# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full MedChemComm _journal_coden_cambridge 1476 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email ffroncz@lsu.edu _publ_contact_author_name 'Frank R. Fronczek' loop_ _publ_author_name 'Benson G. Ongarora' 'Hairong Li' 'Xiaoke Hu' 'Frank R. Fronczek' 'Graca H. Vicente' data_2a _database_code_depnum_ccdc_archive 'CCDC 810389' #TrackingRef '4019_web_deposit_cif_file_0_FrankR.Fronczek_1296247231.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 N3 O3' _chemical_formula_sum 'C19 H17 N3 O3' _chemical_formula_weight 335.36 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_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc ' _symmetry_cell_setting Monoclinic 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 16.266(4) _cell_length_b 11.114(3) _cell_length_c 9.8401(16) _cell_angle_alpha 90 _cell_angle_beta 101.629(13) _cell_angle_gamma 90 _cell_volume 1742.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 90.0(5) _cell_measurement_reflns_used 4885 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 30.0 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(5) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'KappaCCD (with Oxford Cryostream)' _diffrn_measurement_method ' \w and \f scans ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8155 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.8 _diffrn_reflns_theta_max 30.0 _reflns_number_total 5047 _reflns_number_gt 3653 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0548P)^2^+0.4786P] 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 5047 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.074 _refine_ls_R_factor_gt 0.047 _refine_ls_wR_factor_ref 0.121 _refine_ls_wR_factor_gt 0.108 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 O1 O 0.77602(6) 0.44117(9) 0.57164(9) 0.0238(2) Uani 1 1 d . . . O2 O 0.37683(5) 0.83233(9) 0.49619(9) 0.0211(2) Uani 1 1 d . . . O3 O 0.46336(6) 0.79583(9) 0.34507(9) 0.0223(2) Uani 1 1 d . . . N1 N 0.91933(8) 0.26703(13) 0.43906(13) 0.0307(3) Uani 1 1 d . . . N2 N 1.13892(7) 0.36890(13) 0.67320(14) 0.0321(3) Uani 1 1 d . . . N3 N 0.48810(6) 0.71771(11) 0.56449(10) 0.0181(2) Uani 1 1 d . . . H3N H 0.4681(9) 0.7143(14) 0.6398(16) 0.022 Uiso 1 1 d . . . C1 C 0.84860(8) 0.47872(12) 0.65565(13) 0.0194(3) Uani 1 1 d . . . C2 C 0.92240(8) 0.42486(12) 0.63299(12) 0.0187(3) Uani 1 1 d . . . C3 C 0.99972(8) 0.45844(12) 0.71727(13) 0.0201(3) Uani 1 1 d . . . C4 C 1.00319(8) 0.54174(13) 0.82290(14) 0.0232(3) Uani 1 1 d . . . H4 H 1.0555 0.5634 0.8798 0.028 Uiso 1 1 calc R . . C5 C 0.92899(8) 0.59312(13) 0.84425(13) 0.0230(3) Uani 1 1 d . . . H5 H 0.9308 0.6494 0.9174 0.028 Uiso 1 1 calc R . . C6 C 0.85235(8) 0.56373(13) 0.76060(13) 0.0216(3) Uani 1 1 d . . . H6 H 0.8024 0.6016 0.7749 0.026 Uiso 1 1 calc R . . C7 C 0.91940(8) 0.33748(13) 0.52450(13) 0.0212(3) Uani 1 1 d . . . C8 C 1.07670(8) 0.40721(13) 0.69185(14) 0.0234(3) Uani 1 1 d . . . C9 C 0.70373(8) 0.51202(13) 0.56978(13) 0.0204(3) Uani 1 1 d . . . C10 C 0.64662(8) 0.47736(13) 0.64938(13) 0.0209(3) Uani 1 1 d . . . H10 H 0.6561 0.4074 0.7058 0.025 Uiso 1 1 calc R . . C11 C 0.57517(8) 0.54692(13) 0.64503(12) 0.0192(3) Uani 1 1 d . . . H11 H 0.5357 0.5249 0.6999 0.023 Uiso 1 1 calc R . . C12 C 0.56079(7) 0.64889(12) 0.56083(12) 0.0173(3) Uani 1 1 d . . . C13 C 0.61844(8) 0.68053(13) 0.47952(13) 0.0208(3) Uani 1 1 d . . . H13 H 0.6085 0.7489 0.4205 0.025 Uiso 1 1 calc R . . C14 C 0.69045(8) 0.61185(13) 0.48511(13) 0.0223(3) Uani 1 1 d . . . H14 H 0.7303 0.6336 0.4309 0.027 Uiso 1 1 calc R . . C15 C 0.44427(8) 0.78332(12) 0.45787(12) 0.0178(3) Uani 1 1 d . . . C16 C 0.32255(8) 0.91681(13) 0.40143(13) 0.0209(3) Uani 1 1 d . . . C17 C 0.27719(8) 0.85189(14) 0.27185(14) 0.0252(3) Uani 1 1 d . . . H17A H 0.3181 0.8256 0.2172 0.038 Uiso 1 1 calc R . . H17B H 0.2366 0.9066 0.2161 0.038 Uiso 1 1 calc R . . H17C H 0.2477 0.7816 0.2987 0.038 Uiso 1 1 calc R . . C18 C 0.37391(9) 1.02365(14) 0.37012(15) 0.0285(3) Uani 1 1 d . . . H18A H 0.4111 1.0505 0.4558 0.043 Uiso 1 1 calc R . . H18B H 0.3361 1.0895 0.3320 0.043 Uiso 1 1 calc R . . H18C H 0.4076 0.9999 0.3024 0.043 Uiso 1 1 calc R . . C19 C 0.25995(9) 0.95674(16) 0.48835(15) 0.0315(4) Uani 1 1 d . . . H19A H 0.2313 0.8861 0.5163 0.047 Uiso 1 1 calc R . . H19B H 0.2185 1.0109 0.4335 0.047 Uiso 1 1 calc R . . H19C H 0.2897 0.9990 0.5712 0.047 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 0.0135(4) 0.0281(5) 0.0279(5) -0.0085(4) -0.0009(4) 0.0041(4) O2 0.0159(4) 0.0313(6) 0.0164(4) 0.0036(4) 0.0035(3) 0.0066(4) O3 0.0212(5) 0.0320(6) 0.0144(4) 0.0021(4) 0.0054(3) 0.0029(4) N1 0.0262(6) 0.0349(8) 0.0291(6) -0.0039(6) 0.0008(5) 0.0089(5) N2 0.0192(6) 0.0327(7) 0.0451(7) -0.0014(6) 0.0081(5) -0.0018(5) N3 0.0146(5) 0.0265(6) 0.0139(5) 0.0015(4) 0.0048(4) 0.0039(4) C1 0.0134(6) 0.0239(7) 0.0200(6) 0.0011(5) 0.0008(4) 0.0001(5) C2 0.0167(6) 0.0209(7) 0.0184(6) 0.0022(5) 0.0031(4) 0.0013(5) C3 0.0151(6) 0.0215(7) 0.0236(6) 0.0044(5) 0.0037(5) 0.0003(5) C4 0.0170(6) 0.0253(7) 0.0254(6) 0.0006(5) -0.0002(5) -0.0027(5) C5 0.0221(6) 0.0241(7) 0.0220(6) -0.0018(5) 0.0023(5) -0.0015(5) C6 0.0178(6) 0.0234(7) 0.0236(6) -0.0011(5) 0.0040(5) 0.0010(5) C7 0.0147(6) 0.0252(7) 0.0230(6) 0.0020(5) 0.0021(5) 0.0046(5) C8 0.0172(6) 0.0245(7) 0.0280(6) 0.0012(6) 0.0030(5) -0.0028(5) C9 0.0130(6) 0.0252(7) 0.0215(6) -0.0074(5) -0.0002(4) 0.0029(5) C10 0.0190(6) 0.0215(7) 0.0209(6) -0.0016(5) 0.0006(5) 0.0008(5) C11 0.0149(6) 0.0246(7) 0.0180(6) -0.0016(5) 0.0031(4) -0.0006(5) C12 0.0121(5) 0.0241(7) 0.0152(5) -0.0038(5) 0.0016(4) 0.0002(5) C13 0.0183(6) 0.0247(7) 0.0204(6) 0.0005(5) 0.0061(5) 0.0011(5) C14 0.0163(6) 0.0297(8) 0.0220(6) -0.0035(5) 0.0064(5) -0.0006(5) C15 0.0142(6) 0.0226(7) 0.0164(5) -0.0016(5) 0.0023(4) -0.0003(5) C16 0.0165(6) 0.0268(7) 0.0184(6) 0.0007(5) 0.0010(5) 0.0055(5) C17 0.0206(6) 0.0290(8) 0.0233(6) -0.0013(6) -0.0023(5) 0.0029(6) C18 0.0257(7) 0.0254(8) 0.0326(7) 0.0002(6) 0.0018(6) 0.0009(6) C19 0.0227(7) 0.0475(10) 0.0245(7) 0.0024(7) 0.0047(5) 0.0151(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 C1 1.3630(15) . ? O1 C9 1.4122(15) . ? O2 C15 1.3451(15) . ? O2 C16 1.4828(15) . ? O3 C15 1.2192(15) . ? N1 C7 1.1486(18) . ? N2 C8 1.1464(18) . ? N3 C15 1.3562(16) . ? N3 C12 1.4147(16) . ? N3 H3N 0.868(15) . ? C1 C6 1.3920(18) . ? C1 C2 1.3989(18) . ? C2 C3 1.4100(18) . ? C2 C7 1.4367(19) . ? C3 C4 1.3845(19) . ? C3 C8 1.4425(18) . ? C4 C5 1.3889(19) . ? C4 H4 0.9500 . ? C5 C6 1.3874(18) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C9 C14 1.378(2) . ? C9 C10 1.3850(19) . ? C10 C11 1.3894(18) . ? C10 H10 0.9500 . ? C11 C12 1.3955(19) . ? C11 H11 0.9500 . ? C12 C13 1.3948(17) . ? C13 C14 1.3898(18) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C16 C18 1.519(2) . ? C16 C17 1.5204(18) . ? C16 C19 1.5221(18) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C9 117.02(10) . . ? C15 O2 C16 119.73(9) . . ? C15 N3 C12 125.64(10) . . ? C15 N3 H3N 117.1(10) . . ? C12 N3 H3N 117.2(10) . . ? O1 C1 C6 124.11(12) . . ? O1 C1 C2 116.01(11) . . ? C6 C1 C2 119.87(12) . . ? C1 C2 C3 119.03(12) . . ? C1 C2 C7 120.39(11) . . ? C3 C2 C7 120.58(12) . . ? C4 C3 C2 121.00(12) . . ? C4 C3 C8 119.25(12) . . ? C2 C3 C8 119.74(12) . . ? C3 C4 C5 118.90(12) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 121.18(13) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C1 119.98(12) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? N1 C7 C2 178.10(14) . . ? N2 C8 C3 178.32(16) . . ? C14 C9 C10 121.64(12) . . ? C14 C9 O1 119.04(11) . . ? C10 C9 O1 119.29(12) . . ? C9 C10 C11 118.69(13) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? C10 C11 C12 120.61(12) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 119.59(12) . . ? C13 C12 N3 122.70(12) . . ? C11 C12 N3 117.70(11) . . ? C14 C13 C12 119.83(13) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C9 C14 C13 119.62(12) . . ? C9 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? O3 C15 O2 125.51(12) . . ? O3 C15 N3 125.09(12) . . ? O2 C15 N3 109.40(10) . . ? O2 C16 C18 109.91(11) . . ? O2 C16 C17 110.71(11) . . ? C18 C16 C17 113.25(11) . . ? O2 C16 C19 102.25(10) . . ? C18 C16 C19 110.10(13) . . ? C17 C16 C19 110.06(11) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 O1 C1 C6 15.19(18) . . . . ? C9 O1 C1 C2 -165.84(11) . . . . ? O1 C1 C2 C3 -179.27(11) . . . . ? C6 C1 C2 C3 -0.25(19) . . . . ? O1 C1 C2 C7 1.32(19) . . . . ? C6 C1 C2 C7 -179.66(12) . . . . ? C1 C2 C3 C4 1.19(19) . . . . ? C7 C2 C3 C4 -179.40(13) . . . . ? C1 C2 C3 C8 -177.63(12) . . . . ? C7 C2 C3 C8 1.78(19) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? C8 C3 C4 C5 178.25(13) . . . . ? C3 C4 C5 C6 -1.0(2) . . . . ? C4 C5 C6 C1 1.9(2) . . . . ? O1 C1 C6 C5 177.65(13) . . . . ? C2 C1 C6 C5 -1.3(2) . . . . ? C1 O1 C9 C14 83.42(15) . . . . ? C1 O1 C9 C10 -98.70(14) . . . . ? C14 C9 C10 C11 -1.3(2) . . . . ? O1 C9 C10 C11 -179.08(11) . . . . ? C9 C10 C11 C12 0.75(19) . . . . ? C10 C11 C12 C13 0.52(19) . . . . ? C10 C11 C12 N3 -178.12(12) . . . . ? C15 N3 C12 C13 31.2(2) . . . . ? C15 N3 C12 C11 -150.16(13) . . . . ? C11 C12 C13 C14 -1.31(19) . . . . ? N3 C12 C13 C14 177.26(12) . . . . ? C10 C9 C14 C13 0.5(2) . . . . ? O1 C9 C14 C13 178.30(11) . . . . ? C12 C13 C14 C9 0.8(2) . . . . ? C16 O2 C15 O3 -5.02(19) . . . . ? C16 O2 C15 N3 174.88(11) . . . . ? C12 N3 C15 O3 -2.9(2) . . . . ? C12 N3 C15 O2 177.16(11) . . . . ? C15 O2 C16 C18 -58.86(15) . . . . ? C15 O2 C16 C17 67.00(15) . . . . ? C15 O2 C16 C19 -175.78(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3N O3 0.868(15) 2.040(16) 2.8733(14) 160.6(14) 4_576 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.31 _refine_diff_density_min -0.26 _refine_diff_density_rms 0.051 # END OF CIF # Attachment '4020_web_deposit_cif_file_1_FrankR.Fronczek_1296247231.cif' data_2b _database_code_depnum_ccdc_archive 'CCDC 810390' #TrackingRef '4020_web_deposit_cif_file_1_FrankR.Fronczek_1296247231.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 N3 O3' _chemical_formula_sum 'C19 H17 N3 O3' _chemical_formula_weight 335.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 10.139(2) _cell_length_b 8.597(2) _cell_length_c 20.157(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1757.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 90.0(5) _cell_measurement_reflns_used 5696 _cell_measurement_theta_min 4.3 _cell_measurement_theta_max 67.8 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.717 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.814 _exptl_absorpt_correction_T_max 0.864 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(5) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex-II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8771 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 5.1 _diffrn_reflns_theta_max 68.1 _reflns_number_total 2507 _reflns_number_gt 2403 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker Apex2' _computing_data_reduction 'Bruker Apex2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _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^)+(0.0471P)^2^+0.3163P] 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 0.0013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details '935 Friedel pairs (Flack, 1983) ' _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_number_reflns 2507 _refine_ls_number_parameters 233 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.034 _refine_ls_R_factor_gt 0.032 _refine_ls_wR_factor_ref 0.084 _refine_ls_wR_factor_gt 0.083 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 O1 O 0.35271(12) 0.07556(17) 0.42679(8) 0.0295(3) Uani 1 1 d . . . O2 O 0.85512(13) 0.38705(17) 0.58253(8) 0.0337(4) Uani 1 1 d . . . O3 O 0.88125(12) 0.28762(16) 0.68698(7) 0.0293(3) Uani 1 1 d . . . N1 N -0.11108(16) 0.0872(2) 0.26012(10) 0.0320(4) Uani 1 1 d . . . N2 N -0.23441(17) 0.4197(2) 0.37730(10) 0.0366(5) Uani 1 1 d . . . N3 N 0.71161(15) 0.20932(19) 0.62817(9) 0.0237(4) Uani 1 1 d . . . H3N H 0.699(2) 0.159(3) 0.6673(13) 0.028 Uiso 1 1 d . . . C1 C 0.23275(18) 0.1483(2) 0.42261(10) 0.0248(4) Uani 1 1 d . . . C2 C 0.15681(18) 0.1017(2) 0.36862(11) 0.0251(4) Uani 1 1 d . . . H2 H 0.1877 0.0237 0.3391 0.030 Uiso 1 1 calc R . . C3 C 0.03457(19) 0.1719(2) 0.35872(11) 0.0250(4) Uani 1 1 d . . . C4 C -0.01104(18) 0.2865(2) 0.40270(11) 0.0264(4) Uani 1 1 d . . . C5 C 0.06562(19) 0.3278(2) 0.45692(11) 0.0278(4) Uani 1 1 d . . . H5 H 0.0340 0.4033 0.4874 0.033 Uiso 1 1 calc R . . C6 C 0.18818(19) 0.2596(2) 0.46693(11) 0.0274(5) Uani 1 1 d . . . H6 H 0.2409 0.2890 0.5038 0.033 Uiso 1 1 calc R . . C7 C -0.04587(18) 0.1246(2) 0.30355(11) 0.0260(4) Uani 1 1 d . . . C8 C -0.13598(19) 0.3601(2) 0.38956(11) 0.0290(4) Uani 1 1 d . . . C9 C 0.43813(18) 0.1181(2) 0.47865(11) 0.0265(4) Uani 1 1 d . . . C10 C 0.5370(2) 0.2231(2) 0.46590(11) 0.0290(5) Uani 1 1 d . . . H10 H 0.5428 0.2718 0.4237 0.035 Uiso 1 1 calc R . . C11 C 0.62872(18) 0.2580(2) 0.51513(11) 0.0277(4) Uani 1 1 d . . . H11 H 0.6966 0.3316 0.5067 0.033 Uiso 1 1 calc R . . C12 C 0.62094(17) 0.1853(2) 0.57655(10) 0.0227(4) Uani 1 1 d . . . C13 C 0.51863(19) 0.0797(2) 0.58876(12) 0.0290(4) Uani 1 1 d . . . H13 H 0.5113 0.0314 0.6310 0.035 Uiso 1 1 calc R . . C14 C 0.42781(19) 0.0454(2) 0.53930(11) 0.0298(5) Uani 1 1 d . . . H14 H 0.3592 -0.0276 0.5472 0.036 Uiso 1 1 calc R . . C15 C 0.82038(18) 0.3046(2) 0.62777(11) 0.0245(4) Uani 1 1 d . . . C16 C 1.0009(2) 0.3780(2) 0.70288(12) 0.0297(5) Uani 1 1 d . . . C17 C 1.0335(2) 0.3216(3) 0.77200(13) 0.0413(6) Uani 1 1 d . . . H17A H 0.9589 0.3426 0.8016 0.062 Uiso 1 1 calc R . . H17B H 1.1119 0.3761 0.7883 0.062 Uiso 1 1 calc R . . H17C H 1.0507 0.2094 0.7709 0.062 Uiso 1 1 calc R . . C18 C 0.9695(2) 0.5493(2) 0.70392(13) 0.0390(6) Uani 1 1 d . . . H18A H 0.9486 0.5844 0.6589 0.059 Uiso 1 1 calc R . . H18B H 1.0460 0.6071 0.7206 0.059 Uiso 1 1 calc R . . H18C H 0.8936 0.5679 0.7329 0.059 Uiso 1 1 calc R . . C19 C 1.1096(2) 0.3397(3) 0.65413(15) 0.0504(7) Uani 1 1 d . . . H19A H 1.1204 0.2266 0.6515 0.076 Uiso 1 1 calc R . . H19B H 1.1923 0.3872 0.6690 0.076 Uiso 1 1 calc R . . H19C H 1.0863 0.3805 0.6103 0.076 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0210(6) 0.0391(8) 0.0286(9) -0.0081(6) -0.0067(6) 0.0054(5) O2 0.0272(7) 0.0465(9) 0.0273(9) 0.0020(7) 0.0013(7) -0.0131(6) O3 0.0231(7) 0.0339(8) 0.0308(9) 0.0002(6) -0.0059(6) -0.0090(5) N1 0.0298(9) 0.0361(10) 0.0300(12) 0.0043(7) -0.0045(9) -0.0001(7) N2 0.0284(9) 0.0447(10) 0.0367(13) 0.0052(8) 0.0040(8) 0.0072(8) N3 0.0191(8) 0.0312(8) 0.0206(10) 0.0012(7) 0.0010(7) -0.0042(6) C1 0.0198(9) 0.0288(9) 0.0258(12) 0.0003(8) 0.0005(8) -0.0011(7) C2 0.0211(9) 0.0294(9) 0.0248(12) -0.0021(8) 0.0006(8) -0.0007(7) C3 0.0241(9) 0.0274(9) 0.0234(12) 0.0048(8) -0.0009(8) -0.0043(7) C4 0.0216(9) 0.0315(10) 0.0261(12) 0.0043(8) 0.0028(8) 0.0001(7) C5 0.0264(10) 0.0308(10) 0.0262(12) -0.0017(8) 0.0037(9) -0.0004(7) C6 0.0274(10) 0.0302(10) 0.0247(13) -0.0016(8) 0.0000(8) -0.0024(8) C7 0.0219(9) 0.0291(10) 0.0270(12) 0.0037(8) 0.0012(9) 0.0013(7) C8 0.0275(10) 0.0316(10) 0.0279(12) 0.0027(9) 0.0045(9) -0.0011(8) C9 0.0218(9) 0.0336(10) 0.0240(12) -0.0053(8) -0.0030(8) 0.0022(8) C10 0.0265(10) 0.0378(11) 0.0228(13) 0.0017(8) 0.0004(9) -0.0010(8) C11 0.0224(9) 0.0355(11) 0.0252(12) 0.0028(8) 0.0022(8) -0.0041(8) C12 0.0186(8) 0.0294(10) 0.0201(12) -0.0030(7) 0.0016(8) 0.0014(6) C13 0.0275(9) 0.0342(10) 0.0252(12) 0.0039(9) -0.0024(8) -0.0068(8) C14 0.0234(10) 0.0356(11) 0.0303(13) 0.0005(8) -0.0017(9) -0.0062(8) C15 0.0191(9) 0.0296(10) 0.0248(12) -0.0032(8) 0.0017(8) -0.0030(7) C16 0.0226(9) 0.0342(10) 0.0325(13) -0.0050(9) -0.0037(9) -0.0072(8) C17 0.0407(13) 0.0403(12) 0.0429(16) 0.0041(10) -0.0182(12) -0.0106(9) C18 0.0362(12) 0.0336(11) 0.0472(16) -0.0022(10) -0.0088(10) -0.0081(8) C19 0.0242(11) 0.0775(18) 0.0495(19) -0.0241(15) 0.0004(12) -0.0039(10) _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 C1 1.370(2) . ? O1 C9 1.406(2) . ? O2 C15 1.207(3) . ? O3 C15 1.352(3) . ? O3 C16 1.476(2) . ? N1 C7 1.143(3) . ? N2 C8 1.149(3) . ? N3 C15 1.374(2) . ? N3 C12 1.404(2) . ? N3 H3N 0.91(3) . ? C1 C6 1.384(3) . ? C1 C2 1.392(3) . ? C2 C3 1.393(3) . ? C2 H2 0.9500 . ? C3 C4 1.404(3) . ? C3 C7 1.438(3) . ? C4 C5 1.387(3) . ? C4 C8 1.441(3) . ? C5 C6 1.389(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C9 C10 1.374(3) . ? C9 C14 1.377(3) . ? C10 C11 1.393(3) . ? C10 H10 0.9500 . ? C11 C12 1.389(3) . ? C11 H11 0.9500 . ? C12 C13 1.400(3) . ? C13 C14 1.389(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C16 C18 1.507(3) . ? C16 C17 1.512(3) . ? C16 C19 1.512(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C9 118.28(15) . . ? C15 O3 C16 120.68(16) . . ? C15 N3 C12 127.52(17) . . ? C15 N3 H3N 113.7(14) . . ? C12 N3 H3N 118.8(14) . . ? O1 C1 C6 124.44(19) . . ? O1 C1 C2 114.05(17) . . ? C6 C1 C2 121.51(18) . . ? C1 C2 C3 118.67(18) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C2 C3 C4 120.43(19) . . ? C2 C3 C7 119.55(18) . . ? C4 C3 C7 120.01(17) . . ? C5 C4 C3 119.50(18) . . ? C5 C4 C8 121.69(19) . . ? C3 C4 C8 118.80(19) . . ? C4 C5 C6 120.53(19) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 119.34(19) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? N1 C7 C3 179.2(2) . . ? N2 C8 C4 178.1(2) . . ? C10 C9 C14 121.33(19) . . ? C10 C9 O1 118.78(19) . . ? C14 C9 O1 119.69(17) . . ? C9 C10 C11 119.72(19) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 120.00(18) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 119.37(18) . . ? C11 C12 N3 123.86(17) . . ? C13 C12 N3 116.76(18) . . ? C14 C13 C12 120.2(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C9 C14 C13 119.38(19) . . ? C9 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? O2 C15 O3 126.66(17) . . ? O2 C15 N3 126.07(18) . . ? O3 C15 N3 107.27(16) . . ? O3 C16 C18 110.12(16) . . ? O3 C16 C17 102.16(17) . . ? C18 C16 C17 110.30(19) . . ? O3 C16 C19 110.05(17) . . ? C18 C16 C19 112.1(2) . . ? C17 C16 C19 111.7(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 O1 C1 C6 -1.3(3) . . . . ? C9 O1 C1 C2 178.24(18) . . . . ? O1 C1 C2 C3 -178.20(17) . . . . ? C6 C1 C2 C3 1.4(3) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C1 C2 C3 C7 -179.51(18) . . . . ? C2 C3 C4 C5 -1.1(3) . . . . ? C7 C3 C4 C5 178.01(18) . . . . ? C2 C3 C4 C8 177.94(18) . . . . ? C7 C3 C4 C8 -3.0(3) . . . . ? C3 C4 C5 C6 1.7(3) . . . . ? C8 C4 C5 C6 -177.31(18) . . . . ? O1 C1 C6 C5 178.72(18) . . . . ? C2 C1 C6 C5 -0.8(3) . . . . ? C4 C5 C6 C1 -0.8(3) . . . . ? C1 O1 C9 C10 -98.0(2) . . . . ? C1 O1 C9 C14 87.0(2) . . . . ? C14 C9 C10 C11 -0.3(3) . . . . ? O1 C9 C10 C11 -175.19(17) . . . . ? C9 C10 C11 C12 0.8(3) . . . . ? C10 C11 C12 C13 -1.4(3) . . . . ? C10 C11 C12 N3 177.73(18) . . . . ? C15 N3 C12 C11 -0.1(3) . . . . ? C15 N3 C12 C13 179.01(18) . . . . ? C11 C12 C13 C14 1.6(3) . . . . ? N3 C12 C13 C14 -177.62(18) . . . . ? C10 C9 C14 C13 0.4(3) . . . . ? O1 C9 C14 C13 175.31(17) . . . . ? C12 C13 C14 C9 -1.1(3) . . . . ? C16 O3 C15 O2 1.9(3) . . . . ? C16 O3 C15 N3 -178.58(16) . . . . ? C12 N3 C15 O2 1.5(3) . . . . ? C12 N3 C15 O3 -178.00(16) . . . . ? C15 O3 C16 C18 63.1(2) . . . . ? C15 O3 C16 C17 -179.70(17) . . . . ? C15 O3 C16 C19 -60.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3N N1 0.91(3) 2.16(3) 3.036(3) 161(2) 4 _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 66.6 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.19 _refine_diff_density_min -0.15 _refine_diff_density_rms 0.033 # END OF CIF # Attachment '4021_web_deposit_cif_file_2_FrankR.Fronczek_1296247231.cif' data_Compound10 _database_code_depnum_ccdc_archive 'CCDC 810391' #TrackingRef '4021_web_deposit_cif_file_2_FrankR.Fronczek_1296247231.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H30 N4 O6' _chemical_formula_sum 'C30 H30 N4 O6' _chemical_formula_weight 542.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0348(5) _cell_length_b 12.0728(6) _cell_length_c 13.3158(10) _cell_angle_alpha 110.460(5) _cell_angle_beta 102.622(4) _cell_angle_gamma 101.132(4) _cell_volume 1409.38(15) _cell_formula_units_Z 2 _cell_measurement_temperature 90.0(5) _cell_measurement_reflns_used 4782 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 68.2 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 0.743 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.836 _exptl_absorpt_correction_T_max 0.964 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(5) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex-II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12770 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.7 _diffrn_reflns_theta_max 68.6 _reflns_number_total 4972 _reflns_number_gt 4271 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker Apex2' _computing_data_reduction 'Bruker Apex2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _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^)+(0.0531P)^2^+0.4513P] 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 ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4972 _refine_ls_number_parameters 373 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.044 _refine_ls_R_factor_gt 0.037 _refine_ls_wR_factor_ref 0.102 _refine_ls_wR_factor_gt 0.096 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.31046(10) 0.35893(9) 0.26258(8) 0.0237(2) Uani 1 1 d . . . O2 O -0.08441(10) 0.80440(9) 0.12917(8) 0.0242(2) Uani 1 1 d . . . O3 O 0.10569(11) 0.85091(9) 0.28263(8) 0.0271(2) Uani 1 1 d . . . O4 O 0.41225(10) 0.18842(9) 0.29573(8) 0.0244(2) Uani 1 1 d . . . O5 O 0.81239(11) -0.21492(9) 0.50617(8) 0.0263(2) Uani 1 1 d . . . O6 O 0.63038(11) -0.27150(10) 0.34481(9) 0.0308(3) Uani 1 1 d . . . N1 N 0.67810(13) 0.46891(13) -0.00439(11) 0.0309(3) Uani 1 1 d . . . N2 N 0.78295(14) 0.17440(12) 0.00377(12) 0.0316(3) Uani 1 1 d . . . N3 N -0.00328(13) 0.65443(11) 0.14529(10) 0.0220(3) Uani 1 1 d . . . H3N H -0.0767(19) 0.6137(16) 0.0861(15) 0.026 Uiso 1 1 d . . . N4 N 0.71777(13) -0.07252(11) 0.48012(10) 0.0231(3) Uani 1 1 d . . . H4N H 0.7825(19) -0.0253(16) 0.5455(15) 0.028 Uiso 1 1 d . . . C1 C 0.41146(14) 0.33107(13) 0.21269(11) 0.0198(3) Uani 1 1 d . . . C2 C 0.46313(14) 0.38979(13) 0.15053(11) 0.0211(3) Uani 1 1 d . . . H2 H 0.4294 0.4552 0.1417 0.025 Uiso 1 1 calc R . . C3 C 0.56463(14) 0.35276(13) 0.10098(11) 0.0213(3) Uani 1 1 d . . . C4 C 0.61242(14) 0.25492(13) 0.11228(11) 0.0214(3) Uani 1 1 d . . . C5 C 0.56346(14) 0.19853(13) 0.17796(12) 0.0218(3) Uani 1 1 d . . . H5 H 0.5975 0.1334 0.1872 0.026 Uiso 1 1 calc R . . C6 C 0.46525(14) 0.23746(13) 0.22977(11) 0.0202(3) Uani 1 1 d . . . C7 C 0.62415(15) 0.41696(14) 0.04048(12) 0.0240(3) Uani 1 1 d . . . C8 C 0.70865(15) 0.21039(13) 0.05327(12) 0.0239(3) Uani 1 1 d . . . C9 C 0.23609(14) 0.43645(13) 0.23273(12) 0.0217(3) Uani 1 1 d . . . C10 C 0.29256(15) 0.56335(14) 0.28685(12) 0.0244(3) Uani 1 1 d . . . H10 H 0.3839 0.5993 0.3426 0.029 Uiso 1 1 calc R . . C11 C 0.21526(15) 0.63852(14) 0.25952(12) 0.0238(3) Uani 1 1 d . . . H11 H 0.2542 0.7260 0.2958 0.029 Uiso 1 1 calc R . . C12 C 0.08085(14) 0.58516(13) 0.17896(11) 0.0202(3) Uani 1 1 d . . . C13 C 0.02588(15) 0.45697(13) 0.12550(12) 0.0222(3) Uani 1 1 d . . . H13 H -0.0660 0.4204 0.0705 0.027 Uiso 1 1 calc R . . C14 C 0.10368(15) 0.38204(13) 0.15156(12) 0.0225(3) Uani 1 1 d . . . H14 H 0.0664 0.2945 0.1141 0.027 Uiso 1 1 calc R . . C15 C 0.01513(14) 0.77818(13) 0.19476(11) 0.0209(3) Uani 1 1 d . . . C16 C -0.09973(15) 0.93019(13) 0.16357(12) 0.0245(3) Uani 1 1 d . . . C17 C 0.03446(16) 1.02080(14) 0.17165(13) 0.0291(3) Uani 1 1 d . . . H17A H 0.1105 1.0383 0.2403 0.044 Uiso 1 1 calc R . . H17B H 0.0143 1.0979 0.1743 0.044 Uiso 1 1 calc R . . H17C H 0.0651 0.9847 0.1056 0.044 Uiso 1 1 calc R . . C18 C -0.13884(17) 0.96505(15) 0.27189(14) 0.0326(4) Uani 1 1 d . . . H18A H -0.2182 0.8979 0.2643 0.049 Uiso 1 1 calc R . . H18B H -0.1676 1.0409 0.2868 0.049 Uiso 1 1 calc R . . H18C H -0.0560 0.9789 0.3345 0.049 Uiso 1 1 calc R . . C19 C -0.22460(17) 0.91287(15) 0.06632(15) 0.0366(4) Uani 1 1 d . . . H19A H -0.2012 0.8826 -0.0042 0.055 Uiso 1 1 calc R . . H19B H -0.2443 0.9922 0.0785 0.055 Uiso 1 1 calc R . . H19C H -0.3092 0.8526 0.0617 0.055 Uiso 1 1 calc R . . C20 C 0.48979(15) 0.12001(13) 0.33799(12) 0.0225(3) Uani 1 1 d . . . C21 C 0.61250(16) 0.18272(14) 0.42933(12) 0.0256(3) Uani 1 1 d . . . H21 H 0.6458 0.2705 0.4613 0.031 Uiso 1 1 calc R . . C22 C 0.68627(15) 0.11625(13) 0.47372(12) 0.0250(3) Uani 1 1 d . . . H22 H 0.7713 0.1588 0.5359 0.030 Uiso 1 1 calc R . . C23 C 0.63708(15) -0.01260(13) 0.42819(12) 0.0217(3) Uani 1 1 d . . . C24 C 0.51361(15) -0.07435(13) 0.33607(12) 0.0237(3) Uani 1 1 d . . . H24 H 0.4796 -0.1621 0.3040 0.028 Uiso 1 1 calc R . . C25 C 0.43969(15) -0.00714(14) 0.29086(12) 0.0242(3) Uani 1 1 d . . . H25 H 0.3553 -0.0489 0.2280 0.029 Uiso 1 1 calc R . . C26 C 0.71194(15) -0.19462(13) 0.43480(12) 0.0232(3) Uani 1 1 d . . . C27 C 0.83103(16) -0.33968(13) 0.47547(13) 0.0268(3) Uani 1 1 d . . . C28 C 0.95199(18) -0.32190(15) 0.57711(14) 0.0342(4) Uani 1 1 d . . . H28A H 1.0389 -0.2630 0.5833 0.051 Uiso 1 1 calc R . . H28B H 0.9696 -0.4015 0.5675 0.051 Uiso 1 1 calc R . . H28C H 0.9251 -0.2898 0.6458 0.051 Uiso 1 1 calc R . . C29 C 0.87678(19) -0.37546(16) 0.36970(14) 0.0362(4) Uani 1 1 d . . . H29A H 0.7985 -0.3855 0.3055 0.054 Uiso 1 1 calc R . . H29B H 0.9005 -0.4535 0.3549 0.054 Uiso 1 1 calc R . . H29C H 0.9609 -0.3104 0.3807 0.054 Uiso 1 1 calc R . . C30 C 0.69591(18) -0.43204(14) 0.46286(14) 0.0327(4) Uani 1 1 d . . . H30A H 0.6639 -0.3992 0.5288 0.049 Uiso 1 1 calc R . . H30B H 0.7153 -0.5102 0.4570 0.049 Uiso 1 1 calc R . . H30C H 0.6212 -0.4464 0.3946 0.049 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 0.0248(5) 0.0318(6) 0.0286(5) 0.0197(4) 0.0141(4) 0.0184(4) O2 0.0257(5) 0.0210(5) 0.0269(5) 0.0107(4) 0.0045(4) 0.0114(4) O3 0.0277(5) 0.0242(5) 0.0272(5) 0.0099(4) 0.0033(4) 0.0100(4) O4 0.0234(5) 0.0318(6) 0.0320(5) 0.0226(5) 0.0136(4) 0.0151(4) O5 0.0300(5) 0.0230(5) 0.0275(5) 0.0124(4) 0.0051(4) 0.0115(4) O6 0.0339(6) 0.0264(5) 0.0305(6) 0.0128(5) 0.0033(5) 0.0109(5) N1 0.0275(6) 0.0416(8) 0.0404(7) 0.0283(7) 0.0157(6) 0.0188(6) N2 0.0316(7) 0.0305(7) 0.0408(7) 0.0167(6) 0.0184(6) 0.0144(6) N3 0.0209(6) 0.0220(6) 0.0234(6) 0.0103(5) 0.0033(5) 0.0092(5) N4 0.0250(6) 0.0230(6) 0.0233(6) 0.0122(5) 0.0046(5) 0.0093(5) C1 0.0175(6) 0.0236(7) 0.0195(6) 0.0093(5) 0.0053(5) 0.0084(5) C2 0.0217(7) 0.0227(7) 0.0233(7) 0.0126(6) 0.0061(5) 0.0113(6) C3 0.0199(6) 0.0247(7) 0.0226(7) 0.0130(6) 0.0062(5) 0.0076(6) C4 0.0190(6) 0.0239(7) 0.0244(7) 0.0115(6) 0.0072(5) 0.0092(6) C5 0.0207(6) 0.0223(7) 0.0264(7) 0.0131(6) 0.0067(6) 0.0099(6) C6 0.0192(6) 0.0231(7) 0.0203(6) 0.0117(6) 0.0045(5) 0.0067(6) C7 0.0212(7) 0.0299(8) 0.0297(7) 0.0173(6) 0.0098(6) 0.0149(6) C8 0.0243(7) 0.0231(7) 0.0296(7) 0.0147(6) 0.0095(6) 0.0096(6) C9 0.0234(7) 0.0297(8) 0.0252(7) 0.0180(6) 0.0134(6) 0.0170(6) C10 0.0194(6) 0.0291(8) 0.0256(7) 0.0110(6) 0.0062(6) 0.0106(6) C11 0.0222(7) 0.0239(7) 0.0278(7) 0.0109(6) 0.0088(6) 0.0103(6) C12 0.0217(6) 0.0248(7) 0.0218(7) 0.0130(6) 0.0108(5) 0.0122(6) C13 0.0205(6) 0.0258(7) 0.0235(7) 0.0124(6) 0.0069(5) 0.0091(6) C14 0.0252(7) 0.0228(7) 0.0250(7) 0.0125(6) 0.0111(6) 0.0105(6) C15 0.0208(6) 0.0251(7) 0.0227(7) 0.0135(6) 0.0088(6) 0.0100(6) C16 0.0261(7) 0.0201(7) 0.0307(7) 0.0115(6) 0.0087(6) 0.0122(6) C17 0.0302(8) 0.0272(8) 0.0359(8) 0.0161(7) 0.0136(7) 0.0115(6) C18 0.0335(8) 0.0301(8) 0.0416(9) 0.0150(7) 0.0203(7) 0.0147(7) C19 0.0334(8) 0.0255(8) 0.0476(10) 0.0162(7) -0.0007(7) 0.0143(7) C20 0.0231(7) 0.0295(8) 0.0279(7) 0.0197(6) 0.0132(6) 0.0148(6) C21 0.0312(8) 0.0224(7) 0.0272(7) 0.0129(6) 0.0094(6) 0.0111(6) C22 0.0266(7) 0.0254(7) 0.0240(7) 0.0113(6) 0.0062(6) 0.0094(6) C23 0.0237(7) 0.0269(7) 0.0243(7) 0.0162(6) 0.0123(6) 0.0123(6) C24 0.0221(7) 0.0244(7) 0.0297(7) 0.0148(6) 0.0102(6) 0.0079(6) C25 0.0192(6) 0.0292(8) 0.0276(7) 0.0152(6) 0.0075(6) 0.0074(6) C26 0.0247(7) 0.0250(7) 0.0252(7) 0.0146(6) 0.0089(6) 0.0095(6) C27 0.0326(8) 0.0228(7) 0.0294(8) 0.0133(6) 0.0085(6) 0.0142(6) C28 0.0407(9) 0.0270(8) 0.0339(8) 0.0136(7) 0.0040(7) 0.0146(7) C29 0.0416(9) 0.0400(9) 0.0354(9) 0.0174(7) 0.0165(7) 0.0211(8) C30 0.0396(9) 0.0267(8) 0.0323(8) 0.0162(7) 0.0075(7) 0.0074(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 C1 1.3606(16) . ? O1 C9 1.4110(16) . ? O2 C15 1.3397(17) . ? O2 C16 1.4746(16) . ? O3 C15 1.2144(17) . ? O4 C6 1.3605(16) . ? O4 C20 1.4092(16) . ? O5 C26 1.3486(17) . ? O5 C27 1.4773(17) . ? O6 C26 1.2115(18) . ? N1 C7 1.1470(19) . ? N2 C8 1.148(2) . ? N3 C15 1.3611(18) . ? N3 C12 1.4080(18) . ? N3 H3N 0.861(18) . ? N4 C26 1.3675(19) . ? N4 C23 1.4100(18) . ? N4 H4N 0.876(18) . ? C1 C2 1.3830(19) . ? C1 C6 1.4077(19) . ? C2 C3 1.391(2) . ? C2 H2 0.9500 . ? C3 C4 1.3998(19) . ? C3 C7 1.4405(19) . ? C4 C5 1.3944(19) . ? C4 C8 1.441(2) . ? C5 C6 1.385(2) . ? C5 H5 0.9500 . ? C9 C10 1.379(2) . ? C9 C14 1.380(2) . ? C10 C11 1.392(2) . ? C10 H10 0.9500 . ? C11 C12 1.391(2) . ? C11 H11 0.9500 . ? C12 C13 1.391(2) . ? C13 C14 1.386(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C16 C19 1.514(2) . ? C16 C18 1.516(2) . ? C16 C17 1.519(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C25 1.376(2) . ? C20 C21 1.382(2) . ? C21 C22 1.383(2) . ? C21 H21 0.9500 . ? C22 C23 1.394(2) . ? C22 H22 0.9500 . ? C23 C24 1.391(2) . ? C24 C25 1.396(2) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C27 C30 1.515(2) . ? C27 C29 1.521(2) . ? C27 C28 1.526(2) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C9 117.57(10) . . ? C15 O2 C16 121.09(11) . . ? C6 O4 C20 116.64(10) . . ? C26 O5 C27 119.72(11) . . ? C15 N3 C12 128.50(12) . . ? C15 N3 H3N 115.1(11) . . ? C12 N3 H3N 116.4(11) . . ? C26 N4 C23 126.36(12) . . ? C26 N4 H4N 117.2(11) . . ? C23 N4 H4N 116.3(11) . . ? O1 C1 C2 124.20(12) . . ? O1 C1 C6 115.51(12) . . ? C2 C1 C6 120.28(12) . . ? C1 C2 C3 119.79(12) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 120.14(12) . . ? C2 C3 C7 120.29(12) . . ? C4 C3 C7 119.55(12) . . ? C5 C4 C3 119.88(12) . . ? C5 C4 C8 120.22(12) . . ? C3 C4 C8 119.87(12) . . ? C6 C5 C4 120.00(12) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? O4 C6 C5 124.07(12) . . ? O4 C6 C1 116.15(12) . . ? C5 C6 C1 119.76(12) . . ? N1 C7 C3 176.63(15) . . ? N2 C8 C4 178.30(15) . . ? C10 C9 C14 121.20(13) . . ? C10 C9 O1 120.47(12) . . ? C14 C9 O1 118.28(13) . . ? C9 C10 C11 119.74(13) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 119.77(13) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C13 C12 C11 119.53(13) . . ? C13 C12 N3 117.10(12) . . ? C11 C12 N3 123.34(13) . . ? C14 C13 C12 120.72(13) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C9 C14 C13 119.02(13) . . ? C9 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? O3 C15 O2 126.62(13) . . ? O3 C15 N3 125.76(13) . . ? O2 C15 N3 107.62(11) . . ? O2 C16 C19 101.52(11) . . ? O2 C16 C18 109.40(11) . . ? C19 C16 C18 110.36(13) . . ? O2 C16 C17 110.32(11) . . ? C19 C16 C17 110.97(13) . . ? C18 C16 C17 113.60(13) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 121.19(13) . . ? C25 C20 O4 119.78(12) . . ? C21 C20 O4 118.98(13) . . ? C20 C21 C22 119.28(13) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C21 C22 C23 120.68(13) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C24 C23 C22 119.33(13) . . ? C24 C23 N4 123.91(13) . . ? C22 C23 N4 116.76(12) . . ? C23 C24 C25 119.93(13) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C20 C25 C24 119.59(13) . . ? C20 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? O6 C26 O5 125.76(13) . . ? O6 C26 N4 125.38(13) . . ? O5 C26 N4 108.85(12) . . ? O5 C27 C30 110.35(12) . . ? O5 C27 C29 109.68(12) . . ? C30 C27 C29 112.80(13) . . ? O5 C27 C28 102.60(12) . . ? C30 C27 C28 110.48(13) . . ? C29 C27 C28 110.46(13) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 O1 C1 C2 11.69(19) . . . . ? C9 O1 C1 C6 -169.54(12) . . . . ? O1 C1 C2 C3 -178.75(12) . . . . ? C6 C1 C2 C3 2.5(2) . . . . ? C1 C2 C3 C4 1.2(2) . . . . ? C1 C2 C3 C7 -177.10(13) . . . . ? C2 C3 C4 C5 -3.2(2) . . . . ? C7 C3 C4 C5 175.09(13) . . . . ? C2 C3 C4 C8 174.95(13) . . . . ? C7 C3 C4 C8 -6.8(2) . . . . ? C3 C4 C5 C6 1.5(2) . . . . ? C8 C4 C5 C6 -176.65(13) . . . . ? C20 O4 C6 C5 18.02(19) . . . . ? C20 O4 C6 C1 -163.74(12) . . . . ? C4 C5 C6 O4 -179.62(12) . . . . ? C4 C5 C6 C1 2.2(2) . . . . ? O1 C1 C6 O4 -1.37(18) . . . . ? C2 C1 C6 O4 177.45(12) . . . . ? O1 C1 C6 C5 176.95(12) . . . . ? C2 C1 C6 C5 -4.2(2) . . . . ? C1 O1 C9 C10 -85.17(16) . . . . ? C1 O1 C9 C14 97.33(14) . . . . ? C14 C9 C10 C11 0.0(2) . . . . ? O1 C9 C10 C11 -177.47(12) . . . . ? C9 C10 C11 C12 0.9(2) . . . . ? C10 C11 C12 C13 -0.8(2) . . . . ? C10 C11 C12 N3 -179.03(12) . . . . ? C15 N3 C12 C13 169.21(13) . . . . ? C15 N3 C12 C11 -12.5(2) . . . . ? C11 C12 C13 C14 -0.1(2) . . . . ? N3 C12 C13 C14 178.24(12) . . . . ? C10 C9 C14 C13 -0.8(2) . . . . ? O1 C9 C14 C13 176.64(11) . . . . ? C12 C13 C14 C9 0.9(2) . . . . ? C16 O2 C15 O3 -4.2(2) . . . . ? C16 O2 C15 N3 175.69(11) . . . . ? C12 N3 C15 O3 -4.5(2) . . . . ? C12 N3 C15 O2 175.63(12) . . . . ? C15 O2 C16 C19 -178.68(12) . . . . ? C15 O2 C16 C18 -62.05(16) . . . . ? C15 O2 C16 C17 63.61(16) . . . . ? C6 O4 C20 C25 -104.27(14) . . . . ? C6 O4 C20 C21 78.20(16) . . . . ? C25 C20 C21 C22 0.2(2) . . . . ? O4 C20 C21 C22 177.71(12) . . . . ? C20 C21 C22 C23 -0.8(2) . . . . ? C21 C22 C23 C24 1.0(2) . . . . ? C21 C22 C23 N4 -178.91(13) . . . . ? C26 N4 C23 C24 17.6(2) . . . . ? C26 N4 C23 C22 -162.47(13) . . . . ? C22 C23 C24 C25 -0.6(2) . . . . ? N4 C23 C24 C25 179.31(12) . . . . ? C21 C20 C25 C24 0.2(2) . . . . ? O4 C20 C25 C24 -177.29(12) . . . . ? C23 C24 C25 C20 0.0(2) . . . . ? C27 O5 C26 O6 1.1(2) . . . . ? C27 O5 C26 N4 -178.42(11) . . . . ? C23 N4 C26 O6 -4.1(2) . . . . ? C23 N4 C26 O5 175.37(12) . . . . ? C26 O5 C27 C30 -62.14(16) . . . . ? C26 O5 C27 C29 62.72(16) . . . . ? C26 O5 C27 C28 -179.86(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3N N1 0.861(18) 2.477(18) 3.2466(18) 149.3(15) 1_455 N4 H4N O3 0.876(18) 2.350(18) 3.1767(16) 157.3(15) 2_666 _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 66.60 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.29 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.040 # END OF CIF data_Ongarora6 _database_code_depnum_ccdc_archive 'CCDC 835347' #TrackingRef '6354_web_deposit_cif_file_0_M.GracaH.Vicente_ #1311007632.Ongarora6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H14 N4 O2, 2.4(C H2 Cl2)' _chemical_formula_sum 'C30.40 H18.80 Cl4.80 N4 O2' _chemical_formula_weight 642.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9371(4) _cell_length_b 10.3208(5) _cell_length_c 16.1899(7) _cell_angle_alpha 77.863(2) _cell_angle_beta 81.983(2) _cell_angle_gamma 78.622(2) _cell_volume 1423.75(11) _cell_formula_units_Z 2 _cell_measurement_temperature 90.0(5) _cell_measurement_reflns_used 8021 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 68.83 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 654 _exptl_absorpt_coefficient_mu 4.776 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.328 _exptl_absorpt_correction_T_max 0.406 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(5) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13001 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 69.38 _reflns_number_total 5068 _reflns_number_gt 4603 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker (2006) Apex-II' _computing_cell_refinement 'Bruker (2006) Apex-II ' _computing_data_reduction 'Bruker (2006) Apex-II ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0006P)^2^+4.5477P] 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 5068 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_ref 0.1451 _refine_ls_wR_factor_gt 0.1435 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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 0.5945(3) 0.1810(2) 0.34574(13) 0.0214(5) Uani 1 1 d . . . O2 O 0.9644(2) 0.2085(2) 0.33653(13) 0.0223(5) Uani 1 1 d . . . N1 N 0.2851(3) 0.4303(3) 0.29396(18) 0.0297(7) Uani 1 1 d . . . N2 N 0.3051(3) 0.4709(3) 0.04757(18) 0.0308(7) Uani 1 1 d . . . N3 N 1.2889(3) 0.0091(3) 0.25812(18) 0.0283(6) Uani 1 1 d . . . N4 N 1.2666(4) 0.1162(4) 0.0059(2) 0.0396(8) Uani 1 1 d . . . C1 C 0.4917(3) 0.2717(3) 0.21738(19) 0.0191(6) Uani 1 1 d . . . C2 C 0.4939(4) 0.2801(3) 0.1292(2) 0.0220(7) Uani 1 1 d . . . C3 C 0.5975(4) 0.1902(3) 0.0876(2) 0.0265(7) Uani 1 1 d . . . H3 H 0.5996 0.1958 0.0282 0.032 Uiso 1 1 calc R . . C4 C 0.6982(4) 0.0919(3) 0.1347(2) 0.0271(7) Uani 1 1 d . . . H4 H 0.7679 0.0288 0.1067 0.033 Uiso 1 1 calc R . . C5 C 0.7003(4) 0.0830(3) 0.2206(2) 0.0231(7) Uani 1 1 d . . . H5 H 0.7716 0.0156 0.2512 0.028 Uiso 1 1 calc R . . C6 C 0.5963(4) 0.1741(3) 0.26238(19) 0.0190(6) Uani 1 1 d . . . C7 C 0.3791(4) 0.3605(3) 0.26115(19) 0.0197(6) Uani 1 1 d . . . C8 C 0.3889(4) 0.3867(3) 0.08289(19) 0.0236(7) Uani 1 1 d . . . C9 C 0.6544(4) 0.0673(3) 0.40253(19) 0.0206(6) Uani 1 1 d . . . C10 C 0.6084(4) -0.0554(3) 0.4079(2) 0.0219(7) Uani 1 1 d . . . H10 H 0.5414 -0.0656 0.3699 0.026 Uiso 1 1 calc R . . C11 C 0.6623(4) -0.1626(3) 0.4697(2) 0.0233(7) Uani 1 1 d . . . H11 H 0.6344 -0.2479 0.4731 0.028 Uiso 1 1 calc R . . C12 C 0.7565(4) -0.1471(3) 0.5269(2) 0.0239(7) Uani 1 1 d . . . H12 H 0.7921 -0.2210 0.5695 0.029 Uiso 1 1 calc R . . C13 C 0.7986(3) -0.0226(3) 0.52160(19) 0.0206(6) Uani 1 1 d . . . H13 H 0.8624 -0.0119 0.5611 0.025 Uiso 1 1 calc R . . C14 C 0.7484(3) 0.0863(3) 0.45936(18) 0.0185(6) Uani 1 1 d . . . C15 C 0.7826(3) 0.2234(3) 0.45792(19) 0.0201(6) Uani 1 1 d . . . C16 C 0.7134(4) 0.2936(3) 0.5226(2) 0.0230(7) Uani 1 1 d . . . H16 H 0.6458 0.2534 0.5668 0.028 Uiso 1 1 calc R . . C17 C 0.7419(4) 0.4200(4) 0.5232(2) 0.0287(7) Uani 1 1 d . . . H17 H 0.6940 0.4659 0.5677 0.034 Uiso 1 1 calc R . . C18 C 0.8400(4) 0.4802(3) 0.4594(2) 0.0253(7) Uani 1 1 d . . . H18 H 0.8567 0.5685 0.4589 0.030 Uiso 1 1 calc R . . C19 C 0.9145(4) 0.4106(3) 0.3955(2) 0.0238(7) Uani 1 1 d . . . H19 H 0.9857 0.4490 0.3527 0.029 Uiso 1 1 calc R . . C20 C 0.8822(3) 0.2851(3) 0.39602(19) 0.0186(6) Uani 1 1 d . . . C21 C 0.9588(4) 0.2602(3) 0.25156(19) 0.0195(6) Uani 1 1 d . . . C22 C 1.0711(4) 0.1957(3) 0.19741(19) 0.0205(6) Uani 1 1 d . . . C23 C 1.0646(4) 0.2348(3) 0.1087(2) 0.0229(7) Uani 1 1 d . . . C24 C 0.9522(4) 0.3368(4) 0.0759(2) 0.0278(7) Uani 1 1 d . . . H24 H 0.9480 0.3625 0.0162 0.033 Uiso 1 1 calc R . . C25 C 0.8456(4) 0.4013(4) 0.1310(2) 0.0298(8) Uani 1 1 d . . . H25 H 0.7693 0.4732 0.1087 0.036 Uiso 1 1 calc R . . C26 C 0.8476(4) 0.3634(4) 0.2184(2) 0.0271(7) Uani 1 1 d . . . H26 H 0.7726 0.4084 0.2553 0.033 Uiso 1 1 calc R . . C27 C 1.1898(4) 0.0907(3) 0.2321(2) 0.0234(7) Uani 1 1 d . . . C28 C 1.1773(4) 0.1670(4) 0.0525(2) 0.0281(7) Uani 1 1 d . . . C29 C 0.5702(5) 0.7599(4) 0.1937(2) 0.0370(9) Uani 1 1 d . . . H29A H 0.6687 0.7807 0.1626 0.044 Uiso 1 1 calc R . . H29B H 0.5005 0.8460 0.1983 0.044 Uiso 1 1 calc R . . Cl1 Cl 0.48815(11) 0.66793(9) 0.13661(5) 0.0344(2) Uani 1 1 d . . . Cl2 Cl 0.60227(12) 0.66728(11) 0.29625(6) 0.0449(3) 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 0.0274(12) 0.0206(11) 0.0149(10) -0.0037(8) -0.0102(9) 0.0050(9) O2 0.0213(11) 0.0234(11) 0.0176(11) -0.0026(9) 0.0009(9) 0.0035(9) N1 0.0332(16) 0.0302(16) 0.0241(15) -0.0082(12) -0.0024(12) 0.0010(13) N2 0.0271(15) 0.0349(17) 0.0248(15) 0.0006(13) -0.0121(12) 0.0077(13) N3 0.0246(15) 0.0286(15) 0.0272(15) -0.0044(12) -0.0045(12) 0.0070(12) N4 0.0387(18) 0.052(2) 0.0284(17) -0.0157(15) -0.0014(14) -0.0018(16) C1 0.0200(15) 0.0196(15) 0.0188(15) -0.0063(12) -0.0036(12) -0.0020(12) C2 0.0195(15) 0.0272(17) 0.0183(15) -0.0036(13) -0.0058(12) 0.0001(13) C3 0.0322(18) 0.0322(18) 0.0156(15) -0.0086(13) -0.0047(13) -0.0005(14) C4 0.0289(18) 0.0283(18) 0.0240(17) -0.0113(14) -0.0031(14) 0.0025(14) C5 0.0232(16) 0.0244(16) 0.0209(16) -0.0041(13) -0.0106(13) 0.0035(13) C6 0.0252(16) 0.0195(15) 0.0139(14) -0.0042(12) -0.0061(12) -0.0034(12) C7 0.0223(16) 0.0198(15) 0.0159(14) 0.0000(12) -0.0065(12) -0.0009(13) C8 0.0243(17) 0.0327(18) 0.0152(15) -0.0069(13) -0.0027(13) -0.0050(14) C9 0.0212(16) 0.0233(16) 0.0150(15) -0.0025(12) -0.0060(12) 0.0031(12) C10 0.0220(16) 0.0229(16) 0.0222(16) -0.0067(13) -0.0065(13) -0.0017(13) C11 0.0222(16) 0.0199(16) 0.0259(17) 0.0003(13) -0.0070(13) -0.0007(13) C12 0.0240(16) 0.0204(16) 0.0236(16) 0.0022(13) -0.0050(13) 0.0001(13) C13 0.0177(15) 0.0270(17) 0.0147(14) -0.0022(12) -0.0036(12) 0.0015(12) C14 0.0153(14) 0.0266(16) 0.0136(14) -0.0048(12) -0.0010(11) -0.0028(12) C15 0.0174(15) 0.0253(16) 0.0170(15) -0.0037(12) -0.0052(12) 0.0001(12) C16 0.0236(16) 0.0285(17) 0.0165(15) -0.0054(13) -0.0015(12) -0.0027(13) C17 0.0317(18) 0.0328(19) 0.0249(17) -0.0152(15) -0.0035(14) -0.0023(15) C18 0.0264(17) 0.0206(16) 0.0310(18) -0.0071(14) -0.0101(14) -0.0013(13) C19 0.0229(16) 0.0256(17) 0.0213(16) 0.0005(13) -0.0064(13) -0.0031(13) C20 0.0176(15) 0.0201(15) 0.0166(15) -0.0053(12) -0.0034(12) 0.0035(12) C21 0.0203(15) 0.0205(15) 0.0167(15) -0.0014(12) -0.0027(12) -0.0033(12) C22 0.0219(16) 0.0202(15) 0.0189(15) -0.0051(12) -0.0023(12) -0.0007(12) C23 0.0213(16) 0.0278(17) 0.0196(16) -0.0070(13) -0.0012(12) -0.0021(13) C24 0.0304(18) 0.0332(18) 0.0180(16) -0.0002(14) -0.0057(13) -0.0040(15) C25 0.0266(18) 0.0314(18) 0.0267(18) -0.0014(14) -0.0065(14) 0.0040(14) C26 0.0267(17) 0.0314(18) 0.0221(17) -0.0060(14) -0.0034(13) -0.0002(14) C27 0.0276(17) 0.0254(17) 0.0174(15) -0.0074(13) 0.0024(13) -0.0050(14) C28 0.0258(17) 0.040(2) 0.0181(16) -0.0068(15) -0.0017(14) -0.0038(15) C29 0.042(2) 0.034(2) 0.035(2) -0.0111(16) -0.0002(17) -0.0051(17) Cl1 0.0404(5) 0.0377(5) 0.0252(4) -0.0057(3) -0.0071(3) -0.0047(4) Cl2 0.0533(6) 0.0492(6) 0.0326(5) -0.0197(4) -0.0138(4) 0.0100(5) _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 C6 1.364(4) . ? O1 C9 1.395(4) . ? O2 C21 1.371(4) . ? O2 C20 1.409(4) . ? N1 C7 1.142(4) . ? N2 C8 1.139(4) . ? N3 C27 1.154(4) . ? N4 C28 1.147(5) . ? C1 C6 1.388(4) . ? C1 C2 1.410(4) . ? C1 C7 1.438(4) . ? C2 C3 1.386(5) . ? C2 C8 1.447(4) . ? C3 C4 1.388(5) . ? C3 H3 0.9500 . ? C4 C5 1.378(5) . ? C4 H4 0.9500 . ? C5 C6 1.398(4) . ? C5 H5 0.9500 . ? C9 C10 1.389(5) . ? C9 C14 1.396(4) . ? C10 C11 1.385(4) . ? C10 H10 0.9500 . ? C11 C12 1.388(5) . ? C11 H11 0.9500 . ? C12 C13 1.390(5) . ? C12 H12 0.9500 . ? C13 C14 1.390(4) . ? C13 H13 0.9500 . ? C14 C15 1.500(4) . ? C15 C20 1.382(4) . ? C15 C16 1.402(4) . ? C16 C17 1.380(5) . ? C16 H16 0.9500 . ? C17 C18 1.384(5) . ? C17 H17 0.9500 . ? C18 C19 1.400(5) . ? C18 H18 0.9500 . ? C19 C20 1.379(5) . ? C19 H19 0.9500 . ? C21 C26 1.379(5) . ? C21 C22 1.398(4) . ? C22 C23 1.415(4) . ? C22 C27 1.439(5) . ? C23 C24 1.377(5) . ? C23 C28 1.437(5) . ? C24 C25 1.383(5) . ? C24 H24 0.9500 . ? C25 C26 1.388(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C29 Cl2 1.764(4) . ? C29 Cl1 1.768(4) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? 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 C6 O1 C9 119.6(2) . . ? C21 O2 C20 119.0(2) . . ? C6 C1 C2 119.6(3) . . ? C6 C1 C7 120.0(3) . . ? C2 C1 C7 120.4(3) . . ? C3 C2 C1 120.5(3) . . ? C3 C2 C8 120.9(3) . . ? C1 C2 C8 118.6(3) . . ? C2 C3 C4 118.6(3) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 122.0(3) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C4 C5 C6 119.2(3) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? O1 C6 C1 115.4(3) . . ? O1 C6 C5 124.4(3) . . ? C1 C6 C5 120.0(3) . . ? N1 C7 C1 177.1(3) . . ? N2 C8 C2 179.0(4) . . ? C10 C9 O1 120.9(3) . . ? C10 C9 C14 121.9(3) . . ? O1 C9 C14 116.8(3) . . ? C11 C10 C9 118.6(3) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? C10 C11 C12 120.8(3) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C13 119.6(3) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 120.9(3) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C9 118.1(3) . . ? C13 C14 C15 121.0(3) . . ? C9 C14 C15 120.7(3) . . ? C20 C15 C16 117.2(3) . . ? C20 C15 C14 123.3(3) . . ? C16 C15 C14 119.6(3) . . ? C17 C16 C15 121.1(3) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C18 120.3(3) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C19 119.8(3) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C20 C19 C18 118.5(3) . . ? C20 C19 H19 120.7 . . ? C18 C19 H19 120.7 . . ? C19 C20 C15 123.0(3) . . ? C19 C20 O2 119.7(3) . . ? C15 C20 O2 117.0(3) . . ? O2 C21 C26 124.3(3) . . ? O2 C21 C22 115.4(3) . . ? C26 C21 C22 120.2(3) . . ? C21 C22 C23 118.8(3) . . ? C21 C22 C27 120.1(3) . . ? C23 C22 C27 121.1(3) . . ? C24 C23 C22 120.8(3) . . ? C24 C23 C28 120.0(3) . . ? C22 C23 C28 119.2(3) . . ? C23 C24 C25 119.0(3) . . ? C23 C24 H24 120.5 . . ? C25 C24 H24 120.5 . . ? C24 C25 C26 121.4(3) . . ? C24 C25 H25 119.3 . . ? C26 C25 H25 119.3 . . ? C21 C26 C25 119.8(3) . . ? C21 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? N3 C27 C22 177.5(4) . . ? N4 C28 C23 178.0(4) . . ? Cl2 C29 Cl1 110.8(2) . . ? Cl2 C29 H29A 109.5 . . ? Cl1 C29 H29A 109.5 . . ? Cl2 C29 H29B 109.5 . . ? Cl1 C29 H29B 109.5 . . ? H29A C29 H29B 108.1 . . ? 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 C1 C2 C3 1.3(5) . . . . ? C7 C1 C2 C3 -176.8(3) . . . . ? C6 C1 C2 C8 -177.0(3) . . . . ? C7 C1 C2 C8 4.9(5) . . . . ? C1 C2 C3 C4 0.2(5) . . . . ? C8 C2 C3 C4 178.5(3) . . . . ? C2 C3 C4 C5 -1.4(5) . . . . ? C3 C4 C5 C6 1.1(5) . . . . ? C9 O1 C6 C1 158.8(3) . . . . ? C9 O1 C6 C5 -25.3(4) . . . . ? C2 C1 C6 O1 174.5(3) . . . . ? C7 C1 C6 O1 -7.4(4) . . . . ? C2 C1 C6 C5 -1.6(5) . . . . ? C7 C1 C6 C5 176.5(3) . . . . ? C4 C5 C6 O1 -175.3(3) . . . . ? C4 C5 C6 C1 0.5(5) . . . . ? C6 O1 C9 C10 -51.2(4) . . . . ? C6 O1 C9 C14 135.6(3) . . . . ? O1 C9 C10 C11 -175.1(3) . . . . ? C14 C9 C10 C11 -2.3(5) . . . . ? C9 C10 C11 C12 1.9(5) . . . . ? C10 C11 C12 C13 -0.6(5) . . . . ? C11 C12 C13 C14 -0.5(5) . . . . ? C12 C13 C14 C9 0.2(4) . . . . ? C12 C13 C14 C15 174.8(3) . . . . ? C10 C9 C14 C13 1.2(5) . . . . ? O1 C9 C14 C13 174.4(3) . . . . ? C10 C9 C14 C15 -173.4(3) . . . . ? O1 C9 C14 C15 -0.3(4) . . . . ? C13 C14 C15 C20 110.9(4) . . . . ? C9 C14 C15 C20 -74.5(4) . . . . ? C13 C14 C15 C16 -68.0(4) . . . . ? C9 C14 C15 C16 106.5(3) . . . . ? C20 C15 C16 C17 1.2(5) . . . . ? C14 C15 C16 C17 -179.8(3) . . . . ? C15 C16 C17 C18 0.1(5) . . . . ? C16 C17 C18 C19 -2.1(5) . . . . ? C17 C18 C19 C20 2.9(5) . . . . ? C18 C19 C20 C15 -1.7(5) . . . . ? C18 C19 C20 O2 -175.0(3) . . . . ? C16 C15 C20 C19 -0.4(5) . . . . ? C14 C15 C20 C19 -179.3(3) . . . . ? C16 C15 C20 O2 173.2(3) . . . . ? C14 C15 C20 O2 -5.8(4) . . . . ? C21 O2 C20 C19 -59.4(4) . . . . ? C21 O2 C20 C15 126.8(3) . . . . ? C20 O2 C21 C26 -19.0(4) . . . . ? C20 O2 C21 C22 164.6(3) . . . . ? O2 C21 C22 C23 174.2(3) . . . . ? C26 C21 C22 C23 -2.4(5) . . . . ? O2 C21 C22 C27 -5.3(4) . . . . ? C26 C21 C22 C27 178.2(3) . . . . ? C21 C22 C23 C24 1.6(5) . . . . ? C27 C22 C23 C24 -178.9(3) . . . . ? C21 C22 C23 C28 -178.6(3) . . . . ? C27 C22 C23 C28 0.8(5) . . . . ? C22 C23 C24 C25 0.3(5) . . . . ? C28 C23 C24 C25 -179.5(3) . . . . ? C23 C24 C25 C26 -1.5(6) . . . . ? O2 C21 C26 C25 -175.0(3) . . . . ? C22 C21 C26 C25 1.3(5) . . . . ? C24 C25 C26 C21 0.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 66.6 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.639 _refine_diff_density_min -0.409 _refine_diff_density_rms 0.072 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 1.000 236 117 ' ' _platon_squeeze_details ; The contribution from 117 electrons removed by SQUEEZE amounts to approximately 2.8 molecules per DCM per cell (1.4 per main molecule). These are included in the formula, calculated density, etc., but are not present in the model. ; # END OF CIF