# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name J.Gavette J.Lara O.Berryman L.Zakharov M.Haley D.Johnson _publ_contact_author_name 'Dr Darren Johnson' _publ_contact_author_email dwj@uoregon.edu data_jgar1 _database_code_depnum_ccdc_archive 'CCDC 824327' #TrackingRef '- jgar1.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H49 N6 O12 P' _chemical_formula_weight 644.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.1651(19) _cell_length_b 13.264(2) _cell_length_c 13.360(2) _cell_angle_alpha 93.405(3) _cell_angle_beta 109.288(3) _cell_angle_gamma 111.239(3) _cell_volume 1704.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2286 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 21.95 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9746 _exptl_absorpt_correction_T_max 0.9971 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CBruker Apex CD 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 16644 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0615 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6003 _reflns_number_gt 4435 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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. The distances of 1.009 and 1.00 were used in the refinements as targets for N-H and O-H bond lengths, respectively. ; _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^)+(0.0561P)^2^+0.7124P] 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 6003 _refine_ls_number_parameters 428 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0729 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1320 _refine_ls_wR_factor_gt 0.1097 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.014 _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 0.84819(7) 0.31461(5) 0.35806(6) 0.02078(18) Uani 1 1 d . . . O1 O 0.79518(18) 0.40025(14) 0.37382(15) 0.0269(4) Uani 1 1 d . . . O2 O 1.01304(19) 0.19256(14) 0.56904(14) 0.0267(4) Uani 1 1 d . . . O3 O 0.90563(19) 0.48285(16) 0.78565(17) 0.0380(5) Uani 1 1 d . . . O4 O 0.8113(2) 0.31135(15) 0.67819(16) 0.0349(5) Uani 1 1 d . . . O5 O 0.65707(18) 0.02562(14) 0.19109(14) 0.0258(4) Uani 1 1 d . . . O6 O 1.20185(19) 0.08132(15) 0.43707(16) 0.0340(5) Uani 1 1 d . . . O7 O 1.08805(19) 0.16956(15) 0.32517(15) 0.0283(5) Uani 1 1 d . . . O8 O 0.72074(19) 0.40305(15) 0.08874(15) 0.0291(5) Uani 1 1 d . . . O9 O 0.2864(2) -0.00543(15) 0.04560(16) 0.0369(5) Uani 1 1 d . . . O10 O 0.3939(2) 0.16461(16) 0.15724(16) 0.0410(6) Uani 1 1 d . . . N1 N 1.0501(2) 0.37018(18) 0.56054(17) 0.0225(5) Uani 1 1 d D . . N2 N 1.0439(2) 0.40550(19) 0.76714(19) 0.0272(5) Uani 1 1 d D . . N3 N 0.8033(2) 0.10159(17) 0.36531(18) 0.0216(5) Uani 1 1 d D . . N4 N 0.9751(2) -0.00193(18) 0.34996(18) 0.0253(5) Uani 1 1 d D . . N5 N 0.7071(2) 0.24167(18) 0.14219(17) 0.0235(5) Uani 1 1 d D . . N6 N 0.4322(2) 0.13261(19) 0.00406(18) 0.0280(6) Uani 1 1 d D . . C1 C 1.0282(3) 0.3549(2) 0.4458(2) 0.0222(6) Uani 1 1 d . . . H1B H 1.0593 0.2974 0.4284 0.027 Uiso 1 1 calc R . . H1C H 1.0860 0.4247 0.4315 0.027 Uiso 1 1 calc R . . C2 C 1.0417(3) 0.2876(2) 0.6135(2) 0.0221(6) Uani 1 1 d . . . C3 C 1.0729(3) 0.3142(2) 0.7332(2) 0.0282(7) Uani 1 1 d . . . H3A H 1.0178 0.2476 0.7537 0.034 Uiso 1 1 calc R . . H3B H 1.1722 0.3313 0.7734 0.034 Uiso 1 1 calc R . . C4 C 0.9102(3) 0.3923(2) 0.7386(2) 0.0281(7) Uani 1 1 d . . . C5 C 0.7712(3) 0.4865(2) 0.7781(3) 0.0371(8) Uani 1 1 d . . . C6 C 0.6910(3) 0.3909(3) 0.8182(3) 0.0451(8) Uani 1 1 d . . . H6A H 0.6613 0.3217 0.7681 0.068 Uiso 1 1 calc R . . H6B H 0.6093 0.3999 0.8223 0.068 Uiso 1 1 calc R . . H6C H 0.7503 0.3889 0.8903 0.068 Uiso 1 1 calc R . . C7 C 0.6922(3) 0.4912(3) 0.6637(3) 0.0472(9) Uani 1 1 d . . . H7A H 0.6622 0.4208 0.6154 0.071 Uiso 1 1 calc R . . H7B H 0.7524 0.5511 0.6404 0.071 Uiso 1 1 calc R . . H7C H 0.6106 0.5048 0.6610 0.071 Uiso 1 1 calc R . . C8 C 0.8188(4) 0.5953(3) 0.8546(4) 0.0699(13) Uani 1 1 d . . . H8A H 0.8705 0.6565 0.8273 0.105 Uiso 1 1 calc R . . H8B H 0.8789 0.5943 0.9268 0.105 Uiso 1 1 calc R . . H8C H 0.7377 0.6051 0.8591 0.105 Uiso 1 1 calc R . . C9 C 0.7477(3) 0.1817(2) 0.3811(2) 0.0230(6) Uani 1 1 d . . . H9A H 0.7500 0.1908 0.4559 0.028 Uiso 1 1 calc R . . H9B H 0.6498 0.1547 0.3305 0.028 Uiso 1 1 calc R . . C10 C 0.7611(3) 0.0361(2) 0.2700(2) 0.0209(6) Uani 1 1 d . . . C11 C 0.8482(3) -0.0252(2) 0.2583(2) 0.0259(6) Uani 1 1 d . . . H11A H 0.7900 -0.1054 0.2424 0.031 Uiso 1 1 calc R . . H11B H 0.8726 -0.0083 0.1946 0.031 Uiso 1 1 calc R . . C12 C 1.0899(3) 0.0910(2) 0.3673(2) 0.0246(6) Uani 1 1 d . . . C13 C 1.3388(3) 0.1764(2) 0.4875(2) 0.0307(7) Uani 1 1 d . . . C14 C 1.3281(3) 0.2584(3) 0.5634(3) 0.0490(9) Uani 1 1 d . . . H14A H 1.2680 0.2920 0.5215 0.074 Uiso 1 1 calc R . . H14B H 1.4207 0.3160 0.6051 0.074 Uiso 1 1 calc R . . H14C H 1.2886 0.2204 0.6131 0.074 Uiso 1 1 calc R . . C15 C 1.3899(3) 0.2278(3) 0.4033(3) 0.0414(8) Uani 1 1 d . . . H15A H 1.3301 0.2631 0.3644 0.062 Uiso 1 1 calc R . . H15B H 1.3873 0.1704 0.3520 0.062 Uiso 1 1 calc R . . H15C H 1.4854 0.2834 0.4391 0.062 Uiso 1 1 calc R . . C16 C 1.4308(3) 0.1218(3) 0.5480(3) 0.0526(10) Uani 1 1 d . . . H16A H 1.3972 0.0885 0.6024 0.079 Uiso 1 1 calc R . . H16B H 1.5263 0.1772 0.5840 0.079 Uiso 1 1 calc R . . H16C H 1.4283 0.0642 0.4969 0.079 Uiso 1 1 calc R . . C17 C 0.8473(3) 0.2855(2) 0.2227(2) 0.0236(6) Uani 1 1 d . . . H17A H 0.9044 0.3542 0.2063 0.028 Uiso 1 1 calc R . . H17B H 0.8887 0.2314 0.2198 0.028 Uiso 1 1 calc R . . C18 C 0.6545(3) 0.3047(2) 0.0831(2) 0.0228(6) Uani 1 1 d . . . C19 C 0.5046(3) 0.2486(2) 0.0047(2) 0.0280(7) Uani 1 1 d . . . H19A H 0.4527 0.2894 0.0217 0.034 Uiso 1 1 calc R . . H19B H 0.5021 0.2553 -0.0693 0.034 Uiso 1 1 calc R . . C20 C 0.3724(3) 0.1026(2) 0.0765(2) 0.0293(7) Uani 1 1 d . . . C21 C 0.2240(3) -0.0650(2) 0.1182(2) 0.0319(7) Uani 1 1 d . . . C22 C 0.3378(3) -0.0642(3) 0.2191(3) 0.0430(8) Uani 1 1 d . . . H22A H 0.3914 0.0112 0.2620 0.065 Uiso 1 1 calc R . . H22B H 0.3992 -0.0909 0.1984 0.065 Uiso 1 1 calc R . . H22C H 0.2964 -0.1126 0.2621 0.065 Uiso 1 1 calc R . . C23 C 0.1391(4) -0.1807(3) 0.0495(3) 0.0518(10) Uani 1 1 d . . . H23A H 0.0661 -0.1793 -0.0153 0.078 Uiso 1 1 calc R . . H23B H 0.0967 -0.2299 0.0915 0.078 Uiso 1 1 calc R . . H23C H 0.1996 -0.2077 0.0279 0.078 Uiso 1 1 calc R . . C24 C 0.1307(3) -0.0170(3) 0.1434(3) 0.0440(8) Uani 1 1 d . . . H24A H 0.0590 -0.0193 0.0757 0.066 Uiso 1 1 calc R . . H24B H 0.1861 0.0597 0.1828 0.066 Uiso 1 1 calc R . . H24C H 0.0865 -0.0603 0.1882 0.066 Uiso 1 1 calc R . . O1S O 0.5333(2) 0.40208(18) 0.25533(19) 0.0401(5) Uani 1 1 d D . . O2S O 0.5843(3) 0.5568(3) 0.1216(3) 0.0699(9) Uani 1 1 d D . . H1N H 1.089(3) 0.4469(16) 0.598(2) 0.053(10) Uiso 1 1 d D . . H2N H 1.119(3) 0.470(2) 0.820(2) 0.051(10) Uiso 1 1 d D . . H3N H 0.887(2) 0.105(2) 0.420(2) 0.043(9) Uiso 1 1 d D . . H4N H 0.987(3) -0.0635(19) 0.381(2) 0.039(9) Uiso 1 1 d D . . H5N H 0.648(3) 0.1653(15) 0.134(2) 0.036(8) Uiso 1 1 d D . . H6N H 0.409(3) 0.0776(19) -0.0578(18) 0.032(8) Uiso 1 1 d D . . H1S H 0.623(2) 0.406(3) 0.299(3) 0.073(12) Uiso 1 1 d D . . H2S H 0.476(4) 0.3257(18) 0.220(3) 0.092(15) Uiso 1 1 d D . . H3S H 0.557(4) 0.501(3) 0.163(3) 0.102(16) Uiso 1 1 d D . . H4S H 0.610(5) 0.522(4) 0.070(3) 0.13(2) 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 0.0221(4) 0.0167(4) 0.0212(4) 0.0023(3) 0.0058(3) 0.0078(3) O1 0.0284(11) 0.0199(10) 0.0303(11) 0.0012(8) 0.0069(9) 0.0118(8) O2 0.0326(11) 0.0182(10) 0.0244(10) 0.0023(8) 0.0050(9) 0.0104(9) O3 0.0244(11) 0.0293(11) 0.0519(14) -0.0112(10) 0.0127(10) 0.0063(9) O4 0.0277(11) 0.0252(11) 0.0396(12) -0.0047(9) 0.0090(10) 0.0025(9) O5 0.0220(10) 0.0234(10) 0.0251(11) 0.0007(8) 0.0018(9) 0.0086(8) O6 0.0227(11) 0.0289(11) 0.0410(12) 0.0114(9) 0.0024(9) 0.0084(9) O7 0.0319(11) 0.0237(10) 0.0296(11) 0.0087(9) 0.0098(9) 0.0128(9) O8 0.0294(11) 0.0213(11) 0.0276(11) 0.0065(8) 0.0047(9) 0.0059(9) O9 0.0440(13) 0.0237(11) 0.0300(12) -0.0016(9) 0.0179(10) -0.0029(9) O10 0.0541(14) 0.0288(12) 0.0305(12) -0.0036(10) 0.0206(11) 0.0035(10) N1 0.0248(12) 0.0183(12) 0.0209(12) 0.0020(10) 0.0048(10) 0.0087(10) N2 0.0260(13) 0.0238(13) 0.0262(13) -0.0036(10) 0.0071(11) 0.0079(11) N3 0.0242(13) 0.0169(11) 0.0224(13) 0.0028(10) 0.0061(10) 0.0097(10) N4 0.0246(13) 0.0198(12) 0.0267(13) 0.0044(10) 0.0025(10) 0.0100(10) N5 0.0249(13) 0.0192(12) 0.0199(12) 0.0044(10) 0.0039(10) 0.0060(10) N6 0.0297(14) 0.0236(13) 0.0200(13) -0.0008(10) 0.0073(11) 0.0017(11) C1 0.0242(15) 0.0179(13) 0.0229(15) 0.0027(11) 0.0077(12) 0.0081(12) C2 0.0188(14) 0.0203(14) 0.0257(15) 0.0028(12) 0.0066(12) 0.0080(11) C3 0.0329(16) 0.0238(15) 0.0265(16) 0.0033(12) 0.0092(13) 0.0122(13) C4 0.0278(16) 0.0250(16) 0.0293(16) 0.0012(13) 0.0140(13) 0.0059(13) C5 0.0227(16) 0.0337(17) 0.053(2) -0.0031(15) 0.0175(15) 0.0078(14) C6 0.042(2) 0.055(2) 0.042(2) 0.0112(17) 0.0227(17) 0.0187(17) C7 0.040(2) 0.045(2) 0.068(3) 0.0229(18) 0.0303(19) 0.0194(17) C8 0.039(2) 0.049(2) 0.110(4) -0.029(2) 0.030(2) 0.0092(18) C9 0.0235(15) 0.0189(14) 0.0247(15) 0.0019(11) 0.0092(12) 0.0068(12) C10 0.0225(14) 0.0125(13) 0.0229(15) 0.0042(11) 0.0069(12) 0.0033(11) C11 0.0260(15) 0.0218(14) 0.0232(15) -0.0022(12) 0.0035(12) 0.0088(12) C12 0.0263(15) 0.0231(15) 0.0247(15) 0.0022(12) 0.0078(12) 0.0124(13) C13 0.0193(15) 0.0312(16) 0.0313(17) 0.0047(13) 0.0043(13) 0.0042(13) C14 0.0310(18) 0.063(2) 0.038(2) -0.0102(17) 0.0083(15) 0.0101(17) C15 0.0345(18) 0.045(2) 0.0348(18) 0.0025(15) 0.0127(15) 0.0063(15) C16 0.0262(18) 0.054(2) 0.065(2) 0.0238(19) 0.0040(17) 0.0115(16) C17 0.0234(15) 0.0197(14) 0.0246(15) 0.0044(12) 0.0061(12) 0.0082(12) C18 0.0285(15) 0.0210(15) 0.0171(14) 0.0021(11) 0.0090(12) 0.0078(12) C19 0.0292(16) 0.0245(15) 0.0219(15) 0.0050(12) 0.0039(13) 0.0069(13) C20 0.0296(16) 0.0253(15) 0.0253(16) 0.0004(13) 0.0072(13) 0.0062(13) C21 0.0309(17) 0.0262(15) 0.0316(17) 0.0040(13) 0.0148(14) 0.0018(13) C22 0.0379(19) 0.044(2) 0.045(2) 0.0161(16) 0.0144(16) 0.0136(16) C23 0.056(2) 0.0336(19) 0.051(2) 0.0009(16) 0.0302(19) -0.0048(17) C24 0.0411(19) 0.051(2) 0.041(2) 0.0126(16) 0.0161(16) 0.0196(17) O1S 0.0353(13) 0.0377(13) 0.0492(14) 0.0115(11) 0.0135(11) 0.0187(11) O2S 0.0535(17) 0.079(2) 0.096(2) 0.0542(19) 0.0303(17) 0.0398(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 O1 1.4920(18) . ? P1 C1 1.814(3) . ? P1 C17 1.823(3) . ? P1 C9 1.822(3) . ? O2 C2 1.240(3) . ? O3 C4 1.347(3) . ? O3 C5 1.490(3) . ? O4 C4 1.214(3) . ? O5 C10 1.239(3) . ? O6 C12 1.345(3) . ? O6 C13 1.484(3) . ? O7 C12 1.217(3) . ? O8 C18 1.228(3) . ? O9 C20 1.348(3) . ? O9 C21 1.480(3) . ? O10 C20 1.215(3) . ? N1 C2 1.331(3) . ? N1 C1 1.459(3) . ? N1 H1N 0.975(18) . ? N2 C4 1.352(3) . ? N2 C3 1.447(3) . ? N2 H2N 0.977(18) . ? N3 C10 1.332(3) . ? N3 C9 1.448(3) . ? N3 H3N 0.961(17) . ? N4 C12 1.357(3) . ? N4 C11 1.448(3) . ? N4 H4N 0.969(17) . ? N5 C18 1.339(3) . ? N5 C17 1.449(3) . ? N5 H5N 0.962(17) . ? N6 C20 1.350(4) . ? N6 C19 1.453(3) . ? N6 H6N 0.967(17) . ? C1 H1B 0.9900 . ? C1 H1C 0.9900 . ? C2 C3 1.509(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 C7 1.510(5) . ? C5 C6 1.507(4) . ? C5 C8 1.523(4) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.513(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C13 C14 1.507(4) . ? C13 C15 1.513(4) . ? C13 C16 1.514(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.516(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C21 C24 1.515(4) . ? C21 C23 1.516(4) . ? C21 C22 1.513(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? O1S H1S 0.959(19) . ? O1S H2S 0.964(19) . ? O2S H3S 0.968(19) . ? O2S H4S 0.975(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C1 112.71(11) . . ? O1 P1 C17 114.27(12) . . ? C1 P1 C17 103.57(12) . . ? O1 P1 C9 112.72(12) . . ? C1 P1 C9 107.45(12) . . ? C17 P1 C9 105.37(12) . . ? C4 O3 C5 121.3(2) . . ? C12 O6 C13 122.2(2) . . ? C20 O9 C21 121.4(2) . . ? C2 N1 C1 121.8(2) . . ? C2 N1 H1N 122.0(19) . . ? C1 N1 H1N 115.0(19) . . ? C4 N2 C3 119.0(2) . . ? C4 N2 H2N 120.7(19) . . ? C3 N2 H2N 119.5(19) . . ? C10 N3 C9 123.0(2) . . ? C10 N3 H3N 116.4(18) . . ? C9 N3 H3N 119.3(18) . . ? C12 N4 C11 120.0(2) . . ? C12 N4 H4N 118.4(17) . . ? C11 N4 H4N 117.7(17) . . ? C18 N5 C17 122.4(2) . . ? C18 N5 H5N 119.0(17) . . ? C17 N5 H5N 118.5(17) . . ? C20 N6 C19 120.6(2) . . ? C20 N6 H6N 119.0(17) . . ? C19 N6 H6N 119.0(17) . . ? N1 C1 P1 112.80(18) . . ? N1 C1 H1B 109.0 . . ? P1 C1 H1B 109.0 . . ? N1 C1 H1C 109.0 . . ? P1 C1 H1C 109.0 . . ? H1B C1 H1C 107.8 . . ? O2 C2 N1 122.7(2) . . ? O2 C2 C3 120.0(2) . . ? N1 C2 C3 117.2(2) . . ? N2 C3 C2 115.0(2) . . ? N2 C3 H3A 108.5 . . ? C2 C3 H3A 108.5 . . ? N2 C3 H3B 108.5 . . ? C2 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? O4 C4 N2 124.2(3) . . ? O4 C4 O3 126.2(3) . . ? N2 C4 O3 109.6(2) . . ? O3 C5 C7 109.4(2) . . ? O3 C5 C6 110.4(3) . . ? C7 C5 C6 113.5(3) . . ? O3 C5 C8 102.1(2) . . ? C7 C5 C8 110.3(3) . . ? C6 C5 C8 110.6(3) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 P1 110.68(18) . . ? N3 C9 H9A 109.5 . . ? P1 C9 H9A 109.5 . . ? N3 C9 H9B 109.5 . . ? P1 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? O5 C10 N3 123.2(2) . . ? O5 C10 C11 119.3(2) . . ? N3 C10 C11 117.4(2) . . ? N4 C11 C10 116.8(2) . . ? N4 C11 H11A 108.1 . . ? C10 C11 H11A 108.1 . . ? N4 C11 H11B 108.1 . . ? C10 C11 H11B 108.1 . . ? H11A C11 H11B 107.3 . . ? O7 C12 O6 126.8(2) . . ? O7 C12 N4 123.9(2) . . ? O6 C12 N4 109.4(2) . . ? O6 C13 C14 108.7(2) . . ? O6 C13 C15 111.8(2) . . ? C14 C13 C15 112.3(3) . . ? O6 C13 C16 102.0(2) . . ? C14 C13 C16 111.8(3) . . ? C15 C13 C16 109.8(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N5 C17 P1 110.80(18) . . ? N5 C17 H17A 109.5 . . ? P1 C17 H17A 109.5 . . ? N5 C17 H17B 109.5 . . ? P1 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? O8 C18 N5 123.9(2) . . ? O8 C18 C19 119.4(2) . . ? N5 C18 C19 116.7(2) . . ? N6 C19 C18 116.3(2) . . ? N6 C19 H19A 108.2 . . ? C18 C19 H19A 108.2 . . ? N6 C19 H19B 108.2 . . ? C18 C19 H19B 108.2 . . ? H19A C19 H19B 107.4 . . ? O10 C20 N6 124.5(3) . . ? O10 C20 O9 125.7(3) . . ? N6 C20 O9 109.7(2) . . ? O9 C21 C24 111.0(2) . . ? O9 C21 C23 101.9(2) . . ? C24 C21 C23 110.5(3) . . ? O9 C21 C22 109.5(2) . . ? C24 C21 C22 112.6(3) . . ? C23 C21 C22 110.9(3) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? H1S O1S H2S 107(3) . . ? H3S O2S H4S 104(4) . . ? 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 C2 N1 C1 P1 90.0(3) . . . . ? O1 P1 C1 N1 62.5(2) . . . . ? C17 P1 C1 N1 -173.47(18) . . . . ? C9 P1 C1 N1 -62.3(2) . . . . ? C1 N1 C2 O2 -1.1(4) . . . . ? C1 N1 C2 C3 177.2(2) . . . . ? C4 N2 C3 C2 70.5(3) . . . . ? O2 C2 C3 N2 -153.4(2) . . . . ? N1 C2 C3 N2 28.2(3) . . . . ? C3 N2 C4 O4 -6.3(4) . . . . ? C3 N2 C4 O3 174.8(2) . . . . ? C5 O3 C4 O4 7.8(4) . . . . ? C5 O3 C4 N2 -173.3(2) . . . . ? C4 O3 C5 C7 -70.7(3) . . . . ? C4 O3 C5 C6 54.9(4) . . . . ? C4 O3 C5 C8 172.4(3) . . . . ? C10 N3 C9 P1 -90.1(3) . . . . ? O1 P1 C9 N3 -179.79(17) . . . . ? C1 P1 C9 N3 -55.0(2) . . . . ? C17 P1 C9 N3 55.0(2) . . . . ? C9 N3 C10 O5 -11.5(4) . . . . ? C9 N3 C10 C11 166.8(2) . . . . ? C12 N4 C11 C10 -79.2(3) . . . . ? O5 C10 C11 N4 174.6(2) . . . . ? N3 C10 C11 N4 -3.8(4) . . . . ? C13 O6 C12 O7 10.9(4) . . . . ? C13 O6 C12 N4 -168.8(2) . . . . ? C11 N4 C12 O7 16.4(4) . . . . ? C11 N4 C12 O6 -163.8(2) . . . . ? C12 O6 C13 C14 67.4(3) . . . . ? C12 O6 C13 C15 -57.1(3) . . . . ? C12 O6 C13 C16 -174.4(3) . . . . ? C18 N5 C17 P1 98.5(3) . . . . ? O1 P1 C17 N5 -62.4(2) . . . . ? C1 P1 C17 N5 174.61(18) . . . . ? C9 P1 C17 N5 61.9(2) . . . . ? C17 N5 C18 O8 2.7(4) . . . . ? C17 N5 C18 C19 -177.9(2) . . . . ? C20 N6 C19 C18 84.1(3) . . . . ? O8 C18 C19 N6 -178.8(2) . . . . ? N5 C18 C19 N6 1.7(4) . . . . ? C19 N6 C20 O10 -13.8(4) . . . . ? C19 N6 C20 O9 166.2(2) . . . . ? C21 O9 C20 O10 -9.8(5) . . . . ? C21 O9 C20 N6 170.2(2) . . . . ? C20 O9 C21 C24 62.8(3) . . . . ? C20 O9 C21 C23 -179.6(3) . . . . ? C20 O9 C21 C22 -62.1(3) . . . . ? 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 H1N O1 0.975(18) 1.90(2) 2.810(3) 154(3) 2_766 N2 H2N O8 0.977(18) 1.910(19) 2.882(3) 172(3) 2_766 N3 H3N O2 0.961(17) 1.99(2) 2.775(3) 137(2) . N3 H3N N4 0.961(17) 2.31(3) 2.782(3) 109(2) . N4 H4N O2 0.969(17) 1.874(18) 2.838(3) 173(3) 2_756 N5 H5N O5 0.962(17) 2.07(2) 2.873(3) 140(2) . N6 H6N O5 0.967(17) 1.923(18) 2.883(3) 172(2) 2_655 O1S H1S O1 0.959(19) 1.88(2) 2.838(3) 174(3) . O1S H2S O10 0.964(19) 1.99(2) 2.945(3) 169(4) . O2S H3S O1S 0.968(19) 1.87(2) 2.826(4) 171(4) . O2S H4S O8 0.975(19) 2.31(4) 3.043(4) 131(4) . O2S H4S O2S 0.975(19) 2.59(5) 3.114(7) 114(4) 2_665 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.226 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.057 # Attachment '- ob177n.cif' data_ob177n _database_code_depnum_ccdc_archive 'CCDC 824328' #TrackingRef '- ob177n.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H36 N9 O19 P S3' _chemical_formula_weight 953.83 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M R3 _symmetry_space_group_name_Hall 'R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' _cell_length_a 26.969(4) _cell_length_b 26.969(4) _cell_length_c 4.7896(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3016.8(8) _cell_formula_units_Z 3 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1229 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 18.97 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1482 _exptl_absorpt_coefficient_mu 0.315 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7867 _exptl_absorpt_correction_T_max 0.9969 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker Apex 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 8003 _diffrn_reflns_av_R_equivalents 0.0874 _diffrn_reflns_av_sigmaI/netI 0.1222 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2156 _reflns_number_gt 1633 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.17(12) _refine_ls_number_reflns 2156 _refine_ls_number_parameters 191 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.0768 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 0.838 _refine_ls_restrained_S_all 0.838 _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 0.6667 0.3333 0.8582(4) 0.0164(5) Uani 1 3 d S . . O1 O 0.6667 0.3333 1.1649(11) 0.0251(13) Uani 1 3 d S . . O2 O 0.72202(14) 0.47807(14) 1.0849(7) 0.0341(9) Uani 1 1 d . . . O3 O 0.47441(17) 0.44224(16) 1.1985(7) 0.0427(10) Uani 1 1 d . . . O4 O 0.48278(15) 0.49287(17) 1.5602(8) 0.0469(11) Uani 1 1 d . . . O5 O 0.67032(16) 0.61508(15) 1.9544(7) 0.0365(10) Uani 1 1 d . . . O6 O 0.74454(15) 0.61941(15) 1.7543(8) 0.0385(10) Uani 1 1 d . . . N1 N 0.63686(17) 0.41761(16) 0.8814(7) 0.0233(10) Uani 1 1 d D . . N2 N 0.50224(17) 0.47484(18) 1.3850(9) 0.0298(10) Uani 1 1 d . . . N3 N 0.69313(18) 0.59994(17) 1.7773(9) 0.0281(10) Uani 1 1 d . . . C1 C 0.6630(2) 0.3935(2) 0.7000(10) 0.0251(11) Uani 1 1 d . . . H1A H 0.7023 0.4240 0.6516 0.030 Uiso 1 1 calc R . . H1B H 0.6408 0.3803 0.5245 0.030 Uiso 1 1 calc R . . C2 C 0.6704(2) 0.45955(19) 1.0599(9) 0.0209(10) Uani 1 1 d . . . C3 C 0.64289(19) 0.48616(19) 1.2356(9) 0.0205(11) Uani 1 1 d . . . C4 C 0.5848(2) 0.4673(2) 1.2258(9) 0.0222(11) Uani 1 1 d . . . H4A H 0.5600 0.4365 1.1071 0.027 Uiso 1 1 calc R . . C5 C 0.5637(2) 0.4943(2) 1.3935(10) 0.0247(11) Uani 1 1 d . . . C6 C 0.5971(2) 0.5380(2) 1.5799(9) 0.0242(11) Uani 1 1 d . . . H6A H 0.5815 0.5552 1.6970 0.029 Uiso 1 1 calc R . . C7 C 0.6555(2) 0.55490(19) 1.5829(9) 0.0230(11) Uani 1 1 d . . . C8 C 0.67865(19) 0.5310(2) 1.4123(8) 0.0204(11) Uani 1 1 d . . . H8A H 0.7187 0.5448 1.4144 0.024 Uiso 1 1 calc R . . S1S S 0.46579(6) 0.33014(6) 0.8359(3) 0.0341(3) Uani 1 1 d . . . O1S O 0.52131(14) 0.37732(13) 0.7221(7) 0.0375(9) Uani 1 1 d . . . C1S C 0.4115(2) 0.3420(3) 0.6917(16) 0.061(2) Uani 1 1 d . . . H1SA H 0.4136 0.3760 0.7781 0.092 Uiso 1 1 calc R . . H1SB H 0.3738 0.3086 0.7280 0.092 Uiso 1 1 calc R . . H1SC H 0.4173 0.3480 0.4898 0.092 Uiso 1 1 calc R . . C2S C 0.4494(2) 0.2683(2) 0.6354(11) 0.0408(14) Uani 1 1 d . . . H2SA H 0.4755 0.2544 0.6872 0.061 Uiso 1 1 calc R . . H2SB H 0.4539 0.2781 0.4364 0.061 Uiso 1 1 calc R . . H2SC H 0.4098 0.2384 0.6720 0.061 Uiso 1 1 calc R . . H1N H 0.5935(9) 0.4030(17) 0.873(8) 0.023(12) 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 0.0174(7) 0.0174(7) 0.0145(11) 0.000 0.000 0.0087(3) O1 0.028(2) 0.028(2) 0.020(3) 0.000 0.000 0.0138(10) O2 0.024(2) 0.037(2) 0.043(2) -0.0074(18) 0.0003(17) 0.0156(17) O3 0.036(2) 0.052(2) 0.043(2) -0.018(2) -0.0135(18) 0.024(2) O4 0.036(2) 0.061(3) 0.050(3) -0.019(2) 0.0046(19) 0.029(2) O5 0.047(2) 0.035(2) 0.027(2) -0.0098(18) 0.0013(18) 0.020(2) O6 0.030(2) 0.038(2) 0.046(2) -0.0126(19) -0.0093(19) 0.0160(19) N1 0.035(3) 0.026(2) 0.017(2) 0.0016(18) 0.0043(19) 0.021(2) N2 0.027(2) 0.037(3) 0.031(3) 0.001(2) 0.003(2) 0.020(2) N3 0.038(3) 0.022(2) 0.022(2) -0.0003(18) 0.002(2) 0.013(2) C1 0.033(3) 0.019(3) 0.025(3) 0.005(2) 0.007(2) 0.015(2) C2 0.025(3) 0.022(3) 0.021(3) 0.005(2) 0.004(2) 0.015(2) C3 0.033(3) 0.024(3) 0.013(2) 0.006(2) 0.003(2) 0.020(2) C4 0.029(3) 0.023(3) 0.017(2) -0.005(2) -0.003(2) 0.015(2) C5 0.026(3) 0.025(3) 0.026(3) 0.004(2) -0.002(2) 0.015(2) C6 0.037(3) 0.018(3) 0.020(3) 0.003(2) 0.005(2) 0.016(2) C7 0.037(3) 0.019(3) 0.017(3) -0.003(2) -0.001(2) 0.017(2) C8 0.027(3) 0.020(3) 0.016(3) 0.000(2) -0.001(2) 0.013(2) S1S 0.0330(8) 0.0310(8) 0.0285(7) -0.0041(6) -0.0022(6) 0.0088(6) O1S 0.030(2) 0.027(2) 0.041(2) -0.0029(18) 0.0007(18) 0.0035(17) C1S 0.036(4) 0.050(4) 0.095(6) 0.001(4) -0.001(4) 0.021(3) C2S 0.042(4) 0.034(3) 0.044(4) -0.011(3) -0.010(3) 0.018(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.469(5) . ? P1 C1 1.838(4) 3_665 ? P1 C1 1.838(4) 2_655 ? P1 C1 1.838(4) . ? O2 C2 1.227(6) . ? O3 N2 1.214(5) . ? O4 N2 1.213(5) . ? O5 N3 1.231(5) . ? O6 N3 1.217(5) . ? N1 C2 1.344(6) . ? N1 C1 1.461(5) . ? N1 H1N 1.032(19) . ? N2 C5 1.466(6) . ? N3 C7 1.463(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.519(6) . ? C3 C4 1.385(6) . ? C3 C8 1.393(6) . ? C4 C5 1.385(6) . ? C4 H4A 0.9500 . ? C5 C6 1.391(6) . ? C6 C7 1.406(7) . ? C6 H6A 0.9500 . ? C7 C8 1.369(6) . ? C8 H8A 0.9500 . ? S1S O1S 1.501(3) . ? S1S C1S 1.788(6) . ? S1S C2S 1.778(5) . ? C1S H1SA 0.9800 . ? C1S H1SB 0.9800 . ? C1S H1SC 0.9800 . ? C2S H2SA 0.9800 . ? C2S H2SB 0.9800 . ? C2S H2SC 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C1 114.35(16) . 3_665 ? O1 P1 C1 114.35(16) . 2_655 ? C1 P1 C1 104.18(18) 3_665 2_655 ? O1 P1 C1 114.35(16) . . ? C1 P1 C1 104.18(18) 3_665 . ? C1 P1 C1 104.18(18) 2_655 . ? C2 N1 C1 118.7(4) . . ? C2 N1 H1N 120(2) . . ? C1 N1 H1N 121(2) . . ? O4 N2 O3 124.4(4) . . ? O4 N2 C5 118.3(4) . . ? O3 N2 C5 117.3(4) . . ? O6 N3 O5 124.7(4) . . ? O6 N3 C7 117.9(4) . . ? O5 N3 C7 117.4(4) . . ? N1 C1 P1 113.5(3) . . ? N1 C1 H1A 108.9 . . ? P1 C1 H1A 108.9 . . ? N1 C1 H1B 108.9 . . ? P1 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? O2 C2 N1 123.7(4) . . ? O2 C2 C3 118.5(4) . . ? N1 C2 C3 117.9(4) . . ? C4 C3 C8 120.3(4) . . ? C4 C3 C2 122.5(4) . . ? C8 C3 C2 117.1(4) . . ? C5 C4 C3 118.3(4) . . ? C5 C4 H4A 120.8 . . ? C3 C4 H4A 120.8 . . ? C4 C5 C6 123.8(4) . . ? C4 C5 N2 118.9(4) . . ? C6 C5 N2 117.3(4) . . ? C5 C6 C7 115.3(4) . . ? C5 C6 H6A 122.3 . . ? C7 C6 H6A 122.3 . . ? C8 C7 C6 122.9(5) . . ? C8 C7 N3 118.8(4) . . ? C6 C7 N3 118.4(4) . . ? C7 C8 C3 119.4(5) . . ? C7 C8 H8A 120.3 . . ? C3 C8 H8A 120.3 . . ? O1S S1S C1S 105.5(3) . . ? O1S S1S C2S 105.9(2) . . ? C1S S1S C2S 96.8(3) . . ? S1S C1S H1SA 109.5 . . ? S1S C1S H1SB 109.5 . . ? H1SA C1S H1SB 109.5 . . ? S1S C1S H1SC 109.5 . . ? H1SA C1S H1SC 109.5 . . ? H1SB C1S H1SC 109.5 . . ? S1S C2S H2SA 109.5 . . ? S1S C2S H2SB 109.5 . . ? H2SA C2S H2SB 109.5 . . ? S1S C2S H2SC 109.5 . . ? H2SA C2S H2SC 109.5 . . ? H2SB C2S H2SC 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 P1 88.5(5) . . . . ? O1 P1 C1 N1 -24.7(4) . . . . ? C1 P1 C1 N1 -150.2(4) 3_665 . . . ? C1 P1 C1 N1 100.8(5) 2_655 . . . ? C1 N1 C2 O2 -1.9(7) . . . . ? C1 N1 C2 C3 176.8(3) . . . . ? O2 C2 C3 C4 -178.6(5) . . . . ? N1 C2 C3 C4 2.7(6) . . . . ? O2 C2 C3 C8 1.0(6) . . . . ? N1 C2 C3 C8 -177.8(4) . . . . ? C8 C3 C4 C5 0.5(6) . . . . ? C2 C3 C4 C5 -179.9(4) . . . . ? C3 C4 C5 C6 -2.6(7) . . . . ? C3 C4 C5 N2 179.9(4) . . . . ? O4 N2 C5 C4 169.4(4) . . . . ? O3 N2 C5 C4 -11.8(7) . . . . ? O4 N2 C5 C6 -8.2(7) . . . . ? O3 N2 C5 C6 170.6(4) . . . . ? C4 C5 C6 C7 1.9(7) . . . . ? N2 C5 C6 C7 179.4(4) . . . . ? C5 C6 C7 C8 1.0(7) . . . . ? C5 C6 C7 N3 -178.9(4) . . . . ? O6 N3 C7 C8 9.3(6) . . . . ? O5 N3 C7 C8 -170.1(4) . . . . ? O6 N3 C7 C6 -170.8(4) . . . . ? O5 N3 C7 C6 9.8(6) . . . . ? C6 C7 C8 C3 -2.9(7) . . . . ? N3 C7 C8 C3 177.0(4) . . . . ? C4 C3 C8 C7 2.1(6) . . . . ? C2 C3 C8 C7 -177.5(4) . . . . ? 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 H1N O1S 1.032(19) 1.85(2) 2.844(5) 159(3) . _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.920 _refine_diff_density_max 0.251 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.050