Total syntheses of (±)-β-erythroidine and (±)-8-oxo-β-erythroidine by an intramolecular Diels-Alder cycloaddition of a 2-amidoacrolein
He, Yong; Funk, Raymond L.; Organic Letters 8 (2006) 3689–3692; doi:10.1021/ol061267r

data_1506116
_publ_section_title
;
 Total syntheses of (+-)-\b-erythroidine and (+-)-8-oxo-\b-erythroidine by
 an intramolecular Diels-Alder cycloaddition of a 2-amidoacrolein
;
_journal_coden_ASTM              ORLEF7
_journal_issue                   17
_journal_name_full               'Organic Letters'
_journal_page_first              3689
_journal_page_last               3692
_journal_paper_doi               10.1021/ol061267r
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C19 H19 Br1 N5 O5, C1 H2 Cl2'
_chemical_formula_sum            'C20 H21 Br Cl2 N5 O5'
_chemical_formula_weight         562.23
_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                74.69(2)
_cell_angle_beta                 77.23(2)
_cell_angle_gamma                85.51(2)
_cell_formula_units_Z            2
_cell_length_a                   8.044(10)
_cell_length_b                   11.217(14)
_cell_length_c                   13.883(18)
_cell_measurement_reflns_used    4007
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.229
_cell_measurement_theta_min      2.602
_cell_volume                     1178(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0807
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9874
_diffrn_reflns_theta_full        28.49
_diffrn_reflns_theta_max         28.49
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    2.013
_exptl_absorpt_correction_T_max  0.770
_exptl_absorpt_correction_T_min  0.552
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             570
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.063
_refine_diff_density_min         -1.022
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0740
_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^)+(0.1315P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1969
_refine_ls_wR_factor_ref         0.2061
_reflns_number_gt                3734
_reflns_number_total             5650
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061267rsi20060524_063543.cif
_cod_data_source_block           yxh12s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-20
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1506116