Total Synthesis of (+)-Lyconadin A and Related Compounds via Oxidative C-N Bond Formation
Scott P. West; Alakesh Bisai; Andrew D. Lim; Raja R. Narayan; Richmond Sarpong; Journal of the American Chemical Society 131 (2009) 11187–11194; doi:10.1021/ja903868n

data_4104833
_publ_section_title
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 Total Synthesis of (+)-Lyconadin A and Related Compounds via Oxidative
 C-N Bond Formation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11187
_journal_page_last               11194
_journal_paper_doi               10.1021/ja903868n
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C22 H24 N2 O2 S'
_chemical_formula_weight         380.49
_chemical_name_common            SW-V-172b
_chemical_name_systematic
;
 sarpong09
;
_space_group.centring_type       P
_space_group_IT_number           2
_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                107.145(5)
_cell_angle_beta                 95.759(5)
_cell_angle_gamma                105.904(4)
_cell_formula_units_Z            2
_cell_length_a                   7.6286(7)
_cell_length_b                   11.1810(12)
_cell_length_c                   12.0135(13)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.08
_cell_measurement_theta_min      4.37
_cell_volume                     923.21(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'HELIOS multilayer mirrors'
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_refln_scan_rate          5
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13774
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         3.93
_exptl_absorpt_coefficient_mu    1.715
_exptl_absorpt_correction_T_max  0.9041
_exptl_absorpt_correction_T_min  0.8750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       needle
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0563P)^2^+0.5853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                3215
_reflns_number_total             3271
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja903868n_si_001.cif
_cod_data_source_block           sarpong09
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_original_cell_volume        923.21(16)
_cod_database_code               4104833