# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Philip Gale' _publ_contact_author_address ; School of Chemistry University of Southampton Southampton SO17 1BJ UNITED KINGDOM ; _publ_contact_author_email PHILIP.GALE@SOTON.AC.UK _publ_section_title ; Carboxylate complexation by 1,1'-(1,2-phenylene)bis(3-phenylurea) in solution and the solid state ; loop_ _publ_author_name 'Mark E. Light' 'Simon J. Brooks' 'Philip Gale' data_2005sot0664 _database_code_depnum_ccdc_archive 'CCDC 278725' _chemical_compound_source 'Simon Brooks' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H53 N5 O4' _chemical_formula_weight 595.81 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.577(3) _cell_length_b 19.020(8) _cell_length_c 18.309(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.73(3) _cell_angle_gamma 90.00 _cell_volume 3328.0(18) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6033 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.02 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9807 _exptl_absorpt_correction_T_max 0.9883 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 14586 reflections reduced R(int) from 0.1160 to 0.0677 Ratio of minimum to maximum apparent transmission: 0.599186 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37336 _diffrn_reflns_av_R_equivalents 0.1337 _diffrn_reflns_av_sigmaI/netI 0.1370 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 26.24 _reflns_number_total 6567 _reflns_number_gt 3128 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0856P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0056(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6567 _refine_ls_number_parameters 394 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1754 _refine_ls_R_factor_gt 0.0683 _refine_ls_wR_factor_ref 0.1791 _refine_ls_wR_factor_gt 0.1406 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.976 _refine_ls_shift/su_max 0.000 _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 0.3157(2) 0.52824(12) 0.24733(12) 0.0376(6) Uani 1 1 d . . . H91 H 0.3852 0.5531 0.2678 0.045 Uiso 1 1 calc R . . N2 N 0.4780(2) 0.38686(12) 0.15004(12) 0.0353(6) Uani 1 1 d . . . H92 H 0.3997 0.3731 0.1265 0.042 Uiso 1 1 calc R . . N3 N 0.4695(2) 0.24196(12) 0.11640(12) 0.0354(6) Uani 1 1 d . . . H93 H 0.3964 0.2627 0.0941 0.042 Uiso 1 1 calc R . . N4 N 0.2035(3) 0.17050(13) 0.08738(12) 0.0398(6) Uani 1 1 d . . . H94 H 0.2045 0.2094 0.0614 0.048 Uiso 1 1 calc R . . O1 O 0.5730(2) 0.46513(10) 0.23400(10) 0.0413(5) Uani 1 1 d . . . O2 O 0.5456(2) 0.14621(11) 0.18184(10) 0.0426(6) Uani 1 1 d . . . O3 O 0.2838(3) 0.33305(12) 0.04768(13) 0.0669(7) Uani 1 1 d . . . C1 C 0.1780(3) 0.54384(17) 0.25040(15) 0.0420(8) Uani 1 1 d . . . H1 H 0.1407 0.5832 0.2745 0.050 Uiso 1 1 calc R . . C2 C 0.1021(3) 0.49306(18) 0.21281(16) 0.0467(8) Uani 1 1 d . . . H2 H 0.0030 0.4906 0.2061 0.056 Uiso 1 1 calc R . . C3 C 0.1983(3) 0.44500(17) 0.18583(15) 0.0413(8) Uani 1 1 d . . . H3 H 0.1760 0.4041 0.1577 0.050 Uiso 1 1 calc R . . C4 C 0.3303(3) 0.46827(15) 0.20773(14) 0.0331(7) Uani 1 1 d . . . C5 C 0.4707(3) 0.44070(16) 0.19804(15) 0.0340(7) Uani 1 1 d . . . C6 C 0.6028(3) 0.35111(16) 0.13503(14) 0.0324(7) Uani 1 1 d . . . C7 C 0.7295(3) 0.38695(17) 0.13385(15) 0.0405(8) Uani 1 1 d . . . H7 H 0.7327 0.4361 0.1428 0.049 Uiso 1 1 calc R . . C8 C 0.8503(3) 0.35132(19) 0.11971(16) 0.0476(9) Uani 1 1 d . . . H8 H 0.9363 0.3762 0.1194 0.057 Uiso 1 1 calc R . . C9 C 0.8476(3) 0.28055(18) 0.10618(16) 0.0457(8) Uani 1 1 d . . . H9 H 0.9314 0.2564 0.0969 0.055 Uiso 1 1 calc R . . C10 C 0.7226(3) 0.24444(17) 0.10602(15) 0.0403(8) Uani 1 1 d . . . H10 H 0.7207 0.1954 0.0962 0.048 Uiso 1 1 calc R . . C11 C 0.5991(3) 0.27902(16) 0.12012(14) 0.0347(7) Uani 1 1 d . . . C12 C 0.4509(3) 0.17723(16) 0.14467(15) 0.0367(8) Uani 1 1 d . . . C13 C 0.3134(3) 0.14412(16) 0.13152(14) 0.0348(7) Uani 1 1 d . . . C14 C 0.2700(3) 0.08291(16) 0.16211(16) 0.0407(8) Uani 1 1 d . . . H14 H 0.3242 0.0535 0.1949 0.049 Uiso 1 1 calc R . . C15 C 0.1316(3) 0.07164(17) 0.13623(17) 0.0470(9) Uani 1 1 d . . . H15 H 0.0742 0.0331 0.1480 0.056 Uiso 1 1 calc R . . C16 C 0.0939(3) 0.12608(18) 0.09095(17) 0.0441(8) Uani 1 1 d . . . H16 H 0.0047 0.1320 0.0658 0.053 Uiso 1 1 calc R . . O4 O 0.1154(2) 0.27488(13) -0.01155(11) 0.0563(6) Uani 1 1 d . . . C17 C 0.1220(3) 0.39938(18) -0.02628(17) 0.0549(9) Uani 1 1 d . . . H17A H 0.1837 0.4156 -0.0635 0.082 Uiso 1 1 calc R . . H17B H 0.1201 0.4345 0.0128 0.082 Uiso 1 1 calc R . . H17C H 0.0272 0.3927 -0.0487 0.082 Uiso 1 1 calc R . . C18 C 0.1756(3) 0.33098(18) 0.00515(15) 0.0398(8) Uani 1 1 d . . . N5 N 0.5160(2) 0.20979(12) 0.87203(11) 0.0351(6) Uani 1 1 d . . . C19 C 0.6386(3) 0.17660(16) 0.83621(15) 0.0364(7) Uani 1 1 d . . . H19A H 0.6058 0.1321 0.8128 0.044 Uiso 1 1 calc R . . H19B H 0.6661 0.2084 0.7968 0.044 Uiso 1 1 calc R . . C20 C 0.7677(3) 0.16064(16) 0.88541(15) 0.0387(8) Uani 1 1 d . . . H20A H 0.8052 0.2046 0.9080 0.046 Uiso 1 1 calc R . . H20B H 0.7434 0.1284 0.9251 0.046 Uiso 1 1 calc R . . C21 C 0.8766(3) 0.12700(17) 0.84076(16) 0.0414(8) Uani 1 1 d . . . H21A H 0.8964 0.1585 0.7997 0.050 Uiso 1 1 calc R . . H21B H 0.8391 0.0824 0.8198 0.050 Uiso 1 1 calc R . . C22 C 1.0124(3) 0.11214(17) 0.88610(16) 0.0466(9) Uani 1 1 d . . . H22A H 1.0497 0.1562 0.9073 0.070 Uiso 1 1 calc R . . H22B H 1.0807 0.0916 0.8547 0.070 Uiso 1 1 calc R . . H22C H 0.9942 0.0792 0.9255 0.070 Uiso 1 1 calc R . . C23 C 0.4580(3) 0.16019(15) 0.92772(14) 0.0373(8) Uani 1 1 d . . . H23A H 0.5307 0.1539 0.9682 0.045 Uiso 1 1 calc R . . H23B H 0.3772 0.1836 0.9485 0.045 Uiso 1 1 calc R . . C24 C 0.4112(3) 0.08806(15) 0.90174(15) 0.0371(8) Uani 1 1 d . . . H24A H 0.4928 0.0608 0.8869 0.045 Uiso 1 1 calc R . . H24B H 0.3437 0.0925 0.8587 0.045 Uiso 1 1 calc R . . C25 C 0.3427(3) 0.04994(15) 0.96318(15) 0.0377(8) Uani 1 1 d . . . H25A H 0.4117 0.0453 1.0056 0.045 Uiso 1 1 calc R . . H25B H 0.2639 0.0787 0.9789 0.045 Uiso 1 1 calc R . . C26 C 0.2885(3) -0.02234(16) 0.94144(16) 0.0447(8) Uani 1 1 d . . . H26A H 0.2159 -0.0179 0.9015 0.067 Uiso 1 1 calc R . . H26B H 0.2490 -0.0449 0.9836 0.067 Uiso 1 1 calc R . . H26C H 0.3657 -0.0510 0.9252 0.067 Uiso 1 1 calc R . . C27 C 0.4067(3) 0.22535(16) 0.81032(14) 0.0373(8) Uani 1 1 d . . . H27A H 0.4515 0.2534 0.7727 0.045 Uiso 1 1 calc R . . H27B H 0.3768 0.1802 0.7874 0.045 Uiso 1 1 calc R . . C28 C 0.2773(3) 0.26431(17) 0.83143(16) 0.0425(8) Uani 1 1 d . . . H28A H 0.2991 0.3149 0.8377 0.051 Uiso 1 1 calc R . . H28B H 0.2478 0.2460 0.8787 0.051 Uiso 1 1 calc R . . C29 C 0.1585(3) 0.25527(17) 0.77273(15) 0.0431(8) Uani 1 1 d . . . H29A H 0.1911 0.2698 0.7248 0.052 Uiso 1 1 calc R . . H29B H 0.1320 0.2050 0.7693 0.052 Uiso 1 1 calc R . . C30 C 0.0310(3) 0.29852(18) 0.78921(18) 0.0541(9) Uani 1 1 d . . . H30A H -0.0011 0.2846 0.8369 0.081 Uiso 1 1 calc R . . H30B H -0.0439 0.2903 0.7511 0.081 Uiso 1 1 calc R . . H30C H 0.0557 0.3485 0.7903 0.081 Uiso 1 1 calc R . . C31 C 0.5600(3) 0.27556(15) 0.91322(15) 0.0381(8) Uani 1 1 d . . . H31A H 0.6239 0.2620 0.9555 0.046 Uiso 1 1 calc R . . H31B H 0.4759 0.2969 0.9328 0.046 Uiso 1 1 calc R . . C32 C 0.6318(3) 0.33103(16) 0.86983(15) 0.0421(8) Uani 1 1 d . . . H32A H 0.5653 0.3496 0.8309 0.051 Uiso 1 1 calc R . . H32B H 0.7116 0.3096 0.8462 0.051 Uiso 1 1 calc R . . C33 C 0.6844(3) 0.39114(16) 0.91934(16) 0.0461(8) Uani 1 1 d . . . H33A H 0.7433 0.3714 0.9608 0.055 Uiso 1 1 calc R . . H33B H 0.7444 0.4223 0.8914 0.055 Uiso 1 1 calc R . . C34 C 0.5703(4) 0.43431(18) 0.94909(18) 0.0613(10) Uani 1 1 d . . . H34A H 0.5060 0.4503 0.9087 0.092 Uiso 1 1 calc R . . H34B H 0.6112 0.4752 0.9751 0.092 Uiso 1 1 calc R . . H34C H 0.5191 0.4057 0.9829 0.092 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 0.0347(16) 0.0375(17) 0.0410(14) 0.0018(12) 0.0044(11) -0.0002(12) N2 0.0273(14) 0.0350(15) 0.0434(14) -0.0060(12) 0.0011(11) -0.0023(12) N3 0.0343(15) 0.0313(16) 0.0403(14) -0.0008(12) 0.0002(11) 0.0033(12) N4 0.0397(16) 0.0367(16) 0.0438(14) -0.0007(12) 0.0093(12) 0.0008(14) O1 0.0340(12) 0.0437(14) 0.0458(12) -0.0068(10) -0.0007(10) 0.0000(10) O2 0.0433(13) 0.0403(14) 0.0443(12) 0.0037(10) 0.0033(10) 0.0057(11) O3 0.0660(17) 0.0464(16) 0.0830(17) -0.0004(13) -0.0350(14) 0.0028(13) C1 0.038(2) 0.046(2) 0.0437(18) 0.0048(16) 0.0105(15) 0.0100(17) C2 0.0315(19) 0.059(2) 0.0500(19) -0.0002(18) 0.0060(15) -0.0025(18) C3 0.0359(19) 0.043(2) 0.0455(18) -0.0034(16) 0.0083(15) -0.0030(16) C4 0.0328(18) 0.0286(19) 0.0382(16) -0.0022(14) 0.0035(13) -0.0002(15) C5 0.0338(19) 0.0321(19) 0.0357(16) 0.0070(15) 0.0003(14) -0.0017(15) C6 0.0282(17) 0.037(2) 0.0316(15) -0.0006(14) 0.0013(12) 0.0016(15) C7 0.0374(19) 0.044(2) 0.0409(17) -0.0011(15) 0.0054(14) -0.0036(16) C8 0.0309(19) 0.060(3) 0.0521(19) -0.0044(18) 0.0062(15) -0.0030(18) C9 0.0331(19) 0.050(2) 0.055(2) -0.0035(17) 0.0100(15) 0.0041(17) C10 0.0405(19) 0.039(2) 0.0422(17) -0.0019(15) 0.0066(14) 0.0066(17) C11 0.0294(17) 0.041(2) 0.0336(16) 0.0012(14) 0.0032(13) -0.0010(16) C12 0.047(2) 0.030(2) 0.0337(16) -0.0045(15) 0.0089(15) 0.0060(17) C13 0.0359(18) 0.033(2) 0.0358(16) -0.0016(14) 0.0058(14) 0.0034(15) C14 0.040(2) 0.035(2) 0.0486(18) 0.0004(15) 0.0089(15) 0.0005(16) C15 0.044(2) 0.036(2) 0.063(2) -0.0018(18) 0.0173(17) -0.0034(17) C16 0.0327(19) 0.047(2) 0.0532(19) -0.0079(17) 0.0091(15) -0.0008(17) O4 0.0641(16) 0.0518(16) 0.0517(13) 0.0051(12) -0.0055(11) -0.0143(13) C17 0.052(2) 0.058(2) 0.054(2) 0.0100(18) -0.0037(17) 0.0098(18) C18 0.039(2) 0.045(2) 0.0356(17) -0.0016(16) 0.0077(15) 0.0045(17) N5 0.0339(14) 0.0375(16) 0.0345(13) 0.0010(12) 0.0064(11) -0.0001(12) C19 0.0353(18) 0.0387(19) 0.0364(16) -0.0008(14) 0.0104(14) 0.0024(15) C20 0.0315(17) 0.044(2) 0.0408(17) 0.0029(15) 0.0054(14) 0.0014(15) C21 0.0359(18) 0.043(2) 0.0453(17) -0.0010(15) 0.0034(14) 0.0029(16) C22 0.0367(19) 0.049(2) 0.0538(19) -0.0012(17) 0.0039(15) 0.0030(16) C23 0.0350(17) 0.041(2) 0.0364(16) 0.0030(14) 0.0077(13) -0.0001(15) C24 0.0304(17) 0.042(2) 0.0394(16) -0.0011(14) 0.0066(14) 0.0037(15) C25 0.0350(18) 0.040(2) 0.0387(16) -0.0009(15) 0.0054(14) -0.0014(15) C26 0.0441(19) 0.045(2) 0.0456(18) 0.0021(15) 0.0057(15) -0.0004(16) C27 0.0353(18) 0.044(2) 0.0323(16) 0.0026(14) 0.0031(13) 0.0017(15) C28 0.0376(18) 0.045(2) 0.0451(17) 0.0027(15) 0.0074(15) 0.0032(16) C29 0.0377(19) 0.050(2) 0.0427(17) 0.0095(15) 0.0087(14) 0.0015(16) C30 0.042(2) 0.054(2) 0.066(2) 0.0087(18) 0.0007(17) 0.0079(17) C31 0.0431(18) 0.0366(19) 0.0350(16) -0.0033(14) 0.0061(14) -0.0020(15) C32 0.047(2) 0.041(2) 0.0396(17) 0.0003(15) 0.0098(15) -0.0011(16) C33 0.053(2) 0.041(2) 0.0443(18) 0.0064(16) 0.0055(16) -0.0038(17) C34 0.078(3) 0.044(2) 0.064(2) 0.0015(19) 0.025(2) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.356(3) . ? N1 C4 1.363(3) . ? N2 C5 1.354(3) . ? N2 C6 1.418(3) . ? N3 C12 1.352(4) . ? N3 C11 1.426(3) . ? N4 C16 1.353(4) . ? N4 C13 1.379(3) . ? O1 C5 1.235(3) . ? O2 C12 1.246(3) . ? O3 C18 1.255(3) . ? C1 C2 1.367(4) . ? C2 C3 1.410(4) . ? C3 C4 1.375(4) . ? C4 C5 1.465(4) . ? C6 C7 1.393(4) . ? C6 C11 1.398(4) . ? C7 C8 1.380(4) . ? C8 C9 1.369(4) . ? C9 C10 1.381(4) . ? C10 C11 1.392(4) . ? C12 C13 1.466(4) . ? C13 C14 1.368(4) . ? C14 C15 1.395(4) . ? C15 C16 1.361(4) . ? O4 C18 1.242(4) . ? C17 C18 1.500(4) . ? N5 C31 1.507(4) . ? N5 C27 1.518(3) . ? N5 C19 1.519(3) . ? N5 C23 1.520(3) . ? C19 C20 1.513(4) . ? C20 C21 1.509(4) . ? C21 C22 1.523(4) . ? C23 C24 1.510(4) . ? C24 C25 1.522(4) . ? C25 C26 1.514(4) . ? C27 C28 1.516(4) . ? C28 C29 1.523(4) . ? C29 C30 1.519(4) . ? C31 C32 1.513(4) . ? C32 C33 1.524(4) . ? C33 C34 1.498(4) . ? 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 C1 N1 C4 109.8(3) . . ? C5 N2 C6 124.6(2) . . ? C12 N3 C11 124.6(2) . . ? C16 N4 C13 108.0(3) . . ? N1 C1 C2 108.1(3) . . ? C1 C2 C3 107.2(3) . . ? C4 C3 C2 107.4(3) . . ? N1 C4 C3 107.5(3) . . ? N1 C4 C5 119.4(3) . . ? C3 C4 C5 133.1(3) . . ? O1 C5 N2 123.9(3) . . ? O1 C5 C4 120.2(3) . . ? N2 C5 C4 115.8(3) . . ? C7 C6 C11 119.2(3) . . ? C7 C6 N2 121.0(3) . . ? C11 C6 N2 119.8(2) . . ? C8 C7 C6 120.3(3) . . ? C9 C8 C7 120.7(3) . . ? C8 C9 C10 119.7(3) . . ? C9 C10 C11 120.8(3) . . ? C10 C11 C6 119.3(3) . . ? C10 C11 N3 120.3(3) . . ? C6 C11 N3 120.3(2) . . ? O2 C12 N3 122.1(3) . . ? O2 C12 C13 120.0(3) . . ? N3 C12 C13 117.9(3) . . ? C14 C13 N4 108.0(3) . . ? C14 C13 C12 126.3(3) . . ? N4 C13 C12 125.7(3) . . ? C13 C14 C15 107.4(3) . . ? C16 C15 C14 107.4(3) . . ? N4 C16 C15 109.2(3) . . ? O4 C18 O3 122.1(3) . . ? O4 C18 C17 120.6(3) . . ? O3 C18 C17 117.3(3) . . ? C31 N5 C27 111.6(2) . . ? C31 N5 C19 111.2(2) . . ? C27 N5 C19 105.94(19) . . ? C31 N5 C23 106.4(2) . . ? C27 N5 C23 110.8(2) . . ? C19 N5 C23 111.0(2) . . ? C20 C19 N5 116.8(2) . . ? C21 C20 C19 109.3(2) . . ? C20 C21 C22 112.3(2) . . ? C24 C23 N5 117.8(2) . . ? C23 C24 C25 109.5(2) . . ? C26 C25 C24 113.3(2) . . ? C28 C27 N5 116.2(2) . . ? C27 C28 C29 110.5(2) . . ? C30 C29 C28 111.8(3) . . ? N5 C31 C32 116.0(2) . . ? C31 C32 C33 110.8(2) . . ? C34 C33 C32 114.0(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H91 O2 0.88 2.08 2.874(3) 148.7 2_655 N2 H92 O3 0.88 1.92 2.751(3) 156.7 . N3 H93 O3 0.88 1.89 2.731(3) 160.2 . N4 H94 O4 0.88 1.98 2.781(3) 151.0 . N4 H94 O3 0.88 2.49 3.279(4) 149.7 . _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 26.24 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.292 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.055 #===end data_2005sot0431 _database_code_depnum_ccdc_archive 'CCDC 278726' _chemical_compound_source 'Simon Brooks' _database_code_CSD 5SOT0431 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H58 N5 O4' _chemical_formula_weight 708.94 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.478(2) _cell_length_b 38.654(10) _cell_length_c 24.402(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.68(3) _cell_angle_gamma 90.00 _cell_volume 7980(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 13463 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.02 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3064 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9812 _exptl_absorpt_correction_T_max 0.9909 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 18252 reflections reduced R(int) from 0.0917 to 0.0578 Ratio of minimum to maximum apparent transmission: 0.306586 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 60181 _diffrn_reflns_av_R_equivalents 0.1747 _diffrn_reflns_av_sigmaI/netI 0.2724 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -47 _diffrn_reflns_limit_k_max 47 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 26.11 _reflns_number_total 15477 _reflns_number_gt 5576 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0783P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0013(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 15477 _refine_ls_number_parameters 946 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2583 _refine_ls_R_factor_gt 0.0795 _refine_ls_wR_factor_ref 0.2035 _refine_ls_wR_factor_gt 0.1442 _refine_ls_goodness_of_fit_ref 0.926 _refine_ls_restrained_S_all 0.926 _refine_ls_shift/su_max 0.000 _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 N101 N 0.8985(4) 0.15490(9) 0.72110(15) 0.0358(9) Uani 1 1 d . . . H901 H 0.8493 0.1747 0.7148 0.043 Uiso 1 1 calc R . . N102 N 0.8086(3) 0.14410(8) 0.63334(14) 0.0288(9) Uani 1 1 d . . . H902 H 0.7793 0.1659 0.6342 0.035 Uiso 1 1 calc R . . N103 N 0.7902(3) 0.17945(8) 0.53335(13) 0.0278(9) Uani 1 1 d . . . H903 H 0.7585 0.1921 0.5606 0.033 Uiso 1 1 calc R . . N104 N 0.8666(4) 0.23106(9) 0.49851(14) 0.0351(9) Uani 1 1 d . . . H904 H 0.8165 0.2390 0.5263 0.042 Uiso 1 1 calc R . . O101 O 0.9444(3) 0.10229(8) 0.68234(11) 0.0390(8) Uani 1 1 d . . . O102 O 0.9271(3) 0.18034(7) 0.45511(12) 0.0358(8) Uani 1 1 d . . . C101 C 1.0202(5) 0.11980(12) 0.79632(19) 0.0438(13) Uani 1 1 d . . . H101 H 0.9907 0.0990 0.7776 0.053 Uiso 1 1 calc R . . C102 C 1.1026(5) 0.11840(15) 0.8473(2) 0.0524(14) Uani 1 1 d . . . H102 H 1.1294 0.0966 0.8632 0.063 Uiso 1 1 calc R . . C103 C 1.1454(5) 0.14804(17) 0.8746(2) 0.0575(15) Uani 1 1 d . . . H103 H 1.2002 0.1468 0.9098 0.069 Uiso 1 1 calc R . . C104 C 1.1096(6) 0.17920(16) 0.8517(2) 0.0686(17) Uani 1 1 d . . . H104 H 1.1412 0.1998 0.8706 0.082 Uiso 1 1 calc R . . C105 C 1.0273(6) 0.18131(13) 0.8007(2) 0.0581(14) Uani 1 1 d . . . H105 H 1.0025 0.2033 0.7849 0.070 Uiso 1 1 calc R . . C106 C 0.9813(4) 0.15130(12) 0.77296(18) 0.0312(11) Uani 1 1 d . . . C107 C 0.8864(5) 0.13102(12) 0.67975(19) 0.0288(11) Uani 1 1 d . . . C108 C 0.7714(4) 0.12562(11) 0.58426(18) 0.0254(10) Uani 1 1 d . . . C109 C 0.7405(4) 0.09020(11) 0.58497(18) 0.0287(11) Uani 1 1 d . . . H109 H 0.7462 0.0780 0.6188 0.034 Uiso 1 1 calc R . . C110 C 0.7017(4) 0.07284(11) 0.53650(19) 0.0332(11) Uani 1 1 d . . . H110 H 0.6834 0.0486 0.5371 0.040 Uiso 1 1 calc R . . C111 C 0.6893(4) 0.09042(11) 0.48751(19) 0.0352(12) Uani 1 1 d . . . H111 H 0.6626 0.0783 0.4544 0.042 Uiso 1 1 calc R . . C112 C 0.7154(4) 0.12562(11) 0.48624(18) 0.0319(11) Uani 1 1 d . . . H112 H 0.7031 0.1378 0.4524 0.038 Uiso 1 1 calc R . . C113 C 0.7597(4) 0.14326(11) 0.53410(18) 0.0270(11) Uani 1 1 d . . . C114 C 0.8666(4) 0.19588(12) 0.49238(19) 0.0291(11) Uani 1 1 d . . . C115 C 0.9367(5) 0.25612(12) 0.46602(19) 0.0356(12) Uani 1 1 d . . . C116 C 0.9258(5) 0.29019(11) 0.48306(19) 0.0391(12) Uani 1 1 d . . . H116 H 0.8716 0.2955 0.5149 0.047 Uiso 1 1 calc R . . C117 C 0.9929(5) 0.31638(12) 0.4542(2) 0.0476(13) Uani 1 1 d . . . H117 H 0.9863 0.3396 0.4667 0.057 Uiso 1 1 calc R . . C118 C 1.0696(5) 0.30919(13) 0.4075(2) 0.0518(14) Uani 1 1 d . . . H118 H 1.1146 0.3273 0.3873 0.062 Uiso 1 1 calc R . . C119 C 1.0800(5) 0.27533(13) 0.3904(2) 0.0495(14) Uani 1 1 d . . . H119 H 1.1340 0.2702 0.3584 0.059 Uiso 1 1 calc R . . C120 C 1.0131(5) 0.24834(12) 0.41894(19) 0.0420(13) Uani 1 1 d . . . H120 H 1.0198 0.2251 0.4064 0.050 Uiso 1 1 calc R . . N201 N 1.7167(3) 0.12062(8) 0.27589(14) 0.0307(9) Uani 1 1 d . . . H801 H 1.7466 0.1185 0.2422 0.037 Uiso 1 1 calc R . . N202 N 1.8052(3) 0.06514(8) 0.28635(14) 0.0287(9) Uani 1 1 d . . . H802 H 1.8239 0.0672 0.2514 0.034 Uiso 1 1 calc R . . N203 N 1.8211(3) 0.00518(8) 0.22341(14) 0.0286(9) Uani 1 1 d . . . H803 H 1.8510 0.0231 0.2045 0.034 Uiso 1 1 calc R . . N204 N 1.7348(4) -0.01679(9) 0.14025(15) 0.0344(9) Uani 1 1 d . . . H804 H 1.7908 0.0005 0.1282 0.041 Uiso 1 1 calc R . . O201 O 1.6927(3) 0.09268(7) 0.35764(12) 0.0387(8) Uani 1 1 d . . . O202 O 1.6717(3) -0.04418(7) 0.21918(12) 0.0376(8) Uani 1 1 d . . . C201 C 1.7043(4) 0.16921(11) 0.33941(17) 0.0302(11) Uani 1 1 d . . . H201 H 1.7856 0.1592 0.3628 0.036 Uiso 1 1 calc R . . C202 C 1.6388(5) 0.20056(11) 0.35293(18) 0.0365(12) Uani 1 1 d . . . H202 H 1.6753 0.2118 0.3859 0.044 Uiso 1 1 calc R . . C203 C 1.5221(5) 0.21567(12) 0.3196(2) 0.0400(12) Uani 1 1 d . . . H203 H 1.4779 0.2372 0.3294 0.048 Uiso 1 1 calc R . . C204 C 1.4694(5) 0.19933(12) 0.2715(2) 0.0404(13) Uani 1 1 d . . . H204 H 1.3892 0.2097 0.2480 0.048 Uiso 1 1 calc R . . C205 C 1.5332(4) 0.16782(11) 0.25755(18) 0.0343(11) Uani 1 1 d . . . H205 H 1.4965 0.1566 0.2245 0.041 Uiso 1 1 calc R . . C206 C 1.6507(4) 0.15257(11) 0.29166(17) 0.0274(11) Uani 1 1 d . . . C207 C 1.7361(4) 0.09283(11) 0.31082(19) 0.0289(11) Uani 1 1 d . . . C208 C 1.8485(4) 0.03383(11) 0.31233(18) 0.0269(10) Uani 1 1 d . . . C209 C 1.8894(4) 0.03223(11) 0.36901(18) 0.0307(11) Uani 1 1 d . . . H209 H 1.8865 0.0526 0.3907 0.037 Uiso 1 1 calc R . . C210 C 1.9341(4) 0.00100(12) 0.39332(19) 0.0352(11) Uani 1 1 d . . . H210 H 1.9570 -0.0002 0.4319 0.042 Uiso 1 1 calc R . . C211 C 1.9455(4) -0.02839(11) 0.36160(18) 0.0317(11) Uani 1 1 d . . . H211 H 1.9780 -0.0496 0.3784 0.038 Uiso 1 1 calc R . . C212 C 1.9097(4) -0.02715(11) 0.30540(18) 0.0292(11) Uani 1 1 d . . . H212 H 1.9188 -0.0474 0.2837 0.035 Uiso 1 1 calc R . . C213 C 1.8603(4) 0.00401(11) 0.28069(18) 0.0269(10) Uani 1 1 d . . . C214 C 1.7378(5) -0.02093(12) 0.19650(19) 0.0302(11) Uani 1 1 d . . . C215 C 1.6518(5) -0.03718(11) 0.09971(19) 0.0329(11) Uani 1 1 d . . . C216 C 1.6586(5) -0.02677(12) 0.04542(19) 0.0488(13) Uani 1 1 d . . . H216 H 1.7188 -0.0070 0.0367 0.059 Uiso 1 1 calc R . . C217 C 1.5771(6) -0.04527(14) 0.0039(2) 0.0600(15) Uani 1 1 d . . . H217 H 1.5830 -0.0382 -0.0332 0.072 Uiso 1 1 calc R . . C218 C 1.4884(5) -0.07357(13) 0.0158(2) 0.0481(13) Uani 1 1 d . . . H218 H 1.4318 -0.0860 -0.0127 0.058 Uiso 1 1 calc R . . C219 C 1.4824(5) -0.08366(12) 0.06914(19) 0.0408(12) Uani 1 1 d . . . H219 H 1.4207 -0.1033 0.0774 0.049 Uiso 1 1 calc R . . C220 C 1.5632(5) -0.06625(11) 0.11124(19) 0.0377(12) Uani 1 1 d . . . H220 H 1.5586 -0.0740 0.1480 0.045 Uiso 1 1 calc R . . O301 O 1.2105(3) 0.29281(8) 0.16940(14) 0.0541(9) Uani 1 1 d . . . O302 O 1.2170(3) 0.25874(8) 0.09713(14) 0.0549(10) Uani 1 1 d . . . C301 C 1.0868(5) 0.24080(12) 0.23262(19) 0.0389(12) Uani 1 1 d . . . H301 H 1.0948 0.2634 0.2478 0.047 Uiso 1 1 calc R . . C302 C 1.0290(5) 0.21434(15) 0.2629(2) 0.0523(14) Uani 1 1 d . . . H302 H 0.9972 0.2187 0.2989 0.063 Uiso 1 1 calc R . . C303 C 1.0170(5) 0.18185(15) 0.2413(2) 0.0540(15) Uani 1 1 d . . . H303 H 0.9756 0.1636 0.2622 0.065 Uiso 1 1 calc R . . C304 C 1.0643(5) 0.17537(12) 0.1898(2) 0.0474(13) Uani 1 1 d . . . H304 H 1.0577 0.1526 0.1752 0.057 Uiso 1 1 calc R . . C305 C 1.1217(5) 0.20196(12) 0.1587(2) 0.0406(12) Uani 1 1 d . . . H305 H 1.1529 0.1975 0.1227 0.049 Uiso 1 1 calc R . . C306 C 1.1339(4) 0.23483(11) 0.17984(18) 0.0272(10) Uani 1 1 d . . . C307 C 1.1935(4) 0.26392(12) 0.1462(2) 0.0340(12) Uani 1 1 d . . . O401 O 2.0868(3) -0.04620(8) -0.13626(12) 0.0401(8) Uani 1 1 d . . . O402 O 2.1500(4) -0.09285(8) -0.18216(13) 0.0518(9) Uani 1 1 d . . . C401 C 2.0546(5) -0.08533(12) -0.04098(19) 0.0407(12) Uani 1 1 d . . . H401 H 2.0159 -0.0623 -0.0415 0.049 Uiso 1 1 calc R . . C402 C 2.0495(5) -0.10515(14) 0.0065(2) 0.0543(14) Uani 1 1 d . . . H402 H 2.0065 -0.0956 0.0382 0.065 Uiso 1 1 calc R . . C403 C 2.1062(6) -0.13825(14) 0.0076(2) 0.0543(14) Uani 1 1 d . . . H403 H 2.1018 -0.1518 0.0400 0.065 Uiso 1 1 calc R . . C404 C 2.1692(5) -0.15196(13) -0.0379(2) 0.0523(14) Uani 1 1 d . . . H404 H 2.2105 -0.1748 -0.0369 0.063 Uiso 1 1 calc R . . C405 C 2.1726(5) -0.13225(12) -0.08559(19) 0.0401(12) Uani 1 1 d . . . H405 H 2.2147 -0.1419 -0.1173 0.048 Uiso 1 1 calc R . . C406 C 2.1157(4) -0.09906(11) -0.08722(17) 0.0291(11) Uani 1 1 d . . . C407 C 2.1181(4) -0.07785(13) -0.13874(19) 0.0320(11) Uani 1 1 d . . . N501 N 0.2843(3) 0.16812(8) 0.59753(14) 0.0305(9) Uani 1 1 d . . . C501 C 0.1793(4) 0.14075(11) 0.56963(18) 0.0359(12) Uani 1 1 d . . . H50A H 0.1152 0.1301 0.5976 0.043 Uiso 1 1 calc R . . H50B H 0.1054 0.1523 0.5424 0.043 Uiso 1 1 calc R . . C502 C 0.2631(4) 0.11235(11) 0.54081(18) 0.0369(12) Uani 1 1 d . . . H50C H 0.3223 0.0977 0.5683 0.044 Uiso 1 1 calc R . . H50D H 0.3400 0.1226 0.5166 0.044 Uiso 1 1 calc R . . C503 C 0.1462(5) 0.09031(11) 0.50695(18) 0.0384(12) Uani 1 1 d . . . H50E H 0.0914 0.1048 0.4782 0.046 Uiso 1 1 calc R . . H50F H 0.0657 0.0812 0.5309 0.046 Uiso 1 1 calc R . . C504 C 0.2267(5) 0.06036(11) 0.48019(19) 0.0480(13) Uani 1 1 d . . . H50G H 0.3035 0.0693 0.4554 0.072 Uiso 1 1 calc R . . H50H H 0.1473 0.0464 0.4593 0.072 Uiso 1 1 calc R . . H50I H 0.2812 0.0460 0.5086 0.072 Uiso 1 1 calc R . . C505 C 0.3991(4) 0.15144(11) 0.64001(17) 0.0342(11) Uani 1 1 d . . . H50J H 0.4710 0.1362 0.6205 0.041 Uiso 1 1 calc R . . H50K H 0.4645 0.1700 0.6579 0.041 Uiso 1 1 calc R . . C506 C 0.3281(5) 0.13036(12) 0.68443(18) 0.0453(13) Uani 1 1 d . . . H50L H 0.2710 0.1102 0.6677 0.054 Uiso 1 1 calc R . . H50M H 0.2510 0.1447 0.7032 0.054 Uiso 1 1 calc R . . C507 C 0.4575(5) 0.11770(13) 0.72648(19) 0.0534(14) Uani 1 1 d . . . H50N H 0.4170 0.0978 0.7469 0.064 Uiso 1 1 calc R . . H50O H 0.5493 0.1096 0.7069 0.064 Uiso 1 1 calc R . . C508 C 0.5107(6) 0.14551(14) 0.7666(2) 0.0667(16) Uani 1 1 d . . . H50P H 0.5486 0.1655 0.7465 0.100 Uiso 1 1 calc R . . H50Q H 0.5964 0.1366 0.7916 0.100 Uiso 1 1 calc R . . H50R H 0.4218 0.1525 0.7878 0.100 Uiso 1 1 calc R . . C509 C 0.1771(4) 0.19370(10) 0.62402(17) 0.0342(11) Uani 1 1 d . . . H50S H 0.1150 0.2062 0.5946 0.041 Uiso 1 1 calc R . . H50T H 0.1015 0.1806 0.6453 0.041 Uiso 1 1 calc R . . C510 C 0.2593(5) 0.22000(11) 0.66167(18) 0.0424(13) Uani 1 1 d . . . H51A H 0.3507 0.2298 0.6437 0.051 Uiso 1 1 calc R . . H51B H 0.2994 0.2085 0.6960 0.051 Uiso 1 1 calc R . . C511 C 0.1467(5) 0.24908(12) 0.67528(19) 0.0440(13) Uani 1 1 d . . . H51C H 0.0446 0.2388 0.6844 0.053 Uiso 1 1 calc R . . H51D H 0.1912 0.2615 0.7082 0.053 Uiso 1 1 calc R . . C512 C 0.1162(6) 0.27502(12) 0.6291(2) 0.0626(15) Uani 1 1 d . . . H51E H 0.2153 0.2866 0.6215 0.094 Uiso 1 1 calc R . . H51F H 0.0393 0.2923 0.6399 0.094 Uiso 1 1 calc R . . H51G H 0.0741 0.2629 0.5960 0.094 Uiso 1 1 calc R . . C513 C 0.3820(4) 0.18619(11) 0.55623(17) 0.0344(12) Uani 1 1 d . . . H51H H 0.4389 0.2056 0.5751 0.041 Uiso 1 1 calc R . . H51I H 0.4626 0.1697 0.5446 0.041 Uiso 1 1 calc R . . C514 C 0.2941(5) 0.20027(12) 0.50531(17) 0.0397(12) Uani 1 1 d . . . H51J H 0.2092 0.2160 0.5160 0.048 Uiso 1 1 calc R . . H51K H 0.2444 0.1809 0.4839 0.048 Uiso 1 1 calc R . . C515 C 0.4049(5) 0.21982(12) 0.46976(18) 0.0445(13) Uani 1 1 d . . . H51L H 0.5055 0.2069 0.4692 0.053 Uiso 1 1 calc R . . H51M H 0.3571 0.2206 0.4317 0.053 Uiso 1 1 calc R . . C516 C 0.4407(6) 0.25648(13) 0.4889(2) 0.0686(16) Uani 1 1 d . . . H51N H 0.3428 0.2700 0.4872 0.103 Uiso 1 1 calc R . . H51O H 0.5159 0.2671 0.4650 0.103 Uiso 1 1 calc R . . H51P H 0.4866 0.2560 0.5267 0.103 Uiso 1 1 calc R . . N601 N 2.3253(3) 0.03753(9) 0.24252(14) 0.0303(9) Uani 1 1 d . . . C601 C 2.4224(4) 0.05890(11) 0.20517(17) 0.0358(12) Uani 1 1 d . . . H60A H 2.4887 0.0430 0.1847 0.043 Uiso 1 1 calc R . . H60B H 2.4946 0.0738 0.2283 0.043 Uiso 1 1 calc R . . C602 C 2.3293(5) 0.08184(11) 0.16386(18) 0.0426(13) Uani 1 1 d . . . H60C H 2.2561 0.0675 0.1402 0.051 Uiso 1 1 calc R . . H60D H 2.2658 0.0987 0.1835 0.051 Uiso 1 1 calc R . . C603 C 2.4431(5) 0.10086(12) 0.12874(18) 0.0430(13) Uani 1 1 d . . . H60E H 2.5237 0.1127 0.1531 0.052 Uiso 1 1 calc R . . H60F H 2.4984 0.0838 0.1066 0.052 Uiso 1 1 calc R . . C604 C 2.3628(5) 0.12720(12) 0.0905(2) 0.0626(16) Uani 1 1 d . . . H60G H 2.2873 0.1154 0.0647 0.094 Uiso 1 1 calc R . . H60H H 2.4423 0.1391 0.0701 0.094 Uiso 1 1 calc R . . H60I H 2.3066 0.1441 0.1121 0.094 Uiso 1 1 calc R . . C605 C 2.2198(4) 0.01209(11) 0.21007(18) 0.0381(12) Uani 1 1 d . . . H60J H 2.1488 0.0254 0.1841 0.046 Uiso 1 1 calc R . . H60K H 2.1526 0.0002 0.2359 0.046 Uiso 1 1 calc R . . C606 C 2.3027(5) -0.01528(12) 0.17778(19) 0.0455(13) Uani 1 1 d . . . H60L H 2.3636 -0.0309 0.2034 0.055 Uiso 1 1 calc R . . H60M H 2.3776 -0.0040 0.1539 0.055 Uiso 1 1 calc R . . C607 C 2.1798(5) -0.03661(12) 0.1421(2) 0.0463(13) Uani 1 1 d . . . H60N H 2.2231 -0.0599 0.1357 0.056 Uiso 1 1 calc R . . H60O H 2.0826 -0.0394 0.1621 0.056 Uiso 1 1 calc R . . C608 C 2.1388(6) -0.01935(13) 0.0877(2) 0.0652(16) Uani 1 1 d . . . H60P H 2.1012 0.0042 0.0939 0.098 Uiso 1 1 calc R . . H60Q H 2.0557 -0.0326 0.0673 0.098 Uiso 1 1 calc R . . H60R H 2.2329 -0.0184 0.0664 0.098 Uiso 1 1 calc R . . C609 C 2.4420(4) 0.01861(11) 0.28112(17) 0.0342(12) Uani 1 1 d . . . H60S H 2.4998 0.0360 0.3045 0.041 Uiso 1 1 calc R . . H60T H 2.5202 0.0071 0.2589 0.041 Uiso 1 1 calc R . . C610 C 2.3745(5) -0.00831(11) 0.31835(18) 0.0399(12) Uani 1 1 d . . . H61A H 2.3409 -0.0289 0.2966 0.048 Uiso 1 1 calc R . . H61B H 2.2806 0.0012 0.3352 0.048 Uiso 1 1 calc R . . C611 C 2.4990(5) -0.01861(11) 0.36319(18) 0.0377(12) Uani 1 1 d . . . H61C H 2.4713 -0.0415 0.3782 0.045 Uiso 1 1 calc R . . H61D H 2.6027 -0.0208 0.3470 0.045 Uiso 1 1 calc R . . C612 C 2.5127(5) 0.00770(11) 0.40974(18) 0.0448(13) Uani 1 1 d . . . H61E H 2.5348 0.0306 0.3948 0.067 Uiso 1 1 calc R . . H61F H 2.5989 0.0010 0.4363 0.067 Uiso 1 1 calc R . . H61G H 2.4132 0.0085 0.4281 0.067 Uiso 1 1 calc R . . C613 C 2.2173(4) 0.06033(11) 0.27395(17) 0.0332(11) Uani 1 1 d . . . H61H H 2.1361 0.0702 0.2474 0.040 Uiso 1 1 calc R . . H61I H 2.1619 0.0455 0.2996 0.040 Uiso 1 1 calc R . . C614 C 2.2937(5) 0.08985(11) 0.30645(18) 0.0409(12) Uani 1 1 d . . . H61J H 2.3391 0.1067 0.2812 0.049 Uiso 1 1 calc R . . H61K H 2.3803 0.0809 0.3317 0.049 Uiso 1 1 calc R . . C615 C 2.1684(5) 0.10780(10) 0.33955(18) 0.0361(12) Uani 1 1 d . . . C616 C 2.2416(5) 0.13888(11) 0.37126(18) 0.0504(14) Uani 1 1 d . . . H61L H 2.3297 0.1309 0.3961 0.076 Uiso 1 1 calc R . . H61M H 2.1613 0.1498 0.3926 0.076 Uiso 1 1 calc R . . H61N H 2.2806 0.1557 0.3452 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 N101 0.043(2) 0.031(2) 0.032(2) -0.005(2) -0.0043(19) 0.0096(18) N102 0.034(2) 0.022(2) 0.030(2) -0.0032(19) 0.0027(18) 0.0023(16) N103 0.031(2) 0.026(2) 0.028(2) -0.0035(18) 0.0098(17) -0.0002(16) N104 0.041(2) 0.026(2) 0.039(3) -0.001(2) 0.0104(18) -0.0010(18) O101 0.0471(19) 0.032(2) 0.036(2) -0.0023(17) -0.0084(15) 0.0120(15) O102 0.0365(17) 0.040(2) 0.032(2) -0.0057(17) 0.0085(15) -0.0022(14) C101 0.059(3) 0.042(3) 0.030(3) -0.004(3) -0.007(2) 0.014(3) C102 0.049(3) 0.072(4) 0.035(3) 0.004(3) -0.005(3) 0.013(3) C103 0.053(3) 0.086(5) 0.032(3) 0.010(4) -0.008(3) -0.011(3) C104 0.100(4) 0.071(5) 0.033(4) -0.005(3) -0.013(3) -0.018(4) C105 0.092(4) 0.039(3) 0.041(4) 0.000(3) -0.010(3) -0.004(3) C106 0.029(2) 0.039(3) 0.025(3) -0.002(3) 0.003(2) 0.003(2) C107 0.027(3) 0.030(3) 0.031(3) 0.003(3) 0.006(2) -0.001(2) C108 0.022(2) 0.030(3) 0.024(3) -0.001(2) 0.001(2) 0.004(2) C109 0.027(2) 0.030(3) 0.029(3) 0.004(2) 0.004(2) -0.003(2) C110 0.039(3) 0.030(3) 0.031(3) -0.001(3) 0.005(2) -0.007(2) C111 0.034(3) 0.039(3) 0.033(3) -0.010(3) 0.008(2) -0.009(2) C112 0.032(3) 0.036(3) 0.028(3) 0.003(2) 0.004(2) -0.005(2) C113 0.022(2) 0.029(3) 0.031(3) -0.003(2) 0.004(2) 0.000(2) C114 0.023(2) 0.034(3) 0.029(3) 0.005(3) -0.005(2) 0.000(2) C115 0.029(3) 0.041(3) 0.036(3) 0.007(3) 0.000(2) -0.008(2) C116 0.049(3) 0.028(3) 0.039(3) 0.002(3) -0.001(2) -0.005(2) C117 0.065(3) 0.034(3) 0.042(4) 0.002(3) -0.008(3) -0.011(3) C118 0.061(3) 0.048(4) 0.045(4) 0.021(3) -0.009(3) -0.019(3) C119 0.059(3) 0.052(4) 0.037(3) 0.007(3) 0.004(3) -0.013(3) C120 0.043(3) 0.042(3) 0.041(3) 0.004(3) 0.008(2) -0.010(2) N201 0.041(2) 0.028(2) 0.023(2) 0.0009(19) 0.0055(17) 0.0050(17) N202 0.035(2) 0.027(2) 0.024(2) 0.0007(19) 0.0075(17) -0.0008(17) N203 0.034(2) 0.026(2) 0.025(2) -0.0005(19) -0.0010(17) -0.0069(17) N204 0.037(2) 0.037(2) 0.029(3) -0.001(2) 0.0033(18) -0.0083(17) O201 0.0469(18) 0.041(2) 0.029(2) 0.0038(17) 0.0123(15) 0.0074(15) O202 0.0393(18) 0.039(2) 0.034(2) 0.0047(17) 0.0016(15) -0.0122(15) C201 0.030(2) 0.034(3) 0.027(3) 0.001(2) 0.001(2) -0.003(2) C202 0.043(3) 0.039(3) 0.028(3) -0.004(3) 0.007(2) 0.002(2) C203 0.045(3) 0.031(3) 0.045(4) 0.005(3) 0.011(3) 0.006(2) C204 0.030(3) 0.042(3) 0.049(4) 0.017(3) 0.004(2) 0.007(2) C205 0.032(3) 0.037(3) 0.034(3) 0.001(2) 0.002(2) 0.001(2) C206 0.029(2) 0.029(3) 0.025(3) 0.003(2) 0.004(2) 0.001(2) C207 0.026(2) 0.029(3) 0.032(3) -0.001(3) 0.000(2) 0.001(2) C208 0.021(2) 0.025(3) 0.034(3) 0.003(2) 0.002(2) -0.0040(19) C209 0.030(2) 0.036(3) 0.026(3) -0.001(2) 0.002(2) -0.005(2) C210 0.038(3) 0.037(3) 0.030(3) 0.003(3) -0.001(2) -0.004(2) C211 0.031(2) 0.033(3) 0.032(3) 0.010(3) 0.005(2) 0.003(2) C212 0.026(2) 0.025(3) 0.037(3) 0.000(2) 0.005(2) -0.001(2) C213 0.021(2) 0.034(3) 0.027(3) 0.004(2) 0.003(2) 0.000(2) C214 0.027(3) 0.035(3) 0.028(3) -0.004(3) 0.001(2) 0.004(2) C215 0.031(3) 0.036(3) 0.032(3) -0.006(3) 0.000(2) 0.007(2) C216 0.065(3) 0.052(4) 0.029(3) -0.002(3) 0.002(3) -0.010(3) C217 0.082(4) 0.074(4) 0.023(3) -0.004(3) -0.010(3) -0.013(3) C218 0.053(3) 0.054(4) 0.036(4) -0.015(3) -0.005(3) -0.011(3) C219 0.037(3) 0.047(3) 0.038(3) -0.013(3) 0.001(2) -0.003(2) C220 0.036(3) 0.036(3) 0.040(3) -0.004(3) -0.003(2) 0.000(2) O301 0.067(2) 0.031(2) 0.062(3) 0.0046(19) -0.0078(18) -0.0116(17) O302 0.071(2) 0.056(2) 0.041(2) 0.009(2) 0.0191(19) -0.0001(18) C301 0.043(3) 0.038(3) 0.035(3) 0.001(3) 0.001(2) 0.005(2) C302 0.052(3) 0.058(4) 0.048(4) 0.015(3) 0.011(3) 0.002(3) C303 0.035(3) 0.058(4) 0.069(5) 0.033(4) 0.004(3) -0.007(3) C304 0.049(3) 0.026(3) 0.066(4) 0.002(3) -0.007(3) -0.008(2) C305 0.040(3) 0.039(3) 0.043(3) -0.001(3) 0.003(2) 0.001(2) C306 0.027(2) 0.022(3) 0.031(3) 0.000(2) -0.006(2) -0.004(2) C307 0.030(3) 0.030(3) 0.042(4) 0.004(3) 0.000(2) 0.004(2) O401 0.0516(19) 0.032(2) 0.037(2) 0.0049(17) 0.0062(15) 0.0025(15) O402 0.085(2) 0.044(2) 0.029(2) 0.0047(18) 0.0173(18) 0.0110(17) C401 0.057(3) 0.032(3) 0.034(3) 0.002(3) 0.004(2) 0.002(2) C402 0.078(4) 0.057(4) 0.029(3) 0.001(3) 0.014(3) -0.005(3) C403 0.078(4) 0.052(4) 0.033(4) 0.010(3) 0.004(3) -0.002(3) C404 0.070(3) 0.043(3) 0.044(4) 0.009(3) 0.006(3) 0.012(3) C405 0.046(3) 0.040(3) 0.035(3) 0.002(3) 0.007(2) 0.004(2) C406 0.031(2) 0.032(3) 0.024(3) -0.003(2) 0.001(2) -0.003(2) C407 0.029(3) 0.038(3) 0.029(3) 0.000(3) 0.002(2) -0.003(2) N501 0.0258(19) 0.033(2) 0.033(2) 0.000(2) 0.0031(17) -0.0005(17) C501 0.029(3) 0.038(3) 0.041(3) -0.003(3) -0.001(2) -0.008(2) C502 0.029(3) 0.038(3) 0.043(3) -0.003(3) 0.001(2) 0.004(2) C503 0.037(3) 0.036(3) 0.041(3) -0.002(3) -0.002(2) -0.006(2) C504 0.055(3) 0.034(3) 0.053(4) -0.005(3) -0.012(3) 0.001(2) C505 0.027(2) 0.034(3) 0.041(3) 0.001(2) 0.005(2) -0.001(2) C506 0.040(3) 0.050(3) 0.047(4) 0.007(3) 0.004(2) -0.008(2) C507 0.062(3) 0.062(4) 0.036(3) 0.017(3) 0.000(3) -0.013(3) C508 0.068(4) 0.083(4) 0.048(4) -0.001(3) -0.002(3) 0.000(3) C509 0.030(2) 0.035(3) 0.038(3) -0.009(2) 0.004(2) 0.002(2) C510 0.034(3) 0.055(3) 0.039(3) -0.015(3) 0.004(2) 0.001(2) C511 0.036(3) 0.051(3) 0.045(3) -0.019(3) 0.000(2) 0.003(2) C512 0.073(4) 0.054(4) 0.060(4) 0.001(3) -0.001(3) 0.004(3) C513 0.028(2) 0.041(3) 0.035(3) -0.005(2) 0.008(2) -0.008(2) C514 0.035(3) 0.054(3) 0.030(3) -0.007(3) -0.001(2) -0.001(2) C515 0.038(3) 0.061(4) 0.035(3) 0.012(3) 0.008(2) 0.005(3) C516 0.071(4) 0.063(4) 0.070(4) 0.018(3) -0.009(3) -0.018(3) N601 0.0223(19) 0.039(2) 0.030(2) -0.007(2) 0.0051(17) -0.0045(17) C601 0.029(2) 0.044(3) 0.035(3) 0.002(3) 0.007(2) -0.006(2) C602 0.037(3) 0.047(3) 0.045(3) 0.001(3) 0.010(2) 0.004(2) C603 0.048(3) 0.045(3) 0.037(3) -0.008(3) 0.008(2) -0.007(2) C604 0.070(4) 0.053(4) 0.068(4) 0.013(3) 0.024(3) 0.009(3) C605 0.026(2) 0.044(3) 0.044(3) -0.006(3) 0.002(2) -0.001(2) C606 0.031(3) 0.053(3) 0.053(4) -0.016(3) 0.006(2) 0.003(2) C607 0.037(3) 0.050(3) 0.051(4) -0.020(3) -0.002(2) 0.004(2) C608 0.064(4) 0.071(4) 0.060(4) -0.020(4) 0.003(3) 0.002(3) C609 0.025(2) 0.041(3) 0.036(3) 0.001(3) -0.001(2) 0.000(2) C610 0.035(3) 0.041(3) 0.044(3) 0.002(3) 0.001(2) -0.001(2) C611 0.036(3) 0.037(3) 0.041(3) 0.001(3) 0.011(2) -0.002(2) C612 0.052(3) 0.037(3) 0.046(3) 0.008(3) 0.013(2) -0.003(2) C613 0.028(2) 0.042(3) 0.031(3) 0.000(2) 0.009(2) 0.000(2) C614 0.038(3) 0.042(3) 0.043(3) -0.004(3) 0.005(2) -0.013(2) C615 0.045(3) 0.025(3) 0.040(3) -0.013(2) 0.013(2) -0.004(2) C616 0.056(3) 0.050(3) 0.046(4) -0.005(3) 0.013(3) -0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N101 C107 1.366(5) . ? N101 C106 1.414(5) . ? N102 C107 1.370(5) . ? N102 C108 1.413(5) . ? N103 C114 1.380(5) . ? N103 C113 1.423(5) . ? N104 C114 1.368(5) . ? N104 C115 1.407(5) . ? O101 C107 1.214(4) . ? O102 C114 1.229(5) . ? C101 C106 1.376(5) . ? C101 C102 1.387(6) . ? C102 C103 1.363(6) . ? C103 C104 1.354(6) . ? C104 C105 1.389(6) . ? C105 C106 1.386(6) . ? C108 C109 1.394(5) . ? C108 C113 1.399(5) . ? C109 C110 1.381(5) . ? C110 C111 1.373(5) . ? C111 C112 1.380(5) . ? C112 C113 1.383(5) . ? C115 C116 1.386(5) . ? C115 C120 1.388(6) . ? C116 C117 1.377(6) . ? C117 C118 1.378(6) . ? C118 C119 1.378(6) . ? C119 C120 1.395(5) . ? N201 C207 1.375(5) . ? N201 C206 1.419(5) . ? N202 C207 1.375(5) . ? N202 C208 1.404(5) . ? N203 C214 1.375(5) . ? N203 C213 1.417(5) . ? N204 C214 1.381(5) . ? N204 C215 1.416(5) . ? O201 C207 1.222(4) . ? O202 C214 1.211(5) . ? C201 C202 1.381(5) . ? C201 C206 1.382(5) . ? C202 C203 1.371(5) . ? C203 C204 1.381(6) . ? C204 C205 1.384(5) . ? C205 C206 1.388(5) . ? C208 C213 1.394(5) . ? C208 C209 1.406(5) . ? C209 C210 1.387(5) . ? C210 C211 1.382(5) . ? C211 C212 1.386(5) . ? C212 C213 1.399(5) . ? C215 C216 1.389(6) . ? C215 C220 1.390(5) . ? C216 C217 1.387(6) . ? C217 C218 1.369(6) . ? C218 C219 1.362(6) . ? C219 C220 1.374(5) . ? O301 C307 1.256(5) . ? O302 C307 1.243(5) . ? C301 C302 1.371(6) . ? C301 C306 1.392(5) . ? C302 C303 1.363(6) . ? C303 C304 1.369(6) . ? C304 C305 1.383(6) . ? C305 C306 1.372(5) . ? C306 C307 1.499(6) . ? O401 C407 1.254(5) . ? O402 C407 1.252(5) . ? C401 C406 1.378(5) . ? C401 C402 1.392(6) . ? C402 C403 1.366(6) . ? C403 C404 1.369(6) . ? C404 C405 1.393(6) . ? C405 C406 1.370(5) . ? C406 C407 1.502(6) . ? N501 C509 1.515(4) . ? N501 C513 1.515(5) . ? N501 C501 1.515(5) . ? N501 C505 1.520(5) . ? C501 C502 1.506(5) . ? C502 C503 1.512(5) . ? C503 C504 1.513(5) . ? C505 C506 1.512(5) . ? C506 C507 1.534(6) . ? C507 C508 1.503(6) . ? C509 C510 1.510(5) . ? C510 C511 1.525(5) . ? C511 C512 1.519(6) . ? C513 C514 1.509(5) . ? C514 C515 1.520(5) . ? C515 C516 1.517(6) . ? N601 C609 1.510(5) . ? N601 C601 1.512(5) . ? N601 C613 1.515(4) . ? N601 C605 1.518(5) . ? C601 C602 1.524(5) . ? C602 C603 1.520(5) . ? C603 C604 1.513(6) . ? C605 C606 1.518(5) . ? C606 C607 1.551(5) . ? C607 C608 1.507(6) . ? C609 C610 1.517(5) . ? C610 C611 1.524(5) . ? C611 C612 1.524(5) . ? C613 C614 1.512(5) . ? C614 C615 1.540(5) . ? C615 C616 1.538(5) . ? 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 C107 N101 C106 127.1(4) . . ? C107 N102 C108 125.7(4) . . ? C114 N103 C113 123.8(3) . . ? C114 N104 C115 128.3(4) . . ? C106 C101 C102 120.0(5) . . ? C103 C102 C101 120.6(5) . . ? C104 C103 C102 120.0(5) . . ? C103 C104 C105 120.6(5) . . ? C106 C105 C104 119.8(5) . . ? C101 C106 C105 119.1(4) . . ? C101 C106 N101 123.4(4) . . ? C105 C106 N101 117.5(4) . . ? O101 C107 N101 124.6(4) . . ? O101 C107 N102 123.5(4) . . ? N101 C107 N102 111.7(4) . . ? C109 C108 C113 119.1(4) . . ? C109 C108 N102 121.2(4) . . ? C113 C108 N102 119.7(4) . . ? C110 C109 C108 120.1(4) . . ? C111 C110 C109 120.4(4) . . ? C110 C111 C112 120.3(4) . . ? C111 C112 C113 120.2(4) . . ? C112 C113 C108 119.9(4) . . ? C112 C113 N103 120.9(4) . . ? C108 C113 N103 119.2(4) . . ? O102 C114 N104 124.7(4) . . ? O102 C114 N103 123.3(4) . . ? N104 C114 N103 112.0(4) . . ? C116 C115 C120 119.9(4) . . ? C116 C115 N104 116.5(4) . . ? C120 C115 N104 123.6(4) . . ? C117 C116 C115 120.5(4) . . ? C116 C117 C118 120.5(5) . . ? C117 C118 C119 119.0(5) . . ? C118 C119 C120 121.6(5) . . ? C115 C120 C119 118.5(4) . . ? C207 N201 C206 123.1(3) . . ? C207 N202 C208 125.5(4) . . ? C214 N203 C213 121.9(4) . . ? C214 N204 C215 127.3(4) . . ? C202 C201 C206 119.6(4) . . ? C203 C202 C201 121.2(4) . . ? C202 C203 C204 119.4(4) . . ? C203 C204 C205 120.1(4) . . ? C204 C205 C206 120.2(4) . . ? C201 C206 C205 119.5(4) . . ? C201 C206 N201 121.3(4) . . ? C205 C206 N201 119.2(4) . . ? O201 C207 N201 123.5(4) . . ? O201 C207 N202 124.4(4) . . ? N201 C207 N202 112.1(4) . . ? C213 C208 N202 119.2(4) . . ? C213 C208 C209 119.1(4) . . ? N202 C208 C209 121.5(4) . . ? C210 C209 C208 120.2(4) . . ? C211 C210 C209 120.2(4) . . ? C210 C211 C212 120.5(4) . . ? C211 C212 C213 119.8(4) . . ? C208 C213 C212 120.2(4) . . ? C208 C213 N203 120.0(4) . . ? C212 C213 N203 119.8(4) . . ? O202 C214 N203 124.4(4) . . ? O202 C214 N204 124.1(4) . . ? N203 C214 N204 111.5(4) . . ? C216 C215 C220 118.9(4) . . ? C216 C215 N204 117.1(4) . . ? C220 C215 N204 124.0(4) . . ? C217 C216 C215 119.9(5) . . ? C218 C217 C216 120.8(5) . . ? C219 C218 C217 119.1(5) . . ? C218 C219 C220 121.8(5) . . ? C219 C220 C215 119.6(4) . . ? C302 C301 C306 120.6(4) . . ? C303 C302 C301 120.0(5) . . ? C302 C303 C304 120.3(5) . . ? C303 C304 C305 120.1(5) . . ? C306 C305 C304 120.2(4) . . ? C305 C306 C301 118.8(4) . . ? C305 C306 C307 120.6(4) . . ? C301 C306 C307 120.6(4) . . ? O302 C307 O301 123.8(4) . . ? O302 C307 C306 119.2(4) . . ? O301 C307 C306 117.0(4) . . ? C406 C401 C402 120.2(4) . . ? C403 C402 C401 120.2(5) . . ? C402 C403 C404 120.1(5) . . ? C403 C404 C405 119.7(5) . . ? C406 C405 C404 120.7(4) . . ? C405 C406 C401 119.1(4) . . ? C405 C406 C407 120.8(4) . . ? C401 C406 C407 120.1(4) . . ? O402 C407 O401 123.4(4) . . ? O402 C407 C406 118.1(4) . . ? O401 C407 C406 118.5(4) . . ? C509 N501 C513 110.6(3) . . ? C509 N501 C501 107.2(3) . . ? C513 N501 C501 110.7(3) . . ? C509 N501 C505 111.2(3) . . ? C513 N501 C505 107.2(3) . . ? C501 N501 C505 110.0(3) . . ? C502 C501 N501 115.9(3) . . ? C501 C502 C503 110.7(3) . . ? C502 C503 C504 111.7(3) . . ? C506 C505 N501 116.8(3) . . ? C505 C506 C507 110.5(3) . . ? C508 C507 C506 112.3(4) . . ? C510 C509 N501 115.7(3) . . ? C509 C510 C511 111.0(3) . . ? C512 C511 C510 113.8(4) . . ? C514 C513 N501 116.9(3) . . ? C513 C514 C515 111.1(3) . . ? C516 C515 C514 114.1(4) . . ? C609 N601 C601 106.3(3) . . ? C609 N601 C613 111.0(3) . . ? C601 N601 C613 111.0(3) . . ? C609 N601 C605 110.6(3) . . ? C601 N601 C605 111.4(3) . . ? C613 N601 C605 106.6(3) . . ? N601 C601 C602 115.9(3) . . ? C603 C602 C601 109.5(3) . . ? C604 C603 C602 113.3(4) . . ? N601 C605 C606 116.5(3) . . ? C605 C606 C607 110.2(3) . . ? C608 C607 C606 111.6(4) . . ? N601 C609 C610 116.6(3) . . ? C609 C610 C611 109.8(3) . . ? C612 C611 C610 112.2(4) . . ? C614 C613 N601 116.9(3) . . ? C613 C614 C615 109.2(3) . . ? C616 C615 C614 110.2(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N101 H901 O301 0.88 2.01 2.821(5) 153.6 4_566 N102 H902 O301 0.88 1.92 2.740(4) 154.3 4_566 N103 H903 O302 0.88 2.14 2.939(4) 151.0 4_566 N104 H904 O302 0.88 1.97 2.820(5) 161.1 4_566 N201 H801 O402 0.88 2.02 2.827(5) 152.9 3_955 N202 H802 O402 0.88 1.98 2.807(4) 155.1 3_955 N203 H803 O401 0.88 1.99 2.803(4) 153.3 3_955 N204 H804 O401 0.88 2.05 2.871(4) 154.3 3_955 _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 26.11 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.450 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.061