Total synthesis of (+/-)-herbertenolide by stereospecific formation of vicinal quaternary centers in a crystalline ketone.
Ng, Danny; Yang, Zhe; Garcia-Garibay, Miguel A; Organic letters 6 (2004) 645–647; doi:10.1021/ol0499250

data_1507127
_publ_section_title
;
 Total synthesis of (+/-)-herbertenolide by stereospecific formation of
 vicinal quaternary centers in a crystalline ketone.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              645
_journal_page_last               647
_journal_paper_doi               10.1021/ol0499250
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C18 H24 O4'
_chemical_formula_weight         304.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 95.806(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7539(13)
_cell_length_b                   14.491(2)
_cell_length_c                   13.0722(19)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      2.81
_cell_volume                     1649.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.766
_diffrn_measured_fraction_theta_max 0.766
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7269
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.87477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs(Bruker)
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+0.0536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0975
_reflns_number_gt                2276
_reflns_number_total             2915
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0499250si20040113_115029.cif
_cod_data_source_block           gg202
_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_sg_symbol_H-M      P2(1)/c
_cod_database_code               1507127