# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Aleksander Filarowski' _publ_contact_author_email AFIL@RUC.DK _publ_section_title ; The conformational analysis of 2-hydroxyaryl Schiff thiosemicarbazones. ; loop_ _publ_author_name 'Aleksander Filarowski' 'A Kochel' 'M Krasowska' # Attachment '19ORR.CIF' data_19orr _database_code_depnum_ccdc_archive 'CCDC 749539' #TrackingRef '19ORR.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1--(2--hydroxyphenyl)ethan--1--one thiosemicarbazone methanol slovate' ; _chemical_name_common ; '1--(2--hydroxyphenyl)ethan--1--one thiosemicarbazone methanol slovate' ; _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 N3 O S, C H4 O' _chemical_formula_sum 'C10 H15 N3 O2 S' _chemical_formula_weight 241.32 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 Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' 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' '-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 14.688(3) _cell_length_b 12.574(3) _cell_length_c 12.574(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2322.3(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2520 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 31.01 _exptl_crystal_description bkock _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.789 _exptl_absorpt_correction_T_max 0.890 _exptl_absorpt_process_details 'CrysAlis RED, Oxford Diffraction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32108 _diffrn_reflns_av_R_equivalents 0.0904 _diffrn_reflns_av_sigmaI/netI 0.1429 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 37.01 _reflns_number_total 5195 _reflns_number_gt 2613 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, date)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, date)' _computing_data_reduction 'CrysAlis RED ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXL-97 _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^)+(0.0471P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5195 _refine_ls_number_parameters 175 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1393 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.956 _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 -0.07592(3) -0.77371(3) -0.06744(3) 0.01874(11) Uani 1 1 d . . . O1 O -0.10524(9) -0.60004(8) 0.15468(9) 0.0198(3) Uani 1 1 d D . . H1O H -0.0950(14) -0.6064(17) 0.0845(12) 0.035(6) Uiso 1 1 d D . . N1 N -0.09834(9) -0.54287(10) -0.03823(9) 0.0139(3) Uani 1 1 d . . . N2 N -0.06915(10) -0.57129(10) -0.13667(10) 0.0148(3) Uani 1 1 d D . . H2N H -0.0592(14) -0.5239(15) -0.1892(15) 0.042(6) Uiso 1 1 d D . . N3 N -0.02819(11) -0.69741(11) -0.25611(10) 0.0189(3) Uani 1 1 d D . . H3N H -0.0203(15) -0.6430(14) -0.3000(14) 0.038(6) Uiso 1 1 d D . . H4N H -0.0380(14) -0.7624(12) -0.2819(14) 0.026(5) Uiso 1 1 d D . . C1 C -0.15785(11) -0.42718(11) 0.09052(11) 0.0129(3) Uani 1 1 d . . . C2 C -0.14559(11) -0.50338(11) 0.17164(12) 0.0149(3) Uani 1 1 d . . . C3 C -0.17506(11) -0.48157(12) 0.27443(12) 0.0173(3) Uani 1 1 d . . . H3 H -0.1661 -0.5359 0.3257 0.023(5) Uiso 1 1 d R . . C4 C -0.21844(11) -0.38627(12) 0.29738(12) 0.0179(3) Uani 1 1 d . . . H4 H -0.2387 -0.3726 0.3664 0.017(4) Uiso 1 1 d R . . C5 C -0.23297(11) -0.31085(12) 0.21850(12) 0.0178(3) Uani 1 1 d . . . H5 H -0.2619 -0.2457 0.2325 0.016(4) Uiso 1 1 d R . . C6 C -0.20237(11) -0.33134(11) 0.11668(12) 0.0169(3) Uani 1 1 d . . . H6 H -0.2138 -0.2823 0.0638 0.024(5) Uiso 1 1 d R . . C7 C -0.12805(11) -0.44694(11) -0.01947(11) 0.0140(3) Uani 1 1 d . . . C8 C -0.05665(11) -0.67642(11) -0.15776(12) 0.0151(3) Uani 1 1 d . . . C9 C -0.13487(13) -0.35875(12) -0.09935(12) 0.0208(4) Uani 1 1 d . . . H9A H -0.1119 -0.3777 -0.1683 0.031(5) Uiso 1 1 d R . . H9B H -0.0992 -0.2996 -0.0762 0.030(5) Uiso 1 1 d R . . H9C H -0.1989 -0.3365 -0.1044 0.039(6) Uiso 1 1 d R . . O2 O -0.04131(9) -0.02775(9) 0.15936(9) 0.0217(3) Uani 1 1 d D . . H2 H 0.0000(13) -0.0804(14) 0.1482(15) 0.033(6) Uiso 1 1 d D . . C10 C -0.11593(13) -0.03525(15) 0.08717(15) 0.0286(4) Uani 1 1 d . . . H10A H -0.1502 0.0268 0.0945 0.054(7) Uiso 1 1 d R . . H10B H -0.0912 -0.0437 0.0138 0.066(8) Uiso 1 1 d R . . H10C H -0.1543 -0.0945 0.1060 0.054(7) Uiso 1 1 d 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 0.0270(2) 0.01199(16) 0.01719(17) 0.00046(13) 0.00172(17) 0.00187(16) O1 0.0303(7) 0.0123(5) 0.0167(5) 0.0018(4) 0.0016(5) 0.0058(5) N1 0.0151(7) 0.0145(6) 0.0122(5) -0.0008(4) 0.0003(5) 0.0011(5) N2 0.0192(8) 0.0123(5) 0.0128(5) -0.0001(4) 0.0019(5) -0.0003(5) N3 0.0248(9) 0.0145(6) 0.0173(6) -0.0033(5) 0.0043(6) -0.0005(6) C1 0.0117(8) 0.0139(6) 0.0131(6) -0.0009(5) -0.0018(6) -0.0011(6) C2 0.0131(9) 0.0132(6) 0.0186(7) -0.0002(5) 0.0010(6) -0.0018(6) C3 0.0173(9) 0.0182(7) 0.0165(7) 0.0012(5) 0.0004(6) -0.0028(6) C4 0.0160(9) 0.0224(8) 0.0153(7) -0.0046(6) 0.0041(6) -0.0036(7) C5 0.0161(9) 0.0167(7) 0.0205(7) -0.0037(6) -0.0009(7) 0.0021(6) C6 0.0181(9) 0.0126(7) 0.0199(7) 0.0000(5) -0.0029(6) 0.0009(6) C7 0.0138(9) 0.0132(7) 0.0150(7) 0.0003(5) -0.0026(6) -0.0003(6) C8 0.0134(9) 0.0140(7) 0.0179(7) -0.0022(5) -0.0005(6) 0.0000(6) C9 0.0316(11) 0.0149(7) 0.0160(7) 0.0022(6) 0.0026(7) 0.0028(7) O2 0.0238(7) 0.0216(6) 0.0198(5) -0.0042(4) -0.0025(5) 0.0065(5) C10 0.0235(11) 0.0287(9) 0.0336(10) -0.0017(7) -0.0062(8) 0.0015(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C8 1.6931(15) . ? O1 C2 1.3690(19) . ? O1 H1O 0.898(15) . ? N1 C7 1.3043(19) . ? N1 N2 1.3578(17) . ? N2 C8 1.3606(18) . ? N2 H2N 0.902(15) . ? N3 C8 1.3319(19) . ? N3 H3N 0.887(15) . ? N3 H4N 0.891(14) . ? C1 C6 1.410(2) . ? C1 C2 1.411(2) . ? C1 C7 1.472(2) . ? C2 C3 1.390(2) . ? C3 C4 1.387(2) . ? C3 H3 0.9488 . ? C4 C5 1.389(2) . ? C4 H4 0.9335 . ? C5 C6 1.381(2) . ? C5 H5 0.9399 . ? C6 H6 0.9228 . ? C7 C9 1.500(2) . ? C9 H9A 0.9604 . ? C9 H9B 0.9555 . ? C9 H9C 0.9833 . ? O2 C10 1.426(2) . ? O2 H2 0.909(15) . ? C10 H10A 0.9330 . ? C10 H10B 0.9970 . ? C10 H10C 0.9640 . ? 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 O1 H1O 107.7(14) . . ? C7 N1 N2 120.92(12) . . ? N1 N2 C8 118.42(12) . . ? N1 N2 H2N 123.1(14) . . ? C8 N2 H2N 118.5(14) . . ? C8 N3 H3N 117.8(13) . . ? C8 N3 H4N 118.0(12) . . ? H3N N3 H4N 120.2(18) . . ? C6 C1 C2 118.10(13) . . ? C6 C1 C7 120.09(13) . . ? C2 C1 C7 121.79(13) . . ? O1 C2 C3 117.04(13) . . ? O1 C2 C1 123.06(13) . . ? C3 C2 C1 119.89(14) . . ? C4 C3 C2 120.44(14) . . ? C4 C3 H3 123.0 . . ? C2 C3 H3 116.5 . . ? C3 C4 C5 120.78(14) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.3 . . ? C6 C5 C4 118.99(14) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 122.1 . . ? C5 C6 C1 121.78(14) . . ? C5 C6 H6 119.0 . . ? C1 C6 H6 119.2 . . ? N1 C7 C1 115.19(12) . . ? N1 C7 C9 125.81(14) . . ? C1 C7 C9 119.00(13) . . ? N3 C8 N2 114.57(13) . . ? N3 C8 S1 122.15(11) . . ? N2 C8 S1 123.28(12) . . ? C7 C9 H9A 113.5 . . ? C7 C9 H9B 109.6 . . ? H9A C9 H9B 106.0 . . ? C7 C9 H9C 108.5 . . ? H9A C9 H9C 110.4 . . ? H9B C9 H9C 108.8 . . ? C10 O2 H2 111.5(13) . . ? O2 C10 H10A 107.3 . . ? O2 C10 H10B 108.4 . . ? H10A C10 H10B 112.1 . . ? O2 C10 H10C 110.2 . . ? H10A C10 H10C 107.8 . . ? H10B C10 H10C 111.0 . . ? 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 C7 N1 N2 C8 -166.72(14) . . . . ? C6 C1 C2 O1 178.45(14) . . . . ? C7 C1 C2 O1 0.3(2) . . . . ? C6 C1 C2 C3 -1.6(2) . . . . ? C7 C1 C2 C3 -179.78(14) . . . . ? O1 C2 C3 C4 -178.55(14) . . . . ? C1 C2 C3 C4 1.5(2) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C3 C4 C5 C6 -0.9(2) . . . . ? C4 C5 C6 C1 0.8(2) . . . . ? C2 C1 C6 C5 0.5(2) . . . . ? C7 C1 C6 C5 178.66(15) . . . . ? N2 N1 C7 C1 179.77(13) . . . . ? N2 N1 C7 C9 0.5(2) . . . . ? C6 C1 C7 N1 -171.55(14) . . . . ? C2 C1 C7 N1 6.6(2) . . . . ? C6 C1 C7 C9 7.8(2) . . . . ? C2 C1 C7 C9 -174.13(15) . . . . ? N1 N2 C8 N3 179.85(14) . . . . ? N1 N2 C8 S1 0.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.878 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.484 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.081 # start Validation Reply Form _vrf_PLAT153_190rr ; PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ...3.26 Ratio. RESPONSE: poor data, not adequate for the refinement of individual displacement parameters. ; # end Validation Reply Form # Attachment 'nn3dc.cif' data_nn3dc _database_code_depnum_ccdc_archive 'CCDC 749540' #TrackingRef 'nn3dc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1-(2-hydroxyphenyl)ethan-1-one N-methylthiosemicarbazone' ; _chemical_name_common "'1-(2-hydroxyphenyl)ethan-1-one N-methylthiosemicarbazone'" _chemical_melting_point ? _chemical_formula_moiety 'C10 H13 N3 O S' _chemical_formula_sum 'C10 H13 N3 O S' _chemical_formula_weight 223.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.914(5) _cell_length_b 13.613(5) _cell_length_c 18.028(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2187.6(16) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1450 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 25.04 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.273 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.876 _exptl_absorpt_correction_T_max 0.910 _exptl_absorpt_process_details 'CrysAlis RED, Oxford Diffraction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13834 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.04 _reflns_number_total 1936 _reflns_number_gt 1534 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, date)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, date)' _computing_data_reduction 'CrysAlis RED ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXL-97 _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^)+(0.0425P)^2^+0.7818P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1936 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0803 _refine_ls_wR_factor_gt 0.0746 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.20400(5) 0.80414(3) 0.08141(2) 0.02030(15) Uani 1 1 d . . . O1 O 0.30523(15) 1.01601(11) -0.01642(7) 0.0264(3) Uani 1 1 d . . . C1 C 0.14972(19) 1.03280(13) -0.12728(9) 0.0195(4) Uani 1 1 d . . . C2 C 0.27516(19) 1.05787(12) -0.08323(10) 0.0216(4) Uani 1 1 d . . . C3 C 0.3766(2) 1.12900(13) -0.10694(10) 0.0269(4) Uani 1 1 d . . . H3 H 0.4617 1.1441 -0.0773 0.032 Uiso 1 1 calc R . . C4 C 0.3543(2) 1.17781(14) -0.17318(11) 0.0291(5) Uani 1 1 d . . . H4 H 0.4236 1.2267 -0.1887 0.035 Uiso 1 1 calc R . . C5 C 0.2314(2) 1.15579(14) -0.21703(10) 0.0289(5) Uani 1 1 d . . . H5 H 0.2159 1.1896 -0.2625 0.035 Uiso 1 1 calc R . . C6 C 0.1315(2) 1.08427(13) -0.19431(9) 0.0246(4) Uani 1 1 d . . . H6 H 0.0479 1.0694 -0.2250 0.029 Uiso 1 1 calc R . . N1 N -0.05973(17) 0.71439(11) 0.06492(8) 0.0213(4) Uani 1 1 d . . . N2 N 0.07807(16) 0.90715(10) -0.04660(8) 0.0197(3) Uani 1 1 d . . . N3 N -0.01247(17) 0.83479(11) -0.01902(8) 0.0193(3) Uani 1 1 d . . . C7 C 0.04152(19) 0.95605(12) -0.10531(9) 0.0187(4) Uani 1 1 d . . . C8 C -0.0988(2) 0.93906(13) -0.14995(10) 0.0264(4) Uani 1 1 d . . . H8A H -0.1604 0.8888 -0.1256 0.040 Uiso 1 1 calc R . . H8B H -0.0717 0.9168 -0.1999 0.040 Uiso 1 1 calc R . . H8C H -0.1558 1.0005 -0.1534 0.040 Uiso 1 1 calc R . . C9 C 0.03579(19) 0.78240(12) 0.04109(9) 0.0182(4) Uani 1 1 d . . . C10 C -0.0298(2) 0.64867(14) 0.12663(10) 0.0266(4) Uani 1 1 d . . . H10A H 0.0329 0.5940 0.1097 0.040 Uiso 1 1 calc R . . H10B H -0.1248 0.6230 0.1459 0.040 Uiso 1 1 calc R . . H10C H 0.0226 0.6847 0.1659 0.040 Uiso 1 1 calc R . . H1N H -0.099(2) 0.8219(13) -0.0367(11) 0.025(5) Uiso 1 1 d . . . H2N H -0.143(2) 0.7054(15) 0.0401(12) 0.033(6) Uiso 1 1 d . . . H1O H 0.245(3) 0.9731(17) -0.0088(12) 0.035(7) 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 0.0166(2) 0.0241(3) 0.0202(2) -0.00020(19) -0.00154(18) 0.00027(19) O1 0.0226(7) 0.0295(8) 0.0271(7) 0.0034(6) -0.0042(6) -0.0073(6) C1 0.0199(9) 0.0180(9) 0.0206(9) -0.0025(7) 0.0032(8) 0.0020(8) C2 0.0227(9) 0.0186(9) 0.0234(9) -0.0036(8) 0.0032(8) 0.0026(8) C3 0.0223(10) 0.0257(10) 0.0326(10) -0.0069(9) 0.0029(9) -0.0025(8) C4 0.0293(10) 0.0246(10) 0.0336(11) -0.0009(9) 0.0146(9) -0.0033(8) C5 0.0351(11) 0.0268(11) 0.0248(10) 0.0038(9) 0.0087(9) -0.0004(9) C6 0.0249(10) 0.0271(10) 0.0216(10) -0.0011(8) 0.0024(8) 0.0006(8) N1 0.0183(8) 0.0240(8) 0.0215(8) 0.0028(6) -0.0023(6) -0.0027(7) N2 0.0185(7) 0.0199(7) 0.0206(8) -0.0007(6) 0.0013(6) -0.0011(6) N3 0.0151(8) 0.0221(8) 0.0207(8) 0.0017(6) -0.0018(6) -0.0027(6) C7 0.0187(9) 0.0188(9) 0.0186(9) -0.0017(7) 0.0014(7) 0.0017(7) C8 0.0252(10) 0.0256(10) 0.0284(10) 0.0039(8) -0.0050(8) -0.0024(8) C9 0.0184(9) 0.0194(9) 0.0168(9) -0.0036(7) 0.0027(7) 0.0023(7) C10 0.0278(10) 0.0268(10) 0.0252(10) 0.0065(8) -0.0004(8) -0.0064(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C9 1.6924(19) . ? O1 C2 1.359(2) . ? O1 H1O 0.80(2) . ? C1 C6 1.406(2) . ? C1 C2 1.413(2) . ? C1 C7 1.476(2) . ? C2 C3 1.392(3) . ? C3 C4 1.381(3) . ? C3 H3 0.9500 . ? C4 C5 1.384(3) . ? C4 H4 0.9500 . ? C5 C6 1.382(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? N1 C9 1.329(2) . ? N1 C10 1.452(2) . ? N1 H2N 0.87(2) . ? N2 C7 1.292(2) . ? N2 N3 1.367(2) . ? N3 C9 1.367(2) . ? N3 H1N 0.85(2) . ? C7 C8 1.505(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? 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 O1 H1O 109.0(16) . . ? C6 C1 C2 116.99(16) . . ? C6 C1 C7 120.52(16) . . ? C2 C1 C7 122.49(16) . . ? O1 C2 C3 115.82(16) . . ? O1 C2 C1 123.56(16) . . ? C3 C2 C1 120.62(17) . . ? C4 C3 C2 120.44(18) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.25(18) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 119.57(18) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C1 122.11(17) . . ? C5 C6 H6 118.9 . . ? C1 C6 H6 118.9 . . ? C9 N1 C10 123.99(16) . . ? C9 N1 H2N 118.3(14) . . ? C10 N1 H2N 117.6(14) . . ? C7 N2 N3 121.35(15) . . ? C9 N3 N2 118.59(14) . . ? C9 N3 H1N 118.3(13) . . ? N2 N3 H1N 123.1(13) . . ? N2 C7 C1 114.82(15) . . ? N2 C7 C8 124.63(16) . . ? C1 C7 C8 120.55(15) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 N3 114.72(15) . . ? N1 C9 S1 123.41(13) . . ? N3 C9 S1 121.87(13) . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.266 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.045 # Attachment 'olek7dc.cif' data_olek7dc _database_code_depnum_ccdc_archive 'CCDC 749541' #TrackingRef 'olek7dc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl) ethan-1-one thiosemicarbazone di dimethylaminium cation sulfate' ; _chemical_name_common ; '1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl) ethan-1-one thiosemicarbazone di dimethylaminium cation sulfate' ; _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 N3 O3 S, 2(C2 H8 N), O4 S' _chemical_formula_sum 'C13 H27 N5 O7 S2' _chemical_formula_weight 429.54 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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.863(2) _cell_length_b 7.992(3) _cell_length_c 22.218(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.65(2) _cell_angle_gamma 90.00 _cell_volume 2004.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5200 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 36.87 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.310 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.789 _exptl_absorpt_correction_T_max 0.890 _exptl_absorpt_process_details 'CrysAlis RED, Oxford Diffraction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 Km4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37694 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0577 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 36.87 _reflns_number_total 9450 _reflns_number_gt 5976 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, date)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, date)' _computing_data_reduction 'CrysAlis RED ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXL-97 _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^)+(0.0531P)^2^+0.0097P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9450 _refine_ls_number_parameters 280 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.15091(3) 0.43376(4) 0.697763(16) 0.02498(8) Uani 1 1 d . . . O1 O -0.13667(8) 0.11654(12) 0.34987(4) 0.02306(18) Uani 1 1 d . . . O2 O -0.04466(9) 0.19984(13) 0.54927(5) 0.0268(2) Uani 1 1 d D . . H1 H 0.0249 0.2532 0.5657 0.101(10) Uiso 1 1 d RD . . O3 O 0.03076(8) 0.21141(12) 0.35943(4) 0.0258(2) Uani 1 1 d . . . N1 N 0.14008(9) 0.33869(13) 0.56640(5) 0.01974(19) Uani 1 1 d . . . N2 N 0.24050(9) 0.42379(14) 0.61109(5) 0.0207(2) Uani 1 1 d D . . H1A H 0.3072(13) 0.428(2) 0.6062(8) 0.031(4) Uiso 1 1 d D . . N3 N 0.36374(10) 0.52470(16) 0.71680(6) 0.0286(2) Uani 1 1 d D . . H2A H 0.4174(16) 0.533(2) 0.7017(10) 0.049(5) Uiso 1 1 d D . . H3A H 0.3747(15) 0.579(2) 0.7553(8) 0.036(5) Uiso 1 1 d D . . C1 C 0.00413(10) 0.23498(15) 0.45907(6) 0.0180(2) Uani 1 1 d . . . C2 C -0.06946(11) 0.17756(15) 0.48547(6) 0.0202(2) Uani 1 1 d . . . C3 C -0.17712(11) 0.09164(16) 0.44188(6) 0.0228(2) Uani 1 1 d . . . H3 H -0.2252 0.0530 0.4595 0.032(4) Uiso 1 1 d R . . C4 C -0.20911(10) 0.06682(16) 0.37552(6) 0.0213(2) Uani 1 1 d . . . C5 C -0.02672(10) 0.19198(15) 0.38955(6) 0.0189(2) Uani 1 1 d . . . C6 C 0.11183(10) 0.33032(15) 0.50149(6) 0.0173(2) Uani 1 1 d . . . C7 C 0.18166(12) 0.41861(18) 0.47351(7) 0.0261(3) Uani 1 1 d . . . H7A H 0.2473 0.3500 0.4797 0.054(6) Uiso 1 1 d R . . H7B H 0.1319 0.4401 0.4255 0.047(5) Uiso 1 1 d R . . H7C H 0.2106 0.5227 0.4973 0.058(6) Uiso 1 1 d R . . C8 C 0.25648(10) 0.46237(16) 0.67474(6) 0.0197(2) Uani 1 1 d . . . C9 C -0.31879(12) -0.01305(19) 0.32254(7) 0.0295(3) Uani 1 1 d . . . H9A H -0.3665 -0.0480 0.3428 0.034(4) Uiso 1 1 d R . . H9B H -0.3623 0.0657 0.2864 0.049(5) Uiso 1 1 d R . . H9C H -0.2986 -0.1087 0.3041 0.034(4) Uiso 1 1 d R . . N4 N 0.15051(9) 0.70079(14) 0.28674(5) 0.0223(2) Uani 1 1 d . . . H4A H 0.0978 0.7325 0.2439 0.039(5) Uiso 1 1 d R . . H4B H 0.2235 0.7221 0.2926 0.035(5) Uiso 1 1 d R . . C10 C 0.13120(12) 0.80161(18) 0.33650(7) 0.0266(3) Uani 1 1 d . . . H10A H 0.1906 0.7740 0.3823 0.029(4) Uiso 1 1 d R . . H10B H 0.1363 0.9185 0.3282 0.034(4) Uiso 1 1 d R . . H10C H 0.0542 0.7775 0.3313 0.035(4) Uiso 1 1 d R . . C11 C 0.13850(12) 0.51859(17) 0.29388(7) 0.0273(3) Uani 1 1 d . . . H11A H 0.0624 0.4956 0.2901 0.037(5) Uiso 1 1 d R . . H11B H 0.1457 0.4603 0.2583 0.036(4) Uiso 1 1 d R . . H11C H 0.1996 0.4817 0.3378 0.028(4) Uiso 1 1 d R . . N5 N 0.54872(10) 0.75407(13) 0.05917(5) 0.0226(2) Uani 1 1 d . . . H5A H 0.5583 0.8652 0.0664 0.035(5) Uiso 1 1 d R . . H5B H 0.5506 0.7315 0.0200 0.029(4) Uiso 1 1 d R . . C12 C 0.43164(13) 0.70507(18) 0.05115(8) 0.0301(3) Uani 1 1 d . . . H12A H 0.4272 0.7356 0.0916 0.045(5) Uiso 1 1 d R . . H12B H 0.3702 0.7614 0.0121 0.038(5) Uiso 1 1 d R . . H12C H 0.4217 0.5862 0.0445 0.032(4) Uiso 1 1 d R . . C13 C 0.64771(15) 0.6661(2) 0.11659(8) 0.0410(4) Uani 1 1 d . . . H13A H 0.6361 0.5474 0.1101 0.068(7) Uiso 1 1 d R . . H13B H 0.7210 0.6963 0.1179 0.053(6) Uiso 1 1 d R . . H13C H 0.6503 0.6973 0.1590 0.052(6) Uiso 1 1 d R . . S2 S 0.53131(2) 0.17366(4) 0.113165(14) 0.01637(6) Uani 1 1 d . . . O4 O 0.59803(8) 0.09253(11) 0.08244(4) 0.02025(17) Uani 1 1 d . . . O5 O 0.44540(9) 0.29331(12) 0.06376(5) 0.0275(2) Uani 1 1 d . . . O6 O 0.61543(8) 0.26316(13) 0.17599(5) 0.0277(2) Uani 1 1 d . . . O7 O 0.46790(8) 0.04419(12) 0.13014(5) 0.0265(2) 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 0.02125(14) 0.03520(18) 0.02131(14) -0.00651(12) 0.01247(12) -0.00427(12) O1 0.0214(4) 0.0295(5) 0.0155(4) -0.0019(3) 0.0066(3) -0.0053(4) O2 0.0266(5) 0.0369(5) 0.0201(4) -0.0064(4) 0.0137(4) -0.0070(4) O3 0.0250(4) 0.0370(5) 0.0171(4) -0.0033(4) 0.0114(4) -0.0050(4) N1 0.0196(5) 0.0230(5) 0.0154(4) -0.0041(4) 0.0074(4) -0.0026(4) N2 0.0169(4) 0.0289(5) 0.0157(4) -0.0050(4) 0.0074(4) -0.0035(4) N3 0.0207(5) 0.0433(7) 0.0223(5) -0.0146(5) 0.0108(4) -0.0056(5) C1 0.0174(5) 0.0206(5) 0.0145(5) 0.0002(4) 0.0065(4) -0.0004(4) C2 0.0184(5) 0.0219(6) 0.0197(5) -0.0016(4) 0.0088(4) 0.0021(4) C3 0.0177(5) 0.0269(6) 0.0227(6) -0.0014(5) 0.0089(5) -0.0014(5) C4 0.0169(5) 0.0216(6) 0.0216(5) 0.0003(4) 0.0062(4) 0.0011(4) C5 0.0186(5) 0.0220(6) 0.0151(5) 0.0008(4) 0.0073(4) 0.0012(4) C6 0.0165(5) 0.0207(5) 0.0149(5) 0.0007(4) 0.0076(4) 0.0021(4) C7 0.0251(6) 0.0339(7) 0.0197(6) -0.0013(5) 0.0109(5) -0.0078(5) C8 0.0198(5) 0.0233(6) 0.0171(5) -0.0036(4) 0.0098(4) 0.0013(4) C9 0.0231(6) 0.0334(7) 0.0248(6) -0.0029(5) 0.0058(5) -0.0081(5) N4 0.0198(5) 0.0307(6) 0.0165(4) 0.0040(4) 0.0088(4) 0.0014(4) C10 0.0254(6) 0.0352(7) 0.0221(6) -0.0015(5) 0.0136(5) 0.0003(5) C11 0.0245(6) 0.0307(7) 0.0247(6) 0.0030(5) 0.0102(5) -0.0029(5) N5 0.0280(5) 0.0170(5) 0.0205(5) 0.0004(4) 0.0097(4) -0.0005(4) C12 0.0315(7) 0.0234(6) 0.0389(8) -0.0005(6) 0.0197(6) -0.0026(5) C13 0.0373(8) 0.0322(8) 0.0363(8) 0.0136(6) 0.0040(7) -0.0013(6) S2 0.01583(12) 0.01688(12) 0.01654(12) -0.00261(10) 0.00786(10) -0.00095(10) O4 0.0211(4) 0.0208(4) 0.0207(4) -0.0037(3) 0.0115(3) -0.0010(3) O5 0.0289(5) 0.0237(5) 0.0256(5) 0.0019(4) 0.0095(4) 0.0085(4) O6 0.0228(4) 0.0345(5) 0.0234(4) -0.0133(4) 0.0092(4) -0.0034(4) O7 0.0250(4) 0.0275(5) 0.0333(5) 0.0023(4) 0.0190(4) -0.0034(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C8 1.6805(12) . ? O1 C4 1.3639(15) . ? O1 C5 1.3947(15) . ? O2 C2 1.3075(15) . ? O2 H1 0.8961 . ? O3 C5 1.2219(14) . ? N1 C6 1.3092(14) . ? N1 N2 1.3737(14) . ? N2 C8 1.3633(15) . ? N2 H1A 0.916(13) . ? N3 C8 1.3374(17) . ? N3 H2A 0.903(14) . ? N3 H3A 0.907(13) . ? C1 C2 1.4082(17) . ? C1 C5 1.4400(16) . ? C1 C6 1.4616(16) . ? C2 C3 1.4287(18) . ? C3 C4 1.3418(18) . ? C3 H3 0.9300 . ? C4 C9 1.4802(18) . ? C6 C7 1.4921(17) . ? C7 H7A 0.9599 . ? C7 H7B 0.9599 . ? C7 H7C 0.9601 . ? C9 H9A 0.9600 . ? C9 H9B 0.9601 . ? C9 H9C 0.9600 . ? N4 C11 1.4808(18) . ? N4 C10 1.4821(16) . ? N4 H4A 0.9000 . ? N4 H4B 0.8999 . ? C10 H10A 0.9600 . ? C10 H10B 0.9601 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9599 . ? N5 C13 1.4785(18) . ? N5 C12 1.4818(18) . ? N5 H5A 0.9002 . ? N5 H5B 0.9000 . ? C12 H12A 0.9599 . ? C12 H12B 0.9600 . ? C12 H12C 0.9602 . ? C13 H13A 0.9602 . ? C13 H13B 0.9601 . ? C13 H13C 0.9600 . ? S2 O7 1.4741(10) . ? S2 O5 1.4755(10) . ? S2 O6 1.4773(10) . ? S2 O4 1.4781(9) . ? 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 C4 O1 C5 123.41(9) . . ? C2 O2 H1 100.5 . . ? C6 N1 N2 119.32(10) . . ? C8 N2 N1 118.92(10) . . ? C8 N2 H1A 115.5(11) . . ? N1 N2 H1A 123.0(11) . . ? C8 N3 H2A 118.9(13) . . ? C8 N3 H3A 118.6(11) . . ? H2A N3 H3A 121.0(17) . . ? C2 C1 C5 118.32(11) . . ? C2 C1 C6 121.32(10) . . ? C5 C1 C6 120.31(10) . . ? O2 C2 C1 122.95(11) . . ? O2 C2 C3 116.98(11) . . ? C1 C2 C3 120.06(11) . . ? C4 C3 C2 120.18(12) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 O1 120.34(11) . . ? C3 C4 C9 127.65(12) . . ? O1 C4 C9 112.02(11) . . ? O3 C5 O1 113.91(10) . . ? O3 C5 C1 128.99(11) . . ? O1 C5 C1 117.11(10) . . ? N1 C6 C1 114.43(10) . . ? N1 C6 C7 122.02(11) . . ? C1 C6 C7 123.48(10) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.4 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 N2 113.64(10) . . ? N3 C8 S1 123.46(9) . . ? N2 C8 S1 122.89(9) . . ? C4 C9 H9A 109.4 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 N4 C10 113.03(10) . . ? C11 N4 H4A 109.0 . . ? C10 N4 H4A 108.9 . . ? C11 N4 H4B 109.0 . . ? C10 N4 H4B 109.0 . . ? H4A N4 H4B 107.8 . . ? N4 C10 H10A 109.4 . . ? N4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.4 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 N5 C12 112.53(11) . . ? C13 N5 H5A 109.1 . . ? C12 N5 H5A 109.0 . . ? C13 N5 H5B 109.1 . . ? C12 N5 H5B 109.1 . . ? H5A N5 H5B 107.9 . . ? N5 C12 H12A 109.5 . . ? N5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N5 C12 H12C 109.4 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N5 C13 H13A 109.5 . . ? N5 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N5 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O7 S2 O5 109.65(6) . . ? O7 S2 O6 110.03(6) . . ? O5 S2 O6 109.70(6) . . ? O7 S2 O4 108.98(6) . . ? O5 S2 O4 109.53(5) . . ? O6 S2 O4 108.93(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 N1 N2 C8 166.37(11) . . . . ? C5 C1 C2 O2 175.08(11) . . . . ? C6 C1 C2 O2 -2.56(19) . . . . ? C5 C1 C2 C3 -5.38(17) . . . . ? C6 C1 C2 C3 176.98(11) . . . . ? O2 C2 C3 C4 178.91(12) . . . . ? C1 C2 C3 C4 -0.67(19) . . . . ? C2 C3 C4 O1 2.98(19) . . . . ? C2 C3 C4 C9 -177.44(13) . . . . ? C5 O1 C4 C3 1.03(18) . . . . ? C5 O1 C4 C9 -178.61(11) . . . . ? C4 O1 C5 O3 172.59(11) . . . . ? C4 O1 C5 C1 -7.04(16) . . . . ? C2 C1 C5 O3 -170.64(13) . . . . ? C6 C1 C5 O3 7.0(2) . . . . ? C2 C1 C5 O1 8.93(16) . . . . ? C6 C1 C5 O1 -173.41(10) . . . . ? N2 N1 C6 C1 179.29(10) . . . . ? N2 N1 C6 C7 -3.52(17) . . . . ? C2 C1 C6 N1 7.92(16) . . . . ? C5 C1 C6 N1 -169.68(11) . . . . ? C2 C1 C6 C7 -169.23(12) . . . . ? C5 C1 C6 C7 13.18(18) . . . . ? N1 N2 C8 N3 171.51(11) . . . . ? N1 N2 C8 S1 -8.44(16) . . . . ? _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.499 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.068 # start Validation Reply Form _vrf_PLAT222_olek7dc ; PROBLEM: The su's on the Cell Axes are Equal (x 100000) 300 Ang. RESPONSE: is correct calculated from software default value. ; # end Validation Reply Form # Attachment 'olo33.cif' data_olo33 _database_code_depnum_ccdc_archive 'CCDC 749542' #TrackingRef 'olo33.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1-(2-hydroxyphenyl)ethan-1-one N,N-dimethylthiosemicarbazone' ; _chemical_name_common ; '1-(2-hydroxyphenyl)ethan-1-one N,N-dimethylthiosemicarbazone' ; _chemical_melting_point ? _chemical_formula_moiety 'C11 H15 N3 O S' _chemical_formula_sum 'C11 H15 N3 O S' _chemical_formula_weight 237.32 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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.82700(10) _cell_length_b 7.29170(10) _cell_length_c 16.3656(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.7290(10) _cell_angle_gamma 90.00 _cell_volume 1172.15(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1751 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 25.07 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.259 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.765 _exptl_absorpt_correction_T_max 0.830 _exptl_absorpt_process_details 'CrysAlis RED, Oxford Diffraction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13582 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0102 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.07 _reflns_number_total 2077 _reflns_number_gt 1853 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, date)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, date)' _computing_data_reduction 'CrysAlis RED ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXL-97 _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^)+(0.0476P)^2^+0.5442P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2077 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0852 _refine_ls_wR_factor_gt 0.0820 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.71747(3) 0.24930(5) 0.06065(2) 0.02243(14) Uani 1 1 d . . . O1 O 0.44685(10) 0.43978(15) 0.17147(6) 0.0250(3) Uani 1 1 d . . . H1O H 0.474(2) 0.390(3) 0.1280(13) 0.043(6) Uiso 1 1 d . . . N1 N 0.42348(12) 0.28213(16) 0.03229(7) 0.0195(3) Uani 1 1 d . . . N2 N 0.49207(12) 0.21961(17) -0.03361(8) 0.0204(3) Uani 1 1 d . . . N3 N 0.68862(12) 0.13781(17) -0.09496(7) 0.0219(3) Uani 1 1 d . . . C1 C 0.30905(14) 0.4318(2) 0.16993(9) 0.0212(3) Uani 1 1 d . . . C2 C 0.22964(14) 0.37057(18) 0.10129(8) 0.0193(3) Uani 1 1 d . . . C3 C 0.08713(14) 0.3697(2) 0.10871(9) 0.0233(3) Uani 1 1 d . . . H3 H 0.0316 0.3298 0.0636 0.028 Uiso 1 1 calc R . . C4 C 0.02556(15) 0.4251(2) 0.17950(9) 0.0263(3) Uani 1 1 d . . . H4 H -0.0707 0.4214 0.1829 0.032 Uiso 1 1 calc R . . C5 C 0.10530(16) 0.4862(2) 0.24551(9) 0.0270(3) Uani 1 1 d . . . H5 H 0.0635 0.5252 0.2942 0.032 Uiso 1 1 calc R . . C6 C 0.24535(15) 0.4903(2) 0.24047(9) 0.0255(3) Uani 1 1 d . . . H6 H 0.2991 0.5335 0.2857 0.031 Uiso 1 1 calc R . . C7 C 0.29332(14) 0.30649(18) 0.02586(8) 0.0191(3) Uani 1 1 d . . . C8 C 0.21154(15) 0.2701(2) -0.05162(9) 0.0235(3) Uani 1 1 d . . . H8A H 0.2584 0.3229 -0.0981 0.035 Uiso 1 1 calc R . . H8B H 0.1213 0.3262 -0.0478 0.035 Uiso 1 1 calc R . . H8C H 0.2016 0.1375 -0.0595 0.035 Uiso 1 1 calc R . . C9 C 0.63069(14) 0.19989(19) -0.02719(8) 0.0191(3) Uani 1 1 d . . . C10 C 0.83630(15) 0.1242(2) -0.10010(9) 0.0264(3) Uani 1 1 d . . . H10A H 0.8708 0.2309 -0.1295 0.040 Uiso 1 1 calc R . . H10B H 0.8597 0.0119 -0.1294 0.040 Uiso 1 1 calc R . . H10C H 0.8776 0.1207 -0.0449 0.040 Uiso 1 1 calc R . . C11 C 0.60772(16) 0.0896(2) -0.16866(9) 0.0278(4) Uani 1 1 d . . . H11A H 0.5436 -0.0084 -0.1557 0.042 Uiso 1 1 calc R . . H11B H 0.6684 0.0475 -0.2112 0.042 Uiso 1 1 calc R . . H11C H 0.5571 0.1976 -0.1882 0.042 Uiso 1 1 calc R . . H1N H 0.451(2) 0.198(3) -0.0761(14) 0.043(6) 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 0.0213(2) 0.0252(2) 0.0205(2) -0.00030(14) -0.00408(15) -0.00095(14) O1 0.0197(5) 0.0357(6) 0.0194(5) -0.0049(5) -0.0015(4) 0.0003(4) N1 0.0211(6) 0.0203(6) 0.0171(6) 0.0005(5) 0.0011(5) 0.0001(5) N2 0.0193(6) 0.0264(7) 0.0154(6) -0.0023(5) -0.0015(5) -0.0003(5) N3 0.0209(6) 0.0241(6) 0.0208(6) -0.0022(5) 0.0016(5) -0.0015(5) C1 0.0222(7) 0.0195(7) 0.0219(7) 0.0031(6) -0.0003(6) 0.0002(6) C2 0.0219(7) 0.0153(7) 0.0207(7) 0.0026(5) -0.0001(6) 0.0003(5) C3 0.0221(7) 0.0202(7) 0.0275(8) 0.0013(6) -0.0020(6) -0.0014(6) C4 0.0222(7) 0.0237(8) 0.0334(8) 0.0035(6) 0.0063(6) 0.0006(6) C5 0.0307(8) 0.0255(8) 0.0252(8) 0.0030(6) 0.0088(6) 0.0021(6) C6 0.0289(8) 0.0278(8) 0.0196(7) 0.0004(6) -0.0003(6) 0.0005(6) C7 0.0214(7) 0.0144(6) 0.0212(7) 0.0024(5) -0.0021(5) -0.0012(6) C8 0.0233(7) 0.0248(7) 0.0221(7) -0.0021(6) -0.0032(6) 0.0011(6) C9 0.0212(7) 0.0154(6) 0.0208(7) 0.0029(5) 0.0002(5) -0.0016(5) C10 0.0220(7) 0.0295(8) 0.0279(8) -0.0004(6) 0.0054(6) 0.0004(6) C11 0.0287(8) 0.0334(8) 0.0213(8) -0.0070(6) 0.0015(6) -0.0037(7) _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 C9 1.6881(14) . ? O1 C1 1.3549(17) . ? O1 H1O 0.85(2) . ? N1 C7 1.2925(18) . ? N1 N2 1.3673(17) . ? N2 C9 1.3706(19) . ? N2 H1N 0.81(2) . ? N3 C9 1.3405(19) . ? N3 C10 1.4596(18) . ? N3 C11 1.4671(18) . ? C1 C6 1.396(2) . ? C1 C2 1.420(2) . ? C2 C3 1.4094(19) . ? C2 C7 1.477(2) . ? C3 C4 1.383(2) . ? C3 H3 0.9500 . ? C4 C5 1.389(2) . ? C4 H4 0.9500 . ? C5 C6 1.382(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.5041(19) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1O 107.9(13) . . ? C7 N1 N2 119.45(12) . . ? N1 N2 C9 119.14(12) . . ? N1 N2 H1N 120.0(15) . . ? C9 N2 H1N 120.8(15) . . ? C9 N3 C10 121.23(12) . . ? C9 N3 C11 121.86(12) . . ? C10 N3 C11 116.83(11) . . ? O1 C1 C6 116.37(13) . . ? O1 C1 C2 123.60(13) . . ? C6 C1 C2 120.03(13) . . ? C3 C2 C1 117.19(13) . . ? C3 C2 C7 121.19(12) . . ? C1 C2 C7 121.61(12) . . ? C4 C3 C2 122.12(14) . . ? C4 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? C3 C4 C5 119.63(14) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 120.01(14) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 121.00(14) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? N1 C7 C2 114.75(12) . . ? N1 C7 C8 123.14(13) . . ? C2 C7 C8 122.10(12) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 N2 114.70(12) . . ? N3 C9 S1 124.08(11) . . ? N2 C9 S1 121.22(11) . . ? 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 . . ? 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 . . ? 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 C7 N1 N2 C9 177.85(12) . . . . ? O1 C1 C2 C3 179.97(13) . . . . ? C6 C1 C2 C3 -0.9(2) . . . . ? O1 C1 C2 C7 1.3(2) . . . . ? C6 C1 C2 C7 -179.56(13) . . . . ? C1 C2 C3 C4 -0.2(2) . . . . ? C7 C2 C3 C4 178.47(13) . . . . ? C2 C3 C4 C5 0.9(2) . . . . ? C3 C4 C5 C6 -0.4(2) . . . . ? C4 C5 C6 C1 -0.7(2) . . . . ? O1 C1 C6 C5 -179.43(14) . . . . ? C2 C1 C6 C5 1.4(2) . . . . ? N2 N1 C7 C2 178.77(12) . . . . ? N2 N1 C7 C8 -0.3(2) . . . . ? C3 C2 C7 N1 -167.70(13) . . . . ? C1 C2 C7 N1 10.92(19) . . . . ? C3 C2 C7 C8 11.4(2) . . . . ? C1 C2 C7 C8 -169.99(13) . . . . ? C10 N3 C9 N2 174.78(12) . . . . ? C11 N3 C9 N2 -2.0(2) . . . . ? C10 N3 C9 S1 -5.9(2) . . . . ? C11 N3 C9 S1 177.38(11) . . . . ? N1 N2 C9 N3 179.99(12) . . . . ? N1 N2 C9 S1 0.62(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.256 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.044 # start Validation Reply Form _vrf_PLAT420_olo33 ; PROBLEM: D-H Without Accepto N2 - H1N ...? RESPONSE: thr H atom was found from dif. maps and refined freely. ; # end Validation Reply Form # Attachment 'olodc.cif' data_olodc _database_code_depnum_ccdc_archive 'CCDC 749543' #TrackingRef 'olodc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1-(2-hydroxyphenyl)ethan-1-one N-phenylthiosemicarbazone' ; _chemical_name_common ;'1-(2-hydroxyphenyl)ethan-1-one N-phenylthiosemicarbazone' ; _chemical_melting_point ? _chemical_formula_moiety 'C15 H15 N3 O S' _chemical_formula_sum 'C15 H15 N3 O S' _chemical_formula_weight 285.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.5243(2) _cell_length_b 10.5902(4) _cell_length_c 12.2174(5) _cell_angle_alpha 73.835(3) _cell_angle_beta 86.048(3) _cell_angle_gamma 87.208(3) _cell_volume 684.54(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1750 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 25.07 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.235 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.789 _exptl_absorpt_correction_T_max 0.860 _exptl_absorpt_process_details 'CrysAlis RED, Oxford Diffraction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6809 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.07 _reflns_number_total 2441 _reflns_number_gt 1893 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, date)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, date)' _computing_data_reduction 'CrysAlis RED ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXL-97 _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^)+(0.0532P)^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 2441 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0854 _refine_ls_wR_factor_gt 0.0812 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.04962(7) 0.41050(4) 0.35891(4) 0.01837(14) Uani 1 1 d . . . O1 O 0.9359(2) 0.74069(12) 0.19814(10) 0.0241(3) Uani 1 1 d . . . N1 N 0.5502(2) 0.66778(13) 0.33530(12) 0.0158(3) Uani 1 1 d . . . N2 N 0.3578(2) 0.58509(13) 0.37380(12) 0.0171(3) Uani 1 1 d . . . N3 N 0.4797(2) 0.47263(14) 0.24284(12) 0.0173(3) Uani 1 1 d . . . C1 C 0.7809(3) 0.84906(16) 0.34080(14) 0.0150(4) Uani 1 1 d . . . C2 C 0.9457(3) 0.83826(16) 0.24992(14) 0.0171(4) Uani 1 1 d . . . C3 C 1.1295(3) 0.92808(17) 0.21010(15) 0.0209(4) Uani 1 1 d . . . H3 H 1.2411 0.9182 0.1501 0.025 Uiso 1 1 calc R . . C4 C 1.1512(3) 1.03134(16) 0.25681(14) 0.0198(4) Uani 1 1 d . . . H4 H 1.2772 1.0921 0.2290 0.024 Uiso 1 1 calc R . . C5 C 0.9891(3) 1.04617(17) 0.34432(15) 0.0204(4) Uani 1 1 d . . . H5 H 1.0022 1.1175 0.3763 0.024 Uiso 1 1 calc R . . C6 C 0.8082(3) 0.95657(16) 0.38478(15) 0.0184(4) Uani 1 1 d . . . H6 H 0.6978 0.9680 0.4447 0.022 Uiso 1 1 calc R . . C7 C 0.5835(3) 0.75635(16) 0.38724(14) 0.0153(4) Uani 1 1 d . . . C8 C 0.4280(3) 0.76903(17) 0.48917(14) 0.0185(4) Uani 1 1 d . . . H8A H 0.2864 0.8266 0.4639 0.028 Uiso 1 1 calc R . . H8B H 0.5220 0.8069 0.5368 0.028 Uiso 1 1 calc R . . H8C H 0.3737 0.6820 0.5336 0.028 Uiso 1 1 calc R . . C9 C 0.3084(3) 0.49353(16) 0.31982(14) 0.0155(4) Uani 1 1 d . . . C10 C 0.4623(3) 0.39144(16) 0.16759(14) 0.0159(4) Uani 1 1 d . . . C11 C 0.6542(3) 0.30424(17) 0.15876(15) 0.0199(4) Uani 1 1 d . . . H11 H 0.7869 0.2941 0.2063 0.024 Uiso 1 1 calc R . . C12 C 0.6504(3) 0.23193(17) 0.07968(15) 0.0215(4) Uani 1 1 d . . . H12 H 0.7820 0.1731 0.0723 0.026 Uiso 1 1 calc R . . C13 C 0.4550(3) 0.24559(17) 0.01164(14) 0.0203(4) Uani 1 1 d . . . H13 H 0.4522 0.1958 -0.0420 0.024 Uiso 1 1 calc R . . C14 C 0.2634(3) 0.33192(17) 0.02192(14) 0.0199(4) Uani 1 1 d . . . H14 H 0.1291 0.3404 -0.0244 0.024 Uiso 1 1 calc R . . C15 C 0.2661(3) 0.40603(16) 0.09916(14) 0.0181(4) Uani 1 1 d . . . H15 H 0.1356 0.4660 0.1053 0.022 Uiso 1 1 calc R . . H1N H 0.2350 0.6020 0.4264 0.027(5) Uiso 1 1 d R . . H2N H 0.6374 0.5071 0.2452 0.041(6) Uiso 1 1 d R . . H3O H 0.8196 0.6844 0.2401 0.055(7) Uiso 1 1 d 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 0.0159(2) 0.0201(2) 0.0209(2) -0.00825(18) 0.00155(17) -0.00619(17) O1 0.0291(7) 0.0241(7) 0.0231(7) -0.0141(6) 0.0079(6) -0.0095(6) N1 0.0142(7) 0.0149(7) 0.0189(7) -0.0053(6) -0.0009(6) -0.0038(6) N2 0.0146(7) 0.0185(8) 0.0206(8) -0.0090(6) 0.0027(6) -0.0057(6) N3 0.0160(7) 0.0181(7) 0.0199(8) -0.0085(6) 0.0021(6) -0.0059(6) C1 0.0138(8) 0.0149(9) 0.0165(9) -0.0039(7) -0.0033(7) -0.0011(7) C2 0.0197(9) 0.0159(9) 0.0163(8) -0.0051(7) -0.0032(7) -0.0008(7) C3 0.0196(9) 0.0251(10) 0.0162(9) -0.0029(8) 0.0022(7) -0.0030(8) C4 0.0198(9) 0.0156(9) 0.0218(9) -0.0004(7) -0.0020(7) -0.0052(7) C5 0.0243(9) 0.0155(9) 0.0226(9) -0.0066(7) -0.0032(8) -0.0030(7) C6 0.0192(9) 0.0168(9) 0.0196(9) -0.0063(7) 0.0001(7) 0.0001(7) C7 0.0140(8) 0.0145(9) 0.0171(8) -0.0036(7) -0.0034(7) 0.0015(7) C8 0.0191(9) 0.0177(9) 0.0199(9) -0.0074(7) 0.0020(7) -0.0036(7) C9 0.0168(8) 0.0135(8) 0.0159(8) -0.0031(7) -0.0040(7) -0.0003(7) C10 0.0183(9) 0.0155(9) 0.0139(8) -0.0036(7) 0.0025(7) -0.0066(7) C11 0.0163(8) 0.0224(10) 0.0218(9) -0.0068(8) -0.0021(7) -0.0029(7) C12 0.0182(9) 0.0220(10) 0.0257(10) -0.0102(8) 0.0016(8) 0.0009(7) C13 0.0234(9) 0.0228(10) 0.0172(9) -0.0098(8) 0.0021(7) -0.0047(8) C14 0.0203(9) 0.0248(10) 0.0145(9) -0.0045(8) -0.0014(7) -0.0035(8) C15 0.0182(9) 0.0178(9) 0.0171(9) -0.0029(7) 0.0006(7) -0.0013(7) _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 C9 1.6852(16) . ? O1 C2 1.358(2) . ? O1 H3O 0.9230 . ? N1 C7 1.296(2) . ? N1 N2 1.3819(18) . ? N2 C9 1.362(2) . ? N2 H1N 0.9473 . ? N3 C9 1.342(2) . ? N3 C10 1.433(2) . ? N3 H2N 0.9660 . ? C1 C6 1.406(2) . ? C1 C2 1.413(2) . ? C1 C7 1.478(2) . ? C2 C3 1.393(2) . ? C3 C4 1.380(2) . ? C3 H3 0.9500 . ? C4 C5 1.385(2) . ? C4 H4 0.9500 . ? C5 C6 1.381(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.497(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C10 C11 1.390(2) . ? C10 C15 1.391(2) . ? C11 C12 1.392(2) . ? C11 H11 0.9500 . ? C12 C13 1.385(2) . ? C12 H12 0.9500 . ? C13 C14 1.387(2) . ? C13 H13 0.9500 . ? C14 C15 1.386(2) . ? C14 H14 0.9500 . ? C15 H15 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 O1 H3O 105.9 . . ? C7 N1 N2 118.23(13) . . ? C9 N2 N1 120.80(13) . . ? C9 N2 H1N 116.2 . . ? N1 N2 H1N 121.5 . . ? C9 N3 C10 126.84(13) . . ? C9 N3 H2N 116.2 . . ? C10 N3 H2N 116.5 . . ? C6 C1 C2 116.53(14) . . ? C6 C1 C7 120.24(14) . . ? C2 C1 C7 123.20(14) . . ? O1 C2 C3 116.83(14) . . ? O1 C2 C1 122.45(14) . . ? C3 C2 C1 120.72(15) . . ? C4 C3 C2 120.76(16) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.83(15) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 119.57(15) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C1 122.56(15) . . ? C5 C6 H6 118.7 . . ? C1 C6 H6 118.7 . . ? N1 C7 C1 117.55(14) . . ? N1 C7 C8 122.64(14) . . ? C1 C7 C8 119.79(14) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 N2 116.08(13) . . ? N3 C9 S1 125.32(12) . . ? N2 C9 S1 118.50(12) . . ? C11 C10 C15 120.71(15) . . ? C11 C10 N3 118.38(15) . . ? C15 C10 N3 120.75(15) . . ? C10 C11 C12 119.46(16) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C13 C12 C11 120.09(16) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 119.97(15) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 120.63(16) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C10 119.12(16) . . ? C14 C15 H15 120.4 . . ? C10 C15 H15 120.4 . . ? 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 C7 N1 N2 C9 177.47(14) . . . . ? C6 C1 C2 O1 -178.54(15) . . . . ? C7 C1 C2 O1 -0.3(3) . . . . ? C6 C1 C2 C3 2.2(2) . . . . ? C7 C1 C2 C3 -179.57(16) . . . . ? O1 C2 C3 C4 179.20(15) . . . . ? C1 C2 C3 C4 -1.5(3) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? C2 C1 C6 C5 -1.6(3) . . . . ? C7 C1 C6 C5 -179.87(16) . . . . ? N2 N1 C7 C1 -176.44(14) . . . . ? N2 N1 C7 C8 2.2(2) . . . . ? C6 C1 C7 N1 172.51(15) . . . . ? C2 C1 C7 N1 -5.7(3) . . . . ? C6 C1 C7 C8 -6.2(2) . . . . ? C2 C1 C7 C8 175.58(15) . . . . ? C10 N3 C9 N2 -173.71(15) . . . . ? C10 N3 C9 S1 9.8(2) . . . . ? N1 N2 C9 N3 11.8(2) . . . . ? N1 N2 C9 S1 -171.47(12) . . . . ? C9 N3 C10 C11 -132.99(18) . . . . ? C9 N3 C10 C15 51.4(2) . . . . ? C15 C10 C11 C12 0.6(2) . . . . ? N3 C10 C11 C12 -174.92(15) . . . . ? C10 C11 C12 C13 -0.9(2) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? C13 C14 C15 C10 -0.9(2) . . . . ? C11 C10 C15 C14 0.3(2) . . . . ? N3 C10 C15 C14 175.72(14) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.311 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.050