Photo- and Thermal Interconversion of Multiconfigurational Strained Hydrocarbons Exhibiting Completely Switchable Oxidation to Stable Dicationic Dyes.
Ishigaki, Yusuke; Hayashi, Yuki; Suzuki, Takanori; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b09646

data_4129059
_publ_section_title
;
 Photo- and Thermal Interconversion of Multiconfigurational Strained
 Hydrocarbons Exhibiting Completely Switchable Oxidation to Stable
 Dicationic Dyes.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b09646
_journal_year                    2019
_chemical_formula_moiety         'C52 H32'
_chemical_formula_sum            'C52 H32'
_chemical_formula_weight         656.77
_chemical_name_systematic        yi190108-hys-293K
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.488(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   18.0595(6)
_cell_length_b                   6.7674(2)
_cell_length_c                   14.6897(6)
_cell_measurement_reflns_used    3627
_cell_measurement_temperature    293
_cell_measurement_theta_max      75.6920
_cell_measurement_theta_min      3.0890
_cell_volume                     1738.22(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45h (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45h (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45h (Rigaku OD, 2018)'
_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      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.956
_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    -57.00 -25.00   0.50    4.28    --  -42.55 -19.00  49.00   64
  2  \w    -97.00 -60.00   0.50    4.28    --  -42.55 -19.00  49.00   74
  3  \w   -125.00 -55.00   0.50    6.17    --  -84.50 -19.00  49.00  140
  4  \w    -40.00 -15.00   0.50    4.28    --  -42.55  19.00-142.00   50
  5  \w    -64.00 -39.00   0.50    6.17    --  -84.50  19.00-142.00   50
  6  \w    -76.00 -34.00   0.50    6.17    --  -84.50 125.00-120.00   84
  7  \w     13.00 107.00   0.50    4.28    --   42.55  19.00-142.00  188
  8  \w     84.00 166.00   0.50    6.17    --  108.63  19.00-142.00  164
  9  \w     58.00  84.00   0.50    6.17    --  108.63 -94.00 -30.00   52
 10  \w     53.00 106.00   0.50    6.17    --  108.63 -94.00  30.00  106
 11  \w     39.00  73.00   0.50    6.17    --  108.63 -45.00 -90.00   68
 12  \w     40.00  65.00   0.50    6.17    --  108.63 -30.00 -90.00   50
 13  \w     31.00  58.00   0.50    6.17    --  108.63 -30.00-150.00   54
 14  \w     30.00  58.00   0.50    6.17    --  108.63 -30.00-120.00   56
 15  \w     34.00  74.00   0.50    6.17    --  108.63 -45.00-180.00   80
 16  \w     28.00  96.00   0.50    4.28    --   42.55-125.00-120.00  136
 17  \w     31.00  60.00   0.50    6.17    --  108.63 -30.00 -60.00   58
 18  \w     30.00  55.00   0.50    6.17    --  108.63 -30.00 -30.00   50
 19  \w     43.00  69.00   0.50    6.17    --  108.63 -45.00  30.00   52
 20  \w     31.00  63.00   0.50    6.17    --  108.63 -19.00  49.00   64
 21  \w     31.00  65.00   0.50    6.17    --  108.63 -30.00  90.00   68
 22  \w     39.00 109.00   0.50    6.17    --  108.63-125.00  30.00  140
 23  \w     -6.00  19.00   0.50    4.28    --   42.55 -19.00  49.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0001562000
_diffrn_orient_matrix_UB_12      -0.0415599000
_diffrn_orient_matrix_UB_13      -0.1031803000
_diffrn_orient_matrix_UB_21      0.0866334000
_diffrn_orient_matrix_UB_22      0.0406653000
_diffrn_orient_matrix_UB_23      0.0229356000
_diffrn_orient_matrix_UB_31      0.0160826000
_diffrn_orient_matrix_UB_32      -0.2200614000
_diffrn_orient_matrix_UB_33      0.0236495000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4913
_diffrn_reflns_point_group_measured_fraction_full 0.705
_diffrn_reflns_point_group_measured_fraction_max 0.665
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.961
_diffrn_reflns_theta_min         3.107
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.540
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45h (Rigaku Oxford Diffraction, 2018)
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    1.255
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method CH2Cl2/pentane
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.182
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.174
_refine_ls_abs_structure_details
;
 Flack x determined using 503 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.511
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.510
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.1191
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2996
_refine_ls_wR_factor_ref         0.3010
_reflns_Friedel_coverage         0.279
_reflns_Friedel_fraction_full    0.354
_reflns_Friedel_fraction_max     0.318
_reflns_number_gt                2325
_reflns_number_total             2418
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b09646_si_006.cif
_cod_data_source_block           yi190108-hys-293
_cod_database_code               4129059
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C52 H32'
_chemical_oxdiff_usercomment     '293 K'
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C10(H10), C23(H23), C19(H19), C12(H12), C22(H22), C13(H13),
 C25(H25), C5(H5), C17(H17), C6(H6), C4(H4), C18(H18), C3(H3), C11(H11),
 C24(H24)
;
_shelx_res_checksum              74769
_shelx_hkl_checksum              39663
_olex2_submission_original_sample_id yi190108-hys-293K
_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 2.164
_oxdiff_exptl_absorpt_empirical_full_min 0.436