#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:44:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178404 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/25/4022502.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_4022502
loop_
_publ_author_name
'María Ruiz'
'M. Carmen Fernández'
'Aniana Díaz'
'José M. Quintela'
'Vicente Ojea'
_publ_section_title
;
 Diastereoselective Synthesis of 2-Amino-4-phosphonobutanoic
 Acids by Conjugate Addition of Lithiated Schöllkopf's
 Bislactim Ethers to Vinylphosphonates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7634
_journal_page_last               7645
_journal_paper_doi               10.1021/jo034707q
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C8 H20 N O6 P'
_chemical_formula_weight         257.22
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.0033(14)
_cell_length_b                   11.559(3)
_cell_length_c                   26.542(5)
_cell_measurement_temperature    298(2)
_cell_volume                     2455.4(9)
_computing_cell_refinement       'Siemens SMART'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SAINT'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10557
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         1.53
_diffrn_standards_decay_%        0.19
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.804694
_exptl_absorpt_correction_type   Sadabs
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0338P)²+0.8147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0887
_reflns_number_gt                3706
_reflns_number_total             4365
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034707qsi20030529_013815.cif
_cod_data_source_block           398dcl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4022502
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
P1 P 0.29944(9) 0.90451(6) 0.84629(3) 0.02216(17) Uani 1 1 d .
P2 P 0.08597(10) 1.29993(6) 0.83310(3) 0.02397(18) Uani 1 1 d .
O1 O -0.2348(3) 1.04827(17) 0.79805(9) 0.0407(6) Uani 1 1 d .
O2 O -0.1691(3) 1.0892(2) 0.87792(8) 0.0395(6) Uani 1 1 d .
H2A H -0.1687 1.1561 0.8677 0.18(3) Uiso 1 1 calc R
O3 O 0.3988(2) 0.92200(17) 0.79905(7) 0.0295(5) Uani 1 1 d .
O4 O 0.2819(3) 1.01787(17) 0.87807(8) 0.0321(5) Uani 1 1 d .
H4A H 0.2346 1.0675 0.8612 0.063(14) Uiso 1 1 calc R
O5 O 0.3807(3) 0.81888(18) 0.88329(8) 0.0337(5) Uani 1 1 d .
O6 O 0.3841(3) 1.61614(19) 0.85419(9) 0.0417(6) Uani 1 1 d .
H6A H 0.4137 1.6823 0.8610 0.27(5) Uiso 1 1 calc R
O7 O 0.6563(2) 1.59180(17) 0.83763(8) 0.0330(5) Uani 1 1 d .
O8 O 0.0992(3) 1.37099(18) 0.78216(7) 0.0315(5) Uani 1 1 d .
H8A H 0.0683 1.4377 0.7870 0.050(12) Uiso 1 1 calc R
O9 O 0.1598(2) 1.18291(17) 0.82050(8) 0.0331(5) Uani 1 1 d .
O10 O -0.0913(2) 1.29817(16) 0.85185(8) 0.0291(5) Uani 1 1 d .
N1 N -0.2813(3) 0.8242(2) 0.81574(9) 0.0257(6) Uani 1 1 d .
H1A H -0.2846 0.7499 0.8245 0.042(10) Uiso 1 1 calc R
H1B H -0.2174 0.8325 0.7885 0.027(8) Uiso 1 1 calc R
H1C H -0.3843 0.8487 0.8090 0.044(10) Uiso 1 1 calc R
N2 N 0.6165(3) 1.3735(2) 0.80393(9) 0.0275(6) Uani 1 1 d .
H2B H 0.5900 1.3009 0.7963 0.069(13) Uiso 1 1 calc R
H2C H 0.7004 1.3738 0.8259 0.062(12) Uiso 1 1 calc R
H2D H 0.6473 1.4109 0.7761 0.039(10) Uiso 1 1 calc R
C1 C -0.2078(4) 1.0197(2) 0.84100(11) 0.0259(6) Uani 1 1 d .
C2 C -0.2104(4) 0.8935(2) 0.85801(10) 0.0233(6) Uani 1 1 d .
H2E H -0.2856 0.8868 0.8870 0.028 Uiso 1 1 calc R
C3 C -0.0348(4) 0.8539(2) 0.87443(11) 0.0238(7) Uani 1 1 d .
H3A H 0.0035 0.9087 0.9001 0.029 Uiso 1 1 calc R
C4 C 0.0915(4) 0.8600(2) 0.83047(11) 0.0251(6) Uani 1 1 d .
H4B H 0.0481 0.9131 0.8054 0.030 Uiso 1 1 calc R
H4C H 0.0976 0.7842 0.8149 0.030 Uiso 1 1 calc R
C5 C -0.0323(4) 0.7333(2) 0.89869(11) 0.0311(7) Uani 1 1 d .
H5A H 0.0822 0.7158 0.9080 0.037 Uiso 1 1 calc R
H5B H -0.0652 0.6775 0.8733 0.037 Uiso 1 1 calc R
C6 C -0.1428(5) 0.7144(3) 0.94524(13) 0.0409(9) Uani 1 1 d .
H6B H -0.2599 0.7188 0.9347 0.049 Uiso 1 1 calc R
C7 C -0.1096(6) 0.5923(3) 0.96577(17) 0.0678(13) Uani 1 1 d .
H7A H -0.1252 0.5367 0.9393 0.102 Uiso 1 1 calc R
H7B H -0.1860 0.5762 0.9928 0.102 Uiso 1 1 calc R
H7C H 0.0030 0.5877 0.9781 0.102 Uiso 1 1 calc R
C8 C -0.1137(6) 0.8048(4) 0.98587(14) 0.0622(12) Uani 1 1 d .
H8B H -0.1553 0.8783 0.9746 0.093 Uiso 1 1 calc R
H8C H 0.0038 0.8109 0.9927 0.093 Uiso 1 1 calc R
H8D H -0.1713 0.7824 1.0161 0.093 Uiso 1 1 calc R
C9 C 0.5092(4) 1.5578(2) 0.84029(11) 0.0272(7) Uani 1 1 d .
C10 C 0.4675(3) 1.4327(2) 0.82670(11) 0.0228(6) Uani 1 1 d .
H10A H 0.3784 1.4339 0.8014 0.027 Uiso 1 1 calc R
C11 C 0.4043(4) 1.3618(2) 0.87270(10) 0.0226(6) Uani 1 1 d .
H11A H 0.4279 1.2802 0.8657 0.027 Uiso 1 1 calc R
C12 C 0.2137(4) 1.3732(2) 0.87915(11) 0.0260(7) Uani 1 1 d .
H12A H 0.1855 1.4548 0.8785 0.031 Uiso 1 1 calc R
H12B H 0.1841 1.3441 0.9122 0.031 Uiso 1 1 calc R
C13 C 0.5002(4) 1.3939(3) 0.92104(11) 0.0280(7) Uani 1 1 d .
H13A H 0.6187 1.3940 0.9134 0.034 Uiso 1 1 calc R
H13B H 0.4697 1.4723 0.9304 0.034 Uiso 1 1 calc R
C14 C 0.4713(4) 1.3155(3) 0.96648(11) 0.0338(8) Uani 1 1 d .
H14A H 0.3508 1.3118 0.9729 0.041 Uiso 1 1 calc R
C15 C 0.5557(6) 1.3670(3) 1.01312(12) 0.0528(11) Uani 1 1 d .
H15A H 0.5165 1.4447 1.0182 0.079 Uiso 1 1 calc R
H15B H 0.6746 1.3679 1.0083 0.079 Uiso 1 1 calc R
H15C H 0.5289 1.3209 1.0421 0.079 Uiso 1 1 calc R
C16 C 0.5343(6) 1.1931(3) 0.95786(14) 0.0565(11) Uani 1 1 d .
H16A H 0.5158 1.1478 0.9876 0.085 Uiso 1 1 calc R
H16B H 0.6516 1.1951 0.9504 0.085 Uiso 1 1 calc R
H16C H 0.4752 1.1592 0.9301 0.085 Uiso 1 1 calc R
O1S O -0.0669(3) 1.5680(2) 0.77502(9) 0.0469(6) Uani 1 1 d .
H1SA H -0.1748 1.5774 0.7889 0.14(2) Uiso 1 1 d R
H1SB H -0.0794 1.6173 0.7478 0.087(15) Uiso 1 1 d R
O2S O 0.4649(4) 1.1743(2) 0.76892(8) 0.0478(6) Uani 1 1 d .
H2SA H 0.3509 1.1589 0.7871 0.16(3) Uiso 1 1 d R
H2SB H 0.5363 1.1181 0.7702 0.098(19) Uiso 1 1 d R
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
O3 P1 O5 113.37(12)
O3 P1 O4 112.70(12)
O5 P1 O4 103.46(12)
O3 P1 C4 109.59(13)
O5 P1 C4 110.96(13)
O4 P1 C4 106.45(13)
O10 P2 O9 115.43(12)
O10 P2 O8 110.60(12)
O9 P2 O8 104.39(12)
O10 P2 C12 108.47(13)
O9 P2 C12 110.39(14)
O8 P2 C12 107.25(13)
O1 C1 O2 125.8(3)
O1 C1 C2 122.5(3)
O2 C1 C2 111.7(3)
N1 C2 C1 107.2(2)
N1 C2 C3 113.6(2)
C1 C2 C3 110.8(2)
C5 C3 C2 113.6(2)
C5 C3 C4 110.4(2)
C2 C3 C4 111.7(2)
C3 C4 P1 116.3(2)
C3 C5 C6 117.3(3)
C8 C6 C7 110.7(3)
C8 C6 C5 112.7(3)
C7 C6 C5 108.5(3)
O7 C9 O6 126.8(3)
O7 C9 C10 119.6(3)
O6 C9 C10 113.7(3)
N2 C10 C9 110.7(2)
N2 C10 C11 109.5(2)
C9 C10 C11 112.7(2)
C12 C11 C13 112.3(2)
C12 C11 C10 111.3(2)
C13 C11 C10 111.4(2)
C11 C12 P2 116.4(2)
C14 C13 C11 116.1(2)
C16 C14 C13 112.6(3)
C16 C14 C15 109.8(3)
C13 C14 C15 110.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O3 1.498(2)
P1 O5 1.539(2)
P1 O4 1.565(2)
P1 C4 1.792(3)
P2 O10 1.504(2)
P2 O9 1.513(2)
P2 O8 1.586(2)
P2 C12 1.805(3)
O1 C1 1.206(4)
O2 C1 1.304(4)
O6 C9 1.262(4)
O7 C9 1.243(3)
N1 C2 1.491(3)
N2 C10 1.501(4)
C1 C2 1.528(4)
C2 C3 1.540(4)
C3 C5 1.536(4)
C3 C4 1.546(4)
C5 C6 1.535(4)
C6 C8 1.520(5)
C6 C7 1.536(5)
C9 C10 1.527(4)
C10 C11 1.555(4)
C11 C12 1.541(4)
C11 C13 1.541(4)
C13 C14 1.526(4)
C14 C16 1.519(5)
C14 C15 1.531(5)
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 C1 C2 N1 -10.4(4)
O2 C1 C2 N1 171.2(2)
O1 C1 C2 C3 114.1(3)
O2 C1 C2 C3 -64.2(3)
N1 C2 C3 C5 -67.0(3)
C1 C2 C3 C5 172.2(2)
N1 C2 C3 C4 58.7(3)
C1 C2 C3 C4 -62.1(3)
C5 C3 C4 P1 -89.7(3)
C2 C3 C4 P1 142.9(2)
O3 P1 C4 C3 -172.08(19)
O5 P1 C4 C3 62.0(2)
O4 P1 C4 C3 -49.9(2)
C2 C3 C5 C6 -57.4(4)
C4 C3 C5 C6 176.3(2)
C3 C5 C6 C8 -52.3(4)
C3 C5 C6 C7 -175.2(3)
O7 C9 C10 N2 -8.7(4)
O6 C9 C10 N2 172.3(2)
O7 C9 C10 C11 114.2(3)
O6 C9 C10 C11 -64.8(3)
N2 C10 C11 C12 -148.5(2)
C9 C10 C11 C12 87.9(3)
N2 C10 C11 C13 85.3(3)
C9 C10 C11 C13 -38.3(3)
C13 C11 C12 P2 -162.60(19)
C10 C11 C12 P2 71.7(3)
O10 P2 C12 C11 167.4(2)
O9 P2 C12 C11 40.0(3)
O8 P2 C12 C11 -73.1(2)
C12 C11 C13 C14 64.8(3)
C10 C11 C13 C14 -169.5(2)
C11 C13 C14 C16 64.8(4)
C11 C13 C14 C15 -172.5(3)
