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_1506018
_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         'C30 H37 F3 O3 '
_chemical_formula_sum            'C30 H37 F3 O3'
_chemical_formula_weight         502.62
_chemical_melting_point          369
_chemical_name_common
;
3,3,3-trifluoro-2-methoxy-2-phenyl-propionic acid 1-isopropyl-4,7,11-trimethyl-
5,6,7,8,9,10-hexahydro-benzocyclodecen-8-yl ester 
;
_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                 105.59(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.863(4)
_cell_length_b                   8.753(3)
_cell_length_c                   14.460(5)
_cell_measurement_reflns_used    8905
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1324.3(8)
_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 0.9963
_diffrn_measured_fraction_theta_max 0.9963
_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  0.100
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13145
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.64
_refine_diff_density_min         -0.61
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     362
_refine_ls_number_reflns         3223
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[0.2980\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0430
_reflns_number_gt                1254
_reflns_number_total             3223
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol0608404si20060407_025358.cif
_cod_data_source_block           '_compound10'
_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        'C30 H37 F3 O3 '
_cod_database_code               1506018