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_7250048
_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
'2(C59 H57 N15 O3), 5(C7 H8), 2(C H Cl3), 2(H2 O)'
_chemical_formula_sum            'C155 H160 Cl6 N30 O8'
_chemical_formula_weight         2783.82
_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.cc2mbq4v
_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                71.658(2)
_cell_angle_beta                 79.5378(19)
_cell_angle_gamma                82.7903(17)
_cell_formula_units_Z            1
_cell_length_a                   14.3812(3)
_cell_length_b                   15.4937(3)
_cell_length_c                   17.2333(4)
_cell_measurement_reflns_used    17720
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      55.0310
_cell_measurement_theta_min      2.3970
_cell_volume                     3574.58(14)
_computing_cell_refinement       'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.116a (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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_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 0.972
_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     21.00 110.00   0.50    1.40    --   65.46-125.00 -30.00  178
  2  \w     76.00 102.00   0.50    1.40    --   65.46-125.00  60.00   52
  3  \w     -5.00  76.00   0.50    1.40    --   65.46 -96.00  68.00  162
  4  \w     -6.00  19.00   0.50    1.40    --   65.46 -38.00 120.00   50
  5  \w     44.00 139.00   0.50    1.40    --   65.46  57.00 150.00  190
  6  \w     88.00 113.00   0.50    1.40    --   65.46  96.00 176.00   50
  7  \w     -5.00  87.00   0.50    1.40    --   65.46 -57.00 -30.00  184
  8  \w    -12.00  27.00   0.50    1.40    --   65.46 -38.00-180.00   78
  9  \w     38.00  64.00   0.50    1.40    --   65.46 -38.00-180.00   52
 10  \w     -6.00  37.00   0.50    0.35    --   -1.17 -99.00-120.00   86
 11  \w     -3.00  35.00   0.50    0.35    --   -1.17 -96.00  68.00   76
 12  \w    -75.00 -10.00   0.50    0.35    --   -1.17 -77.00  30.00  130
 13  \w   -140.00 -62.00   0.50    1.40    --  -67.80 -57.00 -30.00  156
 14  \w   -141.00 -85.00   0.50    1.40    --  -67.80 -96.00  68.00  112
 15  \w   -140.00 -90.00   0.50    1.40    --  -67.80 -99.00  90.00  100
 16  \w   -135.00 -92.00   0.50    1.40    --  -67.80 -99.00 150.00   86
 17  \w   -138.00 -80.00   0.50    1.40    --  -67.80-125.00 -30.00  116
 18  \w   -132.00 -89.00   0.50    1.40    --  -67.80 -99.00 -60.00   86
 19  \w    -57.00 -10.00   0.50    1.40    --  -67.80  57.00   0.00   94
 20  \w     35.00  72.00   0.50    0.35    --   -1.17  57.00 -90.00   74
 21  \w    -96.00 -14.00   0.50    1.40    --  -67.80  77.00  30.00  164
 22  \w    -96.00 -13.00   0.50    1.40    --  -67.80  77.00-180.00  166
 23  \w   -109.00 -39.00   0.50    1.40    --  -67.80 125.00-150.00  140
 24  \w    -90.00 -30.00   0.50    1.40    --  -67.80  96.00 176.00  120
 25  \w    -35.00  23.00   0.50    0.35    --   -1.17  96.00 176.00  116
;
_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      -0.0183075000
_diffrn_orient_matrix_UB_12      0.0876229000
_diffrn_orient_matrix_UB_13      -0.0416694000
_diffrn_orient_matrix_UB_21      0.0108575000
_diffrn_orient_matrix_UB_22      0.0245233000
_diffrn_orient_matrix_UB_23      0.0655393000
_diffrn_orient_matrix_UB_31      0.0925344000
_diffrn_orient_matrix_UB_32      0.0075969000
_diffrn_orient_matrix_UB_33      -0.0287569000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            40828
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         55.126
_diffrn_reflns_theta_min         2.376
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    1.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.116a (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    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             1466
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.200
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1165
_refine_ls_number_reflns         13351
_refine_ls_number_restraints     790
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1928
_refine_ls_R_factor_gt           0.1378
_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^)+(0.0849P)^2^+25.3942P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3414
_refine_ls_wR_factor_ref         0.3586
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9413
_reflns_number_total             13351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00038f2.cif
_cod_data_source_block           PhMe
_cod_depositor_comments
'Adding full bibliography for 7250046--7250051.cif.'
_cod_original_cell_volume        3574.59(15)
_cod_database_code               7250048
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N Cl'
_shelx_estimated_absorpt_t_max   0.899
_shelx_estimated_absorpt_t_min   0.872
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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
 C61-C60 \\sim C65-C60 \\sim C65-C64 \\sim C64-C63 \\sim C62-C61 \\sim C63-C62
 with sigma of 0.02
 C67-C69 \\sim C68-C70 \\sim C69-C71 \\sim C70-C72 \\sim C71-C67 \\sim C72-C68
 with sigma of 0.02
 C68-C67 \\sim C69-C68 \\sim C70-C69 \\sim C71-C70 \\sim C72-C71 \\sim C72-C67
 with sigma of 0.02
 C66-C60 \\sim C73-C67
 with sigma of 0.02
 C73-C72 \\sim C73-C68
 with sigma of 0.02
 C60-C62 \\sim C61-C63 \\sim C62-C64 \\sim C63-C65 \\sim C64-C60 \\sim C65-C61
 with sigma of 0.02
 C66-C65 \\sim C66-C61
 with sigma of 0.02
3. Restrained planarity
 C67, C68, C69, C70, C71, C72, C73
 with sigma of 0.01
 C60, C61, C62, C63, C64, C65, C66
 with sigma of 0.01
 C60A, C61A, C62A, C63A, C64A, C65A, C66A
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C40 \\sim C41 \\sim C41A \\sim C42 \\sim C42A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
C67 \\sim C67A \\sim C68 \\sim C68A \\sim C69 \\sim C69A \\sim C70 \\sim C70A
\\sim C71 \\sim C71A \\sim C72 \\sim C72A \\sim C73 \\sim C73A \\sim C78A \\sim
C78B \\sim Cl1A \\sim Cl1B \\sim Cl2A \\sim Cl2B \\sim Cl3A \\sim Cl3B \\sim
C78 \\sim Cl1 \\sim Cl2 \\sim Cl3: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
C23 \\sim C24 \\sim C24A \\sim C25 \\sim C25A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
C60 \\sim C61 \\sim C62 \\sim C63 \\sim C64 \\sim C65 \\sim C66 \\sim C60A
\\sim C61A \\sim C62A \\sim C63A \\sim C64A \\sim C65A \\sim C66A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C72A) \\sim Ueq, Uanis(C67A) \\sim Ueq, Uanis(C68A) \\sim Ueq,
Uanis(C73A) \\sim Ueq, Uanis(C69A) \\sim Ueq, Uanis(C71A) \\sim Ueq,
Uanis(C70A) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C67) \\sim Ueq, Uanis(C72)
\\sim Ueq, Uanis(C73) \\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C71) \\sim Ueq,
Uanis(C70) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
5. Same fragment restrains
{C23, C24, C25} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C23, C24A, C25A}
{C60A, C61A, C62A, C63A, C64A, C65A, C66A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C60, C61, C62, C63, C64, C65, C66}
{C78A, Cl1A, Cl2A, Cl3A} sigma for 1-2: 0.01, 1-3: 0.01
{C78B, Cl1B, Cl2B, Cl3B} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C78, Cl1, Cl2, Cl3}
{C40, C41A, C42A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C40, C41, C42}
{C67A, C68A, C69A, C70A, C71A, C72A, C73A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C67, C68, C69, C70, C71, C72, C73}
6. Others
 1*[Sof(C78)+Sof(H78)+Sof(Cl1)+Sof(Cl2)+Sof(Cl3)]+1*[Sof(C78A)+Sof(H78A)+
 Sof(Cl1A)+Sof(Cl2A)+Sof(Cl3A)]+1*[Sof(C78B)+Sof(H78B)+Sof(Cl1B)+Sof(Cl2B)+
 Sof(Cl3B)]=1 with esd of 0
 Sof(C78)=Sof(H78)=Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=FVAR(1)
 Sof(C60A)=Sof(C61A)=Sof(H61A)=Sof(C62A)=Sof(H62A)=Sof(C63A)=Sof(H63A)=
 Sof(C64A)=Sof(H64A)=Sof(C65A)=Sof(H65A)=Sof(C66A)=Sof(H66D)=Sof(H66E)=
 Sof(H66F)=1-FVAR(2)
 Sof(C60)=Sof(C61)=Sof(H61)=Sof(C62)=Sof(H62)=Sof(C63)=Sof(H63)=Sof(C64)=
 Sof(H64)=Sof(C65)=Sof(H65)=Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(H66C)=FVAR(2)
 Sof(H23A)=Sof(C24)=Sof(H24D)=Sof(H24E)=Sof(H24F)=Sof(C25)=Sof(H25D)=Sof(H25E)=
 Sof(H25F)=1-FVAR(3)
 Sof(H23)=Sof(C24A)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25A)=Sof(H25A)=
 Sof(H25B)=Sof(H25C)=FVAR(3)
 Sof(H40A)=Sof(C41A)=Sof(H41D)=Sof(H41E)=Sof(H41F)=Sof(C42A)=Sof(H42D)=
 Sof(H42E)=Sof(H42F)=1-FVAR(4)
 Sof(H40)=Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(H41C)=Sof(C42)=Sof(H42A)=Sof(H42B)=
 Sof(H42C)=FVAR(4)
 Sof(C67A)=Sof(C68A)=Sof(H68A)=Sof(C69A)=Sof(H69A)=Sof(C70A)=Sof(H70A)=
 Sof(C71A)=Sof(H71A)=Sof(C72A)=Sof(H72A)=Sof(C73A)=Sof(H73D)=Sof(H73E)=
 Sof(H73F)=1-FVAR(5)
 Sof(C67)=Sof(C68)=Sof(H68)=Sof(C69)=Sof(H69)=Sof(C70)=Sof(H70)=Sof(C71)=
 Sof(H71)=Sof(C72)=Sof(H72)=Sof(C73)=Sof(H73A)=Sof(H73B)=Sof(H73C)=FVAR(5)
 Sof(C78A)=Sof(H78A)=Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=FVAR(6)
 Sof(C78B)=Sof(H78B)=Sof(Cl1B)=Sof(Cl2B)=Sof(Cl3B)=FVAR(7)
 Fixed Sof: C74(0.5) H74A(0.5) H74B(0.5) H74C(0.5) H75(0.5)
7.a Riding coordinates:
 C73(H73A,H73B,H73C), C73A(H73D,H73E,H73F)
7.b Ternary CH refined with riding coordinates:
 C23(H23), C23(H23A), C40(H40), C40(H40A), C57(H57), C78A(H78A), C78B(H78B),
 C78(H78)
7.c 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), C43(H43),
  C45(H45), C46(H46), C49(H49), C53(H53), C54(H54), C55(H55), N5(H5), N10(H10A),
  N15(H15A), C61(H61), C62(H62), C63(H63), C64(H64), C65(H65), C61A(H61A),
 C62A(H62A), C63A(H63A), C64A(H64A), C65A(H65A), C68(H68), C69(H69), C70(H70),
 C71(H71), C72(H72), C68A(H68A), C69A(H69A), C70A(H70A), C71A(H71A), C72A(H72A),
  C75(H75), C76(H76), C77(H77)
7.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C24A(H24A,
 H24B,H24C), C25A(H25A,H25B,H25C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C),
 C58(H58A,H58B,H58C), C59(H59A,H59B,H59C), C66(H66A,H66B,H66C), C66A(H66D,H66E,
 H66F), C74(H74A,H74B,H74C), C24(H24D,H24E,H24F), C25(H25D,H25E,H25F),
 C41A(H41D,H41E,H41F), C42A(H42D,H42E,H42F)
;
_shelx_res_checksum              69289
_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 4.794
_oxdiff_exptl_absorpt_empirical_full_min 0.344