Diverse tetracyanodihydrodipyrazinopyrazine clathrate crystals assembled from weak intermolecular interactions
Watanabe, Kosuke; Sugiyama, Haruki; Segawa, Yasutomo; CrystEngComm 27 (2025) 3552–3559; doi:10.1039/D5CE00289C

data_7250313
_publ_section_title
;
 Diverse tetracyanodihydrodipyrazinopyrazine clathrate crystals assembled
 from weak intermolecular interactions
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              3552
_journal_page_last               3559
_journal_paper_doi               10.1039/D5CE00289C
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         '4(C4 H4 S), C30 H22 N10'
_chemical_formula_sum            'C46 H38 N10 S4'
_chemical_formula_weight         859.10
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-02-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                68.012(4)
_cell_angle_beta                 68.117(4)
_cell_angle_gamma                86.081(4)
_cell_formula_units_Z            1
_cell_length_a                   10.4879(5)
_cell_length_b                   10.8573(5)
_cell_length_c                   11.2117(5)
_cell_measurement_reflns_used    4426
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      29.1590
_cell_measurement_theta_min      3.4400
_cell_volume                     1094.75(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      143.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     24.00  51.00   0.50    0.07    --  -19.87  23.00 -27.00   54
  2  \w     16.00  46.00   0.50    0.07    --   21.12 -57.00   0.00   60
  3  \w    -10.00  16.00   0.50    0.07    --  -19.87 -99.00 -90.00   52
  4  \w    -11.00  29.00   0.50    0.07    --  -19.87 -99.00 -30.00   80
  5  \w    -14.00  11.00   0.50    0.07    --  -19.87 -99.00  30.00   50
  6  \w    -12.00  29.00   0.50    0.07    --  -19.87 -99.00  90.00   82
  7  \w     -1.00  65.00   0.50    0.07    --  -19.87 -23.00 167.00  132
  8  \w    -12.00  14.00   0.50    0.07    --  -19.87 -99.00-180.00   52
  9  \w    -43.00 -11.00   0.50    0.07    --   21.12 -57.00   0.00   64
 10  \w    -77.00  15.00   0.50    0.07    --  -19.87 -57.00  90.00  184
 11  \w   -102.00  17.00   0.50    0.07    --  -19.87  23.00 -27.00  238
 12  \w   -108.00  -5.00   0.50    0.07    --  -19.87 -23.00 167.00  206
 13  \w   -115.00 -44.00   0.50    0.07    --  -19.87 179.00-150.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13745
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.040
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.514
_refine_diff_density_min         -1.012
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4471
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0997
_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^)+(0.1619P)^2^+2.6623P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2861
_refine_ls_wR_factor_ref         0.3140
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3282
_reflns_number_total             4471
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00289c2.cif
_cod_data_source_block           TCDP-thiophene
_cod_depositor_comments
'Adding full bibliography for 7250300--7250316.cif.'
_cod_database_code               7250313
_shelx_shelxl_version_number     2019/3
_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. Restrained distances
 S26-C30 = S26-C27 = S21-C22 = S21-C25
 1.73 with sigma of 0.01
 C29-C28
 1.53 with sigma of 0.01
 S26-C30 \\sim S26-C27
 with sigma of 0.001
 C30-C29 \\sim C28-C27
 with sigma of 0.001
 S21-C22 \\sim S21-C25
 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C3(H3), C5(H5), C24(H24), C30(H30), C28(H28), C25(H25), C22(H22),
 C29(H29), C27(H27)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              55420
_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
;