# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'V Pedireddi' _publ_contact_author_email VR.PEDIREDDI@NCL.RES.IN _publ_section_title ; Supramolecular Synthesis of Some Molecular Adducts of 4,4'-Bipyridine N,N'-Dioxide ; loop_ _publ_author_name 'V Pedireddi' 'Kapildev K Arora' 'Mayura S. Talwelkar' # Attachment '1a.cif' data_datam _database_code_depnum_ccdc_archive 'CCDC 672332' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'BPDO + CA' _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 N2 O2, 2(C3 H3 N3 O3)' _chemical_formula_sum 'C16 H14 N8 O8' _chemical_formula_weight 446.35 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 8.218(3) _cell_length_b 9.299(4) _cell_length_c 12.168(5) _cell_angle_alpha 91.93(1) _cell_angle_beta 91.44(1) _cell_angle_gamma 108.10(1) _cell_volume 882.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block-like _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS; Sheldrick, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD Area detector' _diffrn_measurement_method SMART _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3845 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 23.30 _reflns_number_total 2526 _reflns_number_gt 1983 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1173P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2526 _refine_ls_number_parameters 345 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0731 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1656 _refine_ls_wR_factor_gt 0.1520 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 -0.1721(4) -0.4591(3) 0.5693(2) 0.0186(7) Uani 1 1 d . . . C2 C -0.0726(4) -0.3253(3) 0.5313(2) 0.0183(7) Uani 1 1 d . . . C3 C 0.0818(3) -0.2433(3) 0.5835(2) 0.0179(7) Uani 1 1 d . . . C4 C 0.1309(4) -0.3056(3) 0.6760(2) 0.0190(7) Uani 1 1 d . . . C5 C 0.0284(4) -0.4394(4) 0.7129(2) 0.0194(7) Uani 1 1 d . . . C6 C 0.1914(4) -0.0983(3) 0.5422(2) 0.0183(7) Uani 1 1 d . . . C7 C 0.1649(4) -0.0525(4) 0.4368(2) 0.0202(7) Uani 1 1 d . . . C8 C 0.2693(4) 0.0807(3) 0.3992(2) 0.0188(7) Uani 1 1 d . . . C9 C 0.4282(4) 0.1312(4) 0.5660(2) 0.0188(7) Uani 1 1 d . . . C10 C 0.3249(4) 0.0004(3) 0.6056(2) 0.0185(7) Uani 1 1 d . . . C11 C 0.1778(4) 0.9643(3) -0.0530(2) 0.0186(7) Uani 1 1 d . . . C12 C 0.3102(4) 0.9315(3) 0.1210(2) 0.0183(7) Uani 1 1 d . . . C13 C 0.0452(4) 0.7479(3) 0.0554(2) 0.0197(7) Uani 1 1 d . . . C21 C 0.4529(4) 0.6320(3) 0.0796(2) 0.0190(7) Uani 1 1 d . . . C22 C 0.5998(4) 0.5883(3) 0.2447(2) 0.0191(7) Uani 1 1 d . . . C23 C 0.3446(4) 0.3973(3) 0.1723(2) 0.0176(7) Uani 1 1 d . . . N1 N -0.1213(3) -0.5151(3) 0.65972(19) 0.0188(6) Uani 1 1 d . . . N2 N 0.4001(3) 0.1712(3) 0.46331(19) 0.0190(6) Uani 1 1 d . . . N11 N 0.0530(3) 0.8312(3) -0.0365(2) 0.0198(6) Uani 1 1 d . . . N12 N 0.1721(3) 0.8048(3) 0.1330(2) 0.0205(6) Uani 1 1 d . . . N13 N 0.3024(3) 1.0091(3) 0.0275(2) 0.0197(6) Uani 1 1 d . . . N21 N 0.3372(3) 0.4922(3) 0.08965(19) 0.0185(6) Uani 1 1 d . . . N22 N 0.4769(3) 0.4481(3) 0.24623(19) 0.0199(6) Uani 1 1 d . . . N23 N 0.5797(3) 0.6749(3) 0.1591(2) 0.0198(6) Uani 1 1 d . . . O1 O -0.2222(3) -0.6446(2) 0.69672(17) 0.0256(6) Uani 1 1 d . . . O2 O 0.5038(3) 0.2976(2) 0.42634(17) 0.0262(6) Uani 1 1 d . . . O11 O 0.1739(3) 1.0381(2) -0.13388(16) 0.0245(6) Uani 1 1 d . . . O12 O 0.4289(3) 0.9746(2) 0.18739(16) 0.0255(6) Uani 1 1 d . . . O13 O -0.0712(3) 0.6295(2) 0.06647(16) 0.0257(6) Uani 1 1 d . . . O21 O 0.4428(2) 0.7122(2) 0.00319(15) 0.0222(5) Uani 1 1 d . . . O22 O 0.7152(3) 0.6317(2) 0.31316(17) 0.0268(6) Uani 1 1 d . . . O23 O 0.2344(3) 0.2737(2) 0.17824(16) 0.0241(6) Uani 1 1 d . . . H1 H -0.280(4) -0.515(3) 0.536(2) 0.019(8) Uiso 1 1 d . . . H2 H -0.104(3) -0.292(3) 0.472(2) 0.008(7) Uiso 1 1 d . . . H4 H 0.239(3) -0.261(3) 0.716(2) 0.006(7) Uiso 1 1 d . . . H5 H 0.054(3) -0.490(3) 0.770(2) 0.016(7) Uiso 1 1 d . . . H7 H 0.072(4) -0.115(3) 0.385(2) 0.016(7) Uiso 1 1 d . . . H8 H 0.263(3) 0.121(3) 0.326(2) 0.012(7) Uiso 1 1 d . . . H9 H 0.527(4) 0.201(4) 0.601(3) 0.027(9) Uiso 1 1 d . . . H10 H 0.352(3) -0.025(3) 0.675(2) 0.016(7) Uiso 1 1 d . . . H11 H -0.038(4) 0.796(4) -0.088(3) 0.037(10) Uiso 1 1 d . . . H12 H 0.183(5) 0.747(5) 0.198(3) 0.059(12) Uiso 1 1 d . . . H13 H 0.384(4) 1.084(4) 0.021(3) 0.031(10) Uiso 1 1 d . . . H21 H 0.247(4) 0.455(4) 0.037(3) 0.030(9) Uiso 1 1 d . . . H22 H 0.478(4) 0.386(4) 0.309(3) 0.039(10) Uiso 1 1 d . . . H23 H 0.656(4) 0.759(4) 0.156(3) 0.033(10) 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 C1 0.0235(17) 0.0198(17) 0.0131(15) -0.0046(13) -0.0014(13) 0.0083(14) C2 0.0255(17) 0.0215(18) 0.0099(15) -0.0014(14) -0.0016(13) 0.0107(14) C3 0.0237(16) 0.0187(16) 0.0136(15) -0.0049(13) 0.0010(13) 0.0105(14) C4 0.0200(16) 0.0173(17) 0.0201(16) -0.0016(14) 0.0000(14) 0.0067(14) C5 0.0250(17) 0.0200(18) 0.0137(16) -0.0013(14) -0.0019(13) 0.0083(14) C6 0.0258(16) 0.0191(17) 0.0137(15) -0.0012(13) 0.0026(13) 0.0127(14) C7 0.0243(16) 0.0197(17) 0.0182(16) -0.0064(14) -0.0020(14) 0.0103(14) C8 0.0245(16) 0.0192(18) 0.0138(16) -0.0017(14) 0.0003(13) 0.0084(14) C9 0.0218(16) 0.0198(18) 0.0168(16) -0.0046(14) -0.0003(13) 0.0100(15) C10 0.0261(17) 0.0197(18) 0.0117(16) -0.0028(14) -0.0004(13) 0.0104(14) C11 0.0258(17) 0.0165(17) 0.0159(16) -0.0047(14) 0.0007(13) 0.0108(14) C12 0.0229(16) 0.0189(17) 0.0146(16) -0.0049(13) 0.0000(14) 0.0096(14) C13 0.0221(16) 0.0186(18) 0.0205(17) -0.0016(14) 0.0023(13) 0.0094(15) C21 0.0271(17) 0.0152(17) 0.0178(16) -0.0025(14) 0.0036(13) 0.0111(14) C22 0.0227(16) 0.0183(17) 0.0163(16) -0.0045(13) -0.0010(13) 0.0073(14) C23 0.0228(16) 0.0157(17) 0.0157(16) -0.0033(13) 0.0031(13) 0.0084(14) N1 0.0254(14) 0.0167(14) 0.0150(13) -0.0011(11) 0.0037(11) 0.0076(12) N2 0.0248(13) 0.0184(14) 0.0152(13) -0.0010(11) 0.0008(11) 0.0090(12) N11 0.0243(14) 0.0187(15) 0.0147(13) 0.0010(12) -0.0022(12) 0.0043(12) N12 0.0233(14) 0.0227(15) 0.0146(13) -0.0029(12) -0.0015(11) 0.0064(12) N13 0.0230(15) 0.0151(15) 0.0196(14) -0.0014(12) -0.0012(12) 0.0042(13) N21 0.0249(14) 0.0162(14) 0.0131(13) -0.0023(11) -0.0039(12) 0.0050(12) N22 0.0265(14) 0.0166(14) 0.0156(13) -0.0016(11) -0.0017(11) 0.0056(12) N23 0.0232(14) 0.0160(15) 0.0184(14) -0.0031(12) -0.0036(11) 0.0043(13) O1 0.0302(12) 0.0192(12) 0.0233(12) 0.0055(10) -0.0014(9) 0.0015(10) O2 0.0304(12) 0.0204(12) 0.0242(12) 0.0092(10) -0.0004(10) 0.0017(10) O11 0.0333(12) 0.0193(12) 0.0195(12) 0.0029(10) -0.0026(9) 0.0065(10) O12 0.0300(12) 0.0255(13) 0.0191(12) -0.0028(10) -0.0060(10) 0.0069(10) O13 0.0292(12) 0.0209(13) 0.0226(12) 0.0024(10) -0.0032(10) 0.0018(11) O21 0.0301(12) 0.0177(12) 0.0182(11) 0.0005(10) -0.0023(9) 0.0069(10) O22 0.0314(12) 0.0238(13) 0.0230(12) -0.0038(10) -0.0100(10) 0.0069(10) O23 0.0292(12) 0.0196(13) 0.0207(12) -0.0002(9) -0.0035(9) 0.0041(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.344(4) . ? C1 C2 1.363(4) . ? C1 H1 0.95(3) . ? C2 C3 1.386(4) . ? C2 H2 0.86(3) . ? C3 C4 1.390(4) . ? C3 C6 1.482(4) . ? C4 C5 1.365(4) . ? C4 H4 0.97(3) . ? C5 N1 1.349(4) . ? C5 H5 0.91(3) . ? C6 C10 1.387(4) . ? C6 C7 1.398(4) . ? C7 C8 1.369(4) . ? C7 H7 0.99(3) . ? C8 N2 1.350(4) . ? C8 H8 0.98(3) . ? C9 N2 1.351(4) . ? C9 C10 1.360(4) . ? C9 H9 0.95(3) . ? C10 H10 0.93(3) . ? C11 O11 1.224(3) . ? C11 N13 1.356(4) . ? C11 N11 1.365(4) . ? C12 O12 1.208(3) . ? C12 N12 1.373(4) . ? C12 N13 1.379(4) . ? C13 O13 1.228(4) . ? C13 N12 1.354(4) . ? C13 N11 1.373(4) . ? C21 O21 1.229(3) . ? C21 N23 1.358(4) . ? C21 N21 1.363(4) . ? C22 O22 1.206(3) . ? C22 N23 1.375(4) . ? C22 N22 1.380(4) . ? C23 O23 1.228(3) . ? C23 N22 1.349(4) . ? C23 N21 1.372(4) . ? N1 O1 1.333(3) . ? N2 O2 1.320(3) . ? N11 H11 0.93(4) . ? N12 H12 0.99(4) . ? N13 H13 0.81(4) . ? N21 H21 0.94(3) . ? N22 H22 0.98(4) . ? N23 H23 0.84(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 N1 C1 C2 120.0(3) . . ? N1 C1 H1 117.0(17) . . ? C2 C1 H1 122.9(17) . . ? C1 C2 C3 121.8(3) . . ? C1 C2 H2 119.5(19) . . ? C3 C2 H2 118.7(19) . . ? C2 C3 C4 116.5(3) . . ? C2 C3 C6 122.1(3) . . ? C4 C3 C6 121.4(3) . . ? C5 C4 C3 120.6(3) . . ? C5 C4 H4 116.1(15) . . ? C3 C4 H4 123.2(15) . . ? N1 C5 C4 120.9(3) . . ? N1 C5 H5 113.3(19) . . ? C4 C5 H5 125.6(18) . . ? C10 C6 C7 116.0(3) . . ? C10 C6 C3 122.3(3) . . ? C7 C6 C3 121.7(3) . . ? C8 C7 C6 120.9(3) . . ? C8 C7 H7 117.2(16) . . ? C6 C7 H7 121.9(16) . . ? N2 C8 C7 120.8(3) . . ? N2 C8 H8 112.3(16) . . ? C7 C8 H8 126.9(16) . . ? N2 C9 C10 120.3(3) . . ? N2 C9 H9 111.9(19) . . ? C10 C9 H9 127.7(18) . . ? C9 C10 C6 122.0(3) . . ? C9 C10 H10 117.5(18) . . ? C6 C10 H10 120.3(18) . . ? O11 C11 N13 123.2(3) . . ? O11 C11 N11 121.7(3) . . ? N13 C11 N11 115.1(3) . . ? O12 C12 N12 123.4(3) . . ? O12 C12 N13 121.8(3) . . ? N12 C12 N13 114.8(3) . . ? O13 C13 N12 122.3(3) . . ? O13 C13 N11 121.7(3) . . ? N12 C13 N11 116.1(3) . . ? O21 C21 N23 122.9(3) . . ? O21 C21 N21 121.8(3) . . ? N23 C21 N21 115.3(3) . . ? O22 C22 N23 122.7(3) . . ? O22 C22 N22 122.7(3) . . ? N23 C22 N22 114.6(3) . . ? O23 C23 N22 122.5(3) . . ? O23 C23 N21 121.1(3) . . ? N22 C23 N21 116.5(3) . . ? O1 N1 C1 119.0(2) . . ? O1 N1 C5 120.8(2) . . ? C1 N1 C5 120.2(3) . . ? O2 N2 C8 120.9(2) . . ? O2 N2 C9 119.1(2) . . ? C8 N2 C9 119.9(3) . . ? C11 N11 C13 124.4(3) . . ? C11 N11 H11 119(2) . . ? C13 N11 H11 117(2) . . ? C13 N12 C12 124.2(2) . . ? C13 N12 H12 121(2) . . ? C12 N12 H12 114(2) . . ? C11 N13 C12 125.2(3) . . ? C11 N13 H13 121(2) . . ? C12 N13 H13 114(2) . . ? C21 N21 C23 124.1(3) . . ? C21 N21 H21 119.8(19) . . ? C23 N21 H21 116(2) . . ? C23 N22 C22 124.2(2) . . ? C23 N22 H22 117(2) . . ? C22 N22 H22 118(2) . . ? C21 N23 C22 125.3(3) . . ? C21 N23 H23 120(2) . . ? C22 N23 H23 115(2) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 23.30 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.378 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.105 # Attachment '1b.cif' data_datam2 _database_code_depnum_ccdc_archive 'CCDC 672333' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'BPDO + TCA + WATER' _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 N2 O2, 2(C3 H3 N3 S3), 2(H2 O)' _chemical_formula_sum 'C16 H18 N8 O4 S6' _chemical_formula_weight 578.74 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.129(8) _cell_length_b 13.217(5) _cell_length_c 8.531(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.82(1) _cell_angle_gamma 90.00 _cell_volume 2400.6(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block-like _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.612 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS; Sheldrick, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD Area detector' _diffrn_measurement_method SMART _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5055 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 23.34 _reflns_number_total 1739 _reflns_number_gt 1539 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0718P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1739 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.1046 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _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 C1 C 0.54420(11) -0.04508(19) 0.2000(3) 0.0258(6) Uani 1 1 d . . . C2 C 0.54482(11) 0.05781(19) 0.1993(3) 0.0242(6) Uani 1 1 d . . . C3 C 0.5000 0.1132(3) 0.2500 0.0202(7) Uani 1 2 d S . . C4 C 0.5000 0.2243(2) 0.2500 0.0222(8) Uani 1 2 d S . . C5 C 0.52327(12) 0.27961(19) 0.1406(3) 0.0304(6) Uani 1 1 d . . . C6 C 0.52288(12) 0.3831(2) 0.1417(3) 0.0331(6) Uani 1 1 d . . . C11 C 0.29314(11) 0.23554(18) 0.3723(3) 0.0222(5) Uani 1 1 d . . . C12 C 0.21816(11) 0.32565(17) 0.1582(3) 0.0245(6) Uani 1 1 d . . . C13 C 0.29798(11) 0.41749(17) 0.3592(3) 0.0235(6) Uani 1 1 d . . . N1 N 0.5000 -0.0963(2) 0.2500 0.0240(7) Uani 1 2 d S . . N2 N 0.5000 0.4337(2) 0.2500 0.0288(7) Uani 1 2 d S . . N11 N 0.24220(9) 0.23905(16) 0.2406(2) 0.0238(5) Uani 1 1 d . . . N12 N 0.31967(9) 0.32595(13) 0.4281(2) 0.0234(5) Uani 1 1 d . . . N13 N 0.24840(9) 0.41201(16) 0.2242(2) 0.0257(5) Uani 1 1 d . . . O1 O 0.5000 -0.19616(17) 0.2500 0.0355(6) Uani 1 2 d S . . O2 O 0.5000 0.53373(18) 0.2500 0.0379(7) Uani 1 2 d S . . O100 O 0.40441(9) 0.67052(14) 0.2092(2) 0.0314(5) Uani 1 1 d . . . S1 S 0.15830(3) 0.32491(5) -0.00593(8) 0.0335(3) Uani 1 1 d . . . S2 S 0.32151(3) 0.12690(5) 0.46277(7) 0.0252(2) Uani 1 1 d . . . S3 S 0.33113(3) 0.52549(5) 0.43509(8) 0.0312(3) Uani 1 1 d . . . H1 H 0.5739(12) -0.087(2) 0.171(3) 0.034(7) Uiso 1 1 d . . . H2 H 0.5763(11) 0.0903(18) 0.163(3) 0.025(6) Uiso 1 1 d . . . H5 H 0.5365(12) 0.2476(19) 0.063(3) 0.029(7) Uiso 1 1 d . . . H6 H 0.5356(12) 0.4234(19) 0.064(3) 0.035(7) Uiso 1 1 d . . . H11 H 0.2249(13) 0.1794(19) 0.208(3) 0.030(7) Uiso 1 1 d . . . H12 H 0.3547(16) 0.332(2) 0.524(4) 0.053(9) Uiso 1 1 d . . . H13 H 0.2329(12) 0.471(2) 0.185(3) 0.042(8) Uiso 1 1 d . . . H1W H 0.4290(13) 0.716(2) 0.224(3) 0.040(9) Uiso 1 1 d . . . H2W H 0.4297(17) 0.616(3) 0.220(4) 0.083(13) 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 C1 0.0201(13) 0.0237(14) 0.0315(14) -0.0028(11) 0.0038(11) 0.0031(11) C2 0.0187(12) 0.0257(15) 0.0268(13) -0.0001(11) 0.0038(11) -0.0024(11) C3 0.0156(16) 0.0238(18) 0.0172(16) 0.000 -0.0022(13) 0.000 C4 0.0144(17) 0.0229(19) 0.0251(17) 0.000 -0.0018(14) 0.000 C5 0.0344(15) 0.0240(15) 0.0333(15) 0.0001(12) 0.0101(12) 0.0017(12) C6 0.0349(15) 0.0251(15) 0.0394(16) 0.0045(12) 0.0105(13) -0.0019(12) C11 0.0175(12) 0.0251(13) 0.0258(13) -0.0004(10) 0.0087(11) 0.0031(10) C12 0.0211(14) 0.0269(15) 0.0262(14) 0.0002(10) 0.0078(11) 0.0024(10) C13 0.0193(12) 0.0254(14) 0.0261(12) 0.0040(10) 0.0064(11) 0.0010(10) N1 0.0169(14) 0.0195(17) 0.0308(15) 0.000 -0.0017(12) 0.000 N2 0.0222(15) 0.0197(17) 0.0396(17) 0.000 0.0000(13) 0.000 N11 0.0206(12) 0.0218(12) 0.0266(11) -0.0018(9) 0.0023(10) 0.0007(9) N12 0.0173(11) 0.0229(13) 0.0273(12) 0.0014(8) 0.0017(9) -0.0012(8) N13 0.0229(12) 0.0241(13) 0.0279(11) 0.0050(10) 0.0031(9) 0.0011(9) O1 0.0275(14) 0.0133(13) 0.0610(17) 0.000 0.0041(12) 0.000 O2 0.0305(14) 0.0172(14) 0.0601(18) 0.000 0.0023(13) 0.000 O100 0.0247(10) 0.0234(11) 0.0386(11) 0.0005(8) -0.0039(9) -0.0027(9) S1 0.0259(4) 0.0415(5) 0.0275(4) -0.0004(3) -0.0024(3) 0.0042(3) S2 0.0219(4) 0.0218(4) 0.0298(4) 0.0016(2) 0.0035(3) 0.0029(3) S3 0.0270(4) 0.0223(4) 0.0391(4) 0.0022(3) 0.0001(3) -0.0022(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 C1 N1 1.351(3) . ? C1 C2 1.360(4) . ? C1 H1 0.95(3) . ? C2 C3 1.393(3) . ? C2 H2 0.94(2) . ? C3 C2 1.393(3) 2_655 ? C3 C4 1.468(5) . ? C4 C5 1.391(3) . ? C4 C5 1.391(3) 2_655 ? C5 C6 1.368(4) . ? C5 H5 0.90(2) . ? C6 N2 1.346(3) . ? C6 H6 0.95(2) . ? C11 N11 1.358(3) . ? C11 N12 1.359(3) . ? C11 S2 1.670(2) . ? C12 N13 1.365(3) . ? C12 N11 1.372(3) . ? C12 S1 1.644(3) . ? C13 N13 1.359(3) . ? C13 N12 1.373(3) . ? C13 S3 1.654(2) . ? N1 O1 1.320(3) . ? N1 C1 1.351(3) 2_655 ? N2 O2 1.322(4) . ? N2 C6 1.346(3) 2_655 ? N11 H11 0.89(3) . ? N12 H12 0.96(4) . ? N13 H13 0.88(3) . ? O100 H1W 0.80(3) . ? O100 H2W 0.90(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 N1 C1 C2 120.8(2) . . ? N1 C1 H1 113.6(15) . . ? C2 C1 H1 125.5(15) . . ? C1 C2 C3 121.0(2) . . ? C1 C2 H2 117.8(14) . . ? C3 C2 H2 121.2(14) . . ? C2 C3 C2 116.6(3) . 2_655 ? C2 C3 C4 121.70(16) . . ? C2 C3 C4 121.70(16) 2_655 . ? C5 C4 C5 116.5(3) . 2_655 ? C5 C4 C3 121.74(15) . . ? C5 C4 C3 121.74(15) 2_655 . ? C6 C5 C4 121.1(2) . . ? C6 C5 H5 118.8(16) . . ? C4 C5 H5 120.0(16) . . ? N2 C6 C5 120.4(2) . . ? N2 C6 H6 116.1(15) . . ? C5 C6 H6 123.3(15) . . ? N11 C11 N12 116.2(2) . . ? N11 C11 S2 122.30(18) . . ? N12 C11 S2 121.49(19) . . ? N13 C12 N11 114.1(2) . . ? N13 C12 S1 123.16(18) . . ? N11 C12 S1 122.75(18) . . ? N13 C13 N12 115.0(2) . . ? N13 C13 S3 123.17(18) . . ? N12 C13 S3 121.81(19) . . ? O1 N1 C1 120.09(15) . 2_655 ? O1 N1 C1 120.09(15) . . ? C1 N1 C1 119.8(3) 2_655 . ? O2 N2 C6 119.79(15) . . ? O2 N2 C6 119.79(15) . 2_655 ? C6 N2 C6 120.4(3) . 2_655 ? C11 N11 C12 124.8(2) . . ? C11 N11 H11 114.9(17) . . ? C12 N11 H11 120.3(17) . . ? C11 N12 C13 123.9(2) . . ? C11 N12 H12 122.4(16) . . ? C13 N12 H12 113.6(16) . . ? C13 N13 C12 125.9(2) . . ? C13 N13 H13 114.4(18) . . ? C12 N13 H13 119.3(18) . . ? H1W O100 H2W 102(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.34 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.440 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.100 # Attachment '1c.cif' data_datam3 _database_code_depnum_ccdc_archive 'CCDC 672334' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'BPDO + PhgOH' _chemical_melting_point ? _chemical_formula_moiety '1.5(C10 H8 N2 O2), C6 H6 O3' _chemical_formula_sum 'C21 H18 N3 O6' _chemical_formula_weight 408.38 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 10.111(2) _cell_length_b 10.377(2) _cell_length_c 10.405(2) _cell_angle_alpha 70.61(1) _cell_angle_beta 84.88(1) _cell_angle_gamma 61.60(1) _cell_volume 902.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block-like _exptl_crystal_colour Pale-yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 426 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS; Sheldrick, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD Area detector' _diffrn_measurement_method SMART _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10278 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 28.17 _reflns_number_total 4062 _reflns_number_gt 3342 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1076P)^2^+0.0712P] 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 0.039(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4062 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1650 _refine_ls_wR_factor_gt 0.1571 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.75207(19) 0.1597(2) 0.54235(15) 0.0445(4) Uani 1 1 d . . . C2 C 0.71943(18) 0.1349(2) 0.43023(15) 0.0434(4) Uani 1 1 d . . . C3 C 0.80044(14) 0.14584(15) 0.31467(12) 0.0317(3) Uani 1 1 d . . . C4 C 0.90963(18) 0.1890(2) 0.31833(15) 0.0434(4) Uani 1 1 d . . . C5 C 0.93953(19) 0.2139(2) 0.43190(15) 0.0446(4) Uani 1 1 d . . . C6 C 0.76880(15) 0.11438(15) 0.19573(13) 0.0324(3) Uani 1 1 d . . . C7 C 0.67775(19) 0.0458(2) 0.20451(15) 0.0451(4) Uani 1 1 d . . . C8 C 0.6419(2) 0.0222(2) 0.09335(16) 0.0493(4) Uani 1 1 d . . . C9 C 0.78964(17) 0.12473(18) -0.03967(15) 0.0415(3) Uani 1 1 d . . . C10 C 0.82661(17) 0.15086(18) 0.06997(14) 0.0394(3) Uani 1 1 d . . . C11 C 0.06716(16) 0.52139(17) 0.28129(14) 0.0378(3) Uani 1 1 d . . . C12 C 0.06951(17) 0.45658(18) 0.18346(14) 0.0400(3) Uani 1 1 d . . . C13 C 0.17461(16) 0.30315(17) 0.20205(13) 0.0372(3) Uani 1 1 d . . . C14 C 0.27841(17) 0.21463(17) 0.31529(14) 0.0369(3) Uani 1 1 d . . . C15 C 0.27409(15) 0.28233(16) 0.41244(13) 0.0333(3) Uani 1 1 d . . . C16 C 0.16732(15) 0.43455(17) 0.39750(14) 0.0360(3) Uani 1 1 d . . . C21 C 0.47506(17) 0.52427(18) 0.28931(14) 0.0396(3) Uani 1 1 d . . . C22 C 0.44410(17) 0.49438(18) 0.17973(13) 0.0379(3) Uani 1 1 d . . . C23 C 0.51597(14) 0.51588(14) 0.05952(12) 0.0300(3) Uani 1 1 d . . . C24 C 0.61815(17) 0.57031(19) 0.05803(15) 0.0412(4) Uani 1 1 d . . . C25 C 0.64710(19) 0.5992(2) 0.16922(15) 0.0435(4) Uani 1 1 d . . . N1 N 0.86330(14) 0.19584(14) 0.54337(11) 0.0363(3) Uani 1 1 d . . . N2 N 0.69614(15) 0.06372(14) -0.02774(12) 0.0402(3) Uani 1 1 d . . . N21 N 0.57597(14) 0.57536(14) 0.28422(11) 0.0365(3) Uani 1 1 d . . . O1 O 0.89806(14) 0.21026(15) 0.65448(11) 0.0520(3) Uani 1 1 d . . . O2 O 0.65467(15) 0.04630(14) -0.13579(11) 0.0541(3) Uani 1 1 d . . . O11 O -0.03865(13) 0.67186(13) 0.25892(13) 0.0542(3) Uani 1 1 d . . . O13 O 0.17016(15) 0.24677(16) 0.10223(11) 0.0516(3) Uani 1 1 d . . . O15 O 0.37765(12) 0.19295(12) 0.52301(10) 0.0445(3) Uani 1 1 d . . . O21 O 0.60713(15) 0.59792(15) 0.39167(10) 0.0534(3) Uani 1 1 d . . . H1 H 0.706(2) 0.153(2) 0.626(2) 0.063(5) Uiso 1 1 d . . . H2 H 0.639(2) 0.112(2) 0.4386(17) 0.053(5) Uiso 1 1 d . . . H4 H 0.968(3) 0.204(3) 0.239(2) 0.073(6) Uiso 1 1 d . . . H5 H 1.014(2) 0.241(2) 0.4404(19) 0.059(5) Uiso 1 1 d . . . H7 H 0.643(2) 0.007(2) 0.292(2) 0.065(6) Uiso 1 1 d . . . H8 H 0.580(2) -0.020(2) 0.0945(19) 0.059(5) Uiso 1 1 d . . . H9 H 0.821(2) 0.149(2) -0.1307(18) 0.048(4) Uiso 1 1 d . . . H10 H 0.893(2) 0.196(2) 0.0575(17) 0.047(4) Uiso 1 1 d . . . H11 H 0.002(3) 0.709(3) 0.310(2) 0.091(8) Uiso 1 1 d . . . H12 H -0.004(2) 0.517(2) 0.1038(18) 0.049(4) Uiso 1 1 d . . . H13 H 0.234(3) 0.147(3) 0.121(3) 0.101(9) Uiso 1 1 d . . . H14 H 0.349(2) 0.113(2) 0.3301(18) 0.050(5) Uiso 1 1 d . . . H15 H 0.374(3) 0.260(3) 0.568(2) 0.077(7) Uiso 1 1 d . . . H16 H 0.1680(19) 0.4773(19) 0.4638(17) 0.044(4) Uiso 1 1 d . . . H21 H 0.437(2) 0.506(2) 0.376(2) 0.053(5) Uiso 1 1 d . . . H22 H 0.373(2) 0.458(2) 0.1908(17) 0.049(5) Uiso 1 1 d . . . H24 H 0.674(2) 0.588(2) -0.023(2) 0.064(6) Uiso 1 1 d . . . H25 H 0.713(2) 0.634(2) 0.1761(18) 0.056(5) 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 C1 0.0539(9) 0.0623(9) 0.0333(7) -0.0228(7) 0.0131(6) -0.0368(8) C2 0.0476(8) 0.0640(10) 0.0357(7) -0.0225(7) 0.0093(6) -0.0367(8) C3 0.0346(7) 0.0344(7) 0.0277(6) -0.0120(5) 0.0018(5) -0.0164(5) C4 0.0518(9) 0.0623(9) 0.0362(7) -0.0240(7) 0.0136(6) -0.0392(8) C5 0.0535(9) 0.0649(10) 0.0387(8) -0.0248(7) 0.0111(6) -0.0422(8) C6 0.0347(7) 0.0345(6) 0.0290(6) -0.0123(5) 0.0013(5) -0.0158(5) C7 0.0609(10) 0.0584(9) 0.0322(7) -0.0157(7) 0.0053(6) -0.0404(8) C8 0.0679(10) 0.0625(10) 0.0393(8) -0.0182(7) 0.0032(7) -0.0465(9) C9 0.0478(8) 0.0483(8) 0.0334(7) -0.0198(6) 0.0081(6) -0.0235(7) C10 0.0438(8) 0.0495(8) 0.0350(7) -0.0204(6) 0.0089(6) -0.0264(7) C11 0.0382(7) 0.0451(7) 0.0402(7) -0.0209(6) 0.0048(5) -0.0234(6) C12 0.0452(8) 0.0522(8) 0.0333(7) -0.0191(6) 0.0017(6) -0.0278(7) C13 0.0484(8) 0.0514(8) 0.0332(7) -0.0245(6) 0.0139(6) -0.0350(7) C14 0.0445(8) 0.0417(7) 0.0371(7) -0.0192(6) 0.0130(6) -0.0276(6) C15 0.0380(7) 0.0438(7) 0.0304(6) -0.0135(5) 0.0064(5) -0.0284(6) C16 0.0409(7) 0.0466(8) 0.0349(7) -0.0225(6) 0.0067(5) -0.0266(6) C21 0.0502(8) 0.0529(8) 0.0264(7) -0.0165(6) 0.0078(6) -0.0311(7) C22 0.0463(8) 0.0539(8) 0.0274(6) -0.0170(6) 0.0078(5) -0.0327(7) C23 0.0335(7) 0.0346(6) 0.0238(6) -0.0107(5) 0.0024(5) -0.0170(5) C24 0.0486(8) 0.0601(9) 0.0318(7) -0.0217(7) 0.0115(6) -0.0358(8) C25 0.0501(8) 0.0632(10) 0.0370(8) -0.0225(7) 0.0081(6) -0.0390(8) N1 0.0458(7) 0.0405(6) 0.0301(6) -0.0168(5) 0.0031(5) -0.0228(5) N2 0.0516(7) 0.0411(6) 0.0325(6) -0.0179(5) -0.0009(5) -0.0211(6) N21 0.0452(6) 0.0442(6) 0.0262(5) -0.0150(5) -0.0005(5) -0.0230(5) O1 0.0741(8) 0.0706(8) 0.0360(6) -0.0283(5) 0.0069(5) -0.0467(7) O2 0.0755(8) 0.0623(7) 0.0389(6) -0.0273(5) -0.0025(5) -0.0356(6) O11 0.0524(7) 0.0481(6) 0.0615(7) -0.0294(6) -0.0120(5) -0.0133(5) O13 0.0711(8) 0.0608(7) 0.0402(6) -0.0318(5) 0.0069(5) -0.0352(7) O15 0.0522(6) 0.0446(6) 0.0381(6) -0.0123(5) -0.0032(4) -0.0238(5) O21 0.0765(8) 0.0742(8) 0.0326(6) -0.0259(5) 0.0012(5) -0.0477(7) _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 N1 1.346(2) . ? C1 C2 1.3727(19) . ? C1 H1 0.95(2) . ? C2 C3 1.3970(19) . ? C2 H2 0.938(19) . ? C3 C4 1.382(2) . ? C3 C6 1.4761(17) . ? C4 C5 1.3768(19) . ? C4 H4 0.99(2) . ? C5 N1 1.3446(19) . ? C5 H5 0.94(2) . ? C6 C7 1.388(2) . ? C6 C10 1.3936(19) . ? C7 C8 1.370(2) . ? C7 H7 0.97(2) . ? C8 N2 1.347(2) . ? C8 H8 0.91(2) . ? C9 N2 1.344(2) . ? C9 C10 1.3758(19) . ? C9 H9 0.962(18) . ? C10 H10 0.968(18) . ? C11 O11 1.3604(18) . ? C11 C12 1.3871(18) . ? C11 C16 1.388(2) . ? C12 C13 1.387(2) . ? C12 H12 0.977(18) . ? C13 O13 1.3638(15) . ? C13 C14 1.385(2) . ? C14 C15 1.3970(18) . ? C14 H14 0.917(19) . ? C15 O15 1.3649(17) . ? C15 C16 1.389(2) . ? C16 H16 0.938(17) . ? C21 N21 1.3458(19) . ? C21 C22 1.3731(18) . ? C21 H21 0.946(19) . ? C22 C23 1.3960(18) . ? C22 H22 0.939(18) . ? C23 C24 1.390(2) . ? C23 C23 1.480(2) 2_665 ? C24 C25 1.3742(19) . ? C24 H24 0.98(2) . ? C25 N21 1.3525(19) . ? C25 H25 0.91(2) . ? N1 O1 1.3114(14) . ? N2 O2 1.3281(14) . ? N21 O21 1.3079(14) . ? O11 H11 0.96(3) . ? O13 H13 0.88(3) . ? O15 H15 0.94(2) . ? 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 N1 C1 C2 120.58(13) . . ? N1 C1 H1 111.5(12) . . ? C2 C1 H1 127.9(12) . . ? C1 C2 C3 121.23(13) . . ? C1 C2 H2 114.4(11) . . ? C3 C2 H2 124.3(11) . . ? C4 C3 C2 116.13(12) . . ? C4 C3 C6 122.53(12) . . ? C2 C3 C6 121.33(12) . . ? C5 C4 C3 121.38(13) . . ? C5 C4 H4 117.8(12) . . ? C3 C4 H4 120.8(12) . . ? N1 C5 C4 120.65(13) . . ? N1 C5 H5 114.5(11) . . ? C4 C5 H5 124.8(11) . . ? C7 C6 C10 116.32(12) . . ? C7 C6 C3 120.71(12) . . ? C10 C6 C3 122.97(12) . . ? C8 C7 C6 121.39(14) . . ? C8 C7 H7 118.3(12) . . ? C6 C7 H7 120.2(12) . . ? N2 C8 C7 120.45(14) . . ? N2 C8 H8 115.7(12) . . ? C7 C8 H8 123.9(12) . . ? N2 C9 C10 120.51(13) . . ? N2 C9 H9 112.5(10) . . ? C10 C9 H9 127.0(11) . . ? C9 C10 C6 121.00(13) . . ? C9 C10 H10 118.4(10) . . ? C6 C10 H10 120.6(10) . . ? O11 C11 C12 117.04(13) . . ? O11 C11 C16 122.02(12) . . ? C12 C11 C16 120.93(14) . . ? C11 C12 C13 119.25(14) . . ? C11 C12 H12 120.5(10) . . ? C13 C12 H12 120.3(10) . . ? O13 C13 C14 122.68(13) . . ? O13 C13 C12 116.14(13) . . ? C14 C13 C12 121.18(12) . . ? C13 C14 C15 118.60(14) . . ? C13 C14 H14 122.8(11) . . ? C15 C14 H14 118.6(11) . . ? O15 C15 C16 121.32(12) . . ? O15 C15 C14 117.55(13) . . ? C16 C15 C14 121.13(13) . . ? C11 C16 C15 118.87(12) . . ? C11 C16 H16 121.8(10) . . ? C15 C16 H16 119.2(10) . . ? N21 C21 C22 120.96(12) . . ? N21 C21 H21 112.3(11) . . ? C22 C21 H21 126.5(11) . . ? C21 C22 C23 121.25(13) . . ? C21 C22 H22 116.4(11) . . ? C23 C22 H22 122.4(11) . . ? C24 C23 C22 115.94(12) . . ? C24 C23 C23 122.11(14) . 2_665 ? C22 C23 C23 121.95(14) . 2_665 ? C25 C24 C23 121.62(13) . . ? C25 C24 H24 117.2(12) . . ? C23 C24 H24 121.2(12) . . ? N21 C25 C24 120.51(13) . . ? N21 C25 H25 112.9(12) . . ? C24 C25 H25 126.6(12) . . ? O1 N1 C5 120.63(11) . . ? O1 N1 C1 119.43(11) . . ? C5 N1 C1 119.92(12) . . ? O2 N2 C9 120.20(12) . . ? O2 N2 C8 119.54(12) . . ? C9 N2 C8 120.25(12) . . ? O21 N21 C21 119.71(11) . . ? O21 N21 C25 120.55(12) . . ? C21 N21 C25 119.73(12) . . ? C11 O11 H11 104.6(15) . . ? C13 O13 H13 113.2(17) . . ? C15 O15 H15 107.1(14) . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 28.17 _diffrn_measured_fraction_theta_full 0.918 _refine_diff_density_max 0.262 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.088 # Attachment '1d.cif' data_datam4 _database_code_depnum_ccdc_archive 'CCDC 672335' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common BPDO+ResOH+water _chemical_melting_point ? _chemical_formula_moiety '2(C10 H8 N2 O2), 2(C6 H6 O2), 4(H2 O)' _chemical_formula_sum 'C32 H36 N4 O12' _chemical_formula_weight 668.65 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 7.129(1) _cell_length_b 10.253(2) _cell_length_c 23.220(4) _cell_angle_alpha 82.15(1) _cell_angle_beta 85.26(1) _cell_angle_gamma 70.40(1) _cell_volume 1582.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Rectangular block' _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS; Sheldrick, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD Area detector' _diffrn_measurement_method SMART _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6950 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.1139 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 0.89 _diffrn_reflns_theta_max 23.27 _reflns_number_total 4524 _reflns_number_gt 1999 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0672P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4524 _refine_ls_number_parameters 465 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1095 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1494 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 0.821 _refine_ls_restrained_S_all 0.821 _refine_ls_shift/su_max 0.002 _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 0.1595(8) -0.3365(6) 0.0991(2) 0.0604(14) Uani 1 1 d . . . C2 C 0.1675(7) -0.2160(5) 0.0660(2) 0.0580(14) Uani 1 1 d . . . H2A H 0.1898 -0.2143 0.0259 0.070 Uiso 1 1 calc R . . C3 C 0.1421(7) -0.0972(5) 0.0924(2) 0.0529(13) Uani 1 1 d . . . C4 C 0.1075(7) -0.0969(5) 0.1519(2) 0.0531(13) Uani 1 1 d . . . H4A H 0.0918 -0.0177 0.1696 0.064 Uiso 1 1 calc R . . C5 C 0.0971(7) -0.2178(5) 0.18405(19) 0.0557(13) Uani 1 1 d . . . H5A H 0.0705 -0.2187 0.2240 0.067 Uiso 1 1 calc R . . C6 C 0.1250(7) -0.3383(5) 0.1586(2) 0.0597(14) Uani 1 1 d . . . H6A H 0.1206 -0.4193 0.1813 0.072 Uiso 1 1 calc R . . C11 C 0.7232(8) 0.6652(5) 0.0246(2) 0.0668(16) Uani 1 1 d . . . H11A H 0.7599 0.6572 -0.0145 0.080 Uiso 1 1 calc R . . C12 C 0.6876(7) 0.7900(5) 0.0454(2) 0.0573(14) Uani 1 1 d . . . H12A H 0.6983 0.8657 0.0200 0.069 Uiso 1 1 calc R . . C13 C 0.6361(6) 0.8067(4) 0.10351(19) 0.0387(11) Uani 1 1 d . . . C14 C 0.6133(6) 0.6899(4) 0.13749(18) 0.0454(12) Uani 1 1 d . . . H14A H 0.5733 0.6954 0.1765 0.054 Uiso 1 1 calc R . . C15 C 0.6484(7) 0.5671(4) 0.1149(2) 0.0515(13) Uani 1 1 d . . . H15A H 0.6316 0.4910 0.1388 0.062 Uiso 1 1 calc R . . C16 C 0.6212(7) 1.0579(5) 0.09497(19) 0.0544(14) Uani 1 1 d . . . H16A H 0.6448 1.0574 0.0550 0.065 Uiso 1 1 calc R . . C17 C 0.6017(7) 1.1764(5) 0.1191(2) 0.0566(14) Uani 1 1 d . . . H17A H 0.6088 1.2554 0.0953 0.068 Uiso 1 1 calc R . . C18 C 0.5541(8) 1.0678(5) 0.2098(2) 0.0609(15) Uani 1 1 d . . . H18A H 0.5295 1.0716 0.2496 0.073 Uiso 1 1 calc R . . C19 C 0.5704(7) 0.9490(5) 0.18720(19) 0.0572(14) Uani 1 1 d . . . H19A H 0.5568 0.8729 0.2118 0.069 Uiso 1 1 calc R . . C20 C 0.6068(6) 0.9389(4) 0.12824(18) 0.0394(11) Uani 1 1 d . . . C21 C -0.5182(7) 1.1911(4) 0.66352(17) 0.0422(12) Uani 1 1 d . . . C22 C -0.7243(7) 1.2392(4) 0.66616(16) 0.0383(11) Uani 1 1 d . . . H22A H -0.7945 1.1879 0.6531 0.046 Uiso 1 1 calc R . . C23 C -0.8258(7) 1.3637(4) 0.68823(16) 0.0372(11) Uani 1 1 d . . . C24 C -0.7215(7) 1.4405(4) 0.70808(17) 0.0428(12) Uani 1 1 d . . . H24A H -0.7891 1.5243 0.7230 0.051 Uiso 1 1 calc R . . C25 C -0.5164(7) 1.3902(5) 0.70531(17) 0.0477(12) Uani 1 1 d . . . H25A H -0.4457 1.4406 0.7188 0.057 Uiso 1 1 calc R . . C26 C -0.4139(7) 1.2673(5) 0.68301(17) 0.0482(12) Uani 1 1 d . . . H26A H -0.2753 1.2357 0.6810 0.058 Uiso 1 1 calc R . . C31 C 0.5518(6) 0.1644(4) 0.48291(19) 0.0433(12) Uani 1 1 d . . . H31A H 0.6269 0.0882 0.5072 0.052 Uiso 1 1 calc R . . C32 C 0.4462(6) 0.2866(4) 0.50534(18) 0.0414(12) Uani 1 1 d . . . H32A H 0.4492 0.2911 0.5450 0.050 Uiso 1 1 calc R . . C33 C 0.3347(6) 0.4042(4) 0.47019(18) 0.0354(11) Uani 1 1 d . . . C34 C 0.3361(7) 0.3868(4) 0.41162(18) 0.0475(12) Uani 1 1 d . . . H34A H 0.2641 0.4614 0.3860 0.057 Uiso 1 1 calc R . . C35 C 0.4404(7) 0.2629(5) 0.39073(19) 0.0513(13) Uani 1 1 d . . . H35A H 0.4370 0.2543 0.3515 0.062 Uiso 1 1 calc R . . C36 C 0.2051(6) 0.5532(4) 0.55210(17) 0.0403(11) Uani 1 1 d . . . H36A H 0.2710 0.4777 0.5783 0.048 Uiso 1 1 calc R . . C37 C 0.0965(7) 0.6765(5) 0.57251(18) 0.0465(12) Uani 1 1 d . . . H37A H 0.0909 0.6835 0.6122 0.056 Uiso 1 1 calc R . . C38 C 0.0094(7) 0.7792(4) 0.47853(19) 0.0464(12) Uani 1 1 d . . . H38A H -0.0563 0.8566 0.4532 0.056 Uiso 1 1 calc R . . C39 C 0.1176(6) 0.6568(4) 0.45676(18) 0.0426(12) Uani 1 1 d . . . H39A H 0.1232 0.6530 0.4169 0.051 Uiso 1 1 calc R . . C40 C 0.2195(6) 0.5381(4) 0.49300(18) 0.0336(10) Uani 1 1 d . . . N11 N 0.7059(6) 0.5545(4) 0.05946(17) 0.0541(11) Uani 1 1 d . . . N12 N 0.5728(5) 1.1797(4) 0.17572(17) 0.0483(10) Uani 1 1 d . . . N31 N 0.5469(5) 0.1546(4) 0.42637(16) 0.0430(10) Uani 1 1 d . . . N32 N -0.0029(6) 0.7886(4) 0.53594(17) 0.0463(10) Uani 1 1 d . . . O1 O 0.1862(6) -0.4549(4) 0.07518(14) 0.0882(13) Uani 1 1 d . . . H1A H 0.2059 -0.4413 0.0399 0.132 Uiso 1 1 calc R . . O3 O 0.1569(5) 0.0181(3) 0.05763(13) 0.0725(11) Uani 1 1 d . . . H3A H 0.1307 0.0835 0.0770 0.109 Uiso 1 1 calc R . . O11 O 0.7481(6) 0.4331(3) 0.04002(13) 0.0799(12) Uani 1 1 d . . . O12 O 0.5595(5) 1.2939(3) 0.19934(13) 0.0596(9) Uani 1 1 d . . . O21 O -0.4108(5) 1.0698(3) 0.64233(13) 0.0663(10) Uani 1 1 d . . . H21A H -0.4858 1.0389 0.6279 0.099 Uiso 1 1 calc R . . O23 O -1.0286(4) 1.4066(3) 0.68840(11) 0.0480(8) Uani 1 1 d . . . H23A H -1.0745 1.4797 0.7031 0.072 Uiso 1 1 calc R . . O31 O 0.6472(4) 0.0354(3) 0.40508(13) 0.0564(9) Uani 1 1 d . . . O32 O -0.1127(5) 0.9028(3) 0.55677(13) 0.0647(10) Uani 1 1 d . . . O100 O 0.0821(10) 0.2470(5) 0.1114(3) 0.113(2) Uani 1 1 d . . . O200 O 0.9834(9) 0.0323(5) 0.3316(2) 0.0899(15) Uani 1 1 d . . . O300 O 0.9463(7) 1.2275(5) 0.2339(2) 0.0805(13) Uani 1 1 d . . . O400 O -1.2131(6) 1.6453(3) 0.73423(15) 0.0594(10) Uani 1 1 d . . . H302 H 0.801(13) 1.256(7) 0.214(3) 0.19(3) Uiso 1 1 d . . . H301 H 0.965(8) 1.171(5) 0.2610(19) 0.06(2) Uiso 1 1 d . . . H402 H -1.350(11) 1.670(6) 0.768(3) 0.14(2) Uiso 1 1 d . . . H401 H -1.146(8) 1.694(5) 0.749(2) 0.10(2) Uiso 1 1 d . . . H102 H 0.067(11) 0.276(7) 0.152(3) 0.16(3) Uiso 1 1 d . . . H202 H 0.892(9) 0.045(6) 0.351(3) 0.08(3) Uiso 1 1 d . . . H201 H 1.071(12) 0.060(8) 0.338(4) 0.19(5) Uiso 1 1 d . . . H101 H -0.006(8) 0.295(6) 0.098(2) 0.06(2) 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 C1 0.065(4) 0.069(4) 0.045(3) 0.012(3) -0.007(3) -0.025(3) C2 0.061(4) 0.082(4) 0.034(3) -0.004(3) -0.001(3) -0.028(3) C3 0.043(3) 0.069(4) 0.044(3) 0.017(3) -0.005(3) -0.022(3) C4 0.049(3) 0.062(3) 0.046(3) 0.002(3) -0.004(3) -0.018(3) C5 0.048(3) 0.078(4) 0.035(3) 0.007(3) -0.003(2) -0.018(3) C6 0.063(4) 0.068(4) 0.049(3) 0.010(3) -0.005(3) -0.029(3) C11 0.102(5) 0.051(3) 0.043(3) -0.011(3) 0.023(3) -0.023(3) C12 0.070(4) 0.050(3) 0.045(3) 0.008(3) 0.008(3) -0.017(3) C13 0.030(3) 0.038(3) 0.044(3) 0.004(2) -0.003(2) -0.009(2) C14 0.052(3) 0.047(3) 0.038(3) -0.001(2) 0.002(2) -0.020(3) C15 0.072(4) 0.040(3) 0.043(3) 0.003(2) 0.002(3) -0.022(3) C16 0.069(4) 0.052(3) 0.047(3) 0.007(3) -0.011(3) -0.030(3) C17 0.078(4) 0.043(3) 0.053(3) 0.003(3) -0.005(3) -0.028(3) C18 0.087(4) 0.047(3) 0.049(3) -0.009(3) 0.014(3) -0.026(3) C19 0.084(4) 0.044(3) 0.044(3) -0.001(2) 0.012(3) -0.026(3) C20 0.037(3) 0.037(3) 0.044(3) 0.000(2) -0.005(2) -0.013(2) C21 0.045(3) 0.045(3) 0.034(3) -0.006(2) -0.002(2) -0.010(3) C22 0.042(3) 0.040(3) 0.033(3) -0.006(2) -0.007(2) -0.013(2) C23 0.037(3) 0.043(3) 0.030(3) 0.003(2) -0.005(2) -0.013(2) C24 0.050(4) 0.042(3) 0.039(3) -0.009(2) -0.002(2) -0.017(3) C25 0.054(4) 0.059(3) 0.042(3) -0.007(2) -0.003(3) -0.034(3) C26 0.041(3) 0.064(3) 0.041(3) -0.008(2) 0.004(2) -0.020(3) C31 0.043(3) 0.033(3) 0.048(3) 0.001(2) -0.006(2) -0.007(2) C32 0.047(3) 0.043(3) 0.034(3) -0.001(2) 0.001(2) -0.017(3) C33 0.035(3) 0.034(3) 0.039(3) -0.001(2) -0.003(2) -0.016(2) C34 0.051(3) 0.045(3) 0.039(3) -0.001(2) -0.013(2) -0.005(2) C35 0.059(4) 0.048(3) 0.038(3) -0.011(2) -0.010(3) -0.001(3) C36 0.045(3) 0.039(3) 0.037(3) 0.001(2) -0.005(2) -0.015(2) C37 0.058(4) 0.044(3) 0.037(3) -0.004(2) -0.004(3) -0.017(3) C38 0.053(3) 0.040(3) 0.040(3) 0.000(2) -0.010(3) -0.008(3) C39 0.049(3) 0.042(3) 0.034(3) -0.002(2) -0.007(2) -0.011(2) C40 0.030(3) 0.036(3) 0.037(3) -0.002(2) -0.001(2) -0.014(2) N11 0.070(3) 0.039(3) 0.050(3) -0.002(2) 0.009(2) -0.017(2) N12 0.047(3) 0.045(3) 0.054(3) -0.005(2) 0.003(2) -0.017(2) N31 0.041(3) 0.038(2) 0.047(3) -0.008(2) -0.008(2) -0.007(2) N32 0.048(3) 0.037(2) 0.053(3) -0.010(2) -0.004(2) -0.010(2) O1 0.133(4) 0.075(3) 0.066(2) -0.016(2) 0.002(2) -0.044(3) O3 0.089(3) 0.075(3) 0.053(2) 0.0096(18) 0.0028(19) -0.033(2) O11 0.130(3) 0.039(2) 0.067(2) -0.0226(18) 0.021(2) -0.024(2) O12 0.067(3) 0.042(2) 0.077(2) -0.0213(17) 0.005(2) -0.0230(18) O21 0.053(2) 0.058(2) 0.081(2) -0.0367(18) -0.0098(19) 0.0031(18) O23 0.046(2) 0.0470(19) 0.0488(19) -0.0109(14) -0.0062(16) -0.0098(17) O31 0.051(2) 0.0396(19) 0.073(2) -0.0235(17) -0.0032(18) -0.0013(16) O32 0.073(3) 0.043(2) 0.066(2) -0.0205(17) -0.0017(19) 0.0017(18) O100 0.111(5) 0.073(4) 0.122(5) 0.001(3) 0.034(4) -0.001(3) O200 0.068(4) 0.116(4) 0.088(4) -0.014(3) -0.002(3) -0.033(3) O300 0.085(4) 0.073(3) 0.093(3) -0.009(3) -0.007(3) -0.039(3) O400 0.061(3) 0.054(2) 0.064(2) -0.0232(17) 0.002(2) -0.0159(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 C1 O1 1.353(5) . ? C1 C2 1.379(6) . ? C1 C6 1.381(6) . ? C2 C3 1.391(6) . ? C2 H2A 0.9300 . ? C3 O3 1.368(5) . ? C3 C4 1.382(6) . ? C4 C5 1.378(6) . ? C4 H4A 0.9300 . ? C5 C6 1.390(6) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C11 N11 1.336(5) . ? C11 C12 1.366(6) . ? C11 H11A 0.9300 . ? C12 C13 1.387(5) . ? C12 H12A 0.9300 . ? C13 C14 1.392(5) . ? C13 C20 1.487(5) . ? C14 C15 1.367(5) . ? C14 H14A 0.9300 . ? C15 N11 1.329(5) . ? C15 H15A 0.9300 . ? C16 C17 1.367(5) . ? C16 C20 1.382(5) . ? C16 H16A 0.9300 . ? C17 N12 1.318(5) . ? C17 H17A 0.9300 . ? C18 N12 1.340(5) . ? C18 C19 1.357(5) . ? C18 H18A 0.9300 . ? C19 C20 1.383(5) . ? C19 H19A 0.9300 . ? C21 O21 1.357(5) . ? C21 C26 1.382(6) . ? C21 C22 1.383(6) . ? C22 C23 1.383(5) . ? C22 H22A 0.9300 . ? C23 O23 1.362(5) . ? C23 C24 1.391(5) . ? C24 C25 1.377(6) . ? C24 H24A 0.9300 . ? C25 C26 1.374(6) . ? C25 H25A 0.9300 . ? C26 H26A 0.9300 . ? C31 N31 1.334(5) . ? C31 C32 1.374(5) . ? C31 H31A 0.9300 . ? C32 C33 1.395(5) . ? C32 H32A 0.9300 . ? C33 C34 1.395(5) . ? C33 C40 1.487(5) . ? C34 C35 1.369(5) . ? C34 H34A 0.9300 . ? C35 N31 1.335(5) . ? C35 H35A 0.9300 . ? C36 C37 1.367(5) . ? C36 C40 1.394(5) . ? C36 H36A 0.9300 . ? C37 N32 1.353(5) . ? C37 H37A 0.9300 . ? C38 N32 1.343(5) . ? C38 C39 1.372(5) . ? C38 H38A 0.9300 . ? C39 C40 1.395(5) . ? C39 H39A 0.9300 . ? N11 O11 1.312(4) . ? N12 O12 1.331(4) . ? N31 O31 1.330(4) . ? N32 O32 1.302(4) . ? O1 H1A 0.8200 . ? O3 H3A 0.8200 . ? O21 H21A 0.8200 . ? O23 H23A 0.8200 . ? O100 H102 1.02(6) . ? O100 H101 0.71(5) . ? O200 H202 0.75(5) . ? O200 H201 0.80(7) . ? O300 H302 1.10(8) . ? O300 H301 0.78(4) . ? O400 H402 1.18(7) . ? O400 H401 0.91(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 O1 C1 C2 121.9(5) . . ? O1 C1 C6 118.4(5) . . ? C2 C1 C6 119.7(5) . . ? C1 C2 C3 120.1(5) . . ? C1 C2 H2A 120.0 . . ? C3 C2 H2A 120.0 . . ? O3 C3 C4 121.4(5) . . ? O3 C3 C2 117.5(5) . . ? C4 C3 C2 121.1(5) . . ? C5 C4 C3 117.9(5) . . ? C5 C4 H4A 121.0 . . ? C3 C4 H4A 121.0 . . ? C4 C5 C6 121.9(5) . . ? C4 C5 H5A 119.0 . . ? C6 C5 H5A 119.0 . . ? C1 C6 C5 119.3(5) . . ? C1 C6 H6A 120.4 . . ? C5 C6 H6A 120.4 . . ? N11 C11 C12 121.1(4) . . ? N11 C11 H11A 119.5 . . ? C12 C11 H11A 119.5 . . ? C11 C12 C13 121.7(4) . . ? C11 C12 H12A 119.1 . . ? C13 C12 H12A 119.1 . . ? C12 C13 C14 114.9(4) . . ? C12 C13 C20 123.1(4) . . ? C14 C13 C20 122.0(4) . . ? C15 C14 C13 121.6(4) . . ? C15 C14 H14A 119.2 . . ? C13 C14 H14A 119.2 . . ? N11 C15 C14 121.3(4) . . ? N11 C15 H15A 119.4 . . ? C14 C15 H15A 119.4 . . ? C17 C16 C20 122.0(4) . . ? C17 C16 H16A 119.0 . . ? C20 C16 H16A 119.0 . . ? N12 C17 C16 120.6(4) . . ? N12 C17 H17A 119.7 . . ? C16 C17 H17A 119.7 . . ? N12 C18 C19 121.2(4) . . ? N12 C18 H18A 119.4 . . ? C19 C18 H18A 119.4 . . ? C18 C19 C20 121.3(4) . . ? C18 C19 H19A 119.4 . . ? C20 C19 H19A 119.4 . . ? C16 C20 C19 115.2(4) . . ? C16 C20 C13 123.0(4) . . ? C19 C20 C13 121.7(4) . . ? O21 C21 C26 117.5(4) . . ? O21 C21 C22 122.5(4) . . ? C26 C21 C22 120.0(4) . . ? C23 C22 C21 120.0(4) . . ? C23 C22 H22A 120.0 . . ? C21 C22 H22A 120.0 . . ? O23 C23 C22 117.0(4) . . ? O23 C23 C24 122.8(4) . . ? C22 C23 C24 120.3(4) . . ? C25 C24 C23 118.8(4) . . ? C25 C24 H24A 120.6 . . ? C23 C24 H24A 120.6 . . ? C26 C25 C24 121.5(4) . . ? C26 C25 H25A 119.2 . . ? C24 C25 H25A 119.2 . . ? C25 C26 C21 119.5(4) . . ? C25 C26 H26A 120.3 . . ? C21 C26 H26A 120.3 . . ? N31 C31 C32 120.3(4) . . ? N31 C31 H31A 119.9 . . ? C32 C31 H31A 119.9 . . ? C31 C32 C33 121.7(4) . . ? C31 C32 H32A 119.1 . . ? C33 C32 H32A 119.1 . . ? C34 C33 C32 115.0(4) . . ? C34 C33 C40 121.9(4) . . ? C32 C33 C40 123.1(4) . . ? C35 C34 C33 121.9(4) . . ? C35 C34 H34A 119.1 . . ? C33 C34 H34A 119.1 . . ? N31 C35 C34 120.3(4) . . ? N31 C35 H35A 119.8 . . ? C34 C35 H35A 119.8 . . ? C37 C36 C40 121.6(4) . . ? C37 C36 H36A 119.2 . . ? C40 C36 H36A 119.2 . . ? N32 C37 C36 121.1(4) . . ? N32 C37 H37A 119.5 . . ? C36 C37 H37A 119.5 . . ? N32 C38 C39 120.9(4) . . ? N32 C38 H38A 119.5 . . ? C39 C38 H38A 119.5 . . ? C38 C39 C40 121.7(4) . . ? C38 C39 H39A 119.2 . . ? C40 C39 H39A 119.2 . . ? C36 C40 C39 115.5(4) . . ? C36 C40 C33 122.2(4) . . ? C39 C40 C33 122.3(4) . . ? O11 N11 C15 119.6(4) . . ? O11 N11 C11 121.0(4) . . ? C15 N11 C11 119.4(4) . . ? C17 N12 O12 120.5(4) . . ? C17 N12 C18 119.7(4) . . ? O12 N12 C18 119.7(4) . . ? O31 N31 C31 120.0(4) . . ? O31 N31 C35 119.3(4) . . ? C31 N31 C35 120.7(4) . . ? O32 N32 C38 120.9(4) . . ? O32 N32 C37 119.8(4) . . ? C38 N32 C37 119.3(4) . . ? C1 O1 H1A 109.5 . . ? C3 O3 H3A 109.5 . . ? C21 O21 H21A 109.5 . . ? C23 O23 H23A 109.5 . . ? H102 O100 H101 102(6) . . ? H202 O200 H201 121(8) . . ? H302 O300 H301 116(6) . . ? H402 O400 H401 97(4) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.238 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.068 # Attachment '1e.cif' data_datam5 _database_code_depnum_ccdc_archive 'CCDC 672336' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H14 N2 O10' _chemical_formula_weight 442.33 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 ? _symmetry_space_group_name_H-M ? 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 12.926(5) _cell_length_b 7.948(3) _cell_length_c 19.059(7) _cell_angle_alpha 90.00 _cell_angle_beta 106.540(10) _cell_angle_gamma 90.00 _cell_volume 1877.0(12) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10778 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4347 _reflns_number_gt 3401 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0714P)^2^+0.2800P] 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 4347 _refine_ls_number_parameters 345 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1196 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 C1 C 1.07686(15) 0.0604(3) 0.22550(11) 0.0525(5) Uani 1 1 d . . . C2 C 1.04706(15) 0.0614(3) 0.28854(11) 0.0543(6) Uani 1 1 d . . . C3 C 0.93914(14) 0.0600(2) 0.28731(10) 0.0382(4) Uani 1 1 d . . . C4 C 0.86441(15) 0.0538(3) 0.21894(10) 0.0457(5) Uani 1 1 d . . . C5 C 0.89616(15) 0.0526(3) 0.15618(11) 0.0457(5) Uani 1 1 d . . . C6 C 0.90840(13) 0.0720(2) 0.35613(10) 0.0375(4) Uani 1 1 d . . . C7 C 0.97323(14) 0.1594(2) 0.41548(10) 0.0378(4) Uani 1 1 d . . . C8 C 0.94433(14) 0.1772(2) 0.47880(10) 0.0382(4) Uani 1 1 d . . . C9 C 0.78796(15) 0.0192(3) 0.42930(11) 0.0462(5) Uani 1 1 d . . . C10 C 0.81383(15) 0.0018(3) 0.36465(11) 0.0471(5) Uani 1 1 d . . . C11 C 0.47894(12) 0.70483(19) 0.52699(7) 0.0255(3) Uani 1 1 d . . . C12 C 0.56625(12) 0.76132(19) 0.58380(8) 0.0266(3) Uani 1 1 d . . . C13 C 0.56178(13) 0.7501(2) 0.65582(8) 0.0296(3) Uani 1 1 d . . . C14 C 0.47235(12) 0.6820(2) 0.67172(8) 0.0284(3) Uani 1 1 d . . . C15 C 0.38724(12) 0.61833(19) 0.61523(8) 0.0273(3) Uani 1 1 d . . . C16 C 0.39088(12) 0.6322(2) 0.54332(8) 0.0277(3) Uani 1 1 d . . . C17 C 0.47803(12) 0.72702(19) 0.44889(8) 0.0274(3) Uani 1 1 d . . . C18 C 0.66806(12) 0.8310(2) 0.57198(8) 0.0287(3) Uani 1 1 d . . . C19 C 0.46760(12) 0.6948(2) 0.74951(8) 0.0301(3) Uani 1 1 d . . . C20 C 0.29586(12) 0.5291(2) 0.63268(8) 0.0315(3) Uani 1 1 d . . . N1 N 1.00172(12) 0.05751(19) 0.15996(8) 0.0375(3) Uani 1 1 d . . . N2 N 0.85275(11) 0.10732(18) 0.48512(8) 0.0361(3) Uani 1 1 d . . . O1 O 1.03005(10) 0.06005(19) 0.09867(7) 0.0492(4) Uani 1 1 d . . . O2 O 0.82887(11) 0.12922(17) 0.54775(7) 0.0481(3) Uani 1 1 d . . . O171 O 0.39663(9) 0.65993(15) 0.40086(6) 0.0348(3) Uani 1 1 d . . . O172 O 0.55035(9) 0.80436(18) 0.43298(6) 0.0416(3) Uani 1 1 d . . . O181 O 0.66872(11) 0.99362(16) 0.57072(8) 0.0452(3) Uani 1 1 d . . . O182 O 0.74155(10) 0.74260(17) 0.56843(8) 0.0503(4) Uani 1 1 d . . . O191 O 0.54778(10) 0.62705(19) 0.79748(6) 0.0465(3) Uani 1 1 d . . . O192 O 0.39523(11) 0.77247(19) 0.76448(6) 0.0507(4) Uani 1 1 d . . . O201 O 0.20655(10) 0.5361(2) 0.57968(7) 0.0494(4) Uani 1 1 d . . . O202 O 0.30613(10) 0.4577(2) 0.68991(7) 0.0577(4) Uani 1 1 d . . . H1 H 1.1480(18) 0.062(3) 0.2224(11) 0.050(6) Uiso 1 1 d . . . H2 H 1.0980(19) 0.058(3) 0.3297(13) 0.055(6) Uiso 1 1 d . . . H4 H 0.788(2) 0.060(3) 0.2100(12) 0.056(6) Uiso 1 1 d . . . H5 H 0.8508(17) 0.051(2) 0.1104(12) 0.045(5) Uiso 1 1 d . . . H7 H 1.0420(17) 0.211(3) 0.4164(11) 0.047(5) Uiso 1 1 d . . . H8 H 0.9841(17) 0.239(2) 0.5215(12) 0.047(5) Uiso 1 1 d . . . H9 H 0.7265(18) -0.032(3) 0.4401(12) 0.055(6) Uiso 1 1 d . . . H10 H 0.7679(17) -0.061(3) 0.3268(12) 0.050(6) Uiso 1 1 d . . . H13 H 0.6194(16) 0.789(2) 0.6940(11) 0.038(5) Uiso 1 1 d . . . H16 H 0.3346(15) 0.591(2) 0.5072(10) 0.030(4) Uiso 1 1 d . . . H171 H 0.397(2) 0.687(3) 0.3525(16) 0.080(8) Uiso 1 1 d . . . H181 H 0.737(3) 1.034(4) 0.5604(17) 0.103(10) Uiso 1 1 d . . . H191 H 0.550(2) 0.654(4) 0.8469(17) 0.089(9) Uiso 1 1 d . . . H201 H 0.146(2) 0.496(4) 0.5925(15) 0.083(8) 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 C1 0.0288(9) 0.0915(17) 0.0386(10) -0.0015(10) 0.0118(8) 0.0045(10) C2 0.0307(9) 0.0991(18) 0.0324(10) -0.0027(10) 0.0079(8) 0.0035(10) C3 0.0332(8) 0.0482(10) 0.0355(9) -0.0008(7) 0.0136(7) -0.0008(7) C4 0.0292(9) 0.0692(13) 0.0396(10) 0.0010(9) 0.0111(7) 0.0014(8) C5 0.0335(9) 0.0680(13) 0.0334(10) 0.0017(9) 0.0058(7) 0.0053(9) C6 0.0307(8) 0.0463(10) 0.0380(9) 0.0016(7) 0.0140(7) 0.0010(7) C7 0.0342(9) 0.0438(10) 0.0393(9) 0.0006(7) 0.0167(7) -0.0063(8) C8 0.0377(9) 0.0406(10) 0.0395(9) -0.0036(7) 0.0162(7) -0.0093(8) C9 0.0358(9) 0.0626(12) 0.0446(11) -0.0066(9) 0.0185(8) -0.0162(9) C10 0.0374(9) 0.0661(13) 0.0393(10) -0.0091(9) 0.0134(8) -0.0138(9) C11 0.0291(7) 0.0303(7) 0.0184(7) 0.0016(5) 0.0088(6) 0.0031(6) C12 0.0288(7) 0.0305(8) 0.0217(7) 0.0003(6) 0.0091(6) 0.0017(6) C13 0.0304(8) 0.0386(9) 0.0197(7) -0.0032(6) 0.0070(6) -0.0025(7) C14 0.0324(8) 0.0357(8) 0.0186(7) 0.0012(6) 0.0095(6) 0.0024(6) C15 0.0277(7) 0.0331(8) 0.0228(7) 0.0026(6) 0.0099(6) 0.0016(6) C16 0.0273(7) 0.0349(8) 0.0200(7) 0.0003(6) 0.0052(6) 0.0008(6) C17 0.0300(7) 0.0342(8) 0.0196(7) 0.0001(6) 0.0094(6) 0.0025(6) C18 0.0285(7) 0.0386(9) 0.0191(7) 0.0013(6) 0.0069(6) -0.0005(7) C19 0.0340(8) 0.0385(9) 0.0198(7) -0.0003(6) 0.0107(6) -0.0018(7) C20 0.0310(8) 0.0391(9) 0.0270(8) 0.0016(6) 0.0124(6) -0.0002(7) N1 0.0373(7) 0.0466(8) 0.0314(7) 0.0045(6) 0.0142(6) 0.0102(6) N2 0.0363(7) 0.0409(8) 0.0362(8) 0.0001(6) 0.0186(6) -0.0040(6) O1 0.0459(7) 0.0736(9) 0.0328(7) 0.0117(6) 0.0188(6) 0.0228(7) O2 0.0533(8) 0.0586(8) 0.0427(7) -0.0096(6) 0.0302(6) -0.0189(6) O171 0.0414(6) 0.0446(7) 0.0182(5) -0.0010(5) 0.0083(5) -0.0076(5) O172 0.0369(6) 0.0691(9) 0.0204(5) 0.0028(5) 0.0108(5) -0.0126(6) O181 0.0448(7) 0.0366(7) 0.0654(9) -0.0032(6) 0.0337(7) -0.0049(6) O182 0.0342(6) 0.0474(8) 0.0740(10) 0.0074(7) 0.0231(6) 0.0071(6) O191 0.0486(7) 0.0727(9) 0.0188(6) 0.0033(6) 0.0106(5) 0.0193(7) O192 0.0507(8) 0.0808(10) 0.0237(6) 0.0033(6) 0.0156(5) 0.0240(7) O201 0.0303(6) 0.0799(10) 0.0369(7) 0.0148(6) 0.0079(5) -0.0111(6) O202 0.0416(7) 0.0893(11) 0.0415(8) 0.0312(7) 0.0109(6) -0.0084(7) _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 N1 1.347(2) . ? C1 C2 1.362(3) . ? C1 H1 0.94(2) . ? C2 C3 1.389(3) . ? C2 H2 0.87(2) . ? C3 C4 1.384(3) . ? C3 C6 1.478(2) . ? C4 C5 1.371(3) . ? C4 H4 0.95(2) . ? C5 N1 1.346(2) . ? C5 H5 0.90(2) . ? C6 C7 1.388(3) . ? C6 C10 1.394(3) . ? C7 C8 1.368(2) . ? C7 H7 0.97(2) . ? C8 N2 1.343(2) . ? C8 H8 0.96(2) . ? C9 N2 1.348(2) . ? C9 C10 1.373(3) . ? C9 H9 0.96(2) . ? C10 H10 0.94(2) . ? C11 C16 1.388(2) . ? C11 C12 1.397(2) . ? C11 C17 1.496(2) . ? C12 C13 1.393(2) . ? C12 C18 1.503(2) . ? C13 C14 1.386(2) . ? C13 H13 0.93(2) . ? C14 C15 1.397(2) . ? C14 C19 1.505(2) . ? C15 C16 1.389(2) . ? C15 C20 1.494(2) . ? C16 H16 0.907(19) . ? C17 O172 1.2269(18) . ? C17 O171 1.2965(19) . ? C18 O182 1.199(2) . ? C18 O181 1.293(2) . ? C19 O192 1.2205(19) . ? C19 O191 1.288(2) . ? C20 O202 1.203(2) . ? C20 O201 1.301(2) . ? N1 O1 1.3202(19) . ? N2 O2 1.3269(18) . ? O171 H171 0.95(3) . ? O181 H181 1.01(3) . ? O191 H191 0.96(3) . ? O201 H201 0.94(3) . ? 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 N1 C1 C2 120.52(17) . . ? N1 C1 H1 113.7(13) . . ? C2 C1 H1 125.8(13) . . ? C1 C2 C3 121.33(18) . . ? C1 C2 H2 117.7(15) . . ? C3 C2 H2 120.9(15) . . ? C4 C3 C2 116.40(16) . . ? C4 C3 C6 123.07(16) . . ? C2 C3 C6 120.47(16) . . ? C5 C4 C3 121.30(17) . . ? C5 C4 H4 113.3(14) . . ? C3 C4 H4 125.2(14) . . ? N1 C5 C4 120.25(17) . . ? N1 C5 H5 114.9(13) . . ? C4 C5 H5 124.8(13) . . ? C7 C6 C10 116.82(16) . . ? C7 C6 C3 120.21(15) . . ? C10 C6 C3 122.94(16) . . ? C8 C7 C6 121.16(16) . . ? C8 C7 H7 114.6(12) . . ? C6 C7 H7 124.2(12) . . ? N2 C8 C7 120.34(17) . . ? N2 C8 H8 113.9(12) . . ? C7 C8 H8 125.7(12) . . ? N2 C9 C10 120.36(16) . . ? N2 C9 H9 114.4(13) . . ? C10 C9 H9 125.2(13) . . ? C9 C10 C6 120.67(18) . . ? C9 C10 H10 118.8(13) . . ? C6 C10 H10 120.5(13) . . ? C16 C11 C12 119.53(13) . . ? C16 C11 C17 119.83(13) . . ? C12 C11 C17 120.61(13) . . ? C13 C12 C11 119.48(14) . . ? C13 C12 C18 117.07(13) . . ? C11 C12 C18 123.43(13) . . ? C14 C13 C12 120.77(14) . . ? C14 C13 H13 119.4(12) . . ? C12 C13 H13 119.9(12) . . ? C13 C14 C15 119.73(13) . . ? C13 C14 C19 117.36(13) . . ? C15 C14 C19 122.67(13) . . ? C16 C15 C14 119.42(13) . . ? C16 C15 C20 120.55(14) . . ? C14 C15 C20 119.97(13) . . ? C11 C16 C15 120.96(14) . . ? C11 C16 H16 120.7(11) . . ? C15 C16 H16 118.3(11) . . ? O172 C17 O171 123.63(13) . . ? O172 C17 C11 120.96(13) . . ? O171 C17 C11 115.41(13) . . ? O182 C18 O181 125.11(15) . . ? O182 C18 C12 122.32(15) . . ? O181 C18 C12 112.45(13) . . ? O192 C19 O191 124.11(14) . . ? O192 C19 C14 120.89(14) . . ? O191 C19 C14 114.88(13) . . ? O202 C20 O201 124.66(15) . . ? O202 C20 C15 122.38(15) . . ? O201 C20 C15 112.96(13) . . ? O1 N1 C5 119.03(14) . . ? O1 N1 C1 120.80(15) . . ? C5 N1 C1 120.17(15) . . ? O2 N2 C8 117.58(14) . . ? O2 N2 C9 121.80(14) . . ? C8 N2 C9 120.62(15) . . ? C17 O171 H171 111.2(16) . . ? C18 O181 H181 109.6(18) . . ? C19 O191 H191 113.3(17) . . ? C20 O201 H201 113.9(17) . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 0.249 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.057