Intramolecular Hydrogen Bond in Alkoxyamines. Influence on the C-ON Bond Homolysis
Paul Brémond; Teddy Butscher; Valérie Roubaud; Didier Siri; Stéphane Viel; Journal of Organic Chemistry 78 (2013) 10524–10529; doi:10.1021/jo401681w

data_4028668
_publ_section_title
;
 Intramolecular Hydrogen Bond in Alkoxyamines. Influence on the C-ON Bond
 Homolysis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10524
_journal_page_last               10529
_journal_paper_doi               10.1021/jo401681w
_journal_volume                  78
_journal_year                    2013
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H40 N1 O5 P1'
_chemical_formula_sum            'C22 H40 N O5 P'
_chemical_formula_weight         429.52
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-02-15T10:54:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                93.028(1)
_cell_angle_beta                 105.023(1)
_cell_angle_gamma                92.048(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5099(2)
_cell_length_b                   10.6736(3)
_cell_length_c                   14.6871(5)
_cell_measurement_reflns_used    15286
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.02
_cell_measurement_theta_min      3.06
_cell_measurement_wavelength     0.71073
_cell_volume                     1284.96(6)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15286
_diffrn_reflns_theta_full        25.
_diffrn_reflns_theta_max         29.02
_diffrn_reflns_theta_min         3.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.11
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         6475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.114
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0615P)^2^+0.7291P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1784
_reflns_number_gt                4150
_reflns_number_total             6475
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo401681w_si_003.cif
_cod_data_source_block           stomedia2
_cod_original_formula_sum        'C22 H40 N1 O5 P1'
_cod_database_code               4028668