Intramolecular Cyclobutadiene Cycloaddition/Cyclopropanation/Thermal Rearrangement: An Effective Strategy for the Asymmetric Syntheses of Pleocarpenene and Pleocarpenone
Michael J. Williams; Holly L. Deak; Marc L. Snapper; Journal of the American Chemical Society 129 (2007) 486–487; doi:10.1021/ja0674340

data_4108993
_publ_section_title
;
 Intramolecular Cyclobutadiene Cycloaddition/Cyclopropanation/Thermal
 Rearrangement: An Effective Strategy for the Asymmetric Syntheses of
 Pleocarpenene and Pleocarpenone
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              486
_journal_page_last               487
_journal_paper_doi               10.1021/ja0674340
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C15.5 H25.5 O3'
_chemical_formula_weight         259.86
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.124(3)
_cell_length_b                   6.0143(9)
_cell_length_c                   12.8665(19)
_cell_measurement_reflns_used    3968
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.86
_cell_volume                     1325.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4924
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       chunk
_exptl_crystal_F_000             570
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2632
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0747P)^2^+0.2664P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1069
_reflns_number_gt                2566
_reflns_number_total             2632
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0674340si20061017_070046.cif
_cod_data_source_block           mw01a
_cod_original_cell_volume        1325.1(3)
_cod_original_formula_sum        'C15.50 H25.50 O3'
_cod_database_code               4108993