Supplementary Material (ESI) for The Analyst This journal is © The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 91 loop_ _publ_author_name 'Duncan Graham' 'A. R. Kennedy' 'Callum McHugh' 'W. Smith' _publ_contact_author_name 'Duncan Graham' _publ_contact_author_address ; Department of Pure and Applied Chemistry University of Strathclyde Thomas Graham Building 295 Cathedral Street Glasgow G1 1XL UNITED KINGDOM ; _publ_contact_author_email DUNCAN.GRAHAM@STRATH.AC.UK _publ_section_title ; TNT Stilbene Derivatives as SERRS Active Species ; data_cal _database_code_depnum_ccdc_archive 'CCDC 604872' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H9 N3 O6 S' _chemical_formula_weight 335.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.1035(2) _cell_length_b 8.6768(3) _cell_length_c 22.2831(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.802(1) _cell_angle_gamma 90.00 _cell_volume 1368.61(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11181 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 27.47 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.275 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.873 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details Sortav _exptl_special_details ; Data collected at EPSRC service, University of Southampton. ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD' _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 11181 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_sigmaI/netI 0.0820 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3099 _reflns_number_gt 2016 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Denzo & Collect' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3099 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0899 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1141 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.986 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.26680(7) 0.81127(7) 0.08669(2) 0.02542(18) Uani 1 1 d . . . O1 O 0.4079(2) 0.1338(2) 0.02847(7) 0.0369(4) Uani 1 1 d . . . O2 O 0.1105(2) 0.1717(2) 0.03830(7) 0.0387(5) Uani 1 1 d . . . O3 O 0.1262(3) 0.1839(2) -0.25573(7) 0.0430(5) Uani 1 1 d . . . O4 O 0.2160(3) -0.0096(2) -0.19967(7) 0.0476(5) Uani 1 1 d . . . O5 O 0.0139(2) 0.6790(2) -0.15684(7) 0.0380(4) Uani 1 1 d . . . O6 O 0.2709(2) 0.7263(2) -0.10022(7) 0.0377(4) Uani 1 1 d . . . N1 N 0.2529(3) 0.1824(2) 0.01078(8) 0.0264(4) Uani 1 1 d . . . N2 N 0.1745(3) 0.1249(3) -0.20687(8) 0.0299(5) Uani 1 1 d . . . N3 N 0.1501(3) 0.6395(2) -0.12320(8) 0.0267(5) Uani 1 1 d . . . C1 C 0.3069(4) 1.0272(3) 0.18029(11) 0.0390(6) Uani 1 1 d . . . H1A H 0.3243 1.0331 0.2243 0.058 Uiso 1 1 calc R . . H1B H 0.1829 1.0692 0.1663 0.058 Uiso 1 1 calc R . . H1C H 0.4059 1.0870 0.1629 0.058 Uiso 1 1 calc R . . C2 C 0.3184(3) 0.8624(3) 0.16091(10) 0.0268(5) Uani 1 1 d . . . C3 C 0.3727(3) 0.7368(3) 0.19445(10) 0.0299(6) Uani 1 1 d . . . H3 H 0.4069 0.7416 0.2366 0.036 Uiso 1 1 calc R . . C4 C 0.3738(3) 0.5998(3) 0.16136(9) 0.0271(5) Uani 1 1 d . . . H4 H 0.4097 0.5029 0.1787 0.033 Uiso 1 1 calc R . . C5 C 0.3181(3) 0.6193(3) 0.10166(9) 0.0216(5) Uani 1 1 d . . . C6 C 0.3057(3) 0.5032(3) 0.05510(9) 0.0228(5) Uani 1 1 d . . . H6 H 0.3583 0.4047 0.0647 0.027 Uiso 1 1 calc R . . C7 C 0.2245(3) 0.5255(3) -0.00088(9) 0.0212(5) Uani 1 1 d . . . H7 H 0.1684 0.6238 -0.0084 0.025 Uiso 1 1 calc R . . C8 C 0.2113(3) 0.4187(3) -0.05157(9) 0.0199(5) Uani 1 1 d . . . C9 C 0.2314(3) 0.2590(3) -0.04840(9) 0.0211(5) Uani 1 1 d . . . C10 C 0.2240(3) 0.1602(3) -0.09714(9) 0.0243(5) Uani 1 1 d . . . H10 H 0.2455 0.0528 -0.0922 0.029 Uiso 1 1 calc R . . C11 C 0.1838(3) 0.2249(3) -0.15350(9) 0.0228(5) Uani 1 1 d . . . C12 C 0.1531(3) 0.3796(3) -0.16138(9) 0.0234(5) Uani 1 1 d . . . H12 H 0.1206 0.4212 -0.2003 0.028 Uiso 1 1 calc R . . C13 C 0.1709(3) 0.4735(3) -0.11114(9) 0.0208(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 S1 0.0321(3) 0.0232(4) 0.0206(3) -0.0018(2) 0.0001(2) 0.0029(3) O1 0.0448(10) 0.0340(11) 0.0308(9) 0.0047(8) -0.0042(8) 0.0089(8) O2 0.0469(10) 0.0423(12) 0.0284(9) 0.0079(8) 0.0118(8) 0.0021(9) O3 0.0750(13) 0.0349(12) 0.0182(9) -0.0024(8) -0.0020(8) -0.0048(10) O4 0.0850(14) 0.0267(11) 0.0311(10) -0.0068(8) 0.0042(9) 0.0059(10) O5 0.0449(10) 0.0350(11) 0.0324(9) 0.0067(8) -0.0076(8) 0.0120(8) O6 0.0537(10) 0.0261(11) 0.0320(9) 0.0013(8) -0.0041(8) -0.0105(8) N1 0.0379(11) 0.0192(11) 0.0218(10) 0.0001(8) 0.0017(9) 0.0021(9) N2 0.0388(11) 0.0284(13) 0.0230(11) -0.0029(9) 0.0050(8) -0.0050(9) N3 0.0376(11) 0.0238(12) 0.0194(9) 0.0005(8) 0.0059(8) 0.0017(9) C1 0.0486(15) 0.0342(17) 0.0331(13) -0.0117(12) -0.0024(11) 0.0080(12) C2 0.0272(11) 0.0299(15) 0.0237(11) -0.0077(11) 0.0048(9) -0.0015(10) C3 0.0345(12) 0.0381(16) 0.0168(11) -0.0020(11) 0.0002(10) -0.0043(11) C4 0.0331(12) 0.0270(15) 0.0207(11) 0.0028(10) -0.0008(9) -0.0014(10) C5 0.0232(10) 0.0196(13) 0.0222(11) 0.0014(9) 0.0030(9) 0.0008(9) C6 0.0254(11) 0.0179(13) 0.0252(11) -0.0004(9) 0.0027(9) 0.0009(9) C7 0.0230(10) 0.0209(13) 0.0198(11) -0.0003(9) 0.0027(8) 0.0020(9) C8 0.0184(10) 0.0236(14) 0.0178(11) -0.0007(9) 0.0015(8) 0.0006(9) C9 0.0224(10) 0.0236(13) 0.0172(10) 0.0024(9) 0.0018(8) 0.0028(9) C10 0.0264(11) 0.0221(14) 0.0251(12) -0.0003(9) 0.0051(9) 0.0003(10) C11 0.0260(11) 0.0244(14) 0.0187(11) -0.0034(9) 0.0058(9) -0.0024(10) C12 0.0273(11) 0.0256(14) 0.0172(10) 0.0001(10) 0.0021(9) -0.0018(10) C13 0.0229(10) 0.0192(13) 0.0204(11) 0.0017(9) 0.0015(8) 0.0018(9) _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 C2 1.722(2) . ? S1 C5 1.732(2) . ? O1 N1 1.214(2) . ? O2 N1 1.230(2) . ? O3 N2 1.226(2) . ? O4 N2 1.212(3) . ? O5 N3 1.223(2) . ? O6 N3 1.221(2) . ? N1 C9 1.473(3) . ? N2 C11 1.469(3) . ? N3 C13 1.470(3) . ? C1 C2 1.497(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.359(3) . ? C3 C4 1.399(3) . ? C3 H3 0.9500 . ? C4 C5 1.367(3) . ? C4 H4 0.9500 . ? C5 C6 1.443(3) . ? C6 C7 1.344(3) . ? C6 H6 0.9500 . ? C7 C8 1.458(3) . ? C7 H7 0.9500 . ? C8 C9 1.394(3) . ? C8 C13 1.417(3) . ? C9 C10 1.381(3) . ? C10 C11 1.383(3) . ? C10 H10 0.9500 . ? C11 C12 1.369(3) . ? C12 C13 1.382(3) . ? C12 H12 0.9500 . ? 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 S1 C5 92.21(11) . . ? O1 N1 O2 125.02(19) . . ? O1 N1 C9 118.09(17) . . ? O2 N1 C9 116.89(18) . . ? O4 N2 O3 124.5(2) . . ? O4 N2 C11 117.91(19) . . ? O3 N2 C11 117.6(2) . . ? O6 N3 O5 125.2(2) . . ? O6 N3 C13 118.13(19) . . ? O5 N3 C13 116.68(19) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 128.8(2) . . ? C3 C2 S1 110.45(18) . . ? C1 C2 S1 120.70(18) . . ? C2 C3 C4 113.9(2) . . ? C2 C3 H3 123.0 . . ? C4 C3 H3 123.0 . . ? C5 C4 C3 113.2(2) . . ? C5 C4 H4 123.4 . . ? C3 C4 H4 123.4 . . ? C4 C5 C6 127.5(2) . . ? C4 C5 S1 110.23(17) . . ? C6 C5 S1 122.26(16) . . ? C7 C6 C5 124.2(2) . . ? C7 C6 H6 117.9 . . ? C5 C6 H6 117.9 . . ? C6 C7 C8 128.5(2) . . ? C6 C7 H7 115.8 . . ? C8 C7 H7 115.8 . . ? C9 C8 C13 113.14(19) . . ? C9 C8 C7 126.36(18) . . ? C13 C8 C7 120.5(2) . . ? C10 C9 C8 125.43(19) . . ? C10 C9 N1 114.7(2) . . ? C8 C9 N1 119.76(18) . . ? C9 C10 C11 117.0(2) . . ? C9 C10 H10 121.5 . . ? C11 C10 H10 121.5 . . ? C12 C11 C10 122.2(2) . . ? C12 C11 N2 118.65(19) . . ? C10 C11 N2 119.2(2) . . ? C11 C12 C13 118.1(2) . . ? C11 C12 H12 120.9 . . ? C13 C12 H12 120.9 . . ? C12 C13 C8 124.0(2) . . ? C12 C13 N3 115.38(18) . . ? C8 C13 N3 120.63(18) . . ? 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 S1 C2 C3 0.31(17) . . . . ? C5 S1 C2 C1 178.26(19) . . . . ? C1 C2 C3 C4 -177.7(2) . . . . ? S1 C2 C3 C4 0.1(2) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C3 C4 C5 C6 179.1(2) . . . . ? C3 C4 C5 S1 0.8(2) . . . . ? C2 S1 C5 C4 -0.61(16) . . . . ? C2 S1 C5 C6 -179.04(17) . . . . ? C4 C5 C6 C7 170.1(2) . . . . ? S1 C5 C6 C7 -11.8(3) . . . . ? C5 C6 C7 C8 177.33(19) . . . . ? C6 C7 C8 C9 19.7(3) . . . . ? C6 C7 C8 C13 -161.6(2) . . . . ? C13 C8 C9 C10 3.3(3) . . . . ? C7 C8 C9 C10 -177.94(18) . . . . ? C13 C8 C9 N1 -173.31(17) . . . . ? C7 C8 C9 N1 5.4(3) . . . . ? O1 N1 C9 C10 76.8(3) . . . . ? O2 N1 C9 C10 -102.6(2) . . . . ? O1 N1 C9 C8 -106.2(2) . . . . ? O2 N1 C9 C8 74.3(3) . . . . ? C8 C9 C10 C11 -3.5(3) . . . . ? N1 C9 C10 C11 173.32(18) . . . . ? C9 C10 C11 C12 0.2(3) . . . . ? C9 C10 C11 N2 179.90(18) . . . . ? O4 N2 C11 C12 174.5(2) . . . . ? O3 N2 C11 C12 -5.2(3) . . . . ? O4 N2 C11 C10 -5.2(3) . . . . ? O3 N2 C11 C10 175.19(19) . . . . ? C10 C11 C12 C13 2.6(3) . . . . ? N2 C11 C12 C13 -177.02(18) . . . . ? C11 C12 C13 C8 -2.7(3) . . . . ? C11 C12 C13 N3 175.62(18) . . . . ? C9 C8 C13 C12 -0.1(3) . . . . ? C7 C8 C13 C12 -178.94(19) . . . . ? C9 C8 C13 N3 -178.37(18) . . . . ? C7 C8 C13 N3 2.8(3) . . . . ? O6 N3 C13 C12 -130.2(2) . . . . ? O5 N3 C13 C12 48.2(2) . . . . ? O6 N3 C13 C8 48.2(3) . . . . ? O5 N3 C13 C8 -133.37(19) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.324 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.064 #----------------------------------------------------------------- data_dg2 _database_code_depnum_ccdc_archive 'CCDC 604873' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H8 N4 O6' _chemical_formula_weight 316.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.1622(2) _cell_length_b 9.0664(3) _cell_length_c 20.6429(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1340.45(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1753 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description 'hexagonal prism' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.128 _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 150(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 'Nonius Kappa CCD' _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 9932 _diffrn_reflns_av_R_equivalents 0.057 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1786 _reflns_number_gt 1350 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Denzo & Collect' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.1322P] 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 1786 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0660 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2276(3) -0.0190(2) 0.19796(10) 0.0374(5) Uani 1 1 d . . . O2 O 0.4413(3) 0.0520(2) 0.13015(9) 0.0386(5) Uani 1 1 d . . . O3 O 0.1796(3) 0.4148(2) 0.34982(8) 0.0332(5) Uani 1 1 d . . . O4 O 0.1715(3) 0.6337(2) 0.30701(9) 0.0363(5) Uani 1 1 d . . . O5 O 0.0327(5) 0.6742(3) 0.08527(10) 0.0713(10) Uani 1 1 d . . . O6 O 0.0671(4) 0.5009(2) 0.01712(10) 0.0494(7) Uani 1 1 d . . . N1 N 0.3073(3) 0.0749(3) 0.16503(10) 0.0268(5) Uani 1 1 d . . . N2 N 0.1793(3) 0.4980(3) 0.30339(10) 0.0263(6) Uani 1 1 d . . . N3 N 0.0763(4) 0.5494(3) 0.07141(11) 0.0326(6) Uani 1 1 d . . . N4 N 0.0928(4) -0.0876(3) -0.15365(11) 0.0306(6) Uani 1 1 d . . . C1 C 0.1879(4) 0.3055(3) 0.11420(11) 0.0227(6) Uani 1 1 d . . . C2 C 0.2377(4) 0.2284(3) 0.17034(12) 0.0222(6) Uani 1 1 d . . . C3 C 0.2345(4) 0.2857(3) 0.23234(12) 0.0235(6) Uani 1 1 d . . . H3 H 0.2654 0.2275 0.2690 0.028 Uiso 1 1 calc R . . C4 C 0.1840(4) 0.4320(3) 0.23819(11) 0.0226(6) Uani 1 1 d . . . C5 C 0.1378(4) 0.5175(3) 0.18597(12) 0.0251(6) Uani 1 1 d . . . H5 H 0.1067 0.6187 0.1911 0.030 Uiso 1 1 calc R . . C6 C 0.1378(4) 0.4515(3) 0.12511(12) 0.0244(6) Uani 1 1 d . . . C7 C 0.1884(4) 0.2353(3) 0.04944(12) 0.0240(6) Uani 1 1 d . . . H7 H 0.2581 0.2818 0.0160 0.029 Uiso 1 1 calc R . . C8 C 0.0982(4) 0.1116(3) 0.03485(12) 0.0252(6) Uani 1 1 d . . . H8 H 0.0315 0.0628 0.0683 0.030 Uiso 1 1 calc R . . C9 C 0.0961(4) 0.0461(3) -0.03044(11) 0.0225(6) Uani 1 1 d . . . C10 C 0.0368(4) -0.0993(3) -0.03887(13) 0.0289(7) Uani 1 1 d . . . H10 H -0.0045 -0.1559 -0.0029 0.035 Uiso 1 1 calc R . . C11 C 0.0393(4) -0.1601(3) -0.10075(13) 0.0321(7) Uani 1 1 d . . . H11 H 0.0003 -0.2596 -0.1056 0.038 Uiso 1 1 calc R . . C12 C 0.1473(4) 0.0526(3) -0.14507(12) 0.0252(6) Uani 1 1 d . . . H12 H 0.1850 0.1071 -0.1822 0.030 Uiso 1 1 calc R . . C13 C 0.1521(4) 0.1231(3) -0.08553(12) 0.0237(6) Uani 1 1 d . . . H13 H 0.1930 0.2225 -0.0823 0.028 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 0.0484(13) 0.0261(10) 0.0378(11) 0.0053(10) 0.0006(11) 0.0010(10) O2 0.0315(11) 0.0394(12) 0.0450(12) -0.0029(11) 0.0067(10) 0.0113(11) O3 0.0439(12) 0.0364(11) 0.0192(9) 0.0005(9) 0.0010(9) 0.0047(11) O4 0.0448(13) 0.0243(11) 0.0397(11) -0.0089(10) -0.0037(11) 0.0011(10) O5 0.134(3) 0.0449(15) 0.0353(13) 0.0130(12) 0.0055(15) 0.0462(18) O6 0.0747(18) 0.0480(14) 0.0255(11) 0.0047(11) -0.0135(12) 0.0031(14) N1 0.0306(13) 0.0255(12) 0.0243(11) -0.0012(11) -0.0070(11) 0.0010(13) N2 0.0271(12) 0.0296(14) 0.0221(11) -0.0055(11) -0.0007(11) 0.0018(12) N3 0.0343(14) 0.0365(15) 0.0272(12) 0.0089(12) 0.0022(11) 0.0028(13) N4 0.0367(13) 0.0290(13) 0.0261(11) -0.0036(11) 0.0024(11) 0.0013(13) C1 0.0191(13) 0.0267(15) 0.0222(13) 0.0017(12) -0.0008(11) -0.0027(12) C2 0.0230(14) 0.0218(13) 0.0218(13) -0.0005(11) 0.0004(11) -0.0006(12) C3 0.0242(14) 0.0265(14) 0.0197(12) 0.0048(12) -0.0023(11) -0.0027(13) C4 0.0228(13) 0.0243(13) 0.0206(12) -0.0016(12) 0.0011(11) -0.0021(13) C5 0.0237(15) 0.0222(14) 0.0295(14) 0.0017(13) 0.0010(11) 0.0009(12) C6 0.0210(14) 0.0308(16) 0.0213(13) 0.0066(13) 0.0002(11) -0.0005(13) C7 0.0229(14) 0.0313(15) 0.0178(12) 0.0013(12) 0.0012(11) 0.0001(13) C8 0.0273(14) 0.0275(15) 0.0209(13) 0.0056(12) 0.0005(12) 0.0021(13) C9 0.0235(13) 0.0245(14) 0.0195(13) -0.0019(12) 0.0015(11) 0.0060(13) C10 0.0354(16) 0.0252(15) 0.0260(14) 0.0065(13) 0.0019(13) -0.0007(14) C11 0.0385(18) 0.0221(15) 0.0356(15) -0.0011(13) 0.0014(14) -0.0023(15) C12 0.0279(15) 0.0242(15) 0.0234(13) 0.0013(12) 0.0026(11) -0.0002(13) C13 0.0249(15) 0.0222(14) 0.0240(14) -0.0016(11) 0.0014(11) 0.0025(12) _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 N1 1.230(3) . ? O2 N1 1.218(3) . ? O3 N2 1.220(3) . ? O4 N2 1.234(3) . ? O5 N3 1.208(3) . ? O6 N3 1.206(3) . ? N1 C2 1.482(4) . ? N2 C4 1.474(3) . ? N3 C6 1.487(3) . ? N4 C11 1.331(3) . ? N4 C12 1.342(3) . ? C1 C6 1.390(4) . ? C1 C2 1.399(3) . ? C1 C7 1.481(3) . ? C2 C3 1.382(3) . ? C3 C4 1.380(4) . ? C3 H3 0.9500 . ? C4 C5 1.368(3) . ? C5 C6 1.391(3) . ? C5 H5 0.9500 . ? C7 C8 1.329(4) . ? C7 H7 0.9500 . ? C8 C9 1.473(4) . ? C8 H8 0.9500 . ? C9 C13 1.393(3) . ? C9 C10 1.395(4) . ? C10 C11 1.391(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.386(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? 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 N1 O1 125.1(2) . . ? O2 N1 C2 117.9(2) . . ? O1 N1 C2 117.0(2) . . ? O3 N2 O4 124.7(2) . . ? O3 N2 C4 117.8(2) . . ? O4 N2 C4 117.5(2) . . ? O6 N3 O5 123.2(3) . . ? O6 N3 C6 119.4(2) . . ? O5 N3 C6 117.3(2) . . ? C11 N4 C12 116.3(2) . . ? C6 C1 C2 114.0(2) . . ? C6 C1 C7 123.8(2) . . ? C2 C1 C7 122.2(2) . . ? C3 C2 C1 125.1(2) . . ? C3 C2 N1 115.3(2) . . ? C1 C2 N1 119.6(2) . . ? C4 C3 C2 116.5(2) . . ? C4 C3 H3 121.7 . . ? C2 C3 H3 121.7 . . ? C5 C4 C3 122.6(2) . . ? C5 C4 N2 118.9(2) . . ? C3 C4 N2 118.5(2) . . ? C4 C5 C6 117.9(2) . . ? C4 C5 H5 121.1 . . ? C6 C5 H5 121.1 . . ? C1 C6 C5 123.8(2) . . ? C1 C6 N3 121.6(2) . . ? C5 C6 N3 114.6(2) . . ? C8 C7 C1 124.5(2) . . ? C8 C7 H7 117.8 . . ? C1 C7 H7 117.8 . . ? C7 C8 C9 123.6(2) . . ? C7 C8 H8 118.2 . . ? C9 C8 H8 118.2 . . ? C13 C9 C10 117.3(2) . . ? C13 C9 C8 122.8(2) . . ? C10 C9 C8 119.9(2) . . ? C11 C10 C9 119.0(3) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? N4 C11 C10 124.2(3) . . ? N4 C11 H11 117.9 . . ? C10 C11 H11 117.9 . . ? N4 C12 C13 124.1(3) . . ? N4 C12 H12 117.9 . . ? C13 C12 H12 117.9 . . ? C12 C13 C9 119.1(2) . . ? C12 C13 H13 120.5 . . ? C9 C13 H13 120.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.8(4) . . . . ? C7 C1 C2 C3 -177.8(3) . . . . ? C6 C1 C2 N1 -175.6(2) . . . . ? C7 C1 C2 N1 4.8(4) . . . . ? O2 N1 C2 C3 -122.1(3) . . . . ? O1 N1 C2 C3 55.8(3) . . . . ? O2 N1 C2 C1 55.5(3) . . . . ? O1 N1 C2 C1 -126.5(3) . . . . ? C1 C2 C3 C4 -2.3(4) . . . . ? N1 C2 C3 C4 175.2(2) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C2 C3 C4 N2 -179.8(2) . . . . ? O3 N2 C4 C5 164.0(2) . . . . ? O4 N2 C4 C5 -14.6(4) . . . . ? O3 N2 C4 C3 -15.8(4) . . . . ? O4 N2 C4 C3 165.6(3) . . . . ? C3 C4 C5 C6 1.7(4) . . . . ? N2 C4 C5 C6 -178.1(2) . . . . ? C2 C1 C6 C5 0.5(4) . . . . ? C7 C1 C6 C5 -179.8(3) . . . . ? C2 C1 C6 N3 -178.5(2) . . . . ? C7 C1 C6 N3 1.1(4) . . . . ? C4 C5 C6 C1 -2.2(4) . . . . ? C4 C5 C6 N3 176.9(2) . . . . ? O6 N3 C6 C1 1.0(4) . . . . ? O5 N3 C6 C1 179.0(3) . . . . ? O6 N3 C6 C5 -178.1(3) . . . . ? O5 N3 C6 C5 -0.1(4) . . . . ? C6 C1 C7 C8 -125.7(3) . . . . ? C2 C1 C7 C8 53.9(4) . . . . ? C1 C7 C8 C9 178.1(3) . . . . ? C7 C8 C9 C13 -14.8(4) . . . . ? C7 C8 C9 C10 164.9(3) . . . . ? C13 C9 C10 C11 1.0(4) . . . . ? C8 C9 C10 C11 -178.8(3) . . . . ? C12 N4 C11 C10 0.1(4) . . . . ? C9 C10 C11 N4 -0.9(5) . . . . ? C11 N4 C12 C13 0.6(4) . . . . ? N4 C12 C13 C9 -0.5(4) . . . . ? C10 C9 C13 C12 -0.3(4) . . . . ? C8 C9 C13 C12 179.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.192 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.050 #===END