A Synthetic Approach to the Fusicoccane A-B Ring Fragment Based on a Pauson-Khand Cycloaddition/Norrish Type 1 Fragmentation
Gregory R. Dake; Erik E. Fenster; Brian O. Patrick; Journal of Organic Chemistry 73 (2008) 6711–6715; doi:10.1021/jo800933f

data_4023637
_publ_section_title
;
 A Synthetic Approach to the Fusicoccane A-B Ring Fragment Based
 on a Pauson-Khand Cycloaddition/Norrish Type 1 Fragmentation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6711
_journal_page_last               6715
_journal_paper_doi               10.1021/jo800933f
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_sum            'C18 H31 N O2'
_chemical_formula_weight         293.44
_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                 96.002(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.1125(12)
_cell_length_b                   5.8190(5)
_cell_length_c                   13.5233(14)
_cell_measurement_reflns_used    5414
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      2.50
_cell_volume                     869.67(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'area detector'
_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  0.0627
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14299
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3932
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0625P)^2^+0.0927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                3420
_reflns_number_total             3932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800933f-file003.cif
_cod_data_source_block           gd012
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023637