Precise assembly/disassembly of homo-type and hetero-type macrocycles with photoresponsive and non-photoresponsive dynamic covalent bonds.
Deng, Junmiao; Lu, Hanwei; Ye, Hebo; Hai, Yu; Liu, Zimu; You, Lei; Organic & biomolecular chemistry 23 (2025) 2498–2509; doi:10.1039/d5ob00094g

data_7160356
_publ_section_title
;
 Precise assembly/disassembly of homo-type and hetero-type macrocycles
 with photoresponsive and non-photoresponsive dynamic covalent bonds.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2498
_journal_page_last               2509
_journal_paper_doi               10.1039/d5ob00094g
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C28 H17 F3.002 O4 S2, C28 H19 F3 O4 S2'
_chemical_formula_sum            'C56 H38 F6 O8 S4'
_chemical_formula_weight         1081.10
_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             2024-06-04
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2024-10-31 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                63.307(3)
_cell_angle_beta                 80.700(2)
_cell_angle_gamma                87.091(2)
_cell_formula_units_Z            2
_cell_length_a                   10.8235(3)
_cell_length_b                   15.9748(5)
_cell_length_c                   17.4694(5)
_cell_measurement_reflns_used    12757
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.8170
_cell_measurement_theta_min      2.6850
_cell_volume                     2662.32(15)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28842
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.805
_diffrn_reflns_theta_min         1.321
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_refine_diff_density_max         0.877
_refine_diff_density_min         -0.814
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     767
_refine_ls_number_reflns         10000
_refine_ls_number_restraints     844
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0656
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1137P)^2^+1.9754P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1833
_refine_ls_wR_factor_ref         0.1947
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7356
_reflns_number_total             10000
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00094g2.cif
_cod_data_source_block           1o
_cod_depositor_comments          'Adding full bibliography for 7160356.cif.'
_cod_database_code               7160356
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C025-C01X \\sim C2-C0
 with sigma of 0.02
 O023-C025 \\sim O0-C0
 with sigma of 0.02
 O00G-C00W \\sim O00H-C00W
 with sigma of 0.02
3. Rigid bond restraints
 C021, F01U
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
Uanis(C01S) \\sim Ueq, Uanis(C01X) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(F01U) \\sim Ueq, Uanis(C021) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C021) \\sim Ueq, Uanis(F01U) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
5. Rigid body (RIGU) restrains
 C013, C4, C01Q, C01U, C3, C2, C1, C0, O0
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C013, C01S, C01X, C025, O023, C01Y, C01T, C01P
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C00W, O00H
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C00W, O00G
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
6. Others
 Sof(C0)=Sof(H0)=Sof(O0)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(C3)=Sof(H3)=Sof(C01U)=
 Sof(H01U)=Sof(C01Q)=Sof(H01Q)=1-FVAR(1)
 Sof(C01P)=Sof(H01P)=Sof(C01T)=Sof(H01T)=Sof(C01Y)=Sof(H01Y)=Sof(C01X)=
 Sof(C01S)=Sof(H01S)=Sof(O023)=Sof(C025)=Sof(H025)=FVAR(1)
 Sof(O00H)=1-FVAR(2)
 Sof(O00G)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C00M(H00M)
7.b Aromatic/amide H refined with riding coordinates:
 C00N(H00N), C00O(H00O), C00V(H00V), C00Y(H00Y), C00Z(H00Z), C014(H014),
 C018(H018), C01A(H01I), C01P(H01P), C01T(H01T), C01Y(H01Y), C01S(H01S),
 C01D(H01G), C01F(H01J), C01G(H01H), C01H(H01K), C01K(H01L), C01R(H01X),
 C01V(H01Z), C01Z(H01), C020(H020), C025(H025), C0(H0), C1(H1), C3(H3),
 C01U(H01U), C01Q(H01Q)
7.c Fitted hexagon refined as free rotating group:
 C4(C1,C2,C3,C01U,C01Q)
7.d Idealised Me refined as rotating group:
 C015(H01A,H01B,H01C), C01B(H01D,H01E,H01F), C01M(H01M,H01N,H01O), C01N(H01R,
 H01V,H01W)
7.e Idealised tetrahedral OH refined as rotating group:
 O007(H007)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              87230
_shelx_fab_checksum              44702
_olex2_submission_special_instructions 'No special instructions were received'