Assembly of a Key Dienic Intermediate for Tetrodotoxin via a Machetti-DeSarlo Reaction
Jaclyn Chau; Sanjia Xu; Marco A. Ciufolini; Journal of Organic Chemistry 78 (2013) 11901–11910; doi:10.1021/jo401960p

data_4028802
_publ_section_title
;
 Assembly of a Key Dienic Intermediate for Tetrodotoxin via a
 Machetti-DeSarlo Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11901
_journal_page_last               11910
_journal_paper_doi               10.1021/jo401960p
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C29 H36 Cl2 N2 O5 Si'
_chemical_formula_weight         591.59
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.541(2)
_cell_angle_beta                 77.525(2)
_cell_angle_gamma                69.229(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5513(11)
_cell_length_b                   10.1186(11)
_cell_length_c                   17.6081(19)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    90.0(1)
_cell_measurement_theta_max      30.40
_cell_measurement_theta_min      2.62
_cell_volume                     1539.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90.0(1)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX DUO'
_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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34341
_diffrn_reflns_theta_full        30.52
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         9366
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.052
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+0.5909P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                7568
_reflns_number_total             9366
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401960p_si_003.cif
_cod_data_source_block           mc044
_cod_database_code               4028802