Enantioselective Total Synthesis of (-)-Acetylaranotin, a Dihydrooxepine Epidithiodiketopiperazine
Julian A. Codelli; Angela L. A. Puchlopek; Sarah E. Reisman; Journal of the American Chemical Society 134 (2012) 1930–1933; doi:10.1021/ja209354e

data_4117364
_publ_section_title
;
 Enantioselective Total Synthesis of (-)-Acetylaranotin, a Dihydrooxepine
 Epidithiodiketopiperazine
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1930
_journal_page_last               1933
_journal_paper_doi               10.1021/ja209354e
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H18 N2 O8, 0.5(C6 H6), H2 O'
_chemical_formula_sum            'C21 H23 N2 O9'
_chemical_formula_weight         447.41
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.41(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.744(4)
_cell_length_b                   7.7389(15)
_cell_length_c                   12.557(3)
_cell_measurement_temperature    100(2)
_cell_volume                     1999.0(7)
_computing_cell_refinement       'Bruker SAINT-Plus v7.68A'
_computing_data_collection       'Bruker APEX2 v2009.7-0'
_computing_data_reduction        'Bruker SAINT-Plus v7.68A'
_computing_molecular_graphics    'Bruker XP v5.1'
_computing_publication_material  'Bruker XCIF 2008'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker KAPPA APEX II'
_diffrn_measurement_method       '\w scans; 8 settings'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4904
_diffrn_reflns_theta_full        30.52
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS v2008/4, Bruker-AXS, Madison, WI'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       Blade
_exptl_crystal_F_000             940
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.523
_refine_ls_hydrogen_treatment    Riding
_refine_ls_matrix_type           'Full matrix'
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4905
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      2.522
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/s^2^(Fo^2^)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0570
_refine_ls_wR_factor_ref         0.0586
_reflns_number_gt                3856
_reflns_number_total             4905
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja209354e_si_006.cif
_cod_data_source_block           jac06
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'direct methods' was changed to
'direct'.

'_atom_sites_solution_secondary' value 'Difference Fourier map' was
changed to 'difmap'.

'_atom_sites_solution_hydrogens' value 'Geometric positions' was
changed to 'geom'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_database_code               4117364