data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Liangjie Yuan' _publ_contact_author_email LJYUAN@WHU.EDU.CN _publ_section_title ; Hydrogen-bonded assembly of aminophosphonic anions: Different 1D, 2D and 3D supramolecular architectures ; loop_ _publ_author_name 'Liangjie Yuan.' 'Shuoping Chen.' 'Hong-zhen He.' 'Le Hu.' 'Yu-qin Zhang.' # Attachment '7.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 682745' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H11 N O7 P2' _chemical_formula_weight 223.06 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 monoclinic _symmetry_space_group_name_H-M P2(1)/C 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' _cell_length_a 7.3372(6) _cell_length_b 10.6553(8) _cell_length_c 10.6128(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.7050(10) _cell_angle_gamma 90.00 _cell_volume 822.22(11) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3640 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.802 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.534 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8311 _exptl_absorpt_correction_T_max 0.9101 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5340 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0153 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 28.00 _reflns_number_total 1972 _reflns_number_gt 1837 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0452P)^2^+0.8063P] 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 SHELXL _refine_ls_extinction_coef 0.024(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1972 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0885 _refine_ls_wR_factor_gt 0.0863 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.010 _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 0.78594(5) 0.47061(4) 0.18354(4) 0.01363(14) Uani 1 1 d . . . P2 P 1.21301(5) 0.47175(4) 0.26318(4) 0.01382(14) Uani 1 1 d . . . O5 O 1.20387(16) 0.37078(12) 0.35945(12) 0.0207(3) Uani 1 1 d . . . O2 O 0.75558(17) 0.37256(12) 0.27920(12) 0.0211(3) Uani 1 1 d . . . O4 O 1.23163(17) 0.41014(12) 0.13104(12) 0.0211(3) Uani 1 1 d . . . O6 O 1.36086(16) 0.56985(12) 0.29438(12) 0.0202(3) Uani 1 1 d . . . O3 O 0.80235(17) 0.42564(12) 0.05068(11) 0.0211(3) Uani 1 1 d . . . O1 O 0.63603(17) 0.57628(12) 0.17128(13) 0.0210(3) Uani 1 1 d . . . N1 N 1.0164(2) 0.66547(13) 0.14934(13) 0.0155(3) Uani 1 1 d . . . C1 C 0.9948(2) 0.56112(15) 0.24269(15) 0.0133(3) Uani 1 1 d . . . C2 C 0.9672(3) 0.62358(18) 0.36845(17) 0.0213(4) Uani 1 1 d . . . O1W O 0.4462(2) 0.70218(17) 0.52445(16) 0.0369(4) Uani 1 1 d . . . H4 H 1.103(4) 0.714(3) 0.176(2) 0.032(6) Uiso 1 1 d . . . H6 H 0.922(3) 0.720(2) 0.139(2) 0.027(6) Uiso 1 1 d . . . H5 H 1.039(3) 0.638(2) 0.072(2) 0.031(6) Uiso 1 1 d . . . H3 H 0.862(4) 0.679(3) 0.358(3) 0.040(7) Uiso 1 1 d . . . H2 H 0.943(4) 0.568(3) 0.434(3) 0.054(8) Uiso 1 1 d . . . H1 H 1.071(4) 0.674(3) 0.404(3) 0.050(8) Uiso 1 1 d . . . H7 H 1.228(4) 0.457(3) 0.076(3) 0.053(9) Uiso 1 1 d . . . H8 H 0.559(4) 0.569(3) 0.210(3) 0.046(8) Uiso 1 1 d . . . H9 H 0.586(5) 0.695(4) 0.560(3) 0.044(10) Uiso 0.75 1 d P . . H10 H 0.412(5) 0.798(4) 0.506(3) 0.044(10) Uiso 0.75 1 d P . . H11 H 0.373(5) 0.667(4) 0.599(4) 0.044(10) Uiso 0.75 1 d P . . H12 H 0.422(5) 0.654(4) 0.433(4) 0.044(10) Uiso 0.75 1 d P . . 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 0.0130(2) 0.0127(2) 0.0154(2) 0.00126(14) 0.00252(15) -0.00030(14) P2 0.0125(2) 0.0128(2) 0.0161(2) 0.00007(14) 0.00170(15) 0.00020(14) O5 0.0193(6) 0.0191(6) 0.0232(6) 0.0067(5) 0.0005(5) 0.0009(5) O2 0.0213(6) 0.0167(6) 0.0263(6) 0.0073(5) 0.0069(5) 0.0001(5) O4 0.0249(6) 0.0185(6) 0.0204(6) -0.0036(5) 0.0051(5) 0.0018(5) O6 0.0152(5) 0.0196(6) 0.0261(6) -0.0050(5) 0.0038(4) -0.0038(5) O3 0.0219(6) 0.0240(6) 0.0172(6) -0.0039(5) 0.0022(5) -0.0006(5) O1 0.0156(6) 0.0201(6) 0.0285(7) 0.0065(5) 0.0072(5) 0.0044(5) N1 0.0171(7) 0.0121(6) 0.0179(7) 0.0019(5) 0.0040(5) -0.0004(5) C1 0.0147(7) 0.0116(7) 0.0139(7) 0.0008(6) 0.0032(5) -0.0005(5) C2 0.0257(9) 0.0219(8) 0.0167(8) -0.0044(6) 0.0044(6) 0.0029(7) O1W 0.0359(8) 0.0393(9) 0.0345(8) -0.0002(7) 0.0010(6) 0.0013(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 O2 1.4942(12) . ? P1 O3 1.5092(12) . ? P1 O1 1.5672(13) . ? P1 C1 1.8480(16) . ? P2 O5 1.4915(12) . ? P2 O6 1.5108(12) . ? P2 O4 1.5708(13) . ? P2 C1 1.8502(16) . ? O4 H7 0.76(3) . ? O1 H8 0.74(3) . ? N1 C1 1.512(2) . ? N1 H4 0.84(3) . ? N1 H6 0.90(3) . ? N1 H5 0.90(3) . ? C1 C2 1.529(2) . ? C2 H3 0.97(3) . ? C2 H2 0.95(3) . ? C2 H1 0.97(3) . ? O1W H9 1.04(4) . ? O1W H10 1.06(4) . ? O1W H11 1.08(4) . ? O1W H12 1.09(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 O2 P1 O3 116.78(8) . . ? O2 P1 O1 113.07(7) . . ? O3 P1 O1 107.07(7) . . ? O2 P1 C1 109.05(7) . . ? O3 P1 C1 108.46(7) . . ? O1 P1 C1 101.20(7) . . ? O5 P2 O6 116.48(7) . . ? O5 P2 O4 109.11(8) . . ? O6 P2 O4 109.81(7) . . ? O5 P2 C1 109.52(7) . . ? O6 P2 C1 104.73(7) . . ? O4 P2 C1 106.72(7) . . ? P2 O4 H7 114(2) . . ? P1 O1 H8 117(2) . . ? C1 N1 H4 112.0(17) . . ? C1 N1 H6 114.3(15) . . ? H4 N1 H6 100(2) . . ? C1 N1 H5 113.8(17) . . ? H4 N1 H5 106(2) . . ? H6 N1 H5 109(2) . . ? N1 C1 C2 106.84(13) . . ? N1 C1 P1 108.44(10) . . ? C2 C1 P1 108.83(11) . . ? N1 C1 P2 106.88(10) . . ? C2 C1 P2 109.59(11) . . ? P1 C1 P2 115.88(9) . . ? C1 C2 H3 111.6(16) . . ? C1 C2 H2 115.1(19) . . ? H3 C2 H2 104(2) . . ? C1 C2 H1 113.3(18) . . ? H3 C2 H1 106(2) . . ? H2 C2 H1 106(2) . . ? H9 O1W H10 109(3) . . ? H9 O1W H11 106(3) . . ? H10 O1W H11 110(3) . . ? H9 O1W H12 109(3) . . ? H10 O1W H12 106(3) . . ? H11 O1W H12 117(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 O2 P1 C1 N1 -176.16(10) . . . . ? O3 P1 C1 N1 55.68(12) . . . . ? O1 P1 C1 N1 -56.76(12) . . . . ? O2 P1 C1 C2 -60.29(13) . . . . ? O3 P1 C1 C2 171.55(11) . . . . ? O1 P1 C1 C2 59.11(12) . . . . ? O2 P1 C1 P2 63.71(10) . . . . ? O3 P1 C1 P2 -64.45(10) . . . . ? O1 P1 C1 P2 -176.89(8) . . . . ? O5 P2 C1 N1 177.25(10) . . . . ? O6 P2 C1 N1 51.64(12) . . . . ? O4 P2 C1 N1 -64.78(12) . . . . ? O5 P2 C1 C2 61.82(13) . . . . ? O6 P2 C1 C2 -63.79(13) . . . . ? O4 P2 C1 C2 179.80(11) . . . . ? O5 P2 C1 P1 -61.78(11) . . . . ? O6 P2 C1 P1 172.61(8) . . . . ? O4 P2 C1 P1 56.19(10) . . . . ? 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 N1 H4 O2 0.84(3) 2.01(3) 2.8111(19) 161(2) 2_755 N1 H6 O5 0.90(3) 1.85(3) 2.7142(19) 159(2) 2_755 N1 H5 O3 0.90(3) 1.98(3) 2.8237(19) 154(2) 3_765 O4 H7 O3 0.76(3) 1.83(3) 2.5913(19) 174(3) 3_765 O1 H8 O6 0.74(3) 1.81(3) 2.5486(18) 172(3) 1_455 O1W H9 O5 1.04(4) 1.81(4) 2.804(2) 159(3) 3_766 O1W H10 O3 1.06(4) 2.11(4) 3.040(2) 145(3) 2_655 O1W H11 O2 1.08(4) 1.75(4) 2.828(2) 173(3) 3_666 O1W H12 O6 1.09(4) 1.73(4) 2.816(2) 173(3) 1_455 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.397 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.072 # Attachment '8.cif' data_80519csp1_0m _database_code_depnum_ccdc_archive 'CCDC 703024' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H13 N O7 P2' _chemical_formula_weight 237.08 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 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 10.9976(9) _cell_length_b 6.9889(6) _cell_length_c 12.5997(10) _cell_angle_alpha 90.00 _cell_angle_beta 113.5640(10) _cell_angle_gamma 90.00 _cell_volume 887.67(13) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.774 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.500 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8484 _exptl_absorpt_correction_T_max 0.8979 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5668 _diffrn_reflns_av_R_equivalents 0.0143 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2123 _reflns_number_gt 2000 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0508P)^2^+0.6533P] 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 SHELXL _refine_ls_extinction_coef 0.016(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2123 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0879 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.010 _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 C1 C 0.38949(14) 0.7210(2) 0.17252(12) 0.0128(3) Uani 1 1 d . . . C2 C 0.44517(18) 0.8823(2) 0.12104(14) 0.0212(3) Uani 1 1 d . . . H2A H 0.4165 0.8594 0.0387 0.025 Uiso 1 1 calc R . . H2B H 0.4064 1.0025 0.1302 0.025 Uiso 1 1 calc R . . C3 C 0.5959(2) 0.9037(3) 0.17398(19) 0.0301(4) Uani 1 1 d . . . H3A H 0.6279 0.8987 0.2569 0.045 Uiso 1 1 calc R . . H3B H 0.6197 1.0242 0.1511 0.045 Uiso 1 1 calc R . . H3C H 0.6349 0.8016 0.1473 0.045 Uiso 1 1 calc R . . H3 H 0.281(2) 0.698(4) 0.354(2) 0.023(6) Uiso 1 1 d . . . H5 H 0.592(2) 0.474(3) 0.111(2) 0.025(6) Uiso 1 1 d . . . H1W1 H 0.617(3) 0.286(5) 0.304(3) 0.042(9) Uiso 0.75 1 d P . . H2W1 H 0.598(4) 0.382(6) 0.417(3) 0.043(9) Uiso 0.75 1 d P . . H3W1 H 0.708(4) 0.187(5) 0.434(3) 0.041(9) Uiso 0.75 1 d P . . H4W1 H 0.540(4) 0.152(6) 0.375(3) 0.042(9) Uiso 0.75 1 d P . . N1 N 0.23959(13) 0.74451(19) 0.12109(11) 0.0151(3) Uani 1 1 d . . . H1A H 0.2184 0.8512 0.1482 0.023 Uiso 1 1 calc R . . H1B H 0.2027 0.6446 0.1406 0.023 Uiso 1 1 calc R . . H1C H 0.2099 0.7515 0.0443 0.023 Uiso 1 1 calc R . . O1 O 0.43101(12) 0.96082(17) 0.35107(10) 0.0197(3) Uani 1 1 d . . . O2 O 0.57555(11) 0.65745(18) 0.39366(10) 0.0209(3) Uani 1 1 d . . . O3 O 0.33604(12) 0.63802(17) 0.36012(10) 0.0180(2) Uani 1 1 d . . . O4 O 0.37018(12) 0.33922(17) 0.19055(11) 0.0207(3) Uani 1 1 d . . . O5 O 0.56852(11) 0.45308(19) 0.16182(10) 0.0201(3) Uani 1 1 d . . . O6 O 0.34347(11) 0.47787(18) -0.00509(10) 0.0200(3) Uani 1 1 d . . . O1W O 0.61750(16) 0.2514(2) 0.38661(15) 0.0360(4) Uani 1 1 d . . . P1 P 0.44452(4) 0.75146(5) 0.33203(3) 0.01309(13) Uani 1 1 d . . . P2 P 0.41591(4) 0.48090(6) 0.12530(3) 0.01331(13) Uani 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 C1 0.0123(7) 0.0132(7) 0.0120(6) 0.0004(5) 0.0038(5) 0.0005(5) C2 0.0281(8) 0.0176(8) 0.0199(7) 0.0025(6) 0.0118(7) -0.0040(6) C3 0.0293(9) 0.0259(9) 0.0434(11) -0.0036(8) 0.0234(8) -0.0088(7) N1 0.0143(6) 0.0149(6) 0.0137(6) 0.0000(4) 0.0030(5) 0.0021(4) O1 0.0225(6) 0.0149(6) 0.0220(6) -0.0045(4) 0.0091(5) -0.0015(4) O2 0.0169(6) 0.0245(6) 0.0159(5) -0.0010(4) 0.0009(4) 0.0045(4) O3 0.0203(6) 0.0168(6) 0.0195(6) 0.0021(4) 0.0107(5) 0.0004(5) O4 0.0220(6) 0.0157(6) 0.0271(6) 0.0014(4) 0.0126(5) -0.0020(4) O5 0.0139(5) 0.0279(7) 0.0189(6) 0.0023(5) 0.0069(5) 0.0032(4) O6 0.0171(5) 0.0272(6) 0.0146(5) -0.0056(4) 0.0052(4) -0.0017(4) O1W 0.0314(8) 0.0324(8) 0.0386(8) 0.0007(6) 0.0082(6) 0.0018(6) P1 0.0138(2) 0.0133(2) 0.0108(2) -0.00062(13) 0.00345(15) 0.00039(13) P2 0.0127(2) 0.0136(2) 0.0139(2) -0.00139(13) 0.00560(15) -0.00009(13) _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 C1 N1 1.5200(18) . ? C1 C2 1.544(2) . ? C1 P2 1.8418(16) . ? C1 P1 1.8650(15) . ? C2 C3 1.527(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? O1 P1 1.4997(12) . ? O2 P1 1.4888(12) . ? O3 P1 1.5858(12) . ? O3 H3 0.72(2) . ? O4 P2 1.4966(12) . ? O5 P2 1.5649(12) . ? O5 H5 0.79(2) . ? O6 P2 1.5125(12) . ? O1W H1W1 1.06(4) . ? O1W H2W1 1.05(4) . ? O1W H3W1 1.04(4) . ? O1W H4W1 1.07(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 106.66(12) . . ? N1 C1 P2 104.18(9) . . ? C2 C1 P2 112.90(11) . . ? N1 C1 P1 106.05(9) . . ? C2 C1 P1 110.92(10) . . ? P2 C1 P1 115.28(8) . . ? C3 C2 C1 115.59(14) . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2B 108.4 . . ? C1 C2 H2B 108.4 . . ? H2A C2 H2B 107.4 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? P1 O3 H3 111.8(19) . . ? P2 O5 H5 113.2(17) . . ? H1W1 O1W H2W1 104(3) . . ? H1W1 O1W H3W1 107(3) . . ? H2W1 O1W H3W1 117(3) . . ? H1W1 O1W H4W1 109(3) . . ? H2W1 O1W H4W1 111(3) . . ? H3W1 O1W H4W1 109(3) . . ? O2 P1 O1 118.97(7) . . ? O2 P1 O3 108.70(7) . . ? O1 P1 O3 108.70(7) . . ? O2 P1 C1 109.94(7) . . ? O1 P1 C1 105.87(7) . . ? O3 P1 C1 103.56(6) . . ? O4 P2 O6 116.15(7) . . ? O4 P2 O5 108.22(7) . . ? O6 P2 O5 110.79(7) . . ? O4 P2 C1 107.11(7) . . ? O6 P2 C1 106.32(7) . . ? O5 P2 C1 107.90(7) . . ? 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 N1 C1 C2 C3 171.63(14) . . . . ? P2 C1 C2 C3 -74.54(16) . . . . ? P1 C1 C2 C3 56.58(17) . . . . ? N1 C1 P1 O2 157.47(10) . . . . ? C2 C1 P1 O2 -87.11(12) . . . . ? P2 C1 P1 O2 42.77(10) . . . . ? N1 C1 P1 O1 -72.83(10) . . . . ? C2 C1 P1 O1 42.59(12) . . . . ? P2 C1 P1 O1 172.47(8) . . . . ? N1 C1 P1 O3 41.46(11) . . . . ? C2 C1 P1 O3 156.89(11) . . . . ? P2 C1 P1 O3 -73.23(9) . . . . ? N1 C1 P2 O4 -70.34(10) . . . . ? C2 C1 P2 O4 174.33(11) . . . . ? P1 C1 P2 O4 45.42(10) . . . . ? N1 C1 P2 O6 54.45(10) . . . . ? C2 C1 P2 O6 -60.87(12) . . . . ? P1 C1 P2 O6 170.22(8) . . . . ? N1 C1 P2 O5 173.34(9) . . . . ? C2 C1 P2 O5 58.02(12) . . . . ? P1 C1 P2 O5 -70.89(9) . . . . ? 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 O3 H3 O4 0.72(2) 1.82(2) 2.5240(17) 169(3) 2 O5 H5 O6 0.79(2) 1.78(2) 2.5686(17) 176(2) 3_665 O1W H1W1 O5 1.06(4) 2.03(4) 3.013(2) 153(3) . O1W H2W1 O2 1.05(4) 1.95(4) 2.882(2) 147(3) . O1W H3W1 O6 1.04(4) 1.79(4) 2.810(2) 165(3) 4_666 O1W H4W1 O1 1.07(4) 1.73(4) 2.792(2) 170(3) 1_545 N1 H1A O3 0.89 2.08 2.9102(17) 154.4 2 N1 H1A O4 0.89 2.58 3.1336(18) 121.0 2 N1 H1B O1 0.89 1.99 2.8461(18) 161.9 2_545 N1 H1C O2 0.89 1.99 2.7932(17) 149.9 4_575 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.415 _refine_diff_density_min -0.643 _refine_diff_density_rms 0.075 # Attachment '6.cif' data_080618cm _database_code_depnum_ccdc_archive 'CCDC 703025' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H15 N2 O6 P2' _chemical_formula_weight 249.12 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 5.6936(7) _cell_length_b 8.1718(10) _cell_length_c 10.6221(12) _cell_angle_alpha 72.749(2) _cell_angle_beta 79.075(2) _cell_angle_gamma 84.784(2) _cell_volume 463.11(10) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2831 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 28.30 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.787 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 262 _exptl_absorpt_coefficient_mu 0.479 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8696 _exptl_absorpt_correction_T_max 0.9103 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2948 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1779 _reflns_number_gt 1723 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0399P)^2^+0.3101P] 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 SHELXL _refine_ls_extinction_coef 0.040(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1779 _refine_ls_number_parameters 139 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0780 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 C1 C 0.6284(3) 0.6251(2) 0.22676(15) 0.0143(3) Uani 1 1 d . . . C2 C 0.6846(3) 0.7634(2) 0.09142(17) 0.0203(4) Uani 1 1 d . . . H2A H 0.8268 0.7258 0.0394 0.024 Uiso 1 1 calc R . . H2B H 0.5533 0.7718 0.0432 0.024 Uiso 1 1 calc R . . C3 C 0.7245(3) 0.9416(2) 0.09985(19) 0.0258(4) Uani 1 1 d . . . H3A H 0.5846 0.9811 0.1505 0.039 Uiso 1 1 calc R . . H3B H 0.7545 1.0193 0.0113 0.039 Uiso 1 1 calc R . . H3C H 0.8596 0.9367 0.1431 0.039 Uiso 1 1 calc R . . C4 C 0.0801(3) 0.0740(2) 0.45984(18) 0.0239(4) Uani 1 1 d . . . H4A H 0.0329 0.1732 0.4924 0.029 Uiso 1 1 calc R . . H4B H 0.2450 0.0419 0.4705 0.029 Uiso 1 1 calc R . . H3 H 0.481(5) 0.755(3) 0.4954(10) 0.044(7) Uiso 1 1 d D . . H6 H 0.730(5) 0.455(4) 0.009(3) 0.049(8) Uiso 1 1 d . . . N1 N 0.8491(2) 0.58805(18) 0.29180(14) 0.0159(3) Uani 1 1 d . . . H1A H 0.9531 0.5224 0.2527 0.024 Uiso 1 1 calc R . . H1B H 0.8082 0.5338 0.3784 0.024 Uiso 1 1 calc R . . H1C H 0.9158 0.6862 0.2826 0.024 Uiso 1 1 calc R . . N2 N 0.0593(3) 0.1170(2) 0.31646(16) 0.0251(3) Uani 1 1 d . . . H2C H 0.1038 0.0259 0.2869 0.038 Uiso 1 1 calc R . . H2D H 0.1534 0.2033 0.2695 0.038 Uiso 1 1 calc R . . H2E H -0.0918 0.1477 0.3070 0.038 Uiso 1 1 calc R . . O1 O 0.2635(2) 0.53898(16) 0.44053(12) 0.0209(3) Uani 1 1 d . . . O2 O 0.2152(2) 0.81655(15) 0.25823(12) 0.0201(3) Uani 1 1 d . . . O3 O 0.5091(2) 0.79652(16) 0.41196(12) 0.0211(3) Uani 1 1 d D . . O4 O 0.3107(2) 0.43997(16) 0.16427(12) 0.0213(3) Uani 1 1 d . . . O5 O 0.5980(2) 0.27635(15) 0.32293(12) 0.0217(3) Uani 1 1 d . . . O6 O 0.7572(2) 0.39668(17) 0.08395(13) 0.0227(3) Uani 1 1 d . . . P1 P 0.37761(7) 0.69373(5) 0.34202(4) 0.01473(16) Uani 1 1 d . . . P2 P 0.55599(7) 0.42109(5) 0.20264(4) 0.01570(15) Uani 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 C1 0.0118(7) 0.0161(8) 0.0148(7) -0.0041(6) -0.0030(6) 0.0003(6) C2 0.0201(8) 0.0224(9) 0.0161(8) -0.0026(7) -0.0021(6) 0.0001(6) C3 0.0246(9) 0.0212(9) 0.0270(9) 0.0007(7) -0.0042(7) -0.0039(7) C4 0.0213(9) 0.0233(9) 0.0297(10) -0.0123(8) -0.0034(7) -0.0003(7) N1 0.0126(7) 0.0174(7) 0.0178(7) -0.0048(5) -0.0035(5) -0.0003(5) N2 0.0246(8) 0.0205(7) 0.0298(9) -0.0082(6) -0.0024(6) 0.0008(6) O1 0.0188(6) 0.0246(6) 0.0171(6) -0.0031(5) -0.0005(5) -0.0042(5) O2 0.0167(6) 0.0208(6) 0.0231(6) -0.0067(5) -0.0059(5) 0.0038(5) O3 0.0243(7) 0.0229(6) 0.0187(6) -0.0084(5) -0.0053(5) -0.0020(5) O4 0.0178(6) 0.0279(7) 0.0205(6) -0.0095(5) -0.0047(5) -0.0018(5) O5 0.0270(7) 0.0178(6) 0.0196(6) -0.0044(5) -0.0045(5) 0.0012(5) O6 0.0221(7) 0.0277(7) 0.0190(6) -0.0099(5) -0.0016(5) 0.0034(5) P1 0.0126(2) 0.0172(2) 0.0147(2) -0.00547(17) -0.00200(16) 0.00062(16) P2 0.0155(2) 0.0173(2) 0.0154(2) -0.00625(17) -0.00309(16) 0.00005(16) _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 C1 N1 1.511(2) . ? C1 C2 1.541(2) . ? C1 P2 1.8524(16) . ? C1 P1 1.8578(16) . ? C2 C3 1.526(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 N2 1.483(2) . ? C4 C4 1.522(4) 2_556 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? N2 H2C 0.8900 . ? N2 H2D 0.8900 . ? N2 H2E 0.8900 . ? O1 P1 1.4908(12) . ? O2 P1 1.5061(12) . ? O3 P1 1.5853(12) . ? O3 H3 0.839(10) . ? O4 P2 1.5100(13) . ? O5 P2 1.5023(13) . ? O6 P2 1.5818(13) . ? O6 H6 0.83(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 N1 C1 C2 108.86(13) . . ? N1 C1 P2 106.67(10) . . ? C2 C1 P2 110.87(11) . . ? N1 C1 P1 108.80(10) . . ? C2 C1 P1 112.14(11) . . ? P2 C1 P1 109.34(8) . . ? C3 C2 C1 115.41(14) . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2B 108.4 . . ? C1 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 C4 109.51(19) . 2_556 ? N2 C4 H4A 109.8 . . ? C4 C4 H4A 109.8 2_556 . ? N2 C4 H4B 109.8 . . ? C4 C4 H4B 109.8 2_556 . ? H4A C4 H4B 108.2 . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C4 N2 H2C 109.5 . . ? C4 N2 H2D 109.5 . . ? H2C N2 H2D 109.5 . . ? C4 N2 H2E 109.5 . . ? H2C N2 H2E 109.5 . . ? H2D N2 H2E 109.5 . . ? P1 O3 H3 110.6(19) . . ? P2 O6 H6 113(2) . . ? O1 P1 O2 115.92(7) . . ? O1 P1 O3 111.54(7) . . ? O2 P1 O3 108.81(7) . . ? O1 P1 C1 109.20(7) . . ? O2 P1 C1 107.88(7) . . ? O3 P1 C1 102.60(7) . . ? O5 P2 O4 117.27(7) . . ? O5 P2 O6 105.66(7) . . ? O4 P2 O6 111.21(7) . . ? O5 P2 C1 108.88(7) . . ? O4 P2 C1 109.16(7) . . ? O6 P2 C1 103.79(7) . . ? 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 N1 C1 C2 C3 -68.30(18) . . . . ? P2 C1 C2 C3 174.66(12) . . . . ? P1 C1 C2 C3 52.14(18) . . . . ? N1 C1 P1 O1 -83.94(11) . . . . ? C2 C1 P1 O1 155.59(11) . . . . ? P2 C1 P1 O1 32.20(10) . . . . ? N1 C1 P1 O2 149.29(10) . . . . ? C2 C1 P1 O2 28.82(13) . . . . ? P2 C1 P1 O2 -94.57(9) . . . . ? N1 C1 P1 O3 34.50(12) . . . . ? C2 C1 P1 O3 -85.97(12) . . . . ? P2 C1 P1 O3 150.64(8) . . . . ? N1 C1 P2 O5 39.46(12) . . . . ? C2 C1 P2 O5 157.83(11) . . . . ? P1 C1 P2 O5 -78.03(9) . . . . ? N1 C1 P2 O4 168.61(10) . . . . ? C2 C1 P2 O4 -73.01(12) . . . . ? P1 C1 P2 O4 51.12(10) . . . . ? N1 C1 P2 O6 -72.73(11) . . . . ? C2 C1 P2 O6 45.65(13) . . . . ? P1 C1 P2 O6 169.78(8) . . . . ? 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 O3 H3 O5 0.839(10) 1.841(12) 2.6603(17) 165(3) 2_666 O6 H6 O4 0.83(3) 1.83(3) 2.6624(19) 173(3) 2_665 N1 H1A O4 0.89 2.21 3.0417(19) 155.4 1_655 N1 H1B O1 0.89 1.81 2.6930(18) 169.2 2_666 N1 H1C O2 0.89 2.03 2.8267(18) 149.0 1_655 N2 H2C O2 0.89 1.86 2.738(2) 168.5 1_545 N2 H2D O4 0.89 2.11 2.984(2) 167.9 . N2 H2E O5 0.89 1.98 2.821(2) 158.0 1_455 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.412 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.063 # Attachment '5.cif' data_80918csp1_0m _database_code_depnum_ccdc_archive 'CCDC 703026' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H16 N2 O6 P2' _chemical_formula_weight 262.14 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.5570(17) _cell_length_b 5.7463(4) _cell_length_c 18.8938(13) _cell_angle_alpha 90.00 _cell_angle_beta 121.9600(10) _cell_angle_gamma 90.00 _cell_volume 2169.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 4272 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 29.47 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.414 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8422 _exptl_absorpt_correction_T_max 0.9219 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6933 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2611 _reflns_number_gt 2409 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0530P)^2^+1.8606P] 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 SHELXL _refine_ls_extinction_coef 0.0060(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2611 _refine_ls_number_parameters 158 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.167 _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 C3 C 0.08511(18) 0.3226(7) 0.3439(3) 0.0493(11) Uani 0.618(6) 1 d PD A 1 H3A H 0.0595 0.3831 0.3659 0.074 Uiso 0.618(6) 1 calc PR A 1 H3B H 0.1118 0.1941 0.3776 0.074 Uiso 0.618(6) 1 calc PR A 1 H3C H 0.0554 0.2707 0.2877 0.074 Uiso 0.618(6) 1 calc PR A 1 C3' C 0.0750(3) 0.6569(10) 0.3099(4) 0.0470(16) Uani 0.382(6) 1 d PD A 2 H3'1 H 0.0492 0.6367 0.2505 0.071 Uiso 0.382(6) 1 calc PR A 2 H3'2 H 0.0923 0.8127 0.3230 0.071 Uiso 0.382(6) 1 calc PR A 2 H3'3 H 0.0471 0.6301 0.3320 0.071 Uiso 0.382(6) 1 calc PR A 2 C1 C 0.17443(7) 0.4563(3) 0.31249(9) 0.0198(3) Uani 1 1 d . A . C2 C 0.12759(10) 0.5001(4) 0.34497(13) 0.0440(5) Uani 1 1 d D . . C5 C 0.05285(10) 0.8566(4) 0.00810(14) 0.0448(5) Uani 1 1 d . . . H5A H 0.0284 0.7382 -0.0339 0.054 Uiso 1 1 calc R . . H5B H 0.1003 0.8234 0.0350 0.054 Uiso 1 1 calc R . . C7 C -0.03803(11) 0.9072(4) 0.03288(14) 0.0457(5) Uani 1 1 d . . . H7A H -0.0488 0.9073 0.0758 0.055 Uiso 1 1 calc R . . H7B H -0.0654 0.7903 -0.0082 0.055 Uiso 1 1 calc R . . H2 H 0.2840(16) 0.437(6) 0.5031(14) 0.083(11) Uiso 1 1 d D . . H4 H 0.1826(15) 0.488(2) 0.1632(19) 0.069(9) Uiso 1 1 d D . . N4 N 0.20029(7) 0.6913(2) 0.30628(8) 0.0233(3) Uani 1 1 d . . . H4A H 0.2178 0.7654 0.3548 0.035 Uiso 1 1 calc R A . H4B H 0.1667 0.7748 0.2664 0.035 Uiso 1 1 calc R . . H4C H 0.2316 0.6721 0.2939 0.035 Uiso 1 1 calc R . . N6 N 0.03344(8) 0.8501(3) 0.07032(10) 0.0398(4) Uani 1 1 d . . . H6A H 0.0585 0.9525 0.1113 0.048 Uiso 1 1 calc R . . H6B H 0.0415 0.7072 0.0932 0.048 Uiso 1 1 calc R . . O1 O 0.22795(6) 0.0746(2) 0.41501(7) 0.0283(3) Uani 1 1 d . A . O2 O 0.28793(6) 0.4636(2) 0.46192(7) 0.0290(3) Uani 1 1 d D A . O3 O 0.29005(6) 0.2450(2) 0.35013(7) 0.0303(3) Uani 1 1 d . A . O4 O 0.17751(7) 0.3494(2) 0.17376(8) 0.0321(3) Uani 1 1 d D A . O5 O 0.06695(6) 0.4619(2) 0.15390(8) 0.0334(3) Uani 1 1 d . A . O6 O 0.11970(6) 0.0706(2) 0.21490(7) 0.0288(3) Uani 1 1 d . A . P1 P 0.24915(2) 0.28655(7) 0.38836(2) 0.02103(14) Uani 1 1 d . . . P2 P 0.129527(19) 0.32432(7) 0.20707(2) 0.02161(14) Uani 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 C3 0.0402(18) 0.058(2) 0.062(2) 0.0170(18) 0.0350(18) 0.0035(16) C3' 0.048(3) 0.045(3) 0.054(4) -0.002(3) 0.031(3) 0.007(3) C1 0.0212(6) 0.0184(7) 0.0186(6) 0.0004(5) 0.0096(5) 0.0001(5) C2 0.0341(9) 0.0692(15) 0.0379(10) -0.0028(10) 0.0253(8) 0.0050(9) C5 0.0330(9) 0.0402(11) 0.0440(11) 0.0008(9) 0.0086(8) 0.0080(8) C7 0.0451(11) 0.0457(12) 0.0393(11) 0.0036(9) 0.0175(9) -0.0073(9) N4 0.0278(6) 0.0165(6) 0.0197(6) -0.0010(5) 0.0085(5) 0.0000(5) N6 0.0440(9) 0.0228(7) 0.0230(7) 0.0038(6) -0.0025(6) -0.0026(6) O1 0.0421(7) 0.0188(5) 0.0206(5) 0.0008(4) 0.0142(5) -0.0010(5) O2 0.0343(6) 0.0274(6) 0.0186(5) -0.0029(5) 0.0094(5) -0.0059(5) O3 0.0300(6) 0.0344(7) 0.0278(6) 0.0024(5) 0.0161(5) 0.0074(5) O4 0.0424(7) 0.0313(7) 0.0267(6) -0.0006(5) 0.0211(6) -0.0001(6) O5 0.0271(6) 0.0276(6) 0.0292(6) 0.0086(5) 0.0038(5) 0.0022(5) O6 0.0339(6) 0.0176(5) 0.0233(5) 0.0004(4) 0.0072(5) -0.0028(4) P1 0.0242(2) 0.0188(2) 0.0160(2) 0.00056(13) 0.00788(16) 0.00150(14) P2 0.0234(2) 0.0174(2) 0.0167(2) 0.00081(13) 0.00561(16) -0.00144(13) _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 C3 C2 1.422(4) . ? C3' C2 1.385(5) . ? C1 N4 1.5114(19) . ? C1 C2 1.541(2) . ? C1 P2 1.8521(15) . ? C1 P1 1.8531(15) . ? C5 N6 1.470(3) . ? C5 C7 1.509(3) 5_575 ? C7 N6 1.477(3) . ? C7 C5 1.509(3) 5_575 ? O1 P1 1.5007(12) . ? O2 P1 1.5676(12) . ? O3 P1 1.4979(12) . ? O4 P2 1.5645(13) . ? O5 P2 1.4963(12) . ? O6 P2 1.4960(12) . ? 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 N4 C1 C2 106.74(14) . . ? N4 C1 P2 107.86(10) . . ? C2 C1 P2 111.93(11) . . ? N4 C1 P1 105.87(9) . . ? C2 C1 P1 111.41(11) . . ? P2 C1 P1 112.60(8) . . ? C3' C2 C3 90.9(3) . . ? C3' C2 C1 124.3(3) . . ? C3 C2 C1 121.6(2) . . ? N6 C5 C7 110.35(18) . 5_575 ? N6 C7 C5 109.93(17) . 5_575 ? C5 N6 C7 111.68(15) . . ? O3 P1 O1 116.46(7) . . ? O3 P1 O2 108.02(7) . . ? O1 P1 O2 111.75(7) . . ? O3 P1 C1 107.52(7) . . ? O1 P1 C1 109.76(7) . . ? O2 P1 C1 102.31(7) . . ? O6 P2 O5 115.61(7) . . ? O6 P2 O4 108.18(8) . . ? O5 P2 O4 110.24(7) . . ? O6 P2 C1 108.85(7) . . ? O5 P2 C1 107.74(7) . . ? O4 P2 C1 105.78(7) . . ? 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 N4 C1 C2 C3' 52.1(4) . . . . ? P2 C1 C2 C3' -65.7(4) . . . . ? P1 C1 C2 C3' 167.2(4) . . . . ? N4 C1 C2 C3 168.4(2) . . . . ? P2 C1 C2 C3 50.6(3) . . . . ? P1 C1 C2 C3 -76.5(3) . . . . ? C7 C5 N6 C7 57.4(2) 5_575 . . . ? C5 C7 N6 C5 -57.2(3) 5_575 . . . ? N4 C1 P1 O3 -66.50(11) . . . . ? C2 C1 P1 O3 177.84(12) . . . . ? P2 C1 P1 O3 51.13(10) . . . . ? N4 C1 P1 O1 165.92(9) . . . . ? C2 C1 P1 O1 50.25(14) . . . . ? P2 C1 P1 O1 -76.46(9) . . . . ? N4 C1 P1 O2 47.14(11) . . . . ? C2 C1 P1 O2 -68.53(13) . . . . ? P2 C1 P1 O2 164.76(8) . . . . ? N4 C1 P2 O6 164.82(10) . . . . ? C2 C1 P2 O6 -78.06(14) . . . . ? P1 C1 P2 O6 48.38(10) . . . . ? N4 C1 P2 O5 -69.12(11) . . . . ? C2 C1 P2 O5 48.00(14) . . . . ? P1 C1 P2 O5 174.44(8) . . . . ? N4 C1 P2 O4 48.78(11) . . . . ? C2 C1 P2 O4 165.90(13) . . . . ? P1 C1 P2 O4 -67.67(9) . . . . ? 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 N6 H6B O5 0.90 1.71 2.6030(19) 169.2 . N6 H6A O6 0.90 1.84 2.7053(19) 160.8 1_565 N4 H4C O3 0.89 2.52 3.0971(18) 122.7 4 N4 H4C O4 0.89 2.15 2.8469(19) 134.9 4 N4 H4B O6 0.89 1.98 2.8043(18) 153.4 1_565 N4 H4A O1 0.89 2.05 2.8425(17) 147.0 1_565 O4 H4 O3 0.847(11) 1.681(12) 2.5141(19) 167(3) 4 O2 H2 O1 0.844(11) 1.715(12) 2.5527(16) 172(4) 7_556 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.608 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.070 # Attachment '1.cif' data_81210x_0m _database_code_depnum_ccdc_archive 'CCDC 761327' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H21 N3 O7 P2' _chemical_formula_weight 297.19 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 orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 8.7719(6) _cell_length_b 11.5346(8) _cell_length_c 12.2848(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1242.98(15) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.379 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8757 _exptl_absorpt_correction_T_max 0.9146 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7916 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2324 _reflns_number_gt 2278 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0416P)^2^+0.0942P] 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 SHELXL _refine_ls_extinction_coef 0.0125(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(6) _refine_ls_number_reflns 2324 _refine_ls_number_parameters 171 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0217 _refine_ls_R_factor_gt 0.0212 _refine_ls_wR_factor_ref 0.0592 _refine_ls_wR_factor_gt 0.0588 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.14404(4) 0.54924(3) 0.23867(4) 0.01683(10) Uani 1 1 d . . . P2 P 0.42154(4) 0.58515(3) 0.08984(3) 0.01826(10) Uani 1 1 d . . . N1 N 0.30038(13) 0.75182(10) 0.22065(11) 0.0183(2) Uani 1 1 d . . . H1A H 0.2776 0.7758 0.2876 0.028 Uiso 1 1 calc R . . H1B H 0.2229 0.7672 0.1762 0.028 Uiso 1 1 calc R . . H1C H 0.3835 0.7885 0.1973 0.028 Uiso 1 1 calc R . . O2 O 0.03614(12) 0.60307(9) 0.15738(10) 0.0213(2) Uani 1 1 d . . . O3 O 0.09124(13) 0.55516(11) 0.35532(11) 0.0280(3) Uani 1 1 d . . . O1 O 0.18140(14) 0.42107(9) 0.20924(13) 0.0289(3) Uani 1 1 d D . . O4 O 0.58943(11) 0.61028(10) 0.10186(12) 0.0256(3) Uani 1 1 d . . . C1 C 0.32951(15) 0.62294(12) 0.22211(13) 0.0163(3) Uani 1 1 d . . . C2 C 0.43448(18) 0.59429(14) 0.31842(16) 0.0247(3) Uani 1 1 d . . . H2A H 0.5319 0.6304 0.3076 0.037 Uiso 1 1 calc R . . H2B H 0.4475 0.5118 0.3234 0.037 Uiso 1 1 calc R . . H2C H 0.3897 0.6227 0.3845 0.037 Uiso 1 1 calc R . . O6 O 0.34680(13) 0.66082(11) 0.00537(11) 0.0286(3) Uani 1 1 d . . . O5 O 0.38861(15) 0.45520(10) 0.07583(13) 0.0323(3) Uani 1 1 d . . . N3 N 0.05754(16) 0.67801(13) 0.92211(13) 0.0263(3) Uani 1 1 d . . . H3A H 0.0132 0.6091 0.9143 0.039 Uiso 1 1 calc R . . H3B H -0.0077 0.7271 0.9530 0.039 Uiso 1 1 calc R . . H3C H 0.1398 0.6708 0.9640 0.039 Uiso 1 1 calc R . . C5 C 0.19647(18) 0.63430(14) 0.75245(15) 0.0252(3) Uani 1 1 d . . . H5A H 0.1553 0.5575 0.7658 0.030 Uiso 1 1 calc R . . H5B H 0.3005 0.6356 0.7793 0.030 Uiso 1 1 calc R . . C6 C 0.1028(2) 0.72279(14) 0.81438(16) 0.0271(3) Uani 1 1 d . . . H6A H 0.1620 0.7931 0.8236 0.032 Uiso 1 1 calc R . . H6B H 0.0123 0.7419 0.7727 0.032 Uiso 1 1 calc R . . N2 N 0.18977(15) 0.54746(11) 0.56906(12) 0.0230(3) Uani 1 1 d . . . H2D H 0.2763 0.5084 0.5784 0.034 Uiso 1 1 calc R . . H2E H 0.1767 0.5623 0.4986 0.034 Uiso 1 1 calc R . . H2F H 0.1120 0.5052 0.5934 0.034 Uiso 1 1 calc R . . O1W O 0.30796(18) 0.84999(14) 0.42592(14) 0.0459(4) Uani 1 1 d D . . C4 C 0.1970(2) 0.65765(15) 0.63011(16) 0.0341(4) Uani 1 1 d . . . H4A H 0.1103 0.7057 0.6111 0.041 Uiso 1 1 calc R . . H4B H 0.2891 0.6993 0.6104 0.041 Uiso 1 1 calc R . . H2W1 H 0.252(2) 0.8923(18) 0.4651(19) 0.050(8) Uiso 1 1 d D . . H1 H 0.254(3) 0.426(2) 0.161(2) 0.066(9) Uiso 1 1 d D . . H1W1 H 0.3888(19) 0.888(2) 0.417(3) 0.069(10) Uiso 1 1 d 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 0.01424(16) 0.01945(17) 0.01681(19) 0.00277(15) -0.00028(14) -0.00176(12) P2 0.01566(17) 0.02031(17) 0.0188(2) -0.00219(15) 0.00115(15) -0.00068(12) N1 0.0175(5) 0.0176(5) 0.0200(7) -0.0015(5) 0.0009(5) -0.0010(4) O2 0.0169(4) 0.0251(5) 0.0218(6) 0.0033(5) -0.0027(5) 0.0000(4) O3 0.0232(6) 0.0421(7) 0.0186(6) 0.0037(5) 0.0021(5) -0.0066(4) O1 0.0280(5) 0.0175(5) 0.0411(8) 0.0034(5) 0.0045(6) -0.0019(4) O4 0.0155(5) 0.0310(5) 0.0302(7) -0.0052(6) 0.0024(5) 0.0003(4) C1 0.0146(5) 0.0178(6) 0.0166(7) 0.0007(5) 0.0002(5) -0.0006(4) C2 0.0198(7) 0.0326(9) 0.0216(9) 0.0040(7) -0.0050(6) -0.0001(6) O6 0.0230(5) 0.0429(7) 0.0198(6) 0.0066(5) -0.0002(5) 0.0013(5) O5 0.0362(6) 0.0246(6) 0.0360(8) -0.0105(6) 0.0079(6) -0.0055(4) N3 0.0275(6) 0.0286(7) 0.0228(7) -0.0015(6) 0.0020(6) 0.0003(5) C5 0.0276(7) 0.0266(7) 0.0215(8) -0.0007(6) 0.0021(7) -0.0014(6) C6 0.0322(8) 0.0245(7) 0.0245(9) 0.0007(7) 0.0027(7) 0.0017(6) N2 0.0217(6) 0.0279(6) 0.0193(7) 0.0016(5) 0.0007(6) 0.0007(5) O1W 0.0484(8) 0.0500(8) 0.0392(9) -0.0187(7) 0.0123(7) -0.0068(7) C4 0.0537(11) 0.0255(8) 0.0232(9) 0.0013(7) 0.0071(8) -0.0014(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 1.5076(14) . ? P1 O2 1.5095(12) . ? P1 O1 1.5569(12) . ? P1 C1 1.8469(14) . ? P2 O6 1.5061(13) . ? P2 O4 1.5082(10) . ? P2 O5 1.5361(11) . ? P2 C1 1.8660(16) . ? N1 C1 1.5085(17) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? O1 H1 0.871(10) . ? C1 C2 1.535(2) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? N3 C6 1.475(2) . ? N3 H3A 0.8900 . ? N3 H3B 0.8900 . ? N3 H3C 0.8900 . ? C5 C6 1.515(2) . ? C5 C4 1.527(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? N2 C4 1.477(2) . ? N2 H2D 0.8900 . ? N2 H2E 0.8900 . ? N2 H2F 0.8900 . ? O1W H2W1 0.844(10) . ? O1W H1W1 0.840(10) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? 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 O2 114.68(7) . . ? O3 P1 O1 109.17(8) . . ? O2 P1 O1 111.66(7) . . ? O3 P1 C1 110.76(7) . . ? O2 P1 C1 106.87(6) . . ? O1 P1 C1 103.06(7) . . ? O6 P2 O4 112.40(7) . . ? O6 P2 O5 113.98(8) . . ? O4 P2 O5 112.47(7) . . ? O6 P2 C1 106.03(7) . . ? O4 P2 C1 107.00(7) . . ? O5 P2 C1 104.13(7) . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? P1 O1 H1 104.1(19) . . ? N1 C1 C2 108.84(12) . . ? N1 C1 P1 107.80(9) . . ? C2 C1 P1 110.14(10) . . ? N1 C1 P2 107.05(9) . . ? C2 C1 P2 111.18(10) . . ? P1 C1 P2 111.69(7) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C6 N3 H3A 109.5 . . ? C6 N3 H3B 109.5 . . ? H3A N3 H3B 109.5 . . ? C6 N3 H3C 109.5 . . ? H3A N3 H3C 109.5 . . ? H3B N3 H3C 109.5 . . ? C6 C5 C4 112.17(15) . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5B 109.2 . . ? C4 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? N3 C6 C5 111.14(14) . . ? N3 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? N3 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C4 N2 H2D 109.5 . . ? C4 N2 H2E 109.5 . . ? H2D N2 H2E 109.5 . . ? C4 N2 H2F 109.5 . . ? H2D N2 H2F 109.5 . . ? H2E N2 H2F 109.5 . . ? H2W1 O1W H1W1 105.8(15) . . ? N2 C4 C5 110.36(14) . . ? N2 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? N2 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? 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 C1 N1 -77.43(11) . . . . ? O2 P1 C1 N1 48.13(11) . . . . ? O1 P1 C1 N1 165.92(10) . . . . ? O3 P1 C1 C2 41.19(12) . . . . ? O2 P1 C1 C2 166.75(10) . . . . ? O1 P1 C1 C2 -75.46(12) . . . . ? O3 P1 C1 P2 165.25(7) . . . . ? O2 P1 C1 P2 -69.19(8) . . . . ? O1 P1 C1 P2 48.60(10) . . . . ? O6 P2 C1 N1 -36.98(10) . . . . ? O4 P2 C1 N1 83.18(10) . . . . ? O5 P2 C1 N1 -157.54(9) . . . . ? O6 P2 C1 C2 -155.73(10) . . . . ? O4 P2 C1 C2 -35.57(12) . . . . ? O5 P2 C1 C2 83.71(11) . . . . ? O6 P2 C1 P1 80.79(9) . . . . ? O4 P2 C1 P1 -159.04(7) . . . . ? O5 P2 C1 P1 -39.76(9) . . . . ? C4 C5 C6 N3 159.60(15) . . . . ? C6 C5 C4 N2 -141.56(15) . . . . ? 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 O1W H1W1 O3 0.840(10) 2.038(11) 2.850(2) 163(3) 3_565 O1 H1 O5 0.871(10) 1.614(11) 2.479(2) 172(3) . O1W H2W1 O5 0.844(10) 1.973(11) 2.800(2) 166(2) 4 N2 H2F O2 0.89 1.97 2.8494(17) 171.3 2_565 N2 H2E O3 0.89 1.91 2.766(2) 159.4 . N2 H2D O4 0.89 1.83 2.6877(17) 161.5 2_665 N3 H3C O6 0.89 1.89 2.7430(18) 160.1 1_556 N3 H3B O6 0.89 1.93 2.8141(19) 174.2 3_466 N3 H3A O3 0.89 2.23 3.1000(19) 167.2 2_565 N1 H1C O2 0.89 1.90 2.7718(16) 167.1 3_565 N1 H1B O2 0.89 2.51 2.9867(16) 113.8 . N1 H1B O4 0.89 2.05 2.8433(17) 147.9 3_465 N1 H1A O1W 0.89 1.92 2.765(2) 157.6 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.259 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.041 # Attachment '2.cif' data_81201csp_0m _database_code_depnum_ccdc_archive 'CCDC 761328' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H21 N3 O7 P2' _chemical_formula_weight 297.19 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 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 9.9533(8) _cell_length_b 6.9947(6) _cell_length_c 18.0126(15) _cell_angle_alpha 90.00 _cell_angle_beta 103.3600(10) _cell_angle_gamma 90.00 _cell_volume 1220.11(18) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 5609 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 29.70 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.386 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8930 _exptl_absorpt_correction_T_max 0.9165 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7760 _diffrn_reflns_av_R_equivalents 0.0140 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2930 _reflns_number_gt 2737 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0471P)^2^+0.4344P] 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 SHELXL _refine_ls_extinction_coef 0.0099(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2930 _refine_ls_number_parameters 172 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0809 _refine_ls_wR_factor_gt 0.0798 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.039 _refine_ls_shift/su_mean 0.004 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.87808(13) 0.75394(17) 0.17620(7) 0.0146(2) Uani 1 1 d . . . C2 C 0.95349(14) 0.6002(2) 0.14060(8) 0.0222(3) Uani 1 1 d . . . H2A H 1.0508 0.6076 0.1627 0.033 Uiso 1 1 calc R . . H2B H 0.9369 0.6206 0.0865 0.033 Uiso 1 1 calc R . . H2C H 0.9200 0.4761 0.1503 0.033 Uiso 1 1 calc R . . C3 C 0.69746(18) 0.4663(2) 0.94304(9) 0.0310(3) Uani 1 1 d . . . H3A H 0.6096 0.4654 0.9071 0.046 Uiso 1 1 calc R . . H3B H 0.7685 0.4995 0.9173 0.046 Uiso 1 1 calc R . . H3C H 0.6958 0.5586 0.9823 0.046 Uiso 1 1 calc R . . C4 C 0.72642(15) 0.27034(19) 0.97843(8) 0.0215(3) Uani 1 1 d . . . H4 H 0.8215 0.2667 1.0092 0.026 Uiso 1 1 calc R . . C5 C 0.70939(15) 0.1191(2) 0.91626(8) 0.0235(3) Uani 1 1 d . . . H5A H 0.6117 0.0984 0.8949 0.028 Uiso 1 1 calc R . . H5B H 0.7500 0.1657 0.8757 0.028 Uiso 1 1 calc R . . H1W1 H 0.2819(18) 0.676(3) 0.2919(13) 0.059(7) Uiso 1 1 d D . . H2W1 H 0.189(2) 0.830(2) 0.2777(11) 0.042(6) Uiso 1 1 d D . . H3 H 0.858(2) 1.201(3) 0.2175(8) 0.056(7) Uiso 1 1 d D . . N1 N 0.90995(11) 0.71753(16) 0.26162(6) 0.0172(2) Uani 1 1 d . . . H1A H 0.8769 0.6037 0.2705 0.026 Uiso 1 1 calc R . . H1B H 0.8707 0.8080 0.2842 0.026 Uiso 1 1 calc R . . H1C H 1.0009 0.7196 0.2801 0.026 Uiso 1 1 calc R . . N2 N 0.77452(13) -0.06504(17) 0.94454(7) 0.0240(2) Uani 1 1 d . . . H2D H 0.8659 -0.0512 0.9570 0.036 Uiso 1 1 calc R . . H2E H 0.7516 -0.1533 0.9082 0.036 Uiso 1 1 calc R . . H2F H 0.7453 -0.1015 0.9855 0.036 Uiso 1 1 calc R . . N3 N 0.62885(13) 0.23334(16) 1.02920(6) 0.0212(2) Uani 1 1 d . . . H3D H 0.6375 0.3255 1.0640 0.032 Uiso 1 1 calc R . . H3E H 0.6487 0.1211 1.0524 0.032 Uiso 1 1 calc R . . H3F H 0.5425 0.2315 1.0012 0.032 Uiso 1 1 calc R . . O1 O 0.62762(9) 0.83240(13) 0.20265(5) 0.0187(2) Uani 1 1 d . . . O2 O 0.64635(10) 0.83318(14) 0.06487(5) 0.0200(2) Uani 1 1 d . . . O3 O 0.65590(10) 0.51963(13) 0.13752(5) 0.0197(2) Uani 1 1 d . . . O4 O 0.84227(10) 1.14030(13) 0.17611(5) 0.0203(2) Uani 1 1 d D . . O5 O 0.96098(10) 1.00131(14) 0.08022(5) 0.0225(2) Uani 1 1 d . . . O6 O 1.08379(10) 1.01096(14) 0.22140(6) 0.0227(2) Uani 1 1 d . . . O1W O 0.21599(12) 0.73359(17) 0.30508(7) 0.0322(3) Uani 1 1 d D . . P1 P 0.68703(3) 0.73188(4) 0.141935(17) 0.01382(10) Uani 1 1 d . . . P2 P 0.95063(3) 0.99149(4) 0.161641(17) 0.01456(10) Uani 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 C1 0.0161(6) 0.0131(5) 0.0144(5) 0.0002(4) 0.0032(4) 0.0005(4) C2 0.0229(6) 0.0177(6) 0.0273(6) -0.0036(5) 0.0086(5) 0.0030(5) C3 0.0392(9) 0.0195(7) 0.0361(8) 0.0055(6) 0.0126(7) 0.0018(6) C4 0.0235(6) 0.0187(6) 0.0224(6) 0.0002(5) 0.0057(5) -0.0003(5) C5 0.0284(7) 0.0222(7) 0.0199(6) -0.0006(5) 0.0055(5) 0.0045(5) N1 0.0176(5) 0.0173(5) 0.0162(5) 0.0031(4) 0.0026(4) -0.0006(4) N2 0.0268(6) 0.0192(6) 0.0245(5) -0.0032(5) 0.0031(5) 0.0000(5) N3 0.0267(6) 0.0184(5) 0.0181(5) -0.0001(4) 0.0045(4) 0.0008(4) O1 0.0207(4) 0.0168(4) 0.0200(4) -0.0015(3) 0.0076(3) 0.0011(3) O2 0.0217(4) 0.0209(5) 0.0159(4) 0.0034(3) 0.0010(3) -0.0005(4) O3 0.0231(5) 0.0135(4) 0.0219(5) -0.0018(3) 0.0041(4) -0.0033(3) O4 0.0211(5) 0.0162(5) 0.0230(5) -0.0025(4) 0.0037(4) 0.0025(3) O5 0.0254(5) 0.0262(5) 0.0174(4) 0.0021(4) 0.0079(4) -0.0020(4) O6 0.0181(5) 0.0217(5) 0.0245(5) 0.0045(4) -0.0028(4) -0.0030(4) O1W 0.0339(6) 0.0352(6) 0.0292(6) 0.0108(5) 0.0108(5) 0.0156(5) P1 0.01504(17) 0.01231(16) 0.01374(16) -0.00016(10) 0.00254(11) -0.00074(10) P2 0.01482(17) 0.01390(17) 0.01474(17) 0.00164(11) 0.00300(12) -0.00061(10) _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 C1 N1 1.5189(15) . ? C1 C2 1.5343(17) . ? C1 P2 1.8544(12) . ? C1 P1 1.8650(13) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.5114(19) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 N3 1.5023(17) . ? C4 C5 1.5214(18) . ? C4 H4 0.9800 . ? C5 N2 1.4784(18) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? N2 H2D 0.8900 . ? N2 H2E 0.8900 . ? N2 H2F 0.8900 . ? N3 H3D 0.8900 . ? N3 H3E 0.8900 . ? N3 H3F 0.8900 . ? O1 P1 1.5293(9) . ? O2 P1 1.5275(9) . ? O3 P1 1.5150(9) . ? O4 P2 1.5635(10) . ? O4 H3 0.841(10) . ? O5 P2 1.4954(10) . ? O6 P2 1.5081(10) . ? O1W H1W1 0.848(10) . ? O1W H2W1 0.841(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 107.34(10) . . ? N1 C1 P2 107.25(8) . . ? C2 C1 P2 108.96(9) . . ? N1 C1 P1 106.24(8) . . ? C2 C1 P1 111.32(8) . . ? P2 C1 P1 115.34(6) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N3 C4 C3 109.02(12) . . ? N3 C4 C5 110.52(11) . . ? C3 C4 C5 110.02(12) . . ? N3 C4 H4 109.1 . . ? C3 C4 H4 109.1 . . ? C5 C4 H4 109.1 . . ? N2 C5 C4 112.75(11) . . ? N2 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? N2 C5 H5B 109.0 . . ? C4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C5 N2 H2D 109.5 . . ? C5 N2 H2E 109.5 . . ? H2D N2 H2E 109.5 . . ? C5 N2 H2F 109.5 . . ? H2D N2 H2F 109.5 . . ? H2E N2 H2F 109.5 . . ? C4 N3 H3D 109.5 . . ? C4 N3 H3E 109.5 . . ? H3D N3 H3E 109.5 . . ? C4 N3 H3F 109.5 . . ? H3D N3 H3F 109.5 . . ? H3E N3 H3F 109.5 . . ? P2 O4 H3 119.2(17) . . ? H1W1 O1W H2W1 112(2) . . ? O3 P1 O2 113.51(5) . . ? O3 P1 O1 112.33(5) . . ? O2 P1 O1 111.81(5) . . ? O3 P1 C1 106.20(5) . . ? O2 P1 C1 107.36(5) . . ? O1 P1 C1 104.98(5) . . ? O5 P2 O6 116.58(6) . . ? O5 P2 O4 109.84(6) . . ? O6 P2 O4 110.32(6) . . ? O5 P2 C1 107.29(6) . . ? O6 P2 C1 106.66(5) . . ? O4 P2 C1 105.47(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 N3 C4 C5 N2 -76.49(15) . . . . ? C3 C4 C5 N2 163.06(12) . . . . ? N1 C1 P1 O3 -77.67(8) . . . . ? C2 C1 P1 O3 38.88(10) . . . . ? P2 C1 P1 O3 163.67(6) . . . . ? N1 C1 P1 O2 160.60(7) . . . . ? C2 C1 P1 O2 -82.86(9) . . . . ? P2 C1 P1 O2 41.94(8) . . . . ? N1 C1 P1 O1 41.49(9) . . . . ? C2 C1 P1 O1 158.03(9) . . . . ? P2 C1 P1 O1 -77.17(7) . . . . ? N1 C1 P2 O5 162.04(8) . . . . ? C2 C1 P2 O5 46.15(10) . . . . ? P1 C1 P2 O5 -79.86(8) . . . . ? N1 C1 P2 O6 36.42(9) . . . . ? C2 C1 P2 O6 -79.47(10) . . . . ? P1 C1 P2 O6 154.53(7) . . . . ? N1 C1 P2 O4 -80.89(9) . . . . ? C2 C1 P2 O4 163.22(8) . . . . ? P1 C1 P2 O4 37.21(8) . . . . ? 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 H3F O2 0.89 2.03 2.9061(15) 167.7 3_666 N3 H3E O4 0.89 2.59 3.0563(15) 113.5 1_546 N3 H3E O2 0.89 2.03 2.8680(15) 157.1 1_546 N3 H3D O3 0.89 1.88 2.7653(14) 179.9 1_556 N2 H2F O2 0.89 1.97 2.8479(16) 169.3 1_546 N2 H2E O1W 0.89 1.89 2.7136(16) 152.2 4_666 N2 H2D O5 0.89 2.23 2.7453(15) 116.2 1_546 N2 H2D O5 0.89 2.02 2.8055(16) 146.7 3_766 N1 H1C O1W 0.89 2.09 2.9669(17) 170.5 1_655 N1 H1B O3 0.89 2.10 2.9573(14) 160.7 2_655 N1 H1A O4 0.89 2.59 3.0254(15) 110.9 2_645 N1 H1A O1 0.89 1.96 2.8147(14) 160.1 2_645 O4 H3 O1 0.841(10) 1.685(10) 2.5223(13) 174(3) 2_655 O1W H2W1 O6 0.841(9) 1.799(11) 2.6174(14) 164(2) 1_455 O1W H1W1 O6 0.848(10) 1.825(11) 2.6576(15) 167(2) 2_645 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.438 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.057 # Attachment '3.cif' data_91207csp_0m _database_code_depnum_ccdc_archive 'CCDC 761329' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H21 N3 O7 P2' _chemical_formula_weight 309.20 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 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 5.7306(5) _cell_length_b 19.9861(18) _cell_length_c 11.2688(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.3420(10) _cell_angle_gamma 90.00 _cell_volume 1265.44(19) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 6023 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 29.57 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.376 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8673 _exptl_absorpt_correction_T_max 0.8861 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8302 _diffrn_reflns_av_R_equivalents 0.0122 _diffrn_reflns_av_sigmaI/netI 0.0135 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 28.00 _reflns_number_total 3046 _reflns_number_gt 2848 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0434P)^2^+0.5170P] 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 3046 _refine_ls_number_parameters 177 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0800 _refine_ls_wR_factor_gt 0.0786 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.082 _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 C1 C 0.2993(2) 0.00279(5) 0.77207(10) 0.0140(2) Uani 1 1 d . . . N1 N 0.56120(19) 0.00367(5) 0.82758(10) 0.0165(2) Uani 1 1 d . . . H1A H 0.6238 -0.0363 0.8187 0.025 Uiso 1 1 calc R . . H1B H 0.5805 0.0134 0.9060 0.025 Uiso 1 1 calc R . . H1C H 0.6339 0.0345 0.7908 0.025 Uiso 1 1 calc R . . C3 C 0.2482(3) 0.73067(7) 0.15706(13) 0.0283(3) Uani 1 1 d . . . H3C H 0.3757 0.7412 0.2248 0.034 Uiso 1 1 calc R . . H3D H 0.1038 0.7239 0.1883 0.034 Uiso 1 1 calc R . . C4 C 0.5206(3) 0.67789(7) 0.04430(14) 0.0281(3) Uani 1 1 d . . . H4A H 0.5469 0.6377 0.0006 0.034 Uiso 1 1 calc R . . H4B H 0.6585 0.6846 0.1085 0.034 Uiso 1 1 calc R . . C5 C 0.4954(2) 0.73689(7) -0.04092(13) 0.0249(3) Uani 1 1 d . . . H5A H 0.6452 0.7442 -0.0667 0.030 Uiso 1 1 calc R . . H5B H 0.3755 0.7268 -0.1122 0.030 Uiso 1 1 calc R . . C6 C 0.2131(3) 0.78865(7) 0.06912(14) 0.0292(3) Uani 1 1 d . . . H6A H 0.0767 0.7799 0.0050 0.035 Uiso 1 1 calc R . . H6B H 0.1812 0.8291 0.1109 0.035 Uiso 1 1 calc R . . H3 H 0.064(5) 0.0732(13) 0.980(2) 0.074(8) Uiso 1 1 d . . . H1W1 H 0.690(2) 0.1341(10) 0.6311(17) 0.052(6) Uiso 1 1 d D . . H2W1 H 0.480(3) 0.1521(11) 0.6561(15) 0.056(6) Uiso 1 1 d D . . C2 C 0.2787(3) -0.00442(7) 0.63496(12) 0.0230(3) Uani 1 1 d . . . H2A H 0.3565 0.0327 0.6049 0.035 Uiso 1 1 calc R . . H2B H 0.1138 -0.0050 0.5962 0.035 Uiso 1 1 calc R . . H2C H 0.3530 -0.0454 0.6178 0.035 Uiso 1 1 calc R . . N2 N 0.3070(2) 0.66873(6) 0.09814(10) 0.0227(2) Uani 1 1 d . . . H2D H 0.1829 0.6568 0.0399 0.027 Uiso 1 1 calc R . . H2E H 0.3335 0.6355 0.1531 0.027 Uiso 1 1 calc R . . N3 N 0.4274(2) 0.79870(5) 0.01589(11) 0.0235(2) Uani 1 1 d . . . H3A H 0.3986 0.8313 -0.0401 0.028 Uiso 1 1 calc R . . H3B H 0.5493 0.8120 0.0743 0.028 Uiso 1 1 calc R . . O1 O -0.09083(16) 0.08200(5) 0.74133(9) 0.0240(2) Uani 1 1 d . . . O2 O 0.31671(17) 0.13891(5) 0.77509(9) 0.0228(2) Uani 1 1 d . . . O3 O 0.18976(17) 0.08559(5) 0.94696(8) 0.0211(2) Uani 1 1 d . . . O4 O 0.32451(16) -0.13035(5) 0.80998(8) 0.0220(2) Uani 1 1 d . . . O5 O 0.17402(17) -0.06048(5) 0.96478(8) 0.0221(2) Uani 1 1 d . . . O6 O -0.08657(16) -0.07741(4) 0.75874(9) 0.0211(2) Uani 1 1 d . . . O1W O 0.56372(19) 0.15566(6) 0.60260(9) 0.0307(2) Uani 1 1 d D . . P1 P 0.16359(5) 0.082698(15) 0.80623(3) 0.01514(9) Uani 1 1 d . . . P2 P 0.16727(5) -0.072433(15) 0.83079(3) 0.01478(9) Uani 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 C1 0.0126(5) 0.0148(5) 0.0144(5) -0.0006(4) 0.0020(4) 0.0000(4) N1 0.0136(5) 0.0171(5) 0.0188(5) -0.0010(4) 0.0034(4) 0.0003(3) C3 0.0332(7) 0.0280(7) 0.0257(7) -0.0011(5) 0.0109(6) 0.0012(6) C4 0.0300(7) 0.0229(7) 0.0330(7) 0.0070(6) 0.0105(6) 0.0084(5) C5 0.0285(7) 0.0233(7) 0.0245(6) 0.0035(5) 0.0088(5) 0.0022(5) C6 0.0289(7) 0.0220(7) 0.0376(8) 0.0011(6) 0.0092(6) 0.0071(5) C2 0.0290(7) 0.0249(6) 0.0150(6) -0.0004(5) 0.0041(5) -0.0028(5) N2 0.0276(6) 0.0184(5) 0.0210(5) 0.0047(4) 0.0022(4) -0.0005(4) N3 0.0252(6) 0.0160(5) 0.0273(6) 0.0033(4) 0.0004(4) -0.0007(4) O1 0.0161(4) 0.0249(5) 0.0297(5) 0.0034(4) 0.0008(4) 0.0034(3) O2 0.0251(5) 0.0174(4) 0.0279(5) 0.0018(4) 0.0100(4) -0.0034(3) O3 0.0215(5) 0.0230(5) 0.0198(5) -0.0026(3) 0.0067(4) -0.0009(3) O4 0.0236(5) 0.0175(4) 0.0257(5) 0.0014(3) 0.0071(4) 0.0047(3) O5 0.0253(5) 0.0257(5) 0.0164(4) -0.0010(3) 0.0072(3) -0.0056(4) O6 0.0162(4) 0.0200(4) 0.0265(5) -0.0068(3) 0.0028(4) -0.0020(3) O1W 0.0242(5) 0.0421(6) 0.0262(5) 0.0131(4) 0.0056(4) 0.0047(4) P1 0.01325(16) 0.01387(15) 0.01854(16) 0.00104(11) 0.00370(11) 0.00071(10) P2 0.01517(16) 0.01383(15) 0.01570(16) -0.00059(10) 0.00392(11) -0.00141(10) _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 C1 N1 1.5081(15) . ? C1 C2 1.5331(16) . ? C1 P1 1.8497(12) . ? C1 P2 1.8623(12) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? C3 N2 1.4748(18) . ? C3 C6 1.512(2) . ? C3 H3C 0.9700 . ? C3 H3D 0.9700 . ? C4 N2 1.4803(18) . ? C4 C5 1.5097(18) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N3 1.4785(17) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N3 1.4825(18) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? N2 H2D 0.9000 . ? N2 H2E 0.9000 . ? N3 H3A 0.9000 . ? N3 H3B 0.9000 . ? O1 P1 1.4971(9) . ? O2 P1 1.5088(9) . ? O3 P1 1.5643(10) . ? O3 H3 0.91(3) . ? O4 P2 1.5133(9) . ? O5 P2 1.5216(9) . ? O6 P2 1.5233(9) . ? O1W H1W1 0.848(9) . ? O1W H2W1 0.843(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 106.99(10) . . ? N1 C1 P1 109.18(7) . . ? C2 C1 P1 109.80(8) . . ? N1 C1 P2 107.62(7) . . ? C2 C1 P2 109.03(8) . . ? P1 C1 P2 113.96(6) . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? N2 C3 C6 111.15(11) . . ? N2 C3 H3C 109.4 . . ? C6 C3 H3C 109.4 . . ? N2 C3 H3D 109.4 . . ? C6 C3 H3D 109.4 . . ? H3C C3 H3D 108.0 . . ? N2 C4 C5 111.96(11) . . ? N2 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? N2 C4 H4B 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? N3 C5 C4 112.19(11) . . ? N3 C5 H5A 109.2 . . ? C4 C5 H5A 109.2 . . ? N3 C5 H5B 109.2 . . ? C4 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? N3 C6 C3 110.80(11) . . ? N3 C6 H6A 109.5 . . ? C3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C3 N2 C4 111.18(11) . . ? C3 N2 H2D 109.4 . . ? C4 N2 H2D 109.4 . . ? C3 N2 H2E 109.4 . . ? C4 N2 H2E 109.4 . . ? H2D N2 H2E 108.0 . . ? C5 N3 C6 111.81(11) . . ? C5 N3 H3A 109.3 . . ? C6 N3 H3A 109.3 . . ? C5 N3 H3B 109.3 . . ? C6 N3 H3B 109.3 . . ? H3A N3 H3B 107.9 . . ? P1 O3 H3 118.7(17) . . ? H1W1 O1W H2W1 104.3(13) . . ? O1 P1 O2 116.64(6) . . ? O1 P1 O3 112.68(6) . . ? O2 P1 O3 105.31(5) . . ? O1 P1 C1 107.41(5) . . ? O2 P1 C1 107.87(5) . . ? O3 P1 C1 106.41(5) . . ? O4 P2 O5 111.97(5) . . ? O4 P2 O6 113.75(5) . . ? O5 P2 O6 111.99(5) . . ? O4 P2 C1 105.45(5) . . ? O5 P2 C1 107.04(5) . . ? O6 P2 C1 105.99(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 N2 C4 C5 N3 52.34(16) . . . . ? N2 C3 C6 N3 -56.79(16) . . . . ? C6 C3 N2 C4 56.52(16) . . . . ? C5 C4 N2 C3 -54.18(16) . . . . ? C4 C5 N3 C6 -52.75(15) . . . . ? C3 C6 N3 C5 54.75(15) . . . . ? N1 C1 P1 O1 175.50(8) . . . . ? C2 C1 P1 O1 58.49(9) . . . . ? P2 C1 P1 O1 -64.14(8) . . . . ? N1 C1 P1 O2 48.99(9) . . . . ? C2 C1 P1 O2 -68.01(9) . . . . ? P2 C1 P1 O2 169.36(6) . . . . ? N1 C1 P1 O3 -63.60(9) . . . . ? C2 C1 P1 O3 179.39(8) . . . . ? P2 C1 P1 O3 56.76(7) . . . . ? N1 C1 P2 O4 -50.70(9) . . . . ? C2 C1 P2 O4 65.02(9) . . . . ? P1 C1 P2 O4 -171.93(6) . . . . ? N1 C1 P2 O5 68.69(8) . . . . ? C2 C1 P2 O5 -175.59(8) . . . . ? P1 C1 P2 O5 -52.54(8) . . . . ? N1 C1 P2 O6 -171.62(7) . . . . ? C2 C1 P2 O6 -55.91(9) . . . . ? P1 C1 P2 O6 67.14(7) . . . . ? 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 H3B O3 0.90 2.57 3.1583(15) 123.2 3_666 N3 H3B O2 0.90 1.98 2.8096(15) 152.5 3_666 N3 H3A O5 0.90 2.52 3.1673(15) 129.1 1_564 N3 H3A O4 0.90 1.83 2.6841(15) 158.3 1_564 N2 H2E O6 0.90 1.66 2.5581(14) 173.5 4_665 N2 H2D O1W 0.90 1.92 2.7944(15) 163.8 2 O1W H2W1 O2 0.843(9) 1.800(10) 2.6412(14) 175(2) . O1W H1W1 O1 0.848(9) 1.895(12) 2.7043(14) 158.9(18) 1_655 O3 H3 O5 0.91(3) 1.63(3) 2.5303(14) 173(3) 3_557 N1 H1C O1 0.89 2.01 2.8520(15) 156.9 1_655 N1 H1B O5 0.89 2.04 2.7695(14) 137.9 3_657 N1 H1A O6 0.89 2.08 2.8138(14) 139.1 1_655 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.380 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.054 # Attachment '4.cif' data_91109csp_0m _database_code_depnum_ccdc_archive 'CCDC 761330' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H20 N2 O9 P2' _chemical_formula_weight 302.16 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.629(8) _cell_length_b 6.963(3) _cell_length_c 20.786(11) _cell_angle_alpha 90.00 _cell_angle_beta 117.990(5) _cell_angle_gamma 90.00 _cell_volume 2508.8(19) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 4782 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 29.67 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.386 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8158 _exptl_absorpt_correction_T_max 0.9165 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6990 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2468 _reflns_number_gt 2269 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0367P)^2^+2.5724P] 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 SHELXL _refine_ls_extinction_coef 0.0135(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2468 _refine_ls_number_parameters 185 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0784 _refine_ls_wR_factor_gt 0.0765 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.34775(9) 0.2254(2) 0.23617(8) 0.0183(3) Uani 1 1 d . . . C2 C 0.40328(10) 0.3802(2) 0.23720(10) 0.0268(4) Uani 1 1 d . . . H2A H 0.3832 0.5045 0.2392 0.040 Uiso 1 1 calc R . . H2B H 0.4089 0.3706 0.1938 0.040 Uiso 1 1 calc R . . H2C H 0.4526 0.3628 0.2792 0.040 Uiso 1 1 calc R . . C3 C 0.31611(11) 0.6497(3) 0.05309(10) 0.0335(4) Uani 1 1 d . . . H3A H 0.3002 0.5163 0.0435 0.040 Uiso 1 1 calc R . . H3B H 0.3682 0.6532 0.0932 0.040 Uiso 1 1 calc R . . C4 C 0.18440(11) 0.7643(3) 0.01346(10) 0.0318(4) Uani 1 1 d . . . H4A H 0.1529 0.8419 0.0280 0.038 Uiso 1 1 calc R . . H4B H 0.1625 0.6362 0.0022 0.038 Uiso 1 1 calc R . . H1 H 0.1848(19) 0.202(4) 0.2031(15) 0.085(8) Uiso 1 1 d D . . H5 H 0.4978(10) -0.024(5) 0.3126(18) 0.085(8) Uiso 1 1 d D . . H1W1 H 0.4775(19) 0.773(4) 0.3962(16) 0.133(12) Uiso 1 1 d D . . H2W1 H 0.483(2) 0.593(3) 0.422(2) 0.133(12) Uiso 1 1 d D . . H1W2 H 0.5263(12) 0.281(8) 0.437(2) 0.163(15) Uiso 1 1 d D . . H2W2 H 0.483(2) 0.282(8) 0.4709(13) 0.163(15) Uiso 1 1 d D . . H1W3 H 0.1504(13) 0.324(4) 0.9338(12) 0.070(6) Uiso 1 1 d D . . H2W3 H 0.1630(11) 0.255(4) 0.9988(8) 0.070(6) Uiso 1 1 d D . . N1 N 0.33998(8) 0.24482(19) 0.30484(7) 0.0205(3) Uani 1 1 d . . . H1A H 0.3866 0.2445 0.3434 0.031 Uiso 1 1 calc R . . H1B H 0.3126 0.1468 0.3080 0.031 Uiso 1 1 calc R . . H1C H 0.3161 0.3546 0.3035 0.031 Uiso 1 1 calc R . . N2 N 0.26388(9) 0.7544(2) 0.07400(8) 0.0300(3) Uani 1 1 d . . . H2D H 0.2634 0.6951 0.1123 0.036 Uiso 1 1 calc R . . H2E H 0.2819 0.8743 0.0879 0.036 Uiso 1 1 calc R . . O1 O 0.19504(7) 0.14755(16) 0.17743(7) 0.0243(3) Uani 1 1 d D . . O2 O 0.23476(7) 0.47172(16) 0.15246(6) 0.0239(3) Uani 1 1 d . . . O3 O 0.25235(7) 0.16763(17) 0.09252(6) 0.0270(3) Uani 1 1 d . . . O4 O 0.32698(7) -0.15809(16) 0.23063(6) 0.0257(3) Uani 1 1 d . . . O5 O 0.45924(7) -0.03006(19) 0.31255(6) 0.0286(3) Uani 1 1 d D . . O6 O 0.40737(7) -0.02281(18) 0.17578(6) 0.0272(3) Uani 1 1 d . . . O1W O 0.50574(11) 0.6995(3) 0.43051(10) 0.0623(5) Uani 1 1 d D . . O2W O 0.48059(9) 0.3003(3) 0.42934(9) 0.0558(4) Uani 1 1 d D . . O3W O 0.12829(9) 0.3006(3) 0.95900(8) 0.0468(4) Uani 1 1 d D . . P1 P 0.38714(2) -0.01551(6) 0.23805(2) 0.01938(14) Uani 1 1 d . . . P2 P 0.25168(2) 0.26064(5) 0.15688(2) 0.01843(14) Uani 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 C1 0.0202(7) 0.0193(7) 0.0178(7) -0.0009(6) 0.0110(6) -0.0004(6) C2 0.0261(8) 0.0250(8) 0.0326(9) -0.0003(7) 0.0163(7) -0.0043(7) C3 0.0379(10) 0.0350(10) 0.0275(9) 0.0051(7) 0.0151(8) 0.0059(8) C4 0.0364(10) 0.0330(9) 0.0302(9) 0.0002(7) 0.0191(8) -0.0008(8) N1 0.0227(7) 0.0211(7) 0.0189(7) -0.0019(5) 0.0109(5) 0.0001(5) N2 0.0424(9) 0.0301(8) 0.0196(7) -0.0006(6) 0.0163(7) -0.0030(6) O1 0.0233(6) 0.0217(6) 0.0302(6) -0.0015(5) 0.0145(5) -0.0025(4) O2 0.0287(6) 0.0199(6) 0.0262(6) 0.0031(4) 0.0156(5) 0.0028(4) O3 0.0308(6) 0.0300(6) 0.0198(6) -0.0028(5) 0.0115(5) 0.0033(5) O4 0.0290(6) 0.0211(6) 0.0300(6) -0.0012(5) 0.0163(5) -0.0020(5) O5 0.0236(6) 0.0387(7) 0.0224(6) 0.0025(5) 0.0098(5) 0.0056(5) O6 0.0278(6) 0.0360(7) 0.0220(6) -0.0008(5) 0.0151(5) 0.0050(5) O1W 0.0597(11) 0.0666(12) 0.0493(10) 0.0108(9) 0.0162(8) -0.0026(9) O2W 0.0424(9) 0.0743(12) 0.0360(8) -0.0135(8) 0.0062(7) 0.0035(8) O3W 0.0472(9) 0.0589(10) 0.0354(8) 0.0088(7) 0.0203(7) 0.0025(8) P1 0.0204(2) 0.0203(2) 0.0197(2) -0.00068(15) 0.01130(17) 0.00149(15) P2 0.0203(2) 0.0183(2) 0.0172(2) -0.00006(14) 0.00921(17) 0.00047(14) _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 C1 N1 1.511(2) . ? C1 C2 1.526(2) . ? C1 P1 1.8396(17) . ? C1 P2 1.8482(17) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 N2 1.480(2) . ? C3 C4 1.503(3) 7_565 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N2 1.476(2) . ? C4 C3 1.503(3) 7_565 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? N2 H2D 0.9000 . ? N2 H2E 0.9000 . ? O1 P2 1.5763(12) . ? O1 H1 0.754(10) . ? O2 P2 1.5002(13) . ? O3 P2 1.4919(13) . ? O4 P1 1.4944(13) . ? O5 P1 1.5344(13) . ? O5 H5 0.758(10) . ? O6 P1 1.5224(13) . ? O1W H1W1 0.840(10) . ? O1W H2W1 0.841(10) . ? O2W H1W2 0.848(10) . ? O2W H2W2 0.853(10) . ? O3W H1W3 0.839(10) . ? O3W H2W3 0.847(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 108.15(12) . . ? N1 C1 P1 106.83(10) . . ? C2 C1 P1 110.70(11) . . ? N1 C1 P2 108.51(10) . . ? C2 C1 P2 109.97(11) . . ? P1 C1 P2 112.51(8) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 C4 111.57(15) . 7_565 ? N2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 7_565 . ? N2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 7_565 . ? H3A C3 H3B 108.0 . . ? N2 C4 C3 110.54(15) . 7_565 ? N2 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 7_565 . ? N2 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 7_565 . ? H4A C4 H4B 108.1 . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C4 N2 C3 111.92(14) . . ? C4 N2 H2D 109.2 . . ? C3 N2 H2D 109.2 . . ? C4 N2 H2E 109.2 . . ? C3 N2 H2E 109.2 . . ? H2D N2 H2E 107.9 . . ? P2 O1 H1 113(3) . . ? P1 O5 H5 116(3) . . ? H1W1 O1W H2W1 106.7(16) . . ? H1W2 O2W H2W2 104.2(16) . . ? H1W3 O3W H2W3 105.5(15) . . ? O4 P1 O6 113.51(7) . . ? O4 P1 O5 111.73(7) . . ? O6 P1 O5 111.76(8) . . ? O4 P1 C1 107.43(7) . . ? O6 P1 C1 106.69(7) . . ? O5 P1 C1 105.13(7) . . ? O3 P2 O2 117.73(7) . . ? O3 P2 O1 109.29(7) . . ? O2 P2 O1 110.00(7) . . ? O3 P2 C1 107.90(7) . . ? O2 P2 C1 106.79(7) . . ? O1 P2 C1 104.25(7) . . ? 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 C3 C4 N2 C3 -55.0(2) 7_565 . . . ? C4 C3 N2 C4 55.5(2) 7_565 . . . ? N1 C1 P1 O4 67.12(11) . . . . ? C2 C1 P1 O4 -175.35(11) . . . . ? P2 C1 P1 O4 -51.85(10) . . . . ? N1 C1 P1 O6 -170.83(9) . . . . ? C2 C1 P1 O6 -53.29(12) . . . . ? P2 C1 P1 O6 70.20(10) . . . . ? N1 C1 P1 O5 -52.01(11) . . . . ? C2 C1 P1 O5 65.52(12) . . . . ? P2 C1 P1 O5 -170.98(8) . . . . ? N1 C1 P2 O3 -157.83(10) . . . . ? C2 C1 P2 O3 84.06(12) . . . . ? P1 C1 P2 O3 -39.84(10) . . . . ? N1 C1 P2 O2 74.72(11) . . . . ? C2 C1 P2 O2 -43.39(12) . . . . ? P1 C1 P2 O2 -167.29(7) . . . . ? N1 C1 P2 O1 -41.72(11) . . . . ? C2 C1 P2 O1 -159.83(11) . . . . ? P1 C1 P2 O1 76.27(9) . . . . ? 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 O1 H1 O4 0.754(10) 1.789(11) 2.5388(18) 173(4) 4 O5 H5 O6 0.758(10) 1.760(11) 2.5141(19) 172(4) 2_655 O1W H1W1 O5 0.840(10) 2.11(2) 2.879(2) 152(4) 1_565 O1W H2W1 O2W 0.841(10) 2.047(19) 2.821(3) 153(4) . O2W H1W2 O3W 0.848(10) 1.915(13) 2.757(3) 171(5) 8 O2W H2W2 O1W 0.853(10) 1.960(16) 2.797(3) 167(5) 5_666 O3W H1W3 O3 0.839(10) 2.219(14) 3.007(2) 156(2) 7_556 O3W H1W3 O6 0.839(10) 2.44(2) 2.982(2) 123(2) 7_556 O3W H2W3 O3 0.847(10) 2.010(11) 2.854(2) 174(3) 1_556 N1 H1A O2W 0.89 1.91 2.786(2) 167.2 . N1 H1B O2 0.89 1.93 2.7891(18) 160.4 4_545 N1 H1C O1 0.89 2.11 2.951(2) 157.6 4 N1 H1C O4 0.89 2.56 3.078(2) 118.2 4 N2 H2D O2 0.90 1.97 2.781(2) 149.5 . N2 H2D O4 0.90 2.40 2.953(2) 119.6 1_565 N2 H2E O3 0.90 2.14 2.926(2) 145.8 1_565 N2 H2E O6 0.90 2.39 3.037(2) 129.3 1_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.390 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.056