Iminoxyl Radical-Promoted Dichotomous Cyclizations: Efficient Oxyoximation and Aminooximation of Alkenes.
Peng, Xie-Xue; Deng, Yun-Jing; Yang, Xiu-Long; Zhang, Lin; Yu, Wei; Han, Bing; Organic letters 16 (2014) 4650–; doi:10.1021/ol502258n

data_1517436
_publ_section_title
;
 Iminoxyl Radical-Promoted Dichotomous Cyclizations: Efficient
 Oxyoximation and Aminooximation of Alkenes.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4650
_journal_paper_doi               10.1021/ol502258n
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C19 H20 N2 O2'
_chemical_formula_sum            'C19 H20 N2 O2'
_chemical_formula_weight         308.37
_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     iterative
_audit_creation_date             2014-08-15
_audit_creation_method
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Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                102.268(12)
_cell_angle_beta                 103.727(10)
_cell_angle_gamma                110.298(11)
_cell_formula_units_Z            2
_cell_length_a                   8.4089(8)
_cell_length_b                   10.0499(15)
_cell_length_c                   12.6368(17)
_cell_measurement_reflns_used    1859
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7660
_cell_measurement_theta_min      3.5030
_cell_volume                     920.7(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
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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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, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -93.00  -57.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  178.0000  -90.0000 24

  2 omega  -17.00   26.50   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -99.0000   30.0000 29

  3 omega  -46.00   48.50   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -57.0000  120.0000 63

  4 omega   -9.00   85.50   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   77.0000  -90.0000 63

  5 omega  -44.00   85.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075    0.0000  -60.0000 86
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0078461000
_diffrn_orient_matrix_UB_12      -0.0103460000
_diffrn_orient_matrix_UB_13      -0.0555187000
_diffrn_orient_matrix_UB_21      0.0097381000
_diffrn_orient_matrix_UB_22      -0.0671526000
_diffrn_orient_matrix_UB_23      0.0007966000
_diffrn_orient_matrix_UB_31      -0.0947878000
_diffrn_orient_matrix_UB_32      -0.0413313000
_diffrn_orient_matrix_UB_33      -0.0254153000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6743
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         3.147
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40167
_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_density_diffrn    1.112
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.049(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3615
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0619
_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^)+(0.0896P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2311
_reflns_number_total             3615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502258n_si_003.cif
_cod_data_source_block           pengxx0507
_cod_depositor_comments
'Adding full bibliography for 1517435--1517439.cif.'
_cod_database_code               1517436
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.76
_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. Uiso/Uaniso restraints and constraints
Uanis(C13) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C1(H1), C2(H2A), C16(H16), C5(H5), C4(H4), C14(H14), C15(H15),
 C3(H3), C13(H13)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              91906
_shelx_hkl_checksum              80906
_olex2_submission_special_instructions 'No special instructions were received'