A self-assembled supramolecular capsule that cocrystallizes with 1,4-disubstituted benzene derivatives
Wu, Yingcong; Ma, Wanzun; Wei, Dehui; Liu, Gen; Wei, Huiqi; Zhao, Xinyun; Wu, Lamei; Huang, Zhengxi; Zhang, Zhan; CrystEngComm 27 (2025) 2287–2291; doi:10.1039/D5CE00115C

data_7250641
_publ_section_title
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 A self-assembled supramolecular capsule that cocrystallizes with
 1,4-disubstituted benzene derivatives
;
_journal_issue                   15
_journal_name_full               CrystEngComm
_journal_page_first              2287
_journal_page_last               2291
_journal_paper_doi               10.1039/D5CE00115C
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         '2(C43 H57 N5 O4), 4(C H4 O), 2(C H2 Cl2)'
_chemical_formula_sum            'C92 H134 Cl4 N10 O12'
_chemical_formula_weight         1713.88
_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             2021-03-16
_audit_creation_method
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Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) 
;
_audit_update_record
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2025-01-23 deposited with the CCDC.	2025-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                102.794(2)
_cell_angle_beta                 90.793(2)
_cell_angle_gamma                113.600(2)
_cell_formula_units_Z            2
_cell_length_a                   15.1531(9)
_cell_length_b                   17.6198(11)
_cell_length_c                   19.7365(12)
_cell_measurement_reflns_used    9690
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.73
_cell_measurement_theta_min      3.62
_cell_volume                     4677.8(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XM  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            62623
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         59.998
_diffrn_reflns_theta_min         2.010
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.086
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.817
_refine_diff_density_min         -1.507
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1161
_refine_ls_number_reflns         20537
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0727
_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^)+(0.0914P)^2^+5.1600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1909
_refine_ls_wR_factor_ref         0.1933
_reflns_Friedel_coverage         0.000
_reflns_number_gt                19085
_reflns_number_total             20537
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00115c2.cif
_cod_data_source_block           210315e_0m
_cod_database_code               7250641
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.899
_shelx_estimated_absorpt_t_min   0.881
_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) groups 
2. Restrained distances 
 C3A-C11A \\sim C3B-C11B 
 with sigma of 0.04 
 C1A-N1A \\sim C1B-N1B 
 with sigma of 0.02 
 C1A-C2A \\sim C1B-C2B 
 with sigma of 0.02 
 C1A-C5A \\sim C1B-C5A 
 with sigma of 0.02 
 C4A-N1A \\sim C4B-N1B 
 with sigma of 0.02 
 C10A-C11A \\sim C10B-C11B 
 with sigma of 0.02 
 C2A-C9A \\sim C2B-C9B 
 with sigma of 0.04 
 C12A-N1A \\sim C12A-N1B 
 with sigma of 0.04 
 C8A-C9A \\sim C8B-C9B 
 with sigma of 0.02 
 C2A-N1A \\sim C2B-N1B 
 with sigma of 0.04 
 C1A-C3A \\sim C1B-C3B 
 with sigma of 0.04 
 C1A-C4A \\sim C1B-C4B 
 with sigma of 0.04 
 C5A-N1A \\sim C5A-N1B 
 with sigma of 0.04 
 C3A-N1A \\sim C3B-N1B 
 with sigma of 0.04 
 C1A-C8A \\sim C1B-C8B 
 with sigma of 0.04 
 C5A-C1A \\sim C5A-C1B 
 with sigma of 0.005 
 C3A-C10A \\sim C3B-C10B 
 with sigma of 0.02 
 C2A-C8A \\sim C2B-C8B 
 with sigma of 0.02 
 C3A-C4A \\sim C3B-C4B 
 with sigma of 0.02 
 C2A-C3A \\sim C2B-C3B 
 with sigma of 0.02 
 C4A-C10A \\sim C4B-C10B 
 with sigma of 0.04 
 C4A-C12A \\sim C4B-C12A 
 with sigma of 0.02 
 C2A-C4A \\sim C2B-C4B 
 with sigma of 0.04 
 C2A-C5A \\sim C2B-C5A 
 with sigma of 0.04 
 C2A-C10A \\sim C2B-C10B 
 with sigma of 0.04 
 C3A-C8A \\sim C3B-C8B 
 with sigma of 0.04 
 C3A-C12A \\sim C3B-C12A 
 with sigma of 0.04 
3. Uiso/Uaniso restraints and constraints 
Uanis(N1A) = Uanis(N1B) 
Uanis(C1A) = Uanis(C1B) 
4. Others 
 Sof(C1B)=Sof(C2B)=Sof(C3B)=Sof(C4B)=Sof(N1B)=Sof(H1B)=Sof(C8B)=Sof(H8BA)= 
 Sof(H8BB)=Sof(C9B)=Sof(H9BA)=Sof(H9BB)=Sof(H9BC)=Sof(C10B)=Sof(H10C)=Sof(H10D)= 
 Sof(C11B)=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1) 
 Sof(C1A)=Sof(C2A)=Sof(C3A)=Sof(C4A)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C9A)= 
 Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(C10A)=Sof(H10A)=Sof(H10B)=Sof(C11A)= 
 Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(N1A)=Sof(H1A)=FVAR(1) 
5.a Secondary CH2 refined with riding coordinates: 
 C6(H6A,H6B), C8(H8A,H8B), C10(H10E,H10F), C16(H16C,H16D), C18(H18C,H18D), 
 C29(H29C,H29D), C31(H31C,H31D), C37(H37C,H37D), C39(H39C,H39D), C42(H42C,H42D), 
  C6A(H6AA,H6AB), C8A(H8AA,H8AB), C10A(H10A,H10B), C16A(H16A,H16B), C18A(H18A, 
 H18B), C29A(H29A,H29B), C31A(H31A,H31B), C37A(H37A,H37B), C39A(H39A,H39B), 
 C42A(H42A,H42B), C5S(H5SA,H5SB), C6S(H6SA,H6SB), C8B(H8BA,H8BB), C10B(H10C, 
 H10D) 
5.b Aromatic/amide H refined with riding coordinates: 
 C21(H21), C22(H22), C23(H23), N1(H1), N2(H2), N4(H4), N5(H5), C21A(H21A), 
 C22A(H22A), C23A(H23A), N1A(H1A), N2A(H2A), N4A(H4A), N5A(H5A), N1B(H1B) 
5.c Tetrahedral OH refined with riding coordinates: 
 O1S(H1S), O4S(H4S) 
5.d Idealised Me refined as rotating group: 
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C11(H11G,H11H,H11I), C17(H17D,H17E,H17F), 
 C19(H19D,H19E,H19F), C30(H30D,H30E,H30F), C32(H32D,H32E,H32F), C38(H38D,H38E, 
 H38F), C40(H40D,H40E,H40F), C43(H43D,H43E,H43F), C7A(H7AA,H7AB,H7AC), C9A(H9AA, 
 H9AB,H9AC), C11A(H11A,H11B,H11C), C17A(H17A,H17B,H17C), C19A(H19A,H19B,H19C), 
 C30A(H30A,H30B,H30C), C32A(H32A,H32B,H32C), C38A(H38A,H38B,H38C), C40A(H40A, 
 H40B,H40C), C43A(H43A,H43B,H43C), C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,H2SC), 
 C3S(H3SA,H3SB,H3SC), C4S(H4SA,H4SB,H4SC), C9B(H9BA,H9BB,H9BC), C11B(H11D,H11E, 
 H11F) 
5.e Idealised tetrahedral OH refined as rotating group: 
 O2S(H2S), O3S(H3S) 
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_shelx_res_checksum              81078
_olex2_submission_special_instructions 'No special instructions were received'