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_7250308
_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         'C6 H4 Cl2, C30 H22 N10'
_chemical_formula_sum            'C36 H26 Cl2 N10'
_chemical_formula_weight         669.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 103.244(3)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   11.7987(4)
_cell_length_b                   19.0987(4)
_cell_length_c                   23.8997(6)
_cell_measurement_reflns_used    14428
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      31.2230
_cell_measurement_theta_min      2.4410
_cell_volume                     5242.3(3)
_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     -5.00  57.00   0.50   10.00    --  -11.26  57.00 -30.00  124
  2  \w     -2.00  90.00   0.50   10.00    --   12.67  37.00 -90.00  184
  3  \w     39.00  90.00   0.50   10.00    --   12.67 179.00-120.00  102
  4  \w    -54.00 -29.00   0.50   10.00    --   12.67 -37.00  60.00   50
  5  \w    -82.00  16.00   0.50   10.00    --  -11.26 -77.00 -30.00  196
  6  \w     22.00  47.00   0.50   10.00    --   12.67-136.00  -2.00   50
  7  \w     33.00  67.00   0.50   10.00    --   12.67-133.00 175.00   68
;
_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  0.0687
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            53311
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.434
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59485
_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    1.273
_exptl_crystal_description       plate
_exptl_crystal_F_000             2076
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.320
_refine_diff_density_min         -0.797
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     670
_refine_ls_number_reflns         11561
_refine_ls_number_restraints     148
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0775
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1217P)^2^+4.7722P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2194
_refine_ls_wR_factor_ref         0.2429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7710
_reflns_number_total             11561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00289c2.cif
_cod_data_source_block           TCDP-o-DCB
_cod_depositor_comments
'Adding full bibliography for 7250300--7250316.cif.'
_cod_database_code               7250308
_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
 Cl1-C69 = Cl9-C68
 1.74 with sigma of 0.01
 C73-Cl1 \\sim Cl1-C68
 with sigma of 0.02
 Cl7-C1 \\sim Cl8-C6
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C70 \\sim C68 \\sim C69 \\sim C73 \\sim C72 \\sim C71 \\sim Cl1 \\sim Cl9:
within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
Uanis(Cl9) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C70) \\sim Ueq, Uanis(C72)
\\sim Ueq, Uanis(C71) \\sim Ueq, Uanis(C73) \\sim Ueq, Uanis(C69) \\sim Ueq,
Uanis(Cl1) \\sim Ueq, Uanis(Cl9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C1) \\sim
Ueq, Uanis(C6) \\sim Ueq, Uanis(Cl8) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(Cl7)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: Cl9(0.5) C68(0.5) C69(0.5) C73(0.5) H73(0.5) C72(0.5) H72(0.5)
 C71(0.5) H71(0.5) C70(0.5) H70(0.5) Cl1(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C54(H54), C13(H13), C56(H56), C47(H47), C11(H11), C45(H45), C5(H5), C4(H4),
 C3(H3), C2(H2), C73(H73), C72(H72), C71(H71), C70(H70)
5.b Fitted hexagon refined as free rotating group:
 C1(C6,C5,C4,C3,C2), C68(C69,C73,C72,C71,C70)
5.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C50(H50A,H50B,H50C), C26(H26A,H26B,H26C), C59(H59A,H59B,
 H59C), C60(H60A,H60B,H60C), C58(H58A,H58B,H58C), C49(H49A,H49B,H49C), C51(H51A,
 H51B,H51C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              76416
_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
;