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_1517439
_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         'C18 H24 N2 O2'
_chemical_formula_sum            'C18 H24 N2 O2'
_chemical_formula_weight         300.39
_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'
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Olex2 1.2
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_cell_length_b                   11.048(2)
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_cell_measurement_reflns_used    1365
_cell_measurement_temperature    293(2)
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_cell_measurement_theta_min      3.8520
_cell_volume                     811.4(3)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
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_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)
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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)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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_diffrn_ambient_temperature      293(2)
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_diffrn_measured_fraction_theta_full 0.996
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_diffrn_orient_matrix_UB_23      0.0242035000
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_diffrn_orient_matrix_UB_32      0.0167078000
_diffrn_orient_matrix_UB_33      -0.0135062000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
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_diffrn_reflns_limit_k_min       -10
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_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4820
_diffrn_reflns_point_group_measured_fraction_full 0.996
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_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         3.107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
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_exptl_absorpt_process_details
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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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       block
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_exptl_crystal_size_max          0.34
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_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.026(5)
_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   1.056
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_refine_ls_number_reflns         3181
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_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0949
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.1292P]
 where P=(Fo^2^+2Fc^2^)/3
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_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502258n_si_006.cif
_cod_data_source_block           pengxx_0512
_cod_depositor_comments
'Adding full bibliography for 1517435--1517439.cif.'
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_shelxl_version_number           2013-2
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_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 Ternary CH refined with riding coordinates:
 C12(H12), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C9(H9A,H9B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C5(H5), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
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