# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/235 data_global _publ_section_title ; Tautomerism of Schiff bases derived from 3-hydroxysalicylaldehyde. Combined X-ray diffraction, solution and solid state NMR study ; _publ_contact_author_name 'helene PIZZALA' _publ_contact_author_address ; Laboratoire Spectrometries et Dynamiques Moleculaires Case 542 Universite de Provence Avenue Escadrille Normandie Niemen 13397 Marseille cedex 20 France ; _publ_requested_journal 'Perkin Transactions 2' _publ_contact_author_email 'helene@piimsdm3.univ-mrs.fr' _publ_contact_author_fax '(33) 4 91 63 65 10' _publ_contact_author_phone '(33) 4 91 28 85 80' #============================================================== data_crystal_compound1 _computing_data_collection 'KappaCCD' _computing_structure_refinement 'maxus(Mackay et al., 1999)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_molecular_graphics 'Ortep (Johnson, 1976)' _computing_publication_material 'maxus(Mackay et al., 1999)' _chemical_compound_source 'Local laboratory' _chemical_formula_sum 'C16 H18 N2 O4 ' _chemical_formula_weight 302.24 _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 6.8550(10) _cell_length_b 7.5510(10) _cell_length_c 14.6220(10) _cell_angle_alpha 80.660(10) _cell_angle_beta 88.460(10) _cell_angle_gamma 87.170(10) _cell_volume 746.0(10) _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _diffrn_radiation_wavelength 0.71073 _cell_measurement_reflns_used 6788 _cell_measurement_theta_min '1' _cell_measurement_theta_max 25 _cell_measurement_temperature 298 _exptl_absorpt_coefficient_mu 0.098 _exptl_crystal_F_000 324 _exptl_crystal_description 'plate' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_colour 'yellow' _refine_ls_hydrogen_treatment 'noref' _diffrn_measurement_device 'KappaCCD' _diffrn_measurement_method 'phi-scan' _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'fine-focus sealed tube' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 2795 _reflns_number_total 2795 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_av_R_equivalents 0.06 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 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 'Waasmaier & Kirfel, 1995' 'H ' 'H ' 0.0000 0.0000 'Waasmaier & Kirfel, 1995' 'O ' 'O ' 0.0106 0.0060 'Waasmaier & Kirfel, 1995' 'N ' 'N ' 0.0061 0.0033 'Waasmaier & Kirfel, 1995' _reflns_number_gt 2166 _reflns_threshold_expression 'I> 3.00 sigma(I)' _reflns_d_resolution_low 1.90 _reflns_d_resolution_high 0.63 _reflns_limit_h_max 8 _reflns_limit_h_min 0 _reflns_limit_k_max 9 _reflns_limit_k_min -9 _reflns_limit_l_max 8 _reflns_limit_l_min 0 _refine_ls_matrix_type full _refine_ls_R_factor_all 0.056 _refine_ls_wR_factor_all 0.063 _refine_ls_R_factor_gt 0.042 _refine_ls_wR_factor_gt 0.063 _refine_ls_wR_factor_ref 0.063 _refine_ls_goodness_of_fit_gt 1.023 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_goodness_of_fit_all 0.976 _refine_ls_number_parameters 199 _refine_ls_number_reflns 2166 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef F^2^ _refine_special_details ; Refinement on F^2^. ; _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ; w = 1 / ( s^2^(Fo^2^) + 0.03000 * Fo^2^) ; _refine_ls_extinction_method 'none' _atom_sites_solution_hydrogens difmap _refine_diff_density_max 0.31 _refine_diff_density_min -0.24 _refine_diff_density_rms 0.07 #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O2 0.33415(6) -0.13357(5) 0.65302(3) 0.0355(2) 1.00 Uij O33 0.27939(6) 0.19669(5) 0.70177(2) 0.0386(2) 1.00 Uij O3 0.58848(6) -0.21507(6) 0.79787(3) 0.0442(2) 1.00 Uij O22 0.26840(6) -0.05305(5) 0.85995(2) 0.0344(2) 1.00 Uij N11 0.25331(7) -0.12003(6) 1.03893(3) 0.0307(2) 1.00 Uij N1 0.25956(7) -0.14951(6) 0.48277(3) 0.0327(2) 1.00 Uij C33 0.26169(8) 0.24970(7) 0.78645(4) 0.0281(3) 1.00 Uij C11 0.24028(8) 0.17745(7) 0.95401(4) 0.0273(3) 1.00 Uij C22 0.25693(7) 0.11549(7) 0.86730(4) 0.0261(3) 1.00 Uij C7 0.42870(9) -0.23403(7) 0.47795(4) 0.0325(3) 1.00 Uij C77 0.23881(8) 0.05209(8) 1.03781(4) 0.0316(3) 1.00 Uij C3 0.63159(8) -0.26725(7) 0.71479(4) 0.0320(3) 1.00 Uij C44 0.24968(8) 0.42798(7) 0.79260(4) 0.0329(3) 1.00 Uij C88 0.25338(9) -0.25363(8) 1.12369(4) 0.0405(3) 1.00 Uij C1 0.55287(8) -0.27601(7) 0.55487(4) 0.0290(3) 1.00 Uij C2 0.49726(8) -0.22126(7) 0.64099(4) 0.0283(3) 1.00 Uij C66 0.22650(9) 0.36361(8) 0.95841(4) 0.0385(3) 1.00 Uij C4 0.80349(9) -0.35989(8) 0.70353(4) 0.0373(3) 1.00 Uij C6 0.73421(9) -0.37074(7) 0.54508(4) 0.0373(3) 1.00 Uij C55 0.23048(9) 0.48658(7) 0.87881(4) 0.0399(3) 1.00 Uij C5 0.85616(9) -0.41222(8) 0.61780(4) 0.0417(3) 1.00 Uij C8 0.12790(10) -0.10455(8) 0.40515(4) 0.0443(3) 1.00 Uij H7 0.4659(9) -0.2643(8) 0.4123(4) 0.06232 1.00 Uiso H77 0.2280(9) 0.0982(8) 1.1072(4) 0.06152 1.00 Uiso H44 0.2547(8) 0.5153(7) 0.7359(4) 0.06224 1.00 Uiso H66 0.2163(9) 0.4009(8) 1.0227(4) 0.06870 1.00 Uiso H4 0.8945(9) -0.3868(8) 0.7587(4) 0.06673 1.00 Uiso H6 0.7608(9) -0.4009(8) 0.4824(4) 0.06727 1.00 Uiso H55 0.2219(9) 0.6145(8) 0.8771(4) 0.06968 1.00 Uiso H5 0.9750(10) -0.4801(9) 0.6231(5) 0.07123 1.00 Uiso H33 0.3010(10) 0.0510(10) 0.7116(6) 0.06810 1.00 Uiso H3 0.4580(10) -0.1570(10) 0.7930(5) 0.07408 1.00 Uiso H8A 0.1920(10) -0.1440(10) 0.3411(6) 0.07366 1.00 Uiso H8B 0.1000(10) 0.0320(10) 0.3864(5) 0.07366 1.00 Uiso H88A 0.1360(10) -0.3310(9) 1.1313(5) 0.06922 1.00 Uiso H8C 0.0190(10) -0.1470(10) 0.4144(5) 0.07366 1.00 Uiso H88B 0.3700(10) -0.3350(10) 1.1284(5) 0.06922 1.00 Uiso H88C 0.2560(10) -0.1888(9) 1.1842(5) 0.06922 1.00 Uiso H1 0.2320(10) -0.1162(9) 0.5526(5) 0.06240 1.00 Uiso H11 0.2670(10) -0.1562(9) 0.9733(5) 0.06022 1.00 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O2 0.0335(2) 0.0417(2) 0.0311(2) 0.0061(2) 0.0001(2) -.0134(2) O33 0.0537(3) 0.0366(2) 0.0238(2) -.0015(2) 0.0034(2) -.0025(2) O3 0.0394(3) 0.0634(3) 0.0294(2) 0.0056(2) -.0039(2) -.0157(2) O22 0.0487(3) 0.0251(2) 0.0288(2) -.0012(2) 0.0058(2) -.0071(2) N11 0.0290(3) 0.0351(3) 0.0266(2) -.0023(2) 0.0007(2) -.0015(2) N1 0.0385(3) 0.0305(3) 0.0281(3) -.0036(2) -.0006(2) -.0040(2) C33 0.0253(3) 0.0322(3) 0.0260(3) -.0021(2) -.0002(2) -.0046(2) C11 0.0250(3) 0.0288(3) 0.0279(3) -.0015(2) -.0002(2) -.0077(2) C22 0.0221(3) 0.0278(3) 0.0276(3) -.0006(2) 0.0012(2) -.0056(2) C7 0.0411(3) 0.0277(3) 0.0281(3) -.0096(2) 0.0077(3) -.0056(2) C77 0.0266(3) 0.0395(3) 0.0285(3) -.0034(2) -.0011(3) -.0094(2) C3 0.0349(3) 0.0331(3) 0.0272(3) -.0033(2) 0.0030(3) -.0063(2) C44 0.0279(3) 0.0289(3) 0.0400(3) -.0014(2) -.0006(3) 0.0006(2) C88 0.0388(4) 0.0467(4) 0.0322(3) -.0024(3) -.0022(3) 0.0098(3) C1 0.0325(3) 0.0246(3) 0.0293(3) -.0055(2) 0.0062(3) -.0057(2) C2 0.0296(3) 0.0248(3) 0.0298(3) -.0042(2) 0.0034(3) -.0048(2) C66 0.0422(4) 0.0341(3) 0.0397(3) -.0025(3) 0.0019(3) -.0166(3) C4 0.0360(3) 0.0353(3) 0.0388(3) 0.0012(3) -.0006(3) -.0023(3) C6 0.0383(3) 0.0336(3) 0.0398(3) -.0028(3) 0.0103(3) -.0127(3) C55 0.0415(4) 0.0256(3) 0.0518(4) -.0020(3) 0.0017(3) -.0099(3) C5 0.0350(3) 0.0366(3) 0.0520(4) 0.0056(3) 0.0041(3) -.0087(3) C8 0.0471(4) 0.0465(4) 0.0372(3) -.0050(3) -.0091(3) -.0001(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C2 1.2950(10) . . ? O33 C33 1.3640(10) . . ? O3 C3 1.3590(10) . . ? O22 C22 1.2960(10) . . ? N11 C77 1.2990(10) . . ? N11 C88 1.4670(10) . . ? N1 C7 1.3020(10) . . ? N1 C8 1.4560(10) . . ? C33 C22 1.4290(10) . . ? C33 C44 1.3650(10) . . ? C11 C22 1.4220(10) . . ? C11 C77 1.4230(10) . . ? C11 C66 1.4190(10) . . ? C7 C1 1.4140(10) . . ? C3 C2 1.4270(10) . . ? C3 C4 1.3610(10) . . ? C44 C55 1.4050(10) . . ? C1 C2 1.4260(10) . . ? C1 C6 1.4200(10) . . ? C66 C55 1.3680(10) . . ? C4 C5 1.4090(10) . . ? C6 C5 1.3570(10) . . ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C77 N11 C88 124.20(10) . . . ? C7 N1 C8 123.80(10) . . . ? O33 C33 C22 118.70(10) . . . ? O33 C33 C44 119.90(10) . . . ? C22 C33 C44 121.40(10) . . . ? C22 C11 C77 119.90(10) . . . ? C22 C11 C66 120.90(10) . . . ? C77 C11 C66 119.20(10) . . . ? O22 C22 C33 120.50(10) . . . ? O22 C22 C11 123.00(10) . . . ? C33 C22 C11 116.60(10) . . . ? N1 C7 C1 122.40(10) . . . ? N11 C77 C11 122.40(10) . . . ? O3 C3 C2 119.30(10) . . . ? O3 C3 C4 119.20(10) . . . ? C2 C3 C4 121.50(10) . . . ? C33 C44 C55 121.20(10) . . . ? C7 C1 C2 120.20(10) . . . ? C7 C1 C6 119.40(10) . . . ? C2 C1 C6 120.50(10) . . . ? O2 C2 C3 120.70(10) . . . ? O2 C2 C1 122.70(10) . . . ? C3 C2 C1 116.60(10) . . . ? C11 C66 C55 120.20(10) . . . ? C3 C4 C5 121.00(10) . . . ? C1 C6 C5 120.50(10) . . . ? C44 C55 C66 119.70(10) . . . ? C4 C5 C6 119.90(10) . . . ? #==============================================END data_crystal_compound4 _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'maxus(Mackay et al., 1999)' _computing_molecular_graphics 'Ortep (Johnson, 1976)' _computing_publication_material 'maxus(Mackay et al., 1999)' _chemical_compound_source 'Local laboratory' _chemical_formula_sum 'C13 H10 N2 O4 ' _chemical_formula_weight 258.233 _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 7.005(1) _cell_length_b 7.180(1) _cell_length_c 12.018(1) _cell_angle_alpha 83.21(1) _cell_angle_beta 79.16(1) _cell_angle_gamma 72.66(1) _cell_volume 565.(2) _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _cell_measurement_reflns_used 3628 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25 _cell_measurement_temperature 298 _exptl_crystal_description 'Cube' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_colour 'black' _diffrn_measurement_device 'KappaCCD' _diffrn_measurement_method 'phi-scan' _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'fine-focus sealed tube' _exptl_absorpt_correction_type none _diffrn_reflns_number 1968 _reflns_number_total 1968 _diffrn_reflns_theta_max 26.36 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_coefficient_mu 0.115 _exptl_crystal_F_000 268 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 'Waasmaier & Kirfel, 1995' 'H ' 'H ' 0.0000 0.0000 'Waasmaier & Kirfel, 1995' 'O ' 'O ' 0.0106 0.0060 'Waasmaier & Kirfel, 1995' 'N ' 'N ' 0.0061 0.0033 'Waasmaier & Kirfel, 1995' _reflns_number_gt 1039 _reflns_threshold_expression 'I> 3.00 sigma(I)' _reflns_d_resolution_low 1.76 _reflns_d_resolution_high 0.63 _reflns_limit_h_max 8 _reflns_limit_h_min 0 _reflns_limit_k_max 8 _reflns_limit_k_min -6 _reflns_limit_l_max 8 _reflns_limit_l_min 0 _refine_ls_matrix_type full _refine_ls_R_factor_all 0.136 _refine_ls_wR_factor_all 0.150 _refine_ls_R_factor_gt 0.074 _refine_ls_wR_factor_gt 0.150 _refine_ls_wR_factor_ref 0.150 _refine_ls_goodness_of_fit_gt 1.445 _refine_ls_goodness_of_fit_ref 1.445 _refine_ls_goodness_of_fit_all 1.266 _refine_ls_number_reflns 1039 _refine_ls_number_parameters 173 _refine_ls_hydrogen_treatment 'noref' _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.18 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.04 _refine_ls_structure_factor_coef F^2^ _refine_special_details ; Refinement on F^2^. ; _refine_ls_weighting_scheme 'sigma' _refine_ls_weighting_details ; w = 1 / ( s^2^(Fo^2^) + 0.03000 * Fo^2^) ; _refine_ls_extinction_method 'Zachariasen' _refine_ls_extinction_expression 'equ(22) p292 Crystallographic Computing (1970) ' _refine_ls_extinction_coef 39620(688) _atom_sites_solution_hydrogens difmap #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O2 -0.1464(2) -0.2829(1) 0.02712(7) 0.0509(6) 1.00 Uij O4 -0.3056(2) 0.6310(2) 0.47601(9) 0.0778(8) 1.00 Uij O3 -0.1597(2) -0.5032(1) -0.14052(7) 0.0565(6) 1.00 Uij O1 -0.1651(2) 0.3492(2) 0.56310(8) 0.0894(9) 1.00 Uij N2 -0.2371(2) 0.4514(2) 0.48095(9) 0.0578(9) 1.00 Uij C1 -0.2731(2) 0.0146(2) -0.0839(1) 0.0397(8) 1.00 Uij N1 -0.2275(2) 0.0550(2) 0.10228(8) 0.0413(7) 1.00 Uij C12 -0.1871(3) 0.1471(2) 0.3905(1) 0.0465(9) 1.00 Uij C2 -0.2093(3) -0.1925(2) -0.0668(1) 0.0437(9) 1.00 Uij C3 -0.2146(3) -0.3043(2) -0.1564(1) 0.0448(9) 1.00 Uij C4 -0.2790(3) -0.2114(2) -0.2558(1) 0.0433(9) 1.00 Uij C5 -0.3386(3) -0.0070(2) -0.2721(1) 0.0453(9) 1.00 Uij C10 -0.2847(3) 0.4593(2) 0.2840(1) 0.0430(9) 1.00 Uij C9 -0.2822(3) 0.3643(2) 0.1893(1) 0.0453(9) 1.00 Uij C11 -0.2351(3) 0.3467(2) 0.3817(1) 0.0448(9) 1.00 Uij C13 -0.1857(3) 0.0483(2) 0.2966(1) 0.0461(9) 1.00 Uij C6 -0.3363(3) 0.1049(2) -0.1890(1) 0.0445(9) 1.00 Uij C7 -0.2819(2) 0.1327(2) 0.0034(1) 0.0413(9) 1.00 Uij C8 -0.2344(3) 0.1615(2) 0.1963(1) 0.0416(9) 1.00 Uij H13 -0.13253 -0.11125 0.30036 0.06672 1.00 Uiso H6 -0.37195 0.26611 -0.19637 0.06461 1.00 Uiso H7 -0.33316 0.29236 -0.00963 0.06261 1.00 Uiso H10 -0.32690 0.61565 0.27436 0.06377 1.00 Uiso H9 -0.33060 0.44344 0.11685 0.06812 1.00 Uiso H12 -0.16472 0.05243 0.46365 0.06818 1.00 Uiso H5 -0.37295 0.03559 -0.34266 0.06613 1.00 Uiso H4 -0.28250 -0.29768 -0.31893 0.06541 1.00 Uiso H3 -0.04184 -0.54017 -0.10842 0.07439 1.00 Uiso H1 -0.17632 -0.10067 0.11248 0.06103 1.00 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O2 0.0790(9) 0.0319(6) 0.0351(5) -.0138(6) -.0181(5) 0.0024(4) O4 0.110(1) 0.0589(9) 0.0566(7) -.0187(8) -.0237(7) -.0223(6) O3 0.083(1) 0.0328(7) 0.0496(6) -.0206(6) -.0225(6) -.0016(4) O1 0.146(1) 0.0747(9) 0.0408(6) -.0414(9) -.0392(8) 0.0031(6) N2 0.072(1) 0.057(1) 0.0389(8) -.0244(9) -.0078(8) -.0086(7) C1 0.057(1) 0.0270(9) 0.0298(7) -.0124(8) -.0102(7) -.0018(6) N1 0.056(1) 0.0280(7) 0.0352(6) -.0121(6) -.0109(6) -.0026(5) C12 0.060(1) 0.038(1) 0.0362(8) -.0161(9) -.0134(8) 0.0058(6) C2 0.061(1) 0.035(1) 0.0310(8) -.0166(8) -.0126(8) 0.0008(6) C3 0.061(1) 0.033(1) 0.0347(8) -.0171(9) -.0092(8) 0.0006(7) C4 0.053(1) 0.037(1) 0.0360(8) -.0152(8) -.0099(8) -.0074(6) C5 0.064(1) 0.036(1) 0.0293(7) -.0140(8) -.0116(7) -.0006(6) C10 0.054(1) 0.034(1) 0.0359(8) -.0108(8) -.0091(8) -.0066(6) C9 0.063(1) 0.034(1) 0.0343(8) -.0160(8) -.0130(8) 0.0003(6) C11 0.050(1) 0.051(1) 0.0291(8) -.0160(9) -.0043(7) -.0114(7) C13 0.062(1) 0.039(1) 0.0312(7) -.0142(8) -.0090(7) -.0029(6) C6 0.056(1) 0.036(1) 0.0352(8) -.0133(8) -.0111(8) 0.0058(6) C7 0.052(1) 0.033(1) 0.0323(8) -.0095(8) -.0095(7) 0.0044(6) C8 0.054(1) 0.040(1) 0.0273(7) -.0175(8) -.0115(7) -.0019(6) _geom_special_details ; All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C2 1.317(2) . . ? O4 N2 1.233(2) . . ? O3 C3 1.364(2) . . ? O1 N2 1.250(2) . . ? N2 C11 1.479(2) . . ? C1 C2 1.421(2) . . ? C1 C6 1.434(2) . . ? C1 C7 1.407(2) . . ? N1 C7 1.325(2) . . ? N1 C8 1.424(2) . . ? C12 C11 1.367(2) . . ? C12 C13 1.400(2) . . ? C2 C3 1.428(2) . . ? C3 C4 1.383(2) . . ? C4 C5 1.401(2) . . ? C5 C6 1.359(2) . . ? C10 C9 1.389(2) . . ? C10 C11 1.384(2) . . ? C9 C8 1.389(2) . . ? C13 C8 1.409(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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 N2 O1 125.1(2) . . . ? O4 N2 C11 118.2(2) . . . ? O1 N2 C11 116.7(2) . . . ? C2 C1 C6 120.2(2) . . . ? C2 C1 C7 120.4(2) . . . ? C6 C1 C7 119.4(2) . . . ? C7 N1 C8 125.6(2) . . . ? C11 C12 C13 119.3(2) . . . ? O2 C2 C1 122.6(2) . . . ? O2 C2 C3 119.7(2) . . . ? C1 C2 C3 117.7(2) . . . ? O3 C3 C2 118.7(2) . . . ? O3 C3 C4 121.0(2) . . . ? C2 C3 C4 120.3(2) . . . ? C3 C4 C5 121.3(2) . . . ? C4 C5 C6 120.3(2) . . . ? C9 C10 C11 118.2(2) . . . ? C10 C9 C8 119.3(2) . . . ? N2 C11 C12 119.4(2) . . . ? N2 C11 C10 117.2(2) . . . ? C12 C11 C10 123.5(2) . . . ? C12 C13 C8 117.7(2) . . . ? C1 C6 C5 120.2(2) . . . ? C1 C7 N1 121.3(2) . . . ? N1 C8 C9 122.2(2) . . . ? N1 C8 C13 115.8(2) . . . ? C9 C8 C13 122.0(2) . . . ? #===================================================END data_crystal_compound6 _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'maxus(Mackay et al., 1999)' _computing_molecular_graphics 'Ortep (Johnson, 1976)' _computing_publication_material 'maxus(Mackay et al., 1999)' _chemical_compound_source 'Local laboratory' _chemical_formula_sum 'C15 H16 N2 O2 ' _chemical_formula_weight 256.305 _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P 21/c ' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X,-Y,-Z' '-X,+Y+ 1/2,-Z+ 1/2' '+X,-Y+ 1/2,+Z+ 1/2' _cell_length_a 10.2460(10) _cell_length_b 6.1060(10) _cell_length_c 20.8630(10) _cell_angle_alpha 90.000(10) _cell_angle_beta 90.420(10) _cell_angle_gamma 90.000(10) _cell_volume 1305.2(3) _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _diffrn_radiation_wavelength 0.71073 _cell_measurement_reflns_used 8926 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25 _cell_measurement_temperature 298 _exptl_crystal_F_000 544 _exptl_crystal_description 'Cube' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_colour 'red' _refine_ls_hydrogen_treatment 'noref' _diffrn_measurement_device 'KappaCCD' _diffrn_measurement_method 'phi-scan' _diffrn_radiation_type ' MoK\a' _diffrn_radiation_source 'fine-focus sealed tube' _exptl_absorpt_correction_type 'none' _diffrn_reflns_number 2881 _reflns_number_total 2628 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_av_R_equivalents 0.041 _reflns_limit_h_max 12 _reflns_limit_h_min 0 _reflns_limit_k_max 7 _reflns_limit_k_min 0 _reflns_limit_l_max 12 _reflns_limit_l_min 0 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_coefficient_mu 0.088 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 'Waasmaier & Kirfel, 1995' 'H ' 'H ' 0.0000 0.0000 'Waasmaier & Kirfel, 1995' 'O ' 'O ' 0.0106 0.0060 'Waasmaier & Kirfel, 1995' 'N ' 'N ' 0.0061 0.0033 'Waasmaier & Kirfel, 1995' _reflns_number_gt 1391 _reflns_threshold_expression 'I> 3.00 sigma(I)' _reflns_d_resolution_low 1.91 _reflns_d_resolution_high 0.63 _refine_ls_matrix_type full _refine_ls_R_factor_all 0.099 _refine_ls_wR_factor_all 0.068 _refine_ls_R_factor_gt 0.048 _refine_ls_wR_factor_gt 0.068 _refine_ls_wR_factor_ref 0.068 _refine_ls_goodness_of_fit_gt 1.163 _refine_ls_goodness_of_fit_ref 1.163 _refine_ls_goodness_of_fit_all 1.072 _refine_ls_number_parameters 172 _refine_ls_number_reflns 1391 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef F^2^ _refine_special_details ; Refinement on F^2^. ; _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ; w = 1 / ( s^2^(Fo^2^) + 0.03000 * Fo^2^) ; _refine_ls_extinction_method none _atom_sites_solution_hydrogens 'geom, diff' _refine_diff_density_max 0.16 _refine_diff_density_min -0.17 _refine_diff_density_rms 0.03 #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O2 1.02010(4) 0.31380(7) 0.05730(2) 0.0610(3) 1.00 Uij O3 1.17140(5) 0.36000(8) -0.04920(2) 0.0743(3) 1.00 Uij N1 0.94590(5) 0.07330(9) 0.15000(2) 0.0490(3) 1.00 Uij N2 0.56560(5) -0.00890(10) 0.34050(3) 0.0603(4) 1.00 Uij C1 1.11730(6) -0.03500(10) 0.08080(3) 0.0482(4) 1.00 Uij C2 1.10530(6) 0.15530(10) 0.04360(3) 0.0486(4) 1.00 Uij C3 1.18390(6) 0.18020(10) -0.01050(3) 0.0539(4) 1.00 Uij C4 1.27440(7) 0.02260(10) -0.02560(3) 0.0622(5) 1.00 Uij C5 1.28830(7) -0.16450(10) 0.01240(4) 0.0694(5) 1.00 Uij C6 1.20960(7) -0.19390(10) 0.06470(3) 0.0633(5) 1.00 Uij C7 1.03220(6) -0.07050(10) 0.13430(3) 0.0527(4) 1.00 Uij C8 0.85520(6) 0.04490(10) 0.20040(3) 0.0464(4) 1.00 Uij C9 0.85090(6) -0.13190(10) 0.24100(3) 0.0603(4) 1.00 Uij C10 0.75700(6) -0.14830(10) 0.28780(3) 0.0604(4) 1.00 Uij C11 0.66220(6) 0.01190(10) 0.29540(3) 0.0472(4) 1.00 Uij C12 0.66840(7) 0.19380(10) 0.25510(3) 0.0609(5) 1.00 Uij C13 0.76330(7) 0.20760(10) 0.20820(3) 0.0593(4) 1.00 Uij C14 0.56370(7) -0.18850(10) 0.38470(4) 0.0784(5) 1.00 Uij C15 0.47170(7) 0.16520(10) 0.34990(4) 0.0750(5) 1.00 Uij H6 1.21990 -0.32290 0.09060 0.09330 1.00 Uiso H5 1.35240 -0.27230 0.00130 0.09960 1.00 Uiso H4 1.32820 0.04120 -0.06270 0.09210 1.00 Uiso H7 1.04080 -0.20290 0.15880 0.08280 1.00 Uiso H9 0.91550 -0.24440 0.23610 0.09060 1.00 Uiso H10 0.75820 -0.27350 0.31570 0.09060 1.00 Uiso H13 0.76650 0.33400 0.18090 0.08930 1.00 Uiso H12 0.60570 0.30930 0.26000 0.09110 1.00 Uiso H15A 0.40510 0.11510 0.37870 0.10530 1.00 Uiso H15B 0.50850 0.30110 0.36180 0.10530 1.00 Uiso H3 1.08970 0.46150 -0.02890 0.10450 1.00 Uiso H15C 0.41780 0.18470 0.30830 0.10530 1.00 Uiso H2 0.95640 0.26210 0.10110 0.09110 1.00 Uiso H14A 0.48340 -0.17650 0.42150 0.10720 1.00 Uiso H14B 0.54580 -0.32470 0.35120 0.10720 1.00 Uiso H14C 0.65780 -0.21330 0.40940 0.10720 1.00 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O2 0.0693(3) 0.0528(3) 0.0609(3) 0.0092(3) 0.0196(2) 0.0093(3) O3 0.0940(4) 0.0555(3) 0.0736(3) 0.0067(3) 0.0360(3) 0.0155(3) N1 0.0483(3) 0.0542(4) 0.0444(3) 0.0004(3) 0.0025(3) 0.0042(3) N2 0.0557(4) 0.0563(4) 0.0691(4) 0.0015(3) 0.0176(3) 0.0028(3) C1 0.0480(4) 0.0522(4) 0.0443(4) 0.0029(3) 0.0018(3) 0.0041(3) C2 0.0464(4) 0.0521(5) 0.0473(4) -.0002(3) 0.0075(3) -.0038(4) C3 0.0605(5) 0.0491(5) 0.0522(4) -.0032(4) 0.0084(4) 0.0012(4) C4 0.0641(5) 0.0627(5) 0.0600(5) -.0011(4) 0.0160(4) -.0001(4) C5 0.0693(5) 0.0696(6) 0.0695(5) 0.0163(4) 0.0179(4) 0.0005(5) C6 0.0683(5) 0.0637(5) 0.0579(5) 0.0147(4) 0.0083(4) 0.0084(4) C7 0.0547(4) 0.0559(5) 0.0475(4) 0.0012(4) -.0012(3) 0.0057(3) C8 0.0439(4) 0.0494(4) 0.0458(4) 0.0020(3) 0.0017(3) 0.0034(3) C9 0.0564(5) 0.0594(5) 0.0653(5) 0.0163(4) 0.0122(4) 0.0173(4) C10 0.0592(5) 0.0568(5) 0.0653(5) 0.0093(4) 0.0153(4) 0.0214(4) C11 0.0451(4) 0.0494(4) 0.0472(4) -.0038(3) 0.0043(3) -.0001(3) C12 0.0612(5) 0.0525(5) 0.0691(5) 0.0101(4) 0.0140(4) 0.0094(4) C13 0.0661(5) 0.0477(4) 0.0641(5) 0.0069(4) 0.0102(4) 0.0123(4) C14 0.0722(5) 0.0842(6) 0.0790(6) -.0001(5) 0.0229(4) 0.0239(5) C15 0.0601(5) 0.0701(5) 0.0951(6) 0.0040(4) 0.0243(4) -.0073(5) _geom_special_details ; All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C2 1.3360(10) . . ? O3 C3 1.3680(10) . . ? N1 C7 1.2900(10) . . ? N1 C8 1.4180(10) . . ? N2 C11 1.3760(10) . . ? N2 C14 1.4330(10) . . ? N2 C15 1.4480(10) . . ? C1 C2 1.4030(10) . . ? C1 C6 1.3970(10) . . ? C1 C7 1.4380(10) . . ? C2 C3 1.4000(10) . . ? C3 C4 1.3740(10) . . ? C4 C5 1.3970(10) . . ? C5 C6 1.3730(10) . . ? C8 C9 1.3740(10) . . ? C8 C13 1.3790(10) . . ? C9 C10 1.3790(10) . . ? C10 C11 1.3890(10) . . ? C11 C12 1.3940(10) . . ? C12 C13 1.3870(10) . . ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C8 124.00(10) . . . ? C11 N2 C14 121.60(10) . . . ? C11 N2 C15 120.50(10) . . . ? C14 N2 C15 117.50(10) . . . ? C2 C1 C6 119.90(10) . . . ? C2 C1 C7 120.20(10) . . . ? C6 C1 C7 119.80(10) . . . ? O2 C2 C1 122.40(10) . . . ? O2 C2 C3 118.40(10) . . . ? C1 C2 C3 119.20(10) . . . ? O3 C3 C2 120.70(10) . . . ? O3 C3 C4 119.20(10) . . . ? C2 C3 C4 120.10(10) . . . ? C3 C4 C5 120.60(10) . . . ? C4 C5 C6 120.00(10) . . . ? C1 C6 C5 120.20(10) . . . ? N1 C7 C1 121.00(10) . . . ? N1 C8 C9 125.20(10) . . . ? N1 C8 C13 116.90(10) . . . ? C9 C8 C13 117.90(10) . . . ? C8 C9 C10 121.30(10) . . . ? C9 C10 C11 121.40(10) . . . ? N2 C11 C10 121.30(10) . . . ? N2 C11 C12 121.40(10) . . . ? C10 C11 C12 117.20(10) . . . ? C11 C12 C13 120.50(10) . . . ? C8 C13 C12 121.60(10) . . . ? #===================================================END _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Waasmaier, D. & Kirfel, A. (1995). Acta Cryst. A51, 416-431. ;