Regio- and diastereoselective synthesis and X-ray structure determination of (+)-2-deoxyoryzalexin S from (+)-podocarpic acid. Structural nonidentity with its nominal natural isolated enantiomer.
Leonelli, Francesca; Latini, Valentina; Trombetta, Andrea; Bartoli, Gabriele; Ceccacci, Francesca; La Bella, Angela; Sferrazza, Alessio; Lamba, Doriano; Migneco, Luisa M.; Bettolo, Rinaldo Marini; Journal of natural products 75 (2012) 1944–1950; doi:10.1021/np300518j

data_1508559
_publ_section_title
;
 Regio- and diastereoselective synthesis and X-ray structure determination
 of (+)-2-deoxyoryzalexin S from (+)-podocarpic acid. Structural
 nonidentity with its nominal natural isolated enantiomer.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              1944
_journal_page_last               1950
_journal_paper_doi               10.1021/np300518j
_journal_volume                  75
_journal_year                    2012
_chemical_formula_moiety         'C22 H34 O2'
_chemical_formula_sum            'C22 H34 O2'
_chemical_formula_weight         330.49
_chemical_name_systematic
;  
 (+)2-deoxy,2-acetyloryzalexin S
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.580(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6800(10)
_cell_length_b                   7.5300(10)
_cell_length_c                   13.0100(10)
_cell_measurement_temperature    293(2)
_cell_volume                     932.18(18)
_computing_cell_refinement       'Mosflm, iMosflm'
_computing_data_reduction        'Scala, Truncate, CCP4'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.888
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_device_type  'Pilatus 2M - Dectris'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_monochromator  'Si 111'
_diffrn_radiation_source         'XRD-1 Elettra, Trieste(Italy)'
_diffrn_radiation_type           'Synchrotron Radiation'
_diffrn_radiation_wavelength     0.900
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1380
_diffrn_reflns_theta_full        30.75
_diffrn_reflns_theta_max         30.75
_diffrn_reflns_theta_min         3.66
_exptl_absorpt_coefficient_mu    0.121
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.150
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(5)
_refine_ls_extinction_coef       0.04(3)
_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   1.988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         1380
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.987
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0994
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3610
_refine_ls_wR_factor_ref         0.3614
_reflns_number_gt                1356
_reflns_number_total             1380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np300518j_si_002.cif
_cod_data_source_block           fsa2
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

 Adding full bibliography for 1508559.cif.
;
_cod_original_cell_volume        932.18(17)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1508559