#------------------------------------------------------------------------------
#$Date: 2016-01-15 10:04:32 +0200 (Fri, 15 Jan 2016) $
#$Revision: 174503 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/38/7223890.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_7223890
loop_
_publ_author_name
'Audran, Gérard'
'Bosco, Lionel'
'Brémond, Paul'
'Butscher, Teddy'
'Franconi, Jean-Michel'
'Kabitaev, Kuanysh'
'Marque, Sylvain R. A.'
'Mellet, Philippe'
'Parzy, Elodie'
'Santelli, Maurice'
'Thiaudière, Eric'
'Viel, Stéphane'
_publ_section_title
;
 β-Phosphorus hyperfine coupling constant in nitroxides: 5. Solvent
 effect
;
_journal_issue                   7
_journal_name_full               'RSC Adv.'
_journal_page_first              5653
_journal_paper_doi               10.1039/C5RA23521A
_journal_volume                  6
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C11 H23 N1 O5 P1'
_chemical_formula_sum            'C11 H23 N O5 P'
_chemical_formula_weight         280.27
_chemical_name_systematic
;
 ?
;
_chemical_properties_physical    Heat-sensitive
_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             2013-03-22T10:41:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-07-09 deposited with the CCDC.
2015-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 130.745(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3979(2)
_cell_length_b                   13.6246(3)
_cell_length_c                   13.7301(2)
_cell_measurement_reflns_used    14033
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.01
_cell_measurement_theta_min      2.46
_cell_measurement_wavelength     0.71073
_cell_volume                     1473.65(5)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.951
_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  0.047
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14033
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         29.01
_diffrn_reflns_theta_min         2.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             604
_exptl_crystal_preparation       'Magnetic properties'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.37
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0519
_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)+(0.0957P)²+0.3081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1718
_reflns_number_gt                2742
_reflns_number_total             3739
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5ra23521a2.cif
_cod_data_source_block           lbtrans
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C11 H23 N1 O5 P1'
_cod_database_code               7223890
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
C1 C 0.6134(2) 0.19618(14) 0.06984(18) 0.0441(4) Uani 1 1 d .
C2 C 0.7618(3) 0.12469(17) 0.1586(2) 0.0620(6) Uani 1 1 d .
H2A H 0.7462 0.0875 0.2104 0.074 Uiso 1 1 calc R
H2B H 0.7699 0.0791 0.1085 0.074 Uiso 1 1 calc R
C3 C 0.9202(3) 0.1875(2) 0.2432(2) 0.0682(6) Uani 1 1 d .
H3A H 1.0166 0.1523 0.2641 0.082 Uiso 1 1 calc R
H3B H 0.9446 0.2035 0.3227 0.082 Uiso 1 1 calc R
C4 C 0.8882(2) 0.28064(16) 0.1695(2) 0.0505(5) Uani 1 1 d .
C5 C 0.9546(4) 0.3724(2) 0.2522(3) 0.0850(9) Uani 1 1 d .
H5A H 0.9296 0.4287 0.2005 0.128 Uiso 1 1 calc R
H5B H 1.0752 0.367 0.3204 0.128 Uiso 1 1 calc R
H5C H 0.9011 0.3794 0.2882 0.128 Uiso 1 1 calc R
C6 C 0.9541(3) 0.2785(2) 0.0978(3) 0.0648(6) Uani 1 1 d .
H6A H 0.9108 0.3352 0.0417 0.078 Uiso 1 1 calc R
H6B H 1.077 0.2831 0.1595 0.078 Uiso 1 1 calc R
C7 C 0.4811(3) 0.15877(19) -0.0676(2) 0.0631(6) Uani 1 1 d .
H7A H 0.3931 0.2069 -0.1185 0.095 Uiso 1 1 calc R
H7B H 0.433 0.0987 -0.0676 0.095 Uiso 1 1 calc R
H7C H 0.534 0.1472 -0.1034 0.095 Uiso 1 1 calc R
C8 C 0.3236(4) 0.13219(19) 0.1608(3) 0.0685(7) Uani 1 1 d .
H8A H 0.395 0.1407 0.253 0.082 Uiso 1 1 calc R
H8B H 0.2407 0.1849 0.1188 0.082 Uiso 1 1 calc R
C9 C 0.2374(3) 0.0379(2) 0.1230(3) 0.0769(8) Uani 1 1 d .
H9A H 0.1654 0.0304 0.0315 0.115 Uiso 1 1 calc R
H9B H 0.1699 0.0349 0.1478 0.115 Uiso 1 1 calc R
H9C H 0.32 -0.0139 0.1647 0.115 Uiso 1 1 calc R
C10 C 0.3723(3) 0.40841(16) 0.0495(2) 0.0600(6) Uani 1 1 d .
H10A H 0.3285 0.4378 -0.0314 0.072 Uiso 1 1 calc R
H10B H 0.4895 0.4288 0.1151 0.072 Uiso 1 1 calc R
C11 C 0.2710(4) 0.4427(2) 0.0842(3) 0.0725(7) Uani 1 1 d .
H11A H 0.1552 0.4222 0.0193 0.109 Uiso 1 1 calc R
H11B H 0.2758 0.513 0.0902 0.109 Uiso 1 1 calc R
H11C H 0.3167 0.415 0.1655 0.109 Uiso 1 1 calc R
N1 N 0.70090(19) 0.28337(12) 0.07406(15) 0.0437(4) Uani 1 1 d .
O1 O 0.6382(2) 0.27540(13) 0.26637(15) 0.0630(4) Uani 1 1 d .
O2 O 0.4272(2) 0.13552(10) 0.12375(16) 0.0573(4) Uani 1 1 d .
O3 O 0.36398(18) 0.30223(11) 0.03791(14) 0.0547(4) Uani 1 1 d .
O4 O 0.6199(2) 0.35522(12) -0.00282(17) 0.0634(4) Uani 1 1 d .
O5 O 0.9067(2) 0.19271(15) 0.02376(17) 0.0759(5) Uani 1 1 d .
H5 H 0.8181 0.2027 -0.0498 0.114 Uiso 1 1 calc R
P1 P 0.51688(6) 0.23319(4) 0.13750(5) 0.04434(18) 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
N1 C1 C7 110.66(16)
N1 C1 C2 101.84(16)
C7 C1 C2 113.40(18)
N1 C1 P1 106.69(13)
C7 C1 P1 111.75(14)
C2 C1 P1 111.85(14)
C3 C2 C1 106.06(18)
C3 C2 H2A 110.5
C1 C2 H2A 110.5
C3 C2 H2B 110.5
C1 C2 H2B 110.5
H2A C2 H2B 108.7
C2 C3 C4 107.75(18)
C2 C3 H3A 110.2
C4 C3 H3A 110.2
C2 C3 H3B 110.2
C4 C3 H3B 110.2
H3A C3 H3B 108.5
N1 C4 C5 109.62(18)
N1 C4 C3 101.60(17)
C5 C4 C3 113.2(2)
N1 C4 C6 108.43(17)
C5 C4 C6 108.8(2)
C3 C4 C6 114.8(2)
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
O5 C6 C4 112.9(2)
O5 C6 H6A 109
C4 C6 H6A 109
O5 C6 H6B 109
C4 C6 H6B 109
H6A C6 H6B 107.8
C1 C7 H7A 109.5
C1 C7 H7B 109.5
H7A C7 H7B 109.5
C1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 O2 109.0(2)
C9 C8 H8A 109.9
O2 C8 H8A 109.9
C9 C8 H8B 109.9
O2 C8 H8B 109.9
H8A C8 H8B 108.3
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
O3 C10 C11 110.1(2)
O3 C10 H10A 109.6
C11 C10 H10A 109.6
O3 C10 H10B 109.6
C11 C10 H10B 109.6
H10A C10 H10B 108.1
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
O4 N1 C1 121.98(15)
O4 N1 C4 122.05(16)
C1 N1 C4 115.93(15)
C8 O2 P1 120.08(14)
C10 O3 P1 123.35(14)
C6 O5 H5 109.5
O1 P1 O3 113.79(10)
O1 P1 O2 117.14(10)
O3 P1 O2 102.74(9)
O1 P1 C1 113.38(10)
O3 P1 C1 107.68(9)
O2 P1 C1 100.71(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.474(2)
C1 C7 1.525(3)
C1 C2 1.536(3)
C1 P1 1.8279(19)
C2 C3 1.516(4)
C2 H2A 0.97
C2 H2B 0.97
C3 C4 1.519(3)
C3 H3A 0.97
C3 H3B 0.97
C4 N1 1.476(2)
C4 C5 1.518(3)
C4 C6 1.524(3)
C5 H5A 0.96
C5 H5B 0.96
C5 H5C 0.96
C6 O5 1.409(3)
C6 H6A 0.97
C6 H6B 0.97
C7 H7A 0.96
C7 H7B 0.96
C7 H7C 0.96
C8 C9 1.455(3)
C8 O2 1.462(3)
C8 H8A 0.97
C8 H8B 0.97
C9 H9A 0.96
C9 H9B 0.96
C9 H9C 0.96
C10 O3 1.452(3)
C10 C11 1.487(3)
C10 H10A 0.97
C10 H10B 0.97
C11 H11A 0.96
C11 H11B 0.96
C11 H11C 0.96
N1 O4 1.273(2)
O1 P1 1.4626(16)
O2 P1 1.5639(15)
O3 P1 1.5634(15)
O5 H5 0.82
