Guest-adaptive hydrogen-bonded dimerization of a C3-symmetric tribenzotriquinacene molecular bowl
Yang, Tian-Shu; Duan, Xiao-Fang; Yin, Fan; Cai, Li-Xuan; Zhou, Li-Peng; Hu, Shao-Jun; Guo, Xiao-Qing; Sun, Qing-Fu; CrystEngComm 27 (2025) 2025–2032; doi:10.1039/D5CE00038F

data_7250050
_publ_section_title
;
 Guest-adaptive hydrogen-bonded dimerization of a C3-symmetric
 tribenzotriquinacene molecular bowl
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              2025
_journal_page_last               2032
_journal_paper_doi               10.1039/D5CE00038F
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C59 H57 N15 O3, 3(C8 H10), H2 O'
_chemical_formula_sum            'C83 H89 N15 O4'
_chemical_formula_weight         1360.69
_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   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc2m121t
_audit_creation_date             2025-02-14
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-14 deposited with the CCDC.	2025-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                71.798(3)
_cell_angle_beta                 80.271(3)
_cell_angle_gamma                79.849(3)
_cell_formula_units_Z            2
_cell_length_a                   14.6409(5)
_cell_length_b                   15.4829(5)
_cell_length_c                   17.0956(5)
_cell_measurement_reflns_used    21813
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.8950
_cell_measurement_theta_min      2.7470
_cell_volume                     3596.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.127a 64-bit (release 16-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.939
_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    -27.00   0.00   0.50    0.06    --   45.97 -19.00-180.00   54
  2  \w    -23.00  17.00   0.50    0.06    --   45.97 -19.00-150.00   80
  3  \w    -28.00  30.00   0.50    0.06    --   45.97 -38.00  30.00  116
  4  \w    -26.00  23.00   0.50    0.06    --   45.97 -19.00  60.00   98
  5  \w    -28.00  18.00   0.50    0.06    --   45.97 -19.00 120.00   92
  6  \w    -24.00  23.00   0.50    0.06    --   45.97 -19.00 150.00   94
  7  \w     38.00  89.00   0.50    0.22    --  107.47 -86.00 121.00  102
  8  \w     48.00  86.00   0.50    0.22    --  107.47 -95.00  90.00   76
  9  \w     40.00 111.00   0.50    0.22    --  107.47-125.00 150.00  142
 10  \w     47.00 106.00   0.50    0.22    --  107.47-125.00  60.00  118
 11  \w     56.00 109.00   0.50    0.22    --  107.47-125.00  30.00  106
 12  \w     35.00  97.00   0.50    0.22    --  107.47 -95.00 -60.00  124
 13  \w     75.00 108.00   0.50    0.22    --  107.47-125.00 -60.00   66
 14  \w     48.00 105.00   0.50    0.22    --  107.47 -95.00-150.00  114
 15  \w     36.00  67.00   0.50    0.22    --  107.47 -61.00-150.00   62
 16  \w     44.00  90.00   0.50    0.06    --   45.97-125.00 -60.00   92
 17  \w    -26.00  72.00   0.50    0.06    --   45.97 -86.00 121.00  196
 18  \w     45.00  89.00   0.50    0.22    --  107.47 -77.00 -60.00   88
 19  \w    103.00 174.00   0.50    0.22    --  107.47  45.00 150.00  142
 20  \w     94.00 167.00   0.50    0.22    --  107.47  45.00  30.00  146
 21  \w     96.00 131.00   0.50    0.22    --  107.47  45.00-180.00   70
 22  \w    134.00 174.00   0.50    0.22    --  107.47  45.00-180.00   80
 23  \w     83.00 149.00   0.50    0.22    --  107.47  86.00-120.00  132
 24  \w    -99.00 -74.00   0.50    0.22    --  -97.00  86.00-120.00   50
 25  \w    -63.00 -29.00   0.50    0.22    --  -97.00 137.00-108.61   68
 26  \w   -120.00 -94.00   0.50    0.22    --  -97.00 137.00-108.61   52
 27  \w    -67.00 -31.00   0.50    0.22    --  -97.00 125.00  30.00   72
 28  \w   -108.00 -73.00   0.50    0.22    --  -97.00 125.00  30.00   70
 29  \w   -108.00 -69.00   0.50    0.22    --  -97.00 109.00  42.25   78
 30  \w    -68.00 -34.00   0.50    0.22    --  -97.00 142.00 121.03   68
 31  \w   -124.00 -73.00   0.50    0.22    --  -97.00 142.00 121.03  102
 32  \w   -106.00 -79.00   0.50    0.22    --  -97.00 108.00  83.18   54
 33  \w    -55.00  24.00   0.50    0.06    --  -45.97  86.00-120.00  158
 34  \w   -106.00 -81.00   0.50    0.22    --  -97.00 107.00-114.48   50
 35  \w    -76.00 -30.00   0.50    0.22    --  -97.00 107.00-114.48   92
 36  \w    -53.00 -25.00   0.50    0.22    --  -97.00  45.00-180.00   56
 37  \w    -54.00 -29.00   0.50    0.22    --  -97.00  45.00-150.00   50
 38  \w    -50.00 -24.00   0.50    0.22    --  -97.00  45.00-120.00   52
 39  \w    -74.00 -25.00   0.50    0.22    --  -97.00  61.00-120.00   98
 40  \w    -53.00 -28.00   0.50    0.22    --  -97.00  45.00   0.00   50
 41  \w    -50.00 -25.00   0.50    0.22    --  -97.00  45.00 -90.00   50
 42  \w    -53.00 -24.00   0.50    0.22    --  -97.00  45.00  30.00   58
 43  \w    -54.00 -29.00   0.50    0.22    --  -97.00  45.00  60.00   50
 44  \w    -72.00 -36.00   0.50    0.22    --  -97.00  61.00  90.00   72
 45  \w    -53.00 -25.00   0.50    0.22    --  -97.00  45.00 150.00   56
 46  \w    -50.00 -24.00   0.50    0.22    --  -97.00  45.00  90.00   52
 47  \w   -143.00-101.00   0.50    0.22    --  -97.00 -30.00 -30.00   84
 48  \w   -142.00 -89.00   0.50    0.22    --  -97.00 -95.00-180.00  106
 49  \w   -162.00 -90.00   0.50    0.22    --  -97.00 -86.00 121.00  144
;
_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      -0.0146927000
_diffrn_orient_matrix_UB_12      -0.0718828000
_diffrn_orient_matrix_UB_13      0.0852311000
_diffrn_orient_matrix_UB_21      0.1066918000
_diffrn_orient_matrix_UB_22      -0.0238875000
_diffrn_orient_matrix_UB_23      0.0000252000
_diffrn_orient_matrix_UB_31      -0.0001083000
_diffrn_orient_matrix_UB_32      0.0736704000
_diffrn_orient_matrix_UB_33      0.0432435000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            48157
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.085
_diffrn_reflns_theta_min         2.741
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.127a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1128
_refine_ls_number_reflns         14306
_refine_ls_number_restraints     593
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0739
_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^)+(0.1034P)^2^+3.4300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1878
_refine_ls_wR_factor_ref         0.1980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11859
_reflns_number_total             14306
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00038f2.cif
_cod_data_source_block           p-xylene
_cod_depositor_comments
'Adding full bibliography for 7250046--7250051.cif.'
_cod_database_code               7250050
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N Cl'
_shelx_estimated_absorpt_t_max   0.884
_shelx_estimated_absorpt_t_min   0.787
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C86-C81 = C82-C81 = C83-C82 = C84-C83 = C85-C84 = C86-C85
 1.39 with sigma of 0.01
 C87-C81 = C88-C84
 1.5 with sigma of 0.01
 C30-C29 = C30-C31 = C30-H30
 1.5 with sigma of 0.01
 C81-C83 \\sim C82-C84 \\sim C83-C85 \\sim C84-C86 \\sim C85-C81 \\sim C86-C82
 with sigma of 0.02
3. Restrained planarity
 C64A, C65A, C66A, C67A, C68A, C69A, C70A, C71A
 with sigma of 0.01
 C81A, C82A, C83A, C84A, C85A, C86A, C87A, C88A
 with sigma of 0.01
 C81, C82, C83, C84, C85, C86, C87, C88
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C64 \\sim C64A \\sim C65 \\sim C65A \\sim C66 \\sim C66A \\sim C67 \\sim C67A
\\sim C68 \\sim C68A \\sim C69 \\sim C69A \\sim C70 \\sim C70A \\sim C71 \\sim
C71A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
2A
C81 \\sim C81A \\sim C82 \\sim C82A \\sim C83 \\sim C83A \\sim C84 \\sim C84A
\\sim C85 \\sim C85A \\sim C86 \\sim C86A \\sim C87 \\sim C87A \\sim C88 \\sim
C88A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
2A
Uanis(C70A) \\sim Ueq, Uanis(C86) \\sim Ueq, Uanis(C87) \\sim Ueq: with sigma
of 0.003 and sigma for terminal atoms of 0.006
5. Same fragment restrains
{C81A, C82A, C83A, C84A, C85A, C86A, C87A, C88A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C81, C82, C83, C84, C85, C86, C87, C88}
{C64A, C65A, C66A, C67A, C68A, C69A, C70A, C71A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C64, C65, C66, C67, C68, C69, C70, C71}
6. Others
 Sof(C64A)=Sof(C65A)=Sof(H65A)=Sof(C66A)=Sof(H66A)=Sof(C67A)=Sof(C68A)=
 Sof(H68A)=Sof(C69A)=Sof(H69A)=Sof(C70A)=Sof(H70D)=Sof(H70E)=Sof(H70F)=
 Sof(C71A)=Sof(H71D)=Sof(H71E)=Sof(H71F)=1-FVAR(1)
 Sof(C64)=Sof(C65)=Sof(H65)=Sof(C66)=Sof(H66)=Sof(C67)=Sof(C68)=Sof(H68)=
 Sof(C69)=Sof(H69)=Sof(C70)=Sof(H70A)=Sof(H70B)=Sof(H70C)=Sof(C71)=Sof(H71A)=
 Sof(H71B)=Sof(H71C)=FVAR(1)
 Sof(C81A)=Sof(C82A)=Sof(H82A)=Sof(C83A)=Sof(H83A)=Sof(C84A)=Sof(C85A)=
 Sof(H85A)=Sof(C86A)=Sof(H86A)=Sof(C87A)=Sof(H87D)=Sof(H87E)=Sof(H87F)=
 Sof(C88A)=Sof(H88D)=Sof(H88E)=Sof(H88F)=0.5*(1-FVAR(3))
 Sof(C81)=Sof(C82)=Sof(H82)=Sof(C83)=Sof(H83)=Sof(C84)=Sof(C85)=Sof(H85)=
 Sof(C86)=Sof(H86)=Sof(C87)=Sof(H87A)=Sof(H87B)=Sof(H87C)=Sof(C88)=Sof(H88A)=
 Sof(H88B)=Sof(H88C)=0.5*FVAR(3)
7.a Ternary CH refined with riding coordinates:
 C23(H23), C40(H40), C57(H57)
7.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C15(H15), C19(H19), C20(H20), C21(H21),
 C27(H27), C29(H29), C30(H30), C32(H32), C36(H36), C37(H37), C38(H38), C44(H44),
  C46(H46), C47(H47), C49(H49), C53(H53), C54(H54), C55(H55), N5(H5), N10(H10A),
  N15(H15A), C62(H62), C63(H63), C65(H65), C66(H66), C68(H68), C69(H69),
 C65A(H65A), C66A(H66A), C68A(H68A), C69A(H69A), C73(H73), C74(H74), C76(H76),
 C77(H77), C82(H82), C83(H83), C85(H85), C86(H86), C82A(H82A), C83A(H83A),
 C85A(H85A), C86A(H86A)
7.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C24(H24A,
 H24B,H24C), C25(H25A,H25B,H25C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C),
 C58(H58A,H58B,H58C), C59(H59A,H59B,H59C), C60(H60A,H60B,H60C), C70(H70A,H70B,
 H70C), C71(H71A,H71B,H71C), C70A(H70D,H70E,H70F), C71A(H71D,H71E,H71F),
 C78(H78A,H78B,H78C), C79(H79A,H79B,H79C), C87(H87A,H87B,H87C), C88(H88A,H88B,
 H88C), C87A(H87D,H87E,H87F), C88A(H88D,H88E,H88F)
;
_shelx_res_checksum              74164
_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 1.786
_oxdiff_exptl_absorpt_empirical_full_min 0.490