Aplydactone, a New Sesquiterpenoid with an Unprecedented Carbon Skeleton from the Sea Hare Aplysia dactylomela, and Its Cargill-Like Rearrangement
Sergey N. Fedorov; Oleg S. Radchenko; Larisa K. Shubina; Anatoly I. Kalinovsky; Andrey V. Gerasimenko; Dmitry Y. Popov; Valentin A. Stonik; Journal of the American Chemical Society 123 (2001) 504–505; doi:10.1021/ja003254t

data_4115422
_publ_section_title
;
 Aplydactone, a New Sesquiterpenoid with an Unprecedented Carbon Skeleton
 from the Sea Hare Aplysia dactylomela, and Its Cargill-Like Rearrangement
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              504
_journal_page_last               505
_journal_paper_doi               10.1021/ja003254t
_journal_volume                  123
_journal_year                    2001
_chemical_formula_moiety         C15H21BrO
_chemical_formula_sum            'C15 H21 Br O'
_chemical_formula_weight         297.23
_chemical_melting_point          468(1)
_chemical_name_common            aplydactone
_chemical_name_systematic
; 
 (1R,3S,6S,8R,11S)-8-bromo-3,7,7-trimethyltetracyclo[4.4.2.01,6.03,11]
  dodecan-4-one
;
_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                 93.202(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.1894(11)
_cell_length_b                   12.3968(19)
_cell_length_c                   7.6376(11)
_cell_measurement_reflns_used    698
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.4
_cell_measurement_theta_min      5.3
_cell_volume                     679.64(18)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1998)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL/PC (Sheldrick, 1998)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area detector diffractometer'
_diffrn_measurement_method       '\w scan'
_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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3199
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    3.007
_exptl_absorpt_correction_T_max  0.801
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       'Transparent crystals'
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.064(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1837
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.610
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0670
_reflns_number_gt                1737
_reflns_number_total             1837
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja003254t.cif
_cod_data_source_block           tibox01j
_cod_database_code               4115422