Dioxygen Activation via Cu-Catalyzed Cascade Radical Reaction: An Approach to Isoxazoline/Cyclic Nitrone-Featured α-Ketols
Peng, Xie-Xue; Wei, Dian; Han, Wen-Jun; Chen, Fei; Yu, Wei; Han, Bing; ACS Catalysis 7 (2017) 7830–; doi:10.1021/acscatal.7b03078

data_4514247
_publ_section_title
;
 Dioxygen Activation via Cu-Catalyzed Cascade Radical Reaction: An
 Approach to Isoxazoline/Cyclic Nitrone-Featured \a-Ketols
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              7830
_journal_paper_doi               10.1021/acscatal.7b03078
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C19 H19 N O3'
_chemical_formula_sum            'C19 H19 N O3'
_chemical_formula_weight         309.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.176(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3432(5)
_cell_length_b                   12.1755(6)
_cell_length_c                   14.6611(8)
_cell_measurement_reflns_used    1264
_cell_measurement_temperature    294.33(10)
_cell_measurement_theta_max      21.9960
_cell_measurement_theta_min      3.6230
_cell_volume                     1630.30(15)
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.33(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   20.00   47.55   1.4500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  120.0000 19

  2 omega  -20.00   11.90   1.4500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000   60.0000 22

  3 omega  -40.00   97.75   1.4500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000 -150.0000 95

  4 omega    1.00   59.00   1.4500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -90.0000 40
;
_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      0.0746291000
_diffrn_orient_matrix_UB_12      0.0128426000
_diffrn_orient_matrix_UB_13      0.0019535000
_diffrn_orient_matrix_UB_21      0.0117454000
_diffrn_orient_matrix_UB_22      0.0051404000
_diffrn_orient_matrix_UB_23      0.0492190000
_diffrn_orient_matrix_UB_31      0.0179865000
_diffrn_orient_matrix_UB_32      -0.0565875000
_diffrn_orient_matrix_UB_33      0.0049009000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6847
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.34
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78751
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0429P)^2^+0.2701P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1460
_reflns_number_gt                1866
_reflns_number_total             3202
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs7b03078_si_004.cif
_cod_data_source_block           pengxx_0905
_cod_depositor_comments
'Adding full bibliography for 4514247--4514249.cif.'
_cod_original_cell_volume        1630.31(15)
_cod_database_code               4514247
_reflns_odcompleteness_completeness 99.69
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C16(H16), C2(H2A), C4(H4), C15(H15), C3(H3), C17(H17),
 C14(H14), C13(H13)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_date_sample_data_collection 2016-09-05
_olex2_submission_special_instructions 'No special instructions were received'