# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Valery Brel' 'Vitaly K. Belsky' 'Peter J. Stang' 'Adam I. Stash' 'Valery E. Zavodnik' _publ_contact_author_name 'Prof Valery Brel' _publ_contact_author_address ; Laboratory of chemistry of fluorine compounds Institute of Physiologically Active Compounds Russian Academy of Sciences Severny proezd, 1 Chernogolovka Moscow region 142432 RUSSIAN FEDERATION ; _publ_contact_author_email BREL@IPAC.AC.RU _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; SYNTHESIS AND MOLECULAR STRUCTURE OF NEW ACYCLIC ANALOGUES OF NUCLEOTIDES WITH A 1,2-ALKADIENIC SKELETON. ; data_Compound_18 _database_code_CSD 218714 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H26 N5 O3 P' _chemical_formula_weight 379.40 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 28.047(6) _cell_length_b 11.272(2) _cell_length_c 13.562(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.05(3) _cell_angle_gamma 90.00 _cell_volume 4176.8(15) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 11.2 _cell_measurement_theta_max 12.5 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 beta-filter _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method theta/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1018 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 24.79 _reflns_number_total 997 _reflns_number_gt 997 _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^)+(0.1128P)^2^+14.4371P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 997 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1621 _refine_ls_wR_factor_gt 0.1621 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 P P 0.35774(11) 0.0797(4) 0.0526(3) 0.1042(12) Uani 1 1 d . . . O1 O 0.3084(2) 0.0932(8) 0.0643(5) 0.122(3) Uani 1 1 d . . . O2 O 0.3976(3) 0.0992(9) 0.1513(7) 0.126(3) Uani 1 1 d . . . O3 O 0.3721(3) -0.0469(9) 0.0161(8) 0.136(3) Uani 1 1 d . . . N1 N 0.3204(2) 0.4541(6) -0.0159(4) 0.063(2) Uani 1 1 d . . . N2 N 0.3342(3) 0.4657(7) 0.1534(5) 0.071(2) Uani 1 1 d . . . N3 N 0.4553(2) 0.5604(7) 0.1199(4) 0.066(2) Uani 1 1 d . . . N4 N 0.3997(2) 0.5204(7) -0.0392(4) 0.067(2) Uani 1 1 d . . . N5 N 0.4356(2) 0.5427(7) 0.2761(5) 0.072(2) Uani 1 1 d . . . C1 C 0.3732(5) 0.1721(12) -0.0406(10) 0.108(4) Uani 1 1 d . . . C2 C 0.3392(4) 0.2352(12) -0.0956(8) 0.087(3) Uani 1 1 d . . . C3 C 0.3050(4) 0.3010(12) -0.1472(7) 0.081(3) Uani 1 1 d . . . C4 C 0.2954(3) 0.4254(10) -0.1197(6) 0.075(3) Uani 1 1 d . . . C5 C 0.2712(5) 0.2588(12) -0.2446(8) 0.130(4) Uani 1 1 d . . . C6 C 0.4325(10) 0.1803(19) -0.0365(14) 0.191(10) Uani 1 1 d . . . C7 C 0.4388(8) 0.134(2) -0.1136(19) 0.232(10) Uani 1 1 d . . . C8 C 0.4975(6) 0.1383(16) -0.1067(15) 0.198(8) Uani 1 1 d . . . C9 C 0.3023(3) 0.4381(9) 0.0691(6) 0.071(3) Uani 1 1 d . . . C10 C 0.3754(3) 0.4994(8) 0.1215(5) 0.058(2) Uani 1 1 d . . . C11 C 0.4219(3) 0.5342(8) 0.1743(6) 0.060(2) Uani 1 1 d . . . C12 C 0.4418(3) 0.5529(9) 0.0187(6) 0.070(3) Uani 1 1 d . . . C13 C 0.3676(3) 0.4932(8) 0.0181(6) 0.057(2) Uani 1 1 d . . . C14 C 0.3939(7) 0.182(2) 0.2187(19) 0.232(12) Uani 1 1 d . . . C15 C 0.4270(11) 0.2114(17) 0.2880(18) 0.255(12) Uani 1 1 d . . . C16 C 0.3619(6) -0.154(2) 0.0639(13) 0.156(6) Uani 1 1 d . . . C17 C 0.3205(6) -0.2098(16) 0.0053(13) 0.175(6) Uani 1 1 d . . . H1N H 0.4121 0.5059 0.3163 0.085 Uiso 1 1 d . . . H2N H 0.4738 0.5720 0.3007 0.085 Uiso 1 1 d . . . H41 H 0.2576 0.4470 -0.1290 0.085 Uiso 1 1 d . . . H42 H 0.3075 0.4927 -0.1586 0.085 Uiso 1 1 d . . . H51 H 0.2356 0.2628 -0.2462 0.085 Uiso 1 1 d . . . H52 H 0.2821 0.1757 -0.2593 0.085 Uiso 1 1 d . . . H53 H 0.2795 0.3183 -0.2909 0.085 Uiso 1 1 d . . . H61 H 0.4550 0.1416 0.0253 0.085 Uiso 1 1 d . . . H62 H 0.4468 0.2614 -0.0359 0.085 Uiso 1 1 d . . . H71 H 0.4151 0.1653 -0.1697 0.085 Uiso 1 1 d . . . H72 H 0.4242 0.0459 -0.1084 0.085 Uiso 1 1 d . . . H81 H 0.5082 0.0979 -0.1660 0.085 Uiso 1 1 d . . . H82 H 0.5106 0.2192 -0.1086 0.085 Uiso 1 1 d . . . H83 H 0.5197 0.1002 -0.0474 0.085 Uiso 1 1 d . . . H9 H 0.2645 0.4265 0.0595 0.085 Uiso 1 1 d . . . H12 H 0.4715 0.5644 -0.0254 0.085 Uiso 1 1 d . . . H141 H 0.3655 0.1681 0.2520 0.085 Uiso 1 1 d . . . H142 H 0.3841 0.2614 0.1862 0.085 Uiso 1 1 d . . . H151 H 0.4218 0.2760 0.3416 0.085 Uiso 1 1 d . . . H152 H 0.4394 0.1440 0.3417 0.085 Uiso 1 1 d . . . H153 H 0.4582 0.2388 0.2750 0.085 Uiso 1 1 d . . . H161 H 0.3555 -0.1430 0.1332 0.085 Uiso 1 1 d . . . H162 H 0.3890 -0.2135 0.0766 0.085 Uiso 1 1 d . . . H171 H 0.3091 -0.2853 0.0287 0.085 Uiso 1 1 d . . . H172 H 0.2907 -0.1581 -0.0083 0.085 Uiso 1 1 d . . . H173 H 0.3244 -0.2290 -0.0653 0.085 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 P 0.0667(19) 0.128(3) 0.118(2) 0.002(3) 0.0200(17) -0.002(2) O1 0.067(4) 0.180(8) 0.124(6) 0.028(6) 0.031(4) 0.010(5) O2 0.084(5) 0.146(8) 0.139(7) -0.008(6) 0.004(5) 0.005(5) O3 0.139(8) 0.097(8) 0.180(9) 0.015(7) 0.050(7) 0.003(6) N1 0.052(4) 0.096(7) 0.040(4) -0.006(4) 0.009(3) 0.001(4) N2 0.062(5) 0.103(7) 0.048(4) -0.007(4) 0.013(4) 0.000(5) N3 0.058(4) 0.099(7) 0.039(4) 0.008(4) 0.010(3) -0.004(4) N4 0.054(5) 0.109(6) 0.041(4) 0.004(4) 0.012(4) -0.005(5) N5 0.058(4) 0.111(7) 0.045(4) 0.001(4) 0.011(3) -0.017(4) C1 0.076(8) 0.119(12) 0.144(11) 0.007(9) 0.056(8) 0.000(8) C2 0.071(7) 0.113(11) 0.081(8) -0.026(8) 0.025(6) -0.014(8) C3 0.068(7) 0.116(11) 0.056(6) -0.016(6) 0.008(5) -0.015(7) C4 0.059(5) 0.112(10) 0.049(5) 0.000(6) 0.002(4) 0.002(6) C5 0.146(10) 0.156(12) 0.078(7) -0.025(8) 0.001(7) -0.043(9) C6 0.29(3) 0.158(17) 0.134(15) 0.000(13) 0.067(17) 0.028(16) C7 0.19(2) 0.27(3) 0.23(2) 0.02(2) 0.03(2) -0.07(2) C8 0.132(12) 0.184(16) 0.31(2) 0.054(15) 0.112(14) 0.011(12) C9 0.055(5) 0.102(9) 0.058(6) -0.004(6) 0.016(5) -0.003(6) C10 0.053(5) 0.080(7) 0.040(5) -0.005(4) 0.009(4) -0.002(5) C11 0.065(5) 0.074(7) 0.041(5) 0.002(5) 0.012(4) -0.001(5) C12 0.056(5) 0.105(9) 0.049(5) 0.004(5) 0.010(4) 0.000(6) C13 0.053(6) 0.075(7) 0.041(5) 0.008(4) 0.008(4) 0.007(5) C14 0.165(17) 0.20(2) 0.29(3) -0.139(19) -0.055(16) 0.059(15) C15 0.40(4) 0.115(14) 0.22(2) -0.065(15) 0.01(2) 0.00(2) C16 0.105(11) 0.196(19) 0.155(14) 0.024(13) 0.001(10) 0.024(12) C17 0.153(14) 0.181(17) 0.180(16) 0.023(13) 0.014(12) 0.009(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 P O1 1.435(6) . ? P O2 1.554(8) . ? P O3 1.591(9) . ? P C1 1.766(13) . ? O2 C14 1.323(19) . ? O3 C16 1.427(18) . ? N1 C13 1.372(9) . ? N1 C9 1.373(9) . ? N1 C4 1.460(10) . ? N2 C9 1.320(9) . ? N2 C10 1.377(9) . ? N3 C12 1.342(9) . ? N3 C11 1.350(9) . ? N4 C12 1.315(10) . ? N4 C13 1.348(9) . ? N5 C11 1.351(9) . ? C1 C2 1.285(15) . ? C1 C6 1.65(3) . ? C2 C3 1.288(15) . ? C3 C4 1.491(13) . ? C3 C5 1.518(13) . ? C6 C7 1.22(2) . ? C7 C8 1.63(2) . ? C10 C13 1.371(10) . ? C10 C11 1.395(11) . ? C14 C15 1.21(2) . ? C16 C17 1.40(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P O2 114.4(5) . . ? O1 P O3 116.5(5) . . ? O2 P O3 102.2(6) . . ? O1 P C1 114.6(6) . . ? O2 P C1 106.7(6) . . ? O3 P C1 100.7(6) . . ? C14 O2 P 122.8(11) . . ? C16 O3 P 121.8(10) . . ? C13 N1 C9 105.8(6) . . ? C13 N1 C4 127.7(7) . . ? C9 N1 C4 126.3(7) . . ? C9 N2 C10 104.2(6) . . ? C12 N3 C11 118.4(7) . . ? C12 N4 C13 110.3(6) . . ? C2 C1 C6 126.7(12) . . ? C2 C1 P 118.1(9) . . ? C6 C1 P 114.6(11) . . ? C1 C2 C3 177.5(12) . . ? C2 C3 C4 124.0(9) . . ? C2 C3 C5 122.3(12) . . ? C4 C3 C5 113.6(11) . . ? N1 C4 C3 112.1(8) . . ? C7 C6 C1 107(2) . . ? C6 C7 C8 106(2) . . ? N2 C9 N1 113.0(7) . . ? C13 C10 N2 110.9(7) . . ? C13 C10 C11 117.0(8) . . ? N2 C10 C11 132.1(7) . . ? N3 C11 N5 118.1(7) . . ? N3 C11 C10 117.7(7) . . ? N5 C11 C10 124.2(8) . . ? N4 C12 N3 129.4(7) . . ? N4 C13 C10 127.2(8) . . ? N4 C13 N1 126.7(7) . . ? C10 C13 N1 106.1(7) . . ? C15 C14 O2 124(2) . . ? C17 C16 O3 110.3(14) . . ? _diffrn_measured_fraction_theta_max 0.278 _diffrn_reflns_theta_full 24.79 _diffrn_measured_fraction_theta_full 0.278 _refine_diff_density_max 0.173 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.043 data_compound_2f _database_code_CSD 218715 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 N2 O5 P' _chemical_formula_weight 327.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 14.135(3) _cell_length_b 8.272(2) _cell_length_c 14.408(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.97(3) _cell_angle_gamma 90.00 _cell_volume 1611.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 11.3 _cell_measurement_theta_max 12.7 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 0.195 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 beta-filter _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method theta/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1890 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1810 _reflns_number_gt 1810 _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^)+(0.0734P)^2^+0.6170P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0047(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1810 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 P P 0.16812(7) 0.66743(10) 0.66819(7) 0.0712(3) Uani 1 1 d . . . O1 O 0.47928(15) 0.7044(2) 0.50469(12) 0.0577(5) Uani 1 1 d . . . O2 O 0.51811(17) 0.3514(2) 0.75229(15) 0.0711(6) Uani 1 1 d . . . O3A O 0.1900(5) 0.8325(9) 0.7410(4) 0.0653(15) Uani 0.559(11) 1 d P . . O3B O 0.2229(5) 0.7485(11) 0.7479(3) 0.059(2) Uani 0.441(11) 1 d P . . O4A O 0.0473(5) 0.7064(9) 0.6222(5) 0.0577(15) Uani 0.559(11) 1 d P . . O4B O 0.0663(6) 0.6489(10) 0.6531(6) 0.0539(19) Uani 0.441(11) 1 d P . . O5A O 0.2262(7) 0.5316(7) 0.7290(5) 0.110(3) Uani 0.559(11) 1 d P . . O5B O 0.1641(4) 0.4778(6) 0.6725(5) 0.062(2) Uani 0.441(11) 1 d P . . N1 N 0.45821(14) 0.7984(2) 0.64553(14) 0.0429(5) Uani 1 1 d . . . N2 N 0.49922(16) 0.5328(3) 0.63198(15) 0.0480(5) Uani 1 1 d . . . C1 C 0.20749(19) 0.7044(3) 0.56336(18) 0.0478(6) Uani 1 1 d . . . C2 C 0.25818(18) 0.8351(3) 0.56024(17) 0.0424(6) Uani 1 1 d . . . C3 C 0.31238(18) 0.9624(3) 0.56070(15) 0.0396(5) Uani 1 1 d . . . C4 C 0.4229(2) 0.9556(3) 0.6028(2) 0.0477(6) Uani 1 1 d . . . C5 C 0.2715(3) 1.1245(3) 0.5225(2) 0.0569(8) Uani 1 1 d . . . C6 C 0.1816(3) 0.5768(4) 0.4848(2) 0.0647(8) Uani 1 1 d . . . C7 C 0.2118(2) 0.6151(4) 0.3957(2) 0.0585(7) Uani 1 1 d . . . C8 C 0.1858(4) 0.4829(4) 0.3203(3) 0.0788(10) Uani 1 1 d . . . C9 C 0.2092(4) 0.5236(7) 0.2273(3) 0.0904(12) Uani 1 1 d . . . C10 C 0.47872(18) 0.6807(3) 0.58848(18) 0.0432(6) Uani 1 1 d . . . C11 C 0.49957(18) 0.4923(3) 0.72453(18) 0.0478(6) Uani 1 1 d . . . C12 C 0.47894(18) 0.6225(3) 0.78156(17) 0.0452(6) Uani 1 1 d . . . C13 C 0.45850(18) 0.7669(3) 0.73914(16) 0.0453(6) Uani 1 1 d . . . C14 C 0.4795(3) 0.5954(5) 0.8847(2) 0.0630(8) Uani 1 1 d . . . H2N H 0.511(2) 0.456(4) 0.598(2) 0.060(8) Uiso 1 1 d . . . H41 H 0.4450(19) 1.035(3) 0.654(2) 0.054(7) Uiso 1 1 d . . . H42 H 0.4518(19) 0.977(3) 0.5517(19) 0.051(7) Uiso 1 1 d . . . H51 H 0.281(3) 1.202(5) 0.580(3) 0.096(11) Uiso 1 1 d . . . H52 H 0.304(3) 1.165(4) 0.478(3) 0.088(11) Uiso 1 1 d . . . H53 H 0.203(3) 1.113(5) 0.483(3) 0.105(13) Uiso 1 1 d . . . H61 H 0.109(3) 0.546(5) 0.469(3) 0.106(13) Uiso 1 1 d . . . H62 H 0.207(3) 0.471(5) 0.513(3) 0.103(12) Uiso 1 1 d . . . H71 H 0.178(2) 0.724(4) 0.368(2) 0.072(9) Uiso 1 1 d . . . H72 H 0.276(3) 0.638(4) 0.412(2) 0.069(9) Uiso 1 1 d . . . H81 H 0.113(3) 0.465(5) 0.309(3) 0.109(14) Uiso 1 1 d . . . H82 H 0.230(3) 0.400(6) 0.345(3) 0.114(15) Uiso 1 1 d . . . H91 H 0.282(4) 0.544(6) 0.244(3) 0.127(16) Uiso 1 1 d . . . H92 H 0.187(4) 0.437(7) 0.181(4) 0.142(18) Uiso 1 1 d . . . H93 H 0.177(3) 0.627(6) 0.201(3) 0.120(16) Uiso 1 1 d . . . H13 H 0.4387(18) 0.860(3) 0.7725(18) 0.046(7) Uiso 1 1 d . . . H141 H 0.466(3) 0.698(5) 0.916(3) 0.099(12) Uiso 1 1 d . . . H142 H 0.429(3) 0.524(4) 0.892(2) 0.077(10) Uiso 1 1 d . . . H143 H 0.546(4) 0.563(5) 0.922(3) 0.119(15) 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 P 0.0892(7) 0.0555(5) 0.0860(6) 0.0281(4) 0.0525(5) 0.0023(4) O1 0.0873(15) 0.0484(10) 0.0500(10) 0.0031(8) 0.0396(10) 0.0092(9) O2 0.1024(17) 0.0546(12) 0.0758(13) 0.0189(10) 0.0563(12) 0.0230(11) O3A 0.080(3) 0.064(3) 0.060(3) -0.011(2) 0.032(2) -0.002(3) O3B 0.069(4) 0.073(5) 0.032(2) 0.003(3) 0.007(2) -0.016(3) O4A 0.064(3) 0.059(4) 0.051(3) -0.003(2) 0.019(2) 0.007(3) O4B 0.059(4) 0.050(4) 0.063(5) -0.013(3) 0.033(4) -0.024(3) O5A 0.172(8) 0.084(4) 0.077(4) 0.044(3) 0.040(5) 0.004(4) O5B 0.064(4) 0.050(3) 0.072(4) 0.030(3) 0.019(3) -0.007(2) N1 0.0487(12) 0.0409(11) 0.0437(10) -0.0030(8) 0.0210(9) 0.0031(9) N2 0.0637(14) 0.0413(12) 0.0494(12) 0.0020(10) 0.0330(10) 0.0104(10) C1 0.0543(15) 0.0357(13) 0.0571(14) 0.0136(11) 0.0219(12) 0.0036(11) C2 0.0539(15) 0.0368(13) 0.0404(12) 0.0089(10) 0.0200(11) 0.0069(11) C3 0.0572(14) 0.0335(12) 0.0351(11) 0.0028(9) 0.0243(10) 0.0007(11) C4 0.0628(16) 0.0344(13) 0.0544(15) -0.0012(11) 0.0302(13) -0.0030(12) C5 0.084(2) 0.0375(14) 0.0547(16) 0.0129(12) 0.0294(17) 0.0063(14) C6 0.080(2) 0.0374(15) 0.080(2) 0.0050(15) 0.0279(17) -0.0081(14) C7 0.0566(18) 0.0520(17) 0.0663(17) -0.0036(14) 0.0167(14) -0.0041(14) C8 0.099(3) 0.057(2) 0.078(2) -0.0094(17) 0.022(2) 0.002(2) C9 0.095(3) 0.098(3) 0.080(3) -0.018(2) 0.028(2) 0.007(3) C10 0.0471(14) 0.0430(14) 0.0465(13) -0.0010(11) 0.0249(11) 0.0014(10) C11 0.0495(14) 0.0498(15) 0.0515(14) 0.0051(11) 0.0264(11) 0.0052(11) C12 0.0438(13) 0.0525(15) 0.0408(12) -0.0021(11) 0.0150(11) -0.0012(11) C13 0.0464(14) 0.0505(15) 0.0418(13) -0.0084(12) 0.0169(11) -0.0014(12) C14 0.076(2) 0.074(2) 0.0406(14) -0.0023(14) 0.0205(14) -0.0033(18) _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 P O3B 1.360(6) . ? P O4B 1.400(8) . ? P O5A 1.511(5) . ? P O5B 1.572(5) . ? P O4A 1.673(7) . ? P O3A 1.694(6) . ? P C1 1.782(3) . ? O1 C10 1.225(3) . ? O2 C11 1.235(3) . ? O3A O3B 0.826(6) . ? O3B O5A 1.818(9) . ? O4A O4B 0.653(7) . ? O5A O5B 1.102(7) . ? N1 C10 1.359(3) . ? N1 C13 1.373(3) . ? N1 C4 1.463(3) . ? N2 C10 1.367(3) . ? N2 C11 1.374(3) . ? C1 C2 1.305(3) . ? C1 C6 1.513(4) . ? C2 C3 1.301(3) . ? C3 C5 1.500(3) . ? C3 C4 1.503(4) . ? C6 C7 1.500(4) . ? C7 C8 1.509(4) . ? C8 C9 1.509(6) . ? C11 C12 1.435(3) . ? C12 C13 1.335(4) . ? C12 C14 1.501(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 O3B P O4B 119.4(4) . . ? O3B P O5A 78.3(4) . . ? O4B P O5A 111.7(7) . . ? O3B P O5B 118.5(3) . . ? O4B P O5B 81.3(5) . . ? O5A P O5B 41.8(3) . . ? O3B P O4A 120.2(5) . . ? O4B P O4A 22.4(3) . . ? O5A P O4A 133.8(5) . . ? O5B P O4A 99.4(4) . . ? O3B P O3A 28.8(3) . . ? O4B P O3A 100.2(4) . . ? O5A P O3A 105.7(3) . . ? O5B P O3A 141.4(3) . . ? O4A P O3A 94.1(4) . . ? O3B P C1 113.0(2) . . ? O4B P C1 116.7(4) . . ? O5A P C1 111.5(2) . . ? O5B P C1 103.2(2) . . ? O4A P C1 99.6(3) . . ? O3A P C1 109.9(2) . . ? O3B O3A P 52.5(5) . . ? O3A O3B P 98.7(7) . . ? O3A O3B O5A 148.3(9) . . ? P O3B O5A 54.5(3) . . ? O4B O4A P 54.6(10) . . ? O4A O4B P 103.0(12) . . ? O5B O5A P 72.0(5) . . ? O5B O5A O3B 117.4(6) . . ? P O5A O3B 47.1(2) . . ? O5A O5B P 66.2(4) . . ? C10 N1 C13 121.2(2) . . ? C10 N1 C4 119.26(19) . . ? C13 N1 C4 119.1(2) . . ? C10 N2 C11 127.2(2) . . ? C2 C1 C6 124.6(2) . . ? C2 C1 P 118.8(2) . . ? C6 C1 P 116.60(19) . . ? C3 C2 C1 177.1(3) . . ? C2 C3 C5 124.0(2) . . ? C2 C3 C4 120.9(2) . . ? C5 C3 C4 115.2(2) . . ? N1 C4 C3 112.9(2) . . ? C7 C6 C1 115.2(2) . . ? C6 C7 C8 113.1(3) . . ? C9 C8 C7 114.0(3) . . ? O1 C10 N1 123.0(2) . . ? O1 C10 N2 122.3(2) . . ? N1 C10 N2 114.7(2) . . ? O2 C11 N2 119.0(2) . . ? O2 C11 C12 125.6(2) . . ? N2 C11 C12 115.4(2) . . ? C13 C12 C11 117.6(2) . . ? C13 C12 C14 121.7(2) . . ? C11 C12 C14 120.8(3) . . ? C12 C13 N1 123.9(2) . . ? _diffrn_measured_fraction_theta_max 0.640 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.640 _refine_diff_density_max 0.299 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.040