Divergent Synthesis of Antiviral Diterpenes Wickerols A and B.
Deng, Jiachen; Ning, Yuhan; Tian, Hailong; Gui, Jinghan; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b11838

data_4134263
_publ_section_title
;
 Divergent Synthesis of Antiviral Diterpenes Wickerols A and B.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b11838
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C14 H22 O2'
_chemical_formula_sum            'C14 H22 O2'
_chemical_formula_weight         222.31
_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             2018-01-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.4240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.53900(10)
_cell_length_b                   10.9976(2)
_cell_length_c                   15.3730(3)
_cell_measurement_reflns_used    9758
_cell_measurement_temperature    170
_cell_measurement_theta_max      60.867
_cell_measurement_theta_min      3.498
_cell_volume                     1263.90(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20519
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.837
_diffrn_reflns_theta_min         5.048
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1107 before and 0.0491 after correction. The Ratio of minimum to maximum transmission is 0.8433. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 2683 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5771
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0304
_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^)+(0.0560P)^2^+0.1655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0838
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                5736
_reflns_number_total             5771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b11838_si_003.cif
_cod_data_source_block           mjl18022_0m
_cod_database_code               4134263
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.970
_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:
 C3(H3), C4(H4), C8(H8), C9(H9), C3A(H3A), C4A(H4A), C8A(H8A), C9A(H9A)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C1A(H1AB,H1AC), C2A(H2AB,
 H2AC), C5A(H5AA,H5AB), C6A(H6AA,H6AB)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C11A(H11A), C12A(H12A)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C13A(H13D,H13E,H13F), C14A(H14D,
 H14E,H14F)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1A(H1AA), O2A(H2AA)
;
_shelx_res_checksum              81168
_shelx_hkl_checksum              75490
_olex2_submission_special_instructions 'No special instructions were received'