Synthesis of maleimide-braced peptide macrocycles and their potential anti-SARS-CoV-2 mechanisms.
Li, Jian; Sun, Jina; Zhang, Xianglei; Zhang, Ruxue; Wang, Qian; Wang, Lin; Zhang, Leike; Xie, Xiong; Li, Chunpu; Zhou, Yu; Wang, Jiang; Xiao, Gengfu; Bai, Fang; Liu, Hong; Chemical communications (Cambridge, England) 59 (2023) 868–871; doi:10.1039/d2cc06371a

data_7131086
_publ_section_title
;
 Synthesis of maleimide-braced peptide macrocycles and their potential
 anti-SARS-CoV-2 mechanisms.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              868
_journal_page_last               871
_journal_paper_doi               10.1039/d2cc06371a
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C32 H38 F3 N3 O6 S Si'
_chemical_formula_sum            'C32 H38 F3 N3 O6 S Si'
_chemical_formula_weight         677.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-02-08 deposited with the CCDC.	2022-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.076(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5652(9)
_cell_length_b                   14.6334(11)
_cell_length_c                   12.0301(11)
_cell_measurement_reflns_used    2087
_cell_measurement_temperature    170
_cell_measurement_theta_max      22.953
_cell_measurement_theta_min      2.296
_cell_volume                     1886.7(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_unetI/netI     0.1237
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14406
_diffrn_reflns_point_group_measured_fraction_full 0.854
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.416
_diffrn_reflns_theta_min         2.297
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1020 before and 0.0712 after correction. The Ratio of minimum to maximum transmission is 0.9072. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
TITL mo_22020750_0m_a.res in P2(1)
CELL   11.5652   14.6334   12.0301     90.00    112.08     90.00
SPGR P21
C101 0.358 0.334 0.359 !       7.49 eA-3
C102 0.579 0.848 0.632 !       5.84 eA-3
C103 0.718 0.989 0.785 !       5.55 eA-3
C104 0.388 0.512 0.251 !       4.57 eA-3
C105 0.410 0.439 0.347 !       3.29 eA-3
Q106 0.427 0.350 0.449 !       1.36 eA-3
Q107 0.687 1.000 0.685 !       1.25 eA-3
C108 0.357 0.389 0.283 !       1.24 eA-3
Q109 0.641 0.768 0.689 !       1.18 eA-3
Q110 0.657 0.683 0.637 !       1.18 eA-3
Q111 0.084 0.449 0.140 !       1.17 eA-3
C112 0.334 0.231 0.412 !       1.13 eA-3
Q113 0.676 0.063 0.715 !       1.11 eA-3
Q114 0.635 0.893 0.552 !       1.10 eA-3
Q115 0.340 0.406 0.195 !       1.09 eA-3
Q116 0.506 0.951 0.622 !       1.09 eA-3
Q117 0.309 0.301 0.231 !       1.04 eA-3
Q118 0.374 0.367 0.200 !       1.03 eA-3
Q119 0.709 0.847 0.796 !       1.03 eA-3
Q120 0.596 0.796 0.700 !       1.00 eA-3
C121 0.495 0.409 0.438 !       0.99 eA-3
Q122 0.979 0.422 0.100 !       0.99 eA-3
C123 0.688 0.937 0.864 !       0.96 eA-3
Q124 0.502 0.089 0.732 !       0.96 eA-3
Q125 0.815 1.000 0.692 !       0.95 eA-3
Q126 0.654 0.108 0.732 !       0.94 eA-3
Q127 0.592 0.899 0.852 !       0.94 eA-3
Q128 0.922 1.002 0.691 !       0.92 eA-3
Q129 0.377 0.111 0.507 !       0.91 eA-3
C130 0.467 0.488 0.470 !       0.91 eA-3
Q131 1.000 0.872 0.834 !       0.90 eA-3
C132 0.219 0.422 0.135 !       0.89 eA-3
Q133 0.263 0.393 0.457 !       0.89 eA-3
Q134 0.515 0.585 0.193 !       0.88 eA-3
Q135 0.489 0.981 0.741 !       0.87 eA-3
Q136 0.120 0.379 0.128 !       0.87 eA-3
Q137 0.339 0.830 0.571 !       0.86 eA-3
Q138 0.278 0.494 0.399 !       0.85 eA-3
Q139 0.802 0.785 0.682 !       0.85 eA-3
Q140 0.936 0.347 0.638 !       0.84 eA-3
Q141 0.782 0.347 0.653 !       0.81 eA-3
Q142 0.158 0.454 0.160 !       0.80 eA-3
Q143 0.229 0.332 0.332 !       0.77 eA-3
Q144 0.233 0.540 0.319 !       0.76 eA-3
Q145 0.762 0.771 0.614 !       0.76 eA-3
Q146 0.858 0.857 0.581 !       0.74 eA-3
C147 0.313 0.439 0.311 !       0.74 eA-3
Q148 0.027 0.486 0.087 !       0.74 eA-3
Q149 0.297 0.532 0.084 !       0.73 eA-3
Q150 0.550 0.031 0.467 !       0.73 eA-3
C151 0.971 0.954 0.788 !       0.72 eA-3
Q152 0.732 0.734 0.691 !       0.70 eA-3
Q153 0.626 0.648 0.578 !       0.70 eA-3
Q154 0.691 0.834 0.562 !       0.69 eA-3
Q155 0.576 0.952 0.500 !       0.69 eA-3
Q156 0.754 0.799 0.749 !       0.69 eA-3
Q157 0.137 0.391 0.042 !       0.69 eA-3
Q158 0.768 1.000 0.939 !       0.69 eA-3
Q159 0.472 0.230 0.470 !       0.68 eA-3
Q160 0.472 0.900 0.735 !       0.67 eA-3
Q161 0.464 0.035 0.488 !       0.67 eA-3
Q162 0.093 0.938 0.755 !       0.66 eA-3
Q163 0.957 0.517 0.283 !       0.66 eA-3
Q164 0.486 0.425 0.206 !       0.66 eA-3
Q165 0.998 0.072 0.751 !       0.66 eA-3
Q166 0.143 0.567 0.226 !       0.65 eA-3
Q167 0.494 0.274 0.420 !       0.65 eA-3
Q168 0.158 0.822 0.888 !       0.64 eA-3
Q169 0.682 0.798 0.547 !       0.64 eA-3
Q170 0.504 0.016 0.830 !       0.64 eA-3
Q171 0.375 0.485 0.469 !       0.63 eA-3
Q172 0.796 0.856 0.801 !       0.63 eA-3
Q173 0.014 0.354 0.099 !       0.62 eA-3
Q174 0.814 0.889 0.690 !       0.62 eA-3
Q175 0.281 0.352 0.133 !       0.61 eA-3
Q176 0.501 0.606 0.440 !       0.61 eA-3
Q177 0.063 0.039 0.808 !       0.60 eA-3
Q178 0.432 0.214 0.358 !       0.60 eA-3
Q179 0.923 0.314 0.163 !       0.60 eA-3
Q180 0.174 0.838 0.811 !       0.60 eA-3
Q181 0.814 0.401-0.004 !       0.59 eA-3
Q182 0.372 0.282 0.543 !       0.58 eA-3
Q183 0.424 0.625 0.342 !       0.58 eA-3
Q184 0.740 0.098 0.813 !       0.57 eA-3
Q185 0.439 0.533 0.437 !       0.57 eA-3
Q186 0.110 0.355 0.263 !       0.56 eA-3
Q187 0.343 0.877 0.582 !       0.56 eA-3
Q188 0.098 0.263 0.736 !       0.56 eA-3
Q189 0.344 0.546 0.374 !       0.55 eA-3
Q190 0.358 0.415 0.057 !       0.55 eA-3
Q191 0.672 0.570 0.468 !       0.54 eA-3
C192 0.090 0.947 0.855 !       0.53 eA-3
Q193 0.605 0.065 0.080 !       0.53 eA-3
Q194 0.203 0.611 0.047 !       0.53 eA-3
Q195 0.344 0.627 0.344 !       0.53 eA-3
Q196 0.033 0.930 0.773 !       0.52 eA-3
Q197 0.596 0.560 0.445 !       0.52 eA-3
Q198 0.772 0.245 0.972 !       0.51 eA-3
Q199 0.846 0.816 0.644 !       0.51 eA-3
;
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1066 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         6469
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1539
_refine_ls_R_factor_gt           0.0857
_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^)+(0.1186P)^2^+1.3002P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2045
_refine_ls_wR_factor_ref         0.2526
_reflns_Friedel_coverage         0.620
_reflns_Friedel_fraction_full    0.707
_reflns_Friedel_fraction_max     0.664
_reflns_number_gt                3728
_reflns_number_total             6469
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06371a3.cif
_cod_data_source_block           mo_22020750_0m_sq
_cod_depositor_comments          'Adding full bibliography for 7131086.cif.'
_cod_database_code               7131086
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2)
2.b Ternary CH refined with riding coordinates:
 C20(H20), C26(H26), C23(H23), C29(H29)
2.c Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.d Aromatic/amide H refined with riding coordinates:
 C14(H14), C18(H18), C15(H15), C9(H9), C16(H16), C5(H5), C4(H4), C1(H1),
 C3(H3), C2(H2A)
2.e Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C32(H32A,H32B,
 H32C), C25(H25A,H25B,H25C), C31(H31A,H31B,H31C), C27(H27A,H27B,H27C)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'