Formation of γ-Oxoacids and 1H-Pyrrol-2(5H)-ones from α,β-Unsaturated Ketones and Ethyl Nitroacetate
Maialen Aginagalde; Tamara Bello; Carme Masdeu; Yosu Vara; Ana Arrieta; Fernando P. Cossío; Journal of Organic Chemistry 75 (2010) 7435–7438; doi:10.1021/jo101388x

data_4025759
_publ_section_title
;
 Formation of \g-Oxoacids and 1H-Pyrrol-2(5H)-ones from \a,\b-Unsaturated
 Ketones and Ethyl Nitroacetate
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7435
_journal_page_last               7438
_journal_paper_doi               10.1021/jo101388x
_journal_volume                  75
_journal_year                    2010
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H16 O4'
_chemical_formula_sum            'C17 H16 O4'
_chemical_formula_weight         284.3
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-07-14T12:08:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 97.916(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8492(3)
_cell_length_b                   5.82470(10)
_cell_length_c                   16.4716(3)
_cell_measurement_reflns_used    10397
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.5056
_cell_measurement_theta_min      3.009
_cell_measurement_wavelength     0.71073
_cell_volume                     1411.09(5)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2009)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2009)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2009)'
_computing_molecular_graphics    'Diamond v.3.1f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2005)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3504
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -68.00   30.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.1479   37.0000   90.0000 98

  2 omega  -10.00   33.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.1479   77.0000  -30.0000 43

  3 omega   -7.00   91.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       30.6166   37.0000 -120.0000 98

  4 omega  -61.00   70.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       30.6166  -77.0000  -90.0000 131

  5 omega   -7.00  123.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       30.6166   77.0000   90.0000 130

  6 omega   12.00   76.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       30.6166  -95.0000  103.0000 64

  7 omega   -9.00   41.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       30.6166   77.0000    0.0000 50

;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0025731413
_diffrn_orient_matrix_UB_12      -0.0593822647
_diffrn_orient_matrix_UB_13      0.0378015157
_diffrn_orient_matrix_UB_21      0.0282394839
_diffrn_orient_matrix_UB_22      -0.084254996
_diffrn_orient_matrix_UB_23      -0.0146981894
_diffrn_orient_matrix_UB_31      0.0390101358
_diffrn_orient_matrix_UB_32      0.0648563758
_diffrn_orient_matrix_UB_33      0.0155486316
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18113
_diffrn_reflns_theta_full        30.49
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_min         3.47
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
        (compiled May  6 2009,17:20:42)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.638
_exptl_crystal_size_mid          0.4772
_exptl_crystal_size_min          0.3191
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4302
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0877P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                3511
_reflns_number_total             4302
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo101388x_si_001.cif
_cod_data_source_block           myc12
_cod_database_code               4025759