Macrocycle formation-mediated augmentation in reactive oxygen species production.
Liu, Ao; Xin, Youtao; Zhu, Yong-Kang; Jin, Yuan-Hang; Yang, Yue; Chen, Hongzhu; Li, Meng-Hao; Lou, Xin-Yue; Wang, Xin; Gao, Hui; Yang, Ying-Wei; Chemical science 16 (2025) 20968–20977; doi:10.1039/d5sc06637a

data_1575938
_publ_section_title
;
 Macrocycle formation-mediated augmentation in reactive oxygen species
 production.
;
_journal_issue                   44
_journal_name_full               'Chemical science'
_journal_page_first              20968
_journal_page_last               20977
_journal_paper_doi               10.1039/d5sc06637a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         '2(C41 H42 O4), 1.25[C6H14O]'
_chemical_formula_sum            'C89.5 H101.5 O9.25'
_chemical_formula_weight         1325.20
_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             2024-05-26
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-15 deposited with the CCDC.	2025-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                93.260(5)
_cell_angle_beta                 106.450(5)
_cell_angle_gamma                118.165(5)
_cell_formula_units_Z            2
_cell_length_a                   14.788(3)
_cell_length_b                   14.851(3)
_cell_length_c                   21.736(4)
_cell_measurement_reflns_used    5086
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.57
_cell_measurement_theta_min      2.75
_cell_volume                     3932.3(14)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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      100.00
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1099
_diffrn_reflns_av_unetI/netI     0.0982
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            59993
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.676
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_description       block
_exptl_crystal_F_000             1425
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.795
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     699
_refine_ls_number_reflns         13765
_refine_ls_number_restraints     111
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.2302
_refine_ls_R_factor_gt           0.1416
_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^)+(0.2000P)^2^+12.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3471
_refine_ls_wR_factor_ref         0.4308
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5927
_reflns_number_total             13765
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06637a2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1575936--1575938.cif.'
_cod_original_cell_volume        3932.3(12)
_cod_original_formula_sum        'C89.50 H101.50 O9.25'
_cod_database_code               1575938
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.990
_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. Restrained distances
 C2-C1 = C21-C20 = C9-C10 = C19-C18 = C51-C50 = C43-C42 = C60-C59 = C62-C61
 1.53 with sigma of 0.01
 C76-C73 \\sim C82-C79 \\sim C70-C67 \\sim C41-C38 \\sim C35-C32 \\sim C29-C26
\\sim C23-C22 \\sim C22-C15
 \\sim C12-C11 \\sim C7-C11 \\sim C64-C63 \\sim C63-C56 \\sim C53-C52 \\sim
C52-C46
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O1 \\sim C1 \\sim C2: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08 within 2A
C1 \\sim C2: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
4.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C9(H9a,H9b), C11(H11a,H11b), C18(H18a,H18b), C20(H20a,H20b),
 C22(H22a,H22b), C41(H41a,H41b), C43(H43a,H43b), C50(H50a,H50b), C52(H52a,H52b),
  C59(H59a,H59b), C61(H61a,H61b), C63(H63a,H63b), C82(H82a,H82b)
4.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C14(H14), C17(H17), C28(H28), C27(H27), C25(H25), C24(H24),
 C34(H34), C33(H33), C31(H31), C30(H30), C40(H40), C39(H39), C37(H37), C36(H36),
  C48(H48), C45(H45), C58(H58), C55(H55), C69(H69), C68(H68), C66(H66),
 C65(H65), C75(H75), C74(H74), C72(H72), C71(H71), C77(H77), C78(H78), C80(H80),
  C81(H81)
4.c Fitted hexagon refined as free rotating group:
 C3(C8,C7,C6,C5,C4), C12(C13,C14,C15,C16,C17), C23(C28,C27,C26,C25,C24),
 C29(C34,C33,C32,C31,C30), C35(C40,C39,C38,C37,C36), C44(C49,C48,C47,C46,C45),
 C53(C58,C57,C56,C55,C54), C64(C69,C68,C67,C66,C65), C70(C75,C74,C73,C72,C71),
 C76(C77,C78,C79,C80,C81)
4.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C10(H10a,H10b,H10c), C19(H19a,H19b,H19c), C21(H21a,H21b,
 H21c), C42(H42a,H42b,H42c), C51(H51a,H51b,H51c), C60(H60a,H60b,H60c), C62(H62a,
 H62b,H62c)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              41723
_shelx_fab_checksum              51539
_olex2_submission_special_instructions 'No special instructions were received'