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_7250645
_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         '2(C43 H57 N5 O4), C6 Cl4 O2, 2(C H2 Cl2)'
_chemical_formula_sum            'C94 H118 Cl8 N10 O10'
_chemical_formula_weight         1831.58
_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             2021-10-20
_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                103.894(5)
_cell_angle_beta                 91.039(5)
_cell_angle_gamma                114.731(5)
_cell_formula_units_Z            2
_cell_length_a                   15.361(2)
_cell_length_b                   17.925(3)
_cell_length_c                   19.975(3)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      54.92
_cell_measurement_theta_min      2.45
_cell_volume                     4805.4(13)
_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 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0558
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            105514
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.484
_diffrn_reflns_theta_min         2.000
_diffrn_source_current           2.86
_diffrn_source_power             0.200057
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.739
_exptl_absorpt_correction_T_max  0.7509
_exptl_absorpt_correction_T_min  0.5256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.777
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1140
_refine_ls_number_reflns         18551
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0652
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1060P)^2^+2.4155P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1855
_refine_ls_wR_factor_ref         0.1977
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13401
_reflns_number_total             18551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00115c2.cif
_cod_data_source_block           211019l_0m
_cod_original_cell_volume        4805.0(12)
_cod_database_code               7250645
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.845
_shelx_estimated_absorpt_t_min   0.819
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2. Restrained distances 
 Cl3T-C2T = Cl3S-C2S = Cl4T-C2T = Cl4S-C2S 
 1.73 with sigma of 0.02 
 C53-C54 \\sim C53-C54A 
 with sigma of 0.02 
 Cl3S-Cl4S \\sim Cl3T-Cl4T 
 with sigma of 0.04 
 C2S-Cl3S \\sim C2T-Cl3T 
 with sigma of 0.02 
 C2S-Cl4S \\sim C2T-Cl4T 
 with sigma of 0.02 
3. Uiso/Uaniso restraints and constraints 
Uanis(C2S) = Uanis(C2T) 
Uanis(Cl3T) = Uanis(Cl3S) 
Uanis(Cl4S) = Uanis(Cl4T) 
4. Others 
 Sof(H53C)=Sof(H53D)=Sof(C54A)=Sof(H54D)=Sof(H54E)=Sof(H54F)=1-FVAR(1) 
 Sof(H53A)=Sof(H53B)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(H54C)=FVAR(1) 
 Sof(Cl3T)=Sof(C2T)=Sof(H2TA)=Sof(H2TB)=Sof(Cl4T)=1-FVAR(2) 
 Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(Cl3S)=Sof(Cl4S)=FVAR(2) 
5.a Secondary CH2 refined with riding coordinates: 
 C2(H2A,H2B), C8(H8A,H8B), C10(H10A,H10B), C16(H16A,H16B), C18(H18A,H18B), 
 C29(H29A,H29B), C31(H31A,H31B), C37(H37A,H37B), C39(H39A,H39B), C42(H42A,H42B), 
  C45(H45A,H45B), C51(H51A,H51B), C53(H53A,H53B), C53(H53C,H53D), C59(H59A, 
 H59B), C61(H61A,H61B), C72(H72A,H72B), C74(H74A,H74B), C80(H80A,H80B), 
 C82(H82A,H82B), C85(H85A,H85B), C1S(H1SA,H1SB), C2S(H2SA,H2SB), C2T(H2TA,H2TB) 
5.b Aromatic/amide H refined with riding coordinates: 
 C21(H21), C22(H22), C23(H23), C64(H64), C65(H65), C66(H66), N1(H1), N2(H2), 
 N4(H4), N5(H5), N6(H6), N7(H7), N9(H9), N10(H10) 
5.c Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C17(H17A,H17B,H17C), 
 C19(H19A,H19B,H19C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C38(H38A,H38B, 
 H38C), C40(H40A,H40B,H40C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C52(H52A, 
 H52B,H52C), C54(H54A,H54B,H54C), C60(H60A,H60B,H60C), C62(H62A,H62B,H62C), 
 C73(H73A,H73B,H73C), C75(H75A,H75B,H75C), C81(H81A,H81B,H81C), C83(H83A,H83B, 
 H83C), C86(H86A,H86B,H86C), C54A(H54D,H54E,H54F) 
;
_olex2_submission_special_instructions 'No special instructions were received'