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_4028256
_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_absolute_configuration unk
_chemical_compound_source        local
_chemical_formula_moiety         'C17 H11 N O4'
_chemical_formula_sum            'C17 H11 N O4'
_chemical_formula_weight         293.28
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             13-03-05
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2013-03-05 - Report on C17 H11 N O4 
             by Anthony C. Willis
             for  Hye Sun Kim and Martin Banwell

2013-03-05 - passes checkcif tests with few warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9959(1)
_cell_length_b                   15.4251(5)
_cell_length_c                   16.5839(6)
_cell_measurement_reflns_used    27139
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1277.99(7)
_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      200
_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  0.066
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17735
_diffrn_reflns_theta_full        27.468
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         2.641
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1724
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.0003472
_refine_ls_shift/su_mean         0.0000658
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.12P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0911
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0911
_reflns_limit_h_max              6
_reflns_limit_h_min              0
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                1501
_reflns_number_total             1725
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.75
_oxford_diffrn_Wilson_scale      1.32
_oxford_refine_ls_r_factor_ref   0.0437
_oxford_refine_ls_scale          0.884(4)
_oxford_reflns_number_all        1724
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '3051138 ban1309'
_cod_data_source_file            jo4006987_si_002.cif
_cod_data_source_block           ban1309
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4028256