# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 loop_ _publ_author_address ; Centro de Qu\'imica Instituto Venezolano de Investigaciones Cient\'ifica (IVIC) Apartado 21827 Caracas 1020-A Venezuela ; _publ_contact_author_name 'Briceno, Alexander' _publ_contact_author_email abriceno@ivic.ve _publ_section_title ; Solid state synthesis of head-to-tail photodimers from supramolecular assemblies directed by charge assisted hydrogen bonds ; _publ_contact_author_address ; Centro de Qu\'imica Instituto Venezolano de Investigaciones Cient\'ifica (IVIC) Apartado 21827 Caracas 1020-A Venezuela ; _publ_contact_author_fax '(58-212) 504-1350' _publ_contact_author_phone '(58-212) 504-1320' #========================================================================== #========================================================================== # SUBMISSION DETAILS _publ_contact_letter ; Date of submission: 2008-08-20 Please consider this CIF submission for publication in Inorganica Chimica Acta. All authors have seen and approved this submission. The CIF has passed the Chester CHECKCIF routines and gives a satisfactory PRINTCIF file. Best wishes, Dr. Alexander Brice\~no ; _publ_requested_category ? _publ_requested_coeditor_name ? _publ_author_name A.Briceno data_shelxle _database_code_depnum_ccdc_archive 'CCDC 742518' #TrackingRef 'compound1cif.txt' #========================================================================== _audit_creation_method SHELXL-97 _audit_creation_date '20 August 2008' #========================================================================== _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H11 N2, 0.5(C10 H4 O8) ' _chemical_formula_sum 'C17 H13 N2 O4' _chemical_formula_weight 309.29 _chemical_compound_source Synthesis loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.838(2) _cell_length_b 13.7249(17) _cell_length_c 13.4162(17) _cell_angle_alpha 90.00 _cell_angle_beta 94.828(2) _cell_angle_gamma 90.00 _cell_volume 2906.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1202 _cell_measurement_theta_min 2.00 _cell_measurement_theta_max 28.00 _exptl_crystal_description Prism _exptl_crystal_colour Brown _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type 'Multi Scan' _exptl_absorpt_correction_T_min 0.960 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method '\w ' _diffrn_radiation_detector CCD _diffrn_measurement_device 'Mercury (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16416 _diffrn_reflns_av_R_equivalents 0.0706 _diffrn_reflns_av_sigmaI/netI 0.0603 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 28.13 _reflns_number_total 2928 _reflns_number_gt 1671 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _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^)+(0.1152P)^2^+2.5296P] 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 2928 _refine_ls_number_parameters 287 _refine_ls_number_restraints 450 _refine_ls_R_factor_all 0.1440 _refine_ls_R_factor_gt 0.0810 _refine_ls_wR_factor_ref 0.2438 _refine_ls_wR_factor_gt 0.2077 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.006 _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 0.22934(18) 0.57337(17) 0.69950(17) 0.0686(8) Uani 1 1 d . . . C1 C 0.1937(2) 0.5856(2) 0.6140(2) 0.0436(8) Uani 1 1 d . . . O2 O 0.13230(17) 0.53809(19) 0.5757(2) 0.0779(9) Uani 1 1 d . . . C2 C 0.22517(17) 0.6688(2) 0.5536(2) 0.0364(7) Uani 1 1 d . . . O3 O 0.2721(2) 0.49233(18) 0.43574(19) 0.0814(10) Uani 1 1 d . . . C3 C 0.23914(17) 0.65949(19) 0.4524(2) 0.0354(7) Uani 1 1 d . . . O4 O 0.19508(16) 0.56507(16) 0.31231(16) 0.0634(7) Uani 1 1 d . . . H40H H 0.1982 0.5038 0.2703 0.076 Uiso 1 1 d R . . C4 C 0.23631(19) 0.5629(2) 0.4003(2) 0.0418(7) Uani 1 1 d . . . C5 C 0.23652(18) 0.7590(2) 0.5996(2) 0.0375(7) Uani 1 1 d . . . H5A H 0.2276 0.7650 0.6669 0.045 Uiso 1 1 calc R . . C6 C -0.0316(6) 0.0819(6) 0.6303(6) 0.063(2) Uani 0.541(10) 1 d PU A 1 H6A H -0.0897 0.0817 0.6360 0.075 Uiso 0.541(10) 1 calc PR A 1 C7 C 0.0056(6) -0.0055(6) 0.6248(6) 0.059(2) Uani 0.541(10) 1 d PU A 1 H7A H 0.0635 -0.0049 0.6175 0.070 Uiso 0.541(10) 1 calc PR A 1 C8 C 0.0089(5) 0.1774(4) 0.6285(8) 0.052(2) Uani 0.541(10) 1 d PGU A 1 C9 C -0.0386(3) 0.2626(6) 0.6207(10) 0.057(2) Uani 0.541(10) 1 d PGU A 1 H9A H -0.0974 0.2596 0.6189 0.068 Uiso 0.541(10) 1 calc PR A 1 C10 C 0.0017(5) 0.3522(4) 0.6157(11) 0.054(2) Uani 0.541(10) 1 d PGU A 1 H10A H -0.0301 0.4092 0.6105 0.065 Uiso 0.541(10) 1 calc PR A 1 N1 N 0.0895(5) 0.3566(5) 0.6185(11) 0.053(2) Uani 0.541(10) 1 d PGU A 1 H1A H 0.1145 0.4120 0.6153 0.064 Uiso 0.541(10) 1 calc PR A 1 C11 C 0.1371(3) 0.2714(7) 0.6263(10) 0.056(2) Uani 0.541(10) 1 d PGU A 1 H11A H 0.1958 0.2743 0.6281 0.068 Uiso 0.541(10) 1 calc PR A 1 C12 C 0.0967(5) 0.1818(5) 0.6313(8) 0.059(2) Uani 0.541(10) 1 d PGU A 1 H12A H 0.1285 0.1248 0.6365 0.071 Uiso 0.541(10) 1 calc PR A 1 C13 C -0.0342(5) -0.1021(5) 0.6288(11) 0.055(2) Uani 0.541(10) 1 d PGU A 1 C14 C -0.1201(5) -0.1046(5) 0.6435(13) 0.067(3) Uani 0.541(10) 1 d PGU A 1 H14A H -0.1498 -0.0468 0.6498 0.081 Uiso 0.541(10) 1 calc PR A 1 N2 N -0.1614(4) -0.1936(7) 0.6486(13) 0.072(2) Uani 0.541(10) 1 d PGU A 1 C15 C -0.1170(5) -0.2799(5) 0.6391(11) 0.064(2) Uani 0.541(10) 1 d PGU A 1 H15A H -0.1447 -0.3394 0.6426 0.077 Uiso 0.541(10) 1 calc PR A 1 C16 C -0.0312(5) -0.2774(5) 0.6245(10) 0.059(2) Uani 0.541(10) 1 d PGU A 1 H16A H -0.0015 -0.3352 0.6182 0.071 Uiso 0.541(10) 1 calc PR A 1 C17 C 0.0102(4) -0.1885(7) 0.6193(10) 0.057(2) Uani 0.541(10) 1 d PGU A 1 H17A H 0.0676 -0.1868 0.6095 0.068 Uiso 0.541(10) 1 calc PR A 1 C6A C 0.0282(7) 0.0657(7) 0.6243(8) 0.073(3) Uani 0.459(10) 1 d PU A 2 H6AA H 0.0765 0.0271 0.6253 0.087 Uiso 0.459(10) 1 calc PR A 2 C7A C -0.0426(9) 0.0203(8) 0.6215(8) 0.069(2) Uani 0.459(10) 1 d PU A 2 H7AA H -0.0908 0.0593 0.6152 0.083 Uiso 0.459(10) 1 calc PR A 2 C8A C 0.0417(7) 0.1673(5) 0.6261(10) 0.059(3) Uani 0.459(10) 1 d PGU A 2 C9A C -0.0266(5) 0.2311(8) 0.6225(12) 0.063(3) Uani 0.459(10) 1 d PGU A 2 H9AA H -0.0813 0.2071 0.6248 0.076 Uiso 0.459(10) 1 calc PR A 2 C10A C -0.0132(6) 0.3309(7) 0.6155(14) 0.064(3) Uani 0.459(10) 1 d PGU A 2 H10B H -0.0589 0.3736 0.6131 0.077 Uiso 0.459(10) 1 calc PR A 2 N1A N 0.0685(7) 0.3669(5) 0.6120(14) 0.054(3) Uani 0.459(10) 1 d PGU A 2 H1AA H 0.0768 0.4286 0.6077 0.064 Uiso 0.459(10) 1 calc PR A 2 C11A C 0.1369(5) 0.3031(7) 0.6156(12) 0.056(3) Uani 0.459(10) 1 d PGU A 2 H11B H 0.1916 0.3271 0.6133 0.067 Uiso 0.459(10) 1 calc PR A 2 C12A C 0.1235(5) 0.2033(6) 0.6226(10) 0.055(3) Uani 0.459(10) 1 d PGU A 2 H12B H 0.1692 0.1606 0.6250 0.065 Uiso 0.459(10) 1 calc PR A 2 C13A C -0.0582(7) -0.0870(5) 0.6271(14) 0.060(3) Uani 0.459(10) 1 d PGU A 2 C14A C -0.1393(6) -0.1207(7) 0.6405(15) 0.063(3) Uani 0.459(10) 1 d PGU A 2 H14B H -0.1834 -0.0766 0.6453 0.075 Uiso 0.459(10) 1 calc PR A 2 N2A N -0.1544(5) -0.2202(8) 0.6468(15) 0.072(3) Uani 0.459(10) 1 d PGU A 2 C15A C -0.0885(7) -0.2860(5) 0.6396(13) 0.065(3) Uani 0.459(10) 1 d PGU A 2 H15B H -0.0986 -0.3525 0.6438 0.078 Uiso 0.459(10) 1 calc PR A 2 C16A C -0.0074(6) -0.2523(7) 0.6261(12) 0.061(3) Uani 0.459(10) 1 d PGU A 2 H16B H 0.0367 -0.2963 0.6213 0.074 Uiso 0.459(10) 1 calc PR A 2 C17A C 0.0077(5) -0.1528(8) 0.6199(13) 0.064(3) Uani 0.459(10) 1 d PGU A 2 H17B H 0.0619 -0.1303 0.6109 0.077 Uiso 0.459(10) 1 calc PR A 2 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 0.109(2) 0.0503(15) 0.0457(14) 0.0177(11) 0.0015(13) -0.0126(13) C1 0.0570(19) 0.0298(16) 0.0455(19) -0.0001(14) 0.0132(15) 0.0016(14) O2 0.091(2) 0.0616(17) 0.0795(18) 0.0203(14) -0.0026(15) -0.0341(15) C2 0.0418(16) 0.0295(15) 0.0385(16) 0.0047(13) 0.0064(12) 0.0016(12) O3 0.131(2) 0.0399(15) 0.0681(18) -0.0099(12) -0.0227(16) 0.0308(15) C3 0.0451(16) 0.0264(15) 0.0348(16) 0.0003(12) 0.0040(12) 0.0035(12) O4 0.1025(19) 0.0420(14) 0.0428(13) -0.0117(10) -0.0113(12) 0.0109(12) C4 0.0565(18) 0.0300(17) 0.0397(17) -0.0001(13) 0.0081(14) 0.0017(14) C5 0.0516(17) 0.0325(16) 0.0287(14) 0.0017(12) 0.0053(12) 0.0025(12) C6 0.057(4) 0.044(4) 0.088(5) 0.007(4) 0.008(4) -0.004(3) C7 0.049(4) 0.054(4) 0.073(4) 0.005(4) 0.005(4) 0.001(3) C8 0.039(5) 0.044(4) 0.070(4) 0.011(4) -0.002(4) 0.008(3) C9 0.061(4) 0.025(4) 0.084(5) 0.019(5) 0.001(4) -0.003(3) C10 0.041(4) 0.039(4) 0.082(5) 0.011(4) 0.005(4) -0.017(3) N1 0.044(4) 0.047(4) 0.068(4) 0.006(4) 0.001(4) -0.005(3) C11 0.045(4) 0.054(6) 0.070(5) 0.003(6) 0.004(3) 0.002(3) C12 0.049(5) 0.050(4) 0.078(5) 0.007(5) 0.013(5) 0.000(4) C13 0.052(5) 0.054(4) 0.059(4) 0.003(4) 0.009(5) 0.002(3) C14 0.050(4) 0.061(5) 0.093(5) 0.000(5) 0.014(5) -0.005(4) N2 0.069(4) 0.046(5) 0.102(5) 0.005(5) 0.013(4) 0.005(3) C15 0.047(5) 0.053(4) 0.094(5) 0.012(4) 0.013(5) 0.019(3) C16 0.049(5) 0.052(4) 0.077(5) 0.002(5) 0.008(5) -0.015(4) C17 0.061(4) 0.040(5) 0.071(4) 0.001(6) 0.014(4) -0.004(3) C6A 0.065(5) 0.045(4) 0.108(6) 0.001(4) 0.003(5) 0.006(4) C7A 0.075(6) 0.051(5) 0.080(5) 0.014(5) -0.001(5) 0.002(4) C8A 0.044(6) 0.046(4) 0.087(5) 0.001(4) 0.001(6) 0.010(4) C9A 0.051(5) 0.044(6) 0.093(6) 0.012(7) -0.005(5) 0.008(4) C10A 0.051(5) 0.049(5) 0.092(6) 0.003(6) 0.005(5) -0.004(5) N1A 0.048(5) 0.040(4) 0.072(5) -0.005(4) -0.002(5) 0.004(3) C11A 0.063(5) 0.023(5) 0.082(6) 0.004(5) -0.001(4) 0.012(3) C12A 0.054(5) 0.032(4) 0.077(6) 0.000(5) 0.000(5) -0.010(4) C13A 0.056(6) 0.057(4) 0.065(5) 0.007(4) 0.005(6) 0.002(4) C14A 0.073(5) 0.035(4) 0.081(6) 0.006(5) 0.008(6) -0.020(4) N2A 0.068(5) 0.050(5) 0.098(6) 0.010(6) 0.013(5) -0.004(4) C15A 0.052(7) 0.052(5) 0.092(6) 0.003(5) 0.009(7) -0.014(4) C16A 0.059(6) 0.046(5) 0.080(5) 0.001(6) 0.012(6) -0.016(5) C17A 0.070(5) 0.044(6) 0.080(6) 0.004(7) 0.011(5) -0.005(4) _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 1.247(4) . ? C1 O2 1.246(4) . ? C1 C2 1.508(4) . ? C2 C5 1.389(4) . ? C2 C3 1.399(4) . ? O3 C4 1.200(3) . ? C3 C5 1.390(4) 7_566 ? C3 C4 1.498(4) . ? O4 C4 1.301(3) . ? O4 H40H 1.0157 . ? C5 C3 1.390(4) 7_566 ? C5 H5A 0.9300 . ? C6 C7 1.341(14) . ? C6 C8 1.460(9) . ? C6 H6A 0.9300 . ? C7 C13 1.472(10) . ? C7 H7A 0.9300 . ? C8 C9 1.3900 . ? C8 C12 1.3900 . ? C9 C10 1.3900 . ? C9 H9A 0.9300 . ? C10 N1 1.3900 . ? C10 H10A 0.9300 . ? N1 C11 1.3900 . ? N1 H1A 0.8600 . ? C11 C12 1.3900 . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.3900 . ? C13 C17 1.3900 . ? C14 N2 1.3900 . ? C14 H14A 0.9300 . ? N2 C15 1.3900 . ? C15 C16 1.3900 . ? C15 H15A 0.9300 . ? C16 C17 1.3900 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C6A C7A 1.282(19) . ? C6A C8A 1.411(11) . ? C6A H6AA 0.9300 . ? C7A C13A 1.496(13) . ? C7A H7AA 0.9300 . ? C8A C9A 1.3900 . ? C8A C12A 1.3900 . ? C9A C10A 1.3900 . ? C9A H9AA 0.9300 . ? C10A N1A 1.3900 . ? C10A H10B 0.9300 . ? N1A C11A 1.3900 . ? N1A H1AA 0.8600 . ? C11A C12A 1.3900 . ? C11A H11B 0.9300 . ? C12A H12B 0.9300 . ? C13A C14A 1.3900 . ? C13A C17A 1.3900 . ? C14A N2A 1.3900 . ? C14A H14B 0.9300 . ? N2A C15A 1.3900 . ? C15A C16A 1.3900 . ? C15A H15B 0.9300 . ? C16A C17A 1.3900 . ? C16A H16B 0.9300 . ? C17A H17B 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 125.9(3) . . ? O2 C1 C2 117.2(3) . . ? O1 C1 C2 116.9(3) . . ? C5 C2 C3 119.2(3) . . ? C5 C2 C1 118.2(3) . . ? C3 C2 C1 122.6(3) . . ? C5 C3 C2 119.1(3) 7_566 . ? C5 C3 C4 118.5(2) 7_566 . ? C2 C3 C4 122.1(2) . . ? C4 O4 H40H 116.1 . . ? O3 C4 O4 124.2(3) . . ? O3 C4 C3 122.4(3) . . ? O4 C4 C3 113.3(2) . . ? C2 C5 C3 121.7(3) . 7_566 ? C2 C5 H5A 119.1 . . ? C3 C5 H5A 119.1 7_566 . ? C7 C6 C8 127.3(8) . . ? C7 C6 H6A 116.4 . . ? C8 C6 H6A 116.4 . . ? C6 C7 C13 127.7(8) . . ? C6 C7 H7A 116.1 . . ? C13 C7 H7A 116.1 . . ? C9 C8 C12 120.0 . . ? C9 C8 C6 121.4(6) . . ? C12 C8 C6 118.6(6) . . ? C10 C9 C8 120.0 . . ? C10 C9 H9A 120.0 . . ? C8 C9 H9A 120.0 . . ? C9 C10 N1 120.0 . . ? C9 C10 H10A 120.0 . . ? N1 C10 H10A 120.0 . . ? C10 N1 C11 120.0 . . ? C10 N1 H1A 120.0 . . ? C11 N1 H1A 120.0 . . ? C12 C11 N1 120.0 . . ? C12 C11 H11A 120.0 . . ? N1 C11 H11A 120.0 . . ? C11 C12 C8 120.0 . . ? C11 C12 H12A 120.0 . . ? C8 C12 H12A 120.0 . . ? C14 C13 C17 120.0 . . ? C14 C13 C7 117.1(6) . . ? C17 C13 C7 122.9(6) . . ? N2 C14 C13 120.0 . . ? N2 C14 H14A 120.0 . . ? C13 C14 H14A 120.0 . . ? C14 N2 C15 120.0 . . ? N2 C15 C16 120.0 . . ? N2 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C17 C16 C15 120.0 . . ? C17 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C16 C17 C13 120.0 . . ? C16 C17 H17A 120.0 . . ? C13 C17 H17A 120.0 . . ? C7A C6A C8A 127.8(12) . . ? C7A C6A H6AA 116.1 . . ? C8A C6A H6AA 116.1 . . ? C6A C7A C13A 128.7(12) . . ? C6A C7A H7AA 115.6 . . ? C13A C7A H7AA 115.6 . . ? C9A C8A C12A 120.0 . . ? C9A C8A C6A 120.4(8) . . ? C12A C8A C6A 119.4(8) . . ? C8A C9A C10A 120.0 . . ? C8A C9A H9AA 120.0 . . ? C10A C9A H9AA 120.0 . . ? N1A C10A C9A 120.0 . . ? N1A C10A H10B 120.0 . . ? C9A C10A H10B 120.0 . . ? C11A N1A C10A 120.0 . . ? C11A N1A H1AA 120.0 . . ? C10A N1A H1AA 120.0 . . ? N1A C11A C12A 120.0 . . ? N1A C11A H11B 120.0 . . ? C12A C11A H11B 120.0 . . ? C11A C12A C8A 120.0 . . ? C11A C12A H12B 120.0 . . ? C8A C12A H12B 120.0 . . ? C14A C13A C17A 120.0 . . ? C14A C13A C7A 119.5(8) . . ? C17A C13A C7A 120.5(8) . . ? C13A C14A N2A 120.0 . . ? C13A C14A H14B 120.0 . . ? N2A C14A H14B 120.0 . . ? C15A N2A C14A 120.0 . . ? N2A C15A C16A 120.0 . . ? N2A C15A H15B 120.0 . . ? C16A C15A H15B 120.0 . . ? C15A C16A C17A 120.0 . . ? C15A C16A H16B 120.0 . . ? C17A C16A H16B 120.0 . . ? C16A C17A C13A 120.0 . . ? C16A C17A H17B 120.0 . . ? C13A C17A H17B 120.0 . . ? _diffrn_measured_fraction_theta_max 0.825 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.290 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.060 # Attachment 'compound2cif.txt' data_shelxle2 _database_code_depnum_ccdc_archive 'CCDC 742519' #TrackingRef 'compound2cif.txt' #========================================================================== _audit_creation_method SHELXL-97 _audit_creation_date '20 August 2008' #========================================================================== _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H12 N, 0.5(C10 H4 O8)' _chemical_formula_sum 'C18 H14 N O4' _chemical_formula_weight 308.30 _chemical_compound_source Synthesis 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 7.559(4) _cell_length_b 10.106(6) _cell_length_c 11.410(7) _cell_angle_alpha 104.767(10) _cell_angle_beta 106.763(10) _cell_angle_gamma 108.1770(10) _cell_volume 733.8(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1502 _cell_measurement_theta_min 2.00 _cell_measurement_theta_max 27.80 _exptl_crystal_description Prism _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 322 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type 'Multi Scan' _exptl_absorpt_correction_T_min 0.949 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method '\w ' _diffrn_radiation_detector CCD _diffrn_measurement_device 'Mercury (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7661 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.89 _reflns_number_total 2694 _reflns_number_gt 2076 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _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^)+(0.0693P)^2^+0.3306P] 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 2694 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0800 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1642 _refine_ls_wR_factor_gt 0.1504 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.1316(3) 0.40051(18) 0.10206(17) 0.0569(5) Uani 1 1 d . . . O2 O 0.0799(3) 0.34390(19) 0.26789(17) 0.0586(5) Uani 1 1 d . . . O3 O -0.1933(3) 0.1288(2) 0.25887(19) 0.0654(6) Uani 1 1 d . . . H3O3 H -0.0677 0.2181 0.2721 0.078 Uiso 1 1 d R . . O4 O -0.4167(3) -0.0917(2) 0.1059(2) 0.0742(6) Uani 1 1 d . . . N1 N 0.1984(3) 0.6744(2) 0.25063(19) 0.0441(5) Uani 1 1 d . . . HN1 H 0.1764 0.5686 0.1975 0.053 Uiso 1 1 d R . . C1 C 0.0832(4) 0.3085(3) 0.1541(2) 0.0432(6) Uani 1 1 d . . . C2 C 0.0316(3) 0.1462(2) 0.0771(2) 0.0370(5) Uani 1 1 d . . . C3 C -0.1162(4) 0.0186(2) 0.0752(2) 0.0382(5) Uani 1 1 d . . . C4 C -0.2556(4) 0.0162(3) 0.1476(3) 0.0489(6) Uani 1 1 d . . . C5 C 0.1428(4) 0.1233(2) 0.0018(2) 0.0401(5) Uani 1 1 d . . . H5 H 0.2405 0.2074 0.0030 0.048 Uiso 1 1 calc R . . C6 C 0.2503(4) 0.7846(3) 0.2061(2) 0.0493(6) Uani 1 1 d . . . H6 H 0.2681 0.7640 0.1271 0.059 Uiso 1 1 calc R . . C7 C 0.2776(4) 0.9262(3) 0.2739(3) 0.0525(6) Uani 1 1 d . . . H7 H 0.3126 1.0008 0.2405 0.063 Uiso 1 1 calc R . . C8 C 0.2537(4) 0.9603(3) 0.3921(2) 0.0468(6) Uani 1 1 d . . . C9 C 0.2046(4) 0.8435(3) 0.4386(2) 0.0511(6) Uani 1 1 d . . . H9 H 0.1910 0.8620 0.5190 0.061 Uiso 1 1 calc R . . C10 C 0.1765(4) 0.7013(3) 0.3652(2) 0.0491(6) Uani 1 1 d . . . H10 H 0.1421 0.6239 0.3957 0.059 Uiso 1 1 calc R . . C11 C 0.2815(4) 1.1151(3) 0.4607(3) 0.0559(7) Uani 1 1 d . . . H11 H 0.2996 1.1808 0.4167 0.067 Uiso 1 1 calc R . . C12 C 0.2826(4) 1.1667(3) 0.5770(3) 0.0558(7) Uani 1 1 d . . . H12 H 0.2631 1.0996 0.6197 0.067 Uiso 1 1 calc R . . C13 C 0.3117(4) 1.3211(3) 0.6496(3) 0.0503(6) Uani 1 1 d . . . C14 C 0.3284(5) 1.4330(3) 0.5981(3) 0.0622(7) Uani 1 1 d . . . H14 H 0.3255 1.4134 0.5132 0.075 Uiso 1 1 calc R . . C15 C 0.3496(5) 1.5743(3) 0.6723(3) 0.0699(8) Uani 1 1 d . . . H15 H 0.3617 1.6485 0.6370 0.084 Uiso 1 1 calc R . . C16 C 0.3526(4) 1.6041(3) 0.7974(3) 0.0646(8) Uani 1 1 d . . . H16 H 0.3670 1.6983 0.8472 0.078 Uiso 1 1 calc R . . C17 C 0.3342(5) 1.4936(3) 0.8482(3) 0.0653(8) Uani 1 1 d . . . H17 H 0.3347 1.5127 0.9325 0.078 Uiso 1 1 calc R . . C18 C 0.3151(4) 1.3546(3) 0.7751(3) 0.0595(7) Uani 1 1 d . . . H18 H 0.3042 1.2815 0.8116 0.071 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 0.0814(13) 0.0323(9) 0.0597(11) 0.0146(8) 0.0366(10) 0.0216(9) O2 0.0817(14) 0.0435(10) 0.0460(10) 0.0069(8) 0.0315(9) 0.0231(10) O3 0.0978(16) 0.0530(12) 0.0659(12) 0.0223(9) 0.0580(12) 0.0336(11) O4 0.0795(15) 0.0556(13) 0.1038(17) 0.0282(11) 0.0671(13) 0.0219(12) N1 0.0432(11) 0.0327(11) 0.0464(12) 0.0054(8) 0.0173(9) 0.0119(9) C1 0.0478(14) 0.0360(13) 0.0427(13) 0.0100(10) 0.0194(11) 0.0164(11) C2 0.0446(13) 0.0326(12) 0.0360(12) 0.0117(9) 0.0186(10) 0.0175(10) C3 0.0491(13) 0.0344(12) 0.0385(12) 0.0148(9) 0.0235(10) 0.0203(10) C4 0.0674(18) 0.0396(14) 0.0601(16) 0.0241(12) 0.0415(14) 0.0286(14) C5 0.0467(13) 0.0300(12) 0.0458(13) 0.0146(10) 0.0236(10) 0.0137(10) C6 0.0534(15) 0.0440(14) 0.0464(14) 0.0132(11) 0.0212(11) 0.0174(12) C7 0.0564(16) 0.0402(14) 0.0561(16) 0.0166(12) 0.0208(12) 0.0174(12) C8 0.0366(13) 0.0374(13) 0.0540(15) 0.0065(11) 0.0126(11) 0.0140(11) C9 0.0486(15) 0.0518(15) 0.0454(14) 0.0069(11) 0.0219(11) 0.0182(12) C10 0.0512(15) 0.0392(14) 0.0518(15) 0.0148(11) 0.0223(12) 0.0130(12) C11 0.0541(16) 0.0500(16) 0.0573(17) 0.0130(13) 0.0213(13) 0.0210(13) C12 0.0501(16) 0.0503(16) 0.0578(17) 0.0117(12) 0.0185(12) 0.0195(13) C13 0.0421(14) 0.0418(14) 0.0548(16) 0.0052(11) 0.0113(11) 0.0206(12) C14 0.0673(19) 0.0611(18) 0.0506(16) 0.0103(13) 0.0234(13) 0.0261(15) C15 0.080(2) 0.0489(17) 0.074(2) 0.0196(15) 0.0233(16) 0.0293(16) C16 0.0614(18) 0.0474(17) 0.0625(18) -0.0027(13) 0.0073(13) 0.0298(14) C17 0.072(2) 0.069(2) 0.0466(16) 0.0073(13) 0.0130(13) 0.0407(17) C18 0.0674(18) 0.0546(17) 0.0540(16) 0.0142(13) 0.0168(13) 0.0344(15) _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 1.243(3) . ? O2 C1 1.266(3) . ? O3 C4 1.308(3) . ? O4 C4 1.213(3) . ? N1 C10 1.335(3) . ? N1 C6 1.335(3) . ? C1 C2 1.511(3) . ? C2 C5 1.391(3) . ? C2 C3 1.408(3) . ? C3 C5 1.394(3) 2 ? C3 C4 1.514(3) . ? C5 C3 1.394(3) 2 ? C6 C7 1.360(3) . ? C7 C8 1.383(4) . ? C8 C9 1.404(4) . ? C8 C11 1.477(4) . ? C9 C10 1.380(3) . ? C11 C12 1.293(4) . ? C12 C13 1.480(4) . ? C13 C18 1.376(4) . ? C13 C14 1.390(4) . ? C14 C15 1.395(4) . ? C15 C16 1.373(4) . ? C16 C17 1.372(4) . ? C17 C18 1.377(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 C10 N1 C6 120.8(2) . . ? O1 C1 O2 123.8(2) . . ? O1 C1 C2 117.3(2) . . ? O2 C1 C2 118.9(2) . . ? C5 C2 C3 118.0(2) . . ? C5 C2 C1 115.7(2) . . ? C3 C2 C1 126.3(2) . . ? C5 C3 C2 118.3(2) 2 . ? C5 C3 C4 114.5(2) 2 . ? C2 C3 C4 127.2(2) . . ? O4 C4 O3 121.3(2) . . ? O4 C4 C3 120.1(2) . . ? O3 C4 C3 118.5(2) . . ? C2 C5 C3 123.7(2) . 2 ? N1 C6 C7 121.3(2) . . ? C6 C7 C8 120.6(2) . . ? C7 C8 C9 117.0(2) . . ? C7 C8 C11 118.5(2) . . ? C9 C8 C11 124.5(2) . . ? C10 C9 C8 120.0(2) . . ? N1 C10 C9 120.3(2) . . ? C12 C11 C8 125.3(3) . . ? C11 C12 C13 126.9(3) . . ? C18 C13 C14 117.6(2) . . ? C18 C13 C12 117.7(3) . . ? C14 C13 C12 124.6(3) . . ? C13 C14 C15 120.8(3) . . ? C16 C15 C14 120.1(3) . . ? C17 C16 C15 119.4(3) . . ? C16 C17 C18 120.4(3) . . ? C13 C18 C17 121.7(3) . . ? _diffrn_measured_fraction_theta_max 0.771 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.486 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.049 # Attachment 'compound3cif.txt' data_shelxle3 _database_code_depnum_ccdc_archive 'CCDC 742520' #TrackingRef 'compound3cif.txt' #========================================================================== _audit_creation_method SHELXL-97 _audit_creation_date '20 August 2008' #========================================================================== _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H11 Cl N, 0.5(C10 H4 O8)' _chemical_formula_sum 'C18 H13 Cl N O4' _chemical_formula_weight 342.74 _chemical_compound_source Synthesis 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 7.4116(15) _cell_length_b 9.874(2) _cell_length_c 12.082(2) _cell_angle_alpha 66.39(3) _cell_angle_beta 73.94(3) _cell_angle_gamma 79.39(3) _cell_volume 775.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1320 _cell_measurement_theta_min 1.4978 _cell_measurement_theta_max 28.00 _exptl_crystal_description Prism _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 354 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type 'Multi Scan' _exptl_absorpt_correction_T_min 0.920 _exptl_absorpt_correction_T_max 0.945 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method '\w ' _diffrn_radiation_detector CCD _diffrn_measurement_device 'Mercury (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8867 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0911 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.09 _reflns_number_total 2956 _reflns_number_gt 1763 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _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^)+(0.0441P)^2^+0.4522P] 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 2956 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1380 _refine_ls_R_factor_gt 0.0780 _refine_ls_wR_factor_ref 0.1759 _refine_ls_wR_factor_gt 0.1496 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.137 _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 Cl1 Cl 0.10868(17) 0.93492(14) 0.89177(12) 0.0770(4) Uani 1 1 d . . . O1 O 1.2363(4) 0.3082(3) 0.0805(2) 0.0606(8) Uani 1 1 d . . . O2 O 1.2158(4) 0.1217(3) 0.2607(2) 0.0628(8) Uani 1 1 d . . . N1 N 1.0128(5) 0.4464(4) 0.2274(3) 0.0559(9) Uani 1 1 d . . . H1N H 1.0940 0.3981 0.1810 0.068(14) Uiso 1 1 d R . . C17 C 1.3868(5) -0.0796(4) 0.1161(3) 0.0427(9) Uani 1 1 d . . . O4 O 1.2586(4) -0.3096(3) 0.2437(3) 0.0724(10) Uani 1 1 d . . . O3 O 1.1998(5) -0.1415(3) 0.3285(2) 0.0739(10) Uani 1 1 d . . . H3O H 1.2121 -0.0223 0.3033 0.110(18) Uiso 1 1 d R . . C19 C 1.5030(5) -0.1489(4) 0.0393(3) 0.0456(10) Uani 1 1 d . . . H19A H 1.5050 -0.2515 0.0667 0.055 Uiso 1 1 calc R . . C2 C 0.6455(6) 0.6792(5) 0.4395(4) 0.0599(12) Uani 1 1 d . . . H2A H 0.5947 0.7725 0.3951 0.072 Uiso 1 1 calc R . . C10 C 0.7754(6) 0.5946(4) 0.3685(4) 0.0498(10) Uani 1 1 d . . . C14 C 0.8133(6) 0.6550(5) 0.2398(4) 0.0572(11) Uani 1 1 d . . . H14A H 0.7573 0.7481 0.2000 0.069 Uiso 1 1 calc R . . C3 C 0.4709(6) 0.7073(5) 0.6394(4) 0.0552(11) Uani 1 1 d . . . C11 C 0.8641(6) 0.4552(4) 0.4229(4) 0.0518(10) Uani 1 1 d . . . H11A H 0.8436 0.4108 0.5088 0.062 Uiso 1 1 calc R . . C12 C 0.9804(6) 0.3838(4) 0.3513(4) 0.0542(11) Uani 1 1 d . . . H12A H 1.0381 0.2905 0.3886 0.065 Uiso 1 1 calc R . . C16 C 1.3830(5) 0.0761(4) 0.0759(3) 0.0419(9) Uani 1 1 d . . . C1 C 0.5968(6) 0.6313(5) 0.5614(4) 0.0595(11) Uani 1 1 d . . . H1A H 0.6489 0.5374 0.6033 0.071 Uiso 1 1 calc R . . C15 C 1.2691(6) 0.1746(5) 0.1440(4) 0.0528(11) Uani 1 1 d . . . C18 C 1.2744(6) -0.1860(5) 0.2364(4) 0.0547(11) Uani 1 1 d . . . C8 C 0.3718(6) 0.8435(5) 0.5918(4) 0.0629(12) Uani 1 1 d . . . H8A H 0.3815 0.8885 0.5066 0.075 Uiso 1 1 calc R . . C7 C 0.2589(6) 0.9133(5) 0.6688(4) 0.0605(12) Uani 1 1 d . . . H7A H 0.1927 1.0043 0.6360 0.073 Uiso 1 1 calc R . . C6 C 0.2457(6) 0.8463(5) 0.7943(4) 0.0571(11) Uani 1 1 d . . . C13 C 0.9311(6) 0.5799(5) 0.1712(4) 0.0585(12) Uani 1 1 d . . . H13A H 0.9546 0.6217 0.0851 0.070 Uiso 1 1 calc R . . C4 C 0.4512(6) 0.6414(5) 0.7659(4) 0.0605(12) Uani 1 1 d . . . H4A H 0.5147 0.5493 0.7995 0.073 Uiso 1 1 calc R . . C5 C 0.3388(6) 0.7098(5) 0.8435(4) 0.0624(12) Uani 1 1 d . . . H5A H 0.3260 0.6639 0.9289 0.075 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 Cl1 0.0681(8) 0.0937(10) 0.0889(9) -0.0649(8) -0.0090(6) 0.0060(7) O1 0.075(2) 0.0491(17) 0.0569(18) -0.0289(15) -0.0111(15) 0.0137(15) O2 0.077(2) 0.0631(19) 0.0480(17) -0.0306(15) -0.0022(15) 0.0017(16) N1 0.061(2) 0.056(2) 0.057(2) -0.035(2) -0.0067(18) 0.0035(18) C17 0.042(2) 0.045(2) 0.040(2) -0.0154(18) -0.0106(17) 0.0021(17) O4 0.084(2) 0.0491(18) 0.068(2) -0.0164(16) 0.0049(17) -0.0117(17) O3 0.099(3) 0.059(2) 0.0435(17) -0.0160(15) 0.0052(16) 0.0018(17) C19 0.047(2) 0.041(2) 0.052(2) -0.0225(19) -0.0135(19) 0.0047(18) C2 0.059(3) 0.060(3) 0.064(3) -0.034(2) -0.009(2) 0.006(2) C10 0.049(3) 0.047(2) 0.055(3) -0.023(2) -0.007(2) -0.0038(19) C14 0.059(3) 0.052(2) 0.059(3) -0.025(2) -0.012(2) 0.006(2) C3 0.042(2) 0.059(3) 0.069(3) -0.035(2) -0.002(2) -0.003(2) C11 0.060(3) 0.050(2) 0.046(2) -0.023(2) -0.003(2) -0.006(2) C12 0.065(3) 0.044(2) 0.056(3) -0.023(2) -0.014(2) -0.001(2) C16 0.040(2) 0.045(2) 0.042(2) -0.0196(18) -0.0124(17) 0.0056(17) C1 0.056(3) 0.060(3) 0.070(3) -0.036(2) -0.009(2) -0.001(2) C15 0.052(3) 0.061(3) 0.052(3) -0.031(2) -0.010(2) 0.002(2) C18 0.053(3) 0.053(3) 0.049(2) -0.016(2) -0.008(2) 0.007(2) C8 0.057(3) 0.073(3) 0.058(3) -0.029(2) -0.007(2) -0.003(2) C7 0.052(3) 0.060(3) 0.074(3) -0.037(3) -0.006(2) 0.002(2) C6 0.048(3) 0.066(3) 0.068(3) -0.042(3) -0.001(2) -0.007(2) C13 0.071(3) 0.053(3) 0.051(3) -0.022(2) -0.014(2) 0.002(2) C4 0.057(3) 0.060(3) 0.064(3) -0.031(2) -0.004(2) 0.000(2) C5 0.063(3) 0.068(3) 0.064(3) -0.036(3) -0.007(2) -0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C6 1.738(4) . ? O1 C15 1.250(4) . ? O2 C15 1.262(4) . ? O2 H3O 1.3069 . ? N1 C13 1.335(5) . ? N1 C12 1.339(5) . ? N1 H1N 0.9086 . ? C17 C19 1.386(5) . ? C17 C16 1.412(5) . ? C17 C18 1.529(5) . ? O4 C18 1.213(5) . ? O3 C18 1.303(5) . ? O3 H3O 1.1065 . ? C19 C16 1.393(5) 2_855 ? C19 H19A 0.9300 . ? C2 C1 1.318(6) . ? C2 C10 1.477(5) . ? C2 H2A 0.9300 . ? C10 C14 1.389(5) . ? C10 C11 1.393(5) . ? C14 C13 1.361(5) . ? C14 H14A 0.9300 . ? C3 C4 1.378(6) . ? C3 C8 1.389(6) . ? C3 C1 1.463(6) . ? C11 C12 1.357(5) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C16 C19 1.393(5) 2_855 ? C16 C15 1.514(5) . ? C1 H1A 0.9300 . ? C8 C7 1.382(5) . ? C8 H8A 0.9300 . ? C7 C6 1.373(6) . ? C7 H7A 0.9300 . ? C6 C5 1.374(6) . ? C13 H13A 0.9300 . ? C4 C5 1.378(5) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 O2 H3O 111.6 . . ? C13 N1 C12 121.1(4) . . ? C13 N1 H1N 119.6 . . ? C12 N1 H1N 119.4 . . ? C19 C17 C16 118.2(3) . . ? C19 C17 C18 113.8(3) . . ? C16 C17 C18 128.0(4) . . ? C18 O3 H3O 112.9 . . ? C17 C19 C16 124.7(3) . 2_855 ? C17 C19 H19A 117.6 . . ? C16 C19 H19A 117.6 2_855 . ? C1 C2 C10 124.3(4) . . ? C1 C2 H2A 117.9 . . ? C10 C2 H2A 117.9 . . ? C14 C10 C11 116.9(4) . . ? C14 C10 C2 119.2(4) . . ? C11 C10 C2 123.9(4) . . ? C13 C14 C10 121.0(4) . . ? C13 C14 H14A 119.5 . . ? C10 C14 H14A 119.5 . . ? C4 C3 C8 118.4(4) . . ? C4 C3 C1 118.4(4) . . ? C8 C3 C1 123.2(4) . . ? C12 C11 C10 120.4(4) . . ? C12 C11 H11A 119.8 . . ? C10 C11 H11A 119.8 . . ? N1 C12 C11 120.7(4) . . ? N1 C12 H12A 119.7 . . ? C11 C12 H12A 119.7 . . ? C19 C16 C17 117.0(3) 2_855 . ? C19 C16 C15 115.5(3) 2_855 . ? C17 C16 C15 127.5(3) . . ? C2 C1 C3 128.1(4) . . ? C2 C1 H1A 115.9 . . ? C3 C1 H1A 115.9 . . ? O1 C15 O2 122.7(4) . . ? O1 C15 C16 117.3(3) . . ? O2 C15 C16 119.9(4) . . ? O4 C18 O3 121.9(4) . . ? O4 C18 C17 119.2(4) . . ? O3 C18 C17 118.9(4) . . ? C7 C8 C3 121.1(4) . . ? C7 C8 H8A 119.4 . . ? C3 C8 H8A 119.4 . . ? C6 C7 C8 119.1(4) . . ? C6 C7 H7A 120.5 . . ? C8 C7 H7A 120.5 . . ? C7 C6 C5 120.7(4) . . ? C7 C6 Cl1 119.5(4) . . ? C5 C6 Cl1 119.7(4) . . ? N1 C13 C14 120.0(4) . . ? N1 C13 H13A 120.0 . . ? C14 C13 H13A 120.0 . . ? C5 C4 C3 120.9(4) . . ? C5 C4 H4A 119.5 . . ? C3 C4 H4A 119.5 . . ? C6 C5 C4 119.7(4) . . ? C6 C5 H5A 120.2 . . ? C4 C5 H5A 120.2 . . ? _diffrn_measured_fraction_theta_max 0.783 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.177 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.050 # Attachment 'compound4cif.txt' data_shelxle4 _database_code_depnum_ccdc_archive 'CCDC 742521' #TrackingRef 'compound4cif.txt' #========================================================================== _audit_creation_method SHELXL-97 _audit_creation_date '20 August 2008' #========================================================================== _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H12 N O, 0.5(C10 H4 O8)' _chemical_formula_sum 'C18 H14 N O5' _chemical_formula_weight 324.30 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' 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' H H 0.0000 0.0000 '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 _symmetry_space_group_name_Hall '-P 2yn ' 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 7.037(3) _cell_length_b 19.262(7) _cell_length_c 11.197(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.653(13) _cell_angle_gamma 90.00 _cell_volume 1480.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1132 _cell_measurement_theta_min 2.00 _cell_measurement_theta_max 28.06 _exptl_crystal_description Prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type 'Multi Scan' _exptl_absorpt_correction_T_min 0.956 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method '\w ' _diffrn_radiation_detector CCD _diffrn_measurement_device 'Mercury (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16213 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 28.06 _reflns_number_total 2835 _reflns_number_gt 1841 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _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^)+(0.0811P)^2^+0.5796P] 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 2835 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1275 _refine_ls_R_factor_gt 0.0818 _refine_ls_wR_factor_ref 0.2099 _refine_ls_wR_factor_gt 0.1867 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _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 0.6032(4) 0.18010(12) 0.9489(2) 0.0725(7) Uani 1 1 d . . . O2 O 0.8534(4) 0.14862(12) 1.0927(3) 0.0811(8) Uani 1 1 d . . . O3 O 1.0086(4) 0.04379(14) 1.1755(3) 0.0902(9) Uani 1 1 d . . . H3O H 0.9413 0.0889 1.1501 0.108 Uiso 1 1 d R . . O4 O 0.9651(4) -0.06686(15) 1.1605(3) 0.1182(13) Uani 1 1 d . . . O5 O 1.1301(4) 0.82844(12) 1.2998(2) 0.0778(8) Uani 1 1 d . . . H5O H 1.0804 0.8626 1.2616 0.093 Uiso 1 1 d R . . N1 N 0.7191(4) 0.31056(14) 1.0110(3) 0.0636(8) Uani 1 1 d . . . H1N H 0.6845 0.2698 0.9865 0.076 Uiso 1 1 d R . . C1 C 0.6941(5) 0.13503(16) 1.0176(3) 0.0596(9) Uani 1 1 d . . . C2 C 0.6078(5) 0.06302(15) 1.0129(3) 0.0497(8) Uani 1 1 d . . . C3 C 0.6975(5) 0.00138(15) 1.0639(3) 0.0513(8) Uani 1 1 d . . . C4 C 0.9053(6) -0.00854(19) 1.1369(3) 0.0644(9) Uani 1 1 d . . . C5 C 0.5871(5) -0.05895(15) 1.0481(3) 0.0536(8) Uani 1 1 d . . . H5 H 0.6477 -0.0998 1.0807 0.064 Uiso 1 1 calc R . . C6 C 0.6446(5) 0.36589(17) 0.9470(3) 0.0614(9) Uani 1 1 d . . . H6 H 0.5530 0.3603 0.8739 0.074 Uiso 1 1 calc R . . C7 C 0.7024(5) 0.43130(16) 0.9882(3) 0.0609(9) Uani 1 1 d . . . H7 H 0.6485 0.4700 0.9438 0.073 Uiso 1 1 calc R . . C8 C 0.8432(5) 0.43967(17) 1.0978(3) 0.0579(9) Uani 1 1 d . . . C9 C 0.9155(6) 0.37969(18) 1.1579(3) 0.0688(10) Uani 1 1 d . . . H9 H 1.0102 0.3828 1.2301 0.083 Uiso 1 1 calc R . . C10 C 0.8522(6) 0.31664(19) 1.1147(3) 0.0685(10) Uani 1 1 d . . . H10 H 0.9021 0.2770 1.1579 0.082 Uiso 1 1 calc R . . C11 C 0.9181(6) 0.50696(19) 1.1494(3) 0.0673(10) Uani 1 1 d . . . H11 H 1.0176 0.5058 1.2194 0.081 Uiso 1 1 calc R . . C12 C 0.8603(5) 0.56717(18) 1.1077(3) 0.0624(9) Uani 1 1 d . . . H12 H 0.7617 0.5684 1.0372 0.075 Uiso 1 1 calc R . . C13 C 0.9354(5) 0.63517(16) 1.1608(3) 0.0543(8) Uani 1 1 d . . . C14 C 0.8518(5) 0.69534(17) 1.1058(3) 0.0595(9) Uani 1 1 d . . . H14 H 0.7507 0.6920 1.0369 0.071 Uiso 1 1 calc R . . C15 C 0.9137(5) 0.75993(16) 1.1497(3) 0.0601(9) Uani 1 1 d . . . H15 H 0.8536 0.7995 1.1112 0.072 Uiso 1 1 calc R . . C16 C 1.0654(5) 0.76634(16) 1.2514(3) 0.0559(8) Uani 1 1 d . . . C17 C 1.1522(5) 0.70708(18) 1.3069(3) 0.0626(9) Uani 1 1 d . . . H17 H 1.2547 0.7107 1.3750 0.075 Uiso 1 1 calc R . . C18 C 1.0882(5) 0.64244(17) 1.2624(3) 0.0604(9) Uani 1 1 d . . . H18 H 1.1484 0.6030 1.3011 0.073 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 0.0848(18) 0.0405(14) 0.0841(17) 0.0058(12) 0.0008(14) -0.0115(12) O2 0.0688(18) 0.0490(15) 0.113(2) -0.0063(13) -0.0080(15) -0.0176(12) O3 0.0692(19) 0.0604(17) 0.121(2) 0.0039(15) -0.0227(15) -0.0118(14) O4 0.083(2) 0.0571(19) 0.183(3) 0.0209(18) -0.038(2) -0.0018(15) O5 0.0895(19) 0.0463(14) 0.0813(16) -0.0075(12) -0.0167(13) -0.0003(13) N1 0.069(2) 0.0405(17) 0.084(2) -0.0038(14) 0.0222(17) -0.0079(14) C1 0.068(2) 0.0381(19) 0.071(2) -0.0046(16) 0.0117(18) -0.0101(17) C2 0.055(2) 0.0374(17) 0.0541(18) -0.0052(13) 0.0062(15) -0.0062(14) C3 0.055(2) 0.0394(18) 0.0564(19) -0.0035(13) 0.0058(15) -0.0062(15) C4 0.062(2) 0.046(2) 0.078(2) 0.0008(17) 0.0008(18) -0.0095(18) C5 0.063(2) 0.0340(17) 0.0613(19) 0.0003(13) 0.0084(16) -0.0017(15) C6 0.058(2) 0.053(2) 0.074(2) -0.0014(17) 0.0154(17) -0.0033(17) C7 0.063(2) 0.0379(19) 0.086(2) 0.0054(16) 0.0273(19) 0.0020(16) C8 0.065(2) 0.047(2) 0.067(2) -0.0106(16) 0.0266(18) -0.0129(16) C9 0.080(3) 0.054(2) 0.070(2) -0.0023(17) 0.0113(18) -0.0020(19) C10 0.082(3) 0.049(2) 0.074(2) 0.0039(17) 0.015(2) 0.0032(19) C11 0.070(2) 0.062(2) 0.071(2) 0.0008(18) 0.0197(18) 0.0037(19) C12 0.060(2) 0.056(2) 0.075(2) 0.0048(17) 0.0227(18) 0.0040(17) C13 0.057(2) 0.0435(19) 0.063(2) -0.0032(15) 0.0162(16) -0.0049(15) C14 0.056(2) 0.051(2) 0.066(2) -0.0033(15) 0.0020(16) -0.0076(16) C15 0.063(2) 0.0423(19) 0.068(2) 0.0032(15) -0.0032(17) 0.0023(16) C16 0.061(2) 0.0386(19) 0.064(2) -0.0048(14) 0.0057(16) -0.0005(15) C17 0.066(2) 0.052(2) 0.061(2) -0.0014(16) -0.0034(16) 0.0040(17) C18 0.068(2) 0.044(2) 0.070(2) 0.0103(15) 0.0183(18) 0.0135(16) _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 1.241(4) . ? O2 C1 1.272(4) . ? O2 H3O 1.3949 . ? O3 C4 1.262(4) . ? O3 H3O 1.0001 . ? O4 C4 1.208(4) . ? O5 C16 1.350(4) . ? O5 H5O 0.8200 . ? N1 C6 1.327(4) . ? N1 C10 1.328(4) . ? N1 H1N 0.8500 . ? C1 C2 1.510(4) . ? C2 C5 1.394(5) 3_657 ? C2 C3 1.406(4) . ? C3 C5 1.387(4) . ? C3 C4 1.522(5) . ? C5 C2 1.394(5) 3_657 ? C5 H5 0.9300 . ? C6 C7 1.372(4) . ? C6 H6 0.9300 . ? C7 C8 1.407(5) . ? C7 H7 0.9300 . ? C8 C9 1.377(5) . ? C8 C11 1.469(5) . ? C9 C10 1.346(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.283(5) . ? C11 H11 0.9300 . ? C12 C13 1.487(4) . ? C12 H12 0.9300 . ? C13 C14 1.382(4) . ? C13 C18 1.391(5) . ? C14 C15 1.373(4) . ? C14 H14 0.9300 . ? C15 C16 1.385(4) . ? C15 H15 0.9300 . ? C16 C17 1.377(4) . ? C17 C18 1.379(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 H3O 111.8 . . ? C4 O3 H3O 113.2 . . ? C16 O5 H5O 115.7 . . ? C6 N1 C10 121.4(3) . . ? C6 N1 H1N 121.2 . . ? C10 N1 H1N 117.4 . . ? O1 C1 O2 121.7(3) . . ? O1 C1 C2 118.2(3) . . ? O2 C1 C2 120.1(3) . . ? C5 C2 C3 117.2(3) 3_657 . ? C5 C2 C1 114.5(3) 3_657 . ? C3 C2 C1 128.3(3) . . ? C5 C3 C2 117.8(3) . . ? C5 C3 C4 114.1(3) . . ? C2 C3 C4 128.1(3) . . ? O4 C4 O3 121.4(4) . . ? O4 C4 C3 118.8(3) . . ? O3 C4 C3 119.8(3) . . ? C3 C5 C2 125.0(3) . 3_657 ? C3 C5 H5 117.5 . . ? C2 C5 H5 117.5 3_657 . ? N1 C6 C7 120.2(3) . . ? N1 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C8 119.9(3) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 116.4(3) . . ? C9 C8 C11 119.1(3) . . ? C7 C8 C11 124.6(3) . . ? C10 C9 C8 121.6(4) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? N1 C10 C9 120.5(3) . . ? N1 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C8 126.7(4) . . ? C12 C11 H11 116.7 . . ? C8 C11 H11 116.7 . . ? C11 C12 C13 126.5(4) . . ? C11 C12 H12 116.8 . . ? C13 C12 H12 116.8 . . ? C14 C13 C18 117.2(3) . . ? C14 C13 C12 118.8(3) . . ? C18 C13 C12 124.0(3) . . ? C15 C14 C13 122.0(3) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C14 C15 C16 120.1(3) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? O5 C16 C17 118.4(3) . . ? O5 C16 C15 122.7(3) . . ? C17 C16 C15 118.9(3) . . ? C16 C17 C18 120.5(3) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C17 C18 C13 121.3(3) . . ? C17 C18 H18 119.4 . . ? C13 C18 H18 119.4 . . ? _diffrn_measured_fraction_theta_max 0.788 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.330 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.048 # Attachment 'compound5cif.txt' data_shelxle5 _database_code_depnum_ccdc_archive 'CCDC 742522' #TrackingRef 'compound5cif.txt' #========================================================================== _audit_creation_method SHELXL-97 _audit_creation_date '20 August 2008' #========================================================================== _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H22 Cl2 N2, C10 H4 O8, 2(C2 H6 O S)' _chemical_formula_sum 'C40 H38 Cl2 N2 O10 S2' _chemical_formula_weight 841.74 _chemical_compound_source Synthesis 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 10.786(5) _cell_length_b 9.682(4) _cell_length_c 19.379(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.802(9) _cell_angle_gamma 90.00 _cell_volume 2005.0(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1906 _cell_measurement_theta_min 2.00 _cell_measurement_theta_max 27.61 _exptl_crystal_description Prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 0.326 _exptl_absorpt_correction_type 'Multi Scan' _exptl_absorpt_correction_T_min 0.949 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method '\w ' _diffrn_radiation_detector CCD _diffrn_measurement_device 'Mercury (2x2 bin mode)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22526 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.61 _reflns_number_total 3971 _reflns_number_gt 2940 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _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^)+(0.0700P)^2^+1.3551P] 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 3971 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1662 _refine_ls_wR_factor_gt 0.1486 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 Cl1 Cl 0.41385(12) 1.69009(12) 0.32895(5) 0.0948(4) Uani 1 1 d . . . S1 S 0.96280(12) 0.15192(10) 0.83732(4) 0.0792(4) Uani 1 1 d . . . O1 O 0.9761(3) 0.2651(2) 0.78526(12) 0.0768(7) Uani 1 1 d . . . O2 O 0.76837(19) 0.7592(2) 0.03479(12) 0.0607(6) Uani 1 1 d . . . O3 O 0.88909(19) 0.85228(18) -0.03735(11) 0.0540(5) Uani 1 1 d . . . O4 O 0.9533(2) 0.3228(2) 0.15790(11) 0.0590(6) Uani 1 1 d . . . H4OH H 0.9764 0.2939 0.2014 0.071 Uiso 1 1 d R . . O5 O 1.1595(2) 0.3342(3) 0.15948(12) 0.0711(7) Uani 1 1 d . . . N1 N 0.7464(2) 1.0604(2) -0.02830(12) 0.0457(6) Uani 1 1 d . . . H1N1 H 0.8048 0.9655 -0.0325 0.055 Uiso 1 1 d R . . C1 C 0.8525(2) 0.7520(2) -0.00131(14) 0.0391(6) Uani 1 1 d . . . C2 C 0.9269(2) 0.6205(2) -0.00276(13) 0.0358(6) Uani 1 1 d . . . C3 C 0.9532(2) 0.5457(2) 0.05879(13) 0.0392(6) Uani 1 1 d . . . H3A H 0.9214 0.5759 0.0984 0.047 Uiso 1 1 calc R . . C4 C 1.0259(2) 0.4267(2) 0.06233(13) 0.0372(6) Uani 1 1 d . . . C5 C 1.0563(3) 0.3553(3) 0.13145(14) 0.0428(6) Uani 1 1 d . . . C6 C 0.6247(3) 1.0591(3) -0.05122(17) 0.0549(8) Uani 1 1 d . . . H6A H 0.5910 0.9834 -0.0768 0.066 Uiso 1 1 calc R . . C7 C 0.5471(3) 1.1653(3) -0.03849(16) 0.0499(7) Uani 1 1 d . . . H7A H 0.4624 1.1618 -0.0558 0.060 Uiso 1 1 calc R . . C8 C 0.5949(2) 1.2773(3) 0.00004(13) 0.0398(6) Uani 1 1 d . . . C9 C 0.7211(3) 1.2768(3) 0.02417(16) 0.0501(7) Uani 1 1 d . . . H9A H 0.7568 1.3501 0.0508 0.060 Uiso 1 1 calc R . . C10 C 0.7945(3) 1.1669(3) 0.00864(16) 0.0501(7) Uani 1 1 d . . . H10A H 0.8797 1.1681 0.0246 0.060 Uiso 1 1 calc R . . C11 C 0.5053(3) 1.3906(3) 0.01467(14) 0.0428(6) Uani 1 1 d . . . H11A H 0.4406 1.3524 0.0401 0.051 Uiso 1 1 calc R . . C12 C 0.5584(3) 1.5240(3) 0.05058(14) 0.0429(6) Uani 1 1 d . . . H12A H 0.6497 1.5262 0.0527 0.051 Uiso 1 1 calc R . . C13 C 0.5208(3) 1.5587(3) 0.12130(14) 0.0441(6) Uani 1 1 d . . . C14 C 0.4036(3) 1.5321(3) 0.13808(15) 0.0563(8) Uani 1 1 d . . . H14A H 0.3457 1.4863 0.1062 0.068 Uiso 1 1 calc R . . C15 C 0.3693(3) 1.5726(3) 0.20240(17) 0.0641(9) Uani 1 1 d . . . H15A H 0.2896 1.5538 0.2134 0.077 Uiso 1 1 calc R . . C16 C 0.4554(3) 1.6401(3) 0.24851(15) 0.0579(8) Uani 1 1 d . . . C17 C 0.5725(3) 1.6690(4) 0.23280(18) 0.0659(9) Uani 1 1 d . . . H17A H 0.6301 1.7155 0.2646 0.079 Uiso 1 1 calc R . . C18 C 0.6042(3) 1.6283(3) 0.16896(17) 0.0573(8) Uani 1 1 d . . . H18A H 0.6836 1.6484 0.1581 0.069 Uiso 1 1 calc R . . C19 C 0.8406(5) 0.0422(5) 0.7983(2) 0.1093(16) Uani 1 1 d . . . H19A H 0.7618 0.0892 0.7964 0.164 Uiso 1 1 calc R . . H19B H 0.8388 -0.0405 0.8255 0.164 Uiso 1 1 calc R . . H19C H 0.8552 0.0185 0.7520 0.164 Uiso 1 1 calc R . . C20 C 1.0895(5) 0.0384(5) 0.8330(2) 0.1077(16) Uani 1 1 d . . . H20A H 1.1660 0.0825 0.8525 0.161 Uiso 1 1 calc R . . H20B H 1.0939 0.0149 0.7852 0.161 Uiso 1 1 calc R . . H20C H 1.0775 -0.0440 0.8588 0.161 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 Cl1 0.1362(10) 0.1060(8) 0.0464(5) -0.0248(5) 0.0277(5) 0.0091(7) S1 0.1361(9) 0.0640(6) 0.0396(5) -0.0053(4) 0.0195(5) -0.0221(5) O1 0.135(2) 0.0503(13) 0.0482(13) -0.0034(10) 0.0241(13) -0.0097(13) O2 0.0561(12) 0.0448(11) 0.0886(17) 0.0080(11) 0.0364(12) 0.0109(10) O3 0.0642(13) 0.0327(10) 0.0712(14) 0.0112(9) 0.0315(11) 0.0168(9) O4 0.0705(14) 0.0665(13) 0.0411(12) 0.0143(10) 0.0114(10) 0.0007(11) O5 0.0643(15) 0.0840(17) 0.0615(15) 0.0194(12) -0.0043(12) 0.0101(12) N1 0.0528(14) 0.0339(12) 0.0539(14) 0.0053(10) 0.0194(11) 0.0144(10) C1 0.0415(14) 0.0302(12) 0.0469(15) -0.0018(11) 0.0100(12) 0.0031(11) C2 0.0420(13) 0.0264(11) 0.0397(14) -0.0001(10) 0.0074(11) 0.0037(10) C3 0.0508(15) 0.0304(12) 0.0380(14) -0.0030(10) 0.0116(11) 0.0043(11) C4 0.0475(14) 0.0279(12) 0.0368(13) 0.0000(10) 0.0081(11) 0.0042(11) C5 0.0573(17) 0.0319(13) 0.0387(15) -0.0013(10) 0.0048(13) 0.0043(12) C6 0.065(2) 0.0353(14) 0.065(2) -0.0062(13) 0.0108(15) 0.0029(14) C7 0.0446(15) 0.0445(15) 0.0605(19) -0.0008(13) 0.0064(13) 0.0065(13) C8 0.0504(15) 0.0367(13) 0.0341(13) 0.0037(10) 0.0122(11) 0.0132(12) C9 0.0553(17) 0.0384(15) 0.0550(18) -0.0040(13) 0.0015(14) 0.0061(13) C10 0.0447(15) 0.0434(16) 0.0624(19) 0.0050(13) 0.0076(14) 0.0076(13) C11 0.0471(15) 0.0390(14) 0.0441(15) 0.0007(11) 0.0130(12) 0.0067(12) C12 0.0438(14) 0.0389(14) 0.0466(16) 0.0003(11) 0.0085(12) 0.0066(11) C13 0.0560(16) 0.0380(14) 0.0390(14) 0.0007(11) 0.0096(12) 0.0142(12) C14 0.069(2) 0.0576(18) 0.0411(16) -0.0131(13) 0.0038(14) -0.0055(15) C15 0.070(2) 0.071(2) 0.056(2) -0.0138(16) 0.0242(16) -0.0075(17) C16 0.084(2) 0.0553(18) 0.0359(16) -0.0080(13) 0.0129(15) 0.0077(16) C17 0.078(2) 0.065(2) 0.052(2) -0.0164(15) -0.0015(17) 0.0021(17) C18 0.0580(18) 0.0591(18) 0.0547(19) -0.0050(14) 0.0076(15) 0.0045(15) C19 0.142(4) 0.103(3) 0.085(3) -0.005(3) 0.023(3) -0.049(3) C20 0.162(5) 0.070(3) 0.084(3) 0.004(2) -0.009(3) 0.015(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C16 1.748(3) . ? S1 O1 1.510(2) . ? S1 C20 1.765(5) . ? S1 C19 1.780(5) . ? O2 C1 1.221(3) . ? O3 C1 1.289(3) . ? O3 H1N1 1.4346 . ? O4 C5 1.323(3) . ? O4 H4OH 0.8909 . ? O5 C5 1.188(3) . ? N1 C10 1.320(4) . ? N1 C6 1.328(4) . ? N1 H1N1 1.1239 . ? C1 C2 1.507(3) . ? C2 C3 1.392(3) . ? C2 C4 1.400(3) 3_765 ? C3 C4 1.391(3) . ? C3 H3A 0.9300 . ? C4 C2 1.400(3) 3_765 ? C4 C5 1.503(4) . ? C6 C7 1.370(4) . ? C6 H6A 0.9300 . ? C7 C8 1.376(4) . ? C7 H7A 0.9300 . ? C8 C9 1.378(4) . ? C8 C11 1.514(3) . ? C9 C10 1.384(4) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C12 1.540(4) . ? C11 C12 1.587(4) 3_685 ? C11 H11A 0.9800 . ? C12 C13 1.519(4) . ? C12 C11 1.587(4) 3_685 ? C12 H12A 0.9800 . ? C13 C14 1.371(4) . ? C13 C18 1.375(4) . ? C14 C15 1.404(4) . ? C14 H14A 0.9300 . ? C15 C16 1.365(5) . ? C15 H15A 0.9300 . ? C16 C17 1.367(5) . ? C17 C18 1.385(4) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 S1 C20 106.0(2) . . ? O1 S1 C19 106.4(2) . . ? C20 S1 C19 98.1(3) . . ? C1 O3 H1N1 107.3 . . ? C5 O4 H4OH 107.4 . . ? C10 N1 C6 119.1(2) . . ? C10 N1 H1N1 119.7 . . ? C6 N1 H1N1 120.4 . . ? O2 C1 O3 125.0(2) . . ? O2 C1 C2 119.9(2) . . ? O3 C1 C2 115.0(2) . . ? C3 C2 C4 118.8(2) . 3_765 ? C3 C2 C1 118.1(2) . . ? C4 C2 C1 123.0(2) 3_765 . ? C4 C3 C2 121.4(2) . . ? C4 C3 H3A 119.3 . . ? C2 C3 H3A 119.3 . . ? C3 C4 C2 119.7(2) . 3_765 ? C3 C4 C5 118.5(2) . . ? C2 C4 C5 121.7(2) 3_765 . ? O5 C5 O4 124.5(3) . . ? O5 C5 C4 124.3(3) . . ? O4 C5 C4 111.2(2) . . ? N1 C6 C7 122.2(3) . . ? N1 C6 H6A 118.9 . . ? C7 C6 H6A 118.9 . . ? C6 C7 C8 119.7(3) . . ? C6 C7 H7A 120.1 . . ? C8 C7 H7A 120.1 . . ? C7 C8 C9 117.5(2) . . ? C7 C8 C11 118.1(2) . . ? C9 C8 C11 124.4(2) . . ? C8 C9 C10 119.8(3) . . ? C8 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? N1 C10 C9 121.6(3) . . ? N1 C10 H10A 119.2 . . ? C9 C10 H10A 119.2 . . ? C8 C11 C12 119.0(2) . . ? C8 C11 C12 116.5(2) . 3_685 ? C12 C11 C12 91.0(2) . 3_685 ? C8 C11 H11A 109.6 . . ? C12 C11 H11A 109.6 . . ? C12 C11 H11A 109.6 3_685 . ? C13 C12 C11 117.7(2) . . ? C13 C12 C11 117.6(2) . 3_685 ? C11 C12 C11 89.0(2) . 3_685 ? C13 C12 H12A 110.3 . . ? C11 C12 H12A 110.3 . . ? C11 C12 H12A 110.3 3_685 . ? C14 C13 C18 118.2(3) . . ? C14 C13 C12 122.7(3) . . ? C18 C13 C12 118.9(3) . . ? C13 C14 C15 121.4(3) . . ? C13 C14 H14A 119.3 . . ? C15 C14 H14A 119.3 . . ? C16 C15 C14 118.4(3) . . ? C16 C15 H15A 120.8 . . ? C14 C15 H15A 120.8 . . ? C15 C16 C17 121.3(3) . . ? C15 C16 Cl1 118.8(3) . . ? C17 C16 Cl1 119.9(3) . . ? C16 C17 C18 119.2(3) . . ? C16 C17 H17A 120.4 . . ? C18 C17 H17A 120.4 . . ? C13 C18 C17 121.4(3) . . ? C13 C18 H18A 119.3 . . ? C17 C18 H18A 119.3 . . ? S1 C19 H19A 109.5 . . ? S1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? S1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? S1 C20 H20A 109.5 . . ? S1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? S1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.852 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.550 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.053