Self-Assembly of Azamacrocyclic Ligands into Vesicular Structures: From Design to Functional Properties and Applications.
Arteaga-Vinza, Mercy Elena; Blasco, Salvador; Clares, Maria Paz; Albelda, M. Teresa; Frias, Juan Carlos; Bernat-Just, Lucía; Ta, Phuong Linh; López-Castellano, Alicia; Sessler, Jonathan L.; García-España, Enrique; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D5OB01736J

data_7160862
_publ_section_title
;
 Self-Assembly of Azamacrocyclic Ligands into Vesicular Structures: From
 Design to Functional Properties and Applications.
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01736J
_journal_year                    2025
_chemical_formula_moiety         'C21 H39 Cu N5, 2(Cl O4)'
_chemical_formula_sum            'C21 H39 Cl2 Cu N5 O8'
_chemical_formula_weight         624.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-05-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c185 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-09-20 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.900(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.919(5)
_cell_length_b                   8.778(3)
_cell_length_c                   14.947(4)
_cell_measurement_reflns_used    6463
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      29.528
_cell_measurement_theta_min      2.751
_cell_volume                     2718.6(13)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            58548
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.526
_diffrn_reflns_theta_min         2.520
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.053
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1508 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.7287.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_description       plate
_exptl_crystal_F_000             1308
_exptl_crystal_recrystallization_method
'water solution of pytren-C8 with 1 eq of Cu(ClO4)2 solution. Then vapour diffussion of ethanol.'
_exptl_crystal_size_max          0.138
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.051
_refine_diff_density_max         1.138
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         8299
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0706
_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^)+(0.0746P)^2^+5.4781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1911
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5311
_reflns_number_total             8299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01736j2.cif
_cod_data_source_block           sb18_0ma
_cod_original_cell_volume        2718.7(12)
_cod_database_code               7160862
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.868
_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
 C21A-C20 \\sim C21-C20
 with sigma of 0.02
3. Others
 Sof(H19C)=Sof(H19D)=Sof(H16C)=Sof(H16D)=Sof(C18)=Sof(H18A)=Sof(H18B)=
 Sof(C17A)=Sof(H17C)=Sof(H17D)=1-FVAR(1)
 Sof(H19A)=Sof(H19B)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=
 Sof(C18A)=Sof(H18C)=Sof(H18D)=FVAR(1)
 Sof(H20C)=Sof(H20D)=Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(2)
 Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 N5(H5), N4(H4), N2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C20(H20C,H20D), C20(H20A,H20B), C19(H19A,H19B), C19(H19C,H19D), C12(H12A,
 H12B), C15(H15A,H15B), C14(H14A,H14B), C3(H3A,H3B), C1(H1A,H1B), C4(H4A,H4B),
 C2(H2A,H2B), C6(H6A,H6B), C13(H13A,H13B), C5(H5A,H5B), C16(H16A,H16B),
 C16(H16C,H16D), C17(H17A,H17B), C18(H18A,H18B), C17A(H17C,H17D), C18A(H18C,
 H18D)
4.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C9(H9)
4.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C21A(H21D,H21E,H21F)
;
_shelx_res_checksum              31152
_olex2_date_sample_data_collection 2020-01-29
_olex2_date_sample_submission    2020-01-29
_olex2_submission_original_sample_id sb18_cuc8
_olex2_submission_special_instructions 'No special instructions were received'