How intramolecular coordination bonding (ICB) controls the homolysis of the C–ON bond in alkoxyamines
Audran, Gérard; Bagryanskaya, Elena; Bagryanskaya, Irina; Edeleva, Mariya; Joly, Jean-Patrick; Marque, Sylvain R. A.; Iurchenkova, Anna; Kaletina, Polina; Cherkasov, Sergey; Hai, Tung To; Tretyakov, Evgeny; Zhivetyeva, Svetlana; RSC Advances 9 (2019) 25776–; doi:10.1039/C9RA05334D

data_7233392
_publ_section_title
;
 How intramolecular coordination bonding (ICB) controls the homolysis of
 the C--ON bond in alkoxyamines
;
_journal_issue                   44
_journal_name_full               'RSC Advances'
_journal_page_first              25776
_journal_paper_doi               10.1039/C9RA05334D
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C19 H36 N3 O5 P'
_chemical_formula_sum            'C19 H36 N3 O5 P'
_chemical_formula_weight         417.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-22 deposited with the CCDC.    2019-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.873(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.2198(9)
_cell_length_b                   9.6226(6)
_cell_length_c                   29.4018(18)
_cell_measurement_reflns_used    4415
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8710
_cell_measurement_theta_min      3.6110
_cell_volume                     4578.5(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      2.00  57.00   1.00   30.00    --  -13.35  77.00-150.00   55
  2  \w    -25.00  99.00   1.00   30.00    --   14.06  77.00 -90.00  124
  3  \w      5.00  74.00   1.00   30.00    --   14.06  77.00   0.00   69
  4  \w    -10.00  77.00   1.00   30.00    --   14.06  77.00 120.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0198738000
_diffrn_orient_matrix_UB_12      0.0617225000
_diffrn_orient_matrix_UB_13      -0.0080806000
_diffrn_orient_matrix_UB_21      0.0390396000
_diffrn_orient_matrix_UB_22      0.0320295000
_diffrn_orient_matrix_UB_23      -0.0017190000
_diffrn_orient_matrix_UB_31      0.0009556000
_diffrn_orient_matrix_UB_32      -0.0244223000
_diffrn_orient_matrix_UB_33      -0.0227348000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13148
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.713
_diffrn_reflns_theta_max         24.713
_diffrn_reflns_theta_min         2.792
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0735
_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^)+(0.2000P)^2^+5.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2152
_refine_ls_wR_factor_ref         0.3084
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2769
_reflns_number_total             3887
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra05334d2.cif
_cod_data_source_block           6_RSSR_579f1
_cod_database_code               7233392
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c19 h36 n3 o5 p1'
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.947
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_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:
 C5(H5), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,
 H17C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.661
_oxdiff_exptl_absorpt_empirical_full_min 0.602