Synthesis of 3,4,5-trisubstituted isoxazoles via 1,3-dipolar cycloaddition/SO2 extrusion of benzoisothiazole-2,2-dioxide-3-ylidenes with nitrile oxides
Cao, Guorui; Wang, Yu; Cui, Tao; Huang, Longjiang; Teng, Dawei; RSC Adv.  (2016) –; doi:10.1039/C5RA26718H

data_7224365
_publ_section_title
;
 Synthesis of 3,4,5-trisubstituted isoxazoles via 1,3-dipolar
 cycloaddition/SO2 extrusion of benzoisothiazole-2,2-dioxide-3-ylidenes
 with nitrile oxides
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA26718H
_journal_year                    2016
_chemical_formula_moiety         'C23 H20 N2 O2'
_chemical_formula_sum            'C23 H20 N2 O2'
_chemical_formula_weight         356.41
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_audit_update_record
;
2015-12-10 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                89.408(15)
_cell_angle_beta                 86.301(13)
_cell_angle_gamma                82.719(12)
_cell_formula_units_Z            2
_cell_length_a                   6.184(2)
_cell_length_b                   9.236(4)
_cell_length_c                   16.222(7)
_cell_measurement_reflns_used    3771
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      32.4733
_cell_measurement_theta_min      1.2579
_cell_volume                     917.1(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 40.3253
              2theta: -19.8862
scan:
    Number of images: 356
               Slice: -110.0000 - 68.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 40.3253
              2theta: -19.8862
scan:
    Number of images: 256
               Slice: -110.0000 - 18.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 40.3253
              2theta: -19.8862
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0096
_diffrn_orient_matrix_UB_12      0.1600
_diffrn_orient_matrix_UB_13      -0.0314
_diffrn_orient_matrix_UB_21      -0.0064
_diffrn_orient_matrix_UB_22      0.0069
_diffrn_orient_matrix_UB_23      0.1087
_diffrn_orient_matrix_UB_31      0.0617
_diffrn_orient_matrix_UB_32      0.0004
_diffrn_orient_matrix_UB_33      0.0035
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4112
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.467
_diffrn_reflns_theta_min         1.258
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       rod
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0776
_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^)+(0.0742P)^2^+0.5947P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1989
_refine_ls_wR_factor_ref         0.2069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3540
_reflns_number_total             4112
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra26718h2.cif
_cod_data_source_block           mx3559
_cod_original_cell_volume        917.2(6)
_cod_database_code               7224365
_diffrn_number_total             4112
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.566(6) 0.431(4) 0.003(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22)
3.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              46955
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'