Synthesis of the Core Ring System of the Yuzurimine-Type Daphniphyllum Alkaloids by Cascade Condensation, Cyclization, Cycloaddition Chemistry
Iain Coldham; Luke Watson; Harry Adams; Nathaniel G. Martin; Journal of Organic Chemistry 76 (2011) 2360–2366; doi:10.1021/jo2000868

data_4026171
_publ_section_title
;
 Synthesis of the Core Ring System of the Yuzurimine-Type Daphniphyllum
 Alkaloids by Cascade Condensation, Cyclization, Cycloaddition Chemistry
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2360
_journal_page_last               2366
_journal_paper_doi               10.1021/jo2000868
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C18 H25 N O S'
_chemical_formula_sum            'C18 H25 N O S'
_chemical_formula_weight         303.45
_space_group_IT_number           82
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'I -4'
_symmetry_space_group_name_H-M   'I -4'
_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            8
_cell_length_a                   17.3324(8)
_cell_length_b                   17.3324(8)
_cell_length_c                   10.8249(5)
_cell_measurement_reflns_used    2201
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      18.94
_cell_measurement_theta_min      2.22
_cell_volume                     3251.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0808
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21298
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_correction_T_min  0.9595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       needle
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0643P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1214
_reflns_number_gt                1591
_reflns_number_total             1952
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2000868_si_002.cif
_cod_data_source_block           oic204a_0m
_cod_original_cell_volume        3251.9(4)
_cod_database_code               4026171