Synthesis of substituent-free dioxadiaza[8]circulene to investigate intermolecular interactions and photophysical properties.
Nakagawa, Aoi; Ota, Wataru; Ehara, Takumi; Matsuo, Yusuke; Miyata, Kiyoshi; Onda, Ken; Sato, Tohru; Seki, Shu; Tanaka, Takayuki; Chemical communications (Cambridge, England) 60 (2024) 14770–14773; doi:10.1039/d4cc05539j

data_7133954
_publ_section_title
;
 Synthesis of substituent-free dioxadiaza[8]circulene to investigate
 intermolecular interactions and photophysical properties.
;
_journal_issue                   99
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14770
_journal_page_last               14773
_journal_paper_doi               10.1039/d4cc05539j
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C24 H10 N2 O2'
_chemical_formula_sum            'C24 H10 N2 O2'
_chemical_formula_weight         358.359
_chemical_name_common            opp-dioxadiaza[8]circulene
_chemical_name_systematic        dioxadiaza[8]circulene
_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'
_symmetry_Int_Tables_number      14
_audit_creation_date             2024-05-14
_audit_creation_method
;
Olex2 1.5-dev
(compiled 2024.05.14 svn.rc2abdb5a for OlexSys, GUI svn.r6697)
;
_audit_update_record
;
2024-10-17 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.166(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0418(4)
_cell_length_b                   14.1923(4)
_cell_length_c                   10.9180(3)
_cell_measurement_reflns_used    5293
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      73.7990
_cell_measurement_theta_min      3.10000
_cell_volume                     1494.47(9)
_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  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_diffrn_ambient_temperature      93.15
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9902
_diffrn_measured_fraction_theta_max 0.9902
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.9902
_diffrn_reflns_Laue_measured_fraction_max 0.9902
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10108
_diffrn_reflns_point_group_measured_fraction_full 0.9902
_diffrn_reflns_point_group_measured_fraction_max 0.9902
_diffrn_reflns_theta_full        66.9844
_diffrn_reflns_theta_max         66.98
_diffrn_reflns_theta_min         4.58
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_description       prism
_exptl_crystal_F_000             738.524
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.2453
_refine_diff_density_min         -0.1724
_refine_diff_density_rms         0.0491
_refine_ls_d_res_high            0.8376
_refine_ls_d_res_low             9.6447
_refine_ls_goodness_of_fit_ref   1.1139
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     343
_refine_ls_number_reflns         2631
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.1132
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+0.1915P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1011
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2252
_reflns_number_total             2631
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4cc05539j2.cif
_cod_data_source_block           211030nakagawa
_cod_depositor_comments
'Adding full bibliography for 7133954--7133956.cif.'
_cod_database_code               7133954
_olex2_refinement_description
;
1. Rigid body (RIGU) restrains
 N1, H9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_olex2_refine_details
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      cc-pVTZ
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2024-05-14_18-20-44
;
_olex2_submission_special_instructions 'No special instructions were received'