Making non-emissive [6]cycloparaphenylene fluorescent by simple multiple methyl substitution.
Kato, Tomoki; Imoto, Daiki; Yagi, Akiko; Itami, Kenichiro; Chemical science 16 (2025) 18952–18958; doi:10.1039/d5sc04694g

data_1575694
_publ_section_title
;
 Making non-emissive [6]cycloparaphenylene fluorescent by simple multiple
 methyl substitution.
;
_journal_issue                   40
_journal_name_full               'Chemical science'
_journal_page_first              18952
_journal_page_last               18958
_journal_paper_doi               10.1039/d5sc04694g
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C24 H24'
_chemical_formula_sum            'C24 H24'
_chemical_formula_weight         312.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2'
_space_group_name_H-M_alt        'C m c 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-06 deposited with the CCDC.	2025-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.9328(10)
_cell_length_b                   7.6621(3)
_cell_length_c                   19.9111(8)
_cell_measurement_reflns_used    7916
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.3290
_cell_measurement_theta_min      2.7440
_cell_volume                     3651.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.892
_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    -82.00 -56.00   0.50  481.03    --    1.50  45.00  30.00   52
  2  \w    -39.00 -13.00   0.50  481.03    --    1.50  45.00  30.00   52
  3  \w    -80.00 -43.00   0.50  481.03    --    1.50  45.00 150.00   74
  4  \w     64.00  89.00   0.50  481.03    --    1.50  45.00 150.00   50
  5  \w    -85.00 -13.00   0.50  481.03    --    1.50  45.00   0.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0244644000
_diffrn_orient_matrix_UB_12      -0.0140765000
_diffrn_orient_matrix_UB_13      0.0194099000
_diffrn_orient_matrix_UB_21      0.0163404000
_diffrn_orient_matrix_UB_22      0.0010405000
_diffrn_orient_matrix_UB_23      -0.0296891000
_diffrn_orient_matrix_UB_31      0.0035901000
_diffrn_orient_matrix_UB_32      0.0914795000
_diffrn_orient_matrix_UB_33      0.0033234000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14589
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.070
_diffrn_reflns_theta_min         2.791
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.7(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4873
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0737P)^2^+0.8124P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1070
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.732
_reflns_number_gt                4609
_reflns_number_total             4873
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc04694g2.cif
_cod_data_source_block           ktm354a_in-isomer_thf-etoh_xray
_cod_depositor_comments          'Adding full bibliography for 1575694.cif.'
_cod_database_code               1575694
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.994
_reflns_odcompleteness_completeness 99.34
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C9(H9), C10(H10), C15(H15), C1(H1), C14(H14), C21(H21)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C24(H24A,H24B,H24C), C19(H19A,H19B,H19C), C12(H12A,H12B,
 H12C), C11(H11A,H11B,H11C), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              17901
_olex2_exptl_crystal_mounting_method loop
_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 1.134
_oxdiff_exptl_absorpt_empirical_full_min 0.851