# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 207/354 data_global # 1. SUBMISSION DETAILS _publ_contact_author ; Toupet Loic G.M.C.M.-UMR6626 Universite de Rennes Campus de Beaulieu 35042 RENNES cedex , FRANCE ; _publ_contact_author_email 'loic.toupet@univ-rennes1.fr' _publ_contact_author_fax '(33) 2 99 28 67 17' _publ_contact_author_phone '(33) 2 99 28 60 65' _publ_requested_journal '' _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF as the NEW crystallographic data of the compound 6a in the paper reference 9/03150B/P1P. ; data_diaza _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H19 N3 O2 S' _chemical_formula_weight 329.41 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 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 13.330(2) _cell_length_b 8.404(2) _cell_length_c 15.100(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.200(10) _cell_angle_gamma 90.00 _cell_volume 1664.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.207 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3041 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2909 _reflns_number_gt 2031 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0599P)^2^+0.6055P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0038(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2909 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0771 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.003 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.01612(5) 0.14475(8) 0.19443(4) 0.0446(2) Uani 1 1 d . . . O3 O 0.02708(14) 0.0258(2) 0.25790(12) 0.0596(5) Uani 1 1 d . . . O5 O -0.10944(13) 0.1049(2) 0.13544(12) 0.0599(5) Uani 1 1 d . . . N1 N 0.06074(15) 0.2021(2) 0.12806(12) 0.0444(5) Uani 1 1 d . . . N2 N 0.20332(14) 0.2277(2) 0.24478(12) 0.0430(5) Uani 1 1 d . . . N3 N 0.35224(15) 0.2101(3) 0.34827(12) 0.0476(5) Uani 1 1 d . . . C1 C 0.2962(2) 0.3748(3) 0.09877(17) 0.0489(6) Uani 1 1 d . . . C2 C 0.3492(2) 0.4097(4) 0.03052(19) 0.0579(7) Uani 1 1 d . . . C3 C 0.3265(2) 0.3334(4) -0.05091(19) 0.0604(8) Uani 1 1 d . . . C4 C 0.2493(2) 0.2226(3) -0.06498(17) 0.0545(7) Uani 1 1 d . . . C5 C 0.1944(2) 0.1898(3) 0.00164(15) 0.0444(6) Uani 1 1 d . . . C6 C 0.21761(17) 0.2644(3) 0.08486(14) 0.0392(5) Uani 1 1 d . . . C7 C 0.15859(17) 0.2264(3) 0.15679(14) 0.0399(5) Uani 1 1 d . . . C8 C 0.30015(19) 0.1919(3) 0.26663(16) 0.0444(6) Uani 1 1 d . . . C9 C 0.3071(2) 0.2835(4) 0.41854(18) 0.0730(9) Uani 1 1 d . . . H9A H 0.3600 0.3255 0.4640 0.095 Uiso 1 1 calc R . . H9B H 0.2687 0.2055 0.4448 0.095 Uiso 1 1 calc R . . H9C H 0.2627 0.3683 0.3934 0.095 Uiso 1 1 calc R . . C10 C 0.4583(2) 0.1613(4) 0.3710(2) 0.0782(10) Uani 1 1 d . . . H10A H 0.4842 0.1872 0.4328 0.102 Uiso 1 1 calc R . . H10B H 0.4975 0.2158 0.3329 0.102 Uiso 1 1 calc R . . H10C H 0.4632 0.0485 0.3625 0.102 Uiso 1 1 calc R . . C11 C -0.04144(17) 0.3156(3) 0.25431(15) 0.0411(5) Uani 1 1 d . . . C12 C -0.12757(19) 0.4057(3) 0.22300(17) 0.0502(6) Uani 1 1 d . . . C13 C -0.1479(2) 0.5390(4) 0.27023(19) 0.0556(7) Uani 1 1 d . . . C14 C -0.08307(19) 0.5870(3) 0.34751(17) 0.0522(6) Uani 1 1 d . . . C15 C 0.00283(19) 0.4964(4) 0.37683(17) 0.0530(7) Uani 1 1 d . . . C16 C 0.02355(18) 0.3612(3) 0.33218(15) 0.0473(6) Uani 1 1 d . . . C17 C -0.1062(3) 0.7342(4) 0.3973(2) 0.0803(10) Uani 1 1 d . . . H17A H -0.0561 0.7461 0.4510 0.104 Uiso 1 1 calc R . . H17B H -0.1726 0.7246 0.4130 0.104 Uiso 1 1 calc R . . H17C H -0.1045 0.8258 0.3595 0.104 Uiso 1 1 calc R . . H1 H 0.3123(18) 0.428(3) 0.1550(17) 0.051 Uiso 1 1 d . . . H2 H 0.399(2) 0.483(3) 0.0389(17) 0.055 Uiso 1 1 d . . . H3 H 0.364(2) 0.352(3) -0.0967(18) 0.059 Uiso 1 1 d . . . H4 H 0.2341(19) 0.169(3) -0.1203(17) 0.050 Uiso 1 1 d . . . H5 H 0.1441(18) 0.115(3) -0.0082(15) 0.043 Uiso 1 1 d . . . H8 H 0.3382(17) 0.142(3) 0.2267(15) 0.041 Uiso 1 1 d . . . H12 H -0.1704(19) 0.377(3) 0.1712(17) 0.051 Uiso 1 1 d . . . H13 H -0.204(2) 0.599(3) 0.2481(16) 0.053 Uiso 1 1 d . . . H15 H 0.0465(19) 0.529(3) 0.4277(17) 0.049 Uiso 1 1 d . . . H16 H 0.0780(19) 0.298(3) 0.3524(15) 0.045 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 0.0423(3) 0.0483(4) 0.0410(3) -0.0013(3) 0.0017(2) -0.0050(3) O3 0.0659(12) 0.0500(11) 0.0609(11) 0.0099(9) 0.0056(9) -0.0006(9) O5 0.0471(10) 0.0702(13) 0.0582(11) -0.0129(9) -0.0020(8) -0.0148(9) N1 0.0430(11) 0.0526(12) 0.0360(10) -0.0041(9) 0.0027(8) -0.0008(9) N2 0.0406(11) 0.0525(12) 0.0344(10) -0.0059(9) 0.0031(8) -0.0005(9) N3 0.0437(11) 0.0544(12) 0.0413(11) -0.0049(9) -0.0015(9) -0.0009(10) C1 0.0528(15) 0.0488(15) 0.0446(13) -0.0064(12) 0.0071(11) -0.0039(13) C2 0.0557(17) 0.0569(17) 0.0624(17) 0.0039(14) 0.0138(14) -0.0083(14) C3 0.0651(18) 0.072(2) 0.0488(15) 0.0107(14) 0.0224(14) 0.0094(15) C4 0.0676(18) 0.0602(17) 0.0355(13) -0.0029(12) 0.0084(12) 0.0094(15) C5 0.0505(14) 0.0448(14) 0.0355(12) -0.0020(10) 0.0013(10) 0.0022(12) C6 0.0427(13) 0.0383(13) 0.0354(11) -0.0015(10) 0.0035(10) 0.0046(10) C7 0.0437(13) 0.0391(13) 0.0356(12) -0.0071(10) 0.0037(10) 0.0030(10) C8 0.0449(14) 0.0488(14) 0.0397(12) -0.0056(11) 0.0080(11) -0.0013(11) C9 0.080(2) 0.086(2) 0.0471(15) -0.0240(16) -0.0046(14) 0.0082(18) C10 0.0511(17) 0.099(3) 0.077(2) -0.0029(18) -0.0119(15) 0.0111(17) C11 0.0361(12) 0.0509(14) 0.0361(11) 0.0024(10) 0.0059(9) -0.0025(10) C12 0.0392(14) 0.0646(17) 0.0441(13) 0.0026(13) 0.0000(11) -0.0025(12) C13 0.0408(14) 0.0655(18) 0.0588(16) 0.0066(14) 0.0041(13) 0.0114(13) C14 0.0460(14) 0.0607(16) 0.0520(14) -0.0028(12) 0.0146(12) 0.0028(12) C15 0.0439(14) 0.0736(19) 0.0398(13) -0.0132(13) 0.0032(11) 0.0036(13) C16 0.0376(13) 0.0658(16) 0.0372(12) -0.0018(12) 0.0028(10) 0.0107(12) C17 0.074(2) 0.084(2) 0.083(2) -0.0234(18) 0.0131(17) 0.0226(18) _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 O3 1.4332(18) . ? S1 O5 1.4354(17) . ? S1 N1 1.628(2) . ? S1 C11 1.761(2) . ? N1 C7 1.316(3) . ? N2 C8 1.309(3) . ? N2 C7 1.357(3) . ? N3 C8 1.312(3) . ? N3 C9 1.447(3) . ? N3 C10 1.453(3) . ? C1 C2 1.381(4) . ? C1 C6 1.387(3) . ? C1 H1 0.95(2) . ? C2 C3 1.372(4) . ? C2 H2 0.89(3) . ? C3 C4 1.376(4) . ? C3 H3 0.93(3) . ? C4 C5 1.373(4) . ? C4 H4 0.94(3) . ? C5 C6 1.389(3) . ? C5 H5 0.91(2) . ? C6 C7 1.484(3) . ? C8 H8 0.95(2) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C16 1.385(3) . ? C11 C12 1.386(3) . ? C12 C13 1.380(4) . ? C12 H12 0.92(2) . ? C13 C14 1.383(4) . ? C13 H13 0.92(3) . ? C14 C15 1.381(4) . ? C14 C17 1.507(4) . ? C15 C16 1.374(4) . ? C15 H15 0.92(3) . ? C16 H16 0.91(2) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O5 116.99(11) . . ? O3 S1 N1 113.34(11) . . ? O5 S1 N1 104.94(10) . . ? O3 S1 C11 108.44(11) . . ? O5 S1 C11 106.55(11) . . ? N1 S1 C11 105.85(11) . . ? C7 N1 S1 122.56(16) . . ? C8 N2 C7 119.19(19) . . ? C8 N3 C9 121.3(2) . . ? C8 N3 C10 121.3(2) . . ? C9 N3 C10 117.4(2) . . ? C2 C1 C6 120.1(2) . . ? C2 C1 H1 120.3(15) . . ? C6 C1 H1 119.6(15) . . ? C3 C2 C1 120.6(3) . . ? C3 C2 H2 119.3(17) . . ? C1 C2 H2 120.2(17) . . ? C4 C3 C2 119.7(3) . . ? C4 C3 H3 118.7(17) . . ? C2 C3 H3 121.5(17) . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.9(16) . . ? C3 C4 H4 119.9(15) . . ? C4 C5 C6 120.6(2) . . ? C4 C5 H5 119.4(15) . . ? C6 C5 H5 119.9(15) . . ? C1 C6 C5 118.7(2) . . ? C1 C6 C7 121.1(2) . . ? C5 C6 C7 120.2(2) . . ? N1 C7 N2 124.2(2) . . ? N1 C7 C6 114.52(18) . . ? N2 C7 C6 121.1(2) . . ? N2 C8 N3 123.0(2) . . ? N2 C8 H8 123.7(13) . . ? N3 C8 H8 113.2(14) . . ? N3 C9 H9A 109.5 . . ? N3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 119.6(2) . . ? C16 C11 S1 120.87(18) . . ? C12 C11 S1 119.51(18) . . ? C13 C12 C11 119.6(2) . . ? C13 C12 H12 120.4(16) . . ? C11 C12 H12 120.1(16) . . ? C12 C13 C14 121.5(3) . . ? C12 C13 H13 118.7(16) . . ? C14 C13 H13 119.7(16) . . ? C15 C14 C13 117.9(3) . . ? C15 C14 C17 121.6(2) . . ? C13 C14 C17 120.5(3) . . ? C16 C15 C14 121.7(2) . . ? C16 C15 H15 120.2(16) . . ? C14 C15 H15 118.1(16) . . ? C15 C16 C11 119.7(2) . . ? C15 C16 H16 122.4(15) . . ? C11 C16 H16 117.9(15) . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 S1 N1 C7 -41.1(2) . . . . ? O5 S1 N1 C7 -169.9(2) . . . . ? C11 S1 N1 C7 77.6(2) . . . . ? C6 C1 C2 C3 -1.5(4) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? C3 C4 C5 C6 -1.9(4) . . . . ? C2 C1 C6 C5 0.5(4) . . . . ? C2 C1 C6 C7 -179.2(2) . . . . ? C4 C5 C6 C1 1.2(4) . . . . ? C4 C5 C6 C7 -179.2(2) . . . . ? S1 N1 C7 N2 -9.2(3) . . . . ? S1 N1 C7 C6 174.84(16) . . . . ? C8 N2 C7 N1 154.0(2) . . . . ? C8 N2 C7 C6 -30.3(3) . . . . ? C1 C6 C7 N1 142.4(2) . . . . ? C5 C6 C7 N1 -37.2(3) . . . . ? C1 C6 C7 N2 -33.6(3) . . . . ? C5 C6 C7 N2 146.7(2) . . . . ? C7 N2 C8 N3 170.9(2) . . . . ? C9 N3 C8 N2 -5.0(4) . . . . ? C10 N3 C8 N2 176.7(3) . . . . ? O3 S1 C11 C16 36.6(2) . . . . ? O5 S1 C11 C16 163.3(2) . . . . ? N1 S1 C11 C16 -85.4(2) . . . . ? O3 S1 C11 C12 -143.5(2) . . . . ? O5 S1 C11 C12 -16.7(2) . . . . ? N1 S1 C11 C12 94.6(2) . . . . ? C16 C11 C12 C13 -0.5(4) . . . . ? S1 C11 C12 C13 179.5(2) . . . . ? C11 C12 C13 C14 1.3(4) . . . . ? C12 C13 C14 C15 -0.6(4) . . . . ? C12 C13 C14 C17 179.2(3) . . . . ? C13 C14 C15 C16 -1.0(4) . . . . ? C17 C14 C15 C16 179.3(3) . . . . ? C14 C15 C16 C11 1.7(4) . . . . ? C12 C11 C16 C15 -1.0(4) . . . . ? S1 C11 C16 C15 179.0(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.346 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.041 data_jpp _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H21 N3 O2 S' _chemical_formula_weight 343.44 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' 'S' 'S' 0.1246 0.1234 '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 8.032(3) _cell_length_b 13.044(2) _cell_length_c 17.604(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1844.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.190 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1331 _diffrn_reflns_av_R_equivalents 0.4246 _diffrn_reflns_av_sigmaI/netI 0.0107 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 22.98 _reflns_number_total 1330 _reflns_number_gt 1324 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0668P)^2^+0.5051P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.004(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.45(16) _refine_ls_number_reflns 1330 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0328 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.1070 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.180 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.01047(14) 0.10584(8) 0.26540(6) 0.0537(4) Uani 1 1 d . . . O1 O 1.1608(4) 0.1606(3) 0.28479(19) 0.0732(9) Uani 1 1 d . . . O2 O 1.0271(4) 0.0000(2) 0.24449(19) 0.0764(10) Uani 1 1 d . . . N1 N 0.8884(4) 0.1220(3) 0.34089(18) 0.0521(9) Uani 1 1 d . . . N2 N 0.6630(4) 0.0377(2) 0.28029(19) 0.0550(9) Uani 1 1 d . . . N3 N 0.5058(5) -0.0772(3) 0.2144(2) 0.0587(9) Uani 1 1 d . . . C1 C 0.9167(5) 0.1705(3) 0.1861(2) 0.0458(10) Uani 1 1 d . . . C2 C 0.8453(6) 0.1174(3) 0.1249(2) 0.0527(10) Uani 1 1 d . . . H2 H 0.8415 0.0461 0.1263 0.063 Uiso 1 1 calc R . . C3 C 0.7799(6) 0.1687(4) 0.0623(2) 0.0583(12) Uani 1 1 d . . . H3 H 0.7327 0.1314 0.0227 0.070 Uiso 1 1 calc R . . C4 C 0.7843(5) 0.2748(3) 0.0581(2) 0.0534(10) Uani 1 1 d . . . C5 C 0.8532(6) 0.3270(3) 0.1210(3) 0.0576(11) Uani 1 1 d . . . H5 H 0.8536 0.3983 0.1204 0.069 Uiso 1 1 calc R . . C6 C 0.9208(5) 0.2768(3) 0.1841(2) 0.0510(10) Uani 1 1 d . . . H6 H 0.9675 0.3139 0.2238 0.061 Uiso 1 1 calc R . . C7 C 0.7209(8) 0.3320(4) -0.0124(3) 0.0809(15) Uani 1 1 d . . . H7A H 0.7432 0.4039 -0.0070 0.105 Uiso 1 1 calc R . . H7B H 0.6032 0.3214 -0.0176 0.105 Uiso 1 1 calc R . . H7C H 0.7768 0.3064 -0.0567 0.105 Uiso 1 1 calc R . . C8 C 0.7382(6) 0.0815(3) 0.3418(2) 0.0471(10) Uani 1 1 d . . . C9 C 0.6057(5) -0.0541(3) 0.2742(2) 0.0490(10) Uani 1 1 d . . . C10 C 0.6516(6) -0.1370(3) 0.3305(3) 0.0696(13) Uani 1 1 d . . . H10A H 0.6889 -0.1967 0.3035 0.090 Uiso 1 1 calc R . . H10B H 0.5559 -0.1541 0.3606 0.090 Uiso 1 1 calc R . . H10C H 0.7390 -0.1127 0.3630 0.090 Uiso 1 1 calc R . . C11 C 0.4448(6) 0.0018(4) 0.1622(3) 0.0733(14) Uani 1 1 d . . . H11A H 0.4733 -0.0165 0.1110 0.095 Uiso 1 1 calc R . . H11B H 0.4951 0.0664 0.1747 0.095 Uiso 1 1 calc R . . H11C H 0.3260 0.0074 0.1667 0.095 Uiso 1 1 calc R . . C12 C 0.4548(7) -0.1824(4) 0.1964(4) 0.0894(17) Uani 1 1 d . . . H12A H 0.4000 -0.1834 0.1479 0.116 Uiso 1 1 calc R . . H12B H 0.3797 -0.2067 0.2348 0.116 Uiso 1 1 calc R . . H12C H 0.5512 -0.2258 0.1947 0.116 Uiso 1 1 calc R . . C13 C 0.6422(5) 0.0987(3) 0.4158(2) 0.0479(9) Uani 1 1 d . . . C14 C 0.7216(7) 0.1293(4) 0.4839(2) 0.0621(12) Uani 1 1 d . . . H14 H 0.8370 0.1356 0.4846 0.075 Uiso 1 1 calc R . . C15 C 0.6314(9) 0.1506(4) 0.5503(3) 0.0780(15) Uani 1 1 d . . . H15 H 0.6873 0.1696 0.5943 0.094 Uiso 1 1 calc R . . C16 C 0.4592(9) 0.1432(4) 0.5505(3) 0.0828(16) Uani 1 1 d . . . H16 H 0.3978 0.1575 0.5940 0.099 Uiso 1 1 calc R . . C17 C 0.3804(7) 0.1133(4) 0.4823(3) 0.0772(15) Uani 1 1 d . . . H17 H 0.2649 0.1081 0.4820 0.093 Uiso 1 1 calc R . . C18 C 0.4670(6) 0.0911(3) 0.4147(3) 0.0619(12) Uani 1 1 d . . . H18 H 0.4106 0.0719 0.3709 0.074 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 S1 0.0492(6) 0.0551(6) 0.0567(6) 0.0074(5) 0.0002(5) 0.0051(5) O1 0.0442(16) 0.094(2) 0.082(2) 0.0146(19) -0.0066(17) -0.0059(16) O2 0.091(2) 0.0561(17) 0.082(2) 0.0103(16) 0.006(2) 0.0248(18) N1 0.050(2) 0.055(2) 0.0510(19) -0.0003(17) -0.0062(16) -0.0057(17) N2 0.062(2) 0.0502(19) 0.053(2) 0.0057(16) -0.0013(19) -0.0138(17) N3 0.0514(19) 0.0566(18) 0.068(2) -0.0090(16) -0.010(2) -0.0052(17) C1 0.042(2) 0.045(2) 0.050(2) -0.0015(17) 0.0060(19) 0.0039(18) C2 0.065(3) 0.040(2) 0.053(2) -0.0027(19) -0.002(2) -0.008(2) C3 0.069(3) 0.062(3) 0.043(2) -0.007(2) -0.002(2) -0.016(2) C4 0.052(2) 0.058(2) 0.051(2) 0.003(2) -0.005(2) -0.001(2) C5 0.062(3) 0.043(2) 0.069(3) -0.001(2) 0.004(3) 0.002(2) C6 0.053(2) 0.047(2) 0.054(2) -0.0067(19) -0.009(2) -0.001(2) C7 0.085(4) 0.086(3) 0.072(3) 0.018(3) -0.016(3) 0.004(3) C8 0.058(3) 0.038(2) 0.045(2) 0.0078(17) -0.006(2) -0.0022(18) C9 0.043(2) 0.051(2) 0.054(2) -0.003(2) 0.007(2) -0.0013(18) C10 0.070(3) 0.049(2) 0.090(3) 0.002(2) 0.002(3) 0.003(2) C11 0.061(3) 0.086(3) 0.072(3) -0.001(3) -0.019(2) -0.006(3) C12 0.084(4) 0.073(3) 0.111(4) -0.026(3) -0.006(4) -0.025(3) C13 0.053(2) 0.039(2) 0.051(2) 0.0071(19) 0.004(2) -0.0044(19) C14 0.073(3) 0.060(3) 0.053(3) 0.002(2) 0.001(2) -0.008(2) C15 0.109(5) 0.071(3) 0.053(3) -0.002(2) 0.007(3) -0.008(3) C16 0.105(5) 0.064(3) 0.079(4) -0.003(3) 0.035(4) 0.003(3) C17 0.065(3) 0.062(3) 0.105(4) 0.001(3) 0.022(3) -0.001(3) C18 0.064(3) 0.050(2) 0.072(3) 0.006(2) 0.008(3) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.435(3) . ? S1 O1 1.444(3) . ? S1 N1 1.665(4) . ? S1 C1 1.797(4) . ? N1 C8 1.317(5) . ? N2 C9 1.287(5) . ? N2 C8 1.365(5) . ? N3 C9 1.358(5) . ? N3 C11 1.465(6) . ? N3 C12 1.466(6) . ? C1 C6 1.388(5) . ? C1 C2 1.403(5) . ? C2 C3 1.394(6) . ? C2 H2 0.9300 . ? C3 C4 1.386(6) . ? C3 H3 0.9300 . ? C4 C5 1.413(6) . ? C4 C7 1.534(6) . ? C5 C6 1.399(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C13 1.530(6) . ? C9 C10 1.511(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C18 1.410(7) . ? C13 C14 1.415(6) . ? C14 C15 1.403(7) . ? C14 H14 0.9300 . ? C15 C16 1.386(9) . ? C15 H15 0.9300 . ? C16 C17 1.411(8) . ? C16 H16 0.9300 . ? C17 C18 1.409(7) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 117.3(2) . . ? O2 S1 N1 112.44(19) . . ? O1 S1 N1 103.95(19) . . ? O2 S1 C1 106.93(18) . . ? O1 S1 C1 107.57(19) . . ? N1 S1 C1 108.28(17) . . ? C8 N1 S1 119.9(3) . . ? C9 N2 C8 127.9(4) . . ? C9 N3 C11 121.9(3) . . ? C9 N3 C12 122.7(4) . . ? C11 N3 C12 115.4(4) . . ? C6 C1 C2 119.0(4) . . ? C6 C1 S1 118.6(3) . . ? C2 C1 S1 122.4(3) . . ? C3 C2 C1 121.6(4) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C4 C3 C2 120.8(4) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 116.7(4) . . ? C3 C4 C7 121.3(4) . . ? C5 C4 C7 122.0(4) . . ? C6 C5 C4 123.3(4) . . ? C6 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? C1 C6 C5 118.6(4) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 N2 124.3(4) . . ? N1 C8 C13 114.4(3) . . ? N2 C8 C13 120.9(4) . . ? N2 C9 N3 118.8(4) . . ? N2 C9 C10 121.6(4) . . ? N3 C9 C10 119.6(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 H11A 109.5 . . ? N3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 118.7(4) . . ? C18 C13 C8 118.8(4) . . ? C14 C13 C8 122.3(4) . . ? C15 C14 C13 121.9(5) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C16 C15 C14 120.3(6) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 117.7(5) . . ? C15 C16 H16 121.2 . . ? C17 C16 H16 121.2 . . ? C18 C17 C16 123.6(5) . . ? C18 C17 H17 118.2 . . ? C16 C17 H17 118.2 . . ? C17 C18 C13 117.8(5) . . ? C17 C18 H18 121.1 . . ? C13 C18 H18 121.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 N1 C8 -52.5(4) . . . . ? O1 S1 N1 C8 179.6(3) . . . . ? C1 S1 N1 C8 65.4(3) . . . . ? O2 S1 C1 C6 -165.5(3) . . . . ? O1 S1 C1 C6 -38.7(4) . . . . ? N1 S1 C1 C6 73.1(4) . . . . ? O2 S1 C1 C2 12.0(4) . . . . ? O1 S1 C1 C2 138.8(3) . . . . ? N1 S1 C1 C2 -109.4(3) . . . . ? C6 C1 C2 C3 0.5(6) . . . . ? S1 C1 C2 C3 -177.0(3) . . . . ? C1 C2 C3 C4 0.4(7) . . . . ? C2 C3 C4 C5 -1.8(7) . . . . ? C2 C3 C4 C7 176.8(5) . . . . ? C3 C4 C5 C6 2.5(7) . . . . ? C7 C4 C5 C6 -176.2(4) . . . . ? C2 C1 C6 C5 0.1(6) . . . . ? S1 C1 C6 C5 177.7(3) . . . . ? C4 C5 C6 C1 -1.6(7) . . . . ? S1 N1 C8 N2 -9.5(5) . . . . ? S1 N1 C8 C13 177.7(3) . . . . ? C9 N2 C8 N1 122.8(4) . . . . ? C9 N2 C8 C13 -64.8(6) . . . . ? C8 N2 C9 N3 166.8(4) . . . . ? C8 N2 C9 C10 -15.2(7) . . . . ? C11 N3 C9 N2 -7.8(6) . . . . ? C12 N3 C9 N2 170.7(4) . . . . ? C11 N3 C9 C10 174.2(4) . . . . ? C12 N3 C9 C10 -7.3(6) . . . . ? N1 C8 C13 C18 158.5(4) . . . . ? N2 C8 C13 C18 -14.6(6) . . . . ? N1 C8 C13 C14 -16.7(5) . . . . ? N2 C8 C13 C14 170.2(4) . . . . ? C18 C13 C14 C15 1.1(7) . . . . ? C8 C13 C14 C15 176.3(4) . . . . ? C13 C14 C15 C16 -0.9(8) . . . . ? C14 C15 C16 C17 0.4(9) . . . . ? C15 C16 C17 C18 -0.1(8) . . . . ? C16 C17 C18 C13 0.3(8) . . . . ? C14 C13 C18 C17 -0.8(7) . . . . ? C8 C13 C18 C17 -176.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.890 _diffrn_reflns_theta_full 22.98 _diffrn_measured_fraction_theta_full 0.890 _refine_diff_density_max 0.179 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.042 data_mg _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 N2 O2, H2 O' _chemical_formula_weight 250.29 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 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 12.638(7) _cell_length_b 7.998(2) _cell_length_c 12.9680(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.15(2) _cell_angle_gamma 90.00 _cell_volume 1308.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2770 _diffrn_reflns_av_R_equivalents 0.0110 _diffrn_reflns_av_sigmaI/netI 0.0143 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 26.96 _reflns_number_total 2651 _reflns_number_gt 2143 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0889P)^2^+1.2514P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.007(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2651 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1789 _refine_ls_wR_factor_gt 0.1663 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.172 _refine_ls_shift/su_mean 0.012 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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.57652(15) 0.2652(2) 0.17533(12) 0.0452(5) Uani 1 1 d . . . O2 O 0.32206(14) 0.4426(2) 0.38647(13) 0.0414(5) Uani 1 1 d . . . N1 N 0.50700(14) 0.4341(2) 0.29603(14) 0.0315(5) Uani 1 1 d . . . N2 N 0.52419(15) 0.6163(3) 0.15666(15) 0.0381(5) Uani 1 1 d . . . C1 C 0.59467(18) 0.0020(3) 0.32167(19) 0.0373(6) Uani 1 1 d . . . C2 C 0.6219(2) -0.1157(4) 0.3959(2) 0.0428(6) Uani 1 1 d . . . C3 C 0.6428(2) -0.0674(4) 0.4974(2) 0.0432(6) Uani 1 1 d . . . C4 C 0.6351(2) 0.0979(4) 0.52436(19) 0.0423(6) Uani 1 1 d . . . C5 C 0.60559(18) 0.2169(3) 0.45045(17) 0.0350(5) Uani 1 1 d . . . C6 C 0.58557(16) 0.1688(3) 0.34849(16) 0.0298(5) Uani 1 1 d . . . C7 C 0.55744(16) 0.2909(3) 0.26496(16) 0.0313(5) Uani 1 1 d . . . C8 C 0.46295(17) 0.5534(3) 0.22744(16) 0.0296(5) Uani 1 1 d . . . C9 C 0.35859(17) 0.6026(3) 0.23895(17) 0.0328(5) Uani 1 1 d . . . C10 C 0.29377(18) 0.5445(3) 0.31595(18) 0.0334(5) Uani 1 1 d . . . C11 C 0.1830(2) 0.6140(4) 0.3155(3) 0.0487(7) Uani 1 1 d . . . C12 C 0.6394(2) 0.6057(4) 0.1624(2) 0.0463(6) Uani 1 1 d . . . C13 C 0.4791(3) 0.7160(5) 0.0714(2) 0.0528(7) Uani 1 1 d . . . O3 O 0.7878(2) -0.4823(3) 0.41869(19) 0.0679(7) Uiso 1 1 d . . . H1A H 0.4684(19) 0.421(3) 0.3489(19) 0.024 Uiso 1 1 d . . . H1 H 0.584(2) -0.033(3) 0.251(2) 0.036 Uiso 1 1 d . . . H3 H 0.661(2) -0.146(4) 0.548(2) 0.037 Uiso 1 1 d . . . H4 H 0.648(2) 0.132(3) 0.592(2) 0.034 Uiso 1 1 d . . . H9 H 0.3334(18) 0.689(3) 0.1962(18) 0.026 Uiso 1 1 d . . . H11A H 0.175(2) 0.700(4) 0.270(2) 0.034 Uiso 1 1 d . . . H11B H 0.140(2) 0.542(4) 0.300(2) 0.034 Uiso 1 1 d . . . H11C H 0.159(2) 0.626(3) 0.381(2) 0.034 Uiso 1 1 d . . . H12A H 0.670(2) 0.723(4) 0.1513(19) 0.034 Uiso 1 1 d . . . H12B H 0.665(2) 0.571(3) 0.232(2) 0.034 Uiso 1 1 d . . . H12C H 0.659(2) 0.535(4) 0.119(2) 0.034 Uiso 1 1 d . . . H13A H 0.521(2) 0.706(3) 0.014(2) 0.037 Uiso 1 1 d . . . H13B H 0.407(2) 0.666(3) 0.0525(19) 0.037 Uiso 1 1 d . . . H13C H 0.465(2) 0.815(4) 0.090(2) 0.037 Uiso 1 1 d . . . H5 H 0.6047(18) 0.332(3) 0.4669(17) 0.025 Uiso 1 1 d . . . H2 H 0.625(2) -0.221(4) 0.379(2) 0.041 Uiso 1 1 d . . . H3A H 0.763(2) -0.435(4) 0.487(2) 0.050 Uiso 1 1 d . . . H3B H 0.844(2) -0.378(4) 0.413(2) 0.050 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 O1 0.0621(11) 0.0444(11) 0.0299(8) -0.0001(7) 0.0089(7) 0.0152(9) O2 0.0438(9) 0.0393(11) 0.0421(9) 0.0099(7) 0.0125(7) 0.0093(7) N1 0.0312(9) 0.0355(12) 0.0281(9) 0.0031(7) 0.0051(7) 0.0073(8) N2 0.0383(10) 0.0396(12) 0.0370(10) 0.0086(8) 0.0084(8) 0.0048(9) C1 0.0364(12) 0.0385(15) 0.0372(12) -0.0023(10) 0.0031(9) 0.0041(10) C2 0.0454(13) 0.0286(14) 0.0547(15) 0.0028(11) 0.0058(11) 0.0041(11) C3 0.0377(12) 0.0446(17) 0.0471(14) 0.0177(12) 0.0009(10) 0.0014(11) C4 0.0432(13) 0.0500(17) 0.0331(12) 0.0043(11) -0.0025(9) -0.0020(11) C5 0.0369(11) 0.0332(14) 0.0350(11) -0.0008(9) 0.0018(9) -0.0006(10) C6 0.0246(9) 0.0325(13) 0.0325(10) 0.0022(9) 0.0037(8) 0.0023(8) C7 0.0288(10) 0.0334(13) 0.0319(11) 0.0003(9) 0.0028(8) 0.0021(9) C8 0.0331(10) 0.0281(12) 0.0277(10) -0.0007(8) 0.0027(8) 0.0030(9) C9 0.0327(11) 0.0304(13) 0.0353(11) 0.0055(9) 0.0012(8) 0.0057(9) C10 0.0342(11) 0.0279(13) 0.0383(11) -0.0013(9) 0.0037(9) 0.0022(9) C11 0.0338(13) 0.0489(18) 0.0643(18) 0.0128(15) 0.0117(12) 0.0041(12) C12 0.0387(13) 0.0478(18) 0.0539(16) 0.0004(13) 0.0176(11) 0.0010(12) C13 0.0633(18) 0.0545(19) 0.0414(14) 0.0163(13) 0.0120(13) 0.0096(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.218(3) . ? O2 C10 1.262(3) . ? N1 C7 1.382(3) . ? N1 C8 1.399(3) . ? N1 H1A 0.87(2) . ? N2 C8 1.331(3) . ? N2 C13 1.455(3) . ? N2 C12 1.456(3) . ? C1 C2 1.377(4) . ? C1 C6 1.385(4) . ? C1 H1 0.96(3) . ? C2 C3 1.383(4) . ? C2 H2 0.87(3) . ? C3 C4 1.373(4) . ? C3 H3 0.93(3) . ? C4 C5 1.387(3) . ? C4 H4 0.93(3) . ? C5 C6 1.387(3) . ? C5 H5 0.95(3) . ? C6 C7 1.487(3) . ? C8 C9 1.392(3) . ? C9 C10 1.405(3) . ? C9 H9 0.93(3) . ? C10 C11 1.505(3) . ? C11 H11A 0.91(3) . ? C11 H11B 0.81(3) . ? C11 H11C 0.92(3) . ? C12 H12A 1.03(3) . ? C12 H12B 0.98(3) . ? C12 H12C 0.85(3) . ? C13 H13A 0.94(3) . ? C13 H13B 1.01(3) . ? C13 H13C 0.85(3) . ? O3 H3A 1.03(3) . ? O3 H3B 1.10(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 C7 N1 C8 123.63(18) . . ? C7 N1 H1A 114.5(16) . . ? C8 N1 H1A 111.3(16) . . ? C8 N2 C13 120.9(2) . . ? C8 N2 C12 124.1(2) . . ? C13 N2 C12 114.8(2) . . ? C2 C1 C6 120.3(2) . . ? C2 C1 H1 119.2(16) . . ? C6 C1 H1 120.5(16) . . ? C1 C2 C3 120.1(3) . . ? C1 C2 H2 119.7(19) . . ? C3 C2 H2 120.2(19) . . ? C4 C3 C2 120.0(2) . . ? C4 C3 H3 119.3(17) . . ? C2 C3 H3 120.8(17) . . ? C3 C4 C5 120.3(2) . . ? C3 C4 H4 120.8(16) . . ? C5 C4 H4 118.8(17) . . ? C6 C5 C4 119.8(2) . . ? C6 C5 H5 118.7(14) . . ? C4 C5 H5 121.3(14) . . ? C1 C6 C5 119.5(2) . . ? C1 C6 C7 118.0(2) . . ? C5 C6 C7 122.4(2) . . ? O1 C7 N1 122.5(2) . . ? O1 C7 C6 122.2(2) . . ? N1 C7 C6 115.33(18) . . ? N2 C8 C9 123.9(2) . . ? N2 C8 N1 118.02(19) . . ? C9 C8 N1 118.09(19) . . ? C8 C9 C10 125.1(2) . . ? C8 C9 H9 116.2(14) . . ? C10 C9 H9 118.4(14) . . ? O2 C10 C9 125.1(2) . . ? O2 C10 C11 117.9(2) . . ? C9 C10 C11 116.9(2) . . ? C10 C11 H11A 110.6(16) . . ? C10 C11 H11B 111(2) . . ? H11A C11 H11B 110(3) . . ? C10 C11 H11C 112.8(16) . . ? H11A C11 H11C 119(2) . . ? H11B C11 H11C 93(2) . . ? N2 C12 H12A 108.8(14) . . ? N2 C12 H12B 110.1(15) . . ? H12A C12 H12B 106(2) . . ? N2 C12 H12C 109.6(18) . . ? H12A C12 H12C 113(2) . . ? H12B C12 H12C 109(2) . . ? N2 C13 H13A 109.7(16) . . ? N2 C13 H13B 106.0(15) . . ? H13A C13 H13B 108(2) . . ? N2 C13 H13C 111.9(19) . . ? H13A C13 H13C 116(3) . . ? H13B C13 H13C 104(2) . . ? H3A O3 H3B 90(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 C6 C1 C2 C3 -1.5(4) . . . . ? C1 C2 C3 C4 0.7(4) . . . . ? C2 C3 C4 C5 0.6(4) . . . . ? C3 C4 C5 C6 -1.2(4) . . . . ? C2 C1 C6 C5 0.9(3) . . . . ? C2 C1 C6 C7 179.2(2) . . . . ? C4 C5 C6 C1 0.4(3) . . . . ? C4 C5 C6 C7 -177.7(2) . . . . ? C8 N1 C7 O1 7.3(3) . . . . ? C8 N1 C7 C6 -171.88(19) . . . . ? C1 C6 C7 O1 -25.2(3) . . . . ? C5 C6 C7 O1 152.9(2) . . . . ? C1 C6 C7 N1 153.9(2) . . . . ? C5 C6 C7 N1 -27.9(3) . . . . ? C13 N2 C8 C9 -13.4(4) . . . . ? C12 N2 C8 C9 160.7(3) . . . . ? C13 N2 C8 N1 168.4(2) . . . . ? C12 N2 C8 N1 -17.5(4) . . . . ? C7 N1 C8 N2 -52.9(3) . . . . ? C7 N1 C8 C9 128.7(2) . . . . ? N2 C8 C9 C10 -176.8(2) . . . . ? N1 C8 C9 C10 1.5(4) . . . . ? C8 C9 C10 O2 1.7(4) . . . . ? C8 C9 C10 C11 179.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 26.96 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 1.003 _refine_diff_density_min -0.497 _refine_diff_density_rms 0.056