Highly regioselective synthesis of 2,4,5-(hetero)aryl substituted oxazoles by intermolecular [3+2]-cycloaddition of unsymmetrical internal alkynes
Elli Chatzopoulou; Paul W. Davies; Chem.Commun. 49 (2013) 8617–; doi:10.1039/c3cc45410j

data_7109756
_publ_section_title
;
 Highly regioselective synthesis of 2,4,5-(hetero)aryl substituted
 oxazoles by intermolecular [3+2]-cycloaddition of unsymmetrical internal
 alkynes
;
_journal_name_full               Chem.Commun.
_journal_page_first              8617
_journal_paper_doi               10.1039/c3cc45410j
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C23 H16 N2 O'
_chemical_formula_sum            'C23 H16 N2 O'
_chemical_formula_weight         336.38
_chemical_name_systematic
;
4-(1H-indol-3-yl)-2,5-diphenyloxazole
;
_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                 106.4820(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0222(2)
_cell_length_b                   7.23960(10)
_cell_length_c                   20.9825(3)
_cell_measurement_reflns_used    7545
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.570
_cell_measurement_theta_min      3.835
_cell_volume                     1751.19(5)
_computing_cell_refinement       'SAINT V6.28A (Bruker, 1997)'
_computing_data_collection       'SMART V5.626 (Bruker, 1997)'
_computing_data_reduction        'SAINT V6.28A (Bruker, 1997)'
_computing_molecular_graphics
;
OLEX2 (Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K,
& Puschmann, H., 2009)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART 6000'
_diffrn_measurement_method       'Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_sigmaI/netI    0.0635
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11907
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         6.50
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  0.9290
_exptl_absorpt_correction_T_min  0.8548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.07 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            'Light Brown'
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0525
_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^)+(0.0896P)^2^+0.3860P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1537
_reflns_number_gt                2678
_reflns_number_total             3042
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c3cc45410j.txt
_cod_data_source_block           3aa
_cod_original_sg_symbol_H-M      'P 2(1)/c'
_cod_database_code               7109756