Synthesis of the Tetracyclic Framework of the Erythrina Alkaloids Using a [4 + 2]-Cycloaddition/Rh(I)-Catalyzed Cascade of 2-Imidofurans
Albert Padwa; Qiu Wang; Journal of Organic Chemistry 71 (2006) 7391–7402; doi:10.1021/jo061269p

data_4021967
_publ_section_title
;
 Synthesis of the Tetracyclic Framework of the Erythrina Alkaloids Using
 a [4 + 2]-Cycloaddition/Rh(I)-Catalyzed Cascade of 2-Imidofurans
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7391
_journal_page_last               7402
_journal_paper_doi               10.1021/jo061269p
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C20 H21 N O6'
_chemical_formula_weight         371.38
_space_group_IT_number           1
_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                84.168(3)
_cell_angle_beta                 68.788(2)
_cell_angle_gamma                72.628(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6283(4)
_cell_length_b                   10.2323(5)
_cell_length_c                   11.4766(6)
_cell_measurement_reflns_used    3631
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.01
_cell_measurement_theta_min      4.13
_cell_volume                     901.48(8)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.834
_diffrn_measured_fraction_theta_max 0.834
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4455
_diffrn_reflns_theta_full        67.11
_diffrn_reflns_theta_max         67.11
_diffrn_reflns_theta_min         4.13
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  0.8492
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irreg
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         3677
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.9000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1553
_reflns_number_gt                3522
_reflns_number_total             3677
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061269prom20060621_045625.cif
_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_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_database_code               4021967