The Lyconadins: Enantioselective Total Syntheses of (+)-Lyconadin A and (-)-Lyconadin B
Douglas C. Beshore; Amos B. Smith; Journal of the American Chemical Society 130 (2008) 13778–13789; doi:10.1021/ja804939r

data_4108477
_publ_section_title
;
 The Lyconadins: Enantioselective Total Syntheses of (+)-Lyconadin A and
 (-)-Lyconadin B
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13778
_journal_page_last               13789
_journal_paper_doi               10.1021/ja804939r
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C13 H20 I N O'
_chemical_formula_weight         333.20
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.208(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   11.5465(8)
_cell_length_b                   16.9259(7)
_cell_length_c                   27.4768(15)
_cell_measurement_temperature    143(1)
_cell_volume                     5368.7(5)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0724
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            34107
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    2.368
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4653
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_F_000             2656
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.267
_refine_diff_density_min         -1.906
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.013(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1170
_refine_ls_number_reflns         20757
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+4.0824P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                19066
_reflns_number_total             20757
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja804939r_si_005.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               4108477