data_han321 _audit_creation_method 'SHELXL96 (Sheldrick, 1996)' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C16 H28 N O7 P' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H28 N O7 P' _chemical_formula_weight 377.364 _chemical_melting_point ? _chemical_compound_source 'synthesized by the authors, see text' _publ_section_exptl_prep ; Synthesis was carried out by reaction of ... ; loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.2955 0.4335 '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 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.72760(10) _cell_length_b 10.65140(10) _cell_length_c 21.8479(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2031.01(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10287 _cell_measurement_theta_min 4.05 _cell_measurement_theta_max 72.55 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.2341 _exptl_crystal_density_method none _exptl_crystal_F_000 808.0 _exptl_absorpt_coefficient_mu 1.504 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.4370 _exptl_absorpt_correction_T_max 0.7170 _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a glass fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 2K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu-K\a radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8\%A resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'normal-focus xray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART 2K/Platform' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 58 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.1 _diffrn_reflns_number 12093 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 4.05 _diffrn_reflns_theta_max 72.66 _diffrn_reflns_theta_full 72.55 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measured_fraction_theta_full 0.977 _reflns_number_total 3886 _reflns_number_gt 3610 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL96 (Sheldrick, 1996)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXL96 (Sheldrick, 1996)' _refine_special_details ; Refinement of F^2^ against ALL reflections. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R-factor_obs 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 'w=1/[\s^2^(Fo^2^)+(0.1004P)^2^] 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 'SHELXL96 (Sheldrick, 1996)' _refine_ls_extinction_coef 0.0011(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.02(2) _refine_ls_number_reflns 3886 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_all 0.1286 _refine_ls_wR_factor_ref 0.1264 _refine_ls_goodness_of_fit_all 1.016 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.016 _refine_ls_restrained_S_obs 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _publ_section_exptl_refinement ; Data reduction processing was carried out by the use of the program SAINT (Bruker, 1999), which applied Lorentz and polarization corrections to three-dimensionally integrated diffraction spots. The program SADABS (Sheldrick, 1996) was utilized for the scaling of diffraction data, the application of a decay correction, and an empirical absorption correction based on redundant reflections. The space group was confirmed by XPREP routine in SHELXTL program (Sheldrick, 1997). The structure was solved by direct method using SHELXS97 (Sheldrick, 1997) and difmap synthesis using SHELXL96 (Sheldrick, 1996). All non-hydrogen atoms anisotropic, hydrogen atoms isotropic. Hydrogen atoms constrained to the parent site using a riding model; SHELXL96 defaults, C-H 0.93 to 0.98\%A. The isotropic factors, Uiso, were adjusted to 50% higher value of the parent site (methyl) and 20% higher (others). A final verification of possible voids was performed using the VOID routine of the PLATON program (Spek, 1995). ; 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.83894(7) 0.43932(5) 0.82974(2) 0.05800(18) Uani 1 d . . O1 O 0.8619(2) 0.51000(17) 0.88655(7) 0.0667(4) Uani 1 d . . O2 O 0.9772(2) 0.4518(2) 0.78344(8) 0.0810(6) Uani 1 d . . O3 O 0.8205(3) 0.29445(17) 0.83595(9) 0.0868(6) Uani 1 d . . O6 O 0.7898(2) 0.55400(17) 0.67404(7) 0.0692(4) Uani 1 d . . O7 O 0.65683(19) 0.39306(14) 0.62996(6) 0.0569(3) Uani 1 d . . O11 O 0.36093(18) 0.49250(13) 0.68434(7) 0.0620(4) Uani 1 d . . O12 O 0.3027(2) 0.28966(15) 0.66976(8) 0.0727(5) Uani 1 d . . N1 N 0.6490(2) 0.41597(15) 0.73033(6) 0.0485(4) Uani 1 d . . C2 C 0.5172(3) 0.33128(19) 0.73078(9) 0.0522(5) Uani 1 d . . H2 H 0.5466 0.2470 0.7171 0.063 Uiso 1 calc R . C3 C 0.4687(3) 0.3298(2) 0.79813(9) 0.0628(6) Uani 1 d . . H3A H 0.3593 0.3158 0.8021 0.075 Uiso 1 calc R . H3B H 0.5231 0.2653 0.8207 0.075 Uiso 1 calc R . C4 C 0.5129(3) 0.4606(2) 0.82045(9) 0.0561(5) Uani 1 d . . H4 H 0.4388 0.5193 0.8026 0.067 Uiso 1 calc R . C5 C 0.6666(2) 0.48452(18) 0.78824(8) 0.0474(4) Uani 1 d . . H5 H 0.6736 0.5743 0.7789 0.057 Uiso 1 calc R . C6 C 0.7066(2) 0.46368(19) 0.67720(9) 0.0507(4) Uani 1 d . . C7 C 0.6774(3) 0.4354(2) 0.56608(9) 0.0629(5) Uani 1 d . . C8 C 0.6134(5) 0.5652(3) 0.55795(13) 0.0948(10) Uani 1 d . . H8A H 0.5105 0.5679 0.5735 0.142 Uiso 1 calc R . H8B H 0.6130 0.5865 0.5153 0.142 Uiso 1 calc R . H8C H 0.6756 0.6243 0.5799 0.142 Uiso 1 calc R . C9 C 0.5821(5) 0.3413(3) 0.53075(10) 0.0919(10) Uani 1 d . . H9A H 0.6220 0.2584 0.5373 0.138 Uiso 1 calc R . H9B H 0.5861 0.3609 0.4879 0.138 Uiso 1 calc R . H9C H 0.4778 0.3449 0.5446 0.138 Uiso 1 calc R . C10 C 0.8442(4) 0.4256(5) 0.54903(14) 0.1104(13) Uani 1 d . . H10A H 0.9035 0.4797 0.5750 0.166 Uiso 1 calc R . H10B H 0.8574 0.4505 0.5071 0.166 Uiso 1 calc R . H10C H 0.8779 0.3405 0.5541 0.166 Uiso 1 calc R . C11 C 0.3875(2) 0.38308(19) 0.69189(8) 0.0514(4) Uani 1 d . . C12 C 0.1682(3) 0.3280(3) 0.63519(14) 0.0856(8) Uani 1 d . . H12A H 0.0995 0.3731 0.6615 0.128 Uiso 1 calc R . H12B H 0.1173 0.2551 0.6193 0.128 Uiso 1 calc R . H12C H 0.1989 0.3812 0.6019 0.128 Uiso 1 calc R . C13 C 0.5076(3) 0.4797(3) 0.89008(10) 0.0745(7) Uani 1 d . . H13A H 0.5649 0.4131 0.9099 0.089 Uiso 1 calc R . H13B H 0.5559 0.5589 0.9003 0.089 Uiso 1 calc R . C14 C 0.3459(5) 0.4795(5) 0.91368(14) 0.1143(13) Uani 1 d . . H14 H 0.2799 0.5319 0.8921 0.137 Uiso 1 calc R . C15 C 0.2866(7) 0.4248(7) 0.9548(3) 0.164(2) Uani 1 d . . H15A H 0.3439 0.3702 0.9789 0.197 Uiso 1 calc R . H15B H 0.1830 0.4366 0.9628 0.197 Uiso 1 calc R . C16 C 1.0498(3) 0.5724(4) 0.77543(15) 0.0975(11) Uani 1 d . . H16A H 0.9776 0.6306 0.7583 0.146 Uiso 1 calc R . H16B H 1.1357 0.5638 0.7483 0.146 Uiso 1 calc R . H16C H 1.0844 0.6030 0.8144 0.146 Uiso 1 calc R . C17 C 0.9051(6) 0.2214(3) 0.87903(16) 0.1097(13) Uani 1 d . . H17A H 0.9872 0.1789 0.8584 0.165 Uiso 1 calc R . H17B H 0.8385 0.1607 0.8976 0.165 Uiso 1 calc R . H17C H 0.9465 0.2755 0.9100 0.165 Uiso 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 0.0634(3) 0.0678(3) 0.0428(2) -0.00770(19) -0.0118(2) 0.0147(2) O1 0.0683(9) 0.0874(11) 0.0444(7) -0.0096(6) -0.0118(7) 0.0065(9) O2 0.0679(10) 0.1179(16) 0.0572(9) -0.0156(10) -0.0026(8) 0.0266(11) O3 0.1120(15) 0.0694(11) 0.0789(11) -0.0037(8) -0.0357(12) 0.0217(10) O6 0.0692(9) 0.0895(11) 0.0489(7) 0.0004(7) -0.0043(7) -0.0230(8) O7 0.0661(8) 0.0682(8) 0.0362(6) -0.0056(5) -0.0006(7) -0.0031(7) O11 0.0597(8) 0.0533(8) 0.0731(9) 0.0001(6) -0.0064(8) 0.0014(6) O12 0.0839(11) 0.0590(9) 0.0754(10) 0.0014(7) -0.0299(9) -0.0149(7) N1 0.0553(9) 0.0549(8) 0.0354(7) -0.0052(6) -0.0023(7) 0.0005(7) C2 0.0660(12) 0.0458(9) 0.0449(9) -0.0004(7) -0.0039(9) -0.0018(8) C3 0.0737(14) 0.0699(14) 0.0448(10) 0.0068(9) -0.0006(10) -0.0094(11) C4 0.0592(11) 0.0697(12) 0.0395(9) -0.0033(8) -0.0003(9) 0.0032(9) C5 0.0548(10) 0.0514(9) 0.0360(7) -0.0042(6) -0.0049(8) 0.0063(8) C6 0.0472(9) 0.0652(11) 0.0396(8) -0.0031(7) -0.0037(8) 0.0000(8) C7 0.0680(13) 0.0843(14) 0.0363(8) -0.0016(8) 0.0007(9) -0.0021(12) C8 0.134(3) 0.0892(19) 0.0612(14) 0.0138(13) -0.0239(18) -0.0023(19) C9 0.128(3) 0.106(2) 0.0423(11) -0.0088(12) -0.0115(14) -0.021(2) C10 0.0791(19) 0.195(4) 0.0572(14) -0.0065(18) 0.0161(15) 0.001(3) C11 0.0576(10) 0.0528(11) 0.0439(8) -0.0020(7) -0.0016(8) -0.0050(8) C12 0.0818(17) 0.0845(17) 0.0904(17) 0.0004(14) -0.0378(16) -0.0152(15) C13 0.0715(15) 0.110(2) 0.0422(10) -0.0117(11) 0.0055(11) 0.0020(14) C14 0.092(2) 0.193(4) 0.0585(14) -0.0248(19) 0.0173(17) 0.004(3) C15 0.139(4) 0.224(6) 0.130(4) -0.049(4) 0.070(4) -0.052(4) C16 0.0581(14) 0.157(3) 0.0779(18) -0.015(2) 0.0076(13) -0.0130(18) C17 0.152(3) 0.083(2) 0.094(2) 0.0016(16) -0.043(2) 0.042(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 O1 1.4654(15) . y P1 O3 1.557(2) . y P1 O2 1.580(2) . y P1 C5 1.821(2) . y O2 C16 1.443(5) . y O3 C17 1.427(3) . y O6 C6 1.207(2) . y O7 C6 1.349(2) . y O7 C7 1.478(2) . y O11 C11 1.200(3) . y O12 C11 1.331(3) . y O12 C12 1.455(3) . y N1 C6 1.363(2) . y N1 C2 1.462(3) . y N1 C5 1.469(2) . y C2 C11 1.519(3) . y C2 C3 1.531(3) . y C2 H2 0.9800 . ? C3 C4 1.526(3) . y C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C13 1.535(3) . y C4 C5 1.536(3) . y C4 H4 0.9800 . ? C5 H5 0.9800 . ? C7 C8 1.502(4) . y C7 C10 1.506(4) . y C7 C9 1.514(4) . y C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.502(5) . y C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.189(7) . y C14 H14 0.9300 . ? C15 H15A 0.9300 . ? C15 H15B 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? 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 O3 116.70(11) . . y O1 P1 O2 113.23(11) . . y O3 P1 O2 102.60(12) . . y O1 P1 C5 113.51(9) . . y O3 P1 C5 102.72(10) . . y O2 P1 C5 106.84(9) . . y C16 O2 P1 119.21(18) . . y C17 O3 P1 123.0(2) . . y C6 O7 C7 120.88(16) . . y C11 O12 C12 115.30(18) . . y C6 N1 C2 121.71(15) . . y C6 N1 C5 120.65(16) . . y C2 N1 C5 112.53(15) . . y N1 C2 C11 111.01(15) . . y N1 C2 C3 103.30(16) . . y C11 C2 C3 109.59(19) . . y N1 C2 H2 110.90(10) . . ? C11 C2 H2 110.9 . . ? C3 C2 H2 110.9 . . ? C4 C3 C2 103.19(17) . . y C4 C3 H3A 111.1 . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3B 111.1 . . ? C2 C3 H3B 111.1 . . ? H3A C3 H3B 109.1 . . ? C3 C4 C13 115.4(2) . . y C3 C4 C5 103.03(17) . . y C13 C4 C5 117.28(19) . . y C3 C4 H4 106.8 . . ? C13 C4 H4 106.8 . . ? C5 C4 H4 106.8 . . ? N1 C5 C4 102.76(16) . . y N1 C5 P1 112.57(13) . . y C4 C5 P1 116.72(13) . . y N1 C5 H5 108.1 . . ? C4 C5 H5 108.1 . . ? P1 C5 H5 108.1 . . ? O6 C6 O7 126.46(17) . . y O6 C6 N1 124.56(17) . . y O7 C6 N1 108.97(16) . . y O7 C7 C8 110.35(19) . . y O7 C7 C10 109.2(2) . . y C8 C7 C10 113.2(3) . . y O7 C7 C9 102.27(19) . . y C8 C7 C9 110.2(3) . . y C10 C7 C9 111.0(2) . . y C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O11 C11 O12 124.7(2) . . y O11 C11 C2 125.02(18) . . y O12 C11 C2 110.24(17) . . y O12 C12 H12A 109.5 . . ? O12 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O12 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C4 111.6(2) . . y C14 C13 H13A 109.3 . . ? C4 C13 H13A 109.3 . . ? C14 C13 H13B 109.3 . . ? C4 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? C15 C14 C13 132.0(6) . . y C15 C14 H14 114.0 . . ? C13 C14 H14 114.0 . . ? C14 C15 H15A 120.0 . . ? C14 C15 H15B 120.0 . . ? H15A C15 H15B 120.0 . . ? O2 C16 H16A 109.5 . . ? O2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O3 C17 H17A 109.5 . . ? O3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 O1 P1 O2 C16 -40.8(2) . . . . y O3 P1 O2 C16 -167.4(2) . . . . y C5 P1 O2 C16 84.9(2) . . . . y O1 P1 O3 C17 -37.6(3) . . . . y O2 P1 O3 C17 86.8(3) . . . . y C5 P1 O3 C17 -162.4(3) . . . . y C6 N1 C2 C11 -48.6(2) . . . . y C5 N1 C2 C11 106.28(18) . . . . y C6 N1 C2 C3 -165.93(19) . . . . y C5 N1 C2 C3 -11.1(2) . . . . y N1 C2 C3 C4 30.9(2) . . . . y C11 C2 C3 C4 -87.4(2) . . . . y C2 C3 C4 C13 -168.4(2) . . . . y C2 C3 C4 C5 -39.2(2) . . . . y C6 N1 C5 C4 141.98(18) . . . . y C2 N1 C5 C4 -13.2(2) . . . . y C6 N1 C5 P1 -91.63(19) . . . . y C2 N1 C5 P1 113.23(16) . . . . y C3 C4 C5 N1 32.04(18) . . . . y C13 C4 C5 N1 160.0(2) . . . . y C3 C4 C5 P1 -91.64(17) . . . . y C13 C4 C5 P1 36.3(3) . . . . y O1 P1 C5 N1 177.79(14) . . . . y O3 P1 C5 N1 -55.30(17) . . . . y O2 P1 C5 N1 52.27(16) . . . . y O1 P1 C5 C4 -63.72(18) . . . . y O3 P1 C5 C4 63.18(17) . . . . y O2 P1 C5 C4 170.76(16) . . . . y C7 O7 C6 O6 -11.9(3) . . . . y C7 O7 C6 N1 168.75(18) . . . . y C2 N1 C6 O6 162.2(2) . . . . y C5 N1 C6 O6 9.4(3) . . . . y C2 N1 C6 O7 -18.4(2) . . . . y C5 N1 C6 O7 -171.29(17) . . . . y C6 O7 C7 C8 -53.2(3) . . . . y C6 O7 C7 C10 71.9(3) . . . . y C6 O7 C7 C9 -170.5(2) . . . . y C12 O12 C11 O11 -1.1(3) . . . . y C12 O12 C11 C2 175.9(2) . . . . y N1 C2 C11 O11 -31.2(3) . . . . y C3 C2 C11 O11 82.3(3) . . . . y N1 C2 C11 O12 151.87(17) . . . . y C3 C2 C11 O12 -94.7(2) . . . . y C3 C4 C13 C14 -70.0(4) . . . . y C5 C4 C13 C14 168.2(3) . . . . y C4 C13 C14 C15 130.7(5) . . . . y _refine_diff_density_max 0.260 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.046