Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles.
Di Mauro, Giovanni; Maryasin, Boris; Kaiser, Daniel; Shaaban, Saad; González, Leticia; Maulide, Nuno; Organic letters 19 (2017) 3815–3818; doi:10.1021/acs.orglett.7b01678

data_1547114
_publ_section_title
;
 Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles
 and Imidazoles.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3815
_journal_page_last               3818
_journal_paper_doi               10.1021/acs.orglett.7b01678
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C18 H16 N2 O'
_chemical_formula_sum            'C18 H16 N2 O'
_chemical_formula_weight         276.33
_chemical_name_systematic        5-(indolin-1-yl)-2-methyl-4-phenyloxazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_audit_creation_date             2017-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.206(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1454(5)
_cell_length_b                   7.1266(2)
_cell_length_c                   15.9769(6)
_cell_measurement_reflns_used    4757
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      71.973
_cell_measurement_theta_min      5.582
_cell_volume                     1371.96(9)
_computing_cell_refinement       'APEX2 v2013.6-2'
_computing_data_collection       'APEX2 v2013.6-2'
_computing_data_reduction        'APEX2 v2013.6-2'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10676
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.068
_diffrn_reflns_theta_min         5.582
_diffrn_source                   'sealed  X-ray tube'
_diffrn_source_type              'Incoatec IuSCu'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.0825 before and 0.0436 after correction. 
The Ratio of minimum to maximum transmission is 0.8777. 
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method
'slow evaporation from pentan/ethylacetate'
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.019
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0413P)^2^+0.4157P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2168
_reflns_number_total             2670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01678_si_002.cif
_cod_data_source_block           cu_sash615_p21c
_cod_original_cell_volume        1371.97(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1547114
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.810