Formal total synthesis of (-)-apicularen A via transannular conjugate addition.
Hilli, Ferdows; White, Jonathan M.; Rizzacasa, Mark A.; Organic letters 6 (2004) 1289–1292; doi:10.1021/ol0497943

data_1507118
_publ_section_title
;
 Formal total synthesis of (-)-apicularen A via transannular conjugate
 addition.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1289
_journal_page_last               1292
_journal_paper_doi               10.1021/ol0497943
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C19 H22 O5'
_chemical_formula_weight         330.37
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 116.912(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.939(3)
_cell_length_b                   7.4210(8)
_cell_length_c                   23.556(3)
_cell_measurement_reflns_used    1249
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      20.53
_cell_measurement_theta_min      2.92
_cell_volume                     3575.7(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_sigmaI/netI    0.1042
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10863
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.956
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4057
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1759
_refine_ls_R_factor_gt           0.1061
_refine_ls_shift/su_max          1.461
_refine_ls_shift/su_mean         0.107
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3016
_refine_ls_wR_factor_ref         0.3460
_reflns_number_gt                1957
_reflns_number_total             4057
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0497943si20040204_113830.cif
_cod_data_source_block           ferdowsl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3575.7(7)
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               1507118