# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_requested_category FO _publ_contact_author_email sylvain.marque@univ-provence.fr _publ_contact_author_name 'Sylvain Marque' loop_ _publ_author_name 'Sylvain Marque' 'Paul Bremond' data_pyrnomin _database_code_depnum_ccdc_archive 'CCDC 804939' #TrackingRef '- minordia.cif' _audit_creation_date 2010-11-19T15:01:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H37 N2 O4 P1' _chemical_formula_sum 'C20 H37 N2 O4 P' _chemical_formula_weight 400.49 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.3707(2) _cell_length_b 9.7253(2) _cell_length_c 18.8006(4) _cell_angle_alpha 90 _cell_angle_beta 110.186(1) _cell_angle_gamma 90 _cell_volume 2294.56(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20863 _cell_measurement_theta_min 1.62 _cell_measurement_theta_max 28.72 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 1.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'Omega + Phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_unetI/netI 0.0343 _diffrn_reflns_number 20863 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 28.72 _diffrn_reflns_theta_full 28.72 _diffrn_measured_fraction_theta_full 0.971 _diffrn_measured_fraction_theta_max 0.971 _reflns_number_total 5772 _reflns_number_gt 4537 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1125P)^2^+0.3935P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5772 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1971 _refine_ls_wR_factor_gt 0.1612 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.674 _refine_diff_density_min -0.947 _refine_diff_density_rms 0.284 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.16989(13) 0.40236(17) 0.21970(9) 0.0364(4) Uani 1 1 d . . . H1 H 0.1189 0.4743 0.2202 0.044 Uiso 1 1 calc R . . C2 C 0.12782(16) 0.3427(2) 0.13677(10) 0.0459(4) Uani 1 1 d . . . C3 C 0.0117(2) 0.2989(3) 0.11785(14) 0.0713(7) Uani 1 1 d . . . H3A H -0.0154 0.2641 0.067 0.107 Uiso 1 1 calc R . . H3B H -0.03 0.3767 0.1222 0.107 Uiso 1 1 calc R . . H3C H 0.0074 0.2284 0.1525 0.107 Uiso 1 1 calc R . . C4 C 0.1925(2) 0.2198(2) 0.12642(12) 0.0666(7) Uani 1 1 d . . . H4A H 0.1864 0.1457 0.1584 0.1 Uiso 1 1 calc R . . H4B H 0.2659 0.2459 0.1398 0.1 Uiso 1 1 calc R . . H4C H 0.1658 0.1906 0.0745 0.1 Uiso 1 1 calc R . . C5 C 0.1294(2) 0.4539(3) 0.07888(12) 0.0579(5) Uani 1 1 d . . . H5A H 0.2018 0.4782 0.086 0.087 Uiso 1 1 calc R . . H5B H 0.0918 0.5338 0.0861 0.087 Uiso 1 1 calc R . . H5C H 0.0955 0.4191 0.0285 0.087 Uiso 1 1 calc R . . C6 C 0.3216(2) 0.7332(2) 0.18576(16) 0.0653(6) Uani 1 1 d . . . H6A H 0.3652 0.6864 0.1614 0.078 Uiso 1 1 calc R . . H6B H 0.3684 0.7767 0.2316 0.078 Uiso 1 1 calc R . . C7 C 0.2545(3) 0.8375(3) 0.1344(2) 0.0920(11) Uani 1 1 d . . . H7A H 0.2093 0.7938 0.0889 0.138 Uiso 1 1 calc R . . H7B H 0.2991 0.9038 0.122 0.138 Uiso 1 1 calc R . . H7C H 0.2114 0.8829 0.1589 0.138 Uiso 1 1 calc R . . C8 C 0.4487(2) 0.4799(3) 0.37636(16) 0.0781(8) Uani 1 1 d . . . H8A H 0.4771 0.4154 0.3488 0.094 Uiso 1 1 calc R . . H8B H 0.4394 0.4317 0.4188 0.094 Uiso 1 1 calc R . . C9 C 0.5239(2) 0.5946(4) 0.4045(2) 0.0952(11) Uani 1 1 d . . . H9A H 0.5345 0.6405 0.3624 0.143 Uiso 1 1 calc R . . H9B H 0.5907 0.5597 0.4379 0.143 Uiso 1 1 calc R . . H9C H 0.4953 0.6584 0.4315 0.143 Uiso 1 1 calc R . . C10 C 0.10817(15) 0.3459(2) 0.32997(11) 0.0447(4) Uani 1 1 d . . . C11 C -0.0061(2) 0.3878(3) 0.28384(16) 0.0761(8) Uani 1 1 d . . . H11A H -0.005 0.4671 0.2537 0.114 Uiso 1 1 calc R . . H11B H -0.0438 0.4093 0.3176 0.114 Uiso 1 1 calc R . . H11C H -0.0411 0.3133 0.2513 0.114 Uiso 1 1 calc R . . C12 C 0.1632(2) 0.4641(3) 0.38161(17) 0.0740(7) Uani 1 1 d . . . H12A H 0.2346 0.4376 0.4113 0.111 Uiso 1 1 calc R . . H12B H 0.1246 0.4862 0.4147 0.111 Uiso 1 1 calc R . . H12C H 0.1652 0.543 0.3515 0.111 Uiso 1 1 calc R . . C13 C 0.1003(2) 0.2217(3) 0.37713(15) 0.0639(6) Uani 1 1 d . . . H13A H 0.0718 0.1449 0.3443 0.096 Uiso 1 1 calc R . . H13B H 0.0541 0.243 0.405 0.096 Uiso 1 1 calc R . . H13C H 0.1698 0.1988 0.4118 0.096 Uiso 1 1 calc R . . C14 C 0.29652(14) 0.11817(18) 0.31530(10) 0.0395(4) Uani 1 1 d . . . H14 H 0.2386 0.0765 0.2735 0.047 Uiso 1 1 calc R . . C15 C 0.31252(14) 0.03789(19) 0.38700(10) 0.0394(4) Uani 1 1 d . . . C16 C 0.36047(16) 0.0941(2) 0.45866(11) 0.0474(4) Uani 1 1 d . . . H16 H 0.3801 0.1863 0.464 0.057 Uiso 1 1 calc R . . C17 C 0.37873(19) 0.0122(2) 0.52181(13) 0.0555(5) Uani 1 1 d . . . H17 H 0.4099 0.0525 0.5692 0.067 Uiso 1 1 calc R . . C18 C 0.3096(2) -0.1739(2) 0.45026(15) 0.0671(6) Uani 1 1 d . . . H18 H 0.2925 -0.2669 0.4467 0.081 Uiso 1 1 calc R . . C19 C 0.28661(19) -0.1001(2) 0.38368(13) 0.0547(5) Uani 1 1 d . . . H19 H 0.2541 -0.1429 0.3371 0.066 Uiso 1 1 calc R . . C20 C 0.39928(18) 0.1123(2) 0.29747(13) 0.0550(5) Uani 1 1 d . . . H20A H 0.3905 0.1637 0.2521 0.083 Uiso 1 1 calc R . . H20B H 0.4156 0.0184 0.2903 0.083 Uiso 1 1 calc R . . H20C H 0.4564 0.1513 0.3388 0.083 Uiso 1 1 calc R . . N1 N 0.16335(11) 0.29884(14) 0.27649(8) 0.0356(3) Uani 1 1 d . . . N2 N 0.35455(18) -0.1206(2) 0.51906(12) 0.0641(5) Uani 1 1 d . . . O2 O 0.37630(12) 0.42839(16) 0.21156(9) 0.0552(4) Uani 1 1 d . . . O3 O 0.34672(12) 0.53190(16) 0.32681(9) 0.0559(4) Uani 1 1 d . . . O4 O 0.25267(12) 0.63551(14) 0.20429(9) 0.0529(4) Uani 1 1 d . . . O5 O 0.27242(9) 0.26143(12) 0.32228(7) 0.0375(3) Uani 1 1 d . . . P1 P 0.29869(4) 0.49209(5) 0.24056(3) 0.04145(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0350(8) 0.0340(8) 0.0403(9) 0.0023(6) 0.0130(7) 0.0006(6) C2 0.0458(10) 0.0472(10) 0.0378(9) 0.0033(7) 0.0054(8) 0.0014(8) C3 0.0586(14) 0.0823(17) 0.0587(14) -0.0032(12) 0.0020(11) -0.0208(12) C4 0.0931(18) 0.0550(13) 0.0393(10) -0.0072(9) 0.0070(11) 0.0198(12) C5 0.0621(13) 0.0651(13) 0.0414(11) 0.0121(9) 0.0115(10) 0.0080(10) C6 0.0752(16) 0.0435(11) 0.0927(18) 0.0024(11) 0.0488(14) -0.0122(10) C7 0.116(3) 0.0521(14) 0.139(3) 0.0329(16) 0.085(2) 0.0148(15) C8 0.0588(15) 0.0892(19) 0.0644(16) -0.0037(13) -0.0066(12) -0.0151(13) C9 0.0580(16) 0.121(3) 0.099(2) -0.045(2) 0.0172(15) -0.0312(16) C10 0.0411(10) 0.0453(10) 0.0532(11) 0.0054(8) 0.0234(8) 0.0047(7) C11 0.0510(13) 0.105(2) 0.0826(18) 0.0314(15) 0.0358(13) 0.0280(13) C12 0.0822(18) 0.0696(15) 0.0883(19) -0.0254(14) 0.0527(16) -0.0060(13) C13 0.0702(15) 0.0625(14) 0.0750(15) 0.0200(11) 0.0455(13) 0.0098(11) C14 0.0403(9) 0.0367(9) 0.0392(9) 0.0002(7) 0.0107(7) 0.0059(7) C15 0.0348(8) 0.0395(9) 0.0423(9) 0.0023(7) 0.0113(7) 0.0054(7) C16 0.0496(11) 0.0436(10) 0.0431(10) 0.0018(7) 0.0086(8) 0.0024(8) C17 0.0568(12) 0.0636(13) 0.0427(11) 0.0084(9) 0.0129(9) 0.0091(10) C18 0.0790(17) 0.0457(12) 0.0762(16) 0.0122(11) 0.0260(13) -0.0052(11) C19 0.0578(12) 0.0450(11) 0.0572(12) -0.0009(9) 0.0147(10) -0.0036(9) C20 0.0550(12) 0.0614(13) 0.0555(12) 0.0121(9) 0.0277(10) 0.0214(10) N1 0.0287(7) 0.0369(7) 0.0399(7) 0.0064(6) 0.0100(6) 0.0031(5) N2 0.0710(13) 0.0611(12) 0.0621(12) 0.0203(9) 0.0254(10) 0.0057(9) O2 0.0456(8) 0.0583(9) 0.0687(9) 0.0025(7) 0.0286(7) 0.0031(6) O3 0.0525(9) 0.0551(9) 0.0540(9) -0.0089(6) 0.0108(7) -0.0124(7) O4 0.0564(9) 0.0407(7) 0.0693(9) 0.0091(6) 0.0316(7) -0.0016(6) O5 0.0310(6) 0.0368(6) 0.0406(6) 0.0013(5) 0.0072(5) 0.0032(4) P1 0.0388(3) 0.0392(3) 0.0484(3) 0.00092(18) 0.0177(2) -0.00341(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.492(2) . ? C1 C2 1.575(2) . ? C1 P1 1.8480(17) . ? C1 H1 0.98 . ? C2 C4 1.526(3) . ? C2 C3 1.529(3) . ? C2 C5 1.540(3) . ? C3 H3A 0.96 . ? C3 H3B 0.96 . ? C3 H3C 0.96 . ? C4 H4A 0.96 . ? C4 H4B 0.96 . ? C4 H4C 0.96 . ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? C6 O4 1.447(2) . ? C6 C7 1.472(4) . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? C8 O3 1.452(3) . ? C8 C9 1.472(4) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C9 H9A 0.96 . ? C9 H9B 0.96 . ? C9 H9C 0.96 . ? C10 N1 1.509(2) . ? C10 C12 1.520(3) . ? C10 C13 1.524(3) . ? C10 C11 1.529(3) . ? C11 H11A 0.96 . ? C11 H11B 0.96 . ? C11 H11C 0.96 . ? C12 H12A 0.96 . ? C12 H12B 0.96 . ? C12 H12C 0.96 . ? C13 H13A 0.96 . ? C13 H13B 0.96 . ? C13 H13C 0.96 . ? C14 O5 1.446(2) . ? C14 C15 1.508(2) . ? C14 C20 1.523(3) . ? C14 H14 0.98 . ? C15 C19 1.382(3) . ? C15 C16 1.389(3) . ? C16 C17 1.379(3) . ? C16 H16 0.93 . ? C17 N2 1.328(3) . ? C17 H17 0.93 . ? C18 N2 1.329(3) . ? C18 C19 1.382(3) . ? C18 H18 0.93 . ? C19 H19 0.93 . ? C20 H20A 0.96 . ? C20 H20B 0.96 . ? C20 H20C 0.96 . ? N1 O5 1.4607(17) . ? O2 P1 1.4657(15) . ? O3 P1 1.5725(16) . ? O4 P1 1.5810(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 111.76(14) . . ? N1 C1 P1 116.57(11) . . ? C2 C1 P1 111.88(12) . . ? N1 C1 H1 105.2 . . ? C2 C1 H1 105.2 . . ? P1 C1 H1 105.2 . . ? C4 C2 C3 109.1(2) . . ? C4 C2 C5 108.27(18) . . ? C3 C2 C5 106.95(18) . . ? C4 C2 C1 112.98(15) . . ? C3 C2 C1 108.67(17) . . ? C5 C2 C1 110.70(16) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O4 C6 C7 108.4(2) . . ? O4 C6 H6A 110 . . ? C7 C6 H6A 110 . . ? O4 C6 H6B 110 . . ? C7 C6 H6B 110 . . ? H6A C6 H6B 108.4 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O3 C8 C9 109.9(3) . . ? O3 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? O3 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? 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 . . ? N1 C10 C12 114.49(16) . . ? N1 C10 C13 107.19(16) . . ? C12 C10 C13 110.1(2) . . ? N1 C10 C11 108.99(17) . . ? C12 C10 C11 109.2(2) . . ? C13 C10 C11 106.56(19) . . ? 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 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O5 C14 C15 112.64(14) . . ? O5 C14 C20 107.57(16) . . ? C15 C14 C20 108.48(15) . . ? O5 C14 H14 109.4 . . ? C15 C14 H14 109.4 . . ? C20 C14 H14 109.4 . . ? C19 C15 C16 116.78(18) . . ? C19 C15 C14 120.42(17) . . ? C16 C15 C14 122.62(17) . . ? C17 C16 C15 119.55(19) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? N2 C17 C16 124.0(2) . . ? N2 C17 H17 118 . . ? C16 C17 H17 118 . . ? N2 C18 C19 124.3(2) . . ? N2 C18 H18 117.9 . . ? C19 C18 H18 117.9 . . ? C15 C19 C18 119.3(2) . . ? C15 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? C14 C20 H20A 109.5 . . ? C14 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C14 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O5 N1 C1 107.26(12) . . ? O5 N1 C10 107.53(13) . . ? C1 N1 C10 115.80(13) . . ? C17 N2 C18 116.08(19) . . ? C8 O3 P1 122.34(17) . . ? C6 O4 P1 119.83(15) . . ? C14 O5 N1 113.26(12) . . ? O2 P1 O3 113.45(9) . . ? O2 P1 O4 115.63(9) . . ? O3 P1 O4 100.79(9) . . ? O2 P1 C1 116.68(9) . . ? O3 P1 C1 110.74(8) . . ? O4 P1 C1 97.45(8) . . ? # END of CIF