Fluorescent molecular glass based on hexadehydrotribenzo[12]annulene.
Kasahara, Yotaro; Hisaki, Ichiro; Akutagawa, Tomoyuki; Takeda, Takashi; Chemical communications (Cambridge, England) 57 (2021) 5374–5377; doi:10.1039/d1cc01356d

data_7128262
_publ_section_title
;
 Fluorescent molecular glass based on hexadehydrotribenzo[12]annulene.
;
_journal_issue                   44
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5374
_journal_page_last               5377
_journal_paper_doi               10.1039/d1cc01356d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C72 H48 O12, C7 H8'
_chemical_formula_sum            'C79 H56 O12'
_chemical_formula_weight         1197.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-04-22
_audit_creation_method
;
Olex2 1.5-dev
(compiled 2021.04.12 svn.r67f51adf for OlexSys, GUI svn.r6225)
;
_audit_update_record
;
2021-04-27 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.315(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.3648(9)
_cell_length_b                   9.5584(4)
_cell_length_c                   25.8540(10)
_cell_measurement_reflns_used    24838
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.10
_cell_measurement_theta_min      3.43
_cell_volume                     6004.0(4)
_computing_cell_refinement       'RAPID AUTO ver. 3.1.2 (Rigaku)'
_computing_data_collection       'RAPID AUTO ver. 3.1.2 (Rigaku)'
_computing_data_reduction        'RAPID AUTO ver. 3.1.2 (Rigaku)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1237
_diffrn_reflns_av_unetI/netI     0.1086
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            61595
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        62.498
_diffrn_reflns_theta_max         62.498
_diffrn_reflns_theta_min         3.429
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2504
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     940
_refine_ls_number_reflns         9541
_refine_ls_number_restraints     196
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1689
_refine_ls_R_factor_gt           0.0973
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1101P)^2^+18.4875P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2507
_refine_ls_wR_factor_ref         0.3107
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4912
_reflns_number_total             9541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01356d2.cif
_cod_data_source_block           exp64_c112dbasingletry2
_cod_depositor_comments          'Adding full bibliography for 7128262.cif.'
_cod_original_cell_volume        6004.1(4)
_cod_database_code               7128262
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.870
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H76A,H76B,H76C} of C76, {H86A,H86B,H86C} of C86, {H81A,
  H81B,H81C} of C81, {H80A,H80B,H80C} of C80, {H85A,H85B,H85C} of C85, {H74A,
  H74B,H74C} of C74
 At 1.5 times of:
  {H1A,H1B,H1C} of C1
2. Restrained distances
 C21-C43 \\sim C21-C43A
 with sigma of 0.02
 C71-C5B \\sim C71A-C5C
 with sigma of 0.04
 C53-C61 \\sim C53A-C61A
 with sigma of 0.04
 C43-C53 \\sim C43A-C53A
 with sigma of 0.02
 O12B-H1A \\sim O12C-H1AA
 with sigma of 0.04
 C43-C61 \\sim C43A-C61A
 with sigma of 0.02
 C61-H75 \\sim C61A-H75A
 with sigma of 0.04
 C53-H53 \\sim C53A-H53A
 with sigma of 0.02
 C77-O1B \\sim C77A-O1C
 with sigma of 0.04
 C53-C71 \\sim C53A-C71A
 with sigma of 0.02
 H1A-H1C \\sim H1AA-H1AC
 with sigma of 0.04
 C61-H61 \\sim C61A-H61A
 with sigma of 0.02
 C53-C77 \\sim C53A-C77A
 with sigma of 0.04
 C61-C75 \\sim C61A-C75A
 with sigma of 0.02
 H61-C75 \\sim H61A-C75A
 with sigma of 0.04
 C71-H71 \\sim C71A-H71A
 with sigma of 0.02
 C75-C5B \\sim C75A-C5C
 with sigma of 0.04
 C71-C77 \\sim C71A-C77A
 with sigma of 0.02
 O1B-O12B \\sim O1C-O12C
 with sigma of 0.04
 C75-H75 \\sim C75A-H75A
 with sigma of 0.02
 O12B-H1C \\sim O12C-H1AC
 with sigma of 0.04
 C75-C77 \\sim C75A-C77A
 with sigma of 0.02
 C43-C75 \\sim C43A-C75A
 with sigma of 0.04
 C77-C5B \\sim C77A-C5C
 with sigma of 0.02
 C53-H71 \\sim C53A-H71A
 with sigma of 0.04
 O1B-C5B \\sim O1C-C5C
 with sigma of 0.02
 H53-C71 \\sim H53A-C71A
 with sigma of 0.04
 C5B-O12B \\sim C5C-O12C
 with sigma of 0.02
 C61-C77 \\sim C61A-C77A
 with sigma of 0.04
 O12B-C1 \\sim O12C-C1A
 with sigma of 0.02
 C71-C75 \\sim C71A-C75A
 with sigma of 0.04
 C1-H1A \\sim C1A-H1AA
 with sigma of 0.02
 H71-C77 \\sim H71A-C77A
 with sigma of 0.04
 C1-H1B \\sim C1A-H1AB
 with sigma of 0.02
 H75-C77 \\sim H75A-C77A
 with sigma of 0.04
 C1-H1C \\sim C1A-H1AC
 with sigma of 0.02
 C77-O12B \\sim C77A-O12C
 with sigma of 0.04
 C21-C53 \\sim C21-C53A
 with sigma of 0.04
 C5B-C1 \\sim C5C-C1A
 with sigma of 0.04
 C21-C61 \\sim C21-C61A
 with sigma of 0.04
 O12B-H1B \\sim O12C-H1AB
 with sigma of 0.04
 C43-H53 \\sim C43A-H53A
 with sigma of 0.04
 H1A-H1B \\sim H1AA-H1AB
 with sigma of 0.04
 C43-H61 \\sim C43A-H61A
 with sigma of 0.04
 H1B-H1C \\sim H1AB-H1AC
 with sigma of 0.04
 C43-C71 \\sim C43A-C71A
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C21, C53A, C61A, C71A, C75A, C77A, O1C, C5C, O12C, C1A, C43A
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C53, C61, C71, C75, C77, O1B, C5B, O12B, C1, C43, C21
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
4. Others
 Sof(C53A)=Sof(H53A)=Sof(C61A)=Sof(H61A)=Sof(C71A)=Sof(H71A)=Sof(C75A)=
 Sof(H75A)=Sof(C77A)=Sof(O1C)=Sof(C5C)=Sof(O12C)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=
 Sof(H1AC)=Sof(C43A)=1-FVAR(1)
 Sof(C43)=Sof(C53)=Sof(H53)=Sof(C61)=Sof(H61)=Sof(C71)=Sof(H71)=Sof(C75)=
 Sof(H75)=Sof(C77)=Sof(O1B)=Sof(C5B)=Sof(O12B)=Sof(C1)=Sof(H1A)=Sof(H1B)=
 Sof(H1C)=FVAR(1)
5.a Me refined with riding coordinates:
 C74(H74A,H74B,H74C), C76(H76A,H76B,H76C), C80(H80A,H80B,H80C), C81(H81A,H81B,
 H81C), C85(H85A,H85B,H85C), C86(H86A,H86B,H86C)
5.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C26(H26), C31(H31), C33(H33), C34(H34), C35(H35),
 C40(H40), C41(H41), C45(H45), C49(H49), C51(H51), C53(H53), C55(H55), C56(H56),
  C57(H57), C58(H58), C59(H59), C60(H60), C61(H61), C62(H62), C63(H63),
 C66(H66), C67(H67), C68(H68), C70(H70), C71(H71), C72(H72), C75(H75), C78(H78),
  C82(H82), C84(H84), C87(H87), C88(H88), C89(H89)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
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_shelx_res_checksum              86928
_olex2_submission_special_instructions 'No special instructions were received'