Annulation of β-aryl-α-nitro-α,β-enals and 2,2-dimethyl-1,3-dioxan-5-one: a one-step assembly of nitrocyclitols. Application to a short practical synthesis of (±)-7-deoxy-2-epi-pancratistatin tetraacetate
Juan Carlos Ortiz; Lidia Ozores; Fernando Cagide-Fagín; Ricardo Alonso; Chemical Communications  (2006) –; doi:10.1039/b606277f

data_7101476
_publ_section_title
;Annulation of \b-aryl-\a-nitro-\a,\b-enals and
2,2-dimethyl-1,3-dioxan-5-one: a one-step assembly of
nitrocyclitols. Application to a short practical synthesis of
(+-)-7-deoxy-2-epi-pancratistatin tetraacetate
;
_journal_issue                   40
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/b606277f
_journal_year                    2006
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C13 H15 N1 O7'
_chemical_formula_sum            'C13 H15 N O7'
_chemical_formula_weight         297.26
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2006-07-13T20:46:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.300(4)
_cell_length_b                   6.1987(18)
_cell_length_c                   12.443(4)
_cell_measurement_reflns_used    15
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.91
_cell_measurement_theta_min      18.65
_cell_measurement_wavelength     1.5418
_cell_volume                     1411.5(7)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_orient_matrix_type
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.019302
_diffrn_orient_matrix_UB_12      -0.030565
_diffrn_orient_matrix_UB_13      0.050121
_diffrn_orient_matrix_UB_21      -0.15809
_diffrn_orient_matrix_UB_22      0.007863
_diffrn_orient_matrix_UB_23      0.009196
_diffrn_orient_matrix_UB_31      -0.024867
_diffrn_orient_matrix_UB_32      -0.073967
_diffrn_orient_matrix_UB_33      -0.019771
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2817
_diffrn_reflns_theta_full        72.77
_diffrn_reflns_theta_max         72.77
_diffrn_reflns_theta_min         4.83
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 146
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.986
_exptl_absorpt_correction_T_max  0.9253
_exptl_absorpt_correction_T_min  0.5059
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was 7
Theta correction was applied.
Weighted transmission curves were used.
No Fourier smoothing was applied.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         1480
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1382
_reflns_number_gt                898
_reflns_number_total             1480
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b606277f.txt
_cod_database_code               7101476