# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Hans-Joachim Knolker' _publ_contact_author_email HANS-JOACHIM.KNOELKER@CHEMIE.TU-DRESDEN.DE _publ_section_title ; First total synthesis of the whole series of the antiostatins A and B ; loop_ _publ_author_name 'Hans-Joachim Knolker' 'Stefan Auschill' 'Anne Jager' 'Kerstin E. Knott' # Attachment 'an75.cif' data_an75 _database_code_depnum_ccdc_archive 'CCDC 708519' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H28 N2 O' _chemical_formula_sum 'C21 H28 N2 O' _chemical_formula_weight 324.45 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.921(3) _cell_length_b 4.739(1) _cell_length_c 26.736(5) _cell_angle_alpha 90.00 _cell_angle_beta 113.91(3) _cell_angle_gamma 90.00 _cell_volume 1844.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used 475 _cell_measurement_theta_min 4.096 _cell_measurement_theta_max 23.513 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9022 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details 'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)' _publ_section_references ; !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! These references have to be cited in the publication, because they named software was used for measurement, evaluation of data, solution, refinement and computing the publication material of the structure. They are in ACTACC-format and need to be changed for publication in another journal. !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 331-334. Burla, M. C., Caliandro, R.,Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388. Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96. Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999). WinGX. J. Appl. Cryst. 32, 837-838. Hall, S. R., Allen, F. H. & Brown, I. D. (1991). Acta Cryst. A47, 655-685. Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands. Sheldrick, G. M. (1997). SHELX97. Programs for Crystal Structure Analysis (Release 97-2). University of G\"ottingen, Germany. Sheldrick, G. M. (2002). SADABS, Version 2.10, Bruker Analytical X-Ray Systems, Inc.: Madison, WI. Spek, A. L. (2005). PLATON, A Multipurpose Crystallographic Tool. Utrecht University, Utrecht, The Netherlands. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27882 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3615 _reflns_number_gt 2272 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1999)' _computing_cell_refinement 'Dirax/lsq (Duisenberg, 1992)' _computing_data_reduction 'EvalCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)' _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^)+(0.0485P)^2^+0.6995P] 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 3615 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1027 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1269 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 -0.19953(12) 0.2755(4) 0.07660(8) 0.0367(5) Uani 1 1 d . . . C2 C -0.22457(13) 0.4301(4) 0.02831(8) 0.0409(5) Uani 1 1 d . . . C21 C -0.31803(14) 0.3949(6) -0.01780(9) 0.0592(7) Uani 1 1 d . . . H21A H -0.3287 0.5483 -0.0443 0.089 Uiso 1 1 calc R . . H21B H -0.3653 0.4001 -0.0031 0.089 Uiso 1 1 calc R . . H21C H -0.3208 0.2134 -0.0360 0.089 Uiso 1 1 calc R . . C3 C -0.16277(13) 0.6224(4) 0.02197(8) 0.0392(5) Uani 1 1 d . . . O3 O -0.18872(9) 0.7775(3) -0.02640(5) 0.0501(4) Uani 1 1 d . . . C31 C -0.16299(16) 0.6374(6) -0.06566(9) 0.0604(7) Uani 1 1 d . . . H31A H -0.0967 0.6005 -0.0494 0.091 Uiso 1 1 calc R . . H31B H -0.1783 0.7577 -0.0980 0.091 Uiso 1 1 calc R . . H31C H -0.1963 0.4584 -0.0764 0.091 Uiso 1 1 calc R . . C4 C -0.07626(13) 0.6774(4) 0.06266(8) 0.0355(5) Uani 1 1 d . . . N4 N -0.01770(14) 0.8739(4) 0.05424(9) 0.0444(5) Uani 1 1 d . . . H4A H 0.0197(14) 0.974(5) 0.0862(9) 0.051(7) Uiso 1 1 d . . . H4B H -0.0482(15) 0.992(5) 0.0279(10) 0.063(8) Uiso 1 1 d . . . C4A C -0.04884(12) 0.5162(4) 0.11054(7) 0.0332(4) Uani 1 1 d . . . C4B C 0.03639(12) 0.4908(4) 0.15845(8) 0.0337(5) Uani 1 1 d . . . C5 C 0.12328(13) 0.6167(4) 0.17664(8) 0.0405(5) Uani 1 1 d . . . H5 H 0.1351 0.7602 0.1555 0.049 Uiso 1 1 calc R . . C6 C 0.19144(14) 0.5307(5) 0.22541(9) 0.0465(6) Uani 1 1 d . . . H6 H 0.2505 0.6154 0.2377 0.056 Uiso 1 1 calc R . . C7 C 0.17536(14) 0.3231(5) 0.25685(9) 0.0459(5) Uani 1 1 d . . . H7 H 0.2238 0.2675 0.2902 0.055 Uiso 1 1 calc R . . C8 C 0.09058(13) 0.1949(5) 0.24078(8) 0.0420(5) Uani 1 1 d . . . H8 H 0.0796 0.0535 0.2626 0.050 Uiso 1 1 calc R . . C8A C 0.02209(13) 0.2802(4) 0.19162(8) 0.0353(5) Uani 1 1 d . . . N9 N -0.06740(11) 0.1840(4) 0.16604(7) 0.0377(4) Uani 1 1 d . . . H9 H -0.0914(13) 0.049(5) 0.1790(8) 0.047(6) Uiso 1 1 d . . . C9A C -0.11107(12) 0.3207(4) 0.11625(8) 0.0334(5) Uani 1 1 d . . . C10 C -0.26488(13) 0.0779(4) 0.08714(8) 0.0412(5) Uani 1 1 d . . . H10A H -0.2293 -0.0739 0.1122 0.049 Uiso 1 1 calc R . . H10B H -0.3059 -0.0109 0.0522 0.049 Uiso 1 1 calc R . . C11 C -0.32314(13) 0.2299(4) 0.11217(9) 0.0436(5) Uani 1 1 d . . . H11A H -0.2820 0.3040 0.1485 0.052 Uiso 1 1 calc R . . H11B H -0.3534 0.3934 0.0888 0.052 Uiso 1 1 calc R . . C12 C -0.39633(13) 0.0483(5) 0.11898(9) 0.0440(5) Uani 1 1 d . . . H12A H -0.4371 -0.0286 0.0828 0.053 Uiso 1 1 calc R . . H12B H -0.3662 -0.1131 0.1431 0.053 Uiso 1 1 calc R . . C13 C -0.45431(13) 0.2062(5) 0.14292(9) 0.0461(5) Uani 1 1 d . . . H13A H -0.4129 0.3009 0.1770 0.055 Uiso 1 1 calc R . . H13B H -0.4895 0.3547 0.1168 0.055 Uiso 1 1 calc R . . C14 C -0.52082(13) 0.0232(5) 0.15563(9) 0.0467(5) Uani 1 1 d . . . H14A H -0.5591 -0.0824 0.1222 0.056 Uiso 1 1 calc R . . H14B H -0.4852 -0.1167 0.1838 0.056 Uiso 1 1 calc R . . C15 C -0.58333(15) 0.1801(5) 0.17567(10) 0.0556(6) Uani 1 1 d . . . H15A H -0.6197 0.3185 0.1474 0.067 Uiso 1 1 calc R . . H15B H -0.5453 0.2868 0.2090 0.067 Uiso 1 1 calc R . . C16 C -0.64862(15) -0.0088(6) 0.18856(11) 0.0676(7) Uani 1 1 d . . . H16A H -0.6878 -0.1114 0.1555 0.101 Uiso 1 1 calc R . . H16B H -0.6870 0.1066 0.2014 0.101 Uiso 1 1 calc R . . H16C H -0.6133 -0.1438 0.2171 0.101 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 C1 0.0369(11) 0.0364(11) 0.0444(12) -0.0099(10) 0.0242(10) -0.0039(9) C2 0.0381(11) 0.0472(13) 0.0417(12) -0.0091(10) 0.0207(10) -0.0001(10) C21 0.0456(13) 0.0767(18) 0.0520(14) -0.0055(13) 0.0164(11) -0.0049(12) C3 0.0438(12) 0.0409(12) 0.0380(12) -0.0014(10) 0.0220(10) 0.0073(10) O3 0.0531(9) 0.0587(10) 0.0440(8) 0.0084(8) 0.0252(7) 0.0121(8) C31 0.0630(15) 0.0812(18) 0.0461(13) 0.0004(13) 0.0315(12) 0.0048(13) C4 0.0403(11) 0.0327(11) 0.0443(12) -0.0046(10) 0.0282(10) 0.0004(9) N4 0.0482(11) 0.0432(11) 0.0497(12) 0.0046(10) 0.0280(10) -0.0032(10) C4A 0.0368(11) 0.0317(10) 0.0376(11) -0.0049(9) 0.0218(9) -0.0013(9) C4B 0.0378(11) 0.0322(10) 0.0401(11) -0.0065(9) 0.0249(9) -0.0008(9) C5 0.0412(12) 0.0393(12) 0.0489(13) -0.0056(10) 0.0266(11) -0.0064(9) C6 0.0373(12) 0.0521(14) 0.0520(13) -0.0097(12) 0.0200(11) -0.0069(10) C7 0.0415(12) 0.0525(14) 0.0439(12) -0.0015(11) 0.0174(10) 0.0048(11) C8 0.0471(12) 0.0424(12) 0.0420(12) 0.0001(10) 0.0238(11) 0.0011(10) C8A 0.0380(11) 0.0344(11) 0.0404(11) -0.0068(9) 0.0231(10) -0.0021(9) N9 0.0410(10) 0.0349(10) 0.0445(10) -0.0008(8) 0.0248(8) -0.0076(8) C9A 0.0377(11) 0.0315(10) 0.0380(11) -0.0052(9) 0.0226(9) -0.0019(9) C10 0.0383(11) 0.0405(12) 0.0497(12) -0.0094(10) 0.0230(10) -0.0061(9) C11 0.0416(11) 0.0422(12) 0.0539(13) -0.0064(11) 0.0266(10) -0.0056(10) C12 0.0366(11) 0.0462(13) 0.0542(13) -0.0067(11) 0.0234(10) -0.0056(10) C13 0.0402(11) 0.0478(13) 0.0561(13) -0.0014(11) 0.0255(10) -0.0008(10) C14 0.0406(12) 0.0505(13) 0.0547(13) -0.0023(11) 0.0252(10) -0.0038(10) C15 0.0480(13) 0.0597(15) 0.0683(15) 0.0001(13) 0.0329(12) 0.0003(11) C16 0.0539(14) 0.0772(18) 0.0889(18) 0.0103(15) 0.0467(14) 0.0040(13) _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 C9A 1.394(3) . ? C1 C2 1.395(3) . ? C1 C10 1.509(3) . ? C2 C3 1.401(3) . ? C2 C21 1.508(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C3 C4 1.391(3) . ? C3 O3 1.397(2) . ? O3 C31 1.435(2) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C4 N4 1.399(2) . ? C4 C4A 1.400(3) . ? N4 H4A 0.95(2) . ? N4 H4B 0.88(2) . ? C4A C9A 1.409(3) . ? C4A C4B 1.445(3) . ? C4B C5 1.400(3) . ? C4B C8A 1.413(3) . ? C5 C6 1.377(3) . ? C5 H5 0.9500 . ? C6 C7 1.384(3) . ? C6 H6 0.9500 . ? C7 C8 1.380(3) . ? C7 H7 0.9500 . ? C8 C8A 1.385(3) . ? C8 H8 0.9500 . ? C8A N9 1.384(2) . ? N9 C9A 1.387(2) . ? N9 H9 0.89(2) . ? C10 C11 1.527(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.518(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.517(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.510(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.504(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.514(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9A C1 C2 116.43(17) . . ? C9A C1 C10 120.93(18) . . ? C2 C1 C10 122.60(17) . . ? C1 C2 C3 120.15(18) . . ? C1 C2 C21 121.05(19) . . ? C3 C2 C21 118.79(19) . . ? C2 C21 H21A 109.5 . . ? C2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C4 C3 O3 116.96(17) . . ? C4 C3 C2 123.28(18) . . ? O3 C3 C2 119.72(18) . . ? C3 O3 C31 111.66(16) . . ? O3 C31 H31A 109.5 . . ? O3 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O3 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C3 C4 N4 120.80(19) . . ? C3 C4 C4A 117.14(17) . . ? N4 C4 C4A 121.95(18) . . ? C4 N4 H4A 113.8(13) . . ? C4 N4 H4B 111.5(15) . . ? H4A N4 H4B 110(2) . . ? C4 C4A C9A 119.04(17) . . ? C4 C4A C4B 133.53(17) . . ? C9A C4A C4B 107.35(16) . . ? C5 C4B C8A 118.08(18) . . ? C5 C4B C4A 135.48(18) . . ? C8A C4B C4A 106.42(16) . . ? C6 C5 C4B 119.41(19) . . ? C6 C5 H5 120.3 . . ? C4B C5 H5 120.3 . . ? C5 C6 C7 121.11(19) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C8 C7 C6 121.5(2) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C8A 117.5(2) . . ? C7 C8 H8 121.3 . . ? C8A C8 H8 121.3 . . ? N9 C8A C8 129.02(18) . . ? N9 C8A C4B 108.53(17) . . ? C8 C8A C4B 122.44(18) . . ? C8A N9 C9A 109.61(17) . . ? C8A N9 H9 124.4(13) . . ? C9A N9 H9 125.9(13) . . ? N9 C9A C1 128.10(17) . . ? N9 C9A C4A 108.05(16) . . ? C1 C9A C4A 123.82(18) . . ? C1 C10 C11 112.11(16) . . ? C1 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? C1 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C12 C11 C10 114.68(17) . . ? C12 C11 H11A 108.6 . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11B 108.6 . . ? C10 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C13 C12 C11 113.53(17) . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C12 114.45(18) . . ? C14 C13 H13A 108.6 . . ? C12 C13 H13A 108.6 . . ? C14 C13 H13B 108.6 . . ? C12 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? C15 C14 C13 114.93(19) . . ? C15 C14 H14A 108.5 . . ? C13 C14 H14A 108.5 . . ? C15 C14 H14B 108.5 . . ? C13 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? C14 C15 C16 113.8(2) . . ? C14 C15 H15A 108.8 . . ? C16 C15 H15A 108.8 . . ? C14 C15 H15B 108.8 . . ? C16 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9A C1 C2 C3 -1.2(3) . . . . ? C10 C1 C2 C3 176.39(17) . . . . ? C9A C1 C2 C21 179.00(18) . . . . ? C10 C1 C2 C21 -3.4(3) . . . . ? C1 C2 C3 C4 -2.1(3) . . . . ? C21 C2 C3 C4 177.76(19) . . . . ? C1 C2 C3 O3 -179.59(17) . . . . ? C21 C2 C3 O3 0.2(3) . . . . ? C4 C3 O3 C31 90.4(2) . . . . ? C2 C3 O3 C31 -91.9(2) . . . . ? O3 C3 C4 N4 -1.8(3) . . . . ? C2 C3 C4 N4 -179.36(18) . . . . ? O3 C3 C4 C4A -178.05(16) . . . . ? C2 C3 C4 C4A 4.4(3) . . . . ? C3 C4 C4A C9A -3.4(3) . . . . ? N4 C4 C4A C9A -179.63(17) . . . . ? C3 C4 C4A C4B 173.01(19) . . . . ? N4 C4 C4A C4B -3.2(3) . . . . ? C4 C4A C4B C5 1.5(4) . . . . ? C9A C4A C4B C5 178.2(2) . . . . ? C4 C4A C4B C8A -176.98(19) . . . . ? C9A C4A C4B C8A -0.3(2) . . . . ? C8A C4B C5 C6 0.6(3) . . . . ? C4A C4B C5 C6 -177.8(2) . . . . ? C4B C5 C6 C7 -0.3(3) . . . . ? C5 C6 C7 C8 -0.2(3) . . . . ? C6 C7 C8 C8A 0.5(3) . . . . ? C7 C8 C8A N9 178.95(18) . . . . ? C7 C8 C8A C4B -0.2(3) . . . . ? C5 C4B C8A N9 -179.66(16) . . . . ? C4A C4B C8A N9 -0.9(2) . . . . ? C5 C4B C8A C8 -0.3(3) . . . . ? C4A C4B C8A C8 178.48(17) . . . . ? C8 C8A N9 C9A -177.57(18) . . . . ? C4B C8A N9 C9A 1.7(2) . . . . ? C8A N9 C9A C1 176.31(18) . . . . ? C8A N9 C9A C4A -1.9(2) . . . . ? C2 C1 C9A N9 -175.89(18) . . . . ? C10 C1 C9A N9 6.5(3) . . . . ? C2 C1 C9A C4A 2.0(3) . . . . ? C10 C1 C9A C4A -175.57(17) . . . . ? C4 C4A C9A N9 178.57(16) . . . . ? C4B C4A C9A N9 1.3(2) . . . . ? C4 C4A C9A C1 0.3(3) . . . . ? C4B C4A C9A C1 -176.98(17) . . . . ? C9A C1 C10 C11 90.5(2) . . . . ? C2 C1 C10 C11 -87.0(2) . . . . ? C1 C10 C11 C12 174.69(17) . . . . ? C10 C11 C12 C13 -178.90(18) . . . . ? C11 C12 C13 C14 -173.86(18) . . . . ? C12 C13 C14 C15 -175.88(19) . . . . ? C13 C14 C15 C16 -179.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.173 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.040 _chemical_compound_source synthesis # Attachment 'an82.cif' data_an82 _database_code_depnum_ccdc_archive 'CCDC 708520' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H12 N4 O4' _chemical_formula_sum 'C6 H12 N4 O4' _chemical_formula_weight 204.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_int_tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 10.571(1) _cell_length_b 6.448(1) _cell_length_c 28.570(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1947.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used 256 _cell_measurement_theta_min 4.034 _cell_measurement_theta_max 12.573 _exptl_crystal_description plate _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8422 _exptl_absorpt_correction_T_max 0.9965 _exptl_absorpt_process_details 'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)' _publ_section_references ; !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! These references have to be cited in the publication, because they named software was used for measurement, evaluation of data, solution, refinement and computing the publication material of the structure. They are in ACTACC-format and need to be changed for publication in another journal. !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 331-334. Burla, M. C., Caliandro, R.,Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388. Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96. Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999). WinGX. J. Appl. Cryst. 32, 837-838. Hall, S. R., Allen, F. H. & Brown, I. D. (1991). Acta Cryst. A47, 655-685. Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands. Sheldrick, G. M. (1997). SHELX97. Programs for Crystal Structure Analysis (Release 97-2). University of G\"ottingen, Germany. Sheldrick, G. M. (2002). SADABS, Version 2.10, Bruker Analytical X-Ray Systems, Inc.: Madison, WI. Spek, A. L. (2005). PLATON, A Multipurpose Crystallographic Tool. Utrecht University, Utrecht, The Netherlands. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13855 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1543 _reflns_number_gt 1199 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1999)' _computing_cell_refinement 'Dirax/lsq (Duisenberg, 1992)' _computing_data_reduction 'EvalCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)' _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. Due to the crystal size the diffracting power was limited. ; _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^)+(0.0423P)^2^+0.9400P] 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 1543 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.14054(15) 0.1890(3) 0.82857(5) 0.0386(4) Uani 1 1 d . . . O1 O -0.10254(14) 0.2279(3) 0.86766(5) 0.0600(5) Uani 1 1 d . . . O2 O -0.24727(13) 0.2233(3) 0.81410(5) 0.0473(4) Uani 1 1 d . . . N2 N -0.05437(16) 0.0966(3) 0.79931(6) 0.0355(4) Uani 1 1 d . . . H2 H 0.017(2) 0.104(3) 0.8109(7) 0.039(6) Uiso 1 1 d . . . C3 C -0.06039(17) 0.0829(3) 0.75078(7) 0.0317(4) Uani 1 1 d . . . O3 O 0.03957(12) 0.0515(2) 0.73057(5) 0.0414(4) Uani 1 1 d . . . N4 N -0.17457(15) 0.0965(3) 0.72955(5) 0.0335(4) Uani 1 1 d . . . H4 H -0.235(2) 0.108(3) 0.7472(7) 0.043(6) Uiso 1 1 d . . . C5 C -0.19943(18) 0.0974(3) 0.68125(6) 0.0343(5) Uani 1 1 d . . . O5 O -0.31068(12) 0.1069(3) 0.66885(5) 0.0461(4) Uani 1 1 d . . . N6 N -0.10268(17) 0.0895(3) 0.65196(6) 0.0404(4) Uani 1 1 d . . . H6 H -0.033(2) 0.082(4) 0.6653(7) 0.047(7) Uiso 1 1 d . . . C7 C -0.1213(2) 0.0805(4) 0.60144(7) 0.0470(6) Uani 1 1 d . . . H7A H -0.2132 0.0816 0.5948 0.056 Uiso 1 1 calc R . . H7B H -0.0866 -0.0521 0.5896 0.056 Uiso 1 1 calc R . . C8 C -0.0599(2) 0.2565(4) 0.57530(7) 0.0536(6) Uani 1 1 d . . . H8 H -0.0869 0.3898 0.5901 0.064 Uiso 1 1 calc R . . C9 C 0.0832(2) 0.2446(5) 0.57719(9) 0.0767(9) Uani 1 1 d . . . H9A H 0.1113 0.2534 0.6098 0.115 Uiso 1 1 calc R . . H9B H 0.1195 0.3598 0.5593 0.115 Uiso 1 1 calc R . . H9C H 0.1114 0.1128 0.5637 0.115 Uiso 1 1 calc R . . C10 C -0.1085(3) 0.2533(5) 0.52477(8) 0.0832(10) Uani 1 1 d . . . H10A H -0.0884 0.1193 0.5104 0.125 Uiso 1 1 calc R . . H10B H -0.0679 0.3647 0.5069 0.125 Uiso 1 1 calc R . . H10C H -0.2004 0.2740 0.5247 0.125 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 0.0276(10) 0.0410(11) 0.0471(10) -0.0025(7) 0.0043(7) -0.0026(8) O1 0.0394(9) 0.0922(14) 0.0485(9) -0.0177(8) -0.0020(7) 0.0000(9) O2 0.0225(8) 0.0631(11) 0.0562(8) -0.0079(7) 0.0012(7) 0.0071(7) N2 0.0207(9) 0.0399(10) 0.0457(9) -0.0002(8) 0.0007(7) 0.0018(9) C3 0.0239(10) 0.0240(10) 0.0472(10) 0.0005(8) 0.0029(8) -0.0011(8) O3 0.0228(8) 0.0499(10) 0.0515(8) -0.0032(6) 0.0046(6) 0.0028(7) N4 0.0187(9) 0.0377(10) 0.0441(9) 0.0000(7) 0.0048(7) -0.0003(8) C5 0.0254(11) 0.0302(11) 0.0471(11) 0.0016(8) 0.0022(8) -0.0002(9) O5 0.0239(8) 0.0644(10) 0.0499(8) -0.0008(7) -0.0010(6) 0.0013(7) N6 0.0257(9) 0.0505(11) 0.0448(9) 0.0001(8) 0.0023(8) -0.0022(9) C7 0.0355(12) 0.0608(15) 0.0449(11) -0.0044(10) 0.0008(9) -0.0043(11) C8 0.0536(15) 0.0596(16) 0.0477(12) 0.0049(11) -0.0013(10) 0.0005(13) C9 0.0503(16) 0.121(3) 0.0588(15) 0.0107(16) 0.0040(11) -0.0253(17) C10 0.082(2) 0.109(3) 0.0580(15) 0.0220(16) -0.0116(14) -0.0075(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 O1 1.213(2) . ? N1 O2 1.222(2) . ? N1 N2 1.373(2) . ? N2 C3 1.391(2) . ? N2 H2 0.82(2) . ? C3 O3 1.221(2) . ? C3 N4 1.354(2) . ? N4 C5 1.405(2) . ? N4 H4 0.82(2) . ? C5 O5 1.230(2) . ? C5 N6 1.322(2) . ? N6 C7 1.458(3) . ? N6 H6 0.83(2) . ? C7 C8 1.506(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.515(3) . ? C8 C10 1.532(3) . ? C8 H8 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 N1 O2 125.45(17) . . ? O1 N1 N2 115.50(16) . . ? O2 N1 N2 119.04(16) . . ? N1 N2 C3 127.17(16) . . ? N1 N2 H2 109.6(15) . . ? C3 N2 H2 116.6(14) . . ? O3 C3 N4 124.79(18) . . ? O3 C3 N2 116.25(17) . . ? N4 C3 N2 118.90(16) . . ? C3 N4 C5 127.39(16) . . ? C3 N4 H4 115.4(15) . . ? C5 N4 H4 117.2(15) . . ? O5 C5 N6 124.01(18) . . ? O5 C5 N4 117.52(17) . . ? N6 C5 N4 118.47(17) . . ? C5 N6 C7 121.58(18) . . ? C5 N6 H6 113.5(15) . . ? C7 N6 H6 124.8(15) . . ? N6 C7 C8 113.78(18) . . ? N6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? N6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C9 112.0(2) . . ? C7 C8 C10 108.2(2) . . ? C9 C8 C10 111.6(2) . . ? C7 C8 H8 108.3 . . ? C9 C8 H8 108.3 . . ? C10 C8 H8 108.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 N1 N2 C3 -162.52(19) . . . . ? O2 N1 N2 C3 18.3(3) . . . . ? N1 N2 C3 O3 158.99(19) . . . . ? N1 N2 C3 N4 -23.6(3) . . . . ? O3 C3 N4 C5 -6.5(3) . . . . ? N2 C3 N4 C5 176.33(18) . . . . ? C3 N4 C5 O5 178.62(19) . . . . ? C3 N4 C5 N6 -1.8(3) . . . . ? O5 C5 N6 C7 -3.3(3) . . . . ? N4 C5 N6 C7 177.22(19) . . . . ? C5 N6 C7 C8 121.5(2) . . . . ? N6 C7 C8 C9 67.9(3) . . . . ? N6 C7 C8 C10 -168.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.901 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.901 _refine_diff_density_max 0.163 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.035 _chemical_compound_source synthesis