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_7250300
_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 O2)'
_chemical_formula_sum            'C38 H38 N10 O4'
_chemical_formula_weight         698.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.3360(19)
_cell_length_b                   9.3587(5)
_cell_length_c                   15.4039(8)
_cell_measurement_reflns_used    5407
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      28.3300
_cell_measurement_theta_min      2.9820
_cell_volume                     3796.6(4)
_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    -24.00   2.00   0.50    3.40    --   21.12  19.00 -90.00   52
  2  \w     69.00 109.00   0.50    3.40    --   21.12  -9.00-127.00   80
  3  \w     68.00  94.00   0.50    3.40    --   21.12 153.00 -44.00   52
  4  \w    -72.00  11.00   0.50    3.40    --   21.12  -9.00-127.00  166
  5  \w     16.00  86.00   0.50    3.40    --   21.12-128.00 167.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0111909000
_diffrn_orient_matrix_UB_12      -0.0416610000
_diffrn_orient_matrix_UB_13      -0.0071592000
_diffrn_orient_matrix_UB_21      0.0242902000
_diffrn_orient_matrix_UB_22      -0.0195181000
_diffrn_orient_matrix_UB_23      0.0062670000
_diffrn_orient_matrix_UB_31      -0.0030770000
_diffrn_orient_matrix_UB_32      -0.0022777000
_diffrn_orient_matrix_UB_33      0.0751993000
_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  0.0464
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16645
_diffrn_reflns_point_group_measured_fraction_full 0.852
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.095
_diffrn_reflns_theta_min         2.980
_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  0.65304
_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    1.223
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1370 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         7049
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0603P)^2^+0.5017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1392
_reflns_Friedel_coverage         0.633
_reflns_Friedel_fraction_full    0.694
_reflns_Friedel_fraction_max     0.681
_reflns_number_gt                4575
_reflns_number_total             7049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00289c2.cif
_cod_data_source_block           TCDP-EtOAc
_cod_depositor_comments
'Adding full bibliography for 7250300--7250316.cif.'
_cod_database_code               7250300
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C N H O'
_reflns_odcompleteness_completeness 99.49
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C44(H44A,H44B), C50(H50A,H50B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C28(H28), C26(H26), C17(H17)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C31(H31A,H31B,H31C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C32(H32A,H32B,H32C), C30(H30A,H30B,H30C), C46(H46A,H46B,H46C), C52(H52A,
 H52B,H52C), C45(H45A,H45B,H45C), C51(H51A,H51B,H51C)
;
_shelx_res_checksum              24702
_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 1.348
_oxdiff_exptl_absorpt_empirical_full_min 0.774