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_7250310
_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, 2(C4 H8 O)'
_chemical_formula_sum            'C38 H38 N10 O2'
_chemical_formula_weight         666.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-19
_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                90
_cell_angle_beta                 99.256(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0161(4)
_cell_length_b                   12.1980(6)
_cell_length_c                   16.1054(7)
_cell_measurement_reflns_used    3558
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      27.6090
_cell_measurement_theta_min      3.0540
_cell_volume                     1748.18(14)
_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                 'CCD plate'
_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     -3.00  23.00   0.50   40.00    --   21.12  57.00 120.00   52
  2  \w     75.00 101.00   0.50   40.00    --   21.12  57.00 120.00   52
  3  \w     61.00  87.00   0.50   40.00    --   21.12 179.00 -60.00   52
  4  \w     39.00 108.00   0.50   40.00    --   21.12 179.00 -90.00  138
  5  \w    -39.00  31.00   0.50   40.00    --   21.12 -57.00-150.00  140
  6  \w     30.00  55.00   0.50   40.00    --   21.12-127.00 -73.00   50
  7  \w    -14.00  34.00   0.50   40.00    --  -19.87 -99.00 -90.00   96
  8  \w     28.00  65.00   0.50   40.00    --   21.12-143.00 116.00   74
  9  \w    -99.00  -9.00   0.50   40.00    --  -19.87 -57.00  60.00  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0251938000
_diffrn_orient_matrix_UB_12      -0.0471310000
_diffrn_orient_matrix_UB_13      0.0194467000
_diffrn_orient_matrix_UB_21      -0.0296613000
_diffrn_orient_matrix_UB_22      0.0339877000
_diffrn_orient_matrix_UB_23      0.0290820000
_diffrn_orient_matrix_UB_31      -0.0695528000
_diffrn_orient_matrix_UB_32      0.0025336000
_diffrn_orient_matrix_UB_33      -0.0276936000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13406
_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         27.103
_diffrn_reflns_theta_min         2.954
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90390
_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    1.267
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3855
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0591
_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^)+(0.0452P)^2^+0.9186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1343
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2597
_reflns_number_total             3855
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00289c2.cif
_cod_data_source_block           TCDP-THF
_cod_depositor_comments
'Adding full bibliography for 7250300--7250316.cif.'
_cod_database_code               7250310
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C N H O'
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C23-C22 = C25-C24A
 1.473 with sigma of 0.005
 C24B-C23 = C24A-C23
 1.484 with sigma of 0.005
 C23-C24B \\sim C23-C24A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C24B \\sim O21: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C24A \\sim C25 \\sim O21: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Others
 Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24C)=Sof(H24D)=Sof(H25C)=Sof(H25D)=1-FVAR(1)
 Sof(H23A)=Sof(H23B)=Sof(C24B)=Sof(H24A)=Sof(H24B)=Sof(H25A)=Sof(H25B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B), C23(H23C,H23D), C24B(H24A,H24B), C24A(H24C,
 H24D), C25(H25A,H25B), C25(H25C,H25D)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              27007
_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 1.628
_oxdiff_exptl_absorpt_empirical_full_min 0.805