# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_shelxl _database_code_depnum_ccdc_archive 'CCDC 914529' #TrackingRef 'pance3-2-1_2_hb.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C16 H29 N2 O4, H2 O4 P' _chemical_formula_sum 'C16 H31 N2 O8 P' _chemical_formula_weight 410.40 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 23.7840(6) _cell_length_b 24.4109(6) _cell_length_c 7.39788(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4295.14(17) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.123 _exptl_crystal_size_mid 0.0071 _exptl_crystal_size_min 0.0055 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.403 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'ABSCOR (T.Higashi, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.83073 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'synchrotron radiation SPring-8 BL40XU' _diffrn_radiation_monochromator 'Si(111) Channel Cut' _diffrn_measurement_device_type 'Rigaku Saturn 724' _diffrn_measurement_method 'Oscillation Photograph' _diffrn_detector_area_resol_mean 29 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23930 _diffrn_reflns_av_R_equivalents 0.0966 _diffrn_reflns_av_sigmaI/netI 0.1193 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 30.03 _reflns_number_total 7481 _reflns_number_gt 4930 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku)' _computing_cell_refinement 'Rapid Auto(Rigaku)' _computing_data_reduction 'Rapid Auto(Rigaku)' _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^)+(0.0568P)^2^+0.4731P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.19(13) _refine_ls_number_reflns 7481 _refine_ls_number_parameters 497 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1070 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1449 _refine_ls_wR_factor_gt 0.1187 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 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 0.03159(5) 0.60810(5) 0.27904(15) 0.0300(3) Uani 1 1 d . . . O1 O 0.07538(12) 0.56961(13) 0.1910(4) 0.0340(8) Uani 1 1 d . . . H1 H 0.0815 0.5798 0.0844 0.051 Uiso 1 1 calc R . . O2 O -0.02055(12) 0.61338(13) 0.1665(4) 0.0329(8) Uani 1 1 d . . . O3 O 0.06000(13) 0.66572(13) 0.3018(4) 0.0393(8) Uani 1 1 d . . . H3 H 0.0666 0.6791 0.1995 0.059 Uiso 1 1 calc R . . O4 O 0.02163(13) 0.58822(13) 0.4698(4) 0.0376(8) Uani 1 1 d . . . P2 P 0.11212(5) 0.51839(5) 0.75601(15) 0.0315(3) Uani 1 1 d . . . O5 O 0.11724(13) 0.46253(12) 0.8377(4) 0.0333(7) Uani 1 1 d . . . O6 O 0.08851(13) 0.51341(14) 0.5610(3) 0.0363(8) Uani 1 1 d . . . H6 H 0.0853 0.5448 0.5155 0.054 Uiso 1 1 calc R . . O7 O 0.07734(14) 0.55937(14) 0.8591(4) 0.0396(9) Uani 1 1 d . . . O8 O 0.17368(12) 0.54175(13) 0.7234(4) 0.0371(8) Uani 1 1 d . . . H8 H 0.1908 0.5436 0.8225 0.056 Uiso 1 1 calc R . . N1 N 0.03242(15) 0.38868(15) 0.7975(5) 0.0309(9) Uani 1 1 d . . . H1A H 0.0175 0.3864 0.9105 0.046 Uiso 1 1 calc R . . H1B H 0.0058 0.4011 0.7193 0.046 Uiso 1 1 calc R . . H1C H 0.0620 0.4123 0.7985 0.046 Uiso 1 1 calc R . . N2 N -0.04787(14) 0.30660(16) 0.7125(5) 0.0319(9) Uani 1 1 d . . . H2 H -0.0505 0.3159 0.5978 0.038 Uiso 1 1 calc R . . O9 O -0.01172(13) 0.19584(14) 0.7684(4) 0.0449(9) Uani 1 1 d . . . O10 O 0.19207(15) 0.19298(17) 0.8590(5) 0.0568(10) Uani 1 1 d . . . O11 O 0.21436(13) 0.28176(15) 0.8982(4) 0.0402(9) Uani 1 1 d . . . O12 O -0.09501(13) 0.29840(14) 0.9769(4) 0.0408(8) Uani 1 1 d . . . C1 C 0.05191(17) 0.33393(19) 0.7393(6) 0.0310(10) Uani 1 1 d . . . H1D H 0.0581 0.3350 0.6056 0.037 Uiso 1 1 calc R . . C2 C 0.00699(18) 0.29052(18) 0.7792(6) 0.0314(11) Uani 1 1 d . . . H2A H 0.0043 0.2862 0.9134 0.038 Uiso 1 1 calc R . . C3 C 0.02555(19) 0.23633(19) 0.7004(6) 0.0363(11) Uani 1 1 d . . . H3A H 0.0220 0.2379 0.5658 0.044 Uiso 1 1 calc R . . C4 C 0.08482(19) 0.2235(2) 0.7485(6) 0.0365(11) Uani 1 1 d . . . H4 H 0.0972 0.1867 0.7374 0.044 Uiso 1 1 calc R . . C5 C 0.12166(19) 0.2612(2) 0.8066(6) 0.0346(11) Uani 1 1 d . . . C6 C 0.10732(18) 0.31986(19) 0.8290(6) 0.0304(11) Uani 1 1 d . . . H6A H 0.1375 0.3426 0.7758 0.036 Uiso 1 1 calc R . . H6B H 0.1050 0.3286 0.9595 0.036 Uiso 1 1 calc R . . C7 C -0.0145(3) 0.1449(2) 0.6680(8) 0.0572(16) Uani 1 1 d . . . H7 H 0.0248 0.1339 0.6361 0.069 Uiso 1 1 calc R . . C8 C -0.0381(3) 0.1024(2) 0.7961(9) 0.0692(18) Uani 1 1 d . . . H8A H -0.0755 0.1145 0.8388 0.083 Uiso 1 1 calc R . . H8B H -0.0432 0.0675 0.7299 0.083 Uiso 1 1 calc R . . C9 C -0.0005(3) 0.0925(3) 0.9579(10) 0.092(2) Uani 1 1 d . . . H9A H 0.0352 0.0765 0.9176 0.139 Uiso 1 1 calc R . . H9B H -0.0191 0.0673 1.0418 0.139 Uiso 1 1 calc R . . H9C H 0.0069 0.1274 1.0192 0.139 Uiso 1 1 calc R . . C10 C -0.0474(3) 0.1527(3) 0.4914(9) 0.0727(19) Uani 1 1 d . . . H10A H -0.0272 0.1797 0.4152 0.087 Uiso 1 1 calc R . . H10B H -0.0480 0.1175 0.4252 0.087 Uiso 1 1 calc R . . C11 C -0.1061(3) 0.1717(3) 0.5165(11) 0.092(3) Uani 1 1 d . . . H11A H -0.1287 0.1419 0.5681 0.139 Uiso 1 1 calc R . . H11B H -0.1219 0.1824 0.3994 0.139 Uiso 1 1 calc R . . H11C H -0.1066 0.2032 0.5986 0.139 Uiso 1 1 calc R . . C12 C 0.1791(2) 0.2413(2) 0.8550(6) 0.0362(12) Uani 1 1 d . . . C13 C 0.2720(2) 0.2633(2) 0.9368(7) 0.0469(14) Uani 1 1 d . . . H13A H 0.2889 0.2468 0.8273 0.056 Uiso 1 1 calc R . . H13B H 0.2717 0.2354 1.0339 0.056 Uiso 1 1 calc R . . C14 C 0.3053(2) 0.3124(2) 0.9950(7) 0.0527(15) Uani 1 1 d . . . H14A H 0.3040 0.3403 0.8999 0.079 Uiso 1 1 calc R . . H14B H 0.3444 0.3016 1.0166 0.079 Uiso 1 1 calc R . . H14C H 0.2892 0.3273 1.1066 0.079 Uiso 1 1 calc R . . C15 C -0.09546(19) 0.30847(19) 0.8131(7) 0.0333(11) Uani 1 1 d . . . C16 C -0.14778(19) 0.3217(2) 0.7120(6) 0.0404(12) Uani 1 1 d . . . H16A H -0.1693 0.2880 0.6914 0.061 Uiso 1 1 calc R . . H16B H -0.1380 0.3382 0.5955 0.061 Uiso 1 1 calc R . . H16C H -0.1705 0.3474 0.7825 0.061 Uiso 1 1 calc R . . N3 N 0.11098(15) 0.45443(15) 0.2121(4) 0.0318(9) Uani 1 1 d . . . H3B H 0.1034 0.4888 0.2533 0.048 Uiso 1 1 calc R . . H3C H 0.0787 0.4344 0.2102 0.048 Uiso 1 1 calc R . . H3D H 0.1254 0.4565 0.0984 0.048 Uiso 1 1 calc R . . N4 N 0.20416(15) 0.51658(16) 0.3421(5) 0.0308(9) Uani 1 1 d . . . H4A H 0.1971 0.5315 0.4480 0.037 Uiso 1 1 calc R . . O13 O 0.30073(13) 0.45383(14) 0.4677(4) 0.0402(8) Uani 1 1 d . . . O14 O 0.25049(15) 0.25888(15) 0.4818(5) 0.0479(9) Uani 1 1 d . . . O15 O 0.16872(14) 0.25671(13) 0.3291(4) 0.0410(8) Uani 1 1 d . . . O16 O 0.21856(14) 0.52992(15) 0.0464(4) 0.0444(9) Uani 1 1 d . . . C17 C 0.15266(18) 0.42761(19) 0.3343(6) 0.0293(11) Uani 1 1 d . . . H17 H 0.1375 0.4293 0.4603 0.035 Uiso 1 1 calc R . . C18 C 0.20922(18) 0.45748(19) 0.3317(6) 0.0292(10) Uani 1 1 d . . . H18 H 0.2290 0.4480 0.2166 0.035 Uiso 1 1 calc R . . C19 C 0.24412(19) 0.4355(2) 0.4893(6) 0.0332(11) Uani 1 1 d . . . H19 H 0.2286 0.4498 0.6058 0.040 Uiso 1 1 calc R . . C20 C 0.2425(2) 0.3747(2) 0.4906(6) 0.0381(12) Uani 1 1 d . . . H20 H 0.2695 0.3564 0.5634 0.046 Uiso 1 1 calc R . . C21 C 0.20659(19) 0.3435(2) 0.3991(6) 0.0317(11) Uani 1 1 d . . . C22 C 0.16027(19) 0.36847(18) 0.2857(6) 0.0323(11) Uani 1 1 d . . . H22A H 0.1700 0.3653 0.1560 0.039 Uiso 1 1 calc R . . H22B H 0.1247 0.3484 0.3067 0.039 Uiso 1 1 calc R . . C23 C 0.3212(2) 0.4884(2) 0.6126(7) 0.0473(14) Uani 1 1 d . . . H23 H 0.2917 0.5159 0.6441 0.057 Uiso 1 1 calc R . . C24 C 0.3347(2) 0.4545(3) 0.7786(8) 0.0620(17) Uani 1 1 d . . . H24A H 0.3651 0.4284 0.7484 0.074 Uiso 1 1 calc R . . H24B H 0.3010 0.4329 0.8120 0.074 Uiso 1 1 calc R . . C25 C 0.3528(3) 0.4887(3) 0.9410(8) 0.083(2) Uani 1 1 d . . . H25A H 0.3900 0.5044 0.9180 0.125 Uiso 1 1 calc R . . H25B H 0.3544 0.4653 1.0487 0.125 Uiso 1 1 calc R . . H25C H 0.3256 0.5182 0.9607 0.125 Uiso 1 1 calc R . . C26 C 0.3720(2) 0.5178(3) 0.5359(9) 0.0616(16) Uani 1 1 d . . . H26A H 0.3984 0.4905 0.4847 0.074 Uiso 1 1 calc R . . H26B H 0.3917 0.5374 0.6345 0.074 Uiso 1 1 calc R . . C27 C 0.3556(3) 0.5589(3) 0.3880(9) 0.077(2) Uani 1 1 d . . . H27A H 0.3361 0.5397 0.2901 0.116 Uiso 1 1 calc R . . H27B H 0.3895 0.5765 0.3404 0.116 Uiso 1 1 calc R . . H27C H 0.3306 0.5868 0.4393 0.116 Uiso 1 1 calc R . . C28 C 0.2118(2) 0.2825(2) 0.4090(6) 0.0365(12) Uani 1 1 d . . . C29 C 0.1707(2) 0.1974(2) 0.3358(7) 0.0467(13) Uani 1 1 d . . . H29A H 0.1762 0.1848 0.4617 0.056 Uiso 1 1 calc R . . H29B H 0.2023 0.1836 0.2614 0.056 Uiso 1 1 calc R . . C30 C 0.1156(2) 0.1766(2) 0.2629(7) 0.0553(15) Uani 1 1 d . . . H30A H 0.0846 0.1934 0.3302 0.083 Uiso 1 1 calc R . . H30B H 0.1140 0.1367 0.2765 0.083 Uiso 1 1 calc R . . H30C H 0.1124 0.1862 0.1347 0.083 Uiso 1 1 calc R . . C31 C 0.20967(18) 0.5495(2) 0.1990(7) 0.0356(12) Uani 1 1 d . . . C32 C 0.2047(2) 0.6097(2) 0.2282(7) 0.0440(12) Uani 1 1 d . . . H32A H 0.2394 0.6278 0.1885 0.066 Uiso 1 1 calc R . . H32B H 0.1986 0.6171 0.3570 0.066 Uiso 1 1 calc R . . H32C H 0.1728 0.6239 0.1585 0.066 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0306(6) 0.0358(8) 0.0238(6) 0.0002(5) -0.0003(5) 0.0016(5) O1 0.0367(18) 0.046(2) 0.0196(15) 0.0013(13) 0.0005(14) 0.0083(15) O2 0.0273(16) 0.040(2) 0.0312(16) 0.0011(14) -0.0027(13) 0.0034(15) O3 0.0466(19) 0.040(2) 0.0309(16) -0.0006(14) 0.0017(15) -0.0075(16) O4 0.0408(18) 0.050(2) 0.0216(15) 0.0038(14) 0.0074(14) 0.0095(17) P2 0.0363(6) 0.0329(7) 0.0252(6) -0.0002(5) 0.0022(6) 0.0045(6) O5 0.0368(17) 0.0272(19) 0.0360(16) 0.0043(14) -0.0018(15) -0.0007(15) O6 0.0500(19) 0.040(2) 0.0193(14) -0.0022(14) -0.0001(14) 0.0085(17) O7 0.046(2) 0.047(2) 0.0264(16) -0.0036(15) 0.0005(15) 0.0168(17) O8 0.0405(17) 0.045(2) 0.0258(16) 0.0021(14) 0.0041(15) -0.0064(15) N1 0.0314(19) 0.029(2) 0.0322(19) -0.0039(17) 0.0000(17) 0.0029(17) N2 0.029(2) 0.037(2) 0.029(2) 0.0031(17) -0.0040(18) 0.0055(17) O9 0.0428(18) 0.037(2) 0.055(2) -0.0023(17) -0.0035(18) -0.0073(16) O10 0.041(2) 0.046(3) 0.083(3) 0.005(2) 0.0047(19) 0.0103(19) O11 0.0319(19) 0.045(2) 0.0434(18) 0.0005(16) -0.0008(15) 0.0031(17) O12 0.0407(19) 0.047(2) 0.0349(19) -0.0011(15) 0.0030(16) -0.0044(16) C1 0.030(2) 0.035(3) 0.028(2) -0.002(2) 0.001(2) 0.001(2) C2 0.040(3) 0.023(3) 0.032(2) 0.002(2) -0.004(2) 0.000(2) C3 0.037(3) 0.031(3) 0.041(3) 0.000(2) 0.001(2) -0.004(2) C4 0.042(3) 0.030(3) 0.037(3) -0.005(2) 0.006(2) 0.005(2) C5 0.034(3) 0.033(3) 0.037(3) 0.001(2) -0.002(2) 0.005(2) C6 0.027(2) 0.029(3) 0.035(2) -0.004(2) -0.003(2) 0.002(2) C7 0.056(4) 0.035(4) 0.081(4) -0.012(3) -0.013(3) 0.003(3) C8 0.074(4) 0.036(4) 0.098(5) 0.000(3) -0.002(4) -0.012(3) C9 0.113(6) 0.072(6) 0.093(5) 0.035(4) -0.008(5) -0.021(4) C10 0.069(4) 0.070(5) 0.078(4) -0.017(4) -0.005(4) -0.005(4) C11 0.065(5) 0.088(6) 0.124(6) -0.035(5) -0.031(4) 0.004(4) C12 0.036(3) 0.032(3) 0.041(3) 0.002(2) 0.002(2) 0.010(3) C13 0.032(3) 0.056(4) 0.053(3) 0.008(3) 0.002(3) 0.013(3) C14 0.037(3) 0.068(4) 0.053(3) 0.002(3) -0.001(3) -0.002(3) C15 0.036(3) 0.027(3) 0.037(3) -0.001(2) 0.005(2) -0.006(2) C16 0.031(2) 0.042(3) 0.047(3) 0.005(2) -0.002(2) -0.005(2) N3 0.032(2) 0.032(2) 0.032(2) -0.0004(17) 0.0007(18) -0.0004(17) N4 0.035(2) 0.031(2) 0.0264(19) -0.0006(18) 0.0020(17) -0.0011(19) O13 0.0334(18) 0.041(2) 0.046(2) -0.0120(16) -0.0043(16) -0.0024(16) O14 0.049(2) 0.037(2) 0.058(2) 0.0021(17) -0.0071(18) 0.0097(18) O15 0.048(2) 0.028(2) 0.0466(19) -0.0029(15) -0.0011(16) -0.0025(16) O16 0.043(2) 0.059(3) 0.0308(18) 0.0014(17) -0.0009(16) -0.0008(18) C17 0.029(2) 0.029(3) 0.030(2) 0.003(2) -0.005(2) 0.003(2) C18 0.034(3) 0.025(3) 0.029(2) -0.0003(19) -0.001(2) 0.004(2) C19 0.034(3) 0.030(3) 0.035(3) -0.004(2) 0.001(2) 0.002(2) C20 0.039(3) 0.041(3) 0.034(3) -0.004(2) -0.004(2) 0.005(2) C21 0.035(3) 0.034(3) 0.026(2) 0.001(2) 0.000(2) 0.001(2) C22 0.036(3) 0.031(3) 0.030(2) -0.001(2) -0.001(2) 0.006(2) C23 0.040(3) 0.046(4) 0.056(3) -0.013(3) -0.012(3) 0.006(3) C24 0.051(3) 0.064(4) 0.070(4) -0.015(3) -0.019(3) 0.010(3) C25 0.078(4) 0.107(7) 0.066(4) -0.035(4) -0.026(4) 0.010(4) C26 0.045(3) 0.051(4) 0.089(4) -0.018(4) -0.009(3) -0.006(3) C27 0.073(4) 0.084(6) 0.075(5) -0.011(4) 0.002(4) -0.031(4) C28 0.043(3) 0.037(3) 0.029(3) -0.002(2) 0.006(2) 0.006(3) C29 0.056(3) 0.030(3) 0.055(3) 0.003(2) -0.001(3) 0.006(3) C30 0.074(4) 0.042(4) 0.050(3) -0.003(3) 0.001(3) -0.016(3) C31 0.026(2) 0.039(3) 0.042(3) 0.001(2) -0.002(2) -0.001(2) C32 0.042(3) 0.035(3) 0.055(3) 0.011(3) 0.001(3) -0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O2 1.499(3) . ? P1 O4 1.511(3) . ? P1 O1 1.547(3) . ? P1 O3 1.569(3) . ? O1 H1 0.8400 . ? O3 H3 0.8400 . ? P2 O5 1.496(3) . ? P2 O7 1.506(3) . ? P2 O6 1.553(3) . ? P2 O8 1.590(3) . ? O6 H6 0.8400 . ? O8 H8 0.8400 . ? N1 C1 1.479(5) . ? N1 H1A 0.9100 . ? N1 H1B 0.9100 . ? N1 H1C 0.9100 . ? N2 C15 1.356(5) . ? N2 C2 1.449(5) . ? N2 H2 0.8800 . ? O9 C3 1.420(5) . ? O9 C7 1.449(6) . ? O10 C12 1.219(6) . ? O11 C12 1.335(6) . ? O11 C13 1.471(5) . ? O12 C15 1.237(5) . ? C1 C6 1.515(6) . ? C1 C2 1.533(6) . ? C1 H1D 1.0000 . ? C2 C3 1.511(6) . ? C2 H2A 1.0000 . ? C3 C4 1.487(6) . ? C3 H3A 1.0000 . ? C4 C5 1.340(6) . ? C4 H4 0.9500 . ? C5 C6 1.482(6) . ? C5 C12 1.493(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.514(8) . ? C7 C10 1.534(9) . ? C7 H7 1.0000 . ? C8 C9 1.514(9) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.484(9) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C13 C14 1.500(7) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.487(6) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N3 C17 1.493(5) . ? N3 H3B 0.9100 . ? N3 H3C 0.9100 . ? N3 H3D 0.9100 . ? N4 C31 1.336(6) . ? N4 C18 1.450(6) . ? N4 H4A 0.8800 . ? O13 C19 1.428(5) . ? O13 C23 1.448(6) . ? O14 C28 1.212(6) . ? O15 C28 1.340(6) . ? O15 C29 1.448(6) . ? O16 C31 1.244(5) . ? C17 C22 1.499(6) . ? C17 C18 1.530(6) . ? C17 H17 1.0000 . ? C18 C19 1.529(6) . ? C18 H18 1.0000 . ? C19 C20 1.484(7) . ? C19 H19 1.0000 . ? C20 C21 1.329(6) . ? C20 H20 0.9500 . ? C21 C28 1.497(7) . ? C21 C22 1.512(6) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.514(8) . ? C23 C26 1.516(7) . ? C23 H23 1.0000 . ? C24 C25 1.525(8) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.535(9) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C29 C30 1.506(7) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C32 1.490(7) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 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 O2 P1 O4 114.63(17) . . ? O2 P1 O1 112.05(16) . . ? O4 P1 O1 107.67(17) . . ? O2 P1 O3 109.80(18) . . ? O4 P1 O3 104.77(18) . . ? O1 P1 O3 107.45(18) . . ? P1 O1 H1 109.5 . . ? P1 O3 H3 109.5 . . ? O5 P2 O7 116.47(18) . . ? O5 P2 O6 109.45(18) . . ? O7 P2 O6 108.92(17) . . ? O5 P2 O8 108.26(18) . . ? O7 P2 O8 110.15(19) . . ? O6 P2 O8 102.71(17) . . ? P2 O6 H6 109.5 . . ? P2 O8 H8 109.5 . . ? C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C15 N2 C2 125.0(3) . . ? C15 N2 H2 117.5 . . ? C2 N2 H2 117.5 . . ? C3 O9 C7 116.4(4) . . ? C12 O11 C13 113.9(4) . . ? N1 C1 C6 110.5(3) . . ? N1 C1 C2 110.5(3) . . ? C6 C1 C2 111.4(4) . . ? N1 C1 H1D 108.1 . . ? C6 C1 H1D 108.1 . . ? C2 C1 H1D 108.1 . . ? N2 C2 C3 111.6(4) . . ? N2 C2 C1 112.0(4) . . ? C3 C2 C1 109.1(4) . . ? N2 C2 H2A 108.0 . . ? C3 C2 H2A 108.0 . . ? C1 C2 H2A 108.0 . . ? O9 C3 C4 111.2(4) . . ? O9 C3 C2 106.9(4) . . ? C4 C3 C2 111.6(4) . . ? O9 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3A 109.0 . . ? C5 C4 C3 123.5(4) . . ? C5 C4 H4 118.2 . . ? C3 C4 H4 118.2 . . ? C4 C5 C6 123.2(4) . . ? C4 C5 C12 116.8(4) . . ? C6 C5 C12 119.9(4) . . ? C5 C6 C1 111.7(4) . . ? C5 C6 H6A 109.3 . . ? C1 C6 H6A 109.3 . . ? C5 C6 H6B 109.3 . . ? C1 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? O9 C7 C8 106.5(5) . . ? O9 C7 C10 110.7(5) . . ? C8 C7 C10 115.4(5) . . ? O9 C7 H7 108.0 . . ? C8 C7 H7 108.0 . . ? C10 C7 H7 108.0 . . ? C9 C8 C7 112.7(5) . . ? C9 C8 H8A 109.1 . . ? C7 C8 H8A 109.1 . . ? C9 C8 H8B 109.1 . . ? C7 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C7 114.3(6) . . ? C11 C10 H10A 108.7 . . ? C7 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? C7 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O10 C12 O11 123.4(5) . . ? O10 C12 C5 123.5(5) . . ? O11 C12 C5 113.0(4) . . ? O11 C13 C14 107.6(4) . . ? O11 C13 H13A 110.2 . . ? C14 C13 H13A 110.2 . . ? O11 C13 H13B 110.2 . . ? C14 C13 H13B 110.2 . . ? H13A C13 H13B 108.5 . . ? 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 . . ? O12 C15 N2 121.6(4) . . ? O12 C15 C16 122.9(4) . . ? N2 C15 C16 115.5(4) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C17 N3 H3B 109.5 . . ? C17 N3 H3C 109.5 . . ? H3B N3 H3C 109.5 . . ? C17 N3 H3D 109.5 . . ? H3B N3 H3D 109.5 . . ? H3C N3 H3D 109.5 . . ? C31 N4 C18 123.3(4) . . ? C31 N4 H4A 118.3 . . ? C18 N4 H4A 118.3 . . ? C19 O13 C23 114.7(4) . . ? C28 O15 C29 115.4(4) . . ? N3 C17 C22 110.9(3) . . ? N3 C17 C18 111.5(4) . . ? C22 C17 C18 110.5(4) . . ? N3 C17 H17 107.9 . . ? C22 C17 H17 107.9 . . ? C18 C17 H17 107.9 . . ? N4 C18 C19 110.8(4) . . ? N4 C18 C17 113.6(4) . . ? C19 C18 C17 107.5(4) . . ? N4 C18 H18 108.3 . . ? C19 C18 H18 108.3 . . ? C17 C18 H18 108.3 . . ? O13 C19 C20 109.9(4) . . ? O13 C19 C18 108.4(4) . . ? C20 C19 C18 110.0(4) . . ? O13 C19 H19 109.5 . . ? C20 C19 H19 109.5 . . ? C18 C19 H19 109.5 . . ? C21 C20 C19 125.9(4) . . ? C21 C20 H20 117.1 . . ? C19 C20 H20 117.1 . . ? C20 C21 C28 119.5(4) . . ? C20 C21 C22 121.3(5) . . ? C28 C21 C22 119.2(4) . . ? C17 C22 C21 110.1(4) . . ? C17 C22 H22A 109.6 . . ? C21 C22 H22A 109.7 . . ? C17 C22 H22B 109.6 . . ? C21 C22 H22B 109.7 . . ? H22A C22 H22B 108.2 . . ? O13 C23 C24 110.7(4) . . ? O13 C23 C26 105.5(4) . . ? C24 C23 C26 113.3(5) . . ? O13 C23 H23 109.1 . . ? C24 C23 H23 109.1 . . ? C26 C23 H23 109.1 . . ? C23 C24 C25 113.5(5) . . ? C23 C24 H24A 108.9 . . ? C25 C24 H24A 108.9 . . ? C23 C24 H24B 108.9 . . ? C25 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 C27 112.0(5) . . ? C23 C26 H26A 109.2 . . ? C27 C26 H26A 109.2 . . ? C23 C26 H26B 109.2 . . ? C27 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O14 C28 O15 123.6(5) . . ? O14 C28 C21 123.9(5) . . ? O15 C28 C21 112.5(4) . . ? O15 C29 C30 107.2(4) . . ? O15 C29 H29A 110.3 . . ? C30 C29 H29A 110.3 . . ? O15 C29 H29B 110.3 . . ? C30 C29 H29B 110.3 . . ? H29A C29 H29B 108.5 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O16 C31 N4 120.3(5) . . ? O16 C31 C32 121.6(4) . . ? N4 C31 C32 118.1(4) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 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 C15 N2 C2 C3 111.1(5) . . . . ? C15 N2 C2 C1 -126.3(5) . . . . ? N1 C1 C2 N2 50.0(5) . . . . ? C6 C1 C2 N2 173.2(3) . . . . ? N1 C1 C2 C3 174.0(3) . . . . ? C6 C1 C2 C3 -62.8(5) . . . . ? C7 O9 C3 C4 -77.9(5) . . . . ? C7 O9 C3 C2 160.0(4) . . . . ? N2 C2 C3 O9 -66.1(4) . . . . ? C1 C2 C3 O9 169.6(3) . . . . ? N2 C2 C3 C4 172.1(4) . . . . ? C1 C2 C3 C4 47.8(5) . . . . ? O9 C3 C4 C5 -137.4(4) . . . . ? C2 C3 C4 C5 -18.2(6) . . . . ? C3 C4 C5 C6 -0.1(7) . . . . ? C3 C4 C5 C12 178.0(4) . . . . ? C4 C5 C6 C1 -13.2(6) . . . . ? C12 C5 C6 C1 168.8(4) . . . . ? N1 C1 C6 C5 167.3(4) . . . . ? C2 C1 C6 C5 44.1(5) . . . . ? C3 O9 C7 C8 159.5(4) . . . . ? C3 O9 C7 C10 -74.3(6) . . . . ? O9 C7 C8 C9 -62.7(7) . . . . ? C10 C7 C8 C9 174.0(6) . . . . ? O9 C7 C10 C11 -59.4(7) . . . . ? C8 C7 C10 C11 61.7(8) . . . . ? C13 O11 C12 O10 4.8(6) . . . . ? C13 O11 C12 C5 -176.8(4) . . . . ? C4 C5 C12 O10 -6.4(7) . . . . ? C6 C5 C12 O10 171.7(4) . . . . ? C4 C5 C12 O11 175.2(4) . . . . ? C6 C5 C12 O11 -6.7(6) . . . . ? C12 O11 C13 C14 -176.1(4) . . . . ? C2 N2 C15 O12 3.2(7) . . . . ? C2 N2 C15 C16 -175.0(4) . . . . ? C31 N4 C18 C19 136.6(4) . . . . ? C31 N4 C18 C17 -102.3(5) . . . . ? N3 C17 C18 N4 44.6(5) . . . . ? C22 C17 C18 N4 168.5(3) . . . . ? N3 C17 C18 C19 167.5(4) . . . . ? C22 C17 C18 C19 -68.6(4) . . . . ? C23 O13 C19 C20 -121.3(4) . . . . ? C23 O13 C19 C18 118.4(4) . . . . ? N4 C18 C19 O13 -67.4(5) . . . . ? C17 C18 C19 O13 167.9(4) . . . . ? N4 C18 C19 C20 172.4(4) . . . . ? C17 C18 C19 C20 47.8(5) . . . . ? O13 C19 C20 C21 -134.0(5) . . . . ? C18 C19 C20 C21 -14.7(6) . . . . ? C19 C20 C21 C28 177.6(4) . . . . ? C19 C20 C21 C22 -2.8(7) . . . . ? N3 C17 C22 C21 174.6(3) . . . . ? C18 C17 C22 C21 50.3(5) . . . . ? C20 C21 C22 C17 -15.2(6) . . . . ? C28 C21 C22 C17 164.4(4) . . . . ? C19 O13 C23 C24 75.6(5) . . . . ? C19 O13 C23 C26 -161.5(4) . . . . ? O13 C23 C24 C25 -176.1(5) . . . . ? C26 C23 C24 C25 65.7(7) . . . . ? O13 C23 C26 C27 68.2(6) . . . . ? C24 C23 C26 C27 -170.6(5) . . . . ? C29 O15 C28 O14 0.4(6) . . . . ? C29 O15 C28 C21 -179.2(4) . . . . ? C20 C21 C28 O14 -7.6(7) . . . . ? C22 C21 C28 O14 172.7(4) . . . . ? C20 C21 C28 O15 172.0(4) . . . . ? C22 C21 C28 O15 -7.6(5) . . . . ? C28 O15 C29 C30 172.4(4) . . . . ? C18 N4 C31 O16 1.4(6) . . . . ? C18 N4 C31 C32 -178.7(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 C25 H25C O16 0.98 2.64 3.437(8) 138.8 1_556 C16 H16A O14 0.98 2.57 3.432(6) 147.1 3_456 N4 H4A O8 0.88 2.13 2.976(4) 162.1 . C32 H32A O10 0.98 2.31 3.252(6) 162.0 4_556 C32 H32C O1 0.98 2.68 3.240(6) 116.5 . O8 H8 O16 0.84 1.81 2.633(4) 164.4 1_556 C17 H17 O6 1.00 2.48 3.087(5) 119.0 . N3 H3B O6 0.91 2.38 3.003(4) 125.6 . N3 H3B O1 0.91 2.13 2.940(5) 147.4 . N3 H3C O2 0.91 1.84 2.735(5) 168.1 2_565 N3 H3D O5 0.91 1.94 2.781(4) 152.1 1_554 O3 H3 O12 0.84 1.86 2.691(4) 168.5 2_564 N2 H2 O3 0.88 2.25 3.125(5) 176.3 2_565 N2 H2 O4 0.88 2.62 3.194(5) 124.0 2_565 N1 H1B O4 0.91 1.97 2.801(4) 150.2 2_565 N1 H1B O7 0.91 2.43 2.938(5) 115.3 2_565 N1 H1A O2 0.91 1.89 2.745(4) 154.6 2_566 N1 H1C O5 0.91 1.82 2.722(5) 170.6 . _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.331 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.069