Tandem Diels–Alder reaction overrules entropy: the gate to thermally stable, yet thermally recyclable furan-based polymers
Zakharova, Daria V.; Aysin, Rinat R.; Pavlov, Alexander A.; Khanin, Dmirty A.; Platonova, Elena O.; Nelyubina, Yulia V.; Polezhaev, Alexander V.; Green Chemistry 27 (2025) 2263–2275; doi:10.1039/D4GC04846F

data_7249747
_publ_section_title
;
 Tandem Diels--Alder reaction overrules entropy: the gate to thermally
 stable, yet thermally recyclable furan-based polymers
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              2263
_journal_page_last               2275
_journal_paper_doi               10.1039/D4GC04846F
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C2 H6 O S, 2(C27 H24 N2 O5)'
_chemical_formula_sum            'C56 H54 N4 O11 S'
_chemical_formula_weight         991.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2024-07-11 deposited with the CCDC.	2025-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.016(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8335(10)
_cell_length_b                   18.2519(19)
_cell_length_c                   26.581(3)
_cell_measurement_reflns_used    4005
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.65
_cell_measurement_theta_min      2.36
_cell_volume                     4770.8(9)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 1.000
_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  0.1017
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            42274
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.895
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1502 before and 0.0869 after correction.
The Ratio of minimum to maximum transmission is 0.8160.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       prism
_exptl_crystal_F_000             2088
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         8397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0430P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5473
_reflns_number_total             8397
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc04846f2.cif
_cod_data_source_block           5d
_cod_depositor_comments
'Adding full bibliography for 7249746--7249747.cif.'
_cod_database_code               7249747
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C15(H15), C3A(H3A), C4A(H4A),
 C5A(H5A), C6A(H6A), C8A(H8A), C15A(H15A)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C19A(H19C,H19D), C20A(H20C,H20D)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C22(H22), C23(H23), C25(H25), C26(H26), C10A(H10A), C11A(H11A), C12A(H12A),
 C13A(H13A), C14A(H14A), C16A(H16A), C17A(H17A), C22A(H22A), C23A(H23A),
 C25A(H25A), C26A(H26A)
2.d Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,H2SC), C27(H27A,H27B,H27C), C27A(H27D,H27E,
 H27F)
;
_shelx_res_checksum              96415
_shelx_hkl_checksum              2737
_olex2_submission_special_instructions 'No special instructions were received'