# Electronic Supplementary Material (ESI) for RSC Advances # 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_17 _database_code_depnum_ccdc_archive 'CCDC 912211' #TrackingRef 'depo_wolf.cif' _audit_update_record ; 2012-11-23 # Formatted by publCIF ; #==================================================== _chemical_name_systematic ; diethyl[(2S*,5S*,6S*)-3-benzyl-2-methyl-4-oxo-3,4,5,6- tetrahydro-2H-2,6-methanobenzo[g][1,3]oxazocin-5-yl]phosphonate ; _chemical_formula_moiety 'C23 H28 N O5 P' _chemical_formula_sum 'C23 H28 N O5 P' _chemical_formula_weight 429.43 _chemical_melting_point 402(1) _exptl_crystal_colour colourless _exptl_crystal_description prism _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_preparation ; slow evaporation from acetone and n-heptane ; _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8810 _exptl_absorpt_correction_T_max 0.9426 _exptl_absorpt_process_details 'Bruker SADABS' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _space_group_name_Hall '-P 2ybc' 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 9.1840(10) _cell_length_b 18.429(2) _cell_length_c 13.3004(15) _cell_angle_alpha 90.00 _cell_angle_beta 94.728(2) _cell_angle_gamma 90.00 _cell_volume 2243.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 291(1) _exptl_crystal_density_diffrn 1.271 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_ambient_temperature 291(2) _diffrn_reflns_number 24377 _reflns_number_total 3928 _reflns_number_gt 3428 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _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^)+(0.0596P)^2^+1.6774P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_number_reflns 3933 _refine_ls_number_parameters 343 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1496 _refine_ls_wR_factor_gt 0.1457 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.301 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.045 _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P P 0.33268(7) 0.64317(3) 0.75256(6) 0.0560(2) Uani 1 1 d . A 1 O1 O 0.35349(19) 0.73478(11) 0.55046(12) 0.0623(5) Uani 1 1 d . A 1 O2 O 0.49253(16) 0.90926(9) 0.74937(12) 0.0517(4) Uani 1 1 d . A 1 O3 O 0.4874(2) 0.62905(11) 0.7755(2) 0.0890(7) Uani 1 1 d . A 1 O4 O 0.2569(2) 0.59542(10) 0.66658(16) 0.0726(6) Uani 1 1 d . A 1 O5 O 0.2339(3) 0.63008(11) 0.84114(16) 0.0806(6) Uani 1 1 d . A 1 N N 0.50336(18) 0.80057(10) 0.65710(13) 0.0428(4) Uani 1 1 d . A 1 C1 C 0.2913(2) 0.73679(12) 0.71992(16) 0.0399(5) Uani 1 1 d . A 1 H11 H 0.194(3) 0.7378(12) 0.6915(17) 0.042(6) Uiso 1 1 d . B 1 C2 C 0.3845(2) 0.75765(12) 0.63542(15) 0.0422(5) Uani 1 1 d . A 1 C3 C 0.5431(2) 0.83516(13) 0.75540(17) 0.0465(5) Uani 1 1 d . A 1 C4 C 0.4734(2) 0.79630(14) 0.83875(16) 0.0462(5) Uani 1 1 d . A 1 H41 H 0.519(3) 0.7486(14) 0.8503(17) 0.046(6) Uiso 1 1 d . C 1 H42 H 0.494(3) 0.8239(13) 0.8987(19) 0.049(6) Uiso 1 1 d . D 1 C5 C 0.3115(2) 0.78964(12) 0.80905(15) 0.0404(5) Uani 1 1 d . A 1 H51 H 0.261(3) 0.7686(13) 0.8652(19) 0.049(6) Uiso 1 1 d . E 1 C6 C 0.5823(3) 0.82426(15) 0.57130(19) 0.0521(6) Uani 1 1 d . A 1 H72 H 0.609(3) 0.8771(15) 0.5819(19) 0.054(7) Uiso 1 1 d . F 1 H71 H 0.513(3) 0.8216(15) 0.514(2) 0.066(8) Uiso 1 1 d . G 1 C7 C 0.7164(3) 0.77991(15) 0.55367(18) 0.0532(6) Uani 1 1 d . A 1 C8 C 0.8182(4) 0.8090(2) 0.4945(3) 0.0825(10) Uani 1 1 d . A 1 H81 H 0.797(4) 0.8539(19) 0.465(3) 0.091(11) Uiso 1 1 d . H 1 C9 C 0.9443(4) 0.7711(2) 0.4779(3) 0.0946(12) Uani 1 1 d . A 1 H91 H 1.006(4) 0.792(2) 0.428(3) 0.116(13) Uiso 1 1 d . I 1 C10 C 0.9696(3) 0.7042(2) 0.5191(3) 0.0813(10) Uani 1 1 d . A 1 H101 H 1.059(4) 0.6766(18) 0.507(2) 0.091(10) Uiso 1 1 d . J 1 C11 C 0.8679(4) 0.6741(2) 0.5755(2) 0.0785(9) Uani 1 1 d . A 1 H111 H 0.886(4) 0.626(2) 0.605(3) 0.104(12) Uiso 1 1 d . K 1 C12 C 0.7413(3) 0.71194(17) 0.5924(2) 0.0637(7) Uani 1 1 d . A 1 H121 H 0.672(3) 0.6904(17) 0.626(2) 0.079(9) Uiso 1 1 d . L 1 C13 C 0.7068(3) 0.8400(2) 0.7773(2) 0.0643(7) Uani 1 1 d . A 1 H131 H 0.750(3) 0.8714(16) 0.730(2) 0.073(9) Uiso 1 1 d . M 1 H132 H 0.749(3) 0.7924(17) 0.779(2) 0.072(9) Uiso 1 1 d . N 1 H133 H 0.729(3) 0.8631(16) 0.847(2) 0.077(9) Uiso 1 1 d . O 1 C14 C 0.2517(2) 0.86383(12) 0.78045(16) 0.0416(5) Uani 1 1 d . A 1 C15 C 0.3446(2) 0.91932(12) 0.75438(16) 0.0444(5) Uani 1 1 d . A 1 C16 C 0.2926(3) 0.98906(14) 0.7349(2) 0.0563(6) Uani 1 1 d . A 1 H161 H 0.360(3) 1.0263(15) 0.719(2) 0.063(8) Uiso 1 1 d . P 1 C17 C 0.1468(3) 1.00377(15) 0.7397(2) 0.0647(7) Uani 1 1 d . A 1 H171 H 0.112(3) 1.0531(17) 0.723(2) 0.075(9) Uiso 1 1 d . Q 1 C18 C 0.0522(3) 0.94931(16) 0.7632(2) 0.0651(7) Uani 1 1 d . A 1 H181 H -0.055(4) 0.9579(18) 0.765(2) 0.092(10) Uiso 1 1 d . R 1 C19 C 0.1046(3) 0.88030(14) 0.78305(19) 0.0527(6) Uani 1 1 d . A 1 H191 H 0.035(3) 0.8397(15) 0.802(2) 0.065(8) Uiso 1 1 d . S 1 C20 C 0.3409(5) 0.5598(3) 0.5933(4) 0.1275(17) Uani 1 1 d . A 1 H201 H 0.3878 0.5963 0.5543 0.191 Uiso 1 1 calc R A 1 H202 H 0.4169 0.5306 0.6283 0.191 Uiso 1 1 calc R A 1 C21 C 0.2531(7) 0.5155(3) 0.5277(3) 0.1375(19) Uani 1 1 d . A 1 H211 H 0.3139 0.4870 0.4877 0.206 Uiso 1 1 calc R A 1 H212 H 0.1893 0.5452 0.4843 0.206 Uiso 1 1 calc R A 1 H213 H 0.1959 0.4840 0.5663 0.206 Uiso 1 1 calc R A 1 C22 C 0.2669(9) 0.5600(4) 0.8916(5) 0.110(3) Uani 0.676(9) 1 d PD A 1 H221 H 0.3700 0.5565 0.9135 0.164 Uiso 0.676(9) 1 calc PR A 1 H222 H 0.2406 0.5199 0.8464 0.164 Uiso 0.676(9) 1 calc PR A 1 C23 C 0.1766(11) 0.5592(5) 0.9801(5) 0.157(4) Uani 0.676(9) 1 d PD A 1 H231 H 0.1947 0.5151 1.0175 0.235 Uiso 0.676(9) 1 calc PR A 1 H232 H 0.0750 0.5619 0.9568 0.235 Uiso 0.676(9) 1 calc PR A 1 H233 H 0.2022 0.6000 1.0228 0.235 Uiso 0.676(9) 1 calc PR A 1 C22A C 0.2497(15) 0.5954(7) 0.9382(10) 0.092(4) Uani 0.324(9) 1 d PD A 2 H223 H 0.1733 0.6130 0.9781 0.138 Uiso 0.324(9) 1 calc PR A 2 H224 H 0.3427 0.6098 0.9723 0.138 Uiso 0.324(9) 1 calc PR A 2 C23A C 0.243(3) 0.5143(7) 0.9345(16) 0.208(13) Uani 0.324(9) 1 d PD A 2 H234 H 0.2446 0.4955 1.0019 0.313 Uiso 0.324(9) 1 calc PR A 2 H235 H 0.3253 0.4960 0.9026 0.313 Uiso 0.324(9) 1 calc PR A 2 H236 H 0.1543 0.4994 0.8968 0.313 Uiso 0.324(9) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P 0.0571(4) 0.0434(4) 0.0675(5) -0.0010(3) 0.0037(3) 0.0031(3) O1 0.0605(11) 0.0892(13) 0.0375(9) -0.0170(8) 0.0055(7) -0.0125(9) O2 0.0422(8) 0.0516(9) 0.0620(10) -0.0064(7) 0.0096(7) -0.0109(7) O3 0.0679(13) 0.0591(12) 0.136(2) -0.0031(12) -0.0145(13) 0.0189(10) O4 0.0770(13) 0.0567(11) 0.0849(14) -0.0214(10) 0.0108(10) -0.0054(9) O5 0.1172(18) 0.0582(12) 0.0685(13) 0.0189(9) 0.0208(12) -0.0037(11) N 0.0353(9) 0.0561(11) 0.0379(9) -0.0014(8) 0.0079(7) -0.0022(8) C1 0.0342(11) 0.0447(11) 0.0409(11) -0.0015(9) 0.0038(9) -0.0009(9) C2 0.0380(11) 0.0514(12) 0.0373(11) -0.0033(9) 0.0033(8) 0.0016(9) C3 0.0371(11) 0.0576(14) 0.0443(12) -0.0068(10) 0.0006(9) -0.0031(10) C4 0.0473(12) 0.0567(14) 0.0339(11) -0.0036(10) -0.0020(9) -0.0001(11) C5 0.0415(11) 0.0467(12) 0.0337(10) 0.0008(9) 0.0081(8) -0.0015(9) C6 0.0455(13) 0.0664(16) 0.0460(13) 0.0044(11) 0.0126(10) -0.0029(11) C7 0.0412(12) 0.0712(16) 0.0487(13) -0.0095(12) 0.0117(10) -0.0070(11) C8 0.074(2) 0.078(2) 0.102(3) -0.0031(19) 0.0474(18) -0.0082(17) C9 0.0625(19) 0.111(3) 0.118(3) -0.022(2) 0.053(2) -0.0142(19) C10 0.0502(17) 0.114(3) 0.081(2) -0.030(2) 0.0105(15) 0.0092(17) C11 0.0714(19) 0.097(3) 0.0666(18) -0.0066(17) 0.0056(15) 0.0227(18) C12 0.0556(16) 0.0803(19) 0.0571(15) 0.0037(14) 0.0155(12) 0.0064(14) C13 0.0389(13) 0.088(2) 0.0649(18) -0.0110(16) -0.0021(12) -0.0069(14) C14 0.0428(11) 0.0462(12) 0.0362(11) -0.0053(9) 0.0057(8) -0.0027(9) C15 0.0431(11) 0.0487(12) 0.0417(11) -0.0066(9) 0.0043(9) -0.0059(9) C16 0.0627(15) 0.0455(13) 0.0604(15) -0.0025(11) 0.0032(12) -0.0082(12) C17 0.0674(17) 0.0495(15) 0.0761(18) -0.0032(13) 0.0001(14) 0.0061(13) C18 0.0489(14) 0.0635(17) 0.0825(19) -0.0027(14) 0.0039(13) 0.0085(12) C19 0.0453(13) 0.0544(14) 0.0592(14) -0.0032(11) 0.0089(10) -0.0018(11) C20 0.134(4) 0.111(3) 0.141(4) -0.075(3) 0.031(3) 0.005(3) C21 0.226(6) 0.107(3) 0.079(3) -0.031(2) 0.010(3) -0.012(3) C22 0.192(7) 0.057(4) 0.081(4) 0.020(3) 0.019(4) -0.017(4) C23 0.253(12) 0.124(7) 0.099(6) 0.059(5) 0.051(6) -0.004(7) C22A 0.112(9) 0.099(10) 0.067(8) 0.003(7) 0.019(6) -0.016(8) C23A 0.32(3) 0.18(2) 0.131(18) 0.076(17) 0.085(19) 0.07(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P O3 1.452(2) . ? P O4 1.560(2) . ? P O5 1.564(2) . ? P C1 1.812(2) . ? O1 C2 1.218(3) . ? O2 C15 1.378(3) . ? O2 C3 1.442(3) . ? O4 C20 1.449(4) . ? O5 C22A 1.437(13) . ? O5 C22 1.475(6) . ? N C2 1.360(3) . ? N C6 1.468(3) . ? N C3 1.473(3) . ? C1 C2 1.517(3) . ? C1 C5 1.534(3) . ? C1 H11 0.95(2) . ? C3 C4 1.506(3) . ? C3 C13 1.511(3) . ? C4 C5 1.512(3) . ? C4 H41 0.98(2) . ? C4 H42 0.95(3) . ? C5 C14 1.510(3) . ? C5 H51 0.99(2) . ? C6 C7 1.513(3) . ? C6 H72 1.01(3) . ? C6 H71 0.96(3) . ? C7 C12 1.367(4) . ? C7 C8 1.380(4) . ? C8 C9 1.385(5) . ? C8 H81 0.93(4) . ? C9 C10 1.362(6) . ? C9 H91 0.99(4) . ? C10 C11 1.363(5) . ? C10 H101 0.99(3) . ? C11 C12 1.390(4) . ? C11 H111 0.98(4) . ? C12 H121 0.90(3) . ? C13 H131 0.96(3) . ? C13 H132 0.96(3) . ? C13 H133 1.02(3) . ? C14 C19 1.387(3) . ? C14 C15 1.394(3) . ? C15 C16 1.388(3) . ? C16 C17 1.373(4) . ? C16 H161 0.96(3) . ? C17 C18 1.380(4) . ? C17 H171 0.98(3) . ? C18 C19 1.378(4) . ? C18 H181 1.00(4) . ? C19 H191 1.03(3) . ? C20 C21 1.400(6) . ? C20 H201 0.9700 . ? C20 H202 0.9700 . ? C21 H211 0.9600 . ? C21 H212 0.9600 . ? C21 H213 0.9600 . ? C22 C23 1.494(2) . ? C22 H221 0.9700 . ? C22 H222 0.9700 . ? C23 H231 0.9600 . ? C23 H232 0.9600 . ? C23 H233 0.9600 . ? C22A C23A 1.497(2) . ? C22A H223 0.9700 . ? C22A H224 0.9700 . ? C23A H234 0.9600 . ? C23A H235 0.9600 . ? C23A H236 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 O3 P O4 114.98(13) . . ? O3 P O5 115.63(15) . . ? O4 P O5 102.35(12) . . ? O3 P C1 113.77(12) . . ? O4 P C1 106.83(11) . . ? O5 P C1 101.79(10) . . ? C15 O2 C3 116.02(16) . . ? C20 O4 P 121.2(2) . . ? C22A O5 C22 36.9(5) . . ? C22A O5 P 136.3(6) . . ? C22 O5 P 111.6(3) . . ? C2 N C6 116.57(18) . . ? C2 N C3 125.15(17) . . ? C6 N C3 117.34(19) . . ? C2 C1 C5 111.85(17) . . ? C2 C1 P 107.40(15) . . ? C5 C1 P 114.21(15) . . ? C2 C1 H11 105.9(14) . . ? C5 C1 H11 110.3(14) . . ? P C1 H11 106.7(14) . . ? O1 C2 N 121.4(2) . . ? O1 C2 C1 119.8(2) . . ? N C2 C1 118.83(18) . . ? O2 C3 N 107.78(17) . . ? O2 C3 C4 109.68(18) . . ? N C3 C4 111.00(18) . . ? O2 C3 C13 105.4(2) . . ? N C3 C13 111.5(2) . . ? C4 C3 C13 111.3(2) . . ? C3 C4 C5 108.34(18) . . ? C3 C4 H41 109.8(14) . . ? C5 C4 H41 111.6(14) . . ? C3 C4 H42 107.3(15) . . ? C5 C4 H42 112.5(14) . . ? H41 C4 H42 107(2) . . ? C14 C5 C4 108.77(18) . . ? C14 C5 C1 111.23(17) . . ? C4 C5 C1 107.88(17) . . ? C14 C5 H51 111.1(14) . . ? C4 C5 H51 110.4(14) . . ? C1 C5 H51 107.4(14) . . ? N C6 C7 114.9(2) . . ? N C6 H72 107.9(14) . . ? C7 C6 H72 110.6(14) . . ? N C6 H71 105.6(17) . . ? C7 C6 H71 110.2(17) . . ? H72 C6 H71 107(2) . . ? C12 C7 C8 118.1(3) . . ? C12 C7 C6 123.3(2) . . ? C8 C7 C6 118.5(3) . . ? C7 C8 C9 120.6(4) . . ? C7 C8 H81 117(2) . . ? C9 C8 H81 122(2) . . ? C10 C9 C8 120.7(3) . . ? C10 C9 H91 123(2) . . ? C8 C9 H91 116(2) . . ? C9 C10 C11 119.1(3) . . ? C9 C10 H101 121(2) . . ? C11 C10 H101 120(2) . . ? C10 C11 C12 120.4(4) . . ? C10 C11 H111 119(2) . . ? C12 C11 H111 120(2) . . ? C7 C12 C11 121.0(3) . . ? C7 C12 H121 119(2) . . ? C11 C12 H121 120(2) . . ? C3 C13 H131 111.6(18) . . ? C3 C13 H132 110.0(18) . . ? H131 C13 H132 112(3) . . ? C3 C13 H133 108.9(17) . . ? H131 C13 H133 106(2) . . ? H132 C13 H133 108(2) . . ? C19 C14 C15 117.6(2) . . ? C19 C14 C5 121.8(2) . . ? C15 C14 C5 120.61(19) . . ? O2 C15 C16 116.1(2) . . ? O2 C15 C14 122.7(2) . . ? C16 C15 C14 121.2(2) . . ? C17 C16 C15 119.7(2) . . ? C17 C16 H161 121.4(16) . . ? C15 C16 H161 118.9(16) . . ? C16 C17 C18 120.1(3) . . ? C16 C17 H171 118.3(18) . . ? C18 C17 H171 121.5(18) . . ? C19 C18 C17 119.9(3) . . ? C19 C18 H181 118(2) . . ? C17 C18 H181 122.0(19) . . ? C18 C19 C14 121.5(2) . . ? C18 C19 H191 120.1(16) . . ? C14 C19 H191 118.4(15) . . ? C21 C20 O4 111.8(4) . . ? C21 C20 H201 109.3 . . ? O4 C20 H201 109.3 . . ? C21 C20 H202 109.3 . . ? O4 C20 H202 109.3 . . ? H201 C20 H202 107.9 . . ? O5 C22 C23 105.1(5) . . ? O5 C22 H221 110.7 . . ? C23 C22 H221 110.7 . . ? O5 C22 H222 110.7 . . ? C23 C22 H222 110.7 . . ? H221 C22 H222 108.8 . . ? O5 C22A C23A 114.4(13) . . ? O5 C22A H223 108.6 . . ? C23A C22A H223 108.6 . . ? O5 C22A H224 108.6 . . ? C23A C22A H224 108.7 . . ? H223 C22A H224 107.6 . . ? C22A C23A H234 109.5 . . ? C22A C23A H235 109.5 . . ? H234 C23A H235 109.5 . . ? C22A C23A H236 109.5 . . ? H234 C23A H236 109.5 . . ? H235 C23A H236 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 O3 P O4 C20 -20.8(4) . . . . ? O5 P O4 C20 -147.0(3) . . . . ? C1 P O4 C20 106.5(3) . . . . ? O3 P O5 C22A -13.2(9) . . . . ? O4 P O5 C22A 112.6(8) . . . . ? C1 P O5 C22A -137.0(8) . . . . ? O3 P O5 C22 -47.0(4) . . . . ? O4 P O5 C22 78.8(4) . . . . ? C1 P O5 C22 -170.8(4) . . . . ? O3 P C1 C2 53.3(2) . . . . ? O4 P C1 C2 -74.64(16) . . . . ? O5 P C1 C2 178.42(15) . . . . ? O3 P C1 C5 -71.3(2) . . . . ? O4 P C1 C5 160.72(15) . . . . ? O5 P C1 C5 53.78(18) . . . . ? C6 N C2 O1 6.5(3) . . . . ? C3 N C2 O1 175.1(2) . . . . ? C6 N C2 C1 -174.89(19) . . . . ? C3 N C2 C1 -6.3(3) . . . . ? C5 C1 C2 O1 -159.9(2) . . . . ? P C1 C2 O1 74.1(2) . . . . ? C5 C1 C2 N 21.5(3) . . . . ? P C1 C2 N -104.6(2) . . . . ? C15 O2 C3 N 76.1(2) . . . . ? C15 O2 C3 C4 -44.9(2) . . . . ? C15 O2 C3 C13 -164.7(2) . . . . ? C2 N C3 O2 -98.4(2) . . . . ? C6 N C3 O2 70.1(2) . . . . ? C2 N C3 C4 21.7(3) . . . . ? C6 N C3 C4 -169.76(19) . . . . ? C2 N C3 C13 146.4(2) . . . . ? C6 N C3 C13 -45.1(3) . . . . ? O2 C3 C4 C5 67.0(2) . . . . ? N C3 C4 C5 -52.0(2) . . . . ? C13 C3 C4 C5 -176.8(2) . . . . ? C3 C4 C5 C14 -52.3(2) . . . . ? C3 C4 C5 C1 68.4(2) . . . . ? C2 C1 C5 C14 67.2(2) . . . . ? P C1 C5 C14 -170.55(14) . . . . ? C2 C1 C5 C4 -52.0(2) . . . . ? P C1 C5 C4 70.2(2) . . . . ? C2 N C6 C7 -98.1(3) . . . . ? C3 N C6 C7 92.3(3) . . . . ? N C6 C7 C12 18.4(4) . . . . ? N C6 C7 C8 -162.4(3) . . . . ? C12 C7 C8 C9 -2.2(5) . . . . ? C6 C7 C8 C9 178.6(3) . . . . ? C7 C8 C9 C10 0.5(6) . . . . ? C8 C9 C10 C11 1.2(6) . . . . ? C9 C10 C11 C12 -1.3(5) . . . . ? C8 C7 C12 C11 2.1(4) . . . . ? C6 C7 C12 C11 -178.7(3) . . . . ? C10 C11 C12 C7 -0.4(5) . . . . ? C4 C5 C14 C19 -157.7(2) . . . . ? C1 C5 C14 C19 83.6(2) . . . . ? C4 C5 C14 C15 19.6(3) . . . . ? C1 C5 C14 C15 -99.1(2) . . . . ? C3 O2 C15 C16 -171.51(19) . . . . ? C3 O2 C15 C14 10.4(3) . . . . ? C19 C14 C15 O2 180.0(2) . . . . ? C5 C14 C15 O2 2.6(3) . . . . ? C19 C14 C15 C16 2.0(3) . . . . ? C5 C14 C15 C16 -175.4(2) . . . . ? O2 C15 C16 C17 -179.1(2) . . . . ? C14 C15 C16 C17 -1.0(4) . . . . ? C15 C16 C17 C18 -0.4(4) . . . . ? C16 C17 C18 C19 0.8(4) . . . . ? C17 C18 C19 C14 0.2(4) . . . . ? C15 C14 C19 C18 -1.6(4) . . . . ? C5 C14 C19 C18 175.8(2) . . . . ? P O4 C20 C21 175.5(3) . . . . ? C22A O5 C22 C23 33.8(11) . . . . ? P O5 C22 C23 174.0(6) . . . . ? C22 O5 C22A C23A -17.3(14) . . . . ? P O5 C22A C23A -76.7(17) . . . . ? _refine_special_details ; The C22 and C23 atoms of the diethoxy substitent is disordered over two partially occupied positions ; data_22 _database_code_depnum_ccdc_archive 'CCDC 912212' #TrackingRef 'depo_wolf.cif' _audit_update_record ; 2012-11-23 # Formatted by publCIF ; #==================================================== _chemical_name_systematic ; diethyl ((3aR*,9R*,9aR*,10R*)-12-benzyl-11-oxo-2,3,9,9a-tetrahydro-1H-3a,9- (epiminoethano)cyclopenta[b]chromen-10-yl)phosphonate ; _chemical_formula_moiety 'C25 H30 N O5 P' _chemical_formula_sum 'C25 H30 N O5 P' _chemical_formula_weight 455.47 _chemical_melting_point 378(1) _exptl_crystal_colour colourless _exptl_crystal_description prism _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_preparation ; slow evaporation from diethyl ether solution ; _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 1.361 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6578 _exptl_absorpt_correction_T_max 0.7536 _exptl_absorpt_process_details 'Bruker SADABS' _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 10.2612(1) _cell_length_b 11.1638(1) _cell_length_c 11.3877(1) _cell_angle_alpha 88.850(1) _cell_angle_beta 70.398(1) _cell_angle_gamma 70.439(1) _cell_volume 1151.71(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(1) _exptl_crystal_density_diffrn 1.313 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_ambient_temperature 293(2) _diffrn_reflns_number 24135 _reflns_number_total 4032 _reflns_number_gt 3997 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.14 _diffrn_reflns_theta_max 67.99 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 67.99 _diffrn_measured_fraction_theta_full 0.982 _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^)+(0.0566P)^2^+0.3979P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_number_reflns 4032 _refine_ls_number_parameters 292 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.1094 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.416 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.039 _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' 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 0.45508(4) 0.70940(4) 0.71706(4) 0.04135(15) Uani 1 1 d . . . O1 O -0.04771(11) 0.68613(11) 0.75890(10) 0.0453(3) Uani 1 1 d . . . O2 O 0.20659(13) 0.91677(11) 0.64113(11) 0.0516(3) Uani 1 1 d . . . O3 O 0.51747(13) 0.64104(13) 0.59157(12) 0.0579(3) Uani 1 1 d . . . O4 O 0.49619(13) 0.83169(12) 0.72614(12) 0.0543(3) Uani 1 1 d . . . O5 O 0.50255(12) 0.63211(12) 0.82144(12) 0.0523(3) Uani 1 1 d . . . N1 N 0.14772(14) 0.74224(13) 0.62331(12) 0.0432(3) Uani 1 1 d . . . C1 C 0.10817(16) 0.63650(16) 0.68122(15) 0.0437(4) Uani 1 1 d . . . C2 C 0.1216(2) 0.5263(2) 0.5961(2) 0.0669(6) Uani 1 1 d . . . H2A H 0.2087 0.5074 0.5212 0.080 Uiso 1 1 calc R . . H2B H 0.0352 0.5462 0.5718 0.080 Uiso 1 1 calc R . . C3 C 0.1338(3) 0.4137(2) 0.6763(2) 0.0827(8) Uani 1 1 d . . . H3A H 0.0465 0.3901 0.6962 0.099 Uiso 1 1 calc R . . H3B H 0.2195 0.3401 0.6314 0.099 Uiso 1 1 calc R . . C4 C 0.1482(2) 0.45776(17) 0.7962(2) 0.0603(5) Uani 1 1 d . . . H4A H 0.0541 0.4846 0.8647 0.072 Uiso 1 1 calc R . . H4B H 0.2198 0.3905 0.8207 0.072 Uiso 1 1 calc R . . C5 C 0.20103(17) 0.57051(15) 0.75833(16) 0.0456(4) Uani 1 1 d . . . H5 H 0.3046 0.5369 0.7030 0.055 Uiso 1 1 calc R . . C6 C -0.08206(16) 0.75019(14) 0.87350(14) 0.0399(3) Uani 1 1 d . . . C7 C -0.22973(18) 0.82304(17) 0.93477(17) 0.0509(4) Uani 1 1 d . . . H7 H -0.2990 0.8290 0.8972 0.061 Uiso 1 1 calc R . . C8 C -0.2728(2) 0.88654(18) 1.05192(18) 0.0597(5) Uani 1 1 d . . . H8 H -0.3714 0.9359 1.0929 0.072 Uiso 1 1 calc R . . C9 C -0.1709(2) 0.87718(19) 1.10828(17) 0.0614(5) Uani 1 1 d . . . H9 H -0.2005 0.9193 1.1875 0.074 Uiso 1 1 calc R . . C10 C -0.0241(2) 0.80489(18) 1.04651(16) 0.0523(4) Uani 1 1 d . . . H10 H 0.0443 0.7987 1.0851 0.063 Uiso 1 1 calc R . . C11 C 0.02323(17) 0.74104(15) 0.92766(14) 0.0405(3) Uani 1 1 d . . . C12 C 0.18506(17) 0.66908(15) 0.85557(15) 0.0408(3) Uani 1 1 d . . . H12 H 0.2358 0.6284 0.9128 0.049 Uiso 1 1 calc R . . C13 C 0.25405(16) 0.76510(14) 0.78482(14) 0.0375(3) Uani 1 1 d . . . H13 H 0.2237 0.8388 0.8456 0.045 Uiso 1 1 calc R . . C14 C 0.19874(15) 0.81547(15) 0.67834(14) 0.0391(3) Uani 1 1 d . . . C15 C 0.08394(18) 0.7988(2) 0.52890(16) 0.0534(4) Uani 1 1 d . . . H15A H 0.0218 0.8869 0.5596 0.064 Uiso 1 1 calc R . . H15B H 0.0209 0.7538 0.5204 0.064 Uiso 1 1 calc R . . C16 C 0.19373(18) 0.79648(16) 0.40039(15) 0.0444(4) Uani 1 1 d . . . C17 C 0.1387(2) 0.85841(18) 0.31125(17) 0.0522(4) Uani 1 1 d . . . H17 H 0.0372 0.8968 0.3314 0.063 Uiso 1 1 calc R . . C18 C 0.2325(3) 0.8638(2) 0.19284(19) 0.0645(5) Uani 1 1 d . . . H18 H 0.1942 0.9070 0.1344 0.077 Uiso 1 1 calc R . . C19 C 0.3807(3) 0.8060(3) 0.1620(2) 0.0802(7) Uani 1 1 d . . . H19 H 0.4441 0.8088 0.0822 0.096 Uiso 1 1 calc R . . C20 C 0.4364(2) 0.7437(3) 0.2488(2) 0.0875(8) Uani 1 1 d . . . H20 H 0.5379 0.7043 0.2272 0.105 Uiso 1 1 calc R . . C21 C 0.3441(2) 0.7382(2) 0.36827(18) 0.0646(5) Uani 1 1 d . . . H21 H 0.3834 0.6954 0.4263 0.077 Uiso 1 1 calc R . . C22 C 0.5419(2) 0.8995(2) 0.6179(2) 0.0667(6) Uani 1 1 d . . . H22A H 0.5357 0.8611 0.5452 0.080 Uiso 1 1 calc R . . H22B H 0.4765 0.9881 0.6340 0.080 Uiso 1 1 calc R . . C23 C 0.6922(3) 0.8935(3) 0.5931(3) 0.0905(8) Uani 1 1 d . . . H23A H 0.6977 0.9322 0.6650 0.136 Uiso 1 1 calc R . . H23B H 0.7216 0.9386 0.5220 0.136 Uiso 1 1 calc R . . H23C H 0.7567 0.8059 0.5759 0.136 Uiso 1 1 calc R . . C24 C 0.6620(2) 0.5638(2) 0.7902(2) 0.0666(5) Uani 1 1 d . . . H24A H 0.6961 0.4938 0.7257 0.080 Uiso 1 1 calc R . . H24B H 0.7154 0.6215 0.7584 0.080 Uiso 1 1 calc R . . C25 C 0.6900(2) 0.5144(3) 0.9021(2) 0.0770(7) Uani 1 1 d . . . H25A H 0.6529 0.5836 0.9667 0.116 Uiso 1 1 calc R . . H25B H 0.7943 0.4732 0.8828 0.116 Uiso 1 1 calc R . . H25C H 0.6414 0.4538 0.9306 0.116 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 0.0298(2) 0.0546(3) 0.0425(2) 0.00839(17) -0.01300(17) -0.01801(17) O1 0.0278(5) 0.0617(7) 0.0441(6) -0.0068(5) -0.0077(5) -0.0169(5) O2 0.0479(7) 0.0518(7) 0.0568(7) 0.0162(5) -0.0204(6) -0.0180(5) O3 0.0376(6) 0.0783(8) 0.0502(7) -0.0044(6) -0.0110(5) -0.0147(6) O4 0.0492(7) 0.0695(8) 0.0550(7) 0.0152(6) -0.0161(6) -0.0368(6) O5 0.0347(6) 0.0693(8) 0.0563(7) 0.0199(6) -0.0193(5) -0.0199(5) N1 0.0321(6) 0.0606(8) 0.0379(7) 0.0042(6) -0.0120(5) -0.0176(6) C1 0.0289(7) 0.0542(9) 0.0432(8) -0.0067(7) -0.0044(6) -0.0161(6) C2 0.0506(10) 0.0806(13) 0.0630(12) -0.0280(10) -0.0057(9) -0.0269(10) C3 0.0743(14) 0.0638(13) 0.0967(17) -0.0246(12) 0.0000(13) -0.0356(11) C4 0.0436(9) 0.0445(9) 0.0857(14) 0.0033(9) -0.0111(9) -0.0178(7) C5 0.0294(7) 0.0443(8) 0.0572(10) 0.0008(7) -0.0080(7) -0.0124(6) C6 0.0333(7) 0.0432(8) 0.0406(8) 0.0017(6) -0.0065(6) -0.0164(6) C7 0.0345(8) 0.0553(9) 0.0546(10) 0.0022(8) -0.0060(7) -0.0147(7) C8 0.0466(10) 0.0545(10) 0.0567(11) -0.0049(8) 0.0064(9) -0.0151(8) C9 0.0693(13) 0.0627(11) 0.0437(9) -0.0073(8) 0.0031(9) -0.0347(10) C10 0.0588(10) 0.0663(11) 0.0408(8) 0.0070(7) -0.0129(8) -0.0372(9) C11 0.0380(8) 0.0460(8) 0.0389(8) 0.0063(6) -0.0082(6) -0.0216(6) C12 0.0338(7) 0.0488(8) 0.0444(8) 0.0122(6) -0.0156(7) -0.0184(6) C13 0.0302(7) 0.0461(8) 0.0384(7) 0.0053(6) -0.0115(6) -0.0165(6) C14 0.0263(7) 0.0469(8) 0.0394(8) 0.0047(6) -0.0081(6) -0.0104(6) C15 0.0331(8) 0.0802(12) 0.0432(9) 0.0032(8) -0.0152(7) -0.0133(8) C16 0.0381(8) 0.0530(9) 0.0422(8) 0.0009(7) -0.0150(7) -0.0148(7) C17 0.0490(9) 0.0596(10) 0.0556(10) 0.0079(8) -0.0267(8) -0.0201(8) C18 0.0785(14) 0.0831(13) 0.0542(11) 0.0239(10) -0.0349(11) -0.0447(11) C19 0.0700(14) 0.127(2) 0.0484(11) 0.0199(12) -0.0124(10) -0.0489(14) C20 0.0424(11) 0.138(2) 0.0601(13) 0.0153(13) -0.0046(10) -0.0177(12) C21 0.0396(9) 0.0925(14) 0.0485(10) 0.0117(9) -0.0135(8) -0.0090(9) C22 0.0562(11) 0.0788(13) 0.0741(13) 0.0341(11) -0.0231(10) -0.0358(10) C23 0.0699(15) 0.129(2) 0.0983(18) 0.0485(16) -0.0306(14) -0.0669(15) C24 0.0395(9) 0.0904(15) 0.0677(12) 0.0192(11) -0.0223(9) -0.0171(9) C25 0.0515(11) 0.0985(16) 0.0859(15) 0.0376(13) -0.0335(11) -0.0241(11) _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 O3 1.4618(13) . ? P1 O5 1.5687(12) . ? P1 O4 1.5726(12) . ? P1 C13 1.8246(15) . ? O1 C6 1.3780(18) . ? O1 C1 1.4577(17) . ? O2 C14 1.2181(19) . ? O4 C22 1.458(2) . ? O5 C24 1.473(2) . ? N1 C14 1.365(2) . ? N1 C1 1.450(2) . ? N1 C15 1.467(2) . ? C1 C5 1.512(2) . ? C1 C2 1.522(2) . ? C2 C3 1.534(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.531(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.530(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C12 1.507(2) . ? C5 H5 0.9800 . ? C6 C11 1.389(2) . ? C6 C7 1.390(2) . ? C7 C8 1.382(3) . ? C7 H7 0.9300 . ? C8 C9 1.375(3) . ? C8 H8 0.9300 . ? C9 C10 1.383(3) . ? C9 H9 0.9300 . ? C10 C11 1.393(2) . ? C10 H10 0.9300 . ? C11 C12 1.515(2) . ? C12 C13 1.546(2) . ? C12 H12 0.9800 . ? C13 C14 1.526(2) . ? C13 H13 0.9800 . ? C15 C16 1.512(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C21 1.377(2) . ? C16 C17 1.387(2) . ? C17 C18 1.383(3) . ? C17 H17 0.9300 . ? C18 C19 1.359(3) . ? C18 H18 0.9300 . ? C19 C20 1.368(3) . ? C19 H19 0.9300 . ? C20 C21 1.387(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.450(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.457(3) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 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 O3 P1 O5 116.12(8) . . ? O3 P1 O4 114.56(7) . . ? O5 P1 O4 102.47(7) . . ? O3 P1 C13 114.65(7) . . ? O5 P1 C13 102.55(6) . . ? O4 P1 C13 104.87(7) . . ? C6 O1 C1 116.25(11) . . ? C22 O4 P1 122.59(13) . . ? C24 O5 P1 116.14(11) . . ? C14 N1 C1 122.24(13) . . ? C14 N1 C15 116.89(14) . . ? C1 N1 C15 117.44(13) . . ? N1 C1 O1 107.83(12) . . ? N1 C1 C5 112.70(13) . . ? O1 C1 C5 110.61(13) . . ? N1 C1 C2 118.08(15) . . ? O1 C1 C2 104.25(13) . . ? C5 C1 C2 102.98(15) . . ? C1 C2 C3 104.22(17) . . ? C1 C2 H2A 110.9 . . ? C3 C2 H2A 110.9 . . ? C1 C2 H2B 110.9 . . ? C3 C2 H2B 110.9 . . ? H2A C2 H2B 108.9 . . ? C4 C3 C2 106.88(16) . . ? C4 C3 H3A 110.3 . . ? C2 C3 H3A 110.3 . . ? C4 C3 H3B 110.3 . . ? C2 C3 H3B 110.3 . . ? H3A C3 H3B 108.6 . . ? C5 C4 C3 102.81(17) . . ? C5 C4 H4A 111.2 . . ? C3 C4 H4A 111.2 . . ? C5 C4 H4B 111.2 . . ? C3 C4 H4B 111.2 . . ? H4A C4 H4B 109.1 . . ? C12 C5 C1 108.05(13) . . ? C12 C5 C4 121.14(15) . . ? C1 C5 C4 101.76(14) . . ? C12 C5 H5 108.4 . . ? C1 C5 H5 108.4 . . ? C4 C5 H5 108.4 . . ? O1 C6 C11 122.49(13) . . ? O1 C6 C7 116.44(15) . . ? C11 C6 C7 121.05(15) . . ? C8 C7 C6 119.55(18) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C9 C8 C7 120.42(17) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 119.66(17) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C9 C10 C11 121.35(18) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C6 C11 C10 117.96(15) . . ? C6 C11 C12 120.26(14) . . ? C10 C11 C12 121.71(15) . . ? C5 C12 C11 110.07(13) . . ? C5 C12 C13 107.14(13) . . ? C11 C12 C13 108.23(12) . . ? C5 C12 H12 110.4 . . ? C11 C12 H12 110.4 . . ? C13 C12 H12 110.4 . . ? C14 C13 C12 113.42(12) . . ? C14 C13 P1 105.92(10) . . ? C12 C13 P1 116.55(10) . . ? C14 C13 H13 106.8 . . ? C12 C13 H13 106.8 . . ? P1 C13 H13 106.8 . . ? O2 C14 N1 121.61(14) . . ? O2 C14 C13 119.65(14) . . ? N1 C14 C13 118.67(13) . . ? N1 C15 C16 115.66(13) . . ? N1 C15 H15A 108.4 . . ? C16 C15 H15A 108.4 . . ? N1 C15 H15B 108.4 . . ? C16 C15 H15B 108.4 . . ? H15A C15 H15B 107.4 . . ? C21 C16 C17 118.74(16) . . ? C21 C16 C15 123.69(16) . . ? C17 C16 C15 117.57(15) . . ? C18 C17 C16 120.93(18) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C19 C18 C17 119.91(19) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 119.72(19) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C19 C20 C21 121.2(2) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C16 C21 C20 119.53(19) . . ? C16 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C23 C22 O4 109.78(18) . . ? C23 C22 H22A 109.7 . . ? O4 C22 H22A 109.7 . . ? C23 C22 H22B 109.7 . . ? O4 C22 H22B 109.7 . . ? H22A C22 H22B 108.2 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 O5 109.39(17) . . ? C25 C24 H24A 109.8 . . ? O5 C24 H24A 109.8 . . ? C25 C24 H24B 109.8 . . ? O5 C24 H24B 109.8 . . ? H24A C24 H24B 108.2 . . ? 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 . . ? 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 O3 P1 O4 C22 22.30(16) . . . . ? O5 P1 O4 C22 148.93(14) . . . . ? C13 P1 O4 C22 -104.27(14) . . . . ? O3 P1 O5 C24 48.95(16) . . . . ? O4 P1 O5 C24 -76.67(15) . . . . ? C13 P1 O5 C24 174.76(14) . . . . ? C14 N1 C1 O1 90.18(16) . . . . ? C15 N1 C1 O1 -68.24(16) . . . . ? C14 N1 C1 C5 -32.18(19) . . . . ? C15 N1 C1 C5 169.40(13) . . . . ? C14 N1 C1 C2 -152.12(15) . . . . ? C15 N1 C1 C2 49.5(2) . . . . ? C6 O1 C1 N1 -78.30(16) . . . . ? C6 O1 C1 C5 45.35(17) . . . . ? C6 O1 C1 C2 155.41(15) . . . . ? N1 C1 C2 C3 158.01(16) . . . . ? O1 C1 C2 C3 -82.41(18) . . . . ? C5 C1 C2 C3 33.13(18) . . . . ? C1 C2 C3 C4 -7.6(2) . . . . ? C2 C3 C4 C5 -20.4(2) . . . . ? N1 C1 C5 C12 56.90(16) . . . . ? O1 C1 C5 C12 -63.89(16) . . . . ? C2 C1 C5 C12 -174.78(13) . . . . ? N1 C1 C5 C4 -174.54(13) . . . . ? O1 C1 C5 C4 64.67(16) . . . . ? C2 C1 C5 C4 -46.22(16) . . . . ? C3 C4 C5 C12 160.51(16) . . . . ? C3 C4 C5 C1 40.80(17) . . . . ? C1 O1 C6 C11 -16.2(2) . . . . ? C1 O1 C6 C7 165.28(14) . . . . ? O1 C6 C7 C8 177.93(15) . . . . ? C11 C6 C7 C8 -0.6(2) . . . . ? C6 C7 C8 C9 -0.5(3) . . . . ? C7 C8 C9 C10 0.7(3) . . . . ? C8 C9 C10 C11 0.1(3) . . . . ? O1 C6 C11 C10 -177.04(14) . . . . ? C7 C6 C11 C10 1.4(2) . . . . ? O1 C6 C11 C12 6.0(2) . . . . ? C7 C6 C11 C12 -175.57(14) . . . . ? C9 C10 C11 C6 -1.1(2) . . . . ? C9 C10 C11 C12 175.76(15) . . . . ? C1 C5 C12 C11 52.14(16) . . . . ? C4 C5 C12 C11 -64.43(19) . . . . ? C1 C5 C12 C13 -65.32(15) . . . . ? C4 C5 C12 C13 178.10(14) . . . . ? C6 C11 C12 C5 -25.07(19) . . . . ? C10 C11 C12 C5 158.11(15) . . . . ? C6 C11 C12 C13 91.72(16) . . . . ? C10 C11 C12 C13 -85.10(18) . . . . ? C5 C12 C13 C14 49.90(16) . . . . ? C11 C12 C13 C14 -68.76(16) . . . . ? C5 C12 C13 P1 -73.51(14) . . . . ? C11 C12 C13 P1 167.83(11) . . . . ? O3 P1 C13 C14 -40.84(13) . . . . ? O5 P1 C13 C14 -167.59(10) . . . . ? O4 P1 C13 C14 85.67(11) . . . . ? O3 P1 C13 C12 86.36(13) . . . . ? O5 P1 C13 C12 -40.39(13) . . . . ? O4 P1 C13 C12 -147.13(11) . . . . ? C1 N1 C14 O2 -166.67(14) . . . . ? C15 N1 C14 O2 -8.1(2) . . . . ? C1 N1 C14 C13 16.4(2) . . . . ? C15 N1 C14 C13 174.91(12) . . . . ? C12 C13 C14 O2 157.51(14) . . . . ? P1 C13 C14 O2 -73.43(15) . . . . ? C12 C13 C14 N1 -25.48(18) . . . . ? P1 C13 C14 N1 103.58(13) . . . . ? C14 N1 C15 C16 79.05(19) . . . . ? C1 N1 C15 C16 -121.37(16) . . . . ? N1 C15 C16 C21 4.4(3) . . . . ? N1 C15 C16 C17 -174.70(15) . . . . ? C21 C16 C17 C18 -1.1(3) . . . . ? C15 C16 C17 C18 177.98(18) . . . . ? C16 C17 C18 C19 1.2(3) . . . . ? C17 C18 C19 C20 -0.6(4) . . . . ? C18 C19 C20 C21 0.0(4) . . . . ? C17 C16 C21 C20 0.6(3) . . . . ? C15 C16 C21 C20 -178.5(2) . . . . ? C19 C20 C21 C16 0.0(4) . . . . ? P1 O4 C22 C23 -116.8(2) . . . . ? P1 O5 C24 C25 170.98(16) . . . . ? data_23 _database_code_depnum_ccdc_archive 'CCDC 912213' #==================================================== _chemical_name_systematic ; diethyl ((4aR*,9R*,9aR*,11R*)-13-benzyl-12-oxo-1,2,3,4,9,9a-hexahydro-4a,9- (epiminoethano)xanthen-11-yl)phosphonate ; _chemical_formula_moiety 'C26 H32 N O5 P' _chemical_formula_sum 'C26 H32 N O5 P' _chemical_formula_weight 469.50 _chemical_melting_point 412(1) _exptl_crystal_colour colourless _exptl_crystal_description prism _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_preparation ; slow evaporation from diethyl ether solution ; _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 1.330 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6511 _exptl_absorpt_correction_T_max 0.7662 _exptl_absorpt_process_details 'Bruker SADABS' _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 10.3639(19) _cell_length_b 11.350(2) _cell_length_c 11.563(2) _cell_angle_alpha 87.909(5) _cell_angle_beta 70.260(5) _cell_angle_gamma 69.399(5) _cell_volume 1193.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 291(1) _exptl_crystal_density_diffrn 1.307 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_ambient_temperature 291(2) _diffrn_reflns_number 23765 _reflns_number_total 4157 _reflns_number_gt 4022 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.08 _diffrn_reflns_theta_max 67.95 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 67.95 _diffrn_measured_fraction_theta_full 0.976 _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^)+(0.1176P)^2^+0.4182P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_number_reflns 4157 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0604 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1755 _refine_ls_wR_factor_gt 0.1745 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.567 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.074 _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' 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 0.04545(4) 0.77650(4) 0.78443(4) 0.0443(3) Uani 1 1 d . . . O1 O 0.53795(12) 0.75683(11) 0.80704(11) 0.0444(4) Uani 1 1 d . . . O2 O 0.28745(16) 0.84792(13) 0.57057(12) 0.0541(4) Uani 1 1 d . . . O3 O -0.01476(16) 0.90333(14) 0.84866(15) 0.0613(5) Uani 1 1 d . . . O4 O 0.00131(15) 0.67232(14) 0.86376(14) 0.0555(4) Uani 1 1 d . . . O5 O -0.00171(17) 0.76782(14) 0.67017(15) 0.0603(4) Uani 1 1 d . . . N1 N 0.34707(15) 0.87397(13) 0.73660(13) 0.0408(4) Uani 1 1 d . . . C1 C 0.38084(18) 0.82974(15) 0.84750(16) 0.0412(4) Uani 1 1 d . . . C2 C 0.29518(17) 0.74679(15) 0.91342(15) 0.0398(4) Uani 1 1 d . . . H2 H 0.1903 0.7991 0.9440 0.048 Uiso 1 1 calc R . . C3 C 0.3397(2) 0.69660(18) 1.02403(17) 0.0502(5) Uani 1 1 d . . . H3A H 0.2845 0.6444 1.0654 0.060 Uiso 1 1 calc R . . H3B H 0.4434 0.6444 0.9956 0.060 Uiso 1 1 calc R . . C4 C 0.3107(3) 0.8053(2) 1.11498(19) 0.0606(6) Uani 1 1 d . . . H4A H 0.2058 0.8528 1.1495 0.073 Uiso 1 1 calc R . . H4B H 0.3445 0.7715 1.1821 0.073 Uiso 1 1 calc R . . C5 C 0.3898(2) 0.8923(2) 1.0505(2) 0.0583(5) Uani 1 1 d . . . H5A H 0.4951 0.8476 1.0267 0.070 Uiso 1 1 calc R . . H5B H 0.3629 0.9646 1.1076 0.070 Uiso 1 1 calc R . . C6 C 0.3527(2) 0.93856(17) 0.93647(18) 0.0486(5) Uani 1 1 d . . . H6A H 0.2501 0.9932 0.9614 0.058 Uiso 1 1 calc R . . H6B H 0.4116 0.9879 0.8948 0.058 Uiso 1 1 calc R . . C7 C 0.58137(19) 0.64176(16) 0.74396(15) 0.0422(4) Uani 1 1 d . . . C8 C 0.7310(2) 0.58502(19) 0.67530(18) 0.0518(5) Uani 1 1 d . . . H8 H 0.7955 0.6257 0.6733 0.062 Uiso 1 1 calc R . . C9 C 0.7830(2) 0.4676(2) 0.61008(19) 0.0602(6) Uani 1 1 d . . . H9 H 0.8823 0.4304 0.5631 0.072 Uiso 1 1 calc R . . C10 C 0.6889(2) 0.40619(19) 0.6145(2) 0.0586(6) Uani 1 1 d . . . H10 H 0.7246 0.3269 0.5719 0.070 Uiso 1 1 calc R . . C11 C 0.5406(2) 0.46275(18) 0.68265(19) 0.0519(5) Uani 1 1 d . . . H11 H 0.4775 0.4207 0.6849 0.062 Uiso 1 1 calc R . . C12 C 0.48410(19) 0.58096(16) 0.74781(16) 0.0423(4) Uani 1 1 d . . . C13 C 0.32027(18) 0.64514(15) 0.81776(15) 0.0397(4) Uani 1 1 d . . . H13 H 0.2787 0.5827 0.8580 0.048 Uiso 1 1 calc R . . C14 C 0.24581(18) 0.70853(15) 0.72560(16) 0.0399(4) Uani 1 1 d . . . H14 H 0.2754 0.6444 0.6578 0.048 Uiso 1 1 calc R . . C15 C 0.29589(18) 0.81538(16) 0.67053(15) 0.0408(4) Uani 1 1 d . . . C16 C 0.40935(19) 0.96681(16) 0.67256(16) 0.0460(5) Uani 1 1 d . . . H16A H 0.4525 0.9401 0.5849 0.055 Uiso 1 1 calc R . . H16B H 0.4880 0.9658 0.7006 0.055 Uiso 1 1 calc R . . C17 C 0.30120(19) 1.10122(16) 0.69113(15) 0.0427(4) Uani 1 1 d . . . C18 C 0.1499(2) 1.13412(19) 0.7406(2) 0.0592(6) Uani 1 1 d . . . H18 H 0.1100 1.0729 0.7714 0.071 Uiso 1 1 calc R . . C19 C 0.0583(3) 1.2578(2) 0.7442(3) 0.0742(7) Uani 1 1 d . . . H19 H -0.0430 1.2786 0.7768 0.089 Uiso 1 1 calc R . . C20 C 0.1136(3) 1.3500(2) 0.7008(3) 0.0733(7) Uani 1 1 d . . . H20 H 0.0508 1.4332 0.7056 0.088 Uiso 1 1 calc R . . C21 C 0.2640(3) 1.3183(2) 0.6496(2) 0.0652(6) Uani 1 1 d . . . H21 H 0.3029 1.3795 0.6168 0.078 Uiso 1 1 calc R . . C22 C 0.3562(2) 1.19592(18) 0.64722(19) 0.0511(5) Uani 1 1 d . . . H22 H 0.4574 1.1762 0.6156 0.061 Uiso 1 1 calc R . . C23 C -0.1535(3) 0.7094(3) 0.9430(3) 0.0864(9) Uani 1 1 d . . . H23A H -0.1718 0.7636 1.0142 0.104 Uiso 1 1 calc R . . H23B H -0.2153 0.7574 0.8977 0.104 Uiso 1 1 calc R . . C24 C -0.1917(3) 0.6017(3) 0.9838(3) 0.0837(8) Uani 1 1 d . . . H24A H -0.2934 0.6292 1.0352 0.126 Uiso 1 1 calc R . . H24B H -0.1320 0.5550 1.0300 0.126 Uiso 1 1 calc R . . H24C H -0.1752 0.5486 0.9135 0.126 Uiso 1 1 calc R . . C25 C -0.0454(3) 0.8765(3) 0.6018(3) 0.0744(7) Uani 1 1 d . . . H25A H -0.0452 0.9506 0.6410 0.089 Uiso 1 1 calc R . . H25B H 0.0251 0.8608 0.5183 0.089 Uiso 1 1 calc R . . C26 C -0.1902(3) 0.9004(3) 0.5977(3) 0.0890(9) Uani 1 1 d . . . H26A H -0.2593 0.9124 0.6803 0.134 Uiso 1 1 calc R . . H26B H -0.1886 0.8296 0.5535 0.134 Uiso 1 1 calc R . . H26C H -0.2190 0.9750 0.5566 0.134 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 0.0303(4) 0.0379(4) 0.0620(4) 0.0067(3) -0.0146(3) -0.0108(3) O1 0.0280(7) 0.0401(7) 0.0592(7) -0.0011(5) -0.0104(5) -0.0093(5) O2 0.0528(8) 0.0572(8) 0.0521(7) 0.0135(6) -0.0184(6) -0.0204(7) O3 0.0382(8) 0.0451(8) 0.0861(10) -0.0035(7) -0.0095(7) -0.0088(6) O4 0.0365(8) 0.0517(8) 0.0752(9) 0.0173(6) -0.0147(6) -0.0179(6) O5 0.0540(9) 0.0547(8) 0.0807(10) 0.0149(7) -0.0373(7) -0.0169(7) N1 0.0321(8) 0.0337(7) 0.0507(8) 0.0042(6) -0.0074(6) -0.0116(6) C1 0.0285(8) 0.0375(9) 0.0509(9) -0.0003(7) -0.0084(6) -0.0088(7) C2 0.0291(8) 0.0366(9) 0.0492(9) 0.0035(7) -0.0093(7) -0.0108(7) C3 0.0461(10) 0.0475(10) 0.0519(10) 0.0072(7) -0.0138(7) -0.0143(8) C4 0.0624(13) 0.0653(13) 0.0508(10) 0.0032(9) -0.0205(9) -0.0181(10) C5 0.0540(12) 0.0562(12) 0.0638(12) -0.0082(9) -0.0203(9) -0.0176(9) C6 0.0408(10) 0.0402(9) 0.0602(11) -0.0047(7) -0.0112(7) -0.0143(7) C7 0.0352(9) 0.0387(9) 0.0480(9) 0.0024(7) -0.0132(7) -0.0089(7) C8 0.0353(10) 0.0494(11) 0.0589(10) 0.0033(8) -0.0100(7) -0.0077(8) C9 0.0421(10) 0.0552(12) 0.0577(11) -0.0028(9) -0.0084(8) 0.0044(9) C10 0.0575(12) 0.0413(10) 0.0618(11) -0.0086(8) -0.0229(9) 0.0034(9) C11 0.0502(11) 0.0374(9) 0.0650(11) -0.0014(8) -0.0254(9) -0.0063(8) C12 0.0348(9) 0.0350(9) 0.0519(9) 0.0043(7) -0.0160(7) -0.0058(7) C13 0.0342(9) 0.0329(8) 0.0503(9) 0.0057(6) -0.0134(7) -0.0117(6) C14 0.0322(8) 0.0334(8) 0.0506(9) 0.0019(6) -0.0145(6) -0.0077(6) C15 0.0290(8) 0.0366(9) 0.0487(9) 0.0039(7) -0.0092(6) -0.0066(7) C16 0.0347(9) 0.0386(9) 0.0551(10) 0.0062(7) -0.0044(7) -0.0130(7) C17 0.0397(9) 0.0387(9) 0.0466(9) 0.0038(7) -0.0108(7) -0.0146(7) C18 0.0386(10) 0.0445(10) 0.0836(14) 0.0095(9) -0.0083(9) -0.0149(8) C19 0.0450(11) 0.0490(12) 0.1106(19) 0.0058(11) -0.0146(11) -0.0077(9) C20 0.0629(15) 0.0421(11) 0.114(2) 0.0084(11) -0.0391(13) -0.0105(10) C21 0.0706(15) 0.0461(11) 0.0945(16) 0.0178(10) -0.0379(12) -0.0316(10) C22 0.0471(10) 0.0459(10) 0.0665(11) 0.0086(8) -0.0193(8) -0.0245(8) C23 0.0505(14) 0.0714(17) 0.113(2) 0.0177(14) 0.0004(13) -0.0225(12) C24 0.0552(14) 0.0845(18) 0.1020(19) 0.0277(14) -0.0119(12) -0.0307(13) C25 0.0641(15) 0.0798(17) 0.0914(17) 0.0364(13) -0.0413(13) -0.0292(12) C26 0.0669(17) 0.101(2) 0.110(2) 0.0376(17) -0.0493(15) -0.0277(15) _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 O3 1.4649(15) . ? P1 O4 1.5707(14) . ? P1 O5 1.5728(15) . ? P1 C14 1.8239(17) . ? O1 C7 1.369(2) . ? O1 C1 1.4562(18) . ? O2 C15 1.222(2) . ? O4 C23 1.466(3) . ? O5 C25 1.459(3) . ? N1 C15 1.366(2) . ? N1 C1 1.467(2) . ? N1 C16 1.474(2) . ? C1 C6 1.518(2) . ? C1 C2 1.528(2) . ? C2 C13 1.520(2) . ? C2 C3 1.528(2) . ? C2 H2 0.9800 . ? C3 C4 1.529(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.520(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.520(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.398(2) . ? C7 C12 1.397(3) . ? C8 C9 1.389(3) . ? C8 H8 0.9300 . ? C9 C10 1.372(3) . ? C9 H9 0.9300 . ? C10 C11 1.386(3) . ? C10 H10 0.9300 . ? C11 C12 1.391(3) . ? C11 H11 0.9300 . ? C12 C13 1.521(2) . ? C13 C14 1.535(2) . ? C13 H13 0.9800 . ? C14 C15 1.520(2) . ? C14 H14 0.9800 . ? C16 C17 1.513(2) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C22 1.391(2) . ? C17 C18 1.387(3) . ? C18 C19 1.384(3) . ? C18 H18 0.9300 . ? C19 C20 1.366(4) . ? C19 H19 0.9300 . ? C20 C21 1.380(4) . ? C20 H20 0.9300 . ? C21 C22 1.376(3) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.431(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.446(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 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 O3 P1 O4 115.74(9) . . ? O3 P1 O5 114.63(9) . . ? O4 P1 O5 102.77(8) . . ? O3 P1 C14 113.91(8) . . ? O4 P1 C14 103.10(7) . . ? O5 P1 C14 105.25(8) . . ? C7 O1 C1 115.16(12) . . ? C23 O4 P1 116.06(15) . . ? C25 O5 P1 122.21(16) . . ? C15 N1 C1 125.26(14) . . ? C15 N1 C16 115.60(14) . . ? C1 N1 C16 117.01(14) . . ? O1 C1 N1 106.75(12) . . ? O1 C1 C6 106.44(13) . . ? N1 C1 C6 112.02(14) . . ? O1 C1 C2 109.74(13) . . ? N1 C1 C2 111.68(14) . . ? C6 C1 C2 110.00(14) . . ? C13 C2 C1 107.31(13) . . ? C13 C2 C3 114.64(14) . . ? C1 C2 C3 110.09(14) . . ? C13 C2 H2 108.2 . . ? C1 C2 H2 108.2 . . ? C3 C2 H2 108.2 . . ? C4 C3 C2 110.91(16) . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 110.41(16) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C6 112.22(16) . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5B 109.1 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C1 C6 C5 111.89(16) . . ? C1 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? C1 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? O1 C7 C8 116.56(16) . . ? O1 C7 C12 122.96(15) . . ? C8 C7 C12 120.47(16) . . ? C9 C8 C7 119.65(19) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C10 C9 C8 120.43(17) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 119.75(17) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 121.50(19) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.3 . . ? C11 C12 C7 118.19(16) . . ? C11 C12 C13 121.26(16) . . ? C7 C12 C13 120.52(15) . . ? C2 C13 C12 109.69(13) . . ? C2 C13 C14 108.43(13) . . ? C12 C13 C14 108.42(13) . . ? C2 C13 H13 110.1 . . ? C12 C13 H13 110.1 . . ? C14 C13 H13 110.1 . . ? C15 C14 C13 111.84(14) . . ? C15 C14 P1 105.54(11) . . ? C13 C14 P1 116.63(12) . . ? C15 C14 H14 107.5 . . ? C13 C14 H14 107.5 . . ? P1 C14 H14 107.5 . . ? O2 C15 N1 121.91(16) . . ? O2 C15 C14 119.87(16) . . ? N1 C15 C14 118.21(14) . . ? N1 C16 C17 115.21(13) . . ? N1 C16 H16A 108.5 . . ? C17 C16 H16A 108.5 . . ? N1 C16 H16B 108.5 . . ? C17 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C22 C17 C18 118.04(17) . . ? C22 C17 C16 118.00(16) . . ? C18 C17 C16 123.76(16) . . ? C19 C18 C17 120.09(19) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 121.3(2) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C19 C20 C21 119.2(2) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? C20 C21 C22 119.95(19) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C21 C22 C17 121.35(19) . . ? C21 C22 H22 119.3 . . ? C17 C22 H22 119.3 . . ? C24 C23 O4 111.6(2) . . ? C24 C23 H23A 109.3 . . ? O4 C23 H23A 109.3 . . ? C24 C23 H23B 109.3 . . ? O4 C23 H23B 109.3 . . ? H23A C23 H23B 108.0 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 O5 110.9(2) . . ? C26 C25 H25A 109.4 . . ? O5 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? O5 C25 H25B 109.4 . . ? H25A C25 H25B 108.0 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? data_26 _database_code_depnum_ccdc_archive 'CCDC 912214' #==================================================== _chemical_name_systematic ; diethyl[(3R*,4R*,4aR*))-1-benzyl-4-(2-hydroxyphenyl)-2-oxo-1,2,3,4,4a,5,6,7- octahydroquinolin-3-yl]phosphonate ; _chemical_formula_moiety 'C26 H32 N O5 P' _chemical_formula_sum 'C26 H32 N O5 P' _chemical_formula_weight 469.50 _chemical_melting_point 469(1) _exptl_crystal_colour colourless _exptl_crystal_description prism _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_preparation ; slow evaporation from diethyl ether solution ; _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 1.342 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.648 _exptl_absorpt_correction_T_max 0.874 _exptl_absorpt_process_details 'Bruker SADABS' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.4626(1) _cell_length_b 8.2350(1) _cell_length_c 12.6582(1) _cell_angle_alpha 90.00 _cell_angle_beta 114.56(1) _cell_angle_gamma 90.00 _cell_volume 1181.57(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _exptl_crystal_density_diffrn 1.320 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_ambient_temperature 100(2) _diffrn_reflns_number 12993 _reflns_number_total 2299 _reflns_number_gt 2299 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.84 _diffrn_reflns_theta_max 67.97 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 67.97 _diffrn_measured_fraction_theta_full 0.998 _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^)+(0.0720P)^2^+1.0945P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_number_reflns 2299 _refine_ls_number_parameters 305 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1182 _refine_ls_wR_factor_gt 0.1182 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.11(3) _chemical_absolute_configuration unk _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.471 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.058 _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' 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 0.26415(7) 0.24292(10) 0.09476(7) 0.0174(2) Uani 1 1 d . . . O1 O -0.0387(2) 0.0807(4) 0.0921(2) 0.0219(6) Uani 1 1 d . . . H1 H -0.086(5) 0.003(9) 0.055(5) 0.059(19) Uiso 1 1 d . . . O2 O 0.36610(19) 0.0632(3) 0.3474(2) 0.0185(5) Uani 1 1 d . . . O3 O 0.1732(2) 0.3161(4) -0.0121(2) 0.0292(6) Uani 1 1 d . . . O4 O 0.3751(2) 0.3546(4) 0.1495(3) 0.0383(8) Uani 1 1 d . . . O5 O 0.3150(2) 0.0778(3) 0.0751(2) 0.0196(5) Uani 1 1 d . . . N1 N 0.3303(2) 0.3138(4) 0.4006(2) 0.0147(6) Uani 1 1 d . . . C1 C 0.2713(3) 0.4673(4) 0.3755(3) 0.0148(7) Uani 1 1 d . . . C2 C 0.2996(3) 0.5847(5) 0.4547(3) 0.0187(7) Uani 1 1 d . . . H2 H 0.3593 0.5627 0.5299 0.022 Uiso 1 1 calc R . . C3 C 0.2433(3) 0.7495(5) 0.4327(3) 0.0228(7) Uani 1 1 d . . . H3A H 0.3059 0.8332 0.4618 0.027 Uiso 1 1 calc R . . H3B H 0.1943 0.7600 0.4770 0.027 Uiso 1 1 calc R . . C4 C 0.1664(3) 0.7812(5) 0.3044(3) 0.0264(8) Uani 1 1 d . . . H4A H 0.1125 0.8731 0.2970 0.032 Uiso 1 1 calc R . . H4B H 0.2171 0.8118 0.2647 0.032 Uiso 1 1 calc R . . C5 C 0.0945(3) 0.6317(5) 0.2463(3) 0.0252(8) Uani 1 1 d . . . H5A H 0.0433 0.6562 0.1640 0.030 Uiso 1 1 calc R . . H5B H 0.0433 0.6011 0.2855 0.030 Uiso 1 1 calc R . . C6 C 0.1769(3) 0.4906(4) 0.2529(3) 0.0174(7) Uani 1 1 d . . . H6 H 0.2194 0.5231 0.2044 0.021 Uiso 1 1 calc R . . C7 C 0.1129(3) 0.3311(4) 0.2007(3) 0.0156(7) Uani 1 1 d . . . H7 H 0.0607 0.3525 0.1172 0.019 Uiso 1 1 calc R . . C8 C 0.0367(3) 0.2558(5) 0.2554(3) 0.0150(6) Uani 1 1 d . . . C9 C 0.0403(3) 0.2996(5) 0.3634(3) 0.0199(7) Uani 1 1 d . . . H9 H 0.0922 0.3837 0.4065 0.024 Uiso 1 1 calc R . . C10 C -0.0307(3) 0.2227(5) 0.4096(3) 0.0234(8) Uani 1 1 d . . . H10 H -0.0271 0.2549 0.4831 0.028 Uiso 1 1 calc R . . C11 C -0.1062(3) 0.0994(5) 0.3477(3) 0.0240(8) Uani 1 1 d . . . H11 H -0.1549 0.0472 0.3786 0.029 Uiso 1 1 calc R . . C12 C -0.1109(3) 0.0521(5) 0.2409(3) 0.0213(8) Uani 1 1 d . . . H12 H -0.1631 -0.0322 0.1984 0.026 Uiso 1 1 calc R . . C13 C -0.0391(3) 0.1282(5) 0.1956(3) 0.0178(7) Uani 1 1 d . . . C14 C 0.2074(3) 0.2081(4) 0.2038(3) 0.0143(7) Uani 1 1 d . . . H14 H 0.1671 0.1001 0.1851 0.017 Uiso 1 1 calc R . . C15 C 0.3088(3) 0.1900(4) 0.3238(3) 0.0142(7) Uani 1 1 d . . . C16 C 0.4228(3) 0.2868(4) 0.5182(3) 0.0167(7) Uani 1 1 d . . . H16A H 0.4755 0.3827 0.5418 0.020 Uiso 1 1 calc R . . H16B H 0.4709 0.1918 0.5168 0.020 Uiso 1 1 calc R . . C17 C 0.3729(3) 0.2579(5) 0.6071(3) 0.0176(7) Uani 1 1 d . . . C18 C 0.4208(3) 0.3370(5) 0.7140(3) 0.0256(8) Uani 1 1 d . . . H18 H 0.4846 0.4105 0.7309 0.031 Uiso 1 1 calc R . . C19 C 0.3759(4) 0.3088(6) 0.7960(3) 0.0331(9) Uani 1 1 d . . . H19 H 0.4089 0.3636 0.8686 0.040 Uiso 1 1 calc R . . C20 C 0.2834(4) 0.2015(5) 0.7727(3) 0.0302(9) Uani 1 1 d . . . H20 H 0.2526 0.1830 0.8289 0.036 Uiso 1 1 calc R . . C21 C 0.2363(3) 0.1220(5) 0.6677(3) 0.0268(8) Uani 1 1 d . . . H21 H 0.1733 0.0474 0.6518 0.032 Uiso 1 1 calc R . . C22 C 0.2802(3) 0.1498(5) 0.5845(3) 0.0219(8) Uani 1 1 d . . . H22 H 0.2467 0.0948 0.5121 0.026 Uiso 1 1 calc R . . C23 C 0.4915(4) 0.3144(9) 0.2155(6) 0.0605(15) Uani 1 1 d . . . H23A H 0.4931 0.2128 0.2579 0.073 Uiso 1 1 calc R . . H23B H 0.5268 0.4007 0.2742 0.073 Uiso 1 1 calc R . . C24 C 0.5666(4) 0.2917(8) 0.1543(6) 0.0571(15) Uani 1 1 d . . . H24A H 0.5308 0.2115 0.0923 0.086 Uiso 1 1 calc R . . H24B H 0.6444 0.2531 0.2089 0.086 Uiso 1 1 calc R . . H24C H 0.5753 0.3953 0.1205 0.086 Uiso 1 1 calc R . . C25 C 0.2339(3) -0.0548(5) 0.0150(3) 0.0228(8) Uani 1 1 d . . . H25A H 0.2091 -0.0457 -0.0699 0.027 Uiso 1 1 calc R . . H25B H 0.1627 -0.0492 0.0309 0.027 Uiso 1 1 calc R . . C26 C 0.2968(4) -0.2130(5) 0.0583(4) 0.0340(10) Uani 1 1 d . . . H26A H 0.3665 -0.2182 0.0412 0.051 Uiso 1 1 calc R . . H26B H 0.2436 -0.3032 0.0196 0.051 Uiso 1 1 calc R . . H26C H 0.3212 -0.2209 0.1424 0.051 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 0.0184(4) 0.0149(4) 0.0214(4) 0.0033(4) 0.0107(3) 0.0010(3) O1 0.0205(11) 0.0245(14) 0.0203(11) -0.0058(12) 0.0083(10) -0.0078(12) O2 0.0174(11) 0.0125(12) 0.0217(11) 0.0002(10) 0.0043(9) 0.0041(10) O3 0.0394(14) 0.0292(15) 0.0227(12) 0.0107(12) 0.0168(11) 0.0129(13) O4 0.0274(14) 0.0232(15) 0.076(2) -0.0155(16) 0.0327(15) -0.0112(13) O5 0.0156(11) 0.0177(13) 0.0255(12) -0.0020(11) 0.0085(9) -0.0019(11) N1 0.0120(12) 0.0123(14) 0.0186(13) 0.0003(12) 0.0051(10) 0.0008(12) C1 0.0131(14) 0.0111(16) 0.0209(16) 0.0015(14) 0.0079(13) 0.0000(13) C2 0.0163(14) 0.0134(17) 0.0282(17) 0.0012(15) 0.0111(13) -0.0028(15) C3 0.0245(16) 0.0113(16) 0.0369(19) -0.0021(18) 0.0169(14) -0.0009(15) C4 0.0277(17) 0.0100(19) 0.043(2) 0.0039(16) 0.0159(16) 0.0041(15) C5 0.0214(17) 0.0151(18) 0.0343(19) 0.0035(17) 0.0069(15) 0.0057(16) C6 0.0148(15) 0.0118(17) 0.0240(17) 0.0030(14) 0.0065(13) 0.0012(14) C7 0.0133(14) 0.0139(18) 0.0175(15) 0.0020(14) 0.0043(12) 0.0024(14) C8 0.0105(13) 0.0130(16) 0.0200(14) 0.0029(15) 0.0050(11) 0.0021(13) C9 0.0129(14) 0.0212(18) 0.0240(16) -0.0028(15) 0.0060(12) 0.0003(14) C10 0.0195(15) 0.028(2) 0.0259(16) -0.0043(17) 0.0129(13) 0.0003(16) C11 0.0181(16) 0.028(2) 0.0288(17) 0.0012(17) 0.0128(14) -0.0009(16) C12 0.0150(15) 0.021(2) 0.0268(17) -0.0021(16) 0.0075(13) -0.0035(15) C13 0.0128(14) 0.0195(18) 0.0183(15) -0.0003(15) 0.0038(12) 0.0021(14) C14 0.0127(14) 0.0114(17) 0.0180(14) 0.0019(13) 0.0054(12) -0.0009(13) C15 0.0126(14) 0.0116(16) 0.0190(15) 0.0013(13) 0.0071(12) -0.0017(13) C16 0.0106(13) 0.0142(18) 0.0210(15) -0.0027(14) 0.0024(12) 0.0005(13) C17 0.0164(14) 0.0131(17) 0.0182(14) 0.0023(15) 0.0021(11) 0.0045(14) C18 0.0216(17) 0.023(2) 0.0223(17) -0.0002(16) -0.0004(14) -0.0011(16) C19 0.041(2) 0.028(2) 0.0217(18) -0.0018(17) 0.0050(16) 0.004(2) C20 0.040(2) 0.027(2) 0.0272(18) 0.0103(17) 0.0179(16) 0.0110(19) C21 0.0267(18) 0.0210(19) 0.0356(19) 0.0043(17) 0.0159(16) 0.0046(16) C22 0.0209(17) 0.0163(19) 0.0276(17) -0.0014(15) 0.0091(14) 0.0012(14) C23 0.041(3) 0.054(4) 0.077(4) -0.012(3) 0.015(3) -0.011(3) C24 0.040(2) 0.040(3) 0.101(4) -0.008(3) 0.039(3) -0.006(2) C25 0.0205(16) 0.023(2) 0.0214(17) -0.0060(16) 0.0052(14) -0.0055(16) C26 0.0307(19) 0.022(2) 0.045(2) -0.0045(19) 0.0120(17) -0.0043(17) _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 O3 1.484(3) . ? P1 O4 1.563(3) . ? P1 O5 1.563(3) . ? P1 C14 1.817(3) . ? O1 C13 1.370(4) . ? O1 H1 0.86(7) . ? O2 C15 1.230(4) . ? O4 C23 1.380(6) . ? O5 C25 1.467(4) . ? N1 C15 1.356(4) . ? N1 C1 1.430(4) . ? N1 C16 1.473(4) . ? C1 C2 1.331(5) . ? C1 C6 1.520(4) . ? C2 C3 1.500(5) . ? C2 H2 0.9500 . ? C3 C4 1.527(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.520(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.530(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.536(5) . ? C6 H6 1.0000 . ? C7 C8 1.521(4) . ? C7 C14 1.541(4) . ? C7 H7 1.0000 . ? C8 C9 1.396(5) . ? C8 C13 1.406(5) . ? C9 C10 1.399(5) . ? C9 H9 0.9500 . ? C10 C11 1.385(5) . ? C10 H10 0.9500 . ? C11 C12 1.385(5) . ? C11 H11 0.9500 . ? C12 C13 1.396(5) . ? C12 H12 0.9500 . ? C14 C15 1.527(4) . ? C14 H14 1.0000 . ? C16 C17 1.513(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C22 1.391(5) . ? C17 C18 1.393(5) . ? C18 C19 1.389(6) . ? C18 H18 0.9500 . ? C19 C20 1.383(6) . ? C19 H19 0.9500 . ? C20 C21 1.376(6) . ? C20 H20 0.9500 . ? C21 C22 1.393(5) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.453(8) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.501(6) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 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 O3 P1 O4 111.41(19) . . ? O3 P1 O5 114.47(16) . . ? O4 P1 O5 103.87(14) . . ? O3 P1 C14 111.44(14) . . ? O4 P1 C14 107.98(16) . . ? O5 P1 C14 107.20(15) . . ? C13 O1 H1 117(4) . . ? C23 O4 P1 129.9(4) . . ? C25 O5 P1 119.5(2) . . ? C15 N1 C1 125.1(3) . . ? C15 N1 C16 116.7(3) . . ? C1 N1 C16 118.2(3) . . ? C2 C1 N1 121.6(3) . . ? C2 C1 C6 121.9(3) . . ? N1 C1 C6 116.5(3) . . ? C1 C2 C3 124.1(3) . . ? C1 C2 H2 118.0 . . ? C3 C2 H2 118.0 . . ? C2 C3 C4 113.0(3) . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 111.1(3) . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 109.9(3) . . ? C4 C5 H5A 109.7 . . ? C6 C5 H5A 109.7 . . ? C4 C5 H5B 109.7 . . ? C6 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C1 C6 C5 111.7(3) . . ? C1 C6 C7 112.0(3) . . ? C5 C6 C7 114.1(3) . . ? C1 C6 H6 106.1 . . ? C5 C6 H6 106.1 . . ? C7 C6 H6 106.1 . . ? C8 C7 C6 117.6(3) . . ? C8 C7 C14 109.6(3) . . ? C6 C7 C14 107.3(2) . . ? C8 C7 H7 107.3 . . ? C6 C7 H7 107.3 . . ? C14 C7 H7 107.3 . . ? C9 C8 C13 117.5(3) . . ? C9 C8 C7 124.6(3) . . ? C13 C8 C7 117.8(3) . . ? C8 C9 C10 121.6(3) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C11 C10 C9 119.6(3) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C12 C11 C10 120.1(3) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 120.0(3) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? O1 C13 C12 121.5(3) . . ? O1 C13 C8 117.4(3) . . ? C12 C13 C8 121.1(3) . . ? C15 C14 C7 113.4(3) . . ? C15 C14 P1 110.4(2) . . ? C7 C14 P1 114.3(2) . . ? C15 C14 H14 106.0 . . ? C7 C14 H14 106.0 . . ? P1 C14 H14 106.0 . . ? O2 C15 N1 122.9(3) . . ? O2 C15 C14 118.8(3) . . ? N1 C15 C14 118.3(3) . . ? N1 C16 C17 112.6(2) . . ? N1 C16 H16A 109.1 . . ? C17 C16 H16A 109.1 . . ? N1 C16 H16B 109.1 . . ? C17 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C22 C17 C18 118.8(3) . . ? C22 C17 C16 120.7(3) . . ? C18 C17 C16 120.4(3) . . ? C19 C18 C17 120.3(4) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C20 C19 C18 120.5(4) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C21 C20 C19 119.5(4) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 120.5(4) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C17 C22 C21 120.3(3) . . ? C17 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? O4 C23 C24 117.1(6) . . ? O4 C23 H23A 108.0 . . ? C24 C23 H23A 108.0 . . ? O4 C23 H23B 108.0 . . ? C24 C23 H23B 108.0 . . ? H23A C23 H23B 107.3 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O5 C25 C26 108.3(3) . . ? O5 C25 H25A 110.0 . . ? C26 C25 H25A 110.0 . . ? O5 C25 H25B 110.0 . . ? C26 C25 H25B 110.0 . . ? H25A C25 H25B 108.4 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 O3 P1 O4 C23 -151.4(5) . . . . ? O5 P1 O4 C23 -27.7(5) . . . . ? C14 P1 O4 C23 85.9(5) . . . . ? O3 P1 O5 C25 -53.2(3) . . . . ? O4 P1 O5 C25 -174.9(3) . . . . ? C14 P1 O5 C25 70.9(3) . . . . ? C15 N1 C1 C2 -178.1(3) . . . . ? C16 N1 C1 C2 1.1(4) . . . . ? C15 N1 C1 C6 0.4(4) . . . . ? C16 N1 C1 C6 179.6(3) . . . . ? N1 C1 C2 C3 178.3(3) . . . . ? C6 C1 C2 C3 -0.1(5) . . . . ? C1 C2 C3 C4 -10.8(5) . . . . ? C2 C3 C4 C5 41.1(4) . . . . ? C3 C4 C5 C6 -61.3(4) . . . . ? C2 C1 C6 C5 -19.6(5) . . . . ? N1 C1 C6 C5 161.9(3) . . . . ? C2 C1 C6 C7 -149.1(3) . . . . ? N1 C1 C6 C7 32.4(4) . . . . ? C4 C5 C6 C1 49.4(4) . . . . ? C4 C5 C6 C7 177.7(3) . . . . ? C1 C6 C7 C8 66.7(4) . . . . ? C5 C6 C7 C8 -61.4(4) . . . . ? C1 C6 C7 C14 -57.2(3) . . . . ? C5 C6 C7 C14 174.6(3) . . . . ? C6 C7 C8 C9 -14.7(5) . . . . ? C14 C7 C8 C9 108.1(4) . . . . ? C6 C7 C8 C13 168.2(3) . . . . ? C14 C7 C8 C13 -69.0(4) . . . . ? C13 C8 C9 C10 -1.5(5) . . . . ? C7 C8 C9 C10 -178.6(3) . . . . ? C8 C9 C10 C11 0.4(5) . . . . ? C9 C10 C11 C12 0.3(6) . . . . ? C10 C11 C12 C13 0.3(6) . . . . ? C11 C12 C13 O1 177.8(3) . . . . ? C11 C12 C13 C8 -1.5(5) . . . . ? C9 C8 C13 O1 -177.2(3) . . . . ? C7 C8 C13 O1 0.1(4) . . . . ? C9 C8 C13 C12 2.1(5) . . . . ? C7 C8 C13 C12 179.4(3) . . . . ? C8 C7 C14 C15 -75.9(3) . . . . ? C6 C7 C14 C15 52.8(4) . . . . ? C8 C7 C14 P1 156.4(2) . . . . ? C6 C7 C14 P1 -74.9(3) . . . . ? O3 P1 C14 C15 -160.4(2) . . . . ? O4 P1 C14 C15 -37.7(3) . . . . ? O5 P1 C14 C15 73.7(3) . . . . ? O3 P1 C14 C7 -31.1(3) . . . . ? O4 P1 C14 C7 91.6(3) . . . . ? O5 P1 C14 C7 -157.1(2) . . . . ? C1 N1 C15 O2 176.0(3) . . . . ? C16 N1 C15 O2 -3.3(4) . . . . ? C1 N1 C15 C14 -5.3(4) . . . . ? C16 N1 C15 C14 175.5(3) . . . . ? C7 C14 C15 O2 155.8(3) . . . . ? P1 C14 C15 O2 -74.5(3) . . . . ? C7 C14 C15 N1 -23.0(4) . . . . ? P1 C14 C15 N1 106.7(3) . . . . ? C15 N1 C16 C17 -105.6(3) . . . . ? C1 N1 C16 C17 75.1(4) . . . . ? N1 C16 C17 C22 46.9(5) . . . . ? N1 C16 C17 C18 -134.3(3) . . . . ? C22 C17 C18 C19 -0.5(5) . . . . ? C16 C17 C18 C19 -179.2(4) . . . . ? C17 C18 C19 C20 0.3(6) . . . . ? C18 C19 C20 C21 0.3(6) . . . . ? C19 C20 C21 C22 -0.6(6) . . . . ? C18 C17 C22 C21 0.1(5) . . . . ? C16 C17 C22 C21 178.9(3) . . . . ? C20 C21 C22 C17 0.4(6) . . . . ? P1 O4 C23 C24 93.6(6) . . . . ? P1 O5 C25 C26 -151.5(3) . . . . ? data_33 _database_code_depnum_ccdc_archive 'CCDC 912215' #==================================================== _chemical_name_systematic ; (3aS,9S,9aS)-10-methylene-12-[(R)-1-phenylethyl]-2,3,9,9a-tetrahydro-1H-3a,9- -(epiminoethano)cyclopenta[b]chromen-11-one ; _chemical_formula_moiety '4(C23 H23 N O2), C4 H10 O' _chemical_formula_sum 'C96 H102 N4 O9' _chemical_formula_weight 1455.88 _chemical_melting_point 387(1) _exptl_crystal_colour colourless _exptl_crystal_description plate _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_preparation ; slow evaporation from diethyl ether solution ; _exptl_crystal_F_000 778 _exptl_absorpt_coefficient_mu 0.635 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8324 _exptl_absorpt_correction_T_max 0.9392 _exptl_absorpt_process_details 'Bruker SADABS' _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' _cell_length_a 9.2805(1) _cell_length_b 12.9476(2) _cell_length_c 16.1252(2) _cell_angle_alpha 99.392(1) _cell_angle_beta 91.714(1) _cell_angle_gamma 90.912(1) _cell_volume 1910.35(4) _cell_formula_units_Z 1 _cell_measurement_temperature 100(1) _exptl_crystal_density_diffrn 1.265 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_ambient_temperature 100(2) _diffrn_reflns_number 62988 _reflns_number_total 12999 _reflns_number_gt 12996 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 70.41 _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 68.00 _diffrn_measured_fraction_theta_full 0.966 _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^)+(0.0465P)^2^+0.3153P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_number_reflns 12999 _refine_ls_number_parameters 989 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0257 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0755 _refine_ls_wR_factor_gt 0.0741 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881 for 6958 Fridel pairs' _refine_ls_abs_structure_Flack -0.07(7) _chemical_absolute_configuration rmad _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.182 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.028 _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' 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 N1A N 0.70391(11) 0.21070(9) 0.06079(7) 0.0175(2) Uani 1 1 d . . . O1A O 0.61423(10) 0.37465(7) 0.12357(5) 0.02098(19) Uani 1 1 d . . . O2A O 0.82887(10) 0.12412(7) -0.04657(6) 0.0224(2) Uani 1 1 d . . . C1A C 0.57604(14) 0.26624(10) 0.09014(8) 0.0189(3) Uani 1 1 d . . . C2A C 0.49809(14) 0.22678(12) 0.16167(8) 0.0232(3) Uani 1 1 d . . . H2A1 H 0.5375 0.2616 0.2171 0.028 Uiso 1 1 calc R . . H2A2 H 0.5074 0.1501 0.1579 0.028 Uiso 1 1 calc R . . C3A C 0.33839(15) 0.25606(13) 0.14858(9) 0.0282(3) Uani 1 1 d . . . H3A1 H 0.2750 0.1929 0.1425 0.034 Uiso 1 1 calc R . . H3A2 H 0.3073 0.3067 0.1972 0.034 Uiso 1 1 calc R . . C4A C 0.33036(14) 0.30539(12) 0.06731(9) 0.0269(3) Uani 1 1 d . . . H4A1 H 0.2394 0.2851 0.0347 0.032 Uiso 1 1 calc R . . H4A2 H 0.3387 0.3827 0.0802 0.032 Uiso 1 1 calc R . . C5A C 0.46021(14) 0.25883(11) 0.02039(8) 0.0211(3) Uani 1 1 d . . . H5A H 0.4383 0.1830 -0.0006 0.025 Uiso 1 1 calc R . . C6A C 0.52385(14) 0.30601(11) -0.05104(8) 0.0206(3) Uani 1 1 d . . . H6A H 0.4483 0.3096 -0.0960 0.025 Uiso 1 1 calc R . . C7A C 0.58630(14) 0.41457(11) -0.01816(8) 0.0209(3) Uani 1 1 d . . . C8A C 0.60576(14) 0.48840(11) -0.07120(9) 0.0242(3) Uani 1 1 d . . . H8A H 0.5736 0.4720 -0.1284 0.029 Uiso 1 1 calc R . . C9A C 0.67075(16) 0.58484(12) -0.04241(10) 0.0293(3) Uani 1 1 d . . . H9A H 0.6844 0.6337 -0.0797 0.035 Uiso 1 1 calc R . . C10A C 0.71596(17) 0.60980(12) 0.04135(10) 0.0306(3) Uani 1 1 d . . . H10A H 0.7609 0.6759 0.0615 0.037 Uiso 1 1 calc R . . C11A C 0.69564(15) 0.53837(11) 0.09584(9) 0.0264(3) Uani 1 1 d . . . H11A H 0.7254 0.5559 0.1534 0.032 Uiso 1 1 calc R . . C12A C 0.63182(14) 0.44157(11) 0.06593(8) 0.0210(3) Uani 1 1 d . . . C13A C 0.64225(14) 0.23355(10) -0.08494(8) 0.0197(3) Uani 1 1 d . . . C14A C 0.67076(15) 0.21153(11) -0.16572(8) 0.0231(3) Uani 1 1 d . . . H141 H 0.7465 0.1655 -0.1837 0.028 Uiso 1 1 calc R . . H142 H 0.6155 0.2418 -0.2058 0.028 Uiso 1 1 calc R . . C15A C 0.73213(14) 0.18417(10) -0.02304(8) 0.0184(3) Uani 1 1 d . . . C16A C 0.80869(13) 0.18857(10) 0.12608(8) 0.0185(3) Uani 1 1 d . . . H16A H 0.7824 0.2347 0.1792 0.022 Uiso 1 1 calc R . . C17A C 0.79717(14) 0.07696(11) 0.14412(8) 0.0211(3) Uani 1 1 d . . . C18A C 0.70776(15) 0.00024(11) 0.09768(9) 0.0243(3) Uani 1 1 d . . . H18A H 0.6530 0.0161 0.0508 0.029 Uiso 1 1 calc R . . C19A C 0.69721(19) -0.09938(12) 0.11879(10) 0.0324(3) Uani 1 1 d . . . H19A H 0.6350 -0.1510 0.0868 0.039 Uiso 1 1 calc R . . C20A C 0.7781(2) -0.12324(13) 0.18685(11) 0.0424(4) Uani 1 1 d . . . H20A H 0.7705 -0.1909 0.2021 0.051 Uiso 1 1 calc R . . C21A C 0.8696(2) -0.04782(15) 0.23228(11) 0.0479(5) Uani 1 1 d . . . H21A H 0.9270 -0.0646 0.2778 0.058 Uiso 1 1 calc R . . C22A C 0.87837(19) 0.05163(13) 0.21191(9) 0.0334(3) Uani 1 1 d . . . H22A H 0.9401 0.1031 0.2443 0.040 Uiso 1 1 calc R . . C23A C 0.96401(15) 0.22029(12) 0.10937(9) 0.0271(3) Uani 1 1 d . . . H23A H 0.9997 0.1720 0.0615 0.041 Uiso 1 1 calc R . . H23B H 1.0256 0.2173 0.1593 0.041 Uiso 1 1 calc R . . H23C H 0.9658 0.2917 0.0966 0.041 Uiso 1 1 calc R . . N1B N 0.66088(11) 0.36213(8) 0.60732(6) 0.0172(2) Uani 1 1 d . . . O1B O 0.85324(9) 0.25448(7) 0.55759(5) 0.01996(19) Uani 1 1 d . . . O2B O 0.49902(10) 0.37472(7) 0.71062(5) 0.02016(19) Uani 1 1 d . . . C1B C 0.72290(14) 0.30374(10) 0.53284(8) 0.0189(3) Uani 1 1 d . . . C2B C 0.77212(15) 0.36553(11) 0.46523(8) 0.0234(3) Uani 1 1 d . . . H2B1 H 0.8683 0.3987 0.4801 0.028 Uiso 1 1 calc R . . H2B2 H 0.7025 0.4204 0.4570 0.028 Uiso 1 1 calc R . . C3B C 0.77763(16) 0.28053(12) 0.38535(9) 0.0283(3) Uani 1 1 d . . . H3B1 H 0.7263 0.3042 0.3373 0.034 Uiso 1 1 calc R . . H3B2 H 0.8788 0.2664 0.3702 0.034 Uiso 1 1 calc R . . C4B C 0.70330(16) 0.18037(12) 0.40677(9) 0.0279(3) Uani 1 1 d . . . H4B1 H 0.6379 0.1473 0.3600 0.034 Uiso 1 1 calc R . . H4B2 H 0.7755 0.1289 0.4189 0.034 Uiso 1 1 calc R . . C5B C 0.61913(14) 0.22120(11) 0.48487(8) 0.0214(3) Uani 1 1 d . . . H5B H 0.5319 0.2573 0.4669 0.026 Uiso 1 1 calc R . . C6B C 0.57275(14) 0.14906(11) 0.54582(8) 0.0218(3) Uani 1 1 d . . . H6B H 0.5131 0.0886 0.5159 0.026 Uiso 1 1 calc R . . C7B C 0.70358(15) 0.11118(10) 0.58980(8) 0.0217(3) Uani 1 1 d . . . C8B C 0.83374(14) 0.16803(10) 0.59650(8) 0.0206(3) Uani 1 1 d . . . C9B C 0.95207(15) 0.13958(11) 0.64145(9) 0.0252(3) Uani 1 1 d . . . H9B H 1.0392 0.1798 0.6456 0.030 Uiso 1 1 calc R . . C10B C 0.94240(17) 0.05207(12) 0.68034(10) 0.0305(3) Uani 1 1 d . . . H10B H 1.0230 0.0321 0.7114 0.037 Uiso 1 1 calc R . . C11B C 0.81451(19) -0.00669(12) 0.67397(10) 0.0322(3) Uani 1 1 d . . . H11B H 0.8082 -0.0671 0.7002 0.039 Uiso 1 1 calc R . . C12B C 0.69663(17) 0.02286(11) 0.62951(9) 0.0276(3) Uani 1 1 d . . . H12B H 0.6095 -0.0174 0.6259 0.033 Uiso 1 1 calc R . . C13B C 0.48531(14) 0.21716(11) 0.61064(8) 0.0202(3) Uani 1 1 d . . . C14B C 0.36166(15) 0.18696(11) 0.63859(9) 0.0256(3) Uani 1 1 d . . . H143 H 0.3135 0.2322 0.6807 0.031 Uiso 1 1 calc R . . H144 H 0.3210 0.1200 0.6165 0.031 Uiso 1 1 calc R . . C15B C 0.54724(13) 0.32427(10) 0.64703(8) 0.0175(2) Uani 1 1 d . . . C16B C 0.74518(13) 0.45427(10) 0.65148(8) 0.0173(2) Uani 1 1 d . . . H16B H 0.8263 0.4646 0.6140 0.021 Uiso 1 1 calc R . . C17B C 0.65900(13) 0.55399(10) 0.65934(8) 0.0178(3) Uani 1 1 d . . . C18B C 0.53999(14) 0.56296(11) 0.60594(8) 0.0202(3) Uani 1 1 d . . . H18B H 0.5072 0.5036 0.5670 0.024 Uiso 1 1 calc R . . C19B C 0.46908(14) 0.65641(11) 0.60870(9) 0.0234(3) Uani 1 1 d . . . H19B H 0.3877 0.6602 0.5722 0.028 Uiso 1 1 calc R . . C20B C 0.51552(15) 0.74471(11) 0.66419(9) 0.0233(3) Uani 1 1 d . . . H20B H 0.4675 0.8092 0.6657 0.028 Uiso 1 1 calc R . . C21B C 0.63363(15) 0.73690(11) 0.71756(8) 0.0221(3) Uani 1 1 d . . . H21B H 0.6665 0.7968 0.7559 0.027 Uiso 1 1 calc R . . C22B C 0.70440(14) 0.64303(10) 0.71583(8) 0.0196(3) Uani 1 1 d . . . H22B H 0.7843 0.6392 0.7533 0.024 Uiso 1 1 calc R . . C23B C 0.81593(14) 0.43101(11) 0.73327(8) 0.0206(3) Uani 1 1 d . . . H23D H 0.7412 0.4228 0.7735 0.031 Uiso 1 1 calc R . . H23E H 0.8816 0.4891 0.7571 0.031 Uiso 1 1 calc R . . H23F H 0.8703 0.3663 0.7215 0.031 Uiso 1 1 calc R . . N1C N 0.16811(12) 0.82484(8) 0.48411(7) 0.0184(2) Uani 1 1 d . . . O1C O 0.09384(10) 0.64880(7) 0.43281(5) 0.02020(19) Uani 1 1 d . . . O2C O 0.30331(10) 0.92157(7) 0.58827(6) 0.0225(2) Uani 1 1 d . . . C1C C 0.04539(14) 0.75520(10) 0.45696(8) 0.0190(3) Uani 1 1 d . . . C2C C -0.04276(16) 0.77730(11) 0.38076(9) 0.0255(3) Uani 1 1 d . . . H2C1 H 0.0034 0.7477 0.3278 0.031 Uiso 1 1 calc R . . H2C2 H -0.0542 0.8535 0.3825 0.031 Uiso 1 1 calc R . . C3C C -0.18978(17) 0.72243(14) 0.38833(10) 0.0347(4) Uani 1 1 d . . . H3C1 H -0.1994 0.6571 0.3468 0.042 Uiso 1 1 calc R . . H3C2 H -0.2697 0.7689 0.3780 0.042 Uiso 1 1 calc R . . C4C C -0.19359(15) 0.69754(12) 0.47925(9) 0.0278(3) Uani 1 1 d . . . H4C1 H -0.2856 0.7194 0.5057 0.033 Uiso 1 1 calc R . . H4C2 H -0.1813 0.6218 0.4797 0.033 Uiso 1 1 calc R . . C5C C -0.06671(14) 0.76137(10) 0.52458(8) 0.0210(3) Uani 1 1 d . . . H5C H -0.0964 0.8358 0.5394 0.025 Uiso 1 1 calc R . . C6C C 0.00582(14) 0.72871(10) 0.60180(8) 0.0192(3) Uani 1 1 d . . . H6C H -0.0657 0.7269 0.6467 0.023 Uiso 1 1 calc R . . C7C C 0.07104(13) 0.62182(10) 0.57772(8) 0.0188(3) Uani 1 1 d . . . C8C C 0.11426(13) 0.58905(10) 0.49595(8) 0.0183(3) Uani 1 1 d . . . C9C C 0.17783(14) 0.49263(11) 0.47299(8) 0.0213(3) Uani 1 1 d . . . H9C H 0.2068 0.4711 0.4169 0.026 Uiso 1 1 calc R . . C10C C 0.19862(15) 0.42793(11) 0.53312(9) 0.0244(3) Uani 1 1 d . . . H10C H 0.2414 0.3616 0.5179 0.029 Uiso 1 1 calc R . . C11C C 0.15729(15) 0.45966(11) 0.61516(9) 0.0236(3) Uani 1 1 d . . . H11C H 0.1725 0.4156 0.6562 0.028 Uiso 1 1 calc R . . C12C C 0.09371(14) 0.55589(11) 0.63696(8) 0.0209(3) Uani 1 1 d . . . H12C H 0.0651 0.5773 0.6931 0.025 Uiso 1 1 calc R . . C13C C 0.12333(14) 0.80997(10) 0.63176(8) 0.0188(3) Uani 1 1 d . . . C14C C 0.15884(15) 0.84046(11) 0.71238(8) 0.0231(3) Uani 1 1 d . . . H145 H 0.2344 0.8908 0.7283 0.028 Uiso 1 1 calc R . . H146 H 0.1087 0.8120 0.7542 0.028 Uiso 1 1 calc R . . C15C C 0.20586(14) 0.85732(10) 0.56742(8) 0.0176(3) Uani 1 1 d . . . C16C C 0.26118(14) 0.85468(10) 0.41877(8) 0.0204(3) Uani 1 1 d . . . H16C H 0.2242 0.8125 0.3646 0.024 Uiso 1 1 calc R . . C17C C 0.24583(14) 0.96937(10) 0.40788(8) 0.0185(3) Uani 1 1 d . . . C18C C 0.14364(15) 1.03438(11) 0.44940(8) 0.0224(3) Uani 1 1 d . . . H18C H 0.0841 1.0087 0.4887 0.027 Uiso 1 1 calc R . . C19C C 0.12708(16) 1.13631(11) 0.43438(9) 0.0243(3) Uani 1 1 d . . . H19C H 0.0573 1.1797 0.4637 0.029 Uiso 1 1 calc R . . C20C C 0.21221(16) 1.17453(11) 0.37671(9) 0.0254(3) Uani 1 1 d . . . H20C H 0.2004 1.2439 0.3659 0.030 Uiso 1 1 calc R . . C21C C 0.31456(15) 1.11112(11) 0.33495(8) 0.0251(3) Uani 1 1 d . . . H21C H 0.3730 1.1370 0.2952 0.030 Uiso 1 1 calc R . . C22C C 0.33228(15) 1.00970(11) 0.35088(8) 0.0217(3) Uani 1 1 d . . . H22C H 0.4041 0.9673 0.3226 0.026 Uiso 1 1 calc R . . C23C C 0.41792(16) 0.82169(13) 0.42938(10) 0.0292(3) Uani 1 1 d . . . H23G H 0.4639 0.8662 0.4783 0.044 Uiso 1 1 calc R . . H23H H 0.4705 0.8294 0.3789 0.044 Uiso 1 1 calc R . . H23I H 0.4195 0.7484 0.4377 0.044 Uiso 1 1 calc R . . N1D N 0.18539(12) 0.70371(9) 0.94735(6) 0.0182(2) Uani 1 1 d . . . O1D O 0.38074(10) 0.82099(8) 0.99211(6) 0.0239(2) Uani 1 1 d . . . O2D O 0.01477(10) 0.67688(7) 0.84242(5) 0.02024(19) Uani 1 1 d . . . C1D C 0.25363(15) 0.77033(11) 1.01929(8) 0.0220(3) Uani 1 1 d . . . C2D C 0.31016(17) 0.71789(13) 1.09144(9) 0.0299(3) Uani 1 1 d . . . H2D1 H 0.4074 0.6896 1.0801 0.036 Uiso 1 1 calc R . . H2D2 H 0.2444 0.6603 1.1009 0.036 Uiso 1 1 calc R . . C3D C 0.31517(19) 0.80822(15) 1.16841(9) 0.0378(4) Uani 1 1 d . . . H3D1 H 0.2620 0.7872 1.2155 0.045 Uiso 1 1 calc R . . H3D2 H 0.4162 0.8257 1.1878 0.045 Uiso 1 1 calc R . . C4D C 0.24405(18) 0.90316(14) 1.13872(9) 0.0344(4) Uani 1 1 d . . . H4D1 H 0.1832 0.9409 1.1827 0.041 Uiso 1 1 calc R . . H4D2 H 0.3174 0.9524 1.1233 0.041 Uiso 1 1 calc R . . C5D C 0.15265(15) 0.85290(12) 1.06179(8) 0.0253(3) Uani 1 1 d . . . H5D H 0.0678 0.8163 1.0817 0.030 Uiso 1 1 calc R . . C6D C 0.09930(15) 0.91621(11) 0.99588(8) 0.0232(3) Uani 1 1 d . . . H6D H 0.0417 0.9769 1.0221 0.028 Uiso 1 1 calc R . . C7D C 0.22454(15) 0.95293(11) 0.94900(8) 0.0237(3) Uani 1 1 d . . . C8D C 0.35468(15) 0.90052(11) 0.94653(8) 0.0233(3) Uani 1 1 d . . . C9D C 0.46640(16) 0.92618(12) 0.89758(9) 0.0289(3) Uani 1 1 d . . . H9D H 0.5543 0.8895 0.8967 0.035 Uiso 1 1 calc R . . C10D C 0.44903(18) 1.00535(12) 0.85020(10) 0.0337(4) Uani 1 1 d . . . H10D H 0.5244 1.0223 0.8159 0.040 Uiso 1 1 calc R . . C11D C 0.32136(19) 1.05988(12) 0.85291(10) 0.0349(4) Uani 1 1 d . . . H11D H 0.3101 1.1151 0.8212 0.042 Uiso 1 1 calc R . . C12D C 0.20996(17) 1.03388(11) 0.90186(9) 0.0284(3) Uani 1 1 d . . . H12D H 0.1228 1.0716 0.9033 0.034 Uiso 1 1 calc R . . C13D C 0.00633(14) 0.83986(11) 0.93475(8) 0.0210(3) Uani 1 1 d . . . C14D C -0.12198(16) 0.86189(12) 0.90584(10) 0.0293(3) Uani 1 1 d . . . H147 H -0.1742 0.8113 0.8665 0.035 Uiso 1 1 calc R . . H148 H -0.1622 0.9284 0.9243 0.035 Uiso 1 1 calc R . . C15D C 0.06785(14) 0.73364(10) 0.90436(8) 0.0183(3) Uani 1 1 d . . . C16D C 0.26768(13) 0.61191(10) 0.90811(8) 0.0183(3) Uani 1 1 d . . . H16D H 0.3502 0.6053 0.9481 0.022 Uiso 1 1 calc R . . C17D C 0.17980(13) 0.51006(10) 0.90037(8) 0.0188(3) Uani 1 1 d . . . C18D C 0.06547(15) 0.50031(11) 0.95311(8) 0.0233(3) Uani 1 1 d . . . H18D H 0.0390 0.5590 0.9927 0.028 Uiso 1 1 calc R . . C19D C -0.00989(15) 0.40610(12) 0.94847(9) 0.0261(3) Uani 1 1 d . . . H19D H -0.0881 0.4011 0.9844 0.031 Uiso 1 1 calc R . . C20D C 0.02813(15) 0.31898(11) 0.89161(9) 0.0249(3) Uani 1 1 d . . . H20D H -0.0229 0.2542 0.8886 0.030 Uiso 1 1 calc R . . C21D C 0.14153(15) 0.32833(11) 0.83945(9) 0.0235(3) Uani 1 1 d . . . H21D H 0.1684 0.2693 0.8004 0.028 Uiso 1 1 calc R . . C22D C 0.21681(14) 0.42265(11) 0.84321(8) 0.0202(3) Uani 1 1 d . . . H22D H 0.2940 0.4276 0.8066 0.024 Uiso 1 1 calc R . . C23D C 0.33523(14) 0.63307(11) 0.82659(8) 0.0205(3) Uani 1 1 d . . . H23J H 0.2588 0.6378 0.7842 0.031 Uiso 1 1 calc R . . H23K H 0.3992 0.5758 0.8057 0.031 Uiso 1 1 calc R . . H23L H 0.3908 0.6992 0.8378 0.031 Uiso 1 1 calc R . . O1E O 0.24426(13) 0.48442(9) 0.27467(7) 0.0365(3) Uani 1 1 d . . . C1E C 0.1184(2) 0.50651(16) 0.22907(11) 0.0455(4) Uani 1 1 d . . . H1E1 H 0.1279 0.4799 0.1684 0.055 Uiso 1 1 calc R . . H1E2 H 0.1044 0.5831 0.2363 0.055 Uiso 1 1 calc R . . C2E C -0.0088(2) 0.45364(18) 0.26228(12) 0.0500(5) Uani 1 1 d . . . H2E1 H 0.0109 0.3793 0.2609 0.075 Uiso 1 1 calc R . . H2E2 H -0.0950 0.4606 0.2272 0.075 Uiso 1 1 calc R . . H2E3 H -0.0250 0.4867 0.3203 0.075 Uiso 1 1 calc R . . C3E C 0.3675(2) 0.54429(17) 0.26180(12) 0.0525(5) Uani 1 1 d . . . H3E1 H 0.3476 0.6199 0.2763 0.063 Uiso 1 1 calc R . . H3E2 H 0.3936 0.5294 0.2020 0.063 Uiso 1 1 calc R . . C4E C 0.4896(2) 0.5158(2) 0.31696(14) 0.0606(6) Uani 1 1 d . . . H4E1 H 0.4662 0.5363 0.3762 0.091 Uiso 1 1 calc R . . H4E2 H 0.5781 0.5527 0.3056 0.091 Uiso 1 1 calc R . . H4E3 H 0.5039 0.4401 0.3050 0.091 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 N1A 0.0147(5) 0.0190(5) 0.0189(5) 0.0040(4) -0.0008(4) 0.0007(4) O1A 0.0219(4) 0.0216(5) 0.0195(4) 0.0028(4) 0.0011(3) 0.0033(4) O2A 0.0255(5) 0.0183(4) 0.0241(5) 0.0040(4) 0.0056(4) 0.0040(4) C1A 0.0165(6) 0.0210(7) 0.0196(6) 0.0048(5) 0.0007(5) 0.0009(5) C2A 0.0190(6) 0.0294(7) 0.0228(6) 0.0084(5) 0.0037(5) 0.0021(6) C3A 0.0201(7) 0.0356(8) 0.0305(7) 0.0089(6) 0.0068(5) 0.0048(6) C4A 0.0159(6) 0.0347(8) 0.0321(7) 0.0109(6) 0.0009(5) 0.0041(6) C5A 0.0155(6) 0.0251(7) 0.0235(6) 0.0068(5) -0.0014(5) 0.0013(5) C6A 0.0175(6) 0.0248(7) 0.0201(6) 0.0065(5) -0.0034(5) 0.0009(5) C7A 0.0160(6) 0.0224(7) 0.0249(6) 0.0047(5) 0.0029(5) 0.0060(5) C8A 0.0203(6) 0.0271(7) 0.0268(7) 0.0081(6) 0.0034(5) 0.0082(6) C9A 0.0295(7) 0.0230(7) 0.0383(8) 0.0111(6) 0.0092(6) 0.0093(6) C10A 0.0286(7) 0.0173(7) 0.0450(9) 0.0016(6) 0.0048(6) 0.0028(6) C11A 0.0247(7) 0.0230(7) 0.0300(7) -0.0010(5) 0.0021(5) 0.0051(6) C12A 0.0163(6) 0.0232(7) 0.0244(6) 0.0051(5) 0.0038(5) 0.0069(5) C13A 0.0203(6) 0.0168(6) 0.0220(6) 0.0046(5) -0.0019(5) -0.0061(5) C14A 0.0277(7) 0.0209(7) 0.0212(6) 0.0052(5) 0.0000(5) -0.0054(6) C15A 0.0195(6) 0.0161(6) 0.0195(6) 0.0025(5) 0.0015(5) -0.0052(5) C16A 0.0155(6) 0.0222(7) 0.0174(6) 0.0023(5) -0.0015(5) 0.0020(5) C17A 0.0213(6) 0.0241(7) 0.0183(6) 0.0040(5) 0.0025(5) 0.0045(6) C18A 0.0244(7) 0.0247(7) 0.0247(7) 0.0072(5) -0.0014(5) 0.0020(6) C19A 0.0425(9) 0.0231(7) 0.0323(7) 0.0063(6) 0.0046(6) 0.0002(7) C20A 0.0720(13) 0.0246(8) 0.0341(8) 0.0142(6) 0.0052(8) 0.0061(8) C21A 0.0778(14) 0.0391(10) 0.0298(8) 0.0163(7) -0.0115(8) 0.0075(10) C22A 0.0460(9) 0.0300(8) 0.0240(7) 0.0052(6) -0.0094(6) 0.0049(7) C23A 0.0179(6) 0.0325(8) 0.0311(7) 0.0072(6) -0.0032(5) -0.0027(6) N1B 0.0161(5) 0.0176(5) 0.0177(5) 0.0026(4) 0.0010(4) -0.0001(4) O1B 0.0156(4) 0.0211(5) 0.0231(4) 0.0031(3) 0.0008(3) 0.0022(4) O2B 0.0191(4) 0.0209(5) 0.0203(4) 0.0025(4) 0.0030(3) 0.0005(4) C1B 0.0162(6) 0.0217(6) 0.0188(6) 0.0029(5) 0.0000(5) 0.0025(5) C2B 0.0231(7) 0.0279(7) 0.0198(6) 0.0050(5) 0.0032(5) -0.0014(6) C3B 0.0301(7) 0.0363(8) 0.0183(6) 0.0029(6) 0.0031(5) 0.0009(6) C4B 0.0283(7) 0.0332(8) 0.0200(6) -0.0022(6) 0.0001(5) -0.0007(6) C5B 0.0196(6) 0.0233(7) 0.0200(6) -0.0002(5) -0.0022(5) 0.0012(6) C6B 0.0196(6) 0.0197(6) 0.0242(6) -0.0019(5) 0.0005(5) -0.0030(5) C7B 0.0234(7) 0.0185(6) 0.0215(6) -0.0023(5) 0.0035(5) 0.0028(6) C8B 0.0232(7) 0.0179(6) 0.0192(6) -0.0019(5) 0.0038(5) 0.0041(5) C9B 0.0229(7) 0.0237(7) 0.0272(7) -0.0020(5) 0.0014(5) 0.0049(6) C10B 0.0341(8) 0.0254(8) 0.0312(7) 0.0017(6) -0.0027(6) 0.0141(7) C11B 0.0431(9) 0.0196(7) 0.0348(8) 0.0055(6) 0.0054(6) 0.0089(7) C12B 0.0315(7) 0.0194(7) 0.0306(7) -0.0008(5) 0.0071(6) 0.0008(6) C13B 0.0189(6) 0.0207(7) 0.0211(6) 0.0043(5) -0.0039(5) -0.0004(5) C14B 0.0201(6) 0.0232(7) 0.0324(7) 0.0011(6) 0.0028(5) -0.0027(6) C15B 0.0154(6) 0.0196(6) 0.0183(6) 0.0057(5) -0.0017(4) 0.0019(5) C16B 0.0148(6) 0.0187(6) 0.0186(6) 0.0039(5) 0.0007(4) -0.0018(5) C17B 0.0158(6) 0.0191(6) 0.0198(6) 0.0071(5) 0.0028(5) -0.0019(5) C18B 0.0193(6) 0.0201(6) 0.0214(6) 0.0043(5) -0.0002(5) -0.0013(5) C19B 0.0172(6) 0.0269(7) 0.0275(7) 0.0092(5) -0.0026(5) 0.0002(6) C20B 0.0215(6) 0.0207(7) 0.0293(7) 0.0076(5) 0.0046(5) 0.0037(6) C21B 0.0225(6) 0.0191(6) 0.0245(6) 0.0026(5) 0.0029(5) -0.0009(5) C22B 0.0166(6) 0.0226(7) 0.0199(6) 0.0043(5) 0.0009(5) -0.0005(5) C23B 0.0207(6) 0.0199(6) 0.0216(6) 0.0052(5) -0.0021(5) -0.0001(5) N1C 0.0210(5) 0.0172(5) 0.0176(5) 0.0045(4) 0.0017(4) 0.0003(5) O1C 0.0257(5) 0.0174(4) 0.0176(4) 0.0031(3) 0.0004(3) 0.0003(4) O2C 0.0258(5) 0.0174(5) 0.0240(5) 0.0042(4) -0.0032(4) -0.0031(4) C1C 0.0215(6) 0.0165(6) 0.0192(6) 0.0039(5) -0.0007(5) 0.0007(5) C2C 0.0300(7) 0.0244(7) 0.0229(7) 0.0077(5) -0.0052(5) 0.0011(6) C3C 0.0245(7) 0.0448(10) 0.0357(8) 0.0110(7) -0.0087(6) 0.0001(7) C4C 0.0199(7) 0.0297(8) 0.0351(8) 0.0096(6) -0.0020(6) -0.0010(6) C5C 0.0203(6) 0.0193(6) 0.0243(6) 0.0065(5) 0.0009(5) 0.0028(6) C6C 0.0183(6) 0.0207(6) 0.0198(6) 0.0058(5) 0.0045(5) 0.0016(5) C7C 0.0153(6) 0.0173(6) 0.0235(6) 0.0034(5) -0.0013(5) -0.0027(5) C8C 0.0160(6) 0.0182(6) 0.0211(6) 0.0051(5) -0.0029(5) -0.0033(5) C9C 0.0202(6) 0.0200(7) 0.0225(6) 0.0004(5) -0.0028(5) -0.0025(5) C10C 0.0227(7) 0.0162(6) 0.0334(7) 0.0026(5) -0.0050(5) -0.0005(6) C11C 0.0243(7) 0.0200(7) 0.0272(7) 0.0080(5) -0.0062(5) -0.0046(6) C12C 0.0205(6) 0.0214(6) 0.0209(6) 0.0039(5) -0.0011(5) -0.0044(5) C13C 0.0215(6) 0.0151(6) 0.0207(6) 0.0041(5) 0.0030(5) 0.0065(5) C14C 0.0290(7) 0.0201(7) 0.0210(6) 0.0047(5) 0.0024(5) 0.0060(6) C15C 0.0192(6) 0.0131(6) 0.0210(6) 0.0038(5) 0.0002(5) 0.0047(5) C16C 0.0228(6) 0.0207(7) 0.0179(6) 0.0035(5) 0.0037(5) 0.0006(6) C17C 0.0194(6) 0.0203(6) 0.0154(6) 0.0029(5) -0.0030(5) -0.0019(5) C18C 0.0228(6) 0.0238(7) 0.0222(6) 0.0073(5) 0.0038(5) 0.0006(6) C19C 0.0255(7) 0.0218(7) 0.0262(7) 0.0053(5) 0.0014(5) 0.0039(6) C20C 0.0328(7) 0.0193(7) 0.0246(7) 0.0066(5) -0.0048(5) -0.0025(6) C21C 0.0294(7) 0.0270(7) 0.0198(6) 0.0074(5) 0.0013(5) -0.0065(6) C22C 0.0225(6) 0.0232(7) 0.0190(6) 0.0023(5) 0.0015(5) -0.0006(6) C23C 0.0272(7) 0.0293(8) 0.0340(7) 0.0115(6) 0.0091(6) 0.0093(6) N1D 0.0184(5) 0.0196(5) 0.0166(5) 0.0023(4) 0.0006(4) 0.0029(4) O1D 0.0196(4) 0.0262(5) 0.0244(5) 0.0006(4) -0.0033(4) 0.0017(4) O2D 0.0196(4) 0.0213(5) 0.0191(4) 0.0015(4) -0.0012(3) 0.0006(4) C1D 0.0206(6) 0.0257(7) 0.0189(6) 0.0015(5) -0.0010(5) 0.0019(6) C2D 0.0314(8) 0.0377(8) 0.0204(7) 0.0043(6) -0.0040(6) 0.0047(7) C3D 0.0433(9) 0.0490(10) 0.0189(7) -0.0006(6) -0.0057(6) 0.0055(8) C4D 0.0378(9) 0.0413(9) 0.0208(7) -0.0046(6) -0.0024(6) 0.0057(7) C5D 0.0267(7) 0.0277(7) 0.0196(6) -0.0020(5) 0.0021(5) 0.0031(6) C6D 0.0232(7) 0.0215(7) 0.0228(6) -0.0032(5) 0.0000(5) 0.0045(6) C7D 0.0252(7) 0.0205(7) 0.0224(6) -0.0048(5) -0.0026(5) -0.0022(6) C8D 0.0241(7) 0.0196(6) 0.0232(6) -0.0042(5) -0.0041(5) -0.0031(6) C9D 0.0247(7) 0.0260(7) 0.0323(7) -0.0054(6) 0.0009(6) -0.0069(6) C10D 0.0382(9) 0.0248(7) 0.0351(8) -0.0036(6) 0.0071(6) -0.0125(7) C11D 0.0486(10) 0.0204(7) 0.0340(8) 0.0014(6) -0.0029(7) -0.0096(7) C12D 0.0350(8) 0.0176(7) 0.0297(7) -0.0030(5) -0.0045(6) -0.0013(6) C13D 0.0207(6) 0.0216(7) 0.0203(6) 0.0019(5) 0.0041(5) 0.0013(6) C14D 0.0231(7) 0.0257(7) 0.0363(8) -0.0031(6) -0.0028(6) 0.0058(6) C15D 0.0177(6) 0.0210(6) 0.0166(6) 0.0039(5) 0.0025(5) -0.0004(5) C16D 0.0165(6) 0.0204(6) 0.0182(6) 0.0036(5) 0.0010(5) 0.0027(5) C17D 0.0166(6) 0.0230(7) 0.0183(6) 0.0078(5) -0.0004(5) 0.0034(5) C18D 0.0223(7) 0.0255(7) 0.0238(6) 0.0077(5) 0.0048(5) 0.0053(6) C19D 0.0205(7) 0.0299(8) 0.0312(7) 0.0134(6) 0.0065(5) 0.0030(6) C20D 0.0209(6) 0.0237(7) 0.0321(7) 0.0113(6) -0.0031(5) -0.0026(6) C21D 0.0234(7) 0.0215(7) 0.0254(6) 0.0036(5) -0.0024(5) 0.0034(6) C22D 0.0162(6) 0.0247(7) 0.0205(6) 0.0062(5) 0.0013(5) 0.0023(5) C23D 0.0197(6) 0.0204(7) 0.0219(6) 0.0043(5) 0.0040(5) 0.0010(5) O1E 0.0403(6) 0.0386(6) 0.0307(5) 0.0047(5) 0.0055(5) 0.0052(5) C1E 0.0625(12) 0.0458(10) 0.0273(8) 0.0027(7) -0.0043(7) 0.0166(9) C2E 0.0412(10) 0.0639(13) 0.0393(9) -0.0076(9) -0.0093(8) 0.0098(9) C3E 0.0681(13) 0.0481(11) 0.0387(10) -0.0009(8) 0.0116(9) -0.0133(10) C4E 0.0427(11) 0.0728(15) 0.0578(12) -0.0151(11) 0.0114(9) -0.0119(10) _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 N1A C15A 1.3735(16) . ? N1A C1A 1.4488(17) . ? N1A C16A 1.4773(16) . ? O1A C12A 1.3816(16) . ? O1A C1A 1.4534(16) . ? O2A C15A 1.2251(17) . ? C1A C5A 1.5228(17) . ? C1A C2A 1.5314(17) . ? C2A C3A 1.5525(19) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A C4A 1.549(2) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C4A C5A 1.5222(19) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C5A C6A 1.5191(18) . ? C5A H5A 1.0000 . ? C6A C13A 1.5125(19) . ? C6A C7A 1.5183(18) . ? C6A H6A 1.0000 . ? C7A C12A 1.3948(19) . ? C7A C8A 1.3960(19) . ? C8A C9A 1.382(2) . ? C8A H8A 0.9500 . ? C9A C10A 1.387(2) . ? C9A H9A 0.9500 . ? C10A C11A 1.390(2) . ? C10A H10A 0.9500 . ? C11A C12A 1.384(2) . ? C11A H11A 0.9500 . ? C13A C14A 1.3229(19) . ? C13A C15A 1.5087(18) . ? C14A H141 0.9500 . ? C14A H142 0.9500 . ? C16A C17A 1.5226(18) . ? C16A C23A 1.5361(18) . ? C16A H16A 1.0000 . ? C17A C18A 1.3892(19) . ? C17A C22A 1.395(2) . ? C18A C19A 1.389(2) . ? C18A H18A 0.9500 . ? C19A C20A 1.390(2) . ? C19A H19A 0.9500 . ? C20A C21A 1.384(3) . ? C20A H20A 0.9500 . ? C21A C22A 1.382(2) . ? C21A H21A 0.9500 . ? C22A H22A 0.9500 . ? C23A H23A 0.9800 . ? C23A H23B 0.9800 . ? C23A H23C 0.9800 . ? N1B C15B 1.3744(16) . ? N1B C1B 1.4507(16) . ? N1B C16B 1.4839(15) . ? O1B C8B 1.3816(16) . ? O1B C1B 1.4519(16) . ? O2B C15B 1.2234(16) . ? C1B C5B 1.5234(17) . ? C1B C2B 1.5296(17) . ? C2B C3B 1.5544(19) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C3B C4B 1.552(2) . ? C3B H3B1 0.9900 . ? C3B H3B2 0.9900 . ? C4B C5B 1.5266(18) . ? C4B H4B1 0.9900 . ? C4B H4B2 0.9900 . ? C5B C6B 1.5283(19) . ? C5B H5B 1.0000 . ? C6B C7B 1.516(2) . ? C6B C13B 1.5170(18) . ? C6B H6B 1.0000 . ? C7B C8B 1.3967(18) . ? C7B C12B 1.400(2) . ? C8B C9B 1.385(2) . ? C9B C10B 1.385(2) . ? C9B H9B 0.9500 . ? C10B C11B 1.392(2) . ? C10B H10B 0.9500 . ? C11B C12B 1.383(2) . ? C11B H11B 0.9500 . ? C12B H12B 0.9500 . ? C13B C14B 1.3217(19) . ? C13B C15B 1.5122(17) . ? C14B H143 0.9500 . ? C14B H144 0.9500 . ? C16B C17B 1.5192(19) . ? C16B C23B 1.5315(17) . ? C16B H16B 1.0000 . ? C17B C22B 1.3983(18) . ? C17B C18B 1.3981(18) . ? C18B C19B 1.381(2) . ? C18B H18B 0.9500 . ? C19B C20B 1.386(2) . ? C19B H19B 0.9500 . ? C20B C21B 1.388(2) . ? C20B H20B 0.9500 . ? C21B C22B 1.387(2) . ? C21B H21B 0.9500 . ? C22B H22B 0.9500 . ? C23B H23D 0.9800 . ? C23B H23E 0.9800 . ? C23B H23F 0.9800 . ? N1C C15C 1.3737(17) . ? N1C C1C 1.4527(16) . ? N1C C16C 1.4772(16) . ? O1C C8C 1.3862(16) . ? O1C C1C 1.4515(16) . ? O2C C15C 1.2204(16) . ? C1C C5C 1.5231(17) . ? C1C C2C 1.5241(17) . ? C2C C3C 1.545(2) . ? C2C H2C1 0.9900 . ? C2C H2C2 0.9900 . ? C3C C4C 1.553(2) . ? C3C H3C1 0.9900 . ? C3C H3C2 0.9900 . ? C4C C5C 1.5246(19) . ? C4C H4C1 0.9900 . ? C4C H4C2 0.9900 . ? C5C C6C 1.5209(18) . ? C5C H5C 1.0000 . ? C6C C13C 1.5151(18) . ? C6C C7C 1.5158(19) . ? C6C H6C 1.0000 . ? C7C C8C 1.3907(18) . ? C7C C12C 1.3947(19) . ? C8C C9C 1.389(2) . ? C9C C10C 1.392(2) . ? C9C H9C 0.9500 . ? C10C C11C 1.387(2) . ? C10C H10C 0.9500 . ? C11C C12C 1.384(2) . ? C11C H11C 0.9500 . ? C12C H12C 0.9500 . ? C13C C14C 1.3256(19) . ? C13C C15C 1.5096(17) . ? C14C H145 0.9500 . ? C14C H146 0.9500 . ? C16C C17C 1.5319(19) . ? C16C C23C 1.535(2) . ? C16C H16C 1.0000 . ? C17C C18C 1.3913(19) . ? C17C C22C 1.3959(18) . ? C18C C19C 1.390(2) . ? C18C H18C 0.9500 . ? C19C C20C 1.384(2) . ? C19C H19C 0.9500 . ? C20C C21C 1.383(2) . ? C20C H20C 0.9500 . ? C21C C22C 1.390(2) . ? C21C H21C 0.9500 . ? C22C H22C 0.9500 . ? C23C H23G 0.9800 . ? C23C H23H 0.9800 . ? C23C H23I 0.9800 . ? N1D C15D 1.3699(17) . ? N1D C1D 1.4502(17) . ? N1D C16D 1.4861(17) . ? O1D C8D 1.3796(18) . ? O1D C1D 1.4540(16) . ? O2D C15D 1.2246(16) . ? C1D C2D 1.5239(19) . ? C1D C5D 1.5238(19) . ? C2D C3D 1.559(2) . ? C2D H2D1 0.9900 . ? C2D H2D2 0.9900 . ? C3D C4D 1.541(3) . ? C3D H3D1 0.9900 . ? C3D H3D2 0.9900 . ? C4D C5D 1.5291(19) . ? C4D H4D1 0.9900 . ? C4D H4D2 0.9900 . ? C5D C6D 1.521(2) . ? C5D H5D 1.0000 . ? C6D C13D 1.5157(18) . ? C6D C7D 1.5169(19) . ? C6D H6D 1.0000 . ? C7D C8D 1.393(2) . ? C7D C12D 1.397(2) . ? C8D C9D 1.390(2) . ? C9D C10D 1.383(2) . ? C9D H9D 0.9500 . ? C10D C11D 1.387(3) . ? C10D H10D 0.9500 . ? C11D C12D 1.389(2) . ? C11D H11D 0.9500 . ? C12D H12D 0.9500 . ? C13D C14D 1.318(2) . ? C13D C15D 1.5098(19) . ? C14D H147 0.9500 . ? C14D H148 0.9500 . ? C16D C17D 1.5251(18) . ? C16D C23D 1.5353(17) . ? C16D H16D 1.0000 . ? C17D C22D 1.3925(19) . ? C17D C18D 1.3963(18) . ? C18D C19D 1.387(2) . ? C18D H18D 0.9500 . ? C19D C20D 1.390(2) . ? C19D H19D 0.9500 . ? C20D C21D 1.383(2) . ? C20D H20D 0.9500 . ? C21D C22D 1.3890(19) . ? C21D H21D 0.9500 . ? C22D H22D 0.9500 . ? C23D H23J 0.9800 . ? C23D H23K 0.9800 . ? C23D H23L 0.9800 . ? O1E C3E 1.411(2) . ? O1E C1E 1.420(2) . ? C1E C2E 1.510(3) . ? C1E H1E1 0.9900 . ? C1E H1E2 0.9900 . ? C2E H2E1 0.9800 . ? C2E H2E2 0.9800 . ? C2E H2E3 0.9800 . ? C3E C4E 1.507(3) . ? C3E H3E1 0.9900 . ? C3E H3E2 0.9900 . ? C4E H4E1 0.9800 . ? C4E H4E2 0.9800 . ? C4E H4E3 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 C15A N1A C1A 122.65(11) . . ? C15A N1A C16A 120.73(11) . . ? C1A N1A C16A 116.54(10) . . ? C12A O1A C1A 116.90(10) . . ? N1A C1A O1A 109.67(10) . . ? N1A C1A C5A 111.25(10) . . ? O1A C1A C5A 111.25(11) . . ? N1A C1A C2A 116.52(11) . . ? O1A C1A C2A 104.38(10) . . ? C5A C1A C2A 103.47(10) . . ? C1A C2A C3A 104.24(11) . . ? C1A C2A H2A1 110.9 . . ? C3A C2A H2A1 110.9 . . ? C1A C2A H2A2 110.9 . . ? C3A C2A H2A2 110.9 . . ? H2A1 C2A H2A2 108.9 . . ? C4A C3A C2A 106.66(11) . . ? C4A C3A H3A1 110.4 . . ? C2A C3A H3A1 110.4 . . ? C4A C3A H3A2 110.4 . . ? C2A C3A H3A2 110.4 . . ? H3A1 C3A H3A2 108.6 . . ? C5A C4A C3A 102.22(11) . . ? C5A C4A H4A1 111.3 . . ? C3A C4A H4A1 111.3 . . ? C5A C4A H4A2 111.3 . . ? C3A C4A H4A2 111.3 . . ? H4A1 C4A H4A2 109.2 . . ? C6A C5A C4A 122.02(12) . . ? C6A C5A C1A 107.36(10) . . ? C4A C5A C1A 102.49(11) . . ? C6A C5A H5A 108.1 . . ? C4A C5A H5A 108.1 . . ? C1A C5A H5A 108.1 . . ? C13A C6A C7A 110.09(10) . . ? C13A C6A C5A 105.89(11) . . ? C7A C6A C5A 110.12(11) . . ? C13A C6A H6A 110.2 . . ? C7A C6A H6A 110.2 . . ? C5A C6A H6A 110.2 . . ? C12A C7A C8A 118.06(12) . . ? C12A C7A C6A 120.39(12) . . ? C8A C7A C6A 121.50(12) . . ? C9A C8A C7A 121.49(13) . . ? C9A C8A H8A 119.3 . . ? C7A C8A H8A 119.3 . . ? C8A C9A C10A 119.45(14) . . ? C8A C9A H9A 120.3 . . ? C10A C9A H9A 120.3 . . ? C9A C10A C11A 120.20(13) . . ? C9A C10A H10A 119.9 . . ? C11A C10A H10A 119.9 . . ? C12A C11A C10A 119.73(13) . . ? C12A C11A H11A 120.1 . . ? C10A C11A H11A 120.1 . . ? O1A C12A C11A 116.69(12) . . ? O1A C12A C7A 122.26(12) . . ? C11A C12A C7A 121.04(13) . . ? C14A C13A C15A 118.61(13) . . ? C14A C13A C6A 123.40(13) . . ? C15A C13A C6A 118.00(11) . . ? C13A C14A H141 120.0 . . ? C13A C14A H142 120.0 . . ? H141 C14A H142 120.0 . . ? O2A C15A N1A 121.12(12) . . ? O2A C15A C13A 121.17(11) . . ? N1A C15A C13A 117.69(11) . . ? N1A C16A C17A 113.45(10) . . ? N1A C16A C23A 112.81(10) . . ? C17A C16A C23A 112.33(11) . . ? N1A C16A H16A 105.8 . . ? C17A C16A H16A 105.8 . . ? C23A C16A H16A 105.8 . . ? C18A C17A C22A 118.66(13) . . ? C18A C17A C16A 123.29(12) . . ? C22A C17A C16A 118.04(12) . . ? C19A C18A C17A 120.96(13) . . ? C19A C18A H18A 119.5 . . ? C17A C18A H18A 119.5 . . ? C18A C19A C20A 119.71(15) . . ? C18A C19A H19A 120.1 . . ? C20A C19A H19A 120.1 . . ? C21A C20A C19A 119.61(15) . . ? C21A C20A H20A 120.2 . . ? C19A C20A H20A 120.2 . . ? C22A C21A C20A 120.55(16) . . ? C22A C21A H21A 119.7 . . ? C20A C21A H21A 119.7 . . ? C21A C22A C17A 120.49(15) . . ? C21A C22A H22A 119.8 . . ? C17A C22A H22A 119.8 . . ? C16A C23A H23A 109.5 . . ? C16A C23A H23B 109.5 . . ? H23A C23A H23B 109.5 . . ? C16A C23A H23C 109.5 . . ? H23A C23A H23C 109.5 . . ? H23B C23A H23C 109.5 . . ? C15B N1B C1B 122.79(10) . . ? C15B N1B C16B 118.98(10) . . ? C1B N1B C16B 116.81(10) . . ? C8B O1B C1B 116.11(10) . . ? N1B C1B O1B 108.84(10) . . ? N1B C1B C5B 112.75(10) . . ? O1B C1B C5B 109.90(10) . . ? N1B C1B C2B 117.46(11) . . ? O1B C1B C2B 103.95(10) . . ? C5B C1B C2B 103.44(10) . . ? C1B C2B C3B 103.28(11) . . ? C1B C2B H2B1 111.1 . . ? C3B C2B H2B1 111.1 . . ? C1B C2B H2B2 111.1 . . ? C3B C2B H2B2 111.1 . . ? H2B1 C2B H2B2 109.1 . . ? C4B C3B C2B 106.82(11) . . ? C4B C3B H3B1 110.4 . . ? C2B C3B H3B1 110.4 . . ? C4B C3B H3B2 110.4 . . ? C2B C3B H3B2 110.4 . . ? H3B1 C3B H3B2 108.6 . . ? C5B C4B C3B 103.39(11) . . ? C5B C4B H4B1 111.1 . . ? C3B C4B H4B1 111.1 . . ? C5B C4B H4B2 111.1 . . ? C3B C4B H4B2 111.1 . . ? H4B1 C4B H4B2 109.0 . . ? C1B C5B C4B 102.09(10) . . ? C1B C5B C6B 107.57(10) . . ? C4B C5B C6B 121.49(12) . . ? C1B C5B H5B 108.3 . . ? C4B C5B H5B 108.3 . . ? C6B C5B H5B 108.3 . . ? C7B C6B C13B 108.75(10) . . ? C7B C6B C5B 110.40(11) . . ? C13B C6B C5B 105.05(11) . . ? C7B C6B H6B 110.8 . . ? C13B C6B H6B 110.8 . . ? C5B C6B H6B 110.8 . . ? C8B C7B C12B 117.65(13) . . ? C8B C7B C6B 120.39(12) . . ? C12B C7B C6B 121.84(12) . . ? O1B C8B C9B 116.04(12) . . ? O1B C8B C7B 122.22(12) . . ? C9B C8B C7B 121.72(13) . . ? C8B C9B C10B 119.54(13) . . ? C8B C9B H9B 120.2 . . ? C10B C9B H9B 120.2 . . ? C9B C10B C11B 119.97(14) . . ? C9B C10B H10B 120.0 . . ? C11B C10B H10B 120.0 . . ? C12B C11B C10B 120.04(14) . . ? C12B C11B H11B 120.0 . . ? C10B C11B H11B 120.0 . . ? C11B C12B C7B 121.07(14) . . ? C11B C12B H12B 119.5 . . ? C7B C12B H12B 119.5 . . ? C14B C13B C15B 118.73(12) . . ? C14B C13B C6B 123.86(12) . . ? C15B C13B C6B 117.38(11) . . ? C13B C14B H143 120.0 . . ? C13B C14B H144 120.0 . . ? H143 C14B H144 120.0 . . ? O2B C15B N1B 121.18(11) . . ? O2B C15B C13B 120.90(11) . . ? N1B C15B C13B 117.92(11) . . ? N1B C16B C17B 111.96(10) . . ? N1B C16B C23B 111.10(10) . . ? C17B C16B C23B 115.64(11) . . ? N1B C16B H16B 105.8 . . ? C17B C16B H16B 105.8 . . ? C23B C16B H16B 105.8 . . ? C22B C17B C18B 117.76(12) . . ? C22B C17B C16B 120.47(12) . . ? C18B C17B C16B 121.54(11) . . ? C19B C18B C17B 121.37(12) . . ? C19B C18B H18B 119.3 . . ? C17B C18B H18B 119.3 . . ? C18B C19B C20B 120.62(13) . . ? C18B C19B H19B 119.7 . . ? C20B C19B H19B 119.7 . . ? C19B C20B C21B 118.61(13) . . ? C19B C20B H20B 120.7 . . ? C21B C20B H20B 120.7 . . ? C22B C21B C20B 121.11(12) . . ? C22B C21B H21B 119.4 . . ? C20B C21B H21B 119.4 . . ? C21B C22B C17B 120.53(12) . . ? C21B C22B H22B 119.7 . . ? C17B C22B H22B 119.7 . . ? C16B C23B H23D 109.5 . . ? C16B C23B H23E 109.5 . . ? H23D C23B H23E 109.5 . . ? C16B C23B H23F 109.5 . . ? H23D C23B H23F 109.5 . . ? H23E C23B H23F 109.5 . . ? C15C N1C C1C 122.61(10) . . ? C15C N1C C16C 119.34(10) . . ? C1C N1C C16C 117.87(10) . . ? C8C O1C C1C 117.60(9) . . ? O1C C1C N1C 109.94(10) . . ? O1C C1C C5C 111.28(10) . . ? N1C C1C C5C 111.52(10) . . ? O1C C1C C2C 104.51(10) . . ? N1C C1C C2C 116.62(11) . . ? C5C C1C C2C 102.60(11) . . ? C1C C2C C3C 103.87(11) . . ? C1C C2C H2C1 111.0 . . ? C3C C2C H2C1 111.0 . . ? C1C C2C H2C2 111.0 . . ? C3C C2C H2C2 111.0 . . ? H2C1 C2C H2C2 109.0 . . ? C2C C3C C4C 106.59(11) . . ? C2C C3C H3C1 110.4 . . ? C4C C3C H3C1 110.4 . . ? C2C C3C H3C2 110.4 . . ? C4C C3C H3C2 110.4 . . ? H3C1 C3C H3C2 108.6 . . ? C5C C4C C3C 103.68(11) . . ? C5C C4C H4C1 111.0 . . ? C3C C4C H4C1 111.0 . . ? C5C C4C H4C2 111.0 . . ? C3C C4C H4C2 111.0 . . ? H4C1 C4C H4C2 109.0 . . ? C6C C5C C1C 107.37(11) . . ? C6C C5C C4C 120.49(11) . . ? C1C C5C C4C 102.99(11) . . ? C6C C5C H5C 108.5 . . ? C1C C5C H5C 108.5 . . ? C4C C5C H5C 108.5 . . ? C13C C6C C7C 110.12(10) . . ? C13C C6C C5C 106.54(10) . . ? C7C C6C C5C 109.45(10) . . ? C13C C6C H6C 110.2 . . ? C7C C6C H6C 110.2 . . ? C5C C6C H6C 110.2 . . ? C8C C7C C12C 118.54(12) . . ? C8C C7C C6C 120.15(11) . . ? C12C C7C C6C 121.28(12) . . ? O1C C8C C9C 116.41(11) . . ? O1C C8C C7C 122.40(12) . . ? C9C C8C C7C 121.18(12) . . ? C8C C9C C10C 119.23(12) . . ? C8C C9C H9C 120.4 . . ? C10C C9C H9C 120.4 . . ? C11C C10C C9C 120.41(13) . . ? C11C C10C H10C 119.8 . . ? C9C C10C H10C 119.8 . . ? C12C C11C C10C 119.64(13) . . ? C12C C11C H11C 120.2 . . ? C10C C11C H11C 120.2 . . ? C11C C12C C7C 121.01(12) . . ? C11C C12C H12C 119.5 . . ? C7C C12C H12C 119.5 . . ? C14C C13C C15C 118.17(12) . . ? C14C C13C C6C 122.83(12) . . ? C15C C13C C6C 118.98(11) . . ? C13C C14C H145 120.0 . . ? C13C C14C H146 120.0 . . ? H145 C14C H146 120.0 . . ? O2C C15C N1C 120.95(11) . . ? O2C C15C C13C 121.50(11) . . ? N1C C15C C13C 117.55(11) . . ? N1C C16C C17C 112.95(11) . . ? N1C C16C C23C 112.43(11) . . ? C17C C16C C23C 113.89(11) . . ? N1C C16C H16C 105.5 . . ? C17C C16C H16C 105.5 . . ? C23C C16C H16C 105.5 . . ? C18C C17C C22C 118.02(12) . . ? C18C C17C C16C 122.71(11) . . ? C22C C17C C16C 119.19(12) . . ? C17C C18C C19C 121.20(12) . . ? C17C C18C H18C 119.4 . . ? C19C C18C H18C 119.4 . . ? C20C C19C C18C 120.03(13) . . ? C20C C19C H19C 120.0 . . ? C18C C19C H19C 120.0 . . ? C21C C20C C19C 119.59(13) . . ? C21C C20C H20C 120.2 . . ? C19C C20C H20C 120.2 . . ? C20C C21C C22C 120.29(12) . . ? C20C C21C H21C 119.9 . . ? C22C C21C H21C 119.9 . . ? C21C C22C C17C 120.86(13) . . ? C21C C22C H22C 119.6 . . ? C17C C22C H22C 119.6 . . ? C16C C23C H23G 109.5 . . ? C16C C23C H23H 109.5 . . ? H23G C23C H23H 109.5 . . ? C16C C23C H23I 109.5 . . ? H23G C23C H23I 109.5 . . ? H23H C23C H23I 109.5 . . ? C15D N1D C1D 122.74(11) . . ? C15D N1D C16D 118.77(10) . . ? C1D N1D C16D 116.88(10) . . ? C8D O1D C1D 115.72(10) . . ? N1D C1D O1D 109.00(10) . . ? N1D C1D C2D 117.50(12) . . ? O1D C1D C2D 104.01(11) . . ? N1D C1D C5D 112.52(11) . . ? O1D C1D C5D 109.74(11) . . ? C2D C1D C5D 103.56(11) . . ? C1D C2D C3D 103.62(13) . . ? C1D C2D H2D1 111.0 . . ? C3D C2D H2D1 111.0 . . ? C1D C2D H2D2 111.0 . . ? C3D C2D H2D2 111.0 . . ? H2D1 C2D H2D2 109.0 . . ? C4D C3D C2D 106.73(12) . . ? C4D C3D H3D1 110.4 . . ? C2D C3D H3D1 110.4 . . ? C4D C3D H3D2 110.4 . . ? C2D C3D H3D2 110.4 . . ? H3D1 C3D H3D2 108.6 . . ? C5D C4D C3D 102.87(13) . . ? C5D C4D H4D1 111.2 . . ? C3D C4D H4D1 111.2 . . ? C5D C4D H4D2 111.2 . . ? C3D C4D H4D2 111.2 . . ? H4D1 C4D H4D2 109.1 . . ? C6D C5D C1D 107.76(11) . . ? C6D C5D C4D 121.61(13) . . ? C1D C5D C4D 101.74(11) . . ? C6D C5D H5D 108.3 . . ? C1D C5D H5D 108.3 . . ? C4D C5D H5D 108.3 . . ? C13D C6D C7D 108.61(10) . . ? C13D C6D C5D 104.74(11) . . ? C7D C6D C5D 110.71(12) . . ? C13D C6D H6D 110.9 . . ? C7D C6D H6D 110.9 . . ? C5D C6D H6D 110.9 . . ? C8D C7D C12D 118.08(13) . . ? C8D C7D C6D 120.18(12) . . ? C12D C7D C6D 121.54(13) . . ? O1D C8D C9D 116.16(13) . . ? O1D C8D C7D 122.50(12) . . ? C9D C8D C7D 121.34(14) . . ? C10D C9D C8D 119.73(15) . . ? C10D C9D H9D 120.1 . . ? C8D C9D H9D 120.1 . . ? C9D C10D C11D 119.90(14) . . ? C9D C10D H10D 120.1 . . ? C11D C10D H10D 120.1 . . ? C10D C11D C12D 120.15(15) . . ? C10D C11D H11D 119.9 . . ? C12D C11D H11D 119.9 . . ? C11D C12D C7D 120.78(15) . . ? C11D C12D H12D 119.6 . . ? C7D C12D H12D 119.6 . . ? C14D C13D C15D 118.96(12) . . ? C14D C13D C6D 123.88(13) . . ? C15D C13D C6D 117.14(12) . . ? C13D C14D H147 120.0 . . ? C13D C14D H148 120.0 . . ? H147 C14D H148 120.0 . . ? O2D C15D N1D 121.33(12) . . ? O2D C15D C13D 120.62(12) . . ? N1D C15D C13D 118.04(11) . . ? N1D C16D C17D 112.05(10) . . ? N1D C16D C23D 110.76(11) . . ? C17D C16D C23D 115.25(10) . . ? N1D C16D H16D 106.0 . . ? C17D C16D H16D 106.0 . . ? C23D C16D H16D 106.0 . . ? C22D C17D C18D 118.37(12) . . ? C22D C17D C16D 120.48(11) . . ? C18D C17D C16D 121.07(12) . . ? C19D C18D C17D 120.87(13) . . ? C19D C18D H18D 119.6 . . ? C17D C18D H18D 119.6 . . ? C18D C19D C20D 120.48(13) . . ? C18D C19D H19D 119.8 . . ? C20D C19D H19D 119.8 . . ? C21D C20D C19D 118.77(13) . . ? C21D C20D H20D 120.6 . . ? C19D C20D H20D 120.6 . . ? C20D C21D C22D 121.11(13) . . ? C20D C21D H21D 119.4 . . ? C22D C21D H21D 119.4 . . ? C21D C22D C17D 120.39(12) . . ? C21D C22D H22D 119.8 . . ? C17D C22D H22D 119.8 . . ? C16D C23D H23J 109.5 . . ? C16D C23D H23K 109.5 . . ? H23J C23D H23K 109.5 . . ? C16D C23D H23L 109.5 . . ? H23J C23D H23L 109.5 . . ? H23K C23D H23L 109.5 . . ? C3E O1E C1E 114.53(15) . . ? O1E C1E C2E 108.16(15) . . ? O1E C1E H1E1 110.1 . . ? C2E C1E H1E1 110.1 . . ? O1E C1E H1E2 110.1 . . ? C2E C1E H1E2 110.1 . . ? H1E1 C1E H1E2 108.4 . . ? C1E C2E H2E1 109.5 . . ? C1E C2E H2E2 109.5 . . ? H2E1 C2E H2E2 109.5 . . ? C1E C2E H2E3 109.5 . . ? H2E1 C2E H2E3 109.5 . . ? H2E2 C2E H2E3 109.5 . . ? O1E C3E C4E 108.36(16) . . ? O1E C3E H3E1 110.0 . . ? C4E C3E H3E1 110.0 . . ? O1E C3E H3E2 110.0 . . ? C4E C3E H3E2 110.0 . . ? H3E1 C3E H3E2 108.4 . . ? C3E C4E H4E1 109.5 . . ? C3E C4E H4E2 109.5 . . ? H4E1 C4E H4E2 109.5 . . ? C3E C4E H4E3 109.5 . . ? H4E1 C4E H4E3 109.5 . . ? H4E2 C4E H4E3 109.5 . . ? _refine_special_details ; Asymmetric unit contains four symmetrically independent molecules of the title compound augmented by a single cocrystalized diethyl ether moiety ; data_38 _database_code_depnum_ccdc_archive 'CCDC 912216' #==================================================== _chemical_name_systematic ; (3aR,9R,9aR)-10-methylene-12-[(S)-1-phenylethyl]-2,3,9,9a-tetrahydro-1H-3a,9- -(epiminoethano)cyclopenta[b]chromen-11-one ; _chemical_formula_moiety '4(C23 H23 N O2), C4 H10 O' _chemical_formula_sum 'C96 H102 N4 O9' _chemical_formula_weight 1455.88 _chemical_melting_point 386(1) _exptl_crystal_colour colourless _exptl_crystal_description plate _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_preparation ; slow evaporation from diethyl ether solution ; _exptl_crystal_F_000 778 _exptl_absorpt_coefficient_mu 0.613 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8614 _exptl_absorpt_correction_T_max 0.9412 _exptl_absorpt_process_details 'Bruker SADABS' _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' _cell_length_a 9.3543(1) _cell_length_b 13.0737(2) _cell_length_c 16.3819(2) _cell_angle_alpha 99.063(1) _cell_angle_beta 91.667(1) _cell_angle_gamma 90.832(1) _cell_volume 1977.21(4) _cell_formula_units_Z 1 _cell_measurement_temperature 291(1) _exptl_crystal_density_diffrn 1.223 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_ambient_temperature 291(2) _diffrn_reflns_number 35037 _reflns_number_total 14073 _reflns_number_gt 13950 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 74.14 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 70.14 _diffrn_measured_fraction_theta_full 0.971 _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^)+(0.0739P)^2^+0.1302P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_number_reflns 14073 _refine_ls_number_parameters 989 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.1072 _refine_ls_wR_factor_gt 0.1070 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.055 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(10) _chemical_absolute_configuration rmad _refine_ls_shift/su_max 0.036 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.166 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.031 _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' 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 O1A O 0.75267(13) -0.01774(9) 0.11403(7) 0.0581(3) Uani 1 1 d . . . O2A O 0.53502(15) 0.22530(10) 0.27881(8) 0.0662(3) Uani 1 1 d . . . N1A N 0.66444(13) 0.14380(10) 0.17473(8) 0.0470(3) Uani 1 1 d . . . C1A C 0.79156(16) 0.08857(13) 0.14708(10) 0.0502(3) Uani 1 1 d . . . C2A C 0.87241(19) 0.12819(18) 0.07821(12) 0.0648(4) Uani 1 1 d . . . H2A1 H 0.8665 0.2029 0.0830 0.078 Uiso 1 1 calc R . . H2A2 H 0.8343 0.0968 0.0242 0.078 Uiso 1 1 calc R . . C3A C 1.0276(2) 0.0954(2) 0.09151(16) 0.0823(6) Uani 1 1 d . . . H3A1 H 1.0921 0.1550 0.0963 0.099 Uiso 1 1 calc R . . H3A2 H 1.0558 0.0449 0.0452 0.099 Uiso 1 1 calc R . . C4A C 1.03367(19) 0.0479(2) 0.17203(15) 0.0763(6) Uani 1 1 d . . . H4A1 H 1.0258 -0.0271 0.1605 0.092 Uiso 1 1 calc R . . H4A2 H 1.1214 0.0680 0.2039 0.092 Uiso 1 1 calc R . . C5A C 0.90396(16) 0.09443(15) 0.21669(11) 0.0559(4) Uani 1 1 d . . . H5A H 0.9255 0.1676 0.2375 0.067 Uiso 1 1 calc R . . C6A C 0.83818(18) 0.04660(14) 0.28556(10) 0.0547(4) Uani 1 1 d . . . H6A H 0.9101 0.0424 0.3296 0.066 Uiso 1 1 calc R . . C7A C 0.77646(17) -0.06012(13) 0.25265(11) 0.0549(4) Uani 1 1 d . . . C8A C 0.7575(2) -0.13379(16) 0.30433(14) 0.0684(5) Uani 1 1 d . . . H8A H 0.7878 -0.1184 0.3595 0.082 Uiso 1 1 calc R . . C9A C 0.6948(3) -0.22889(18) 0.27539(19) 0.0844(7) Uani 1 1 d . . . H9A H 0.6820 -0.2772 0.3107 0.101 Uiso 1 1 calc R . . C10A C 0.6515(3) -0.25136(16) 0.1939(2) 0.0895(7) Uani 1 1 d . . . H10A H 0.6084 -0.3154 0.1743 0.107 Uiso 1 1 calc R . . C11A C 0.6704(2) -0.18055(16) 0.13987(16) 0.0754(5) Uani 1 1 d . . . H11A H 0.6416 -0.1970 0.0845 0.090 Uiso 1 1 calc R . . C12A C 0.73314(18) -0.08476(13) 0.17042(11) 0.0565(4) Uani 1 1 d . . . C13A C 0.72020(18) 0.11826(12) 0.31800(10) 0.0507(3) Uani 1 1 d . . . C14A C 0.6905(2) 0.14068(16) 0.39695(11) 0.0648(4) Uani 1 1 d . . . H141 H 0.6170 0.1857 0.4134 0.078 Uiso 1 1 calc R . . H142 H 0.7431 0.1115 0.4362 0.078 Uiso 1 1 calc R . . C15A C 0.63204(18) 0.16748(12) 0.25647(10) 0.0499(3) Uani 1 1 d . . . C16A C 0.56288(17) 0.16652(13) 0.10935(10) 0.0523(3) Uani 1 1 d . . . H16A H 0.5903 0.1223 0.0585 0.063 Uiso 1 1 calc R . . C17A C 0.57532(19) 0.27695(14) 0.09208(10) 0.0562(4) Uani 1 1 d . . . C18A C 0.6555(3) 0.35398(16) 0.14031(13) 0.0701(5) Uani 1 1 d . . . H18A H 0.7034 0.3394 0.1876 0.084 Uiso 1 1 calc R . . C19A C 0.6667(4) 0.45240(19) 0.12014(18) 0.0942(8) Uani 1 1 d . . . H19A H 0.7217 0.5032 0.1535 0.113 Uiso 1 1 calc R . . C20A C 0.5972(6) 0.4747(2) 0.0517(2) 0.1316(15) Uani 1 1 d . . . H20A H 0.6052 0.5405 0.0371 0.158 Uiso 1 1 calc R . . C21A C 0.5147(7) 0.3992(3) 0.0040(2) 0.153(2) Uani 1 1 d . . . H21A H 0.4653 0.4150 -0.0423 0.184 Uiso 1 1 calc R . . C22A C 0.5032(4) 0.3004(2) 0.02306(16) 0.1003(9) Uani 1 1 d . . . H22A H 0.4472 0.2502 -0.0103 0.120 Uiso 1 1 calc R . . C23A C 0.4084(2) 0.1344(2) 0.12410(18) 0.0841(6) Uani 1 1 d . . . H23A H 0.4062 0.0642 0.1348 0.126 Uiso 1 1 calc R . . H23B H 0.3495 0.1394 0.0760 0.126 Uiso 1 1 calc R . . H23C H 0.3728 0.1794 0.1708 0.126 Uiso 1 1 calc R . . O1B O -0.00965(13) 0.53040(11) 0.24825(9) 0.0676(3) Uani 1 1 d . . . O2B O 0.34837(13) 0.67396(9) 0.39619(7) 0.0559(3) Uani 1 1 d . . . N1B N 0.18201(14) 0.64766(10) 0.29202(8) 0.0490(3) Uani 1 1 d . . . C1B C 0.1151(2) 0.58084(16) 0.22144(11) 0.0612(4) Uani 1 1 d . . . C2B C 0.0594(3) 0.6323(2) 0.14997(13) 0.0856(7) Uani 1 1 d . . . H2B1 H 0.1226 0.6886 0.1409 0.103 Uiso 1 1 calc R . . H2B2 H -0.0357 0.6591 0.1603 0.103 Uiso 1 1 calc R . . C3B C 0.0567(4) 0.5438(3) 0.07514(14) 0.1068(10) Uani 1 1 d . . . H3B1 H -0.0412 0.5257 0.0565 0.128 Uiso 1 1 calc R . . H3B2 H 0.1077 0.5650 0.0297 0.128 Uiso 1 1 calc R . . C4B C 0.1290(3) 0.4512(3) 0.10395(15) 0.0973(8) Uani 1 1 d . . . H4B1 H 0.1900 0.4165 0.0618 0.117 Uiso 1 1 calc R . . H4B2 H 0.0587 0.4018 0.1176 0.117 Uiso 1 1 calc R . . C5B C 0.2173(2) 0.49986(17) 0.18098(12) 0.0707(5) Uani 1 1 d . . . H5B H 0.3003 0.5360 0.1629 0.085 Uiso 1 1 calc R . . C6B C 0.2683(2) 0.43700(15) 0.24568(12) 0.0656(5) Uani 1 1 d . . . H6B H 0.3252 0.3786 0.2208 0.079 Uiso 1 1 calc R . . C7B C 0.1451(2) 0.39997(14) 0.29070(13) 0.0658(5) Uani 1 1 d . . . C8B C 0.1595(3) 0.31895(16) 0.33613(16) 0.0829(7) Uani 1 1 d . . . H8B H 0.2445 0.2829 0.3353 0.099 Uiso 1 1 calc R . . C9B C 0.0471(4) 0.2919(2) 0.3826(2) 0.1009(9) Uani 1 1 d . . . H9B H 0.0571 0.2372 0.4123 0.121 Uiso 1 1 calc R . . C10B C -0.0785(4) 0.3452(2) 0.3852(2) 0.0997(9) Uani 1 1 d . . . H10B H -0.1517 0.3279 0.4180 0.120 Uiso 1 1 calc R . . C11B C -0.0968(3) 0.42435(19) 0.33922(17) 0.0820(6) Uani 1 1 d . . . H11B H -0.1828 0.4591 0.3395 0.098 Uiso 1 1 calc R . . C12B C 0.0154(2) 0.45109(14) 0.29261(12) 0.0631(4) Uani 1 1 d . . . C13B C 0.35966(18) 0.51286(14) 0.30641(11) 0.0576(4) Uani 1 1 d . . . C14B C 0.4856(2) 0.49184(19) 0.33532(18) 0.0860(7) Uani 1 1 d . . . H143 H 0.5354 0.5411 0.3731 0.103 Uiso 1 1 calc R . . H144 H 0.5254 0.4276 0.3181 0.103 Uiso 1 1 calc R . . C15B C 0.29745(16) 0.61788(12) 0.33545(9) 0.0483(3) Uani 1 1 d . . . C16B C 0.09940(16) 0.73861(12) 0.33012(9) 0.0483(3) Uani 1 1 d . . . H16B H 0.0194 0.7446 0.2913 0.058 Uiso 1 1 calc R . . C17B C 0.18541(16) 0.83933(12) 0.33666(9) 0.0482(3) Uani 1 1 d . . . C18B C 0.2970(2) 0.85013(15) 0.28427(13) 0.0628(4) Uani 1 1 d . . . H18B H 0.3235 0.7935 0.2463 0.075 Uiso 1 1 calc R . . C19B C 0.3694(2) 0.94422(18) 0.28788(16) 0.0737(5) Uani 1 1 d . . . H19B H 0.4439 0.9501 0.2524 0.088 Uiso 1 1 calc R . . C20B C 0.3320(2) 1.02862(16) 0.34341(15) 0.0705(5) Uani 1 1 d . . . H20B H 0.3808 1.0916 0.3458 0.085 Uiso 1 1 calc R . . C21B C 0.2219(2) 1.01922(15) 0.39542(14) 0.0669(4) Uani 1 1 d . . . H21B H 0.1956 1.0763 0.4329 0.080 Uiso 1 1 calc R . . C22B C 0.14933(18) 0.92528(14) 0.39257(11) 0.0549(4) Uani 1 1 d . . . H22B H 0.0756 0.9200 0.4286 0.066 Uiso 1 1 calc R . . C23B C 0.0323(2) 0.71882(14) 0.40981(11) 0.0574(4) Uani 1 1 d . . . H23D H -0.0155 0.6523 0.4006 0.086 Uiso 1 1 calc R . . H23E H -0.0356 0.7717 0.4269 0.086 Uiso 1 1 calc R . . H23F H 0.1056 0.7199 0.4522 0.086 Uiso 1 1 calc R . . O1C O 0.27288(14) 0.69464(9) 0.80259(7) 0.0560(3) Uani 1 1 d . . . O2C O 0.06144(15) 0.42938(10) 0.64960(9) 0.0647(3) Uani 1 1 d . . . N1C N 0.19793(14) 0.52195(10) 0.75183(8) 0.0489(3) Uani 1 1 d . . . C1C C 0.31988(17) 0.58976(12) 0.77804(10) 0.0506(3) Uani 1 1 d . . . C2C C 0.4088(2) 0.56750(18) 0.85234(13) 0.0722(5) Uani 1 1 d . . . H2C1 H 0.4174 0.4935 0.8514 0.087 Uiso 1 1 calc R . . H2C2 H 0.3659 0.5975 0.9036 0.087 Uiso 1 1 calc R . . C3C C 0.5548(3) 0.6178(3) 0.84372(19) 0.0981(8) Uani 1 1 d . . . H3C1 H 0.6306 0.5702 0.8519 0.118 Uiso 1 1 calc R . . H3C2 H 0.5682 0.6799 0.8845 0.118 Uiso 1 1 calc R . . C4C C 0.5577(2) 0.6452(2) 0.75585(16) 0.0804(6) Uani 1 1 d . . . H4C1 H 0.5471 0.7190 0.7568 0.096 Uiso 1 1 calc R . . H4C2 H 0.6462 0.6237 0.7295 0.096 Uiso 1 1 calc R . . C5C C 0.42928(18) 0.58430(15) 0.71092(11) 0.0578(4) Uani 1 1 d . . . H5C H 0.4567 0.5119 0.6958 0.069 Uiso 1 1 calc R . . C6C C 0.25267(17) 0.75521(12) 0.74091(11) 0.0510(3) Uani 1 1 d . . . C7C C 0.1899(2) 0.85042(14) 0.76431(12) 0.0606(4) Uani 1 1 d . . . H7C H 0.1623 0.8705 0.8185 0.073 Uiso 1 1 calc R . . C8C C 0.1688(2) 0.91546(14) 0.70551(15) 0.0695(5) Uani 1 1 d . . . H8C H 0.1270 0.9795 0.7206 0.083 Uiso 1 1 calc R . . C9C C 0.2092(2) 0.88568(14) 0.62559(13) 0.0665(5) Uani 1 1 d . . . H9C H 0.1947 0.9294 0.5866 0.080 Uiso 1 1 calc R . . C10C C 0.27123(19) 0.79094(14) 0.60332(11) 0.0566(4) Uani 1 1 d . . . H10C H 0.2986 0.7711 0.5491 0.068 Uiso 1 1 calc R . . C11C C 0.29362(16) 0.72431(12) 0.66066(10) 0.0489(3) Uani 1 1 d . . . C12C C 0.35715(18) 0.61851(13) 0.63601(10) 0.0527(3) Uani 1 1 d . . . H12C H 0.4263 0.6207 0.5925 0.063 Uiso 1 1 calc R . . C13C C 0.24012(18) 0.53899(11) 0.60668(9) 0.0495(3) Uani 1 1 d . . . C14C C 0.2050(2) 0.50953(15) 0.52784(11) 0.0652(4) Uani 1 1 d . . . H145 H 0.1318 0.4608 0.5126 0.078 Uiso 1 1 calc R . . H146 H 0.2534 0.5375 0.4875 0.078 Uiso 1 1 calc R . . C15C C 0.15942(17) 0.49199(12) 0.67015(10) 0.0491(3) Uani 1 1 d . . . C16C C 0.10528(18) 0.49276(13) 0.81648(10) 0.0544(4) Uani 1 1 d . . . H16C H 0.1404 0.5342 0.8685 0.065 Uiso 1 1 calc R . . C17C C 0.12183(18) 0.37980(13) 0.82822(9) 0.0503(3) Uani 1 1 d . . . C18C C 0.0419(2) 0.34271(16) 0.88735(11) 0.0656(4) Uani 1 1 d . . . H18C H -0.0241 0.3852 0.9168 0.079 Uiso 1 1 calc R . . C19C C 0.0598(3) 0.24162(19) 0.90310(14) 0.0790(6) Uani 1 1 d . . . H19C H 0.0063 0.2179 0.9435 0.095 Uiso 1 1 calc R . . C20C C 0.1540(3) 0.17752(17) 0.86029(14) 0.0764(6) Uani 1 1 d . . . H20C H 0.1649 0.1104 0.8714 0.092 Uiso 1 1 calc R . . C21C C 0.2326(3) 0.21221(17) 0.80087(14) 0.0744(5) Uani 1 1 d . . . H21C H 0.2966 0.1686 0.7709 0.089 Uiso 1 1 calc R . . C22C C 0.2162(2) 0.31318(15) 0.78542(12) 0.0633(4) Uani 1 1 d . . . H22C H 0.2706 0.3363 0.7451 0.076 Uiso 1 1 calc R . . C23C C -0.0505(2) 0.5242(2) 0.80513(18) 0.0823(6) Uani 1 1 d . . . H23G H -0.0529 0.5943 0.7945 0.123 Uiso 1 1 calc R . . H23H H -0.1012 0.5189 0.8545 0.123 Uiso 1 1 calc R . . H23I H -0.0950 0.4790 0.7593 0.123 Uiso 1 1 calc R . . O1D O 0.51554(12) 0.09795(10) 0.67495(8) 0.0578(3) Uani 1 1 d . . . O2D O 0.86280(13) -0.02312(9) 0.52405(7) 0.0560(3) Uani 1 1 d . . . N1D N 0.70418(13) -0.01031(10) 0.62646(8) 0.0465(3) Uani 1 1 d . . . C1D C 0.64363(18) 0.04766(14) 0.69932(10) 0.0534(3) Uani 1 1 d . . . C2D C 0.5942(2) -0.01232(19) 0.76600(12) 0.0708(5) Uani 1 1 d . . . H2D1 H 0.6602 -0.0669 0.7734 0.085 Uiso 1 1 calc R . . H2D2 H 0.4996 -0.0427 0.7523 0.085 Uiso 1 1 calc R . . C3D C 0.5923(3) 0.0708(2) 0.84460(14) 0.0873(7) Uani 1 1 d . . . H3D1 H 0.4946 0.0855 0.8603 0.105 Uiso 1 1 calc R . . H3D2 H 0.6430 0.0467 0.8902 0.105 Uiso 1 1 calc R . . C4D C 0.6664(3) 0.1684(2) 0.82316(13) 0.0853(7) Uani 1 1 d . . . H4D1 H 0.5968 0.2192 0.8122 0.102 Uiso 1 1 calc R . . H4D2 H 0.7312 0.1995 0.8678 0.102 Uiso 1 1 calc R . . C5D C 0.7483(2) 0.12846(16) 0.74544(11) 0.0627(4) Uani 1 1 d . . . H5D H 0.8329 0.0925 0.7621 0.075 Uiso 1 1 calc R . . C6D C 0.53552(19) 0.18341(13) 0.63711(11) 0.0581(4) Uani 1 1 d . . . C7D C 0.4190(2) 0.21393(17) 0.59338(15) 0.0735(5) Uani 1 1 d . . . H7D H 0.3334 0.1761 0.5896 0.088 Uiso 1 1 calc R . . C8D C 0.4302(3) 0.30013(19) 0.55558(18) 0.0899(7) Uani 1 1 d . . . H8D H 0.3523 0.3203 0.5258 0.108 Uiso 1 1 calc R . . C9D C 0.5554(4) 0.35636(18) 0.5616(2) 0.0950(8) Uani 1 1 d . . . H9D H 0.5618 0.4153 0.5366 0.114 Uiso 1 1 calc R . . C10D C 0.6723(3) 0.32605(16) 0.60446(17) 0.0802(6) Uani 1 1 d . . . H10D H 0.7571 0.3647 0.6077 0.096 Uiso 1 1 calc R . . C11D C 0.6652(2) 0.23859(13) 0.64287(12) 0.0618(4) Uani 1 1 d . . . C12D C 0.7943(2) 0.19924(14) 0.68543(12) 0.0629(4) Uani 1 1 d . . . H12D H 0.8535 0.2572 0.7140 0.076 Uiso 1 1 calc R . . C13D C 0.87910(17) 0.13196(13) 0.62191(11) 0.0551(4) Uani 1 1 d . . . C14D C 1.0020(2) 0.16004(17) 0.59402(16) 0.0751(5) Uani 1 1 d . . . H147 H 1.0416 0.2252 0.6137 0.090 Uiso 1 1 calc R . . H148 H 1.0490 0.1147 0.5547 0.090 Uiso 1 1 calc R . . C15D C 0.81641(15) 0.02651(12) 0.58633(10) 0.0471(3) Uani 1 1 d . . . C16D C 0.61992(15) -0.10136(12) 0.58400(9) 0.0460(3) Uani 1 1 d . . . H16D H 0.5409 -0.1106 0.6203 0.055 Uiso 1 1 calc R . . C17D C 0.70481(15) -0.20078(12) 0.57712(9) 0.0459(3) Uani 1 1 d . . . C18D C 0.82221(18) -0.21003(14) 0.62952(11) 0.0561(4) Uani 1 1 d . . . H18D H 0.8542 -0.1527 0.6669 0.067 Uiso 1 1 calc R . . C19D C 0.8920(2) -0.30288(16) 0.62693(13) 0.0651(4) Uani 1 1 d . . . H19D H 0.9706 -0.3071 0.6622 0.078 Uiso 1 1 calc R . . C20D C 0.8465(2) -0.38875(15) 0.57284(14) 0.0654(4) Uani 1 1 d . . . H20D H 0.8931 -0.4513 0.5715 0.079 Uiso 1 1 calc R . . C21D C 0.7306(2) -0.38098(14) 0.52032(13) 0.0635(4) Uani 1 1 d . . . H21D H 0.6989 -0.4388 0.4834 0.076 Uiso 1 1 calc R . . C22D C 0.66050(17) -0.28772(13) 0.52194(11) 0.0540(3) Uani 1 1 d . . . H22D H 0.5832 -0.2836 0.4857 0.065 Uiso 1 1 calc R . . C23D C 0.54999(19) -0.07936(14) 0.50316(11) 0.0566(4) Uani 1 1 d . . . H23J H 0.5043 -0.0134 0.5127 0.085 Uiso 1 1 calc R . . H23K H 0.4800 -0.1326 0.4835 0.085 Uiso 1 1 calc R . . H23L H 0.6218 -0.0782 0.4626 0.085 Uiso 1 1 calc R . . O1E O 0.1098(4) 0.8646(3) 0.96104(15) 0.1345(10) Uani 1 1 d . . . C1E C -0.0138(14) 0.8033(6) 0.9695(5) 0.234(5) Uani 1 1 d . . . H1E1 H -0.0442 0.8146 1.0263 0.281 Uiso 1 1 calc R . . H1E2 H 0.0053 0.7303 0.9534 0.281 Uiso 1 1 calc R . . C2E C -0.1294(7) 0.8386(9) 0.9116(6) 0.223(4) Uani 1 1 d . . . H2E1 H -0.1228 0.9124 0.9145 0.334 Uiso 1 1 calc R . . H2E2 H -0.2222 0.8196 0.9284 0.334 Uiso 1 1 calc R . . H2E3 H -0.1151 0.8057 0.8559 0.334 Uiso 1 1 calc R . . C3E C 0.2320(9) 0.8376(6) 1.0074(3) 0.187(3) Uani 1 1 d . . . H3E1 H 0.2425 0.7630 0.9989 0.224 Uiso 1 1 calc R . . H3E2 H 0.2209 0.8614 1.0659 0.224 Uiso 1 1 calc R . . C4E C 0.3606(9) 0.8884(9) 0.9776(5) 0.266(6) Uani 1 1 d . . . H4E1 H 0.3669 0.8677 0.9189 0.399 Uiso 1 1 calc R . . H4E2 H 0.4451 0.8679 1.0049 0.399 Uiso 1 1 calc R . . H4E3 H 0.3521 0.9623 0.9898 0.399 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 O1A 0.0583(6) 0.0613(7) 0.0548(6) 0.0086(5) 0.0030(5) 0.0096(5) O2A 0.0714(8) 0.0588(7) 0.0722(7) 0.0175(6) 0.0196(6) 0.0167(6) N1A 0.0399(6) 0.0509(6) 0.0522(6) 0.0149(5) -0.0007(5) 0.0006(5) C1A 0.0423(7) 0.0580(8) 0.0529(8) 0.0165(7) 0.0023(6) 0.0029(6) C2A 0.0521(9) 0.0855(12) 0.0619(10) 0.0256(9) 0.0123(7) 0.0048(9) C3A 0.0535(10) 0.1114(18) 0.0894(14) 0.0348(13) 0.0203(10) 0.0123(11) C4A 0.0396(8) 0.1063(16) 0.0895(13) 0.0345(12) 0.0069(8) 0.0073(9) C5A 0.0400(7) 0.0691(10) 0.0620(9) 0.0224(8) -0.0038(6) -0.0011(7) C6A 0.0487(8) 0.0652(9) 0.0531(8) 0.0204(7) -0.0076(6) 0.0006(7) C7A 0.0466(8) 0.0546(8) 0.0672(9) 0.0189(7) 0.0077(7) 0.0116(7) C8A 0.0640(11) 0.0624(10) 0.0856(12) 0.0297(9) 0.0121(9) 0.0166(9) C9A 0.0871(15) 0.0578(11) 0.1154(19) 0.0314(12) 0.0236(14) 0.0139(10) C10A 0.0911(16) 0.0454(9) 0.131(2) 0.0091(11) 0.0161(15) 0.0031(10) C11A 0.0740(12) 0.0555(10) 0.0930(14) -0.0011(10) 0.0073(11) 0.0081(9) C12A 0.0478(8) 0.0543(8) 0.0681(9) 0.0091(7) 0.0091(7) 0.0120(7) C13A 0.0555(8) 0.0459(7) 0.0521(8) 0.0141(6) -0.0017(6) -0.0099(6) C14A 0.0784(12) 0.0634(10) 0.0539(9) 0.0145(8) 0.0027(8) -0.0139(9) C15A 0.0521(8) 0.0449(7) 0.0541(8) 0.0125(6) 0.0057(6) -0.0053(6) C16A 0.0440(7) 0.0580(8) 0.0553(8) 0.0109(7) -0.0067(6) 0.0026(6) C17A 0.0604(9) 0.0606(9) 0.0504(8) 0.0162(7) 0.0015(7) 0.0111(8) C18A 0.0839(13) 0.0612(10) 0.0682(10) 0.0221(9) -0.0101(9) -0.0028(9) C19A 0.132(2) 0.0615(12) 0.0933(16) 0.0257(11) 0.0055(15) 0.0000(13) C20A 0.238(5) 0.0701(15) 0.0959(19) 0.0421(15) -0.002(2) 0.018(2) C21A 0.269(6) 0.108(2) 0.093(2) 0.0540(19) -0.048(3) 0.031(3) C22A 0.151(3) 0.0821(14) 0.0688(12) 0.0222(11) -0.0348(14) 0.0141(16) C23A 0.0517(10) 0.0979(15) 0.1064(16) 0.0323(13) -0.0177(10) -0.0102(10) O1B 0.0511(6) 0.0740(8) 0.0728(7) -0.0009(6) -0.0117(5) 0.0013(6) O2B 0.0540(6) 0.0552(6) 0.0569(6) 0.0059(5) -0.0077(5) 0.0025(5) N1B 0.0473(6) 0.0536(7) 0.0460(6) 0.0075(5) -0.0005(5) 0.0045(5) C1B 0.0578(9) 0.0724(11) 0.0510(8) 0.0028(8) -0.0050(7) 0.0059(8) C2B 0.0994(17) 0.1048(17) 0.0518(10) 0.0116(10) -0.0141(10) 0.0153(14) C3B 0.122(2) 0.141(3) 0.0516(11) 0.0008(13) -0.0173(12) 0.0101(19) C4B 0.1061(19) 0.114(2) 0.0607(12) -0.0188(12) -0.0094(12) 0.0120(16) C5B 0.0719(11) 0.0799(12) 0.0542(9) -0.0093(9) 0.0046(8) 0.0055(10) C6B 0.0617(10) 0.0603(10) 0.0680(10) -0.0116(8) 0.0020(8) 0.0100(8) C7B 0.0691(11) 0.0517(9) 0.0702(10) -0.0081(8) -0.0064(9) -0.0032(8) C8B 0.1028(17) 0.0480(9) 0.0926(15) -0.0011(10) -0.0162(13) -0.0051(10) C9B 0.136(3) 0.0585(12) 0.1054(19) 0.0074(12) -0.0017(18) -0.0284(15) C10B 0.111(2) 0.0693(14) 0.112(2) -0.0078(14) 0.0196(16) -0.0402(15) C11B 0.0702(12) 0.0706(13) 0.0964(15) -0.0123(12) 0.0022(11) -0.0214(10) C12B 0.0609(10) 0.0561(9) 0.0663(10) -0.0063(8) -0.0053(8) -0.0103(8) C13B 0.0479(8) 0.0579(9) 0.0655(9) 0.0045(8) 0.0042(7) 0.0039(7) C14B 0.0605(11) 0.0747(13) 0.1138(18) -0.0117(12) -0.0132(11) 0.0194(10) C15B 0.0451(7) 0.0513(8) 0.0489(7) 0.0090(6) 0.0018(6) 0.0015(6) C16B 0.0435(7) 0.0536(8) 0.0494(7) 0.0124(6) 0.0018(6) 0.0058(6) C17B 0.0426(7) 0.0539(8) 0.0516(7) 0.0188(6) 0.0019(6) 0.0072(6) C18B 0.0593(9) 0.0621(10) 0.0716(10) 0.0211(8) 0.0192(8) 0.0100(8) C19B 0.0585(10) 0.0727(12) 0.0991(14) 0.0382(11) 0.0215(10) 0.0031(9) C20B 0.0548(10) 0.0624(10) 0.1003(14) 0.0326(10) -0.0012(9) -0.0041(8) C21B 0.0644(10) 0.0577(9) 0.0788(11) 0.0113(9) 0.0014(9) 0.0018(8) C22B 0.0477(8) 0.0584(9) 0.0603(9) 0.0140(7) 0.0053(7) 0.0030(7) C23B 0.0565(9) 0.0556(9) 0.0628(9) 0.0157(7) 0.0133(7) 0.0003(7) O1C 0.0663(7) 0.0521(6) 0.0502(5) 0.0113(5) 0.0000(5) -0.0051(5) O2C 0.0699(8) 0.0541(6) 0.0709(7) 0.0164(6) -0.0117(6) -0.0126(6) N1C 0.0523(7) 0.0463(6) 0.0504(6) 0.0148(5) 0.0044(5) -0.0013(5) C1C 0.0508(8) 0.0517(8) 0.0525(8) 0.0195(6) -0.0025(6) -0.0029(7) C2C 0.0726(12) 0.0797(12) 0.0689(11) 0.0295(10) -0.0154(9) 0.0006(10) C3C 0.0613(12) 0.136(2) 0.1032(18) 0.0441(17) -0.0235(12) -0.0090(14) C4C 0.0469(9) 0.1000(16) 0.1001(15) 0.0361(13) -0.0066(9) -0.0090(10) C5C 0.0467(8) 0.0629(9) 0.0683(10) 0.0234(8) 0.0039(7) 0.0061(7) C6C 0.0472(7) 0.0468(7) 0.0595(8) 0.0126(6) -0.0063(6) -0.0096(6) C7C 0.0653(10) 0.0510(8) 0.0630(9) 0.0027(7) -0.0035(8) -0.0064(7) C8C 0.0725(11) 0.0435(8) 0.0920(13) 0.0120(8) -0.0097(10) 0.0013(8) C9C 0.0739(11) 0.0526(9) 0.0761(11) 0.0228(8) -0.0124(9) -0.0053(8) C10C 0.0573(9) 0.0560(8) 0.0596(9) 0.0204(7) -0.0027(7) -0.0113(7) C11C 0.0454(7) 0.0466(7) 0.0566(8) 0.0147(6) -0.0005(6) -0.0068(6) C12C 0.0511(8) 0.0560(8) 0.0550(8) 0.0196(7) 0.0106(6) 0.0035(7) C13C 0.0578(8) 0.0425(7) 0.0505(7) 0.0133(6) 0.0061(6) 0.0108(6) C14C 0.0857(13) 0.0562(9) 0.0544(9) 0.0102(7) 0.0031(8) 0.0096(9) C15C 0.0515(8) 0.0426(7) 0.0547(8) 0.0132(6) -0.0015(6) 0.0026(6) C16C 0.0557(9) 0.0547(8) 0.0547(8) 0.0134(7) 0.0109(7) 0.0002(7) C17C 0.0537(8) 0.0538(8) 0.0445(7) 0.0122(6) -0.0010(6) -0.0060(7) C18C 0.0776(12) 0.0684(11) 0.0536(9) 0.0166(8) 0.0131(8) -0.0068(9) C19C 0.1001(16) 0.0775(13) 0.0664(11) 0.0339(10) 0.0077(11) -0.0216(12) C20C 0.1007(16) 0.0585(10) 0.0749(12) 0.0273(9) -0.0041(11) -0.0075(10) C21C 0.0890(14) 0.0593(10) 0.0788(12) 0.0206(9) 0.0100(10) 0.0109(10) C22C 0.0664(10) 0.0617(10) 0.0676(10) 0.0257(8) 0.0154(8) 0.0055(8) C23C 0.0619(11) 0.0887(15) 0.1037(16) 0.0326(13) 0.0224(11) 0.0208(11) O1D 0.0450(6) 0.0598(6) 0.0673(7) 0.0049(5) 0.0065(5) 0.0015(5) O2D 0.0527(6) 0.0551(6) 0.0608(6) 0.0094(5) 0.0136(5) -0.0022(5) N1D 0.0412(6) 0.0490(6) 0.0501(6) 0.0102(5) 0.0028(5) -0.0028(5) C1D 0.0484(8) 0.0602(9) 0.0513(8) 0.0077(7) 0.0032(6) -0.0003(7) C2D 0.0696(11) 0.0895(14) 0.0556(9) 0.0184(9) 0.0096(8) -0.0048(10) C3D 0.0933(16) 0.1138(19) 0.0541(10) 0.0096(11) 0.0125(10) 0.0014(14) C4D 0.0872(15) 0.1028(17) 0.0579(10) -0.0111(11) 0.0023(10) -0.0048(13) C5D 0.0579(9) 0.0698(11) 0.0561(9) -0.0014(8) -0.0041(7) -0.0025(8) C6D 0.0556(9) 0.0515(8) 0.0633(9) -0.0045(7) 0.0062(7) 0.0104(7) C7D 0.0638(11) 0.0659(11) 0.0873(13) -0.0003(10) 0.0002(9) 0.0203(9) C8D 0.0986(18) 0.0694(13) 0.1019(17) 0.0119(12) -0.0029(14) 0.0365(13) C9D 0.120(2) 0.0545(11) 0.1137(19) 0.0192(12) 0.0134(16) 0.0277(13) C10D 0.0918(15) 0.0472(9) 0.1000(15) 0.0035(10) 0.0184(12) 0.0036(9) C11D 0.0626(10) 0.0482(8) 0.0708(10) -0.0029(8) 0.0077(8) 0.0028(7) C12D 0.0565(9) 0.0555(9) 0.0714(10) -0.0052(8) -0.0009(8) -0.0108(7) C13D 0.0446(8) 0.0541(8) 0.0667(9) 0.0110(7) -0.0023(7) -0.0056(7) C14D 0.0530(10) 0.0660(11) 0.1039(15) 0.0051(11) 0.0129(10) -0.0117(8) C15D 0.0400(7) 0.0484(7) 0.0543(8) 0.0128(6) 0.0008(6) -0.0001(6) C16D 0.0375(6) 0.0497(7) 0.0519(7) 0.0125(6) 0.0006(5) -0.0021(6) C17D 0.0376(6) 0.0495(7) 0.0531(7) 0.0161(6) 0.0017(6) -0.0034(6) C18D 0.0488(8) 0.0556(8) 0.0654(9) 0.0164(7) -0.0077(7) -0.0035(7) C19D 0.0488(8) 0.0671(10) 0.0838(12) 0.0283(9) -0.0107(8) 0.0010(8) C20D 0.0532(9) 0.0542(9) 0.0937(13) 0.0248(9) 0.0058(9) 0.0071(7) C21D 0.0628(10) 0.0522(9) 0.0746(11) 0.0074(8) 0.0021(8) -0.0019(8) C22D 0.0455(7) 0.0576(9) 0.0586(8) 0.0094(7) -0.0028(6) -0.0025(7) C23D 0.0544(8) 0.0570(8) 0.0603(9) 0.0173(7) -0.0106(7) -0.0014(7) O1E 0.173(3) 0.140(2) 0.0907(13) 0.0151(14) 0.0137(15) 0.044(2) C1E 0.339(13) 0.165(5) 0.189(7) -0.015(5) 0.128(8) -0.074(7) C2E 0.133(4) 0.308(11) 0.204(7) -0.032(7) 0.018(4) -0.025(6) C3E 0.241(7) 0.215(6) 0.105(3) 0.021(3) 0.000(4) 0.114(6) C4E 0.178(6) 0.399(13) 0.168(6) -0.115(7) -0.066(5) 0.099(8) _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 O1A C12A 1.384(2) . ? O1A C1A 1.447(2) . ? O2A C15A 1.217(2) . ? N1A C15A 1.370(2) . ? N1A C1A 1.4469(19) . ? N1A C16A 1.4789(19) . ? C1A C5A 1.521(2) . ? C1A C2A 1.528(2) . ? C2A C3A 1.539(3) . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? C3A C4A 1.544(3) . ? C3A H3A1 0.9700 . ? C3A H3A2 0.9700 . ? C4A C5A 1.520(3) . ? C4A H4A1 0.9700 . ? C4A H4A2 0.9700 . ? C5A C6A 1.515(2) . ? C5A H5A 0.9800 . ? C6A C13A 1.512(2) . ? C6A C7A 1.514(3) . ? C6A H6A 0.9800 . ? C7A C12A 1.382(3) . ? C7A C8A 1.392(3) . ? C8A C9A 1.375(4) . ? C8A H8A 0.9300 . ? C9A C10A 1.368(4) . ? C9A H9A 0.9300 . ? C10A C11A 1.391(4) . ? C10A H10A 0.9300 . ? C11A C12A 1.388(3) . ? C11A H11A 0.9300 . ? C13A C14A 1.319(3) . ? C13A C15A 1.511(2) . ? C14A H141 0.9300 . ? C14A H142 0.9300 . ? C16A C17A 1.518(2) . ? C16A C23A 1.536(3) . ? C16A H16A 0.9800 . ? C17A C18A 1.376(3) . ? C17A C22A 1.378(3) . ? C18A C19A 1.381(3) . ? C18A H18A 0.9300 . ? C19A C20A 1.354(5) . ? C19A H19A 0.9300 . ? C20A C21A 1.370(6) . ? C20A H20A 0.9300 . ? C21A C22A 1.378(5) . ? C21A H21A 0.9300 . ? C22A H22A 0.9300 . ? C23A H23A 0.9600 . ? C23A H23B 0.9600 . ? C23A H23C 0.9600 . ? O1B C12B 1.376(3) . ? O1B C1B 1.445(3) . ? O2B C15B 1.2194(19) . ? N1B C15B 1.371(2) . ? N1B C1B 1.454(2) . ? N1B C16B 1.4905(19) . ? C1B C2B 1.523(3) . ? C1B C5B 1.523(3) . ? C2B C3B 1.547(4) . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ? C3B C4B 1.526(5) . ? C3B H3B1 0.9700 . ? C3B H3B2 0.9700 . ? C4B C5B 1.533(3) . ? C4B H4B1 0.9700 . ? C4B H4B2 0.9700 . ? C5B C6B 1.511(3) . ? C5B H5B 0.9800 . ? C6B C7B 1.501(3) . ? C6B C13B 1.523(2) . ? C6B H6B 0.9800 . ? C7B C12B 1.393(3) . ? C7B C8B 1.393(3) . ? C8B C9B 1.389(5) . ? C8B H8B 0.9300 . ? C9B C10B 1.373(5) . ? C9B H9B 0.9300 . ? C10B C11B 1.382(4) . ? C10B H10B 0.9300 . ? C11B C12B 1.388(3) . ? C11B H11B 0.9300 . ? C13B C14B 1.306(3) . ? C13B C15B 1.511(2) . ? C14B H143 0.9300 . ? C14B H144 0.9300 . ? C16B C17B 1.521(2) . ? C16B C23B 1.521(2) . ? C16B H16B 0.9800 . ? C17B C22B 1.386(2) . ? C17B C18B 1.390(2) . ? C18B C19B 1.388(3) . ? C18B H18B 0.9300 . ? C19B C20B 1.372(3) . ? C19B H19B 0.9300 . ? C20B C21B 1.372(3) . ? C20B H20B 0.9300 . ? C21B C22B 1.388(3) . ? C21B H21B 0.9300 . ? C22B H22B 0.9300 . ? C23B H23D 0.9600 . ? C23B H23E 0.9600 . ? C23B H23F 0.9600 . ? O1C C6C 1.389(2) . ? O1C C1C 1.446(2) . ? O2C C15C 1.224(2) . ? N1C C15C 1.370(2) . ? N1C C1C 1.447(2) . ? N1C C16C 1.480(2) . ? C1C C5C 1.518(2) . ? C1C C2C 1.523(2) . ? C2C C3C 1.527(4) . ? C2C H2C1 0.9700 . ? C2C H2C2 0.9700 . ? C3C C4C 1.538(4) . ? C3C H3C1 0.9700 . ? C3C H3C2 0.9700 . ? C4C C5C 1.534(3) . ? C4C H4C1 0.9700 . ? C4C H4C2 0.9700 . ? C5C C12C 1.515(2) . ? C5C H5C 0.9800 . ? C6C C11C 1.380(2) . ? C6C C7C 1.387(2) . ? C7C C8C 1.394(3) . ? C7C H7C 0.9300 . ? C8C C9C 1.372(3) . ? C8C H8C 0.9300 . ? C9C C10C 1.377(3) . ? C9C H9C 0.9300 . ? C10C C11C 1.392(2) . ? C10C H10C 0.9300 . ? C11C C12C 1.514(2) . ? C12C C13C 1.513(2) . ? C12C H12C 0.9800 . ? C13C C14C 1.319(2) . ? C13C C15C 1.504(2) . ? C14C H145 0.9300 . ? C14C H146 0.9300 . ? C16C C17C 1.529(2) . ? C16C C23C 1.534(3) . ? C16C H16C 0.9800 . ? C17C C22C 1.377(3) . ? C17C C18C 1.383(3) . ? C18C C19C 1.397(3) . ? C18C H18C 0.9300 . ? C19C C20C 1.358(4) . ? C19C H19C 0.9300 . ? C20C C21C 1.366(3) . ? C20C H20C 0.9300 . ? C21C C22C 1.392(3) . ? C21C H21C 0.9300 . ? C22C H22C 0.9300 . ? C23C H23G 0.9600 . ? C23C H23H 0.9600 . ? C23C H23I 0.9600 . ? O1D C6D 1.373(2) . ? O1D C1D 1.451(2) . ? O2D C15D 1.2148(19) . ? N1D C15D 1.375(2) . ? N1D C1D 1.445(2) . ? N1D C16D 1.4840(19) . ? C1D C2D 1.520(3) . ? C1D C5D 1.524(2) . ? C2D C3D 1.549(3) . ? C2D H2D1 0.9700 . ? C2D H2D2 0.9700 . ? C3D C4D 1.538(4) . ? C3D H3D1 0.9700 . ? C3D H3D2 0.9700 . ? C4D C5D 1.530(3) . ? C4D H4D1 0.9700 . ? C4D H4D2 0.9700 . ? C5D C12D 1.519(3) . ? C5D H5D 0.9800 . ? C6D C7D 1.385(3) . ? C6D C11D 1.395(3) . ? C7D C8D 1.373(4) . ? C7D H7D 0.9300 . ? C8D C9D 1.366(4) . ? C8D H8D 0.9300 . ? C9D C10D 1.379(4) . ? C9D H9D 0.9300 . ? C10D C11D 1.391(3) . ? C10D H10D 0.9300 . ? C11D C12D 1.514(3) . ? C12D C13D 1.505(3) . ? C12D H12D 0.9800 . ? C13D C14D 1.317(3) . ? C13D C15D 1.513(2) . ? C14D H147 0.9300 . ? C14D H148 0.9300 . ? C16D C17D 1.524(2) . ? C16D C23D 1.530(2) . ? C16D H16D 0.9800 . ? C17D C22D 1.386(2) . ? C17D C18D 1.393(2) . ? C18D C19D 1.382(3) . ? C18D H18D 0.9300 . ? C19D C20D 1.370(3) . ? C19D H19D 0.9300 . ? C20D C21D 1.380(3) . ? C20D H20D 0.9300 . ? C21D C22D 1.389(3) . ? C21D H21D 0.9300 . ? C22D H22D 0.9300 . ? C23D H23J 0.9600 . ? C23D H23K 0.9600 . ? C23D H23L 0.9600 . ? O1E C1E 1.420(9) . ? O1E C3E 1.433(7) . ? C1E C2E 1.540(13) . ? C1E H1E1 0.9700 . ? C1E H1E2 0.9700 . ? C2E H2E1 0.9600 . ? C2E H2E2 0.9600 . ? C2E H2E3 0.9600 . ? C3E C4E 1.496(13) . ? C3E H3E1 0.9700 . ? C3E H3E2 0.9700 . ? C4E H4E1 0.9600 . ? C4E H4E2 0.9600 . ? C4E H4E3 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 C12A O1A C1A 117.04(12) . . ? C15A N1A C1A 122.84(13) . . ? C15A N1A C16A 120.61(13) . . ? C1A N1A C16A 116.36(13) . . ? O1A C1A N1A 109.23(13) . . ? O1A C1A C5A 111.32(13) . . ? N1A C1A C5A 111.26(13) . . ? O1A C1A C2A 104.91(14) . . ? N1A C1A C2A 116.68(14) . . ? C5A C1A C2A 103.19(14) . . ? C1A C2A C3A 104.11(15) . . ? C1A C2A H2A1 110.9 . . ? C3A C2A H2A1 110.9 . . ? C1A C2A H2A2 110.9 . . ? C3A C2A H2A2 110.9 . . ? H2A1 C2A H2A2 109.0 . . ? C2A C3A C4A 107.21(16) . . ? C2A C3A H3A1 110.3 . . ? C4A C3A H3A1 110.3 . . ? C2A C3A H3A2 110.3 . . ? C4A C3A H3A2 110.3 . . ? H3A1 C3A H3A2 108.5 . . ? C5A C4A C3A 102.26(16) . . ? C5A C4A H4A1 111.3 . . ? C3A C4A H4A1 111.3 . . ? C5A C4A H4A2 111.3 . . ? C3A C4A H4A2 111.3 . . ? H4A1 C4A H4A2 109.2 . . ? C6A C5A C4A 121.51(16) . . ? C6A C5A C1A 107.34(13) . . ? C4A C5A C1A 102.57(15) . . ? C6A C5A H5A 108.2 . . ? C4A C5A H5A 108.2 . . ? C1A C5A H5A 108.2 . . ? C13A C6A C7A 110.00(13) . . ? C13A C6A C5A 105.79(13) . . ? C7A C6A C5A 110.58(14) . . ? C13A C6A H6A 110.1 . . ? C7A C6A H6A 110.1 . . ? C5A C6A H6A 110.1 . . ? C12A C7A C8A 118.68(18) . . ? C12A C7A C6A 120.00(15) . . ? C8A C7A C6A 121.28(17) . . ? C9A C8A C7A 121.3(2) . . ? C9A C8A H8A 119.3 . . ? C7A C8A H8A 119.3 . . ? C10A C9A C8A 119.1(2) . . ? C10A C9A H9A 120.5 . . ? C8A C9A H9A 120.5 . . ? C9A C10A C11A 121.5(2) . . ? C9A C10A H10A 119.3 . . ? C11A C10A H10A 119.3 . . ? C12A C11A C10A 118.5(2) . . ? C12A C11A H11A 120.7 . . ? C10A C11A H11A 120.7 . . ? C7A C12A O1A 122.57(16) . . ? C7A C12A C11A 120.90(19) . . ? O1A C12A C11A 116.51(18) . . ? C14A C13A C15A 118.20(17) . . ? C14A C13A C6A 123.74(16) . . ? C15A C13A C6A 118.05(14) . . ? C13A C14A H141 120.0 . . ? C13A C14A H142 120.0 . . ? H141 C14A H142 120.0 . . ? O2A C15A N1A 121.37(15) . . ? O2A C15A C13A 121.06(15) . . ? N1A C15A C13A 117.56(14) . . ? N1A C16A C17A 113.45(13) . . ? N1A C16A C23A 112.50(16) . . ? C17A C16A C23A 112.69(16) . . ? N1A C16A H16A 105.8 . . ? C17A C16A H16A 105.8 . . ? C23A C16A H16A 105.8 . . ? C18A C17A C22A 118.4(2) . . ? C18A C17A C16A 124.03(15) . . ? C22A C17A C16A 117.55(19) . . ? C17A C18A C19A 121.5(2) . . ? C17A C18A H18A 119.2 . . ? C19A C18A H18A 119.2 . . ? C20A C19A C18A 119.8(3) . . ? C20A C19A H19A 120.1 . . ? C18A C19A H19A 120.1 . . ? C19A C20A C21A 119.2(3) . . ? C19A C20A H20A 120.4 . . ? C21A C20A H20A 120.4 . . ? C20A C21A C22A 121.7(3) . . ? C20A C21A H21A 119.1 . . ? C22A C21A H21A 119.1 . . ? C17A C22A C21A 119.3(3) . . ? C17A C22A H22A 120.3 . . ? C21A C22A H22A 120.3 . . ? C16A C23A H23A 109.5 . . ? C16A C23A H23B 109.5 . . ? H23A C23A H23B 109.5 . . ? C16A C23A H23C 109.5 . . ? H23A C23A H23C 109.5 . . ? H23B C23A H23C 109.5 . . ? C12B O1B C1B 116.37(14) . . ? C15B N1B C1B 122.52(13) . . ? C15B N1B C16B 118.50(12) . . ? C1B N1B C16B 117.12(12) . . ? O1B C1B N1B 109.07(14) . . ? O1B C1B C2B 104.31(17) . . ? N1B C1B C2B 117.24(18) . . ? O1B C1B C5B 109.87(17) . . ? N1B C1B C5B 112.05(14) . . ? C2B C1B C5B 103.86(16) . . ? C1B C2B C3B 103.7(2) . . ? C1B C2B H2B1 111.0 . . ? C3B C2B H2B1 111.0 . . ? C1B C2B H2B2 111.0 . . ? C3B C2B H2B2 111.0 . . ? H2B1 C2B H2B2 109.0 . . ? C4B C3B C2B 107.07(18) . . ? C4B C3B H3B1 110.3 . . ? C2B C3B H3B1 110.3 . . ? C4B C3B H3B2 110.3 . . ? C2B C3B H3B2 110.3 . . ? H3B1 C3B H3B2 108.6 . . ? C3B C4B C5B 103.6(2) . . ? C3B C4B H4B1 111.0 . . ? C5B C4B H4B1 111.0 . . ? C3B C4B H4B2 111.0 . . ? C5B C4B H4B2 111.0 . . ? H4B1 C4B H4B2 109.0 . . ? C6B C5B C1B 108.04(15) . . ? C6B C5B C4B 122.0(2) . . ? C1B C5B C4B 101.30(17) . . ? C6B C5B H5B 108.2 . . ? C1B C5B H5B 108.2 . . ? C4B C5B H5B 108.2 . . ? C7B C6B C5B 111.24(17) . . ? C7B C6B C13B 108.71(15) . . ? C5B C6B C13B 104.43(17) . . ? C7B C6B H6B 110.8 . . ? C5B C6B H6B 110.8 . . ? C13B C6B H6B 110.8 . . ? C12B C7B C8B 118.1(2) . . ? C12B C7B C6B 120.24(18) . . ? C8B C7B C6B 121.5(2) . . ? C9B C8B C7B 120.2(3) . . ? C9B C8B H8B 119.9 . . ? C7B C8B H8B 119.9 . . ? C10B C9B C8B 120.6(3) . . ? C10B C9B H9B 119.7 . . ? C8B C9B H9B 119.7 . . ? C9B C10B C11B 120.4(3) . . ? C9B C10B H10B 119.8 . . ? C11B C10B H10B 119.8 . . ? C10B C11B C12B 118.9(3) . . ? C10B C11B H11B 120.5 . . ? C12B C11B H11B 120.5 . . ? O1B C12B C11B 116.06(19) . . ? O1B C12B C7B 122.19(18) . . ? C11B C12B C7B 121.7(2) . . ? C14B C13B C15B 118.89(17) . . ? C14B C13B C6B 124.11(17) . . ? C15B C13B C6B 116.99(14) . . ? C13B C14B H143 120.0 . . ? C13B C14B H144 120.0 . . ? H143 C14B H144 120.0 . . ? O2B C15B N1B 121.20(14) . . ? O2B C15B C13B 120.66(14) . . ? N1B C15B C13B 118.14(13) . . ? N1B C16B C17B 112.02(12) . . ? N1B C16B C23B 111.25(13) . . ? C17B C16B C23B 115.23(13) . . ? N1B C16B H16B 105.8 . . ? C17B C16B H16B 105.8 . . ? C23B C16B H16B 105.8 . . ? C22B C17B C18B 117.88(16) . . ? C22B C17B C16B 120.52(14) . . ? C18B C17B C16B 121.51(15) . . ? C19B C18B C17B 120.88(18) . . ? C19B C18B H18B 119.6 . . ? C17B C18B H18B 119.6 . . ? C20B C19B C18B 120.49(19) . . ? C20B C19B H19B 119.8 . . ? C18B C19B H19B 119.8 . . ? C19B C20B C21B 119.31(19) . . ? C19B C20B H20B 120.3 . . ? C21B C20B H20B 120.3 . . ? C20B C21B C22B 120.62(19) . . ? C20B C21B H21B 119.7 . . ? C22B C21B H21B 119.7 . . ? C17B C22B C21B 120.82(16) . . ? C17B C22B H22B 119.6 . . ? C21B C22B H22B 119.6 . . ? C16B C23B H23D 109.5 . . ? C16B C23B H23E 109.5 . . ? H23D C23B H23E 109.5 . . ? C16B C23B H23F 109.5 . . ? H23D C23B H23F 109.5 . . ? H23E C23B H23F 109.5 . . ? C6C O1C C1C 117.55(12) . . ? C15C N1C C1C 122.30(13) . . ? C15C N1C C16C 119.57(14) . . ? C1C N1C C16C 117.88(13) . . ? O1C C1C N1C 109.93(13) . . ? O1C C1C C5C 111.24(13) . . ? N1C C1C C5C 111.42(14) . . ? O1C C1C C2C 103.99(14) . . ? N1C C1C C2C 117.19(14) . . ? C5C C1C C2C 102.68(14) . . ? C1C C2C C3C 104.77(17) . . ? C1C C2C H2C1 110.8 . . ? C3C C2C H2C1 110.8 . . ? C1C C2C H2C2 110.8 . . ? C3C C2C H2C2 110.8 . . ? H2C1 C2C H2C2 108.9 . . ? C2C C3C C4C 106.88(18) . . ? C2C C3C H3C1 110.3 . . ? C4C C3C H3C1 110.3 . . ? C2C C3C H3C2 110.3 . . ? C4C C3C H3C2 110.3 . . ? H3C1 C3C H3C2 108.6 . . ? C5C C4C C3C 103.75(18) . . ? C5C C4C H4C1 111.0 . . ? C3C C4C H4C1 111.0 . . ? C5C C4C H4C2 111.0 . . ? C3C C4C H4C2 111.0 . . ? H4C1 C4C H4C2 109.0 . . ? C12C C5C C1C 107.68(13) . . ? C12C C5C C4C 121.03(17) . . ? C1C C5C C4C 102.78(16) . . ? C12C C5C H5C 108.2 . . ? C1C C5C H5C 108.2 . . ? C4C C5C H5C 108.2 . . ? C11C C6C C7C 121.01(16) . . ? C11C C6C O1C 122.66(14) . . ? C7C C6C O1C 116.33(15) . . ? C6C C7C C8C 119.08(18) . . ? C6C C7C H7C 120.5 . . ? C8C C7C H7C 120.5 . . ? C9C C8C C7C 120.46(18) . . ? C9C C8C H8C 119.8 . . ? C7C C8C H8C 119.8 . . ? C8C C9C C10C 119.77(17) . . ? C8C C9C H9C 120.1 . . ? C10C C9C H9C 120.1 . . ? C9C C10C C11C 121.06(18) . . ? C9C C10C H10C 119.5 . . ? C11C C10C H10C 119.5 . . ? C6C C11C C10C 118.62(15) . . ? C6C C11C C12C 119.97(14) . . ? C10C C11C C12C 121.38(15) . . ? C13C C12C C11C 110.26(13) . . ? C13C C12C C5C 106.33(14) . . ? C11C C12C C5C 109.54(14) . . ? C13C C12C H12C 110.2 . . ? C11C C12C H12C 110.2 . . ? C5C C12C H12C 110.2 . . ? C14C C13C C15C 118.47(17) . . ? C14C C13C C12C 122.88(17) . . ? C15C C13C C12C 118.65(13) . . ? C13C C14C H145 120.0 . . ? C13C C14C H146 120.0 . . ? H145 C14C H146 120.0 . . ? O2C C15C N1C 120.84(15) . . ? O2C C15C C13C 121.07(15) . . ? N1C C15C C13C 118.09(14) . . ? N1C C16C C17C 112.71(13) . . ? N1C C16C C23C 112.46(15) . . ? C17C C16C C23C 113.81(16) . . ? N1C C16C H16C 105.7 . . ? C17C C16C H16C 105.7 . . ? C23C C16C H16C 105.7 . . ? C22C C17C C18C 117.57(16) . . ? C22C C17C C16C 123.79(15) . . ? C18C C17C C16C 118.59(16) . . ? C17C C18C C19C 120.3(2) . . ? C17C C18C H18C 119.9 . . ? C19C C18C H18C 119.9 . . ? C20C C19C C18C 121.0(2) . . ? C20C C19C H19C 119.5 . . ? C18C C19C H19C 119.5 . . ? C19C C20C C21C 119.58(19) . . ? C19C C20C H20C 120.2 . . ? C21C C20C H20C 120.2 . . ? C20C C21C C22C 119.7(2) . . ? C20C C21C H21C 120.2 . . ? C22C C21C H21C 120.2 . . ? C17C C22C C21C 121.84(18) . . ? C17C C22C H22C 119.1 . . ? C21C C22C H22C 119.1 . . ? C16C C23C H23G 109.5 . . ? C16C C23C H23H 109.5 . . ? H23G C23C H23H 109.5 . . ? C16C C23C H23I 109.5 . . ? H23G C23C H23I 109.5 . . ? H23H C23C H23I 109.5 . . ? C6D O1D C1D 116.56(13) . . ? C15D N1D C1D 122.98(13) . . ? C15D N1D C16D 118.83(12) . . ? C1D N1D C16D 116.73(12) . . ? N1D C1D O1D 108.87(13) . . ? N1D C1D C2D 117.72(15) . . ? O1D C1D C2D 104.08(15) . . ? N1D C1D C5D 112.31(14) . . ? O1D C1D C5D 109.71(14) . . ? C2D C1D C5D 103.67(15) . . ? C1D C2D C3D 103.76(19) . . ? C1D C2D H2D1 111.0 . . ? C3D C2D H2D1 111.0 . . ? C1D C2D H2D2 111.0 . . ? C3D C2D H2D2 111.0 . . ? H2D1 C2D H2D2 109.0 . . ? C4D C3D C2D 106.75(17) . . ? C4D C3D H3D1 110.4 . . ? C2D C3D H3D1 110.4 . . ? C4D C3D H3D2 110.4 . . ? C2D C3D H3D2 110.4 . . ? H3D1 C3D H3D2 108.6 . . ? C5D C4D C3D 103.85(19) . . ? C5D C4D H4D1 111.0 . . ? C3D C4D H4D1 111.0 . . ? C5D C4D H4D2 111.0 . . ? C3D C4D H4D2 111.0 . . ? H4D1 C4D H4D2 109.0 . . ? C12D C5D C1D 107.83(14) . . ? C12D C5D C4D 122.06(19) . . ? C1D C5D C4D 101.75(16) . . ? C12D C5D H5D 108.1 . . ? C1D C5D H5D 108.1 . . ? C4D C5D H5D 108.1 . . ? O1D C6D C7D 116.61(17) . . ? O1D C6D C11D 122.43(16) . . ? C7D C6D C11D 120.95(19) . . ? C8D C7D C6D 119.8(2) . . ? C8D C7D H7D 120.1 . . ? C6D C7D H7D 120.1 . . ? C9D C8D C7D 120.3(2) . . ? C9D C8D H8D 119.9 . . ? C7D C8D H8D 119.9 . . ? C8D C9D C10D 120.3(2) . . ? C8D C9D H9D 119.8 . . ? C10D C9D H9D 119.8 . . ? C9D C10D C11D 121.0(2) . . ? C9D C10D H10D 119.5 . . ? C11D C10D H10D 119.5 . . ? C10D C11D C6D 117.68(19) . . ? C10D C11D C12D 122.20(19) . . ? C6D C11D C12D 120.02(17) . . ? C13D C12D C11D 108.92(15) . . ? C13D C12D C5D 105.12(15) . . ? C11D C12D C5D 110.62(16) . . ? C13D C12D H12D 110.7 . . ? C11D C12D H12D 110.7 . . ? C5D C12D H12D 110.7 . . ? C14D C13D C12D 124.27(17) . . ? C14D C13D C15D 118.19(17) . . ? C12D C13D C15D 117.51(14) . . ? C13D C14D H147 120.0 . . ? C13D C14D H148 120.0 . . ? H147 C14D H148 120.0 . . ? O2D C15D N1D 121.41(14) . . ? O2D C15D C13D 121.02(14) . . ? N1D C15D C13D 117.57(13) . . ? N1D C16D C17D 112.04(11) . . ? N1D C16D C23D 111.34(13) . . ? C17D C16D C23D 115.33(13) . . ? N1D C16D H16D 105.8 . . ? C17D C16D H16D 105.8 . . ? C23D C16D H16D 105.8 . . ? C22D C17D C18D 117.81(14) . . ? C22D C17D C16D 120.43(13) . . ? C18D C17D C16D 121.60(14) . . ? C19D C18D C17D 121.16(17) . . ? C19D C18D H18D 119.4 . . ? C17D C18D H18D 119.4 . . ? C20D C19D C18D 120.65(16) . . ? C20D C19D H19D 119.7 . . ? C18D C19D H19D 119.7 . . ? C19D C20D C21D 118.99(16) . . ? C19D C20D H20D 120.5 . . ? C21D C20D H20D 120.5 . . ? C20D C21D C22D 120.79(17) . . ? C20D C21D H21D 119.6 . . ? C22D C21D H21D 119.6 . . ? C17D C22D C21D 120.59(15) . . ? C17D C22D H22D 119.7 . . ? C21D C22D H22D 119.7 . . ? C16D C23D H23J 109.5 . . ? C16D C23D H23K 109.5 . . ? H23J C23D H23K 109.5 . . ? C16D C23D H23L 109.5 . . ? H23J C23D H23L 109.5 . . ? H23K C23D H23L 109.5 . . ? C1E O1E C3E 113.2(7) . . ? O1E C1E C2E 105.6(6) . . ? O1E C1E H1E1 110.6 . . ? C2E C1E H1E1 110.6 . . ? O1E C1E H1E2 110.6 . . ? C2E C1E H1E2 110.6 . . ? H1E1 C1E H1E2 108.8 . . ? C1E C2E H2E1 109.5 . . ? C1E C2E H2E2 109.5 . . ? H2E1 C2E H2E2 109.5 . . ? C1E C2E H2E3 109.5 . . ? H2E1 C2E H2E3 109.5 . . ? H2E2 C2E H2E3 109.5 . . ? O1E C3E C4E 107.6(6) . . ? O1E C3E H3E1 110.2 . . ? C4E C3E H3E1 110.2 . . ? O1E C3E H3E2 110.2 . . ? C4E C3E H3E2 110.2 . . ? H3E1 C3E H3E2 108.5 . . ? C3E C4E H4E1 109.5 . . ? C3E C4E H4E2 109.5 . . ? H4E1 C4E H4E2 109.5 . . ? C3E C4E H4E3 109.5 . . ? H4E1 C4E H4E3 109.5 . . ? H4E2 C4E H4E3 109.5 . . ? _refine_special_details ; Asymmetric unit contains four symmetrically independent molecules of the title compound augmented by a single cocrystalized diethyl ether moiety ; data_43 _database_code_depnum_ccdc_archive 'CCDC 912217' #==================================================== _chemical_name_systematic ; diethyl [(3R,4R)-4-(2-hydroxyphenyl)-2-oxo-1-((R)-1- phenylethyl)-1,2,3,4,5,6,7,8-octahydroquinolin-3-yl]phosphonate ; _chemical_formula_moiety '2(C27 H34 N O5 P)' _chemical_formula_sum 'C54 H68 N2 O10 P2' _chemical_formula_weight 967.0861 _chemical_melting_point 487(1) _exptl_crystal_colour colourless _exptl_crystal_description prism _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_preparation ; slow evaporation for benzene and n-heptane 3:1 mixture ; _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 1.235 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6710 _exptl_absorpt_correction_T_max 0.7836 _exptl_absorpt_process_details 'Bruker SADABS' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 15.3327(12) _cell_length_b 9.0849(7) _cell_length_c 19.0305(15) _cell_angle_alpha 90.00 _cell_angle_beta 101.416(3) _cell_angle_gamma 90.00 _cell_volume 2598.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 291(1) _exptl_crystal_density_diffrn 1.236 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_ambient_temperature 291(2) _diffrn_reflns_number 29553 _reflns_number_total 9210 _reflns_number_gt 9034 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 68.00 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 68.00 _diffrn_measured_fraction_theta_full 0.999 _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^)+(0.0834P)^2^+0.2928P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_number_reflns 9210 _refine_ls_number_parameters 681 _refine_ls_number_restraints 37 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.1175 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.037 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.010(14) _chemical_absolute_configuration rmad _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.360 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.036 _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' 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 0.19549(3) 0.30069(7) 1.05063(3) 0.05122(14) Uani 1 1 d . A . O1 O 0.26673(12) 0.48361(18) 0.91304(12) 0.0716(5) Uani 1 1 d . . . O2 O -0.01919(11) 0.4897(2) 0.91906(9) 0.0639(4) Uani 1 1 d . . . H2 H -0.0510 0.5630 0.9146 0.077 Uiso 1 1 calc R . . O3 O 0.28708(13) 0.2207(2) 1.05419(11) 0.0752(5) Uani 1 1 d . . . O4 O 0.12901(13) 0.2225(2) 1.08253(9) 0.0731(5) Uani 1 1 d . . . O5 O 0.22689(10) 0.4491(2) 1.09000(9) 0.0605(4) Uani 1 1 d . . . C1 C 0.15598(12) 0.3464(2) 0.95693(11) 0.0452(4) Uani 1 1 d . . . H11 H 0.1267 0.4425 0.9559 0.054 Uiso 1 1 calc R A . C2 C 0.23160(14) 0.3644(2) 0.91616(13) 0.0501(4) Uani 1 1 d . A . N1 N 0.25446(11) 0.24135(19) 0.88369(10) 0.0490(4) Uani 1 1 d . . . C4 C 0.21470(13) 0.1017(2) 0.89326(11) 0.0460(4) Uani 1 1 d . A . C5 C 0.27112(16) -0.0336(3) 0.89199(15) 0.0608(5) Uani 1 1 d . . . H51 H 0.2754 -0.0551 0.8429 0.073 Uiso 1 1 calc R A . H52 H 0.3307 -0.0144 0.9188 0.073 Uiso 1 1 calc R . . C6 C 0.2339(2) -0.1646(3) 0.9232(3) 0.0939(11) Uani 1 1 d . A . H61 H 0.2619 -0.2525 0.9090 0.113 Uiso 1 1 calc R . . H62 H 0.2494 -0.1580 0.9751 0.113 Uiso 1 1 calc R . . C7 C 0.1370(2) -0.1811(3) 0.9020(2) 0.0852(9) Uani 1 1 d . . . H71 H 0.1183 -0.2642 0.9274 0.102 Uiso 1 1 calc R A . H72 H 0.1219 -0.2028 0.8511 0.102 Uiso 1 1 calc R . . C8 C 0.08636(16) -0.0467(3) 0.91687(14) 0.0582(5) Uani 1 1 d . A . H81 H 0.0765 -0.0522 0.9656 0.070 Uiso 1 1 calc R . . H82 H 0.0286 -0.0469 0.8850 0.070 Uiso 1 1 calc R . . C9 C 0.13260(13) 0.0960(2) 0.90767(11) 0.0463(4) Uani 1 1 d . . . C10 C 0.08535(13) 0.2379(2) 0.91822(11) 0.0455(4) Uani 1 1 d . A . H101 H 0.0441 0.2172 0.9503 0.055 Uiso 1 1 calc R . . C11 C 0.03160(13) 0.3043(3) 0.84925(11) 0.0503(4) Uani 1 1 d . . . C12 C -0.01869(15) 0.4310(3) 0.85283(12) 0.0556(5) Uani 1 1 d . A . C13 C -0.0684(2) 0.4917(4) 0.79091(15) 0.0769(7) Uani 1 1 d . . . H131 H -0.1009 0.5773 0.7937 0.092 Uiso 1 1 calc R A . C14 C -0.0704(2) 0.4270(5) 0.72538(16) 0.0907(10) Uani 1 1 d . A . H141 H -0.1042 0.4685 0.6842 0.109 Uiso 1 1 calc R . . C15 C -0.0223(2) 0.3004(5) 0.72061(15) 0.0861(9) Uani 1 1 d . . . H151 H -0.0244 0.2550 0.6765 0.103 Uiso 1 1 calc R A . C16 C 0.02917(18) 0.2419(3) 0.78214(13) 0.0666(6) Uani 1 1 d . A . H161 H 0.0631 0.1584 0.7786 0.080 Uiso 1 1 calc R . . C17 C 0.31763(16) 0.2605(3) 0.83425(14) 0.0598(5) Uani 1 1 d . A . H171 H 0.3240 0.3671 0.8292 0.072 Uiso 1 1 calc R . . C18 C 0.2775(2) 0.2053(4) 0.75989(16) 0.0838(8) Uani 1 1 d . . . H181 H 0.3146 0.2342 0.7271 0.101 Uiso 1 1 calc R A . H172 H 0.2192 0.2468 0.7447 0.101 Uiso 1 1 calc R . . H173 H 0.2732 0.0999 0.7606 0.101 Uiso 1 1 calc R . . C19 C 0.41039(16) 0.2047(3) 0.86777(16) 0.0634(6) Uani 1 1 d . . . C20 C 0.44815(18) 0.2427(4) 0.93723(19) 0.0836(8) Uani 1 1 d . A . H201 H 0.4167 0.3025 0.9631 0.100 Uiso 1 1 calc R . . C21 C 0.5320(2) 0.1934(6) 0.9691(2) 0.1058(13) Uani 1 1 d . . . H211 H 0.5557 0.2199 1.0162 0.127 Uiso 1 1 calc R A . C22 C 0.5803(2) 0.1075(6) 0.9330(3) 0.1147(15) Uani 1 1 d . A . H221 H 0.6355 0.0713 0.9555 0.138 Uiso 1 1 calc R . . C23 C 0.5463(3) 0.0750(5) 0.8632(3) 0.1165(15) Uani 1 1 d . . . H231 H 0.5806 0.0215 0.8369 0.140 Uiso 1 1 calc R A . C24 C 0.4611(2) 0.1204(4) 0.8301(2) 0.0906(10) Uani 1 1 d . A . H241 H 0.4383 0.0942 0.7828 0.109 Uiso 1 1 calc R . . C25 C 0.16442(19) 0.5616(5) 1.1008(2) 0.0936(11) Uani 1 1 d . A . H251 H 0.1219 0.5202 1.1269 0.112 Uiso 1 1 calc R . . H252 H 0.1319 0.5952 1.0546 0.112 Uiso 1 1 calc R . . C26 C 0.2089(3) 0.6858(5) 1.1404(3) 0.1230(17) Uani 1 1 d . . . H261 H 0.1666 0.7631 1.1420 0.148 Uiso 1 1 calc R A . H262 H 0.2550 0.7211 1.1171 0.148 Uiso 1 1 calc R . . H263 H 0.2347 0.6555 1.1884 0.148 Uiso 1 1 calc R . . C27 C 0.3141(8) 0.0928(13) 1.0938(9) 0.118(4) Uani 0.540(19) 1 d PD A 1 H271 H 0.3017 0.0067 1.0633 0.142 Uiso 0.540(19) 1 calc PR A 1 H272 H 0.2821 0.0833 1.1328 0.142 Uiso 0.540(19) 1 calc PR A 1 C28 C 0.4108(9) 0.105(2) 1.1227(11) 0.146(6) Uani 0.540(19) 1 d PD A 1 H281 H 0.4229 0.0796 1.1727 0.175 Uiso 0.540(19) 1 calc PR A 1 H282 H 0.4299 0.2039 1.1169 0.175 Uiso 0.540(19) 1 calc PR A 1 H283 H 0.4422 0.0386 1.0972 0.175 Uiso 0.540(19) 1 calc PR A 1 C27A C 0.3381(9) 0.1640(19) 1.1189(5) 0.100(4) Uani 0.460(19) 1 d PD A 2 H273 H 0.2984 0.1295 1.1493 0.120 Uiso 0.460(19) 1 calc PR A 2 H274 H 0.3746 0.2420 1.1443 0.120 Uiso 0.460(19) 1 calc PR A 2 C28A C 0.3960(13) 0.0414(14) 1.1053(9) 0.098(4) Uani 0.460(19) 1 d PD A 2 H284 H 0.4420 0.0787 1.0825 0.117 Uiso 0.460(19) 1 calc PR A 2 H285 H 0.3612 -0.0298 1.0746 0.117 Uiso 0.460(19) 1 calc PR A 2 H286 H 0.4224 -0.0043 1.1499 0.117 Uiso 0.460(19) 1 calc PR A 2 P2 P 0.34728(4) 0.56924(7) 0.39102(3) 0.05205(14) Uani 1 1 d . B . O6 O 0.17422(10) 0.73427(19) 0.44749(10) 0.0601(4) Uani 1 1 d . . . O7 O 0.47159(12) 0.7630(2) 0.57348(10) 0.0665(4) Uani 1 1 d . . . H7 H 0.4980 0.8405 0.5850 0.084(10) Uiso 1 1 calc R . . O8 O 0.43936(12) 0.5177(2) 0.39931(11) 0.0711(5) Uani 1 1 d . . . O9 O 0.27469(15) 0.4585(3) 0.35467(11) 0.0865(6) Uani 1 1 d U . . O10 O 0.32550(14) 0.7058(2) 0.34021(10) 0.0743(5) Uani 1 1 d . . . C29 C 0.31645(12) 0.6186(2) 0.47512(11) 0.0463(4) Uani 1 1 d . . . H291 H 0.3380 0.7192 0.4861 0.056 Uiso 1 1 calc R B . C30 C 0.21558(13) 0.6235(2) 0.46829(11) 0.0479(4) Uani 1 1 d . B . N2 N 0.17782(11) 0.4982(2) 0.48774(10) 0.0518(4) Uani 1 1 d . . . C31 C 0.22887(15) 0.3665(2) 0.50682(12) 0.0523(5) Uani 1 1 d . B . C32 C 0.18139(18) 0.2211(3) 0.48973(17) 0.0682(6) Uani 1 1 d . . . H321 H 0.1449 0.2015 0.5249 0.082 Uiso 1 1 calc R B . H322 H 0.1424 0.2272 0.4430 0.082 Uiso 1 1 calc R . . C33 C 0.2454(2) 0.0969(3) 0.4898(2) 0.0894(9) Uani 1 1 d . B . H331 H 0.2138 0.0044 0.4895 0.107 Uiso 1 1 calc R . . H332 H 0.2693 0.1015 0.4463 0.107 Uiso 1 1 calc R . . C34 C 0.3194(3) 0.0999(4) 0.5519(2) 0.0972(11) Uani 1 1 d . . . H341 H 0.3580 0.0162 0.5496 0.117 Uiso 1 1 calc R B . H342 H 0.2960 0.0912 0.5955 0.117 Uiso 1 1 calc R . . C35 C 0.37366(18) 0.2417(3) 0.55473(16) 0.0679(6) Uani 1 1 d . B . H351 H 0.4072 0.2558 0.6031 0.082 Uiso 1 1 calc R . . H352 H 0.4159 0.2319 0.5232 0.082 Uiso 1 1 calc R . . C36 C 0.31645(15) 0.3750(2) 0.53284(12) 0.0527(5) Uani 1 1 d . . . C37 C 0.36278(14) 0.5220(2) 0.53781(11) 0.0492(4) Uani 1 1 d . B . H371 H 0.4237 0.5045 0.5311 0.059 Uiso 1 1 calc R . . C38 C 0.36917(13) 0.6001(2) 0.60961(11) 0.0503(4) Uani 1 1 d . . . C39 C 0.42584(14) 0.7232(3) 0.62507(12) 0.0532(5) Uani 1 1 d . B . C40 C 0.43412(18) 0.7958(3) 0.68938(14) 0.0660(6) Uani 1 1 d . . . H401 H 0.4716 0.8769 0.6988 0.079 Uiso 1 1 calc R B . C41 C 0.38681(19) 0.7489(3) 0.74033(14) 0.0698(6) Uani 1 1 d . B . H411 H 0.3929 0.7984 0.7838 0.084 Uiso 1 1 calc R . . C42 C 0.3309(2) 0.6294(3) 0.72672(14) 0.0704(6) Uani 1 1 d . . . H421 H 0.2992 0.5978 0.7608 0.084 Uiso 1 1 calc R B . C43 C 0.32237(16) 0.5566(3) 0.66158(13) 0.0601(5) Uani 1 1 d . B . H431 H 0.2842 0.4763 0.6525 0.072 Uiso 1 1 calc R . . C441 C 0.08288(15) 0.5084(3) 0.49453(14) 0.0611(5) Uani 1 1 d . B . H441 H 0.0693 0.6139 0.4927 0.073 Uiso 1 1 calc R . . C45 C 0.0704(2) 0.4581(4) 0.56854(17) 0.0834(8) Uani 1 1 d . . . H451 H 0.0157 0.4975 0.5779 0.100 Uiso 1 1 calc R B . H452 H 0.1192 0.4926 0.6043 0.100 Uiso 1 1 calc R . . H453 H 0.0683 0.3525 0.5699 0.100 Uiso 1 1 calc R . . C46 C 0.01909(15) 0.4421(3) 0.43160(15) 0.0610(5) Uani 1 1 d . . . C47 C 0.03977(19) 0.4321(4) 0.36383(17) 0.0811(8) Uani 1 1 d . B . H471 H 0.0952 0.4633 0.3569 0.097 Uiso 1 1 calc R . . C48 C -0.0207(2) 0.3768(5) 0.30714(19) 0.0989(12) Uani 1 1 d . . . H481 H -0.0059 0.3712 0.2622 0.119 Uiso 1 1 calc R B . C49 C -0.1034(2) 0.3293(5) 0.3159(2) 0.1031(12) Uani 1 1 d . B . H491 H -0.1433 0.2888 0.2776 0.124 Uiso 1 1 calc R . . C50 C -0.1261(2) 0.3427(5) 0.3823(2) 0.0939(10) Uani 1 1 d . . . H501 H -0.1827 0.3158 0.3881 0.113 Uiso 1 1 calc R B . C51 C -0.06530(18) 0.3958(3) 0.44007(19) 0.0749(7) Uani 1 1 d . B . H511 H -0.0805 0.4009 0.4849 0.090 Uiso 1 1 calc R . . C52 C 0.3044(5) 0.3463(10) 0.3079(4) 0.0929(10) Uani 0.550(8) 1 d PDU B 1 H522 H 0.3302 0.3922 0.2708 0.111 Uiso 0.550(8) 1 calc PR B 1 H521 H 0.3477 0.2802 0.3355 0.111 Uiso 0.550(8) 1 calc PR B 1 C53 C 0.2214(5) 0.2668(12) 0.2766(4) 0.0979(15) Uani 0.550(8) 1 d PDU B 1 H531 H 0.2328 0.2000 0.2403 0.117 Uiso 0.550(8) 1 calc PR B 1 H532 H 0.1766 0.3364 0.2555 0.117 Uiso 0.550(8) 1 calc PR B 1 H533 H 0.2010 0.2126 0.3135 0.117 Uiso 0.550(8) 1 calc PR B 1 C54 C 0.3780(4) 0.8384(5) 0.3525(3) 0.1241(16) Uani 1 1 d DU B 1 H541 H 0.3460 0.9099 0.3756 0.149 Uiso 1 1 calc R B 1 H542 H 0.4332 0.8161 0.3854 0.149 Uiso 1 1 calc R B 1 C55 C 0.3981(7) 0.9020(10) 0.2917(4) 0.210(4) Uani 1 1 d DU B 1 H551 H 0.4416 0.9780 0.3053 0.252 Uiso 1 1 calc R B 1 H552 H 0.3452 0.9436 0.2632 0.252 Uiso 1 1 calc R B 1 H553 H 0.4215 0.8284 0.2643 0.252 Uiso 1 1 calc R B 1 C52A C 0.2641(7) 0.3949(10) 0.2839(5) 0.0929(10) Uani 0.450(8) 1 d PDU B 2 H523 H 0.3088 0.4340 0.2594 0.112 Uiso 0.450(8) 1 calc PR B 2 H524 H 0.2058 0.4193 0.2559 0.112 Uiso 0.450(8) 1 calc PR B 2 C53A C 0.2736(18) 0.2331(12) 0.2909(11) 0.238(13) Uani 0.450(8) 1 d PD B 2 H534 H 0.2255 0.1862 0.2589 0.285 Uiso 0.450(8) 1 calc PR B 2 H535 H 0.2725 0.2048 0.3394 0.285 Uiso 0.450(8) 1 calc PR B 2 H536 H 0.3291 0.2036 0.2792 0.285 Uiso 0.450(8) 1 calc PR B 2 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 0.0479(2) 0.0449(3) 0.0600(3) -0.0010(2) 0.0085(2) -0.0070(2) O1 0.0731(10) 0.0343(8) 0.1160(15) 0.0031(8) 0.0394(10) -0.0055(8) O2 0.0652(9) 0.0659(10) 0.0609(8) -0.0012(7) 0.0134(7) 0.0284(8) O3 0.0695(10) 0.0703(11) 0.0816(11) 0.0084(10) 0.0052(9) 0.0211(9) O4 0.0786(11) 0.0759(12) 0.0644(9) 0.0027(9) 0.0128(8) -0.0349(10) O5 0.0470(7) 0.0595(10) 0.0742(9) -0.0143(8) 0.0099(7) -0.0096(7) C1 0.0421(9) 0.0344(9) 0.0600(10) -0.0005(8) 0.0119(8) 0.0038(7) C2 0.0479(10) 0.0323(9) 0.0724(12) 0.0066(9) 0.0180(9) 0.0040(8) N1 0.0471(8) 0.0349(8) 0.0698(10) 0.0071(7) 0.0231(7) 0.0037(7) C4 0.0505(10) 0.0305(9) 0.0594(10) 0.0045(7) 0.0165(8) 0.0032(8) C5 0.0604(12) 0.0382(11) 0.0869(15) 0.0036(10) 0.0222(11) 0.0108(10) C6 0.0804(18) 0.0363(13) 0.166(3) 0.0141(16) 0.028(2) 0.0047(12) C7 0.0815(17) 0.0404(13) 0.137(3) 0.0008(15) 0.0292(17) -0.0080(13) C8 0.0574(11) 0.0451(11) 0.0750(14) -0.0026(10) 0.0201(10) -0.0115(9) C9 0.0475(9) 0.0352(10) 0.0570(10) -0.0007(8) 0.0125(8) -0.0006(8) C10 0.0425(9) 0.0401(10) 0.0552(10) -0.0020(8) 0.0125(7) 0.0008(8) C11 0.0468(9) 0.0490(11) 0.0561(10) 0.0009(9) 0.0124(8) 0.0047(9) C12 0.0528(10) 0.0571(13) 0.0583(11) 0.0037(9) 0.0143(9) 0.0112(10) C13 0.0839(17) 0.0757(18) 0.0699(15) 0.0122(13) 0.0122(12) 0.0277(15) C14 0.103(2) 0.106(3) 0.0581(14) 0.0153(15) 0.0042(14) 0.028(2) C15 0.105(2) 0.097(2) 0.0545(13) -0.0063(14) 0.0108(13) 0.0158(19) C16 0.0703(14) 0.0673(15) 0.0620(12) -0.0068(11) 0.0126(10) 0.0127(12) C17 0.0628(12) 0.0450(12) 0.0806(14) 0.0112(10) 0.0356(11) 0.0038(9) C18 0.094(2) 0.089(2) 0.0764(17) 0.0137(16) 0.0349(15) 0.0063(17) C19 0.0551(12) 0.0483(12) 0.0959(18) 0.0056(11) 0.0367(12) 0.0006(10) C20 0.0559(13) 0.097(2) 0.103(2) 0.0010(18) 0.0284(14) 0.0077(15) C21 0.0567(15) 0.135(4) 0.126(3) 0.018(3) 0.0201(17) 0.0086(19) C22 0.0580(16) 0.115(3) 0.177(5) 0.026(3) 0.038(2) 0.017(2) C23 0.074(2) 0.100(3) 0.191(5) -0.014(3) 0.064(3) 0.022(2) C24 0.0724(17) 0.080(2) 0.131(3) -0.0180(19) 0.0489(18) 0.0049(15) C25 0.0588(14) 0.093(2) 0.124(3) -0.045(2) 0.0054(15) 0.0054(15) C26 0.093(2) 0.091(3) 0.180(5) -0.057(3) 0.017(3) 0.011(2) C27 0.162(9) 0.069(6) 0.117(8) 0.024(5) 0.012(6) 0.049(6) C28 0.123(9) 0.143(15) 0.158(13) 0.045(12) -0.006(8) 0.050(10) C27A 0.115(7) 0.107(9) 0.069(4) 0.004(4) -0.001(4) 0.061(7) C28A 0.103(8) 0.082(7) 0.107(7) 0.021(5) 0.018(6) 0.049(6) P2 0.0532(3) 0.0466(3) 0.0572(3) 0.0010(2) 0.0128(2) -0.0008(2) O6 0.0555(8) 0.0448(8) 0.0804(10) 0.0094(7) 0.0144(7) 0.0072(7) O7 0.0665(9) 0.0662(11) 0.0700(10) -0.0134(8) 0.0210(8) -0.0219(8) O8 0.0673(10) 0.0695(11) 0.0799(11) 0.0028(9) 0.0226(8) 0.0160(9) O9 0.0892(12) 0.0969(15) 0.0762(11) -0.0313(11) 0.0229(9) -0.0319(12) O10 0.0810(11) 0.0742(12) 0.0680(10) 0.0160(9) 0.0154(8) 0.0074(10) C29 0.0445(9) 0.0375(10) 0.0555(10) -0.0007(8) 0.0066(8) -0.0020(7) C30 0.0486(10) 0.0384(10) 0.0563(10) -0.0007(8) 0.0097(8) 0.0007(8) N2 0.0453(8) 0.0409(9) 0.0693(10) 0.0009(8) 0.0121(7) -0.0014(7) C31 0.0551(11) 0.0360(10) 0.0664(12) 0.0021(9) 0.0135(9) -0.0001(9) C32 0.0696(14) 0.0415(12) 0.0932(17) -0.0014(12) 0.0153(12) -0.0100(11) C33 0.095(2) 0.0415(14) 0.133(3) -0.0099(15) 0.0250(19) -0.0052(13) C34 0.107(2) 0.0450(15) 0.133(3) 0.0190(17) 0.007(2) 0.0101(15) C35 0.0706(14) 0.0467(13) 0.0827(16) 0.0098(11) 0.0059(12) 0.0110(12) C36 0.0589(11) 0.0381(10) 0.0592(11) 0.0009(8) 0.0069(9) -0.0008(9) C37 0.0486(10) 0.0405(10) 0.0576(11) 0.0038(8) 0.0082(8) 0.0016(8) C38 0.0510(10) 0.0446(11) 0.0529(10) 0.0037(8) 0.0042(8) 0.0032(8) C39 0.0512(10) 0.0492(11) 0.0586(11) 0.0003(9) 0.0093(8) -0.0002(9) C40 0.0689(13) 0.0585(14) 0.0685(13) -0.0088(11) 0.0086(11) -0.0068(12) C41 0.0827(16) 0.0711(16) 0.0568(12) -0.0055(11) 0.0167(11) 0.0067(13) C42 0.0811(16) 0.0693(16) 0.0637(13) 0.0141(12) 0.0215(12) 0.0093(13) C43 0.0634(12) 0.0522(12) 0.0645(12) 0.0104(10) 0.0121(10) -0.0012(10) C441 0.0507(11) 0.0532(12) 0.0838(15) 0.0026(11) 0.0240(10) -0.0005(10) C45 0.0743(16) 0.100(2) 0.0835(18) -0.0011(17) 0.0333(14) -0.0074(17) C46 0.0480(11) 0.0503(12) 0.0838(15) 0.0142(11) 0.0105(10) -0.0012(9) C47 0.0617(13) 0.096(2) 0.0831(17) 0.0126(16) 0.0093(12) -0.0172(15) C48 0.086(2) 0.127(3) 0.0763(18) 0.0220(19) -0.0006(15) -0.029(2) C49 0.0765(18) 0.115(3) 0.104(2) 0.021(2) -0.0150(17) -0.030(2) C50 0.0563(14) 0.101(3) 0.121(3) 0.009(2) 0.0080(15) -0.0257(16) C51 0.0565(13) 0.0639(16) 0.106(2) 0.0095(14) 0.0206(13) -0.0076(12) C52 0.0930(19) 0.101(2) 0.0850(17) -0.0345(16) 0.0187(16) -0.0299(18) C53 0.098(3) 0.109(3) 0.089(3) -0.036(2) 0.024(2) -0.036(3) C54 0.137(4) 0.090(3) 0.137(4) 0.041(3) 0.007(3) -0.013(3) C55 0.264(8) 0.191(7) 0.168(6) 0.058(5) 0.024(6) -0.113(7) C52A 0.0957(19) 0.103(2) 0.0811(18) -0.0308(17) 0.0191(16) -0.0305(18) C53A 0.24(3) 0.22(2) 0.24(2) -0.16(2) 0.05(2) -0.04(2) 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 O4 1.4686(18) . ? P1 O3 1.5706(19) . ? P1 O5 1.5710(17) . ? P1 C1 1.814(2) . ? O1 C2 1.216(3) . ? O2 C12 1.370(3) . ? O2 H2 0.8200 . ? O3 C27 1.403(8) . ? O3 C27A 1.419(8) . ? O5 C25 1.443(4) . ? C1 C2 1.526(3) . ? C1 C10 1.540(3) . ? C1 H11 0.9800 . ? C2 N1 1.357(3) . ? N1 C4 1.435(3) . ? N1 C17 1.488(3) . ? C4 C9 1.341(3) . ? C4 C5 1.506(3) . ? C5 C6 1.493(4) . ? C5 H51 0.9700 . ? C5 H52 0.9700 . ? C6 C7 1.468(5) . ? C6 H61 0.9700 . ? C6 H62 0.9700 . ? C7 C8 1.503(4) . ? C7 H71 0.9700 . ? C7 H72 0.9700 . ? C8 C9 1.505(3) . ? C8 H81 0.9700 . ? C8 H82 0.9700 . ? C9 C10 1.511(3) . ? C10 C11 1.529(3) . ? C10 H101 0.9800 . ? C11 C16 1.391(3) . ? C11 C12 1.394(3) . ? C12 C13 1.385(4) . ? C13 C14 1.374(5) . ? C13 H131 0.9300 . ? C14 C15 1.378(5) . ? C14 H141 0.9300 . ? C15 C16 1.382(4) . ? C15 H151 0.9300 . ? C16 H161 0.9300 . ? C17 C18 1.513(4) . ? C17 C19 1.526(4) . ? C17 H171 0.9800 . ? C18 H181 0.9600 . ? C18 H172 0.9600 . ? C18 H173 0.9600 . ? C19 C20 1.378(5) . ? C19 C24 1.388(4) . ? C20 C21 1.383(5) . ? C20 H201 0.9300 . ? C21 C22 1.353(7) . ? C21 H211 0.9300 . ? C22 C23 1.360(7) . ? C22 H221 0.9300 . ? C23 C24 1.396(6) . ? C23 H231 0.9300 . ? C24 H241 0.9300 . ? C25 C26 1.451(5) . ? C25 H251 0.9700 . ? C25 H252 0.9700 . ? C26 H261 0.9600 . ? C26 H262 0.9600 . ? C26 H263 0.9600 . ? C27 C28 1.479(2) . ? C27 H271 0.9700 . ? C27 H272 0.9700 . ? C28 H281 0.9600 . ? C28 H282 0.9600 . ? C28 H283 0.9600 . ? C27A C28A 1.478(2) . ? C27A H273 0.9700 . ? C27A H274 0.9700 . ? C28A H284 0.9600 . ? C28A H285 0.9600 . ? C28A H286 0.9600 . ? P2 O8 1.4661(19) . ? P2 O9 1.557(2) . ? P2 O10 1.568(2) . ? P2 C29 1.813(2) . ? O6 C30 1.213(3) . ? O7 C39 1.364(3) . ? O7 H7 0.8200 . ? O9 C52A 1.445(8) . ? O9 C52 1.483(8) . ? O10 C54 1.442(5) . ? C29 C30 1.527(3) . ? C29 C37 1.537(3) . ? C29 H291 0.9800 . ? C30 N2 1.361(3) . ? N2 C31 1.436(3) . ? N2 C441 1.490(3) . ? C31 C36 1.338(3) . ? C31 C32 1.513(3) . ? C32 C33 1.495(4) . ? C32 H321 0.9700 . ? C32 H322 0.9700 . ? C33 C34 1.468(5) . ? C33 H331 0.9700 . ? C33 H332 0.9700 . ? C34 C35 1.529(4) . ? C34 H341 0.9700 . ? C34 H342 0.9700 . ? C35 C36 1.505(3) . ? C35 H351 0.9700 . ? C35 H352 0.9700 . ? C36 C37 1.506(3) . ? C37 C38 1.525(3) . ? C37 H371 0.9800 . ? C38 C43 1.389(3) . ? C38 C39 1.411(3) . ? C39 C40 1.374(3) . ? C40 C41 1.388(4) . ? C40 H401 0.9300 . ? C41 C42 1.375(4) . ? C41 H411 0.9300 . ? C42 C43 1.388(4) . ? C42 H421 0.9300 . ? C43 H431 0.9300 . ? C441 C46 1.513(4) . ? C441 C45 1.528(4) . ? C441 H441 0.9800 . ? C45 H451 0.9600 . ? C45 H452 0.9600 . ? C45 H453 0.9600 . ? C46 C47 1.391(4) . ? C46 C51 1.400(3) . ? C47 C48 1.371(5) . ? C47 H471 0.9300 . ? C48 C49 1.380(5) . ? C48 H481 0.9300 . ? C49 C50 1.380(6) . ? C49 H491 0.9300 . ? C50 C51 1.380(5) . ? C50 H501 0.9300 . ? C51 H511 0.9300 . ? C52 C53 1.481(2) . ? C52 H522 0.9700 . ? C52 H521 0.9700 . ? C53 H531 0.9600 . ? C53 H532 0.9600 . ? C53 H533 0.9600 . ? C54 C55 1.382(6) . ? C54 H541 0.9700 . ? C54 H542 0.9700 . ? C55 H551 0.9600 . ? C55 H552 0.9600 . ? C55 H553 0.9600 . ? C52A C53A 1.480(2) . ? C52A H523 0.9700 . ? C52A H524 0.9700 . ? C53A H534 0.9600 . ? C53A H535 0.9600 . ? C53A H536 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 O4 P1 O3 116.52(13) . . ? O4 P1 O5 112.95(11) . . ? O3 P1 O5 100.91(11) . . ? O4 P1 C1 113.14(10) . . ? O3 P1 C1 105.67(10) . . ? O5 P1 C1 106.47(10) . . ? C12 O2 H2 109.5 . . ? C27 O3 C27A 34.8(5) . . ? C27 O3 P1 124.9(5) . . ? C27A O3 P1 122.7(4) . . ? C25 O5 P1 121.76(16) . . ? C2 C1 C10 111.01(17) . . ? C2 C1 P1 112.62(14) . . ? C10 C1 P1 112.96(14) . . ? C2 C1 H11 106.6 . . ? C10 C1 H11 106.6 . . ? P1 C1 H11 106.6 . . ? O1 C2 N1 123.68(19) . . ? O1 C2 C1 120.59(19) . . ? N1 C2 C1 115.72(17) . . ? C2 N1 C4 121.09(16) . . ? C2 N1 C17 116.80(17) . . ? C4 N1 C17 121.98(17) . . ? C9 C4 N1 119.95(17) . . ? C9 C4 C5 122.50(18) . . ? N1 C4 C5 117.39(17) . . ? C6 C5 C4 112.2(2) . . ? C6 C5 H51 109.2 . . ? C4 C5 H51 109.2 . . ? C6 C5 H52 109.2 . . ? C4 C5 H52 109.2 . . ? H51 C5 H52 107.9 . . ? C7 C6 C5 114.7(3) . . ? C7 C6 H61 108.6 . . ? C5 C6 H61 108.6 . . ? C7 C6 H62 108.6 . . ? C5 C6 H62 108.6 . . ? H61 C6 H62 107.6 . . ? C6 C7 C8 113.4(3) . . ? C6 C7 H71 108.9 . . ? C8 C7 H71 108.9 . . ? C6 C7 H72 108.9 . . ? C8 C7 H72 108.9 . . ? H71 C7 H72 107.7 . . ? C7 C8 C9 113.90(19) . . ? C7 C8 H81 108.8 . . ? C9 C8 H81 108.8 . . ? C7 C8 H82 108.8 . . ? C9 C8 H82 108.8 . . ? H81 C8 H82 107.7 . . ? C4 C9 C8 122.66(19) . . ? C4 C9 C10 119.25(17) . . ? C8 C9 C10 118.05(17) . . ? C9 C10 C11 114.44(17) . . ? C9 C10 C1 107.42(15) . . ? C11 C10 C1 111.49(17) . . ? C9 C10 H101 107.7 . . ? C11 C10 H101 107.7 . . ? C1 C10 H101 107.7 . . ? C16 C11 C12 117.8(2) . . ? C16 C11 C10 122.6(2) . . ? C12 C11 C10 119.56(19) . . ? O2 C12 C13 121.7(2) . . ? O2 C12 C11 118.05(19) . . ? C13 C12 C11 120.3(2) . . ? C14 C13 C12 120.7(3) . . ? C14 C13 H131 119.6 . . ? C12 C13 H131 119.6 . . ? C13 C14 C15 120.1(3) . . ? C13 C14 H141 120.0 . . ? C15 C14 H141 120.0 . . ? C14 C15 C16 119.2(3) . . ? C14 C15 H151 120.4 . . ? C16 C15 H151 120.4 . . ? C15 C16 C11 121.9(3) . . ? C15 C16 H161 119.1 . . ? C11 C16 H161 119.1 . . ? N1 C17 C18 110.9(2) . . ? N1 C17 C19 111.5(2) . . ? C18 C17 C19 117.0(2) . . ? N1 C17 H171 105.5 . . ? C18 C17 H171 105.5 . . ? C19 C17 H171 105.5 . . ? C17 C18 H181 109.5 . . ? C17 C18 H172 109.5 . . ? H181 C18 H172 109.5 . . ? C17 C18 H173 109.5 . . ? H181 C18 H173 109.5 . . ? H172 C18 H173 109.5 . . ? C20 C19 C24 117.5(3) . . ? C20 C19 C17 119.9(2) . . ? C24 C19 C17 122.6(3) . . ? C19 C20 C21 121.1(3) . . ? C19 C20 H201 119.4 . . ? C21 C20 H201 119.4 . . ? C22 C21 C20 121.3(5) . . ? C22 C21 H211 119.3 . . ? C20 C21 H211 119.3 . . ? C21 C22 C23 118.6(4) . . ? C21 C22 H221 120.7 . . ? C23 C22 H221 120.7 . . ? C22 C23 C24 121.3(4) . . ? C22 C23 H231 119.3 . . ? C24 C23 H231 119.3 . . ? C19 C24 C23 120.0(4) . . ? C19 C24 H241 120.0 . . ? C23 C24 H241 120.0 . . ? O5 C25 C26 111.6(3) . . ? O5 C25 H251 109.3 . . ? C26 C25 H251 109.3 . . ? O5 C25 H252 109.3 . . ? C26 C25 H252 109.3 . . ? H251 C25 H252 108.0 . . ? C25 C26 H261 109.5 . . ? C25 C26 H262 109.5 . . ? H261 C26 H262 109.5 . . ? C25 C26 H263 109.5 . . ? H261 C26 H263 109.5 . . ? H262 C26 H263 109.5 . . ? O3 C27 C28 107.8(12) . . ? O3 C27 H271 110.1 . . ? C28 C27 H271 110.1 . . ? O3 C27 H272 110.1 . . ? C28 C27 H272 110.1 . . ? H271 C27 H272 108.5 . . ? O3 C27A C28A 111.6(10) . . ? O3 C27A H273 109.3 . . ? C28A C27A H273 109.3 . . ? O3 C27A H274 109.3 . . ? C28A C27A H274 109.3 . . ? H273 C27A H274 108.0 . . ? C27A C28A H284 109.5 . . ? C27A C28A H285 109.5 . . ? H284 C28A H285 109.5 . . ? C27A C28A H286 109.5 . . ? H284 C28A H286 109.5 . . ? H285 C28A H286 109.5 . . ? O8 P2 O9 115.46(13) . . ? O8 P2 O10 113.72(11) . . ? O9 P2 O10 101.00(13) . . ? O8 P2 C29 113.45(10) . . ? O9 P2 C29 105.29(10) . . ? O10 P2 C29 106.73(10) . . ? C39 O7 H7 109.5 . . ? C52A O9 C52 32.5(4) . . ? C52A O9 P2 127.7(4) . . ? C52 O9 P2 115.7(3) . . ? C54 O10 P2 121.2(2) . . ? C30 C29 C37 112.80(16) . . ? C30 C29 P2 111.64(14) . . ? C37 C29 P2 112.51(14) . . ? C30 C29 H291 106.4 . . ? C37 C29 H291 106.4 . . ? P2 C29 H291 106.4 . . ? O6 C30 N2 124.01(18) . . ? O6 C30 C29 120.49(18) . . ? N2 C30 C29 115.50(17) . . ? C30 N2 C31 121.70(17) . . ? C30 N2 C441 116.58(18) . . ? C31 N2 C441 121.50(19) . . ? C36 C31 N2 120.13(19) . . ? C36 C31 C32 122.3(2) . . ? N2 C31 C32 117.29(19) . . ? C33 C32 C31 111.8(2) . . ? C33 C32 H321 109.3 . . ? C31 C32 H321 109.3 . . ? C33 C32 H322 109.3 . . ? C31 C32 H322 109.3 . . ? H321 C32 H322 107.9 . . ? C34 C33 C32 112.9(3) . . ? C34 C33 H331 109.0 . . ? C32 C33 H331 109.0 . . ? C34 C33 H332 109.0 . . ? C32 C33 H332 109.0 . . ? H331 C33 H332 107.8 . . ? C33 C34 C35 111.8(3) . . ? C33 C34 H341 109.3 . . ? C35 C34 H341 109.3 . . ? C33 C34 H342 109.3 . . ? C35 C34 H342 109.3 . . ? H341 C34 H342 107.9 . . ? C36 C35 C34 112.7(2) . . ? C36 C35 H351 109.1 . . ? C34 C35 H351 109.1 . . ? C36 C35 H352 109.1 . . ? C34 C35 H352 109.1 . . ? H351 C35 H352 107.8 . . ? C31 C36 C35 122.9(2) . . ? C31 C36 C37 120.04(19) . . ? C35 C36 C37 117.00(19) . . ? C36 C37 C38 114.48(18) . . ? C36 C37 C29 108.52(17) . . ? C38 C37 C29 111.56(17) . . ? C36 C37 H371 107.3 . . ? C38 C37 H371 107.3 . . ? C29 C37 H371 107.3 . . ? C43 C38 C39 117.4(2) . . ? C43 C38 C37 123.7(2) . . ? C39 C38 C37 118.89(19) . . ? O7 C39 C40 122.9(2) . . ? O7 C39 C38 116.33(19) . . ? C40 C39 C38 120.7(2) . . ? C39 C40 C41 120.4(3) . . ? C39 C40 H401 119.8 . . ? C41 C40 H401 119.8 . . ? C42 C41 C40 120.2(2) . . ? C42 C41 H411 119.9 . . ? C40 C41 H411 119.9 . . ? C41 C42 C43 119.3(2) . . ? C41 C42 H421 120.3 . . ? C43 C42 H421 120.3 . . ? C42 C43 C38 121.9(2) . . ? C42 C43 H431 119.0 . . ? C38 C43 H431 119.0 . . ? N2 C441 C46 113.4(2) . . ? N2 C441 C45 111.4(2) . . ? C46 C441 C45 115.5(2) . . ? N2 C441 H441 105.1 . . ? C46 C441 H441 105.1 . . ? C45 C441 H441 105.1 . . ? C441 C45 H451 109.5 . . ? C441 C45 H452 109.5 . . ? H451 C45 H452 109.5 . . ? C441 C45 H453 109.5 . . ? H451 C45 H453 109.5 . . ? H452 C45 H453 109.5 . . ? C47 C46 C51 118.2(3) . . ? C47 C46 C441 122.0(2) . . ? C51 C46 C441 119.7(3) . . ? C48 C47 C46 120.7(3) . . ? C48 C47 H471 119.7 . . ? C46 C47 H471 119.7 . . ? C47 C48 C49 120.9(4) . . ? C47 C48 H481 119.5 . . ? C49 C48 H481 119.5 . . ? C50 C49 C48 119.1(3) . . ? C50 C49 H491 120.4 . . ? C48 C49 H491 120.4 . . ? C49 C50 C51 120.5(3) . . ? C49 C50 H501 119.7 . . ? C51 C50 H501 119.7 . . ? C50 C51 C46 120.4(3) . . ? C50 C51 H511 119.8 . . ? C46 C51 H511 119.8 . . ? C53 C52 O9 103.6(6) . . ? C53 C52 H522 111.0 . . ? O9 C52 H522 111.0 . . ? C53 C52 H521 111.0 . . ? O9 C52 H521 111.0 . . ? H522 C52 H521 109.0 . . ? C55 C54 O10 115.0(5) . . ? C55 C54 H541 108.5 . . ? O10 C54 H541 108.5 . . ? C55 C54 H542 108.5 . . ? O10 C54 H542 108.5 . . ? H541 C54 H542 107.5 . . ? O9 C52A C53A 108.8(10) . . ? O9 C52A H523 109.9 . . ? C53A C52A H523 109.9 . . ? O9 C52A H524 109.9 . . ? C53A C52A H524 109.9 . . ? H523 C52A H524 108.3 . . ? C52A C53A H534 109.5 . . ? C52A C53A H535 109.5 . . ? H534 C53A H535 109.5 . . ? C52A C53A H536 109.5 . . ? H534 C53A H536 109.5 . . ? H535 C53A H536 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 O4 P1 O3 C27 -9.6(9) . . . . ? O5 P1 O3 C27 113.1(9) . . . . ? C1 P1 O3 C27 -136.1(9) . . . . ? O4 P1 O3 C27A -51.7(10) . . . . ? O5 P1 O3 C27A 71.0(10) . . . . ? C1 P1 O3 C27A -178.2(10) . . . . ? O4 P1 O5 C25 -54.3(3) . . . . ? O3 P1 O5 C25 -179.5(3) . . . . ? C1 P1 O5 C25 70.4(3) . . . . ? O4 P1 C1 C2 -155.15(16) . . . . ? O3 P1 C1 C2 -26.53(18) . . . . ? O5 P1 C1 C2 80.20(15) . . . . ? O4 P1 C1 C10 -28.39(18) . . . . ? O3 P1 C1 C10 100.22(15) . . . . ? O5 P1 C1 C10 -153.04(13) . . . . ? C10 C1 C2 O1 142.9(2) . . . . ? P1 C1 C2 O1 -89.4(2) . . . . ? C10 C1 C2 N1 -36.0(3) . . . . ? P1 C1 C2 N1 91.8(2) . . . . ? O1 C2 N1 C4 175.8(2) . . . . ? C1 C2 N1 C4 -5.4(3) . . . . ? O1 C2 N1 C17 -8.2(3) . . . . ? C1 C2 N1 C17 170.60(19) . . . . ? C2 N1 C4 C9 27.7(3) . . . . ? C17 N1 C4 C9 -148.1(2) . . . . ? C2 N1 C4 C5 -147.8(2) . . . . ? C17 N1 C4 C5 36.4(3) . . . . ? C9 C4 C5 C6 -12.2(4) . . . . ? N1 C4 C5 C6 163.2(3) . . . . ? C4 C5 C6 C7 42.2(5) . . . . ? C5 C6 C7 C8 -54.4(5) . . . . ? C6 C7 C8 C9 34.6(4) . . . . ? N1 C4 C9 C8 178.8(2) . . . . ? C5 C4 C9 C8 -6.0(3) . . . . ? N1 C4 C9 C10 -3.8(3) . . . . ? C5 C4 C9 C10 171.4(2) . . . . ? C7 C8 C9 C4 -5.2(3) . . . . ? C7 C8 C9 C10 177.4(2) . . . . ? C4 C9 C10 C11 88.2(2) . . . . ? C8 C9 C10 C11 -94.2(2) . . . . ? C4 C9 C10 C1 -36.1(3) . . . . ? C8 C9 C10 C1 141.4(2) . . . . ? C2 C1 C10 C9 54.6(2) . . . . ? P1 C1 C10 C9 -72.99(17) . . . . ? C2 C1 C10 C11 -71.5(2) . . . . ? P1 C1 C10 C11 160.88(13) . . . . ? C9 C10 C11 C16 -2.2(3) . . . . ? C1 C10 C11 C16 119.9(2) . . . . ? C9 C10 C11 C12 176.56(19) . . . . ? C1 C10 C11 C12 -61.3(2) . . . . ? C16 C11 C12 O2 177.6(2) . . . . ? C10 C11 C12 O2 -1.2(3) . . . . ? C16 C11 C12 C13 -0.5(4) . . . . ? C10 C11 C12 C13 -179.4(2) . . . . ? O2 C12 C13 C14 -176.8(3) . . . . ? C11 C12 C13 C14 1.2(5) . . . . ? C12 C13 C14 C15 -0.3(6) . . . . ? C13 C14 C15 C16 -1.4(6) . . . . ? C14 C15 C16 C11 2.1(5) . . . . ? C12 C11 C16 C15 -1.1(4) . . . . ? C10 C11 C16 C15 177.7(3) . . . . ? C2 N1 C17 C18 -122.2(2) . . . . ? C4 N1 C17 C18 53.8(3) . . . . ? C2 N1 C17 C19 105.5(2) . . . . ? C4 N1 C17 C19 -78.6(3) . . . . ? N1 C17 C19 C20 -46.3(3) . . . . ? C18 C17 C19 C20 -175.5(3) . . . . ? N1 C17 C19 C24 136.2(3) . . . . ? C18 C17 C19 C24 7.0(4) . . . . ? C24 C19 C20 C21 -2.6(5) . . . . ? C17 C19 C20 C21 179.8(3) . . . . ? C19 C20 C21 C22 0.6(7) . . . . ? C20 C21 C22 C23 2.8(7) . . . . ? C21 C22 C23 C24 -4.2(8) . . . . ? C20 C19 C24 C23 1.2(5) . . . . ? C17 C19 C24 C23 178.7(3) . . . . ? C22 C23 C24 C19 2.2(7) . . . . ? P1 O5 C25 C26 178.1(3) . . . . ? C27A O3 C27 C28 -45.0(15) . . . . ? P1 O3 C27 C28 -143.6(13) . . . . ? C27 O3 C27A C28A 48.6(15) . . . . ? P1 O3 C27A C28A 154.2(13) . . . . ? O8 P2 O9 C52A -59.6(7) . . . . ? O10 P2 O9 C52A 63.6(7) . . . . ? C29 P2 O9 C52A 174.5(6) . . . . ? O8 P2 O9 C52 -23.7(5) . . . . ? O10 P2 O9 C52 99.4(5) . . . . ? C29 P2 O9 C52 -149.7(5) . . . . ? O8 P2 O10 C54 -54.7(3) . . . . ? O9 P2 O10 C54 -179.0(3) . . . . ? C29 P2 O10 C54 71.2(3) . . . . ? O8 P2 C29 C30 -161.66(15) . . . . ? O9 P2 C29 C30 -34.48(19) . . . . ? O10 P2 C29 C30 72.31(16) . . . . ? O8 P2 C29 C37 -33.65(18) . . . . ? O9 P2 C29 C37 93.53(17) . . . . ? O10 P2 C29 C37 -159.69(15) . . . . ? C37 C29 C30 O6 146.4(2) . . . . ? P2 C29 C30 O6 -85.8(2) . . . . ? C37 C29 C30 N2 -32.8(3) . . . . ? P2 C29 C30 N2 95.04(19) . . . . ? O6 C30 N2 C31 175.2(2) . . . . ? C29 C30 N2 C31 -5.6(3) . . . . ? O6 C30 N2 C441 -10.1(3) . . . . ? C29 C30 N2 C441 169.10(19) . . . . ? C30 N2 C31 C36 26.0(3) . . . . ? C441 N2 C31 C36 -148.4(2) . . . . ? C30 N2 C31 C32 -148.4(2) . . . . ? C441 N2 C31 C32 37.2(3) . . . . ? C36 C31 C32 C33 -12.7(4) . . . . ? N2 C31 C32 C33 161.6(3) . . . . ? C31 C32 C33 C34 45.9(4) . . . . ? C32 C33 C34 C35 -60.0(4) . . . . ? C33 C34 C35 C36 38.9(4) . . . . ? N2 C31 C36 C35 179.2(2) . . . . ? C32 C31 C36 C35 -6.7(4) . . . . ? N2 C31 C36 C37 -3.9(3) . . . . ? C32 C31 C36 C37 170.2(2) . . . . ? C34 C35 C36 C31 -6.5(4) . . . . ? C34 C35 C36 C37 176.5(3) . . . . ? C31 C36 C37 C38 92.4(2) . . . . ? C35 C36 C37 C38 -90.5(2) . . . . ? C31 C36 C37 C29 -32.9(3) . . . . ? C35 C36 C37 C29 144.1(2) . . . . ? C30 C29 C37 C36 50.2(2) . . . . ? P2 C29 C37 C36 -77.20(19) . . . . ? C30 C29 C37 C38 -76.8(2) . . . . ? P2 C29 C37 C38 155.78(15) . . . . ? C36 C37 C38 C43 -12.0(3) . . . . ? C29 C37 C38 C43 111.8(2) . . . . ? C36 C37 C38 C39 167.70(18) . . . . ? C29 C37 C38 C39 -68.6(2) . . . . ? C43 C38 C39 O7 179.5(2) . . . . ? C37 C38 C39 O7 -0.2(3) . . . . ? C43 C38 C39 C40 0.3(3) . . . . ? C37 C38 C39 C40 -179.4(2) . . . . ? O7 C39 C40 C41 -179.0(2) . . . . ? C38 C39 C40 C41 0.1(4) . . . . ? C39 C40 C41 C42 -0.2(4) . . . . ? C40 C41 C42 C43 -0.1(4) . . . . ? C41 C42 C43 C38 0.5(4) . . . . ? C39 C38 C43 C42 -0.6(3) . . . . ? C37 C38 C43 C42 179.1(2) . . . . ? C30 N2 C441 C46 102.9(2) . . . . ? C31 N2 C441 C46 -82.4(3) . . . . ? C30 N2 C441 C45 -124.8(3) . . . . ? C31 N2 C441 C45 50.0(3) . . . . ? N2 C441 C46 C47 -25.9(4) . . . . ? C45 C441 C46 C47 -156.2(3) . . . . ? N2 C441 C46 C51 157.5(2) . . . . ? C45 C441 C46 C51 27.2(4) . . . . ? C51 C46 C47 C48 -0.7(5) . . . . ? C441 C46 C47 C48 -177.4(3) . . . . ? C46 C47 C48 C49 -0.2(7) . . . . ? C47 C48 C49 C50 2.2(7) . . . . ? C48 C49 C50 C51 -3.3(7) . . . . ? C49 C50 C51 C46 2.4(6) . . . . ? C47 C46 C51 C50 -0.4(5) . . . . ? C441 C46 C51 C50 176.4(3) . . . . ? C52A O9 C52 C53 -54.8(9) . . . . ? P2 O9 C52 C53 -175.3(6) . . . . ? P2 O10 C54 C55 137.6(6) . . . . ? C52 O9 C52A C53A 39.4(13) . . . . ? P2 O9 C52A C53A 118.3(13) . . . . ? _refine_special_details ; The C27, C28, C52, C53, C54 and C55 atoms of the diethoxy substitents are disordered over two partially occupied positions, respectively ; data_44 _database_code_depnum_ccdc_archive 'CCDC 912218' #==================================================== _chemical_name_systematic ; diethyl [(3S,4S)-4-(2-hydroxyphenyl)-2-oxo-1-((S)-1- phenylethyl)-1,2,3,4,5,6,7,8-octahydroquinolin-3-yl]phosphonate ; _chemical_formula_moiety '2(C27 H34 N O5 P)' _chemical_formula_sum 'C54 H68 N2 O10 P2' _chemical_formula_weight 967.0861 _chemical_melting_point 492(1) _exptl_crystal_colour colourless _exptl_crystal_description prism _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_preparation ; slow evaporation for benzene and n-heptane 3:1 mixture ; _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 1.236 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6430 _exptl_absorpt_correction_T_max 0.7932 _exptl_absorpt_process_details 'Bruker SADABS' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 15.3297(2) _cell_length_b 9.0879(1) _cell_length_c 19.0093(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.437(1) _cell_angle_gamma 90.00 _cell_volume 2595.69(6) _cell_formula_units_Z 2 _cell_measurement_temperature 291(1) _exptl_crystal_density_diffrn 1.236 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_ambient_temperature 291(2) _diffrn_reflns_number 29421 _reflns_number_total 8887 _reflns_number_gt 8719 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 66.53 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 66.53 _diffrn_measured_fraction_theta_full 0.995 _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^)+(0.0625P)^2^+0.3497P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_number_reflns 8887 _refine_ls_number_parameters 681 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0964 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.035 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.002(13) _chemical_absolute_configuration rmad _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.350 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.034 _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' 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 0.80448(3) 0.69947(6) -0.05076(3) 0.05062(13) Uani 1 1 d . A . O1 O 0.73323(12) 0.51671(17) 0.08677(11) 0.0715(5) Uani 1 1 d . . . O2 O 1.01937(10) 0.51085(19) 0.08101(8) 0.0627(4) Uani 1 1 d . . . H2 H 1.0512 0.4376 0.0854 0.075 Uiso 1 1 calc R . . O3 O 0.71300(12) 0.7790(2) -0.05420(10) 0.0740(5) Uani 1 1 d . . . O4 O 0.87085(12) 0.7778(2) -0.08265(9) 0.0723(5) Uani 1 1 d . . . O5 O 0.77290(9) 0.55062(18) -0.09004(9) 0.0599(4) Uani 1 1 d . . . C1 C 0.84395(12) 0.6538(2) 0.04300(11) 0.0446(4) Uani 1 1 d . . . H11 H 0.8732 0.5577 0.0440 0.054 Uiso 1 1 calc R A . C2 C 0.76878(14) 0.6358(2) 0.08371(12) 0.0499(4) Uani 1 1 d . A . N1 N 0.74573(11) 0.75905(18) 0.11634(10) 0.0485(4) Uani 1 1 d . . . C3 C 0.78557(13) 0.8986(2) 0.10672(11) 0.0450(4) Uani 1 1 d . A . C4 C 0.72895(16) 1.0338(2) 0.10800(15) 0.0599(5) Uani 1 1 d . . . H41 H 0.6695 1.0147 0.0808 0.072 Uiso 1 1 calc R A . H42 H 0.7242 1.0546 0.1571 0.072 Uiso 1 1 calc R . . C5 C 0.7665(2) 1.1652(3) 0.0773(2) 0.0952(11) Uani 1 1 d . A . H51 H 0.7502 1.1600 0.0254 0.114 Uiso 1 1 calc R . . H52 H 0.7389 1.2528 0.0923 0.114 Uiso 1 1 calc R . . C6 C 0.8627(2) 1.1814(3) 0.0976(2) 0.0852(8) Uani 1 1 d . . . H61 H 0.8782 1.2046 0.1483 0.102 Uiso 1 1 calc R A . H62 H 0.8809 1.2638 0.0714 0.102 Uiso 1 1 calc R . . C7 C 0.91372(15) 1.0470(2) 0.08330(13) 0.0576(5) Uani 1 1 d . A . H71 H 0.9712 1.0475 0.1157 0.069 Uiso 1 1 calc R . . H72 H 0.9242 1.0523 0.0347 0.069 Uiso 1 1 calc R . . C8 C 0.86724(13) 0.9043(2) 0.09233(11) 0.0466(4) Uani 1 1 d . . . C9 C 0.91484(12) 0.7626(2) 0.08180(10) 0.0449(4) Uani 1 1 d . A . H91 H 0.9561 0.7834 0.0497 0.054 Uiso 1 1 calc R . . C10 C 0.96836(13) 0.6962(2) 0.15069(11) 0.0499(4) Uani 1 1 d . . . C11 C 1.01896(14) 0.5693(3) 0.14709(12) 0.0545(5) Uani 1 1 d . A . C12 C 1.0684(2) 0.5087(3) 0.20922(15) 0.0758(7) Uani 1 1 d . . . H121 H 1.1006 0.4229 0.2065 0.091 Uiso 1 1 calc R A . C13 C 1.0705(2) 0.5731(4) 0.27460(15) 0.0900(9) Uani 1 1 d . A . H131 H 1.1043 0.5316 0.3158 0.108 Uiso 1 1 calc R . . C14 C 1.0221(2) 0.7004(4) 0.27936(14) 0.0855(8) Uani 1 1 d . . . H141 H 1.0242 0.7459 0.3235 0.103 Uiso 1 1 calc R A . C15 C 0.97073(17) 0.7585(3) 0.21770(13) 0.0650(6) Uani 1 1 d . A . H151 H 0.9367 0.8419 0.2212 0.078 Uiso 1 1 calc R . . C16 C 0.68265(16) 0.7398(2) 0.16565(13) 0.0599(5) Uani 1 1 d . A . H161 H 0.6764 0.6331 0.1706 0.072 Uiso 1 1 calc R . . C17 C 0.7231(2) 0.7946(4) 0.24031(15) 0.0824(8) Uani 1 1 d . . . H171 H 0.6864 0.7647 0.2732 0.099 Uiso 1 1 calc R A . H172 H 0.7269 0.9000 0.2398 0.099 Uiso 1 1 calc R . . H173 H 0.7816 0.7538 0.2552 0.099 Uiso 1 1 calc R . . C18 C 0.58992(15) 0.7951(3) 0.13239(15) 0.0623(6) Uani 1 1 d . . . C19 C 0.55190(18) 0.7574(4) 0.06270(18) 0.0820(8) Uani 1 1 d . A . H191 H 0.5834 0.6982 0.0366 0.098 Uiso 1 1 calc R . . C20 C 0.4679(2) 0.8060(5) 0.0310(2) 0.1047(12) Uani 1 1 d . . . H201 H 0.4439 0.7789 -0.0160 0.126 Uiso 1 1 calc R A . C21 C 0.4200(2) 0.8922(5) 0.0671(3) 0.1118(13) Uani 1 1 d . A . H211 H 0.3648 0.9285 0.0445 0.134 Uiso 1 1 calc R . . C22 C 0.4538(2) 0.9249(5) 0.1370(3) 0.1155(14) Uani 1 1 d . . . H221 H 0.4196 0.9786 0.1632 0.139 Uiso 1 1 calc R A . C23 C 0.5390(2) 0.8792(4) 0.1700(2) 0.0895(9) Uani 1 1 d . A . H231 H 0.5618 0.9052 0.2174 0.107 Uiso 1 1 calc R . . C24 C 0.83570(18) 0.4391(4) -0.1008(2) 0.0925(10) Uani 1 1 d . A . H241 H 0.8684 0.4057 -0.0546 0.111 Uiso 1 1 calc R . . H242 H 0.8780 0.4808 -0.1270 0.111 Uiso 1 1 calc R . . C25 C 0.7908(3) 0.3145(5) -0.1406(3) 0.1229(16) Uani 1 1 d . . . H251 H 0.8336 0.2390 -0.1441 0.147 Uiso 1 1 calc R A . H252 H 0.7627 0.3459 -0.1878 0.147 Uiso 1 1 calc R . . H253 H 0.7467 0.2764 -0.1160 0.147 Uiso 1 1 calc R . . C26 C 0.6869(7) 0.9081(13) -0.0939(8) 0.120(4) Uani 0.535(18) 1 d PD A 1 H261 H 0.7184 0.9161 -0.1333 0.145 Uiso 0.535(18) 1 calc PR A 1 H262 H 0.7008 0.9939 -0.0634 0.145 Uiso 0.535(18) 1 calc PR A 1 C27 C 0.5899(9) 0.899(2) -0.1219(12) 0.151(7) Uani 0.535(18) 1 d PD A 1 H271 H 0.5754 0.9492 -0.1672 0.181 Uiso 0.535(18) 1 calc PR A 1 H272 H 0.5588 0.9445 -0.0884 0.181 Uiso 0.535(18) 1 calc PR A 1 H273 H 0.5725 0.7977 -0.1282 0.181 Uiso 0.535(18) 1 calc PR A 1 C26A C 0.6612(9) 0.8363(18) -0.1188(5) 0.099(4) Uani 0.465(18) 1 d PD A 2 H263 H 0.6243 0.7585 -0.1439 0.118 Uiso 0.465(18) 1 calc PR A 2 H264 H 0.7006 0.8702 -0.1495 0.118 Uiso 0.465(18) 1 calc PR A 2 C27A C 0.6037(14) 0.9594(14) -0.1052(9) 0.100(4) Uani 0.465(18) 1 d PD A 2 H274 H 0.5460 0.9223 -0.1020 0.120 Uiso 0.465(18) 1 calc PR A 2 H275 H 0.5980 1.0291 -0.1438 0.120 Uiso 0.465(18) 1 calc PR A 2 H276 H 0.6299 1.0068 -0.0609 0.120 Uiso 0.465(18) 1 calc PR A 2 P2 P 0.65278(3) 0.43061(6) 0.60908(3) 0.05159(13) Uani 1 1 d . B . O6 O 0.82597(10) 0.26566(17) 0.55250(9) 0.0598(4) Uani 1 1 d . . . O7 O 0.52827(11) 0.2368(2) 0.42648(9) 0.0660(4) Uani 1 1 d . . . H7 H 0.5019 0.1593 0.4150 0.081(9) Uiso 1 1 calc R . . O8 O 0.56087(12) 0.4820(2) 0.60113(10) 0.0708(4) Uani 1 1 d . . . O9 O 0.72571(14) 0.5414(3) 0.64552(11) 0.0866(6) Uani 1 1 d U . . O10 O 0.67484(13) 0.2936(2) 0.65999(9) 0.0740(5) Uani 1 1 d . . . C28 C 0.68365(12) 0.3815(2) 0.52499(10) 0.0463(4) Uani 1 1 d . . . H281 H 0.6622 0.2809 0.5140 0.056 Uiso 1 1 calc R B . C29 C 0.78424(13) 0.3768(2) 0.53165(11) 0.0470(4) Uani 1 1 d . B . N2 N 0.82215(11) 0.50194(19) 0.51224(10) 0.0512(4) Uani 1 1 d . . . C30 C 0.77080(14) 0.6336(2) 0.49296(12) 0.0516(5) Uani 1 1 d . B . C31 C 0.81854(17) 0.7788(3) 0.50982(16) 0.0680(6) Uani 1 1 d . . . H311 H 0.8579 0.7727 0.5565 0.082 Uiso 1 1 calc R B . H312 H 0.8547 0.7983 0.4743 0.082 Uiso 1 1 calc R . . C32 C 0.7542(2) 0.9030(3) 0.5100(2) 0.0902(9) Uani 1 1 d . B . H321 H 0.7307 0.8982 0.5537 0.108 Uiso 1 1 calc R . . H322 H 0.7857 0.9955 0.5102 0.108 Uiso 1 1 calc R . . C33 C 0.6804(3) 0.9000(3) 0.4484(2) 0.0974(10) Uani 1 1 d . . . H331 H 0.7036 0.9095 0.4047 0.117 Uiso 1 1 calc R B . H332 H 0.6418 0.9835 0.4511 0.117 Uiso 1 1 calc R . . C34 C 0.62588(17) 0.7578(3) 0.44508(15) 0.0667(6) Uani 1 1 d . B . H341 H 0.5833 0.7672 0.4764 0.080 Uiso 1 1 calc R . . H342 H 0.5928 0.7438 0.3965 0.080 Uiso 1 1 calc R . . C35 C 0.68364(15) 0.6250(2) 0.46722(12) 0.0529(5) Uani 1 1 d . . . C36 C 0.63697(14) 0.4780(2) 0.46220(11) 0.0490(4) Uani 1 1 d . B . H361 H 0.5761 0.4955 0.4689 0.059 Uiso 1 1 calc R . . C37 C 0.63068(13) 0.3999(2) 0.39049(11) 0.0495(4) Uani 1 1 d . . . C38 C 0.57385(14) 0.2768(3) 0.37488(11) 0.0526(4) Uani 1 1 d . B . C39 C 0.56562(17) 0.2046(3) 0.31036(13) 0.0652(6) Uani 1 1 d . . . H391 H 0.5281 0.1236 0.3008 0.078 Uiso 1 1 calc R B . C40 C 0.61271(18) 0.2513(3) 0.25945(13) 0.0689(6) Uani 1 1 d . B . H401 H 0.6065 0.2020 0.2159 0.083 Uiso 1 1 calc R . . C41 C 0.66886(19) 0.3710(3) 0.27336(14) 0.0693(6) Uani 1 1 d . . . H411 H 0.7007 0.4028 0.2393 0.083 Uiso 1 1 calc R B . C42 C 0.67737(16) 0.4434(3) 0.33842(12) 0.0597(5) Uani 1 1 d . B . H421 H 0.7155 0.5238 0.3476 0.072 Uiso 1 1 calc R . . C43 C 0.91690(14) 0.4917(3) 0.50526(14) 0.0606(5) Uani 1 1 d . B . H431 H 0.9304 0.3862 0.5072 0.073 Uiso 1 1 calc R . . C44 C 0.9296(2) 0.5415(4) 0.43137(16) 0.0826(8) Uani 1 1 d . . . H441 H 0.9851 0.5041 0.4227 0.099 Uiso 1 1 calc R B . H442 H 0.9301 0.6470 0.4295 0.099 Uiso 1 1 calc R . . H443 H 0.8816 0.5047 0.3954 0.099 Uiso 1 1 calc R . . C45 C 0.98083(14) 0.5581(3) 0.56833(14) 0.0602(5) Uani 1 1 d . . . C46 C 0.96049(19) 0.5682(4) 0.63609(16) 0.0808(8) Uani 1 1 d . B . H461 H 0.9052 0.5364 0.6432 0.097 Uiso 1 1 calc R . . C47 C 1.0208(2) 0.6244(5) 0.69277(18) 0.0973(11) Uani 1 1 d . . . H471 H 1.0056 0.6313 0.7376 0.117 Uiso 1 1 calc R B . C48 C 1.1033(2) 0.6706(5) 0.6841(2) 0.1023(11) Uani 1 1 d . B . H481 H 1.1436 0.7099 0.7226 0.123 Uiso 1 1 calc R . . C49 C 1.1257(2) 0.6579(4) 0.6177(2) 0.0939(10) Uani 1 1 d . . . H491 H 1.1822 0.6856 0.6118 0.113 Uiso 1 1 calc R B . C50 C 1.06491(17) 0.6042(3) 0.55975(18) 0.0749(7) Uani 1 1 d . B . H501 H 1.0801 0.5989 0.5148 0.090 Uiso 1 1 calc R . . C51 C 0.6980(4) 0.6495(8) 0.6952(3) 0.0968(9) Uani 0.632(6) 1 d PDU B 1 H512 H 0.6527 0.7153 0.6697 0.116 Uiso 0.632(6) 1 calc PR B 1 H511 H 0.6751 0.6002 0.7330 0.116 Uiso 0.632(6) 1 calc PR B 1 C52 C 0.7810(4) 0.7304(8) 0.7246(4) 0.1048(13) Uani 0.632(6) 1 d PDU B 1 H521 H 0.7715 0.7928 0.7632 0.126 Uiso 0.632(6) 1 calc PR B 1 H522 H 0.7977 0.7893 0.6875 0.126 Uiso 0.632(6) 1 calc PR B 1 H523 H 0.8276 0.6615 0.7423 0.126 Uiso 0.632(6) 1 calc PR B 1 C53 C 0.6223(3) 0.1613(5) 0.6478(3) 0.1267(16) Uani 1 1 d DU B 1 H531 H 0.5671 0.1840 0.6147 0.152 Uiso 1 1 calc R B 1 H532 H 0.6541 0.0900 0.6245 0.152 Uiso 1 1 calc R B 1 C54 C 0.6019(6) 0.0973(9) 0.7081(4) 0.213(4) Uani 1 1 d DU B 1 H541 H 0.5648 0.0128 0.6945 0.256 Uiso 1 1 calc R B 1 H542 H 0.5708 0.1670 0.7321 0.256 Uiso 1 1 calc R B 1 H543 H 0.6557 0.0675 0.7398 0.256 Uiso 1 1 calc R B 1 C51A C 0.7413(8) 0.6027(9) 0.7176(5) 0.0956(10) Uani 0.368(6) 1 d PDU B 2 H513 H 0.8015 0.5812 0.7425 0.115 Uiso 0.368(6) 1 calc PR B 2 H514 H 0.7001 0.5604 0.7447 0.115 Uiso 0.368(6) 1 calc PR B 2 C52A C 0.7278(8) 0.7637(10) 0.7105(6) 0.1086(15) Uani 0.368(6) 1 d PDU B 2 H524 H 0.7843 0.8116 0.7143 0.130 Uiso 0.368(6) 1 calc PR B 2 H525 H 0.6992 0.7984 0.7479 0.130 Uiso 0.368(6) 1 calc PR B 2 H526 H 0.6910 0.7856 0.6646 0.130 Uiso 0.368(6) 1 calc PR B 2 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 0.0495(3) 0.0434(3) 0.0582(3) -0.0010(2) 0.0090(2) -0.0067(2) O1 0.0760(10) 0.0324(7) 0.1149(14) 0.0025(8) 0.0401(10) -0.0052(7) O2 0.0670(9) 0.0617(9) 0.0603(8) -0.0011(7) 0.0147(7) 0.0277(8) O3 0.0709(10) 0.0677(10) 0.0798(11) 0.0077(9) 0.0063(8) 0.0202(9) O4 0.0807(11) 0.0722(11) 0.0642(9) 0.0019(8) 0.0147(8) -0.0338(9) O5 0.0483(7) 0.0585(9) 0.0721(9) -0.0142(7) 0.0103(6) -0.0093(7) C1 0.0439(9) 0.0324(9) 0.0582(10) -0.0007(7) 0.0117(8) 0.0037(7) C2 0.0498(10) 0.0308(9) 0.0709(12) 0.0064(8) 0.0169(9) 0.0035(8) N1 0.0493(8) 0.0332(8) 0.0677(10) 0.0065(7) 0.0231(7) 0.0035(7) C3 0.0530(10) 0.0281(9) 0.0563(10) 0.0044(7) 0.0167(8) 0.0029(7) C4 0.0629(12) 0.0366(10) 0.0842(15) 0.0030(10) 0.0241(11) 0.0114(9) C5 0.0839(18) 0.0356(13) 0.167(3) 0.0139(15) 0.0279(19) 0.0046(11) C6 0.0843(17) 0.0386(12) 0.136(3) 0.0011(14) 0.0295(17) -0.0074(12) C7 0.0597(12) 0.0435(11) 0.0730(13) -0.0020(10) 0.0215(10) -0.0102(9) C8 0.0506(10) 0.0347(9) 0.0556(10) -0.0013(8) 0.0131(8) -0.0006(8) C9 0.0439(9) 0.0389(9) 0.0531(10) -0.0016(8) 0.0126(7) 0.0013(8) C10 0.0487(9) 0.0478(10) 0.0547(10) 0.0007(9) 0.0137(8) 0.0044(9) C11 0.0538(10) 0.0550(12) 0.0565(11) 0.0038(9) 0.0152(9) 0.0103(9) C12 0.0837(16) 0.0735(17) 0.0696(15) 0.0131(13) 0.0134(12) 0.0264(14) C13 0.103(2) 0.106(2) 0.0566(14) 0.0150(15) 0.0050(13) 0.0303(19) C14 0.108(2) 0.094(2) 0.0531(13) -0.0073(14) 0.0112(13) 0.0147(18) C15 0.0715(14) 0.0646(14) 0.0594(12) -0.0064(11) 0.0139(10) 0.0123(12) C16 0.0661(12) 0.0434(11) 0.0793(14) 0.0111(10) 0.0365(11) 0.0031(9) C17 0.0935(19) 0.088(2) 0.0729(16) 0.0131(15) 0.0343(14) 0.0061(16) C18 0.0563(12) 0.0473(11) 0.0924(17) 0.0054(11) 0.0366(12) -0.0007(9) C19 0.0593(13) 0.093(2) 0.100(2) 0.0005(17) 0.0301(13) 0.0079(14) C20 0.0560(15) 0.137(3) 0.123(3) 0.018(2) 0.0212(16) 0.0076(18) C21 0.0595(16) 0.109(3) 0.172(4) 0.025(3) 0.037(2) 0.0157(18) C22 0.0746(19) 0.100(3) 0.188(5) -0.017(3) 0.064(3) 0.020(2) C23 0.0741(17) 0.0783(18) 0.128(3) -0.0194(18) 0.0488(17) 0.0040(15) C24 0.0608(14) 0.092(2) 0.120(2) -0.0451(19) 0.0060(14) 0.0072(15) C25 0.097(2) 0.090(3) 0.177(4) -0.059(3) 0.015(2) 0.0116(19) C26 0.172(9) 0.070(5) 0.113(8) 0.025(5) 0.010(6) 0.048(6) C27 0.121(9) 0.147(14) 0.170(15) 0.043(11) -0.004(8) 0.060(10) C26A 0.110(7) 0.108(8) 0.070(4) 0.002(4) 0.000(4) 0.061(6) C27A 0.116(9) 0.089(7) 0.095(6) 0.022(5) 0.021(5) 0.052(7) P2 0.0552(3) 0.0451(3) 0.0556(3) 0.0009(2) 0.0136(2) -0.0009(2) O6 0.0585(8) 0.0433(8) 0.0784(10) 0.0097(7) 0.0158(7) 0.0080(7) O7 0.0697(9) 0.0646(10) 0.0669(9) -0.0137(8) 0.0216(7) -0.0218(8) O8 0.0705(10) 0.0675(10) 0.0785(10) 0.0034(8) 0.0247(8) 0.0141(8) O9 0.0913(12) 0.0951(13) 0.0770(11) -0.0321(10) 0.0256(9) -0.0313(11) O10 0.0832(11) 0.0738(11) 0.0655(9) 0.0162(9) 0.0162(8) 0.0062(9) C28 0.0480(10) 0.0357(9) 0.0536(10) -0.0001(8) 0.0067(8) -0.0033(7) C29 0.0516(10) 0.0361(9) 0.0539(10) -0.0005(8) 0.0116(8) 0.0010(8) N2 0.0487(8) 0.0385(8) 0.0669(10) 0.0008(7) 0.0122(7) -0.0013(7) C30 0.0593(11) 0.0330(9) 0.0640(12) 0.0022(8) 0.0159(9) -0.0003(8) C31 0.0709(14) 0.0410(11) 0.0917(17) -0.0007(11) 0.0158(12) -0.0094(11) C32 0.096(2) 0.0395(13) 0.136(3) -0.0101(14) 0.0248(19) -0.0050(13) C33 0.112(2) 0.0415(14) 0.131(3) 0.0166(15) 0.007(2) 0.0092(14) C34 0.0701(14) 0.0458(12) 0.0804(15) 0.0097(11) 0.0059(11) 0.0088(11) C35 0.0630(12) 0.0371(10) 0.0570(11) 0.0010(8) 0.0078(9) -0.0005(9) C36 0.0503(10) 0.0388(10) 0.0571(11) 0.0043(8) 0.0086(8) 0.0007(8) C37 0.0524(10) 0.0429(10) 0.0509(10) 0.0044(8) 0.0043(8) 0.0029(8) C38 0.0513(10) 0.0484(11) 0.0575(11) -0.0001(9) 0.0094(8) -0.0002(9) C39 0.0702(13) 0.0573(13) 0.0667(13) -0.0088(11) 0.0099(10) -0.0067(11) C40 0.0846(16) 0.0677(15) 0.0560(12) -0.0053(11) 0.0177(11) 0.0068(13) C41 0.0816(15) 0.0667(15) 0.0630(13) 0.0149(11) 0.0227(11) 0.0104(13) C42 0.0653(12) 0.0503(12) 0.0636(12) 0.0114(10) 0.0129(10) -0.0013(10) C43 0.0535(11) 0.0497(11) 0.0835(15) 0.0029(11) 0.0253(10) 0.0004(9) C44 0.0762(16) 0.097(2) 0.0814(17) -0.0011(16) 0.0330(14) -0.0061(16) C45 0.0512(11) 0.0491(12) 0.0798(15) 0.0148(10) 0.0116(10) -0.0003(9) C46 0.0639(14) 0.097(2) 0.0798(17) 0.0127(15) 0.0094(12) -0.0174(14) C47 0.088(2) 0.124(3) 0.0747(17) 0.0197(18) 0.0025(14) -0.027(2) C48 0.0782(18) 0.113(3) 0.102(2) 0.020(2) -0.0151(16) -0.0308(19) C49 0.0611(15) 0.098(2) 0.120(3) 0.011(2) 0.0103(15) -0.0259(16) C50 0.0566(13) 0.0654(16) 0.104(2) 0.0094(14) 0.0199(13) -0.0066(11) C51 0.0976(18) 0.1026(18) 0.0909(16) -0.0367(15) 0.0204(15) -0.0286(17) C52 0.101(3) 0.115(3) 0.099(2) -0.038(2) 0.020(2) -0.032(2) C53 0.145(4) 0.089(3) 0.137(3) 0.045(2) 0.004(3) -0.015(2) C54 0.279(8) 0.187(6) 0.166(5) 0.056(5) 0.027(5) -0.118(6) C51A 0.0977(19) 0.1030(19) 0.0866(17) -0.0338(16) 0.0196(17) -0.0289(18) C52A 0.109(3) 0.113(3) 0.102(3) -0.036(2) 0.014(3) -0.025(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 O4 1.4677(17) . ? P1 O3 1.5673(18) . ? P1 O5 1.5743(16) . ? P1 C1 1.813(2) . ? O1 C2 1.218(3) . ? O2 C11 1.365(3) . ? O2 H2 0.8200 . ? O3 C26 1.409(8) . ? O3 C26A 1.422(8) . ? O5 C24 1.440(3) . ? C1 C2 1.519(3) . ? C1 C9 1.544(3) . ? C1 H11 0.9800 . ? C2 N1 1.361(3) . ? N1 C3 1.435(2) . ? N1 C16 1.484(3) . ? C3 C8 1.335(3) . ? C3 C4 1.507(3) . ? C4 C5 1.494(4) . ? C4 H41 0.9700 . ? C4 H42 0.9700 . ? C5 C6 1.456(4) . ? C5 H51 0.9700 . ? C5 H52 0.9700 . ? C6 C7 1.504(4) . ? C6 H61 0.9700 . ? C6 H62 0.9700 . ? C7 C8 1.506(3) . ? C7 H71 0.9700 . ? C7 H72 0.9700 . ? C8 C9 1.513(3) . ? C9 C10 1.525(3) . ? C9 H91 0.9800 . ? C10 C15 1.388(3) . ? C10 C11 1.399(3) . ? C11 C12 1.385(3) . ? C12 C13 1.369(4) . ? C12 H121 0.9300 . ? C13 C14 1.386(5) . ? C13 H131 0.9300 . ? C14 C15 1.381(4) . ? C14 H141 0.9300 . ? C15 H151 0.9300 . ? C16 C17 1.516(4) . ? C16 C18 1.522(3) . ? C16 H161 0.9800 . ? C17 H171 0.9600 . ? C17 H172 0.9600 . ? C17 H173 0.9600 . ? C18 C19 1.380(4) . ? C18 C23 1.388(4) . ? C19 C20 1.381(4) . ? C19 H191 0.9300 . ? C20 C21 1.350(6) . ? C20 H201 0.9300 . ? C21 C22 1.361(7) . ? C21 H211 0.9300 . ? C22 C23 1.395(6) . ? C22 H221 0.9300 . ? C23 H231 0.9300 . ? C24 C25 1.457(5) . ? C24 H241 0.9700 . ? C24 H242 0.9700 . ? C25 H251 0.9600 . ? C25 H252 0.9600 . ? C25 H253 0.9600 . ? C26 C27 1.479(2) . ? C26 H261 0.9700 . ? C26 H262 0.9700 . ? C27 H271 0.9600 . ? C27 H272 0.9600 . ? C27 H273 0.9600 . ? C26A C27A 1.478(2) . ? C26A H263 0.9700 . ? C26A H264 0.9700 . ? C27A H274 0.9600 . ? C27A H275 0.9600 . ? C27A H276 0.9600 . ? P2 O8 1.4634(18) . ? P2 O9 1.5612(19) . ? P2 O10 1.5720(19) . ? P2 C28 1.811(2) . ? O6 C29 1.219(3) . ? O7 C38 1.362(3) . ? O7 H7 0.8200 . ? O9 C51A 1.453(9) . ? O9 C51 1.482(6) . ? O10 C53 1.440(5) . ? C28 C29 1.523(3) . ? C28 C36 1.539(3) . ? C28 H281 0.9800 . ? C29 N2 1.361(3) . ? N2 C30 1.439(3) . ? N2 C43 1.487(3) . ? C30 C35 1.331(3) . ? C30 C31 1.512(3) . ? C31 C32 1.499(4) . ? C31 H311 0.9700 . ? C31 H312 0.9700 . ? C32 C33 1.458(5) . ? C32 H321 0.9700 . ? C32 H322 0.9700 . ? C33 C34 1.533(4) . ? C33 H331 0.9700 . ? C33 H332 0.9700 . ? C34 C35 1.507(3) . ? C34 H341 0.9700 . ? C34 H342 0.9700 . ? C35 C36 1.509(3) . ? C36 C37 1.523(3) . ? C36 H361 0.9800 . ? C37 C42 1.389(3) . ? C37 C38 1.413(3) . ? C38 C39 1.375(3) . ? C39 C40 1.384(4) . ? C39 H391 0.9300 . ? C40 C41 1.380(4) . ? C40 H401 0.9300 . ? C41 C42 1.384(4) . ? C41 H411 0.9300 . ? C42 H421 0.9300 . ? C43 C45 1.515(4) . ? C43 C44 1.525(4) . ? C43 H431 0.9800 . ? C44 H441 0.9600 . ? C44 H442 0.9600 . ? C44 H443 0.9600 . ? C45 C46 1.387(4) . ? C45 C50 1.396(3) . ? C46 C47 1.371(4) . ? C46 H461 0.9300 . ? C47 C48 1.374(5) . ? C47 H471 0.9300 . ? C48 C49 1.377(5) . ? C48 H481 0.9300 . ? C49 C50 1.383(5) . ? C49 H491 0.9300 . ? C50 H501 0.9300 . ? C51 C52 1.480(2) . ? C51 H512 0.9700 . ? C51 H511 0.9700 . ? C52 H521 0.9600 . ? C52 H522 0.9600 . ? C52 H523 0.9600 . ? C53 C54 1.377(6) . ? C53 H531 0.9700 . ? C53 H532 0.9700 . ? C54 H541 0.9600 . ? C54 H542 0.9600 . ? C54 H543 0.9600 . ? C51A C52A 1.480(2) . ? C51A H513 0.9700 . ? C51A H514 0.9700 . ? C52A H524 0.9600 . ? C52A H525 0.9600 . ? C52A H526 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 O4 P1 O3 116.55(12) . . ? O4 P1 O5 113.22(10) . . ? O3 P1 O5 100.83(10) . . ? O4 P1 C1 113.17(9) . . ? O3 P1 C1 105.54(9) . . ? O5 P1 C1 106.31(9) . . ? C11 O2 H2 109.5 . . ? C26 O3 C26A 35.1(5) . . ? C26 O3 P1 124.2(5) . . ? C26A O3 P1 123.1(4) . . ? C24 O5 P1 121.37(15) . . ? C2 C1 C9 111.02(16) . . ? C2 C1 P1 112.73(14) . . ? C9 C1 P1 112.89(13) . . ? C2 C1 H11 106.6 . . ? C9 C1 H11 106.6 . . ? P1 C1 H11 106.6 . . ? O1 C2 N1 123.39(19) . . ? O1 C2 C1 120.79(19) . . ? N1 C2 C1 115.82(16) . . ? C2 N1 C3 120.91(16) . . ? C2 N1 C16 116.82(16) . . ? C3 N1 C16 122.14(16) . . ? C8 C3 N1 120.09(16) . . ? C8 C3 C4 122.54(18) . . ? N1 C3 C4 117.21(16) . . ? C5 C4 C3 112.2(2) . . ? C5 C4 H41 109.2 . . ? C3 C4 H41 109.2 . . ? C5 C4 H42 109.2 . . ? C3 C4 H42 109.2 . . ? H41 C4 H42 107.9 . . ? C6 C5 C4 115.2(3) . . ? C6 C5 H51 108.5 . . ? C4 C5 H51 108.5 . . ? C6 C5 H52 108.5 . . ? C4 C5 H52 108.5 . . ? H51 C5 H52 107.5 . . ? C5 C6 C7 114.0(2) . . ? C5 C6 H61 108.8 . . ? C7 C6 H61 108.8 . . ? C5 C6 H62 108.8 . . ? C7 C6 H62 108.8 . . ? H61 C6 H62 107.7 . . ? C6 C7 C8 113.83(18) . . ? C6 C7 H71 108.8 . . ? C8 C7 H71 108.8 . . ? C6 C7 H72 108.8 . . ? C8 C7 H72 108.8 . . ? H71 C7 H72 107.7 . . ? C3 C8 C7 122.79(18) . . ? C3 C8 C9 119.37(17) . . ? C7 C8 C9 117.81(16) . . ? C8 C9 C10 114.51(16) . . ? C8 C9 C1 107.23(15) . . ? C10 C9 C1 111.36(16) . . ? C8 C9 H91 107.8 . . ? C10 C9 H91 107.8 . . ? C1 C9 H91 107.8 . . ? C15 C10 C11 117.9(2) . . ? C15 C10 C9 122.56(19) . . ? C11 C10 C9 119.56(18) . . ? O2 C11 C12 121.9(2) . . ? O2 C11 C10 118.00(19) . . ? C12 C11 C10 120.1(2) . . ? C13 C12 C11 121.0(3) . . ? C13 C12 H121 119.5 . . ? C11 C12 H121 119.5 . . ? C12 C13 C14 120.0(3) . . ? C12 C13 H131 120.0 . . ? C14 C13 H131 120.0 . . ? C15 C14 C13 119.1(3) . . ? C15 C14 H141 120.5 . . ? C13 C14 H141 120.5 . . ? C14 C15 C10 122.0(2) . . ? C14 C15 H151 119.0 . . ? C10 C15 H151 119.0 . . ? N1 C16 C17 110.8(2) . . ? N1 C16 C18 111.74(19) . . ? C17 C16 C18 117.1(2) . . ? N1 C16 H161 105.4 . . ? C17 C16 H161 105.4 . . ? C18 C16 H161 105.4 . . ? C16 C17 H171 109.5 . . ? C16 C17 H172 109.5 . . ? H171 C17 H172 109.5 . . ? C16 C17 H173 109.5 . . ? H171 C17 H173 109.5 . . ? H172 C17 H173 109.5 . . ? C19 C18 C23 117.2(3) . . ? C19 C18 C16 119.9(2) . . ? C23 C18 C16 122.8(3) . . ? C18 C19 C20 121.2(3) . . ? C18 C19 H191 119.4 . . ? C20 C19 H191 119.4 . . ? C21 C20 C19 121.2(4) . . ? C21 C20 H201 119.4 . . ? C19 C20 H201 119.4 . . ? C20 C21 C22 118.8(3) . . ? C20 C21 H211 120.6 . . ? C22 C21 H211 120.6 . . ? C21 C22 C23 121.0(3) . . ? C21 C22 H221 119.5 . . ? C23 C22 H221 119.5 . . ? C18 C23 C22 120.3(4) . . ? C18 C23 H231 119.8 . . ? C22 C23 H231 119.8 . . ? O5 C24 C25 111.1(2) . . ? O5 C24 H241 109.4 . . ? C25 C24 H241 109.4 . . ? O5 C24 H242 109.4 . . ? C25 C24 H242 109.4 . . ? H241 C24 H242 108.0 . . ? C24 C25 H251 109.5 . . ? C24 C25 H252 109.5 . . ? H251 C25 H252 109.5 . . ? C24 C25 H253 109.5 . . ? H251 C25 H253 109.5 . . ? H252 C25 H253 109.5 . . ? O3 C26 C27 107.7(12) . . ? O3 C26 H261 110.2 . . ? C27 C26 H261 110.2 . . ? O3 C26 H262 110.2 . . ? C27 C26 H262 110.2 . . ? H261 C26 H262 108.5 . . ? O3 C26A C27A 112.1(10) . . ? O3 C26A H263 109.2 . . ? C27A C26A H263 109.2 . . ? O3 C26A H264 109.2 . . ? C27A C26A H264 109.2 . . ? H263 C26A H264 107.9 . . ? C26A C27A H274 109.5 . . ? C26A C27A H275 109.5 . . ? H274 C27A H275 109.5 . . ? C26A C27A H276 109.5 . . ? H274 C27A H276 109.5 . . ? H275 C27A H276 109.5 . . ? O8 P2 O9 115.48(12) . . ? O8 P2 O10 113.66(11) . . ? O9 P2 O10 100.96(12) . . ? O8 P2 C28 113.72(10) . . ? O9 P2 C28 105.14(10) . . ? O10 P2 C28 106.64(10) . . ? C38 O7 H7 109.5 . . ? C51A O9 C51 32.9(4) . . ? C51A O9 P2 129.4(4) . . ? C51 O9 P2 116.1(2) . . ? C53 O10 P2 121.1(2) . . ? C29 C28 C36 112.85(16) . . ? C29 C28 P2 111.79(13) . . ? C36 C28 P2 112.44(14) . . ? C29 C28 H281 106.4 . . ? C36 C28 H281 106.4 . . ? P2 C28 H281 106.4 . . ? O6 C29 N2 123.76(18) . . ? O6 C29 C28 120.55(18) . . ? N2 C29 C28 115.68(16) . . ? C29 N2 C30 121.49(16) . . ? C29 N2 C43 116.67(17) . . ? C30 N2 C43 121.60(18) . . ? C35 C30 N2 120.24(18) . . ? C35 C30 C31 122.5(2) . . ? N2 C30 C31 117.01(18) . . ? C32 C31 C30 111.5(2) . . ? C32 C31 H311 109.3 . . ? C30 C31 H311 109.3 . . ? C32 C31 H312 109.3 . . ? C30 C31 H312 109.3 . . ? H311 C31 H312 108.0 . . ? C33 C32 C31 113.0(3) . . ? C33 C32 H321 109.0 . . ? C31 C32 H321 109.0 . . ? C33 C32 H322 109.0 . . ? C31 C32 H322 109.0 . . ? H321 C32 H322 107.8 . . ? C32 C33 C34 112.2(3) . . ? C32 C33 H331 109.2 . . ? C34 C33 H331 109.2 . . ? C32 C33 H332 109.2 . . ? C34 C33 H332 109.2 . . ? H331 C33 H332 107.9 . . ? C35 C34 C33 112.2(2) . . ? C35 C34 H341 109.2 . . ? C33 C34 H341 109.2 . . ? C35 C34 H342 109.2 . . ? C33 C34 H342 109.2 . . ? H341 C34 H342 107.9 . . ? C30 C35 C34 123.2(2) . . ? C30 C35 C36 120.25(19) . . ? C34 C35 C36 116.52(18) . . ? C35 C36 C37 114.47(17) . . ? C35 C36 C28 108.28(16) . . ? C37 C36 C28 111.47(16) . . ? C35 C36 H361 107.4 . . ? C37 C36 H361 107.4 . . ? C28 C36 H361 107.4 . . ? C42 C37 C38 117.3(2) . . ? C42 C37 C36 123.71(19) . . ? C38 C37 C36 118.95(18) . . ? O7 C38 C39 123.1(2) . . ? O7 C38 C37 116.31(19) . . ? C39 C38 C37 120.6(2) . . ? C38 C39 C40 120.6(2) . . ? C38 C39 H391 119.7 . . ? C40 C39 H391 119.7 . . ? C41 C40 C39 120.0(2) . . ? C41 C40 H401 120.0 . . ? C39 C40 H401 120.0 . . ? C40 C41 C42 119.4(2) . . ? C40 C41 H411 120.3 . . ? C42 C41 H411 120.3 . . ? C41 C42 C37 122.1(2) . . ? C41 C42 H421 119.0 . . ? C37 C42 H421 119.0 . . ? N2 C43 C45 113.22(19) . . ? N2 C43 C44 111.7(2) . . ? C45 C43 C44 115.5(2) . . ? N2 C43 H431 105.1 . . ? C45 C43 H431 105.1 . . ? C44 C43 H431 105.1 . . ? C43 C44 H441 109.5 . . ? C43 C44 H442 109.5 . . ? H441 C44 H442 109.5 . . ? C43 C44 H443 109.5 . . ? H441 C44 H443 109.5 . . ? H442 C44 H443 109.5 . . ? C46 C45 C50 118.1(2) . . ? C46 C45 C43 122.1(2) . . ? C50 C45 C43 119.7(2) . . ? C47 C46 C45 120.9(3) . . ? C47 C46 H461 119.5 . . ? C45 C46 H461 119.5 . . ? C46 C47 C48 120.9(3) . . ? C46 C47 H471 119.6 . . ? C48 C47 H471 119.6 . . ? C47 C48 C49 119.1(3) . . ? C47 C48 H481 120.4 . . ? C49 C48 H481 120.4 . . ? C48 C49 C50 120.6(3) . . ? C48 C49 H491 119.7 . . ? C50 C49 H491 119.7 . . ? C49 C50 C45 120.3(3) . . ? C49 C50 H501 119.8 . . ? C45 C50 H501 119.8 . . ? C52 C51 O9 103.7(5) . . ? C52 C51 H512 111.0 . . ? O9 C51 H512 111.0 . . ? C52 C51 H511 111.0 . . ? O9 C51 H511 111.0 . . ? H512 C51 H511 109.0 . . ? C54 C53 O10 115.5(5) . . ? C54 C53 H531 108.4 . . ? O10 C53 H531 108.4 . . ? C54 C53 H532 108.4 . . ? O10 C53 H532 108.4 . . ? H531 C53 H532 107.5 . . ? O9 C51A C52A 107.4(8) . . ? O9 C51A H513 110.2 . . ? C52A C51A H513 110.2 . . ? O9 C51A H514 110.2 . . ? C52A C51A H514 110.2 . . ? H513 C51A H514 108.5 . . ? C51A C52A H524 109.5 . . ? C51A C52A H525 109.5 . . ? H524 C52A H525 109.5 . . ? C51A C52A H526 109.5 . . ? H524 C52A H526 109.5 . . ? H525 C52A H526 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 O4 P1 O3 C26 9.2(9) . . . . ? O5 P1 O3 C26 -113.8(9) . . . . ? C1 P1 O3 C26 135.7(9) . . . . ? O4 P1 O3 C26A 51.7(10) . . . . ? O5 P1 O3 C26A -71.3(10) . . . . ? C1 P1 O3 C26A 178.2(9) . . . . ? O4 P1 O5 C24 54.1(3) . . . . ? O3 P1 O5 C24 179.3(2) . . . . ? C1 P1 O5 C24 -70.8(2) . . . . ? O4 P1 C1 C2 155.03(15) . . . . ? O3 P1 C1 C2 26.44(17) . . . . ? O5 P1 C1 C2 -80.08(14) . . . . ? O4 P1 C1 C9 28.23(17) . . . . ? O3 P1 C1 C9 -100.35(15) . . . . ? O5 P1 C1 C9 153.12(13) . . . . ? C9 C1 C2 O1 -143.1(2) . . . . ? P1 C1 C2 O1 89.1(2) . . . . ? C9 C1 C2 N1 36.0(2) . . . . ? P1 C1 C2 N1 -91.7(2) . . . . ? O1 C2 N1 C3 -175.6(2) . . . . ? C1 C2 N1 C3 5.3(3) . . . . ? O1 C2 N1 C16 8.4(3) . . . . ? C1 C2 N1 C16 -170.73(18) . . . . ? C2 N1 C3 C8 -27.6(3) . . . . ? C16 N1 C3 C8 148.2(2) . . . . ? C2 N1 C3 C4 147.8(2) . . . . ? C16 N1 C3 C4 -36.4(3) . . . . ? C8 C3 C4 C5 11.6(4) . . . . ? N1 C3 C4 C5 -163.7(3) . . . . ? C3 C4 C5 C6 -41.2(4) . . . . ? C4 C5 C6 C7 53.0(5) . . . . ? C5 C6 C7 C8 -33.3(4) . . . . ? N1 C3 C8 C7 -178.6(2) . . . . ? C4 C3 C8 C7 6.2(3) . . . . ? N1 C3 C8 C9 3.7(3) . . . . ? C4 C3 C8 C9 -171.5(2) . . . . ? C6 C7 C8 C3 4.4(3) . . . . ? C6 C7 C8 C9 -177.8(2) . . . . ? C3 C8 C9 C10 -88.0(2) . . . . ? C7 C8 C9 C10 94.2(2) . . . . ? C3 C8 C9 C1 36.1(2) . . . . ? C7 C8 C9 C1 -141.70(19) . . . . ? C2 C1 C9 C8 -54.6(2) . . . . ? P1 C1 C9 C8 73.11(17) . . . . ? C2 C1 C9 C10 71.4(2) . . . . ? P1 C1 C9 C10 -160.91(13) . . . . ? C8 C9 C10 C15 1.9(3) . . . . ? C1 C9 C10 C15 -119.9(2) . . . . ? C8 C9 C10 C11 -176.64(18) . . . . ? C1 C9 C10 C11 61.5(2) . . . . ? C15 C10 C11 O2 -177.6(2) . . . . ? C9 C10 C11 O2 1.0(3) . . . . ? C15 C10 C11 C12 0.8(3) . . . . ? C9 C10 C11 C12 179.5(2) . . . . ? O2 C11 C12 C13 176.8(3) . . . . ? C10 C11 C12 C13 -1.6(4) . . . . ? C11 C12 C13 C14 0.5(5) . . . . ? C12 C13 C14 C15 1.4(5) . . . . ? C13 C14 C15 C10 -2.2(5) . . . . ? C11 C10 C15 C14 1.1(4) . . . . ? C9 C10 C15 C14 -177.5(3) . . . . ? C2 N1 C16 C17 122.0(2) . . . . ? C3 N1 C16 C17 -54.0(3) . . . . ? C2 N1 C16 C18 -105.5(2) . . . . ? C3 N1 C16 C18 78.6(3) . . . . ? N1 C16 C18 C19 46.2(3) . . . . ? C17 C16 C18 C19 175.5(3) . . . . ? N1 C16 C18 C23 -136.1(3) . . . . ? C17 C16 C18 C23 -6.8(3) . . . . ? C23 C18 C19 C20 2.3(5) . . . . ? C16 C18 C19 C20 -180.0(3) . . . . ? C18 C19 C20 C21 0.0(6) . . . . ? C19 C20 C21 C22 -3.4(7) . . . . ? C20 C21 C22 C23 4.3(7) . . . . ? C19 C18 C23 C22 -1.3(5) . . . . ? C16 C18 C23 C22 -179.0(3) . . . . ? C21 C22 C23 C18 -2.0(6) . . . . ? P1 O5 C24 C25 -177.9(3) . . . . ? C26A O3 C26 C27 44.6(15) . . . . ? P1 O3 C26 C27 145.1(13) . . . . ? C26 O3 C26A C27A -49.8(15) . . . . ? P1 O3 C26A C27A -153.6(12) . . . . ? O8 P2 O9 C51A 62.4(6) . . . . ? O10 P2 O9 C51A -60.6(6) . . . . ? C28 P2 O9 C51A -171.4(6) . . . . ? O8 P2 O9 C51 26.3(4) . . . . ? O10 P2 O9 C51 -96.7(4) . . . . ? C28 P2 O9 C51 152.5(4) . . . . ? O8 P2 O10 C53 54.6(3) . . . . ? O9 P2 O10 C53 178.9(3) . . . . ? C28 P2 O10 C53 -71.5(3) . . . . ? O8 P2 C28 C29 161.65(14) . . . . ? O9 P2 C28 C29 34.37(18) . . . . ? O10 P2 C28 C29 -72.28(16) . . . . ? O8 P2 C28 C36 33.50(17) . . . . ? O9 P2 C28 C36 -93.78(16) . . . . ? O10 P2 C28 C36 159.57(14) . . . . ? C36 C28 C29 O6 -146.3(2) . . . . ? P2 C28 C29 O6 85.7(2) . . . . ? C36 C28 C29 N2 32.9(2) . . . . ? P2 C28 C29 N2 -95.00(19) . . . . ? O6 C29 N2 C30 -175.4(2) . . . . ? C28 C29 N2 C30 5.3(3) . . . . ? O6 C29 N2 C43 10.2(3) . . . . ? C28 C29 N2 C43 -169.02(18) . . . . ? C29 N2 C30 C35 -25.7(3) . . . . ? C43 N2 C30 C35 148.4(2) . . . . ? C29 N2 C30 C31 148.7(2) . . . . ? C43 N2 C30 C31 -37.2(3) . . . . ? C35 C30 C31 C32 12.9(4) . . . . ? N2 C30 C31 C32 -161.4(2) . . . . ? C30 C31 C32 C33 -46.0(4) . . . . ? C31 C32 C33 C34 59.8(4) . . . . ? C32 C33 C34 C35 -38.3(4) . . . . ? N2 C30 C35 C34 -179.2(2) . . . . ? C31 C30 C35 C34 6.6(4) . . . . ? N2 C30 C35 C36 3.7(3) . . . . ? C31 C30 C35 C36 -170.4(2) . . . . ? C33 C34 C35 C30 5.8(4) . . . . ? C33 C34 C35 C36 -177.0(3) . . . . ? C30 C35 C36 C37 -92.1(2) . . . . ? C34 C35 C36 C37 90.6(2) . . . . ? C30 C35 C36 C28 32.9(3) . . . . ? C34 C35 C36 C28 -144.3(2) . . . . ? C29 C28 C36 C35 -50.1(2) . . . . ? P2 C28 C36 C35 77.50(18) . . . . ? C29 C28 C36 C37 76.7(2) . . . . ? P2 C28 C36 C37 -155.73(14) . . . . ? C35 C36 C37 C42 11.6(3) . . . . ? C28 C36 C37 C42 -111.7(2) . . . . ? C35 C36 C37 C38 -167.78(18) . . . . ? C28 C36 C37 C38 68.9(2) . . . . ? C42 C37 C38 O7 -179.54(19) . . . . ? C36 C37 C38 O7 -0.1(3) . . . . ? C42 C37 C38 C39 -0.2(3) . . . . ? C36 C37 C38 C39 179.2(2) . . . . ? O7 C38 C39 C40 179.1(2) . . . . ? C37 C38 C39 C40 -0.1(4) . . . . ? C38 C39 C40 C41 0.3(4) . . . . ? C39 C40 C41 C42 -0.1(4) . . . . ? C40 C41 C42 C37 -0.3(4) . . . . ? C38 C37 C42 C41 0.5(3) . . . . ? C36 C37 C42 C41 -179.0(2) . . . . ? C29 N2 C43 C45 -103.0(2) . . . . ? C30 N2 C43 C45 82.6(3) . . . . ? C29 N2 C43 C44 124.6(2) . . . . ? C30 N2 C43 C44 -49.8(3) . . . . ? N2 C43 C45 C46 25.9(3) . . . . ? C44 C43 C45 C46 156.4(3) . . . . ? N2 C43 C45 C50 -157.4(2) . . . . ? C44 C43 C45 C50 -26.9(3) . . . . ? C50 C45 C46 C47 1.1(5) . . . . ? C43 C45 C46 C47 177.9(3) . . . . ? C45 C46 C47 C48 -0.8(6) . . . . ? C46 C47 C48 C49 -0.9(6) . . . . ? C47 C48 C49 C50 2.3(6) . . . . ? C48 C49 C50 C45 -1.9(5) . . . . ? C46 C45 C50 C49 0.2(4) . . . . ? C43 C45 C50 C49 -176.6(3) . . . . ? C51A O9 C51 C52 53.1(8) . . . . ? P2 O9 C51 C52 176.1(5) . . . . ? P2 O10 C53 C54 -137.4(5) . . . . ? C51 O9 C51A C52A -39.7(7) . . . . ? P2 O9 C51A C52A -116.8(8) . . . . ? _refine_special_details ; The C27, C28, C52, C53, C54 and C55 atoms of the diethoxy substitents are disordered over two partially occupied positions, respectively ; #