# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'D Boyd' _publ_contact_author_email DR.BOYD@QUB.AC.UK _publ_section_title ; Chemoenzymatic synthesis of chiral 2,2'-bipyridine ligands and their N-oxide derivatives : applications in the asymmetric aminolysis of epoxides and asymmetric allylation of aldehydes. ; loop_ _publ_author_name 'D Boyd' 'Christopher C R Allen' 'John T G Hamilton' 'Stuart L James' 'J Malone' 'Deirdre Murphy' ; L.Sbircea ; 'Narain D Sharma' # Attachment '2J.cif' data_2J _database_code_depnum_ccdc_archive 'CCDC 746347' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 N2 O6' _chemical_formula_sum 'C24 H28 N2 O6' _chemical_formula_weight 440.48 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 36.354(7) _cell_length_b 6.0133(11) _cell_length_c 16.828(3) _cell_angle_alpha 90.00 _cell_angle_beta 117.068(3) _cell_angle_gamma 90.00 _cell_volume 3275.7(10) _cell_formula_units_Z 6 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1021 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 23.2 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1404 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.922 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10583 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 23.27 _reflns_number_total 4687 _reflns_number_gt 4218 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(8) _refine_ls_number_reflns 4687 _refine_ls_number_parameters 439 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0717 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.70598(5) 0.7691(3) 0.80634(10) 0.0275(4) Uani 1 1 d . . . O1 O 0.67837(4) 0.6372(3) 0.74853(8) 0.0334(4) Uani 1 1 d . . . C2 C 0.69363(6) 0.9442(4) 0.84051(12) 0.0272(5) Uani 1 1 d . . . C3 C 0.72284(6) 1.0869(4) 0.90034(13) 0.0314(5) Uani 1 1 d . . . H3 H 0.7142 1.2129 0.9216 0.038 Uiso 1 1 calc R . . C4 C 0.76454(6) 1.0486(4) 0.92972(13) 0.0322(5) Uani 1 1 d . . . H4 H 0.7845 1.1444 0.9725 0.039 Uiso 1 1 calc R . . C4A C 0.77684(6) 0.8684(4) 0.89594(13) 0.0288(5) Uani 1 1 d . . . C5 C 0.82214(6) 0.8157(4) 0.92779(14) 0.0363(6) Uani 1 1 d . . . H5A H 0.8380 0.8616 0.9909 0.044 Uiso 1 1 calc R . . H5B H 0.8326 0.9020 0.8921 0.044 Uiso 1 1 calc R . . C6 C 0.82911(6) 0.5690(4) 0.91950(14) 0.0384(6) Uani 1 1 d . . . H6A H 0.8586 0.5429 0.9360 0.046 Uiso 1 1 calc R . . H6B H 0.8222 0.4837 0.9613 0.046 Uiso 1 1 calc R . . C7 C 0.80260(6) 0.4884(4) 0.82503(13) 0.0327(5) Uani 1 1 d . . . H7 H 0.8073 0.3259 0.8208 0.039 Uiso 1 1 calc R . . O7 O 0.81330(4) 0.6095(3) 0.76551(9) 0.0407(4) Uani 1 1 d . . . C8 C 0.75647(6) 0.5336(4) 0.78943(13) 0.0305(5) Uani 1 1 d . . . H8 H 0.7427 0.3988 0.7984 0.037 Uiso 1 1 calc R . . O8 O 0.74291(4) 0.5672(3) 0.69596(9) 0.0357(4) Uani 1 1 d . . . C8A C 0.74739(6) 0.7314(4) 0.83229(13) 0.0270(5) Uani 1 1 d . . . C9 C 0.77693(6) 0.6410(4) 0.68202(14) 0.0339(5) Uani 1 1 d . . . C10 C 0.77835(7) 0.4984(5) 0.60996(15) 0.0479(7) Uani 1 1 d . . . H10A H 0.8009 0.5488 0.5976 0.072 Uiso 1 1 calc R . . H10B H 0.7520 0.5104 0.5556 0.072 Uiso 1 1 calc R . . H10C H 0.7831 0.3431 0.6298 0.072 Uiso 1 1 calc R . . C11 C 0.77329(8) 0.8854(4) 0.66037(18) 0.0525(7) Uani 1 1 d . . . H11A H 0.7725 0.9696 0.7094 0.079 Uiso 1 1 calc R . . H11B H 0.7479 0.9127 0.6053 0.079 Uiso 1 1 calc R . . H11C H 0.7971 0.9330 0.6522 0.079 Uiso 1 1 calc R . . N1' N 0.63292(4) 0.7988(3) 0.84391(10) 0.0261(4) Uani 1 1 d . . . O1' O 0.65697(4) 0.6424(3) 0.89388(9) 0.0330(4) Uani 1 1 d . . . C2' C 0.64923(6) 0.9652(4) 0.81319(12) 0.0268(5) Uani 1 1 d . . . C3' C 0.62447(6) 1.1392(4) 0.76523(12) 0.0286(5) Uani 1 1 d . . . H3' H 0.6360 1.2580 0.7466 0.034 Uiso 1 1 calc R . . C4' C 0.58294(6) 1.1422(4) 0.74392(12) 0.0269(5) Uani 1 1 d . . . H4' H 0.5658 1.2599 0.7090 0.032 Uiso 1 1 calc R . . C4A' C 0.56647(6) 0.9728(3) 0.77373(12) 0.0240(5) Uani 1 1 d . . . C5' C 0.52165(6) 0.9620(4) 0.75356(13) 0.0278(5) Uani 1 1 d . . . H5'1 H 0.5048 1.0501 0.6993 0.033 Uiso 1 1 calc R . . H5'2 H 0.5182 1.0272 0.8038 0.033 Uiso 1 1 calc R . . C6' C 0.50660(6) 0.7221(3) 0.73924(13) 0.0299(5) Uani 1 1 d . . . H6'1 H 0.4770 0.7185 0.7246 0.036 Uiso 1 1 calc R . . H6'2 H 0.5095 0.6582 0.6882 0.036 Uiso 1 1 calc R . . C7' C 0.53092(6) 0.5833(4) 0.82157(12) 0.0266(5) Uani 1 1 d . . . H7' H 0.5240 0.4227 0.8072 0.032 Uiso 1 1 calc R . . O7' O 0.52110(4) 0.6488(3) 0.89174(8) 0.0309(3) Uani 1 1 d . . . C8' C 0.57835(6) 0.6150(4) 0.86332(12) 0.0247(5) Uani 1 1 d . . . H8' H 0.5918 0.4731 0.8594 0.030 Uiso 1 1 calc R . . O8' O 0.59052(4) 0.6686(2) 0.95550(8) 0.0312(4) Uani 1 1 d . . . C8A' C 0.59195(5) 0.8013(4) 0.82436(12) 0.0231(5) Uani 1 1 d . . . C9' C 0.55732(6) 0.6064(4) 0.97357(13) 0.0281(5) Uani 1 1 d . . . C10' C 0.56014(6) 0.3616(4) 0.99783(14) 0.0370(6) Uani 1 1 d . . . H10D H 0.5360 0.3194 1.0059 0.056 Uiso 1 1 calc R . . H10E H 0.5853 0.3352 1.0534 0.056 Uiso 1 1 calc R . . H10F H 0.5609 0.2723 0.9499 0.056 Uiso 1 1 calc R . . C11' C 0.55813(7) 0.7562(4) 1.04566(14) 0.0390(6) Uani 1 1 d . . . H11D H 0.5530 0.9098 1.0239 0.058 Uiso 1 1 calc R . . H11E H 0.5852 0.7465 1.0980 0.058 Uiso 1 1 calc R . . H11F H 0.5366 0.7099 1.0621 0.058 Uiso 1 1 calc R . . N1" N 0.96675(4) 0.9376(3) 0.53094(10) 0.0239(4) Uani 1 1 d . . . O1" O 0.99430(4) 0.7931(2) 0.58066(8) 0.0303(3) Uani 1 1 d . . . C2" C 0.97851(6) 1.1066(3) 0.49239(12) 0.0232(5) Uani 1 1 d . . . C3" C 0.95033(6) 1.2693(4) 0.44437(12) 0.0280(5) Uani 1 1 d . . . H3" H 0.9588 1.3904 0.4202 0.034 Uiso 1 1 calc R . . C4" C 0.90990(6) 1.2574(4) 0.43113(12) 0.0291(5) Uani 1 1 d . . . H4" H 0.8904 1.3668 0.3962 0.035 Uiso 1 1 calc R . . C4A" C 0.89810(6) 1.0853(4) 0.46911(12) 0.0260(5) Uani 1 1 d . . . C5" C 0.85470(6) 1.0602(4) 0.45722(14) 0.0309(5) Uani 1 1 d . . . H5"1 H 0.8354 1.1413 0.4030 0.037 Uiso 1 1 calc R . . H5"2 H 0.8527 1.1257 0.5091 0.037 Uiso 1 1 calc R . . C6" C 0.84271(6) 0.8161(4) 0.44862(14) 0.0347(5) Uani 1 1 d . . . H6"1 H 0.8139 0.8022 0.4393 0.042 Uiso 1 1 calc R . . H6"2 H 0.8442 0.7516 0.3960 0.042 Uiso 1 1 calc R . . C7" C 0.87114(6) 0.6891(4) 0.53147(13) 0.0311(5) Uani 1 1 d . . . H7" H 0.8660 0.5258 0.5210 0.037 Uiso 1 1 calc R . . O7" O 0.86295(4) 0.7579(3) 0.60343(8) 0.0340(4) Uani 1 1 d . . . C8" C 0.91784(6) 0.7388(4) 0.56640(12) 0.0271(5) Uani 1 1 d . . . H8" H 0.9326 0.6013 0.5633 0.033 Uiso 1 1 calc R . . O8" O 0.93170(4) 0.8027(3) 0.65843(8) 0.0367(4) Uani 1 1 d . . . C8A" C 0.92699(6) 0.9258(3) 0.51980(12) 0.0227(5) Uani 1 1 d . . . C9" C 0.90062(6) 0.7371(4) 0.68324(13) 0.0322(5) Uani 1 1 d . . . C10" C 0.90700(7) 0.4990(4) 0.71633(16) 0.0418(6) Uani 1 1 d . . . H10G H 0.9068 0.4005 0.6697 0.063 Uiso 1 1 calc R . . H10H H 0.8847 0.4564 0.7308 0.063 Uiso 1 1 calc R . . H10I H 0.9336 0.4863 0.7698 0.063 Uiso 1 1 calc R . . C11" C 0.90041(8) 0.8980(4) 0.75119(15) 0.0504(7) Uani 1 1 d . . . H11G H 0.9280 0.9037 0.8023 0.076 Uiso 1 1 calc R . . H11H H 0.8803 0.8493 0.7713 0.076 Uiso 1 1 calc R . . H11I H 0.8928 1.0462 0.7244 0.076 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 N1 0.0211(9) 0.0380(11) 0.0197(9) -0.0003(9) 0.0060(7) -0.0061(8) O1 0.0236(7) 0.0461(10) 0.0270(8) -0.0105(8) 0.0085(6) -0.0102(7) C2 0.0272(12) 0.0347(13) 0.0206(11) -0.0006(10) 0.0117(9) -0.0033(10) C3 0.0317(12) 0.0364(13) 0.0266(11) -0.0013(11) 0.0137(10) -0.0028(10) C4 0.0278(12) 0.0398(14) 0.0244(12) -0.0043(11) 0.0078(10) -0.0090(10) C4A 0.0210(11) 0.0394(14) 0.0240(11) 0.0037(10) 0.0085(9) -0.0049(10) C5 0.0219(11) 0.0481(16) 0.0320(12) -0.0013(11) 0.0061(10) -0.0050(11) C6 0.0231(11) 0.0476(15) 0.0374(13) 0.0059(12) 0.0076(10) -0.0015(11) C7 0.0258(12) 0.0346(13) 0.0370(13) 0.0039(11) 0.0136(10) -0.0002(10) O7 0.0273(8) 0.0580(11) 0.0386(9) 0.0039(9) 0.0165(7) -0.0049(8) C8 0.0275(12) 0.0375(13) 0.0248(11) 0.0027(10) 0.0104(10) -0.0027(10) O8 0.0273(8) 0.0534(10) 0.0265(8) -0.0042(8) 0.0124(7) -0.0048(7) C8A 0.0215(11) 0.0350(13) 0.0232(11) 0.0041(10) 0.0090(9) -0.0035(10) C9 0.0300(12) 0.0399(14) 0.0332(13) -0.0011(11) 0.0156(10) -0.0022(11) C10 0.0511(15) 0.0549(17) 0.0484(15) -0.0101(13) 0.0320(13) -0.0095(13) C11 0.0569(17) 0.0446(17) 0.0541(17) 0.0044(13) 0.0236(14) -0.0030(13) N1' 0.0227(9) 0.0332(11) 0.0198(9) 0.0013(8) 0.0074(8) 0.0011(9) O1' 0.0242(7) 0.0423(9) 0.0288(8) 0.0114(8) 0.0090(6) 0.0093(7) C2' 0.0270(12) 0.0353(12) 0.0183(11) -0.0015(10) 0.0105(9) -0.0056(10) C3' 0.0350(12) 0.0302(12) 0.0220(10) -0.0024(10) 0.0141(9) -0.0058(11) C4' 0.0288(12) 0.0289(12) 0.0223(11) -0.0004(10) 0.0111(9) 0.0011(10) C4A' 0.0262(11) 0.0276(11) 0.0174(10) -0.0025(10) 0.0092(9) 0.0001(10) C5' 0.0241(11) 0.0314(12) 0.0260(11) 0.0036(10) 0.0097(9) 0.0037(10) C6' 0.0224(11) 0.0380(14) 0.0273(12) -0.0008(10) 0.0097(9) 0.0016(9) C7' 0.0251(11) 0.0287(12) 0.0285(11) -0.0016(10) 0.0143(10) -0.0002(10) O7' 0.0289(8) 0.0376(9) 0.0284(8) 0.0023(7) 0.0148(7) 0.0031(7) C8' 0.0257(11) 0.0258(12) 0.0226(11) 0.0002(10) 0.0110(9) 0.0020(9) O8' 0.0281(8) 0.0440(9) 0.0209(7) 0.0013(7) 0.0106(6) -0.0070(7) C8A' 0.0207(11) 0.0303(12) 0.0174(10) -0.0023(10) 0.0080(8) 0.0008(10) C9' 0.0255(11) 0.0312(13) 0.0299(12) 0.0006(10) 0.0147(10) 0.0003(10) C10' 0.0408(14) 0.0348(14) 0.0376(13) 0.0024(11) 0.0197(11) 0.0002(11) C11' 0.0551(14) 0.0338(13) 0.0350(12) 0.0008(12) 0.0266(11) 0.0003(12) N1" 0.0236(10) 0.0279(10) 0.0190(9) 0.0000(8) 0.0087(8) 0.0033(8) O1" 0.0249(7) 0.0346(9) 0.0297(8) 0.0085(7) 0.0109(6) 0.0076(7) C2" 0.0259(10) 0.0270(12) 0.0164(10) -0.0024(9) 0.0095(9) -0.0034(9) C3" 0.0340(12) 0.0312(12) 0.0209(10) 0.0027(10) 0.0143(9) 0.0018(11) C4" 0.0310(12) 0.0334(13) 0.0228(11) 0.0062(11) 0.0121(9) 0.0097(10) C4A" 0.0229(11) 0.0345(13) 0.0182(10) -0.0018(10) 0.0072(9) 0.0014(10) C5" 0.0250(11) 0.0409(13) 0.0243(11) 0.0035(10) 0.0090(9) 0.0030(10) C6" 0.0214(11) 0.0491(15) 0.0304(12) -0.0023(11) 0.0089(9) 0.0001(11) C7" 0.0277(11) 0.0337(13) 0.0334(12) -0.0048(10) 0.0154(10) -0.0036(10) O7" 0.0335(8) 0.0405(9) 0.0319(8) 0.0033(8) 0.0184(7) 0.0035(7) C8" 0.0276(11) 0.0299(12) 0.0235(11) -0.0006(10) 0.0113(9) -0.0010(9) O8" 0.0341(8) 0.0523(10) 0.0228(7) 0.0007(7) 0.0122(7) -0.0123(8) C8A" 0.0207(11) 0.0292(12) 0.0179(10) -0.0025(9) 0.0084(9) -0.0002(9) C9" 0.0320(12) 0.0387(14) 0.0293(12) 0.0020(11) 0.0169(11) -0.0024(10) C10" 0.0427(14) 0.0409(15) 0.0459(15) 0.0105(12) 0.0237(12) 0.0034(12) C11" 0.0766(18) 0.0444(16) 0.0400(14) -0.0023(12) 0.0350(14) -0.0052(14) _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 N1 O1 1.301(2) . ? N1 C2 1.370(3) . ? N1 C8A 1.382(2) . ? C2 C3 1.380(3) . ? C2 C2' 1.469(3) . ? C3 C4 1.384(3) . ? C3 H3 0.9500 . ? C4 C4A 1.388(3) . ? C4 H4 0.9500 . ? C4A C8A 1.389(3) . ? C4A C5 1.515(3) . ? C5 C6 1.522(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.515(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O7 1.428(2) . ? C7 C8 1.526(3) . ? C7 H7 1.0000 . ? O7 C9 1.438(2) . ? C8 O8 1.433(2) . ? C8 C8A 1.504(3) . ? C8 H8 1.0000 . ? O8 C9 1.430(2) . ? C9 C10 1.505(3) . ? C9 C11 1.505(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? N1' O1' 1.299(2) . ? N1' C8A' 1.372(2) . ? N1' C2' 1.378(3) . ? C2' C3' 1.377(3) . ? C3' C4' 1.384(3) . ? C3' H3' 0.9500 . ? C4' C4A' 1.386(3) . ? C4' H4' 0.9500 . ? C4A' C8A' 1.389(3) . ? C4A' C5' 1.507(3) . ? C5' C6' 1.522(3) . ? C5' H5'1 0.9900 . ? C5' H5'2 0.9900 . ? C6' C7' 1.511(3) . ? C6' H6'1 0.9900 . ? C6' H6'2 0.9900 . ? C7' O7' 1.435(2) . ? C7' C8' 1.549(3) . ? C7' H7' 1.0000 . ? O7' C9' 1.430(2) . ? C8' O8' 1.443(2) . ? C8' C8A' 1.491(3) . ? C8' H8' 1.0000 . ? O8' C9' 1.422(2) . ? C9' C11' 1.500(3) . ? C9' C10' 1.518(3) . ? C10' H10D 0.9800 . ? C10' H10E 0.9800 . ? C10' H10F 0.9800 . ? C11' H11D 0.9800 . ? C11' H11E 0.9800 . ? C11' H11F 0.9800 . ? N1" O1" 1.3024(19) . ? N1" C8A" 1.372(2) . ? N1" C2" 1.374(2) . ? C2" C3" 1.381(3) . ? C2" C2" 1.464(4) 2_756 ? C3" C4" 1.385(3) . ? C3" H3" 0.9500 . ? C4" C4A" 1.383(3) . ? C4" H4" 0.9500 . ? C4A" C8A" 1.392(3) . ? C4A" C5" 1.505(3) . ? C5" C6" 1.519(3) . ? C5" H5"1 0.9900 . ? C5" H5"2 0.9900 . ? C6" C7" 1.511(3) . ? C6" H6"1 0.9900 . ? C6" H6"2 0.9900 . ? C7" O7" 1.433(2) . ? C7" C8" 1.552(3) . ? C7" H7" 1.0000 . ? O7" C9" 1.421(2) . ? C8" O8" 1.446(2) . ? C8" C8A" 1.492(3) . ? C8" H8" 1.0000 . ? O8" C9" 1.427(2) . ? C9" C11" 1.501(3) . ? C9" C10" 1.515(3) . ? C10" H10G 0.9800 . ? C10" H10H 0.9800 . ? C10" H10I 0.9800 . ? C11" H11G 0.9800 . ? C11" H11H 0.9800 . ? C11" H11I 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 N1 C2 119.56(15) . . ? O1 N1 C8A 119.67(17) . . ? C2 N1 C8A 120.77(16) . . ? N1 C2 C3 119.60(18) . . ? N1 C2 C2' 117.27(18) . . ? C3 C2 C2' 123.1(2) . . ? C2 C3 C4 120.7(2) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C4A 119.23(19) . . ? C3 C4 H4 120.4 . . ? C4A C4 H4 120.4 . . ? C4 C4A C8A 120.00(18) . . ? C4 C4A C5 121.25(18) . . ? C8A C4A C5 118.75(19) . . ? C4A C5 C6 111.77(18) . . ? C4A C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? C4A C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 110.78(19) . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? O7 C7 C6 109.05(17) . . ? O7 C7 C8 103.61(16) . . ? C6 C7 C8 114.56(18) . . ? O7 C7 H7 109.8 . . ? C6 C7 H7 109.8 . . ? C8 C7 H7 109.8 . . ? C7 O7 C9 109.23(15) . . ? O8 C8 C8A 111.96(17) . . ? O8 C8 C7 102.94(15) . . ? C8A C8 C7 113.22(17) . . ? O8 C8 H8 109.5 . . ? C8A C8 H8 109.5 . . ? C7 C8 H8 109.5 . . ? C9 O8 C8 109.42(15) . . ? N1 C8A C4A 119.53(18) . . ? N1 C8A C8 115.07(17) . . ? C4A C8A C8 125.37(17) . . ? O8 C9 O7 106.17(16) . . ? O8 C9 C10 107.74(18) . . ? O7 C9 C10 111.03(18) . . ? O8 C9 C11 110.82(19) . . ? O7 C9 C11 107.77(19) . . ? C10 C9 C11 113.1(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O1' N1' C8A' 120.04(16) . . ? O1' N1' C2' 119.39(15) . . ? C8A' N1' C2' 120.53(17) . . ? C3' C2' N1' 119.57(17) . . ? C3' C2' C2 125.53(19) . . ? N1' C2' C2 114.80(18) . . ? C2' C3' C4' 120.5(2) . . ? C2' C3' H3' 119.8 . . ? C4' C3' H3' 119.8 . . ? C3' C4' C4A' 119.77(19) . . ? C3' C4' H4' 120.1 . . ? C4A' C4' H4' 120.1 . . ? C4' C4A' C8A' 119.39(18) . . ? C4' C4A' C5' 123.42(18) . . ? C8A' C4A' C5' 117.19(18) . . ? C4A' C5' C6' 110.50(17) . . ? C4A' C5' H5'1 109.6 . . ? C6' C5' H5'1 109.6 . . ? C4A' C5' H5'2 109.6 . . ? C6' C5' H5'2 109.6 . . ? H5'1 C5' H5'2 108.1 . . ? C7' C6' C5' 111.10(16) . . ? C7' C6' H6'1 109.4 . . ? C5' C6' H6'1 109.4 . . ? C7' C6' H6'2 109.4 . . ? C5' C6' H6'2 109.4 . . ? H6'1 C6' H6'2 108.0 . . ? O7' C7' C6' 110.01(16) . . ? O7' C7' C8' 103.61(14) . . ? C6' C7' C8' 114.47(16) . . ? O7' C7' H7' 109.5 . . ? C6' C7' H7' 109.5 . . ? C8' C7' H7' 109.5 . . ? C9' O7' C7' 106.18(14) . . ? O8' C8' C8A' 107.68(16) . . ? O8' C8' C7' 104.39(14) . . ? C8A' C8' C7' 114.58(16) . . ? O8' C8' H8' 110.0 . . ? C8A' C8' H8' 110.0 . . ? C7' C8' H8' 110.0 . . ? C9' O8' C8' 107.22(14) . . ? N1' C8A' C4A' 120.21(18) . . ? N1' C8A' C8' 115.31(17) . . ? C4A' C8A' C8' 124.45(16) . . ? O8' C9' O7' 104.26(15) . . ? O8' C9' C11' 107.98(16) . . ? O7' C9' C11' 110.02(17) . . ? O8' C9' C10' 110.65(17) . . ? O7' C9' C10' 110.58(17) . . ? C11' C9' C10' 112.97(18) . . ? C9' C10' H10D 109.5 . . ? C9' C10' H10E 109.5 . . ? H10D C10' H10E 109.5 . . ? C9' C10' H10F 109.5 . . ? H10D C10' H10F 109.5 . . ? H10E C10' H10F 109.5 . . ? C9' C11' H11D 109.5 . . ? C9' C11' H11E 109.5 . . ? H11D C11' H11E 109.5 . . ? C9' C11' H11F 109.5 . . ? H11D C11' H11F 109.5 . . ? H11E C11' H11F 109.5 . . ? O1" N1" C8A" 120.50(16) . . ? O1" N1" C2" 118.90(15) . . ? C8A" N1" C2" 120.56(16) . . ? N1" C2" C3" 119.54(17) . . ? N1" C2" C2" 116.99(14) . 2_756 ? C3" C2" C2" 123.43(15) . 2_756 ? C2" C3" C4" 120.5(2) . . ? C2" C3" H3" 119.7 . . ? C4" C3" H3" 119.7 . . ? C4A" C4" C3" 119.62(19) . . ? C4A" C4" H4" 120.2 . . ? C3" C4" H4" 120.2 . . ? C4" C4A" C8A" 119.52(17) . . ? C4" C4A" C5" 122.72(18) . . ? C8A" C4A" C5" 117.76(18) . . ? C4A" C5" C6" 110.34(17) . . ? C4A" C5" H5"1 109.6 . . ? C6" C5" H5"1 109.6 . . ? C4A" C5" H5"2 109.6 . . ? C6" C5" H5"2 109.6 . . ? H5"1 C5" H5"2 108.1 . . ? C7" C6" C5" 110.74(18) . . ? C7" C6" H6"1 109.5 . . ? C5" C6" H6"1 109.5 . . ? C7" C6" H6"2 109.5 . . ? C5" C6" H6"2 109.5 . . ? H6"1 C6" H6"2 108.1 . . ? O7" C7" C6" 108.41(16) . . ? O7" C7" C8" 103.67(15) . . ? C6" C7" C8" 115.04(17) . . ? O7" C7" H7" 109.8 . . ? C6" C7" H7" 109.8 . . ? C8" C7" H7" 109.8 . . ? C9" O7" C7" 106.97(14) . . ? O8" C8" C8A" 108.08(16) . . ? O8" C8" C7" 104.17(14) . . ? C8A" C8" C7" 114.39(16) . . ? O8" C8" H8" 110.0 . . ? C8A" C8" H8" 110.0 . . ? C7" C8" H8" 110.0 . . ? C9" O8" C8" 107.68(14) . . ? N1" C8A" C4A" 120.16(17) . . ? N1" C8A" C8" 116.12(16) . . ? C4A" C8A" C8" 123.71(17) . . ? O7" C9" O8" 104.47(15) . . ? O7" C9" C11" 109.06(18) . . ? O8" C9" C11" 108.91(18) . . ? O7" C9" C10" 110.53(18) . . ? O8" C9" C10" 111.07(18) . . ? C11" C9" C10" 112.47(18) . . ? C9" C10" H10G 109.5 . . ? C9" C10" H10H 109.5 . . ? H10G C10" H10H 109.5 . . ? C9" C10" H10I 109.5 . . ? H10G C10" H10I 109.5 . . ? H10H C10" H10I 109.5 . . ? C9" C11" H11G 109.5 . . ? C9" C11" H11H 109.5 . . ? H11G C11" H11H 109.5 . . ? C9" C11" H11I 109.5 . . ? H11G C11" H11I 109.5 . . ? H11H C11" H11I 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 N1 C2 C3 -178.59(17) . . . . ? C8A N1 C2 C3 1.2(3) . . . . ? O1 N1 C2 C2' 3.5(3) . . . . ? C8A N1 C2 C2' -176.72(17) . . . . ? N1 C2 C3 C4 -3.4(3) . . . . ? C2' C2 C3 C4 174.37(19) . . . . ? C2 C3 C4 C4A 2.2(3) . . . . ? C3 C4 C4A C8A 1.1(3) . . . . ? C3 C4 C4A C5 -178.36(19) . . . . ? C4 C4A C5 C6 152.4(2) . . . . ? C8A C4A C5 C6 -27.0(3) . . . . ? C4A C5 C6 C7 54.4(2) . . . . ? C5 C6 C7 O7 60.2(2) . . . . ? C5 C6 C7 C8 -55.3(3) . . . . ? C6 C7 O7 C9 -145.85(18) . . . . ? C8 C7 O7 C9 -23.4(2) . . . . ? O7 C7 C8 O8 29.2(2) . . . . ? C6 C7 C8 O8 147.84(18) . . . . ? O7 C7 C8 C8A -91.91(19) . . . . ? C6 C7 C8 C8A 26.8(3) . . . . ? C8A C8 O8 C9 96.83(19) . . . . ? C7 C8 O8 C9 -25.1(2) . . . . ? O1 N1 C8A C4A -178.12(17) . . . . ? C2 N1 C8A C4A 2.1(3) . . . . ? O1 N1 C8A C8 -0.2(2) . . . . ? C2 N1 C8A C8 -179.94(17) . . . . ? C4 C4A C8A N1 -3.3(3) . . . . ? C5 C4A C8A N1 176.20(18) . . . . ? C4 C4A C8A C8 179.06(19) . . . . ? C5 C4A C8A C8 -1.5(3) . . . . ? O8 C8 C8A N1 68.4(2) . . . . ? C7 C8 C8A N1 -175.81(17) . . . . ? O8 C8 C8A C4A -113.9(2) . . . . ? C7 C8 C8A C4A 2.0(3) . . . . ? C8 O8 C9 O7 11.4(2) . . . . ? C8 O8 C9 C10 130.39(19) . . . . ? C8 O8 C9 C11 -105.4(2) . . . . ? C7 O7 C9 O8 8.5(2) . . . . ? C7 O7 C9 C10 -108.3(2) . . . . ? C7 O7 C9 C11 127.3(2) . . . . ? O1' N1' C2' C3' -175.68(17) . . . . ? C8A' N1' C2' C3' 2.3(3) . . . . ? O1' N1' C2' C2 0.8(2) . . . . ? C8A' N1' C2' C2 178.86(17) . . . . ? N1 C2 C2' C3' -116.6(2) . . . . ? C3 C2 C2' C3' 65.6(3) . . . . ? N1 C2 C2' N1' 67.1(2) . . . . ? C3 C2 C2' N1' -110.7(2) . . . . ? N1' C2' C3' C4' -3.3(3) . . . . ? C2 C2' C3' C4' -179.39(18) . . . . ? C2' C3' C4' C4A' 2.3(3) . . . . ? C3' C4' C4A' C8A' -0.3(3) . . . . ? C3' C4' C4A' C5' -179.81(18) . . . . ? C4' C4A' C5' C6' 143.62(19) . . . . ? C8A' C4A' C5' C6' -35.9(2) . . . . ? C4A' C5' C6' C7' 60.5(2) . . . . ? C5' C6' C7' O7' 69.5(2) . . . . ? C5' C6' C7' C8' -46.7(2) . . . . ? C6' C7' O7' C9' -150.35(16) . . . . ? C8' C7' O7' C9' -27.6(2) . . . . ? O7' C7' C8' O8' 6.7(2) . . . . ? C6' C7' C8' O8' 126.51(17) . . . . ? O7' C7' C8' C8A' -110.81(18) . . . . ? C6' C7' C8' C8A' 9.0(2) . . . . ? C8A' C8' O8' C9' 138.81(16) . . . . ? C7' C8' O8' C9' 16.6(2) . . . . ? O1' N1' C8A' C4A' 177.60(16) . . . . ? C2' N1' C8A' C4A' -0.4(3) . . . . ? O1' N1' C8A' C8' -0.6(2) . . . . ? C2' N1' C8A' C8' -178.60(16) . . . . ? C4' C4A' C8A' N1' -0.6(3) . . . . ? C5' C4A' C8A' N1' 178.92(17) . . . . ? C4' C4A' C8A' C8' 177.42(17) . . . . ? C5' C4A' C8A' C8' -3.1(3) . . . . ? O8' C8' C8A' N1' 79.73(19) . . . . ? C7' C8' C8A' N1' -164.63(16) . . . . ? O8' C8' C8A' C4A' -98.4(2) . . . . ? C7' C8' C8A' C4A' 17.3(3) . . . . ? C8' O8' C9' O7' -34.2(2) . . . . ? C8' O8' C9' C11' -151.15(17) . . . . ? C8' O8' C9' C10' 84.74(19) . . . . ? C7' O7' C9' O8' 38.8(2) . . . . ? C7' O7' C9' C11' 154.38(17) . . . . ? C7' O7' C9' C10' -80.14(19) . . . . ? O1" N1" C2" C3" -175.76(16) . . . . ? C8A" N1" C2" C3" 2.0(3) . . . . ? O1" N1" C2" C2" 2.3(2) . . . 2_756 ? C8A" N1" C2" C2" -179.96(17) . . . 2_756 ? N1" C2" C3" C4" -3.2(3) . . . . ? C2" C2" C3" C4" 178.89(19) 2_756 . . . ? C2" C3" C4" C4A" 2.4(3) . . . . ? C3" C4" C4A" C8A" -0.3(3) . . . . ? C3" C4" C4A" C5" -179.55(18) . . . . ? C4" C4A" C5" C6" 142.63(19) . . . . ? C8A" C4A" C5" C6" -36.6(2) . . . . ? C4A" C5" C6" C7" 60.6(2) . . . . ? C5" C6" C7" O7" 69.5(2) . . . . ? C5" C6" C7" C8" -46.0(2) . . . . ? C6" C7" O7" C9" -149.79(17) . . . . ? C8" C7" O7" C9" -27.1(2) . . . . ? O7" C7" C8" O8" 7.2(2) . . . . ? C6" C7" C8" O8" 125.41(18) . . . . ? O7" C7" C8" C8A" -110.55(18) . . . . ? C6" C7" C8" C8A" 7.6(2) . . . . ? C8A" C8" O8" C9" 137.08(16) . . . . ? C7" C8" O8" C9" 15.0(2) . . . . ? O1" N1" C8A" C4A" 177.75(16) . . . . ? C2" N1" C8A" C4A" 0.0(3) . . . . ? O1" N1" C8A" C8" -0.8(2) . . . . ? C2" N1" C8A" C8" -178.54(16) . . . . ? C4" C4A" C8A" N1" -0.9(3) . . . . ? C5" C4A" C8A" N1" 178.40(17) . . . . ? C4" C4A" C8A" C8" 177.57(18) . . . . ? C5" C4A" C8A" C8" -3.1(3) . . . . ? O8" C8" C8A" N1" 81.33(19) . . . . ? C7" C8" C8A" N1" -163.16(16) . . . . ? O8" C8" C8A" C4A" -97.2(2) . . . . ? C7" C8" C8A" C4A" 18.3(3) . . . . ? C7" O7" C9" O8" 37.3(2) . . . . ? C7" O7" C9" C11" 153.59(18) . . . . ? C7" O7" C9" C10" -82.3(2) . . . . ? C8" O8" C9" O7" -32.2(2) . . . . ? C8" O8" C9" C11" -148.59(18) . . . . ? C8" O8" C9" C10" 87.0(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.123 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.029 # Attachment '3Ip.cif' data_3Ip _database_code_depnum_ccdc_archive 'CCDC 746348' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H32 N2 O5' _chemical_formula_sum 'C26 H32 N2 O5' _chemical_formula_weight 452.54 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 14.0720(1) _cell_length_b 14.2180(1) _cell_length_c 22.8890(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4579.53(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 91614 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.910 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details 'sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 75191 _diffrn_reflns_av_R_equivalents 0.0621 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.51 _reflns_number_total 10491 _reflns_number_gt 9171 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+1.9621P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0060(6) _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' _refine_ls_abs_structure_Flack 0.0(7) _refine_ls_number_reflns 10491 _refine_ls_number_parameters 608 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1179 _refine_ls_wR_factor_gt 0.1115 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1A N 0.33891(12) -0.68840(12) 0.90904(7) 0.0211(3) Uani 1 1 d . . . O1A O 0.31359(12) -0.72540(11) 0.85941(7) 0.0324(4) Uani 1 1 d . . . C2A C 0.33573(14) -0.74115(14) 0.95874(9) 0.0221(4) Uani 1 1 d . . . C3A C 0.36516(15) -0.70382(15) 1.01214(9) 0.0239(4) Uani 1 1 d . . . C31A C 0.36039(18) -0.76228(17) 1.06701(10) 0.0331(5) Uani 1 1 d . . . H31A H 0.4109 -0.8097 1.0663 0.050 Uiso 1 1 calc R . . H31B H 0.2985 -0.7936 1.0692 0.050 Uiso 1 1 calc R . . H31C H 0.3687 -0.7215 1.1012 0.050 Uiso 1 1 calc R . . C4A C 0.39526(14) -0.61045(15) 1.01397(9) 0.0239(4) Uani 1 1 d . . . H4A H 0.4157 -0.5838 1.0499 0.029 Uiso 1 1 calc R . . C4AA C 0.39556(14) -0.55617(14) 0.96353(9) 0.0228(4) Uani 1 1 d . . . C5A C 0.42378(16) -0.45362(15) 0.96409(10) 0.0282(5) Uani 1 1 d . . . H5A1 H 0.4641 -0.4410 0.9986 0.034 Uiso 1 1 calc R . . H5A2 H 0.3661 -0.4141 0.9672 0.034 Uiso 1 1 calc R . . C6A C 0.47789(15) -0.42782(16) 0.90881(10) 0.0294(5) Uani 1 1 d . . . H6A1 H 0.4949 -0.3603 0.9100 0.035 Uiso 1 1 calc R . . H6A2 H 0.5375 -0.4646 0.9070 0.035 Uiso 1 1 calc R . . C7A C 0.41937(15) -0.44718(14) 0.85470(10) 0.0256(4) Uani 1 1 d . . . H7A H 0.4610 -0.4437 0.8193 0.031 Uiso 1 1 calc R . . O7A O 0.34623(11) -0.37759(10) 0.85070(7) 0.0281(3) Uani 1 1 d . . . C8A C 0.36384(15) -0.54224(14) 0.85465(9) 0.0242(4) Uani 1 1 d . . . H8A H 0.3861 -0.5828 0.8217 0.029 Uiso 1 1 calc R . . O8A O 0.26685(11) -0.51461(10) 0.84540(7) 0.0295(3) Uani 1 1 d . . . C8AA C 0.36799(14) -0.59590(14) 0.91103(9) 0.0218(4) Uani 1 1 d . . . C9A C 0.26701(16) -0.42113(14) 0.82276(9) 0.0262(4) Uani 1 1 d . . . C10A C 0.27851(18) -0.42177(16) 0.75664(10) 0.0316(5) Uani 1 1 d . . . H10A H 0.2793 -0.3570 0.7421 0.047 Uiso 1 1 calc R . . H10B H 0.2253 -0.4559 0.7389 0.047 Uiso 1 1 calc R . . H10C H 0.3384 -0.4529 0.7463 0.047 Uiso 1 1 calc R . . C11A C 0.17670(18) -0.37385(18) 0.84138(11) 0.0376(5) Uani 1 1 d . . . H11A H 0.1751 -0.3691 0.8841 0.056 Uiso 1 1 calc R . . H11B H 0.1222 -0.4108 0.8279 0.056 Uiso 1 1 calc R . . H11C H 0.1738 -0.3107 0.8243 0.056 Uiso 1 1 calc R . . N1B N 0.35486(12) -0.90858(12) 0.96629(8) 0.0250(4) Uani 1 1 d . . . C2B C 0.29497(15) -0.83791(14) 0.95438(9) 0.0236(4) Uani 1 1 d . . . C3B C 0.19778(16) -0.85200(16) 0.94408(10) 0.0287(5) Uani 1 1 d . . . C31B C 0.13138(17) -0.77082(18) 0.93380(12) 0.0396(6) Uani 1 1 d . . . H31D H 0.1526 -0.7351 0.8996 0.059 Uiso 1 1 calc R . . H31E H 0.1312 -0.7297 0.9682 0.059 Uiso 1 1 calc R . . H31F H 0.0670 -0.7947 0.9269 0.059 Uiso 1 1 calc R . . C4B C 0.16582(17) -0.94386(17) 0.94367(10) 0.0342(5) Uani 1 1 d . . . H4B H 0.1012 -0.9563 0.9346 0.041 Uiso 1 1 calc R . . C4AB C 0.22631(16) -1.01844(15) 0.95633(9) 0.0299(5) Uani 1 1 d . . . C5B C 0.18994(19) -1.11886(17) 0.95782(11) 0.0402(6) Uani 1 1 d . . . H5B1 H 0.1442 -1.1282 0.9255 0.048 Uiso 1 1 calc R . . H5B2 H 0.1558 -1.1296 0.9950 0.048 Uiso 1 1 calc R . . C6B C 0.2697(2) -1.19017(18) 0.95224(11) 0.0456(7) Uani 1 1 d . . . H6B1 H 0.2445 -1.2540 0.9598 0.055 Uiso 1 1 calc R . . H6B2 H 0.2951 -1.1888 0.9119 0.055 Uiso 1 1 calc R . . C7B C 0.34909(18) -1.16905(16) 0.99514(12) 0.0386(6) Uani 1 1 d . . . H7B H 0.3999 -1.2181 0.9924 0.046 Uiso 1 1 calc R . . O7B O 0.31065(12) -1.16633(12) 1.05317(7) 0.0370(4) Uani 1 1 d . . . C8B C 0.39191(17) -1.07110(16) 0.98815(11) 0.0332(5) Uani 1 1 d . . . H8B H 0.4467 -1.0732 0.9604 0.040 Uiso 1 1 calc R . . O8B O 0.42525(11) -1.05273(11) 1.04627(8) 0.0345(4) Uani 1 1 d . . . C8AB C 0.32028(15) -0.99705(15) 0.96857(9) 0.0258(4) Uani 1 1 d . . . C9B C 0.36434(17) -1.09988(17) 1.08773(11) 0.0360(5) Uani 1 1 d . . . C10B C 0.4228(2) -1.15002(19) 1.13101(13) 0.0457(6) Uani 1 1 d . . . H10D H 0.4640 -1.1952 1.1110 0.069 Uiso 1 1 calc R . . H10E H 0.3814 -1.1835 1.1584 0.069 Uiso 1 1 calc R . . H10F H 0.4620 -1.1047 1.1525 0.069 Uiso 1 1 calc R . . C11B C 0.29544(19) -1.03035(19) 1.11491(12) 0.0425(6) Uani 1 1 d . . . H11D H 0.3311 -0.9817 1.1358 0.064 Uiso 1 1 calc R . . H11E H 0.2536 -1.0634 1.1423 0.064 Uiso 1 1 calc R . . H11F H 0.2571 -1.0011 1.0841 0.064 Uiso 1 1 calc R . . N1C N -0.07652(12) -1.09197(12) 0.84455(7) 0.0215(3) Uani 1 1 d . . . O1C O -0.03593(11) -1.06519(12) 0.89277(7) 0.0327(4) Uani 1 1 d . . . C2C C -0.02547(14) -1.09067(14) 0.79381(9) 0.0226(4) Uani 1 1 d . . . C3C C -0.06667(15) -1.12019(14) 0.74164(9) 0.0235(4) Uani 1 1 d . . . C31C C -0.01071(17) -1.11500(17) 0.68553(10) 0.0322(5) Uani 1 1 d . . . H31G H -0.0508 -1.1355 0.6529 0.048 Uiso 1 1 calc R . . H31H H 0.0450 -1.1561 0.6883 0.048 Uiso 1 1 calc R . . H31I H 0.0100 -1.0501 0.6789 0.048 Uiso 1 1 calc R . . C4C C -0.16050(15) -1.15022(14) 0.74174(9) 0.0237(4) Uani 1 1 d . . . H4C H -0.1889 -1.1719 0.7066 0.028 Uiso 1 1 calc R . . C4AC C -0.21313(14) -1.14868(14) 0.79337(9) 0.0216(4) Uani 1 1 d . . . C5C C -0.31618(15) -1.17631(15) 0.79448(9) 0.0258(4) Uani 1 1 d . . . H5C1 H -0.3294 -1.2198 0.7617 0.031 Uiso 1 1 calc R . . H5C2 H -0.3561 -1.1196 0.7892 0.031 Uiso 1 1 calc R . . C6C C -0.34219(15) -1.22387(15) 0.85185(10) 0.0276(4) Uani 1 1 d . . . H6C1 H -0.4109 -1.2386 0.8519 0.033 Uiso 1 1 calc R . . H6C2 H -0.3069 -1.2838 0.8553 0.033 Uiso 1 1 calc R . . C7C C -0.31936(14) -1.16226(15) 0.90380(9) 0.0248(4) Uani 1 1 d . . . H7C H -0.3270 -1.1994 0.9406 0.030 Uiso 1 1 calc R . . O7C O -0.38275(10) -1.08338(11) 0.90472(7) 0.0283(3) Uani 1 1 d . . . C8C C -0.21946(14) -1.11639(14) 0.90272(9) 0.0228(4) Uani 1 1 d . . . H8C H -0.1785 -1.1458 0.9334 0.027 Uiso 1 1 calc R . . O8C O -0.23698(11) -1.01966(11) 0.91728(7) 0.0330(4) Uani 1 1 d . . . C8AC C -0.16983(14) -1.12019(13) 0.84483(9) 0.0210(4) Uani 1 1 d . . . C9C C -0.33407(15) -1.01052(16) 0.93515(9) 0.0270(4) Uani 1 1 d . . . C10C C -0.34237(16) -1.02212(19) 1.00076(10) 0.0344(5) Uani 1 1 d . . . H10G H -0.4090 -1.0155 1.0124 0.052 Uiso 1 1 calc R . . H10H H -0.3042 -0.9738 1.0203 0.052 Uiso 1 1 calc R . . H10I H -0.3192 -1.0846 1.0120 0.052 Uiso 1 1 calc R . . C11C C -0.3702(2) -0.91691(18) 0.91470(12) 0.0453(6) Uani 1 1 d . . . H11G H -0.3617 -0.9118 0.8723 0.068 Uiso 1 1 calc R . . H11H H -0.3348 -0.8666 0.9342 0.068 Uiso 1 1 calc R . . H11I H -0.4379 -0.9112 0.9242 0.068 Uiso 1 1 calc R . . N1D N 0.14532(12) -1.10728(12) 0.79219(8) 0.0233(4) Uani 1 1 d . . . C2D C 0.07146(15) -1.04818(14) 0.79583(9) 0.0228(4) Uani 1 1 d . . . C3D C 0.08084(15) -0.95000(14) 0.79676(9) 0.0251(4) Uani 1 1 d . . . C31D C -0.00408(17) -0.88628(17) 0.80171(12) 0.0354(5) Uani 1 1 d . . . H31J H 0.0169 -0.8206 0.8008 0.053 Uiso 1 1 calc R . . H31K H -0.0371 -0.8987 0.8386 0.053 Uiso 1 1 calc R . . H31L H -0.0473 -0.8980 0.7690 0.053 Uiso 1 1 calc R . . C4D C 0.17246(16) -0.91432(15) 0.79348(10) 0.0284(4) Uani 1 1 d . . . H4D H 0.1819 -0.8482 0.7941 0.034 Uiso 1 1 calc R . . C4AD C 0.25011(15) -0.97338(14) 0.78927(9) 0.0248(4) Uani 1 1 d . . . C5D C 0.35002(15) -0.93468(16) 0.78569(11) 0.0310(5) Uani 1 1 d . . . H5D1 H 0.3527 -0.8728 0.8054 0.037 Uiso 1 1 calc R . . H5D2 H 0.3677 -0.9255 0.7442 0.037 Uiso 1 1 calc R . . C6D C 0.42022(16) -1.00140(17) 0.81443(11) 0.0343(5) Uani 1 1 d . . . H6D1 H 0.4855 -0.9768 0.8093 0.041 Uiso 1 1 calc R . . H6D2 H 0.4069 -1.0048 0.8568 0.041 Uiso 1 1 calc R . . C7D C 0.41392(15) -1.09828(16) 0.78847(10) 0.0299(5) Uani 1 1 d . . . H7D H 0.4554 -1.1420 0.8113 0.036 Uiso 1 1 calc R . . O7D O 0.44578(11) -1.09532(11) 0.72962(7) 0.0317(4) Uani 1 1 d . . . C8D C 0.31337(15) -1.14087(15) 0.78341(10) 0.0266(4) Uani 1 1 d . . . H8D H 0.3052 -1.1915 0.8133 0.032 Uiso 1 1 calc R . . O8D O 0.31087(10) -1.18136(11) 0.72573(7) 0.0295(3) Uani 1 1 d . . . C8AD C 0.23337(14) -1.07021(14) 0.78873(9) 0.0227(4) Uani 1 1 d . . . C9D C 0.40446(15) -1.17519(16) 0.70179(10) 0.0286(5) Uani 1 1 d . . . C10D C 0.46271(17) -1.26297(17) 0.71438(12) 0.0367(5) Uani 1 1 d . . . H10J H 0.5280 -1.2537 0.7006 0.055 Uiso 1 1 calc R . . H10K H 0.4344 -1.3169 0.6941 0.055 Uiso 1 1 calc R . . H10L H 0.4633 -1.2749 0.7565 0.055 Uiso 1 1 calc R . . C11D C 0.39470(19) -1.15705(19) 0.63740(11) 0.0379(6) Uani 1 1 d . . . H11J H 0.3641 -1.0959 0.6313 0.057 Uiso 1 1 calc R . . H11K H 0.3559 -1.2066 0.6197 0.057 Uiso 1 1 calc R . . H11L H 0.4578 -1.1567 0.6193 0.057 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 0.0208(8) 0.0207(8) 0.0219(8) -0.0028(6) 0.0012(6) 0.0002(6) O1A 0.0429(9) 0.0290(8) 0.0253(8) -0.0033(6) -0.0016(7) -0.0049(7) C2A 0.0206(9) 0.0221(10) 0.0235(10) 0.0006(8) -0.0001(8) -0.0005(8) C3A 0.0216(10) 0.0267(11) 0.0233(10) 0.0010(8) -0.0005(8) 0.0000(8) C31A 0.0373(12) 0.0338(12) 0.0281(11) 0.0041(9) -0.0051(9) -0.0047(10) C4A 0.0211(10) 0.0265(11) 0.0241(10) -0.0028(8) -0.0024(8) -0.0003(8) C4AA 0.0199(9) 0.0219(10) 0.0266(10) -0.0029(8) 0.0005(8) 0.0010(7) C5A 0.0306(11) 0.0241(11) 0.0301(11) -0.0050(8) -0.0022(9) -0.0025(9) C6A 0.0256(11) 0.0254(11) 0.0373(12) 0.0000(9) -0.0010(9) -0.0056(8) C7A 0.0257(10) 0.0216(10) 0.0295(11) 0.0017(8) 0.0045(9) -0.0002(8) O7A 0.0307(8) 0.0216(7) 0.0321(8) -0.0033(6) -0.0021(6) -0.0001(6) C8A 0.0272(10) 0.0205(10) 0.0250(10) -0.0005(8) 0.0005(8) -0.0018(8) O8A 0.0276(8) 0.0262(8) 0.0347(8) 0.0104(6) -0.0036(6) -0.0067(6) C8AA 0.0217(9) 0.0208(10) 0.0229(10) -0.0006(8) 0.0024(8) 0.0005(7) C9A 0.0302(11) 0.0208(10) 0.0274(11) 0.0025(8) -0.0005(8) -0.0023(8) C10A 0.0431(13) 0.0257(11) 0.0259(11) 0.0044(8) 0.0005(9) -0.0020(10) C11A 0.0342(13) 0.0436(14) 0.0349(12) 0.0010(10) 0.0008(10) 0.0055(10) N1B 0.0233(8) 0.0223(9) 0.0293(9) 0.0007(7) 0.0038(7) -0.0024(7) C2B 0.0271(10) 0.0237(10) 0.0199(10) 0.0010(7) 0.0004(8) -0.0022(8) C3B 0.0266(11) 0.0319(11) 0.0276(11) 0.0072(9) -0.0044(9) -0.0028(9) C31B 0.0281(12) 0.0376(14) 0.0531(16) 0.0147(11) -0.0082(11) -0.0002(10) C4B 0.0305(11) 0.0370(13) 0.0352(12) 0.0121(10) -0.0090(10) -0.0103(10) C4AB 0.0355(12) 0.0278(11) 0.0265(11) 0.0045(8) -0.0048(9) -0.0106(9) C5B 0.0469(15) 0.0319(12) 0.0418(13) 0.0108(10) -0.0159(12) -0.0160(11) C6B 0.0757(19) 0.0273(12) 0.0339(13) -0.0026(10) 0.0093(13) -0.0124(12) C7B 0.0373(13) 0.0235(11) 0.0549(16) -0.0024(10) 0.0112(11) 0.0020(10) O7B 0.0373(9) 0.0356(9) 0.0380(9) 0.0096(7) -0.0050(7) -0.0126(7) C8B 0.0311(11) 0.0215(11) 0.0469(14) 0.0046(10) 0.0109(10) 0.0013(9) O8B 0.0263(8) 0.0309(8) 0.0465(10) 0.0118(7) -0.0009(7) -0.0034(6) C8AB 0.0288(10) 0.0238(10) 0.0249(10) 0.0023(8) 0.0039(8) -0.0026(8) C9B 0.0338(12) 0.0348(13) 0.0394(13) 0.0014(10) -0.0006(10) -0.0077(10) C10B 0.0492(16) 0.0370(14) 0.0509(16) 0.0110(12) -0.0053(12) -0.0130(12) C11B 0.0419(14) 0.0430(15) 0.0426(14) -0.0014(11) 0.0020(11) -0.0068(11) N1C 0.0197(8) 0.0235(8) 0.0213(8) -0.0021(7) -0.0016(7) -0.0013(7) O1C 0.0280(8) 0.0445(10) 0.0255(8) -0.0066(7) -0.0039(6) -0.0045(7) C2C 0.0227(10) 0.0199(10) 0.0252(10) -0.0006(8) 0.0024(8) 0.0001(7) C3C 0.0288(11) 0.0195(9) 0.0223(10) -0.0017(7) 0.0025(8) 0.0005(8) C31C 0.0369(13) 0.0328(12) 0.0269(11) -0.0045(9) 0.0064(9) -0.0078(10) C4C 0.0294(11) 0.0196(9) 0.0221(10) -0.0006(7) -0.0041(8) -0.0021(8) C4AC 0.0216(10) 0.0188(9) 0.0244(10) 0.0023(7) -0.0024(8) 0.0002(7) C5C 0.0222(10) 0.0259(10) 0.0293(11) -0.0006(8) -0.0041(8) -0.0027(8) C6C 0.0221(10) 0.0238(10) 0.0371(12) 0.0048(9) -0.0013(9) -0.0034(8) C7C 0.0191(9) 0.0259(10) 0.0295(11) 0.0061(8) -0.0004(8) -0.0006(8) O7C 0.0231(7) 0.0299(8) 0.0320(8) -0.0013(6) -0.0044(6) 0.0028(6) C8C 0.0210(10) 0.0252(10) 0.0222(10) 0.0004(8) -0.0018(8) -0.0017(8) O8C 0.0287(8) 0.0306(8) 0.0398(9) -0.0102(7) 0.0132(7) -0.0073(6) C8AC 0.0180(9) 0.0205(9) 0.0245(9) 0.0005(7) -0.0006(8) 0.0004(7) C9C 0.0231(10) 0.0309(11) 0.0270(10) -0.0010(9) 0.0010(8) 0.0005(8) C10C 0.0288(12) 0.0481(14) 0.0263(11) -0.0016(10) 0.0030(9) -0.0003(10) C11C 0.0613(17) 0.0329(13) 0.0417(14) -0.0058(11) -0.0128(13) 0.0107(12) N1D 0.0215(8) 0.0220(9) 0.0264(9) -0.0011(7) 0.0024(7) -0.0025(7) C2D 0.0241(10) 0.0234(10) 0.0210(10) -0.0014(8) 0.0035(8) -0.0008(8) C3D 0.0265(10) 0.0218(10) 0.0271(10) -0.0034(8) 0.0017(8) -0.0006(8) C31D 0.0302(12) 0.0265(11) 0.0496(14) -0.0039(10) 0.0029(10) 0.0039(9) C4D 0.0308(11) 0.0202(10) 0.0340(11) -0.0043(8) 0.0068(9) -0.0023(8) C4AD 0.0253(10) 0.0228(10) 0.0261(10) -0.0019(8) 0.0053(8) -0.0053(8) C5D 0.0241(11) 0.0244(11) 0.0445(13) -0.0069(9) 0.0082(9) -0.0063(8) C6D 0.0252(11) 0.0385(13) 0.0391(13) -0.0078(10) 0.0009(9) -0.0069(9) C7D 0.0216(10) 0.0293(12) 0.0387(12) 0.0001(10) 0.0004(9) -0.0012(8) O7D 0.0267(8) 0.0276(8) 0.0409(9) -0.0075(7) 0.0066(7) -0.0056(6) C8D 0.0227(10) 0.0223(10) 0.0348(11) -0.0008(8) 0.0005(9) -0.0014(8) O8D 0.0197(7) 0.0282(8) 0.0404(9) -0.0086(6) 0.0056(6) -0.0020(6) C8AD 0.0236(10) 0.0220(10) 0.0226(10) -0.0020(7) 0.0023(8) -0.0020(8) C9D 0.0197(10) 0.0289(11) 0.0372(12) -0.0035(9) 0.0026(9) -0.0012(8) C10D 0.0287(12) 0.0297(12) 0.0516(15) -0.0061(11) 0.0008(11) 0.0022(9) C11D 0.0374(13) 0.0412(14) 0.0351(13) -0.0009(10) 0.0020(10) -0.0043(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 N1A O1A 1.302(2) . ? N1A C2A 1.363(3) . ? N1A C8AA 1.378(3) . ? C2A C3A 1.395(3) . ? C2A C2B 1.494(3) . ? C3A C4A 1.394(3) . ? C3A C31A 1.508(3) . ? C31A H31A 0.9800 . ? C31A H31B 0.9800 . ? C31A H31C 0.9800 . ? C4A C4AA 1.389(3) . ? C4A H4A 0.9500 . ? C4AA C8AA 1.383(3) . ? C4AA C5A 1.511(3) . ? C5A C6A 1.522(3) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C6A C7A 1.513(3) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7A O7A 1.431(2) . ? C7A C8A 1.561(3) . ? C7A H7A 1.0000 . ? O7A C9A 1.426(3) . ? C8A O8A 1.436(3) . ? C8A C8AA 1.500(3) . ? C8A H8A 1.0000 . ? O8A C9A 1.427(2) . ? C9A C11A 1.499(3) . ? C9A C10A 1.522(3) . ? C10A H10A 0.9800 . ? C10A H10B 0.9800 . ? C10A H10C 0.9800 . ? C11A H11A 0.9800 . ? C11A H11B 0.9800 . ? C11A H11C 0.9800 . ? N1B C2B 1.340(3) . ? N1B C8AB 1.350(3) . ? C2B C3B 1.402(3) . ? C3B C4B 1.381(3) . ? C3B C31B 1.504(3) . ? C31B H31D 0.9800 . ? C31B H31E 0.9800 . ? C31B H31F 0.9800 . ? C4B C4AB 1.390(3) . ? C4B H4B 0.9500 . ? C4AB C8AB 1.386(3) . ? C4AB C5B 1.517(3) . ? C5B C6B 1.518(4) . ? C5B H5B1 0.9900 . ? C5B H5B2 0.9900 . ? C6B C7B 1.518(4) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7B O7B 1.435(3) . ? C7B C8B 1.526(3) . ? C7B H7B 1.0000 . ? O7B C9B 1.445(3) . ? C8B O8B 1.435(3) . ? C8B C8AB 1.525(3) . ? C8B H8B 1.0000 . ? O8B C9B 1.444(3) . ? C9B C10B 1.472(4) . ? C9B C11B 1.518(4) . ? C10B H10D 0.9800 . ? C10B H10E 0.9800 . ? C10B H10F 0.9800 . ? C11B H11D 0.9800 . ? C11B H11E 0.9800 . ? C11B H11F 0.9800 . ? N1C O1C 1.300(2) . ? N1C C2C 1.366(3) . ? N1C C8AC 1.373(3) . ? C2C C3C 1.392(3) . ? C2C C2D 1.493(3) . ? C3C C4C 1.388(3) . ? C3C C31C 1.508(3) . ? C31C H31G 0.9800 . ? C31C H31H 0.9800 . ? C31C H31I 0.9800 . ? C4C C4AC 1.395(3) . ? C4C H4C 0.9500 . ? C4AC C8AC 1.387(3) . ? C4AC C5C 1.503(3) . ? C5C C6C 1.522(3) . ? C5C H5C1 0.9900 . ? C5C H5C2 0.9900 . ? C6C C7C 1.512(3) . ? C6C H6C1 0.9900 . ? C6C H6C2 0.9900 . ? C7C O7C 1.433(2) . ? C7C C8C 1.550(3) . ? C7C H7C 1.0000 . ? O7C C9C 1.424(3) . ? C8C O8C 1.436(3) . ? C8C C8AC 1.499(3) . ? C8C H8C 1.0000 . ? O8C C9C 1.432(3) . ? C9C C11C 1.500(3) . ? C9C C10C 1.515(3) . ? C10C H10G 0.9800 . ? C10C H10H 0.9800 . ? C10C H10I 0.9800 . ? C11C H11G 0.9800 . ? C11C H11H 0.9800 . ? C11C H11I 0.9800 . ? N1D C2D 1.339(3) . ? N1D C8AD 1.349(3) . ? C2D C3D 1.402(3) . ? C3D C4D 1.388(3) . ? C3D C31D 1.504(3) . ? C31D H31J 0.9800 . ? C31D H31K 0.9800 . ? C31D H31L 0.9800 . ? C4D C4AD 1.381(3) . ? C4D H4D 0.9500 . ? C4AD C8AD 1.397(3) . ? C4AD C5D 1.512(3) . ? C5D C6D 1.519(3) . ? C5D H5D1 0.9900 . ? C5D H5D2 0.9900 . ? C6D C7D 1.503(3) . ? C6D H6D1 0.9900 . ? C6D H6D2 0.9900 . ? C7D O7D 1.420(3) . ? C7D C8D 1.543(3) . ? C7D H7D 1.0000 . ? O7D C9D 1.426(3) . ? C8D O8D 1.441(3) . ? C8D C8AD 1.514(3) . ? C8D H8D 1.0000 . ? O8D C9D 1.429(2) . ? C9D C11D 1.502(3) . ? C9D C10D 1.521(3) . ? C10D H10J 0.9800 . ? C10D H10K 0.9800 . ? C10D H10L 0.9800 . ? C11D H11J 0.9800 . ? C11D H11K 0.9800 . ? C11D H11L 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 O1A N1A C2A 119.80(16) . . ? O1A N1A C8AA 119.73(16) . . ? C2A N1A C8AA 120.47(17) . . ? N1A C2A C3A 120.79(18) . . ? N1A C2A C2B 117.60(17) . . ? C3A C2A C2B 121.52(18) . . ? C4A C3A C2A 118.61(19) . . ? C4A C3A C31A 120.90(19) . . ? C2A C3A C31A 120.45(19) . . ? C3A C31A H31A 109.5 . . ? C3A C31A H31B 109.5 . . ? H31A C31A H31B 109.5 . . ? C3A C31A H31C 109.5 . . ? H31A C31A H31C 109.5 . . ? H31B C31A H31C 109.5 . . ? C4AA C4A C3A 120.33(19) . . ? C4AA C4A H4A 119.8 . . ? C3A C4A H4A 119.8 . . ? C8AA C4AA C4A 119.63(18) . . ? C8AA C4AA C5A 118.37(19) . . ? C4A C4AA C5A 122.00(19) . . ? C4AA C5A C6A 110.92(18) . . ? C4AA C5A H5A1 109.5 . . ? C6A C5A H5A1 109.5 . . ? C4AA C5A H5A2 109.5 . . ? C6A C5A H5A2 109.5 . . ? H5A1 C5A H5A2 108.0 . . ? C7A C6A C5A 111.39(17) . . ? C7A C6A H6A1 109.4 . . ? C5A C6A H6A1 109.4 . . ? C7A C6A H6A2 109.4 . . ? C5A C6A H6A2 109.4 . . ? H6A1 C6A H6A2 108.0 . . ? O7A C7A C6A 108.55(17) . . ? O7A C7A C8A 103.80(16) . . ? C6A C7A C8A 115.51(18) . . ? O7A C7A H7A 109.6 . . ? C6A C7A H7A 109.6 . . ? C8A C7A H7A 109.6 . . ? C9A O7A C7A 106.91(15) . . ? O8A C8A C8AA 107.64(16) . . ? O8A C8A C7A 103.83(15) . . ? C8AA C8A C7A 114.85(18) . . ? O8A C8A H8A 110.1 . . ? C8AA C8A H8A 110.1 . . ? C7A C8A H8A 110.1 . . ? C9A O8A C8A 107.87(15) . . ? N1A C8AA C4AA 120.12(18) . . ? N1A C8AA C8A 116.44(17) . . ? C4AA C8AA C8A 123.40(18) . . ? O7A C9A O8A 104.05(16) . . ? O7A C9A C11A 109.90(18) . . ? O8A C9A C11A 108.25(18) . . ? O7A C9A C10A 111.42(18) . . ? O8A C9A C10A 110.83(17) . . ? C11A C9A C10A 112.05(19) . . ? C9A C10A H10A 109.5 . . ? C9A C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? C9A C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C9A C11A H11A 109.5 . . ? C9A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? C9A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? C2B N1B C8AB 118.70(18) . . ? N1B C2B C3B 122.73(19) . . ? N1B C2B C2A 115.83(17) . . ? C3B C2B C2A 121.16(19) . . ? C4B C3B C2B 117.0(2) . . ? C4B C3B C31B 121.5(2) . . ? C2B C3B C31B 121.5(2) . . ? C3B C31B H31D 109.5 . . ? C3B C31B H31E 109.5 . . ? H31D C31B H31E 109.5 . . ? C3B C31B H31F 109.5 . . ? H31D C31B H31F 109.5 . . ? H31E C31B H31F 109.5 . . ? C3B C4B C4AB 121.4(2) . . ? C3B C4B H4B 119.3 . . ? C4AB C4B H4B 119.3 . . ? C8AB C4AB C4B 117.3(2) . . ? C8AB C4AB C5B 121.6(2) . . ? C4B C4AB C5B 121.1(2) . . ? C4AB C5B C6B 112.2(2) . . ? C4AB C5B H5B1 109.2 . . ? C6B C5B H5B1 109.2 . . ? C4AB C5B H5B2 109.2 . . ? C6B C5B H5B2 109.2 . . ? H5B1 C5B H5B2 107.9 . . ? C7B C6B C5B 111.0(2) . . ? C7B C6B H6B1 109.4 . . ? C5B C6B H6B1 109.4 . . ? C7B C6B H6B2 109.4 . . ? C5B C6B H6B2 109.4 . . ? H6B1 C6B H6B2 108.0 . . ? O7B C7B C6B 109.1(2) . . ? O7B C7B C8B 102.79(19) . . ? C6B C7B C8B 113.8(2) . . ? O7B C7B H7B 110.3 . . ? C6B C7B H7B 110.3 . . ? C8B C7B H7B 110.3 . . ? C7B O7B C9B 109.10(18) . . ? O8B C8B C8AB 111.28(18) . . ? O8B C8B C7B 101.42(19) . . ? C8AB C8B C7B 113.6(2) . . ? O8B C8B H8B 110.1 . . ? C8AB C8B H8B 110.1 . . ? C7B C8B H8B 110.1 . . ? C8B O8B C9B 109.32(17) . . ? N1B C8AB C4AB 122.7(2) . . ? N1B C8AB C8B 114.62(19) . . ? C4AB C8AB C8B 122.59(19) . . ? O8B C9B O7B 104.73(19) . . ? O8B C9B C10B 109.6(2) . . ? O7B C9B C10B 110.1(2) . . ? O8B C9B C11B 110.3(2) . . ? O7B C9B C11B 108.4(2) . . ? C10B C9B C11B 113.4(2) . . ? C9B C10B H10D 109.5 . . ? C9B C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? C9B C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? C9B C11B H11D 109.5 . . ? C9B C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? C9B C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? O1C N1C C2C 119.15(16) . . ? O1C N1C C8AC 120.12(16) . . ? C2C N1C C8AC 120.73(16) . . ? N1C C2C C3C 120.42(18) . . ? N1C C2C C2D 117.38(17) . . ? C3C C2C C2D 121.95(18) . . ? C4C C3C C2C 119.18(19) . . ? C4C C3C C31C 120.88(19) . . ? C2C C3C C31C 119.88(19) . . ? C3C C31C H31G 109.5 . . ? C3C C31C H31H 109.5 . . ? H31G C31C H31H 109.5 . . ? C3C C31C H31I 109.5 . . ? H31G C31C H31I 109.5 . . ? H31H C31C H31I 109.5 . . ? C3C C4C C4AC 120.12(18) . . ? C3C C4C H4C 119.9 . . ? C4AC C4C H4C 119.9 . . ? C8AC C4AC C4C 119.40(18) . . ? C8AC C4AC C5C 119.08(18) . . ? C4C C4AC C5C 121.52(18) . . ? C4AC C5C C6C 111.28(17) . . ? C4AC C5C H5C1 109.4 . . ? C6C C5C H5C1 109.4 . . ? C4AC C5C H5C2 109.4 . . ? C6C C5C H5C2 109.4 . . ? H5C1 C5C H5C2 108.0 . . ? C7C C6C C5C 111.73(17) . . ? C7C C6C H6C1 109.3 . . ? C5C C6C H6C1 109.3 . . ? C7C C6C H6C2 109.3 . . ? C5C C6C H6C2 109.3 . . ? H6C1 C6C H6C2 107.9 . . ? O7C C7C C6C 109.43(16) . . ? O7C C7C C8C 103.62(16) . . ? C6C C7C C8C 115.09(17) . . ? O7C C7C H7C 109.5 . . ? C6C C7C H7C 109.5 . . ? C8C C7C H7C 109.5 . . ? C9C O7C C7C 106.08(15) . . ? O8C C8C C8AC 108.63(16) . . ? O8C C8C C7C 104.10(15) . . ? C8AC C8C C7C 114.94(17) . . ? O8C C8C H8C 109.7 . . ? C8AC C8C H8C 109.7 . . ? C7C C8C H8C 109.7 . . ? C9C O8C C8C 108.48(15) . . ? N1C C8AC C4AC 120.10(18) . . ? N1C C8AC C8C 116.06(17) . . ? C4AC C8AC C8C 123.83(18) . . ? O7C C9C O8C 104.66(16) . . ? O7C C9C C11C 109.25(18) . . ? O8C C9C C11C 108.4(2) . . ? O7C C9C C10C 111.63(18) . . ? O8C C9C C10C 110.29(17) . . ? C11C C9C C10C 112.3(2) . . ? C9C C10C H10G 109.5 . . ? C9C C10C H10H 109.5 . . ? H10G C10C H10H 109.5 . . ? C9C C10C H10I 109.5 . . ? H10G C10C H10I 109.5 . . ? H10H C10C H10I 109.5 . . ? C9C C11C H11G 109.5 . . ? C9C C11C H11H 109.5 . . ? H11G C11C H11H 109.5 . . ? C9C C11C H11I 109.5 . . ? H11G C11C H11I 109.5 . . ? H11H C11C H11I 109.5 . . ? C2D N1D C8AD 118.13(18) . . ? N1D C2D C3D 123.54(19) . . ? N1D C2D C2C 116.96(17) . . ? C3D C2D C2C 119.30(18) . . ? C4D C3D C2D 116.8(2) . . ? C4D C3D C31D 121.47(19) . . ? C2D C3D C31D 121.7(2) . . ? C3D C31D H31J 109.5 . . ? C3D C31D H31K 109.5 . . ? H31J C31D H31K 109.5 . . ? C3D C31D H31L 109.5 . . ? H31J C31D H31L 109.5 . . ? H31K C31D H31L 109.5 . . ? C4AD C4D C3D 121.10(19) . . ? C4AD C4D H4D 119.5 . . ? C3D C4D H4D 119.5 . . ? C4D C4AD C8AD 117.80(19) . . ? C4D C4AD C5D 121.20(18) . . ? C8AD C4AD C5D 120.99(19) . . ? C4AD C5D C6D 110.73(19) . . ? C4AD C5D H5D1 109.5 . . ? C6D C5D H5D1 109.5 . . ? C4AD C5D H5D2 109.5 . . ? C6D C5D H5D2 109.5 . . ? H5D1 C5D H5D2 108.1 . . ? C7D C6D C5D 111.28(19) . . ? C7D C6D H6D1 109.4 . . ? C5D C6D H6D1 109.4 . . ? C7D C6D H6D2 109.4 . . ? C5D C6D H6D2 109.4 . . ? H6D1 C6D H6D2 108.0 . . ? O7D C7D C6D 109.23(18) . . ? O7D C7D C8D 103.29(17) . . ? C6D C7D C8D 116.32(18) . . ? O7D C7D H7D 109.2 . . ? C6D C7D H7D 109.2 . . ? C8D C7D H7D 109.2 . . ? C7D O7D C9D 105.75(16) . . ? O8D C8D C8AD 108.71(17) . . ? O8D C8D C7D 104.36(17) . . ? C8AD C8D C7D 114.54(17) . . ? O8D C8D H8D 109.7 . . ? C8AD C8D H8D 109.7 . . ? C7D C8D H8D 109.7 . . ? C9D O8D C8D 107.71(16) . . ? N1D C8AD C4AD 122.65(19) . . ? N1D C8AD C8D 115.37(17) . . ? C4AD C8AD C8D 121.97(18) . . ? O7D C9D O8D 104.68(17) . . ? O7D C9D C11D 109.80(19) . . ? O8D C9D C11D 107.60(18) . . ? O7D C9D C10D 110.43(18) . . ? O8D C9D C10D 111.95(19) . . ? C11D C9D C10D 112.1(2) . . ? C9D C10D H10J 109.5 . . ? C9D C10D H10K 109.5 . . ? H10J C10D H10K 109.5 . . ? C9D C10D H10L 109.5 . . ? H10J C10D H10L 109.5 . . ? H10K C10D H10L 109.5 . . ? C9D C11D H11J 109.5 . . ? C9D C11D H11K 109.5 . . ? H11J C11D H11K 109.5 . . ? C9D C11D H11L 109.5 . . ? H11J C11D H11L 109.5 . . ? H11K C11D H11L 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 O1A N1A C2A C3A 178.11(18) . . . . ? C8AA N1A C2A C3A -2.4(3) . . . . ? O1A N1A C2A C2B -5.1(3) . . . . ? C8AA N1A C2A C2B 174.39(17) . . . . ? N1A C2A C3A C4A 1.9(3) . . . . ? C2B C2A C3A C4A -174.79(19) . . . . ? N1A C2A C3A C31A 179.31(19) . . . . ? C2B C2A C3A C31A 2.6(3) . . . . ? C2A C3A C4A C4AA 0.1(3) . . . . ? C31A C3A C4A C4AA -177.3(2) . . . . ? C3A C4A C4AA C8AA -1.6(3) . . . . ? C3A C4A C4AA C5A 177.44(19) . . . . ? C8AA C4AA C5A C6A -37.4(3) . . . . ? C4A C4AA C5A C6A 143.6(2) . . . . ? C4AA C5A C6A C7A 58.4(2) . . . . ? C5A C6A C7A O7A 73.1(2) . . . . ? C5A C6A C7A C8A -42.9(2) . . . . ? C6A C7A O7A C9A -149.18(17) . . . . ? C8A C7A O7A C9A -25.8(2) . . . . ? O7A C7A C8A O8A 4.9(2) . . . . ? C6A C7A C8A O8A 123.64(19) . . . . ? O7A C7A C8A C8AA -112.30(19) . . . . ? C6A C7A C8A C8AA 6.4(3) . . . . ? C8AA C8A O8A C9A 139.83(17) . . . . ? C7A C8A O8A C9A 17.7(2) . . . . ? O1A N1A C8AA C4AA -179.61(18) . . . . ? C2A N1A C8AA C4AA 0.9(3) . . . . ? O1A N1A C8AA C8A 2.8(3) . . . . ? C2A N1A C8AA C8A -176.68(17) . . . . ? C4A C4AA C8AA N1A 1.1(3) . . . . ? C5A C4AA C8AA N1A -177.97(18) . . . . ? C4A C4AA C8AA C8A 178.50(19) . . . . ? C5A C4AA C8AA C8A -0.5(3) . . . . ? O8A C8A C8AA N1A 79.1(2) . . . . ? C7A C8A C8AA N1A -165.81(17) . . . . ? O8A C8A C8AA C4AA -98.4(2) . . . . ? C7A C8A C8AA C4AA 16.7(3) . . . . ? C7A O7A C9A O8A 37.4(2) . . . . ? C7A O7A C9A C11A 153.14(18) . . . . ? C7A O7A C9A C10A -82.0(2) . . . . ? C8A O8A C9A O7A -34.1(2) . . . . ? C8A O8A C9A C11A -150.95(18) . . . . ? C8A O8A C9A C10A 85.8(2) . . . . ? C8AB N1B C2B C3B -0.1(3) . . . . ? C8AB N1B C2B C2A 173.78(18) . . . . ? N1A C2A C2B N1B 116.8(2) . . . . ? C3A C2A C2B N1B -66.4(3) . . . . ? N1A C2A C2B C3B -69.2(3) . . . . ? C3A C2A C2B C3B 107.6(2) . . . . ? N1B C2B C3B C4B -3.3(3) . . . . ? C2A C2B C3B C4B -176.8(2) . . . . ? N1B C2B C3B C31B 176.9(2) . . . . ? C2A C2B C3B C31B 3.3(3) . . . . ? C2B C3B C4B C4AB 3.7(3) . . . . ? C31B C3B C4B C4AB -176.4(2) . . . . ? C3B C4B C4AB C8AB -0.9(3) . . . . ? C3B C4B C4AB C5B 177.9(2) . . . . ? C8AB C4AB C5B C6B -20.3(3) . . . . ? C4B C4AB C5B C6B 161.0(2) . . . . ? C4AB C5B C6B C7B 50.1(3) . . . . ? C5B C6B C7B O7B 56.1(3) . . . . ? C5B C6B C7B C8B -58.0(3) . . . . ? C6B C7B O7B C9B -148.5(2) . . . . ? C8B C7B O7B C9B -27.4(2) . . . . ? O7B C7B C8B O8B 34.9(2) . . . . ? C6B C7B C8B O8B 152.7(2) . . . . ? O7B C7B C8B C8AB -84.6(2) . . . . ? C6B C7B C8B C8AB 33.2(3) . . . . ? C8AB C8B O8B C9B 90.1(2) . . . . ? C7B C8B O8B C9B -31.0(2) . . . . ? C2B N1B C8AB C4AB 3.2(3) . . . . ? C2B N1B C8AB C8B -174.38(19) . . . . ? C4B C4AB C8AB N1B -2.7(3) . . . . ? C5B C4AB C8AB N1B 178.5(2) . . . . ? C4B C4AB C8AB C8B 174.7(2) . . . . ? C5B C4AB C8AB C8B -4.1(3) . . . . ? O8B C8B C8AB N1B 61.6(2) . . . . ? C7B C8B C8AB N1B 175.3(2) . . . . ? O8B C8B C8AB C4AB -116.0(2) . . . . ? C7B C8B C8AB C4AB -2.3(3) . . . . ? C8B O8B C9B O7B 15.0(2) . . . . ? C8B O8B C9B C10B 133.1(2) . . . . ? C8B O8B C9B C11B -101.4(2) . . . . ? C7B O7B C9B O8B 8.9(2) . . . . ? C7B O7B C9B C10B -108.8(2) . . . . ? C7B O7B C9B C11B 126.6(2) . . . . ? O1C N1C C2C C3C 179.11(18) . . . . ? C8AC N1C C2C C3C -1.6(3) . . . . ? O1C N1C C2C C2D -6.6(3) . . . . ? C8AC N1C C2C C2D 172.72(17) . . . . ? N1C C2C C3C C4C 0.5(3) . . . . ? C2D C2C C3C C4C -173.49(18) . . . . ? N1C C2C C3C C31C 177.73(19) . . . . ? C2D C2C C3C C31C 3.7(3) . . . . ? C2C C3C C4C C4AC 1.4(3) . . . . ? C31C C3C C4C C4AC -175.7(2) . . . . ? C3C C4C C4AC C8AC -2.4(3) . . . . ? C3C C4C C4AC C5C 177.04(19) . . . . ? C8AC C4AC C5C C6C -34.1(3) . . . . ? C4C C4AC C5C C6C 146.46(19) . . . . ? C4AC C5C C6C C7C 56.5(2) . . . . ? C5C C6C C7C O7C 69.4(2) . . . . ? C5C C6C C7C C8C -46.8(2) . . . . ? C6C C7C O7C C9C -154.31(16) . . . . ? C8C C7C O7C C9C -31.07(19) . . . . ? O7C C7C C8C O8C 13.4(2) . . . . ? C6C C7C C8C O8C 132.87(18) . . . . ? O7C C7C C8C C8AC -105.25(19) . . . . ? C6C C7C C8C C8AC 14.2(2) . . . . ? C8AC C8C O8C C9C 131.81(17) . . . . ? C7C C8C O8C C9C 8.9(2) . . . . ? O1C N1C C8AC C4AC 179.94(18) . . . . ? C2C N1C C8AC C4AC 0.6(3) . . . . ? O1C N1C C8AC C8C 0.8(3) . . . . ? C2C N1C C8AC C8C -178.47(17) . . . . ? C4C C4AC C8AC N1C 1.3(3) . . . . ? C5C C4AC C8AC N1C -178.08(18) . . . . ? C4C C4AC C8AC C8C -179.64(18) . . . . ? C5C C4AC C8AC C8C 0.9(3) . . . . ? O8C C8C C8AC N1C 72.6(2) . . . . ? C7C C8C C8AC N1C -171.31(17) . . . . ? O8C C8C C8AC C4AC -106.5(2) . . . . ? C7C C8C C8AC C4AC 9.6(3) . . . . ? C7C O7C C9C O8C 37.3(2) . . . . ? C7C O7C C9C C11C 153.21(19) . . . . ? C7C O7C C9C C10C -82.0(2) . . . . ? C8C O8C C9C O7C -28.3(2) . . . . ? C8C O8C C9C C11C -144.81(18) . . . . ? C8C O8C C9C C10C 91.9(2) . . . . ? C8AD N1D C2D C3D -0.6(3) . . . . ? C8AD N1D C2D C2C 174.28(18) . . . . ? N1C C2C C2D N1D 108.0(2) . . . . ? C3C C2C C2D N1D -77.8(3) . . . . ? N1C C2C C2D C3D -76.9(3) . . . . ? C3C C2C C2D C3D 97.3(2) . . . . ? N1D C2D C3D C4D 0.2(3) . . . . ? C2C C2D C3D C4D -174.54(19) . . . . ? N1D C2D C3D C31D -179.2(2) . . . . ? C2C C2D C3D C31D 6.1(3) . . . . ? C2D C3D C4D C4AD 0.3(3) . . . . ? C31D C3D C4D C4AD 179.6(2) . . . . ? C3D C4D C4AD C8AD -0.3(3) . . . . ? C3D C4D C4AD C5D 180.0(2) . . . . ? C4D C4AD C5D C6D 148.2(2) . . . . ? C8AD C4AD C5D C6D -31.4(3) . . . . ? C4AD C5D C6D C7D 55.4(3) . . . . ? C5D C6D C7D O7D 67.0(2) . . . . ? C5D C6D C7D C8D -49.3(3) . . . . ? C6D C7D O7D C9D -157.77(17) . . . . ? C8D C7D O7D C9D -33.4(2) . . . . ? O7D C7D C8D O8D 15.9(2) . . . . ? C6D C7D C8D O8D 135.6(2) . . . . ? O7D C7D C8D C8AD -102.8(2) . . . . ? C6D C7D C8D C8AD 16.8(3) . . . . ? C8AD C8D O8D C9D 129.83(17) . . . . ? C7D C8D O8D C9D 7.2(2) . . . . ? C2D N1D C8AD C4AD 0.5(3) . . . . ? C2D N1D C8AD C8D -178.73(18) . . . . ? C4D C4AD C8AD N1D -0.1(3) . . . . ? C5D C4AD C8AD N1D 179.60(19) . . . . ? C4D C4AD C8AD C8D 179.13(19) . . . . ? C5D C4AD C8AD C8D -1.2(3) . . . . ? O8D C8D C8AD N1D 72.1(2) . . . . ? C7D C8D C8AD N1D -171.59(18) . . . . ? O8D C8D C8AD C4AD -107.1(2) . . . . ? C7D C8D C8AD C4AD 9.2(3) . . . . ? C7D O7D C9D O8D 38.9(2) . . . . ? C7D O7D C9D C11D 154.09(18) . . . . ? C7D O7D C9D C10D -81.8(2) . . . . ? C8D O8D C9D O7D -27.9(2) . . . . ? C8D O8D C9D C11D -144.64(19) . . . . ? C8D O8D C9D C10D 91.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.500 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.076 # Attachment '3Jp.cif' data_3Jp _database_code_depnum_ccdc_archive 'CCDC 746349' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H32 N2 O6' _chemical_formula_sum 'C26 H32 N2 O6' _chemical_formula_weight 468.54 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 14.1616(1) _cell_length_b 14.2969(1) _cell_length_c 22.8822(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4632.89(6) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 101809 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.888 _exptl_absorpt_correction_T_max 0.963 _exptl_absorpt_process_details 'sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 66883 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.49 _reflns_number_total 10614 _reflns_number_gt 10001 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+3.7018P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0179(11) _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' _refine_ls_abs_structure_Flack 0.5(8) _refine_ls_number_reflns 10614 _refine_ls_number_parameters 656 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1461 _refine_ls_wR_factor_gt 0.1431 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1A N 0.33788(14) -0.68707(14) 0.91065(8) 0.0192(4) Uani 1 1 d . . . O1A O 0.31250(13) -0.72340(12) 0.86075(7) 0.0238(4) Uani 1 1 d . . . C2A C 0.33327(16) -0.73992(17) 0.96055(11) 0.0208(5) Uani 1 1 d . . . C3A C 0.36230(17) -0.70377(19) 1.01388(11) 0.0235(5) Uani 1 1 d . . . C31A C 0.3589(2) -0.7644(2) 1.06765(11) 0.0299(6) Uani 1 1 d . . . H31A H 0.3730 -0.7264 1.1022 0.045 Uiso 1 1 calc R . . H31B H 0.4058 -0.8145 1.0642 0.045 Uiso 1 1 calc R . . H31C H 0.2958 -0.7918 1.0716 0.045 Uiso 1 1 calc R . . C4A C 0.39340(17) -0.61172(19) 1.01649(11) 0.0240(5) Uani 1 1 d . . . H4A H 0.4141 -0.5863 1.0526 0.029 Uiso 1 1 calc R . . C4AA C 0.39426(17) -0.55653(18) 0.96620(11) 0.0215(5) Uani 1 1 d . . . C5A C 0.4218(2) -0.45489(18) 0.96727(12) 0.0271(5) Uani 1 1 d . . . H5A1 H 0.4625 -0.4429 1.0016 0.033 Uiso 1 1 calc R . . H5A2 H 0.3643 -0.4161 0.9713 0.033 Uiso 1 1 calc R . . C6A C 0.47411(19) -0.4267(2) 0.91195(12) 0.0292(6) Uani 1 1 d . . . H6A1 H 0.4900 -0.3593 0.9138 0.035 Uiso 1 1 calc R . . H6A2 H 0.5339 -0.4623 0.9092 0.035 Uiso 1 1 calc R . . C7A C 0.41457(19) -0.44533(18) 0.85824(11) 0.0246(5) Uani 1 1 d . . . H7A H 0.4539 -0.4367 0.8223 0.030 Uiso 1 1 calc R . . O7A O 0.33718(14) -0.38077(12) 0.85739(8) 0.0267(4) Uani 1 1 d . . . C8A C 0.36567(17) -0.54304(17) 0.85639(10) 0.0207(5) Uani 1 1 d . . . H8A H 0.3939 -0.5821 0.8246 0.025 Uiso 1 1 calc R . . O8A O 0.26954(13) -0.52176(13) 0.84283(9) 0.0286(4) Uani 1 1 d . . . C8AA C 0.36728(16) -0.59535(17) 0.91283(10) 0.0199(5) Uani 1 1 d . . . C9A C 0.2627(2) -0.42535(18) 0.82639(11) 0.0249(5) Uani 1 1 d . . . C10A C 0.2736(2) -0.4141(2) 0.76080(11) 0.0310(6) Uani 1 1 d . . . H10A H 0.2708 -0.3476 0.7506 0.046 Uiso 1 1 calc R . . H10B H 0.2225 -0.4475 0.7409 0.046 Uiso 1 1 calc R . . H10C H 0.3346 -0.4399 0.7485 0.046 Uiso 1 1 calc R . . C11A C 0.1690(2) -0.3897(2) 0.84794(12) 0.0323(6) Uani 1 1 d . . . H11A H 0.1667 -0.3942 0.8907 0.048 Uiso 1 1 calc R . . H11B H 0.1181 -0.4274 0.8310 0.048 Uiso 1 1 calc R . . H11C H 0.1611 -0.3243 0.8362 0.048 Uiso 1 1 calc R . . N1B N 0.34845(14) -0.90826(15) 0.96220(9) 0.0230(4) Uani 1 1 d . B . O1B O 0.43861(13) -0.89483(14) 0.96696(10) 0.0333(4) Uani 1 1 d . . . C2B C 0.28980(17) -0.83421(18) 0.95511(10) 0.0213(5) Uani 1 1 d . . . C3B C 0.19301(19) -0.8475(2) 0.94774(12) 0.0281(6) Uani 1 1 d . . . C31B C 0.1284(2) -0.7650(2) 0.94040(16) 0.0389(7) Uani 1 1 d . . . H31D H 0.0641 -0.7871 0.9326 0.058 Uiso 1 1 calc R . . H31E H 0.1502 -0.7267 0.9075 0.058 Uiso 1 1 calc R . . H31F H 0.1288 -0.7274 0.9762 0.058 Uiso 1 1 calc R . . C4B C 0.1581(2) -0.9387(2) 0.94735(14) 0.0344(6) Uani 1 1 d . . . H4B H 0.0930 -0.9495 0.9401 0.041 Uiso 1 1 calc R . . C4AB C 0.2176(2) -1.0138(2) 0.95748(12) 0.0289(6) Uani 1 1 d . B . C5B C 0.1793(2) -1.1123(2) 0.95980(15) 0.0393(7) Uani 1 1 d . . . H5B1 H 0.1280 -1.1188 0.9307 0.047 Uiso 1 1 calc R . . H5B2 H 0.1520 -1.1238 0.9990 0.047 Uiso 1 1 calc R . . C6B C 0.2542(3) -1.1851(2) 0.94760(16) 0.0503(9) Uani 1 1 d . B . H6B1 H 0.2741 -1.1808 0.9062 0.060 Uiso 1 1 calc R . . H6B2 H 0.2276 -1.2483 0.9542 0.060 Uiso 1 1 calc R . . C7B C 0.3393(2) -1.1711(2) 0.9869(2) 0.0597(12) Uani 1 1 d . . . H7B H 0.3878 -1.2205 0.9793 0.072 Uiso 1 1 calc R A 2 O7B O 0.3097(2) -1.1739(2) 1.04610(14) 0.0751(11) Uani 1 1 d . B . C8B C 0.3840(2) -1.0728(2) 0.98205(16) 0.0372(7) Uani 1 1 d . B . H8B H 0.4367 -1.0734 0.9530 0.045 Uiso 1 1 calc R . . O8B O 0.42031(15) -1.05920(15) 1.03960(11) 0.0419(6) Uani 1 1 d . . . C8AB C 0.31297(19) -0.99839(18) 0.96622(11) 0.0249(5) Uani 1 1 d . . . C9B C 0.3605(3) -1.1043(3) 1.0846(2) 0.0252(10) Uani 0.656(7) 1 d P B 1 C10B C 0.4220(5) -1.1571(5) 1.1275(4) 0.0358(15) Uani 0.656(7) 1 d P B 1 H10D H 0.4596 -1.2038 1.1065 0.054 Uiso 0.656(7) 1 calc PR B 1 H10E H 0.3820 -1.1885 1.1564 0.054 Uiso 0.656(7) 1 calc PR B 1 H10F H 0.4643 -1.1131 1.1474 0.054 Uiso 0.656(7) 1 calc PR B 1 C11B C 0.2932(3) -1.0355(3) 1.1142(2) 0.0361(12) Uani 0.656(7) 1 d P B 1 H11D H 0.2576 -1.0680 1.1448 0.054 Uiso 0.656(7) 1 calc PR B 1 H11E H 0.2493 -1.0101 1.0851 0.054 Uiso 0.656(7) 1 calc PR B 1 H11F H 0.3296 -0.9843 1.1316 0.054 Uiso 0.656(7) 1 calc PR B 1 C9B' C 0.4110(7) -1.1561(6) 1.0560(4) 0.036(2) Uani 0.344(7) 1 d P B 2 C10' C 0.3884(12) -1.1362(13) 1.1197(8) 0.049(4) Uani 0.344(7) 1 d P B 2 H10G H 0.4402 -1.1004 1.1372 0.074 Uiso 0.344(7) 1 calc PR B 2 H10H H 0.3807 -1.1954 1.1408 0.074 Uiso 0.344(7) 1 calc PR B 2 H10I H 0.3298 -1.0999 1.1222 0.074 Uiso 0.344(7) 1 calc PR B 2 C11' C 0.4977(7) -1.2152(7) 1.0459(5) 0.048(3) Uani 0.344(7) 1 d P B 2 H11G H 0.5181 -1.2086 1.0051 0.072 Uiso 0.344(7) 1 calc PR B 2 H11H H 0.4829 -1.2809 1.0539 0.072 Uiso 0.344(7) 1 calc PR B 2 H11I H 0.5485 -1.1944 1.0719 0.072 Uiso 0.344(7) 1 calc PR B 2 N1C N -0.07401(14) -1.08594(14) 0.84056(8) 0.0190(4) Uani 1 1 d . . . O1C O -0.03414(12) -1.05942(14) 0.88930(7) 0.0244(4) Uani 1 1 d . . . C2C C -0.02357(17) -1.08224(17) 0.78932(11) 0.0208(5) Uani 1 1 d . . . C3C C -0.06274(19) -1.11298(17) 0.73714(11) 0.0237(5) Uani 1 1 d . . . C31C C -0.0040(2) -1.1098(2) 0.68200(12) 0.0331(6) Uani 1 1 d . . . H31G H 0.0221 -1.0469 0.6769 0.050 Uiso 1 1 calc R . . H31H H -0.0438 -1.1255 0.6483 0.050 Uiso 1 1 calc R . . H31I H 0.0477 -1.1551 0.6850 0.050 Uiso 1 1 calc R . . C4C C -0.15510(19) -1.14511(17) 0.73716(11) 0.0230(5) Uani 1 1 d . . . H4C H -0.1827 -1.1673 0.7019 0.028 Uiso 1 1 calc R . . C4AC C -0.20766(17) -1.14492(16) 0.78860(10) 0.0208(5) Uani 1 1 d . . . C5C C -0.30969(18) -1.17388(19) 0.78871(11) 0.0257(5) Uani 1 1 d . . . H5C1 H -0.3210 -1.2182 0.7562 0.031 Uiso 1 1 calc R . . H5C2 H -0.3498 -1.1182 0.7822 0.031 Uiso 1 1 calc R . . C6C C -0.33756(19) -1.21998(18) 0.84611(12) 0.0269(5) Uani 1 1 d . . . H6C1 H -0.4060 -1.2340 0.8456 0.032 Uiso 1 1 calc R . . H6C2 H -0.3031 -1.2799 0.8503 0.032 Uiso 1 1 calc R . . C7C C -0.31549(17) -1.15777(18) 0.89771(11) 0.0232(5) Uani 1 1 d . . . H7C H -0.3272 -1.1929 0.9348 0.028 Uiso 1 1 calc R . . O7C O -0.37508(12) -1.07701(13) 0.89579(8) 0.0253(4) Uani 1 1 d . . . C8C C -0.21486(17) -1.11561(18) 0.89886(10) 0.0206(5) Uani 1 1 d . . . H8C H -0.1753 -1.1493 0.9283 0.025 Uiso 1 1 calc R . . O8C O -0.22897(12) -1.02087(13) 0.91701(8) 0.0275(4) Uani 1 1 d . . . C8AC C -0.16626(17) -1.11618(16) 0.84052(10) 0.0195(4) Uani 1 1 d . . . C9C C -0.32774(17) -1.00602(18) 0.92823(11) 0.0228(5) Uani 1 1 d . . . C10C C -0.34774(19) -1.0147(2) 0.99325(11) 0.0303(6) Uani 1 1 d . . . H10J H -0.4155 -1.0064 1.0003 0.046 Uiso 1 1 calc R . . H10K H -0.3123 -0.9667 1.0145 0.046 Uiso 1 1 calc R . . H10L H -0.3283 -1.0768 1.0069 0.046 Uiso 1 1 calc R . . C11C C -0.3541(2) -0.9113(2) 0.90428(12) 0.0310(6) Uani 1 1 d . . . H11J H -0.3355 -0.9074 0.8631 0.046 Uiso 1 1 calc R . . H11K H -0.3215 -0.8625 0.9266 0.046 Uiso 1 1 calc R . . H11L H -0.4225 -0.9024 0.9076 0.046 Uiso 1 1 calc R . . N1D N 0.14703(15) -1.09774(14) 0.78960(9) 0.0216(4) Uani 1 1 d . . . O1D O 0.13234(14) -1.18723(13) 0.78815(10) 0.0313(4) Uani 1 1 d . . . C2D C 0.07118(17) -1.03818(17) 0.79290(10) 0.0217(5) Uani 1 1 d . . . C3D C 0.08479(19) -0.94197(18) 0.79514(11) 0.0255(5) Uani 1 1 d . . . C31D C 0.0004(2) -0.8776(2) 0.79933(15) 0.0356(7) Uani 1 1 d . . . H31J H 0.0219 -0.8135 0.8065 0.053 Uiso 1 1 calc R . . H31K H -0.0403 -0.8978 0.8316 0.053 Uiso 1 1 calc R . . H31L H -0.0352 -0.8797 0.7626 0.053 Uiso 1 1 calc R . . C4D C 0.1758(2) -0.90715(18) 0.79325(13) 0.0297(6) Uani 1 1 d . . . H4D H 0.1859 -0.8415 0.7949 0.036 Uiso 1 1 calc R . . C4AD C 0.25251(18) -0.96744(18) 0.78895(11) 0.0243(5) Uani 1 1 d . . . C5D C 0.35243(19) -0.93016(19) 0.78673(13) 0.0304(6) Uani 1 1 d . . . H5D1 H 0.3704 -0.9185 0.7455 0.036 Uiso 1 1 calc R . . H5D2 H 0.3554 -0.8698 0.8079 0.036 Uiso 1 1 calc R . . C6D C 0.4212(2) -0.9976(2) 0.81358(13) 0.0335(6) Uani 1 1 d . . . H6D1 H 0.4089 -1.0019 0.8561 0.040 Uiso 1 1 calc R . . H6D2 H 0.4862 -0.9733 0.8083 0.040 Uiso 1 1 calc R . . C7D C 0.41463(19) -1.0938(2) 0.78700(14) 0.0319(6) Uani 1 1 d . . . H7D H 0.4557 -1.1380 0.8093 0.038 Uiso 1 1 calc R . . O7D O 0.44548(14) -1.08924(14) 0.72843(9) 0.0343(5) Uani 1 1 d . . . C8D C 0.31404(18) -1.13543(18) 0.78145(12) 0.0271(5) Uani 1 1 d . . . H8D H 0.3048 -1.1853 0.8116 0.033 Uiso 1 1 calc R . . O8D O 0.31168(13) -1.17617(14) 0.72395(9) 0.0296(4) Uani 1 1 d . . . C8AD C 0.23750(17) -1.06331(17) 0.78686(11) 0.0223(5) Uani 1 1 d . . . C9D C 0.40520(19) -1.1696(2) 0.70051(13) 0.0303(6) Uani 1 1 d . . . C10D C 0.4628(2) -1.2566(2) 0.71259(17) 0.0425(8) Uani 1 1 d . . . H10M H 0.5272 -1.2478 0.6978 0.064 Uiso 1 1 calc R . . H10N H 0.4338 -1.3103 0.6930 0.064 Uiso 1 1 calc R . . H10O H 0.4649 -1.2681 0.7548 0.064 Uiso 1 1 calc R . . C11D C 0.3947(2) -1.1516(3) 0.63562(14) 0.0422(8) Uani 1 1 d . . . H11M H 0.3623 -1.0919 0.6295 0.063 Uiso 1 1 calc R . . H11N H 0.3578 -1.2021 0.6179 0.063 Uiso 1 1 calc R . . H11O H 0.4574 -1.1493 0.6175 0.063 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 0.0196(9) 0.0199(9) 0.0181(9) -0.0008(8) 0.0002(7) -0.0003(8) O1A 0.0306(9) 0.0233(8) 0.0175(8) -0.0030(6) -0.0033(7) -0.0030(7) C2A 0.0176(10) 0.0233(12) 0.0216(11) 0.0023(9) 0.0005(9) 0.0009(9) C3A 0.0175(11) 0.0311(13) 0.0220(11) 0.0027(10) 0.0005(9) 0.0024(10) C31A 0.0332(14) 0.0336(14) 0.0228(12) 0.0049(10) -0.0040(11) -0.0025(12) C4A 0.0193(11) 0.0310(13) 0.0216(11) -0.0043(10) -0.0022(9) 0.0038(10) C4AA 0.0183(10) 0.0240(12) 0.0222(11) -0.0028(9) -0.0006(9) 0.0024(9) C5A 0.0308(13) 0.0245(13) 0.0260(12) -0.0041(10) -0.0012(10) -0.0017(10) C6A 0.0259(12) 0.0262(13) 0.0354(14) -0.0034(11) 0.0006(11) -0.0084(10) C7A 0.0277(12) 0.0211(12) 0.0251(12) -0.0002(10) 0.0052(10) -0.0036(10) O7A 0.0336(10) 0.0197(8) 0.0266(9) -0.0004(7) -0.0036(8) -0.0024(8) C8A 0.0225(11) 0.0198(11) 0.0198(11) -0.0021(9) 0.0018(9) -0.0023(9) O8A 0.0254(9) 0.0217(9) 0.0386(10) 0.0088(8) -0.0062(8) -0.0023(7) C8AA 0.0186(10) 0.0216(11) 0.0194(10) -0.0021(9) 0.0028(8) 0.0005(9) C9A 0.0327(13) 0.0192(11) 0.0228(11) 0.0049(9) -0.0007(10) -0.0025(10) C10A 0.0421(15) 0.0300(14) 0.0207(12) 0.0015(10) -0.0016(11) -0.0041(12) C11A 0.0331(14) 0.0348(14) 0.0289(13) 0.0037(11) -0.0006(11) 0.0072(12) N1B 0.0198(10) 0.0237(10) 0.0253(10) -0.0008(8) 0.0028(8) -0.0025(8) O1B 0.0182(8) 0.0296(10) 0.0521(12) 0.0043(9) 0.0041(8) -0.0020(8) C2B 0.0222(11) 0.0232(12) 0.0186(11) 0.0032(9) 0.0006(9) -0.0011(9) C3B 0.0224(12) 0.0317(14) 0.0302(13) 0.0109(11) -0.0047(10) -0.0010(10) C31B 0.0238(13) 0.0348(16) 0.0582(19) 0.0159(14) -0.0058(13) 0.0009(12) C4B 0.0230(12) 0.0370(15) 0.0433(16) 0.0134(13) -0.0113(11) -0.0087(11) C4AB 0.0307(13) 0.0283(13) 0.0278(12) 0.0083(11) -0.0054(10) -0.0088(11) C5B 0.0387(16) 0.0316(15) 0.0477(17) 0.0158(13) -0.0193(14) -0.0145(13) C6B 0.077(3) 0.0308(16) 0.0433(18) -0.0092(14) 0.0155(17) -0.0197(17) C7B 0.0307(16) 0.0185(13) 0.130(4) -0.0040(19) 0.018(2) -0.0006(12) O7B 0.0633(17) 0.079(2) 0.083(2) 0.0588(17) -0.0457(16) -0.0488(16) C8B 0.0283(14) 0.0220(13) 0.061(2) -0.0001(13) 0.0129(13) -0.0012(11) O8B 0.0263(10) 0.0295(11) 0.0701(15) 0.0204(10) -0.0040(10) -0.0032(8) C8AB 0.0256(12) 0.0245(12) 0.0248(11) -0.0016(10) 0.0033(10) -0.0031(10) C9B 0.0260(19) 0.0215(19) 0.028(2) 0.0039(17) -0.0039(17) -0.0054(16) C10B 0.037(4) 0.032(3) 0.039(3) 0.014(2) -0.010(3) -0.009(3) C11B 0.032(2) 0.038(3) 0.038(2) -0.0030(19) -0.0019(18) -0.0045(19) C9B' 0.040(5) 0.020(4) 0.046(5) 0.011(3) -0.021(4) -0.005(3) C10' 0.049(10) 0.048(10) 0.052(9) 0.007(8) -0.010(8) -0.018(7) C11' 0.035(5) 0.031(5) 0.079(8) 0.008(5) -0.025(5) 0.008(4) N1C 0.0205(9) 0.0193(9) 0.0173(9) -0.0005(7) -0.0015(7) 0.0001(8) O1C 0.0203(8) 0.0349(10) 0.0180(8) -0.0052(7) -0.0034(7) -0.0039(7) C2C 0.0226(11) 0.0192(11) 0.0206(11) 0.0002(9) 0.0032(9) 0.0005(9) C3C 0.0309(13) 0.0180(11) 0.0221(11) -0.0016(9) 0.0014(10) 0.0001(10) C31C 0.0389(15) 0.0324(14) 0.0278(13) -0.0048(11) 0.0083(12) -0.0038(12) C4C 0.0303(13) 0.0182(11) 0.0203(11) -0.0021(9) -0.0031(10) 0.0004(10) C4AC 0.0233(11) 0.0180(11) 0.0210(11) 0.0009(9) -0.0047(9) 0.0004(9) C5C 0.0255(12) 0.0252(12) 0.0265(12) -0.0050(10) -0.0033(10) -0.0020(10) C6C 0.0219(12) 0.0246(12) 0.0341(14) 0.0008(10) -0.0037(10) -0.0045(10) C7C 0.0194(11) 0.0266(12) 0.0236(11) 0.0043(9) 0.0013(9) -0.0014(9) O7C 0.0189(8) 0.0288(9) 0.0281(9) 0.0002(8) -0.0036(7) 0.0003(7) C8C 0.0178(11) 0.0240(12) 0.0199(11) -0.0007(9) -0.0004(9) 0.0013(9) O8C 0.0185(8) 0.0293(10) 0.0346(9) -0.0082(8) 0.0060(7) -0.0016(7) C8AC 0.0196(11) 0.0189(10) 0.0201(10) 0.0017(9) -0.0013(9) 0.0016(9) C9C 0.0167(11) 0.0279(12) 0.0237(11) -0.0033(9) 0.0009(9) 0.0001(9) C10C 0.0256(13) 0.0418(15) 0.0237(12) 0.0018(11) 0.0007(10) -0.0009(12) C11C 0.0346(14) 0.0304(14) 0.0280(13) 0.0008(11) 0.0016(11) 0.0041(11) N1D 0.0236(10) 0.0181(10) 0.0233(10) -0.0008(8) 0.0031(8) -0.0005(8) O1D 0.0283(9) 0.0163(8) 0.0492(12) 0.0024(8) 0.0042(9) -0.0028(7) C2D 0.0231(11) 0.0224(12) 0.0196(11) -0.0014(9) 0.0041(9) -0.0018(9) C3D 0.0280(13) 0.0222(12) 0.0263(12) -0.0047(10) 0.0047(10) 0.0005(10) C31D 0.0291(14) 0.0241(13) 0.0535(18) -0.0054(13) 0.0042(13) 0.0022(11) C4D 0.0305(13) 0.0175(11) 0.0410(15) -0.0034(11) 0.0067(11) -0.0020(10) C4AD 0.0249(12) 0.0254(13) 0.0225(11) -0.0023(10) 0.0058(9) -0.0025(10) C5D 0.0256(13) 0.0234(12) 0.0421(15) -0.0069(11) 0.0076(11) -0.0065(10) C6D 0.0252(13) 0.0381(16) 0.0371(15) -0.0116(12) -0.0024(11) -0.0066(12) C7D 0.0215(12) 0.0311(14) 0.0431(16) -0.0038(12) -0.0031(11) 0.0005(11) O7D 0.0261(9) 0.0322(10) 0.0447(11) -0.0136(9) 0.0072(8) -0.0060(8) C8D 0.0220(12) 0.0221(12) 0.0373(14) -0.0017(10) -0.0021(11) 0.0000(10) O8D 0.0198(8) 0.0277(9) 0.0414(11) -0.0101(8) 0.0069(8) -0.0031(8) C8AD 0.0223(11) 0.0218(12) 0.0227(11) -0.0005(9) 0.0027(9) -0.0003(9) C9D 0.0226(12) 0.0322(14) 0.0362(14) -0.0064(12) 0.0043(11) -0.0014(11) C10D 0.0279(14) 0.0357(16) 0.064(2) -0.0137(16) -0.0023(14) 0.0024(12) C11D 0.0391(17) 0.051(2) 0.0367(16) -0.0001(14) 0.0038(13) -0.0143(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 N1A O1A 1.305(3) . ? N1A C2A 1.371(3) . ? N1A C8AA 1.377(3) . ? C2A C3A 1.388(3) . ? C2A C2B 1.487(3) . ? C3A C4A 1.389(4) . ? C3A C31A 1.506(4) . ? C31A H31A 0.9800 . ? C31A H31B 0.9800 . ? C31A H31C 0.9800 . ? C4A C4AA 1.395(4) . ? C4A H4A 0.9500 . ? C4AA C8AA 1.395(3) . ? C4AA C5A 1.505(4) . ? C5A C6A 1.522(4) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C6A C7A 1.514(4) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7A O7A 1.433(3) . ? C7A C8A 1.560(3) . ? C7A H7A 1.0000 . ? O7A C9A 1.422(3) . ? C8A O8A 1.429(3) . ? C8A C8AA 1.492(3) . ? C8A H8A 1.0000 . ? O8A C9A 1.432(3) . ? C9A C11A 1.505(4) . ? C9A C10A 1.517(3) . ? C10A H10A 0.9800 . ? C10A H10B 0.9800 . ? C10A H10C 0.9800 . ? C11A H11A 0.9800 . ? C11A H11B 0.9800 . ? C11A H11C 0.9800 . ? N1B O1B 1.296(3) . ? N1B C2B 1.355(3) . ? N1B C8AB 1.386(3) . ? C2B C3B 1.394(3) . ? C3B C4B 1.395(4) . ? C3B C31B 1.502(4) . ? C31B H31D 0.9800 . ? C31B H31E 0.9800 . ? C31B H31F 0.9800 . ? C4B C4AB 1.384(4) . ? C4B H4B 0.9500 . ? C4AB C8AB 1.383(4) . ? C4AB C5B 1.510(4) . ? C5B C6B 1.512(5) . ? C5B H5B1 0.9900 . ? C5B H5B2 0.9900 . ? C6B C7B 1.516(6) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7B O7B 1.419(6) . ? C7B C8B 1.545(4) . ? C7B C9B' 1.893(10) . ? C7B H7B 1.0000 . ? O7B C9B' 1.476(9) . ? O7B C9B 1.511(5) . ? C8B O8B 1.427(4) . ? C8B C8AB 1.508(4) . ? C8B H8B 1.0000 . ? O8B C9B' 1.442(8) . ? O8B C9B 1.480(5) . ? C9B C10B 1.515(7) . ? C9B C11B 1.528(6) . ? C10B H10D 0.9800 . ? C10B H10E 0.9800 . ? C10B H10F 0.9800 . ? C11B H11D 0.9800 . ? C11B H11E 0.9800 . ? C11B H11F 0.9800 . ? C9B' C11' 1.508(13) . ? C9B' C10' 1.52(2) . ? C10' H10G 0.9800 . ? C10' H10H 0.9800 . ? C10' H10I 0.9800 . ? C11' H11G 0.9800 . ? C11' H11H 0.9800 . ? C11' H11I 0.9800 . ? N1C O1C 1.306(3) . ? N1C C2C 1.374(3) . ? N1C C8AC 1.376(3) . ? C2C C3C 1.388(3) . ? C2C C2D 1.485(3) . ? C3C C4C 1.386(4) . ? C3C C31C 1.512(4) . ? C31C H31G 0.9800 . ? C31C H31H 0.9800 . ? C31C H31I 0.9800 . ? C4C C4AC 1.393(3) . ? C4C H4C 0.9500 . ? C4AC C8AC 1.387(3) . ? C4AC C5C 1.503(3) . ? C5C C6C 1.522(4) . ? C5C H5C1 0.9900 . ? C5C H5C2 0.9900 . ? C6C C7C 1.511(4) . ? C6C H6C1 0.9900 . ? C6C H6C2 0.9900 . ? C7C O7C 1.431(3) . ? C7C C8C 1.548(3) . ? C7C H7C 1.0000 . ? O7C C9C 1.425(3) . ? C8C O8C 1.431(3) . ? C8C C8AC 1.502(3) . ? C8C H8C 1.0000 . ? O8C C9C 1.438(3) . ? C9C C11C 1.508(4) . ? C9C C10C 1.520(3) . ? C10C H10J 0.9800 . ? C10C H10K 0.9800 . ? C10C H10L 0.9800 . ? C11C H11J 0.9800 . ? C11C H11K 0.9800 . ? C11C H11L 0.9800 . ? N1D O1D 1.297(3) . ? N1D C2D 1.373(3) . ? N1D C8AD 1.374(3) . ? C2D C3D 1.390(4) . ? C3D C4D 1.382(4) . ? C3D C31D 1.512(4) . ? C31D H31J 0.9800 . ? C31D H31K 0.9800 . ? C31D H31L 0.9800 . ? C4D C4AD 1.391(4) . ? C4D H4D 0.9500 . ? C4AD C8AD 1.388(4) . ? C4AD C5D 1.513(4) . ? C5D C6D 1.502(4) . ? C5D H5D1 0.9900 . ? C5D H5D2 0.9900 . ? C6D C7D 1.507(4) . ? C6D H6D1 0.9900 . ? C6D H6D2 0.9900 . ? C7D O7D 1.411(4) . ? C7D C8D 1.549(4) . ? C7D H7D 1.0000 . ? O7D C9D 1.432(3) . ? C8D O8D 1.439(3) . ? C8D C8AD 1.501(3) . ? C8D H8D 1.0000 . ? O8D C9D 1.432(3) . ? C9D C11D 1.514(4) . ? C9D C10D 1.514(4) . ? C10D H10M 0.9800 . ? C10D H10N 0.9800 . ? C10D H10O 0.9800 . ? C11D H11M 0.9800 . ? C11D H11N 0.9800 . ? C11D H11O 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 O1A N1A C2A 119.8(2) . . ? O1A N1A C8AA 119.61(19) . . ? C2A N1A C8AA 120.6(2) . . ? N1A C2A C3A 120.9(2) . . ? N1A C2A C2B 116.7(2) . . ? C3A C2A C2B 122.3(2) . . ? C2A C3A C4A 119.0(2) . . ? C2A C3A C31A 119.7(2) . . ? C4A C3A C31A 121.4(2) . . ? C3A C31A H31A 109.5 . . ? C3A C31A H31B 109.5 . . ? H31A C31A H31B 109.5 . . ? C3A C31A H31C 109.5 . . ? H31A C31A H31C 109.5 . . ? H31B C31A H31C 109.5 . . ? C3A C4A C4AA 120.2(2) . . ? C3A C4A H4A 119.9 . . ? C4AA C4A H4A 119.9 . . ? C8AA C4AA C4A 119.6(2) . . ? C8AA C4AA C5A 118.0(2) . . ? C4A C4AA C5A 122.4(2) . . ? C4AA C5A C6A 111.6(2) . . ? C4AA C5A H5A1 109.3 . . ? C6A C5A H5A1 109.3 . . ? C4AA C5A H5A2 109.3 . . ? C6A C5A H5A2 109.3 . . ? H5A1 C5A H5A2 108.0 . . ? C7A C6A C5A 110.9(2) . . ? C7A C6A H6A1 109.5 . . ? C5A C6A H6A1 109.5 . . ? C7A C6A H6A2 109.5 . . ? C5A C6A H6A2 109.5 . . ? H6A1 C6A H6A2 108.0 . . ? O7A C7A C6A 108.9(2) . . ? O7A C7A C8A 103.7(2) . . ? C6A C7A C8A 115.3(2) . . ? O7A C7A H7A 109.6 . . ? C6A C7A H7A 109.6 . . ? C8A C7A H7A 109.6 . . ? C9A O7A C7A 106.58(19) . . ? O8A C8A C8AA 108.00(19) . . ? O8A C8A C7A 103.78(19) . . ? C8AA C8A C7A 114.7(2) . . ? O8A C8A H8A 110.0 . . ? C8AA C8A H8A 110.0 . . ? C7A C8A H8A 110.0 . . ? C8A O8A C9A 109.03(19) . . ? N1A C8AA C4AA 119.6(2) . . ? N1A C8AA C8A 116.2(2) . . ? C4AA C8AA C8A 124.2(2) . . ? O7A C9A O8A 104.5(2) . . ? O7A C9A C11A 109.8(2) . . ? O8A C9A C11A 107.4(2) . . ? O7A C9A C10A 111.7(2) . . ? O8A C9A C10A 110.8(2) . . ? C11A C9A C10A 112.2(2) . . ? C9A C10A H10A 109.5 . . ? C9A C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? C9A C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C9A C11A H11A 109.5 . . ? C9A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? C9A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? O1B N1B C2B 119.9(2) . . ? O1B N1B C8AB 119.3(2) . . ? C2B N1B C8AB 120.8(2) . . ? N1B C2B C3B 120.7(2) . . ? N1B C2B C2A 116.4(2) . . ? C3B C2B C2A 122.7(2) . . ? C2B C3B C4B 118.4(3) . . ? C2B C3B C31B 120.4(3) . . ? C4B C3B C31B 121.2(2) . . ? C3B C31B H31D 109.5 . . ? C3B C31B H31E 109.5 . . ? H31D C31B H31E 109.5 . . ? C3B C31B H31F 109.5 . . ? H31D C31B H31F 109.5 . . ? H31E C31B H31F 109.5 . . ? C4AB C4B C3B 120.6(2) . . ? C4AB C4B H4B 119.7 . . ? C3B C4B H4B 119.7 . . ? C8AB C4AB C4B 119.7(3) . . ? C8AB C4AB C5B 119.6(3) . . ? C4B C4AB C5B 120.7(3) . . ? C4AB C5B C6B 112.6(3) . . ? C4AB C5B H5B1 109.1 . . ? C6B C5B H5B1 109.1 . . ? C4AB C5B H5B2 109.1 . . ? C6B C5B H5B2 109.1 . . ? H5B1 C5B H5B2 107.8 . . ? C5B C6B C7B 110.9(3) . . ? C5B C6B H6B1 109.5 . . ? C7B C6B H6B1 109.5 . . ? C5B C6B H6B2 109.5 . . ? C7B C6B H6B2 109.5 . . ? H6B1 C6B H6B2 108.0 . . ? O7B C7B C6B 109.1(3) . . ? O7B C7B C8B 102.4(3) . . ? C6B C7B C8B 113.8(3) . . ? O7B C7B C9B' 50.5(4) . . ? C6B C7B C9B' 159.6(4) . . ? C8B C7B C9B' 74.8(3) . . ? O7B C7B H7B 110.4 . . ? C6B C7B H7B 110.4 . . ? C8B C7B H7B 110.4 . . ? C9B' C7B H7B 81.8 . . ? C7B O7B C9B' 81.6(5) . . ? C7B O7B C9B 113.4(3) . . ? C9B' O7B C9B 48.2(4) . . ? O8B C8B C8AB 111.5(2) . . ? O8B C8B C7B 101.9(3) . . ? C8AB C8B C7B 112.7(3) . . ? O8B C8B H8B 110.2 . . ? C8AB C8B H8B 110.2 . . ? C7B C8B H8B 110.2 . . ? C8B O8B C9B' 94.4(4) . . ? C8B O8B C9B 112.0(2) . . ? C9B' O8B C9B 49.3(5) . . ? C4AB C8AB N1B 119.5(2) . . ? C4AB C8AB C8B 125.0(2) . . ? N1B C8AB C8B 115.5(2) . . ? O8B C9B O7B 98.9(3) . . ? O8B C9B C10B 109.8(5) . . ? O7B C9B C10B 108.9(4) . . ? O8B C9B C11B 112.6(3) . . ? O7B C9B C11B 112.7(4) . . ? C10B C9B C11B 113.1(5) . . ? O8B C9B' O7B 102.4(5) . . ? O8B C9B' C11' 115.1(8) . . ? O7B C9B' C11' 132.2(7) . . ? O8B C9B' C10' 95.1(9) . . ? O7B C9B' C10' 88.6(9) . . ? C11' C9B' C10' 115.1(10) . . ? O8B C9B' C7B 86.5(4) . . ? O7B C9B' C7B 47.9(3) . . ? C11' C9B' C7B 104.2(7) . . ? C10' C9B' C7B 135.2(9) . . ? C9B' C10' H10G 109.5 . . ? C9B' C10' H10H 109.5 . . ? H10G C10' H10H 109.5 . . ? C9B' C10' H10I 109.5 . . ? H10G C10' H10I 109.5 . . ? H10H C10' H10I 109.5 . . ? C9B' C11' H11G 109.5 . . ? C9B' C11' H11H 109.5 . . ? H11G C11' H11H 109.5 . . ? C9B' C11' H11I 109.5 . . ? H11G C11' H11I 109.5 . . ? H11H C11' H11I 109.5 . . ? O1C N1C C2C 119.51(19) . . ? O1C N1C C8AC 120.15(19) . . ? C2C N1C C8AC 120.3(2) . . ? N1C C2C C3C 120.9(2) . . ? N1C C2C C2D 116.0(2) . . ? C3C C2C C2D 122.9(2) . . ? C4C C3C C2C 118.8(2) . . ? C4C C3C C31C 122.0(2) . . ? C2C C3C C31C 119.2(2) . . ? C3C C31C H31G 109.5 . . ? C3C C31C H31H 109.5 . . ? H31G C31C H31H 109.5 . . ? C3C C31C H31I 109.5 . . ? H31G C31C H31I 109.5 . . ? H31H C31C H31I 109.5 . . ? C3C C4C C4AC 120.3(2) . . ? C3C C4C H4C 119.9 . . ? C4AC C4C H4C 119.9 . . ? C8AC C4AC C4C 119.9(2) . . ? C8AC C4AC C5C 119.1(2) . . ? C4C C4AC C5C 121.0(2) . . ? C4AC C5C C6C 111.7(2) . . ? C4AC C5C H5C1 109.3 . . ? C6C C5C H5C1 109.3 . . ? C4AC C5C H5C2 109.3 . . ? C6C C5C H5C2 109.3 . . ? H5C1 C5C H5C2 107.9 . . ? C7C C6C C5C 111.5(2) . . ? C7C C6C H6C1 109.3 . . ? C5C C6C H6C1 109.3 . . ? C7C C6C H6C2 109.3 . . ? C5C C6C H6C2 109.3 . . ? H6C1 C6C H6C2 108.0 . . ? O7C C7C C6C 109.2(2) . . ? O7C C7C C8C 103.26(19) . . ? C6C C7C C8C 115.7(2) . . ? O7C C7C H7C 109.5 . . ? C6C C7C H7C 109.5 . . ? C8C C7C H7C 109.5 . . ? C9C O7C C7C 106.33(18) . . ? O8C C8C C8AC 109.1(2) . . ? O8C C8C C7C 104.18(18) . . ? C8AC C8C C7C 113.9(2) . . ? O8C C8C H8C 109.8 . . ? C8AC C8C H8C 109.8 . . ? C7C C8C H8C 109.8 . . ? C8C O8C C9C 109.12(18) . . ? N1C C8AC C4AC 119.7(2) . . ? N1C C8AC C8C 115.6(2) . . ? C4AC C8AC C8C 124.7(2) . . ? O7C C9C O8C 105.04(19) . . ? O7C C9C C11C 109.5(2) . . ? O8C C9C C11C 108.0(2) . . ? O7C C9C C10C 111.3(2) . . ? O8C C9C C10C 110.1(2) . . ? C11C C9C C10C 112.5(2) . . ? C9C C10C H10J 109.5 . . ? C9C C10C H10K 109.5 . . ? H10J C10C H10K 109.5 . . ? C9C C10C H10L 109.5 . . ? H10J C10C H10L 109.5 . . ? H10K C10C H10L 109.5 . . ? C9C C11C H11J 109.5 . . ? C9C C11C H11K 109.5 . . ? H11J C11C H11K 109.5 . . ? C9C C11C H11L 109.5 . . ? H11J C11C H11L 109.5 . . ? H11K C11C H11L 109.5 . . ? O1D N1D C2D 119.2(2) . . ? O1D N1D C8AD 120.1(2) . . ? C2D N1D C8AD 120.7(2) . . ? N1D C2D C3D 120.5(2) . . ? N1D C2D C2C 116.2(2) . . ? C3D C2D C2C 123.2(2) . . ? C4D C3D C2D 119.0(2) . . ? C4D C3D C31D 121.3(2) . . ? C2D C3D C31D 119.7(2) . . ? C3D C31D H31J 109.5 . . ? C3D C31D H31K 109.5 . . ? H31J C31D H31K 109.5 . . ? C3D C31D H31L 109.5 . . ? H31J C31D H31L 109.5 . . ? H31K C31D H31L 109.5 . . ? C3D C4D C4AD 120.5(2) . . ? C3D C4D H4D 119.7 . . ? C4AD C4D H4D 119.7 . . ? C8AD C4AD C4D 119.7(2) . . ? C8AD C4AD C5D 119.3(2) . . ? C4D C4AD C5D 121.0(2) . . ? C6D C5D C4AD 111.5(2) . . ? C6D C5D H5D1 109.3 . . ? C4AD C5D H5D1 109.3 . . ? C6D C5D H5D2 109.3 . . ? C4AD C5D H5D2 109.3 . . ? H5D1 C5D H5D2 108.0 . . ? C5D C6D C7D 112.3(2) . . ? C5D C6D H6D1 109.1 . . ? C7D C6D H6D1 109.1 . . ? C5D C6D H6D2 109.1 . . ? C7D C6D H6D2 109.1 . . ? H6D1 C6D H6D2 107.9 . . ? O7D C7D C6D 108.8(2) . . ? O7D C7D C8D 103.0(2) . . ? C6D C7D C8D 116.2(2) . . ? O7D C7D H7D 109.5 . . ? C6D C7D H7D 109.5 . . ? C8D C7D H7D 109.5 . . ? C7D O7D C9D 105.3(2) . . ? O8D C8D C8AD 109.7(2) . . ? O8D C8D C7D 104.6(2) . . ? C8AD C8D C7D 113.1(2) . . ? O8D C8D H8D 109.8 . . ? C8AD C8D H8D 109.8 . . ? C7D C8D H8D 109.8 . . ? C9D O8D C8D 107.10(19) . . ? N1D C8AD C4AD 119.7(2) . . ? N1D C8AD C8D 115.5(2) . . ? C4AD C8AD C8D 124.8(2) . . ? O7D C9D O8D 104.7(2) . . ? O7D C9D C11D 109.9(3) . . ? O8D C9D C11D 106.7(2) . . ? O7D C9D C10D 111.3(2) . . ? O8D C9D C10D 112.1(2) . . ? C11D C9D C10D 111.8(3) . . ? C9D C10D H10M 109.5 . . ? C9D C10D H10N 109.5 . . ? H10M C10D H10N 109.5 . . ? C9D C10D H10O 109.5 . . ? H10M C10D H10O 109.5 . . ? H10N C10D H10O 109.5 . . ? C9D C11D H11M 109.5 . . ? C9D C11D H11N 109.5 . . ? H11M C11D H11N 109.5 . . ? C9D C11D H11O 109.5 . . ? H11M C11D H11O 109.5 . . ? H11N C11D H11O 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 O1A N1A C2A C3A 178.2(2) . . . . ? C8AA N1A C2A C3A -3.1(3) . . . . ? O1A N1A C2A C2B -5.9(3) . . . . ? C8AA N1A C2A C2B 172.8(2) . . . . ? N1A C2A C3A C4A 2.1(4) . . . . ? C2B C2A C3A C4A -173.5(2) . . . . ? N1A C2A C3A C31A -178.3(2) . . . . ? C2B C2A C3A C31A 6.1(4) . . . . ? C2A C3A C4A C4AA 0.7(4) . . . . ? C31A C3A C4A C4AA -178.9(2) . . . . ? C3A C4A C4AA C8AA -2.5(4) . . . . ? C3A C4A C4AA C5A 176.3(2) . . . . ? C8AA C4AA C5A C6A -36.2(3) . . . . ? C4A C4AA C5A C6A 145.0(2) . . . . ? C4AA C5A C6A C7A 58.1(3) . . . . ? C5A C6A C7A O7A 69.7(3) . . . . ? C5A C6A C7A C8A -46.3(3) . . . . ? C6A C7A O7A C9A -152.5(2) . . . . ? C8A C7A O7A C9A -29.3(2) . . . . ? O7A C7A C8A O8A 11.4(2) . . . . ? C6A C7A C8A O8A 130.3(2) . . . . ? O7A C7A C8A C8AA -106.3(2) . . . . ? C6A C7A C8A C8AA 12.6(3) . . . . ? C8AA C8A O8A C9A 132.7(2) . . . . ? C7A C8A O8A C9A 10.5(2) . . . . ? O1A N1A C8AA C4AA 179.9(2) . . . . ? C2A N1A C8AA C4AA 1.2(3) . . . . ? O1A N1A C8AA C8A 1.3(3) . . . . ? C2A N1A C8AA C8A -177.4(2) . . . . ? C4A C4AA C8AA N1A 1.6(3) . . . . ? C5A C4AA C8AA N1A -177.3(2) . . . . ? C4A C4AA C8AA C8A -179.9(2) . . . . ? C5A C4AA C8AA C8A 1.2(4) . . . . ? O8A C8A C8AA N1A 74.4(3) . . . . ? C7A C8A C8AA N1A -170.4(2) . . . . ? O8A C8A C8AA C4AA -104.2(3) . . . . ? C7A C8A C8AA C4AA 11.0(3) . . . . ? C7A O7A C9A O8A 36.4(2) . . . . ? C7A O7A C9A C11A 151.4(2) . . . . ? C7A O7A C9A C10A -83.4(2) . . . . ? C8A O8A C9A O7A -28.9(3) . . . . ? C8A O8A C9A C11A -145.5(2) . . . . ? C8A O8A C9A C10A 91.6(3) . . . . ? O1B N1B C2B C3B 177.6(2) . . . . ? C8AB N1B C2B C3B -4.4(4) . . . . ? O1B N1B C2B C2A -7.2(3) . . . . ? C8AB N1B C2B C2A 170.8(2) . . . . ? N1A C2A C2B N1B 112.1(2) . . . . ? C3A C2A C2B N1B -72.1(3) . . . . ? N1A C2A C2B C3B -72.8(3) . . . . ? C3A C2A C2B C3B 103.0(3) . . . . ? N1B C2B C3B C4B -0.5(4) . . . . ? C2A C2B C3B C4B -175.4(2) . . . . ? N1B C2B C3B C31B 179.5(3) . . . . ? C2A C2B C3B C31B 4.6(4) . . . . ? C2B C3B C4B C4AB 3.7(4) . . . . ? C31B C3B C4B C4AB -176.3(3) . . . . ? C3B C4B C4AB C8AB -2.1(4) . . . . ? C3B C4B C4AB C5B 177.2(3) . . . . ? C8AB C4AB C5B C6B -23.1(4) . . . . ? C4B C4AB C5B C6B 157.6(3) . . . . ? C4AB C5B C6B C7B 52.5(4) . . . . ? C5B C6B C7B O7B 57.0(4) . . . . ? C5B C6B C7B C8B -56.7(4) . . . . ? C5B C6B C7B C9B' 54.5(11) . . . . ? C6B C7B O7B C9B' -178.8(4) . . . . ? C8B C7B O7B C9B' -57.9(4) . . . . ? C6B C7B O7B C9B -141.7(3) . . . . ? C8B C7B O7B C9B -20.8(4) . . . . ? C9B' C7B O7B C9B 37.1(4) . . . . ? O7B C7B C8B O8B 31.5(3) . . . . ? C6B C7B C8B O8B 149.1(3) . . . . ? C9B' C7B C8B O8B -11.1(4) . . . . ? O7B C7B C8B C8AB -88.1(4) . . . . ? C6B C7B C8B C8AB 29.5(4) . . . . ? C9B' C7B C8B C8AB -130.7(4) . . . . ? C8AB C8B O8B C9B' 134.6(5) . . . . ? C7B C8B O8B C9B' 14.2(5) . . . . ? C8AB C8B O8B C9B 87.0(3) . . . . ? C7B C8B O8B C9B -33.4(3) . . . . ? C4B C4AB C8AB N1B -2.8(4) . . . . ? C5B C4AB C8AB N1B 177.9(3) . . . . ? C4B C4AB C8AB C8B 175.2(3) . . . . ? C5B C4AB C8AB C8B -4.1(4) . . . . ? O1B N1B C8AB C4AB -175.9(2) . . . . ? C2B N1B C8AB C4AB 6.0(4) . . . . ? O1B N1B C8AB C8B 5.9(4) . . . . ? C2B N1B C8AB C8B -172.1(2) . . . . ? O8B C8B C8AB C4AB -113.0(3) . . . . ? C7B C8B C8AB C4AB 0.9(4) . . . . ? O8B C8B C8AB N1B 65.1(3) . . . . ? C7B C8B C8AB N1B 178.9(3) . . . . ? C8B O8B C9B O7B 20.6(4) . . . . ? C9B' O8B C9B O7B -55.5(5) . . . . ? C8B O8B C9B C10B 134.5(4) . . . . ? C9B' O8B C9B C10B 58.3(6) . . . . ? C8B O8B C9B C11B -98.6(4) . . . . ? C9B' O8B C9B C11B -174.8(6) . . . . ? C7B O7B C9B O8B 1.9(4) . . . . ? C9B' O7B C9B O8B 55.1(5) . . . . ? C7B O7B C9B C10B -112.7(5) . . . . ? C9B' O7B C9B C10B -59.5(6) . . . . ? C7B O7B C9B C11B 121.1(4) . . . . ? C9B' O7B C9B C11B 174.3(6) . . . . ? C8B O8B C9B' O7B -56.8(6) . . . . ? C9B O8B C9B' O7B 58.6(5) . . . . ? C8B O8B C9B' C11' 92.7(7) . . . . ? C9B O8B C9B' C11' -151.8(9) . . . . ? C8B O8B C9B' C10' -146.5(7) . . . . ? C9B O8B C9B' C10' -31.0(7) . . . . ? C8B O8B C9B' C7B -11.3(4) . . . . ? C9B O8B C9B' C7B 104.1(5) . . . . ? C7B O7B C9B' O8B 73.7(5) . . . . ? C9B O7B C9B' O8B -58.3(5) . . . . ? C7B O7B C9B' C11' -68.0(10) . . . . ? C9B O7B C9B' C11' 160.0(12) . . . . ? C7B O7B C9B' C10' 168.6(8) . . . . ? C9B O7B C9B' C10' 36.5(7) . . . . ? C9B O7B C9B' C7B -132.0(4) . . . . ? O7B C7B C9B' O8B -110.1(6) . . . . ? C6B C7B C9B' O8B -107.0(10) . . . . ? C8B C7B C9B' O8B 10.8(4) . . . . ? C6B C7B C9B' O7B 3.1(11) . . . . ? C8B C7B C9B' O7B 120.9(4) . . . . ? O7B C7B C9B' C11' 134.9(7) . . . . ? C6B C7B C9B' C11' 138.0(10) . . . . ? C8B C7B C9B' C11' -104.2(6) . . . . ? O7B C7B C9B' C10' -16.4(11) . . . . ? C6B C7B C9B' C10' -13.2(18) . . . . ? C8B C7B C9B' C10' 104.5(12) . . . . ? O1C N1C C2C C3C 177.7(2) . . . . ? C8AC N1C C2C C3C -3.1(3) . . . . ? O1C N1C C2C C2D -6.1(3) . . . . ? C8AC N1C C2C C2D 173.0(2) . . . . ? N1C C2C C3C C4C 1.9(4) . . . . ? C2D C2C C3C C4C -174.0(2) . . . . ? N1C C2C C3C C31C -178.5(2) . . . . ? C2D C2C C3C C31C 5.6(4) . . . . ? C2C C3C C4C C4AC 1.0(4) . . . . ? C31C C3C C4C C4AC -178.5(2) . . . . ? C3C C4C C4AC C8AC -2.7(4) . . . . ? C3C C4C C4AC C5C 176.2(2) . . . . ? C8AC C4AC C5C C6C -32.9(3) . . . . ? C4C C4AC C5C C6C 148.2(2) . . . . ? C4AC C5C C6C C7C 55.1(3) . . . . ? C5C C6C C7C O7C 67.0(3) . . . . ? C5C C6C C7C C8C -48.9(3) . . . . ? C6C C7C O7C C9C -156.5(2) . . . . ? C8C C7C O7C C9C -32.9(2) . . . . ? O7C C7C C8C O8C 18.7(2) . . . . ? C6C C7C C8C O8C 138.0(2) . . . . ? O7C C7C C8C C8AC -100.0(2) . . . . ? C6C C7C C8C C8AC 19.2(3) . . . . ? C8AC C8C O8C C9C 123.9(2) . . . . ? C7C C8C O8C C9C 2.0(2) . . . . ? O1C N1C C8AC C4AC -179.5(2) . . . . ? C2C N1C C8AC C4AC 1.4(3) . . . . ? O1C N1C C8AC C8C 0.2(3) . . . . ? C2C N1C C8AC C8C -178.9(2) . . . . ? C4C C4AC C8AC N1C 1.5(3) . . . . ? C5C C4AC C8AC N1C -177.4(2) . . . . ? C4C C4AC C8AC C8C -178.1(2) . . . . ? C5C C4AC C8AC C8C 2.9(4) . . . . ? O8C C8C C8AC N1C 68.9(3) . . . . ? C7C C8C C8AC N1C -175.2(2) . . . . ? O8C C8C C8AC C4AC -111.4(3) . . . . ? C7C C8C C8AC C4AC 4.5(3) . . . . ? C7C O7C C9C O8C 34.9(2) . . . . ? C7C O7C C9C C11C 150.6(2) . . . . ? C7C O7C C9C C10C -84.3(2) . . . . ? C8C O8C C9C O7C -22.2(2) . . . . ? C8C O8C C9C C11C -139.0(2) . . . . ? C8C O8C C9C C10C 97.8(2) . . . . ? O1D N1D C2D C3D 179.3(2) . . . . ? C8AD N1D C2D C3D -1.8(4) . . . . ? O1D N1D C2D C2C -5.2(3) . . . . ? C8AD N1D C2D C2C 173.7(2) . . . . ? N1C C2C C2D N1D 107.0(2) . . . . ? C3C C2C C2D N1D -76.9(3) . . . . ? N1C C2C C2D C3D -77.6(3) . . . . ? C3C C2C C2D C3D 98.5(3) . . . . ? N1D C2D C3D C4D 0.8(4) . . . . ? C2C C2D C3D C4D -174.4(2) . . . . ? N1D C2D C3D C31D -179.4(2) . . . . ? C2C C2D C3D C31D 5.4(4) . . . . ? C2D C3D C4D C4AD 0.3(4) . . . . ? C31D C3D C4D C4AD -179.5(3) . . . . ? C3D C4D C4AD C8AD -0.4(4) . . . . ? C3D C4D C4AD C5D 179.9(3) . . . . ? C8AD C4AD C5D C6D -30.3(3) . . . . ? C4D C4AD C5D C6D 149.5(3) . . . . ? C4AD C5D C6D C7D 54.0(3) . . . . ? C5D C6D C7D O7D 67.2(3) . . . . ? C5D C6D C7D C8D -48.4(4) . . . . ? C6D C7D O7D C9D -158.8(2) . . . . ? C8D C7D O7D C9D -35.0(3) . . . . ? O7D C7D C8D O8D 17.6(3) . . . . ? C6D C7D C8D O8D 136.4(3) . . . . ? O7D C7D C8D C8AD -101.7(3) . . . . ? C6D C7D C8D C8AD 17.1(4) . . . . ? C8AD C8D O8D C9D 128.0(2) . . . . ? C7D C8D O8D C9D 6.4(3) . . . . ? O1D N1D C8AD C4AD -179.5(2) . . . . ? C2D N1D C8AD C4AD 1.7(4) . . . . ? O1D N1D C8AD C8D 0.8(3) . . . . ? C2D N1D C8AD C8D -178.1(2) . . . . ? C4D C4AD C8AD N1D -0.6(4) . . . . ? C5D C4AD C8AD N1D 179.2(2) . . . . ? C4D C4AD C8AD C8D 179.2(2) . . . . ? C5D C4AD C8AD C8D -1.1(4) . . . . ? O8D C8D C8AD N1D 71.5(3) . . . . ? C7D C8D C8AD N1D -172.2(2) . . . . ? O8D C8D C8AD C4AD -108.3(3) . . . . ? C7D C8D C8AD C4AD 8.1(4) . . . . ? C7D O7D C9D O8D 40.2(3) . . . . ? C7D O7D C9D C11D 154.6(2) . . . . ? C7D O7D C9D C10D -81.1(3) . . . . ? C8D O8D C9D O7D -28.0(3) . . . . ? C8D O8D C9D C11D -144.5(2) . . . . ? C8D O8D C9D C10D 92.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.487 _refine_diff_density_min -0.809 _refine_diff_density_rms 0.145