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_7250309
_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         '2(C15 H11 N5), 2(C5 H5 N)'
_chemical_formula_sum            'C40 H32 N12'
_chemical_formula_weight         680.77
_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             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                70.868(8)
_cell_angle_beta                 83.072(7)
_cell_angle_gamma                82.513(7)
_cell_formula_units_Z            2
_cell_length_a                   9.3409(8)
_cell_length_b                   12.7905(11)
_cell_length_c                   16.1963(14)
_cell_measurement_reflns_used    3000
_cell_measurement_temperature    143.19(13)
_cell_measurement_theta_max      71.4310
_cell_measurement_theta_min      3.6740
_cell_volume                     1806.3(3)
_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 8.1195
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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    -12.00  32.00   1.00    9.55    --  -34.65  37.00 150.00   44
  2  \w     -6.00  22.00   1.00    9.55    --  -34.65  37.00 120.00   28
  3  \w     19.00  47.00   1.00    9.55    --   34.65 -57.00 -60.00   28
  4  \w     56.00 102.00   1.00    9.55    --   34.65  57.00   0.00   46
  5  \w      7.00  73.00   1.00    9.55    --   34.65 -99.00 -60.00   66
  6  \w     26.00  53.00   1.00    9.55    --   34.65  57.00 -90.00   27
  7  \w      7.00  34.00   1.00    9.55    --   34.65 -19.00 -60.00   27
  8  \w    -10.00  17.00   1.00    9.55    --   34.65 -77.00 150.00   27
  9  \w      7.00  71.00   1.00    9.55    --   34.65 -99.00-180.00   64
 10  \w     38.00  65.00   1.00    9.55    --   34.65-125.00-180.00   27
 11  \w    -33.00  29.00   1.00    9.55    --   34.65 -57.00 -90.00   62
 12  \w     17.00  43.00   1.00    9.55    --   34.65  37.00-150.00   26
 13  \w     76.00 102.00   1.00    9.55    --   34.65  57.00 -90.00   26
 14  \w     42.00  85.00   1.00    9.55    --   34.65-125.00  90.00   43
 15  \w    -29.00   1.00   1.00    9.55    --   34.65 -19.00 -60.00   30
 16  \w    -20.00  53.00   1.00    9.55    --   34.65 -77.00  60.00   73
 17  \w    -25.00  44.00   1.00    9.55    --   34.65 -37.00-180.00   69
 18  \w     40.00  71.00   1.00   38.21    --  107.04 -45.00 120.00   31
 19  \w     39.00  72.00   1.00   38.21    --  107.04 -45.00 -60.00   33
 20  \w     44.00  71.00   1.00   38.21    --  107.04 -45.00  30.00   27
 21  \w     39.00 173.00   1.00   38.21    --  107.04   0.00   0.00  134
 22  \w     90.00 151.00   1.00   38.21    --  107.04  61.00-150.00   61
 23  \w     40.00 109.00   1.00   38.21    --  107.04-111.00 -30.00   69
 24  \w     40.00  67.00   1.00   38.21    --  107.04 -45.00 -30.00   27
 25  \w     43.00 102.00   1.00   38.21    --  107.04-111.00 -90.00   59
 26  \w     48.00  75.00   1.00   38.21    --  107.04 -94.00 120.00   27
 27  \w    119.00 168.00   1.00   38.21    --  107.04  77.00-180.00   49
 28  \w    114.00 156.00   1.00   38.21    --  107.04  77.00  30.00   42
 29  \w     40.00  72.00   1.00   38.21    --  107.04 -45.00  90.00   32
 30  \w     40.00  71.00   1.00   38.21    --  107.04 -45.00 -90.00   31
 31  \w     41.00  72.00   1.00   38.21    --  107.04 -45.00  60.00   31
 32  \w     40.00  74.00   1.00   38.21    --  107.04 -61.00  30.00   34
 33  \w     39.00  64.00   1.00   38.21    --  107.04 -45.00 150.00   25
 34  \w     69.00 109.00   1.00   38.21    --  107.04-111.00  90.00   40
 35  \w     45.00  70.00   1.00   38.21    --  107.04 -45.00-150.00   25
 36  \w     65.00 109.00   1.00   38.21    --  107.04-111.00-180.00   44
 37  \w     39.00  70.00   1.00   38.21    --  107.04 -45.00-120.00   31
 38  \w     67.00 109.00   1.00   38.21    --  107.04 -77.00 -60.00   42
 39  \w     90.00 117.00   1.00   38.21    --  107.04 -77.00 120.00   27
 40  \w     52.00  77.00   1.00   38.21    --  107.04 -77.00 120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6592
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         2.898
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58708
_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    1.252
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     476
_refine_ls_number_reflns         6592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0787
_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^)+(0.1398P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2206
_refine_ls_wR_factor_ref         0.2491
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4295
_reflns_number_total             6592
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00289c2.cif
_cod_data_source_block           TCDP-pyridine
_cod_depositor_comments
'Adding full bibliography for 7250300--7250316.cif.'
_cod_database_code               7250309
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.695(8)
 0.305(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C25(H25), C5(H5), C3(H3), C48(H48), C45(H45), C49(H49), C46(H46),
 C42(H42), C43(H43), C52(H52), C51(H51), C44(H44), C50(H50)
3.b Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C27(H27A,H27B,H27C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C),
 C28(H28A,H28B,H28C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              63549
_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
- Detector area scaling
;