Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Jubaraj Baruah' _publ_contact_author_address ; Department of Chemistry Indian Institute of Technology IIT-Guwahati Guwahati assam 781039 INDIA ; _publ_contact_author_email JUBA@IITG.ERNET.IN _publ_section_title ; Solid-state hydrogen bonded assembly of N,N?-bis(glycinyl) pyromellitic diimide stabilized by ?-? stacking interaction with aromatic guests ; _publ_author_name 'Jubaraj Baruah' # Attachment 'IC1.cif' data_rj068_0m _database_code_depnum_ccdc_archive 'CCDC 290283' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H26 N2 O10' _chemical_formula_weight 574.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.9664(9) _cell_length_b 16.5707(18) _cell_length_c 10.5010(11) _cell_angle_alpha 90.00 _cell_angle_beta 107.048(6) _cell_angle_gamma 90.00 _cell_volume 1325.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5871 _cell_measurement_theta_min 3.19 _cell_measurement_theta_max 27.86 _exptl_crystal_description rods _exptl_crystal_colour red _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.109 _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 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14073 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 29.14 _reflns_number_total 3542 _reflns_number_gt 2536 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.2206P] 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 3542 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1148 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 C7 C 0.56072(18) 0.00333(7) 0.14290(12) 0.0416(3) Uani 1 1 d . . . H7 H 0.5998 0.0053 0.2354 0.050 Uiso 1 1 calc R . . C6 C 0.46193(16) 0.06416(7) 0.06702(12) 0.0385(3) Uani 1 1 d . . . C5 C 0.40266(16) 0.06091(7) -0.07120(12) 0.0383(3) Uani 1 1 d . . . C4 C 0.29916(17) 0.13524(8) -0.11978(13) 0.0415(3) Uani 1 1 d . . . C3 C 0.39936(18) 0.14135(8) 0.11045(13) 0.0425(3) Uani 1 1 d . . . C2 C 0.21050(18) 0.25481(8) -0.00943(16) 0.0456(3) Uani 1 1 d . . . C1 C 0.31620(16) 0.33056(7) -0.00575(12) 0.0377(3) Uani 1 1 d . . . C8 C -0.06607(18) 0.50537(8) 0.36230(13) 0.0463(3) Uani 1 1 d . . . H8 H -0.1103 0.5089 0.2701 0.056 Uiso 1 1 calc R . . C9 C 0.03842(16) 0.56769(8) 0.43173(13) 0.0424(3) Uani 1 1 d . . . C10 C 0.08352(19) 0.63663(9) 0.36687(16) 0.0514(3) Uani 1 1 d . . . H10 H 0.0383 0.6416 0.2749 0.062 Uiso 1 1 calc R . . C11 C 0.1906(2) 0.69473(9) 0.43665(18) 0.0573(4) Uani 1 1 d . . . H11 H 0.2200 0.7385 0.3921 0.069 Uiso 1 1 calc R . . C12 C 0.25815(19) 0.68955(9) 0.57629(18) 0.0580(4) Uani 1 1 d . . . H12 H 0.3318 0.7299 0.6233 0.070 Uiso 1 1 calc R . . C13 C 0.21622(19) 0.62614(9) 0.64220(16) 0.0533(4) Uani 1 1 d . . . H13 H 0.2599 0.6241 0.7346 0.064 Uiso 1 1 calc R . . C14 C 0.10657(16) 0.56234(8) 0.57327(13) 0.0422(3) Uani 1 1 d . . . C15 C 0.8243(2) 0.41651(10) 0.9760(2) 0.0644(4) Uani 1 1 d . . . H15A H 0.8858 0.4531 0.9347 0.097 Uiso 1 1 calc R . . H15B H 0.7857 0.3706 0.9192 0.097 Uiso 1 1 calc R . . H15C H 0.9013 0.3990 1.0600 0.097 Uiso 1 1 calc R . . H2A H 0.115(2) 0.2543(9) -0.0912(16) 0.059(4) Uiso 1 1 d . . . H2B H 0.166(2) 0.2567(10) 0.0703(18) 0.072(5) Uiso 1 1 d . . . H2O H 0.612(4) 0.4226(18) 1.021(3) 0.152(12) Uiso 1 1 d . . . H3O H 0.281(4) 0.453(2) -0.022(3) 0.176(12) Uiso 1 1 d . . . N1 N 0.30672(14) 0.18065(6) -0.00638(11) 0.0421(3) Uani 1 1 d . . . O1 O 0.21989(14) 0.15395(6) -0.23182(10) 0.0571(3) Uani 1 1 d . . . O2 O 0.42027(15) 0.16661(6) 0.22134(10) 0.0595(3) Uani 1 1 d . . . O3 O 0.22146(13) 0.39313(6) -0.04340(11) 0.0519(3) Uani 1 1 d . . . O4 O 0.47808(11) 0.33002(6) 0.03413(10) 0.0499(3) Uani 1 1 d . . . O5 O 0.67725(14) 0.45595(7) 0.99673(13) 0.0621(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C7 0.0553(7) 0.0349(7) 0.0324(6) -0.0019(5) 0.0093(5) -0.0082(5) C6 0.0491(7) 0.0284(6) 0.0375(7) -0.0028(5) 0.0120(5) -0.0088(5) C5 0.0477(7) 0.0284(6) 0.0375(7) 0.0003(5) 0.0103(5) -0.0084(5) C4 0.0480(7) 0.0329(6) 0.0429(7) 0.0021(5) 0.0121(6) -0.0078(5) C3 0.0504(7) 0.0330(6) 0.0439(7) -0.0044(5) 0.0135(6) -0.0066(5) C2 0.0408(7) 0.0337(7) 0.0617(9) -0.0022(6) 0.0142(7) -0.0030(5) C1 0.0396(6) 0.0326(6) 0.0426(7) -0.0021(5) 0.0146(5) 0.0008(5) C8 0.0500(7) 0.0482(8) 0.0374(7) -0.0004(6) 0.0077(6) 0.0067(6) C9 0.0412(7) 0.0412(7) 0.0450(7) 0.0002(6) 0.0131(6) 0.0085(5) C10 0.0558(8) 0.0468(8) 0.0547(9) 0.0062(7) 0.0209(7) 0.0085(7) C11 0.0551(8) 0.0426(8) 0.0801(12) 0.0046(7) 0.0289(8) 0.0036(6) C12 0.0457(7) 0.0421(8) 0.0840(12) -0.0103(8) 0.0156(8) 0.0002(6) C13 0.0485(8) 0.0503(9) 0.0554(9) -0.0110(7) 0.0063(6) 0.0039(6) C14 0.0394(6) 0.0405(7) 0.0449(7) -0.0038(6) 0.0092(5) 0.0071(5) C15 0.0566(9) 0.0471(9) 0.0971(13) -0.0034(8) 0.0342(9) 0.0022(7) N1 0.0504(6) 0.0289(5) 0.0458(6) -0.0017(4) 0.0121(5) -0.0036(4) O1 0.0720(7) 0.0490(6) 0.0450(6) 0.0085(5) 0.0088(5) 0.0028(5) O2 0.0809(7) 0.0492(6) 0.0467(6) -0.0127(5) 0.0158(5) 0.0037(5) O3 0.0471(5) 0.0344(5) 0.0682(7) 0.0011(4) 0.0074(5) 0.0077(4) O4 0.0360(5) 0.0433(5) 0.0676(7) 0.0094(5) 0.0108(4) 0.0000(4) O5 0.0487(6) 0.0485(6) 0.0934(9) -0.0061(6) 0.0276(6) 0.0003(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C7 C6 1.3794(18) . ? C7 C5 1.3834(17) 3_655 ? C6 C5 1.3895(17) . ? C6 C3 1.4919(18) . ? C5 C7 1.3835(17) 3_655 ? C5 C4 1.4868(18) . ? C4 O1 1.2015(15) . ? C4 N1 1.3950(17) . ? C3 O2 1.2022(16) . ? C3 N1 1.3939(17) . ? C2 N1 1.4437(17) . ? C2 C1 1.5057(18) . ? C1 O4 1.2336(14) . ? C1 O3 1.2753(15) . ? C8 C9 1.3911(19) . ? C8 C14 1.3960(19) 3_566 ? C9 C14 1.4278(19) . ? C9 C10 1.429(2) . ? C10 C11 1.351(2) . ? C11 C12 1.409(2) . ? C12 C13 1.353(2) . ? C13 C14 1.426(2) . ? C14 C8 1.3960(19) 3_566 ? C15 O5 1.4129(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C7 C5 115.06(11) . 3_655 ? C7 C6 C5 122.46(11) . . ? C7 C6 C3 129.43(11) . . ? C5 C6 C3 108.11(11) . . ? C7 C5 C6 122.48(12) 3_655 . ? C7 C5 C4 129.41(12) 3_655 . ? C6 C5 C4 108.11(11) . . ? O1 C4 N1 125.13(13) . . ? O1 C4 C5 128.99(13) . . ? N1 C4 C5 105.86(11) . . ? O2 C3 N1 125.24(13) . . ? O2 C3 C6 129.11(13) . . ? N1 C3 C6 105.65(11) . . ? N1 C2 C1 114.82(11) . . ? O4 C1 O3 125.16(12) . . ? O4 C1 C2 121.59(11) . . ? O3 C1 C2 113.21(11) . . ? C9 C8 C14 122.04(12) . 3_566 ? C8 C9 C14 119.07(12) . . ? C8 C9 C10 122.63(13) . . ? C14 C9 C10 118.29(13) . . ? C11 C10 C9 121.22(14) . . ? C10 C11 C12 120.60(14) . . ? C13 C12 C11 120.24(14) . . ? C12 C13 C14 121.50(15) . . ? C8 C14 C13 122.96(13) 3_566 . ? C8 C14 C9 118.89(12) 3_566 . ? C13 C14 C9 118.15(13) . . ? C3 N1 C4 112.24(11) . . ? C3 N1 C2 123.91(12) . . ? C4 N1 C2 123.40(12) . . ? 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 C5 C7 C6 C5 0.38(19) 3_655 . . . ? C5 C7 C6 C3 -179.83(12) 3_655 . . . ? C7 C6 C5 C7 -0.4(2) . . . 3_655 ? C3 C6 C5 C7 179.76(11) . . . 3_655 ? C7 C6 C5 C4 179.19(11) . . . . ? C3 C6 C5 C4 -0.64(13) . . . . ? C7 C5 C4 O1 3.0(2) 3_655 . . . ? C6 C5 C4 O1 -176.61(13) . . . . ? C7 C5 C4 N1 -178.70(12) 3_655 . . . ? C6 C5 C4 N1 1.73(13) . . . . ? C7 C6 C3 O2 -0.9(2) . . . . ? C5 C6 C3 O2 178.91(14) . . . . ? C7 C6 C3 N1 179.50(12) . . . . ? C5 C6 C3 N1 -0.69(14) . . . . ? N1 C2 C1 O4 -19.5(2) . . . . ? N1 C2 C1 O3 162.53(12) . . . . ? C14 C8 C9 C14 0.0(2) 3_566 . . . ? C14 C8 C9 C10 178.83(12) 3_566 . . . ? C8 C9 C10 C11 -177.52(13) . . . . ? C14 C9 C10 C11 1.3(2) . . . . ? C9 C10 C11 C12 -1.2(2) . . . . ? C10 C11 C12 C13 -0.1(2) . . . . ? C11 C12 C13 C14 1.3(2) . . . . ? C12 C13 C14 C8 177.55(13) . . . 3_566 ? C12 C13 C14 C9 -1.2(2) . . . . ? C8 C9 C14 C8 0.0(2) . . . 3_566 ? C10 C9 C14 C8 -178.88(12) . . . 3_566 ? C8 C9 C14 C13 178.78(12) . . . . ? C10 C9 C14 C13 -0.07(18) . . . . ? O2 C3 N1 C4 -177.75(13) . . . . ? C6 C3 N1 C4 1.87(14) . . . . ? O2 C3 N1 C2 -5.2(2) . . . . ? C6 C3 N1 C2 174.38(11) . . . . ? O1 C4 N1 C3 176.17(12) . . . . ? C5 C4 N1 C3 -2.26(14) . . . . ? O1 C4 N1 C2 3.6(2) . . . . ? C5 C4 N1 C2 -174.81(11) . . . . ? C1 C2 N1 C3 88.86(16) . . . . ? C1 C2 N1 C4 -99.45(15) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 29.14 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.196 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.041 # Attachment 'IC2.cif' data_nilu08_0m _database_code_depnum_ccdc_archive 'CCDC 290284' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H18 N2 O8' _chemical_formula_weight 510.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5128(4) _cell_length_b 7.8323(5) _cell_length_c 20.1764(14) _cell_angle_alpha 94.067(4) _cell_angle_beta 99.125(4) _cell_angle_gamma 94.832(4) _cell_volume 1163.75(13) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3813 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 29.73 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.109 _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 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8503 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.03 _diffrn_reflns_theta_max 30.02 _reflns_number_total 5510 _reflns_number_gt 4020 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0721P)^2^+0.1750P] 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 5510 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1432 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 C3 C 0.4570(2) 0.4864(2) 0.62723(9) 0.0382(4) Uani 1 1 d . . . C4 C 0.4343(2) 0.57064(19) 0.69394(8) 0.0330(3) Uani 1 1 d . . . C5 C 0.2849(2) 0.6434(2) 0.71210(9) 0.0358(4) Uani 1 1 d . . . C6 C 0.30696(19) 0.70537(19) 0.77913(8) 0.0340(3) Uani 1 1 d . . . C7 C 0.1739(2) 0.7829(2) 0.81710(9) 0.0390(4) Uani 1 1 d . . . C8 C 0.4385(2) 0.7677(2) 0.89211(9) 0.0426(4) Uani 1 1 d . . . C9 C 0.4650(2) 0.6968(2) 0.82427(8) 0.0354(3) Uani 1 1 d . . . C10 C 0.6139(2) 0.6238(2) 0.80598(9) 0.0379(4) Uani 1 1 d . . . C11 C 0.59153(19) 0.56122(19) 0.73924(8) 0.0344(3) Uani 1 1 d . . . C12 C 0.7186(2) 0.4683(2) 0.70351(9) 0.0385(4) Uani 1 1 d . . . C2 C 0.6981(2) 0.3220(2) 0.58833(10) 0.0465(4) Uani 1 1 d . . . H2A H 0.5976 0.2780 0.5533 0.056 Uiso 1 1 calc R . . H2B H 0.7443 0.2244 0.6100 0.056 Uiso 1 1 calc R . . C1 C 0.8443(2) 0.4080(2) 0.55615(8) 0.0359(3) Uani 1 1 d . . . C13 C 0.1725(3) 0.8673(3) 0.93867(11) 0.0514(5) Uani 1 1 d . . . C14 C 0.0901(3) 0.7081(3) 0.96466(10) 0.0509(5) Uani 1 1 d . . . C15 C 0.4028(3) 0.8499(3) 0.17239(11) 0.0541(5) Uani 1 1 d . . . C16 C 0.4592(4) 0.7737(3) 0.11696(13) 0.0681(6) Uani 1 1 d . . . C17 C 0.6318(4) 0.7188(3) 0.12126(13) 0.0660(6) Uani 1 1 d . . . C18 C 0.7452(3) 0.7398(3) 0.18092(13) 0.0588(6) Uani 1 1 d . . . C19 C 0.6921(2) 0.8196(2) 0.23916(10) 0.0443(4) Uani 1 1 d . . . C20 C 0.8126(2) 0.8430(2) 0.30186(11) 0.0532(5) Uani 1 1 d . . . H20 H 0.9264 0.8030 0.3046 0.064 Uiso 1 1 calc R . . C21 C 0.7664(2) 0.9210(2) 0.35672(11) 0.0524(5) Uani 1 1 d . . . H21 H 0.8488 0.9347 0.3967 0.063 Uiso 1 1 calc R . . C22 C 0.5923(2) 0.9842(2) 0.35517(9) 0.0403(4) Uani 1 1 d . . . C23 C 0.5461(3) 1.0707(2) 0.41285(10) 0.0477(4) Uani 1 1 d . . . C24 C 0.3807(3) 1.1330(2) 0.41086(11) 0.0514(5) Uani 1 1 d . . . C25 C 0.2557(3) 1.1090(2) 0.35186(11) 0.0498(5) Uani 1 1 d . . . H25 H 0.1431 1.1508 0.3507 0.060 Uiso 1 1 calc R . . C26 C 0.2962(2) 1.0242(2) 0.29494(10) 0.0442(4) Uani 1 1 d . . . H26 H 0.2102 1.0087 0.2559 0.053 Uiso 1 1 calc R . . C27 C 0.4657(2) 0.96034(19) 0.29477(9) 0.0368(4) Uani 1 1 d . . . C28 C 0.5174(2) 0.8765(2) 0.23482(9) 0.0391(4) Uani 1 1 d . . . H1 H 0.982(4) 0.348(4) 0.4912(15) 0.104(9) Uiso 1 1 d . . . H10 H 0.725(2) 0.615(2) 0.8393(9) 0.043(5) Uiso 1 1 d . . . H5 H 0.172(2) 0.648(2) 0.6790(9) 0.040(5) Uiso 1 1 d . . . H15 H 0.278(3) 0.892(3) 0.1700(11) 0.065(6) Uiso 1 1 d . . . H16 H 0.376(4) 0.758(3) 0.0764(15) 0.092(9) Uiso 1 1 d . . . H17 H 0.667(4) 0.663(4) 0.0788(15) 0.103(9) Uiso 1 1 d . . . H18 H 0.871(3) 0.701(3) 0.1859(11) 0.065(6) Uiso 1 1 d . . . H23 H 0.637(3) 1.086(3) 0.4533(12) 0.067(7) Uiso 1 1 d . . . H24 H 0.350(3) 1.201(3) 0.4507(12) 0.070(7) Uiso 1 1 d . . . H8 H -0.038(4) 0.634(4) 1.0299(16) 0.122(11) Uiso 1 1 d . . . H13A H 0.074(3) 0.937(3) 0.9239(12) 0.076(7) Uiso 1 1 d . . . H13B H 0.260(3) 0.937(3) 0.9782(13) 0.074(7) Uiso 1 1 d . . . N1 N 0.63068(18) 0.43163(17) 0.63759(7) 0.0399(3) Uani 1 1 d . . . N2 N 0.26393(19) 0.81970(19) 0.88310(7) 0.0435(4) Uani 1 1 d . . . O1 O 0.35199(19) 0.46443(18) 0.57510(7) 0.0550(3) Uani 1 1 d . . . O2 O 0.86616(16) 0.42716(17) 0.72537(7) 0.0546(4) Uani 1 1 d . . . O3 O 0.01959(16) 0.80897(17) 0.79767(7) 0.0544(4) Uani 1 1 d . . . O4 O 0.5404(2) 0.7786(2) 0.94498(7) 0.0651(4) Uani 1 1 d . . . O5 O 0.90808(18) 0.29615(15) 0.51742(7) 0.0495(3) Uani 1 1 d . . . O6 O 0.89351(16) 0.56093(14) 0.56467(6) 0.0446(3) Uani 1 1 d . . . O7 O 0.0939(2) 0.56478(19) 0.93914(8) 0.0734(5) Uani 1 1 d . . . O8 O 0.0160(2) 0.7427(2) 1.01808(8) 0.0685(5) 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 C3 0.0443(9) 0.0349(8) 0.0370(9) 0.0055(7) 0.0123(8) 0.0007(6) C4 0.0356(8) 0.0324(7) 0.0326(8) 0.0059(6) 0.0097(7) 0.0032(6) C5 0.0339(8) 0.0390(8) 0.0362(9) 0.0082(7) 0.0073(7) 0.0070(6) C6 0.0319(7) 0.0346(8) 0.0391(9) 0.0089(6) 0.0125(7) 0.0059(6) C7 0.0390(8) 0.0373(8) 0.0453(10) 0.0091(7) 0.0164(8) 0.0079(6) C8 0.0454(9) 0.0499(10) 0.0351(10) 0.0049(8) 0.0113(8) 0.0096(7) C9 0.0357(8) 0.0393(8) 0.0334(8) 0.0057(7) 0.0102(7) 0.0056(6) C10 0.0318(8) 0.0456(9) 0.0375(9) 0.0045(7) 0.0076(7) 0.0061(6) C11 0.0310(7) 0.0351(8) 0.0398(9) 0.0053(7) 0.0123(7) 0.0046(6) C12 0.0340(8) 0.0372(8) 0.0471(10) 0.0022(7) 0.0159(7) 0.0033(6) C2 0.0549(10) 0.0365(8) 0.0515(11) -0.0057(8) 0.0271(9) -0.0014(7) C1 0.0394(8) 0.0353(8) 0.0349(9) 0.0021(7) 0.0112(7) 0.0061(6) C13 0.0614(12) 0.0553(11) 0.0459(11) 0.0043(9) 0.0278(10) 0.0175(9) C14 0.0513(10) 0.0604(11) 0.0472(11) 0.0018(9) 0.0244(9) 0.0136(8) C15 0.0567(12) 0.0566(12) 0.0493(12) 0.0080(9) 0.0043(10) 0.0123(9) C16 0.0864(17) 0.0732(15) 0.0451(13) 0.0059(11) 0.0075(13) 0.0148(12) C17 0.0859(16) 0.0597(13) 0.0590(15) 0.0058(11) 0.0281(13) 0.0134(11) C18 0.0591(12) 0.0505(11) 0.0749(16) 0.0103(10) 0.0298(12) 0.0121(9) C19 0.0412(9) 0.0372(8) 0.0574(11) 0.0101(8) 0.0141(9) 0.0042(7) C20 0.0336(9) 0.0548(11) 0.0718(14) 0.0110(10) 0.0065(9) 0.0073(7) C21 0.0366(9) 0.0549(11) 0.0624(13) 0.0098(9) -0.0028(9) 0.0024(8) C22 0.0385(8) 0.0342(8) 0.0484(10) 0.0094(7) 0.0068(8) -0.0004(6) C23 0.0546(11) 0.0403(9) 0.0454(11) 0.0031(8) 0.0046(9) -0.0036(8) C24 0.0641(12) 0.0363(9) 0.0565(12) 0.0017(8) 0.0201(11) 0.0035(8) C25 0.0471(10) 0.0389(9) 0.0676(13) 0.0099(9) 0.0169(10) 0.0101(7) C26 0.0405(9) 0.0402(9) 0.0529(11) 0.0102(8) 0.0065(8) 0.0069(7) C27 0.0362(8) 0.0306(7) 0.0445(10) 0.0093(7) 0.0074(7) 0.0019(6) C28 0.0401(8) 0.0346(8) 0.0444(10) 0.0111(7) 0.0088(8) 0.0048(6) N1 0.0440(7) 0.0377(7) 0.0415(8) 0.0000(6) 0.0194(7) 0.0034(5) N2 0.0470(8) 0.0501(8) 0.0393(8) 0.0043(6) 0.0201(7) 0.0127(6) O1 0.0626(8) 0.0632(9) 0.0373(7) -0.0008(6) 0.0047(7) 0.0072(6) O2 0.0385(6) 0.0616(8) 0.0653(9) -0.0036(7) 0.0114(6) 0.0164(6) O3 0.0399(7) 0.0627(8) 0.0653(9) 0.0072(7) 0.0147(6) 0.0193(6) O4 0.0676(9) 0.0930(11) 0.0351(8) -0.0028(7) 0.0041(7) 0.0246(8) O5 0.0592(7) 0.0366(6) 0.0595(8) -0.0028(6) 0.0336(7) 0.0041(5) O6 0.0536(7) 0.0354(6) 0.0487(7) -0.0020(5) 0.0248(6) 0.0011(5) O7 0.1076(12) 0.0539(9) 0.0720(10) 0.0011(7) 0.0580(10) 0.0065(8) O8 0.0842(10) 0.0653(9) 0.0674(10) -0.0020(8) 0.0511(9) 0.0070(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 C3 O1 1.203(2) . ? C3 N1 1.397(2) . ? C3 C4 1.497(2) . ? C4 C11 1.385(2) . ? C4 C5 1.388(2) . ? C5 C6 1.384(2) . ? C6 C9 1.387(2) . ? C6 C7 1.495(2) . ? C7 O3 1.203(2) . ? C7 N2 1.393(2) . ? C8 O4 1.203(2) . ? C8 N2 1.394(2) . ? C8 C9 1.490(2) . ? C9 C10 1.386(2) . ? C10 C11 1.379(2) . ? C11 C12 1.490(2) . ? C12 O2 1.205(2) . ? C12 N1 1.387(2) . ? C2 N1 1.4468(19) . ? C2 C1 1.499(2) . ? C1 O6 1.2154(19) . ? C1 O5 1.3039(18) . ? C13 N2 1.448(2) . ? C13 C14 1.510(3) . ? C14 O7 1.206(2) . ? C14 O8 1.312(2) . ? C15 C16 1.373(3) . ? C15 C28 1.400(3) . ? C16 C17 1.392(4) . ? C17 C18 1.351(3) . ? C18 C19 1.420(3) . ? C19 C28 1.413(2) . ? C19 C20 1.425(3) . ? C20 C21 1.335(3) . ? C21 C22 1.433(2) . ? C22 C23 1.410(3) . ? C22 C27 1.412(2) . ? C23 C24 1.369(3) . ? C24 C25 1.385(3) . ? C25 C26 1.375(3) . ? C26 C27 1.407(2) . ? C27 C28 1.457(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 O1 C3 N1 125.30(15) . . ? O1 C3 C4 129.58(15) . . ? N1 C3 C4 105.10(14) . . ? C11 C4 C5 122.66(15) . . ? C11 C4 C3 108.28(13) . . ? C5 C4 C3 129.03(15) . . ? C6 C5 C4 114.20(16) . . ? C5 C6 C9 122.99(14) . . ? C5 C6 C7 129.20(15) . . ? C9 C6 C7 107.76(14) . . ? O3 C7 N2 124.76(14) . . ? O3 C7 C6 129.50(17) . . ? N2 C7 C6 105.74(13) . . ? O4 C8 N2 125.14(15) . . ? O4 C8 C9 129.39(16) . . ? N2 C8 C9 105.46(15) . . ? C10 C9 C6 122.64(15) . . ? C10 C9 C8 128.73(16) . . ? C6 C9 C8 108.54(13) . . ? C11 C10 C9 114.37(16) . . ? C10 C11 C4 123.12(14) . . ? C10 C11 C12 128.74(15) . . ? C4 C11 C12 108.09(14) . . ? O2 C12 N1 124.99(14) . . ? O2 C12 C11 129.20(17) . . ? N1 C12 C11 105.79(13) . . ? N1 C2 C1 114.73(13) . . ? O6 C1 O5 125.39(14) . . ? O6 C1 C2 124.24(13) . . ? O5 C1 C2 110.37(13) . . ? N2 C13 C14 109.98(15) . . ? O7 C14 O8 123.95(19) . . ? O7 C14 C13 123.34(15) . . ? O8 C14 C13 112.71(17) . . ? C16 C15 C28 121.2(2) . . ? C15 C16 C17 121.0(2) . . ? C18 C17 C16 119.6(2) . . ? C17 C18 C19 121.0(2) . . ? C28 C19 C18 119.55(19) . . ? C28 C19 C20 119.59(16) . . ? C18 C19 C20 120.87(17) . . ? C21 C20 C19 121.66(17) . . ? C20 C21 C22 121.32(19) . . ? C23 C22 C27 119.58(16) . . ? C23 C22 C21 121.03(18) . . ? C27 C22 C21 119.39(16) . . ? C24 C23 C22 120.8(2) . . ? C23 C24 C25 119.79(18) . . ? C26 C25 C24 120.75(17) . . ? C25 C26 C27 121.11(18) . . ? C26 C27 C22 117.94(16) . . ? C26 C27 C28 122.93(17) . . ? C22 C27 C28 119.09(14) . . ? C15 C28 C19 117.73(16) . . ? C15 C28 C27 123.35(16) . . ? C19 C28 C27 118.91(16) . . ? C12 N1 C3 112.71(13) . . ? C12 N1 C2 123.25(14) . . ? C3 N1 C2 123.17(15) . . ? C7 N2 C8 112.44(13) . . ? C7 N2 C13 122.97(15) . . ? C8 N2 C13 123.01(16) . . ? 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 C3 C4 C11 178.52(16) . . . . ? N1 C3 C4 C11 -0.16(16) . . . . ? O1 C3 C4 C5 0.5(3) . . . . ? N1 C3 C4 C5 -178.16(15) . . . . ? C11 C4 C5 C6 0.0(2) . . . . ? C3 C4 C5 C6 177.79(14) . . . . ? C4 C5 C6 C9 0.4(2) . . . . ? C4 C5 C6 C7 -176.60(14) . . . . ? C5 C6 C7 O3 -0.4(3) . . . . ? C9 C6 C7 O3 -177.74(17) . . . . ? C5 C6 C7 N2 178.68(15) . . . . ? C9 C6 C7 N2 1.32(17) . . . . ? C5 C6 C9 C10 -0.5(2) . . . . ? C7 C6 C9 C10 177.01(14) . . . . ? C5 C6 C9 C8 -177.45(14) . . . . ? C7 C6 C9 C8 0.11(17) . . . . ? O4 C8 C9 C10 1.0(3) . . . . ? N2 C8 C9 C10 -178.15(16) . . . . ? O4 C8 C9 C6 177.64(19) . . . . ? N2 C8 C9 C6 -1.50(18) . . . . ? C6 C9 C10 C11 0.2(2) . . . . ? C8 C9 C10 C11 176.43(16) . . . . ? C9 C10 C11 C4 0.2(2) . . . . ? C9 C10 C11 C12 -176.83(15) . . . . ? C5 C4 C11 C10 -0.4(2) . . . . ? C3 C4 C11 C10 -178.54(14) . . . . ? C5 C4 C11 C12 177.22(14) . . . . ? C3 C4 C11 C12 -0.93(16) . . . . ? C10 C11 C12 O2 0.7(3) . . . . ? C4 C11 C12 O2 -176.70(17) . . . . ? C10 C11 C12 N1 179.12(15) . . . . ? C4 C11 C12 N1 1.70(16) . . . . ? N1 C2 C1 O6 -6.8(3) . . . . ? N1 C2 C1 O5 174.10(16) . . . . ? N2 C13 C14 O7 -3.9(3) . . . . ? N2 C13 C14 O8 175.62(18) . . . . ? C28 C15 C16 C17 0.6(3) . . . . ? C15 C16 C17 C18 0.4(4) . . . . ? C16 C17 C18 C19 -1.0(3) . . . . ? C17 C18 C19 C28 0.6(3) . . . . ? C17 C18 C19 C20 -179.38(18) . . . . ? C28 C19 C20 C21 -1.4(3) . . . . ? C18 C19 C20 C21 178.54(18) . . . . ? C19 C20 C21 C22 0.4(3) . . . . ? C20 C21 C22 C23 -178.25(17) . . . . ? C20 C21 C22 C27 1.3(3) . . . . ? C27 C22 C23 C24 -0.5(2) . . . . ? C21 C22 C23 C24 179.04(16) . . . . ? C22 C23 C24 C25 0.9(3) . . . . ? C23 C24 C25 C26 -0.4(3) . . . . ? C24 C25 C26 C27 -0.4(3) . . . . ? C25 C26 C27 C22 0.8(2) . . . . ? C25 C26 C27 C28 -177.18(15) . . . . ? C23 C22 C27 C26 -0.3(2) . . . . ? C21 C22 C27 C26 -179.88(15) . . . . ? C23 C22 C27 C28 177.73(14) . . . . ? C21 C22 C27 C28 -1.8(2) . . . . ? C16 C15 C28 C19 -1.0(3) . . . . ? C16 C15 C28 C27 178.51(18) . . . . ? C18 C19 C28 C15 0.4(2) . . . . ? C20 C19 C28 C15 -179.59(16) . . . . ? C18 C19 C28 C27 -179.14(15) . . . . ? C20 C19 C28 C27 0.8(2) . . . . ? C26 C27 C28 C15 -0.8(2) . . . . ? C22 C27 C28 C15 -178.77(15) . . . . ? C26 C27 C28 C19 178.71(14) . . . . ? C22 C27 C28 C19 0.8(2) . . . . ? O2 C12 N1 C3 176.61(16) . . . . ? C11 C12 N1 C3 -1.87(17) . . . . ? O2 C12 N1 C2 7.0(2) . . . . ? C11 C12 N1 C2 -171.47(13) . . . . ? O1 C3 N1 C12 -177.45(15) . . . . ? C4 C3 N1 C12 1.31(16) . . . . ? O1 C3 N1 C2 -7.8(2) . . . . ? C4 C3 N1 C2 170.92(13) . . . . ? C1 C2 N1 C12 -80.7(2) . . . . ? C1 C2 N1 C3 110.74(18) . . . . ? O3 C7 N2 C8 176.74(16) . . . . ? C6 C7 N2 C8 -2.38(18) . . . . ? O3 C7 N2 C13 10.7(3) . . . . ? C6 C7 N2 C13 -168.44(15) . . . . ? O4 C8 N2 C7 -176.75(18) . . . . ? C9 C8 N2 C7 2.44(18) . . . . ? O4 C8 N2 C13 -10.7(3) . . . . ? C9 C8 N2 C13 168.49(16) . . . . ? C14 C13 N2 C7 83.0(2) . . . . ? C14 C13 N2 C8 -81.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.811 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.811 _refine_diff_density_max 0.220 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.073 # Attachment 'IC32.cif' data_rj074_0m_b _database_code_depnum_ccdc_archive 'CCDC 290285' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H20 N2 O8' _chemical_formula_sum 'C34 H20 N2 O8' _chemical_formula_weight 584.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.30190(10) _cell_length_b 8.91020(10) _cell_length_c 10.7840(2) _cell_angle_alpha 80.3110(10) _cell_angle_beta 77.5280(10) _cell_angle_gamma 78.2830(10) _cell_volume 665.083(17) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2025 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 29.01 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 302 _exptl_absorpt_coefficient_mu 0.106 _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 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6206 _diffrn_reflns_av_R_equivalents 0.0137 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 29.15 _reflns_number_total 3241 _reflns_number_gt 2337 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+0.0947P] 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 3241 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1254 _refine_ls_wR_factor_gt 0.1113 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.16951(18) 0.53688(16) -0.08706(14) 0.0444(3) Uani 1 1 d . . . H1 H 0.2787 0.5607 -0.1433 0.053 Uiso 1 1 calc R . . C2 C 0.12703(17) 0.56499(15) 0.03866(13) 0.0418(3) Uani 1 1 d . . . C3 C -0.03656(18) 0.52965(15) 0.12295(13) 0.0421(3) Uani 1 1 d . . . C4 C -0.0357(2) 0.57477(17) 0.24914(15) 0.0507(4) Uani 1 1 d . . . C5 C 0.2351(2) 0.63628(16) 0.10892(15) 0.0493(4) Uani 1 1 d . . . C6 C 0.1765(3) 0.7097(2) 0.3289(2) 0.0642(5) Uani 1 1 d . . . C7 C 0.3267(2) 0.61121(17) 0.39743(14) 0.0467(3) Uani 1 1 d . . . C8 C 0.3634(3) 0.0486(2) -0.2987(2) 0.0774(5) Uani 1 1 d . . . H8 H 0.4700 0.0775 -0.3548 0.093 Uiso 1 1 calc R . . C9 C 0.3247(2) 0.0822(2) -0.17363(18) 0.0643(4) Uani 1 1 d . . . H9 H 0.4059 0.1336 -0.1477 0.077 Uiso 1 1 calc R . . C10 C 0.16797(19) 0.04089(16) -0.08669(15) 0.0493(3) Uani 1 1 d . . . C11 C 0.12672(19) 0.07468(16) 0.04567(15) 0.0485(3) Uani 1 1 d . . . C12 C 0.2458(2) 0.14410(19) 0.09444(19) 0.0617(4) Uani 1 1 d . . . H12 H 0.3571 0.1690 0.0415 0.074 Uiso 1 1 calc R . . C13 C 0.2030(3) 0.1772(2) 0.2198(2) 0.0718(5) Uani 1 1 d . . . H13 H 0.2852 0.2238 0.2495 0.086 Uiso 1 1 calc R . . C14 C 0.0420(3) 0.1421(2) 0.2992(2) 0.0698(5) Uani 1 1 d . . . H14 H 0.0140 0.1664 0.3826 0.084 Uiso 1 1 calc R . . C15 C -0.0835(2) 0.06930(18) 0.25710(17) 0.0588(4) Uani 1 1 d . . . C16 C -0.2481(3) 0.0259(2) 0.34026(19) 0.0735(5) Uani 1 1 d . . . H16 H -0.2774 0.0486 0.4241 0.088 Uiso 1 1 calc R . . C17 C -0.0419(2) 0.03495(15) 0.12913(15) 0.0479(3) Uani 1 1 d . . . H5 H 0.466(5) 0.617(4) 0.537(3) 0.167(12) Uiso 1 1 d . . . H6A H 0.214(3) 0.806(3) 0.295(2) 0.090(7) Uiso 1 1 d . . . H6B H 0.063(4) 0.731(3) 0.391(2) 0.096(7) Uiso 1 1 d . . . N1 N 0.12912(18) 0.63829(14) 0.23219(13) 0.0521(3) Uani 1 1 d . . . O1 O 0.38242(16) 0.68431(14) 0.07127(13) 0.0695(4) Uani 1 1 d . . . O2 O -0.14886(19) 0.56217(16) 0.34794(12) 0.0723(4) Uani 1 1 d . . . O3 O 0.39406(16) 0.47715(12) 0.37524(10) 0.0576(3) Uani 1 1 d . . . O4 O 0.37183(16) 0.68098(12) 0.47709(11) 0.0587(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0376(6) 0.0501(8) 0.0456(8) 0.0003(6) -0.0085(5) -0.0125(5) C2 0.0385(6) 0.0434(7) 0.0458(8) 0.0014(5) -0.0147(6) -0.0111(5) C3 0.0418(7) 0.0445(7) 0.0405(7) 0.0003(5) -0.0122(6) -0.0084(5) C4 0.0541(8) 0.0515(8) 0.0475(9) -0.0050(6) -0.0171(7) -0.0050(6) C5 0.0475(7) 0.0451(8) 0.0613(10) -0.0026(6) -0.0247(7) -0.0100(6) C6 0.0733(11) 0.0584(11) 0.0720(12) -0.0231(9) -0.0400(10) 0.0033(9) C7 0.0539(8) 0.0481(8) 0.0422(8) -0.0086(6) -0.0160(6) -0.0091(6) C8 0.0700(11) 0.0738(12) 0.0775(14) -0.0111(10) 0.0169(10) -0.0191(9) C9 0.0516(9) 0.0615(10) 0.0741(12) -0.0076(8) 0.0037(8) -0.0144(7) C10 0.0415(7) 0.0388(7) 0.0618(10) -0.0010(6) -0.0060(6) -0.0024(5) C11 0.0430(7) 0.0377(7) 0.0611(9) -0.0001(6) -0.0110(6) -0.0025(5) C12 0.0509(8) 0.0530(9) 0.0819(13) -0.0029(8) -0.0164(8) -0.0112(7) C13 0.0792(12) 0.0583(10) 0.0874(14) -0.0142(9) -0.0350(11) -0.0095(9) C14 0.0888(13) 0.0561(10) 0.0649(11) -0.0115(8) -0.0225(10) -0.0021(9) C15 0.0658(10) 0.0440(8) 0.0610(10) -0.0055(7) -0.0100(8) 0.0005(7) C16 0.0853(13) 0.0634(11) 0.0587(11) -0.0108(8) 0.0068(9) -0.0019(9) C17 0.0465(7) 0.0360(7) 0.0551(9) -0.0001(6) -0.0076(6) 0.0000(5) N1 0.0553(7) 0.0556(7) 0.0527(8) -0.0105(5) -0.0251(6) -0.0074(5) O1 0.0559(6) 0.0760(8) 0.0891(9) -0.0093(7) -0.0240(6) -0.0303(6) O2 0.0783(8) 0.0916(9) 0.0456(7) -0.0122(6) -0.0025(6) -0.0188(7) O3 0.0725(7) 0.0518(6) 0.0543(7) -0.0152(5) -0.0281(5) 0.0000(5) O4 0.0784(7) 0.0505(6) 0.0579(7) -0.0120(5) -0.0348(6) -0.0085(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.378(2) . ? C1 C3 1.3845(18) 2_565 ? C2 C3 1.3927(19) . ? C2 C5 1.4916(18) . ? C3 C1 1.3845(18) 2_565 ? C3 C4 1.484(2) . ? C4 O2 1.2032(19) . ? C4 N1 1.396(2) . ? C5 O1 1.2019(18) . ? C5 N1 1.387(2) . ? C6 N1 1.4432(19) . ? C6 C7 1.503(2) . ? C7 O3 1.2380(17) . ? C7 O4 1.2721(16) . ? C8 C16 1.356(3) 2 ? C8 C9 1.387(3) . ? C9 C10 1.384(2) . ? C10 C17 1.433(2) 2 ? C10 C11 1.463(2) . ? C11 C12 1.393(2) . ? C11 C17 1.429(2) . ? C12 C13 1.388(3) . ? C13 C14 1.355(3) . ? C14 C15 1.409(3) . ? C15 C16 1.416(3) . ? C15 C17 1.419(2) . ? C16 C8 1.356(3) 2 ? C17 C10 1.433(2) 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 C3 114.59(13) . 2_565 ? C1 C2 C3 122.78(12) . . ? C1 C2 C5 129.20(13) . . ? C3 C2 C5 108.01(13) . . ? C1 C3 C2 122.62(13) 2_565 . ? C1 C3 C4 129.21(13) 2_565 . ? C2 C3 C4 108.17(12) . . ? O2 C4 N1 124.89(14) . . ? O2 C4 C3 129.54(14) . . ? N1 C4 C3 105.57(13) . . ? O1 C5 N1 125.02(14) . . ? O1 C5 C2 129.42(15) . . ? N1 C5 C2 105.55(12) . . ? N1 C6 C7 114.48(13) . . ? O3 C7 O4 126.08(12) . . ? O3 C7 C6 121.28(12) . . ? O4 C7 C6 112.65(13) . . ? C16 C8 C9 121.03(18) 2 . ? C10 C9 C8 121.47(18) . . ? C9 C10 C17 118.54(16) . 2 ? C9 C10 C11 121.90(15) . . ? C17 C10 C11 119.55(13) 2 . ? C12 C11 C17 118.23(16) . . ? C12 C11 C10 122.64(15) . . ? C17 C11 C10 119.13(13) . . ? C13 C12 C11 121.81(17) . . ? C14 C13 C12 120.44(17) . . ? C13 C14 C15 120.87(18) . . ? C14 C15 C16 121.66(18) . . ? C14 C15 C17 119.37(17) . . ? C16 C15 C17 118.94(17) . . ? C8 C16 C15 120.57(18) 2 . ? C15 C17 C11 119.26(14) . . ? C15 C17 C10 119.44(14) . 2 ? C11 C17 C10 121.30(14) . 2 ? C5 N1 C4 112.69(12) . . ? C5 N1 C6 123.40(15) . . ? C4 N1 C6 123.73(16) . . ? 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 C3 C1 C2 C3 -0.1(2) 2_565 . . . ? C3 C1 C2 C5 -179.16(12) 2_565 . . . ? C1 C2 C3 C1 0.1(2) . . . 2_565 ? C5 C2 C3 C1 179.35(12) . . . 2_565 ? C1 C2 C3 C4 179.85(12) . . . . ? C5 C2 C3 C4 -0.92(14) . . . . ? C1 C3 C4 O2 0.8(3) 2_565 . . . ? C2 C3 C4 O2 -178.91(16) . . . . ? C1 C3 C4 N1 -179.15(13) 2_565 . . . ? C2 C3 C4 N1 1.13(15) . . . . ? C1 C2 C5 O1 -0.1(2) . . . . ? C3 C2 C5 O1 -179.29(15) . . . . ? C1 C2 C5 N1 179.53(13) . . . . ? C3 C2 C5 N1 0.36(14) . . . . ? N1 C6 C7 O3 -3.6(3) . . . . ? N1 C6 C7 O4 176.52(16) . . . . ? C16 C8 C9 C10 0.2(3) 2 . . . ? C8 C9 C10 C17 -1.5(2) . . . 2 ? C8 C9 C10 C11 179.50(15) . . . . ? C9 C10 C11 C12 -2.8(2) . . . . ? C17 C10 C11 C12 178.13(12) 2 . . . ? C9 C10 C11 C17 177.33(13) . . . . ? C17 C10 C11 C17 -1.7(2) 2 . . . ? C17 C11 C12 C13 -1.1(2) . . . . ? C10 C11 C12 C13 179.09(14) . . . . ? C11 C12 C13 C14 0.1(3) . . . . ? C12 C13 C14 C15 1.0(3) . . . . ? C13 C14 C15 C16 177.30(16) . . . . ? C13 C14 C15 C17 -1.1(2) . . . . ? C14 C15 C16 C8 -177.85(17) . . . 2 ? C17 C15 C16 C8 0.6(3) . . . 2 ? C14 C15 C17 C11 0.1(2) . . . . ? C16 C15 C17 C11 -178.33(13) . . . . ? C14 C15 C17 C10 179.18(13) . . . 2 ? C16 C15 C17 C10 0.7(2) . . . 2 ? C12 C11 C17 C15 0.93(19) . . . . ? C10 C11 C17 C15 -179.23(12) . . . . ? C12 C11 C17 C10 -178.11(12) . . . 2 ? C10 C11 C17 C10 1.7(2) . . . 2 ? O1 C5 N1 C4 -179.94(14) . . . . ? C2 C5 N1 C4 0.39(15) . . . . ? O1 C5 N1 C6 4.8(2) . . . . ? C2 C5 N1 C6 -174.89(12) . . . . ? O2 C4 N1 C5 179.10(15) . . . . ? C3 C4 N1 C5 -0.94(15) . . . . ? O2 C4 N1 C6 -5.6(2) . . . . ? C3 C4 N1 C6 174.33(13) . . . . ? C7 C6 N1 C5 -82.0(2) . . . . ? C7 C6 N1 C4 103.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 29.15 _diffrn_measured_fraction_theta_full 0.904 _refine_diff_density_max 0.201 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.045 # Attachment 'IC4.cif' data_adttf_1 _database_code_depnum_ccdc_archive 'CCDC 603958' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H12 N2 O8 S4' _chemical_formula_weight 536.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7829(5) _cell_length_b 9.8027(7) _cell_length_c 15.4096(10) _cell_angle_alpha 97.584(5) _cell_angle_beta 97.404(4) _cell_angle_gamma 107.850(4) _cell_volume 1091.26(13) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2813 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 26.33 _exptl_crystal_description plates _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.633 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 0.488 _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 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12076 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 28.37 _reflns_number_total 4976 _reflns_number_gt 3125 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0469P)^2^+0.1500P] 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 4976 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0824 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.0885 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 S1 S 0.90814(8) 0.50522(7) 0.88883(4) 0.04257(18) Uani 1 1 d . . . S3 S 1.07607(8) 0.46809(7) 0.62838(4) 0.04048(17) Uani 1 1 d . . . S2 S 0.84639(8) 0.25168(7) 0.74712(4) 0.04167(17) Uani 1 1 d . . . S4 S 1.13733(9) 0.71982(7) 0.77110(5) 0.04568(18) Uani 1 1 d . . . O1 O 0.5806(3) 0.9283(3) 0.05303(18) 0.0650(7) Uani 1 1 d . . . O5 O 0.2950(2) 0.4413(2) 0.46643(12) 0.0536(5) Uani 1 1 d . . . O3 O 0.6924(2) 0.5615(2) 0.04893(13) 0.0556(5) Uani 1 1 d . . . O8 O 0.2402(3) -0.0431(2) 0.48327(15) 0.0635(6) Uani 1 1 d . . . O6 O 0.2667(3) 0.0953(2) 0.23235(14) 0.0640(6) Uani 1 1 d . . . O7 O 0.4751(2) 0.1275(2) 0.45260(15) 0.0659(6) Uani 1 1 d . . . O4 O 0.7248(3) 0.9080(2) 0.28442(15) 0.0618(5) Uani 1 1 d . . . O2 O 0.8348(3) 1.0106(3) 0.00199(17) 0.0891(8) Uani 1 1 d . . . N1 N 0.7243(2) 0.7619(2) 0.15434(14) 0.0398(5) Uani 1 1 d . . . N2 N 0.2536(3) 0.2423(2) 0.35868(14) 0.0400(5) Uani 1 1 d . . . C17 C 0.9452(3) 0.4419(3) 0.78381(16) 0.0358(5) Uani 1 1 d . . . C18 C 1.0384(3) 0.5307(2) 0.73394(15) 0.0346(5) Uani 1 1 d . . . C16 C 0.7503(3) 0.2213(3) 0.84205(19) 0.0446(6) Uani 1 1 d . . . C19 C 1.1958(4) 0.6404(3) 0.6113(2) 0.0476(7) Uani 1 1 d . . . C20 C 1.2227(4) 0.7523(3) 0.6745(2) 0.0507(7) Uani 1 1 d . . . C15 C 0.7769(3) 0.3346(3) 0.90452(19) 0.0451(6) Uani 1 1 d . . . C5 C 0.4962(3) 0.6124(3) 0.32969(17) 0.0349(5) Uani 1 1 d . . . C12 C 0.6638(3) 0.6131(3) 0.11856(17) 0.0385(6) Uani 1 1 d . . . C4 C 0.5741(3) 0.6454(2) 0.25640(16) 0.0330(5) Uani 1 1 d . . . C6 C 0.4085(3) 0.4652(2) 0.32720(15) 0.0327(5) Uani 1 1 d . . . C10 C 0.4775(3) 0.3927(3) 0.18196(17) 0.0360(5) Uani 1 1 d . . . C8 C 0.3015(3) 0.2155(3) 0.27621(18) 0.0406(6) Uani 1 1 d . . . C7 C 0.3158(3) 0.3909(3) 0.39475(16) 0.0371(6) Uani 1 1 d . . . C9 C 0.4000(3) 0.3597(2) 0.25571(16) 0.0333(5) Uani 1 1 d . . . C3 C 0.6798(3) 0.7897(3) 0.23785(18) 0.0402(6) Uani 1 1 d . . . C2 C 0.8417(4) 0.8698(4) 0.1135(2) 0.0509(7) Uani 1 1 d . . . C1 C 0.7453(3) 0.9397(3) 0.05196(19) 0.0464(7) Uani 1 1 d . . . C14 C 0.3130(4) 0.0716(3) 0.44916(17) 0.0445(6) Uani 1 1 d . . . C13 C 0.1714(4) 0.1296(4) 0.4064(2) 0.0511(7) Uani 1 1 d . . . C11 C 0.5648(3) 0.5389(2) 0.18507(15) 0.0331(5) Uani 1 1 d . . . H15 H 0.732(3) 0.332(3) 0.9623(17) 0.041(7) Uiso 1 1 d . . . H16 H 0.688(3) 0.122(3) 0.8434(17) 0.052(8) Uiso 1 1 d . . . H19 H 1.237(4) 0.650(3) 0.557(2) 0.072(9) Uiso 1 1 d . . . H20 H 1.281(4) 0.851(3) 0.6696(19) 0.063(9) Uiso 1 1 d . . . H13B H 0.114(4) 0.167(3) 0.453(2) 0.079(10) Uiso 1 1 d . . . H13A H 0.084(4) 0.056(3) 0.369(2) 0.069(10) Uiso 1 1 d . . . H5 H 0.506(3) 0.683(2) 0.3777(15) 0.030(6) Uiso 1 1 d . . . H10 H 0.470(3) 0.321(3) 0.1335(17) 0.044(7) Uiso 1 1 d . . . H2A H 0.921(4) 0.948(3) 0.161(2) 0.076(10) Uiso 1 1 d . . . H2B H 0.914(4) 0.826(3) 0.079(2) 0.072(10) Uiso 1 1 d . . . H8O H 0.323(5) -0.070(4) 0.501(3) 0.108(15) Uiso 1 1 d . . . H1O H 0.563(12) 0.946(10) 0.015(6) 0.29(4) 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 S1 0.0422(3) 0.0482(4) 0.0368(4) 0.0060(3) 0.0109(3) 0.0133(3) S3 0.0469(4) 0.0400(4) 0.0368(4) 0.0079(3) 0.0117(3) 0.0155(3) S2 0.0444(3) 0.0389(4) 0.0439(4) 0.0083(3) 0.0123(3) 0.0146(3) S4 0.0483(4) 0.0383(4) 0.0495(4) 0.0030(3) 0.0140(3) 0.0128(3) O1 0.0396(10) 0.0885(16) 0.0920(17) 0.0612(14) 0.0289(10) 0.0317(10) O5 0.0572(11) 0.0651(13) 0.0437(12) 0.0124(10) 0.0203(9) 0.0220(10) O3 0.0542(11) 0.0750(14) 0.0395(11) 0.0123(10) 0.0156(9) 0.0202(10) O8 0.0548(12) 0.0617(13) 0.0852(17) 0.0501(13) 0.0217(11) 0.0164(11) O6 0.0794(14) 0.0304(10) 0.0764(15) 0.0050(10) 0.0213(12) 0.0087(10) O7 0.0429(11) 0.0656(13) 0.0990(17) 0.0544(13) 0.0164(11) 0.0141(10) O4 0.0687(13) 0.0310(10) 0.0811(15) 0.0066(10) 0.0176(11) 0.0097(10) O2 0.0579(12) 0.143(2) 0.1050(19) 0.0961(18) 0.0449(13) 0.0452(14) N1 0.0325(10) 0.0392(12) 0.0507(14) 0.0222(11) 0.0098(9) 0.0092(9) N2 0.0412(11) 0.0356(11) 0.0457(13) 0.0175(10) 0.0105(10) 0.0107(10) C17 0.0310(11) 0.0415(14) 0.0366(14) 0.0087(12) 0.0065(10) 0.0138(11) C18 0.0330(12) 0.0380(13) 0.0356(14) 0.0087(11) 0.0080(10) 0.0142(11) C16 0.0415(14) 0.0443(16) 0.0541(18) 0.0210(15) 0.0156(13) 0.0150(13) C19 0.0555(16) 0.0485(17) 0.0483(18) 0.0193(15) 0.0217(14) 0.0213(14) C20 0.0562(17) 0.0419(16) 0.060(2) 0.0185(15) 0.0209(14) 0.0172(14) C15 0.0410(14) 0.0585(17) 0.0430(17) 0.0196(15) 0.0152(12) 0.0192(13) C5 0.0377(13) 0.0322(13) 0.0361(15) 0.0040(12) 0.0056(11) 0.0147(11) C12 0.0291(12) 0.0499(15) 0.0380(15) 0.0149(13) 0.0046(11) 0.0130(11) C4 0.0320(11) 0.0316(12) 0.0376(14) 0.0107(11) 0.0049(10) 0.0124(10) C6 0.0308(11) 0.0348(13) 0.0360(14) 0.0113(11) 0.0063(10) 0.0137(10) C10 0.0404(13) 0.0342(13) 0.0344(15) 0.0056(12) 0.0059(11) 0.0142(11) C8 0.0406(13) 0.0359(14) 0.0467(16) 0.0122(13) 0.0081(12) 0.0122(12) C7 0.0332(12) 0.0461(14) 0.0371(16) 0.0129(12) 0.0058(11) 0.0184(11) C9 0.0347(12) 0.0292(12) 0.0368(14) 0.0083(11) 0.0039(10) 0.0116(10) C3 0.0362(13) 0.0352(14) 0.0518(17) 0.0145(13) 0.0067(12) 0.0131(11) C2 0.0341(14) 0.0567(18) 0.068(2) 0.0351(17) 0.0127(14) 0.0123(14) C1 0.0418(14) 0.0517(16) 0.0553(18) 0.0281(14) 0.0165(13) 0.0184(13) C14 0.0505(16) 0.0420(15) 0.0442(16) 0.0209(13) 0.0153(13) 0.0119(13) C13 0.0444(16) 0.0485(17) 0.064(2) 0.0307(17) 0.0150(16) 0.0105(15) C11 0.0299(11) 0.0360(13) 0.0362(14) 0.0106(11) 0.0051(10) 0.0133(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C15 1.739(3) . ? S1 C17 1.747(2) . ? S3 C19 1.734(3) . ? S3 C18 1.754(2) . ? S2 C16 1.746(3) . ? S2 C17 1.766(2) . ? S4 C20 1.735(3) . ? S4 C18 1.758(2) . ? O1 C1 1.255(3) . ? O1 H1O 0.65(8) . ? O5 C7 1.201(3) . ? O3 C12 1.201(3) . ? O8 C14 1.305(3) . ? O8 H8O 0.80(4) . ? O6 C8 1.210(3) . ? O7 C14 1.202(3) . ? O4 C3 1.204(3) . ? O2 C1 1.243(3) . ? N1 C3 1.389(3) . ? N1 C12 1.398(3) . ? N1 C2 1.443(3) . ? N2 C8 1.384(3) . ? N2 C7 1.396(3) . ? N2 C13 1.440(3) . ? C17 C18 1.344(3) . ? C16 C15 1.315(4) . ? C16 H16 0.95(3) . ? C19 C20 1.312(4) . ? C19 H19 0.95(3) . ? C20 H20 0.95(3) . ? C15 H15 1.00(2) . ? C5 C4 1.378(3) . ? C5 C6 1.388(3) . ? C5 H5 0.92(2) . ? C12 C11 1.493(3) . ? C4 C11 1.391(3) . ? C4 C3 1.488(3) . ? C6 C9 1.388(3) . ? C6 C7 1.485(3) . ? C10 C11 1.377(3) . ? C10 C9 1.383(3) . ? C10 H10 0.93(3) . ? C8 C9 1.484(3) . ? C2 C1 1.494(3) . ? C2 H2A 0.98(3) . ? C2 H2B 0.97(3) . ? C1 H1O 1.48(7) . ? C14 C13 1.506(4) . ? C13 H13B 0.98(3) . ? C13 H13A 0.90(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 C15 S1 C17 94.80(13) . . ? C19 S3 C18 94.46(13) . . ? C16 S2 C17 94.35(13) . . ? C20 S4 C18 94.43(13) . . ? C1 O1 H1O 97(7) . . ? C14 O8 H8O 106(3) . . ? C3 N1 C12 112.4(2) . . ? C3 N1 C2 124.6(2) . . ? C12 N1 C2 122.5(2) . . ? C8 N2 C7 111.9(2) . . ? C8 N2 C13 123.7(2) . . ? C7 N2 C13 123.9(2) . . ? C18 C17 S1 122.93(19) . . ? C18 C17 S2 122.44(19) . . ? S1 C17 S2 114.62(13) . . ? C17 C18 S3 123.24(19) . . ? C17 C18 S4 122.20(19) . . ? S3 C18 S4 114.55(13) . . ? C15 C16 S2 117.9(2) . . ? C15 C16 H16 127.3(17) . . ? S2 C16 H16 114.8(16) . . ? C20 C19 S3 118.4(2) . . ? C20 C19 H19 122.7(19) . . ? S3 C19 H19 119.0(19) . . ? C19 C20 S4 118.2(2) . . ? C19 C20 H20 124.1(18) . . ? S4 C20 H20 117.7(18) . . ? C16 C15 S1 118.3(2) . . ? C16 C15 H15 125.9(14) . . ? S1 C15 H15 115.8(14) . . ? C4 C5 C6 115.1(2) . . ? C4 C5 H5 122.4(14) . . ? C6 C5 H5 122.5(14) . . ? O3 C12 N1 124.8(2) . . ? O3 C12 C11 129.6(2) . . ? N1 C12 C11 105.6(2) . . ? C5 C4 C11 122.4(2) . . ? C5 C4 C3 129.3(2) . . ? C11 C4 C3 108.3(2) . . ? C5 C6 C9 122.1(2) . . ? C5 C6 C7 129.6(2) . . ? C9 C6 C7 108.3(2) . . ? C11 C10 C9 114.7(2) . . ? C11 C10 H10 122.7(16) . . ? C9 C10 H10 122.6(16) . . ? O6 C8 N2 124.4(2) . . ? O6 C8 C9 129.1(3) . . ? N2 C8 C9 106.5(2) . . ? O5 C7 N2 124.5(2) . . ? O5 C7 C6 129.8(2) . . ? N2 C7 C6 105.7(2) . . ? C10 C9 C6 122.9(2) . . ? C10 C9 C8 129.4(2) . . ? C6 C9 C8 107.6(2) . . ? O4 C3 N1 125.2(2) . . ? O4 C3 C4 128.9(3) . . ? N1 C3 C4 105.9(2) . . ? N1 C2 C1 115.5(2) . . ? N1 C2 H2A 107.3(19) . . ? C1 C2 H2A 106.6(18) . . ? N1 C2 H2B 110.1(18) . . ? C1 C2 H2B 106.8(18) . . ? H2A C2 H2B 111(3) . . ? O2 C1 O1 122.0(2) . . ? O2 C1 C2 117.7(2) . . ? O1 C1 C2 120.2(2) . . ? O2 C1 H1O 98(3) . . ? C2 C1 H1O 144(3) . . ? O7 C14 O8 124.3(2) . . ? O7 C14 C13 123.1(2) . . ? O8 C14 C13 112.5(2) . . ? N2 C13 C14 110.8(2) . . ? N2 C13 H13B 110.9(19) . . ? C14 C13 H13B 108.6(18) . . ? N2 C13 H13A 110(2) . . ? C14 C13 H13A 108.5(19) . . ? H13B C13 H13A 108(3) . . ? C10 C11 C4 122.8(2) . . ? C10 C11 C12 129.3(2) . . ? C4 C11 C12 107.9(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 C15 S1 C17 C18 177.5(2) . . . . ? C15 S1 C17 S2 -1.39(14) . . . . ? C16 S2 C17 C18 -177.87(19) . . . . ? C16 S2 C17 S1 1.00(14) . . . . ? S1 C17 C18 S3 -179.93(11) . . . . ? S2 C17 C18 S3 -1.2(3) . . . . ? S1 C17 C18 S4 1.5(3) . . . . ? S2 C17 C18 S4 -179.69(11) . . . . ? C19 S3 C18 C17 179.4(2) . . . . ? C19 S3 C18 S4 -2.01(14) . . . . ? C20 S4 C18 C17 -179.2(2) . . . . ? C20 S4 C18 S3 2.13(14) . . . . ? C17 S2 C16 C15 0.0(2) . . . . ? C18 S3 C19 C20 1.1(2) . . . . ? S3 C19 C20 S4 0.3(3) . . . . ? C18 S4 C20 C19 -1.5(2) . . . . ? S2 C16 C15 S1 -1.0(3) . . . . ? C17 S1 C15 C16 1.4(2) . . . . ? C3 N1 C12 O3 -176.8(2) . . . . ? C2 N1 C12 O3 -5.0(3) . . . . ? C3 N1 C12 C11 2.1(2) . . . . ? C2 N1 C12 C11 173.92(19) . . . . ? C6 C5 C4 C11 0.2(3) . . . . ? C6 C5 C4 C3 -178.9(2) . . . . ? C4 C5 C6 C9 -0.2(3) . . . . ? C4 C5 C6 C7 178.0(2) . . . . ? C7 N2 C8 O6 178.4(2) . . . . ? C13 N2 C8 O6 6.1(4) . . . . ? C7 N2 C8 C9 -1.4(2) . . . . ? C13 N2 C8 C9 -173.6(2) . . . . ? C8 N2 C7 O5 -178.3(2) . . . . ? C13 N2 C7 O5 -6.0(3) . . . . ? C8 N2 C7 C6 1.4(2) . . . . ? C13 N2 C7 C6 173.6(2) . . . . ? C5 C6 C7 O5 0.4(4) . . . . ? C9 C6 C7 O5 178.8(2) . . . . ? C5 C6 C7 N2 -179.2(2) . . . . ? C9 C6 C7 N2 -0.8(2) . . . . ? C11 C10 C9 C6 0.3(3) . . . . ? C11 C10 C9 C8 -178.0(2) . . . . ? C5 C6 C9 C10 -0.1(3) . . . . ? C7 C6 C9 C10 -178.63(19) . . . . ? C5 C6 C9 C8 178.56(19) . . . . ? C7 C6 C9 C8 0.0(2) . . . . ? O6 C8 C9 C10 -0.4(4) . . . . ? N2 C8 C9 C10 179.3(2) . . . . ? O6 C8 C9 C6 -178.9(2) . . . . ? N2 C8 C9 C6 0.8(2) . . . . ? C12 N1 C3 O4 175.9(2) . . . . ? C2 N1 C3 O4 4.3(4) . . . . ? C12 N1 C3 C4 -2.3(2) . . . . ? C2 N1 C3 C4 -173.94(19) . . . . ? C5 C4 C3 O4 2.7(4) . . . . ? C11 C4 C3 O4 -176.5(2) . . . . ? C5 C4 C3 N1 -179.2(2) . . . . ? C11 C4 C3 N1 1.6(2) . . . . ? C3 N1 C2 C1 -94.8(3) . . . . ? C12 N1 C2 C1 94.4(3) . . . . ? N1 C2 C1 O2 -165.9(3) . . . . ? N1 C2 C1 O1 15.5(5) . . . . ? C8 N2 C13 C14 77.0(3) . . . . ? C7 N2 C13 C14 -94.4(3) . . . . ? O7 C14 C13 N2 9.6(5) . . . . ? O8 C14 C13 N2 -171.7(3) . . . . ? C9 C10 C11 C4 -0.3(3) . . . . ? C9 C10 C11 C12 179.3(2) . . . . ? C5 C4 C11 C10 0.0(3) . . . . ? C3 C4 C11 C10 179.29(19) . . . . ? C5 C4 C11 C12 -179.66(19) . . . . ? C3 C4 C11 C12 -0.4(2) . . . . ? O3 C12 C11 C10 -1.8(4) . . . . ? N1 C12 C11 C10 179.4(2) . . . . ? O3 C12 C11 C4 177.8(2) . . . . ? N1 C12 C11 C4 -1.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.912 _refine_diff_density_max 0.243 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.051 # Attachment 'Ligand L.cif' data_pmgi_06 _database_code_depnum_ccdc_archive 'CCDC 607637' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H8 N2 O8' _chemical_formula_weight 332.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.1088(5) _cell_length_b 5.3102(6) _cell_length_c 12.3475(15) _cell_angle_alpha 90.588(9) _cell_angle_beta 98.023(8) _cell_angle_gamma 95.211(8) _cell_volume 330.23(6) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1348 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 170 _exptl_absorpt_coefficient_mu 0.141 _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 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2661 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 28.28 _reflns_number_total 1438 _reflns_number_gt 1242 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+0.0793P] 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 1438 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0995 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 C7 C 0.6776(3) 0.1840(3) 0.14602(11) 0.0400(3) Uani 1 1 d . . . C1 C 0.8044(3) 0.2210(3) 0.41419(11) 0.0389(3) Uani 1 1 d . . . C5 C 1.1480(3) -0.2057(3) 0.04193(11) 0.0381(3) Uani 1 1 d . . . H5 H 1.2433 -0.3381 0.0691 0.046 Uiso 1 1 calc R . . C4 C 0.9790(3) -0.0903(3) 0.10076(11) 0.0362(3) Uani 1 1 d . . . C3 C 0.9162(3) -0.1442(3) 0.21280(11) 0.0411(3) Uani 1 1 d . . . C6 C 0.8364(2) 0.1081(3) 0.06064(11) 0.0360(3) Uani 1 1 d . . . C2 C 0.6272(3) 0.0432(3) 0.33503(12) 0.0493(4) Uani 1 1 d . . . H2A H 0.6096 -0.1225 0.3670 0.059 Uiso 1 1 calc R . . H2B H 0.4520 0.1032 0.3216 0.059 Uiso 1 1 calc R . . O1 O 1.0421(2) 0.2639(2) 0.41024(9) 0.0494(3) Uani 1 1 d . . . O2 O 0.6795(2) 0.3166(3) 0.48607(11) 0.0697(4) Uani 1 1 d . . . O3 O 1.0046(3) -0.2953(2) 0.27628(9) 0.0582(3) Uani 1 1 d . . . O4 O 0.5299(2) 0.3487(2) 0.14371(10) 0.0566(3) Uani 1 1 d . . . N1 N 0.7302(2) 0.0219(2) 0.23214(9) 0.0433(3) Uani 1 1 d . . . H2O H 0.787(8) 0.457(8) 0.525(3) 0.167(14) 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 C7 0.0355(6) 0.0442(8) 0.0389(7) -0.0075(6) 0.0004(6) 0.0046(6) C1 0.0391(7) 0.0454(8) 0.0335(7) 0.0000(6) 0.0075(5) 0.0081(6) C5 0.0385(6) 0.0365(7) 0.0384(7) -0.0003(6) -0.0016(6) 0.0092(5) C4 0.0370(6) 0.0358(7) 0.0340(6) -0.0009(5) -0.0014(5) 0.0034(5) C3 0.0448(7) 0.0414(8) 0.0354(7) -0.0019(6) 0.0011(6) 0.0030(6) C6 0.0342(6) 0.0358(7) 0.0366(7) -0.0048(5) -0.0003(5) 0.0053(5) C2 0.0461(8) 0.0606(10) 0.0413(8) -0.0060(7) 0.0114(6) -0.0011(7) O1 0.0399(5) 0.0583(7) 0.0506(6) -0.0078(5) 0.0104(5) 0.0024(5) O2 0.0455(6) 0.0959(11) 0.0685(8) -0.0390(8) 0.0144(6) 0.0050(7) O3 0.0743(8) 0.0580(7) 0.0438(6) 0.0126(5) 0.0063(5) 0.0161(6) O4 0.0543(6) 0.0623(7) 0.0566(7) -0.0051(5) 0.0082(5) 0.0250(6) N1 0.0445(6) 0.0511(7) 0.0341(6) -0.0046(5) 0.0045(5) 0.0056(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C7 O4 1.2039(17) . ? C7 N1 1.3875(19) . ? C7 C6 1.4904(18) . ? C1 O1 1.2226(17) . ? C1 O2 1.2886(17) . ? C1 C2 1.498(2) . ? C5 C4 1.3821(18) . ? C5 C6 1.3833(18) 2_755 ? C5 H5 0.9300 . ? C4 C6 1.3912(18) . ? C4 C3 1.4879(19) . ? C3 O3 1.2007(17) . ? C3 N1 1.3960(19) . ? C6 C5 1.3833(18) 2_755 ? C2 N1 1.4486(18) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? O2 H2O 0.96(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 O4 C7 N1 125.20(13) . . ? O4 C7 C6 128.84(14) . . ? N1 C7 C6 105.96(11) . . ? O1 C1 O2 124.93(14) . . ? O1 C1 C2 122.43(13) . . ? O2 C1 C2 112.63(13) . . ? C4 C5 C6 114.46(12) . 2_755 ? C4 C5 H5 122.8 . . ? C6 C5 H5 122.8 2_755 . ? C5 C4 C6 123.00(12) . . ? C5 C4 C3 129.03(12) . . ? C6 C4 C3 107.97(12) . . ? O3 C3 N1 125.38(14) . . ? O3 C3 C4 128.78(13) . . ? N1 C3 C4 105.83(11) . . ? C5 C6 C4 122.55(12) 2_755 . ? C5 C6 C7 129.48(12) 2_755 . ? C4 C6 C7 107.97(12) . . ? N1 C2 C1 111.79(12) . . ? N1 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N1 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? C1 O2 H2O 111(2) . . ? C7 N1 C3 112.19(12) . . ? C7 N1 C2 123.47(13) . . ? C3 N1 C2 123.96(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C5 C4 C6 -0.1(2) 2_755 . . . ? C6 C5 C4 C3 -179.41(13) 2_755 . . . ? C5 C4 C3 O3 2.0(3) . . . . ? C6 C4 C3 O3 -177.36(15) . . . . ? C5 C4 C3 N1 -178.70(14) . . . . ? C6 C4 C3 N1 1.95(15) . . . . ? C5 C4 C6 C5 0.2(2) . . . 2_755 ? C3 C4 C6 C5 179.56(13) . . . 2_755 ? C5 C4 C6 C7 -179.83(13) . . . . ? C3 C4 C6 C7 -0.42(15) . . . . ? O4 C7 C6 C5 -0.5(3) . . . 2_755 ? N1 C7 C6 C5 178.76(14) . . . 2_755 ? O4 C7 C6 C4 179.44(15) . . . . ? N1 C7 C6 C4 -1.26(16) . . . . ? O1 C1 C2 N1 -25.7(2) . . . . ? O2 C1 C2 N1 155.52(14) . . . . ? O4 C7 N1 C3 -178.06(14) . . . . ? C6 C7 N1 C3 2.61(17) . . . . ? O4 C7 N1 C2 -4.8(2) . . . . ? C6 C7 N1 C2 175.86(12) . . . . ? O3 C3 N1 C7 176.48(14) . . . . ? C4 C3 N1 C7 -2.86(16) . . . . ? O3 C3 N1 C2 3.3(2) . . . . ? C4 C3 N1 C2 -176.07(13) . . . . ? C1 C2 N1 C7 -87.12(18) . . . . ? C1 C2 N1 C3 85.34(18) . . . . ? _diffrn_measured_fraction_theta_max 0.879 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.879 _refine_diff_density_max 0.188 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.043