Charge-transfer crystal with segregated packing structure constructed with hexaarylbenzene and tetracyanoquinodimethane
Ando, Rempei; Jin, Mingoo; Ito, Hajime; CrystEngComm 23 (2021) 5564–5568; doi:10.1039/D1CE00726B

data_7243355
_publ_section_title
;
 Charge-transfer crystal with segregated packing structure constructed
 with hexaarylbenzene and tetracyanoquinodimethane
;
_journal_issue                   33
_journal_name_full               CrystEngComm
_journal_page_first              5564
_journal_page_last               5568
_journal_paper_doi               10.1039/D1CE00726B
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         '0.5(C36 H24 N6), 1.75(C12 H4 N4)'
_chemical_formula_sum            'C39 H19 N10'
_chemical_formula_weight         627.64
_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             2021-02-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-27 deposited with the CCDC.	2021-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                96.4080(10)
_cell_angle_beta                 96.9700(10)
_cell_angle_gamma                94.6330(10)
_cell_formula_units_Z            4
_cell_length_a                   7.74030(10)
_cell_length_b                   17.6776(2)
_cell_length_c                   23.7797(2)
_cell_measurement_reflns_used    17528
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.3940
_cell_measurement_theta_min      3.3180
_cell_volume                     3194.85(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.953
_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    -68.00  12.00   0.50    6.51    --  -47.20  91.00 -27.00  160
  2  \w    -35.00  22.00   0.50    6.51    --  -47.20  37.00 -90.00  114
  3  \w    -58.00 -32.00   0.50   12.83    -- -102.00 103.00-163.14   52
  4  \w    -70.00 -30.00   0.50   12.83    -- -102.00  61.00 -90.00   80
  5  \w    -70.00 -34.00   0.50   12.83    -- -102.00  61.00 -60.00   72
  6  \w    -66.00 -41.00   0.50   12.83    -- -102.00  61.00   0.00   50
  7  \w    -93.00 -67.00   0.50   12.83    -- -102.00  91.00 -27.00   52
  8  \w   -106.00 -62.00   0.50   12.83    -- -102.00 103.00-163.14   88
  9  \w    -64.00 -38.00   0.50   12.83    -- -102.00  61.00-180.00   52
 10  \w   -157.00 -80.00   0.50   12.83    -- -102.00 -91.00-140.00  154
 11  \w   -111.00 -74.00   0.50    6.51    --  -47.20-125.00 -60.00   74
 12  \w   -115.00 -88.00   0.50   12.83    -- -102.00 -94.00 -30.00   54
 13  \w   -120.00 -95.00   0.50    6.51    --  -47.20-125.00  90.00   50
 14  \w   -175.00-141.00   0.50   12.83    -- -102.00 -94.00 -30.00   68
 15  \w   -165.00-121.00   0.50   12.83    -- -102.00 -61.00 -90.00   88
 16  \w    -71.00 -42.00   0.50   12.83    -- -102.00  61.00  90.00   58
 17  \w    -64.00 -39.00   0.50   12.83    -- -102.00  77.00 120.00   50
 18  \w   -124.00 -77.00   0.50   12.83    -- -102.00  77.00 120.00   94
 19  \w    -20.00  57.00   0.50    6.51    --   47.20 -91.00-140.00  154
 20  \w     45.00  70.00   0.50   12.83    --  104.75 -91.00-140.00   50
 21  \w     61.00 105.00   0.50   12.83    --  104.75 -94.00-120.00   88
 22  \w     81.00 106.00   0.50   12.83    --  104.75-125.00-180.00   50
 23  \w     34.00  80.00   0.50   12.83    --  104.75-125.00-180.00   92
 24  \w     32.00 108.00   0.50   12.83    --  104.75-125.00 -90.00  152
 25  \w     81.00 106.00   0.50   12.83    --  104.75 -94.00  30.00   50
 26  \w     47.00  98.00   0.50   12.83    --  104.75 -94.00  90.00  102
 27  \w     35.00 103.00   0.50   12.83    --  104.75 -94.00   0.00  136
 28  \w     46.00 112.00   0.50   12.83    --  104.75-125.00 -30.00  132
 29  \w     32.00  60.00   0.50   12.83    --  104.75 -94.00  30.00   56
 30  \w    -16.00  32.00   0.50    6.51    --   47.20 -37.00 120.00   96
 31  \w    -26.00  13.00   0.50    6.51    --   47.20 -19.00  60.00   78
 32  \w    -24.00   1.00   0.50    6.51    --   47.20 -19.00 -30.00   50
 33  \w    -11.00  38.00   0.50    6.51    --   47.20 -37.00 -90.00   98
 34  \w     92.00 139.00   0.50   12.83    --  104.75  30.00   0.00   94
 35  \w    143.00 177.00   0.50   12.83    --  104.75  30.00   0.00   68
 36  \w    113.00 151.00   0.50   12.83    --  104.75  91.00 -27.00   76
 37  \w    102.00 178.00   0.50   12.83    --  104.75 125.00 -90.00  152
 38  \w    109.00 177.00   0.50   12.83    --  104.75  30.00  90.00  136
 39  \w     86.00 167.00   0.50   12.83    --  104.75  77.00 -60.00  162
 40  \w     96.00 176.00   0.50   12.83    --  104.75  30.00  60.00  160
 41  \w    -20.00   8.00   0.50    6.51    --   47.20 -19.00-150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0839679000
_diffrn_orient_matrix_UB_12      -0.0757925000
_diffrn_orient_matrix_UB_13      -0.0089308000
_diffrn_orient_matrix_UB_21      0.1398918000
_diffrn_orient_matrix_UB_22      0.0279098000
_diffrn_orient_matrix_UB_23      0.0515137000
_diffrn_orient_matrix_UB_31      -0.1181365000
_diffrn_orient_matrix_UB_32      -0.0351853000
_diffrn_orient_matrix_UB_33      0.0398937000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            41505
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.316
_diffrn_reflns_theta_min         2.962
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'bluish blue'
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       plate
_exptl_crystal_F_000             1292
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1042
_refine_ls_number_reflns         12782
_refine_ls_number_restraints     421
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1113P)^2^+0.5653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1940
_refine_ls_wR_factor_ref         0.2108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9328
_reflns_number_total             12782
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00726b2.cif
_cod_data_source_block           adr-277-tcnq-hpyb-3
_cod_depositor_comments
'Adding full bibliography for 7243354--7243355.cif.'
_cod_original_cell_volume        3194.84(6)
_cod_database_code               7243355
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C N H'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.880
_diffrn_oxdiff_digest_frames
;
010be7f3d78d0296d6988b31308b4f38b800025d611
;
_diffrn_oxdiff_digest_hkl
;
01fc364e6415ffa729ef55fa6cf60e5f6771d6
;
_reflns_odcompleteness_completeness 98.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N004-C00E \\sim N0-C00E
 with sigma of 0.02
 N004-C029 \\sim N0-C0
 with sigma of 0.02
 C00E-C02G \\sim C00E-C0AA
 with sigma of 0.02
 C02G-C02P \\sim C0AA-C1AA
 with sigma of 0.02
 C02P-C02H \\sim C1AA-C02H
 with sigma of 0.02
 C02H-C029 \\sim C02H-C0
 with sigma of 0.02
 N004-C02H \\sim N0-C02H
 with sigma of 0.04
 C00E-C02P \\sim C00E-C1AA
 with sigma of 0.04
 C00E-C029 \\sim C00E-C0
 with sigma of 0.04
 C02G-C02H \\sim C0AA-C02H
 with sigma of 0.04
 N01O-C02K \\sim N01P-C2AA
 with sigma of 0.02
 N01O-C01Z \\sim N01P-C01Z
 with sigma of 0.02
 C02K-C02L \\sim C2AA-C02L
 with sigma of 0.02
 C02L-C02M \\sim C02L-C02N
 with sigma of 0.02
 C02M-C02B \\sim C02N-C3AA
 with sigma of 0.02
 C02B-C01Z \\sim C3AA-C01Z
 with sigma of 0.02
 N01O-C02L \\sim N01P-C02L
 with sigma of 0.04
 C02K-C01Z \\sim C2AA-C01Z
 with sigma of 0.04
 C02L-C02B \\sim C02L-C3AA
 with sigma of 0.04
 C02M-C01Z \\sim C02N-C01Z
 with sigma of 0.04
 C025-C02D \\sim C025-C4AA
 with sigma of 0.02
 C025-N02N \\sim C025-N02O
 with sigma of 0.02
 C02D-C02E \\sim C4AA-C5AA
 with sigma of 0.02
 C02E-C02O \\sim C5AA-C02O
 with sigma of 0.02
 C02O-C02Q \\sim C02O-C02R
 with sigma of 0.02
 C02Q-N02N \\sim C02R-N02O
 with sigma of 0.02
 C025-C02E \\sim C025-C5AA
 with sigma of 0.04
 C025-C02Q \\sim C025-C02R
 with sigma of 0.04
 C02D-C02O \\sim C4AA-C02O
 with sigma of 0.04
 C02O-N02N \\sim C02O-N02O
 with sigma of 0.04
 N001-C00D \\sim N1-C00D
 with sigma of 0.02
 N001-C01I \\sim N1-C6AA
 with sigma of 0.02
 C00D-C00B \\sim C00D-C7AA
 with sigma of 0.02
 C00B-C01U \\sim C7AA-C01V
 with sigma of 0.02
 C01U-C01L \\sim C01V-C01L
 with sigma of 0.02
 C01L-C01I \\sim C01L-C6AA
 with sigma of 0.02
 N001-C01L \\sim N1-C01L
 with sigma of 0.04
 C00D-C01U \\sim C00D-C01V
 with sigma of 0.04
 C00D-C01I \\sim C00D-C6AA
 with sigma of 0.04
 C00B-C01L \\sim C7AA-C01L
 with sigma of 0.04
 C021-C023 \\sim C021-C2
 with sigma of 0.02
 N022-C02J \\sim N2-C8AA
 with sigma of 0.02
 N022-C023 \\sim N2-C2
 with sigma of 0.02
 C02J-C02F \\sim C8AA-C9AA
 with sigma of 0.02
 C02F-C02C \\sim C9AA-C0BA
 with sigma of 0.02
 C02C-C026 \\sim C0BA-C1
 with sigma of 0.02
 C026-C023 \\sim C1-C2
 with sigma of 0.02
 C021-N022 \\sim C021-N2
 with sigma of 0.04
 C021-C026 \\sim C021-C1
 with sigma of 0.04
 N022-C02F \\sim N2-C9AA
 with sigma of 0.04
 N022-C026 \\sim N2-C1
 with sigma of 0.04
 C02J-C02C \\sim C8AA-C0BA
 with sigma of 0.04
 C02J-C023 \\sim C8AA-C2
 with sigma of 0.04
 C02F-C026 \\sim C9AA-C1
 with sigma of 0.04
 C02C-C023 \\sim C0BA-C2
 with sigma of 0.04
 C019-N01T \\sim C019-N01U
 with sigma of 0.02
 C019-C027 \\sim C019-C3
 with sigma of 0.02
 N01T-C02I \\sim N01U-C1BA
 with sigma of 0.02
 C02I-C028 \\sim C1BA-C028
 with sigma of 0.02
 C028-C02A \\sim C028-C2BA
 with sigma of 0.02
 C02A-C027 \\sim C2BA-C3
 with sigma of 0.02
 C019-C02I \\sim C019-C1BA
 with sigma of 0.04
 C019-C02A \\sim C019-C2BA
 with sigma of 0.04
 N01T-C028 \\sim N01U-C028
 with sigma of 0.04
 C028-C027 \\sim C028-C3
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C02D \\sim C025 \\sim N02N \\sim C02Q \\sim C02O \\sim C02E: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
C01Z \\sim N01O \\sim C02K \\sim C02L \\sim C02M \\sim C02B: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
C0AA \\sim N0 \\sim C0 \\sim C1AA \\sim C00E \\sim C02H: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08
C01Z \\sim N01P \\sim C2AA \\sim C02L \\sim C02N \\sim C3AA: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
C02B \\sim C01Z \\sim N01O \\sim C02K \\sim C02L \\sim C02M: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
C4AA \\sim C5AA \\sim C15 \\sim C02R \\sim N02O \\sim C025: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
C025 \\sim N02N \\sim C02Q \\sim C02O \\sim C02E \\sim C02D: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 C02Q, N02N, C025, C02D, C02E, C02O
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C02B, N01O, C02K, C02L, C02M
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00E, C02H, C0AA, N0, C0, C1AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N01O, C02K, C02L, C02M, C02B, C01Z
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C02L, C01Z, N01P, C2AA, C02N, C3AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4AA, C5AA, C15, C02R, N02O, C025
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C025, N02N, C02Q, C02E, C02O, C02D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: N001(0.65) C00B(0.65) H00B(0.65) C01U(0.65) H01U(0.65) H01L(0.65)
 H01A(0.35) C01I(0.65) H01I(0.65) N004(0.7) C02G(0.7) H02G(0.7) C02P(0.7)
 H02P(0.7) H02H(0.7) H02I(0.3) C029(0.7) H029(0.7) N01T(0.5) C02I(0.5)
 H02S(0.5) H028(0.5) H02T(0.5) C02A(0.5) H02U(0.5) C027(0.5) H027(0.5)
 N01O(0.7) C02K(0.7) H02K(0.7) H02L(0.7) H02A(0.3) C02M(0.7) H02M(0.7)
 C02B(0.7) H02B(0.7) N022(0.65) C02J(0.65) H02J(0.65) C02F(0.65) H02F(0.65)
 C02C(0.65) H02C(0.65) C026(0.65) H026(0.65) C023(0.65) C02D(0.65) H02D(0.65)
 C02E(0.65) H02E(0.65) C02O(0.65) H02O(0.65) C02Q(0.65) H02Q(0.65) N02N(0.65)
 C0AA(0.3) H0AA(0.3) N0(0.3) C0(0.3) H0(0.3) C1AA(0.3) H1AA(0.3) N01P(0.3)
 C2AA(0.3) H2AA(0.3) C02N(0.3) H02N(0.3) C3AA(0.3) H3AA(0.3) N02O(0.35)
 C02R(0.35) H02R(0.35) C4AA(0.35) H4AA(0.35) C5AA(0.35) H5AA(0.35) C15(0.35)
 H15(0.35) N1(0.35) C6AA(0.35) H6AA(0.35) C01V(0.35) H01V(0.35) C7AA(0.35)
 H7AA(0.35) C1(0.35) H1(0.35) C2(0.35) N2(0.35) C8AA(0.35) H8AA(0.35)
 C9AA(0.35) H9AA(0.35) C0BA(0.35) H0BA(0.35) N01U(0.5) C1BA(0.5) H1BA(0.5)
 C2BA(0.5) H2BA(0.5) C3(0.5) H3(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C01U(H01U), C01L(H01L), C01L(H01A), C01I(H01I), C02G(H02G),
 C02P(H02P), C02H(H02H), C02H(H02I), C029(H029), C005(H005), C00F(H00F),
 C00I(H00I), C00L(H00L), C00M(H00M), C00P(H00P), C00R(H00R), C00U(H00U),
 C00W(H00W), C00Y(H00Y), C011(H011), C016(H016), C02I(H02S), C028(H028),
 C028(H02T), C02A(H02U), C027(H027), C01E(H01E), C01J(H01J), C02K(H02K),
 C02L(H02L), C02L(H02A), C02M(H02M), C02B(H02B), C02J(H02J), C02F(H02F),
 C02C(H02C), C026(H026), C02D(H02D), C02E(H02E), C02O(H02O), C02Q(H02Q),
 C0AA(H0AA), C0(H0), C1AA(H1AA), C2AA(H2AA), C02N(H02N), C3AA(H3AA), C02R(H02R),
  C4AA(H4AA), C5AA(H5AA), C15(H15), C6AA(H6AA), C01V(H01V), C7AA(H7AA), C1(H1),
 C8AA(H8AA), C9AA(H9AA), C0BA(H0BA), C1BA(H1BA), C2BA(H2BA), C3(H3)
6.b Fitted hexagon refined as free rotating group:
 N001(C00D,C00B,C01U,C01L,C01I), N004(C00E,C02G,C02P,C02H,C029), C019(N01T,
 C02I,C028,C02A,C027), N01O(C02K,C02L,C02M,C02B,C01Z), N022(C02J,C02F,C02C,C026,
 C023), C025(C02D,C02E,C02O,C02Q,N02N), C1(C2,N2,C8AA,C9AA,C0BA)
;
_shelx_res_checksum              1243
_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 1.353
_oxdiff_exptl_absorpt_empirical_full_min 0.773