Synthesis of isoxazoline-featured oxindoles by iminoxyl radical-promoted cascade oxyalkylation/alkylarylation of alkenes
Yang, Xiu-Long; Long, Yan; Chen, Fei; Han, Bing; Organic Chemistry Frontiers 3 (2016) 184–; doi:10.1039/C5QO00352K

data_1553208
_publ_section_title
;
 Synthesis of isoxazoline-featured oxindoles by iminoxyl radical-promoted
 cascade oxyalkylation/alkylarylation of alkenes
;
_journal_issue                   2
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              184
_journal_paper_doi               10.1039/C5QO00352K
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C24 H25 N3 O2'
_chemical_formula_sum            'C24 H25 N3 O2'
_chemical_formula_weight         387.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc145fk9
_audit_creation_date             2014-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4866)
;
_audit_update_record
;
2015-02-06 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                94.339(10)
_cell_angle_beta                 100.719(10)
_cell_angle_gamma                105.418(10)
_cell_formula_units_Z            2
_cell_length_a                   7.1121(7)
_cell_length_b                   8.5933(10)
_cell_length_c                   18.426(2)
_cell_measurement_reflns_used    1013
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.4810
_cell_measurement_theta_min      3.9510
_cell_volume                     1057.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega    0.00   26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.2008  -99.0000   30.0000 26

  2 omega   55.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071   57.0000 -150.0000 26

  3 omega  -11.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071  -57.0000 -150.0000 44

  4 omega    3.00   50.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071   57.0000 -180.0000 47

  5 omega   63.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071   57.0000 -180.0000 26

  6 omega   45.00   71.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071  178.0000    0.0000 26

  7 omega   12.00   45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071   57.0000 -150.0000 33

  8 omega    4.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071   57.0000   60.0000 82

  9 omega  -20.00   53.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071  -99.0000  -30.0000 73

 10 omega  -31.00   36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071  -38.0000   60.0000 67
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0337897000
_diffrn_orient_matrix_UB_12      -0.0831725000
_diffrn_orient_matrix_UB_13      -0.0156005000
_diffrn_orient_matrix_UB_21      0.0098935000
_diffrn_orient_matrix_UB_22      -0.0233139000
_diffrn_orient_matrix_UB_23      0.0363144000
_diffrn_orient_matrix_UB_31      -0.0998950000
_diffrn_orient_matrix_UB_32      -0.0003444000
_diffrn_orient_matrix_UB_33      -0.0001117000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.1328
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4555
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.850
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.850
_refine_ls_R_factor_all          0.1438
_refine_ls_R_factor_gt           0.0566
_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^)+(0.0531P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1338
_reflns_number_gt                1955
_reflns_number_total             4555
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00352k2.cif
_cod_data_source_block           yangxl1015_twin1_hklf4
_cod_database_code               1553208
_chemical_oxdiff_formula         'C11 H10 N O'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C19(H19), C20(H20), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'