A concise approach to polysubstituted oxazoles from N-acyl-2-bromo enamides via a copper(i)/amino acid-catalyzed intramolecular C-O bond formation.
Liu, Bingjie; Zhang, Yueteng; Huang, Gang; Zhang, Xinting; Niu, Pengfei; Wu, Jie; Yu, Wenquan; Chang, Junbiao; Organic & biomolecular chemistry 12 (2014) 3912–3923; doi:10.1039/c4ob00309h

data_7153894
_publ_section_title
;
 A concise approach to polysubstituted oxazoles from N-acyl-2-bromo
 enamides via a copper(i)/amino acid-catalyzed intramolecular C-O bond
 formation.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3912
_journal_page_last               3923
_journal_paper_doi               10.1039/c4ob00309h
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C20 H18 N2 O2'
_chemical_formula_weight         318.36
_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                81.46(3)
_cell_angle_beta                 89.70(3)
_cell_angle_gamma                70.47(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7404(15)
_cell_length_b                   8.6624(17)
_cell_length_c                   13.340(3)
_cell_measurement_temperature    293(2)
_cell_volume                     832.7(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0874
_diffrn_reflns_av_sigmaI/netI    0.1680
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5809
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.083
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.275
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.275
_refine_ls_R_factor_all          0.3106
_refine_ls_R_factor_gt           0.2092
_refine_ls_shift/su_max          0.194
_refine_ls_shift/su_mean         0.023
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1169P)^2^+1.5259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3973
_refine_ls_wR_factor_ref         0.4630
_reflns_number_gt                1328
_reflns_number_total             2896
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00309h2.cif
_cod_data_source_block           c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7153894