#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/27/2012767.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2012767 loop_ _publ_author_name 'Forni, Alessandra' 'Gradinaru, Julieta' _publ_section_title ; 1-(1-Benzoylpropen-2-yl)-3-methylisothiosemicarbazide ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o342 _journal_page_last o344 _journal_paper_doi 10.1107/S0108270102007059 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C12 H15 N3 O S' _chemical_formula_moiety 'C12 H15 N3 O S' _chemical_formula_sum 'C12 H15 N3 O S' _chemical_formula_weight 249.33 _chemical_name_common ; benzoylacetone S-methylisothiosemicarbazone ; _chemical_name_systematic ; 1-(1-Benzoylpropen2-yl)-3-methylisothiosemicarbazide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 92.800(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.9320(10) _cell_length_b 5.3240(10) _cell_length_c 26.316(2) _cell_measurement_reflns_used 1875 _cell_measurement_temperature 288(2) _cell_measurement_theta_max 23.05 _cell_measurement_theta_min 2.37 _cell_volume 1249.9(3) _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL97 and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al.,1994)' _diffrn_ambient_temperature 288(2) _diffrn_measured_fraction_theta_full 0.901 _diffrn_measured_fraction_theta_max 0.901 _diffrn_measurement_device_type 'Bruker SMART Apex area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.044 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 11930 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 1.55 _diffrn_standards_decay_% 0.00 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.858 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS in SAINT; Bruker, 1997)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.33 _refine_diff_density_min -0.25 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.881 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 2858 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.881 _refine_ls_R_factor_all 0.085 _refine_ls_R_factor_gt 0.050 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0866P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.140 _refine_ls_wR_factor_ref 0.151 _reflns_number_gt 1566 _reflns_number_total 2858 _reflns_threshold_expression I>2\s(I) _cod_data_source_file na1569.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2012767 _cod_database_fobs_code 2012767 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S 0.72212(8) -0.11508(13) -0.11368(2) 0.0650(3) Uani d . 1 . . S O 0.5825(2) -0.3019(3) 0.10011(7) 0.0680(5) Uani d . 1 . . O N1 0.7209(2) -0.0502(4) 0.03292(7) 0.0580(5) Uani d . 1 . . N H1 0.6639 -0.1750 0.0395 0.070 Uiso calc R 1 . . H N2 0.7548(2) -0.0042(4) -0.01687(7) 0.0566(5) Uani d . 1 . . N N3 0.5951(2) -0.3419(4) -0.03965(8) 0.0762(7) Uani d . 1 . . N H3A 0.5746 -0.3761 -0.0088 0.091 Uiso calc R 1 . . H H3B 0.5560 -0.4297 -0.0643 0.091 Uiso calc R 1 . . H C1 0.6893(3) -0.1490(5) -0.04943(9) 0.0538(6) Uani d . 1 . . C C2 0.5835(3) -0.1658(4) 0.18553(9) 0.0520(6) Uani d . 1 . . C C3 0.6207(3) 0.0079(5) 0.22269(9) 0.0646(7) Uani d . 1 . . C H3 0.6856 0.1384 0.2155 0.078 Uiso calc R 1 . . H C4 0.5637(3) -0.0074(6) 0.27045(10) 0.0724(8) Uani d . 1 . . C H4 0.5906 0.1116 0.2951 0.087 Uiso calc R 1 . . H C5 0.6340(3) -0.1454(5) 0.13273(9) 0.0545(6) Uani d . 1 . . C C6 0.7328(3) 0.0449(5) 0.11928(9) 0.0582(7) Uani d . 1 . . C H6 0.7734 0.1461 0.1453 0.070 Uiso calc R 1 . . H C7 0.7742(2) 0.0936(4) 0.07081(8) 0.0490(6) Uani d . 1 . . C C8 0.8304(4) 0.1644(5) -0.11397(11) 0.0809(9) Uani d . 1 . . C H8A 0.8556 0.2024 -0.1482 0.121 Uiso calc R 1 . . H H8B 0.9207 0.1414 -0.0931 0.121 Uiso calc R 1 . . H H8C 0.7736 0.3005 -0.1007 0.121 Uiso calc R 1 . . H C9 0.4684(3) -0.1962(6) 0.28136(10) 0.0707(8) Uani d . 1 . . C H9 0.4282 -0.2056 0.3132 0.085 Uiso calc R 1 . . H C10 0.4321(3) -0.3720(6) 0.24518(11) 0.0796(9) Uani d . 1 . . C H10 0.3674 -0.5021 0.2527 0.096 Uiso calc R 1 . . H C11 0.4899(3) -0.3596(5) 0.19783(10) 0.0686(7) Uani d . 1 . . C H11 0.4655 -0.4833 0.1739 0.082 Uiso calc R 1 . . H C12 0.8779(3) 0.3000(5) 0.05865(10) 0.0705(8) Uani d . 1 . . C H12A 0.8921 0.3016 0.0227 0.106 Uiso calc R 1 . . H H12B 0.9727 0.2744 0.0767 0.106 Uiso calc R 1 . . H H12C 0.8362 0.4576 0.0686 0.106 Uiso calc R 1 . . H 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 S 0.0756(5) 0.0696(5) 0.0507(4) 0.0015(4) 0.0124(3) 0.0033(3) O 0.0780(12) 0.0660(11) 0.0608(10) -0.0115(10) 0.0122(9) -0.0128(9) N1 0.0599(12) 0.0622(13) 0.0528(12) -0.0061(10) 0.0125(10) 0.0030(10) N2 0.0589(12) 0.0620(13) 0.0493(11) -0.0024(11) 0.0076(10) 0.0007(10) N3 0.0817(16) 0.0959(19) 0.0515(12) -0.0290(14) 0.0082(11) 0.0012(12) C1 0.0480(13) 0.0602(15) 0.0539(14) 0.0026(12) 0.0087(11) 0.0038(12) C2 0.0484(13) 0.0551(15) 0.0525(13) 0.0064(12) 0.0017(11) 0.0052(11) C3 0.0710(17) 0.0646(16) 0.0594(16) -0.0080(14) 0.0144(13) -0.0016(13) C4 0.0811(19) 0.0806(19) 0.0564(16) -0.0020(17) 0.0133(14) -0.0080(14) C5 0.0533(14) 0.0558(15) 0.0542(14) 0.0048(12) 0.0012(11) -0.0030(12) C6 0.0550(14) 0.0664(17) 0.0531(14) -0.0058(13) 0.0006(11) -0.0048(12) C7 0.0452(12) 0.0529(14) 0.0485(13) -0.0007(11) -0.0016(10) -0.0016(11) C8 0.110(2) 0.0616(18) 0.0737(19) -0.0069(17) 0.0291(17) 0.0084(14) C9 0.0684(18) 0.088(2) 0.0565(16) 0.0040(16) 0.0118(14) 0.0127(15) C10 0.078(2) 0.086(2) 0.0747(19) -0.0185(17) 0.0069(16) 0.0226(17) C11 0.0791(19) 0.0664(17) 0.0599(16) -0.0144(15) 0.0005(14) 0.0057(13) C12 0.0699(18) 0.0773(19) 0.0643(16) -0.0130(15) 0.0041(13) 0.0024(14) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C1 S C8 102.05(13) no C7 N1 N2 121.5(2) no C7 N1 H1 119.2 no N2 N1 H1 119.2 no C1 N2 N1 114.6(2) no C1 N3 H3A 120.0 no C1 N3 H3B 120.0 no H3A N3 H3B 120.0 no N2 C1 N3 126.7(2) no N2 C1 S 119.85(19) no N3 C1 S 113.41(19) no C3 C2 C11 117.7(2) no C3 C2 C5 122.8(2) no C11 C2 C5 119.4(2) no C2 C3 C4 121.4(3) no C2 C3 H3 119.3 no C4 C3 H3 119.3 no C9 C4 C3 119.9(3) no C9 C4 H4 120.0 no C3 C4 H4 120.0 no O C5 C6 121.1(2) no O C5 C2 117.9(2) no C6 C5 C2 120.9(2) no C7 C6 C5 125.1(2) no C7 C6 H6 117.5 no C5 C6 H6 117.5 no N1 C7 C6 119.2(2) no N1 C7 C12 118.1(2) no C6 C7 C12 122.8(2) no S C8 H8A 109.5 no S C8 H8B 109.5 no H8A C8 H8B 109.5 no S C8 H8C 109.5 no H8A C8 H8C 109.5 no H8B C8 H8C 109.5 no C4 C9 C10 119.4(3) no C4 C9 H9 120.3 no C10 C9 H9 120.3 no C9 C10 C11 120.9(3) no C9 C10 H10 119.5 no C11 C10 H10 119.5 no C10 C11 C2 120.6(3) no C10 C11 H11 119.7 no C2 C11 H11 119.7 no C7 C12 H12A 109.5 no C7 C12 H12B 109.5 no H12A C12 H12B 109.5 no C7 C12 H12C 109.5 no H12A C12 H12C 109.5 no H12B C12 H12C 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S C1 . 1.739(2) no S C8 . 1.775(3) no O C5 . 1.267(3) no N1 C7 . 1.327(3) no N1 N2 . 1.381(3) no N1 H1 . 0.8600 no N2 C1 . 1.274(3) no N3 C1 . 1.361(3) no N3 H3A . 0.8600 no N3 H3B . 0.8600 no C2 C3 . 1.375(3) no C2 C11 . 1.377(3) no C2 C5 . 1.486(3) no C3 C4 . 1.381(3) no C3 H3 . 0.9300 no C4 C9 . 1.357(4) no C4 H4 . 0.9300 no C5 C6 . 1.400(3) no C6 C7 . 1.370(3) no C6 H6 . 0.9300 no C7 C12 . 1.482(3) no C8 H8A . 0.9600 no C8 H8B . 0.9600 no C8 H8C . 0.9600 no C9 C10 . 1.363(4) no C9 H9 . 0.9300 no C10 C11 . 1.373(4) no C10 H10 . 0.9300 no C11 H11 . 0.9300 no C12 H12A . 0.9600 no C12 H12B . 0.9600 no C12 H12C . 0.9600 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 O . 0.86 1.91 2.581(3) 134 yes N1 H1 N3 . 0.86 2.32 2.667(3) 104 yes N3 H3A N1 . 0.86 2.40 2.667(3) 98 yes C11 H11 O . 0.93 2.45 2.757(4) 99 yes N3 H3B O 3_645 0.86 2.08 2.898(3) 157 yes N3 H3A N3 3_645 0.86 2.52 3.228(4) 140 yes C9 H9 S 4_556 0.93 2.89 3.751(3) 155 yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21181801 2 PubChem 139058588