Regioselective synthesis of 3-arylamino- and 5-arylaminoisoxazoles from enaminones.
Xiang, Dexuan; Xin, Xiaoqing; Liu, Xu; Zhang, Rui; Yang, Jiming; Dong, Dewen; Organic letters 14 (2012) 644–647; doi:10.1021/ol203282h

data_1503590
_publ_section_title
;
 Regioselective synthesis of 3-arylamino- and 5-arylaminoisoxazoles from
 enaminones.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              644
_journal_page_last               647
_journal_paper_doi               10.1021/ol203282h
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C13 H15 Cl N2 O2'
_chemical_formula_sum            'C13 H15 Cl N2 O2'
_chemical_formula_weight         266.72
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000
_cell_angle_beta                 97.661(6)
_cell_angle_gamma                90.000
_cell_formula_units_Z            8
_cell_length_a                   16.142(3)
_cell_length_b                   8.118(4)
_cell_length_c                   20.461(6)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.82
_cell_measurement_theta_min      1.52
_cell_volume                     2657.3(16)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_sigmaI/netI    0.0696
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15121
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        no
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0627P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1352
_reflns_number_gt                3058
_reflns_number_total             4710
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol203282h_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        2657.3(19)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1503590