#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:02:32 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286025 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/94/1569405.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1569405
loop_
_publ_author_name
'Piris, Patricia'
'Buric, Duje'
'Yamasaki, Toshihide'
'Huchedé, Paul'
'Rossi, Maïlys'
'Matteudi, Mélanie'
'Montero, Marie-Pierre'
'Rodallec, Anne'
'Appay, Romain'
'Roux, Christine'
'Combes, Sébastien'
'Pasquier, Eddy'
'Castets, Marie'
'André, Nicolas'
'Brémond, Paul'
'Carré, Manon'
_publ_section_title
;
 Conditional generation of free radicals by selective activation of
 alkoxyamines: towards more effective and less toxic targeting of brain
 tumors.
;
_journal_issue                   29
_journal_name_full               'Chemical science'
_journal_page_first              7988
_journal_page_last               7998
_journal_paper_doi               10.1039/d3sc01315d
_journal_volume                  14
_journal_year                    2023
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C23 H38 F3 N2 O5 P1'
_chemical_formula_sum            'C23 H38 F3 N2 O5 P'
_chemical_formula_weight         510.52
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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             2013-03-25T10:40:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-09-14 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.21
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6414(2)
_cell_length_b                   17.8695(3)
_cell_length_c                   16.8961(4)
_cell_measurement_reflns_used    26568
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.52
_cell_measurement_theta_min      2.52
_cell_measurement_wavelength     0.71073
_cell_volume                     2731.76(10)
_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 0.997
_diffrn_measured_fraction_theta_max 0.967
_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  0.066
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26568
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         28.52
_diffrn_reflns_theta_min         2.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         6706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1355
_refine_ls_R_factor_gt           0.0813
_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/[σ²(Fo²)+(0.1501P)²+1.0120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2216
_refine_ls_wR_factor_ref         0.272
_reflns_number_gt                3905
_reflns_number_total             6706
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d3sc01315d2.cif
_cod_data_source_block           ck3minor
_cod_depositor_comments
'Adding full bibliography for 1569404--1569405.cif.'
_cod_original_cell_volume        2731.72(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C23 H38 F3 N2 O5 P1'
_cod_database_code               1569405
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5081(3) 0.26122(17) 0.57236(17) 0.0500(6) Uani 1 1 d . . .
H1 H 0.4582 0.2154 0.58 0.06 Uiso 1 1 calc R . .
C2 C 0.6520(3) 0.26784(19) 0.64670(19) 0.0579(7) Uani 1 1 d . . .
H2A H 0.6297 0.2652 0.6984 0.069 Uiso 1 1 calc R . .
H2B H 0.7136 0.2251 0.646 0.069 Uiso 1 1 calc R . .
C3 C 0.7535(4) 0.3865(2) 0.7083(2) 0.0610(8) Uani 1 1 d . . .
C4 C 0.8532(5) 0.4510(3) 0.7057(3) 0.0824(11) Uani 1 1 d . . .
C5 C 0.4051(3) 0.32549(17) 0.56634(18) 0.0532(7) Uani 1 1 d . . .
C6 C 0.2957(4) 0.3195(2) 0.6018(2) 0.0706(9) Uani 1 1 d . . .
H6 H 0.2847 0.275 0.6277 0.085 Uiso 1 1 calc R . .
C7 C 0.2025(4) 0.3793(3) 0.5990(3) 0.0901(13) Uani 1 1 d . . .
H7 H 0.1294 0.3749 0.623 0.108 Uiso 1 1 calc R . .
C8 C 0.2179(5) 0.4448(3) 0.5609(3) 0.0938(14) Uani 1 1 d . . .
H8 H 0.1544 0.4846 0.5583 0.113 Uiso 1 1 calc R . .
C9 C 0.3258(5) 0.4518(2) 0.5268(3) 0.0802(11) Uani 1 1 d . . .
H9 H 0.3369 0.4967 0.5018 0.096 Uiso 1 1 calc R . .
C10 C 0.4188(4) 0.39282(19) 0.5291(2) 0.0658(8) Uani 1 1 d . . .
H10 H 0.492 0.3982 0.5054 0.079 Uiso 1 1 calc R . .
C11 C 0.7143(3) 0.18938(16) 0.45579(18) 0.0502(6) Uani 1 1 d . . .
H11 H 0.6919 0.1619 0.4026 0.06 Uiso 1 1 calc R . .
C12 C 0.8558(4) 0.14827(19) 0.5192(2) 0.0630(8) Uani 1 1 d . . .
C13 C 0.9381(5) 0.1093(3) 0.4676(3) 0.0876(12) Uani 1 1 d . . .
H13A H 0.9737 0.1462 0.438 0.131 Uiso 1 1 calc R . .
H13B H 0.8721 0.0758 0.4278 0.131 Uiso 1 1 calc R . .
H13C H 1.0201 0.0816 0.5048 0.131 Uiso 1 1 calc R . .
C14 C 0.9643(4) 0.2011(2) 0.5821(3) 0.0799(11) Uani 1 1 d . . .
H14A H 1.0444 0.1726 0.6198 0.12 Uiso 1 1 calc R . .
H14B H 0.9141 0.2273 0.6138 0.12 Uiso 1 1 calc R . .
H14C H 1.0024 0.2364 0.552 0.12 Uiso 1 1 calc R . .
C15 C 0.8115(5) 0.0874(2) 0.5703(3) 0.0842(11) Uani 1 1 d . . .
H15A H 0.7499 0.0511 0.5325 0.126 Uiso 1 1 calc R . .
H15B H 0.7582 0.1099 0.6028 0.126 Uiso 1 1 calc R . .
H15C H 0.8987 0.0634 0.6075 0.126 Uiso 1 1 calc R . .
C16 C 0.4491(4) 0.14371(18) 0.4132(2) 0.0588(7) Uani 1 1 d . . .
C17 C 0.3286(4) 0.1339(2) 0.4517(2) 0.0713(9) Uani 1 1 d . . .
H17A H 0.3676 0.1068 0.5037 0.107 Uiso 1 1 calc R . .
H17B H 0.2474 0.1066 0.4132 0.107 Uiso 1 1 calc R . .
H17C H 0.295 0.1822 0.4623 0.107 Uiso 1 1 calc R . .
C18 C 0.4960(5) 0.0654(2) 0.3959(3) 0.0826(11) Uani 1 1 d . . .
H18A H 0.5775 0.0692 0.3758 0.124 Uiso 1 1 calc R . .
H18B H 0.4146 0.0411 0.3541 0.124 Uiso 1 1 calc R . .
H18C H 0.5255 0.0366 0.4471 0.124 Uiso 1 1 calc R . .
C19 C 0.3884(4) 0.1859(2) 0.3304(2) 0.0802(11) Uani 1 1 d . . .
H19A H 0.3598 0.2354 0.3408 0.12 Uiso 1 1 calc R . .
H19B H 0.3039 0.1599 0.2932 0.12 Uiso 1 1 calc R . .
H19C H 0.4631 0.1891 0.3049 0.12 Uiso 1 1 calc R . .
C20 C 0.5332(5) 0.3752(2) 0.3352(3) 0.0876(12) Uani 1 1 d . . .
H20A H 0.4453 0.3675 0.3497 0.105 Uiso 1 1 calc R . .
H20B H 0.5924 0.4136 0.3721 0.105 Uiso 1 1 calc R . .
C21 C 0.4913(10) 0.3996(4) 0.2501(4) 0.179(4) Uani 1 1 d . . .
H21A H 0.5753 0.4212 0.2405 0.268 Uiso 1 1 calc R . .
H21B H 0.4145 0.4365 0.2394 0.268 Uiso 1 1 calc R . .
H21C H 0.4557 0.3578 0.213 0.268 Uiso 1 1 calc R . .
C22 C 0.9500(6) 0.3310(3) 0.3682(4) 0.1142(19) Uani 1 1 d . . .
H22A H 0.8755 0.3622 0.3287 0.137 Uiso 1 1 calc R . .
H22B H 1.0014 0.3614 0.4171 0.137 Uiso 1 1 calc R . .
C23 C 1.0484(7) 0.3092(4) 0.3314(4) 0.134(2) Uani 1 1 d . . .
H23A H 1.1407 0.2966 0.3743 0.201 Uiso 1 1 calc R . .
H23B H 1.0635 0.3493 0.2974 0.201 Uiso 1 1 calc R . .
H23C H 1.0105 0.2662 0.2964 0.201 Uiso 1 1 calc R . .
N1 N 0.5786(3) 0.18117(13) 0.47869(15) 0.0492(5) Uani 1 1 d . . .
N2 N 0.7355(3) 0.33508(15) 0.64850(16) 0.0574(6) Uani 1 1 d . . .
H2 H 0.7743 0.3421 0.6103 0.069 Uiso 1 1 calc R . .
O1 O 0.5295(2) 0.25603(10) 0.49199(12) 0.0491(5) Uani 1 1 d . . .
O2 O 0.6993(3) 0.38515(19) 0.76319(17) 0.0915(9) Uani 1 1 d . . .
O3 O 0.7846(3) 0.34405(12) 0.49526(14) 0.0649(6) Uani 1 1 d . . .
O4 O 0.6162(3) 0.30695(12) 0.34808(14) 0.0642(6) Uani 1 1 d . . .
O5 O 0.8774(3) 0.27089(14) 0.39433(16) 0.0718(7) Uani 1 1 d . . .
F1 F 0.8975(3) 0.45438(16) 0.64201(17) 0.1044(8) Uani 1 1 d . . .
F2 F 0.9748(6) 0.4481(4) 0.7699(2) 0.219(3) Uani 1 1 d . . .
F3 F 0.7973(7) 0.5128(2) 0.7112(5) 0.246(4) Uani 1 1 d . . .
P1 P 0.74889(9) 0.28590(4) 0.42985(5) 0.0546(3) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C5 107.0(2) . . ?
O1 C1 C2 113.3(2) . . ?
C5 C1 C2 113.0(3) . . ?
O1 C1 H1 107.8 . . ?
C5 C1 H1 107.8 . . ?
C2 C1 H1 107.8 . . ?
N2 C2 C1 115.2(3) . . ?
N2 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
N2 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
O2 C3 N2 126.1(3) . . ?
O2 C3 C4 119.0(3) . . ?
N2 C3 C4 115.0(3) . . ?
F3 C4 F1 107.3(5) . . ?
F3 C4 F2 105.2(5) . . ?
F1 C4 F2 103.6(4) . . ?
F3 C4 C3 112.2(4) . . ?
F1 C4 C3 117.2(3) . . ?
F2 C4 C3 110.3(4) . . ?
C10 C5 C6 118.0(3) . . ?
C10 C5 C1 122.1(3) . . ?
C6 C5 C1 119.8(3) . . ?
C5 C6 C7 120.4(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.0(4) . . ?
C8 C7 H7 120 . . ?
C6 C7 H7 120 . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.3(4) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
N1 C11 C12 113.8(2) . . ?
N1 C11 P1 113.63(19) . . ?
C12 C11 P1 114.2(2) . . ?
N1 C11 H11 104.6 . . ?
C12 C11 H11 104.6 . . ?
P1 C11 H11 104.6 . . ?
C14 C12 C13 108.1(3) . . ?
C14 C12 C15 107.6(3) . . ?
C13 C12 C15 107.3(3) . . ?
C14 C12 C11 113.8(3) . . ?
C13 C12 C11 108.5(3) . . ?
C15 C12 C11 111.4(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C19 114.4(3) . . ?
N1 C16 C17 107.3(2) . . ?
C19 C16 C17 110.0(3) . . ?
N1 C16 C18 108.8(3) . . ?
C19 C16 C18 108.9(3) . . ?
C17 C16 C18 107.2(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 O4 111.3(4) . . ?
C21 C20 H20A 109.4 . . ?
O4 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
O4 C20 H20B 109.4 . . ?
H20A C20 H20B 108 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 O5 114.8(5) . . ?
C23 C22 H22A 108.6 . . ?
O5 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
O5 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 N1 C11 107.99(19) . . ?
O1 N1 C16 106.8(2) . . ?
C11 N1 C16 115.5(2) . . ?
C3 N2 C2 121.2(3) . . ?
C3 N2 H2 119.4 . . ?
C2 N2 H2 119.4 . . ?
C1 O1 N1 111.22(19) . . ?
C20 O4 P1 125.4(2) . . ?
C22 O5 P1 121.5(3) . . ?
O3 P1 O4 113.61(14) . . ?
O3 P1 O5 113.37(14) . . ?
O4 P1 O5 102.38(14) . . ?
O3 P1 C11 119.94(13) . . ?
O4 P1 C11 105.95(13) . . ?
O5 P1 C11 99.35(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.445(3) . ?
C1 C5 1.498(4) . ?
C1 C2 1.521(4) . ?
C1 H1 0.98 . ?
C2 N2 1.440(4) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 O2 1.212(4) . ?
C3 N2 1.332(4) . ?
C3 C4 1.511(5) . ?
C4 F3 1.246(6) . ?
C4 F1 1.289(4) . ?
C4 F2 1.294(6) . ?
C5 C10 1.385(5) . ?
C5 C6 1.385(4) . ?
C6 C7 1.387(5) . ?
C6 H6 0.93 . ?
C7 C8 1.369(7) . ?
C7 H7 0.93 . ?
C8 C9 1.357(6) . ?
C8 H8 0.93 . ?
C9 C10 1.376(5) . ?
C9 H9 0.93 . ?
C10 H10 0.93 . ?
C11 N1 1.495(3) . ?
C11 C12 1.593(4) . ?
C11 P1 1.838(3) . ?
C11 H11 0.98 . ?
C12 C14 1.531(5) . ?
C12 C13 1.534(5) . ?
C12 C15 1.537(5) . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C16 N1 1.509(4) . ?
C16 C19 1.517(5) . ?
C16 C17 1.525(4) . ?
C16 C18 1.530(5) . ?
C17 H17A 0.96 . ?
C17 H17B 0.96 . ?
C17 H17C 0.96 . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?
C20 C21 1.421(7) . ?
C20 O4 1.433(4) . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?
C22 C23 1.359(6) . ?
C22 O5 1.432(4) . ?
C22 H22A 0.97 . ?
C22 H22B 0.97 . ?
C23 H23A 0.96 . ?
C23 H23B 0.96 . ?
C23 H23C 0.96 . ?
N1 O1 1.462(3) . ?
N2 H2 0.86 . ?
O3 P1 1.469(2) . ?
O4 P1 1.570(2) . ?
O5 P1 1.575(2) . ?
