Total Synthesis and Anti-Tobacco Mosaic Virus Activity of the Furofuran Lignan (±)-Phrymarolin II and Its Analogues.
Chi, Yuan; Zhou, Huan; He, Hong-Wei; Ma, Yi-Dan; Li, Bo; Xu, Dan; Gao, Jin-Ming; Xu, Gong; Journal of natural products 84 (2021) 2937–2944; doi:10.1021/acs.jnatprod.1c00763

data_1565523
_publ_section_title
;
 Total Synthesis and Anti-Tobacco Mosaic Virus Activity of the Furofuran
 Lignan (+-)-Phrymarolin II and Its Analogues.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              2937
_journal_page_last               2944
_journal_paper_doi               10.1021/acs.jnatprod.1c00763
_journal_volume                  84
_journal_year                    2021
_chemical_formula_moiety         'C14 H16 O7'
_chemical_formula_sum            'C14 H16 O7'
_chemical_formula_weight         296.27
_chemical_name_systematic
(1S,3aR,4S,6aS)-4-(6-methoxybenzo[d][1,3]dioxol-5-yl)dihydro-1H,3H-furo[3,4-c]furan-1,6a(6H)-diol
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-18
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.5790(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.2746(7)
_cell_length_b                   5.3528(2)
_cell_length_c                   11.9234(4)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    153
_cell_measurement_theta_max      68.296
_cell_measurement_theta_min      2.189
_cell_volume                     1287.87(8)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      153.0
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method       '/w scans with narrow frames'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22526
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.364
_diffrn_reflns_theta_min         2.190
_diffrn_source                   'Advanced Light Source, station 11.3.1'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.055
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5460
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0053(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0387P)^2^+0.7058P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2279
_reflns_number_total             2337
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00763_si_002.cif
_cod_data_source_block           tianyu20200928_1_0m
_cod_database_code               1565523
_shelx_shelxl_version_number     2018/3
_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.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C9(H9A,H9B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C4(H4)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O7(H7)
;
_shelx_res_checksum              27048
_shelx_hkl_checksum              51483
_olex2_submission_original_sample_id CY-1
_olex2_submission_special_instructions 'No special instructions were received'