Convergent Total Syntheses of the Amaryllidaceae Alkaloids Lycoranine A, Lycoranine B, and 2-Methoxypratosine
Hye Sun Kim; Martin G. Banwell; Anthony C. Willis; Journal of Organic Chemistry 78 (2013) 5103–5109; doi:10.1021/jo4006987

data_4028258
_publ_contact_author_address
;
Research School of Chemistry,
Australian National University,
Canberra, A. C. T. 0200, Australia
;
_publ_contact_author_email       'mgb@rsc.anu.edu.au '
_publ_contact_author_fax         ' 61 2 6125 8114 '
_publ_contact_author_name        'Martin G. Banwell'
_publ_contact_author_phone       ' 61 2 6125 8202 '
_publ_section_title
;
 Convergent Total Syntheses of the Amaryllidaceae Alkaloids Lycoranine A,
 Lycoranine B, and 2-Methoxypratosine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5103
_journal_page_last               5109
_journal_paper_doi               10.1021/jo4006987
_journal_volume                  78
_journal_year                    2013
_chemical_compound_source        local
_chemical_formula_moiety         'C30 H18 Br2 N2 O8'
_chemical_formula_sum            'C30 H18 Br2 N2 O8'
_chemical_formula_weight         694.29
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             12-01-13
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2012-01-13 - Report on C18 H26 N2 O3 Si 
             by Anthony C. Willis
             for  Hye Sun Kim and Martin Banwell

2012-01-13 - passes checkcif tests with few warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 126.4796(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.9693(7)
_cell_length_b                   9.6562(3)
_cell_length_c                   16.0510(5)
_cell_measurement_reflns_used    12429
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3
_cell_volume                     2737.90(16)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;  
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) 
;
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27544
_diffrn_reflns_theta_full        27.505
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.574
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.018
_exptl_absorpt_correction_T_max  0.83
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_description       needle
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.91
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9448
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.0211483
_refine_ls_shift/su_mean         0.0057559
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 4.31P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1116
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1116
_reflns_limit_h_max              22
_reflns_limit_h_min              -28
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2011
_reflns_number_total             3150
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.77
_oxford_diffrn_Wilson_scale      37.68
_oxford_refine_ls_r_factor_ref   0.0774
_oxford_refine_ls_scale          0.18028(13)
_oxford_reflns_number_all        3150
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '12161240 ban1147'
_cod_data_source_file            jo4006987_si_004.cif
_cod_data_source_block           ban1147
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_database_code               4028258