Stereocontrolled Synthesis of (+)-Plagiogyrin A.
Shi, Yunlong; Pierce, Joshua G.; Organic letters 18 (2016) 5308–5311; doi:10.1021/acs.orglett.6b02629

data_1555830
_publ_section_title
;
 Stereocontrolled Synthesis of (+)-Plagiogyrin A.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5308
_journal_page_last               5311
_journal_paper_doi               10.1021/acs.orglett.6b02629
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H20 O7'
_chemical_formula_sum            'C18 H20 O7'
_chemical_formula_weight         348.34
_chemical_name_common            YS-69-53
_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
_cell_angle_alpha                90
_cell_angle_beta                 91.2050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.7535(2)
_cell_length_b                   10.0644(2)
_cell_length_c                   12.3488(3)
_cell_measurement_reflns_used    257
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      32.2445
_cell_measurement_theta_min      3.6252
_cell_volume                     839.16(4)
_computing_cell_refinement       'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24547
_diffrn_reflns_theta_full        33.23
_diffrn_reflns_theta_max         33.23
_diffrn_reflns_theta_min         2.61
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.202
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.185
_refine_ls_abs_structure_details
;
Starting material containing atom C14 was enentiomerically pure with R 
configuration. Synthetic method uses this center to dictate the stereochemistry
 at C3 and C13. Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         6413
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0534P)^2^+0.0463P]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0909
_reflns_number_gt                5825
_reflns_number_total             6413
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02629_si_002.cif
_cod_data_source_block           I
_cod_database_code               1555830
_shelx_res_checksum              40765
_shelx_hkl_checksum              97665