General Stereodivergent Enantioselective Total Synthetic Approach toward Macrosphelides A-G and M.
Häcker, Christine; Plietker, Bernd; The Journal of organic chemistry 80 (2015) 8055–8064; doi:10.1021/acs.joc.5b01171

data_4036248
_publ_section_title
;
 General Stereodivergent Enantioselective Total Synthetic Approach toward
 Macrosphelides A-G and M.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8055
_journal_page_last               8064
_journal_paper_doi               10.1021/acs.joc.5b01171
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H22 O7, 0.125(H2 O)'
_chemical_formula_sum            'C16 H22.25 O7.13'
_chemical_formula_weight         328.59
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8884(7)
_cell_length_b                   14.8186(16)
_cell_length_c                   19.816(2)
_cell_measurement_reflns_used    2511
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.07
_cell_measurement_theta_min      3.72
_cell_volume                     1729.1(3)
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker KAPPA APEXII Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_source         I\mS
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11338
_diffrn_reflns_theta_full        66.07
_diffrn_reflns_theta_max         66.07
_diffrn_reflns_theta_min         3.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             701
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2918
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0303P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0675
_reflns_number_gt                2511
_reflns_number_total             2918
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01171_si_004.cif
_cod_data_source_block           s2098lc
_cod_database_code               4036248