# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name _publ_author_address 'Terence Kee' ;Department of Chemistry University of Leeds Leeds, LS2 9JT, UK ; 'David E Bryant' ;Department of Chemistry University of Leeds Leeds, LS2 9JT, UK ; 'Colin A. Kilner' '' 'Stuart A Macgregor' '' 'Katie E. R. Marriott' '' ; M.A.Pasek ; '' _publ_contact_author_name 'Terence Kee' _publ_contact_author_email T.P.KEE@LEEDS.AC.UK _publ_section_title ; On the prebiotic potential of reduced oxidation state phosphorus. The H-phosphinate-pyruvate system. ; _publ_contact_author_address ; Department of Chemistry University of Leeds Leeds LS2 9JT UK ; _publ_contact_author_phone '+44 (0)113 34 34992' # Attachment 'DEB154C_-_amide_-_compound_4.CIF' data_m:\docume~1\davidb\mydocu~1\x-ray\xray\deb154c\deb154c _database_code_depnum_ccdc_archive 'CCDC 740973' _audit_creation_method SHELXL-97 _chemical_name_systematic ; benzylamine (benzylamino-2-hydroxypropionato)-2-hydroxypropionato phosphonate ; _chemical_name_common ;benzylamine (benzylamino-2-hydroxypropionato)-2- hydroxypropionato phosphonate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H38 N3 O8 P' _chemical_formula_weight 563.57 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1313(13) _cell_length_b 10.6117(15) _cell_length_c 14.621(2) _cell_angle_alpha 99.470(7) _cell_angle_beta 100.513(7) _cell_angle_gamma 99.949(7) _cell_volume 1490.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 32061 _cell_measurement_theta_min 1.99 _cell_measurement_theta_max 26.87 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9640 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 15 degree phi range.The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; Bruker Nonius FR591 rotating anode generator ; _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Mach3 kappa-type 4-circle goniostat. ; _diffrn_measurement_method 'rotation images' _diffrn_detector_area_resol_mean ; 120 microns ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 32061 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.87 _reflns_number_total 6339 _reflns_number_gt 5087 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.4321P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6339 _refine_ls_number_parameters 504 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0929 _refine_ls_wR_factor_gt 0.0852 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 P1 P 0.29166(3) 0.65175(3) 0.43904(2) 0.01410(9) Uani 1 1 d . . . O1 O 0.16127(9) 0.54504(9) 0.41397(7) 0.0177(2) Uani 1 1 d . . . O2 O 0.34982(10) 0.91352(9) 0.42995(7) 0.0212(2) Uani 1 1 d . . . O3 O 0.37909(9) 0.67456(9) 0.53889(7) 0.0194(2) Uani 1 1 d . . . O4 O 0.13599(11) 0.26810(11) 0.37012(8) 0.0249(2) Uani 1 1 d . . . O5 O 0.41274(11) 0.47237(9) 0.36531(8) 0.0248(2) Uani 1 1 d . . . O6 O 0.05244(10) 0.77457(9) 0.50963(7) 0.0219(2) Uani 1 1 d . . . N7 N 0.12948(13) 0.47223(12) 0.58958(9) 0.0186(2) Uani 1 1 d . . . O8 O 0.55638(10) 0.81732(10) 0.40035(9) 0.0321(3) Uani 1 1 d . . . O9 O 0.64965(11) 0.64066(11) 0.39825(10) 0.0387(3) Uani 1 1 d . . . N10 N 0.21518(13) 0.96454(12) 0.56246(9) 0.0212(3) Uani 1 1 d . . . C12 C 0.23463(13) 0.80962(12) 0.42269(9) 0.0159(3) Uani 1 1 d . . . C13 C 0.40460(14) 0.60431(13) 0.35531(10) 0.0177(3) Uani 1 1 d . . . C14 C 0.54958(14) 0.69503(14) 0.38769(10) 0.0199(3) Uani 1 1 d . . . C15 C 0.16060(13) 0.84842(13) 0.50455(9) 0.0159(3) Uani 1 1 d . . . C16 C 0.12963(15) 0.79580(15) 0.32834(10) 0.0212(3) Uani 1 1 d . . . C17 C 0.21826(15) 1.04418(14) 0.73545(10) 0.0233(3) Uani 1 1 d . . . C18 C 0.19061(15) 0.56008(14) 0.76576(10) 0.0229(3) Uani 1 1 d . . . C20 C 0.34850(17) 0.60111(18) 0.24979(11) 0.0273(3) Uani 1 1 d . . . C21 C 0.16935(16) 0.59244(14) 0.66775(10) 0.0224(3) Uani 1 1 d . . . C23 C 0.14679(16) 1.03038(15) 0.63186(11) 0.0243(3) Uani 1 1 d . . . C25 C 0.27545(17) 1.16697(16) 0.79389(12) 0.0321(4) Uani 1 1 d . . . C26 C 0.3234(2) 0.56732(18) 0.81815(14) 0.0396(4) Uani 1 1 d . . . C27 C 0.3366(2) 1.17799(19) 0.89000(13) 0.0411(4) Uani 1 1 d . . . C28 C 0.0782(2) 0.52304(18) 0.80538(12) 0.0379(4) Uani 1 1 d . . . C30 C 0.3419(2) 1.06688(19) 0.92859(13) 0.0407(4) Uani 1 1 d . . . C31 C 0.2256(2) 0.93364(17) 0.77568(13) 0.0397(4) Uani 1 1 d . . . C32 C 0.2869(2) 0.94458(19) 0.87088(14) 0.0455(5) Uani 1 1 d . . . C36 C 0.2278(4) 0.4993(2) 0.94691(15) 0.0681(8) Uani 1 1 d . . . C37 C 0.0973(3) 0.4912(2) 0.89517(15) 0.0601(6) Uani 1 1 d . . . C38 C 0.3407(3) 0.5382(2) 0.90915(17) 0.0635(7) Uani 1 1 d . . . H41 H 0.160(2) 0.353(2) 0.3818(14) 0.046(6) Uiso 1 1 d . . . H42 H 0.1448(15) 1.1195(16) 0.6176(11) 0.021(4) Uiso 1 1 d . . . H44 H 0.1711(18) 0.7695(17) 0.2707(13) 0.036(5) Uiso 1 1 d . . . H49 H 0.082(2) 0.250(2) 0.4087(15) 0.051(6) Uiso 1 1 d . . . N11 N 0.37402(13) 0.16373(13) 0.37131(9) 0.0203(3) Uani 1 1 d . . . C19 C 0.29403(16) 0.04433(14) 0.20028(10) 0.0252(3) Uani 1 1 d . . . C22 C 0.15575(17) 0.05251(17) 0.17454(11) 0.0314(4) Uani 1 1 d . . . C24 C 0.33734(19) -0.06616(16) 0.15888(11) 0.0316(4) Uani 1 1 d . . . C29 C 0.39760(18) 0.15381(16) 0.27179(11) 0.0290(4) Uani 1 1 d . . . C33 C 0.1071(2) -0.15722(18) 0.06614(12) 0.0444(5) Uani 1 1 d . . . C34 C 0.2438(2) -0.16606(17) 0.09135(12) 0.0402(4) Uani 1 1 d . . . C35 C 0.0626(2) -0.04883(19) 0.10826(12) 0.0406(4) Uani 1 1 d . . . H12 H 0.0515(18) 0.9819(16) 0.6185(11) 0.027(4) Uiso 1 1 d . . . H13 H 0.043(2) 0.7305(18) 0.3246(13) 0.038(5) Uiso 1 1 d . . . H15 H 0.1043(18) 0.8803(19) 0.3264(12) 0.037(5) Uiso 1 1 d . . . H16 H 0.4344(19) -0.0728(17) 0.1781(12) 0.034(5) Uiso 1 1 d . . . H17 H 0.291(2) 1.0113(18) 0.5563(13) 0.035(5) Uiso 1 1 d . . . H18 H 0.1364(17) 0.4964(17) 0.5305(13) 0.032(5) Uiso 1 1 d . . . H19 H 0.295(2) 0.1997(18) 0.3771(13) 0.039(5) Uiso 1 1 d . . . H20 H 0.3626(18) 0.0814(19) 0.3883(12) 0.033(5) Uiso 1 1 d . . . H1 H 0.0946(18) 0.6413(17) 0.6582(12) 0.032(5) Uiso 1 1 d . . . H2 H 0.2527(19) 0.6431(17) 0.6589(12) 0.031(4) Uiso 1 1 d . . . H3 H 0.3436(19) 0.689(2) 0.2389(13) 0.041(5) Uiso 1 1 d . . . H4 H 0.4114(18) 0.5668(17) 0.2133(12) 0.034(5) Uiso 1 1 d . . . H5 H 0.1915(19) 0.4196(17) 0.5997(12) 0.031(5) Uiso 1 1 d . . . H6 H 0.041(2) 0.4283(19) 0.5857(13) 0.041(5) Uiso 1 1 d . . . H7 H 0.453(2) 0.2233(19) 0.4153(14) 0.044(5) Uiso 1 1 d . . . H8 H 0.252(2) 0.5422(18) 0.2270(13) 0.038(5) Uiso 1 1 d . . . H9 H 0.3909(19) 0.2406(19) 0.2552(13) 0.039(5) Uiso 1 1 d . . . H10 H 0.491(2) 0.474(2) 0.3966(15) 0.053(6) Uiso 1 1 d . . . H11 H 0.1229(19) 0.1310(19) 0.2019(13) 0.042(5) Uiso 1 1 d . . . H14 H 0.044(2) -0.230(2) 0.0178(16) 0.062(6) Uiso 1 1 d . . . H21 H 0.276(2) -0.242(2) 0.0611(14) 0.050(6) Uiso 1 1 d . . . H22 H -0.018(2) 0.519(2) 0.7684(15) 0.051(6) Uiso 1 1 d . . . H23 H 0.403(2) 0.592(2) 0.7882(15) 0.056(6) Uiso 1 1 d . . . H24 H 0.488(2) 0.1344(19) 0.2730(13) 0.044(5) Uiso 1 1 d . . . H25 H 0.383(2) 1.0731(19) 0.9919(15) 0.046(5) Uiso 1 1 d . . . H26 H 0.2743(19) 1.246(2) 0.7675(13) 0.044(5) Uiso 1 1 d . . . H27 H -0.032(2) -0.040(2) 0.0928(15) 0.057(6) Uiso 1 1 d . . . H28 H 0.183(2) 0.849(2) 0.7388(15) 0.059(6) Uiso 1 1 d . . . H29 H 0.377(2) 1.262(2) 0.9310(15) 0.055(6) Uiso 1 1 d . . . H30 H 0.290(2) 0.867(2) 0.8967(15) 0.058(6) Uiso 1 1 d . . . H31 H 0.242(3) 0.479(3) 1.010(2) 0.087(8) Uiso 1 1 d . . . H32 H 0.429(3) 0.548(3) 0.9412(19) 0.081(8) Uiso 1 1 d . . . H33 H 0.011(3) 0.463(3) 0.9198(18) 0.083(8) Uiso 1 1 d . . . H34 H 0.420(3) 0.879(2) 0.4151(16) 0.068(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.01237(17) 0.01348(17) 0.01703(18) 0.00391(13) 0.00417(13) 0.00247(13) O1 0.0145(5) 0.0163(5) 0.0221(5) 0.0040(4) 0.0043(4) 0.0022(4) O2 0.0179(5) 0.0152(5) 0.0335(6) 0.0063(4) 0.0127(4) 0.0028(4) O3 0.0169(5) 0.0214(5) 0.0194(5) 0.0060(4) 0.0028(4) 0.0019(4) O4 0.0255(6) 0.0189(6) 0.0320(6) 0.0026(5) 0.0131(5) 0.0040(4) O5 0.0220(6) 0.0152(5) 0.0377(6) 0.0043(4) 0.0068(5) 0.0062(4) O6 0.0177(5) 0.0198(5) 0.0283(6) 0.0024(4) 0.0108(4) 0.0006(4) N7 0.0153(6) 0.0198(6) 0.0210(6) 0.0053(5) 0.0035(5) 0.0038(5) O8 0.0188(5) 0.0178(5) 0.0603(8) 0.0028(5) 0.0168(5) 0.0015(4) O9 0.0176(5) 0.0333(6) 0.0692(9) 0.0173(6) 0.0091(5) 0.0103(5) N10 0.0179(6) 0.0193(6) 0.0258(7) -0.0006(5) 0.0100(5) 0.0013(5) C12 0.0145(6) 0.0144(6) 0.0201(7) 0.0045(5) 0.0066(5) 0.0024(5) C13 0.0168(7) 0.0145(6) 0.0228(7) 0.0032(5) 0.0066(5) 0.0045(5) C14 0.0181(7) 0.0215(7) 0.0225(7) 0.0049(6) 0.0092(6) 0.0048(6) C15 0.0142(6) 0.0165(7) 0.0187(7) 0.0054(5) 0.0041(5) 0.0050(5) C16 0.0231(8) 0.0243(8) 0.0194(7) 0.0067(6) 0.0059(6) 0.0106(6) C17 0.0235(7) 0.0218(7) 0.0267(8) 0.0018(6) 0.0126(6) 0.0058(6) C18 0.0275(8) 0.0175(7) 0.0215(7) -0.0001(6) 0.0039(6) 0.0041(6) C20 0.0248(8) 0.0383(9) 0.0205(8) 0.0028(7) 0.0066(6) 0.0125(7) C21 0.0225(8) 0.0194(7) 0.0250(8) 0.0031(6) 0.0065(6) 0.0038(6) C23 0.0231(8) 0.0225(8) 0.0279(8) -0.0008(6) 0.0111(6) 0.0061(6) C25 0.0368(9) 0.0225(8) 0.0338(9) 0.0024(7) 0.0050(7) 0.0041(7) C26 0.0373(10) 0.0341(9) 0.0423(10) 0.0052(8) -0.0057(8) 0.0113(8) C27 0.0471(11) 0.0346(10) 0.0333(10) -0.0052(8) -0.0002(8) 0.0072(8) C28 0.0436(11) 0.0415(10) 0.0271(9) 0.0025(7) 0.0146(8) 0.0015(8) C30 0.0460(11) 0.0538(12) 0.0268(9) 0.0079(8) 0.0092(8) 0.0208(9) C31 0.0608(12) 0.0222(9) 0.0372(10) 0.0034(7) 0.0153(9) 0.0086(8) C32 0.0694(14) 0.0375(10) 0.0397(11) 0.0170(9) 0.0204(10) 0.0206(10) C36 0.141(3) 0.0390(12) 0.0207(10) 0.0051(9) 0.0057(13) 0.0216(14) C37 0.0991(19) 0.0524(13) 0.0306(11) 0.0061(9) 0.0309(12) 0.0050(12) C38 0.0850(18) 0.0428(12) 0.0473(13) 0.0031(10) -0.0299(13) 0.0243(12) N11 0.0194(6) 0.0183(6) 0.0222(6) 0.0041(5) 0.0039(5) 0.0023(5) C19 0.0322(8) 0.0247(8) 0.0191(7) 0.0053(6) 0.0095(6) 0.0024(6) C22 0.0337(9) 0.0346(9) 0.0254(8) 0.0041(7) 0.0064(7) 0.0083(7) C24 0.0416(10) 0.0316(9) 0.0267(8) 0.0095(7) 0.0139(7) 0.0108(7) C29 0.0293(9) 0.0284(9) 0.0274(8) 0.0030(7) 0.0106(7) -0.0012(7) C33 0.0653(13) 0.0344(10) 0.0214(9) 0.0018(7) -0.0007(8) -0.0075(9) C34 0.0694(14) 0.0260(9) 0.0262(9) 0.0038(7) 0.0145(9) 0.0102(9) C35 0.0357(10) 0.0524(11) 0.0273(9) 0.0090(8) -0.0023(7) 0.0005(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 P1 O3 1.5206(10) . ? P1 O1 1.5269(10) . ? P1 C13 1.8891(14) . ? P1 C12 1.9009(14) . ? O2 C12 1.4354(16) . ? O5 C13 1.4463(17) . ? O6 C15 1.2539(16) . ? N7 C21 1.5069(18) . ? O8 C14 1.2682(17) . ? O9 C14 1.2485(18) . ? N10 C15 1.3384(18) . ? N10 C23 1.4794(18) . ? C12 C16 1.5493(19) . ? C12 C15 1.5611(18) . ? C13 C20 1.536(2) . ? C13 C14 1.5543(19) . ? C17 C25 1.398(2) . ? C17 C31 1.403(2) . ? C17 C23 1.526(2) . ? C18 C28 1.396(2) . ? C18 C26 1.404(2) . ? C18 C21 1.514(2) . ? C25 C27 1.406(2) . ? C26 C38 1.402(3) . ? C27 C30 1.393(3) . ? C28 C37 1.397(3) . ? C30 C32 1.387(3) . ? C31 C32 1.394(3) . ? C36 C37 1.379(4) . ? C36 C38 1.387(4) . ? N11 C29 1.507(2) . ? C19 C22 1.404(2) . ? C19 C24 1.405(2) . ? C19 C29 1.524(2) . ? C22 C35 1.400(2) . ? C24 C34 1.402(3) . ? C33 C34 1.390(3) . ? C33 C35 1.397(3) . ? 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 O3 P1 O1 116.97(5) . . ? O3 P1 C13 106.25(6) . . ? O1 P1 C13 107.36(6) . . ? O3 P1 C12 107.89(6) . . ? O1 P1 C12 106.34(6) . . ? C13 P1 C12 112.16(6) . . ? C15 N10 C23 124.42(12) . . ? O2 C12 C16 109.72(11) . . ? O2 C12 C15 108.18(10) . . ? C16 C12 C15 106.60(11) . . ? O2 C12 P1 111.41(9) . . ? C16 C12 P1 113.51(9) . . ? C15 C12 P1 107.15(9) . . ? O5 C13 C20 107.77(11) . . ? O5 C13 C14 110.20(11) . . ? C20 C13 C14 109.20(12) . . ? O5 C13 P1 103.16(9) . . ? C20 C13 P1 116.02(10) . . ? C14 C13 P1 110.25(9) . . ? O9 C14 O8 125.62(13) . . ? O9 C14 C13 116.84(12) . . ? O8 C14 C13 117.54(12) . . ? O6 C15 N10 124.26(12) . . ? O6 C15 C12 119.48(11) . . ? N10 C15 C12 116.16(11) . . ? C25 C17 C31 117.87(15) . . ? C25 C17 C23 121.29(14) . . ? C31 C17 C23 120.83(14) . . ? C28 C18 C26 119.09(16) . . ? C28 C18 C21 120.33(14) . . ? C26 C18 C21 120.58(15) . . ? N7 C21 C18 112.59(12) . . ? N10 C23 C17 114.22(12) . . ? C17 C25 C27 120.52(16) . . ? C38 C26 C18 119.6(2) . . ? C30 C27 C25 120.62(17) . . ? C18 C28 C37 120.5(2) . . ? C32 C30 C27 119.28(17) . . ? C32 C31 C17 121.60(16) . . ? C30 C32 C31 120.11(17) . . ? C37 C36 C38 119.8(2) . . ? C36 C37 C28 120.4(2) . . ? C36 C38 C26 120.7(2) . . ? C22 C19 C24 119.36(15) . . ? C22 C19 C29 120.96(14) . . ? C24 C19 C29 119.68(15) . . ? C35 C22 C19 119.98(16) . . ? C34 C24 C19 120.22(17) . . ? N11 C29 C19 112.87(12) . . ? C34 C33 C35 120.07(17) . . ? C33 C34 C24 120.09(17) . . ? C33 C35 C22 120.26(18) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.87 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.437 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.043 # Attachment 'DEB262NA_-_DIP_-_compound_2.CIF' data_m:\x-ray\xray\temp\deb262na _database_code_depnum_ccdc_archive 'CCDC 740974' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H13 Na2 O10 P, H2 O' _chemical_formula_sum 'C6 H15 Na2 O11 P' _chemical_formula_weight 340.13 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2983(9) _cell_length_b 9.0885(12) _cell_length_c 11.6210(14) _cell_angle_alpha 91.799(5) _cell_angle_beta 92.303(6) _cell_angle_gamma 95.488(6) _cell_volume 661.21(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3880 _cell_measurement_theta_min 5.851 _cell_measurement_theta_max 61.050 _exptl_crystal_description rhombohedral _exptl_crystal_colour colourless _exptl_crystal_size_max 0.295 _exptl_crystal_size_mid 0.212 _exptl_crystal_size_min 0.148 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.326 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; Bruker Nonius FR591 rotating anode generator ; _diffrn_radiation_monochromator ; graphite model mounted in "parallel" mode ; _diffrn_measurement_device_type ; Mach3 kappa-type 4-circle goniostat. ; _diffrn_radiation_detector 'ApexII camera' _diffrn_measurement_method 'rotation images' _diffrn_detector_area_resol_mean ; 120 microns ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 60539 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0110 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 30.26 _reflns_number_total 3880 _reflns_number_gt 3688 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; APEX 2 software, Bruker Nonius 2004 ; _computing_cell_refinement ; APEX 2 software, Bruker Nonius 2004 ; _computing_data_reduction ; SAINT - Bruker Integration program embedded in APEX 2 software, Bruker Nonius 2004 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ; enCIFer: A program for viewing, editing and visualising CIFs. F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Applied Cryst., 37, 331-334, 2004 ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All hydrogens were found in the Fourier displacement map. PLAT780 Alert "Coordinates do not Form a Properly Connected Set" - this is a common error when dealing with coordination polymers and results from Platon. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0295P)^2^+0.1850P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3880 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0210 _refine_ls_R_factor_gt 0.0198 _refine_ls_wR_factor_ref 0.0573 _refine_ls_wR_factor_gt 0.0566 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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 P1 P 0.31784(3) 0.71663(2) 0.231317(15) 0.00807(5) Uani 1 1 d . . . Na2 Na -0.17611(5) 0.63502(4) 0.14250(3) 0.01387(7) Uani 1 1 d . . . Na1 Na -0.21007(6) 0.84633(4) 0.39762(3) 0.02135(8) Uani 1 1 d . . . O2 O -0.00928(9) 0.88343(6) 0.21402(5) 0.01308(11) Uani 1 1 d . . . O3 O 0.55868(9) 0.73241(6) 0.23895(5) 0.01323(11) Uani 1 1 d . . . O4 O 0.44994(9) 0.77683(7) 0.48639(5) 0.01440(11) Uani 1 1 d . . . O6 O 0.20439(9) 0.63190(6) 0.12734(5) 0.01128(10) Uani 1 1 d . . . O7 O 0.48917(10) 1.05888(7) 0.33719(6) 0.01977(13) Uani 1 1 d . . . O8 O -0.01698(9) 0.58821(7) 0.34072(5) 0.01473(11) Uani 1 1 d . . . O10 O 0.15985(9) 1.02076(7) 0.40967(5) 0.01569(12) Uani 1 1 d . . . C12 C 0.21217(11) 0.61796(8) 0.35976(6) 0.00998(13) Uani 1 1 d . . . O13 O 0.13159(11) 0.69115(8) 0.55370(6) 0.02289(14) Uani 1 1 d . . . C14 C 0.28831(12) 1.00188(8) 0.33370(7) 0.01135(13) Uani 1 1 d . . . C15 C 0.22114(11) 0.90606(8) 0.22448(6) 0.00995(13) Uani 1 1 d . . . C16 C 0.26510(12) 0.70338(8) 0.47630(6) 0.01155(13) Uani 1 1 d . . . C17 C 0.31673(14) 0.97539(9) 0.11526(7) 0.01532(14) Uani 1 1 d . . . C18 C 0.32274(13) 0.47227(9) 0.36521(7) 0.01429(14) Uani 1 1 d . . . O11 O 0.08552(10) 0.81636(7) 0.78433(6) 0.01735(12) Uani 1 1 d . . . H5 H 0.184(2) 0.7747(16) 0.8165(13) 0.034(4) Uiso 1 1 d . . . H10 H 0.092(3) 0.7916(18) 0.7151(15) 0.042(4) Uiso 1 1 d . . . O5 O 0.33289(10) 0.62537(7) 0.90323(5) 0.01697(12) Uani 1 1 d . . . H9 H 0.277(2) 1.0745(18) 0.1051(13) 0.039(4) Uiso 1 1 d . . . H1 H 0.467(3) 0.6439(17) 0.9088(13) 0.039(4) Uiso 1 1 d . . . H20 H 0.297(3) 0.6374(18) 0.9712(15) 0.045(4) Uiso 1 1 d . . . O9 O 0.21148(10) 0.34404(7) 0.06522(5) 0.01605(12) Uani 1 1 d . . . H7 H 0.132(2) 0.2900(16) 0.1064(13) 0.031(3) Uiso 1 1 d . . . H11 H 0.201(2) 0.4323(18) 0.0905(13) 0.035(4) Uiso 1 1 d . . . H8 H 0.292(2) 0.4136(16) 0.2950(12) 0.031(3) Uiso 1 1 d . . . H2 H 0.469(2) 0.9804(16) 0.1201(12) 0.034(4) Uiso 1 1 d . . . H15 H 0.261(2) 0.9121(16) 0.0484(12) 0.031(3) Uiso 1 1 d . . . H16 H 0.471(2) 0.4955(15) 0.3749(12) 0.029(3) Uiso 1 1 d . . . H3 H -0.049(2) 0.9645(17) 0.2042(13) 0.034(4) Uiso 1 1 d . . . H4 H 0.515(3) 1.124(2) 0.4039(17) 0.063(5) Uiso 1 1 d . . . H13 H 0.274(2) 0.4173(15) 0.4311(12) 0.029(3) Uiso 1 1 d . . . H6 H -0.051(2) 0.5119(16) 0.3766(12) 0.030(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.00646(8) 0.00925(9) 0.00852(9) -0.00127(6) 0.00112(6) 0.00100(6) Na2 0.00956(14) 0.01766(16) 0.01432(15) -0.00368(12) 0.00088(11) 0.00213(11) Na1 0.01550(16) 0.0300(2) 0.01714(17) -0.00616(14) 0.00469(13) -0.00420(14) O2 0.0083(2) 0.0118(2) 0.0192(3) -0.0004(2) 0.00019(19) 0.00206(19) O3 0.0073(2) 0.0173(3) 0.0151(3) -0.0025(2) 0.00197(19) 0.00138(19) O4 0.0121(2) 0.0173(3) 0.0129(3) -0.0030(2) -0.00050(19) -0.0012(2) O6 0.0116(2) 0.0117(2) 0.0103(2) -0.00255(19) 0.00024(18) 0.00117(18) O7 0.0153(3) 0.0228(3) 0.0189(3) -0.0105(2) 0.0064(2) -0.0087(2) O8 0.0084(2) 0.0186(3) 0.0165(3) 0.0048(2) -0.00078(19) -0.0029(2) O10 0.0139(3) 0.0198(3) 0.0136(3) -0.0029(2) 0.0041(2) 0.0027(2) C12 0.0081(3) 0.0111(3) 0.0106(3) 0.0000(2) -0.0001(2) 0.0005(2) O13 0.0251(3) 0.0249(3) 0.0170(3) -0.0061(2) 0.0110(2) -0.0080(2) C14 0.0120(3) 0.0092(3) 0.0127(3) -0.0007(2) 0.0023(2) 0.0001(2) C15 0.0082(3) 0.0101(3) 0.0114(3) -0.0008(2) 0.0020(2) 0.0000(2) C16 0.0134(3) 0.0103(3) 0.0111(3) 0.0005(2) 0.0009(2) 0.0012(2) C17 0.0202(4) 0.0128(3) 0.0133(3) 0.0022(3) 0.0056(3) 0.0011(3) C18 0.0167(3) 0.0117(3) 0.0148(3) 0.0004(3) -0.0009(3) 0.0040(3) O11 0.0188(3) 0.0173(3) 0.0169(3) 0.0005(2) 0.0029(2) 0.0053(2) O5 0.0157(3) 0.0215(3) 0.0138(3) -0.0003(2) 0.0020(2) 0.0021(2) O9 0.0188(3) 0.0124(3) 0.0170(3) -0.0014(2) 0.0026(2) 0.0015(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 P1 O3 1.5087(6) . ? P1 O6 1.5266(6) . ? P1 C12 1.8775(8) . ? P1 C15 1.8832(8) . ? P1 Na2 3.2476(6) . ? Na2 O3 2.2805(7) 1_455 ? Na2 O6 2.4128(7) . ? Na2 O9 2.4304(8) 2_565 ? Na2 O2 2.5000(7) . ? Na2 O5 2.5080(8) 2_566 ? Na2 O8 2.5395(7) . ? Na2 Na1 3.5064(6) . ? Na1 O3 2.4431(7) 1_455 ? Na1 O4 2.4512(7) 1_455 ? Na1 O10 2.5050(7) 2_576 ? Na1 O2 2.5388(7) . ? Na1 O10 2.6860(8) . ? Na1 O8 2.8164(8) . ? Na1 O7 2.9140(9) 1_455 ? O2 C15 1.4458(9) . ? O2 H3 0.811(16) . ? O3 Na2 2.2805(7) 1_655 ? O3 Na1 2.4431(7) 1_655 ? O4 C16 1.2846(9) . ? O4 Na1 2.4512(7) 1_655 ? O7 C14 1.3189(9) . ? O7 Na1 2.9140(9) 1_655 ? O7 H4 0.96(2) . ? O8 C12 1.4495(9) . ? O8 H6 0.835(15) . ? O10 C14 1.2401(9) . ? O10 Na1 2.5050(7) 2_576 ? C12 C16 1.5479(10) . ? C12 C18 1.5558(11) . ? O13 C16 1.2560(10) . ? C14 C15 1.5380(10) . ? C15 C17 1.5523(11) . ? C17 H9 0.967(16) . ? C17 H2 0.957(15) . ? C17 H15 0.983(14) . ? C18 H8 0.963(15) . ? C18 H16 0.942(14) . ? C18 H13 0.972(14) . ? O11 H5 0.839(16) . ? O11 H10 0.833(17) . ? O5 Na2 2.5080(8) 2_566 ? O5 H1 0.843(17) . ? O5 H20 0.838(18) . ? O9 Na2 2.4304(8) 2_565 ? O9 H7 0.841(15) . ? O9 H11 0.855(16) . ? 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 O3 P1 O6 118.42(3) . . ? O3 P1 C12 109.80(3) . . ? O6 P1 C12 104.86(3) . . ? O3 P1 C15 108.95(3) . . ? O6 P1 C15 103.89(3) . . ? C12 P1 C15 110.67(3) . . ? O3 P1 Na2 163.03(2) . . ? O6 P1 Na2 44.64(2) . . ? C12 P1 Na2 80.12(2) . . ? C15 P1 Na2 78.80(2) . . ? O3 Na2 O6 145.72(2) 1_455 . ? O3 Na2 O9 113.47(3) 1_455 2_565 ? O6 Na2 O9 89.30(2) . 2_565 ? O3 Na2 O2 76.28(2) 1_455 . ? O6 Na2 O2 73.30(2) . . ? O9 Na2 O2 104.35(2) 2_565 . ? O3 Na2 O5 102.40(3) 1_455 2_566 ? O6 Na2 O5 105.68(2) . 2_566 ? O9 Na2 O5 82.99(2) 2_565 2_566 ? O2 Na2 O5 172.50(2) . 2_566 ? O3 Na2 O8 85.66(2) 1_455 . ? O6 Na2 O8 72.00(2) . . ? O9 Na2 O8 160.56(2) 2_565 . ? O2 Na2 O8 75.86(2) . . ? O5 Na2 O8 96.70(2) 2_566 . ? O3 Na2 P1 119.56(2) 1_455 . ? O6 Na2 P1 26.394(14) . . ? O9 Na2 P1 110.18(2) 2_565 . ? O2 Na2 P1 53.626(15) . . ? O5 Na2 P1 122.742(19) 2_566 . ? O8 Na2 P1 53.842(15) . . ? O3 Na2 Na1 43.883(17) 1_455 . ? O6 Na2 Na1 102.311(18) . . ? O9 Na2 Na1 140.39(2) 2_565 . ? O2 Na2 Na1 46.360(17) . . ? O5 Na2 Na1 127.97(2) 2_566 . ? O8 Na2 Na1 52.620(18) . . ? P1 Na2 Na1 75.924(12) . . ? O3 Na1 O4 75.80(2) 1_455 1_455 ? O3 Na1 O10 150.83(3) 1_455 2_576 ? O4 Na1 O10 77.57(2) 1_455 2_576 ? O3 Na1 O2 72.80(2) 1_455 . ? O4 Na1 O2 147.80(2) 1_455 . ? O10 Na1 O2 130.81(3) 2_576 . ? O3 Na1 O10 134.07(2) 1_455 . ? O4 Na1 O10 146.87(2) 1_455 . ? O10 Na1 O10 69.83(2) 2_576 . ? O2 Na1 O10 61.89(2) . . ? O3 Na1 O8 76.86(2) 1_455 . ? O4 Na1 O8 109.07(2) 1_455 . ? O10 Na1 O8 123.66(2) 2_576 . ? O2 Na1 O8 70.48(2) . . ? O10 Na1 O8 94.10(2) . . ? O3 Na1 O7 73.33(2) 1_455 1_455 ? O4 Na1 O7 70.92(2) 1_455 1_455 ? O10 Na1 O7 86.92(2) 2_576 1_455 ? O2 Na1 O7 93.16(2) . 1_455 ? O10 Na1 O7 100.97(2) . 1_455 ? O8 Na1 O7 149.19(2) . 1_455 ? O3 Na1 Na2 40.320(16) 1_455 . ? O4 Na1 Na2 110.03(2) 1_455 . ? O10 Na1 Na2 168.02(2) 2_576 . ? O2 Na1 Na2 45.449(16) . . ? O10 Na1 Na2 103.092(18) . . ? O8 Na1 Na2 45.767(15) . . ? O7 Na1 Na2 104.179(19) 1_455 . ? C15 O2 Na2 117.85(4) . . ? C15 O2 Na1 117.67(4) . . ? Na2 O2 Na1 88.19(2) . . ? C15 O2 H3 105.8(11) . . ? Na2 O2 H3 129.4(11) . . ? Na1 O2 H3 93.6(11) . . ? P1 O3 Na2 136.19(4) . 1_655 ? P1 O3 Na1 127.08(3) . 1_655 ? Na2 O3 Na1 95.80(2) 1_655 1_655 ? C16 O4 Na1 147.11(5) . 1_655 ? P1 O6 Na2 108.97(3) . . ? C14 O7 Na1 113.24(5) . 1_655 ? C14 O7 H4 108.9(11) . . ? Na1 O7 H4 98.2(11) 1_655 . ? C12 O8 Na2 117.77(4) . . ? C12 O8 Na1 108.81(4) . . ? Na2 O8 Na1 81.61(2) . . ? C12 O8 H6 105.5(10) . . ? Na2 O8 H6 123.1(10) . . ? Na1 O8 H6 118.3(10) . . ? C14 O10 Na1 130.87(5) . 2_576 ? C14 O10 Na1 117.30(5) . . ? Na1 O10 Na1 110.17(2) 2_576 . ? O8 C12 C16 110.25(6) . . ? O8 C12 C18 111.45(6) . . ? C16 C12 C18 106.99(6) . . ? O8 C12 P1 107.51(5) . . ? C16 C12 P1 114.38(5) . . ? C18 C12 P1 106.26(5) . . ? O10 C14 O7 124.98(7) . . ? O10 C14 C15 121.04(7) . . ? O7 C14 C15 113.98(6) . . ? O2 C15 C14 109.18(6) . . ? O2 C15 C17 111.61(6) . . ? C14 C15 C17 111.70(6) . . ? O2 C15 P1 106.32(5) . . ? C14 C15 P1 112.06(5) . . ? C17 C15 P1 105.83(5) . . ? O13 C16 O4 125.55(7) . . ? O13 C16 C12 118.71(7) . . ? O4 C16 C12 115.67(6) . . ? C15 C17 H9 111.9(9) . . ? C15 C17 H2 110.6(9) . . ? H9 C17 H2 107.8(12) . . ? C15 C17 H15 107.6(8) . . ? H9 C17 H15 109.2(12) . . ? H2 C17 H15 109.7(11) . . ? C12 C18 H8 110.4(8) . . ? C12 C18 H16 109.3(8) . . ? H8 C18 H16 108.9(12) . . ? C12 C18 H13 109.3(8) . . ? H8 C18 H13 110.5(12) . . ? H16 C18 H13 108.4(11) . . ? H5 O11 H10 103.4(14) . . ? Na2 O5 H1 119.2(10) 2_566 . ? Na2 O5 H20 101.2(12) 2_566 . ? H1 O5 H20 103.0(15) . . ? Na2 O9 H7 126.8(10) 2_565 . ? Na2 O9 H11 103.0(10) 2_565 . ? H7 O9 H11 104.9(13) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 P1 Na2 O3 -169.55(10) . . . 1_455 ? O6 P1 Na2 O3 -173.79(4) . . . 1_455 ? C12 P1 Na2 O3 63.06(3) . . . 1_455 ? C15 P1 Na2 O3 -50.50(3) . . . 1_455 ? O3 P1 Na2 O6 4.24(9) . . . . ? C12 P1 Na2 O6 -123.15(4) . . . . ? C15 P1 Na2 O6 123.29(4) . . . . ? O3 P1 Na2 O9 -35.42(9) . . . 2_565 ? O6 P1 Na2 O9 -39.65(4) . . . 2_565 ? C12 P1 Na2 O9 -162.80(3) . . . 2_565 ? C15 P1 Na2 O9 83.63(3) . . . 2_565 ? O3 P1 Na2 O2 -128.70(9) . . . . ? O6 P1 Na2 O2 -132.94(4) . . . . ? C12 P1 Na2 O2 103.91(3) . . . . ? C15 P1 Na2 O2 -9.65(3) . . . . ? O3 P1 Na2 O5 59.28(9) . . . 2_566 ? O6 P1 Na2 O5 55.04(4) . . . 2_566 ? C12 P1 Na2 O5 -68.11(3) . . . 2_566 ? C15 P1 Na2 O5 178.33(3) . . . 2_566 ? O3 P1 Na2 O8 131.94(9) . . . . ? O6 P1 Na2 O8 127.71(4) . . . . ? C12 P1 Na2 O8 4.56(3) . . . . ? C15 P1 Na2 O8 -109.01(3) . . . . ? O3 P1 Na2 Na1 -174.36(9) . . . . ? O6 P1 Na2 Na1 -178.59(3) . . . . ? C12 P1 Na2 Na1 58.26(3) . . . . ? C15 P1 Na2 Na1 -55.31(2) . . . . ? O6 Na2 Na1 O3 173.33(3) . . . 1_455 ? O9 Na2 Na1 O3 69.20(4) 2_565 . . 1_455 ? O2 Na2 Na1 O3 121.25(3) . . . 1_455 ? O5 Na2 Na1 O3 -65.26(3) 2_566 . . 1_455 ? O8 Na2 Na1 O3 -131.06(3) . . . 1_455 ? P1 Na2 Na1 O3 173.97(3) . . . 1_455 ? O3 Na2 Na1 O4 33.57(3) 1_455 . . 1_455 ? O6 Na2 Na1 O4 -153.11(2) . . . 1_455 ? O9 Na2 Na1 O4 102.76(4) 2_565 . . 1_455 ? O2 Na2 Na1 O4 154.81(3) . . . 1_455 ? O5 Na2 Na1 O4 -31.70(3) 2_566 . . 1_455 ? O8 Na2 Na1 O4 -97.49(3) . . . 1_455 ? P1 Na2 Na1 O4 -152.47(2) . . . 1_455 ? O3 Na2 Na1 O10 161.53(11) 1_455 . . 2_576 ? O6 Na2 Na1 O10 -25.15(11) . . . 2_576 ? O9 Na2 Na1 O10 -129.28(10) 2_565 . . 2_576 ? O2 Na2 Na1 O10 -77.23(10) . . . 2_576 ? O5 Na2 Na1 O10 96.26(10) 2_566 . . 2_576 ? O8 Na2 Na1 O10 30.47(10) . . . 2_576 ? P1 Na2 Na1 O10 -24.51(10) . . . 2_576 ? O3 Na2 Na1 O2 -121.25(3) 1_455 . . . ? O6 Na2 Na1 O2 52.08(3) . . . . ? O9 Na2 Na1 O2 -52.05(4) 2_565 . . . ? O5 Na2 Na1 O2 173.49(3) 2_566 . . . ? O8 Na2 Na1 O2 107.69(3) . . . . ? P1 Na2 Na1 O2 52.72(2) . . . . ? O3 Na2 Na1 O10 -146.06(3) 1_455 . . . ? O6 Na2 Na1 O10 27.27(2) . . . . ? O9 Na2 Na1 O10 -76.86(4) 2_565 . . . ? O2 Na2 Na1 O10 -24.81(2) . . . . ? O5 Na2 Na1 O10 148.68(3) 2_566 . . . ? O8 Na2 Na1 O10 82.88(3) . . . . ? P1 Na2 Na1 O10 27.910(18) . . . . ? O3 Na2 Na1 O8 131.06(3) 1_455 . . . ? O6 Na2 Na1 O8 -55.62(2) . . . . ? O9 Na2 Na1 O8 -159.74(4) 2_565 . . . ? O2 Na2 Na1 O8 -107.69(3) . . . . ? O5 Na2 Na1 O8 65.80(3) 2_566 . . . ? P1 Na2 Na1 O8 -54.975(19) . . . . ? O3 Na2 Na1 O7 -40.97(3) 1_455 . . 1_455 ? O6 Na2 Na1 O7 132.36(2) . . . 1_455 ? O9 Na2 Na1 O7 28.23(4) 2_565 . . 1_455 ? O2 Na2 Na1 O7 80.28(3) . . . 1_455 ? O5 Na2 Na1 O7 -106.23(3) 2_566 . . 1_455 ? O8 Na2 Na1 O7 -172.03(2) . . . 1_455 ? P1 Na2 Na1 O7 132.998(18) . . . 1_455 ? O3 Na2 O2 C15 158.17(5) 1_455 . . . ? O6 Na2 O2 C15 -5.84(5) . . . . ? O9 Na2 O2 C15 -90.68(5) 2_565 . . . ? O5 Na2 O2 C15 77.40(19) 2_566 . . . ? O8 Na2 O2 C15 69.26(5) . . . . ? P1 Na2 O2 C15 14.02(4) . . . . ? Na1 Na2 O2 C15 120.58(5) . . . . ? O3 Na2 O2 Na1 37.59(2) 1_455 . . . ? O6 Na2 O2 Na1 -126.42(2) . . . . ? O9 Na2 O2 Na1 148.74(2) 2_565 . . . ? O5 Na2 O2 Na1 -43.18(19) 2_566 . . . ? O8 Na2 O2 Na1 -51.32(2) . . . . ? P1 Na2 O2 Na1 -106.56(2) . . . . ? O3 Na1 O2 C15 -156.13(5) 1_455 . . . ? O4 Na1 O2 C15 -169.36(5) 1_455 . . . ? O10 Na1 O2 C15 43.75(6) 2_576 . . . ? O10 Na1 O2 C15 31.66(5) . . . . ? O8 Na1 O2 C15 -74.34(5) . . . . ? O7 Na1 O2 C15 132.41(5) 1_455 . . . ? Na2 Na1 O2 C15 -120.74(5) . . . . ? O3 Na1 O2 Na2 -35.39(2) 1_455 . . . ? O4 Na1 O2 Na2 -48.62(5) 1_455 . . . ? O10 Na1 O2 Na2 164.49(3) 2_576 . . . ? O10 Na1 O2 Na2 152.40(3) . . . . ? O8 Na1 O2 Na2 46.41(2) . . . . ? O7 Na1 O2 Na2 -106.85(2) 1_455 . . . ? O6 P1 O3 Na2 -9.79(6) . . . 1_655 ? C12 P1 O3 Na2 110.53(5) . . . 1_655 ? C15 P1 O3 Na2 -128.12(5) . . . 1_655 ? Na2 P1 O3 Na2 -13.17(12) . . . 1_655 ? O6 P1 O3 Na1 -175.87(3) . . . 1_655 ? C12 P1 O3 Na1 -55.56(5) . . . 1_655 ? C15 P1 O3 Na1 65.80(5) . . . 1_655 ? Na2 P1 O3 Na1 -179.26(5) . . . 1_655 ? O3 P1 O6 Na2 -178.60(3) . . . . ? C12 P1 O6 Na2 58.58(4) . . . . ? C15 P1 O6 Na2 -57.64(4) . . . . ? O3 Na2 O6 P1 9.62(6) 1_455 . . . ? O9 Na2 O6 P1 143.20(3) 2_565 . . . ? O2 Na2 O6 P1 37.98(3) . . . . ? O5 Na2 O6 P1 -134.28(3) 2_566 . . . ? O8 Na2 O6 P1 -42.19(3) . . . . ? Na1 Na2 O6 P1 1.40(3) . . . . ? O3 Na2 O8 C12 -138.52(5) 1_455 . . . ? O6 Na2 O8 C12 15.13(5) . . . . ? O9 Na2 O8 C12 31.54(10) 2_565 . . . ? O2 Na2 O8 C12 -61.59(5) . . . . ? O5 Na2 O8 C12 119.48(5) 2_566 . . . ? P1 Na2 O8 C12 -6.58(4) . . . . ? Na1 Na2 O8 C12 -106.90(5) . . . . ? O3 Na2 O8 Na1 -31.61(2) 1_455 . . . ? O6 Na2 O8 Na1 122.03(2) . . . . ? O9 Na2 O8 Na1 138.44(7) 2_565 . . . ? O2 Na2 O8 Na1 45.316(19) . . . . ? O5 Na2 O8 Na1 -133.62(2) 2_566 . . . ? P1 Na2 O8 Na1 100.33(2) . . . . ? O3 Na1 O8 C12 146.63(5) 1_455 . . . ? O4 Na1 O8 C12 -143.69(4) 1_455 . . . ? O10 Na1 O8 C12 -56.17(5) 2_576 . . . ? O2 Na1 O8 C12 70.48(4) . . . . ? O10 Na1 O8 C12 12.26(5) . . . . ? O7 Na1 O8 C12 131.79(5) 1_455 . . . ? Na2 Na1 O8 C12 116.57(5) . . . . ? O3 Na1 O8 Na2 30.067(19) 1_455 . . . ? O4 Na1 O8 Na2 99.75(2) 1_455 . . . ? O10 Na1 O8 Na2 -172.74(2) 2_576 . . . ? O2 Na1 O8 Na2 -46.08(2) . . . . ? O10 Na1 O8 Na2 -104.31(2) . . . . ? O7 Na1 O8 Na2 15.22(5) 1_455 . . . ? O3 Na1 O10 C14 -33.16(7) 1_455 . . . ? O4 Na1 O10 C14 177.68(6) 1_455 . . . ? O10 Na1 O10 C14 166.94(7) 2_576 . . . ? O2 Na1 O10 C14 -22.78(5) . . . . ? O8 Na1 O10 C14 42.50(6) . . . . ? O7 Na1 O10 C14 -110.50(6) 1_455 . . . ? Na2 Na1 O10 C14 -2.97(6) . . . . ? O3 Na1 O10 Na1 159.90(4) 1_455 . . 2_576 ? O4 Na1 O10 Na1 10.74(5) 1_455 . . 2_576 ? O10 Na1 O10 Na1 0.0 2_576 . . 2_576 ? O2 Na1 O10 Na1 170.27(3) . . . 2_576 ? O8 Na1 O10 Na1 -124.45(3) . . . 2_576 ? O7 Na1 O10 Na1 82.56(3) 1_455 . . 2_576 ? Na2 Na1 O10 Na1 -169.91(2) . . . 2_576 ? Na2 O8 C12 C16 134.94(5) . . . . ? Na1 O8 C12 C16 44.65(6) . . . . ? Na2 O8 C12 C18 -106.40(6) . . . . ? Na1 O8 C12 C18 163.30(5) . . . . ? Na2 O8 C12 P1 9.66(6) . . . . ? Na1 O8 C12 P1 -80.64(4) . . . . ? O3 P1 C12 O8 -172.49(5) . . . . ? O6 P1 C12 O8 -44.26(5) . . . . ? C15 P1 C12 O8 67.19(6) . . . . ? Na2 P1 C12 O8 -6.77(4) . . . . ? O3 P1 C12 C16 64.73(6) . . . . ? O6 P1 C12 C16 -167.03(5) . . . . ? C15 P1 C12 C16 -55.59(6) . . . . ? Na2 P1 C12 C16 -129.54(5) . . . . ? O3 P1 C12 C18 -53.06(6) . . . . ? O6 P1 C12 C18 75.18(5) . . . . ? C15 P1 C12 C18 -173.38(5) . . . . ? Na2 P1 C12 C18 112.67(5) . . . . ? Na1 O10 C14 O7 -4.01(12) 2_576 . . . ? Na1 O10 C14 O7 -167.73(6) . . . . ? Na1 O10 C14 C15 175.89(5) 2_576 . . . ? Na1 O10 C14 C15 12.18(9) . . . . ? Na1 O7 C14 O10 102.79(8) 1_655 . . . ? Na1 O7 C14 C15 -77.12(7) 1_655 . . . ? Na2 O2 C15 C14 -141.59(5) . . . . ? Na1 O2 C15 C14 -37.90(7) . . . . ? Na2 O2 C15 C17 94.43(6) . . . . ? Na1 O2 C15 C17 -161.88(5) . . . . ? Na2 O2 C15 P1 -20.52(6) . . . . ? Na1 O2 C15 P1 83.17(5) . . . . ? O10 C14 C15 O2 15.66(9) . . . . ? O7 C14 C15 O2 -164.43(6) . . . . ? O10 C14 C15 C17 139.59(7) . . . . ? O7 C14 C15 C17 -40.50(9) . . . . ? O10 C14 C15 P1 -101.85(7) . . . . ? O7 C14 C15 P1 78.06(7) . . . . ? O3 P1 C15 O2 178.42(4) . . . . ? O6 P1 C15 O2 51.31(5) . . . . ? C12 P1 C15 O2 -60.76(6) . . . . ? Na2 P1 C15 O2 14.08(4) . . . . ? O3 P1 C15 C14 -62.37(6) . . . . ? O6 P1 C15 C14 170.52(5) . . . . ? C12 P1 C15 C14 58.45(6) . . . . ? Na2 P1 C15 C14 133.28(5) . . . . ? O3 P1 C15 C17 59.61(6) . . . . ? O6 P1 C15 C17 -67.51(6) . . . . ? C12 P1 C15 C17 -179.57(5) . . . . ? Na2 P1 C15 C17 -104.74(5) . . . . ? Na1 O4 C16 O13 175.29(7) 1_655 . . . ? Na1 O4 C16 C12 -1.60(13) 1_655 . . . ? O8 C12 C16 O13 24.63(9) . . . . ? C18 C12 C16 O13 -96.72(8) . . . . ? P1 C12 C16 O13 145.91(6) . . . . ? O8 C12 C16 O4 -158.26(6) . . . . ? C18 C12 C16 O4 80.40(8) . . . . ? P1 C12 C16 O4 -36.97(8) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 30.26 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.450 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.045 # Attachment 'KM42A_final_-_compound_3.CIF' data_km42a _database_code_depnum_ccdc_archive 'CCDC 740975' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H16 N, C6 H8 O7 P' _chemical_formula_sum 'C12 H24 N O7 P' _chemical_formula_weight 325.29 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8028(8) _cell_length_b 10.2088(13) _cell_length_c 12.2089(16) _cell_angle_alpha 81.041(6) _cell_angle_beta 86.642(6) _cell_angle_gamma 87.114(6) _cell_volume 835.38(18) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9905 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 27.56 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8970 _exptl_absorpt_correction_T_max 0.9866 _exptl_absorpt_process_details ; See Sheldrick, G. M. (2002). SADABS. University of Gottingen, Germany. ; _exptl_special_details ; The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; Bruker Nonius FR591 rotating anode generator ; _diffrn_radiation_monochromator ; graphite model mounted in "parallel" mode ; _diffrn_measurement_device_type ; Mach3 kappa-type 4-circle goniostat. ; _diffrn_radiation_detector 'ApexII camera' _diffrn_measurement_method 'rotation images' _diffrn_detector_area_resol_mean ; 120 microns ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 37192 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.90 _reflns_number_total 3940 _reflns_number_gt 3221 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; APEX 2 software, Bruker Nonius 2004 ; _computing_cell_refinement ; APEX 2 software, Bruker Nonius 2004 ; _computing_data_reduction ; SAINT - Bruker Integration program embedded in APEX 2 software, Bruker Nonius 2004 ; _computing_structure_solution ; SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112) XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.) ; _computing_structure_refinement ; SHELXL-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112) XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.) ; _computing_molecular_graphics 'ORTEP-III Version 1.08 (Farrugia, 2005)' _computing_publication_material ; enCIFer: A program for viewing, editing and visualising CIFs. F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Applied Cryst., 37, 331-334, 2004 ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+0.2979P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3940 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 P1 P 0.07549(5) 0.23177(4) 0.73168(3) 0.01924(12) Uani 1 1 d . . . O1 O 0.20217(17) 0.11602(11) 0.78563(10) 0.0278(3) Uani 1 1 d . . . N1 N 0.4256(2) 0.89549(13) 0.75487(12) 0.0283(3) Uani 1 1 d . . . H1 H 0.3615 0.9780 0.7558 0.034 Uiso 1 1 calc R . . O2 O -0.10101(15) 0.20363(11) 0.66976(10) 0.0273(3) Uani 1 1 d . . . C2 C 0.0050(2) 0.35400(15) 0.82850(13) 0.0224(3) Uani 1 1 d . . . C3 C 0.0328(2) 0.49119(15) 0.75459(13) 0.0222(3) Uani 1 1 d . . . O4 O 0.15277(16) 0.48788(10) 0.65966(10) 0.0241(3) Uani 1 1 d . . . C5 C 0.2278(2) 0.35631(15) 0.63520(13) 0.0205(3) Uani 1 1 d . . . O21 O -0.19276(17) 0.34276(13) 0.87635(10) 0.0314(3) Uani 1 1 d . . . H21 H -0.2731 0.3601 0.8259 0.038 Uiso 1 1 calc R . . C21 C 0.1442(3) 0.33989(18) 0.92524(15) 0.0312(4) Uani 1 1 d . . . H21A H 0.1134 0.4116 0.9692 0.047 Uiso 1 1 calc R . . H21B H 0.2811 0.3451 0.8955 0.047 Uiso 1 1 calc R . . H21C H 0.1267 0.2540 0.9725 0.047 Uiso 1 1 calc R . . O31 O -0.04229(19) 0.59667(12) 0.77393(11) 0.0331(3) Uani 1 1 d . . . C51 C 0.1991(3) 0.35197(18) 0.51075(14) 0.0293(4) Uani 1 1 d . . . H51A H 0.0591 0.3672 0.4959 0.044 Uiso 1 1 calc R . . H51B H 0.2446 0.2648 0.4928 0.044 Uiso 1 1 calc R . . H51C H 0.2754 0.4211 0.4649 0.044 Uiso 1 1 calc R . . C52 C 0.4463(2) 0.34018(15) 0.66287(13) 0.0220(3) Uani 1 1 d . . . O53 O 0.54174(16) 0.24124(12) 0.62010(11) 0.0317(3) Uani 1 1 d . . . H53 H 0.6582 0.2337 0.6404 0.038 Uiso 1 1 calc R . . O54 O 0.52143(18) 0.41168(13) 0.71989(12) 0.0361(3) Uani 1 1 d . . . C61 C 0.6428(3) 0.91468(18) 0.76688(18) 0.0385(5) Uani 1 1 d . . . H61A H 0.6949 0.9732 0.7003 0.046 Uiso 1 1 calc R . . H61B H 0.7154 0.8277 0.7707 0.046 Uiso 1 1 calc R . . C62 C 0.6804(3) 0.9757(2) 0.8707(2) 0.0465(5) Uani 1 1 d . . . H62A H 0.6036 1.0597 0.8693 0.070 Uiso 1 1 calc R . . H62B H 0.8210 0.9920 0.8717 0.070 Uiso 1 1 calc R . . H62C H 0.6407 0.9143 0.9373 0.070 Uiso 1 1 calc R . . C63 C 0.3922(3) 0.8559(2) 0.64190(16) 0.0407(5) Uani 1 1 d . . . H63A H 0.4758 0.9094 0.5844 0.049 Uiso 1 1 calc R . . H63B H 0.4343 0.7614 0.6432 0.049 Uiso 1 1 calc R . . C64 C 0.1778(3) 0.8753(2) 0.61017(18) 0.0451(5) Uani 1 1 d . . . H64A H 0.0971 0.8121 0.6598 0.068 Uiso 1 1 calc R . . H64B H 0.1684 0.8602 0.5334 0.068 Uiso 1 1 calc R . . H64C H 0.1303 0.9661 0.6170 0.068 Uiso 1 1 calc R . . C65 C 0.3323(2) 0.80097(16) 0.85205(14) 0.0269(3) Uani 1 1 d . . . H65A H 0.3354 0.8413 0.9206 0.032 Uiso 1 1 calc R . . H65B H 0.1924 0.7915 0.8377 0.032 Uiso 1 1 calc R . . C66 C 0.4343(3) 0.66256(17) 0.87180(16) 0.0330(4) Uani 1 1 d . . . H66A H 0.4279 0.6203 0.8054 0.050 Uiso 1 1 calc R . . H66B H 0.3678 0.6084 0.9352 0.050 Uiso 1 1 calc R . . H66C H 0.5725 0.6706 0.8874 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0151(2) 0.0182(2) 0.0248(2) -0.00537(15) -0.00146(14) 0.00295(13) O1 0.0267(6) 0.0215(6) 0.0340(7) -0.0033(5) -0.0019(5) 0.0074(4) N1 0.0277(7) 0.0216(7) 0.0327(8) -0.0009(6) 0.0062(6) 0.0071(5) O2 0.0153(5) 0.0320(6) 0.0374(7) -0.0138(5) -0.0024(5) 0.0000(4) C2 0.0217(8) 0.0216(7) 0.0240(8) -0.0051(6) -0.0009(6) 0.0040(6) C3 0.0185(7) 0.0233(7) 0.0260(8) -0.0070(6) -0.0062(6) 0.0041(6) O4 0.0218(6) 0.0193(5) 0.0302(6) -0.0027(4) -0.0008(4) 0.0047(4) C5 0.0179(7) 0.0200(7) 0.0241(8) -0.0062(6) -0.0015(6) 0.0040(5) O21 0.0236(6) 0.0387(7) 0.0312(7) -0.0070(5) 0.0049(5) 0.0043(5) C21 0.0361(10) 0.0326(9) 0.0261(9) -0.0084(7) -0.0094(7) 0.0091(7) O31 0.0368(7) 0.0237(6) 0.0395(7) -0.0104(5) -0.0026(5) 0.0094(5) C51 0.0253(8) 0.0383(9) 0.0241(9) -0.0054(7) -0.0025(6) 0.0034(7) C52 0.0180(7) 0.0219(7) 0.0262(8) -0.0049(6) 0.0002(6) 0.0006(6) O53 0.0158(6) 0.0380(7) 0.0459(8) -0.0222(6) -0.0048(5) 0.0061(5) O54 0.0225(6) 0.0356(7) 0.0562(9) -0.0242(6) -0.0104(5) 0.0048(5) C61 0.0273(9) 0.0256(9) 0.0569(13) 0.0057(8) 0.0093(8) 0.0038(7) C62 0.0364(11) 0.0393(11) 0.0599(14) 0.0082(10) -0.0101(9) -0.0043(8) C63 0.0514(12) 0.0398(10) 0.0278(10) -0.0046(8) 0.0102(8) 0.0119(9) C64 0.0537(13) 0.0454(12) 0.0404(12) -0.0197(9) -0.0020(9) -0.0035(9) C65 0.0274(8) 0.0247(8) 0.0279(8) -0.0049(6) 0.0052(6) 0.0005(6) C66 0.0391(10) 0.0220(8) 0.0370(10) -0.0028(7) 0.0007(8) 0.0006(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 P1 O1 1.5148(11) . ? P1 O2 1.5180(12) . ? P1 C2 1.8754(16) . ? P1 C5 1.8978(16) . ? N1 C61 1.519(2) . ? N1 C63 1.529(2) . ? N1 C65 1.536(2) . ? N1 H1 0.9300 . ? C2 O21 1.4376(19) . ? C2 C21 1.542(2) . ? C2 C3 1.557(2) . ? C3 O31 1.2189(19) . ? C3 O4 1.3817(19) . ? O4 C5 1.4806(17) . ? C5 C52 1.538(2) . ? C5 C51 1.551(2) . ? O21 H21 0.8400 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C52 O54 1.231(2) . ? C52 O53 1.3315(19) . ? O53 H53 0.8400 . ? C61 C62 1.536(3) . ? C61 H61A 0.9900 . ? C61 H61B 0.9900 . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? C63 C64 1.526(3) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? C65 C66 1.533(2) . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C66 H66A 0.9800 . ? C66 H66B 0.9800 . ? C66 H66C 0.9800 . ? 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 P1 O2 118.84(7) . . ? O1 P1 C2 112.24(7) . . ? O2 P1 C2 110.70(7) . . ? O1 P1 C5 111.72(7) . . ? O2 P1 C5 107.60(7) . . ? C2 P1 C5 92.55(7) . . ? C61 N1 C63 110.73(15) . . ? C61 N1 C65 113.21(14) . . ? C63 N1 C65 112.81(14) . . ? C61 N1 H1 106.5 . . ? C63 N1 H1 106.5 . . ? C65 N1 H1 106.5 . . ? O21 C2 C21 107.28(13) . . ? O21 C2 C3 111.42(12) . . ? C21 C2 C3 109.01(13) . . ? O21 C2 P1 113.93(11) . . ? C21 C2 P1 111.51(11) . . ? C3 C2 P1 103.65(10) . . ? O31 C3 O4 119.58(14) . . ? O31 C3 C2 125.51(15) . . ? O4 C3 C2 114.91(12) . . ? C3 O4 C5 117.58(12) . . ? O4 C5 C52 107.78(12) . . ? O4 C5 C51 107.84(12) . . ? C52 C5 C51 112.11(13) . . ? O4 C5 P1 105.06(9) . . ? C52 C5 P1 110.75(10) . . ? C51 C5 P1 112.88(11) . . ? C2 O21 H21 109.5 . . ? C2 C21 H21A 109.5 . . ? C2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C5 C51 H51A 109.5 . . ? C5 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C5 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? O54 C52 O53 124.53(15) . . ? O54 C52 C5 122.44(14) . . ? O53 C52 C5 113.03(13) . . ? C52 O53 H53 109.5 . . ? N1 C61 C62 112.69(16) . . ? N1 C61 H61A 109.1 . . ? C62 C61 H61A 109.1 . . ? N1 C61 H61B 109.1 . . ? C62 C61 H61B 109.1 . . ? H61A C61 H61B 107.8 . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C64 C63 N1 113.15(15) . . ? C64 C63 H63A 108.9 . . ? N1 C63 H63A 108.9 . . ? C64 C63 H63B 108.9 . . ? N1 C63 H63B 108.9 . . ? H63A C63 H63B 107.8 . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C66 C65 N1 114.13(13) . . ? C66 C65 H65A 108.7 . . ? N1 C65 H65A 108.7 . . ? C66 C65 H65B 108.7 . . ? N1 C65 H65B 108.7 . . ? H65A C65 H65B 107.6 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 P1 C2 O21 -101.62(12) . . . . ? O2 P1 C2 O21 33.74(13) . . . . ? C5 P1 C2 O21 143.64(11) . . . . ? O1 P1 C2 C21 19.99(14) . . . . ? O2 P1 C2 C21 155.35(12) . . . . ? C5 P1 C2 C21 -94.75(12) . . . . ? O1 P1 C2 C3 137.12(10) . . . . ? O2 P1 C2 C3 -87.52(11) . . . . ? C5 P1 C2 C3 22.39(10) . . . . ? O21 C2 C3 O31 37.0(2) . . . . ? C21 C2 C3 O31 -81.21(19) . . . . ? P1 C2 C3 O31 159.93(14) . . . . ? O21 C2 C3 O4 -142.54(13) . . . . ? C21 C2 C3 O4 99.26(15) . . . . ? P1 C2 C3 O4 -19.61(15) . . . . ? O31 C3 O4 C5 -175.29(14) . . . . ? C2 C3 O4 C5 4.27(18) . . . . ? C3 O4 C5 C52 -104.87(14) . . . . ? C3 O4 C5 C51 133.91(14) . . . . ? C3 O4 C5 P1 13.28(15) . . . . ? O1 P1 C5 O4 -136.04(9) . . . . ? O2 P1 C5 O4 91.82(10) . . . . ? C2 P1 C5 O4 -20.85(10) . . . . ? O1 P1 C5 C52 -19.92(12) . . . . ? O2 P1 C5 C52 -152.07(10) . . . . ? C2 P1 C5 C52 95.26(11) . . . . ? O1 P1 C5 C51 106.72(11) . . . . ? O2 P1 C5 C51 -25.43(12) . . . . ? C2 P1 C5 C51 -138.10(11) . . . . ? O4 C5 C52 O54 15.8(2) . . . . ? C51 C5 C52 O54 134.35(17) . . . . ? P1 C5 C52 O54 -98.59(16) . . . . ? O4 C5 C52 O53 -164.90(13) . . . . ? C51 C5 C52 O53 -46.38(18) . . . . ? P1 C5 C52 O53 80.68(15) . . . . ? C63 N1 C61 C62 170.91(15) . . . . ? C65 N1 C61 C62 -61.26(18) . . . . ? C61 N1 C63 C64 -162.70(16) . . . . ? C65 N1 C63 C64 69.25(19) . . . . ? C61 N1 C65 C66 -57.03(19) . . . . ? C63 N1 C65 C66 69.71(19) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.531 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.060 # Attachment 'DEB246_-_MIP_-_compound_1.CIF' data_m:\x-ray\xray\deb246~1\deb246 _database_code_depnum_ccdc_archive 'CCDC 760816' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-hydroxyphosphinoylpropionic acid, sodium salt ; _chemical_name_common '2-hydroxyphosphinoylpropionic acid, sodium salt' _chemical_melting_point ? _chemical_formula_moiety 'C3 H8 Na O6 P' _chemical_formula_sum 'C3 H8 Na O6 P' _chemical_formula_weight 194.05 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n 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' _cell_length_a 6.0112(12) _cell_length_b 9.5047(19) _cell_length_c 12.665(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.49(3) _cell_angle_gamma 90.00 _cell_volume 722.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1653 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description 'flat plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.785 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.421 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8170 _exptl_absorpt_correction_T_max 0.9711 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 15 degree phi range. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; 'Nonius KappaCCD area detector diffractometer' ; _diffrn_measurement_method ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10809 _diffrn_reflns_av_R_equivalents 0.1109 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 27.45 _reflns_number_total 1653 _reflns_number_gt 1282 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP3 for Windows (Farrugia, 1997) XSeed (Barbour, 2001) ; _computing_publication_material 'WC (Thornton-Pett, 2000)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. PLAT780 Alert "Coordinates do not Form a Properly Connected Set" - this is a common error when dealing with coordination polymers and results from Platon. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.2261P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1653 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.0998 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 P1 P 0.07599(9) 0.22281(6) 0.14935(4) 0.01631(18) Uani 1 1 d . . . C4 C -0.2925(3) 0.2493(2) 0.01095(17) 0.0162(5) Uani 1 1 d . . . C6 C -0.2261(3) 0.1863(2) 0.11823(16) 0.0167(4) Uani 1 1 d . . . O1 O 0.1262(3) 0.18444(16) 0.26327(12) 0.0204(4) Uani 1 1 d . . . O3 O 0.1276(2) 0.36907(16) 0.11342(12) 0.0210(4) Uani 1 1 d . . . O4 O -0.3482(3) 0.26260(17) 0.19307(13) 0.0190(4) Uani 1 1 d . . . C5 C -0.2765(4) 0.0285(2) 0.12038(18) 0.0206(5) Uani 1 1 d . . . O2 O -0.2160(3) 0.17876(17) -0.06933(13) 0.0213(4) Uani 1 1 d . . . O5 O -0.4033(3) 0.35557(16) -0.00001(12) 0.0214(4) Uani 1 1 d . . . Na6 Na -0.53022(14) 0.48508(9) 0.14055(6) 0.0186(2) Uani 1 1 d . . . O6 O -0.3413(3) 0.09499(18) 0.37385(13) 0.0214(4) Uani 1 1 d . . . H1 H 0.175(3) 0.130(2) 0.0917(16) 0.011(5) Uiso 1 1 d . . . H2 H -0.177(5) -0.021(3) 0.071(2) 0.034(7) Uiso 1 1 d . . . H3 H -0.249(4) -0.009(3) 0.189(2) 0.024(6) Uiso 1 1 d . . . H5 H -0.342(4) 0.218(3) 0.246(2) 0.029(8) Uiso 1 1 d . . . H4 H -0.431(5) 0.010(3) 0.099(2) 0.039(8) Uiso 1 1 d . . . H7 H -0.262(5) 0.223(3) -0.128(2) 0.044(9) Uiso 1 1 d . . . H6 H -0.432(5) 0.028(4) 0.369(2) 0.050(10) Uiso 1 1 d . . . H8 H -0.320(6) 0.126(4) 0.439(3) 0.069(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0170(3) 0.0181(3) 0.0138(3) 0.0009(2) 0.0002(2) 0.0004(2) C4 0.0153(11) 0.0188(11) 0.0142(11) -0.0001(8) 0.0000(8) -0.0023(8) C6 0.0184(11) 0.0178(11) 0.0139(10) -0.0004(8) 0.0017(8) 0.0023(8) O1 0.0222(8) 0.0240(8) 0.0148(8) 0.0022(6) -0.0023(6) -0.0030(6) O3 0.0174(8) 0.0207(8) 0.0250(9) 0.0042(6) 0.0003(6) -0.0020(6) O4 0.0233(9) 0.0202(8) 0.0139(8) 0.0012(6) 0.0034(7) 0.0035(6) C5 0.0253(12) 0.0185(11) 0.0176(11) 0.0013(9) -0.0010(9) -0.0014(9) O2 0.0262(9) 0.0225(8) 0.0151(8) 0.0007(6) 0.0013(6) 0.0063(7) O5 0.0268(8) 0.0213(8) 0.0159(8) 0.0013(6) 0.0008(6) 0.0062(7) Na6 0.0198(5) 0.0191(5) 0.0169(4) -0.0009(3) 0.0000(3) 0.0000(3) O6 0.0238(9) 0.0215(9) 0.0189(9) 0.0010(6) 0.0016(7) -0.0015(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 P1 O3 1.5009(16) . ? P1 O1 1.5009(16) . ? P1 C6 1.867(2) . ? P1 Na6 3.4441(11) 1_655 ? P1 H1 1.31(2) . ? C4 O5 1.213(3) . ? C4 O2 1.324(3) . ? C4 C6 1.516(3) . ? C6 O4 1.431(3) . ? C6 C5 1.531(3) . ? O1 Na6 2.3437(17) 2_445 ? O3 Na6 2.3408(17) 1_655 ? O4 Na6 2.4541(18) . ? O4 H5 0.79(3) . ? C5 H2 1.00(3) . ? C5 H3 0.95(3) . ? C5 H4 0.97(3) . ? O2 H7 0.89(3) . ? O5 Na6 2.3304(18) . ? O5 Na6 2.3526(17) 3_465 ? Na6 O3 2.3408(17) 1_455 ? Na6 O1 2.3437(17) 2_455 ? Na6 O5 2.3526(17) 3_465 ? Na6 O6 2.4821(18) 2_455 ? Na6 P1 3.4441(11) 1_455 ? O6 Na6 2.4821(18) 2_445 ? O6 H6 0.84(4) . ? O6 H8 0.88(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 O3 P1 O1 118.90(9) . . ? O3 P1 C6 108.93(9) . . ? O1 P1 C6 107.10(9) . . ? O3 P1 Na6 33.36(6) . 1_655 ? O1 P1 Na6 96.23(7) . 1_655 ? C6 P1 Na6 142.12(7) . 1_655 ? O3 P1 H1 110.3(9) . . ? O1 P1 H1 107.4(9) . . ? C6 P1 H1 103.0(9) . . ? Na6 P1 H1 97.7(9) 1_655 . ? O5 C4 O2 123.2(2) . . ? O5 C4 C6 122.98(19) . . ? O2 C4 C6 113.79(18) . . ? O4 C6 C4 105.99(17) . . ? O4 C6 C5 112.01(18) . . ? C4 C6 C5 111.19(18) . . ? O4 C6 P1 107.31(14) . . ? C4 C6 P1 108.39(14) . . ? C5 C6 P1 111.69(15) . . ? P1 O1 Na6 130.89(9) . 2_445 ? P1 O3 Na6 126.00(9) . 1_655 ? C6 O4 Na6 119.70(13) . . ? C6 O4 H5 107(2) . . ? Na6 O4 H5 133(2) . . ? C6 C5 H2 108.8(16) . . ? C6 C5 H3 111.4(15) . . ? H2 C5 H3 108(2) . . ? C6 C5 H4 111.2(16) . . ? H2 C5 H4 110(2) . . ? H3 C5 H4 107(2) . . ? C4 O2 H7 108(2) . . ? C4 O5 Na6 123.73(14) . . ? C4 O5 Na6 133.57(14) . 3_465 ? O5 Na6 O3 87.97(7) . 1_455 ? O5 Na6 O1 157.89(7) . 2_455 ? O3 Na6 O1 102.42(6) 1_455 2_455 ? O5 Na6 O5 79.08(6) . 3_465 ? O3 Na6 O5 94.87(6) 1_455 3_465 ? O1 Na6 O5 80.61(6) 2_455 3_465 ? O5 Na6 O4 65.84(6) . . ? O3 Na6 O4 90.41(6) 1_455 . ? O1 Na6 O4 132.50(7) 2_455 . ? O5 Na6 O4 144.31(7) 3_465 . ? O5 Na6 O6 80.13(6) . 2_455 ? O3 Na6 O6 166.90(7) 1_455 2_455 ? O1 Na6 O6 87.08(6) 2_455 2_455 ? O5 Na6 O6 77.62(6) 3_465 2_455 ? O4 Na6 O6 89.67(6) . 2_455 ? O5 Na6 P1 84.26(5) . 1_455 ? O3 Na6 P1 20.65(4) 1_455 1_455 ? O1 Na6 P1 112.14(5) 2_455 1_455 ? O5 Na6 P1 113.89(5) 3_465 1_455 ? O4 Na6 P1 70.34(5) . 1_455 ? O6 Na6 P1 158.47(5) 2_455 1_455 ? Na6 O6 H6 105(2) 2_445 . ? Na6 O6 H8 97(2) 2_445 . ? H6 O6 H8 112(3) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 C4 C6 O4 9.0(3) . . . . ? O2 C4 C6 O4 -171.79(17) . . . . ? O5 C4 C6 C5 131.0(2) . . . . ? O2 C4 C6 C5 -49.8(2) . . . . ? O5 C4 C6 P1 -105.9(2) . . . . ? O2 C4 C6 P1 73.3(2) . . . . ? O3 P1 C6 O4 -74.50(15) . . . . ? O1 P1 C6 O4 55.30(16) . . . . ? Na6 P1 C6 O4 -70.17(18) 1_655 . . . ? O3 P1 C6 C4 39.56(17) . . . . ? O1 P1 C6 C4 169.35(14) . . . . ? Na6 P1 C6 C4 43.9(2) 1_655 . . . ? O3 P1 C6 C5 162.39(15) . . . . ? O1 P1 C6 C5 -67.82(17) . . . . ? Na6 P1 C6 C5 166.72(11) 1_655 . . . ? O3 P1 O1 Na6 170.09(10) . . . 2_445 ? C6 P1 O1 Na6 46.20(14) . . . 2_445 ? O1 P1 O3 Na6 52.18(15) . . . 1_655 ? C6 P1 O3 Na6 175.16(10) . . . 1_655 ? C4 C6 O4 Na6 -14.4(2) . . . . ? C5 C6 O4 Na6 -135.86(15) . . . . ? P1 C6 O4 Na6 101.22(13) . . . . ? O2 C4 O5 Na6 -178.03(14) . . . . ? C6 C4 O5 Na6 1.1(3) . . . . ? O2 C4 O5 Na6 -16.3(3) . . . 3_465 ? C6 C4 O5 Na6 162.79(14) . . . 3_465 ? C4 O5 Na6 O3 -98.03(17) . . . 1_455 ? C4 O5 Na6 O1 142.98(19) . . . 2_455 ? C4 O5 Na6 O5 166.6(2) . . . 3_465 ? C4 O5 Na6 O4 -6.66(16) . . . . ? C4 O5 Na6 O6 87.45(17) . . . 2_455 ? C4 O5 Na6 P1 -77.67(17) . . . 1_455 ? C6 O4 Na6 O5 11.83(13) . . . . ? C6 O4 Na6 O3 99.42(14) . . . 1_455 ? C6 O4 Na6 O1 -153.22(13) . . . 2_455 ? C6 O4 Na6 O5 0.5(2) . . . 3_465 ? C6 O4 Na6 O6 -67.48(14) . . . 2_455 ? C6 O4 Na6 P1 104.34(14) . . . 1_455 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.411 _refine_diff_density_min -0.605 _refine_diff_density_rms 0.111