C-ON bond homolysis in alkoxyamines. Part 12: the effect of the para-substituent in the 1-phenylethyl fragment.
Audran, Gérard; Brémond, Paul; Joly, Jean-Patrick; Marque, Sylvain R. A.; Yamasaki, Toshihide; Organic & biomolecular chemistry 14 (2016) 3574–3583; doi:10.1039/c6ob00384b

data_7155030
_publ_section_title
;
 C-ON bond homolysis in alkoxyamines. Part 12: the effect of the
 para-substituent in the 1-phenylethyl fragment.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3574
_journal_page_last               3583
_journal_paper_doi               10.1039/c6ob00384b
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C21 H37 F N O4 P'
_chemical_formula_sum            'C21 H37 F N O4 P'
_chemical_formula_weight         417.48
_chemical_melting_point          56
_chemical_name_systematic
'Diethyl (1-(tert-butyl(1-(4-fluorophenyl)ethoxy)amino)-2,2-dimethylpropyl)phosphonate'
_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
_audit_creation_date             2015-12-18
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Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-02-09 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                75.983(2)
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_cell_formula_units_Z            2
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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_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
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;
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  2 omega   34.00   77.00   1.0000    1.0000
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  3 omega   28.00  105.00   1.0000   10.0000
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  4 omega   43.00  115.00   1.0000   10.0000
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  5 omega   62.00   96.00   1.0000   10.0000
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  6 omega   32.00   61.00   1.0000   10.0000
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  7 omega   31.00  101.00   1.0000   10.0000
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  8 omega   51.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega   22.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917  -94.0000   90.0000 74

 10 omega   99.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   55.0000 -128.1384 27

 11 omega  101.00  131.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000 -180.0000 30

 12 omega  101.00  174.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917  111.0000 -180.0000 73

 13 omega   91.00  154.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000 -113.9069 63

 14 omega   97.00  144.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000    0.0000 47

 15 omega  110.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 16 omega  112.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 17 omega  107.00  156.00   1.0000    1.0000
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 18 omega   96.00  170.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000  150.0000 74

 19 omega   64.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000    0.0000 26

 20 omega   67.00   92.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 21 omega   65.00   92.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   61.0000   60.0000 27

 22 omega   64.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000   90.0000 113

 23 omega   64.00  155.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000  120.0000 91

 24 omega   64.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000  -60.0000 113

 25 omega   66.00   94.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000 -180.0000 28

 26 omega   65.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   61.0000 -180.0000 25

 27 omega   65.00  137.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000 -150.0000 72

 28 omega   64.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000  -30.0000 113

 29 omega   64.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000  150.0000 26

 30 omega   64.00  146.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000   60.0000 82

 31 omega   64.00  143.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000  -90.0000 79

 32 omega   64.00  169.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000 -120.0000 105

 33 omega   52.00   82.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   55.0000 -128.1384 30

 34 omega   16.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   82.0000 -148.3664 26

 35 omega   21.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000 -113.9069 27

 36 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   80.0000  -94.7238 25

 37 omega   20.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   79.0000  -59.0022 27

 38 omega   20.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000  -25.4904 26

 39 omega   25.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   66.0000   13.9638 42

 40 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000  101.5362 25

 41 omega   21.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000   61.1465 30

 42 omega   16.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   81.0000   86.3098 25

 43 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000  135.5495 25

 44 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   80.0000  177.4677 25

 45 omega  -26.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.2264  123.0000  127.3260 25

 46 omega   -1.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   94.0000   -8.6886 25

 47 omega    5.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   90.0000  -99.5638 25

 48 omega  -16.00    9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 49 omega  -93.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 50 omega -127.00    2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 51 omega -116.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 52 omega -123.00    3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.2264  -38.0000 -150.0000 126
;
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_diffrn_orient_matrix_UB_31      0.1081344000
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_diffrn_orient_matrix_UB_33      -0.0553307000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
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_diffrn_reflns_limit_k_min       -12
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_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14548
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
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_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.284
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_exptl_absorpt_process_details
;
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_recrystallization_method
'Re-crystallisation from solvent: petroleum ether- ethyl acetate'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0495
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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^)+(0.0838P)^2^+0.2475P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
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_reflns_number_gt                3657
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00384b2.cif
_cod_data_source_block           jp293rssr1
_cod_depositor_comments
'Adding full bibliography for 7155028--7155030.cif.'
_cod_original_cell_volume        1196.51(6)
_cod_database_code               7155030
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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:
 C1(H1), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,
 H19B,H19C), C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'