#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:03:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180166 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/62/7106208.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_7106208
loop_
_publ_author_name
'Paul Bremond'
'Sylvain Marque'
_publ_section_title
;
 First proton triggered C–ON bond homolysis in alkoxyamines
;
_journal_name_full               Chem.Commun.
_journal_page_first              4291
_journal_paper_doi               10.1039/c0cc05637e
_journal_volume                  47
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H37 N2 O4 P1'
_chemical_formula_sum            'C20 H37 N2 O4 P'
_chemical_formula_weight         400.49
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_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             2010-11-19T15:01:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 110.186(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3707(2)
_cell_length_b                   9.7253(2)
_cell_length_c                   18.8006(4)
_cell_measurement_reflns_used    20863
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.72
_cell_measurement_theta_min      1.62
_cell_measurement_wavelength     0.71073
_cell_volume                     2294.56(8)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.042
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20863
_diffrn_reflns_theta_full        28.72
_diffrn_reflns_theta_max         28.72
_diffrn_reflns_theta_min         1.62
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.947
_refine_diff_density_rms         0.284
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         5772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0518
_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)+(0.1125P)²+0.3935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.1971
_reflns_number_gt                4537
_reflns_number_total             5772
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0cc05637e.txt
_cod_data_source_block           pyrnomin
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7106208
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 0.16989(13) 0.40236(17) 0.21970(9) 0.0364(4) Uani 1 1 d . . .
H1 H 0.1189 0.4743 0.2202 0.044 Uiso 1 1 calc R . .
C2 C 0.12782(16) 0.3427(2) 0.13677(10) 0.0459(4) Uani 1 1 d . . .
C3 C 0.0117(2) 0.2989(3) 0.11785(14) 0.0713(7) Uani 1 1 d . . .
H3A H -0.0154 0.2641 0.067 0.107 Uiso 1 1 calc R . .
H3B H -0.03 0.3767 0.1222 0.107 Uiso 1 1 calc R . .
H3C H 0.0074 0.2284 0.1525 0.107 Uiso 1 1 calc R . .
C4 C 0.1925(2) 0.2198(2) 0.12642(12) 0.0666(7) Uani 1 1 d . . .
H4A H 0.1864 0.1457 0.1584 0.1 Uiso 1 1 calc R . .
H4B H 0.2659 0.2459 0.1398 0.1 Uiso 1 1 calc R . .
H4C H 0.1658 0.1906 0.0745 0.1 Uiso 1 1 calc R . .
C5 C 0.1294(2) 0.4539(3) 0.07888(12) 0.0579(5) Uani 1 1 d . . .
H5A H 0.2018 0.4782 0.086 0.087 Uiso 1 1 calc R . .
H5B H 0.0918 0.5338 0.0861 0.087 Uiso 1 1 calc R . .
H5C H 0.0955 0.4191 0.0285 0.087 Uiso 1 1 calc R . .
C6 C 0.3216(2) 0.7332(2) 0.18576(16) 0.0653(6) Uani 1 1 d . . .
H6A H 0.3652 0.6864 0.1614 0.078 Uiso 1 1 calc R . .
H6B H 0.3684 0.7767 0.2316 0.078 Uiso 1 1 calc R . .
C7 C 0.2545(3) 0.8375(3) 0.1344(2) 0.0920(11) Uani 1 1 d . . .
H7A H 0.2093 0.7938 0.0889 0.138 Uiso 1 1 calc R . .
H7B H 0.2991 0.9038 0.122 0.138 Uiso 1 1 calc R . .
H7C H 0.2114 0.8829 0.1589 0.138 Uiso 1 1 calc R . .
C8 C 0.4487(2) 0.4799(3) 0.37636(16) 0.0781(8) Uani 1 1 d . . .
H8A H 0.4771 0.4154 0.3488 0.094 Uiso 1 1 calc R . .
H8B H 0.4394 0.4317 0.4188 0.094 Uiso 1 1 calc R . .
C9 C 0.5239(2) 0.5946(4) 0.4045(2) 0.0952(11) Uani 1 1 d . . .
H9A H 0.5345 0.6405 0.3624 0.143 Uiso 1 1 calc R . .
H9B H 0.5907 0.5597 0.4379 0.143 Uiso 1 1 calc R . .
H9C H 0.4953 0.6584 0.4315 0.143 Uiso 1 1 calc R . .
C10 C 0.10817(15) 0.3459(2) 0.32997(11) 0.0447(4) Uani 1 1 d . . .
C11 C -0.0061(2) 0.3878(3) 0.28384(16) 0.0761(8) Uani 1 1 d . . .
H11A H -0.005 0.4671 0.2537 0.114 Uiso 1 1 calc R . .
H11B H -0.0438 0.4093 0.3176 0.114 Uiso 1 1 calc R . .
H11C H -0.0411 0.3133 0.2513 0.114 Uiso 1 1 calc R . .
C12 C 0.1632(2) 0.4641(3) 0.38161(17) 0.0740(7) Uani 1 1 d . . .
H12A H 0.2346 0.4376 0.4113 0.111 Uiso 1 1 calc R . .
H12B H 0.1246 0.4862 0.4147 0.111 Uiso 1 1 calc R . .
H12C H 0.1652 0.543 0.3515 0.111 Uiso 1 1 calc R . .
C13 C 0.1003(2) 0.2217(3) 0.37713(15) 0.0639(6) Uani 1 1 d . . .
H13A H 0.0718 0.1449 0.3443 0.096 Uiso 1 1 calc R . .
H13B H 0.0541 0.243 0.405 0.096 Uiso 1 1 calc R . .
H13C H 0.1698 0.1988 0.4118 0.096 Uiso 1 1 calc R . .
C14 C 0.29652(14) 0.11817(18) 0.31530(10) 0.0395(4) Uani 1 1 d . . .
H14 H 0.2386 0.0765 0.2735 0.047 Uiso 1 1 calc R . .
C15 C 0.31252(14) 0.03789(19) 0.38700(10) 0.0394(4) Uani 1 1 d . . .
C16 C 0.36047(16) 0.0941(2) 0.45866(11) 0.0474(4) Uani 1 1 d . . .
H16 H 0.3801 0.1863 0.464 0.057 Uiso 1 1 calc R . .
C17 C 0.37873(19) 0.0122(2) 0.52181(13) 0.0555(5) Uani 1 1 d . . .
H17 H 0.4099 0.0525 0.5692 0.067 Uiso 1 1 calc R . .
C18 C 0.3096(2) -0.1739(2) 0.45026(15) 0.0671(6) Uani 1 1 d . . .
H18 H 0.2925 -0.2669 0.4467 0.081 Uiso 1 1 calc R . .
C19 C 0.28661(19) -0.1001(2) 0.38368(13) 0.0547(5) Uani 1 1 d . . .
H19 H 0.2541 -0.1429 0.3371 0.066 Uiso 1 1 calc R . .
C20 C 0.39928(18) 0.1123(2) 0.29747(13) 0.0550(5) Uani 1 1 d . . .
H20A H 0.3905 0.1637 0.2521 0.083 Uiso 1 1 calc R . .
H20B H 0.4156 0.0184 0.2903 0.083 Uiso 1 1 calc R . .
H20C H 0.4564 0.1513 0.3388 0.083 Uiso 1 1 calc R . .
N1 N 0.16335(11) 0.29884(14) 0.27649(8) 0.0356(3) Uani 1 1 d . . .
N2 N 0.35455(18) -0.1206(2) 0.51906(12) 0.0641(5) Uani 1 1 d . . .
O2 O 0.37630(12) 0.42839(16) 0.21156(9) 0.0552(4) Uani 1 1 d . . .
O3 O 0.34672(12) 0.53190(16) 0.32681(9) 0.0559(4) Uani 1 1 d . . .
O4 O 0.25267(12) 0.63551(14) 0.20429(9) 0.0529(4) Uani 1 1 d . . .
O5 O 0.27242(9) 0.26143(12) 0.32228(7) 0.0375(3) Uani 1 1 d . . .
P1 P 0.29869(4) 0.49209(5) 0.24056(3) 0.04145(17) 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'
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
N1 C1 C2 111.76(14) . . ?
N1 C1 P1 116.57(11) . . ?
C2 C1 P1 111.88(12) . . ?
N1 C1 H1 105.2 . . ?
C2 C1 H1 105.2 . . ?
P1 C1 H1 105.2 . . ?
C4 C2 C3 109.1(2) . . ?
C4 C2 C5 108.27(18) . . ?
C3 C2 C5 106.95(18) . . ?
C4 C2 C1 112.98(15) . . ?
C3 C2 C1 108.67(17) . . ?
C5 C2 C1 110.70(16) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O4 C6 C7 108.4(2) . . ?
O4 C6 H6A 110 . . ?
C7 C6 H6A 110 . . ?
O4 C6 H6B 110 . . ?
C7 C6 H6B 110 . . ?
H6A C6 H6B 108.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C8 C9 109.9(3) . . ?
O3 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
O3 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C12 114.49(16) . . ?
N1 C10 C13 107.19(16) . . ?
C12 C10 C13 110.1(2) . . ?
N1 C10 C11 108.99(17) . . ?
C12 C10 C11 109.2(2) . . ?
C13 C10 C11 106.56(19) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 C15 112.64(14) . . ?
O5 C14 C20 107.57(16) . . ?
C15 C14 C20 108.48(15) . . ?
O5 C14 H14 109.4 . . ?
C15 C14 H14 109.4 . . ?
C20 C14 H14 109.4 . . ?
C19 C15 C16 116.78(18) . . ?
C19 C15 C14 120.42(17) . . ?
C16 C15 C14 122.62(17) . . ?
C17 C16 C15 119.55(19) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
N2 C17 C16 124.0(2) . . ?
N2 C17 H17 118 . . ?
C16 C17 H17 118 . . ?
N2 C18 C19 124.3(2) . . ?
N2 C18 H18 117.9 . . ?
C19 C18 H18 117.9 . . ?
C15 C19 C18 119.3(2) . . ?
C15 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 N1 C1 107.26(12) . . ?
O5 N1 C10 107.53(13) . . ?
C1 N1 C10 115.80(13) . . ?
C17 N2 C18 116.08(19) . . ?
C8 O3 P1 122.34(17) . . ?
C6 O4 P1 119.83(15) . . ?
C14 O5 N1 113.26(12) . . ?
O2 P1 O3 113.45(9) . . ?
O2 P1 O4 115.63(9) . . ?
O3 P1 O4 100.79(9) . . ?
O2 P1 C1 116.68(9) . . ?
O3 P1 C1 110.74(8) . . ?
O4 P1 C1 97.45(8) . . ?
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 N1 1.492(2) . ?
C1 C2 1.575(2) . ?
C1 P1 1.8480(17) . ?
C1 H1 0.98 . ?
C2 C4 1.526(3) . ?
C2 C3 1.529(3) . ?
C2 C5 1.540(3) . ?
C3 H3A 0.96 . ?
C3 H3B 0.96 . ?
C3 H3C 0.96 . ?
C4 H4A 0.96 . ?
C4 H4B 0.96 . ?
C4 H4C 0.96 . ?
C5 H5A 0.96 . ?
C5 H5B 0.96 . ?
C5 H5C 0.96 . ?
C6 O4 1.447(2) . ?
C6 C7 1.472(4) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
C8 O3 1.452(3) . ?
C8 C9 1.472(4) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 H9A 0.96 . ?
C9 H9B 0.96 . ?
C9 H9C 0.96 . ?
C10 N1 1.509(2) . ?
C10 C12 1.520(3) . ?
C10 C13 1.524(3) . ?
C10 C11 1.529(3) . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 O5 1.446(2) . ?
C14 C15 1.508(2) . ?
C14 C20 1.523(3) . ?
C14 H14 0.98 . ?
C15 C19 1.382(3) . ?
C15 C16 1.389(3) . ?
C16 C17 1.379(3) . ?
C16 H16 0.93 . ?
C17 N2 1.328(3) . ?
C17 H17 0.93 . ?
C18 N2 1.329(3) . ?
C18 C19 1.382(3) . ?
C18 H18 0.93 . ?
C19 H19 0.93 . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 0.96 . ?
N1 O5 1.4607(17) . ?
O2 P1 1.4657(15) . ?
O3 P1 1.5725(16) . ?
O4 P1 1.5810(15) . ?
