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_4129062
_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         'C Cl2, C52 H31'
_chemical_formula_sum            'C53 H34 Cl2'
_chemical_formula_weight         741.70
_chemical_name_systematic        yi180806-hys
_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             2018-08-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.3243(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.73705(6)
_cell_length_b                   16.80505(11)
_cell_length_c                   25.89795(19)
_cell_measurement_reflns_used    17419
_cell_measurement_temperature    150
_cell_measurement_theta_max      75.6340
_cell_measurement_theta_min      3.1220
_cell_volume                     3779.37(5)
_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      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_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    -65.00  30.00   0.50    0.72    --  -42.80  61.00 -16.00  190
  2  \w    -35.00  -8.00   0.50    1.17    --  -84.50  30.00-180.00   54
  3  \w    -62.00 -36.00   0.50    1.17    --  -84.50  30.00-180.00   52
  4  \w   -110.00 -22.00   0.50    0.72    --  -42.80 -61.00-155.00  176
  5  \w    -83.00 -58.00   0.50    1.17    --  -84.50  61.00 -16.00   50
  6  \w     76.00 113.00   0.50    0.72    --   42.80 125.00-150.00   74
  7  \w     71.00 114.00   0.50    0.72    --   42.80 125.00-120.00   86
  8  \w     85.00 178.00   0.50    1.17    --  108.63  61.00 -16.00  186
  9  \w    128.00 178.00   0.50    1.17    --  108.63  45.00-120.00  100
 10  \w     92.00 127.00   0.50    1.17    --  108.63 -61.00-155.00   70
 11  \w     47.00 104.00   0.50    1.17    --  108.63 -94.00-180.00  114
 12  \w     41.00  86.00   0.50    1.17    --  108.63 -61.00-155.00   90
 13  \w     30.00  61.00   0.50    1.17    --  108.63 -30.00 -90.00   62
 14  \w     31.00  57.00   0.50    1.17    --  108.63 -30.00 -30.00   52
 15  \w     34.00  62.00   0.50    1.17    --  108.63 -30.00  30.00   56
 16  \w     47.00  73.00   0.50    1.17    --  108.63 -45.00  60.00   52
 17  \w     36.00  78.00   0.50    1.17    --  108.63 -45.00  30.00   84
 18  \w     40.00  65.00   0.50    1.17    --  108.63 -30.00  60.00   50
 19  \w     30.00  66.00   0.50    1.17    --  108.63 -30.00  90.00   72
 20  \w     30.00  55.00   0.50    1.17    --  108.63 -30.00 120.00   50
 21  \w     36.00  61.00   0.50    1.17    --  108.63 -30.00   0.00   50
 22  \w     94.00 144.00   0.50    1.17    --  108.63  61.00 -90.00  100
 23  \w     40.00  65.00   0.50    1.17    --  108.63 -30.00-150.00   50
 24  \w     34.00  61.00   0.50    1.17    --  108.63 -30.00-120.00   54
 25  \w     39.00  66.00   0.50    1.17    --  108.63 -30.00-180.00   54
 26  \w     -7.00  18.00   0.50    0.72    --   42.80 -61.00-155.00   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      0.0968616000
_diffrn_orient_matrix_UB_12      -0.0048962000
_diffrn_orient_matrix_UB_13      -0.0461505000
_diffrn_orient_matrix_UB_21      -0.0998189000
_diffrn_orient_matrix_UB_22      0.0656504000
_diffrn_orient_matrix_UB_23      -0.0282734000
_diffrn_orient_matrix_UB_31      0.1101652000
_diffrn_orient_matrix_UB_32      0.0637701000
_diffrn_orient_matrix_UB_33      0.0255505000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23170
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.701
_diffrn_reflns_theta_min         3.141
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46328
_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    1.304
_exptl_crystal_description       plate
_exptl_crystal_F_000             1544
_exptl_crystal_recrystallization_method CH2Cl2/hexane
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.778
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     520
_refine_ls_number_reflns         7628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0595
_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^)+(0.0827P)^2^+3.0745P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1604
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7107
_reflns_number_total             7628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b09646_si_007.cif
_cod_data_source_block           yi180806-hys
_cod_database_code               4129062
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C52H32
_chemical_oxdiff_usercomment     '150 K'
_reflns_odcompleteness_completeness 99.99
_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. Others
 Fixed Sof: Cl2(0.65) C53(0.65) Cl1(0.65) C53A(0.2) Cl2A(0.2) Cl1A(0.2)
 C53B(0.15) Cl2B(0.15) Cl1B(0.15)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C13(H13), C10(H10), C4(H4), C6(H6), C12(H12), C17(H17), C11(H11),
 C51(H51), C29(H29), C30(H30), C5(H5), C36(H36), C31(H31), C42(H42), C20(H20),
 C23(H23), C18(H18), C26(H26), C19(H19), C48(H48), C45(H45), C37(H37), C25(H25),
  C50(H50), C39(H39), C38(H38), C24(H24), C43(H43), C44(H44), C49(H49)
;
_shelx_res_checksum              74550
_shelx_hkl_checksum              67843
_olex2_submission_original_sample_id yi180806-hys
_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 1.656
_oxdiff_exptl_absorpt_empirical_full_min 0.543