Catalyst-free intramolecular oxidative cyclization of N-allylbenzamides: a new route to 2,5-substituted oxazoles.
Zhou, Wei; Xie, Chen; Han, Jianlin; Pan, Yi; Organic letters 14 (2012) 4766–4769; doi:10.1021/ol302031z

data_1508623
_publ_section_title
;
 Catalyst-free intramolecular oxidative cyclization of N-allylbenzamides:
 a new route to 2,5-substituted oxazoles.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4766
_journal_page_last               4769
_journal_paper_doi               10.1021/ol302031z
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C10 H7 Br Cl N O'
_chemical_formula_sum            'C10 H7 Br Cl N O'
_chemical_formula_weight         272.53
_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                91.074(3)
_cell_angle_beta                 99.011(2)
_cell_angle_gamma                102.439(3)
_cell_formula_units_Z            2
_cell_length_a                   5.7402(11)
_cell_length_b                   7.5688(13)
_cell_length_c                   12.262(2)
_cell_measurement_reflns_used    1792
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      3.31
_cell_volume                     513.05(16)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3218
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    4.229
_exptl_absorpt_correction_T_max  0.605
_exptl_absorpt_correction_T_min  0.494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.274(14)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0412
_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^)+(0.06P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                1696
_reflns_number_total             2090
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302031z_si_002.cif
_cod_data_source_block           20120307a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        513.06(16)
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               1508623