Direct access to isoxazolino and isoxazolo benzazepines from 2-((hydroxyimino)methyl) benzoic acid via a post-Ugi heteroannulation
Balalaie, Saeed; Shamakli, Mohammad; Nikbakht, Ali -; S. Alavijeh, Nahid; Rominger, Frank -; Rostamizadeh, Shahnaz; Bijanzadeh, Hamid Raza -; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01142C

data_7155714
_publ_section_title
;
 Direct access to isoxazolino and isoxazolo benzazepines from
 2-((hydroxyimino)methyl) benzoic acid via a post-Ugi heteroannulation
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01142C
_journal_year                    2017
_chemical_formula_sum            'C25 H24 N4 O5'
_chemical_formula_weight         460.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-04-27 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                77.844(3)
_cell_angle_beta                 81.090(3)
_cell_angle_gamma                71.413(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6689(3)
_cell_length_b                   10.6916(4)
_cell_length_c                   13.0284(4)
_cell_measurement_reflns_used    18413
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.67
_cell_measurement_theta_min      3.49
_cell_volume                     1113.85(7)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13869
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.124
_diffrn_reflns_theta_min         3.486
_diffrn_source                   'Genix3D Cu HF'
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  1.395
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.848
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.848
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0482P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0828
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2864
_reflns_number_total             4256
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01142c4.cif
_cod_data_source_block           sba139
_cod_database_code               7155714
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.946
_shelx_estimated_absorpt_t_max   0.953
_exptl_absorpt_special_details   'STOE X-AREA Laue Analyzer'
_shelx_res_checksum              21866