#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:01:32 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180219 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/05/7110525.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7110525
loop_
_publ_author_name
'He, Zhengjie'
'Modro, Tomasz A.'
'Van Rooyen, Petrus H.'
'Bourne, Susan A.'
_publ_section_title
;
 Metallation-induced migration of phosphorus from nitrogen to carbon in
 1-oxo-2,8-diphenyl-2,5,8-triaza-1λ5-phosphabicyclo[3.3.0]octane: unusual
 bonding parameters of the double migration product
;
_journal_issue                   9
_journal_name_full               'Chemical Communications'
_journal_page_first              853
_journal_paper_doi               10.1039/a901877h
_journal_year                    1999
_chemical_formula_sum            'C16 H18 N3 O P'
_chemical_formula_weight         299.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.648(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.201(3)
_cell_length_b                   9.0538(16)
_cell_length_c                   20.266(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      16.96
_cell_measurement_theta_min      14.17
_cell_volume                     1504.1(6)
_computing_cell_refinement       'Enraf Nonius CAD4'
_computing_data_collection       'Enraf Nonius CAD4'
_computing_data_reduction        'Enraf Nonius CAD4'
_computing_molecular_graphics    Ortep
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       omega-2theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            4659
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         3.02
_diffrn_standards_decay_%        2.0
_diffrn_standards_interval_time  3600
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.9710
_exptl_absorpt_correction_T_min  0.9050
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0776
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0584P)²+0.8458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1833
_refine_ls_wR_factor_ref         0.1980
_reflns_number_gt                2899
_reflns_number_total             4380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            901877hsup1.cif
_cod_data_source_block           compound_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.8458P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.8458P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1504.2(7)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7110525
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_calc_flag
_atom_site_refinement_flags
O1 O 0.5991(2) 0.7809(2) 0.13921(11) 0.0635(6) Uani 1 d .
P1 P 0.70292(9) 0.90499(8) 0.11864(4) 0.0517(2) Uani 1 d .
N1 N 0.7319(3) 0.9169(3) 0.03775(12) 0.0576(6) Uani 1 d .
C1 C 0.7752(4) 0.8023(3) -0.00537(15) 0.0571(7) Uani 1 d .
C2 C 0.8471(4) 0.8337(4) -0.06489(17) 0.0719(9) Uani 1 d .
H2 H 0.8673 0.9314 -0.0763 0.103(3) Uiso 1 calc R
C3 C 0.8888(6) 0.7224(5) -0.1072(2) 0.0891(12) Uani 1 d .
H3 H 0.9381 0.7458 -0.1466 0.103(3) Uiso 1 calc R
C4 C 0.8595(7) 0.5795(5) -0.0924(2) 0.1019(15) Uani 1 d .
H4 H 0.8869 0.5046 -0.1215 0.103(3) Uiso 1 calc R
C5 C 0.7891(7) 0.5474(5) -0.0342(2) 0.1128(18) Uani 1 d .
H5 H 0.7702 0.4491 -0.0235 0.103(3) Uiso 1 calc R
C6 C 0.7449(6) 0.6557(4) 0.00938(18) 0.0877(13) Uani 1 d .
H6 H 0.6950 0.6307 0.0485 0.103(3) Uiso 1 calc R
C7 C 0.7250(4) 1.0703(3) 0.01364(18) 0.0685(9) Uani 1 d .
H7A H 0.6602 1.0760 -0.0271 0.103(3) Uiso 1 calc R
H7B H 0.8339 1.1062 0.0053 0.103(3) Uiso 1 calc R
C8 C 0.6487(5) 1.1609(4) 0.0663(2) 0.0832(11) Uani 1 d .
H8A H 0.7164 1.2461 0.0766 0.103(3) Uiso 1 calc R
H8B H 0.5424 1.1957 0.0510 0.103(3) Uiso 1 calc R
N2 N 0.6323(4) 1.0730(3) 0.12356(17) 0.0806(9) Uani 1 d .
C9 C 0.5772(6) 1.1383(5) 0.1841(2) 0.1027(15) Uani 1 d .
H9A H 0.4593 1.1312 0.1853 0.103(3) Uiso 1 calc R
H9B H 0.6065 1.2421 0.1851 0.103(3) Uiso 1 calc R
C10 C 0.6518(6) 1.0623(5) 0.2437(2) 0.0991(15) Uani 1 d .
H11A H 0.6056 1.1037 0.2832 0.103(3) Uiso 1 calc R
H11B H 0.6238 0.9583 0.2421 0.103(3) Uiso 1 calc R
N3 N 0.8284(6) 1.0771(4) 0.24805(19) 0.1004(13) Uani 1 d .
HN3 H 0.868(6) 1.118(5) 0.279(2) 0.103(3) Uiso 1 d .
C11 C 0.9374(4) 0.9853(4) 0.21784(16) 0.0683(9) Uani 1 d .
C12 C 1.0996(6) 0.9763(5) 0.24339(19) 0.0919(14) Uani 1 d .
H12 H 1.1288 1.0316 0.2805 0.103(3) Uiso 1 calc R
C13 C 1.2141(5) 0.8895(5) 0.2155(2) 0.0911(13) Uani 1 d .
H13 H 1.3193 0.8870 0.2340 0.103(3) Uiso 1 calc R
C14 C 1.1774(4) 0.8055(4) 0.16055(18) 0.0709(10) Uani 1 d .
H14 H 1.2559 0.7462 0.1415 0.103(3) Uiso 1 calc R
C15 C 1.0206(3) 0.8120(3) 0.13462(15) 0.0548(7) Uani 1 d .
H15 H 0.9941 0.7551 0.0977 0.103(3) Uiso 1 calc R
C16 C 0.8991(3) 0.9007(3) 0.16141(13) 0.0490(6) Uani 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 0.0000 0.0000 '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 0.0060 '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
O1 P1 N2 118.89(14)
O1 P1 N1 115.25(13)
N2 P1 N1 93.48(15)
O1 P1 C16 111.17(12)
N2 P1 C16 107.69(16)
N1 P1 C16 108.85(13)
C1 N1 C7 119.8(3)
C1 N1 P1 127.5(2)
C7 N1 P1 112.5(2)
C6 C1 C2 117.9(3)
C6 C1 N1 121.5(3)
C2 C1 N1 120.6(3)
C3 C2 C1 120.8(3)
C4 C3 C2 121.1(4)
C3 C4 C5 118.6(4)
C4 C5 C6 122.1(4)
C5 C6 C1 119.5(4)
N1 C7 C8 107.0(3)
N2 C8 C7 109.2(3)
C8 N2 C9 120.3(3)
C8 N2 P1 115.6(2)
C9 N2 P1 123.6(3)
N2 C9 C10 111.4(3)
N3 C10 C9 112.8(4)
C11 N3 C10 125.1(3)
N3 C11 C16 124.0(3)
N3 C11 C12 119.2(4)
C16 C11 C12 116.9(3)
C13 C12 C11 122.3(4)
C12 C13 C14 121.2(4)
C15 C14 C13 117.8(4)
C14 C15 C16 122.9(3)
C15 C16 C11 118.9(3)
C15 C16 P1 117.4(2)
C11 C16 P1 123.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 P1 1.477(2)
P1 N2 1.631(3)
P1 N1 1.667(3)
P1 C16 1.806(3)
N1 C1 1.408(4)
N1 C7 1.473(4)
C1 C6 1.385(5)
C1 C2 1.387(4)
C2 C3 1.372(5)
C3 C4 1.351(6)
C4 C5 1.361(6)
C5 C6 1.375(5)
C7 C8 1.497(5)
C8 N2 1.416(5)
N2 C9 1.445(5)
C9 C10 1.505(7)
C10 N3 1.455(6)
N3 C11 1.377(5)
C11 C16 1.404(4)
C11 C12 1.416(6)
C12 C13 1.360(6)
C13 C14 1.375(6)
C14 C15 1.377(4)
C15 C16 1.401(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 HN3 O1 0.79(4) 2.23(4) 2.983(4) 160(5) 2_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 P1 N1 C1 -47.3(3)
N2 P1 N1 C1 -171.6(3)
C16 P1 N1 C1 78.4(3)
O1 P1 N1 C7 139.0(2)
N2 P1 N1 C7 14.7(2)
C16 P1 N1 C7 -95.3(2)
C7 N1 C1 C6 -163.8(3)
P1 N1 C1 C6 22.9(4)
C7 N1 C1 C2 14.9(4)
P1 N1 C1 C2 -158.4(2)
C6 C1 C2 C3 -0.9(5)
N1 C1 C2 C3 -179.7(3)
C1 C2 C3 C4 0.7(7)
C2 C3 C4 C5 -0.7(8)
C3 C4 C5 C6 1.0(8)
C4 C5 C6 C1 -1.2(8)
C2 C1 C6 C5 1.2(6)
N1 C1 C6 C5 180.0(4)
C1 N1 C7 C8 170.4(3)
P1 N1 C7 C8 -15.4(3)
N1 C7 C8 N2 8.4(4)
C7 C8 N2 C9 173.6(4)
C7 C8 N2 P1 1.9(4)
O1 P1 N2 C8 -131.1(3)
N1 P1 N2 C8 -9.7(3)
C16 P1 N2 C8 101.4(3)
O1 P1 N2 C9 57.5(4)
N1 P1 N2 C9 178.9(3)
C16 P1 N2 C9 -70.0(4)
C8 N2 C9 C10 -148.4(4)
P1 N2 C9 C10 22.7(5)
N2 C9 C10 N3 63.2(5)
C9 C10 N3 C11 -86.2(5)
C10 N3 C11 C16 24.0(6)
C10 N3 C11 C12 -157.5(4)
N3 C11 C12 C13 -179.1(4)
C16 C11 C12 C13 -0.5(5)
C11 C12 C13 C14 0.0(6)
C12 C13 C14 C15 0.0(6)
C13 C14 C15 C16 0.5(5)
C14 C15 C16 C11 -1.0(4)
C14 C15 C16 P1 176.5(2)
N3 C11 C16 C15 179.5(3)
C12 C11 C16 C15 0.9(4)
N3 C11 C16 P1 2.2(5)
C12 C11 C16 P1 -176.3(2)
O1 P1 C16 C15 85.1(2)
N2 P1 C16 C15 -143.0(2)
N1 P1 C16 C15 -42.9(2)
O1 P1 C16 C11 -97.6(3)
N2 P1 C16 C11 34.3(3)
N1 P1 C16 C11 134.5(2)
