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_7155713
_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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-04-26 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.191(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0879(14)
_cell_length_b                   17.9838(17)
_cell_length_c                   8.8566(9)
_cell_measurement_reflns_used    3317
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      23.37
_cell_measurement_theta_min      2.62
_cell_volume                     2339.7(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14592
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.060
_diffrn_reflns_theta_max         25.060
_diffrn_reflns_theta_min         1.386
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9579
_exptl_absorpt_correction_T_min  0.8490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       needle
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4147
_refine_ls_number_restraints     316
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0635P)^2^+1.2676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1632
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2754
_reflns_number_total             4147
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01142c4.cif
_cod_data_source_block           sba138
_cod_database_code               7155713
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.946
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              1468