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_7250315
_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         'C30 H22 N10, C6 H5 Cl'
_chemical_formula_sum            'C36 H27 Cl N10'
_chemical_formula_weight         635.12
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-03-10 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                82.417(5)
_cell_angle_beta                 78.205(5)
_cell_angle_gamma                77.833(5)
_cell_formula_units_Z            1
_cell_length_a                   8.1115(4)
_cell_length_b                   8.9633(6)
_cell_length_c                   11.3830(7)
_cell_measurement_reflns_used    3566
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      30.2050
_cell_measurement_theta_min      2.6470
_cell_volume                     788.51(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      143.15
_diffrn_detector_type            HyPix
_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    -21.00   5.00   0.50    2.86    --  -11.11  57.00  30.00   52
  2  \w    -12.00  80.00   0.50    2.86    --   12.51  72.00  42.00  184
  3  \w     32.00  57.00   0.50    2.86    --  -11.11  57.00  30.00   50
  4  \w     49.00  75.00   0.50    2.86    --   12.51 179.00  30.00   52
  5  \w     39.00  70.00   0.50    2.86    --   12.51 179.00-120.00   62
  6  \w     -5.00  49.00   0.50    2.86    --   12.51  57.00-150.00  108
  7  \w    -53.00  39.00   0.50    2.86    --   12.51 -72.00 -87.00  184
  8  \w     -1.00  51.00   0.50    2.86    --   12.51 -99.00-180.00  104
  9  \w    -90.00 -65.00   0.50    2.86    --  -11.11 179.00-120.00   50
 10  \w    -75.00 -47.00   0.50    2.86    --  -11.11 179.00 -90.00   56
;
_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  0.0461
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9331
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         2.335
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
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    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             330
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.358
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0864
_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^)+(0.1639P)^2^+0.6693P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2622
_refine_ls_wR_factor_ref         0.2888
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2430
_reflns_number_total             3480
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00289c2.cif
_cod_data_source_block           TCDP-PhCl
_cod_depositor_comments
'Adding full bibliography for 7250300--7250316.cif.'
_cod_database_code               7250315
_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
 C26-C25 = C26-C27 = C22-C23 = C27-C22 = C24-C23
 1.39 with sigma of 0.01
 C25-C24
 1.39 with sigma of 0.01
 C27-Cl21 \\sim Cl21-C23
 with sigma of 0.005
3. Rigid bond restraints
 Cl21, C22, C23, C25, C24, C26, C27
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
Uanis(Cl21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C25)
\\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq:
with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: Cl21(0.5) C23(0.5) H23(0.5) C22(0.5) C27(0.5) H27(0.5) C26(0.5)
 H26(0.5) C25(0.5) H25(0.5) C24(0.5) H24(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C23(H23), C27(H27), C26(H26), C25(H25), C24(H24)
6.b Fitted hexagon refined as free rotating group:
 C6(C1,C2,C3,C4,C5), C23(C22,C27,C26,C25,C24)
6.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              64244
_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
;