Catalytic one-pot synthesis of 4-(hetero)aryl substituted 5-(2-oxoethyl) oxazol-2(3H)-ones by coupling–isomerization–elimination (CIE) sequence
Görgen née Boersch, Christina; Lutsenko, Kiril; Merkul, Eugen; Frank, Walter; Müller, Thomas J. J.; Organic Chemistry Frontiers 3 (2016) 887–; doi:10.1039/C6QO00138F

data_1553452
_publ_section_title
;
 Catalytic one-pot synthesis of 4-(hetero)aryl substituted 5-(2-oxoethyl)
 oxazol-2(3H)-ones by coupling--isomerization--elimination (CIE) sequence
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              887
_journal_paper_doi               10.1039/C6QO00138F
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C19 H17 N O5'
_chemical_formula_sum            'C19 H17 N O5'
_chemical_formula_weight         339.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-03-14 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.649(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.5013(10)
_cell_length_b                   18.6052(13)
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_cell_measurement_reflns_used    8000
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      19.65
_cell_measurement_theta_min      5.10
_cell_volume                     3275.9(4)
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 2000)'
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_computing_data_reduction        'IPDS Software (Stoe & Cie, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       \f-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_Laue_measured_fraction_full 0.947
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_diffrn_reflns_limit_k_max       22
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_diffrn_reflns_point_group_measured_fraction_full 0.947
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_diffrn_reflns_theta_max         25.074
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_exptl_absorpt_coefficient_mu    0.100
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_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       isometric
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_exptl_crystal_size_max          0.30
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_refine_diff_density_max         0.115
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.028
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         5610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.800
_refine_ls_R_factor_all          0.0705
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_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.0581
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_reflns_number_total             5610
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00138f2.cif
_cod_data_source_block           opus774b
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1553452
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.970
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_shelx_hkl_checksum              37395