Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Liangjie Yuan' _publ_contact_author_address ; college of chemistry and molecular science, wuhan university wuhan 430072 china ; _publ_contact_author_phone +86-27-87218264 _publ_contact_author_fax +86-27-68754067 _publ_contact_author_email ljyuan@whu.edu.cn _publ_section_title ;Self-Assembly of Organic Acid-Base Compounds from 2-D Layered Network to 3-D Supramolecular: Synthesis, Structure and Photoluminescence ; loop_ _publ_author_name 'Simin Wu.' 'Shuoping Chen.' 'Ming Li.' 'Jiangfeng Xiang.' 'Yong Xiao.' ; Liangjie Yuan ; # ----------------------------------------------------------- data_70111csp_0m _database_code_depnum_ccdc_archive 'CCDC 633788' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H30 N4 O14 P4' _chemical_formula_weight 602.30 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 5.4669(13) _cell_length_b 9.497(2) _cell_length_c 11.694(3) _cell_angle_alpha 83.366(3) _cell_angle_beta 89.406(4) _cell_angle_gamma 77.092(4) _cell_volume 587.8(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2281 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 29.12 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.702 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 314 _exptl_absorpt_coefficient_mu 0.400 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.7923 _exptl_absorpt_correction_T_max 0.9573 _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 3733 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2574 _reflns_number_gt 2354 _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^)+(0.0000P)^2^+3.7790P] 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 0.034(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2574 _refine_ls_number_parameters 189 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1579 _refine_ls_wR_factor_gt 0.1569 _refine_ls_goodness_of_fit_ref 1.172 _refine_ls_restrained_S_all 1.171 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.4840(2) 0.72434(11) -0.00384(9) 0.0164(3) Uani 1 1 d . . . P2 P 0.3883(2) 0.84894(12) 0.23155(9) 0.0174(3) Uani 1 1 d . . . O1 O 0.7036(6) 0.6171(4) -0.0584(3) 0.0243(7) Uani 1 1 d . . . O2 O 0.2571(6) 0.6598(3) 0.0152(3) 0.0237(7) Uani 1 1 d . . . O3 O 0.4456(6) 0.8690(3) -0.0760(3) 0.0253(7) Uani 1 1 d . . . O4 O 0.2382(6) 0.9803(4) 0.1480(3) 0.0234(7) Uani 1 1 d . . . O5 O 0.5461(6) 0.9003(4) 0.3145(3) 0.0278(7) Uani 1 1 d . . . O6 O 0.2061(6) 0.7624(4) 0.2792(3) 0.0265(7) Uani 1 1 d . . . O7 O 0.2411(12) 0.5668(6) 0.4756(4) 0.0692(16) Uani 1 1 d D . . N1 N 0.8244(6) 0.8204(4) 0.1142(3) 0.0197(7) Uani 1 1 d . . . H1A H 0.9080 0.8182 0.1795 0.030 Uiso 1 1 calc R . . H1B H 0.7608 0.9124 0.0861 0.030 Uiso 1 1 calc R . . H1C H 0.9284 0.7770 0.0633 0.030 Uiso 1 1 calc R . . N2 N 0.7930(7) 0.8743(4) 0.5037(3) 0.0237(8) Uani 1 1 d . . . C1 C 0.6139(7) 0.7418(4) 0.1373(3) 0.0167(8) Uani 1 1 d . . . C2 C 0.7250(9) 0.5922(5) 0.2034(4) 0.0264(10) Uani 1 1 d . . . H2A H 0.8561 0.5397 0.1592 0.040 Uiso 1 1 calc R . . H2B H 0.5958 0.5386 0.2164 0.040 Uiso 1 1 calc R . . H2C H 0.7927 0.6047 0.2760 0.040 Uiso 1 1 calc R . . C3 C 0.7168(9) 0.7680(5) 0.5688(4) 0.0294(10) Uani 1 1 d . . . H1 H 0.5946 0.7264 0.5404 0.035 Uiso 1 1 calc R . . C4 C 0.8173(10) 0.7190(5) 0.6777(4) 0.0303(10) Uani 1 1 d . . . H2 H 0.7628 0.6460 0.7240 0.036 Uiso 1 1 calc R . . C5 C 1.0011(10) 0.7818(5) 0.7159(4) 0.0294(10) Uani 1 1 d . . . H3 H 1.0731 0.7501 0.7887 0.035 Uiso 1 1 calc R . . C6 C 1.0790(9) 0.8911(5) 0.6473(4) 0.0252(9) Uani 1 1 d . . . H4 H 1.2041 0.9322 0.6734 0.030 Uiso 1 1 calc R . . C7 C 0.9701(8) 0.9394(5) 0.5392(4) 0.0218(9) Uani 1 1 d . . . H5 H 0.731(14) 0.890(8) 0.435(6) 0.06(2) Uiso 1 1 d . . . H6 H 0.222(14) 0.622(6) 0.412(4) 0.06(2) Uiso 1 1 d D . . H7B H 0.369(16) 0.501(10) 0.467(8) 0.09(5) Uiso 0.50 1 d PD . . H8 H 0.722(12) 0.526(7) -0.028(6) 0.047(18) Uiso 1 1 d . . . H9 H 0.314(15) 1.033(8) 0.130(7) 0.07(3) Uiso 1 1 d . . . H7A H 0.119(15) 0.528(13) 0.480(9) 0.09(5) Uiso 0.50 1 d PD . . 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 0.0165(5) 0.0158(5) 0.0173(5) -0.0019(4) 0.0004(4) -0.0046(4) P2 0.0156(5) 0.0215(5) 0.0155(5) -0.0022(4) -0.0007(4) -0.0047(4) O1 0.0255(17) 0.0219(16) 0.0267(17) -0.0051(13) 0.0088(13) -0.0071(13) O2 0.0179(15) 0.0251(16) 0.0304(17) -0.0053(13) 0.0011(12) -0.0084(12) O3 0.0300(17) 0.0207(15) 0.0232(16) 0.0034(12) -0.0038(13) -0.0042(13) O4 0.0215(16) 0.0223(16) 0.0247(16) -0.0018(12) -0.0021(12) -0.0014(13) O5 0.0269(17) 0.0368(18) 0.0221(16) -0.0080(13) -0.0038(13) -0.0097(14) O6 0.0224(16) 0.0349(18) 0.0229(16) 0.0035(13) 0.0034(12) -0.0118(14) O7 0.097(4) 0.050(3) 0.050(3) 0.014(2) 0.007(3) -0.007(3) N1 0.0146(16) 0.0235(18) 0.0218(18) -0.0042(14) 0.0008(13) -0.0052(13) N2 0.026(2) 0.0271(19) 0.0186(18) -0.0036(15) -0.0013(15) -0.0071(15) C1 0.0158(18) 0.0182(19) 0.0167(18) 0.0001(14) -0.0005(14) -0.0061(15) C2 0.027(2) 0.020(2) 0.029(2) 0.0064(17) -0.0058(18) -0.0027(17) C3 0.030(2) 0.031(2) 0.029(2) -0.0045(19) 0.0012(19) -0.009(2) C4 0.037(3) 0.028(2) 0.025(2) -0.0004(18) 0.002(2) -0.008(2) C5 0.037(3) 0.028(2) 0.020(2) -0.0032(17) -0.0018(19) -0.001(2) C6 0.028(2) 0.026(2) 0.022(2) -0.0060(17) -0.0049(18) -0.0043(18) C7 0.022(2) 0.022(2) 0.020(2) -0.0063(16) -0.0014(16) -0.0002(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 P1 O3 1.500(3) . ? P1 O2 1.505(3) . ? P1 O1 1.573(3) . ? P1 C1 1.842(4) . ? P2 O6 1.492(3) . ? P2 O5 1.496(3) . ? P2 O4 1.569(3) . ? P2 C1 1.855(4) . ? N1 C1 1.512(5) . ? N2 C3 1.332(6) . ? N2 C7 1.351(6) . ? C1 C2 1.535(6) . ? C3 C4 1.380(7) . ? C4 C5 1.379(7) . ? C5 C6 1.379(7) . ? C6 C7 1.386(6) . ? C7 C7 1.480(9) 2_776 ? 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 116.73(19) . . ? O3 P1 O1 107.45(18) . . ? O2 P1 O1 111.27(18) . . ? O3 P1 C1 108.31(18) . . ? O2 P1 C1 108.73(18) . . ? O1 P1 C1 103.52(18) . . ? O6 P2 O5 118.13(19) . . ? O6 P2 O4 107.41(19) . . ? O5 P2 O4 110.66(19) . . ? O6 P2 C1 110.04(19) . . ? O5 P2 C1 105.40(19) . . ? O4 P2 C1 104.36(18) . . ? C3 N2 C7 122.8(4) . . ? N1 C1 C2 108.0(3) . . ? N1 C1 P1 106.9(3) . . ? C2 C1 P1 111.3(3) . . ? N1 C1 P2 107.0(3) . . ? C2 C1 P2 108.5(3) . . ? P1 C1 P2 114.7(2) . . ? N2 C3 C4 120.7(5) . . ? C5 C4 C3 117.9(5) . . ? C6 C5 C4 120.7(4) . . ? C5 C6 C7 119.7(4) . . ? N2 C7 C6 118.2(4) . . ? N2 C7 C7 117.5(5) . 2_776 ? C6 C7 C7 124.3(5) . 2_776 ? 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 -46.7(3) . . . . ? O2 P1 C1 N1 -174.5(2) . . . . ? O1 P1 C1 N1 67.1(3) . . . . ? O3 P1 C1 C2 -164.4(3) . . . . ? O2 P1 C1 C2 67.8(3) . . . . ? O1 P1 C1 C2 -50.6(3) . . . . ? O3 P1 C1 P2 71.8(3) . . . . ? O2 P1 C1 P2 -56.0(3) . . . . ? O1 P1 C1 P2 -174.4(2) . . . . ? O6 P2 C1 N1 -167.5(2) . . . . ? O5 P2 C1 N1 -39.1(3) . . . . ? O4 P2 C1 N1 77.5(3) . . . . ? O6 P2 C1 C2 -51.2(3) . . . . ? O5 P2 C1 C2 77.2(3) . . . . ? O4 P2 C1 C2 -166.2(3) . . . . ? O6 P2 C1 P1 74.1(3) . . . . ? O5 P2 C1 P1 -157.5(2) . . . . ? O4 P2 C1 P1 -40.9(3) . . . . ? C7 N2 C3 C4 0.2(7) . . . . ? N2 C3 C4 C5 -1.1(7) . . . . ? C3 C4 C5 C6 0.7(7) . . . . ? C4 C5 C6 C7 0.6(7) . . . . ? C3 N2 C7 C6 1.1(7) . . . . ? C3 N2 C7 C7 -177.3(5) . . . 2_776 ? C5 C6 C7 N2 -1.5(7) . . . . ? C5 C6 C7 C7 176.8(5) . . . 2_776 ? 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 O4 H9 O3 0.73(8) 1.84(8) 2.558(5) 167(9) 2_675 O1 H8 O2 0.88(7) 1.73(7) 2.581(4) 161(6) 2_665 O7 H7B O7 0.84(2) 2.17(9) 2.865(13) 139(13) 2_666 O7 H6 O6 0.85(2) 1.92(2) 2.762(6) 172(7) . N2 H5 O5 0.86(7) 1.72(8) 2.563(5) 165(7) . N1 H1C O2 0.89 2.00 2.829(5) 153.6 1_655 N1 H1B O3 0.89 2.12 2.974(5) 160.3 2_675 N1 H1A O4 0.89 2.62 3.045(5) 110.3 1_655 N1 H1A O6 0.89 1.95 2.776(5) 153.5 1_655 _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.736 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.119 # Attachment '2.cif' data_60427lm3_0m _database_code_depnum_ccdc_archive 'CCDC 633789' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H21 N3 O8 P2' _chemical_formula_weight 421.28 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 7.0561(6) _cell_length_b 9.9086(8) _cell_length_c 13.0837(10) _cell_angle_alpha 83.7770(10) _cell_angle_beta 79.4440(10) _cell_angle_gamma 85.2130(10) _cell_volume 892.09(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3022 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.294 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.8644 _exptl_absorpt_correction_T_max 0.9489 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 5800 _diffrn_reflns_av_R_equivalents 0.0121 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3964 _reflns_number_gt 3490 _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^)+(0.0683P)^2^+0.9181P] 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 0.004(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3964 _refine_ls_number_parameters 310 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1295 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.009 _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 0.3173(3) 0.3603(2) 0.33641(16) 0.0287(4) Uani 1 1 d . . . C2 C 0.1837(4) 0.4833(3) 0.3694(2) 0.0413(6) Uani 1 1 d . . . C3 C 0.6448(5) 0.3238(4) 0.0046(2) 0.0584(8) Uani 1 1 d . . . C4 C 0.6616(5) 0.2990(4) -0.0998(3) 0.0648(9) Uani 1 1 d . . . C5 C 0.7021(4) 0.1703(4) -0.1265(2) 0.0600(9) Uani 1 1 d . . . C6 C 0.7293(4) 0.0633(3) -0.04894(19) 0.0451(6) Uani 1 1 d . . . C7 C 0.7084(3) 0.0991(3) 0.05419(18) 0.0355(5) Uani 1 1 d . . . C8 C 0.7391(3) -0.0064(2) 0.13480(17) 0.0317(5) Uani 1 1 d . . . C9 C 0.7865(3) -0.1417(3) 0.1128(2) 0.0395(5) Uani 1 1 d . . . C10 C 0.8167(4) -0.2393(3) 0.1955(3) 0.0480(7) Uani 1 1 d . . . C11 C 0.8032(4) -0.2025(3) 0.2942(2) 0.0444(6) Uani 1 1 d . . . C12 C 0.7562(4) -0.0672(3) 0.31214(19) 0.0373(5) Uani 1 1 d . . . C13 C 0.7769(4) -0.0749(4) -0.0698(2) 0.0552(8) Uani 1 1 d . . . C14 C 0.8040(4) -0.1729(4) 0.0066(3) 0.0541(8) Uani 1 1 d . . . N1 N 0.3638(3) 0.37430(18) 0.22441(12) 0.0272(4) Uani 1 1 d . . . H1A H 0.2693 0.3439 0.1983 0.041 Uiso 1 1 calc R . . H1B H 0.4738 0.3262 0.2038 0.041 Uiso 1 1 calc R . . H1C H 0.3771 0.4615 0.2017 0.041 Uiso 1 1 calc R . . N2 N 0.6643(3) 0.2270(2) 0.08127(17) 0.0431(5) Uani 1 1 d . . . N3 N 0.7260(3) 0.0246(2) 0.23446(15) 0.0316(4) Uani 1 1 d . . . O1 O 0.6875(2) 0.26223(17) 0.32640(13) 0.0368(4) Uani 1 1 d . . . O2 O 0.6155(3) 0.50375(18) 0.35831(14) 0.0411(4) Uani 1 1 d . . . O3 O 0.5013(2) 0.32428(16) 0.50411(12) 0.0323(3) Uani 1 1 d . . . O4 O 0.3377(3) 0.08847(19) 0.3501(2) 0.0600(6) Uani 1 1 d . . . O5 O 0.0448(3) 0.2051(3) 0.29997(16) 0.0556(6) Uani 1 1 d . . . O6 O 0.0858(3) 0.2022(2) 0.48743(15) 0.0494(5) Uani 1 1 d . . . O1W O 0.2571(3) 0.84972(19) 0.39920(16) 0.0457(5) Uani 1 1 d D . . O2W O 0.9916(6) 0.4462(4) 0.1298(3) 0.1092(11) Uani 1 1 d . . . P1 P 0.54322(8) 0.35702(5) 0.38780(4) 0.02681(17) Uani 1 1 d . . . P2 P 0.18518(8) 0.20623(6) 0.37810(5) 0.03558(19) Uani 1 1 d . . . H1 H 0.574(5) 0.557(4) 0.406(3) 0.058(9) Uiso 1 1 d . . . H2 H -0.086(7) 0.247(4) 0.314(3) 0.094(14) Uiso 1 1 d . . . H3 H 0.620(6) 0.423(4) 0.026(3) 0.085(13) Uiso 1 1 d . . . H4 H 0.634(6) 0.374(4) -0.152(3) 0.089(13) Uiso 1 1 d . . . H5 H 0.716(5) 0.144(4) -0.194(3) 0.071(11) Uiso 1 1 d . . . H2A H 0.065(5) 0.483(3) 0.343(3) 0.057(9) Uiso 1 1 d . . . H2B H 0.156(5) 0.484(3) 0.442(3) 0.050(8) Uiso 1 1 d . . . H2C H 0.243(5) 0.562(3) 0.343(3) 0.054(9) Uiso 1 1 d . . . H3A H 0.705(4) 0.103(3) 0.246(2) 0.047(8) Uiso 1 1 d . . . H1W1 H 0.147(3) 0.839(4) 0.440(2) 0.070(11) Uiso 1 1 d D . . H2W1 H 0.336(4) 0.810(4) 0.435(3) 0.089(14) Uiso 1 1 d D . . H10 H 0.854(5) -0.325(4) 0.181(3) 0.065(10) Uiso 1 1 d . . . H11 H 0.822(5) -0.264(4) 0.353(3) 0.057(9) Uiso 1 1 d . . . H12 H 0.742(4) -0.036(3) 0.381(2) 0.044(8) Uiso 1 1 d . . . H13 H 0.794(6) -0.094(4) -0.134(3) 0.078(12) Uiso 1 1 d . . . H14 H 0.839(6) -0.264(4) -0.008(3) 0.076(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0291(10) 0.0296(10) 0.0264(10) -0.0042(8) -0.0041(8) 0.0029(8) C2 0.0378(14) 0.0374(13) 0.0470(15) -0.0101(11) -0.0059(11) 0.0115(10) C3 0.066(2) 0.0579(19) 0.0479(16) 0.0094(14) -0.0096(14) -0.0025(15) C4 0.061(2) 0.086(3) 0.0423(16) 0.0177(17) -0.0074(14) -0.0055(17) C5 0.0440(16) 0.107(3) 0.0284(13) -0.0001(15) -0.0038(11) -0.0141(16) C6 0.0300(12) 0.0743(19) 0.0320(12) -0.0132(12) -0.0002(9) -0.0100(12) C7 0.0291(11) 0.0483(13) 0.0301(11) -0.0073(10) -0.0037(8) -0.0063(9) C8 0.0257(10) 0.0369(12) 0.0336(11) -0.0111(9) -0.0025(8) -0.0041(8) C9 0.0306(12) 0.0419(13) 0.0474(14) -0.0191(11) -0.0011(10) -0.0034(10) C10 0.0421(15) 0.0327(13) 0.0685(19) -0.0144(12) -0.0032(12) -0.0007(10) C11 0.0432(14) 0.0352(13) 0.0524(15) 0.0015(11) -0.0058(11) -0.0018(10) C12 0.0389(13) 0.0386(12) 0.0334(12) -0.0036(10) -0.0036(9) -0.0021(10) C13 0.0442(15) 0.088(2) 0.0370(14) -0.0307(15) 0.0008(11) -0.0090(15) C14 0.0431(15) 0.0632(19) 0.0599(18) -0.0391(16) -0.0012(13) -0.0016(13) N1 0.0309(9) 0.0304(9) 0.0187(8) -0.0010(6) -0.0048(6) 0.0062(7) N2 0.0499(13) 0.0417(12) 0.0371(11) -0.0007(9) -0.0086(9) -0.0003(9) N3 0.0333(10) 0.0301(10) 0.0321(9) -0.0085(8) -0.0055(7) -0.0001(8) O1 0.0238(8) 0.0435(9) 0.0474(9) -0.0257(8) -0.0070(7) 0.0027(6) O2 0.0475(10) 0.0340(9) 0.0399(9) -0.0130(7) 0.0079(8) -0.0145(7) O3 0.0353(8) 0.0310(8) 0.0320(8) -0.0087(6) -0.0069(6) -0.0001(6) O4 0.0278(9) 0.0347(10) 0.1116(19) -0.0114(11) 0.0059(10) -0.0010(7) O5 0.0245(9) 0.0919(16) 0.0571(12) -0.0422(11) -0.0048(8) -0.0034(9) O6 0.0367(10) 0.0642(13) 0.0457(10) 0.0030(9) -0.0023(8) -0.0158(9) O1W 0.0379(10) 0.0393(10) 0.0543(11) 0.0089(8) -0.0021(9) 0.0000(8) O2W 0.132(3) 0.088(2) 0.116(3) -0.0324(19) -0.038(2) 0.011(2) P1 0.0236(3) 0.0263(3) 0.0313(3) -0.0108(2) -0.0023(2) -0.00101(19) P2 0.0220(3) 0.0374(3) 0.0476(4) -0.0103(3) -0.0027(2) -0.0032(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.436(2) . ? C1 C2 1.527(3) . ? C1 P2 1.835(2) . ? C1 P1 1.836(2) . ? C2 H2A 0.96(4) . ? C2 H2B 0.94(3) . ? C2 H2C 0.92(3) . ? C3 N2 1.329(4) . ? C3 C4 1.396(5) . ? C3 H3 1.05(4) . ? C4 C5 1.352(6) . ? C4 H4 0.98(4) . ? C5 C6 1.412(5) . ? C5 H5 0.93(4) . ? C6 C7 1.411(3) . ? C6 C13 1.426(4) . ? C7 N2 1.349(3) . ? C7 C8 1.435(3) . ? C8 N3 1.357(3) . ? C8 C9 1.401(3) . ? C9 C10 1.406(4) . ? C9 C14 1.437(4) . ? C10 C11 1.364(4) . ? C10 H10 0.90(4) . ? C11 C12 1.389(4) . ? C11 H11 0.95(3) . ? C12 N3 1.323(3) . ? C12 H12 0.97(3) . ? C13 C14 1.344(5) . ? C13 H13 0.86(4) . ? C14 H14 0.95(4) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? N3 H3A 0.81(3) . ? O1 P1 1.5059(16) . ? O2 P1 1.5663(17) . ? O2 H1 0.86(4) . ? O3 P1 1.5009(16) . ? O4 P2 1.5469(19) . ? O5 P2 1.550(2) . ? O5 H2 0.98(5) . ? O6 P2 1.471(2) . ? O1W H1W1 0.863(18) . ? O1W H2W1 0.839(18) . ? 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 107.44(18) . . ? N1 C1 P2 108.49(14) . . ? C2 C1 P2 108.46(17) . . ? N1 C1 P1 108.16(14) . . ? C2 C1 P1 110.69(16) . . ? P2 C1 P1 113.42(11) . . ? C1 C2 H2A 110(2) . . ? C1 C2 H2B 112(2) . . ? H2A C2 H2B 110(3) . . ? C1 C2 H2C 110(2) . . ? H2A C2 H2C 109(3) . . ? H2B C2 H2C 107(3) . . ? N2 C3 C4 123.7(3) . . ? N2 C3 H3 116(2) . . ? C4 C3 H3 120(2) . . ? C5 C4 C3 119.3(3) . . ? C5 C4 H4 121(2) . . ? C3 C4 H4 119(3) . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5 126(2) . . ? C6 C5 H5 115(2) . . ? C7 C6 C5 116.5(3) . . ? C7 C6 C13 119.7(3) . . ? C5 C6 C13 123.9(3) . . ? N2 C7 C6 123.9(2) . . ? N2 C7 C8 118.0(2) . . ? C6 C7 C8 118.1(2) . . ? N3 C8 C9 118.7(2) . . ? N3 C8 C7 119.9(2) . . ? C9 C8 C7 121.4(2) . . ? C8 C9 C10 118.3(2) . . ? C8 C9 C14 118.2(3) . . ? C10 C9 C14 123.5(3) . . ? C11 C10 C9 120.7(2) . . ? C11 C10 H10 120(2) . . ? C9 C10 H10 119(2) . . ? C10 C11 C12 118.9(3) . . ? C10 C11 H11 124(2) . . ? C12 C11 H11 117(2) . . ? N3 C12 C11 120.4(2) . . ? N3 C12 H12 117.5(18) . . ? C11 C12 H12 122.0(18) . . ? C14 C13 C6 121.6(2) . . ? C14 C13 H13 120(3) . . ? C6 C13 H13 118(3) . . ? C13 C14 C9 120.9(3) . . ? C13 C14 H14 121(2) . . ? C9 C14 H14 118(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 . . ? C3 N2 C7 116.9(3) . . ? C12 N3 C8 123.0(2) . . ? C12 N3 H3A 119(2) . . ? C8 N3 H3A 118(2) . . ? P1 O2 H1 112(2) . . ? P2 O5 H2 121(3) . . ? H1W1 O1W H2W1 103(2) . . ? O3 P1 O1 116.89(10) . . ? O3 P1 O2 111.00(9) . . ? O1 P1 O2 106.94(10) . . ? O3 P1 C1 109.04(9) . . ? O1 P1 C1 107.04(9) . . ? O2 P1 C1 105.25(11) . . ? O6 P2 O4 116.58(13) . . ? O6 P2 O5 112.95(11) . . ? O4 P2 O5 104.19(13) . . ? O6 P2 C1 112.52(11) . . ? O4 P2 C1 104.13(10) . . ? O5 P2 C1 105.39(12) . . ? 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 C3 C4 C5 -0.8(6) . . . . ? C3 C4 C5 C6 -0.8(5) . . . . ? C4 C5 C6 C7 1.1(4) . . . . ? C4 C5 C6 C13 -178.5(3) . . . . ? C5 C6 C7 N2 0.2(4) . . . . ? C13 C6 C7 N2 179.8(2) . . . . ? C5 C6 C7 C8 -178.7(2) . . . . ? C13 C6 C7 C8 0.9(3) . . . . ? N2 C7 C8 N3 -0.9(3) . . . . ? C6 C7 C8 N3 178.0(2) . . . . ? N2 C7 C8 C9 -179.6(2) . . . . ? C6 C7 C8 C9 -0.6(3) . . . . ? N3 C8 C9 C10 0.6(3) . . . . ? C7 C8 C9 C10 179.3(2) . . . . ? N3 C8 C9 C14 -178.7(2) . . . . ? C7 C8 C9 C14 0.0(4) . . . . ? C8 C9 C10 C11 -1.1(4) . . . . ? C14 C9 C10 C11 178.2(3) . . . . ? C9 C10 C11 C12 0.9(4) . . . . ? C10 C11 C12 N3 -0.3(4) . . . . ? C7 C6 C13 C14 -0.5(4) . . . . ? C5 C6 C13 C14 179.1(3) . . . . ? C6 C13 C14 C9 -0.2(5) . . . . ? C8 C9 C14 C13 0.5(4) . . . . ? C10 C9 C14 C13 -178.8(3) . . . . ? C4 C3 N2 C7 2.1(5) . . . . ? C6 C7 N2 C3 -1.8(4) . . . . ? C8 C7 N2 C3 177.2(2) . . . . ? C11 C12 N3 C8 -0.2(4) . . . . ? C9 C8 N3 C12 0.1(3) . . . . ? C7 C8 N3 C12 -178.7(2) . . . . ? N1 C1 P1 O3 -172.71(13) . . . . ? C2 C1 P1 O3 69.84(19) . . . . ? P2 C1 P1 O3 -52.33(13) . . . . ? N1 C1 P1 O1 -45.39(17) . . . . ? C2 C1 P1 O1 -162.84(17) . . . . ? P2 C1 P1 O1 74.99(13) . . . . ? N1 C1 P1 O2 68.14(16) . . . . ? C2 C1 P1 O2 -49.31(19) . . . . ? P2 C1 P1 O2 -171.47(11) . . . . ? N1 C1 P2 O6 -164.40(14) . . . . ? C2 C1 P2 O6 -47.99(19) . . . . ? P1 C1 P2 O6 75.41(14) . . . . ? N1 C1 P2 O4 68.46(17) . . . . ? C2 C1 P2 O4 -175.13(18) . . . . ? P1 C1 P2 O4 -51.73(15) . . . . ? N1 C1 P2 O5 -40.90(16) . . . . ? C2 C1 P2 O5 75.51(18) . . . . ? P1 C1 P2 O5 -161.09(11) . . . . ? 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 H1A O5 0.89 2.32 2.883(3) 121.5 . N1 H1A O2W 0.89 2.41 3.102(4) 135.4 1_455 N1 H1B N2 0.89 2.16 2.959(3) 148.7 . N1 H1B O1 0.89 2.40 2.933(2) 118.8 . O2 H1 O3 0.86(4) 1.74(4) 2.590(2) 175(3) 2_666 O5 H2 O1 0.98(5) 1.57(5) 2.506(2) 159(4) 1_455 N3 H3A O1 0.81(3) 1.97(3) 2.730(2) 157(3) . O1W H1W1 O6 0.863(18) 1.798(19) 2.655(3) 171(4) 2_566 O1W H2W1 O3 0.839(18) 1.89(2) 2.703(2) 163(4) 2_666 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.598 _refine_diff_density_min -0.668 _refine_diff_density_rms 0.065 # Attachment '3.cif' data_60426lm2_0m _database_code_depnum_ccdc_archive 'CCDC 633790' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H24 N3 O11 P3' _chemical_formula_weight 491.26 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 7.4045(5) _cell_length_b 11.7344(8) _cell_length_c 12.4850(8) _cell_angle_alpha 74.1490(10) _cell_angle_beta 85.3890(10) _cell_angle_gamma 72.9030(10) _cell_volume 997.42(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4063 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 29.50 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.363 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.8989 _exptl_absorpt_correction_T_max 0.9475 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 6745 _diffrn_reflns_av_R_equivalents 0.0094 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4656 _reflns_number_gt 4171 _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^)+(0.0532P)^2^+0.4944P] 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 0.0027(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4656 _refine_ls_number_parameters 368 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.1004 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.086 _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 0.1673(3) 0.6550(2) 0.6572(2) 0.0476(5) Uani 1 1 d . . . C2 C 0.2273(4) 0.5838(2) 0.5852(2) 0.0525(6) Uani 1 1 d . . . C3 C 0.2989(4) 0.6340(2) 0.4836(2) 0.0532(6) Uani 1 1 d . . . C4 C 0.3089(4) 0.7541(2) 0.45644(18) 0.0459(5) Uani 1 1 d . . . C5 C 0.2463(3) 0.82448(18) 0.53207(15) 0.0343(4) Uani 1 1 d . . . C6 C 0.2460(3) 0.95425(18) 0.51457(15) 0.0338(4) Uani 1 1 d . . . C7 C 0.2961(3) 1.0218(2) 0.41344(18) 0.0422(5) Uani 1 1 d . . . C8 C 0.2955(4) 1.1416(2) 0.4045(2) 0.0505(5) Uani 1 1 d . . . C9 C 0.2439(3) 1.1893(2) 0.4944(2) 0.0532(6) Uani 1 1 d . . . C10 C 0.1917(4) 1.1158(2) 0.5919(2) 0.0517(6) Uani 1 1 d . . . C11 C 0.3640(2) 0.28142(14) 0.95542(13) 0.0224(3) Uani 1 1 d . . . C12 C 0.4418(2) 0.39273(15) 0.90168(15) 0.0273(3) Uani 1 1 d . . . C13 C 0.6247(3) 0.36079(17) 0.83668(16) 0.0313(4) Uani 1 1 d . . . N1 N 0.17560(19) 0.33147(13) 1.00690(12) 0.0240(3) Uani 1 1 d . . . N2 N 0.1789(2) 0.77121(17) 0.63014(14) 0.0371(4) Uani 1 1 d . . . N3 N 0.1929(3) 0.99911(17) 0.60297(15) 0.0435(4) Uani 1 1 d . . . O1 O 0.49127(18) 0.13762(12) 0.80765(12) 0.0351(3) Uani 1 1 d . . . O2 O 0.18147(17) 0.13241(12) 0.90873(11) 0.0313(3) Uani 1 1 d . . . O3 O 0.20403(19) 0.32127(12) 0.75944(11) 0.0350(3) Uani 1 1 d . . . O4 O 0.69235(18) 0.10037(12) 1.02652(12) 0.0398(3) Uani 1 1 d . . . O5 O 0.39448(19) 0.09480(13) 1.14043(12) 0.0362(3) Uani 1 1 d . . . O6 O 0.5581(2) 0.25626(13) 1.13624(13) 0.0430(3) Uani 1 1 d . . . O7 O 0.8755(2) 0.45105(16) 0.70057(12) 0.0386(3) Uani 1 1 d . . . O8 O 0.5921(2) 0.60254(13) 0.74337(12) 0.0372(3) Uani 1 1 d . . . O9 O 0.84169(18) 0.48611(12) 0.89342(11) 0.0334(3) Uani 1 1 d . . . O1W O 0.0356(2) 0.81361(17) 0.83491(13) 0.0440(4) Uani 1 1 d . . . O2W O 0.8993(2) 0.06514(18) 0.81094(16) 0.0557(4) Uani 1 1 d D . . P1 P 0.30926(6) 0.21295(4) 0.84874(4) 0.02496(12) Uani 1 1 d . . . P2 P 0.51615(6) 0.17483(4) 1.07298(4) 0.02720(12) Uani 1 1 d . . . P3 P 0.74137(6) 0.47987(4) 0.79711(3) 0.02565(12) Uani 1 1 d . . . H1 H 0.187(3) 0.384(2) 1.051(2) 0.045(6) Uiso 1 1 d . . . H2 H 0.089(3) 0.377(2) 0.955(2) 0.037(6) Uiso 1 1 d . . . H3 H 0.135(3) 0.268(2) 1.054(2) 0.043(6) Uiso 1 1 d . . . H4 H 0.236(6) 0.034(4) 0.934(4) 0.136(16) Uiso 1 1 d . . . H5 H 0.434(5) 0.019(4) 1.145(3) 0.102(13) Uiso 1 1 d . . . H6 H 0.452(3) 0.424(2) 0.9608(19) 0.037(6) Uiso 1 1 d . . . H7 H 0.346(3) 0.455(2) 0.8533(18) 0.035(5) Uiso 1 1 d . . . H8 H 0.598(4) 0.343(2) 0.767(2) 0.055(7) Uiso 1 1 d . . . H9 H 0.717(4) 0.296(3) 0.877(2) 0.061(8) Uiso 1 1 d . . . H10 H 0.544(6) 0.650(4) 0.789(3) 0.103(13) Uiso 1 1 d . . . H11 H 0.967(4) 0.405(3) 0.722(3) 0.064(10) Uiso 1 1 d . . . H12 H 0.147(3) 0.813(2) 0.6744(19) 0.032(6) Uiso 1 1 d . . . H13 H 0.121(4) 0.628(2) 0.727(2) 0.050(7) Uiso 1 1 d . . . H14 H 0.223(4) 0.504(3) 0.607(2) 0.067(8) Uiso 1 1 d . . . H15 H 0.349(5) 0.581(3) 0.429(3) 0.078(9) Uiso 1 1 d . . . H16 H 0.354(4) 0.790(3) 0.386(2) 0.061(8) Uiso 1 1 d . . . H17 H 0.330(4) 0.984(3) 0.350(3) 0.070(9) Uiso 1 1 d . . . H18 H 0.335(4) 1.187(3) 0.333(3) 0.071(9) Uiso 1 1 d . . . H19 H 0.235(4) 1.274(3) 0.490(3) 0.072(9) Uiso 1 1 d . . . H20 H 0.147(4) 1.143(3) 0.653(2) 0.059(8) Uiso 1 1 d . . . H1W1 H -0.017(4) 0.889(3) 0.834(2) 0.053(8) Uiso 1 1 d . . . H2W1 H 0.153(6) 0.798(3) 0.862(3) 0.096(12) Uiso 1 1 d . . . H1W2 H 0.795(3) 0.095(4) 0.845(4) 0.136(17) Uiso 1 1 d D . . H2W2 H 0.984(3) 0.105(2) 0.848(2) 0.050(7) 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 C1 0.0430(11) 0.0437(12) 0.0460(12) 0.0079(9) 0.0000(9) -0.0151(9) C2 0.0584(14) 0.0380(12) 0.0594(14) -0.0004(10) -0.0075(11) -0.0205(10) C3 0.0731(16) 0.0449(12) 0.0474(12) -0.0123(10) -0.0085(11) -0.0230(12) C4 0.0649(14) 0.0444(12) 0.0320(10) -0.0070(9) 0.0013(9) -0.0238(11) C5 0.0339(9) 0.0386(10) 0.0300(9) -0.0014(7) -0.0039(7) -0.0155(8) C6 0.0327(9) 0.0373(10) 0.0319(9) -0.0056(7) -0.0008(7) -0.0135(7) C7 0.0473(11) 0.0411(11) 0.0365(10) -0.0021(8) 0.0020(9) -0.0178(9) C8 0.0511(13) 0.0416(12) 0.0549(13) 0.0020(10) -0.0006(10) -0.0210(10) C9 0.0458(12) 0.0384(12) 0.0786(17) -0.0127(11) -0.0077(11) -0.0173(10) C10 0.0521(13) 0.0534(14) 0.0578(14) -0.0257(12) 0.0006(11) -0.0172(11) C11 0.0212(7) 0.0182(7) 0.0283(8) -0.0059(6) 0.0031(6) -0.0074(5) C12 0.0302(8) 0.0194(7) 0.0332(9) -0.0055(6) 0.0029(7) -0.0103(6) C13 0.0365(9) 0.0268(9) 0.0359(9) -0.0112(7) 0.0104(7) -0.0168(7) N1 0.0219(6) 0.0232(7) 0.0276(7) -0.0088(6) 0.0007(5) -0.0059(5) N2 0.0346(8) 0.0393(9) 0.0326(8) -0.0019(7) 0.0007(6) -0.0104(7) N3 0.0468(10) 0.0479(10) 0.0403(9) -0.0138(8) 0.0032(8) -0.0190(8) O1 0.0309(6) 0.0322(7) 0.0487(8) -0.0210(6) 0.0135(6) -0.0126(5) O2 0.0284(6) 0.0286(6) 0.0415(7) -0.0107(5) 0.0047(5) -0.0147(5) O3 0.0414(7) 0.0308(7) 0.0309(6) -0.0060(5) -0.0026(5) -0.0084(5) O4 0.0279(6) 0.0286(7) 0.0499(8) 0.0013(6) 0.0110(6) -0.0021(5) O5 0.0298(6) 0.0306(7) 0.0393(7) 0.0025(6) 0.0071(5) -0.0077(5) O6 0.0440(8) 0.0334(7) 0.0530(9) -0.0129(6) -0.0198(7) -0.0061(6) O7 0.0338(7) 0.0551(9) 0.0304(7) -0.0098(6) 0.0059(6) -0.0207(7) O8 0.0394(7) 0.0300(7) 0.0384(7) 0.0016(6) -0.0094(6) -0.0118(6) O9 0.0341(6) 0.0302(6) 0.0378(7) -0.0131(5) -0.0099(5) -0.0054(5) O1W 0.0338(7) 0.0512(10) 0.0471(8) -0.0070(7) -0.0042(6) -0.0166(7) O2W 0.0427(9) 0.0661(11) 0.0675(11) -0.0306(9) 0.0105(8) -0.0199(8) P1 0.0277(2) 0.0205(2) 0.0284(2) -0.00843(16) 0.00406(16) -0.00859(16) P2 0.0243(2) 0.0210(2) 0.0335(2) -0.00406(16) -0.00167(16) -0.00456(16) P3 0.0285(2) 0.0256(2) 0.0255(2) -0.00333(16) -0.00159(16) -0.01438(17) _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 N2 1.339(3) . ? C1 C2 1.353(4) . ? C1 H13 0.92(3) . ? C2 C3 1.380(4) . ? C2 H14 0.91(3) . ? C3 C4 1.380(3) . ? C3 H15 1.02(3) . ? C4 C5 1.385(3) . ? C4 H16 0.95(3) . ? C5 N2 1.344(2) . ? C5 C6 1.477(3) . ? C6 N3 1.333(3) . ? C6 C7 1.382(3) . ? C7 C8 1.379(3) . ? C7 H17 0.99(3) . ? C8 C9 1.366(4) . ? C8 H18 0.97(3) . ? C9 C10 1.386(4) . ? C9 H19 0.96(3) . ? C10 N3 1.336(3) . ? C10 H20 0.90(3) . ? C11 N1 1.5116(19) . ? C11 C12 1.546(2) . ? C11 P2 1.8499(17) . ? C11 P1 1.8566(17) . ? C12 C13 1.525(2) . ? C12 H6 0.93(2) . ? C12 H7 0.96(2) . ? C13 P3 1.7906(18) . ? C13 H8 1.00(3) . ? C13 H9 0.92(3) . ? N1 H1 0.95(3) . ? N1 H2 0.89(2) . ? N1 H3 0.93(3) . ? N2 H12 0.81(2) . ? O1 P1 1.5156(12) . ? O2 P1 1.5410(12) . ? O2 H4 1.07(5) . ? O3 P1 1.4997(13) . ? O4 P2 1.5123(13) . ? O5 P2 1.5318(13) . ? O5 H5 0.83(4) . ? O6 P2 1.5032(14) . ? O7 P3 1.5449(14) . ? O7 H11 0.75(3) . ? O8 P3 1.5490(14) . ? O8 H10 0.89(4) . ? O9 P3 1.4922(13) . ? O1W H1W1 0.85(3) . ? O1W H2W1 0.91(4) . ? O2W H1W2 0.878(19) . ? O2W H2W2 1.077(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 C2 120.4(2) . . ? N2 C1 H13 115.6(17) . . ? C2 C1 H13 124.0(16) . . ? C1 C2 C3 118.6(2) . . ? C1 C2 H14 118.6(19) . . ? C3 C2 H14 122.8(19) . . ? C4 C3 C2 120.5(2) . . ? C4 C3 H15 119.2(18) . . ? C2 C3 H15 120.2(18) . . ? C3 C4 C5 119.5(2) . . ? C3 C4 H16 121.1(17) . . ? C5 C4 H16 119.4(17) . . ? N2 C5 C4 117.74(19) . . ? N2 C5 C6 116.50(18) . . ? C4 C5 C6 125.76(18) . . ? N3 C6 C7 123.87(19) . . ? N3 C6 C5 114.60(17) . . ? C7 C6 C5 121.53(19) . . ? C8 C7 C6 117.9(2) . . ? C8 C7 H17 122.0(17) . . ? C6 C7 H17 120.1(17) . . ? C9 C8 C7 119.3(2) . . ? C9 C8 H18 124.2(18) . . ? C7 C8 H18 116.5(18) . . ? C8 C9 C10 118.9(2) . . ? C8 C9 H19 121.5(19) . . ? C10 C9 H19 119.5(19) . . ? N3 C10 C9 123.0(2) . . ? N3 C10 H20 113.2(18) . . ? C9 C10 H20 123.8(18) . . ? N1 C11 C12 106.86(12) . . ? N1 C11 P2 105.47(10) . . ? C12 C11 P2 110.23(11) . . ? N1 C11 P1 105.05(10) . . ? C12 C11 P1 111.44(11) . . ? P2 C11 P1 117.00(8) . . ? C13 C12 C11 114.05(14) . . ? C13 C12 H6 114.2(14) . . ? C11 C12 H6 103.9(14) . . ? C13 C12 H7 109.8(13) . . ? C11 C12 H7 108.1(13) . . ? H6 C12 H7 106.4(18) . . ? C12 C13 P3 114.65(12) . . ? C12 C13 H8 109.6(15) . . ? P3 C13 H8 107.0(15) . . ? C12 C13 H9 113.4(17) . . ? P3 C13 H9 101.5(18) . . ? H8 C13 H9 110(2) . . ? C11 N1 H1 110.4(15) . . ? C11 N1 H2 111.4(14) . . ? H1 N1 H2 107(2) . . ? C11 N1 H3 110.9(15) . . ? H1 N1 H3 107(2) . . ? H2 N1 H3 110(2) . . ? C1 N2 C5 123.3(2) . . ? C1 N2 H12 120.5(16) . . ? C5 N2 H12 116.2(16) . . ? C6 N3 C10 117.0(2) . . ? P1 O2 H4 121(2) . . ? P2 O5 H5 117(3) . . ? P3 O7 H11 111(2) . . ? P3 O8 H10 115(3) . . ? H1W1 O1W H2W1 104(3) . . ? H1W2 O2W H2W2 95(2) . . ? O3 P1 O1 113.14(8) . . ? O3 P1 O2 111.59(8) . . ? O1 P1 O2 112.16(7) . . ? O3 P1 C11 104.86(7) . . ? O1 P1 C11 109.53(7) . . ? O2 P1 C11 104.95(7) . . ? O6 P2 O4 112.57(9) . . ? O6 P2 O5 112.20(9) . . ? O4 P2 O5 112.70(8) . . ? O6 P2 C11 105.38(8) . . ? O4 P2 C11 108.58(8) . . ? O5 P2 C11 104.76(7) . . ? O9 P3 O7 112.97(8) . . ? O9 P3 O8 113.43(8) . . ? O7 P3 O8 104.62(9) . . ? O9 P3 C13 111.44(9) . . ? O7 P3 C13 106.06(8) . . ? O8 P3 C13 107.78(9) . . ? 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 C1 C2 C3 -0.5(4) . . . . ? C1 C2 C3 C4 0.0(4) . . . . ? C2 C3 C4 C5 0.0(4) . . . . ? C3 C4 C5 N2 0.4(3) . . . . ? C3 C4 C5 C6 -179.3(2) . . . . ? N2 C5 C6 N3 5.4(3) . . . . ? C4 C5 C6 N3 -174.9(2) . . . . ? N2 C5 C6 C7 -174.15(19) . . . . ? C4 C5 C6 C7 5.5(3) . . . . ? N3 C6 C7 C8 1.7(3) . . . . ? C5 C6 C7 C8 -178.8(2) . . . . ? C6 C7 C8 C9 -0.8(4) . . . . ? C7 C8 C9 C10 -0.6(4) . . . . ? C8 C9 C10 N3 1.3(4) . . . . ? N1 C11 C12 C13 -175.00(15) . . . . ? P2 C11 C12 C13 70.87(17) . . . . ? P1 C11 C12 C13 -60.77(17) . . . . ? C11 C12 C13 P3 -168.36(13) . . . . ? C2 C1 N2 C5 0.9(3) . . . . ? C4 C5 N2 C1 -0.9(3) . . . . ? C6 C5 N2 C1 178.84(18) . . . . ? C7 C6 N3 C10 -1.0(3) . . . . ? C5 C6 N3 C10 179.42(19) . . . . ? C9 C10 N3 C6 -0.5(4) . . . . ? N1 C11 P1 O3 69.49(11) . . . . ? C12 C11 P1 O3 -45.86(13) . . . . ? P2 C11 P1 O3 -173.95(9) . . . . ? N1 C11 P1 O1 -168.80(10) . . . . ? C12 C11 P1 O1 75.84(12) . . . . ? P2 C11 P1 O1 -52.25(11) . . . . ? N1 C11 P1 O2 -48.21(11) . . . . ? C12 C11 P1 O2 -163.57(11) . . . . ? P2 C11 P1 O2 68.34(10) . . . . ? N1 C11 P2 O6 -71.22(12) . . . . ? C12 C11 P2 O6 43.78(13) . . . . ? P1 C11 P2 O6 172.46(9) . . . . ? N1 C11 P2 O4 167.95(10) . . . . ? C12 C11 P2 O4 -77.05(13) . . . . ? P1 C11 P2 O4 51.63(11) . . . . ? N1 C11 P2 O5 47.32(12) . . . . ? C12 C11 P2 O5 162.32(11) . . . . ? P1 C11 P2 O5 -69.01(10) . . . . ? C12 C13 P3 O9 76.37(16) . . . . ? C12 C13 P3 O7 -160.31(14) . . . . ? C12 C13 P3 O8 -48.70(17) . . . . ? 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 O2W H2W2 O2 1.077(16) 1.846(17) 2.896(2) 164(2) 1_655 O2W H1W2 O4 0.878(19) 2.34(3) 3.055(2) 139(4) . O2W H1W2 O1 0.878(19) 2.21(3) 2.888(2) 133(3) . O1W H2W1 O4 0.91(4) 2.58(4) 3.283(2) 135(3) 2_667 O1W H2W1 O6 0.91(4) 2.05(4) 2.901(2) 157(3) 2_667 O1W H1W1 O2W 0.85(3) 1.93(3) 2.763(3) 169(3) 1_465 N2 H12 N3 0.81(2) 2.24(2) 2.634(3) 110.6(19) . N2 H12 O1W 0.81(2) 2.11(2) 2.803(3) 144(2) . O7 H11 O3 0.75(3) 1.76(3) 2.505(2) 168(3) 1_655 O8 H10 O6 0.89(4) 1.61(4) 2.500(2) 175(4) 2_667 O5 H5 O1 0.83(4) 1.70(4) 2.5179(19) 165(4) 2_657 O2 H4 O4 1.07(5) 1.46(5) 2.5302(18) 177(4) 2_657 N1 H3 O5 0.93(3) 2.42(2) 2.894(2) 112.1(18) . N1 H3 O1W 0.93(3) 2.03(3) 2.911(2) 158(2) 2_567 N1 H2 O9 0.89(2) 1.97(2) 2.8167(19) 157(2) 1_455 N1 H1 O9 0.95(3) 1.79(3) 2.7232(19) 164(2) 2_667 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.352 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.057 # Attachment '4.cif' data_61122csp2_0m _database_code_depnum_ccdc_archive 'CCDC 633791' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H28 N3 O13 P3' _chemical_formula_weight 551.31 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 7.2243(5) _cell_length_b 12.3575(8) _cell_length_c 13.2057(9) _cell_angle_alpha 80.9570(10) _cell_angle_beta 89.5590(10) _cell_angle_gamma 78.9530(10) _cell_volume 1142.40(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yallowy _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.51 _exptl_crystal_size_min 0.49 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.603 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.333 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.8381 _exptl_absorpt_correction_T_max 0.8539 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7621 _diffrn_reflns_av_R_equivalents 0.0116 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5329 _reflns_number_gt 4907 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+0.7214P] 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 0.0068(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5329 _refine_ls_number_parameters 378 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.1062 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.068 _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 0.6757(2) 0.72176(12) 0.01002(12) 0.0170(3) Uani 1 1 d . . . C2 C 0.5727(2) 0.63376(13) 0.06950(13) 0.0208(3) Uani 1 1 d . . . C3 C 0.3952(3) 0.68109(13) 0.12377(14) 0.0231(3) Uani 1 1 d . . . C4 C 0.7992(3) 1.17425(17) 0.63925(17) 0.0367(4) Uani 1 1 d . . . H8 H 0.8120 1.1960 0.7027 0.044 Uiso 1 1 calc R . . C5 C 0.8007(3) 1.25394(17) 0.55165(19) 0.0400(5) Uani 1 1 d . . . H9 H 0.8140 1.3261 0.5575 0.048 Uiso 1 1 calc R . . C6 C 0.7824(3) 1.22468(17) 0.45776(17) 0.0381(5) Uani 1 1 d . . . H10 H 0.7840 1.2763 0.3986 0.046 Uiso 1 1 calc R . . C7 C 0.7609(3) 1.11463(16) 0.45134(14) 0.0298(4) Uani 1 1 d . . . C8 C 0.7612(2) 1.04077(15) 0.54431(13) 0.0247(3) Uani 1 1 d . . . C9 C 0.7402(2) 0.92842(15) 0.53857(13) 0.0238(3) Uani 1 1 d . . . C10 C 0.7201(3) 0.89410(16) 0.44325(14) 0.0284(4) Uani 1 1 d . . . C11 C 0.7029(3) 0.78252(18) 0.44253(16) 0.0349(4) Uani 1 1 d . . . H13 H 0.6876 0.7581 0.3806 0.042 Uiso 1 1 calc R . . C12 C 0.7088(3) 0.71022(18) 0.53240(17) 0.0385(5) Uani 1 1 d . . . H14 H 0.7008 0.6361 0.5319 0.046 Uiso 1 1 calc R . . C13 C 0.7268(3) 0.74814(17) 0.62423(16) 0.0347(4) Uani 1 1 d . . . H15 H 0.7297 0.6993 0.6857 0.042 Uiso 1 1 calc R . . C14 C 0.7177(3) 0.97271(19) 0.35132(15) 0.0367(5) Uani 1 1 d . . . H12 H 0.7015 0.9511 0.2881 0.044 Uiso 1 1 calc R . . C15 C 0.7388(3) 1.07795(19) 0.35540(15) 0.0379(5) Uani 1 1 d . . . H11 H 0.7391 1.1277 0.2947 0.046 Uiso 1 1 calc R . . O1 O 0.7903(2) 0.74422(11) 0.19969(9) 0.0256(3) Uani 1 1 d . . . O2 O 0.92235(18) 0.85124(10) 0.04578(10) 0.0254(3) Uani 1 1 d . . . O3 O 0.58185(18) 0.90953(10) 0.10051(10) 0.0267(3) Uani 1 1 d . . . O4 O 0.69091(19) 0.85033(10) -0.17302(9) 0.0259(3) Uani 1 1 d . . . O5 O 0.37503(18) 0.87948(10) -0.08619(10) 0.0249(3) Uani 1 1 d . . . O6 O 0.47981(19) 0.70433(10) -0.15772(10) 0.0274(3) Uani 1 1 d . . . O7 O 0.12077(18) 0.62685(11) 0.24798(10) 0.0271(3) Uani 1 1 d . . . O8 O 0.17008(19) 0.54089(10) 0.08433(10) 0.0280(3) Uani 1 1 d . . . O9 O 0.39871(19) 0.47629(11) 0.23414(10) 0.0262(3) Uani 1 1 d . . . O1W O 0.5752(3) 0.5269(2) 0.40631(16) 0.0650(6) Uani 1 1 d D . . O2W O 0.9356(13) 0.4651(11) 0.350(3) 0.115(10) Uani 0.52(4) 1 d P A 2 O3W O 0.1074(4) 0.6775(3) 0.8011(2) 0.0915(9) Uani 1 1 d D . . O4W O 0.8206(2) 0.03258(13) 0.88374(13) 0.0421(4) Uani 1 1 d D . . O2W' O 0.9600(14) 0.5046(18) 0.4087(12) 0.084(5) Uani 0.48(4) 1 d P A 1 N1 N 0.85559(19) 0.65689(11) -0.02694(11) 0.0201(3) Uani 1 1 d . . . H3A H 0.9383 0.6335 0.0252 0.030 Uiso 1 1 calc R . . H3B H 0.9038 0.7007 -0.0759 0.030 Uiso 1 1 calc R . . H3C H 0.8306 0.5982 -0.0518 0.030 Uiso 1 1 calc R . . N2 N 0.7809(2) 1.06990(13) 0.63789(12) 0.0304(3) Uani 1 1 d . . . N3 N 0.7398(2) 0.85347(13) 0.62556(12) 0.0271(3) Uani 1 1 d . . . P1 P 0.74650(6) 0.81768(3) 0.09113(3) 0.01770(11) Uani 1 1 d . . . P2 P 0.55130(6) 0.79341(3) -0.11240(3) 0.01859(12) Uani 1 1 d . . . P3 P 0.25656(6) 0.57863(3) 0.17213(3) 0.01844(12) Uani 1 1 d . . . H1 H 0.885(4) 0.714(2) 0.208(2) 0.042(8) Uiso 1 1 d . . . H2 H 0.397(4) 0.945(3) -0.090(2) 0.052(8) Uiso 1 1 d . . . H3 H 0.659(3) 0.5837(19) 0.1205(18) 0.029(6) Uiso 1 1 d . . . H4 H 0.537(3) 0.5867(19) 0.0209(18) 0.030(6) Uiso 1 1 d . . . H5 H 0.422(3) 0.716(2) 0.1765(19) 0.037(6) Uiso 1 1 d . . . H6 H 0.310(4) 0.736(2) 0.0746(19) 0.037(6) Uiso 1 1 d . . . H7 H 0.436(4) 0.428(3) 0.204(2) 0.056(9) Uiso 1 1 d . . . H16 H 0.746(4) 0.872(2) 0.680(2) 0.038(7) Uiso 1 1 d . . . H1W1 H 0.521(5) 0.507(3) 0.359(2) 0.096(10) Uiso 1 1 d D . . H2W1 H 0.690(3) 0.510(4) 0.395(3) 0.096(10) Uiso 1 1 d D . . H1W3 H 0.173(3) 0.6374(14) 0.8577(14) 0.024(4) Uiso 1 1 d D . . H2W3 H 0.101(3) 0.7445(13) 0.8324(16) 0.024(4) Uiso 1 1 d D . . H1W4 H 0.814(4) 0.011(2) 0.8226(13) 0.026(4) Uiso 0.75 1 d PD . . H2W4 H 0.701(2) 0.0602(19) 0.8959(19) 0.026(4) Uiso 0.75 1 d PD . . H3W4 H 0.886(3) 0.0798(17) 0.905(2) 0.026(4) Uiso 0.75 1 d PD . . H4W4 H 0.854(3) -0.0278(14) 0.9285(16) 0.026(4) Uiso 0.75 1 d PD . . 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 0.0193(7) 0.0145(6) 0.0181(7) -0.0043(5) 0.0005(5) -0.0043(5) C2 0.0246(8) 0.0147(7) 0.0243(8) -0.0037(6) 0.0033(6) -0.0062(6) C3 0.0264(8) 0.0164(7) 0.0287(8) -0.0065(6) 0.0054(7) -0.0075(6) C4 0.0460(12) 0.0313(10) 0.0370(10) -0.0131(8) 0.0024(9) -0.0114(9) C5 0.0449(12) 0.0248(9) 0.0515(13) -0.0066(9) 0.0018(10) -0.0092(8) C6 0.0413(11) 0.0281(9) 0.0409(11) 0.0043(8) 0.0018(9) -0.0049(8) C7 0.0287(9) 0.0295(9) 0.0286(9) -0.0013(7) 0.0009(7) -0.0017(7) C8 0.0238(8) 0.0255(8) 0.0246(8) -0.0056(7) 0.0023(6) -0.0035(6) C9 0.0227(8) 0.0268(8) 0.0221(8) -0.0066(6) 0.0027(6) -0.0033(6) C10 0.0275(9) 0.0346(9) 0.0242(8) -0.0107(7) 0.0016(7) -0.0036(7) C11 0.0370(10) 0.0410(11) 0.0321(10) -0.0196(8) 0.0034(8) -0.0096(9) C12 0.0477(12) 0.0324(10) 0.0418(11) -0.0166(9) 0.0078(9) -0.0156(9) C13 0.0463(12) 0.0287(9) 0.0320(9) -0.0065(8) 0.0082(8) -0.0132(8) C14 0.0433(11) 0.0448(11) 0.0208(8) -0.0087(8) -0.0016(8) -0.0023(9) C15 0.0453(12) 0.0408(11) 0.0229(9) 0.0022(8) -0.0007(8) -0.0022(9) O1 0.0274(7) 0.0294(6) 0.0184(6) -0.0034(5) -0.0003(5) -0.0018(5) O2 0.0273(6) 0.0258(6) 0.0268(6) -0.0052(5) 0.0002(5) -0.0130(5) O3 0.0276(6) 0.0184(5) 0.0350(7) -0.0104(5) -0.0028(5) -0.0011(5) O4 0.0338(7) 0.0265(6) 0.0188(5) -0.0030(5) 0.0020(5) -0.0098(5) O5 0.0253(6) 0.0186(6) 0.0303(6) -0.0058(5) -0.0015(5) -0.0014(5) O6 0.0331(7) 0.0206(6) 0.0303(6) -0.0100(5) -0.0091(5) -0.0041(5) O7 0.0266(6) 0.0273(6) 0.0274(6) -0.0058(5) 0.0058(5) -0.0047(5) O8 0.0309(7) 0.0228(6) 0.0320(7) -0.0097(5) -0.0090(5) -0.0047(5) O9 0.0329(7) 0.0195(6) 0.0249(6) -0.0041(5) -0.0049(5) -0.0009(5) O1W 0.0598(13) 0.0982(17) 0.0488(11) -0.0304(11) -0.0024(9) -0.0288(12) O2W 0.060(3) 0.055(4) 0.21(2) 0.046(8) 0.051(6) -0.005(3) O3W 0.0532(14) 0.145(3) 0.0759(17) -0.0027(17) 0.0098(12) -0.0317(16) O4W 0.0483(9) 0.0364(8) 0.0450(9) -0.0078(7) -0.0010(7) -0.0159(7) O2W' 0.068(4) 0.072(7) 0.094(7) 0.029(5) 0.033(4) 0.001(3) N1 0.0208(7) 0.0190(6) 0.0216(6) -0.0071(5) -0.0004(5) -0.0034(5) N2 0.0390(9) 0.0285(8) 0.0261(7) -0.0080(6) 0.0024(6) -0.0095(7) N3 0.0350(8) 0.0274(7) 0.0213(7) -0.0078(6) 0.0044(6) -0.0092(6) P1 0.0212(2) 0.01493(19) 0.0183(2) -0.00520(14) -0.00077(15) -0.00462(15) P2 0.0233(2) 0.01549(19) 0.0177(2) -0.00455(14) -0.00224(15) -0.00377(15) P3 0.0202(2) 0.01607(19) 0.0202(2) -0.00395(15) -0.00025(15) -0.00541(15) _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 1.545(2) . ? C1 P1 1.8583(15) . ? C1 P2 1.8635(16) . ? C2 C3 1.526(2) . ? C2 H3 0.98(2) . ? C2 H4 1.00(2) . ? C3 P3 1.7989(17) . ? C3 H5 0.92(3) . ? C3 H6 0.98(3) . ? C4 N2 1.324(3) . ? C4 C5 1.398(3) . ? C4 H8 0.9300 . ? C5 C6 1.359(3) . ? C5 H9 0.9300 . ? C6 C7 1.413(3) . ? C6 H10 0.9300 . ? C7 C8 1.410(3) . ? C7 C15 1.431(3) . ? C8 N2 1.356(2) . ? C8 C9 1.439(2) . ? C9 N3 1.358(2) . ? C9 C10 1.407(2) . ? C10 C11 1.409(3) . ? C10 C14 1.429(3) . ? C11 C12 1.364(3) . ? C11 H13 0.9300 . ? C12 C13 1.383(3) . ? C12 H14 0.9300 . ? C13 N3 1.326(2) . ? C13 H15 0.9300 . ? C14 C15 1.348(3) . ? C14 H12 0.9300 . ? C15 H11 0.9300 . ? O1 P1 1.5708(13) . ? O1 H1 0.71(3) . ? O2 P1 1.5022(13) . ? O3 P1 1.4977(13) . ? O4 P2 1.4951(13) . ? O5 P2 1.5693(13) . ? O5 H2 0.84(3) . ? O6 P2 1.5055(12) . ? O7 P3 1.5064(13) . ? O8 P3 1.4983(12) . ? O9 P3 1.5856(13) . ? O9 H7 0.77(3) . ? O1W H1W1 0.828(18) . ? O1W H2W1 0.833(18) . ? O3W H1W3 0.911(15) . ? O3W H2W3 0.975(15) . ? O4W H1W4 0.894(15) . ? O4W H2W4 0.890(14) . ? O4W H3W4 0.896(15) . ? O4W H4W4 0.871(14) . ? N1 H3A 0.8900 . ? N1 H3B 0.8900 . ? N1 H3C 0.8900 . ? N3 H16 0.79(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 105.92(12) . . ? N1 C1 P1 106.74(10) . . ? C2 C1 P1 113.48(11) . . ? N1 C1 P2 102.45(10) . . ? C2 C1 P2 112.75(11) . . ? P1 C1 P2 114.30(8) . . ? C3 C2 C1 115.17(13) . . ? C3 C2 H3 108.4(13) . . ? C1 C2 H3 109.4(13) . . ? C3 C2 H4 108.3(13) . . ? C1 C2 H4 108.7(13) . . ? H3 C2 H4 106.5(18) . . ? C2 C3 P3 113.72(11) . . ? C2 C3 H5 112.1(16) . . ? P3 C3 H5 108.7(16) . . ? C2 C3 H6 109.7(15) . . ? P3 C3 H6 104.2(14) . . ? H5 C3 H6 108(2) . . ? N2 C4 C5 124.38(19) . . ? N2 C4 H8 117.8 . . ? C5 C4 H8 117.8 . . ? C6 C5 C4 119.17(19) . . ? C6 C5 H9 120.4 . . ? C4 C5 H9 120.4 . . ? C5 C6 C7 119.09(19) . . ? C5 C6 H10 120.5 . . ? C7 C6 H10 120.5 . . ? C8 C7 C6 117.22(18) . . ? C8 C7 C15 120.44(18) . . ? C6 C7 C15 122.34(18) . . ? N2 C8 C7 123.60(17) . . ? N2 C8 C9 118.75(16) . . ? C7 C8 C9 117.64(16) . . ? N3 C9 C10 118.83(16) . . ? N3 C9 C8 120.30(15) . . ? C10 C9 C8 120.87(16) . . ? C9 C10 C11 118.23(17) . . ? C9 C10 C14 119.28(18) . . ? C11 C10 C14 122.49(17) . . ? C12 C11 C10 120.24(18) . . ? C12 C11 H13 119.9 . . ? C10 C11 H13 119.9 . . ? C11 C12 C13 119.41(19) . . ? C11 C12 H14 120.3 . . ? C13 C12 H14 120.3 . . ? N3 C13 C12 120.65(19) . . ? N3 C13 H15 119.7 . . ? C12 C13 H15 119.7 . . ? C15 C14 C10 120.54(18) . . ? C15 C14 H12 119.7 . . ? C10 C14 H12 119.7 . . ? C14 C15 C7 121.22(18) . . ? C14 C15 H11 119.4 . . ? C7 C15 H11 119.4 . . ? P1 O1 H1 115(2) . . ? P2 O5 H2 112(2) . . ? P3 O9 H7 116(2) . . ? H1W1 O1W H2W1 105(3) . . ? H1W3 O3W H2W3 88.5(15) . . ? H1W4 O4W H2W4 103.3(19) . . ? H1W4 O4W H3W4 131(3) . . ? H2W4 O4W H3W4 104.4(19) . . ? H1W4 O4W H4W4 107.0(19) . . ? H2W4 O4W H4W4 106.3(19) . . ? H3W4 O4W H4W4 102.7(17) . . ? C1 N1 H3A 109.5 . . ? C1 N1 H3B 109.5 . . ? H3A N1 H3B 109.5 . . ? C1 N1 H3C 109.5 . . ? H3A N1 H3C 109.5 . . ? H3B N1 H3C 109.5 . . ? C4 N2 C8 116.53(17) . . ? C13 N3 C9 122.60(17) . . ? C13 N3 H16 117.4(19) . . ? C9 N3 H16 120.0(19) . . ? O3 P1 O2 117.10(7) . . ? O3 P1 O1 108.03(8) . . ? O2 P1 O1 110.78(8) . . ? O3 P1 C1 109.21(7) . . ? O2 P1 C1 106.56(7) . . ? O1 P1 C1 104.42(7) . . ? O4 P2 O6 117.16(8) . . ? O4 P2 O5 111.62(7) . . ? O6 P2 O5 107.55(7) . . ? O4 P2 C1 105.90(7) . . ? O6 P2 C1 105.85(7) . . ? O5 P2 C1 108.31(7) . . ? O8 P3 O7 115.97(8) . . ? O8 P3 O9 109.28(7) . . ? O7 P3 O9 107.20(8) . . ? O8 P3 C3 109.66(8) . . ? O7 P3 C3 108.04(8) . . ? O9 P3 C3 106.25(8) . . ? 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 173.96(13) . . . . ? P1 C1 C2 C3 57.18(17) . . . . ? P2 C1 C2 C3 -74.78(16) . . . . ? C1 C2 C3 P3 169.32(12) . . . . ? N2 C4 C5 C6 0.0(4) . . . . ? C4 C5 C6 C7 0.5(3) . . . . ? C5 C6 C7 C8 -0.5(3) . . . . ? C5 C6 C7 C15 179.3(2) . . . . ? C6 C7 C8 N2 0.0(3) . . . . ? C15 C7 C8 N2 -179.78(19) . . . . ? C6 C7 C8 C9 -179.75(17) . . . . ? C15 C7 C8 C9 0.5(3) . . . . ? N2 C8 C9 N3 0.1(3) . . . . ? C7 C8 C9 N3 179.90(16) . . . . ? N2 C8 C9 C10 -179.79(17) . . . . ? C7 C8 C9 C10 0.0(3) . . . . ? N3 C9 C10 C11 -0.9(3) . . . . ? C8 C9 C10 C11 179.03(17) . . . . ? N3 C9 C10 C14 179.15(17) . . . . ? C8 C9 C10 C14 -0.9(3) . . . . ? C9 C10 C11 C12 -0.9(3) . . . . ? C14 C10 C11 C12 179.0(2) . . . . ? C10 C11 C12 C13 1.7(3) . . . . ? C11 C12 C13 N3 -0.5(4) . . . . ? C9 C10 C14 C15 1.5(3) . . . . ? C11 C10 C14 C15 -178.5(2) . . . . ? C10 C14 C15 C7 -1.1(3) . . . . ? C8 C7 C15 C14 0.1(3) . . . . ? C6 C7 C15 C14 -179.7(2) . . . . ? C5 C4 N2 C8 -0.4(3) . . . . ? C7 C8 N2 C4 0.4(3) . . . . ? C9 C8 N2 C4 -179.82(18) . . . . ? C12 C13 N3 C9 -1.4(3) . . . . ? C10 C9 N3 C13 2.1(3) . . . . ? C8 C9 N3 C13 -177.85(18) . . . . ? N1 C1 P1 O3 160.84(10) . . . . ? C2 C1 P1 O3 -82.87(13) . . . . ? P2 C1 P1 O3 48.33(11) . . . . ? N1 C1 P1 O2 33.48(12) . . . . ? C2 C1 P1 O2 149.77(11) . . . . ? P2 C1 P1 O2 -79.03(10) . . . . ? N1 C1 P1 O1 -83.83(11) . . . . ? C2 C1 P1 O1 32.47(13) . . . . ? P2 C1 P1 O1 163.67(9) . . . . ? N1 C1 P2 O4 -51.31(11) . . . . ? C2 C1 P2 O4 -164.71(11) . . . . ? P1 C1 P2 O4 63.73(10) . . . . ? N1 C1 P2 O6 73.74(11) . . . . ? C2 C1 P2 O6 -39.66(13) . . . . ? P1 C1 P2 O6 -171.22(8) . . . . ? N1 C1 P2 O5 -171.16(9) . . . . ? C2 C1 P2 O5 75.44(12) . . . . ? P1 C1 P2 O5 -56.12(10) . . . . ? C2 C3 P3 O8 -68.63(15) . . . . ? C2 C3 P3 O7 164.12(12) . . . . ? C2 C3 P3 O9 49.36(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 O4W H3W4 O2 0.896(15) 1.925(16) 2.801(2) 165(2) 2_766 O4W H4W4 O2 0.871(14) 1.969(15) 2.833(2) 171(2) 1_546 O4W H2W4 O3 0.890(14) 2.007(16) 2.872(2) 164(2) 2_666 O4W H1W4 O4 0.894(15) 2.32(3) 2.804(2) 114(2) 1_546 O4W H1W4 N2 0.894(15) 2.433(18) 3.214(2) 146(2) 1_545 O3W H2W3 O4 0.975(15) 3.00(2) 3.388(3) 105.1(15) 1_456 O1W H1W1 O9 0.828(18) 2.003(19) 2.825(2) 172(4) . N3 H16 O4 0.79(3) 1.97(3) 2.676(2) 149(3) 1_556 O9 H7 O6 0.77(3) 1.83(3) 2.5912(18) 169(3) 2_665 O1 H1 O7 0.71(3) 1.86(3) 2.572(2) 172(3) 1_655 O5 H2 O3 0.84(3) 1.82(3) 2.6621(18) 174(3) 2_675 N1 H3C O8 0.89 1.84 2.7093(18) 166.0 2_665 N1 H3B O4 0.89 2.37 2.8890(19) 117.2 . N1 H3B O3W 0.89 2.20 2.909(3) 136.6 1_654 N1 H3A O8 0.89 1.93 2.7417(19) 150.7 1_655 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.447 _refine_diff_density_min -0.628 _refine_diff_density_rms 0.067