Copper nitrate-mediated synthesis of 3-aryl isoxazolines and isoxazoles from olefinic azlactones.
Lin, Yifan; Zhang, Ke; Gao, Mingchun; Jiang, Zheyi; Liu, Jiajie; Ma, Yurui; Wang, Haoyu; Tan, Qitao; Xiao, Junjie; Xu, Bin; Organic & biomolecular chemistry 17 (2019) 5509–5513; doi:10.1039/c9ob00857h

data_7156876
_publ_section_title
;
 Copper nitrate-mediated synthesis of 3-aryl isoxazolines and isoxazoles
 from olefinic azlactones.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5509
_journal_page_last               5513
_journal_paper_doi               10.1039/c9ob00857h
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C11 H9 N3 O6 S'
_chemical_formula_weight         311.27
_chemical_melting_point          533.5(5)
_chemical_name_systematic
'5-methyl-3-(4-nitrophenyl)-5,6a-dihydroisothiazolo[5,4-d]isoxazol-6(3aH)-one 4,4-dioxide'
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-12-12 deposited with the CCDC.    2019-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.495(3)
_cell_length_b                   17.713(8)
_cell_length_c                   21.586(10)
_cell_measurement_reflns_used    2890
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.30
_cell_volume                     2483(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14604
_diffrn_reflns_theta_full        27.78
_diffrn_reflns_theta_max         27.78
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_count 0.0
_diffrn_standards_interval_time  0.0
_diffrn_standards_number         0.0
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+0.8699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                2306
_reflns_number_total             2926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob00857h2.cif
_cod_data_source_block           zk-4-125
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '533-534' was changed to '533.5(5)' -
the average value was taken and precision was estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156876.cif.
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7156876