Unusual transannular cyclization products of sarcophytoxide, a 14-membered marine cembranoid: anomalous stereochemistry of epoxide-ketone rearrangement.
Nii, Keiji; Tagami, Keiko; Matsuoka, Keisuke; Munakata, Tatsuo; Ooi, Takashi; Kusumi, Takenori; Organic letters 8 (2006) 2957–2960; doi:10.1021/ol0608404

data_1506017
_publ_section_title
;
 Unusual transannular cyclization products of sarcophytoxide, a
 14-membered marine cembranoid: anomalous stereochemistry of
 epoxide-ketone rearrangement.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2957
_journal_page_last               2960
_journal_paper_doi               10.1021/ol0608404
_journal_volume                  8
_journal_year                    2006
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H30 O2 '
_chemical_formula_sum            'C20 H30 O2'
_chemical_formula_weight         302.44
_chemical_melting_point          363
_chemical_name_common            '2S,3Z,8R-7-Oxo-deepoxysarcophytoxide '
_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'
_cell_angle_alpha                90
_cell_angle_beta                 93.41(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.928(2)
_cell_length_b                   16.368(6)
_cell_length_c                   10.973(4)
_cell_measurement_reflns_used    7174
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     883.5(6)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9976
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.072
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8466
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             332.00
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2101
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[0.6050\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0560
_reflns_number_gt                1195
_reflns_number_total             2101
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol0608404si20060407_025333.cif
_cod_data_source_block           '_compound6'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'syn ' changed to 'syn'
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_formula_sum        'C20 H30 O2 '
_cod_database_code               1506017