Enzymatic triggering of C–ON bond homolysis of alkoxyamines
Audran, Gérard; Bosco, Lionel; Brémond, Paul; Jugniot, Natacha; Marque, Sylvain R. A.; Massot, Philippe; Mellet, Philippe; Moussounda Moussounda Koumba, Tataye; Parzy, Elodie; Rivot, Angélique; Thiaudière, Eric; Voisin, Pierre; Wedl, Carina; Yamasaki, Toshihide; Organic Chemistry Frontiers 6 (2019) 3663–; doi:10.1039/C9QO00899C

data_1555120
_publ_section_title
;
 Enzymatic triggering of C--ON bond homolysis of alkoxyamines
;
_journal_issue                   21
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3663
_journal_paper_doi               10.1039/C9QO00899C
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C20 H38 N3 O4 P, H2 O'
_chemical_formula_sum            'C20 H40 N3 O5 P'
_chemical_formula_weight         433.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date
;
'Thu Jul 03 17:58:51 2014'
;
_audit_creation_method
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_audit_update_record
;
2018-11-22 deposited with the CCDC.	2019-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                75.673(4)
_cell_angle_beta                 76.438(4)
_cell_angle_gamma                71.300(5)
_cell_formula_units_Z            2
_cell_length_a                   9.2786(6)
_cell_length_b                   9.5213(6)
_cell_length_c                   15.4265(6)
_cell_measurement_reflns_used    3506
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7970
_cell_measurement_theta_min      4.9730
_cell_volume                     1232.75(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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 0.983
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details
;
  1 omega  -49.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146   38.0000    0.0000 78

  2 omega  -46.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146   38.0000 -150.0000 81

  3 omega  -96.00  -13.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146  125.0000 -180.0000 83

  4 omega -114.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146  -57.0000   60.0000 103

  5 omega   43.00   90.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -30.0000  -30.0000 47

  6 omega   78.00  178.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719   30.0000   30.0000 100

  7 omega   78.00  174.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719   30.0000  120.0000 96

  8 omega   61.00  121.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719 -125.0000  -60.0000 60

  9 omega   36.00   93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -45.0000   90.0000 57

 10 omega   42.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -94.0000  120.0000 67

 11 omega   33.00   92.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -45.0000  150.0000 59

 12 omega   31.00  130.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -77.0000  -30.0000 99

 13 omega   31.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -30.0000 -150.0000 60
;
_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      -0.1112558000
_diffrn_orient_matrix_UB_12      -0.0998790000
_diffrn_orient_matrix_UB_13      0.0282288000
_diffrn_orient_matrix_UB_21      0.1349476000
_diffrn_orient_matrix_UB_22      -0.1396812000
_diffrn_orient_matrix_UB_23      0.0233858000
_diffrn_orient_matrix_UB_31      -0.0322591000
_diffrn_orient_matrix_UB_32      0.0274009000
_diffrn_orient_matrix_UB_33      0.0979402000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7179
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.728
_diffrn_reflns_theta_min         4.992
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.256
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_F_000             472
_exptl_crystal_size_max          .22
_exptl_crystal_size_mid          .14
_exptl_crystal_size_min          .03
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0792P)^2^+0.2551P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1561
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4032
_reflns_number_total             4718
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00899c2.cif
_cod_data_source_block           pyethsg1nh2_b
_cod_original_cell_volume        1232.76(11)
_cod_database_code               1555120
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 98.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H3A,H3B} of O5, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, {H5A,H5B} of O5
2.a Free rotating group:
 O5(H3A,H3B,H5A,H5B)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C12(H12)
2.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C17(H17A,H17B), C19(H19A,H19B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,
 H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'