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_7155028
_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 H39 N2 O4 P'
_chemical_formula_sum            'C21 H39 N2 O4 P'
_chemical_formula_weight         414.51
_chemical_melting_point          110
_chemical_name_systematic
'Diethyl (1-((1-(4-aminophenyl)ethoxy)(tert-butyl)amino)-2,2-dimethylpropyl)phosphonate '
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-12-10 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.1629(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.0189(3)
_cell_length_b                   13.8383(3)
_cell_length_c                   19.9173(4)
_cell_measurement_reflns_used    6920
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9480
_cell_measurement_theta_min      4.0030
_cell_volume                     4958.83(17)
_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
;
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)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega   87.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5600   38.0000  120.0000 30

  2 omega   95.00  175.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  124.0000  174.0000 80

  3 omega  149.00  174.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  111.0000  -30.0000 25

  4 omega   67.00  149.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  178.0000    0.0000 82

  5 omega   57.00  125.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  178.0000 -120.0000 68

  6 omega   65.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393   30.0000  -90.0000 112

  7 omega   60.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393 -111.0000  120.0000 53

  8 omega   51.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  -30.0000  120.0000 26

  9 omega   22.00   48.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393 -111.0000  120.0000 26

 10 omega   40.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  -45.0000  -60.0000 57

 11 omega -122.00  -51.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.5600 -178.0000  150.0000 71

 12 omega -122.00   -6.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.5600  -77.0000   90.0000 116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0071067000
_diffrn_orient_matrix_UB_12      -0.0775732000
_diffrn_orient_matrix_UB_13      -0.0554894000
_diffrn_orient_matrix_UB_21      0.0032421000
_diffrn_orient_matrix_UB_22      0.0793095000
_diffrn_orient_matrix_UB_23      -0.0540249000
_diffrn_orient_matrix_UB_31      0.0852573000
_diffrn_orient_matrix_UB_32      -0.0094951000
_diffrn_orient_matrix_UB_33      0.0017268000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19407
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.044
_diffrn_reflns_theta_min         3.892
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77927
_exptl_absorpt_correction_type   multi-scan
_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            'pale yellow'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_F_000             1808
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: pentane/ethyl acetate'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         9194
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0641
_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^)+(0.1053P)^2^+1.5358P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.1972
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7140
_reflns_number_total             9194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00384b2.cif
_cod_data_source_block           ty001dia2
_cod_depositor_comments
;
Adding full bibliography for 7155028--7155030.cif

2017-03-03
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        4958.84(17)
_cod_original_formula_moiety     '2(C21 H39 N2 O4 P)'
_cod_original_formula_sum        'C42 H78 N4 O8 P2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     829.02
_cod_database_code               7155028
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.94
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C20-C21
 1.4 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C18 \\sim C19: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
4.a Rotating group:
 N2(H2A,H2B), N4(H4A,H4B)
4.b Ternary CH refined with riding coordinates:
 C1(H1), C13(H13), C22(H22), C34(H34)
4.c Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B), C39(H39A,H39B), C41(H41A,H41B)
4.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C24(H24), C25(H25), C27(H27), C28(H28)
4.e Idealised Me refined with riding coordinates:
 C21(H21A,H21B,H21C)
4.f 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), C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C),
 C33(H33A,H33B,H33C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,
 H38C), C40(H40A,H40B,H40C), C42(H42A,H42B,H42C)
;
_olex2_submission_special_instructions 'No special instructions were received'