Chemical Synthesis Enables Structural Reengineering of Aglaroxin C Leading to Inhibition Bias for Hepatitis C Viral Infection.
Zhang, Wenhan; Liu, Shufeng; Maiga, Rayelle I.; Pelletier, Jerry; Brown, Lauren E.; Wang, Tony T.; Porco, Jr, John A; Journal of the American Chemical Society 141 (2019) 1312–1323; doi:10.1021/jacs.8b11477

data_4133586
_publ_section_title
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 Chemical Synthesis Enables Structural Reengineering of Aglaroxin C
 Leading to Inhibition Bias for Hepatitis C Viral Infection.
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_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1312
_journal_page_last               1323
_journal_paper_doi               10.1021/jacs.8b11477
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C35 H31 N O8'
_chemical_formula_sum            'C35 H31 N O8'
_chemical_formula_weight         593.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-08 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 94.776(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.6128(17)
_cell_length_b                   10.4020(7)
_cell_length_c                   21.3640(14)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      66.67
_cell_measurement_theta_min      3.33
_cell_volume                     5893.6(7)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2006)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 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      100(1)
_diffrn_measured_fraction_theta_full 0.997
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33704
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         3.333
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0960 before and 0.0758 after correction.
The Ratio of minimum to maximum transmission is 0.8247.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       prism
_exptl_crystal_F_000             2496
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         5217
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0685
_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^)+(0.0400P)^2^+18.1830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1606
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4678
_reflns_number_total             5217
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {0d6253a4-724b-4c18-b8aa-bc30ae16e73b}
_cod_data_source_file            ja8b11477_si_002.cif
_cod_data_source_block           zhang3a_0m
_cod_database_code               4133586
_shelx_shelxl_version_number     2016/6
_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, All O(H) groups
2. Restrained distances
 C30B-C23
 1.51 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C27B) = Uanis(C27A)
Uanis(C28B) = Uanis(C28A)
Uanis(C26B) = Uanis(C26A)
Uanis(C25B) = Uanis(C25A)
Uanis(C29B) = Uanis(C29A)
Uanis(C24B) = Uanis(C24A)
Uanis(C5B) = Uanis(C5A)
Uanis(C4B) = Uanis(C4A)
Uanis(C3B) = Uanis(C3A)
Uanis(C2B) = Uanis(C2A)
Uanis(C7B) = Uanis(C7A)
Uanis(C6B) = Uanis(C6A)
Uanis(C30B) = Uanis(C30A)
Uanis(C31B) = Uanis(C31A)
Uanis(C32B) = Uanis(C32A)
Uanis(C33B) = Uanis(C33A)
Uanis(C34B) = Uanis(C34A)
Uanis(C35B) = Uanis(C35A)
4. Others
 Sof(C24B)=Sof(C25B)=Sof(H25B)=Sof(C26B)=Sof(H26B)=Sof(C27B)=Sof(H27B)=
 Sof(C28B)=Sof(H28B)=Sof(C29B)=Sof(H29B)=1-FVAR(1)
 Sof(C24A)=Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27A)=
 Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(H29A)=FVAR(1)
 Sof(O1B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C5B)=Sof(C6B)=Sof(H6B)=
 Sof(C7B)=Sof(H7B)=Sof(C2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4B)=1-FVAR(2)
 Sof(O1A)=Sof(C5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C2A)=Sof(C3A)=
 Sof(H3A)=Sof(C4A)=Sof(H4A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=FVAR(2)
 Sof(H23A)=Sof(C30B)=Sof(C35B)=Sof(H35B)=Sof(C34B)=Sof(H34B)=Sof(C33B)=
 Sof(H33B)=Sof(C32B)=Sof(H32B)=Sof(C31B)=Sof(H31B)=1-FVAR(3)
 Sof(H23)=Sof(C30A)=Sof(C31A)=Sof(H31A)=Sof(C35A)=Sof(H35A)=Sof(C32A)=
 Sof(H32A)=Sof(C34A)=Sof(H34A)=Sof(C33A)=Sof(H33A)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C20(H20), C23(H23), C23(H23A)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C6A(H6A), C7A(H7A), C3A(H3A), C4A(H4A), C14(H14), C31A(H31A),
 C25A(H25A), C26A(H26A), C27A(H27A), C28A(H28A), C29A(H29A), C35A(H35A),
 C32A(H32A), C34A(H34A), C33A(H33A), C25B(H25B), C26B(H26B), C27B(H27B),
 C28B(H28B), C29B(H29B), C6B(H6B), C7B(H7B), C3B(H3B), C4B(H4B), C35B(H35B),
 C34B(H34B), C33B(H33B), C32B(H32B), C31B(H31B)
5.c Fitted hexagon refined as free rotating group:
 C5A(C6A,C7A,C2A,C3A,C4A), C24A(C25A,C26A,C27A,C28A,C29A), C24B(C25B,C26B,C27B,
 C28B,C29B), C5B(C6B,C7B,C2B,C3B,C4B), C30B(C35B,C34B,C33B,C32B,C31B)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C1A(H1AA,H1AB,H1AC), C22(H22A,H22B,
 H22C), C1B(H1BA,H1BB,H1BC)
5.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
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_shelx_res_checksum              87008
_shelx_hkl_checksum              55361
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
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