Stereocontrolled synthesis of the oxathiabicyclo[3.3.1]nonane core structure of tagetitoxin
Hitomi Yamada; Masaatsu Adachi; Toshio Nishikawa; Chem.Commun. 49 (2013) 11221–; doi:10.1039/c3cc46949b

data_7110054
_publ_section_title
;
 Stereocontrolled synthesis of the oxathiabicyclo[3.3.1]nonane core
 structure of tagetitoxin
;
_journal_name_full               Chem.Commun.
_journal_page_first              11221
_journal_paper_doi               10.1039/c3cc46949b
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_formula_sum            'C19 H18 N2 O6'
_chemical_formula_weight         370.35
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                   10.4965(6)
_cell_length_b                   11.6262(7)
_cell_length_c                   14.6325(9)
_cell_measurement_reflns_used    4436
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.24
_cell_volume                     1785.67(18)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'Bruker Instrument Service (Bruker AXS)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8700
_diffrn_reflns_theta_full        25.17
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_correction_T_min  0.9805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008) SADABS. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(8)
_refine_ls_extinction_coef       0.0094(10)
_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   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3208
_refine_ls_number_restraints     71
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0303P)^2^+0.4954P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0720
_reflns_number_gt                3058
_reflns_number_total             3208
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc46949b.txt
_cod_data_source_block           p212121_a_a
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7110054