Iminoxyl Radical-Promoted Oxycyanation and Aminocyanation of Unactivated Alkenes: Synthesis of Cyano-Featured Isoxazolines and Cyclic Nitrones.
Chen, Fei; Zhu, Fei-Fei; Zhang, Man; Liu, Rui-Hua; Yu, Wei; Han, Bing; Organic letters 19 (2017) 3255–3258; doi:10.1021/acs.orglett.7b00826

data_1546274
_publ_section_title
;
 Iminoxyl Radical-Promoted Oxycyanation and Aminocyanation of Unactivated
 Alkenes: Synthesis of Cyano-Featured Isoxazolines and Cyclic Nitrones.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3255
_journal_page_last               3258
_journal_paper_doi               10.1021/acs.orglett.7b00826
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C14 H16 N2 O2'
_chemical_formula_sum            'C14 H16 N2 O2'
_chemical_formula_weight         244.29
_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             2017-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.790(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7785(12)
_cell_length_b                   8.8637(5)
_cell_length_c                   13.5121(10)
_cell_measurement_reflns_used    698
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.0160
_cell_measurement_theta_min      3.9260
_cell_volume                     1309.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9923
_diffrn_measured_fraction_theta_max 0.8795
_diffrn_measurement_details
;
  1 omega  -86.00  -56.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000 -180.0000 15

  2 omega   44.00   92.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000 -180.0000 24

  3 omega  -26.00   94.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000 -180.0000 60

  4 omega   60.00   90.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000 -150.0000 15
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0287007000
_diffrn_orient_matrix_UB_12      -0.0049325000
_diffrn_orient_matrix_UB_13      -0.0377199000
_diffrn_orient_matrix_UB_21      0.0460720000
_diffrn_orient_matrix_UB_22      -0.0467206000
_diffrn_orient_matrix_UB_23      0.0354305000
_diffrn_orient_matrix_UB_31      -0.0354647000
_diffrn_orient_matrix_UB_32      -0.0647558000
_diffrn_orient_matrix_UB_33      -0.0227655000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0781
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4658
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.69
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0634
_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^)+(0.0479P)^2^+0.2844P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1648
_reflns_number_gt                1408
_reflns_number_total             2550
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b00826_si_002.cif
_cod_data_source_block           chenf_0117
_cod_depositor_comments          'Adding full bibliography for 1546274.cif.'
_cod_original_cell_volume        1309.87(18)
_cod_database_code               1546274
_reflns_odcompleteness_completeness 99.23
_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:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_olex2_date_sample_data_collection 2017-01-18
_olex2_submission_special_instructions 'No special instructions were received'