Short Total Syntheses of Both the Putative and Actual Structures of the Clerodane Diterpenoid (±)-Sacacarin by Double Annulation
Grossman, Robert B.; Rasne, Ravindra M.; Organic Letters 3 (2001) 4027–; doi:10.1021/ol016748j

data_1507541
_publ_section_title
;
 Short Total Syntheses of Both the Putative and Actual Structures of the
 Clerodane Diterpenoid (+-)-Sacacarin by Double Annulation
;
_journal_issue                   25
_journal_name_full               'Organic Letters'
_journal_page_first              4027
_journal_paper_doi               10.1021/ol016748j
_journal_volume                  3
_journal_year                    2001
_chemical_formula_sum            'C18 H24 N2 O5'
_chemical_formula_weight         348.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.495(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7580(10)
_cell_length_b                   12.1860(10)
_cell_length_c                   13.1720(10)
_cell_measurement_reflns_used    16402
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1886.7(3)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material
'SHELX97-2 (Sheldrick, 1997) and local procedures'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(1)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '\w scans at fixed \c = 55\%'
_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  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7931
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
 Tmin = 0.967 Tmax = 0.982 estimated from dimensions and \m.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block cut from needle'
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         .247
_refine_diff_density_min         -.154
_refine_diff_density_rms         .034
_refine_ls_extinction_coef       0.0066(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0411P)^2^+0.4936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1004
_reflns_number_gt                3291
_reflns_number_total             4316
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol016748j_s2.cif
_cod_data_source_block           k00132
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1507541