogen; Bohle, D. Scott; Kakkar, Ashok; Maysinger, Dusica; Nanoscale 18 (2026) 3194–3208; doi:10.1039/d5nr04595a

data_1576548
_publ_section_title
;
 Aggregation-induced emission active seminaphthofluoresceins: a new class
 of xanthene luminogens for bioimaging.
;
_journal_issue                   6
_journal_name_full               Nanoscale
_journal_page_first              3194
_journal_page_last               3208
_journal_paper_doi               10.1039/d5nr04595a
_journal_volume                  18
_journal_year                    2026
_chemical_formula_moiety         'C34 H20 O7, C3 H6 O'
_chemical_formula_sum            'C37 H26 O8'
_chemical_formula_weight         598.58
_chemical_name_systematic
'3-(propargyloxy)-7-(2,4-di(propargylester)phenyl)-xanth-10-one acetone solvate(1:1)'
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2psrv3
_audit_creation_date             2025-10-17
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-10-20 deposited with the CCDC.	2026-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                108.425(10)
_cell_angle_beta                 93.040(11)
_cell_angle_gamma                102.406(11)
_cell_formula_units_Z            2
_cell_length_a                   9.689(10)
_cell_length_b                   12.113(12)
_cell_length_c                   13.682(14)
_cell_measurement_reflns_used    1589
_cell_measurement_temperature    80
_cell_measurement_theta_max      20.85
_cell_measurement_theta_min      2.75
_cell_volume                     1475(3)
_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      80
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1699
_diffrn_reflns_av_unetI/netI     0.1487
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7606
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        21.347
_diffrn_reflns_theta_max         21.347
_diffrn_reflns_theta_min         2.791
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.5778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Multiscan absorption correction performed via SADABS in BRUKER APEX II, refined to a minimum as a medium absorber with 50 refinement cycles'
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_preparation
'Propargyl chloride reaction with xanthone precursor'
_exptl_crystal_recrystallization_method
'Compound crystallized via slow evaporation of acetone from a screwcap vial'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         3143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0517P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1532
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2029
_reflns_number_total             3143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nr04595a2.cif
_cod_data_source_block           s1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1576548
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.963
_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:
 C31(H31A,H31B), C28(H28A,H28B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C18(H18), C3(H3), C7(H7), C9(H9), C1(H1), C4(H4), C21(H21), C5(H5),
 C22(H22), C6(H6)
2.c Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C3S(H3SA,H3SB,H3SC)
2.d :
 C33(H33), C27(H27), C30(H30)
;
_olex2_date_sample_completion    2024-01-09
_olex2_date_sample_data_collection 2024-01-08
_olex2_date_sample_submission    2024-01-08
_olex2_exptl_crystal_mounting_method
;
150-micrometer MitoGen loop with paratone-N oil from Hampton research.
;
_olex2_submission_original_sample_id GS_4L_Fluor
_olex2_submission_special_instructions 'No special instructions were received'