First studies directed towards the diastereoselective synthesis of the BCD tricyclic core of brownin F.
Rodier, Fabien; Parrain, Jean-Luc; Chouraqui, Gaëlle; Commeiras, Laurent; Organic & biomolecular chemistry 11 (2013) 4178–4185; doi:10.1039/c3ob40363g

data_7152987
_publ_section_title
;
 First studies directed towards the diastereoselective synthesis of the
 BCD tricyclic core of brownin F.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4178
_journal_page_last               4185
_journal_paper_doi               10.1039/c3ob40363g
_journal_volume                  11
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C13 H14 O5'
_chemical_formula_sum            'C13 H14 O5'
_chemical_formula_weight         250.24
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-03-02T16:27:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2012-10-19 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 94.451(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6438(3)
_cell_length_b                   7.4285(2)
_cell_length_c                   8.7806(4)
_cell_measurement_reflns_used    5158
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7
_cell_measurement_theta_min      2.33
_cell_measurement_wavelength     0.71073
_cell_volume                     562.11(4)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5158
_diffrn_reflns_theta_full        28.7
_diffrn_reflns_theta_max         28.7
_diffrn_reflns_theta_min         2.33
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1493
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0975P)^2^+0.0402P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1548
_reflns_number_gt                1293
_reflns_number_total             1493
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob40363g.txt
_cod_data_source_block           fr93
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7152987