A double-helical S,C-bridged tetraphenyl-<i>para</i>-phenylenediamine and its persistent radical cation.
Harada, Kaho; Hasegawa, Chika; Matsumoto, Taisuke; Sugishita, Hiroki; Kitamura, Chitoshi; Higashibayashi, Shuhei; Hasegawa, Masashi; Suzuki, Shuichi; Kato, Shin-Ichiro; Chemical communications (Cambridge, England) 59 (2023) 1301–1304; doi:10.1039/d2cc06144a

data_7131150
_publ_section_title
;
 A double-helical S,C-bridged tetraphenyl-<i>para</i>-phenylenediamine and
 its persistent radical cation.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1301
_journal_page_last               1304
_journal_paper_doi               10.1039/d2cc06144a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C2 F6 N O4 S2, C30 H24 N2'
_chemical_formula_sum            'C32 H24 F6 N3 O4 S2'
_chemical_formula_weight         692.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-18
_audit_creation_method
;
Olex2 1.5-ac5-020
(compiled 2021.11.16 svn.r5db059d7 for Rigaku Oxford Diffraction, GUI svn.r6430)
;
_audit_update_record
;
2022-06-13 deposited with the CCDC.	2022-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.7930(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.5219(3)
_cell_length_b                   7.73607(11)
_cell_length_c                   22.8391(4)
_cell_measurement_reflns_used    9328
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.2660
_cell_measurement_theta_min      3.9530
_cell_volume                     3019.00(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.41a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.41a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.41a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.970
_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     99.00 138.00   0.50    0.05    --  107.00  15.00 150.00   78
  2  \w    107.00 178.00   0.50    0.05    --  107.00  77.00  60.00  142
  3  \w     99.00 138.00   0.50    0.05    --  107.00  15.00-120.00   78
  4  \w     99.00 130.00   0.50    0.05    --  107.00  15.00-180.00   62
  5  \w     33.00  92.00   0.50    0.05    --  107.00 -94.00-120.00  118
  6  \w     33.00  92.00   0.50    0.05    --  107.00 -94.00-150.00  118
  7  \w     33.00  92.00   0.50    0.05    --  107.00 -94.00 -90.00  118
  8  \w     38.00  70.00   0.50    0.05    --  107.00 -77.00-180.00   64
  9  \w     49.00  77.00   0.50    0.05    --  107.00 -77.00 -90.00   56
 10  \w     39.00  77.00   0.50    0.05    --  107.00 -77.00 -60.00   76
 11  \w     33.00  77.00   0.50    0.05    --  107.00 -77.00 150.00   88
 12  \w   -134.00 -95.00   0.50    0.05    -- -104.00 -15.00-150.00   78
 13  \w   -134.00 -95.00   0.50    0.05    -- -104.00 -15.00-180.00   78
 14  \w   -175.00 -92.00   0.50    0.05    -- -104.00 -56.00 -51.08  166
 15  \w   -175.00 -94.00   0.50    0.05    -- -104.00 -47.00  23.24  162
 16  \w    -17.00  32.00   0.50    0.05    --  -44.36  38.00-120.00   98
 17  \w    -17.00  32.00   0.50    0.05    --  -44.36  38.00 -90.00   98
 18  \w    -17.00  32.00   0.50    0.05    --  -44.36  38.00-150.00   98
 19  \w    -17.00  32.00   0.50    0.05    --  -44.36  38.00 -60.00   98
 20  \w    -17.00  32.00   0.50    0.05    --  -44.36  38.00   0.00   98
 21  \w    -65.00  20.00   0.50    0.05    --  -44.36  77.00 150.00  170
 22  \w   -116.00 -91.00   0.50    0.05    --  -44.48 -51.00 -42.02   50
 23  \w    -27.00  -1.00   0.50    0.05    --  -44.48  57.00-120.00   52
 24  \w     33.00  59.00   0.50    0.05    --  107.00-100.00 -88.53   52
 25  \w     69.00  94.00   0.50    0.05    --  107.00-100.00 -88.53   50
 26  \w     99.00 124.00   0.50    0.05    --  107.00  15.00-150.00   50
 27  \w     67.00  92.00   0.50    0.05    --  107.00 -94.00-180.00   50
 28  \w     69.00  95.00   0.50    0.05    --  107.00 -89.00 138.60   52
 29  \w     69.00  95.00   0.50    0.05    --  107.00 -89.00-166.99   52
 30  \w   -118.00 -67.00   0.50    0.05    --  -44.48 -50.00  54.66  102
 31  \w   -118.00 -34.00   0.50    0.05    --  -44.48 -50.00 134.88  168
 32  \w   -118.00 -34.00   0.50    0.05    --  -44.48 -50.00 -20.62  168
 33  \w   -117.00 -33.00   0.50    0.05    --  -44.48 -52.00-143.71  168
 34  \w      1.00  76.00   0.50    0.05    --   44.48 -99.00  90.00  150
 35  \w     33.00  59.00   0.50    0.05    --   44.48  53.00  83.70   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0697469000
_diffrn_orient_matrix_UB_12      -0.0080688000
_diffrn_orient_matrix_UB_13      -0.0545417000
_diffrn_orient_matrix_UB_21      -0.0570151000
_diffrn_orient_matrix_UB_22      -0.0040439000
_diffrn_orient_matrix_UB_23      0.0425851000
_diffrn_orient_matrix_UB_31      -0.0039803000
_diffrn_orient_matrix_UB_32      0.1987866000
_diffrn_orient_matrix_UB_33      -0.0013132000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14341
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.492
_diffrn_reflns_theta_min         3.970
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.326
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.41a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       plate
_exptl_crystal_F_000             1420
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0617P)^2^+3.2010P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2731
_reflns_number_total             3028
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06144a2.cif
_cod_data_source_block           ks2203b_auto
_cod_depositor_comments
'Adding full bibliography for 7131149--7131152.cif.'
_cod_original_cell_volume        3019.01(8)
_cod_database_code               7131150
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.617
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 S1-C17 \\sim S1-C16
 with sigma of 0.02
 F6-C17 \\sim F3-C16
 with sigma of 0.02
 F4-C17 \\sim F1-C16
 with sigma of 0.02
 F6-F5 \\sim F3-F2
 with sigma of 0.04
 C17-F5 \\sim C16-F2
 with sigma of 0.02
 F4-F5 \\sim F1-F2
 with sigma of 0.04
 S1-F6 \\sim S1-F3
 with sigma of 0.04
 S1-F4 \\sim S1-F1
 with sigma of 0.04
 S1-F5 \\sim S1-F2
 with sigma of 0.04
 F6-F4 \\sim F3-F1
 with sigma of 0.04
3. Others
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(C16)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=Sof(C17)=FVAR(1)
 Fixed Sof: O1(0.5) O2(0.5) N2(0.5) O3(0.5) O4(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15)
;
_shelx_res_checksum              87599
_shelx_hkl_checksum              6422
_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 1.344
_oxdiff_exptl_absorpt_empirical_full_min 0.724