Toward the Total Synthesis of Vinigrol: Synthesis of epi-C-8-Dihydrovinigrol
Lionel Gentric; Xavier Le Goff; Louis Ricard; Issam Hanna; Journal of Organic Chemistry 74 (2009) 9337–9344; doi:10.1021/jo901971f

data_4025094
_publ_contact_author_address
;Laboratoire DCPH
Ecole Polytechnique
Route de Saclay
F91128 Palaiseau
France
;
_publ_contact_author_email       xavier-frederic.legoff@polytechnique.edu
_publ_contact_author_fax         330169334440
_publ_contact_author_name        'Xavier F. Le Goff'
_publ_contact_author_phone       330169334413
_publ_section_title
;
Toward the Total Synthesis of Vinigrol: Synthesis of epi-C-8-Dihydrovinigrol
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9337
_journal_page_last               9344
_journal_paper_doi               10.1021/jo901971f
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C24 H38 O5'
_chemical_formula_weight         406.54
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-09-15
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.2310(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4050(10)
_cell_length_b                   14.6640(10)
_cell_length_c                   13.7140(10)
_cell_measurement_reflns_used    4776
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      2.910
_cell_volume                     2190.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150.0(1)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  KappaCCD
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10183
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_correction_T_min  0.9817
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0074(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         6309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0546P)^2^+0.2546P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                4911
_reflns_number_total             6309
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901971f_si_001.cif
_cod_data_source_block           c24o5
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P21/n     '
_cod_database_code               4025094