Biradicaloid Behavior of a Twisted Double Bond.
Hamamoto, Yosuke; Hirao, Yasukazu; Kubo, Takashi; The journal of physical chemistry letters 12 (2021) 4729–4734; doi:10.1021/acs.jpclett.1c00664

data_8000497
_publ_section_title
;
 Biradicaloid Behavior of a Twisted Double Bond.
;
_journal_issue                   19
_journal_name_full               'The journal of physical chemistry letters'
_journal_page_first              4729
_journal_page_last               4734
_journal_paper_doi               10.1021/acs.jpclett.1c00664
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C60 H80 O6'
_chemical_formula_sum            'C60 H80 O6'
_chemical_formula_weight         897.24
_chemical_name_common
;
3,3',6,6'-tetra-n-octoxybianthrone (Twisted conformer)
;
_chemical_name_systematic
;
3,3',6,6'-tetraoctoxy-10H,10'H-[9,9'-bianthracenylidene]-10,10'-dione
;
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.159(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7405(2)
_cell_length_b                   38.8619(13)
_cell_length_c                   19.7039(7)
_cell_measurement_reflns_used    7033
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      73.8030
_cell_measurement_theta_min      2.2550
_cell_volume                     5153.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.41a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.41a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.41a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.976
_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    -64.00  37.00   0.50   10.00    --  -43.30  19.00 -90.00  202
  2  \w    -40.00 -14.00   0.50   10.00    --  -43.30  37.00 150.00   52
  3  \w     36.00  78.00   0.50   10.00    --   43.30-125.00 120.00   84
  4  \w     11.00  45.00   0.50   10.00    --   43.30 -37.00 -90.00   68
  5  \w    -54.00 -28.00   0.50   40.00    -- -100.00  61.00  60.00   52
  6  \w    -60.00 -28.00   0.50   40.00    -- -100.00  61.00 -30.00   64
  7  \w    -50.00 -21.00   0.50   40.00    -- -100.00  30.00 150.00   58
  8  \w    -48.00 -22.00   0.50   40.00    -- -100.00  30.00 120.00   52
  9  \w   -126.00 -91.00   0.50   40.00    -- -100.00 -15.00 150.00   70
 10  \w    -83.00 -26.00   0.50   40.00    -- -100.00  77.00   0.00  114
 11  \w    -75.00 -50.00   0.50   40.00    -- -100.00 -15.00 150.00   50
 12  \w    -83.00 -58.00   0.50   40.00    -- -100.00  77.00 -30.00   50
 13  \w   -111.00 -34.00   0.50   40.00    -- -100.00 125.00-150.00  154
 14  \w   -174.00-142.00   0.50   40.00    -- -100.00 -15.00 150.00   64
 15  \w     32.00  61.00   0.50   40.00    --  107.75 -45.00 -60.00   58
 16  \w    136.00 168.00   0.50   40.00    --  107.75  45.00-120.00   64
 17  \w     29.00  55.00   0.50   40.00    --  107.75 -30.00 150.00   52
 18  \w     37.00  86.00   0.50   40.00    --  107.75 -77.00   0.00   98
 19  \w     29.00  54.00   0.50   40.00    --  107.75 -30.00  90.00   50
 20  \w     69.00 112.00   0.50   40.00    --  107.75-125.00 120.00   86
 21  \w     34.00  65.00   0.50   40.00    --  107.75-125.00 120.00   62
 22  \w     93.00 120.00   0.50   40.00    --  107.75  45.00-120.00   54
 23  \w     40.00  68.00   0.50   40.00    --  107.75 -77.00 -90.00   56
 24  \w     33.00  61.00   0.50   40.00    --  107.75 -45.00 -90.00   56
 25  \w   -126.00 -78.00   0.50   40.00    -- -100.00-125.00 150.00   96
 26  \w    -88.00 -62.00   0.50   40.00    -- -100.00 125.00 -90.00   52
 27  \w     59.00  85.00   0.50   40.00    --  107.75 -77.00  30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-Custom'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0477771000
_diffrn_orient_matrix_UB_12      0.0329915000
_diffrn_orient_matrix_UB_13      0.0410008000
_diffrn_orient_matrix_UB_21      0.0035010000
_diffrn_orient_matrix_UB_22      -0.0209087000
_diffrn_orient_matrix_UB_23      0.0664688000
_diffrn_orient_matrix_UB_31      0.2239544000
_diffrn_orient_matrix_UB_32      -0.0067200000
_diffrn_orient_matrix_UB_33      -0.0053692000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25524
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.250
_diffrn_reflns_theta_min         2.274
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.41a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_description       fibrous
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     693
_refine_ls_number_reflns         9200
_refine_ls_number_restraints     162
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1462
_refine_ls_R_factor_gt           0.1102
_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^)+(0.1306P)^2^+20.9462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3056
_refine_ls_wR_factor_ref         0.3269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6075
_reflns_number_total             9200
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jz1c00664_si_002.cif
_cod_data_source_block           BA3-Twisted
_cod_depositor_comments
'Adding full bibliography for 8000496--8000497.cif.'
_cod_database_code               8000497
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C60 H80 O6'
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.840
_diffrn_oxdiff_digest_frames
;
01c960bcb7259b092a05f84d2a97419afb019706c07
;
_diffrn_oxdiff_digest_hkl
;
01bc6448dea41fd9990d00405beb6c0e7a33e9
;
_reflns_odcompleteness_completeness 97.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C47 \\sim C52 \\sim C49 \\sim C50 \\sim C48 \\sim C51 \\sim C48A \\sim C49A
\\sim C50A \\sim C51A \\sim C52A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C56 \\sim C57 \\sim C59 \\sim C58 \\sim C60: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
3. Others
 Sof(H47C)=Sof(H47D)=Sof(C48A)=Sof(H48C)=Sof(H48D)=Sof(C49A)=Sof(H49C)=
 Sof(H49D)=Sof(C50A)=Sof(H50C)=Sof(H50D)=Sof(C51A)=Sof(H51C)=Sof(H51D)=
 Sof(C52A)=Sof(H52D)=Sof(H52E)=Sof(H52F)=1-FVAR(1)
 Sof(H47A)=Sof(H47B)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=Sof(C49)=Sof(H49A)=
 Sof(H49B)=Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(C51)=
 Sof(H51A)=Sof(H51B)=FVAR(1)
 Sof(H55A)=Sof(H55B)=Sof(C56A)=Sof(H56C)=Sof(H56D)=Sof(C57A)=Sof(H57C)=
 Sof(H57D)=Sof(C58A)=Sof(H58C)=Sof(H58D)=Sof(C59A)=Sof(H59C)=Sof(H59D)=
 Sof(C60A)=Sof(H60D)=Sof(H60E)=Sof(H60F)=1-FVAR(2)
 Sof(H55C)=Sof(H55D)=Sof(C60)=Sof(H60A)=Sof(H60B)=Sof(H60C)=Sof(C59)=Sof(H59A)=
 Sof(H59B)=Sof(C58)=Sof(H58A)=Sof(H58B)=Sof(C56)=Sof(H56A)=Sof(H56B)=Sof(C57)=
 Sof(H57A)=Sof(H57B)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C23(H23A,H23B), C16(H16A,H16B), C17(H17A,H17B), C25(H25A,
 H25B), C18(H18A,H18B), C24(H24A,H24B), C28(H28A,H28B), C53(H53A,H53B),
 C29(H29A,H29B), C19(H19A,H19B), C27(H27A,H27B), C26(H26A,H26B), C20(H20A,H20B),
  C21(H21A,H21B), C45(H45A,H45B), C54(H54A,H54B), C47(H47A,H47B), C47(H47C,
 H47D), C46(H46A,H46B), C55(H55C,H55D), C55(H55A,H55B), C49(H49A,H49B),
 C50(H50A,H50B), C48(H48A,H48B), C51(H51A,H51B), C59(H59A,H59B), C58(H58A,H58B),
  C56(H56A,H56B), C57(H57A,H57B), C48A(H48C,H48D), C49A(H49C,H49D), C50A(H50C,
 H50D), C51A(H51C,H51D), C56A(H56C,H56D), C57A(H57C,H57D), C58A(H58C,H58D),
 C59A(H59C,H59D)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C36(H36), C3(H3), C10(H10), C43(H43), C33(H33), C6(H6), C13(H13),
 C11(H11), C40(H40), C35(H35), C41(H41)
4.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C22(H22A,H22B,H22C), C52(H52A,H52B,H52C), C60(H60A,H60B,
 H60C), C52A(H52D,H52E,H52F), C60A(H60D,H60E,H60F)
;
_shelx_res_checksum              99384
_shelx_hkl_checksum              76387
_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 1.821
_oxdiff_exptl_absorpt_empirical_full_min 0.494