# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jack Harrowfield' _publ_contact_author_email harrowfield@isis.u-strasbg.fr loop_ _publ_author_name J.Harrowfield K.Rissanen 'Xiao Cao' L.Russo L.Brelot J.-M.Lehn data_cao2 _database_code_depnum_ccdc_archive 'CCDC 799323' #TrackingRef 'cao2.cif' _audit_update_record ; 2010-09-01 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H34 N2 O9' _chemical_formula_sum 'C25 H34 N2 O9' _chemical_formula_weight 506.54 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1761(3) _cell_length_b 11.7881(7) _cell_length_c 11.8683(7) _cell_angle_alpha 103.977(2) _cell_angle_beta 97.401(3) _cell_angle_gamma 94.414(3) _cell_volume 1227.58(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5771 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 0.104 _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 173(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 KappaCCD _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 11839 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_sigmaI/netI 0.0825 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5615 _reflns_number_gt 3129 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0908P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.019(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5615 _refine_ls_number_parameters 338 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1154 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1717 _refine_ls_wR_factor_gt 0.1226 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7218(2) 0.3404(2) 0.1620(2) 0.0315(6) Uani 1 1 d . . . C2 C 0.7932(2) 0.3393(2) 0.2717(2) 0.0391(6) Uani 1 1 d . . . H2 H 0.7623 0.2806 0.3088 0.047 Uiso 1 1 calc R . . C3 C 0.9107(3) 0.4247(2) 0.3274(2) 0.0472(7) Uani 1 1 d . . . H3 H 0.9607 0.4236 0.4023 0.057 Uiso 1 1 calc R . . C4 C 0.9545(3) 0.5104(2) 0.2747(2) 0.0478(7) Uani 1 1 d . . . H4 H 1.0349 0.5682 0.3131 0.057 Uiso 1 1 calc R . . C5 C 0.8813(2) 0.5128(2) 0.1649(2) 0.0412(6) Uani 1 1 d . . . H5 H 0.9111 0.5730 0.1291 0.049 Uiso 1 1 calc R . . C6 C 0.7654(2) 0.4278(2) 0.1078(2) 0.0317(6) Uani 1 1 d . . . C7 C 0.7188(2) 0.5189(2) -0.0503(2) 0.0359(6) Uani 1 1 d . . . H7A H 0.8190 0.5167 -0.0726 0.043 Uiso 1 1 calc R . . H7B H 0.7166 0.5947 0.0075 0.043 Uiso 1 1 calc R . . C8 C 0.6074(3) 0.5090(2) -0.1562(2) 0.0379(6) Uani 1 1 d . . . H8A H 0.5068 0.4944 -0.1373 0.046 Uiso 1 1 calc R . . H8B H 0.6141 0.5838 -0.1802 0.046 Uiso 1 1 calc R . . C9 C 0.5325(3) 0.4097(2) -0.3542(2) 0.0396(6) Uani 1 1 d . . . H9A H 0.5326 0.4883 -0.3702 0.048 Uiso 1 1 calc R . . H9B H 0.4308 0.3827 -0.3451 0.048 Uiso 1 1 calc R . . C10 C 0.5828(2) 0.3246(2) -0.4532(2) 0.0438(7) Uani 1 1 d . . . H10A H 0.6825 0.3543 -0.4642 0.053 Uiso 1 1 calc R . . H10B H 0.5891 0.2478 -0.4340 0.053 Uiso 1 1 calc R . . C11 C 0.3607(2) 0.2220(2) -0.5742(2) 0.0418(6) Uani 1 1 d . . . H11A H 0.3434 0.2083 -0.4976 0.050 Uiso 1 1 calc R . . H11B H 0.3800 0.1469 -0.6258 0.050 Uiso 1 1 calc R . . C12 C 0.2296(2) 0.2682(2) -0.6296(2) 0.0386(6) Uani 1 1 d . . . H12A H 0.1936 0.3283 -0.5689 0.046 Uiso 1 1 calc R . . H12B H 0.2600 0.3067 -0.6897 0.046 Uiso 1 1 calc R . . C13 C 0.0116(2) 0.1433(2) -0.6183(2) 0.0316(5) Uani 1 1 d . . . C14 C -0.1015(2) 0.05651(19) -0.68271(19) 0.0301(5) Uani 1 1 d . . . H14 H -0.1022 0.0239 -0.7642 0.036 Uiso 1 1 calc R . . C15 C -0.2122(2) 0.01852(19) -0.62734(19) 0.0275(5) Uani 1 1 d . . . C16 C -0.2126(2) 0.06523(19) -0.50756(19) 0.0285(5) Uani 1 1 d . . . H16 H -0.2908 0.0415 -0.4702 0.034 Uiso 1 1 calc R . . C17 C -0.0960(2) 0.14714(19) -0.44440(19) 0.0277(5) Uani 1 1 d . . . C18 C 0.0154(2) 0.1880(2) -0.49972(19) 0.0304(5) Uani 1 1 d . . . H18 H 0.0928 0.2460 -0.4557 0.037 Uiso 1 1 calc R . . C19 C -0.1828(2) 0.1524(2) -0.26117(19) 0.0314(5) Uani 1 1 d . . . H19A H -0.1853 0.0659 -0.2752 0.038 Uiso 1 1 calc R . . H19B H -0.2832 0.1710 -0.2868 0.038 Uiso 1 1 calc R . . C20 C -0.1344(2) 0.2106(2) -0.13358(19) 0.0331(6) Uani 1 1 d . . . H20A H -0.1212 0.2971 -0.1212 0.040 Uiso 1 1 calc R . . H20B H -0.2104 0.1906 -0.0873 0.040 Uiso 1 1 calc R . . C21 C 0.0348(2) 0.1866(2) 0.02709(18) 0.0343(6) Uani 1 1 d . . . H21A H -0.0546 0.1629 0.0582 0.041 Uiso 1 1 calc R . . H21B H 0.0680 0.2705 0.0660 0.041 Uiso 1 1 calc R . . C22 C 0.1558(2) 0.1116(2) 0.0510(2) 0.0340(6) Uani 1 1 d . . . H22A H 0.1349 0.0745 0.1146 0.041 Uiso 1 1 calc R . . H22B H 0.1584 0.0482 -0.0204 0.041 Uiso 1 1 calc R . . C23 C 0.4109(2) 0.1089(2) 0.0887(2) 0.0391(6) Uani 1 1 d . . . H23A H 0.4297 0.0741 0.0079 0.047 Uiso 1 1 calc R . . H23B H 0.3812 0.0438 0.1233 0.047 Uiso 1 1 calc R . . C24 C 0.5490(2) 0.1786(2) 0.1605(2) 0.0360(6) Uani 1 1 d . . . H24A H 0.5276 0.2221 0.2379 0.043 Uiso 1 1 calc R . . H24B H 0.6238 0.1252 0.1738 0.043 Uiso 1 1 calc R . . C25 C -0.3358(2) -0.0731(2) -0.69436(19) 0.0300(5) Uani 1 1 d . . . N1 N -0.2998(2) -0.15467(18) -0.78348(18) 0.0372(5) Uani 1 1 d . . . N2 N -0.3990(2) -0.25509(18) -0.8457(2) 0.0379(5) Uani 1 1 d . . . O1 O 0.68573(15) 0.42329(14) 0.00077(13) 0.0337(4) Uani 1 1 d . . . O2 O 0.63221(16) 0.41550(14) -0.25011(13) 0.0371(4) Uani 1 1 d . . . O3 O 0.48231(17) 0.30996(16) -0.55848(14) 0.0455(5) Uani 1 1 d . . . O4 O 0.11189(17) 0.17657(16) -0.68345(14) 0.0462(5) Uani 1 1 d . . . O5 O -0.07902(15) 0.19565(14) -0.32537(12) 0.0333(4) Uani 1 1 d . . . O6 O 0.00214(15) 0.17050(15) -0.09613(13) 0.0384(4) Uani 1 1 d . . . O7 O 0.29498(15) 0.18145(13) 0.08459(14) 0.0363(4) Uani 1 1 d . . . O8 O 0.60474(15) 0.25945(13) 0.09978(13) 0.0333(4) Uani 1 1 d . . . O9 O -0.46075(16) -0.07404(16) -0.66970(15) 0.0485(5) Uani 1 1 d . . . H2N H -0.473(3) -0.266(3) -0.794(3) 0.073(10) Uiso 1 1 d . . . H1N H -0.218(3) -0.162(2) -0.788(2) 0.042(8) Uiso 1 1 d . . . H3N H -0.447(3) -0.239(3) -0.911(3) 0.065(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0262(11) 0.0299(13) 0.0360(13) 0.0040(11) 0.0037(10) 0.0040(9) C2 0.0379(13) 0.0356(15) 0.0409(15) 0.0081(12) -0.0016(11) 0.0041(11) C3 0.0419(14) 0.0444(17) 0.0470(16) 0.0048(14) -0.0107(12) 0.0044(12) C4 0.0369(13) 0.0400(16) 0.0554(18) -0.0011(14) -0.0043(12) -0.0032(11) C5 0.0346(13) 0.0366(15) 0.0494(16) 0.0067(12) 0.0058(12) 0.0005(11) C6 0.0276(11) 0.0321(14) 0.0320(13) 0.0010(11) 0.0043(10) 0.0055(9) C7 0.0426(13) 0.0262(13) 0.0385(14) 0.0037(11) 0.0142(11) 0.0031(10) C8 0.0485(14) 0.0270(14) 0.0401(14) 0.0075(11) 0.0123(11) 0.0093(11) C9 0.0419(13) 0.0393(15) 0.0395(14) 0.0135(12) 0.0041(11) 0.0077(11) C10 0.0339(12) 0.0608(18) 0.0341(14) 0.0091(13) 0.0005(11) 0.0058(12) C11 0.0397(13) 0.0426(16) 0.0406(15) 0.0101(12) 0.0042(11) -0.0051(11) C12 0.0349(12) 0.0455(16) 0.0338(13) 0.0098(12) 0.0068(10) -0.0075(11) C13 0.0279(11) 0.0349(14) 0.0316(13) 0.0081(11) 0.0042(10) 0.0019(10) C14 0.0308(11) 0.0331(14) 0.0248(12) 0.0051(10) 0.0021(9) 0.0036(10) C15 0.0249(11) 0.0257(12) 0.0306(12) 0.0062(10) 0.0001(9) 0.0054(9) C16 0.0268(11) 0.0289(13) 0.0305(12) 0.0085(10) 0.0052(9) 0.0032(9) C17 0.0272(11) 0.0286(13) 0.0272(12) 0.0064(10) 0.0026(9) 0.0065(9) C18 0.0288(11) 0.0288(13) 0.0303(12) 0.0030(10) 0.0031(9) -0.0003(9) C19 0.0252(11) 0.0385(14) 0.0312(13) 0.0095(11) 0.0054(9) 0.0026(9) C20 0.0240(11) 0.0403(15) 0.0345(13) 0.0076(11) 0.0054(10) 0.0055(10) C21 0.0353(12) 0.0395(15) 0.0226(12) 0.0005(10) 0.0024(10) -0.0025(10) C22 0.0326(12) 0.0330(14) 0.0319(13) 0.0048(11) 0.0004(10) -0.0050(10) C23 0.0367(12) 0.0312(14) 0.0506(16) 0.0124(12) 0.0068(11) 0.0047(10) C24 0.0362(12) 0.0338(14) 0.0400(14) 0.0140(11) 0.0045(11) 0.0029(10) C25 0.0289(11) 0.0312(13) 0.0279(12) 0.0066(10) 0.0005(9) 0.0013(9) N1 0.0278(11) 0.0370(13) 0.0396(12) -0.0022(10) 0.0046(9) -0.0021(9) N2 0.0397(11) 0.0330(12) 0.0345(12) 0.0018(10) 0.0002(10) -0.0040(9) O1 0.0356(8) 0.0306(9) 0.0336(9) 0.0075(7) 0.0056(7) -0.0018(7) O2 0.0407(9) 0.0383(10) 0.0310(9) 0.0049(8) 0.0045(7) 0.0106(7) O3 0.0363(9) 0.0588(13) 0.0394(10) 0.0177(9) -0.0018(8) -0.0103(8) O4 0.0384(9) 0.0607(13) 0.0322(9) 0.0035(9) 0.0079(7) -0.0176(8) O5 0.0337(8) 0.0369(10) 0.0255(8) 0.0025(7) 0.0056(7) -0.0038(7) O6 0.0287(8) 0.0591(12) 0.0264(9) 0.0072(8) 0.0041(7) 0.0102(7) O7 0.0292(8) 0.0285(9) 0.0479(10) 0.0055(8) 0.0040(7) -0.0001(7) O8 0.0307(8) 0.0337(10) 0.0323(9) 0.0067(7) 0.0002(7) -0.0027(7) O9 0.0303(9) 0.0520(12) 0.0505(11) -0.0092(9) 0.0103(8) -0.0082(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 C1 O8 1.381(2) . ? C1 C2 1.383(3) . ? C1 C6 1.399(3) . ? C2 C3 1.393(3) . ? C2 H2 0.9500 . ? C3 C4 1.371(4) . ? C3 H3 0.9500 . ? C4 C5 1.396(3) . ? C4 H4 0.9500 . ? C5 C6 1.384(3) . ? C5 H5 0.9500 . ? C6 O1 1.369(3) . ? C7 O1 1.434(3) . ? C7 C8 1.489(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O2 1.421(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O2 1.423(3) . ? C9 C10 1.497(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O3 1.420(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O3 1.425(3) . ? C11 C12 1.499(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O4 1.432(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O4 1.368(3) . ? C13 C18 1.373(3) . ? C13 C14 1.401(3) . ? C14 C15 1.381(3) . ? C14 H14 0.9500 . ? C15 C16 1.396(3) . ? C15 C25 1.500(3) . ? C16 C17 1.387(3) . ? C16 H16 0.9500 . ? C17 O5 1.373(3) . ? C17 C18 1.399(3) . ? C18 H18 0.9500 . ? C19 O5 1.431(3) . ? C19 C20 1.496(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O6 1.428(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 O6 1.417(3) . ? C21 C22 1.513(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 O7 1.420(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 O7 1.419(3) . ? C23 C24 1.493(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 O8 1.429(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 O9 1.220(3) . ? C25 N1 1.341(3) . ? N1 N2 1.419(3) . ? N1 H1N 0.77(2) . ? N2 H2N 0.99(3) . ? N2 H3N 0.91(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O8 C1 C2 123.9(2) . . ? O8 C1 C6 115.71(19) . . ? C2 C1 C6 120.4(2) . . ? C1 C2 C3 119.7(2) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 120.3(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.2(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 120.1(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? O1 C6 C5 124.6(2) . . ? O1 C6 C1 116.09(18) . . ? C5 C6 C1 119.3(2) . . ? O1 C7 C8 109.29(18) . . ? O1 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? O1 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? O2 C8 C7 110.37(18) . . ? O2 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? O2 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? O2 C9 C10 107.67(17) . . ? O2 C9 H9A 110.2 . . ? C10 C9 H9A 110.2 . . ? O2 C9 H9B 110.2 . . ? C10 C9 H9B 110.2 . . ? H9A C9 H9B 108.5 . . ? O3 C10 C9 110.20(18) . . ? O3 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? O3 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? O3 C11 C12 106.0(2) . . ? O3 C11 H11A 110.5 . . ? C12 C11 H11A 110.5 . . ? O3 C11 H11B 110.5 . . ? C12 C11 H11B 110.5 . . ? H11A C11 H11B 108.7 . . ? O4 C12 C11 111.8(2) . . ? O4 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? O4 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? O4 C13 C18 125.3(2) . . ? O4 C13 C14 114.45(19) . . ? C18 C13 C14 120.2(2) . . ? C15 C14 C13 119.8(2) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.80(19) . . ? C14 C15 C25 121.0(2) . . ? C16 C15 C25 118.2(2) . . ? C17 C16 C15 118.4(2) . . ? C17 C16 H16 120.8 . . ? C15 C16 H16 120.8 . . ? O5 C17 C16 124.4(2) . . ? O5 C17 C18 114.27(18) . . ? C16 C17 C18 121.3(2) . . ? C13 C18 C17 119.3(2) . . ? C13 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? O5 C19 C20 107.70(17) . . ? O5 C19 H19A 110.2 . . ? C20 C19 H19A 110.2 . . ? O5 C19 H19B 110.2 . . ? C20 C19 H19B 110.2 . . ? H19A C19 H19B 108.5 . . ? O6 C20 C19 108.70(17) . . ? O6 C20 H20A 109.9 . . ? C19 C20 H20A 109.9 . . ? O6 C20 H20B 109.9 . . ? C19 C20 H20B 109.9 . . ? H20A C20 H20B 108.3 . . ? O6 C21 C22 108.02(18) . . ? O6 C21 H21A 110.1 . . ? C22 C21 H21A 110.1 . . ? O6 C21 H21B 110.1 . . ? C22 C21 H21B 110.1 . . ? H21A C21 H21B 108.4 . . ? O7 C22 C21 110.28(19) . . ? O7 C22 H22A 109.6 . . ? C21 C22 H22A 109.6 . . ? O7 C22 H22B 109.6 . . ? C21 C22 H22B 109.6 . . ? H22A C22 H22B 108.1 . . ? O7 C23 C24 110.56(19) . . ? O7 C23 H23A 109.5 . . ? C24 C23 H23A 109.5 . . ? O7 C23 H23B 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? O8 C24 C23 109.16(19) . . ? O8 C24 H24A 109.8 . . ? C23 C24 H24A 109.8 . . ? O8 C24 H24B 109.8 . . ? C23 C24 H24B 109.8 . . ? H24A C24 H24B 108.3 . . ? O9 C25 N1 121.9(2) . . ? O9 C25 C15 122.5(2) . . ? N1 C25 C15 115.55(19) . . ? C25 N1 N2 122.2(2) . . ? C25 N1 H1N 120.1(19) . . ? N2 N1 H1N 114(2) . . ? N1 N2 H2N 106.7(17) . . ? N1 N2 H3N 108.1(19) . . ? H2N N2 H3N 108(2) . . ? C6 O1 C7 116.77(17) . . ? C8 O2 C9 111.03(16) . . ? C10 O3 C11 114.23(19) . . ? C13 O4 C12 120.26(17) . . ? C17 O5 C19 117.62(16) . . ? C21 O6 C20 113.94(16) . . ? C23 O7 C22 110.35(17) . . ? C1 O8 C24 115.76(17) . . ? 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 O8 C1 C2 C3 179.8(2) . . . . ? C6 C1 C2 C3 -1.0(3) . . . . ? C1 C2 C3 C4 0.7(4) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C3 C4 C5 C6 -0.8(4) . . . . ? C4 C5 C6 O1 179.3(2) . . . . ? C4 C5 C6 C1 0.6(3) . . . . ? O8 C1 C6 O1 0.8(3) . . . . ? C2 C1 C6 O1 -178.45(18) . . . . ? O8 C1 C6 C5 179.58(18) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? O1 C7 C8 O2 -73.2(2) . . . . ? O2 C9 C10 O3 176.6(2) . . . . ? O3 C11 C12 O4 161.83(18) . . . . ? O4 C13 C14 C15 -177.86(19) . . . . ? C18 C13 C14 C15 2.0(3) . . . . ? C13 C14 C15 C16 -0.2(3) . . . . ? C13 C14 C15 C25 179.19(19) . . . . ? C14 C15 C16 C17 -2.6(3) . . . . ? C25 C15 C16 C17 177.93(18) . . . . ? C15 C16 C17 O5 -176.70(19) . . . . ? C15 C16 C17 C18 3.8(3) . . . . ? O4 C13 C18 C17 179.0(2) . . . . ? C14 C13 C18 C17 -0.9(3) . . . . ? O5 C17 C18 C13 178.39(19) . . . . ? C16 C17 C18 C13 -2.1(3) . . . . ? O5 C19 C20 O6 -66.9(2) . . . . ? O6 C21 C22 O7 99.7(2) . . . . ? O7 C23 C24 O8 -68.8(3) . . . . ? C14 C15 C25 O9 -147.2(2) . . . . ? C16 C15 C25 O9 32.2(3) . . . . ? C14 C15 C25 N1 33.0(3) . . . . ? C16 C15 C25 N1 -147.6(2) . . . . ? O9 C25 N1 N2 -7.9(4) . . . . ? C15 C25 N1 N2 172.0(2) . . . . ? C5 C6 O1 C7 -5.0(3) . . . . ? C1 C6 O1 C7 173.73(18) . . . . ? C8 C7 O1 C6 -171.38(17) . . . . ? C7 C8 O2 C9 -176.3(2) . . . . ? C10 C9 O2 C8 170.0(2) . . . . ? C9 C10 O3 C11 -86.7(3) . . . . ? C12 C11 O3 C10 142.7(2) . . . . ? C18 C13 O4 C12 -2.6(3) . . . . ? C14 C13 O4 C12 177.24(19) . . . . ? C11 C12 O4 C13 85.8(3) . . . . ? C16 C17 O5 C19 4.7(3) . . . . ? C18 C17 O5 C19 -175.74(18) . . . . ? C20 C19 O5 C17 175.29(17) . . . . ? C22 C21 O6 C20 164.37(18) . . . . ? C19 C20 O6 C21 -160.06(19) . . . . ? C24 C23 O7 C22 -161.0(2) . . . . ? C21 C22 O7 C23 -170.63(19) . . . . ? C2 C1 O8 C24 6.2(3) . . . . ? C6 C1 O8 C24 -172.98(19) . . . . ? C23 C24 O8 C1 172.11(17) . . . . ? 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 N2 H2N O2 0.99(3) 2.40(3) 3.238(3) 142(2) 2_554 N1 H1N O6 0.77(2) 2.55(3) 3.239(3) 151(2) 2_554 N2 H3N O8 0.91(3) 2.46(3) 3.332(3) 162(3) 2_554 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.319 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.076 # Attachment 'cao3.cif' data_cao3 _database_code_depnum_ccdc_archive 'CCDC 799324' #TrackingRef 'cao3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H26 N2 O7, 2(C H Cl3)' _chemical_formula_sum 'C19 H28 Cl6 N2 O7' _chemical_formula_weight 609.13 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' Cl Cl 0.1484 0.1585 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1087(6) _cell_length_b 10.8879(4) _cell_length_c 14.3670(10) _cell_angle_alpha 98.432(3) _cell_angle_beta 94.188(3) _cell_angle_gamma 116.888(3) _cell_volume 1377.56(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10317 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.664 _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 173(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 KappaCCD _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 14265 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0724 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 27.53 _reflns_number_total 6290 _reflns_number_gt 3729 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1174P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6290 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1152 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.2061 _refine_ls_wR_factor_gt 0.1637 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0081(3) 0.3566(3) 1.1073(2) 0.0302(7) Uani 1 1 d . . . H1A H 0.0979 0.4354 1.1486 0.036 Uiso 1 1 calc R . . H1B H -0.0242 0.2733 1.1372 0.036 Uiso 1 1 calc R . . C2 C -0.1162(3) 0.3954(3) 1.0955(2) 0.0295(7) Uani 1 1 d . . . H2A H -0.1364 0.4268 1.1587 0.035 Uiso 1 1 calc R . . H2B H -0.0876 0.4730 1.0602 0.035 Uiso 1 1 calc R . . C3 C -0.3850(3) 0.2757(3) 1.0513(3) 0.0341(7) Uani 1 1 d . . . H3A H -0.3878 0.3053 1.1194 0.041 Uiso 1 1 calc R . . H3B H -0.4681 0.1789 1.0290 0.041 Uiso 1 1 calc R . . C4 C -0.4125(3) 0.3714(3) 0.9958(2) 0.0336(7) Uani 1 1 d . . . H4A H -0.5082 0.3707 1.0072 0.040 Uiso 1 1 calc R . . H4B H -0.3304 0.4689 1.0171 0.040 Uiso 1 1 calc R . . C5 C -0.4553(4) 0.4041(3) 0.8397(3) 0.0337(7) Uani 1 1 d . . . H5A H -0.3827 0.5052 0.8602 0.040 Uiso 1 1 calc R . . H5B H -0.5571 0.3920 0.8460 0.040 Uiso 1 1 calc R . . C6 C -0.4495(3) 0.3531(3) 0.7380(3) 0.0378(8) Uani 1 1 d . . . H6A H -0.5139 0.2501 0.7197 0.045 Uiso 1 1 calc R . . H6B H -0.4874 0.3981 0.6956 0.045 Uiso 1 1 calc R . . C7 C -0.2865(4) 0.3308(4) 0.6354(3) 0.0412(8) Uani 1 1 d . . . H7A H -0.3221 0.3698 0.5870 0.049 Uiso 1 1 calc R . . H7B H -0.3488 0.2273 0.6208 0.049 Uiso 1 1 calc R . . C8 C -0.1236(4) 0.3688(3) 0.6325(3) 0.0386(8) Uani 1 1 d . . . H8A H -0.1089 0.3454 0.5661 0.046 Uiso 1 1 calc R . . H8B H -0.0594 0.4709 0.6568 0.046 Uiso 1 1 calc R . . C9 C 0.0620(4) 0.3072(3) 0.6853(2) 0.0346(7) Uani 1 1 d . . . H9A H 0.1376 0.4066 0.7099 0.042 Uiso 1 1 calc R . . H9B H 0.0717 0.2808 0.6182 0.042 Uiso 1 1 calc R . . C10 C 0.0897(4) 0.2153(3) 0.7435(2) 0.0336(7) Uani 1 1 d . . . H10A H 0.0095 0.1169 0.7226 0.040 Uiso 1 1 calc R . . H10B H 0.1872 0.2180 0.7349 0.040 Uiso 1 1 calc R . . C11 C 0.1297(3) 0.2033(3) 0.9071(2) 0.0248(6) Uani 1 1 d . . . C12 C 0.1860(3) 0.1091(3) 0.8878(2) 0.0273(7) Uani 1 1 d . . . H12 H 0.1970 0.0809 0.8243 0.033 Uiso 1 1 calc R . . C13 C 0.2266(3) 0.0556(3) 0.9605(2) 0.0274(7) Uani 1 1 d . . . H13 H 0.2627 -0.0107 0.9462 0.033 Uiso 1 1 calc R . . C14 C 0.2149(3) 0.0983(3) 1.0533(2) 0.0257(7) Uani 1 1 d . . . C15 C 0.1582(3) 0.1930(3) 1.0737(2) 0.0249(6) Uani 1 1 d . . . H15 H 0.1524 0.2245 1.1378 0.030 Uiso 1 1 calc R . . C16 C 0.1103(3) 0.2412(3) 1.0012(2) 0.0239(6) Uani 1 1 d . . . C17 C 0.2633(3) 0.0526(3) 1.1371(2) 0.0273(7) Uani 1 1 d . . . C18 C 0.4094(4) 0.8509(3) 0.6763(2) 0.0349(7) Uani 1 1 d . . . H18 H 0.5180 0.9013 0.7050 0.042 Uiso 1 1 calc R . . C19 C 0.7880(4) 0.7908(4) 0.5948(3) 0.0474(9) Uani 1 1 d . . . H19 H 0.7420 0.8014 0.6528 0.057 Uiso 1 1 calc R . . N1 N 0.2687(3) -0.0687(3) 1.1185(2) 0.0311(6) Uani 1 1 d . . . N2 N 0.3135(4) -0.1199(3) 1.1929(2) 0.0341(7) Uani 1 1 d . . . O1 O 0.0431(2) 0.3258(2) 1.01396(16) 0.0289(5) Uani 1 1 d . . . O2 O -0.2464(2) 0.27348(19) 1.04380(16) 0.0292(5) Uani 1 1 d . . . O3 O -0.4191(2) 0.3252(2) 0.89764(17) 0.0348(5) Uani 1 1 d . . . O4 O -0.2998(2) 0.3875(2) 0.72844(16) 0.0363(5) Uani 1 1 d . . . O5 O -0.0837(2) 0.2916(2) 0.69019(17) 0.0383(6) Uani 1 1 d . . . O6 O 0.0912(2) 0.2656(2) 0.84143(16) 0.0313(5) Uani 1 1 d . . . O7 O 0.2949(3) 0.1230(3) 1.21836(18) 0.0485(7) Uani 1 1 d . . . Cl1 Cl 0.35769(15) 0.67343(10) 0.63359(9) 0.0720(4) Uani 1 1 d . . . Cl2 Cl 0.30305(12) 0.86556(11) 0.76406(8) 0.0588(3) Uani 1 1 d . . . Cl3 Cl 0.38262(12) 0.92790(10) 0.58265(7) 0.0592(3) Uani 1 1 d . . . Cl4 Cl 0.67560(13) 0.62508(11) 0.52526(11) 0.0834(4) Uani 1 1 d . . . Cl5 Cl 0.96840(13) 0.81537(13) 0.63038(11) 0.0832(4) Uani 1 1 d . . . Cl6 Cl 0.79695(18) 0.91783(14) 0.52970(13) 0.1015(5) Uani 1 1 d . . . H2N H 0.345(4) -0.180(4) 1.166(3) 0.052(11) Uiso 1 1 d . . . H3N H 0.250(4) -0.159(4) 1.215(3) 0.044(13) Uiso 1 1 d . . . H1N H 0.239(4) -0.113(4) 1.074(3) 0.034(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0327(16) 0.0330(15) 0.0236(18) -0.0018(13) 0.0033(13) 0.0167(13) C2 0.0316(15) 0.0267(14) 0.0292(18) 0.0001(13) 0.0036(14) 0.0146(12) C3 0.0278(16) 0.0429(17) 0.033(2) 0.0079(15) 0.0057(14) 0.0177(14) C4 0.0331(16) 0.0380(16) 0.034(2) 0.0043(14) 0.0061(14) 0.0210(14) C5 0.0315(16) 0.0363(16) 0.036(2) 0.0064(14) 0.0008(14) 0.0187(13) C6 0.0346(17) 0.0415(17) 0.035(2) 0.0067(15) -0.0033(15) 0.0177(14) C7 0.049(2) 0.054(2) 0.0249(19) 0.0055(16) 0.0011(16) 0.0299(17) C8 0.0496(19) 0.0446(18) 0.028(2) 0.0122(15) 0.0049(16) 0.0263(16) C9 0.0418(18) 0.0416(17) 0.0262(19) 0.0095(14) 0.0093(15) 0.0232(15) C10 0.0401(17) 0.0388(16) 0.0270(19) 0.0053(14) 0.0054(14) 0.0230(14) C11 0.0230(14) 0.0239(14) 0.0254(17) 0.0061(12) 0.0034(12) 0.0089(11) C12 0.0314(15) 0.0283(14) 0.0222(17) 0.0011(12) 0.0042(13) 0.0151(12) C13 0.0279(15) 0.0241(14) 0.0309(19) 0.0035(13) 0.0035(13) 0.0135(12) C14 0.0217(14) 0.0234(14) 0.0284(18) 0.0029(12) 0.0000(12) 0.0088(11) C15 0.0238(14) 0.0253(13) 0.0220(17) -0.0003(12) 0.0023(12) 0.0103(11) C16 0.0228(14) 0.0190(13) 0.0298(18) 0.0035(12) 0.0055(12) 0.0097(11) C17 0.0271(15) 0.0296(15) 0.0259(18) 0.0027(13) 0.0037(13) 0.0148(12) C18 0.0395(17) 0.0395(17) 0.0279(19) 0.0058(14) 0.0046(14) 0.0207(14) C19 0.051(2) 0.048(2) 0.044(2) -0.0014(17) 0.0036(18) 0.0269(17) N1 0.0387(15) 0.0281(14) 0.0250(17) 0.0020(13) -0.0041(13) 0.0166(12) N2 0.0404(17) 0.0357(15) 0.0328(18) 0.0116(13) 0.0055(14) 0.0222(14) O1 0.0353(11) 0.0319(11) 0.0276(13) 0.0079(9) 0.0078(9) 0.0216(9) O2 0.0257(10) 0.0320(10) 0.0301(13) 0.0005(9) 0.0008(9) 0.0159(8) O3 0.0429(12) 0.0361(11) 0.0314(14) 0.0056(10) 0.0029(10) 0.0243(10) O4 0.0354(12) 0.0443(12) 0.0268(13) 0.0010(10) 0.0007(10) 0.0190(10) O5 0.0396(12) 0.0485(13) 0.0364(15) 0.0201(11) 0.0105(11) 0.0250(10) O6 0.0442(12) 0.0332(11) 0.0242(12) 0.0078(9) 0.0066(10) 0.0237(10) O7 0.0776(17) 0.0563(14) 0.0273(15) -0.0048(12) -0.0042(13) 0.0506(13) Cl1 0.1089(9) 0.0456(6) 0.0616(8) 0.0017(5) 0.0109(7) 0.0393(6) Cl2 0.0704(7) 0.0810(7) 0.0448(6) 0.0195(5) 0.0279(5) 0.0475(6) Cl3 0.0769(7) 0.0528(6) 0.0345(6) 0.0176(4) 0.0015(5) 0.0174(5) Cl4 0.0716(8) 0.0548(6) 0.0925(11) -0.0121(6) 0.0097(7) 0.0113(5) Cl5 0.0638(7) 0.0905(8) 0.0923(11) -0.0089(7) -0.0142(7) 0.0454(6) Cl6 0.1199(12) 0.0773(8) 0.1099(14) 0.0353(8) -0.0061(10) 0.0472(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 C1 O1 1.442(4) . ? C1 C2 1.503(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O2 1.427(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O2 1.424(3) . ? C3 C4 1.508(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O3 1.412(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O3 1.419(4) . ? C5 C6 1.499(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 O4 1.408(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O4 1.431(4) . ? C7 C8 1.510(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O5 1.420(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O5 1.413(4) . ? C9 C10 1.497(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O6 1.430(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O6 1.369(4) . ? C11 C12 1.385(4) . ? C11 C16 1.410(4) . ? C12 C13 1.390(4) . ? C12 H12 0.9500 . ? C13 C14 1.377(4) . ? C13 H13 0.9500 . ? C14 C15 1.397(4) . ? C14 C17 1.499(4) . ? C15 C16 1.382(4) . ? C15 H15 0.9500 . ? C16 O1 1.370(3) . ? C17 O7 1.231(4) . ? C17 N1 1.335(4) . ? C18 Cl2 1.750(3) . ? C18 Cl3 1.752(3) . ? C18 Cl1 1.754(3) . ? C18 H18 1.0000 . ? C19 Cl4 1.731(4) . ? C19 Cl5 1.744(4) . ? C19 Cl6 1.753(4) . ? C19 H19 1.0000 . ? N1 N2 1.411(4) . ? N1 H1N 0.70(4) . ? N2 H2N 0.91(4) . ? N2 H3N 0.72(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 107.8(3) . . ? O1 C1 H1A 110.2 . . ? C2 C1 H1A 110.2 . . ? O1 C1 H1B 110.2 . . ? C2 C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? O2 C2 C1 107.5(2) . . ? O2 C2 H2A 110.2 . . ? C1 C2 H2A 110.2 . . ? O2 C2 H2B 110.2 . . ? C1 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? O2 C3 C4 114.7(3) . . ? O2 C3 H3A 108.6 . . ? C4 C3 H3A 108.6 . . ? O2 C3 H3B 108.6 . . ? C4 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? O3 C4 C3 109.5(2) . . ? O3 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? O3 C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.2 . . ? O3 C5 C6 108.8(3) . . ? O3 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? O3 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? O4 C6 C5 108.9(3) . . ? O4 C6 H6A 109.9 . . ? C5 C6 H6A 109.9 . . ? O4 C6 H6B 109.9 . . ? C5 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? O4 C7 C8 108.8(3) . . ? O4 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? O4 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? O5 C8 C7 108.4(3) . . ? O5 C8 H8A 110.0 . . ? C7 C8 H8A 110.0 . . ? O5 C8 H8B 110.0 . . ? C7 C8 H8B 110.0 . . ? H8A C8 H8B 108.4 . . ? O5 C9 C10 109.6(3) . . ? O5 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? O5 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? O6 C10 C9 108.5(2) . . ? O6 C10 H10A 110.0 . . ? C9 C10 H10A 110.0 . . ? O6 C10 H10B 110.0 . . ? C9 C10 H10B 110.0 . . ? H10A C10 H10B 108.4 . . ? O6 C11 C12 125.2(3) . . ? O6 C11 C16 115.8(2) . . ? C12 C11 C16 119.0(3) . . ? C11 C12 C13 120.6(3) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 120.3(3) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 119.6(3) . . ? C13 C14 C17 124.3(3) . . ? C15 C14 C17 116.0(3) . . ? C16 C15 C14 120.4(3) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? O1 C16 C15 124.2(3) . . ? O1 C16 C11 115.9(3) . . ? C15 C16 C11 119.8(2) . . ? O7 C17 N1 122.2(3) . . ? O7 C17 C14 121.5(3) . . ? N1 C17 C14 116.3(3) . . ? Cl2 C18 Cl3 109.99(18) . . ? Cl2 C18 Cl1 110.04(18) . . ? Cl3 C18 Cl1 110.18(19) . . ? Cl2 C18 H18 108.9 . . ? Cl3 C18 H18 108.9 . . ? Cl1 C18 H18 108.9 . . ? Cl4 C19 Cl5 111.1(2) . . ? Cl4 C19 Cl6 109.2(2) . . ? Cl5 C19 Cl6 109.9(2) . . ? Cl4 C19 H19 108.9 . . ? Cl5 C19 H19 108.9 . . ? Cl6 C19 H19 108.9 . . ? C17 N1 N2 120.3(3) . . ? C17 N1 H1N 121(3) . . ? N2 N1 H1N 118(3) . . ? N1 N2 H2N 107(3) . . ? N1 N2 H3N 110(3) . . ? H2N N2 H3N 108(4) . . ? C16 O1 C1 117.9(2) . . ? C3 O2 C2 115.2(2) . . ? C4 O3 C5 113.0(2) . . ? C6 O4 C7 112.4(2) . . ? C9 O5 C8 113.7(2) . . ? C11 O6 C10 117.2(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 O1 C1 C2 O2 65.7(3) . . . . ? O2 C3 C4 O3 62.2(3) . . . . ? O3 C5 C6 O4 -67.0(3) . . . . ? O4 C7 C8 O5 69.6(3) . . . . ? O5 C9 C10 O6 -65.6(3) . . . . ? O6 C11 C12 C13 177.7(3) . . . . ? C16 C11 C12 C13 -1.7(4) . . . . ? C11 C12 C13 C14 -1.6(4) . . . . ? C12 C13 C14 C15 1.7(4) . . . . ? C12 C13 C14 C17 -176.7(3) . . . . ? C13 C14 C15 C16 1.6(4) . . . . ? C17 C14 C15 C16 -179.9(2) . . . . ? C14 C15 C16 O1 175.0(2) . . . . ? C14 C15 C16 C11 -5.0(4) . . . . ? O6 C11 C16 O1 5.5(3) . . . . ? C12 C11 C16 O1 -175.0(2) . . . . ? O6 C11 C16 C15 -174.5(2) . . . . ? C12 C11 C16 C15 5.0(4) . . . . ? C13 C14 C17 O7 157.0(3) . . . . ? C15 C14 C17 O7 -21.4(4) . . . . ? C13 C14 C17 N1 -23.6(4) . . . . ? C15 C14 C17 N1 158.0(3) . . . . ? O7 C17 N1 N2 -0.8(5) . . . . ? C14 C17 N1 N2 179.8(3) . . . . ? C15 C16 O1 C1 -5.7(4) . . . . ? C11 C16 O1 C1 174.3(2) . . . . ? C2 C1 O1 C16 -156.7(2) . . . . ? C4 C3 O2 C2 74.0(4) . . . . ? C1 C2 O2 C3 161.1(3) . . . . ? C3 C4 O3 C5 175.8(2) . . . . ? C6 C5 O3 C4 176.3(2) . . . . ? C5 C6 O4 C7 174.5(3) . . . . ? C8 C7 O4 C6 -178.3(3) . . . . ? C10 C9 O5 C8 -176.5(3) . . . . ? C7 C8 O5 C9 173.8(3) . . . . ? C12 C11 O6 C10 9.0(4) . . . . ? C16 C11 O6 C10 -171.6(2) . . . . ? C9 C10 O6 C11 -173.8(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 N2 H2N O3 0.91(4) 2.15(4) 3.056(4) 179(4) 2_557 N2 H3N O5 0.72(4) 2.34(4) 3.045(4) 167(4) 2_557 N1 H1N O2 0.70(4) 2.28(4) 2.899(4) 150(4) 2_557 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.575 _refine_diff_density_min -0.668 _refine_diff_density_rms 0.098 data_jmh001 _database_code_depnum_ccdc_archive 'CCDC 799325' #TrackingRef 'jmhKR.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H33 Cl3 N4 O4' _chemical_formula_weight 403.77 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' Cl Cl 0.1484 0.1585 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7106(2) _cell_length_b 19.4586(4) _cell_length_c 11.0090(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.8270(10) _cell_angle_gamma 90.00 _cell_volume 1902.90(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.505 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8236 _exptl_absorpt_correction_T_max 0.9058 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13031 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.42 _reflns_number_total 4316 _reflns_number_gt 3709 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0163P)^2^+2.0439P] 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 4316 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0807 _refine_ls_wR_factor_gt 0.0757 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.61678(19) -0.04378(9) -0.28055(17) 0.0153(3) Uani 1 1 d . . . H1 H 0.6074 0.0048 -0.3126 0.018 Uiso 1 1 calc R . . C2 C 0.78137(19) -0.05618(9) -0.18671(17) 0.0161(4) Uani 1 1 d . . . H2A H 0.8075 -0.0258 -0.1084 0.019 Uiso 1 1 calc R . . H2B H 0.7927 -0.1043 -0.1550 0.019 Uiso 1 1 calc R . . N3 N 0.88917(16) -0.04328(8) -0.24970(14) 0.0156(3) Uani 1 1 d . . . H3A H 0.8707 -0.0750 -0.3164 0.019 Uiso 1 1 calc R . . H3B H 0.9849 -0.0513 -0.1871 0.019 Uiso 1 1 calc R . . C4 C 0.8865(2) 0.02656(9) -0.30702(17) 0.0167(4) Uani 1 1 d . . . H4A H 0.7856 0.0349 -0.3782 0.020 Uiso 1 1 calc R . . H4B H 0.9607 0.0280 -0.3477 0.020 Uiso 1 1 calc R . . C5 C 0.9225(2) 0.08361(9) -0.20380(18) 0.0188(4) Uani 1 1 d . . . H5A H 1.0258 0.0771 -0.1351 0.023 Uiso 1 1 calc R . . H5B H 0.8517 0.0810 -0.1598 0.023 Uiso 1 1 calc R . . C6 C 0.9106(2) 0.15434(10) -0.26722(19) 0.0202(4) Uani 1 1 d . . . H6A H 0.9735 0.1872 -0.1986 0.024 Uiso 1 1 calc R . . H6B H 0.9516 0.1517 -0.3361 0.024 Uiso 1 1 calc R . . N7 N 0.75242(17) 0.18132(8) -0.32928(15) 0.0179(3) Uani 1 1 d . . . H7A H 0.7462 0.2136 -0.3923 0.021 Uiso 1 1 calc R . . H7B H 0.6884 0.1458 -0.3716 0.021 Uiso 1 1 calc R . . C8 C 0.7018(2) 0.21303(10) -0.23079(18) 0.0207(4) Uani 1 1 d . . . H8A H 0.7669 0.2530 -0.1890 0.025 Uiso 1 1 calc R . . H8B H 0.7141 0.1792 -0.1601 0.025 Uiso 1 1 calc R . . C9 C 0.5395(2) 0.23650(10) -0.29233(19) 0.0213(4) Uani 1 1 d . . . H9A H 0.5222 0.2686 -0.2301 0.026 Uiso 1 1 calc R . . H9B H 0.5230 0.2624 -0.3745 0.026 Uiso 1 1 calc R . . N10 N 0.42532(18) 0.17994(8) -0.32586(15) 0.0200(3) Uani 1 1 d . . . H10A H 0.4303 0.1542 -0.3941 0.024 Uiso 1 1 calc R . . H10B H 0.3308 0.1991 -0.3556 0.024 Uiso 1 1 calc R . . C11 C 0.4466(2) 0.13307(10) -0.21074(19) 0.0244(4) Uani 1 1 d . . . H11A H 0.4584 0.1612 -0.1322 0.029 Uiso 1 1 calc R . . H11B H 0.5400 0.1061 -0.1886 0.029 Uiso 1 1 calc R . . C12 C 0.3152(2) 0.08433(10) -0.2411(2) 0.0236(4) Uani 1 1 d . . . H12A H 0.2211 0.1115 -0.2768 0.028 Uiso 1 1 calc R . . H12B H 0.3228 0.0634 -0.1566 0.028 Uiso 1 1 calc R . . C13 C 0.3021(2) 0.02657(9) -0.33878(18) 0.0193(4) Uani 1 1 d . . . H13A H 0.1951 0.0217 -0.4006 0.023 Uiso 1 1 calc R . . H13B H 0.3594 0.0396 -0.3919 0.023 Uiso 1 1 calc R . . N14 N 0.35806(16) -0.04149(8) -0.27497(15) 0.0162(3) Uani 1 1 d . . . H14A H 0.3266 -0.0743 -0.3408 0.019 Uiso 1 1 calc R . . H14B H 0.3108 -0.0507 -0.2192 0.019 Uiso 1 1 calc R . . C15 C 0.5234(2) -0.05121(10) -0.19712(17) 0.0176(4) Uani 1 1 d . . . H15A H 0.5408 -0.0975 -0.1563 0.021 Uiso 1 1 calc R . . H15B H 0.5590 -0.0170 -0.1243 0.021 Uiso 1 1 calc R . . C16 C 0.5634(2) -0.09141(9) -0.40294(17) 0.0164(4) Uani 1 1 d . . . O17 O 0.42783(14) -0.08491(7) -0.48467(12) 0.0219(3) Uani 1 1 d . . . O18 O 0.65668(15) -0.13093(7) -0.41801(13) 0.0240(3) Uani 1 1 d . . . O19 O 0.18057(19) 0.30913(9) -0.21939(16) 0.0331(4) Uani 1 1 d . . . H19A H 0.272(3) 0.3257(15) -0.189(3) 0.050 Uiso 1 1 d . . . H19B H 0.187(3) 0.2761(15) -0.160(3) 0.050 Uiso 1 1 d . . . O20 O 0.16090(18) 0.24720(9) -0.45059(16) 0.0322(4) Uiso 1 1 d . . . H20A H 0.148(3) 0.2668(14) -0.390(3) 0.048 Uiso 1 1 d . . . H20B H 0.090(3) 0.2141(14) -0.481(3) 0.048 Uiso 1 1 d . . . Cl21 Cl 0.77450(5) 0.06697(3) 0.06076(4) 0.02158(11) Uani 1 1 d . . . Cl22 Cl -0.02107(5) 0.11268(2) -0.56057(4) 0.02294(11) Uani 1 1 d . . . Cl23 Cl 0.25510(6) 0.19666(2) 0.00042(5) 0.02555(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0143(8) 0.0168(8) 0.0151(8) -0.0001(7) 0.0061(7) -0.0004(7) C2 0.0140(8) 0.0204(9) 0.0141(8) 0.0003(7) 0.0060(7) -0.0015(7) N3 0.0132(7) 0.0177(7) 0.0146(7) -0.0001(6) 0.0044(6) 0.0018(6) C4 0.0159(8) 0.0185(9) 0.0157(8) 0.0011(7) 0.0064(7) -0.0001(7) C5 0.0203(9) 0.0204(9) 0.0158(8) 0.0001(7) 0.0073(7) 0.0001(7) C6 0.0182(9) 0.0203(9) 0.0219(9) -0.0015(7) 0.0080(8) -0.0021(7) N7 0.0198(8) 0.0170(8) 0.0171(7) -0.0005(6) 0.0077(6) -0.0024(6) C8 0.0214(9) 0.0212(9) 0.0202(9) -0.0050(7) 0.0092(8) -0.0024(7) C9 0.0245(10) 0.0160(9) 0.0247(10) -0.0023(8) 0.0112(8) -0.0010(7) N10 0.0216(8) 0.0195(8) 0.0201(8) -0.0029(6) 0.0097(7) -0.0007(6) C11 0.0288(10) 0.0245(10) 0.0180(9) -0.0012(8) 0.0075(8) -0.0027(8) C12 0.0272(10) 0.0226(10) 0.0244(10) -0.0009(8) 0.0138(8) 0.0003(8) C13 0.0218(9) 0.0181(9) 0.0186(9) 0.0014(7) 0.0086(7) 0.0016(7) N14 0.0142(7) 0.0184(8) 0.0169(7) -0.0009(6) 0.0072(6) -0.0004(6) C15 0.0153(9) 0.0209(9) 0.0152(8) 0.0022(7) 0.0047(7) 0.0000(7) C16 0.0184(9) 0.0171(9) 0.0145(8) 0.0009(7) 0.0073(7) -0.0031(7) O17 0.0158(6) 0.0274(7) 0.0175(6) -0.0046(6) 0.0013(5) 0.0004(5) O18 0.0204(7) 0.0277(8) 0.0233(7) -0.0072(6) 0.0083(6) 0.0032(6) O19 0.0327(9) 0.0293(8) 0.0313(8) 0.0045(7) 0.0066(7) -0.0054(7) Cl21 0.0170(2) 0.0315(3) 0.0156(2) 0.00012(18) 0.00592(17) 0.00215(18) Cl22 0.0234(2) 0.0252(2) 0.0206(2) -0.00276(18) 0.00935(18) 0.00161(18) Cl23 0.0342(3) 0.0197(2) 0.0220(2) -0.00053(18) 0.0106(2) 0.00037(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.532(2) . ? C1 C15 1.536(2) . ? C1 C16 1.542(2) . ? C2 N3 1.492(2) . ? N3 C4 1.494(2) . ? C4 C5 1.525(2) . ? C5 C6 1.526(3) . ? C6 N7 1.501(2) . ? N7 C8 1.493(2) . ? C8 C9 1.513(3) . ? C9 N10 1.499(2) . ? N10 C11 1.506(2) . ? C11 C12 1.514(3) . ? C12 C13 1.525(3) . ? C13 N14 1.495(2) . ? N14 C15 1.495(2) . ? C16 O18 1.249(2) . ? C16 O17 1.266(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C15 106.82(14) . . ? C2 C1 C16 112.65(15) . . ? C15 C1 C16 113.25(14) . . ? N3 C2 C1 113.39(14) . . ? C2 N3 C4 116.99(14) . . ? N3 C4 C5 112.82(14) . . ? C4 C5 C6 111.31(15) . . ? N7 C6 C5 113.46(15) . . ? C8 N7 C6 112.99(14) . . ? N7 C8 C9 112.87(15) . . ? N10 C9 C8 114.95(16) . . ? C9 N10 C11 113.65(15) . . ? N10 C11 C12 112.12(16) . . ? C11 C12 C13 116.14(17) . . ? N14 C13 C12 114.25(15) . . ? C13 N14 C15 118.95(14) . . ? N14 C15 C1 113.70(14) . . ? O18 C16 O17 124.67(17) . . ? O18 C16 C1 118.72(15) . . ? O17 C16 C1 116.53(16) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.391 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.059