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_7133956
_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         '2(C20 H21 N O), 2(C4 H8 O), 3.5[C4H8O]'
_chemical_formula_sum            'C62 H86 N2 O7.5'
_chemical_formula_weight         979.383
_chemical_name_common            tetra-tert-butyl-opp-dioxadiaza[8]circulene
_chemical_name_systematic        tetra-tert-butyldioxadiaza[8]circulene
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_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                109.901(2)
_cell_angle_beta                 90.100(1)
_cell_angle_gamma                106.501(2)
_cell_formula_units_Z            2
_cell_length_a                   10.2049(1)
_cell_length_b                   16.5666(3)
_cell_length_c                   17.5296(2)
_cell_measurement_reflns_used    40778
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      74.1940
_cell_measurement_theta_min      3.2160
_cell_volume                     2655.85(8)
_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 0.9815
_diffrn_measured_fraction_theta_max 0.9815
_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  0.0391
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.9815
_diffrn_reflns_Laue_measured_fraction_max 0.9815
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33819
_diffrn_reflns_point_group_measured_fraction_full 0.9815
_diffrn_reflns_point_group_measured_fraction_max 0.9815
_diffrn_reflns_theta_full        65.9949
_diffrn_reflns_theta_max         65.99
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       prism
_exptl_crystal_F_000             1067.297
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.2832
_refine_diff_density_min         -0.2865
_refine_diff_density_rms         0.0739
_refine_ls_d_res_high            0.8439
_refine_ls_d_res_low             13.6861
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0369
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    84
_refine_ls_number_parameters     500
_refine_ls_number_reflns         9071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0369
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0970P)^2^+1.3486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1682
_refine_ls_wR_factor_ref         0.1724
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              18
_reflns_limit_k_min              -19
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                7752
_reflns_number_total             9071
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4cc05539j2.cif
_cod_data_source_block           210703nakagawa
_cod_depositor_comments
'Adding full bibliography for 7133954--7133956.cif.'
_cod_database_code               7133956
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
3. Uiso/Uaniso restraints and constraints
: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed X: Hh(-10) Hi(10) Hj(10) Hk(-10) Hl(-10) Hm(-10) Ho(10) Hn(-10)
 Fixed Y: Hh(-10) Hi(-10) Hj(10) Hk(10) Hl(-10) Hm(10) Hn(10) Ho(10)
 Fixed Z: Hh(-10) Hi(-10) Hj(10) Hk(-10) Hl(10) Hm(10) Hn(-10) Ho(10)
6.a Secondary CH2 refined with riding coordinates:
 C41(H41a,H41b), C42(H42a,H42b), C43(H43a,H43b), C44(H44a,H44b), C45(H45a,
 H45b), C46(H46a,H46b), C47(H47a,H47b), C48(H48a,H48b)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), N1(H1), C24(H24), C29(H29), N2(H2)
6.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C18(H18a,H18b,
 H18c), C19(H19a,H19b,H19c), C20(H20a,H20b,H20c), C34(H34a,H34b,H34c), C35(H35a,
 H35b,H35c), C36(H36a,H36b,H36c), C38(H38a,H38b,H38c), C39(H39a,H39b,H39c),
 C40(H40a,H40b,H40c)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'