Regioselective Formation of 2,5-Disubstituted Oxazoles Via Copper(I)-Catalyzed Cycloaddition of Acyl Azides and 1-Alkynes
Israel Cano; Eleuterio Álvarez; M. Carmen Nicasio; Pedro J. Pérez; Journal of the American Chemical Society 133 (2011) 191–193; doi:10.1021/ja109732s

data_4105525
_publ_section_title
;
 Regioselective Formation of 2,5-Disubstituted Oxazoles Via
 Copper(I)-Catalyzed Cycloaddition of Acyl Azides and 1-Alkynes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              191
_journal_page_last               193
_journal_paper_doi               10.1021/ja109732s
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C23 H15 N O'
_chemical_formula_sum            'C23 H15 N O'
_chemical_formula_weight         321.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.31(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.772(9)
_cell_length_b                   6.001(4)
_cell_length_c                   19.196(9)
_cell_measurement_reflns_used    895
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      18.29
_cell_measurement_theta_min      2.77
_cell_volume                     1694.4(17)
_computing_cell_refinement       'Bruker (2006). APEX 2. Version 2.1.'
_computing_data_collection       'Bruker (2006). APEX 2. Version 2.1.'
_computing_data_reduction        'Bruker (2006). APEX 2. Version 2.1.'
_computing_molecular_graphics    'XP, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_publication_material  'XCIF, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_structure_refinement  'XL, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_structure_solution    'Bruker (2006). APEX 2. Version 2.1.'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
 Bruker-Nonius X8kappa APEX II CCD area detector'
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_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  0.0823
_diffrn_reflns_av_sigmaI/netI    0.0865
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12808
_diffrn_reflns_theta_full        26.29
_diffrn_reflns_theta_max         26.29
_diffrn_reflns_theta_min         1.38
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical
 X-ray Solutions, Madison, Wisconsin, USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.046(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0720
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1798P)^2^+6.4534P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1969
_refine_ls_wR_factor_ref         0.2343
_reflns_number_gt                2257
_reflns_number_total             3387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja109732s_si_003.cif
_cod_data_source_block           ea04410a
_cod_original_cell_volume        1694.3(17)
_cod_database_code               4105525