C-ON Bond Homolysis of Alkoxyamines, Part 11: Activation of the Nitroxyl Fragment.
Audran, Gérard; Brémond, Paul; Marque, Sylvain R. A.; Yamasaki, Toshihide; The Journal of organic chemistry 81 (2016) 1981–1988; doi:10.1021/acs.joc.5b02790

data_4036570
_publ_section_title
;
 C-ON Bond Homolysis of Alkoxyamines, Part 11: Activation of the Nitroxyl
 Fragment.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1981
_journal_page_last               1988
_journal_paper_doi               10.1021/acs.joc.5b02790
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C21 H36 N O6 P'
_chemical_formula_sum            'C21 H36 N O6 P'
_chemical_formula_weight         429.48
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-16
_audit_creation_method
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Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
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_cell_formula_units_Z            4
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_cell_length_b                   8.81848(11)
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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;
  1 omega  -14.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -84.0000   69.0000 26

  2 omega   14.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  120.0000 27

  3 omega  -34.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245   38.0000  150.0000 61

  4 omega  -85.00  -23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245  -57.0000   90.0000 62

  5 omega    1.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -90.0000 25

  6 omega   32.00   88.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega   57.00   83.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   58.00   89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega   80.00  107.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   45.0000  120.0000 27

 10 omega   84.00  162.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   45.0000  150.0000 78

 11 omega  153.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   61.0000  120.0000 25

 12 omega  112.00  138.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   57.0000  150.0000 26

 13 omega  106.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245  125.0000   60.0000 35

 14 omega  104.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245  125.0000   30.0000 37

 15 omega  106.00  132.00   1.0000    1.0000
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    -       57.0245  125.0000  -30.0000 26

 16 omega   77.00  106.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   61.0000   60.0000 29

 17 omega  103.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   77.0000   30.0000 75

 18 omega  113.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   77.0000   60.0000 62

 19 omega  108.00  173.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   77.0000   90.0000 65

 20 omega   91.00  172.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   61.0000    0.0000 81

 21 omega  102.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   84.0000 -169.0000 25

 22 omega  101.00  177.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  111.0000 -180.0000 76

 23 omega   87.00  157.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   61.0000 -120.0000 70

 24 omega   79.00  106.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   61.0000   30.0000 27

 25 omega   77.00  107.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   61.0000   90.0000 30

 26 omega   79.00  105.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   45.0000   90.0000 26

 27 omega   77.00  103.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   61.0000  120.0000 26

 28 omega   75.00  101.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   77.0000   60.0000 26

 29 omega   75.00  101.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   77.0000   30.0000 26

 30 omega   75.00  101.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   77.0000   90.0000 26

 31 omega   28.00   54.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000   30.0000 26

 32 omega   80.00  153.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   45.0000  -60.0000 73

 33 omega   39.00   64.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -45.0000  150.0000 25

 34 omega   21.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   57.0000  150.0000 26

 35 omega  -94.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   30.0000 37

 36 omega  -95.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 37 omega -152.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245    0.0000    0.0000 181

 38 omega -146.00  -83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245  -99.0000  -60.0000 63
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      -0.0658741000
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_diffrn_orient_matrix_UB_23      -0.0604845000
_diffrn_orient_matrix_UB_31      0.0473146000
_diffrn_orient_matrix_UB_32      -0.1391212000
_diffrn_orient_matrix_UB_33      0.0431602000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0231
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_diffrn_source                   'sealed X-ray tube'
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_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
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_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
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_refine_ls_R_factor_gt           0.0409
_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^)+(0.0650P)^2^+0.3999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_total             4845
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02790_si_004.cif
_cod_data_source_block           coohstr2
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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. Uiso/Uaniso restraints and constraints
C20 \\sim C21 \\sim C22 \\sim C23: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04
3. Others
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=1-FVAR(1)
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C0AA(H0AA), C13(H13)
4.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B), C22(H22A,H22B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C5(H5), C6(H6), C7(H7)
4.d Idealised Me refined with riding coordinates:
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C)
4.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
4.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'