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_1553209
_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         'C28 H26 N2 O3'
_chemical_formula_sum            'C28 H26 N2 O3'
_chemical_formula_weight         438.51
_chemical_melting_point          427.5(5)
_chemical_name_systematic
3-((4,4-dimethyl-3-phenyl-4,5-dihydroisoxazol-5-yl)methyl)-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc145fnd
_audit_creation_date             2015-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.09 svn.r3130 for OlexSys, GUI svn.r4987)
;
_audit_update_record
;
2015-02-06 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.402(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.8733(11)
_cell_length_b                   11.8466(6)
_cell_length_c                   12.3385(8)
_cell_measurement_reflns_used    1254
_cell_measurement_temperature    293.69(10)
_cell_measurement_theta_max      22.5840
_cell_measurement_theta_min      3.7750
_cell_volume                     2289.0(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_environment      air
_diffrn_ambient_temperature      293.69(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -13.00   14.60   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -90.0000 23

  2 omega   18.00   90.00   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000  120.0000 60

  3 omega  -52.00   64.40   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000  150.0000 97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0423080000
_diffrn_orient_matrix_UB_12      0.0074089000
_diffrn_orient_matrix_UB_13      0.0281885000
_diffrn_orient_matrix_UB_21      -0.0161983000
_diffrn_orient_matrix_UB_22      0.0174438000
_diffrn_orient_matrix_UB_23      0.0475881000
_diffrn_orient_matrix_UB_31      0.0005502000
_diffrn_orient_matrix_UB_32      -0.0568001000
_diffrn_orient_matrix_UB_33      0.0182743000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0851
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8698
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.39
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Petroleum ether, DCM'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1327
_refine_ls_R_factor_gt           0.0649
_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^)+(0.0485P)^2^+0.4541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1683
_reflns_number_gt                2326
_reflns_number_total             4502
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00352k2.cif
_cod_data_source_block           yangxl0120
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '427-428' was changed to
'427.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1553209
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C17(H17A,H17B,H17C)
;
_olex2_date_sample_data_collection 2015-01-22
_olex2_submission_special_instructions 'No special instructions were received'