# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Philip Gale' 'Matthew G. Fisher' 'Mark E. Light' _publ_contact_author_name 'Philip Gale' _publ_contact_author_address ; Department of Chemistry University of Southampton Southampton SO17 1BJ UNITED KINGDOM ; _publ_contact_author_email PHILIP.GALE@SOTON.AC.UK _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; A simple benzimidazole-based receptor for barbiturate and urea neutral guests that functions in polar solvent mixtures ; _journal_name_full 'Private Communication ' _journal_year 2007 data_2007sot0234 _database_code_depnum_ccdc_archive 'CCDC 651651' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H39 N9 O7 S2' _chemical_formula_weight 737.85 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9882(4) _cell_length_b 14.1537(5) _cell_length_c 14.7208(8) _cell_angle_alpha 64.158(2) _cell_angle_beta 86.751(3) _cell_angle_gamma 70.732(3) _cell_volume 1758.73(13) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 17300 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9297 _exptl_absorpt_correction_T_max 0.9853 _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 11970 reflections reduced R(int) from 0.0594 to 0.0458 Ratio of minimum to maximum apparent transmission: 0.769243 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 20558 _diffrn_reflns_av_R_equivalents 0.0609 _diffrn_reflns_av_sigmaI/netI 0.0823 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7607 _reflns_number_gt 5105 _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^)+(0.0604P)^2^+0.9820P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7607 _refine_ls_number_parameters 499 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0976 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1467 _refine_ls_wR_factor_gt 0.1274 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.002 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 O1 O 0.35340(2) 0.141053(17) 0.098908(17) 0.02867(8) Uani 1 1 d . . . O2 O 1.06024(2) -0.229947(17) 0.214364(17) 0.02640(8) Uani 1 1 d . . . N1 N 0.25796(3) 0.280017(19) -0.09726(2) 0.02224(9) Uani 1 1 d . . . N2 N 0.42223(3) 0.261214(19) -0.204073(19) 0.02197(9) Uani 1 1 d . . . N3 N 0.49365(3) 0.142829(19) -0.029220(19) 0.02054(8) Uani 1 1 d . . . N4 N 0.71165(3) -0.030195(18) 0.112513(19) 0.01947(8) Uani 1 1 d . . . N5 N 0.96470(3) -0.124953(19) 0.049102(19) 0.02136(9) Uani 1 1 d . . . N6 N 1.08956(3) -0.119996(19) -0.09315(2) 0.02065(8) Uani 1 1 d . . . N7 N 1.19837(3) -0.25618(2) 0.05785(2) 0.02477(9) Uani 1 1 d . . . C1 C 0.19096(3) 0.35523(2) -0.19373(2) 0.02153(10) Uani 1 1 d . . . C2 C 0.05185(4) 0.42800(2) -0.22789(2) 0.02537(10) Uani 1 1 d . . . H2 H -0.0180 0.4345 -0.1824 0.030 Uiso 1 1 calc R . . C3 C 0.02044(4) 0.49053(2) -0.33192(3) 0.02743(11) Uani 1 1 d . . . H3 H -0.0733 0.5420 -0.3584 0.033 Uiso 1 1 calc R . . C4 C 0.12278(4) 0.48011(3) -0.39932(3) 0.02819(11) Uani 1 1 d . . . H4 H 0.0971 0.5250 -0.4702 0.034 Uiso 1 1 calc R . . C5 C 0.26080(4) 0.40552(2) -0.36460(3) 0.02612(11) Uani 1 1 d . . . H5 H 0.3298 0.3977 -0.4103 0.031 Uiso 1 1 calc R . . C6 C 0.29427(3) 0.34248(2) -0.25983(2) 0.02230(10) Uani 1 1 d . . . C7 C 0.39354(3) 0.22707(2) -0.10834(2) 0.01952(10) Uani 1 1 d . . . C8 C 0.46835(3) 0.10362(2) 0.07059(2) 0.02118(10) Uani 1 1 d . . . C9 C 0.58899(3) 0.01177(2) 0.14578(2) 0.02000(9) Uani 1 1 d . . . C10 C 0.56758(4) -0.02608(2) 0.24838(2) 0.02484(11) Uani 1 1 d . . . H10 H 0.4791 0.0064 0.2686 0.030 Uiso 1 1 calc R . . C11 C 0.67632(4) -0.11124(3) 0.32011(2) 0.02773(11) Uani 1 1 d . . . H11 H 0.6636 -0.1396 0.3903 0.033 Uiso 1 1 calc R . . C12 C 0.80473(4) -0.15449(2) 0.28706(2) 0.02535(11) Uani 1 1 d . . . H12 H 0.8822 -0.2126 0.3344 0.030 Uiso 1 1 calc R . . C13 C 0.81814(3) -0.11156(2) 0.18386(2) 0.02049(10) Uani 1 1 d . . . C14 C 0.95960(3) -0.16070(2) 0.15109(2) 0.02155(10) Uani 1 1 d . . . C15 C 1.08280(3) -0.16599(2) 0.00554(2) 0.01971(10) Uani 1 1 d . . . C16 C 1.21943(3) -0.18574(2) -0.10720(2) 0.02131(10) Uani 1 1 d . . . C17 C 1.28310(4) -0.17638(2) -0.19625(2) 0.02563(11) Uani 1 1 d . . . H17 H 1.2373 -0.1187 -0.2606 0.031 Uiso 1 1 calc R . . C18 C 1.41582(4) -0.25467(2) -0.18699(3) 0.02758(11) Uani 1 1 d . . . H18 H 1.4622 -0.2493 -0.2463 0.033 Uiso 1 1 calc R . . C19 C 1.48322(4) -0.34113(3) -0.09314(3) 0.02874(11) Uani 1 1 d . . . H19 H 1.5735 -0.3938 -0.0901 0.034 Uiso 1 1 calc R . . C20 C 1.42056(4) -0.35158(3) -0.00388(3) 0.02879(11) Uani 1 1 d . . . H20 H 1.4658 -0.4101 0.0603 0.035 Uiso 1 1 calc R . . C21 C 1.28854(3) -0.27209(2) -0.01345(2) 0.02295(10) Uani 1 1 d . . . O3 O 0.75045(2) 0.063823(16) -0.124470(16) 0.02377(7) Uani 1 1 d . . . O4 O 0.98195(3) -0.031582(19) -0.359996(18) 0.03633(9) Uani 1 1 d . . . O5 O 0.55480(3) 0.27705(2) -0.450067(18) 0.03607(9) Uani 1 1 d . . . N8 N 0.87274(3) 0.02373(2) -0.245195(19) 0.02359(9) Uani 1 1 d . . . N9 N 0.65347(3) 0.16886(2) -0.288223(19) 0.02233(9) Uani 1 1 d . . . C22 C 0.75921(3) 0.08501(2) -0.21455(2) 0.02030(10) Uani 1 1 d . . . C23 C 0.88722(4) 0.03758(2) -0.34323(2) 0.02425(11) Uani 1 1 d . . . C24 C 0.78957(4) 0.14390(2) -0.42742(2) 0.02345(10) Uani 1 1 d . . . C25 C 0.65573(4) 0.20104(2) -0.39065(2) 0.02470(11) Uani 1 1 d . . . C26 C 0.74999(4) 0.12125(3) -0.51358(2) 0.02890(11) Uani 1 1 d . . . H26A H 0.6966 0.1933 -0.5710 0.035 Uiso 1 1 calc R . . H26B H 0.8387 0.0865 -0.5376 0.035 Uiso 1 1 calc R . . C27 C 0.66030(4) 0.04541(3) -0.48238(3) 0.04416(13) Uani 1 1 d . . . H27A H 0.7111 -0.0253 -0.4242 0.066 Uiso 1 1 calc R . . H27B H 0.6432 0.0309 -0.5392 0.066 Uiso 1 1 calc R . . H27C H 0.5689 0.0819 -0.4637 0.066 Uiso 1 1 calc R . . C28 C 0.87164(4) 0.22926(3) -0.46533(3) 0.02620(11) Uani 1 1 d . . . H28A H 0.8067 0.3020 -0.5157 0.031 Uiso 1 1 calc R . . H28B H 0.8962 0.2400 -0.4071 0.031 Uiso 1 1 calc R . . C29 C 1.00806(4) 0.19592(3) -0.51323(3) 0.03439(12) Uani 1 1 d . . . H29A H 1.0740 0.1242 -0.4640 0.052 Uiso 1 1 calc R . . H29B H 1.0529 0.2531 -0.5330 0.052 Uiso 1 1 calc R . . H29C H 0.9848 0.1890 -0.5734 0.052 Uiso 1 1 calc R . . S1A S 0.381514(11) 0.454845(7) 0.313770(7) 0.02670(3) Uani 0.8807(2) 1 d P A 1 O6A O 0.29819(3) 0.51789(2) 0.21113(2) 0.02945(9) Uani 0.8807(2) 1 d P A 1 C30A C 0.33864(5) 0.55023(3) 0.36733(3) 0.03327(9) Uani 0.8807(2) 1 d P A 1 H30A H 0.3590 0.6177 0.3213 0.050 Uiso 0.8807(2) 1 calc PR A 1 H30B H 0.3960 0.5157 0.4327 0.050 Uiso 0.8807(2) 1 calc PR A 1 H30C H 0.2372 0.5701 0.3776 0.050 Uiso 0.8807(2) 1 calc PR A 1 C31A C 0.56173(4) 0.44904(3) 0.29112(3) 0.03327(9) Uani 0.8807(2) 1 d P A 1 H31A H 0.6005 0.4035 0.2549 0.050 Uiso 0.8807(2) 1 calc PR A 1 H31B H 0.6196 0.4157 0.3561 0.050 Uiso 0.8807(2) 1 calc PR A 1 H31C H 0.5635 0.5247 0.2500 0.050 Uiso 0.8807(2) 1 calc PR A 1 S1B S 0.38429(8) 0.53082(5) 0.25775(5) 0.02670(3) Uani 0.1193(2) 1 d P A 2 O6B O 0.3084(2) 0.45655(15) 0.25090(15) 0.02945(9) Uani 0.1193(2) 1 d P A 2 C30B C 0.3816(3) 0.5542(2) 0.3735(2) 0.03327(9) Uani 0.1193(2) 1 d P A 2 H30D H 0.2859 0.6017 0.3760 0.050 Uiso 0.1193(2) 1 calc PR A 2 H30E H 0.4504 0.5909 0.3711 0.050 Uiso 0.1193(2) 1 calc PR A 2 H30F H 0.4072 0.4823 0.4342 0.050 Uiso 0.1193(2) 1 calc PR A 2 C31B C 0.5573(3) 0.4492(2) 0.3081(2) 0.03327(9) Uani 0.1193(2) 1 d P A 2 H31D H 0.5588 0.3994 0.3800 0.050 Uiso 0.1193(2) 1 calc PR A 2 H31E H 0.6129 0.4969 0.3016 0.050 Uiso 0.1193(2) 1 calc PR A 2 H31F H 0.5988 0.4045 0.2715 0.050 Uiso 0.1193(2) 1 calc PR A 2 S2 S 0.032310(10) 0.297044(7) 0.128539(7) 0.03113(3) Uani 1 1 d . . . O7 O 0.04928(3) 0.335914(19) 0.017107(18) 0.03527(9) Uani 1 1 d . . . C32 C -0.12541(4) 0.40173(3) 0.13347(3) 0.04258(13) Uani 1 1 d . . . H32A H -0.1176 0.4757 0.0935 0.064 Uiso 1 1 calc R . . H32B H -0.1357 0.3890 0.2041 0.064 Uiso 1 1 calc R . . H32C H -0.2089 0.3976 0.1055 0.064 Uiso 1 1 calc R . . C33 C 0.15937(4) 0.33145(3) 0.17776(3) 0.05397(14) Uani 1 1 d . . . H33A H 0.2558 0.2823 0.1790 0.081 Uiso 1 1 calc R . . H33B H 0.1408 0.3217 0.2468 0.081 Uiso 1 1 calc R . . H33C H 0.1513 0.4092 0.1345 0.081 Uiso 1 1 calc R . . H98 H 0.5761(4) 0.1142(3) -0.0460(3) 0.0283(10) Uiso 1 1 d . . . H97 H 0.8899(4) -0.0716(3) 0.0084(3) 0.0372(11) Uiso 1 1 d . . . H94 H 0.9423(5) -0.0304(3) -0.1904(3) 0.0550(14) Uiso 1 1 d . . . H96 H 1.2096(4) -0.3005(3) 0.1234(3) 0.0374(11) Uiso 1 1 d . . . H99 H 0.2258(4) 0.2700(3) -0.0420(3) 0.0452(12) Uiso 1 1 d . . . H95 H 0.5767(5) 0.2044(3) -0.2646(3) 0.0576(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.02388(11) 0.03191(9) 0.02941(10) -0.01520(7) 0.01044(9) -0.00748(8) O2 0.02314(11) 0.02905(9) 0.02477(10) -0.01207(7) 0.00084(9) -0.00568(8) N1 0.02037(12) 0.02521(9) 0.02482(11) -0.01437(7) 0.00781(10) -0.00850(9) N2 0.01759(12) 0.02361(10) 0.02321(11) -0.01142(8) 0.00368(10) -0.00400(9) N3 0.01669(12) 0.02280(9) 0.02275(11) -0.01222(7) 0.00667(10) -0.00524(8) N4 0.01963(11) 0.02037(9) 0.02339(11) -0.01211(7) 0.00459(10) -0.00982(8) N5 0.01674(12) 0.02437(10) 0.02330(11) -0.01307(7) 0.00428(10) -0.00425(9) N6 0.01922(12) 0.01881(9) 0.02303(11) -0.00947(7) 0.00656(10) -0.00580(8) N7 0.02132(13) 0.02957(11) 0.02042(11) -0.01273(8) 0.00240(10) -0.00277(10) C1 0.01945(14) 0.01920(11) 0.02776(14) -0.01147(9) 0.00356(12) -0.00747(10) C2 0.02023(14) 0.02742(11) 0.03442(14) -0.01952(9) 0.00696(12) -0.00788(10) C3 0.01826(14) 0.02765(12) 0.03710(16) -0.01657(10) 0.00087(13) -0.00524(11) C4 0.02510(15) 0.02885(12) 0.02948(15) -0.01222(10) -0.00094(13) -0.00815(11) C5 0.02313(15) 0.02754(12) 0.02791(14) -0.01343(9) 0.00588(13) -0.00781(11) C6 0.01915(14) 0.02317(11) 0.02762(14) -0.01343(9) 0.00482(12) -0.00820(10) C7 0.01820(13) 0.02025(10) 0.02416(13) -0.01265(8) 0.00599(11) -0.00811(9) C8 0.02170(14) 0.02134(10) 0.02560(13) -0.01407(8) 0.00705(12) -0.00912(10) C9 0.02205(14) 0.02134(10) 0.02409(13) -0.01411(8) 0.00678(11) -0.01147(9) C10 0.02306(15) 0.02883(12) 0.02659(14) -0.01541(9) 0.00914(12) -0.01030(11) C11 0.03176(16) 0.03532(13) 0.01859(14) -0.01197(10) 0.00934(13) -0.01544(11) C12 0.02427(15) 0.02963(12) 0.02359(14) -0.01168(9) 0.00444(12) -0.01136(11) C13 0.02188(13) 0.02188(10) 0.02351(13) -0.01300(8) 0.00561(11) -0.01085(9) C14 0.02371(14) 0.01987(10) 0.02543(13) -0.01182(8) 0.00489(12) -0.01055(9) C15 0.01671(13) 0.02015(10) 0.02509(13) -0.01285(8) 0.00324(11) -0.00590(9) C16 0.02192(14) 0.02030(10) 0.02696(13) -0.01336(8) 0.00660(12) -0.01015(9) C17 0.02689(15) 0.02500(12) 0.02698(15) -0.01181(9) 0.00911(13) -0.01182(11) C18 0.02689(15) 0.02899(12) 0.03388(15) -0.01908(9) 0.01388(13) -0.01253(11) C19 0.02079(15) 0.03035(12) 0.03849(16) -0.02020(10) 0.00643(13) -0.00645(11) C20 0.02118(16) 0.03122(13) 0.03005(15) -0.01448(10) 0.00100(13) -0.00264(12) C21 0.01881(14) 0.02931(11) 0.02579(13) -0.01674(9) 0.00388(12) -0.00823(10) O3 0.02400(10) 0.02621(8) 0.01875(9) -0.00949(6) 0.00703(8) -0.00713(8) O4 0.03846(14) 0.03126(10) 0.02796(11) -0.01523(7) 0.01002(10) 0.00365(10) O5 0.02448(12) 0.04647(11) 0.02587(11) -0.01817(8) -0.00077(10) 0.00521(10) N8 0.02364(13) 0.02353(10) 0.01859(11) -0.01013(8) 0.00532(10) -0.00138(9) N9 0.01836(12) 0.02636(10) 0.02029(11) -0.01190(7) 0.00316(10) -0.00322(9) C22 0.02247(14) 0.02036(11) 0.02053(13) -0.01049(8) 0.00770(12) -0.00914(10) C23 0.02471(15) 0.02434(12) 0.02334(14) -0.01191(9) 0.00707(13) -0.00675(11) C24 0.02207(15) 0.02689(12) 0.02020(13) -0.01148(9) 0.00342(12) -0.00563(11) C25 0.02046(15) 0.03297(12) 0.02173(13) -0.01520(9) 0.00342(12) -0.00628(11) C26 0.02630(16) 0.03987(13) 0.02521(14) -0.01974(10) 0.00728(13) -0.01024(12) C27 0.03692(18) 0.06766(16) 0.05398(17) -0.04511(11) 0.01839(15) -0.02620(13) C28 0.02466(16) 0.02603(12) 0.02336(14) -0.00968(10) 0.00247(13) -0.00485(11) C29 0.03116(17) 0.04380(14) 0.03575(16) -0.02284(11) 0.01406(14) -0.01630(12) S1A 0.02697(4) 0.02419(3) 0.02497(4) -0.00832(3) 0.00213(4) -0.00736(3) O6A 0.02287(12) 0.03189(11) 0.02696(12) -0.01065(8) -0.00293(10) -0.00372(9) C30A 0.03043(13) 0.03833(10) 0.03411(12) -0.01996(8) 0.00132(11) -0.00960(9) C31A 0.03043(13) 0.03833(10) 0.03411(12) -0.01996(8) 0.00132(11) -0.00960(9) S1B 0.02697(4) 0.02419(3) 0.02497(4) -0.00832(3) 0.00213(4) -0.00736(3) O6B 0.02287(12) 0.03189(11) 0.02696(12) -0.01065(8) -0.00293(10) -0.00372(9) C30B 0.03043(13) 0.03833(10) 0.03411(12) -0.01996(8) 0.00132(11) -0.00960(9) C31B 0.03043(13) 0.03833(10) 0.03411(12) -0.01996(8) 0.00132(11) -0.00960(9) S2 0.03186(4) 0.03867(3) 0.03543(4) -0.02417(2) 0.01387(3) -0.01804(3) O7 0.03245(13) 0.03952(10) 0.02997(11) -0.01764(8) 0.01245(10) -0.00595(10) C32 0.03269(17) 0.06282(14) 0.06128(17) -0.04834(10) 0.02311(15) -0.02526(12) C33 0.03168(19) 0.08711(17) 0.07836(19) -0.06625(12) 0.01746(16) -0.02347(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 O1 C8 1.2286(4) . ? O2 C14 1.2242(3) . ? N1 C7 1.3542(4) . ? N1 C1 1.3848(4) . ? N2 C7 1.3242(4) . ? N2 C6 1.3985(4) . ? N3 C8 1.3676(4) . ? N3 C7 1.3830(3) . ? N4 C9 1.3412(4) . ? N4 C13 1.3508(3) . ? N5 C14 1.3634(4) . ? N5 C15 1.3881(4) . ? N6 C15 1.3161(4) . ? N6 C16 1.3900(4) . ? N7 C15 1.3514(3) . ? N7 C21 1.3888(5) . ? C1 C2 1.3883(4) . ? C1 C6 1.4002(5) . ? C2 C3 1.3844(5) . ? C3 C4 1.4015(5) . ? C4 C5 1.3875(4) . ? C5 C6 1.3959(4) . ? C8 C9 1.4933(4) . ? C9 C10 1.3955(5) . ? C10 C11 1.3798(4) . ? C11 C12 1.3883(5) . ? C12 C13 1.3860(5) . ? C13 C14 1.5098(5) . ? C16 C17 1.3964(5) . ? C16 C21 1.3984(4) . ? C17 C18 1.3868(4) . ? C18 C19 1.3954(4) . ? C19 C20 1.3923(5) . ? C20 C21 1.3886(4) . ? O3 C22 1.2302(4) . ? O4 C23 1.2196(4) . ? O5 C25 1.2258(3) . ? N8 C22 1.3695(4) . ? N8 C23 1.3749(5) . ? N9 C22 1.3714(3) . ? N9 C25 1.3732(4) . ? C23 C24 1.5147(4) . ? C24 C25 1.5232(5) . ? C24 C26 1.5371(6) . ? C24 C28 1.5674(5) . ? C26 C27 1.5244(6) . ? C28 C29 1.5274(5) . ? S1A O6A 1.4996(3) . ? S1A C30A 1.7709(5) . ? S1A C31A 1.7934(5) . ? S1B O6B 1.522(3) . ? S1B C31B 1.718(3) . ? S1B C30B 1.870(4) . ? S2 O7 1.5052(3) . ? S2 C33 1.7868(5) . ? S2 C32 1.7951(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 C7 N1 C1 106.92(3) . . ? C7 N2 C6 104.40(3) . . ? C8 N3 C7 124.01(3) . . ? C9 N4 C13 116.77(3) . . ? C14 N5 C15 123.80(2) . . ? C15 N6 C16 104.67(2) . . ? C15 N7 C21 106.49(2) . . ? N1 C1 C2 131.93(3) . . ? N1 C1 C6 105.42(2) . . ? C2 C1 C6 122.59(3) . . ? C3 C2 C1 116.35(3) . . ? C2 C3 C4 121.95(3) . . ? C5 C4 C3 121.30(3) . . ? C4 C5 C6 117.37(3) . . ? C5 C6 N2 129.86(3) . . ? C5 C6 C1 120.41(3) . . ? N2 C6 C1 109.73(3) . . ? N2 C7 N1 113.54(2) . . ? N2 C7 N3 121.89(3) . . ? N1 C7 N3 124.55(3) . . ? O1 C8 N3 122.85(2) . . ? O1 C8 C9 120.52(3) . . ? N3 C8 C9 116.62(3) . . ? N4 C9 C10 123.17(2) . . ? N4 C9 C8 119.26(3) . . ? C10 C9 C8 117.57(3) . . ? C11 C10 C9 119.27(3) . . ? C10 C11 C12 118.30(3) . . ? C13 C12 C11 118.96(3) . . ? N4 C13 C12 123.50(3) . . ? N4 C13 C14 119.20(3) . . ? C12 C13 C14 117.30(2) . . ? O2 C14 N5 123.77(3) . . ? O2 C14 C13 120.42(3) . . ? N5 C14 C13 115.80(2) . . ? N6 C15 N7 113.79(3) . . ? N6 C15 N5 121.70(2) . . ? N7 C15 N5 124.50(3) . . ? N6 C16 C17 130.10(2) . . ? N6 C16 C21 109.72(3) . . ? C17 C16 C21 120.18(3) . . ? C18 C17 C16 117.37(3) . . ? C17 C18 C19 121.95(3) . . ? C20 C19 C18 121.19(3) . . ? C21 C20 C19 116.61(3) . . ? C20 C21 N7 132.00(3) . . ? C20 C21 C16 122.68(3) . . ? N7 C21 C16 105.32(2) . . ? C22 N8 C23 125.28(2) . . ? C22 N9 C25 125.58(3) . . ? O3 C22 N8 121.46(2) . . ? O3 C22 N9 121.34(3) . . ? N8 C22 N9 117.16(3) . . ? O4 C23 N8 119.71(2) . . ? O4 C23 C24 122.44(3) . . ? N8 C23 C24 117.71(3) . . ? C23 C24 C25 113.17(3) . . ? C23 C24 C26 110.65(3) . . ? C25 C24 C26 110.50(3) . . ? C23 C24 C28 106.72(3) . . ? C25 C24 C28 104.04(3) . . ? C26 C24 C28 111.53(3) . . ? O5 C25 N9 120.20(3) . . ? O5 C25 C24 121.72(3) . . ? N9 C25 C24 118.00(2) . . ? C27 C26 C24 113.49(3) . . ? C29 C28 C24 115.31(3) . . ? O6A S1A C30A 105.510(17) . . ? O6A S1A C31A 105.728(18) . . ? C30A S1A C31A 98.46(2) . . ? O6B S1B C31B 108.04(15) . . ? O6B S1B C30B 120.45(14) . . ? C31B S1B C30B 81.99(16) . . ? O7 S2 C33 105.825(19) . . ? O7 S2 C32 104.332(16) . . ? C33 S2 C32 97.77(2) . . ? 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 N3 H98 O3 0.864(4) 2.132(4) 2.9769(4) 165.5(3) . N5 H97 O3 0.878(3) 2.172(3) 3.0235(3) 163.2(4) . N8 H94 N6 0.946(4) 1.802(4) 2.7406(4) 171.6(5) . N1 H99 O7 0.827(4) 2.046(4) 2.7349(4) 140.4(3) . N1 H99 O1 0.827(4) 2.173(3) 2.6906(3) 120.6(3) . N7 H96 O2 0.881(3) 2.229(4) 2.7198(4) 114.9(3) . N7 H96 O6A 0.881(3) 2.189(3) 2.8586(3) 132.4(4) 1_645 N7 H96 S1B 0.881(3) 2.486(3) 3.2229(6) 141.6(3) 1_645 N9 H95 N2 0.912(5) 1.862(5) 2.7700(4) 173.5(3) . _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.898 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.073 #===END data_2007sot0175 _database_code_depnum_ccdc_archive 'CCDC 651652' _chemical_compound_source 'Matthew Fisher' _database_code_CSD 7SOT0175 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H21 N7 O3 S' _chemical_formula_weight 475.53 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' S S 0.1246 0.1234 '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 19.3932(4) _cell_length_b 5.87740(10) _cell_length_c 19.4872(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.8420(10) _cell_angle_gamma 90.00 _cell_volume 2165.62(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 28999 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Slab _exptl_crystal_colour 'Pale Yellow' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.193 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9256 _exptl_absorpt_correction_T_max 0.9923 _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 20112 reflections reduced R(int) from 0.0841 to 0.0498 Ratio of minimum to maximum apparent transmission: 0.721540 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 29058 _diffrn_reflns_av_R_equivalents 0.0594 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4975 _reflns_number_gt 3961 _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^)+(0.0732P)^2^+0.7640P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.030(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4975 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1377 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 C1 C 0.78162(10) 0.0694(3) 0.42217(9) 0.0214(4) Uani 1 1 d . . . C2 C 0.84514(10) 0.1610(3) 0.41209(10) 0.0250(4) Uani 1 1 d . . . H2 H 0.8464 0.3059 0.3909 0.030 Uiso 1 1 calc R . . C3 C 0.90626(10) 0.0337(4) 0.43403(10) 0.0279(4) Uani 1 1 d . . . H3 H 0.9498 0.0911 0.4267 0.033 Uiso 1 1 calc R . . C4 C 0.90499(11) -0.1780(4) 0.46681(10) 0.0286(4) Uani 1 1 d . . . H4 H 0.9479 -0.2605 0.4813 0.034 Uiso 1 1 calc R . . C5 C 0.84299(10) -0.2704(3) 0.47877(10) 0.0260(4) Uani 1 1 d . . . H5 H 0.8424 -0.4122 0.5020 0.031 Uiso 1 1 calc R . . C6 C 0.78157(10) -0.1438(3) 0.45480(10) 0.0227(4) Uani 1 1 d . . . C7 C 0.67409(10) -0.0023(3) 0.42299(9) 0.0223(4) Uani 1 1 d . . . C8 C 0.55947(10) -0.1466(3) 0.43350(10) 0.0242(4) Uani 1 1 d . . . C9 C 0.48142(10) -0.1028(3) 0.41286(10) 0.0219(4) Uani 1 1 d . . . C10 C 0.43565(11) -0.2452(3) 0.43886(10) 0.0259(4) Uani 1 1 d . . . H10 H 0.4532 -0.3717 0.4678 0.031 Uiso 1 1 calc R . . C11 C 0.36408(10) -0.1977(3) 0.42140(10) 0.0267(4) Uani 1 1 d . . . H11 H 0.3316 -0.2893 0.4391 0.032 Uiso 1 1 calc R . . C12 C 0.34027(10) -0.0142(3) 0.37753(10) 0.0249(4) Uani 1 1 d . . . H12 H 0.2913 0.0217 0.3644 0.030 Uiso 1 1 calc R . . C13 C 0.38999(10) 0.1154(3) 0.35333(9) 0.0200(4) Uani 1 1 d . . . C14 C 0.36580(9) 0.3156(3) 0.30577(9) 0.0198(4) Uani 1 1 d . . . C15 C 0.40947(9) 0.6148(3) 0.24018(9) 0.0194(4) Uani 1 1 d . . . C16 C 0.36056(10) 0.9087(3) 0.17829(9) 0.0200(4) Uani 1 1 d . . . C17 C 0.31839(10) 1.0842(3) 0.14445(10) 0.0232(4) Uani 1 1 d . . . H17 H 0.2698 1.0956 0.1458 0.028 Uiso 1 1 calc R . . C18 C 0.35018(10) 1.2416(3) 0.10875(10) 0.0251(4) Uani 1 1 d . . . H18 H 0.3231 1.3650 0.0854 0.030 Uiso 1 1 calc R . . C19 C 0.42161(11) 1.2223(3) 0.10635(10) 0.0254(4) Uani 1 1 d . . . H19 H 0.4418 1.3324 0.0810 0.030 Uiso 1 1 calc R . . C20 C 0.46336(10) 1.0471(3) 0.14000(10) 0.0236(4) Uani 1 1 d . . . H20 H 0.5116 1.0343 0.1376 0.028 Uiso 1 1 calc R . . C21 C 0.43253(10) 0.8893(3) 0.17770(9) 0.0200(4) Uani 1 1 d . . . C22 C 0.66393(11) 0.2200(4) 0.22734(11) 0.0303(5) Uani 1 1 d . . . H22A H 0.6943 0.1947 0.2741 0.045 Uiso 1 1 calc R . . H22B H 0.6912 0.2958 0.1972 0.045 Uiso 1 1 calc R . . H22C H 0.6464 0.0735 0.2065 0.045 Uiso 1 1 calc R . . C23 C 0.64058(12) 0.6259(4) 0.28050(12) 0.0331(5) Uani 1 1 d . . . H23A H 0.6085 0.7450 0.2897 0.050 Uiso 1 1 calc R . . H23B H 0.6714 0.6881 0.2515 0.050 Uiso 1 1 calc R . . H23C H 0.6695 0.5711 0.3252 0.050 Uiso 1 1 calc R . . N1 N 0.71131(9) -0.1846(3) 0.45539(9) 0.0243(4) Uani 1 1 d . . . N2 N 0.71293(8) 0.1571(3) 0.40309(8) 0.0234(4) Uani 1 1 d . . . N3 N 0.60084(8) 0.0084(3) 0.40964(9) 0.0235(4) Uani 1 1 d . . . N4 N 0.45930(8) 0.0751(3) 0.37086(8) 0.0205(3) Uani 1 1 d . . . N5 N 0.41804(8) 0.4234(3) 0.28278(8) 0.0205(3) Uani 1 1 d . . . N6 N 0.46253(8) 0.7033(3) 0.21753(8) 0.0215(3) Uani 1 1 d . . . N7 N 0.34680(8) 0.7273(3) 0.21902(8) 0.0202(3) Uani 1 1 d . . . H99 H 0.4623(15) 0.357(5) 0.2899(14) 0.055(8) Uiso 1 1 d . . . H97 H 0.3072(14) 0.689(4) 0.2316(13) 0.041(7) Uiso 1 1 d . . . H96 H 0.6919(14) -0.308(5) 0.4705(14) 0.049(8) Uiso 1 1 d . . . H98 H 0.5807(14) 0.113(4) 0.3795(14) 0.045(7) Uiso 1 1 d . . . O1 O 0.58349(7) -0.3101(2) 0.47066(8) 0.0317(4) Uani 1 1 d . . . O2 O 0.30305(7) 0.3732(2) 0.29044(7) 0.0246(3) Uani 1 1 d . . . O3 O 0.55772(7) 0.2817(2) 0.28960(7) 0.0280(3) Uani 1 1 d . . . S1 S 0.59041(2) 0.39605(8) 0.23520(2) 0.02120(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0213(9) 0.0262(10) 0.0161(8) -0.0006(7) 0.0026(7) 0.0009(7) C2 0.0241(10) 0.0271(10) 0.0237(10) -0.0024(8) 0.0050(8) -0.0029(8) C3 0.0209(10) 0.0371(11) 0.0253(10) -0.0084(8) 0.0046(8) -0.0036(8) C4 0.0232(10) 0.0347(11) 0.0259(10) -0.0056(8) 0.0014(8) 0.0041(8) C5 0.0268(10) 0.0267(10) 0.0228(9) 0.0003(8) 0.0024(8) 0.0051(8) C6 0.0235(10) 0.0269(10) 0.0181(9) -0.0009(7) 0.0056(7) -0.0005(7) C7 0.0234(10) 0.0242(9) 0.0195(9) 0.0034(7) 0.0051(7) 0.0022(7) C8 0.0252(10) 0.0253(10) 0.0232(10) 0.0048(8) 0.0073(8) -0.0002(8) C9 0.0222(9) 0.0221(9) 0.0211(9) 0.0015(7) 0.0043(7) -0.0006(7) C10 0.0278(10) 0.0246(10) 0.0243(10) 0.0056(8) 0.0039(8) -0.0044(8) C11 0.0252(10) 0.0287(10) 0.0261(10) 0.0048(8) 0.0054(8) -0.0080(8) C12 0.0210(9) 0.0295(10) 0.0235(9) 0.0015(8) 0.0033(8) -0.0057(8) C13 0.0211(9) 0.0209(9) 0.0189(9) -0.0010(7) 0.0062(7) -0.0028(7) C14 0.0192(9) 0.0212(9) 0.0196(9) -0.0023(7) 0.0056(7) -0.0009(7) C15 0.0186(9) 0.0185(9) 0.0207(9) -0.0007(7) 0.0038(7) 0.0008(7) C16 0.0212(9) 0.0204(9) 0.0184(9) -0.0016(7) 0.0042(7) -0.0013(7) C17 0.0239(10) 0.0238(10) 0.0215(9) 0.0010(7) 0.0042(8) 0.0042(7) C18 0.0296(11) 0.0232(9) 0.0206(9) 0.0034(7) 0.0018(8) 0.0036(8) C19 0.0325(11) 0.0219(9) 0.0213(9) 0.0023(7) 0.0050(8) -0.0052(8) C20 0.0215(9) 0.0249(9) 0.0244(9) -0.0004(8) 0.0054(8) -0.0040(7) C21 0.0189(9) 0.0207(9) 0.0202(9) -0.0013(7) 0.0037(7) -0.0005(7) C22 0.0314(11) 0.0331(11) 0.0283(10) 0.0045(9) 0.0105(9) 0.0077(9) C23 0.0294(11) 0.0306(11) 0.0396(12) -0.0063(9) 0.0086(9) -0.0058(9) N1 0.0227(8) 0.0244(9) 0.0258(8) 0.0050(7) 0.0053(7) 0.0026(7) N2 0.0230(8) 0.0250(8) 0.0213(8) 0.0025(6) 0.0034(6) -0.0001(6) N3 0.0201(8) 0.0256(8) 0.0245(8) 0.0088(7) 0.0044(7) 0.0023(7) N4 0.0202(8) 0.0218(8) 0.0198(8) 0.0007(6) 0.0051(6) -0.0011(6) N5 0.0168(8) 0.0197(8) 0.0256(8) 0.0035(6) 0.0058(6) 0.0011(6) N6 0.0175(8) 0.0204(8) 0.0272(8) 0.0028(6) 0.0062(6) -0.0005(6) N7 0.0168(8) 0.0213(8) 0.0231(8) 0.0035(6) 0.0058(6) 0.0011(6) O1 0.0269(8) 0.0300(8) 0.0383(8) 0.0153(6) 0.0071(6) 0.0007(6) O2 0.0176(7) 0.0270(7) 0.0304(7) 0.0024(6) 0.0078(6) 0.0009(5) O3 0.0215(7) 0.0361(8) 0.0277(7) 0.0123(6) 0.0081(6) 0.0018(6) S1 0.0196(3) 0.0231(3) 0.0217(3) 0.00317(17) 0.00615(18) 0.00055(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.398(3) . ? C1 N2 1.399(2) . ? C1 C6 1.405(3) . ? C2 C3 1.386(3) . ? C3 C4 1.401(3) . ? C4 C5 1.385(3) . ? C5 C6 1.394(3) . ? C6 N1 1.386(2) . ? C7 N2 1.314(2) . ? C7 N1 1.366(2) . ? C7 N3 1.388(2) . ? C8 O1 1.231(2) . ? C8 N3 1.362(2) . ? C8 C9 1.500(3) . ? C9 N4 1.339(2) . ? C9 C10 1.395(3) . ? C10 C11 1.382(3) . ? C11 C12 1.390(3) . ? C12 C13 1.391(3) . ? C13 N4 1.332(2) . ? C13 C14 1.507(3) . ? C14 O2 1.234(2) . ? C14 N5 1.353(2) . ? C15 N6 1.314(2) . ? C15 N7 1.364(2) . ? C15 N5 1.386(2) . ? C16 C17 1.389(3) . ? C16 N7 1.390(2) . ? C16 C21 1.403(3) . ? C17 C18 1.382(3) . ? C18 C19 1.401(3) . ? C19 C20 1.382(3) . ? C20 C21 1.398(3) . ? C21 N6 1.391(2) . ? C22 S1 1.795(2) . ? C23 S1 1.780(2) . ? O3 S1 1.5085(13) . ? 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 C2 C1 N2 129.61(17) . . ? C2 C1 C6 119.75(18) . . ? N2 C1 C6 110.63(16) . . ? C3 C2 C1 117.95(18) . . ? C2 C3 C4 121.28(19) . . ? C5 C4 C3 121.90(19) . . ? C4 C5 C6 116.33(18) . . ? N1 C6 C5 132.33(18) . . ? N1 C6 C1 104.93(16) . . ? C5 C6 C1 122.75(18) . . ? N2 C7 N1 114.66(17) . . ? N2 C7 N3 122.86(17) . . ? N1 C7 N3 122.42(17) . . ? O1 C8 N3 123.26(18) . . ? O1 C8 C9 121.28(17) . . ? N3 C8 C9 115.44(16) . . ? N4 C9 C10 123.21(17) . . ? N4 C9 C8 117.73(16) . . ? C10 C9 C8 119.05(17) . . ? C11 C10 C9 118.34(18) . . ? C10 C11 C12 119.10(17) . . ? C11 C12 C13 118.23(18) . . ? N4 C13 C12 123.48(17) . . ? N4 C13 C14 117.06(15) . . ? C12 C13 C14 119.46(17) . . ? O2 C14 N5 124.19(17) . . ? O2 C14 C13 121.24(16) . . ? N5 C14 C13 114.57(16) . . ? N6 C15 N7 114.73(16) . . ? N6 C15 N5 121.58(16) . . ? N7 C15 N5 123.68(16) . . ? C17 C16 N7 132.33(17) . . ? C17 C16 C21 122.60(17) . . ? N7 C16 C21 105.06(15) . . ? C18 C17 C16 117.04(17) . . ? C17 C18 C19 121.18(18) . . ? C20 C19 C18 121.58(18) . . ? C19 C20 C21 118.04(18) . . ? N6 C21 C20 129.80(17) . . ? N6 C21 C16 110.67(15) . . ? C20 C21 C16 119.53(17) . . ? C7 N1 C6 106.26(16) . . ? C7 N2 C1 103.49(15) . . ? C8 N3 C7 124.17(16) . . ? C13 N4 C9 117.61(16) . . ? C14 N5 C15 125.42(16) . . ? C15 N6 C21 103.68(15) . . ? C15 N7 C16 105.85(15) . . ? O3 S1 C23 104.96(10) . . ? O3 S1 C22 105.60(9) . . ? C23 S1 C22 97.05(10) . . ? 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 N5 H99 O3 0.92(3) 1.90(3) 2.809(2) 166(3) . N5 H99 S1 0.92(3) 2.92(3) 3.6658(16) 139(2) . N7 H97 O2 0.89(3) 2.19(2) 2.741(2) 120(2) . N7 H97 O2 0.89(3) 2.35(3) 2.996(2) 130(2) 2 N1 H96 O1 0.90(3) 2.10(3) 2.666(2) 120(2) . N3 H98 O3 0.88(3) 1.98(3) 2.808(2) 157(2) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.490 _refine_diff_density_min -0.612 _refine_diff_density_rms 0.166 #===END data_2007sot0568 _database_code_depnum_ccdc_archive 'CCDC 651653' _chemical_compound_source 'Matthew Fisher' _database_code_CSD 7SOT0568 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C49 H49.67 N15 O7.34' _chemical_formula_weight 966.06 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5481(3) _cell_length_b 13.6951(4) _cell_length_c 16.4507(6) _cell_angle_alpha 87.777(2) _cell_angle_beta 80.974(2) _cell_angle_gamma 77.225(2) _cell_volume 2288.88(13) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 56716 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Shard _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1015 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9611 _exptl_absorpt_correction_T_max 0.9806 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; ; _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 50681 _diffrn_reflns_av_R_equivalents 0.0708 _diffrn_reflns_av_sigmaI/netI 0.0647 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.48 _reflns_number_total 10471 _reflns_number_gt 7038 _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. The DMF solvent moelcule shows a high degree of thermal motion, the peaks of residual density are located near by. ; _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^)+(0.1482P)^2^+2.8301P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0753(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 10471 _refine_ls_number_parameters 662 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.1353 _refine_ls_R_factor_gt 0.0970 _refine_ls_wR_factor_ref 0.2727 _refine_ls_wR_factor_gt 0.2437 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.108 _refine_ls_shift/su_mean 0.010 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 O1 O 0.45681(9) 0.07052(7) 0.16063(6) 0.0298(3) Uani 1 1 d . . . O2 O 0.74201(9) 0.27186(7) 0.21357(6) 0.0323(3) Uani 1 1 d . . . N1 N 0.24609(11) -0.01395(8) -0.00447(7) 0.0254(3) Uani 1 1 d . . . N2 N 0.31946(10) -0.05661(8) 0.11315(7) 0.0245(3) Uani 1 1 d . . . N3 N 0.37414(10) 0.08827(8) 0.03726(7) 0.0243(3) Uani 1 1 d . . . H103 H 0.3675 0.1237 -0.0083 0.029 Uiso 1 1 calc R . . N4 N 0.56781(10) 0.23167(8) 0.12180(7) 0.0234(3) Uani 1 1 d . . . N5 N 0.72723(10) 0.42974(8) 0.15401(7) 0.0258(3) Uani 1 1 d . . . H105 H 0.6984 0.4704 0.1150 0.031 Uiso 1 1 calc R . . N6 N 0.85991(11) 0.40431(9) 0.26521(7) 0.0301(3) Uani 1 1 d . . . N7 N 0.81614(10) 0.55281(8) 0.20676(7) 0.0272(3) Uani 1 1 d . . . C1 C 0.24337(12) -0.12373(9) 0.10001(8) 0.0249(3) Uani 1 1 d . . . C2 C 0.20986(13) -0.20332(10) 0.14689(9) 0.0279(4) Uani 1 1 d . . . H2 H 0.2413 -0.2215 0.1976 0.033 Uiso 1 1 calc R . . C3 C 0.12837(13) -0.25519(10) 0.11630(9) 0.0310(4) Uani 1 1 d . . . H3 H 0.1029 -0.3098 0.1469 0.037 Uiso 1 1 calc R . . C4 C 0.08311(13) -0.22875(10) 0.04154(9) 0.0318(4) Uani 1 1 d . . . H4 H 0.0279 -0.2662 0.0225 0.038 Uiso 1 1 calc R . . C5 C 0.11627(13) -0.14923(10) -0.00610(9) 0.0306(4) Uani 1 1 d . . . H5 H 0.0859 -0.1320 -0.0573 0.037 Uiso 1 1 calc R . . C6 C 0.19601(12) -0.09645(9) 0.02512(8) 0.0247(3) Uani 1 1 d . . . C7 C 0.22726(14) 0.03773(11) -0.08274(8) 0.0305(4) Uani 1 1 d . . . H7A H 0.1424 0.0858 -0.0759 0.046 Uiso 1 1 calc R . . H7B H 0.2285 -0.0113 -0.1248 0.046 Uiso 1 1 calc R . . H7C H 0.2982 0.0733 -0.0998 0.046 Uiso 1 1 calc R . . C8 C 0.31992(12) 0.01013(9) 0.04986(8) 0.0234(3) Uani 1 1 d . . . C9 C 0.43957(12) 0.11392(9) 0.09393(8) 0.0236(3) Uani 1 1 d . . . C10 C 0.49359(12) 0.20639(9) 0.07052(8) 0.0227(3) Uani 1 1 d . . . C11 C 0.46598(13) 0.26142(9) -0.00046(8) 0.0251(3) Uani 1 1 d . . . H11 H 0.4165 0.2398 -0.0370 0.030 Uiso 1 1 calc R . . C12 C 0.51262(13) 0.34798(10) -0.01591(8) 0.0287(4) Uani 1 1 d . . . H12 H 0.4939 0.3879 -0.0629 0.034 Uiso 1 1 calc R . . C13 C 0.58642(13) 0.37588(10) 0.03738(8) 0.0273(3) Uani 1 1 d . . . H13 H 0.6176 0.4360 0.0284 0.033 Uiso 1 1 calc R . . C14 C 0.61480(12) 0.31481(9) 0.10473(8) 0.0230(3) Uani 1 1 d . . . C15 C 0.70172(13) 0.33701(10) 0.16296(8) 0.0256(3) Uani 1 1 d . . . C16 C 0.79707(12) 0.45753(10) 0.20586(8) 0.0260(3) Uani 1 1 d . . . C17 C 0.76542(14) 0.63416(10) 0.15292(9) 0.0336(4) Uani 1 1 d . . . H17A H 0.7346 0.6069 0.1073 0.050 Uiso 1 1 calc R . . H17B H 0.8354 0.6690 0.1311 0.050 Uiso 1 1 calc R . . H17C H 0.6921 0.6814 0.1842 0.050 Uiso 1 1 calc R . . C18 C 0.89136(13) 0.56068(11) 0.26738(8) 0.0303(4) Uani 1 1 d . . . C19 C 0.93322(14) 0.64175(12) 0.29336(9) 0.0378(4) Uani 1 1 d . . . H19 H 0.9108 0.7063 0.2694 0.045 Uiso 1 1 calc R . . C20 C 1.00954(15) 0.62398(14) 0.35624(10) 0.0463(5) Uani 1 1 d . . . H20 H 1.0406 0.6775 0.3756 0.056 Uiso 1 1 calc R . . C21 C 1.04155(15) 0.52883(15) 0.39162(10) 0.0487(5) Uani 1 1 d . . . H21 H 1.0943 0.5194 0.4343 0.058 Uiso 1 1 calc R . . C22 C 0.99851(14) 0.44776(14) 0.36629(10) 0.0405(5) Uani 1 1 d . . . H22 H 1.0203 0.3833 0.3905 0.049 Uiso 1 1 calc R . . C23 C 0.92145(13) 0.46623(11) 0.30322(9) 0.0313(4) Uani 1 1 d . . . O3 O 0.44267(9) 0.64497(7) 0.22975(6) 0.0300(3) Uani 1 1 d . . . O4 O 0.62920(10) 0.88652(7) 0.33666(6) 0.0311(3) Uani 1 1 d . . . N8 N 0.33236(10) 0.37636(8) 0.25177(7) 0.0233(3) Uani 1 1 d . . . N9 N 0.31548(10) 0.51772(8) 0.18189(7) 0.0252(3) Uani 1 1 d . . . N10 N 0.44304(10) 0.49148(8) 0.29489(7) 0.0233(3) Uani 1 1 d . . . H110 H 0.4705 0.4509 0.3344 0.028 Uiso 1 1 calc R . . N11 N 0.57178(10) 0.70017(7) 0.34424(6) 0.0221(3) Uani 1 1 d . . . N12 N 0.65296(10) 0.87203(8) 0.47451(7) 0.0242(3) Uani 1 1 d . . . H112 H 0.6574 0.8323 0.5178 0.029 Uiso 1 1 calc R . . N13 N 0.66453(10) 1.04005(8) 0.42156(7) 0.0228(3) Uani 1 1 d . . . N14 N 0.67369(10) 1.00576(8) 0.55304(7) 0.0244(3) Uani 1 1 d . . . C24 C 0.24162(12) 0.46086(9) 0.14819(8) 0.0244(3) Uani 1 1 d . . . C25 C 0.16695(13) 0.47919(10) 0.08435(9) 0.0294(4) Uani 1 1 d . . . H25 H 0.1601 0.5393 0.0529 0.035 Uiso 1 1 calc R . . C26 C 0.10286(14) 0.40491(10) 0.06896(9) 0.0320(4) Uani 1 1 d . . . H26 H 0.0502 0.4150 0.0262 0.038 Uiso 1 1 calc R . . C27 C 0.11348(13) 0.31540(10) 0.11455(9) 0.0310(4) Uani 1 1 d . . . H27 H 0.0682 0.2665 0.1020 0.037 Uiso 1 1 calc R . . C28 C 0.18871(13) 0.29717(10) 0.17745(9) 0.0273(3) Uani 1 1 d . . . H28 H 0.1963 0.2368 0.2086 0.033 Uiso 1 1 calc R . . C29 C 0.25283(12) 0.37162(9) 0.19294(8) 0.0235(3) Uani 1 1 d . . . C30 C 0.37274(14) 0.29691(10) 0.30937(9) 0.0296(4) Uani 1 1 d . . . H30A H 0.4319 0.3172 0.3426 0.044 Uiso 1 1 calc R . . H30B H 0.4186 0.2359 0.2789 0.044 Uiso 1 1 calc R . . H30C H 0.2950 0.2840 0.3455 0.044 Uiso 1 1 calc R . . C31 C 0.36969(12) 0.46548(9) 0.24493(8) 0.0221(3) Uani 1 1 d . . . C32 C 0.47494(12) 0.58234(9) 0.28380(8) 0.0228(3) Uani 1 1 d . . . C33 C 0.55193(12) 0.60666(9) 0.34754(8) 0.0209(3) Uani 1 1 d . . . C34 C 0.59142(12) 0.53767(9) 0.40784(8) 0.0235(3) Uani 1 1 d . . . H34 H 0.5769 0.4717 0.4075 0.028 Uiso 1 1 calc R . . C35 C 0.65252(13) 0.56744(10) 0.46848(8) 0.0253(3) Uani 1 1 d . . . H35 H 0.6829 0.5216 0.5097 0.030 Uiso 1 1 calc R . . C36 C 0.66846(12) 0.66540(9) 0.46778(8) 0.0244(3) Uani 1 1 d . . . H36 H 0.7071 0.6885 0.5096 0.029 Uiso 1 1 calc R . . C37 C 0.62685(12) 0.72913(9) 0.40481(8) 0.0209(3) Uani 1 1 d . . . C38 C 0.63714(12) 0.83763(9) 0.40163(8) 0.0228(3) Uani 1 1 d . . . C39 C 0.66167(11) 0.96709(9) 0.47959(8) 0.0224(3) Uani 1 1 d . . . C40 C 0.68369(12) 1.12518(9) 0.45680(8) 0.0226(3) Uani 1 1 d . . . C41 C 0.70037(13) 1.21688(9) 0.42288(9) 0.0271(3) Uani 1 1 d . . . H41 H 0.6940 1.2325 0.3667 0.033 Uiso 1 1 calc R . . C42 C 0.72677(13) 1.28449(10) 0.47520(9) 0.0298(4) Uani 1 1 d . . . H42 H 0.7407 1.3474 0.4539 0.036 Uiso 1 1 calc R . . C43 C 0.73343(13) 1.26275(10) 0.55832(9) 0.0287(4) Uani 1 1 d . . . H43 H 0.7518 1.3111 0.5921 0.034 Uiso 1 1 calc R . . C44 C 0.71375(13) 1.17171(10) 0.59273(9) 0.0282(3) Uani 1 1 d . . . H44 H 0.7163 1.1572 0.6495 0.034 Uiso 1 1 calc R . . C45 C 0.69030(12) 1.10339(9) 0.54028(8) 0.0229(3) Uani 1 1 d . . . C46 C 0.66578(14) 0.95299(10) 0.63138(9) 0.0302(4) Uani 1 1 d . . . H46A H 0.5998 0.9121 0.6342 0.045 Uiso 1 1 calc R . . H46B H 0.6405 1.0016 0.6764 0.045 Uiso 1 1 calc R . . H46C H 0.7516 0.9097 0.6363 0.045 Uiso 1 1 calc R . . O5 O 0.64899(10) 0.09251(7) 0.25909(6) 0.0381(2) Uani 1 1 d D . . H95 H 0.5918(7) 0.0813(7) 0.2321(7) 0.057 Uiso 1 1 d D . . H94 H 0.6714(9) 0.1466(5) 0.2462(10) 0.057 Uiso 1 1 d D . . O6 O 0.48722(10) 0.84680(7) 0.21479(6) 0.0381(2) Uani 1 1 d D . . H97 H 0.5322(8) 0.8625(7) 0.2484(6) 0.057 Uiso 1 1 d D . . H96 H 0.4748(10) 0.7874(5) 0.2248(9) 0.057 Uiso 1 1 d D . . O8 O 0.0894(3) 0.2337(2) 0.46431(19) 0.0381(2) Uani 0.33 1 d PD . . H99 H 0.1051(9) 0.2729(7) 0.4989(7) 0.057 Uiso 0.33 1 d PD . . H98 H 0.0114(7) 0.2237(10) 0.4781(14) 0.057 Uiso 0.33 1 d PD . . O7 O 0.00355(16) 0.20531(13) 0.32691(12) 0.0862(6) Uani 1 1 d . . . N15 N -0.01501(16) 0.04623(18) 0.30719(11) 0.1050(7) Uani 1 1 d U . . C48 C -0.0342(3) -0.0517(2) 0.3235(2) 0.1638(13) Uani 1 1 d U . . H48A H -0.0381 -0.0656 0.3826 0.246 Uiso 1 1 calc R . . H48B H 0.0391 -0.0998 0.2931 0.246 Uiso 1 1 calc R . . H48C H -0.1168 -0.0578 0.3062 0.246 Uiso 1 1 calc R . . C49 C -0.0042(2) 0.1157(3) 0.3524(2) 0.1117(13) Uani 1 1 d U . . H49 H -0.0016 0.1012 0.4092 0.134 Uiso 1 1 calc R . . C47 C -0.0082(3) 0.0704(3) 0.2179(2) 0.1097(13) Uani 1 1 d . . . H47A H -0.0502 0.1409 0.2108 0.164 Uiso 1 1 calc R . . H47B H -0.0538 0.0278 0.1920 0.164 Uiso 1 1 calc R . . H47C H 0.0841 0.0584 0.1919 0.164 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 O1 0.0408(5) 0.0269(4) 0.0256(4) 0.0070(4) -0.0106(4) -0.0131(4) O2 0.0369(5) 0.0305(5) 0.0318(5) 0.0051(4) -0.0123(4) -0.0081(4) N1 0.0291(5) 0.0239(5) 0.0233(5) 0.0010(4) -0.0055(4) -0.0051(4) N2 0.0304(5) 0.0216(5) 0.0219(5) -0.0011(4) -0.0028(4) -0.0070(4) N3 0.0300(5) 0.0218(5) 0.0212(5) -0.0002(4) -0.0039(4) -0.0053(4) N4 0.0271(5) 0.0229(5) 0.0202(5) -0.0014(4) -0.0035(4) -0.0053(4) N5 0.0298(5) 0.0266(5) 0.0227(5) 0.0014(4) -0.0060(4) -0.0087(4) N6 0.0280(5) 0.0392(6) 0.0235(5) -0.0021(5) -0.0050(4) -0.0069(5) N7 0.0280(5) 0.0329(5) 0.0230(5) -0.0028(4) -0.0022(4) -0.0124(4) C1 0.0249(5) 0.0223(5) 0.0266(6) -0.0039(5) -0.0015(5) -0.0045(5) C2 0.0290(6) 0.0270(6) 0.0268(6) -0.0040(5) -0.0025(5) -0.0049(5) C3 0.0292(6) 0.0259(6) 0.0368(7) -0.0047(6) 0.0013(6) -0.0075(5) C4 0.0295(6) 0.0303(6) 0.0370(7) -0.0070(6) -0.0028(6) -0.0100(5) C5 0.0294(6) 0.0325(6) 0.0314(7) -0.0069(6) -0.0068(5) -0.0069(5) C6 0.0247(5) 0.0217(5) 0.0262(6) -0.0052(5) -0.0009(5) -0.0034(5) C7 0.0356(6) 0.0343(7) 0.0220(6) 0.0030(5) -0.0069(5) -0.0070(5) C8 0.0254(5) 0.0221(5) 0.0220(6) -0.0039(5) -0.0030(5) -0.0035(5) C9 0.0249(5) 0.0209(5) 0.0244(6) -0.0021(5) -0.0032(5) -0.0037(5) C10 0.0239(5) 0.0226(5) 0.0202(6) -0.0010(5) -0.0012(5) -0.0034(5) C11 0.0281(6) 0.0262(6) 0.0212(6) -0.0017(5) -0.0048(5) -0.0059(5) C12 0.0352(6) 0.0302(6) 0.0222(6) 0.0055(5) -0.0062(5) -0.0099(5) C13 0.0317(6) 0.0247(6) 0.0257(6) 0.0024(5) -0.0007(5) -0.0096(5) C14 0.0244(5) 0.0216(5) 0.0221(6) -0.0006(5) 0.0003(5) -0.0059(4) C15 0.0262(6) 0.0270(6) 0.0222(6) -0.0021(5) -0.0006(5) -0.0050(5) C16 0.0250(6) 0.0316(6) 0.0214(6) -0.0031(5) 0.0012(5) -0.0088(5) C17 0.0406(7) 0.0346(6) 0.0303(7) 0.0012(6) -0.0061(6) -0.0182(5) C18 0.0249(6) 0.0458(7) 0.0220(6) -0.0051(6) 0.0004(5) -0.0131(5) C19 0.0346(6) 0.0538(8) 0.0297(7) -0.0070(6) -0.0025(6) -0.0201(6) C20 0.0384(7) 0.0696(9) 0.0379(8) -0.0119(7) -0.0032(6) -0.0268(6) C21 0.0313(7) 0.0839(11) 0.0367(8) -0.0101(8) -0.0120(6) -0.0182(7) C22 0.0302(6) 0.0618(9) 0.0303(7) -0.0020(7) -0.0068(6) -0.0102(6) C23 0.0228(6) 0.0443(7) 0.0264(7) -0.0052(6) 0.0002(5) -0.0081(5) O3 0.0442(5) 0.0229(4) 0.0281(4) 0.0045(4) -0.0164(4) -0.0119(4) O4 0.0471(5) 0.0247(4) 0.0262(5) 0.0027(4) -0.0115(4) -0.0143(4) N8 0.0299(5) 0.0206(4) 0.0205(5) -0.0009(4) -0.0032(4) -0.0079(4) N9 0.0322(5) 0.0222(5) 0.0244(5) -0.0004(4) -0.0108(4) -0.0078(4) N10 0.0277(5) 0.0198(5) 0.0230(5) 0.0003(4) -0.0077(4) -0.0038(4) N11 0.0262(5) 0.0202(4) 0.0208(5) -0.0018(4) -0.0039(4) -0.0067(4) N12 0.0301(5) 0.0205(5) 0.0232(5) 0.0012(4) -0.0057(4) -0.0072(4) N13 0.0257(5) 0.0200(5) 0.0228(5) -0.0025(4) -0.0048(4) -0.0041(4) N14 0.0299(5) 0.0225(5) 0.0227(5) -0.0015(4) -0.0080(4) -0.0071(4) C24 0.0261(5) 0.0226(5) 0.0259(6) -0.0033(5) -0.0042(5) -0.0075(4) C25 0.0358(6) 0.0253(6) 0.0294(6) -0.0005(5) -0.0110(5) -0.0077(5) C26 0.0341(6) 0.0312(6) 0.0334(7) -0.0060(6) -0.0126(5) -0.0070(5) C27 0.0308(6) 0.0303(6) 0.0343(7) -0.0083(6) -0.0053(5) -0.0101(5) C28 0.0309(6) 0.0255(6) 0.0271(6) -0.0051(5) -0.0026(5) -0.0102(5) C29 0.0236(5) 0.0237(5) 0.0225(6) -0.0048(5) -0.0006(5) -0.0047(5) C30 0.0403(7) 0.0222(6) 0.0276(7) 0.0033(5) -0.0067(6) -0.0092(5) C31 0.0238(5) 0.0198(5) 0.0221(6) -0.0039(5) -0.0020(5) -0.0042(4) C32 0.0267(5) 0.0198(5) 0.0216(6) -0.0016(5) -0.0052(5) -0.0033(4) C33 0.0224(5) 0.0205(5) 0.0194(6) -0.0032(5) -0.0027(4) -0.0036(4) C34 0.0265(6) 0.0206(5) 0.0235(6) -0.0022(5) -0.0043(5) -0.0043(4) C35 0.0293(6) 0.0240(6) 0.0228(6) 0.0025(5) -0.0075(5) -0.0040(5) C36 0.0288(6) 0.0254(6) 0.0203(6) -0.0009(5) -0.0044(5) -0.0084(5) C37 0.0219(5) 0.0197(5) 0.0211(6) -0.0034(5) -0.0024(5) -0.0047(4) C38 0.0239(5) 0.0210(5) 0.0235(6) -0.0020(5) -0.0027(5) -0.0051(4) C39 0.0209(5) 0.0243(5) 0.0226(6) -0.0019(5) -0.0052(5) -0.0043(4) C40 0.0229(5) 0.0203(5) 0.0247(6) -0.0018(5) -0.0054(5) -0.0038(4) C41 0.0278(6) 0.0214(6) 0.0319(7) 0.0006(5) -0.0057(5) -0.0039(5) C42 0.0271(6) 0.0210(6) 0.0414(8) -0.0006(6) -0.0052(6) -0.0052(5) C43 0.0257(6) 0.0231(6) 0.0378(7) -0.0078(5) -0.0074(5) -0.0035(5) C44 0.0285(6) 0.0285(6) 0.0294(6) -0.0059(5) -0.0075(5) -0.0066(5) C45 0.0220(5) 0.0208(5) 0.0271(6) -0.0016(5) -0.0074(5) -0.0045(4) C46 0.0392(7) 0.0263(6) 0.0271(6) -0.0001(5) -0.0093(5) -0.0083(5) O5 0.0571(4) 0.0283(3) 0.0354(3) 0.0059(3) -0.0204(3) -0.0150(3) O6 0.0571(4) 0.0283(3) 0.0354(3) 0.0059(3) -0.0204(3) -0.0150(3) O8 0.0571(4) 0.0283(3) 0.0354(3) 0.0059(3) -0.0204(3) -0.0150(3) O7 0.0671(9) 0.0878(11) 0.0925(12) 0.0205(10) 0.0100(9) -0.0124(8) N15 0.0310(7) 0.1908(17) 0.0868(9) -0.0919(9) -0.0209(7) 0.0130(10) C48 0.0612(13) 0.1175(18) 0.243(3) 0.1063(18) 0.0758(15) 0.0403(13) C49 0.0516(12) 0.178(3) 0.0961(19) 0.038(2) -0.0181(13) -0.0078(16) C47 0.0920(19) 0.128(2) 0.102(2) 0.011(2) -0.0199(17) -0.0077(18) _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 O1 C9 1.2469(16) . ? O2 C15 1.2473(16) . ? N1 C8 1.3670(18) . ? N1 C6 1.3903(18) . ? N1 C7 1.4649(17) . ? N2 C8 1.3587(17) . ? N2 C1 1.3899(19) . ? N3 C8 1.3158(18) . ? N3 C9 1.3428(18) . ? N4 C10 1.3396(18) . ? N4 C14 1.3425(17) . ? N5 C16 1.3272(19) . ? N5 C15 1.3531(18) . ? N6 C16 1.3630(18) . ? N6 C23 1.394(2) . ? N7 C16 1.3646(18) . ? N7 C18 1.3891(19) . ? N7 C17 1.4562(18) . ? C1 C2 1.3884(19) . ? C1 C6 1.4078(19) . ? C2 C3 1.389(2) . ? C3 C4 1.395(2) . ? C4 C5 1.392(2) . ? C5 C6 1.388(2) . ? C9 C10 1.5129(19) . ? C10 C11 1.3991(18) . ? C11 C12 1.381(2) . ? C12 C13 1.376(2) . ? C13 C14 1.3921(18) . ? C14 C15 1.507(2) . ? C18 C19 1.387(2) . ? C18 C23 1.393(2) . ? C19 C20 1.390(2) . ? C20 C21 1.400(3) . ? C21 C22 1.389(3) . ? C22 C23 1.398(2) . ? O3 C32 1.2445(15) . ? O4 C38 1.2431(16) . ? N8 C31 1.3584(17) . ? N8 C29 1.3886(18) . ? N8 C30 1.4508(17) . ? N9 C31 1.3646(17) . ? N9 C24 1.3994(19) . ? N10 C31 1.3209(18) . ? N10 C32 1.3576(17) . ? N11 C33 1.3402(17) . ? N11 C37 1.3423(18) . ? N12 C39 1.3319(17) . ? N12 C38 1.3522(18) . ? N13 C39 1.3568(16) . ? N13 C40 1.3891(17) . ? N14 C39 1.3726(17) . ? N14 C45 1.3901(17) . ? N14 C46 1.4528(17) . ? C24 C25 1.392(2) . ? C24 C29 1.3940(18) . ? C25 C26 1.391(2) . ? C26 C27 1.404(2) . ? C27 C28 1.383(2) . ? C28 C29 1.393(2) . ? C32 C33 1.5113(19) . ? C33 C34 1.3903(18) . ? C34 C35 1.388(2) . ? C35 C36 1.3879(19) . ? C36 C37 1.3894(18) . ? C37 C38 1.5120(18) . ? C40 C41 1.3899(18) . ? C40 C45 1.4032(19) . ? C41 C42 1.388(2) . ? C42 C43 1.397(2) . ? C43 C44 1.3931(19) . ? C44 C45 1.383(2) . ? O7 C49 1.297(4) . ? N15 C49 1.266(4) . ? N15 C48 1.409(4) . ? N15 C47 1.488(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 C8 N1 C6 109.35(11) . . ? C8 N1 C7 124.76(12) . . ? C6 N1 C7 125.86(12) . . ? C8 N2 C1 109.23(11) . . ? C8 N3 C9 119.96(11) . . ? C10 N4 C14 118.03(11) . . ? C16 N5 C15 118.04(12) . . ? C16 N6 C23 109.08(12) . . ? C16 N7 C18 109.49(11) . . ? C16 N7 C17 125.53(12) . . ? C18 N7 C17 124.97(12) . . ? C2 C1 N2 131.58(13) . . ? C2 C1 C6 121.41(13) . . ? N2 C1 C6 106.99(11) . . ? C1 C2 C3 117.03(13) . . ? C2 C3 C4 121.37(13) . . ? C5 C4 C3 122.12(14) . . ? C6 C5 C4 116.48(14) . . ? C5 C6 N1 132.06(13) . . ? C5 C6 C1 121.57(13) . . ? N1 C6 C1 106.37(12) . . ? N3 C8 N2 130.84(13) . . ? N3 C8 N1 121.08(12) . . ? N2 C8 N1 108.05(12) . . ? O1 C9 N3 126.75(13) . . ? O1 C9 C10 120.09(12) . . ? N3 C9 C10 113.16(11) . . ? N4 C10 C11 122.86(12) . . ? N4 C10 C9 115.95(11) . . ? C11 C10 C9 121.19(12) . . ? C12 C11 C10 118.20(13) . . ? C13 C12 C11 119.37(13) . . ? C12 C13 C14 119.08(13) . . ? N4 C14 C13 122.36(13) . . ? N4 C14 C15 115.43(11) . . ? C13 C14 C15 122.21(12) . . ? O2 C15 N5 126.49(14) . . ? O2 C15 C14 119.43(12) . . ? N5 C15 C14 114.08(11) . . ? N5 C16 N6 130.41(13) . . ? N5 C16 N7 121.97(12) . . ? N6 C16 N7 107.62(12) . . ? C19 C18 N7 131.18(13) . . ? C19 C18 C23 122.10(14) . . ? N7 C18 C23 106.71(13) . . ? C18 C19 C20 116.74(15) . . ? C19 C20 C21 121.32(17) . . ? C22 C21 C20 122.03(16) . . ? C21 C22 C23 116.35(16) . . ? C18 C23 N6 107.05(13) . . ? C18 C23 C22 121.44(15) . . ? N6 C23 C22 131.50(15) . . ? C31 N8 C29 109.29(10) . . ? C31 N8 C30 125.56(12) . . ? C29 N8 C30 125.11(11) . . ? C31 N9 C24 109.29(11) . . ? C31 N10 C32 118.34(11) . . ? C33 N11 C37 117.64(11) . . ? C39 N12 C38 118.81(11) . . ? C39 N13 C40 109.26(11) . . ? C39 N14 C45 109.02(11) . . ? C39 N14 C46 124.73(11) . . ? C45 N14 C46 126.22(11) . . ? C25 C24 C29 121.27(13) . . ? C25 C24 N9 132.49(12) . . ? C29 C24 N9 106.24(12) . . ? C26 C25 C24 116.52(13) . . ? C25 C26 C27 122.10(14) . . ? C28 C27 C26 121.16(14) . . ? C27 C28 C29 116.75(12) . . ? N8 C29 C28 130.41(12) . . ? N8 C29 C24 107.38(12) . . ? C28 C29 C24 122.19(13) . . ? N10 C31 N8 122.39(11) . . ? N10 C31 N9 129.79(12) . . ? N8 C31 N9 107.80(12) . . ? O3 C32 N10 126.25(13) . . ? O3 C32 C33 119.99(12) . . ? N10 C32 C33 113.71(11) . . ? N11 C33 C34 123.26(12) . . ? N11 C33 C32 115.24(11) . . ? C34 C33 C32 121.38(12) . . ? C35 C34 C33 118.49(12) . . ? C36 C35 C34 118.77(12) . . ? C35 C36 C37 118.85(13) . . ? N11 C37 C36 122.89(12) . . ? N11 C37 C38 115.36(11) . . ? C36 C37 C38 121.72(12) . . ? O4 C38 N12 126.34(12) . . ? O4 C38 C37 120.35(12) . . ? N12 C38 C37 113.30(11) . . ? N12 C39 N13 131.37(12) . . ? N12 C39 N14 120.62(11) . . ? N13 C39 N14 107.98(11) . . ? N13 C40 C41 131.48(12) . . ? N13 C40 C45 107.07(11) . . ? C41 C40 C45 121.40(13) . . ? C42 C41 C40 116.68(13) . . ? C41 C42 C43 121.90(13) . . ? C44 C43 C42 121.39(14) . . ? C45 C44 C43 116.77(13) . . ? C44 C45 N14 131.54(12) . . ? C44 C45 C40 121.83(12) . . ? N14 C45 C40 106.59(11) . . ? C49 N15 C48 133.3(3) . . ? C49 N15 C47 115.5(3) . . ? C48 N15 C47 111.2(3) . . ? N15 C49 O7 124.7(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 O5 H95 O1 0.846(9) 2.015(9) 2.8568(16) 173.0(10) . O5 H94 O2 0.836(8) 2.038(8) 2.8721(15) 175.2(8) . O5 H94 N4 0.836(8) 2.587(14) 3.0028(15) 112.1(11) . O6 H97 O4 0.846(9) 1.978(9) 2.8187(16) 172.7(9) . O6 H96 O3 0.857(8) 2.049(8) 2.8994(14) 171.1(14) . O6 H96 N11 0.857(8) 2.499(14) 2.9723(14) 115.7(11) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.865 _refine_diff_density_min -1.038 _refine_diff_density_rms 0.244 #==END