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_7131149
_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         'C36 H28 N2 S2'
_chemical_formula_sum            'C36 H28 N2 S2'
_chemical_formula_weight         552.72
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-13 deposited with the CCDC.	2022-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.8351(9)
_cell_length_b                   12.3566(5)
_cell_length_c                   8.2933(3)
_cell_measurement_reflns_used    10845
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.6810
_cell_measurement_theta_min      2.2350
_cell_volume                     2647.50(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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      100
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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      5.00  79.00   0.50   10.00    --  -10.20  45.00  90.00  148
  2  \w    -99.00 -31.00   0.50   10.00    --  -10.20  45.00 150.00  136
  3  \w    -15.00  79.00   0.50   10.00    --  -10.20  45.00 150.00  188
  4  \w    -99.00 -19.00   0.50   10.00    --  -10.20  45.00  90.00  160
  5  \w    -17.00  10.00   0.50   10.00    --  -10.20  45.00 -18.33   54
  6  \w    -56.00 -30.00   0.50   10.00    --  -10.20  45.00 -18.33   52
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0073326000
_diffrn_orient_matrix_UB_12      0.0532156000
_diffrn_orient_matrix_UB_13      0.0226531000
_diffrn_orient_matrix_UB_21      -0.0261247000
_diffrn_orient_matrix_UB_22      0.0170823000
_diffrn_orient_matrix_UB_23      -0.0072710000
_diffrn_orient_matrix_UB_31      -0.0043203000
_diffrn_orient_matrix_UB_32      -0.0128990000
_diffrn_orient_matrix_UB_33      0.0821495000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            28457
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.281
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       prism
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 2234 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5846
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+0.6279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0768
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                5402
_reflns_number_total             5846
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06144a2.cif
_cod_data_source_block           ks2110b
_cod_depositor_comments
'Adding full bibliography for 7131149--7131152.cif.'
_cod_database_code               7131149
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     100K
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C26(H26), C27(H27), C28(H28), C32(H32), C33(H33), C34(H34), C35(H35)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_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 1.043
_oxdiff_exptl_absorpt_empirical_full_min 0.962