# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Miao Du' _publ_contact_author_email DUMIAO@PUBLIC.TPT.TJ.CN _publ_section_title ; Cocrystallization of a versatile building block 4-amino-3,5-bis(4-pyridyl)-1,2,4-triazole with R-isophthalic acids (R = -H, -NH2, -SO3H, and -COOH): Polymorphism and substituent effect on structural diversity ; loop_ _publ_author_name 'Miao Du.' 'Hua Cai.' 'Xiu-Juan Jiang.' 'Xue Tan.' 'Zhi-Hui Zhang.' data_1 _database_code_depnum_ccdc_archive 'CCDC 693289' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 N6 O4' _chemical_formula_weight 404.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.5354(9) _cell_length_b 6.5819(3) _cell_length_c 14.7391(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.9870(10) _cell_angle_gamma 90.00 _cell_volume 1797.06(15) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3366 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 27.31 _exptl_crystal_description Rod _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9614 _exptl_absorpt_correction_T_max 0.9802 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8833 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.10 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3165 _reflns_number_gt 2584 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0478P)^2^+0.4497P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0060(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3165 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0992 _refine_ls_wR_factor_gt 0.0858 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 O1 O 0.35821(6) 0.88762(19) 0.62120(9) 0.0519(4) Uani 1 1 d . . . O2 O 0.32241(6) 0.64876(19) 0.52272(9) 0.0483(3) Uani 1 1 d . . . H2 H 0.3585 0.5910 0.5435 0.072 Uiso 1 1 calc R . . O3 O 0.06795(6) 0.67717(18) 0.41019(10) 0.0528(4) Uani 1 1 d . . . H3 H 0.0313 0.6372 0.3829 0.079 Uiso 1 1 calc R . . O4 O 0.01521(6) 0.97903(19) 0.39120(9) 0.0515(3) Uani 1 1 d . . . N1 N 0.43820(7) 0.4669(2) 0.58612(9) 0.0393(3) Uani 1 1 d . . . N2 N 0.62087(7) -0.0649(2) 0.68097(11) 0.0464(4) Uani 1 1 d . . . N3 N 0.68816(7) -0.1334(2) 0.70915(11) 0.0444(4) Uani 1 1 d . . . N4 N 0.69231(6) 0.19795(18) 0.69896(8) 0.0306(3) Uani 1 1 d . . . N5 N 0.72159(7) 0.3948(2) 0.69415(11) 0.0423(4) Uani 1 1 d . . . H5A H 0.7112 0.4477 0.6352 0.063 Uiso 1 1 d R . . H5B H 0.7008 0.4707 0.7415 0.063 Uiso 1 1 d R . . N6 N 0.94637(7) -0.0573(2) 0.82122(10) 0.0412(4) Uani 1 1 d . . . C1 C 0.55131(9) 0.4608(3) 0.66954(12) 0.0397(4) Uani 1 1 d . . . H1 H 0.5856 0.5301 0.7052 0.048 Uiso 1 1 calc R . . C2 C 0.48889(9) 0.5574(3) 0.63829(12) 0.0412(4) Uani 1 1 d . . . H2A H 0.4820 0.6923 0.6545 0.049 Uiso 1 1 calc R . . C3 C 0.44808(9) 0.2726(3) 0.56504(12) 0.0437(4) Uani 1 1 d . . . H3A H 0.4131 0.2074 0.5289 0.052 Uiso 1 1 calc R . . C4 C 0.50771(9) 0.1644(3) 0.59434(12) 0.0424(4) Uani 1 1 d . . . H4 H 0.5120 0.0279 0.5792 0.051 Uiso 1 1 calc R . . C5 C 0.56164(8) 0.2591(2) 0.64666(11) 0.0331(4) Uani 1 1 d . . . C6 C 0.62421(8) 0.1343(2) 0.67546(11) 0.0340(4) Uani 1 1 d . . . C7 C 0.73045(8) 0.0260(2) 0.71903(10) 0.0324(4) Uani 1 1 d . . . C8 C 0.80661(8) 0.0091(2) 0.75051(10) 0.0320(4) Uani 1 1 d . . . C9 C 0.84587(8) 0.1641(3) 0.79272(11) 0.0374(4) Uani 1 1 d . . . H9 H 0.8260 0.2932 0.7980 0.045 Uiso 1 1 calc R . . C10 C 0.91489(9) 0.1241(3) 0.82684(12) 0.0410(4) Uani 1 1 d . . . H10 H 0.9406 0.2291 0.8551 0.049 Uiso 1 1 calc R . . C11 C 0.90914(8) -0.2045(3) 0.77804(11) 0.0402(4) Uani 1 1 d . . . H11 H 0.9310 -0.3307 0.7719 0.048 Uiso 1 1 calc R . . C12 C 0.84019(8) -0.1790(2) 0.74232(11) 0.0362(4) Uani 1 1 d . . . H12 H 0.8163 -0.2860 0.7131 0.043 Uiso 1 1 calc R . . C13 C 0.25025(8) 0.9432(2) 0.53373(10) 0.0327(4) Uani 1 1 d . . . C14 C 0.24727(9) 1.1475(2) 0.55625(11) 0.0385(4) Uani 1 1 d . . . H14 H 0.2858 1.2077 0.5882 0.046 Uiso 1 1 calc R . . C15 C 0.18720(9) 1.2622(3) 0.53136(12) 0.0423(4) Uani 1 1 d . . . H15 H 0.1863 1.4003 0.5447 0.051 Uiso 1 1 calc R . . C16 C 0.12882(9) 1.1726(3) 0.48697(11) 0.0387(4) Uani 1 1 d . . . H16 H 0.0883 1.2499 0.4712 0.046 Uiso 1 1 calc R . . C17 C 0.13033(8) 0.9674(2) 0.46575(10) 0.0329(4) Uani 1 1 d . . . C18 C 0.19161(8) 0.8535(2) 0.48753(10) 0.0327(4) Uani 1 1 d . . . H18 H 0.1935 0.7171 0.4712 0.039 Uiso 1 1 calc R . . C19 C 0.31524(8) 0.8243(2) 0.56328(11) 0.0365(4) Uani 1 1 d . . . C20 C 0.06527(8) 0.8759(3) 0.41891(11) 0.0369(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0403(7) 0.0507(8) 0.0629(8) -0.0062(6) -0.0230(6) 0.0029(6) O2 0.0366(7) 0.0414(7) 0.0655(8) -0.0066(6) -0.0187(6) 0.0120(5) O3 0.0364(7) 0.0402(7) 0.0801(9) -0.0016(6) -0.0230(6) -0.0016(6) O4 0.0365(7) 0.0494(8) 0.0672(8) 0.0013(6) -0.0185(6) 0.0086(6) N1 0.0289(7) 0.0392(8) 0.0493(8) 0.0047(6) -0.0045(6) 0.0048(6) N2 0.0315(7) 0.0291(8) 0.0774(11) 0.0023(7) -0.0166(7) 0.0021(6) N3 0.0309(7) 0.0292(8) 0.0719(10) 0.0030(7) -0.0153(7) 0.0032(6) N4 0.0260(6) 0.0246(7) 0.0406(7) 0.0001(5) -0.0069(5) 0.0007(5) N5 0.0330(7) 0.0273(7) 0.0657(10) 0.0033(7) -0.0102(7) -0.0035(6) N6 0.0286(7) 0.0437(9) 0.0508(8) 0.0027(7) -0.0077(6) 0.0008(6) C1 0.0340(9) 0.0338(9) 0.0505(10) -0.0031(7) -0.0099(7) 0.0025(7) C2 0.0386(9) 0.0328(9) 0.0518(10) -0.0010(8) -0.0041(8) 0.0080(7) C3 0.0306(9) 0.0394(10) 0.0601(11) 0.0002(8) -0.0130(8) -0.0006(7) C4 0.0356(9) 0.0300(9) 0.0605(11) -0.0019(8) -0.0114(8) 0.0019(7) C5 0.0272(8) 0.0306(8) 0.0410(9) 0.0028(7) -0.0041(6) 0.0010(6) C6 0.0288(8) 0.0288(8) 0.0440(9) -0.0002(7) -0.0071(7) 0.0011(7) C7 0.0292(8) 0.0273(8) 0.0402(8) 0.0006(6) -0.0064(6) 0.0024(7) C8 0.0281(8) 0.0338(9) 0.0339(8) 0.0043(6) -0.0040(6) 0.0017(7) C9 0.0335(8) 0.0339(9) 0.0441(9) 0.0007(7) -0.0068(7) 0.0018(7) C10 0.0345(9) 0.0406(10) 0.0473(10) 0.0001(8) -0.0091(7) -0.0038(8) C11 0.0314(8) 0.0386(10) 0.0502(10) 0.0006(8) -0.0040(7) 0.0069(7) C12 0.0315(8) 0.0341(9) 0.0425(9) -0.0006(7) -0.0063(7) 0.0010(7) C13 0.0270(8) 0.0349(9) 0.0360(8) 0.0036(7) -0.0017(6) 0.0004(7) C14 0.0325(8) 0.0374(9) 0.0452(9) -0.0039(7) -0.0048(7) -0.0030(7) C15 0.0428(10) 0.0319(9) 0.0522(10) -0.0042(8) -0.0001(8) 0.0033(8) C16 0.0325(8) 0.0392(9) 0.0443(9) 0.0018(7) -0.0015(7) 0.0089(7) C17 0.0285(8) 0.0352(9) 0.0348(8) 0.0033(7) -0.0016(6) 0.0020(7) C18 0.0297(8) 0.0299(8) 0.0383(8) 0.0023(7) -0.0025(6) 0.0004(7) C19 0.0294(8) 0.0352(9) 0.0446(9) 0.0044(7) -0.0039(7) -0.0015(7) C20 0.0297(8) 0.0392(10) 0.0416(9) 0.0023(7) -0.0038(7) 0.0024(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 O1 C19 1.2206(18) . ? O2 C19 1.310(2) . ? O2 H2 0.8200 . ? O3 C20 1.316(2) . ? O3 H3 0.8200 . ? O4 C20 1.2090(19) . ? N1 C3 1.330(2) . ? N1 C2 1.334(2) . ? N2 C6 1.315(2) . ? N2 N3 1.3766(18) . ? N3 C7 1.314(2) . ? N4 C7 1.3616(19) . ? N4 C6 1.3632(19) . ? N4 N5 1.4075(17) . ? N5 H5A 0.9500 . ? N5 H5B 0.9499 . ? N6 C10 1.333(2) . ? N6 C11 1.338(2) . ? C1 C5 1.385(2) . ? C1 C2 1.385(2) . ? C1 H1 0.9300 . ? C2 H2A 0.9300 . ? C3 C4 1.372(2) . ? C3 H3A 0.9300 . ? C4 C5 1.389(2) . ? C4 H4 0.9300 . ? C5 C6 1.472(2) . ? C7 C8 1.475(2) . ? C8 C9 1.388(2) . ? C8 C12 1.392(2) . ? C9 C10 1.384(2) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.376(2) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.387(2) . ? C13 C18 1.394(2) . ? C13 C19 1.489(2) . ? C14 C15 1.384(2) . ? C14 H14 0.9300 . ? C15 C16 1.378(2) . ? C15 H15 0.9300 . ? C16 C17 1.387(2) . ? C16 H16 0.9300 . ? C17 C18 1.389(2) . ? C17 C20 1.495(2) . ? C18 H18 0.9300 . ? 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 C19 O2 H2 109.5 . . ? C20 O3 H3 109.5 . . ? C3 N1 C2 117.63(14) . . ? C6 N2 N3 107.50(13) . . ? C7 N3 N2 107.64(13) . . ? C7 N4 C6 105.61(12) . . ? C7 N4 N5 125.30(12) . . ? C6 N4 N5 128.71(12) . . ? N4 N5 H5A 108.5 . . ? N4 N5 H5B 106.3 . . ? H5A N5 H5B 113.9 . . ? C10 N6 C11 117.32(14) . . ? C5 C1 C2 118.69(15) . . ? C5 C1 H1 120.7 . . ? C2 C1 H1 120.7 . . ? N1 C2 C1 123.42(16) . . ? N1 C2 H2A 118.3 . . ? C1 C2 H2A 118.3 . . ? N1 C3 C4 122.78(16) . . ? N1 C3 H3A 118.6 . . ? C4 C3 H3A 118.6 . . ? C3 C4 C5 119.90(16) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C1 C5 C4 117.54(14) . . ? C1 C5 C6 125.39(14) . . ? C4 C5 C6 117.04(14) . . ? N2 C6 N4 109.62(13) . . ? N2 C6 C5 122.41(14) . . ? N4 C6 C5 127.97(14) . . ? N3 C7 N4 109.63(13) . . ? N3 C7 C8 122.36(14) . . ? N4 C7 C8 127.98(14) . . ? C9 C8 C12 117.61(14) . . ? C9 C8 C7 124.51(14) . . ? C12 C8 C7 117.76(14) . . ? C10 C9 C8 119.12(15) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? N6 C10 C9 123.32(16) . . ? N6 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? N6 C11 C12 123.39(16) . . ? N6 C11 H11 118.3 . . ? C12 C11 H11 118.3 . . ? C11 C12 C8 119.19(15) . . ? C11 C12 H12 120.4 . . ? C8 C12 H12 120.4 . . ? C14 C13 C18 119.41(14) . . ? C14 C13 C19 118.56(14) . . ? C18 C13 C19 121.98(14) . . ? C15 C14 C13 120.26(15) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C16 C15 C14 120.23(16) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 120.17(15) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C18 119.76(15) . . ? C16 C17 C20 118.29(14) . . ? C18 C17 C20 121.95(14) . . ? C17 C18 C13 120.11(15) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? O1 C19 O2 123.11(14) . . ? O1 C19 C13 121.80(15) . . ? O2 C19 C13 115.09(13) . . ? O4 C20 O3 123.80(15) . . ? O4 C20 C17 121.81(15) . . ? O3 C20 C17 114.39(14) . . ? 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 C6 N2 N3 C7 -0.6(2) . . . . ? C3 N1 C2 C1 1.4(3) . . . . ? C5 C1 C2 N1 -0.8(3) . . . . ? C2 N1 C3 C4 -0.3(3) . . . . ? N1 C3 C4 C5 -1.5(3) . . . . ? C2 C1 C5 C4 -0.9(2) . . . . ? C2 C1 C5 C6 -178.99(16) . . . . ? C3 C4 C5 C1 2.0(3) . . . . ? C3 C4 C5 C6 -179.76(16) . . . . ? N3 N2 C6 N4 0.3(2) . . . . ? N3 N2 C6 C5 179.67(14) . . . . ? C7 N4 C6 N2 0.10(19) . . . . ? N5 N4 C6 N2 173.19(15) . . . . ? C7 N4 C6 C5 -179.22(15) . . . . ? N5 N4 C6 C5 -6.1(3) . . . . ? C1 C5 C6 N2 154.88(18) . . . . ? C4 C5 C6 N2 -23.2(2) . . . . ? C1 C5 C6 N4 -25.9(3) . . . . ? C4 C5 C6 N4 156.03(16) . . . . ? N2 N3 C7 N4 0.68(19) . . . . ? N2 N3 C7 C8 178.74(14) . . . . ? C6 N4 C7 N3 -0.49(18) . . . . ? N5 N4 C7 N3 -173.89(15) . . . . ? C6 N4 C7 C8 -178.41(15) . . . . ? N5 N4 C7 C8 8.2(3) . . . . ? N3 C7 C8 C9 -155.71(16) . . . . ? N4 C7 C8 C9 22.0(3) . . . . ? N3 C7 C8 C12 20.2(2) . . . . ? N4 C7 C8 C12 -162.08(15) . . . . ? C12 C8 C9 C10 -2.0(2) . . . . ? C7 C8 C9 C10 174.00(15) . . . . ? C11 N6 C10 C9 1.8(3) . . . . ? C8 C9 C10 N6 0.2(3) . . . . ? C10 N6 C11 C12 -2.0(3) . . . . ? N6 C11 C12 C8 0.3(3) . . . . ? C9 C8 C12 C11 1.7(2) . . . . ? C7 C8 C12 C11 -174.50(14) . . . . ? C18 C13 C14 C15 -1.4(2) . . . . ? C19 C13 C14 C15 -178.87(15) . . . . ? C13 C14 C15 C16 2.4(3) . . . . ? C14 C15 C16 C17 -1.0(3) . . . . ? C15 C16 C17 C18 -1.5(2) . . . . ? C15 C16 C17 C20 179.01(15) . . . . ? C16 C17 C18 C13 2.5(2) . . . . ? C20 C17 C18 C13 -177.99(14) . . . . ? C14 C13 C18 C17 -1.1(2) . . . . ? C19 C13 C18 C17 176.33(14) . . . . ? C14 C13 C19 O1 15.3(2) . . . . ? C18 C13 C19 O1 -162.16(16) . . . . ? C14 C13 C19 O2 -164.78(15) . . . . ? C18 C13 C19 O2 17.8(2) . . . . ? C16 C17 C20 O4 7.7(2) . . . . ? C18 C17 C20 O4 -171.80(15) . . . . ? C16 C17 C20 O3 -172.90(15) . . . . ? C18 C17 C20 O3 7.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.200 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.035 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 693290' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 N6 O4' _chemical_formula_weight 404.39 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 6.255(2) _cell_length_b 7.187(2) _cell_length_c 20.272(4) _cell_angle_alpha 83.78(3) _cell_angle_beta 86.62(3) _cell_angle_gamma 79.03(2) _cell_volume 888.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 457 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 26.56 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9801 _exptl_absorpt_correction_T_max 0.9954 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4675 _diffrn_reflns_av_R_equivalents 0.0609 _diffrn_reflns_av_sigmaI/netI 0.1930 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.01 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3073 _reflns_number_gt 1237 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0261P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3073 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1681 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1037 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 O1 O 0.2222(4) 0.1792(4) 0.76837(12) 0.0528(9) Uani 1 1 d . . . H1 H 0.1768 0.1716 0.7318 0.079 Uiso 1 1 calc R . . O2 O 0.5319(4) 0.0352(4) 0.72196(12) 0.0576(9) Uani 1 1 d . . . O3 O 0.5041(4) 0.2938(4) 1.05453(12) 0.0636(10) Uani 1 1 d . . . O4 O 0.1981(4) 0.3393(4) 1.00011(12) 0.0552(9) Uani 1 1 d . . . H4 H 0.1439 0.3722 1.0358 0.083 Uiso 1 1 calc R . . N1 N 0.0471(6) 0.3989(5) 0.12637(15) 0.0484(10) Uani 1 1 d . . . N2 N -0.3186(5) 0.3860(4) 0.35837(15) 0.0481(10) Uani 1 1 d . . . N3 N -0.3130(5) 0.3586(4) 0.42752(15) 0.0443(9) Uani 1 1 d . . . N4 N 0.0211(5) 0.2884(4) 0.38511(14) 0.0370(9) Uani 1 1 d . . . N5 N 0.2486(5) 0.2109(5) 0.38198(14) 0.0463(10) Uani 1 1 d . . . H5A H 0.2843 0.1637 0.3426 0.059(12) Uiso 1 1 d R . . H5B H 0.3317 0.2988 0.3851 0.16(3) Uiso 1 1 d R . . N6 N 0.0663(6) 0.1880(4) 0.64605(15) 0.0498(10) Uani 1 1 d . . . C1 C -0.1973(6) 0.3286(5) 0.21783(18) 0.0456(12) Uani 1 1 d . . . H1A H -0.3280 0.2913 0.2323 0.055 Uiso 1 1 calc R . . C2 C -0.1392(7) 0.3516(6) 0.1501(2) 0.0514(14) Uani 1 1 d . . . H2 H -0.2374 0.3325 0.1199 0.062 Uiso 1 1 calc R . . C3 C 0.1847(6) 0.4298(5) 0.16984(19) 0.0485(12) Uani 1 1 d . . . H3 H 0.3154 0.4648 0.1540 0.058 Uiso 1 1 calc R . . C4 C 0.1401(7) 0.4117(5) 0.23855(18) 0.0439(12) Uani 1 1 d . . . H4A H 0.2412 0.4322 0.2675 0.053 Uiso 1 1 calc R . . C5 C -0.0533(6) 0.3635(5) 0.26280(18) 0.0398(12) Uani 1 1 d . . . C6 C -0.1162(6) 0.3434(5) 0.33447(18) 0.0382(11) Uani 1 1 d . . . C7 C -0.1058(6) 0.2983(5) 0.44214(19) 0.0395(12) Uani 1 1 d . . . C8 C -0.0385(6) 0.2561(5) 0.51151(18) 0.0405(12) Uani 1 1 d . . . C9 C 0.1717(6) 0.1842(5) 0.52964(18) 0.0526(13) Uani 1 1 d . . . H9 H 0.2830 0.1571 0.4977 0.063 Uiso 1 1 calc R . . C10 C 0.2139(7) 0.1527(6) 0.5971(2) 0.0609(14) Uani 1 1 d . . . H10 H 0.3567 0.1032 0.6087 0.073 Uiso 1 1 calc R . . C11 C -0.1362(7) 0.2569(6) 0.62735(19) 0.0536(13) Uani 1 1 d . . . H11 H -0.2450 0.2807 0.6603 0.064 Uiso 1 1 calc R . . C12 C -0.1948(6) 0.2953(5) 0.56183(19) 0.0456(12) Uani 1 1 d . . . H12 H -0.3383 0.3471 0.5517 0.055 Uiso 1 1 calc R . . C13 C 0.4326(7) 0.1087(5) 0.76907(19) 0.0433(12) Uani 1 1 d . . . C14 C 0.5360(6) 0.1270(5) 0.83114(17) 0.0366(11) Uani 1 1 d . . . C15 C 0.7602(7) 0.0672(5) 0.83403(19) 0.0478(12) Uani 1 1 d . . . H15 H 0.8398 0.0188 0.7975 0.057 Uiso 1 1 calc R . . C16 C 0.8659(6) 0.0794(5) 0.89115(19) 0.0515(13) Uani 1 1 d . . . H16 H 1.0158 0.0380 0.8930 0.062 Uiso 1 1 calc R . . C17 C 0.7494(6) 0.1527(5) 0.94527(19) 0.0467(12) Uani 1 1 d . . . H17 H 0.8208 0.1611 0.9835 0.056 Uiso 1 1 calc R . . C18 C 0.5249(6) 0.2143(5) 0.94276(18) 0.0383(11) Uani 1 1 d . . . C19 C 0.4104(7) 0.2856(5) 1.00484(19) 0.0424(11) Uani 1 1 d . . . C20 C 0.4190(6) 0.2013(5) 0.88600(17) 0.0423(12) Uani 1 1 d . . . H20 H 0.2690 0.2423 0.8844 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0440(19) 0.078(2) 0.0347(18) -0.0144(16) -0.0057(14) 0.0007(17) O2 0.0532(19) 0.077(2) 0.0389(18) -0.0229(16) 0.0043(15) 0.0053(17) O3 0.054(2) 0.103(2) 0.0397(18) -0.0235(17) -0.0105(16) -0.0161(18) O4 0.051(2) 0.081(2) 0.0290(17) -0.0131(16) -0.0001(15) 0.0017(18) N1 0.048(2) 0.055(2) 0.038(2) -0.0021(19) -0.012(2) 0.002(2) N2 0.042(2) 0.067(2) 0.033(2) -0.0096(18) -0.0042(18) -0.002(2) N3 0.034(2) 0.064(2) 0.034(2) -0.0073(18) -0.0013(17) -0.0037(19) N4 0.035(2) 0.045(2) 0.031(2) -0.0110(17) -0.0048(17) -0.0016(18) N5 0.029(2) 0.070(2) 0.035(2) -0.0117(19) -0.0033(17) 0.004(2) N6 0.051(2) 0.062(2) 0.036(2) -0.0091(19) -0.003(2) -0.006(2) C1 0.043(3) 0.052(3) 0.040(3) -0.010(2) -0.009(2) 0.002(2) C2 0.047(3) 0.059(3) 0.046(3) -0.016(3) -0.020(3) 0.008(3) C3 0.041(3) 0.056(3) 0.046(3) -0.009(2) -0.005(2) -0.001(2) C4 0.041(3) 0.052(3) 0.037(3) -0.011(2) -0.007(2) 0.001(2) C5 0.040(3) 0.043(3) 0.035(3) -0.013(2) -0.008(2) 0.003(2) C6 0.035(3) 0.049(3) 0.031(3) -0.011(2) -0.001(2) -0.005(2) C7 0.039(3) 0.044(3) 0.035(3) -0.016(2) -0.005(2) 0.002(2) C8 0.040(3) 0.048(3) 0.036(3) -0.016(2) -0.003(2) -0.006(2) C9 0.044(3) 0.078(3) 0.031(3) -0.013(2) 0.000(2) 0.006(3) C10 0.049(3) 0.085(4) 0.046(3) -0.017(3) -0.009(3) 0.004(3) C11 0.053(3) 0.074(3) 0.038(3) -0.018(2) 0.013(2) -0.020(3) C12 0.041(3) 0.054(3) 0.041(3) -0.008(2) -0.003(2) -0.007(2) C13 0.046(3) 0.042(3) 0.040(3) -0.002(2) 0.000(2) -0.005(2) C14 0.043(3) 0.035(2) 0.029(2) -0.004(2) -0.004(2) 0.001(2) C15 0.051(3) 0.045(3) 0.044(3) -0.009(2) -0.002(2) 0.001(2) C16 0.036(3) 0.059(3) 0.058(3) -0.009(2) -0.005(2) -0.003(2) C17 0.041(3) 0.052(3) 0.047(3) -0.010(2) -0.012(2) -0.003(2) C18 0.042(3) 0.036(2) 0.036(2) -0.004(2) -0.004(2) -0.002(2) C19 0.044(3) 0.043(3) 0.040(3) -0.004(2) -0.008(2) -0.006(2) C20 0.036(3) 0.047(3) 0.043(3) -0.011(2) 0.000(2) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.317(4) . ? O1 H1 0.8200 . ? O2 C13 1.221(4) . ? O3 C19 1.207(4) . ? O4 C19 1.317(4) . ? O4 H4 0.8200 . ? N1 C2 1.325(5) . ? N1 C3 1.331(4) . ? N2 C6 1.320(4) . ? N2 N3 1.396(4) . ? N3 C7 1.326(4) . ? N4 C6 1.355(4) . ? N4 C7 1.364(4) . ? N4 N5 1.426(4) . ? N5 H5A 0.9000 . ? N5 H5B 0.9000 . ? N6 C10 1.326(4) . ? N6 C11 1.331(5) . ? C1 C5 1.392(4) . ? C1 C2 1.400(5) . ? C1 H1A 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.401(5) . ? C3 H3 0.9300 . ? C4 C5 1.370(5) . ? C4 H4A 0.9300 . ? C5 C6 1.482(5) . ? C7 C8 1.475(5) . ? C8 C9 1.374(5) . ? C8 C12 1.384(5) . ? C9 C10 1.394(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.383(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.478(5) . ? C14 C15 1.389(5) . ? C14 C20 1.393(4) . ? C15 C16 1.386(4) . ? C15 H15 0.9300 . ? C16 C17 1.377(5) . ? C16 H16 0.9300 . ? C17 C18 1.392(5) . ? C17 H17 0.9300 . ? C18 C20 1.381(4) . ? C18 C19 1.501(5) . ? C20 H20 0.9300 . ? 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 C13 O1 H1 109.5 . . ? C19 O4 H4 109.5 . . ? C2 N1 C3 117.6(4) . . ? C6 N2 N3 107.6(3) . . ? C7 N3 N2 106.7(3) . . ? C6 N4 C7 106.2(3) . . ? C6 N4 N5 128.5(3) . . ? C7 N4 N5 124.8(3) . . ? N4 N5 H5A 109.3 . . ? N4 N5 H5B 112.7 . . ? H5A N5 H5B 106.9 . . ? C10 N6 C11 115.5(4) . . ? C5 C1 C2 117.9(4) . . ? C5 C1 H1A 121.1 . . ? C2 C1 H1A 121.1 . . ? N1 C2 C1 124.0(3) . . ? N1 C2 H2 118.0 . . ? C1 C2 H2 118.0 . . ? N1 C3 C4 122.5(4) . . ? N1 C3 H3 118.7 . . ? C4 C3 H3 118.7 . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 C1 118.3(4) . . ? C4 C5 C6 123.6(3) . . ? C1 C5 C6 118.1(4) . . ? N2 C6 N4 109.8(3) . . ? N2 C6 C5 123.9(3) . . ? N4 C6 C5 126.3(4) . . ? N3 C7 N4 109.8(3) . . ? N3 C7 C8 121.5(4) . . ? N4 C7 C8 128.7(4) . . ? C9 C8 C12 117.5(4) . . ? C9 C8 C7 124.1(3) . . ? C12 C8 C7 118.4(4) . . ? C8 C9 C10 118.4(4) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? N6 C10 C9 125.1(4) . . ? N6 C10 H10 117.5 . . ? C9 C10 H10 117.5 . . ? N6 C11 C12 123.9(4) . . ? N6 C11 H11 118.0 . . ? C12 C11 H11 118.0 . . ? C11 C12 C8 119.6(4) . . ? C11 C12 H12 120.2 . . ? C8 C12 H12 120.2 . . ? O2 C13 O1 122.2(3) . . ? O2 C13 C14 123.4(4) . . ? O1 C13 C14 114.3(3) . . ? C15 C14 C20 119.3(3) . . ? C15 C14 C13 117.7(3) . . ? C20 C14 C13 123.0(4) . . ? C16 C15 C14 120.3(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C15 120.2(4) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 120.0(3) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C20 C18 C17 119.9(3) . . ? C20 C18 C19 123.7(4) . . ? C17 C18 C19 116.3(3) . . ? O3 C19 O4 123.0(4) . . ? O3 C19 C18 123.2(4) . . ? O4 C19 C18 113.9(3) . . ? C18 C20 C14 120.3(3) . . ? C18 C20 H20 119.9 . . ? C14 C20 H20 119.9 . . ? 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 C6 N2 N3 C7 -0.6(4) . . . . ? C3 N1 C2 C1 -1.4(6) . . . . ? C5 C1 C2 N1 2.1(6) . . . . ? C2 N1 C3 C4 0.8(6) . . . . ? N1 C3 C4 C5 -1.1(6) . . . . ? C3 C4 C5 C1 1.8(5) . . . . ? C3 C4 C5 C6 -179.2(3) . . . . ? C2 C1 C5 C4 -2.2(5) . . . . ? C2 C1 C5 C6 178.7(3) . . . . ? N3 N2 C6 N4 0.3(4) . . . . ? N3 N2 C6 C5 -176.9(3) . . . . ? C7 N4 C6 N2 0.1(4) . . . . ? N5 N4 C6 N2 172.5(3) . . . . ? C7 N4 C6 C5 177.3(3) . . . . ? N5 N4 C6 C5 -10.3(6) . . . . ? C4 C5 C6 N2 146.7(4) . . . . ? C1 C5 C6 N2 -34.3(5) . . . . ? C4 C5 C6 N4 -30.1(6) . . . . ? C1 C5 C6 N4 148.9(3) . . . . ? N2 N3 C7 N4 0.7(4) . . . . ? N2 N3 C7 C8 179.4(3) . . . . ? C6 N4 C7 N3 -0.6(4) . . . . ? N5 N4 C7 N3 -173.3(3) . . . . ? C6 N4 C7 C8 -179.1(3) . . . . ? N5 N4 C7 C8 8.1(5) . . . . ? N3 C7 C8 C9 176.6(4) . . . . ? N4 C7 C8 C9 -5.0(6) . . . . ? N3 C7 C8 C12 -5.1(5) . . . . ? N4 C7 C8 C12 173.4(3) . . . . ? C12 C8 C9 C10 0.9(6) . . . . ? C7 C8 C9 C10 179.3(4) . . . . ? C11 N6 C10 C9 0.7(6) . . . . ? C8 C9 C10 N6 -0.4(6) . . . . ? C10 N6 C11 C12 -1.5(6) . . . . ? N6 C11 C12 C8 2.0(6) . . . . ? C9 C8 C12 C11 -1.6(5) . . . . ? C7 C8 C12 C11 179.9(3) . . . . ? O2 C13 C14 C15 3.9(6) . . . . ? O1 C13 C14 C15 -175.9(4) . . . . ? O2 C13 C14 C20 -176.3(4) . . . . ? O1 C13 C14 C20 4.0(5) . . . . ? C20 C14 C15 C16 0.7(6) . . . . ? C13 C14 C15 C16 -179.4(3) . . . . ? C14 C15 C16 C17 -0.6(6) . . . . ? C15 C16 C17 C18 0.2(6) . . . . ? C16 C17 C18 C20 0.2(6) . . . . ? C16 C17 C18 C19 177.9(3) . . . . ? C20 C18 C19 O3 178.9(4) . . . . ? C17 C18 C19 O3 1.3(6) . . . . ? C20 C18 C19 O4 -1.4(6) . . . . ? C17 C18 C19 O4 -179.0(4) . . . . ? C17 C18 C20 C14 -0.1(6) . . . . ? C19 C18 C20 C14 -177.6(4) . . . . ? C15 C14 C20 C18 -0.3(6) . . . . ? C13 C14 C20 C18 179.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.320 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.081 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 693291' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H17 N7 O4' _chemical_formula_weight 419.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.5638(13) _cell_length_b 7.3710(6) _cell_length_c 14.4866(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.0100(10) _cell_angle_gamma 90.00 _cell_volume 1872.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2542 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 27.46 _exptl_crystal_description Block _exptl_crystal_colour Brown _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8987 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9849 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3302 _reflns_number_gt 2338 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0551P)^2^+0.2035P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3302 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 O1 O 0.27304(7) -0.32428(18) 0.00052(9) 0.0451(4) Uani 1 1 d . . . O2 O 0.32301(7) -0.06809(17) -0.05254(10) 0.0458(4) Uani 1 1 d . . . H2 H 0.3587 -0.1354 -0.0632 0.069 Uiso 1 1 calc R . . O3 O 0.01481(7) -0.31371(18) 0.09825(11) 0.0539(4) Uani 1 1 d . . . H3 H -0.0249 -0.3600 0.1142 0.081 Uiso 1 1 calc R . . O4 O -0.03737(8) -0.06270(18) 0.15351(11) 0.0578(4) Uani 1 1 d . . . N1 N 0.43487(9) 0.7225(2) 0.90969(11) 0.0410(4) Uani 1 1 d . . . N2 N 0.58631(8) 0.1668(2) 0.84415(11) 0.0402(4) Uani 1 1 d . . . N3 N 0.64609(8) 0.0702(2) 0.81131(11) 0.0400(4) Uani 1 1 d . . . N4 N 0.66564(8) 0.35906(19) 0.78559(10) 0.0317(4) Uani 1 1 d . . . N5 N 0.69460(8) 0.52526(19) 0.75480(11) 0.0397(4) Uani 1 1 d . . . H5A H 0.6994 0.5204 0.6933 0.048 Uiso 1 1 d R . . H5B H 0.7357 0.5731 0.7854 0.048 Uiso 1 1 d R . . N6 N 0.89049(9) -0.0187(2) 0.65239(11) 0.0421(4) Uani 1 1 d . . . N7 N 0.16817(9) 0.4172(2) 0.10274(12) 0.0464(4) Uani 1 1 d . . . H7A H 0.1245 0.4769 0.1120 0.056 Uiso 1 1 d R . . H7B H 0.1977 0.4747 0.0631 0.056 Uiso 1 1 d R . . C1 C 0.54470(10) 0.4806(2) 0.85433(12) 0.0336(4) Uani 1 1 d . . . C2 C 0.47304(10) 0.4211(3) 0.87930(13) 0.0397(5) Uani 1 1 d . . . H2A H 0.4610 0.2983 0.8773 0.048 Uiso 1 1 calc R . . C3 C 0.42070(10) 0.5452(3) 0.90669(13) 0.0411(5) Uani 1 1 d . . . H3A H 0.3734 0.5039 0.9239 0.049 Uiso 1 1 calc R . . C4 C 0.50336(11) 0.7804(3) 0.88599(14) 0.0462(5) Uani 1 1 d . . . H4 H 0.5135 0.9042 0.8880 0.055 Uiso 1 1 calc R . . C5 C 0.55924(10) 0.6649(3) 0.85883(13) 0.0419(5) Uani 1 1 d . . . H5 H 0.6064 0.7101 0.8436 0.050 Uiso 1 1 calc R . . C6 C 0.59868(10) 0.3399(2) 0.82768(12) 0.0341(4) Uani 1 1 d . . . C7 C 0.69311(10) 0.1867(2) 0.77642(12) 0.0329(4) Uani 1 1 d . . . C8 C 0.76247(10) 0.1262(2) 0.73245(12) 0.0322(4) Uani 1 1 d . . . C9 C 0.82442(10) 0.2345(2) 0.71331(13) 0.0391(5) Uani 1 1 d . . . H9 H 0.8242 0.3578 0.7271 0.047 Uiso 1 1 calc R . . C10 C 0.88634(11) 0.1567(3) 0.67348(13) 0.0433(5) Uani 1 1 d . . . H10 H 0.9273 0.2309 0.6607 0.052 Uiso 1 1 calc R . . C11 C 0.83103(11) -0.1218(3) 0.67087(13) 0.0429(5) Uani 1 1 d . . . H11 H 0.8332 -0.2449 0.6572 0.052 Uiso 1 1 calc R . . C12 C 0.76670(10) -0.0560(2) 0.70910(13) 0.0396(5) Uani 1 1 d . . . H12 H 0.7261 -0.1332 0.7193 0.047 Uiso 1 1 calc R . . C13 C 0.27107(10) -0.1595(3) -0.01102(12) 0.0365(4) Uani 1 1 d . . . C14 C 0.20733(10) -0.0478(2) 0.02357(12) 0.0340(4) Uani 1 1 d . . . C15 C 0.14100(10) -0.1352(2) 0.04533(12) 0.0358(4) Uani 1 1 d . . . H15 H 0.1349 -0.2579 0.0320 0.043 Uiso 1 1 calc R . . C16 C 0.08377(10) -0.0419(2) 0.08676(13) 0.0353(4) Uani 1 1 d . . . C17 C 0.01389(10) -0.1381(3) 0.11610(13) 0.0392(5) Uani 1 1 d . . . C18 C 0.09269(10) 0.1416(2) 0.10479(13) 0.0372(5) Uani 1 1 d . . . H18 H 0.0545 0.2044 0.1335 0.045 Uiso 1 1 calc R . . C19 C 0.15780(10) 0.2334(2) 0.08062(13) 0.0349(4) Uani 1 1 d . . . C20 C 0.21553(10) 0.1365(2) 0.03995(12) 0.0360(4) Uani 1 1 d . . . H20 H 0.2596 0.1958 0.0238 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0427(8) 0.0325(8) 0.0619(9) 0.0007(7) 0.0180(7) 0.0042(6) O2 0.0373(8) 0.0420(8) 0.0602(9) 0.0065(7) 0.0225(7) 0.0073(6) O3 0.0408(8) 0.0350(8) 0.0881(11) -0.0035(7) 0.0259(8) -0.0063(6) O4 0.0395(8) 0.0441(9) 0.0925(12) -0.0064(8) 0.0295(8) -0.0026(7) N1 0.0373(9) 0.0392(10) 0.0475(10) 0.0044(7) 0.0133(8) 0.0055(7) N2 0.0320(8) 0.0325(9) 0.0573(10) 0.0023(8) 0.0141(7) 0.0005(7) N3 0.0327(8) 0.0330(9) 0.0552(10) 0.0009(7) 0.0123(7) 0.0017(7) N4 0.0289(8) 0.0261(8) 0.0406(9) 0.0001(7) 0.0080(7) 0.0001(6) N5 0.0422(9) 0.0270(9) 0.0514(10) -0.0008(7) 0.0163(8) -0.0053(7) N6 0.0396(9) 0.0377(10) 0.0502(10) 0.0010(8) 0.0130(8) 0.0072(7) N7 0.0411(9) 0.0292(9) 0.0704(12) -0.0016(8) 0.0180(8) -0.0004(7) C1 0.0301(10) 0.0353(10) 0.0359(10) 0.0020(8) 0.0064(8) 0.0034(8) C2 0.0334(10) 0.0343(11) 0.0522(12) -0.0017(9) 0.0089(9) -0.0001(8) C3 0.0322(10) 0.0414(12) 0.0506(12) 0.0004(9) 0.0093(9) 0.0008(9) C4 0.0453(12) 0.0344(12) 0.0605(13) 0.0057(9) 0.0204(10) 0.0028(9) C5 0.0347(10) 0.0354(11) 0.0573(13) 0.0037(10) 0.0178(9) 0.0014(9) C6 0.0278(9) 0.0353(11) 0.0397(11) 0.0008(9) 0.0072(8) -0.0001(8) C7 0.0301(9) 0.0301(10) 0.0389(11) -0.0005(8) 0.0042(8) 0.0013(8) C8 0.0303(10) 0.0309(10) 0.0356(10) 0.0021(8) 0.0040(8) 0.0039(8) C9 0.0350(11) 0.0293(10) 0.0537(12) -0.0023(9) 0.0077(9) 0.0004(8) C10 0.0350(11) 0.0394(12) 0.0566(13) 0.0013(10) 0.0126(9) -0.0007(9) C11 0.0430(11) 0.0315(11) 0.0553(13) -0.0040(9) 0.0116(10) 0.0044(9) C12 0.0360(11) 0.0301(10) 0.0535(12) 0.0005(9) 0.0105(9) -0.0002(8) C13 0.0338(10) 0.0386(12) 0.0376(11) 0.0009(9) 0.0079(8) -0.0002(9) C14 0.0328(10) 0.0344(11) 0.0354(10) 0.0042(8) 0.0069(8) 0.0031(8) C15 0.0378(11) 0.0282(10) 0.0418(11) 0.0026(8) 0.0064(8) 0.0015(8) C16 0.0293(10) 0.0329(11) 0.0441(11) 0.0041(8) 0.0059(8) 0.0019(8) C17 0.0326(10) 0.0331(11) 0.0524(12) 0.0025(9) 0.0076(9) -0.0001(8) C18 0.0314(10) 0.0325(11) 0.0484(12) 0.0007(9) 0.0084(9) 0.0047(8) C19 0.0337(10) 0.0288(10) 0.0427(11) 0.0014(8) 0.0051(8) 0.0005(8) C20 0.0296(10) 0.0352(11) 0.0438(11) 0.0052(8) 0.0076(8) -0.0033(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.226(2) . ? O2 C13 1.306(2) . ? O2 H2 0.8200 . ? O3 C17 1.320(2) . ? O3 H3 0.8200 . ? O4 C17 1.210(2) . ? N1 C3 1.330(2) . ? N1 C4 1.338(2) . ? N2 C6 1.318(2) . ? N2 N3 1.3741(19) . ? N3 C7 1.311(2) . ? N4 C6 1.360(2) . ? N4 C7 1.368(2) . ? N4 N5 1.4080(19) . ? N5 H5A 0.9000 . ? N5 H5B 0.8998 . ? N6 C11 1.330(2) . ? N6 C10 1.331(2) . ? N7 C19 1.402(2) . ? N7 H7A 0.9000 . ? N7 H7B 0.9000 . ? C1 C5 1.383(3) . ? C1 C2 1.398(2) . ? C1 C6 1.470(2) . ? C2 C3 1.370(2) . ? C2 H2A 0.9300 . ? C3 H3A 0.9300 . ? C4 C5 1.372(2) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.473(2) . ? C8 C12 1.388(2) . ? C8 C9 1.389(2) . ? C9 C10 1.382(2) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.373(2) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.497(2) . ? C14 C15 1.382(2) . ? C14 C20 1.385(2) . ? C15 C16 1.381(2) . ? C15 H15 0.9300 . ? C16 C18 1.385(2) . ? C16 C17 1.498(2) . ? C18 C19 1.389(2) . ? C18 H18 0.9300 . ? C19 C20 1.396(2) . ? C20 H20 0.9300 . ? 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 C13 O2 H2 109.5 . . ? C17 O3 H3 109.5 . . ? C3 N1 C4 118.31(16) . . ? C6 N2 N3 107.63(14) . . ? C7 N3 N2 107.58(15) . . ? C6 N4 C7 105.36(14) . . ? C6 N4 N5 124.58(14) . . ? C7 N4 N5 129.96(14) . . ? N4 N5 H5A 109.5 . . ? N4 N5 H5B 118.6 . . ? H5A N5 H5B 112.9 . . ? C11 N6 C10 117.11(16) . . ? C19 N7 H7A 113.9 . . ? C19 N7 H7B 112.4 . . ? H7A N7 H7B 112.9 . . ? C5 C1 C2 117.54(16) . . ? C5 C1 C6 125.82(16) . . ? C2 C1 C6 116.63(16) . . ? C3 C2 C1 119.48(18) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? N1 C3 C2 122.54(17) . . ? N1 C3 H3A 118.7 . . ? C2 C3 H3A 118.7 . . ? N1 C4 C5 122.79(18) . . ? N1 C4 H4 118.6 . . ? C5 C4 H4 118.6 . . ? C4 C5 C1 119.33(17) . . ? C4 C5 H5 120.3 . . ? C1 C5 H5 120.3 . . ? N2 C6 N4 109.64(15) . . ? N2 C6 C1 121.38(15) . . ? N4 C6 C1 128.98(16) . . ? N3 C7 N4 109.79(15) . . ? N3 C7 C8 121.33(16) . . ? N4 C7 C8 128.84(16) . . ? C12 C8 C9 117.06(16) . . ? C12 C8 C7 117.03(16) . . ? C9 C8 C7 125.90(16) . . ? C10 C9 C8 119.11(17) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? N6 C10 C9 123.55(18) . . ? N6 C10 H10 118.2 . . ? C9 C10 H10 118.2 . . ? N6 C11 C12 123.42(18) . . ? N6 C11 H11 118.3 . . ? C12 C11 H11 118.3 . . ? C11 C12 C8 119.74(17) . . ? C11 C12 H12 120.1 . . ? C8 C12 H12 120.1 . . ? O1 C13 O2 123.95(16) . . ? O1 C13 C14 121.02(16) . . ? O2 C13 C14 115.03(16) . . ? C15 C14 C20 119.96(16) . . ? C15 C14 C13 118.30(16) . . ? C20 C14 C13 121.59(16) . . ? C16 C15 C14 120.57(17) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C18 119.38(16) . . ? C15 C16 C17 120.90(17) . . ? C18 C16 C17 119.67(16) . . ? O4 C17 O3 123.72(17) . . ? O4 C17 C16 123.33(18) . . ? O3 C17 C16 112.94(15) . . ? C16 C18 C19 120.97(16) . . ? C16 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C18 C19 C20 118.89(17) . . ? C18 C19 N7 120.77(16) . . ? C20 C19 N7 120.17(16) . . ? C14 C20 C19 120.19(16) . . ? C14 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? 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 C6 N2 N3 C7 0.3(2) . . . . ? C5 C1 C2 C3 0.1(3) . . . . ? C6 C1 C2 C3 178.65(17) . . . . ? C4 N1 C3 C2 -0.8(3) . . . . ? C1 C2 C3 N1 0.8(3) . . . . ? C3 N1 C4 C5 0.0(3) . . . . ? N1 C4 C5 C1 0.8(3) . . . . ? C2 C1 C5 C4 -0.8(3) . . . . ? C6 C1 C5 C4 -179.25(18) . . . . ? N3 N2 C6 N4 -0.6(2) . . . . ? N3 N2 C6 C1 179.82(16) . . . . ? C7 N4 C6 N2 0.6(2) . . . . ? N5 N4 C6 N2 177.20(15) . . . . ? C7 N4 C6 C1 -179.83(18) . . . . ? N5 N4 C6 C1 -3.3(3) . . . . ? C5 C1 C6 N2 165.16(19) . . . . ? C2 C1 C6 N2 -13.3(3) . . . . ? C5 C1 C6 N4 -14.3(3) . . . . ? C2 C1 C6 N4 167.25(18) . . . . ? N2 N3 C7 N4 0.1(2) . . . . ? N2 N3 C7 C8 -178.04(16) . . . . ? C6 N4 C7 N3 -0.4(2) . . . . ? N5 N4 C7 N3 -176.73(16) . . . . ? C6 N4 C7 C8 177.50(18) . . . . ? N5 N4 C7 C8 1.2(3) . . . . ? N3 C7 C8 C12 15.4(3) . . . . ? N4 C7 C8 C12 -162.32(18) . . . . ? N3 C7 C8 C9 -163.76(18) . . . . ? N4 C7 C8 C9 18.5(3) . . . . ? C12 C8 C9 C10 -0.6(3) . . . . ? C7 C8 C9 C10 178.58(17) . . . . ? C11 N6 C10 C9 0.3(3) . . . . ? C8 C9 C10 N6 -0.3(3) . . . . ? C10 N6 C11 C12 0.6(3) . . . . ? N6 C11 C12 C8 -1.6(3) . . . . ? C9 C8 C12 C11 1.5(3) . . . . ? C7 C8 C12 C11 -177.76(17) . . . . ? O1 C13 C14 C15 -17.7(3) . . . . ? O2 C13 C14 C15 162.89(16) . . . . ? O1 C13 C14 C20 157.84(18) . . . . ? O2 C13 C14 C20 -21.6(3) . . . . ? C20 C14 C15 C16 -2.6(3) . . . . ? C13 C14 C15 C16 173.00(16) . . . . ? C14 C15 C16 C18 1.3(3) . . . . ? C14 C15 C16 C17 -176.03(17) . . . . ? C15 C16 C17 O4 179.19(19) . . . . ? C18 C16 C17 O4 1.9(3) . . . . ? C15 C16 C17 O3 0.3(3) . . . . ? C18 C16 C17 O3 -177.05(18) . . . . ? C15 C16 C18 C19 0.9(3) . . . . ? C17 C16 C18 C19 178.27(17) . . . . ? C16 C18 C19 C20 -1.8(3) . . . . ? C16 C18 C19 N7 -177.08(18) . . . . ? C15 C14 C20 C19 1.7(3) . . . . ? C13 C14 C20 C19 -173.75(16) . . . . ? C18 C19 C20 C14 0.5(3) . . . . ? N7 C19 C20 C14 175.80(17) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.185 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.043 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 693292' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 N6 O9 S' _chemical_formula_weight 520.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.1997(8) _cell_length_b 21.912(2) _cell_length_c 14.1960(15) _cell_angle_alpha 90.00 _cell_angle_beta 98.1160(10) _cell_angle_gamma 90.00 _cell_volume 2217.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3017 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 23.27 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9122 _exptl_absorpt_correction_T_max 0.9564 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12004 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3903 _reflns_number_gt 2902 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. Standard geometry constraints were applied for sulfonate in order to improve the refinement stability. In addition, the soft "SADI" restraint was imposed on the disordered oxygen atoms of sulfonate, and "EADP" constraint was applied separately to the O5/O5' and O7/O7' atoms. ; _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^)+(0.0555P)^2^+1.1982P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3903 _refine_ls_number_parameters 343 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1264 _refine_ls_wR_factor_gt 0.1171 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.146 _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 S1 S 0.26734(11) 0.59226(3) 0.66802(5) 0.0432(2) Uani 1 1 d D . . O1 O 0.2273(4) 0.85601(9) 0.47864(14) 0.0654(7) Uani 1 1 d . . . H1 H 0.2371 0.8918 0.4956 0.098 Uiso 1 1 calc R . . O2 O 0.3286(4) 0.83817(10) 0.63067(15) 0.0710(7) Uani 1 1 d . . . O3 O -0.0097(4) 0.70341(10) 0.26100(14) 0.0706(8) Uani 1 1 d . A . H3' H -0.0674 0.6916 0.2103 0.106 Uiso 1 1 calc R . . O4 O -0.0355(4) 0.60658(9) 0.30104(15) 0.0630(7) Uani 1 1 d . A . O5 O 0.1257(5) 0.54427(12) 0.63972(19) 0.0547(8) Uani 0.803(4) 1 d PDU A 1 O6 O 0.4522(4) 0.56872(13) 0.6650(2) 0.0571(8) Uani 0.803(4) 1 d PDU A 1 O7 O 0.2450(4) 0.62162(14) 0.75732(19) 0.0455(7) Uani 0.803(4) 1 d PDU A 1 O5' O 0.2495(18) 0.5369(4) 0.6269(7) 0.0547(8) Uani 0.197(4) 1 d PDU A 2 O6' O 0.4761(12) 0.6075(6) 0.7005(8) 0.065(4) Uani 0.197(4) 1 d PDU A 2 O7' O 0.1810(17) 0.6109(6) 0.7484(8) 0.0455(7) Uani 0.197(4) 1 d PDU A 2 N1 N 0.4482(4) 0.44025(11) 0.62474(18) 0.0543(7) Uani 1 1 d . . . H1A H 0.4725 0.4766 0.6457 0.065 Uiso 1 1 calc R . . N2 N 0.2318(3) 0.25811(10) 0.43022(15) 0.0395(6) Uani 1 1 d . . . N3 N 0.2014(3) 0.19699(10) 0.41420(15) 0.0408(6) Uani 1 1 d . . . N4 N 0.3480(3) 0.20814(9) 0.55850(14) 0.0328(5) Uani 1 1 d . . . N5 N 0.4457(3) 0.19784(10) 0.65066(15) 0.0436(6) Uani 1 1 d . . . H5A H 0.3626 0.1810 0.6848 0.052 Uiso 1 1 d R . . H5B H 0.5385 0.1721 0.6409 0.052 Uiso 1 1 d R . . N6 N 0.2493(4) -0.02671(11) 0.49903(17) 0.0507(7) Uani 1 1 d . . . C1 C 0.3710(4) 0.32467(12) 0.55850(18) 0.0336(6) Uani 1 1 d . . . C2 C 0.3184(4) 0.37537(12) 0.5020(2) 0.0434(7) Uani 1 1 d . . . H2 H 0.2578 0.3702 0.4403 0.052 Uiso 1 1 calc R . . C3 C 0.3558(5) 0.43267(14) 0.5372(2) 0.0527(8) Uani 1 1 d . . . H3 H 0.3168 0.4665 0.5001 0.063 Uiso 1 1 calc R . . C4 C 0.5039(5) 0.39298(13) 0.6805(2) 0.0521(8) Uani 1 1 d . . . H4 H 0.5697 0.3997 0.7408 0.062 Uiso 1 1 calc R . . C5 C 0.4651(4) 0.33435(13) 0.64981(19) 0.0432(7) Uani 1 1 d . . . H5 H 0.5013 0.3015 0.6896 0.052 Uiso 1 1 calc R . . C6 C 0.3209(4) 0.26437(11) 0.51714(17) 0.0326(6) Uani 1 1 d . . . C7 C 0.2714(4) 0.16721(12) 0.49177(17) 0.0349(6) Uani 1 1 d . . . C8 C 0.2663(4) 0.09998(12) 0.49852(18) 0.0371(6) Uani 1 1 d . . . C9 C 0.2472(5) 0.06713(13) 0.4147(2) 0.0513(8) Uani 1 1 d . . . H9 H 0.2400 0.0872 0.3565 0.062 Uiso 1 1 calc R . . C10 C 0.2391(5) 0.00458(14) 0.4181(2) 0.0549(9) Uani 1 1 d . . . H10 H 0.2259 -0.0170 0.3611 0.066 Uiso 1 1 calc R . . C11 C 0.2641(5) 0.00509(14) 0.5793(2) 0.0562(9) Uani 1 1 d . . . H11 H 0.2680 -0.0162 0.6363 0.067 Uiso 1 1 calc R . . C12 C 0.2741(5) 0.06810(13) 0.5829(2) 0.0499(8) Uani 1 1 d . . . H12 H 0.2857 0.0885 0.6409 0.060 Uiso 1 1 calc R . . C13 C 0.2659(4) 0.82054(12) 0.55255(19) 0.0409(7) Uani 1 1 d . . . C14 C 0.2253(4) 0.75484(11) 0.52969(17) 0.0336(6) Uani 1 1 d . A . C15 C 0.1463(4) 0.73767(12) 0.43841(18) 0.0350(6) Uani 1 1 d . . . H15 H 0.1208 0.7671 0.3912 0.042 Uiso 1 1 calc R . . C16 C 0.1056(4) 0.67694(11) 0.41746(17) 0.0340(6) Uani 1 1 d . A . C17 C 0.1437(4) 0.63297(12) 0.48786(17) 0.0353(6) Uani 1 1 d . . . H17 H 0.1167 0.5922 0.4739 0.042 Uiso 1 1 calc R A . C18 C 0.2219(4) 0.64985(11) 0.57905(17) 0.0331(6) Uani 1 1 d . A . C19 C 0.2631(4) 0.71063(12) 0.60028(18) 0.0354(6) Uani 1 1 d . . . H19 H 0.3157 0.7218 0.6615 0.042 Uiso 1 1 calc R A . C20 C 0.0147(4) 0.65775(13) 0.32099(18) 0.0398(7) Uani 1 1 d . . . O8 O 0.2121(4) 0.49402(14) 0.3114(2) 0.1011(10) Uani 1 1 d . . . H8A H 0.0998 0.4881 0.3214 0.152 Uiso 1 1 d R . . H8B H 0.2862 0.4637 0.3186 0.152 Uiso 1 1 d R . . O9 O 0.1464(4) 0.15787(11) 0.75819(18) 0.0740(7) Uani 1 1 d . . . H9A H 0.1586 0.1824 0.8051 0.111 Uiso 1 1 d R . . H9B H 0.0366 0.1447 0.7388 0.111 Uiso 1 1 d 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 S1 0.0544(5) 0.0354(4) 0.0388(4) 0.0077(3) 0.0035(3) 0.0063(3) O1 0.121(2) 0.0269(11) 0.0440(12) 0.0013(9) -0.0046(12) -0.0038(12) O2 0.119(2) 0.0421(12) 0.0448(12) -0.0055(10) -0.0150(13) -0.0174(13) O3 0.120(2) 0.0438(12) 0.0378(11) 0.0039(10) -0.0248(12) -0.0136(13) O4 0.0951(19) 0.0371(12) 0.0489(12) -0.0047(9) -0.0174(12) -0.0062(12) O5 0.0607(14) 0.0452(11) 0.0574(12) 0.0028(9) 0.0056(11) -0.0126(11) O6 0.0554(15) 0.0484(14) 0.0675(15) 0.0089(12) 0.0085(12) 0.0137(12) O7 0.0507(14) 0.0449(12) 0.0394(10) 0.0033(9) 0.0012(10) -0.0067(11) O5' 0.0607(14) 0.0452(11) 0.0574(12) 0.0028(9) 0.0056(11) -0.0126(11) O6' 0.066(4) 0.063(4) 0.064(4) 0.001(2) 0.005(2) 0.001(2) O7' 0.0507(14) 0.0449(12) 0.0394(10) 0.0033(9) 0.0012(10) -0.0067(11) N1 0.078(2) 0.0357(14) 0.0477(15) -0.0015(11) 0.0043(13) -0.0106(13) N2 0.0495(15) 0.0305(12) 0.0365(12) 0.0018(10) -0.0009(11) 0.0007(10) N3 0.0543(15) 0.0313(12) 0.0338(12) -0.0001(10) -0.0045(10) 0.0032(11) N4 0.0370(13) 0.0297(11) 0.0298(11) 0.0023(9) -0.0021(9) 0.0001(9) N5 0.0543(15) 0.0382(13) 0.0342(12) 0.0068(10) -0.0081(11) -0.0021(11) N6 0.0645(18) 0.0314(13) 0.0533(15) 0.0000(11) -0.0012(13) 0.0018(12) C1 0.0309(15) 0.0337(14) 0.0364(14) 0.0011(11) 0.0057(11) -0.0008(11) C2 0.0518(18) 0.0367(16) 0.0397(15) 0.0031(12) 0.0000(13) -0.0055(13) C3 0.071(2) 0.0368(16) 0.0481(17) 0.0085(14) 0.0016(16) -0.0029(15) C4 0.068(2) 0.0426(17) 0.0422(16) -0.0017(14) -0.0038(15) -0.0063(15) C5 0.0528(19) 0.0361(16) 0.0387(15) 0.0019(12) -0.0010(13) -0.0018(13) C6 0.0331(15) 0.0324(14) 0.0320(13) 0.0034(11) 0.0030(11) 0.0017(11) C7 0.0395(16) 0.0318(14) 0.0325(13) -0.0013(11) 0.0018(11) 0.0006(12) C8 0.0413(16) 0.0291(14) 0.0387(14) -0.0006(11) -0.0016(12) 0.0006(11) C9 0.075(2) 0.0374(16) 0.0401(16) 0.0018(13) 0.0019(15) 0.0032(15) C10 0.076(2) 0.0381(17) 0.0475(17) -0.0096(14) -0.0008(16) 0.0014(16) C11 0.079(3) 0.0373(16) 0.0493(18) 0.0077(14) -0.0009(16) -0.0011(16) C12 0.077(2) 0.0328(15) 0.0378(15) -0.0005(12) 0.0016(15) -0.0006(15) C13 0.0486(18) 0.0342(15) 0.0395(15) 0.0004(12) 0.0045(13) -0.0025(13) C14 0.0366(15) 0.0295(13) 0.0342(13) -0.0002(11) 0.0032(11) -0.0011(11) C15 0.0402(16) 0.0304(14) 0.0331(13) 0.0032(11) 0.0012(11) 0.0014(11) C16 0.0360(15) 0.0331(14) 0.0314(13) -0.0010(11) -0.0004(11) 0.0003(11) C17 0.0379(16) 0.0295(13) 0.0370(14) -0.0018(11) 0.0003(12) 0.0012(11) C18 0.0322(15) 0.0328(14) 0.0340(13) 0.0014(11) 0.0035(11) 0.0023(11) C19 0.0381(16) 0.0359(14) 0.0308(13) -0.0017(11) 0.0000(11) -0.0004(12) C20 0.0461(17) 0.0368(15) 0.0349(14) 0.0000(12) 0.0003(12) 0.0043(13) O8 0.084(2) 0.090(2) 0.124(2) 0.0000(19) -0.0007(18) -0.0165(17) O9 0.0725(17) 0.0727(16) 0.0806(17) -0.0289(14) 0.0243(13) -0.0068(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 S1 O5' 1.344(8) . ? S1 O7' 1.433(9) . ? S1 O6 1.434(3) . ? S1 O7 1.451(3) . ? S1 O5 1.480(3) . ? S1 O6' 1.545(8) . ? S1 C18 1.783(3) . ? O1 C13 1.304(3) . ? O1 H1 0.8200 . ? O2 C13 1.201(3) . ? O3 C20 1.310(3) . ? O3 H3' 0.8200 . ? O4 C20 1.200(3) . ? N1 C4 1.330(4) . ? N1 C3 1.334(4) . ? N1 H1A 0.8600 . ? N2 C6 1.315(3) . ? N2 N3 1.371(3) . ? N3 C7 1.317(3) . ? N4 C7 1.363(3) . ? N4 C6 1.367(3) . ? N4 N5 1.413(3) . ? N5 H5A 0.9000 . ? N5 H5B 0.9001 . ? N6 C11 1.327(4) . ? N6 C10 1.331(4) . ? C1 C2 1.391(4) . ? C1 C5 1.391(4) . ? C1 C6 1.470(4) . ? C2 C3 1.364(4) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.372(4) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.477(4) . ? C8 C9 1.381(4) . ? C8 C12 1.381(4) . ? C9 C10 1.373(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.383(4) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.496(4) . ? C14 C15 1.391(3) . ? C14 C19 1.393(4) . ? C15 C16 1.386(4) . ? C15 H15 0.9300 . ? C16 C17 1.387(3) . ? C16 C20 1.492(4) . ? C17 C18 1.387(3) . ? C17 H17 0.9300 . ? C18 C19 1.388(4) . ? C19 H19 0.9300 . ? O8 H8A 0.8502 . ? O8 H8B 0.8491 . ? O9 H9A 0.8503 . ? O9 H9B 0.8506 . ? 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 O5' S1 O7' 125.2(7) . . ? O5' S1 O6 72.2(5) . . ? O7' S1 O6 129.4(6) . . ? O5' S1 O7 139.8(5) . . ? O6 S1 O7 113.84(17) . . ? O7' S1 O5 93.4(5) . . ? O6 S1 O5 110.05(17) . . ? O7 S1 O5 113.26(16) . . ? O5' S1 O6' 110.7(6) . . ? O7' S1 O6' 102.3(6) . . ? O7 S1 O6' 82.3(5) . . ? O5 S1 O6' 146.9(5) . . ? O5' S1 C18 109.5(5) . . ? O7' S1 C18 107.8(6) . . ? O6 S1 C18 108.15(14) . . ? O7 S1 C18 105.86(15) . . ? O5 S1 C18 105.08(14) . . ? O6' S1 C18 97.6(5) . . ? C13 O1 H1 109.5 . . ? C20 O3 H3' 109.5 . . ? C4 N1 C3 121.7(3) . . ? C4 N1 H1A 119.1 . . ? C3 N1 H1A 119.1 . . ? C6 N2 N3 107.6(2) . . ? C7 N3 N2 108.2(2) . . ? C7 N4 C6 106.0(2) . . ? C7 N4 N5 129.6(2) . . ? C6 N4 N5 124.3(2) . . ? N4 N5 H5A 106.4 . . ? N4 N5 H5B 104.0 . . ? H5A N5 H5B 112.9 . . ? C11 N6 C10 117.3(3) . . ? C2 C1 C5 118.2(2) . . ? C2 C1 C6 117.2(2) . . ? C5 C1 C6 124.7(2) . . ? C3 C2 C1 120.1(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? N1 C3 C2 120.1(3) . . ? N1 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? N1 C4 C5 120.6(3) . . ? N1 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C1 119.3(3) . . ? C4 C5 H5 120.4 . . ? C1 C5 H5 120.4 . . ? N2 C6 N4 109.3(2) . . ? N2 C6 C1 121.9(2) . . ? N4 C6 C1 128.8(2) . . ? N3 C7 N4 108.9(2) . . ? N3 C7 C8 122.5(2) . . ? N4 C7 C8 128.5(2) . . ? C9 C8 C12 118.1(3) . . ? C9 C8 C7 117.7(2) . . ? C12 C8 C7 124.2(2) . . ? C10 C9 C8 119.3(3) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? N6 C10 C9 123.1(3) . . ? N6 C10 H10 118.4 . . ? C9 C10 H10 118.4 . . ? N6 C11 C12 123.6(3) . . ? N6 C11 H11 118.2 . . ? C12 C11 H11 118.2 . . ? C8 C12 C11 118.5(3) . . ? C8 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? O2 C13 O1 124.1(3) . . ? O2 C13 C14 123.1(2) . . ? O1 C13 C14 112.7(2) . . ? C15 C14 C19 119.7(2) . . ? C15 C14 C13 120.3(2) . . ? C19 C14 C13 120.1(2) . . ? C16 C15 C14 120.4(2) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 119.9(2) . . ? C15 C16 C20 121.3(2) . . ? C17 C16 C20 118.8(2) . . ? C16 C17 C18 120.0(2) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C19 120.3(2) . . ? C17 C18 S1 118.8(2) . . ? C19 C18 S1 120.87(19) . . ? C18 C19 C14 119.8(2) . . ? C18 C19 H19 120.1 . . ? C14 C19 H19 120.1 . . ? O4 C20 O3 123.5(2) . . ? O4 C20 C16 123.9(2) . . ? O3 C20 C16 112.5(2) . . ? H8A O8 H8B 117.2 . . ? H9A O9 H9B 117.2 . . ? 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 C6 N2 N3 C7 0.3(3) . . . . ? C5 C1 C2 C3 -1.4(4) . . . . ? C6 C1 C2 C3 178.1(3) . . . . ? C4 N1 C3 C2 -1.0(5) . . . . ? C1 C2 C3 N1 2.2(5) . . . . ? C3 N1 C4 C5 -1.0(5) . . . . ? N1 C4 C5 C1 1.7(5) . . . . ? C2 C1 C5 C4 -0.6(4) . . . . ? C6 C1 C5 C4 -179.9(3) . . . . ? N3 N2 C6 N4 -0.4(3) . . . . ? N3 N2 C6 C1 -178.3(2) . . . . ? C7 N4 C6 N2 0.3(3) . . . . ? N5 N4 C6 N2 177.5(2) . . . . ? C7 N4 C6 C1 178.0(3) . . . . ? N5 N4 C6 C1 -4.9(4) . . . . ? C2 C1 C6 N2 0.7(4) . . . . ? C5 C1 C6 N2 -179.9(3) . . . . ? C2 C1 C6 N4 -176.7(3) . . . . ? C5 C1 C6 N4 2.7(5) . . . . ? N2 N3 C7 N4 -0.1(3) . . . . ? N2 N3 C7 C8 -178.7(2) . . . . ? C6 N4 C7 N3 -0.1(3) . . . . ? N5 N4 C7 N3 -177.0(2) . . . . ? C6 N4 C7 C8 178.4(3) . . . . ? N5 N4 C7 C8 1.4(5) . . . . ? N3 C7 C8 C9 22.1(4) . . . . ? N4 C7 C8 C9 -156.1(3) . . . . ? N3 C7 C8 C12 -156.0(3) . . . . ? N4 C7 C8 C12 25.7(5) . . . . ? C12 C8 C9 C10 -0.8(5) . . . . ? C7 C8 C9 C10 -179.0(3) . . . . ? C11 N6 C10 C9 1.4(5) . . . . ? C8 C9 C10 N6 -0.2(5) . . . . ? C10 N6 C11 C12 -1.7(5) . . . . ? C9 C8 C12 C11 0.6(5) . . . . ? C7 C8 C12 C11 178.7(3) . . . . ? N6 C11 C12 C8 0.7(5) . . . . ? O2 C13 C14 C15 177.7(3) . . . . ? O1 C13 C14 C15 -2.8(4) . . . . ? O2 C13 C14 C19 -1.1(5) . . . . ? O1 C13 C14 C19 178.4(3) . . . . ? C19 C14 C15 C16 -0.1(4) . . . . ? C13 C14 C15 C16 -178.9(3) . . . . ? C14 C15 C16 C17 0.0(4) . . . . ? C14 C15 C16 C20 177.8(2) . . . . ? C15 C16 C17 C18 0.2(4) . . . . ? C20 C16 C17 C18 -177.7(2) . . . . ? C16 C17 C18 C19 -0.2(4) . . . . ? C16 C17 C18 S1 179.5(2) . . . . ? O5' S1 C18 C17 11.8(6) . . . . ? O7' S1 C18 C17 -127.4(6) . . . . ? O6 S1 C18 C17 88.8(3) . . . . ? O7 S1 C18 C17 -148.9(2) . . . . ? O5 S1 C18 C17 -28.8(3) . . . . ? O6' S1 C18 C17 127.0(5) . . . . ? O5' S1 C18 C19 -168.5(6) . . . . ? O7' S1 C18 C19 52.3(6) . . . . ? O6 S1 C18 C19 -91.5(3) . . . . ? O7 S1 C18 C19 30.9(3) . . . . ? O5 S1 C18 C19 151.0(2) . . . . ? O6' S1 C18 C19 -53.3(5) . . . . ? C17 C18 C19 C14 0.1(4) . . . . ? S1 C18 C19 C14 -179.6(2) . . . . ? C15 C14 C19 C18 0.1(4) . . . . ? C13 C14 C19 C18 178.8(3) . . . . ? C15 C16 C20 O4 -174.5(3) . . . . ? C17 C16 C20 O4 3.3(4) . . . . ? C15 C16 C20 O3 3.5(4) . . . . ? C17 C16 C20 O3 -178.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.472 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.049 #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 693293' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 N6 O8' _chemical_formula_weight 484.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3454(7) _cell_length_b 37.522(3) _cell_length_c 8.5441(8) _cell_angle_alpha 90.00 _cell_angle_beta 113.3500(10) _cell_angle_gamma 90.00 _cell_volume 2162.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 6645 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 27.84 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9219 _exptl_absorpt_correction_T_max 0.9689 _exptl_absorpt_process_details SADABS _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 'APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11617 _diffrn_reflns_av_R_equivalents 0.0141 _diffrn_reflns_av_sigmaI/netI 0.0137 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -44 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3803 _reflns_number_gt 3427 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0490P)^2^+0.9451P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3803 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 O1 O 0.8761(2) 0.30544(4) 0.54899(18) 0.0578(4) Uani 1 1 d . . . O2 O 0.8541(2) 0.24702(3) 0.50116(16) 0.0465(3) Uani 1 1 d . . . H2 H 0.9434 0.2464 0.5967 0.070 Uiso 1 1 calc R . . O3 O 0.3271(2) 0.19605(3) 0.02139(16) 0.0481(4) Uani 1 1 d . . . H3 H 0.2583 0.1798 -0.0365 0.072 Uiso 1 1 calc R . . O4 O 0.13253(18) 0.22838(3) -0.19684(15) 0.0439(3) Uani 1 1 d . . . O5 O 0.1893(2) 0.36005(3) -0.13815(18) 0.0568(4) Uani 1 1 d . . . H5' H 0.1538 0.3809 -0.1556 0.085 Uiso 1 1 calc R . . O6 O 0.4586(2) 0.38405(3) 0.05737(19) 0.0581(4) Uani 1 1 d . . . O7 O 0.0617(2) 0.42522(3) 0.78777(19) 0.0635(5) Uani 1 1 d . . . H7A H -0.0437 0.4290 0.6999 0.095 Uiso 1 1 d R . . H7B H 0.1174 0.4432 0.8484 0.095 Uiso 1 1 d R . . O8 O 0.6630(3) 0.35680(5) 0.6743(3) 0.0930(6) Uani 1 1 d . . . H8B H 0.7622 0.3487 0.6579 0.139 Uiso 1 1 d R . . H8A H 0.5696 0.3423 0.6622 0.139 Uiso 1 1 d R . . N1 N 1.1236(2) 0.14407(4) 0.8500(2) 0.0457(4) Uani 1 1 d . . . N2 N 0.9069(2) 0.01959(4) 0.65458(18) 0.0406(4) Uani 1 1 d . . . N3 N 0.7961(2) -0.00610(4) 0.54362(18) 0.0385(3) Uani 1 1 d . . . N4 N 0.6933(2) 0.04587(3) 0.42849(16) 0.0314(3) Uani 1 1 d . . . N5 N 0.5731(2) 0.07168(4) 0.31397(19) 0.0441(4) Uani 1 1 d . . . H5A H 0.5277 0.0860 0.3750 0.066 Uiso 1 1 d R . . H5B H 0.6536 0.0831 0.2737 0.066 Uiso 1 1 d R . . N6 N 0.2670(2) -0.05002(4) -0.01042(19) 0.0436(4) Uani 1 1 d . . . C1 C 1.0159(3) 0.14579(5) 0.6835(3) 0.0477(5) Uani 1 1 d . . . H1 H 1.0053 0.1676 0.6286 0.057 Uiso 1 1 calc R . . C2 C 0.9191(3) 0.11663(5) 0.5884(2) 0.0439(4) Uani 1 1 d . . . H2A H 0.8458 0.1187 0.4717 0.053 Uiso 1 1 calc R . . C3 C 0.9329(2) 0.08421(4) 0.6694(2) 0.0341(4) Uani 1 1 d . . . C4 C 1.0434(3) 0.08289(5) 0.8442(2) 0.0468(5) Uani 1 1 d . . . H4 H 1.0546 0.0617 0.9034 0.056 Uiso 1 1 calc R . . C5 C 1.1356(3) 0.11307(5) 0.9285(2) 0.0532(5) Uani 1 1 d . . . H5 H 1.2096 0.1118 1.0454 0.064 Uiso 1 1 calc R . . C6 C 0.8447(2) 0.05070(4) 0.5845(2) 0.0328(4) Uani 1 1 d . . . C7 C 0.6675(2) 0.00996(4) 0.4081(2) 0.0304(3) Uani 1 1 d . . . C8 C 0.5256(2) -0.00957(4) 0.2612(2) 0.0314(3) Uani 1 1 d . . . C9 C 0.3654(3) 0.00601(5) 0.1326(2) 0.0406(4) Uani 1 1 d . . . H9 H 0.3408 0.0303 0.1348 0.049 Uiso 1 1 calc R . . C10 C 0.2426(3) -0.01508(5) 0.0011(2) 0.0440(4) Uani 1 1 d . . . H10 H 0.1359 -0.0042 -0.0851 0.053 Uiso 1 1 calc R . . C11 C 0.4207(3) -0.06475(5) 0.1149(2) 0.0478(5) Uani 1 1 d . . . H11 H 0.4406 -0.0891 0.1103 0.057 Uiso 1 1 calc R . . C12 C 0.5523(3) -0.04585(5) 0.2511(2) 0.0420(4) Uani 1 1 d . . . H12 H 0.6579 -0.0574 0.3354 0.050 Uiso 1 1 calc R . . C13 C 0.8006(2) 0.28038(5) 0.4588(2) 0.0361(4) Uani 1 1 d . . . C14 C 0.6346(2) 0.28376(4) 0.2867(2) 0.0318(4) Uani 1 1 d . . . C15 C 0.5760(2) 0.31747(4) 0.2184(2) 0.0357(4) Uani 1 1 d . . . H15 H 0.6429 0.3375 0.2779 0.043 Uiso 1 1 calc R . . C16 C 0.4179(3) 0.32154(4) 0.0617(2) 0.0343(4) Uani 1 1 d . . . C17 C 0.3586(3) 0.35816(4) -0.0055(2) 0.0391(4) Uani 1 1 d . . . C18 C 0.3175(2) 0.29162(4) -0.0277(2) 0.0335(4) Uani 1 1 d . . . H18 H 0.2109 0.2942 -0.1321 0.040 Uiso 1 1 calc R . . C19 C 0.3772(2) 0.25790(4) 0.0397(2) 0.0304(3) Uani 1 1 d . . . C20 C 0.2676(2) 0.22598(4) -0.0564(2) 0.0325(4) Uani 1 1 d . . . C21 C 0.5353(2) 0.25408(4) 0.1964(2) 0.0309(3) Uani 1 1 d . . . H21 H 0.5748 0.2314 0.2411 0.037 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0553(9) 0.0475(8) 0.0448(8) -0.0112(6) -0.0075(6) -0.0020(7) O2 0.0462(8) 0.0416(7) 0.0331(7) 0.0051(5) -0.0040(6) 0.0016(6) O3 0.0514(8) 0.0262(6) 0.0415(7) 0.0003(5) -0.0084(6) -0.0055(5) O4 0.0433(7) 0.0372(7) 0.0326(6) -0.0003(5) -0.0050(5) -0.0014(5) O5 0.0616(9) 0.0304(7) 0.0498(8) 0.0043(6) -0.0083(7) 0.0065(6) O6 0.0640(9) 0.0281(7) 0.0601(9) 0.0026(6) 0.0012(7) -0.0046(6) O7 0.0684(10) 0.0312(7) 0.0535(8) 0.0035(6) -0.0158(7) 0.0105(6) O8 0.0835(13) 0.0684(12) 0.1082(15) -0.0391(11) 0.0181(11) -0.0001(10) N1 0.0494(9) 0.0352(8) 0.0416(9) -0.0075(7) 0.0062(7) -0.0099(7) N2 0.0435(8) 0.0312(8) 0.0320(8) -0.0007(6) -0.0011(6) -0.0052(6) N3 0.0415(8) 0.0292(7) 0.0308(7) -0.0006(6) -0.0004(6) -0.0041(6) N4 0.0333(7) 0.0257(7) 0.0267(7) -0.0004(5) 0.0028(6) -0.0004(5) N5 0.0481(9) 0.0297(8) 0.0367(8) 0.0013(6) -0.0022(7) 0.0041(6) N6 0.0451(9) 0.0384(8) 0.0341(8) -0.0052(6) 0.0015(7) -0.0086(7) C1 0.0506(11) 0.0341(9) 0.0467(11) 0.0002(8) 0.0067(9) -0.0083(8) C2 0.0481(11) 0.0361(9) 0.0345(9) -0.0017(7) 0.0027(8) -0.0082(8) C3 0.0323(8) 0.0315(9) 0.0331(9) -0.0043(7) 0.0072(7) -0.0048(7) C4 0.0575(12) 0.0352(10) 0.0342(9) 0.0000(7) 0.0039(8) -0.0105(8) C5 0.0639(13) 0.0438(11) 0.0344(10) -0.0063(8) 0.0009(9) -0.0131(9) C6 0.0331(8) 0.0301(8) 0.0285(8) -0.0017(7) 0.0051(7) -0.0044(7) C7 0.0319(8) 0.0269(8) 0.0272(8) -0.0006(6) 0.0062(7) -0.0018(6) C8 0.0324(8) 0.0300(8) 0.0274(8) -0.0019(6) 0.0074(7) -0.0040(6) C9 0.0410(10) 0.0317(9) 0.0362(9) -0.0019(7) 0.0015(8) -0.0002(7) C10 0.0390(10) 0.0417(10) 0.0354(9) 0.0001(8) -0.0022(8) -0.0015(8) C11 0.0547(12) 0.0301(9) 0.0418(10) -0.0046(8) 0.0013(9) -0.0031(8) C12 0.0433(10) 0.0310(9) 0.0353(9) 0.0007(7) -0.0019(8) -0.0002(7) C13 0.0331(9) 0.0373(9) 0.0317(9) -0.0014(7) 0.0063(7) -0.0014(7) C14 0.0304(8) 0.0322(8) 0.0284(8) -0.0005(6) 0.0068(7) -0.0004(6) C15 0.0370(9) 0.0291(8) 0.0346(9) -0.0035(7) 0.0073(7) -0.0035(7) C16 0.0378(9) 0.0275(8) 0.0327(8) 0.0014(7) 0.0088(7) 0.0012(7) C17 0.0467(10) 0.0285(9) 0.0351(9) 0.0005(7) 0.0089(8) 0.0007(7) C18 0.0345(9) 0.0305(8) 0.0284(8) 0.0010(6) 0.0048(7) 0.0015(7) C19 0.0310(8) 0.0283(8) 0.0279(8) -0.0015(6) 0.0075(7) -0.0008(6) C20 0.0320(8) 0.0294(8) 0.0303(8) -0.0006(7) 0.0061(7) 0.0002(6) C21 0.0317(8) 0.0267(8) 0.0303(8) 0.0018(6) 0.0079(7) 0.0009(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.203(2) . ? O2 C13 1.319(2) . ? O2 H2 0.8200 . ? O3 C20 1.2898(19) . ? O3 H3 0.8200 . ? O4 C20 1.220(2) . ? O5 C17 1.311(2) . ? O5 H5' 0.8200 . ? O6 C17 1.208(2) . ? O7 H7A 0.8501 . ? O7 H7B 0.8501 . ? O8 H8B 0.8501 . ? O8 H8A 0.8501 . ? N1 C1 1.327(2) . ? N1 C5 1.328(3) . ? N2 C6 1.309(2) . ? N2 N3 1.3706(19) . ? N3 C7 1.315(2) . ? N4 C7 1.362(2) . ? N4 C6 1.368(2) . ? N4 N5 1.4106(19) . ? N5 H5A 0.9001 . ? N5 H5B 0.9001 . ? N6 C11 1.330(2) . ? N6 C10 1.332(2) . ? C1 C2 1.380(2) . ? C1 H1 0.9300 . ? C2 C3 1.384(2) . ? C2 H2A 0.9300 . ? C3 C4 1.389(2) . ? C3 C6 1.468(2) . ? C4 C5 1.369(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.471(2) . ? C8 C9 1.381(2) . ? C8 C12 1.383(2) . ? C9 C10 1.378(2) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.378(2) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.498(2) . ? C14 C21 1.386(2) . ? C14 C15 1.388(2) . ? C15 C16 1.390(2) . ? C15 H15 0.9300 . ? C16 C18 1.393(2) . ? C16 C17 1.486(2) . ? C18 C19 1.387(2) . ? C18 H18 0.9300 . ? C19 C21 1.389(2) . ? C19 C20 1.494(2) . ? C21 H21 0.9300 . ? 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 C13 O2 H2 109.5 . . ? C20 O3 H3 109.5 . . ? C17 O5 H5' 109.5 . . ? H7A O7 H7B 117.0 . . ? H8B O8 H8A 117.0 . . ? C1 N1 C5 118.42(16) . . ? C6 N2 N3 107.87(13) . . ? C7 N3 N2 108.01(13) . . ? C7 N4 C6 105.90(13) . . ? C7 N4 N5 124.97(13) . . ? C6 N4 N5 128.93(13) . . ? N4 N5 H5A 106.4 . . ? N4 N5 H5B 105.4 . . ? H5A N5 H5B 112.9 . . ? C11 N6 C10 116.47(15) . . ? N1 C1 C2 122.82(17) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 118.91(17) . . ? C1 C2 H2A 120.5 . . ? C3 C2 H2A 120.5 . . ? C2 C3 C4 117.73(15) . . ? C2 C3 C6 125.12(15) . . ? C4 C3 C6 117.13(15) . . ? C5 C4 C3 119.51(17) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? N1 C5 C4 122.60(18) . . ? N1 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? N2 C6 N4 109.20(14) . . ? N2 C6 C3 122.16(14) . . ? N4 C6 C3 128.64(15) . . ? N3 C7 N4 109.01(14) . . ? N3 C7 C8 122.82(14) . . ? N4 C7 C8 128.16(14) . . ? C9 C8 C12 117.66(15) . . ? C9 C8 C7 124.06(15) . . ? C12 C8 C7 118.28(15) . . ? C10 C9 C8 118.77(16) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? N6 C10 C9 124.16(17) . . ? N6 C10 H10 117.9 . . ? C9 C10 H10 117.9 . . ? N6 C11 C12 123.61(17) . . ? N6 C11 H11 118.2 . . ? C12 C11 H11 118.2 . . ? C11 C12 C8 119.33(16) . . ? C11 C12 H12 120.3 . . ? C8 C12 H12 120.3 . . ? O1 C13 O2 123.70(15) . . ? O1 C13 C14 123.50(16) . . ? O2 C13 C14 112.80(14) . . ? C21 C14 C15 119.42(15) . . ? C21 C14 C13 121.50(15) . . ? C15 C14 C13 119.06(14) . . ? C14 C15 C16 120.42(15) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C18 119.89(15) . . ? C15 C16 C17 118.60(15) . . ? C18 C16 C17 121.51(15) . . ? O6 C17 O5 122.83(16) . . ? O6 C17 C16 122.55(16) . . ? O5 C17 C16 114.61(15) . . ? C19 C18 C16 119.72(15) . . ? C19 C18 H18 120.1 . . ? C16 C18 H18 120.1 . . ? C18 C19 C21 120.02(14) . . ? C18 C19 C20 119.35(14) . . ? C21 C19 C20 120.63(14) . . ? O4 C20 O3 123.28(15) . . ? O4 C20 C19 122.15(14) . . ? O3 C20 C19 114.57(13) . . ? C14 C21 C19 120.53(15) . . ? C14 C21 H21 119.7 . . ? C19 C21 H21 119.7 . . ? 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 C6 N2 N3 C7 -0.3(2) . . . . ? C5 N1 C1 C2 -1.2(3) . . . . ? N1 C1 C2 C3 0.6(3) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C1 C2 C3 C6 -177.58(18) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C6 C3 C4 C5 177.34(19) . . . . ? C1 N1 C5 C4 0.8(3) . . . . ? C3 C4 C5 N1 0.3(3) . . . . ? N3 N2 C6 N4 0.2(2) . . . . ? N3 N2 C6 C3 -179.65(15) . . . . ? C7 N4 C6 N2 -0.02(19) . . . . ? N5 N4 C6 N2 175.09(16) . . . . ? C7 N4 C6 C3 179.81(17) . . . . ? N5 N4 C6 C3 -5.1(3) . . . . ? C2 C3 C6 N2 159.82(18) . . . . ? C4 C3 C6 N2 -18.3(3) . . . . ? C2 C3 C6 N4 -20.0(3) . . . . ? C4 C3 C6 N4 161.92(18) . . . . ? N2 N3 C7 N4 0.29(19) . . . . ? N2 N3 C7 C8 179.17(15) . . . . ? C6 N4 C7 N3 -0.17(19) . . . . ? N5 N4 C7 N3 -175.52(16) . . . . ? C6 N4 C7 C8 -178.97(16) . . . . ? N5 N4 C7 C8 5.7(3) . . . . ? N3 C7 C8 C9 167.12(17) . . . . ? N4 C7 C8 C9 -14.2(3) . . . . ? N3 C7 C8 C12 -12.3(3) . . . . ? N4 C7 C8 C12 166.38(17) . . . . ? C12 C8 C9 C10 -0.7(3) . . . . ? C7 C8 C9 C10 179.90(17) . . . . ? C11 N6 C10 C9 0.1(3) . . . . ? C8 C9 C10 N6 0.5(3) . . . . ? C10 N6 C11 C12 -0.4(3) . . . . ? N6 C11 C12 C8 0.2(3) . . . . ? C9 C8 C12 C11 0.3(3) . . . . ? C7 C8 C12 C11 179.78(17) . . . . ? O1 C13 C14 C21 -171.72(18) . . . . ? O2 C13 C14 C21 7.9(2) . . . . ? O1 C13 C14 C15 6.6(3) . . . . ? O2 C13 C14 C15 -173.76(16) . . . . ? C21 C14 C15 C16 0.7(3) . . . . ? C13 C14 C15 C16 -177.72(15) . . . . ? C14 C15 C16 C18 -0.1(3) . . . . ? C14 C15 C16 C17 179.24(16) . . . . ? C15 C16 C17 O6 11.0(3) . . . . ? C18 C16 C17 O6 -169.73(18) . . . . ? C15 C16 C17 O5 -168.92(17) . . . . ? C18 C16 C17 O5 10.4(3) . . . . ? C15 C16 C18 C19 -0.6(3) . . . . ? C17 C16 C18 C19 -179.84(16) . . . . ? C16 C18 C19 C21 0.6(2) . . . . ? C16 C18 C19 C20 179.50(15) . . . . ? C18 C19 C20 O4 3.6(3) . . . . ? C21 C19 C20 O4 -177.49(16) . . . . ? C18 C19 C20 O3 -176.14(16) . . . . ? C21 C19 C20 O3 2.8(2) . . . . ? C15 C14 C21 C19 -0.6(2) . . . . ? C13 C14 C21 C19 177.71(15) . . . . ? C18 C19 C21 C14 0.0(2) . . . . ? C20 C19 C21 C14 -178.88(15) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.180 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.053 #===END