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_7250643
_publ_section_title
;
 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         'C43 H57 N5 O4, C5 H5 O'
_chemical_formula_sum            'C48 H62 N5 O5'
_chemical_formula_weight         789.02
_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             2021-12-02
_audit_creation_method
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) 
;
_audit_update_record
;
2025-01-23 deposited with the CCDC.	2025-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                102.7380(10)
_cell_angle_beta                 110.4360(10)
_cell_angle_gamma                93.011(2)
_cell_formula_units_Z            2
_cell_length_a                   12.1319(6)
_cell_length_b                   14.3099(7)
_cell_length_c                   15.1788(7)
_cell_measurement_reflns_used    9834
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      61.04
_cell_measurement_theta_min      3.40
_cell_volume                     2384.2(2)
_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      200(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            53638
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         61.086
_diffrn_reflns_theta_min         2.795
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6733
_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    1.099
_exptl_crystal_description       block
_exptl_crystal_F_000             850
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     677
_refine_ls_number_reflns         10992
_refine_ls_number_restraints     95
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0632
_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^)+(0.1379P)^2^+0.3152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1992
_refine_ls_wR_factor_ref         0.2143
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8687
_reflns_number_total             10992
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00115c2.cif
_cod_data_source_block           211028f_0m
_cod_database_code               7250643
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.900
_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 
2. Restrained distances 
 C16-C15 \\sim C16A-C15A 
 with sigma of 0.02 
 C26-C31 \\sim C26A-C31A 
 with sigma of 0.04 
 C12-C15 \\sim C12A-C15A 
 with sigma of 0.02 
 C13-C18 \\sim C13A-C18A 
 with sigma of 0.04 
 C17-C18 \\sim C17A-C18A 
 with sigma of 0.02 
 C12-C16 \\sim C12A-C16A 
 with sigma of 0.04 
 C25-C29 \\sim C25A-C29A 
 with sigma of 0.04 
 C11-C15 \\sim C11-C15A 
 with sigma of 0.04 
 C30-C31 \\sim C30A-C31A 
 with sigma of 0.02 
 C28-C29 \\sim C28A-C29A 
 with sigma of 0.02 
 C13-C15 \\sim C13A-C15A 
 with sigma of 0.04 
 C11-C13 \\sim C11-C13A 
 with sigma of 0.04 
 C14-C12 \\sim C14-C12A 
 with sigma of 0.04 
 C14-C17 \\sim C14-C17A 
 with sigma of 0.04 
 C13-C12 \\sim C13A-C12A 
 with sigma of 0.02 
 C11-C12 \\sim C11-C12A 
 with sigma of 0.02 
 C14-C13 \\sim C14-C13A 
 with sigma of 0.02 
 C13-C17 \\sim C13A-C17A 
 with sigma of 0.02 
 C12-C17 \\sim C12A-C17A 
 with sigma of 0.04 
 O2-C1 \\sim O2A-C1A 
 with sigma of 0.04 
 C2-C52 \\sim C2A-C52 
 with sigma of 0.04 
 O2-C2 \\sim O2A-C2A 
 with sigma of 0.02 
 O2-C52 \\sim O2A-C52 
 with sigma of 0.02 
 C2-C1 \\sim C2A-C1A 
 with sigma of 0.02 
 C25-C28 \\sim C25A-C28A 
 with sigma of 0.02 
 C25-C30 \\sim C25A-C30A 
 with sigma of 0.04 
 C24-C25 \\sim C24-C25A 
 with sigma of 0.02 
 C27-C26 \\sim C27-C26A 
 with sigma of 0.02 
 C26-C25 \\sim C26A-C25A 
 with sigma of 0.02 
 C24-C26 \\sim C24-C26A 
 with sigma of 0.04 
 C26-C30 \\sim C26A-C30A 
 with sigma of 0.02 
 C24-C28 \\sim C24-C28A 
 with sigma of 0.04 
 C27-C25 \\sim C27-C25A 
 with sigma of 0.04 
 C27-C30 \\sim C27-C30A 
 with sigma of 0.04 
 C26-C28 \\sim C26A-C28A 
 with sigma of 0.04 
3. Uiso/Uaniso restraints and constraints 
Uanis(C31) \\sim Ueq, Uanis(C31A) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C2) 
\\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(O2A) \\sim Ueq, 
Uanis(O2) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C16A) \\sim Ueq: with sigma of 
0.01 and sigma for terminal atoms of 0.02 
4. Others 
 Sof(C12A)=Sof(C13A)=Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16D)= 
 Sof(H16E)=Sof(H16F)=Sof(C17A)=Sof(H17C)=Sof(H17D)=Sof(C18A)=Sof(H18D)= 
 Sof(H18E)=Sof(H18F)=1-FVAR(1) 
 Sof(C12)=Sof(C13)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)= 
 Sof(H16C)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)= 
 FVAR(1) 
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(O2A)= 
 1-FVAR(2) 
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(O2)=FVAR(2) 
 Sof(C25A)=Sof(C26A)=Sof(C28A)=Sof(H28C)=Sof(H28D)=Sof(C29A)=Sof(H29D)= 
 Sof(H29E)=Sof(H29F)=Sof(C30A)=Sof(H30C)=Sof(H30D)=Sof(C31A)=Sof(H31D)= 
 Sof(H31E)=Sof(H31F)=1-FVAR(3) 
 Sof(C25)=Sof(C26)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(C29)=Sof(H29A)=Sof(H29B)= 
 Sof(H29C)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)= 
 FVAR(3) 
5.a Secondary CH2 refined with riding coordinates: 
 C2(H2A,H2B), C2A(H2AA,H2AB), C7(H7A,H7B), C9(H9A,H9B), C15(H15A,H15B), 
 C15A(H15C,H15D), C17(H17A,H17B), C17A(H17C,H17D), C28(H28A,H28B), C28A(H28C, 
 H28D), C30(H30A,H30B), C30A(H30C,H30D), C36(H36A,H36B), C38(H38A,H38B), 
 C41(H41A,H41B) 
5.b Aromatic/amide H refined with riding coordinates: 
 C20(H20), C21(H21), C22(H22), N1(H1), N2(H2), N4(H4), N5(H5), C44(H44), 
 C45(H45) 
5.c Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), 
 C16(H16A,H16B,H16C), C16A(H16D,H16E,H16F), C18(H18A,H18B,H18C), C18A(H18D,H18E, 
 H18F), C29(H29A,H29B,H29C), C29A(H29D,H29E,H29F), C31(H31A,H31B,H31C), 
 C31A(H31D,H31E,H31F), C37(H37A,H37B,H37C), C39(H39A,H39B,H39C), C42(H42A,H42B, 
 H42C), C47(H47A,H47B,H47C) 
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'