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_7243354
_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         '3.5(C12 H4 N4), 2(C18 H12 N3)'
_chemical_formula_sum            'C78 H38 N20'
_chemical_formula_weight         1255.28
_chemical_name_systematic        HPyB-TCNQ
_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             2021-02-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-09 deposited with the CCDC.	2021-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                96.381(2)
_cell_angle_beta                 96.351(2)
_cell_angle_gamma                94.418(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7083(2)
_cell_length_b                   17.6112(5)
_cell_length_c                   23.3347(4)
_cell_measurement_reflns_used    7686
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      75.5710
_cell_measurement_theta_min      3.8260
_cell_volume                     3115.98(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_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      123
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.955
_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   -111.00 -19.00   0.50   15.93    --  -42.55 -29.00 161.00  184
  2  \w    -13.00  38.00   0.50   15.93    --  -42.55  19.00  30.00  102
  3  \w    -27.00   0.00   0.50   15.93    --  -42.55  29.00 -37.00   54
  4  \w    -30.00  29.00   0.50   15.93    --  -42.55  57.00 -30.00  118
  5  \w     18.00 119.00   0.50   15.93    --   42.55  29.00 -37.00  202
  6  \w    120.00 175.00   0.50   15.93    --  108.75  29.00 -37.00  110
  7  \w     92.00 158.00   0.50   15.93    --  108.75  45.00   0.00  132
  8  \w     88.00 117.00   0.50   15.93    --  108.75  29.00 -37.00   58
  9  \w     85.00 178.00   0.50   15.93    --  108.75  30.00 -90.00  186
 10  \w     80.00 106.00   0.50   15.93    --  108.75 -94.00-150.00   52
 11  \w     50.00  76.00   0.50   15.93    --  108.75 -94.00-150.00   52
 12  \w     36.00  75.00   0.50   15.93    --  108.75 -61.00 -90.00   78
 13  \w     54.00  80.00   0.50   15.93    --  108.75 -94.00 -60.00   52
 14  \w     65.00 110.00   0.50   15.93    --  108.75-125.00   0.00   90
 15  \w     70.00  95.00   0.50   15.93    --  108.75 -94.00   0.00   50
 16  \w     38.00  69.00   0.50   15.93    --  108.75 -61.00  30.00   62
 17  \w     38.00  71.00   0.50   15.93    --  108.75 -61.00   0.00   66
 18  \w     36.00  72.00   0.50   15.93    --  108.75 -61.00 -30.00   72
 19  \w     43.00  72.00   0.50   15.93    --  108.75 -61.00-120.00   58
 20  \w     38.00  72.00   0.50   15.93    --  108.75 -61.00-180.00   68
 21  \w     42.00 107.00   0.50   15.93    --  108.75-103.00-176.06  130
 22  \w     37.00  72.00   0.50   15.93    --  108.75 -61.00-150.00   70
 23  \w    -31.00  18.00   0.50   15.93    --   42.55 -19.00   0.00   98
 24  \w    -29.00  -4.00   0.50   15.93    --   42.55 -29.00 161.00   50
 25  \w     38.00  86.00   0.50   15.93    --  108.75 -94.00 150.00   96
 26  \w    124.00 150.00   0.50   15.93    --  108.75  30.00 120.00   52
 27  \w     93.00 119.00   0.50   15.93    --  108.75  30.00 120.00   52
 28  \w    -62.00 -37.00   0.50   15.93    --  -42.55  57.00 -30.00   50
 29  \w    -85.00 -16.00   0.50   15.93    --  -42.55 125.00  60.00  138
 30  \w    -65.00 -27.00   0.50   15.93    -- -102.00 116.00 -28.91   76
 31  \w    -63.00 -28.00   0.50   15.93    -- -102.00  61.00   0.00   70
 32  \w    -96.00 -38.00   0.50   15.93    --  -42.55 125.00 150.00  116
 33  \w    -71.00 -28.00   0.50   15.93    -- -102.00  61.00 150.00   86
 34  \w   -112.00 -63.00   0.50   15.93    -- -102.00 125.00  60.00   98
 35  \w   -109.00 -80.00   0.50   15.93    -- -102.00 116.00 -28.91   58
 36  \w   -112.00 -64.00   0.50   15.93    -- -102.00 125.00  30.00   96
 37  \w    -68.00 -28.00   0.50   15.93    -- -102.00 125.00-180.00   80
 38  \w    -64.00 -28.00   0.50   15.93    -- -102.00  61.00-180.00   72
 39  \w   -110.00 -78.00   0.50   15.93    -- -102.00 125.00-180.00   64
 40  \w   -163.00 -78.00   0.50   15.93    -- -102.00 -30.00  60.00  170
 41  \w   -173.00-120.00   0.50   15.93    -- -102.00 -94.00 -90.00  106
 42  \w   -167.00-122.00   0.50   15.93    -- -102.00-125.00 -30.00   90
 43  \w   -174.00 -83.00   0.50   15.93    -- -102.00 -29.00 161.00  182
;
_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      0.0219957000
_diffrn_orient_matrix_UB_12      0.0882182000
_diffrn_orient_matrix_UB_13      0.0120469000
_diffrn_orient_matrix_UB_21      -0.1808753000
_diffrn_orient_matrix_UB_22      -0.0007701000
_diffrn_orient_matrix_UB_23      0.0222788000
_diffrn_orient_matrix_UB_31      0.0870183000
_diffrn_orient_matrix_UB_32      -0.0053506000
_diffrn_orient_matrix_UB_33      0.0619393000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            37815
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.335
_diffrn_reflns_theta_min         2.535
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark blue'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       plate
_exptl_crystal_F_000             1292
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1057
_refine_ls_number_reflns         12488
_refine_ls_number_restraints     265
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0640
_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^)+(0.1056P)^2^+0.6037P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1731
_refine_ls_wR_factor_ref         0.2055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7214
_reflns_number_total             12488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00726b2.cif
_cod_data_source_block           adr-229-tcnq-3
_cod_depositor_comments
'Adding full bibliography for 7243354--7243355.cif.'
_cod_original_cell_volume        3115.97(13)
_cod_database_code               7243354
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C N H'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.823
_diffrn_oxdiff_digest_frames
;
018f86ba203e9148ed9c6f268f504b12480394613fd
;
_diffrn_oxdiff_digest_hkl
;
012a27f37a6ab494a36086ae2aa513e761c45d
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N01X-C02L \\sim N01Y-C2AA
 with sigma of 0.02
 N01X-C026 \\sim N01Y-C2
 with sigma of 0.02
 C02L-C02P \\sim C2AA-C3AA
 with sigma of 0.02
 C02P-C02M \\sim C3AA-C4AA
 with sigma of 0.02
 C02M-C02G \\sim C4AA-C5AA
 with sigma of 0.02
 C02G-C026 \\sim C5AA-C2
 with sigma of 0.02
 C026-C021 \\sim C2-C021
 with sigma of 0.02
 N01X-C02P \\sim N01Y-C3AA
 with sigma of 0.04
 N01X-C02G \\sim N01Y-C5AA
 with sigma of 0.04
 N01X-C021 \\sim N01Y-C021
 with sigma of 0.04
 C02L-C02M \\sim C2AA-C4AA
 with sigma of 0.04
 C02L-C026 \\sim C2AA-C2
 with sigma of 0.04
 C02P-C02G \\sim C3AA-C5AA
 with sigma of 0.04
 C02M-C026 \\sim C4AA-C2
 with sigma of 0.04
 C02G-C021 \\sim C5AA-C021
 with sigma of 0.04
 C02O-C02Q \\sim C1AA-C02R
 with sigma of 0.02
 C02Q-C02J \\sim C02R-C0AA
 with sigma of 0.02
 C01Z-N02B \\sim C01Z-N02C
 with sigma of 0.04
 C01Z-C02J \\sim C01Z-C0AA
 with sigma of 0.04
 N02B-C02O \\sim N02C-C1AA
 with sigma of 0.04
 N02B-C02J \\sim N02C-C0AA
 with sigma of 0.04
 C02O-C02J \\sim C1AA-C0AA
 with sigma of 0.04
 N02B-C02E \\sim N02C-C8AA
 with sigma of 0.02
 C02E-C02O \\sim C8AA-C1AA
 with sigma of 0.02
 C02E-C02Q \\sim C8AA-C02R
 with sigma of 0.04
 N005-C01C \\sim N0-C01C
 with sigma of 0.02
 N005-C01Y \\sim N0-C9AA
 with sigma of 0.02
 C01C-C012 \\sim C01C-C0
 with sigma of 0.02
 C012-C01U \\sim C0-C01V
 with sigma of 0.02
 C01U-C01W \\sim C01V-C01W
 with sigma of 0.02
 C01W-C01Y \\sim C01W-C9AA
 with sigma of 0.02
 N005-C01W \\sim N0-C01W
 with sigma of 0.04
 C01C-C01U \\sim C01C-C01V
 with sigma of 0.04
 C01C-C01Y \\sim C01C-C9AA
 with sigma of 0.04
 C012-C01W \\sim C0-C01W
 with sigma of 0.04
 C020-C022 \\sim C3-C4
 with sigma of 0.02
 C020-C02A \\sim C3-C02B
 with sigma of 0.02
 C022-N023 \\sim C4-N1
 with sigma of 0.02
 C022-C025 \\sim C4-C025
 with sigma of 0.02
 N023-C02K \\sim N1-C0BA
 with sigma of 0.02
 C02K-C02F \\sim C0BA-C1BA
 with sigma of 0.02
 C02F-C02A \\sim C1BA-C02B
 with sigma of 0.02
 C020-N023 \\sim C3-N1
 with sigma of 0.04
 C020-C02F \\sim C3-C1BA
 with sigma of 0.04
 C020-C025 \\sim C3-C025
 with sigma of 0.04
 C022-C02K \\sim C4-C0BA
 with sigma of 0.04
 C022-C02A \\sim C4-C02B
 with sigma of 0.04
 N023-C02F \\sim N1-C1BA
 with sigma of 0.04
 N023-C025 \\sim N1-C025
 with sigma of 0.04
 C02K-C02A \\sim C0BA-C02B
 with sigma of 0.04
 C02H-C02N \\sim C6AA-C7AA
 with sigma of 0.02
 C02N-C02C \\sim C7AA-C2BA
 with sigma of 0.02
 C02C-C028 \\sim C2BA-C1
 with sigma of 0.02
 C028-N01H \\sim C1-N01I
 with sigma of 0.02
 C018-C02H \\sim C018-C6AA
 with sigma of 0.04
 C018-N01H \\sim C018-N01I
 with sigma of 0.04
 C02H-C02C \\sim C6AA-C2BA
 with sigma of 0.04
 C02H-N01H \\sim C6AA-N01I
 with sigma of 0.04
 C02N-C028 \\sim C7AA-C1
 with sigma of 0.04
 C02C-N01H \\sim C2BA-N01I
 with sigma of 0.04
 N01V-C02I \\sim N01W-C5BA
 with sigma of 0.02
 C02D-C029 \\sim C4BA-C5
 with sigma of 0.02
 C01E-N01V \\sim C01E-N01W
 with sigma of 0.04
 C01E-C029 \\sim C01E-C5
 with sigma of 0.04
 N01V-C029 \\sim N01W-C5
 with sigma of 0.04
 C02I-C02D \\sim C5BA-C4BA
 with sigma of 0.04
3. Rigid bond restraints
 C2, N01Y, C2AA, C3AA, C4AA, C5AA
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C0AA, N02C, C8AA, C1AA, C02R
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C024 \\sim N02B \\sim C02E \\sim C02O \\sim C02Q \\sim C02J: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
N01X \\sim C02L \\sim C02P \\sim C02M \\sim C02G \\sim C026: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
C02P \\sim C026: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C2 \\sim N01Y \\sim C2AA \\sim C3AA \\sim C4AA \\sim C5AA: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
C0AA \\sim N02C \\sim C8AA \\sim C1AA \\sim C02R: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
C0AA \\sim C8AA \\sim C1AA \\sim C02R \\sim N02C: within 1.7A with sigma of
0.02 and sigma for terminal atoms of 0.04
C0 \\sim C01V \\sim C9AA \\sim N0: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
N01I \\sim C1 \\sim C2BA \\sim C7AA \\sim C6AA: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
C1 \\sim C2BA \\sim C7AA \\sim C01D \\sim C6AA \\sim N01I: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
5. Others
 Fixed Sof: N005(0.6) C012(0.6) H012(0.6) C01U(0.6) H01U(0.6) H01W(0.6)
 H01A(0.4) C01Y(0.6) H01Y(0.6) C02H(0.6) H02H(0.6) C02N(0.6) H02N(0.6)
 C02C(0.6) H02C(0.6) C028(0.6) H028(0.6) N01H(0.6) N01V(0.5) C02I(0.5)
 H02I(0.5) H6A(0.5) H6B(0.5) C02D(0.5) H02D(0.5) C029(0.5) H029(0.5) N01X(0.63)
 C02L(0.63) H02L(0.63) C02P(0.63) H02P(0.63) C02M(0.63) H02M(0.63) C02G(0.63)
 H02G(0.63) C026(0.63) C020(0.57) H020(0.57) C022(0.57) N023(0.57) C02K(0.57)
 H02K(0.57) C02F(0.57) H02F(0.57) C02A(0.57) H02A(0.57) N02B(0.65) C02E(0.65)
 H02E(0.65) C02O(0.65) H02O(0.65) C02Q(0.65) H02Q(0.65) C02J(0.65) H02J(0.65)
 C2(0.37) N01Y(0.37) C2AA(0.37) H2AA(0.37) C3AA(0.37) H3AA(0.37) C4AA(0.37)
 H4AA(0.37) C5AA(0.37) H5AA(0.37) C0AA(0.35) H0AA(0.35) N02C(0.35) C8AA(0.35)
 H8AA(0.35) C1AA(0.35) H1AA(0.35) C02R(0.35) H02R(0.35) N0(0.4) C9AA(0.4)
 H9AA(0.4) C01V(0.4) H01V(0.4) C0(0.4) H0(0.4) C4(0.43) N1(0.43) C0BA(0.43)
 H0BA(0.43) C1BA(0.43) H1BA(0.43) C02B(0.43) H02B(0.43) C3(0.43) H3(0.43)
 C6AA(0.4) H6AA(0.4) C7AA(0.4) H7AA(0.4) C2BA(0.4) H2BA(0.4) C1(0.4) H1(0.4)
 N01I(0.4) C5(0.5) H5(0.5) N01W(0.5) C5BA(0.5) H5BA(0.5) C4BA(0.5) H4BA(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C012(H012), C01U(H01U), C01W(H01W), C01W(H01A), C01Y(H01Y), C00B(H00B),
 C00G(H00G), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O), C00Q(H00Q),
 C00V(H00V), C00W(H00W), C00X(H00X), C010(H010), C011(H011), C014(H014),
 C02H(H02H), C02N(H02N), C02C(H02C), C028(H028), C01F(H01F), C02I(H02I),
 C6(H6A), C6(H6B), C02D(H02D), C029(H029), C02L(H02L), C02P(H02P), C02M(H02M),
 C02G(H02G), C020(H020), C02K(H02K), C02F(H02F), C02A(H02A), C02E(H02E),
 C02O(H02O), C02Q(H02Q), C02J(H02J), C2AA(H2AA), C3AA(H3AA), C4AA(H4AA),
 C5AA(H5AA), C0AA(H0AA), C8AA(H8AA), C1AA(H1AA), C02R(H02R), C9AA(H9AA),
 C01V(H01V), C0(H0), C0BA(H0BA), C1BA(H1BA), C02B(H02B), C3(H3), C6AA(H6AA),
 C7AA(H7AA), C2BA(H2BA), C1(H1), C5(H5), C5BA(H5BA), C4BA(H4BA)
6.b Fitted hexagon refined as free rotating group:
 N005(C01C,C012,C01U,C01W,C01Y), C01D(C02H,C02N,C02C,C028,N01H), C01O(N01V,
 C02I,C6,C02D,C029), N01X(C02L,C02P,C02M,C02G,C026), C020(C022,N023,C02K,C02F,
 C02A), C024(N02B,C02E,C02O,C02Q,C02J), C2(N01Y,C2AA,C3AA,C4AA,C5AA), C4(N1,
 C0BA,C1BA,C02B,C3)
;
_shelx_res_checksum              96191
_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 1.447
_oxdiff_exptl_absorpt_empirical_full_min 0.683