#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:52:15 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301804 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/44/2214408.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_2214408 loop_ _publ_author_name 'Guo-Xiang Liu' 'Wen-Shi Wu' 'Hai-Ping Li' 'Guo-Dong Yang' _publ_section_title ; 3-Methyl-N'-(2-thienylcarboxyl)butyrohydrazide ; _journal_coeditor_code WK2059 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3225 _journal_page_last o3225 _journal_paper_doi 10.1107/S1600536807028498 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C10 H14 N2 O2 S , H2 O' _chemical_formula_moiety 'C10 H14 N2 O2 S , H2 O' _chemical_formula_sum 'C10 H16 N2 O3 S' _chemical_formula_weight 244.31 _chemical_name_systematic ; 3-Methyl-N'-(2-thienylcarboxyl)butyrohydrazide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 96.387(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.5648(5) _cell_length_b 7.3451(7) _cell_length_c 25.956(2) _cell_measurement_reflns_used 2785 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.4835 _cell_measurement_theta_min 2.7712 _cell_volume 1243.81(18) _computing_cell_refinement CrystalClear _computing_data_collection 'CrystalClear (Rigaku, 2000)' _computing_data_reduction CrystalClear _computing_molecular_graphics 'SHELXTL (Sheldrick, 2000)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 14.6306 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Rigaku Mercury70 (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 8853 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 2.88 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.255 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8007 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrystalClear; Rigaku, 2000)' _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.400 _refine_diff_density_min -0.292 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 194 _refine_ls_number_reflns 2849 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.999 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0442 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.5306P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1155 _refine_ls_wR_factor_ref 0.1228 _reflns_number_gt 2423 _reflns_number_total 2849 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wk2059.cif _cod_data_source_block I _cod_original_sg_symbol_H-M P21/c _cod_database_code 2214408 _cod_database_fobs_code 2214408 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' loop_ _atom_site_type_symbol _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 S S1 0.81975(8) 0.28733(9) 0.210206(18) 0.0589(2) Uani d . 1 N N1 0.8807(2) 0.15490(19) 0.06560(5) 0.0356(3) Uani d . 1 H H1A 1.0116 0.1423 0.0682 0.043 Uiso calc R 1 N N2 0.7661(2) 0.14048(19) 0.01749(5) 0.0358(3) Uani d . 1 H H2B 0.7293 0.0353 0.0052 0.043 Uiso calc R 1 O O1 0.59982(18) 0.1910(2) 0.10851(5) 0.0484(3) Uani d . 1 O O2 0.7541(2) 0.44417(16) 0.00794(5) 0.0480(3) Uani d . 1 C C1 0.9259(2) 0.2181(2) 0.15619(6) 0.0351(3) Uani d . 1 C C2 1.1373(3) 0.2035(2) 0.16588(6) 0.0409(4) Uani d . 1 H H2A 1.2229 0.1678 0.1415 0.049 Uiso calc R 1 C C3 1.2057(3) 0.2505(3) 0.21810(8) 0.0549(5) Uani d . 1 C C4 1.0527(4) 0.2977(3) 0.24551(8) 0.0613(6) Uani d . 1 C C5 0.7868(2) 0.1886(2) 0.10829(6) 0.0331(3) Uani d . 1 C C6 0.7127(2) 0.2931(2) -0.01001(6) 0.0348(3) Uani d . 1 C C7 0.5979(3) 0.2597(3) -0.06275(7) 0.0429(4) Uani d . 1 C C8 0.6887(3) 0.3566(3) -0.10687(7) 0.0471(4) Uani d . 1 O O3 0.27168(19) 0.21322(16) 0.03360(5) 0.0376(3) Uani d . 1 C C9 0.9125(4) 0.3120(4) -0.10852(10) 0.0646(6) Uani d . 1 H H9A 0.960(5) 0.370(4) -0.1390(12) 0.095(9) Uiso d . 1 H H9B 0.924(6) 0.192(5) -0.1161(14) 0.114 Uiso d . 1 H H9C 1.004(5) 0.348(5) -0.0758(14) 0.114 Uiso d . 1 C C10 0.5614(5) 0.3099(4) -0.15790(9) 0.0717(7) Uani d . 1 H H3A 1.349(4) 0.253(3) 0.2300(10) 0.064(7) Uiso d . 1 H H4A 1.060(4) 0.340(4) 0.2795(11) 0.082(8) Uiso d . 1 H H7A 0.591(3) 0.127(4) -0.0702(9) 0.065(7) Uiso d . 1 H H7B 0.467(5) 0.303(4) -0.0612(11) 0.085(9) Uiso d . 1 H H8A 0.680(3) 0.493(3) -0.1014(9) 0.068(7) Uiso d . 1 H H10A 0.566(4) 0.174(4) -0.1630(11) 0.081 Uiso d . 1 H H10B 0.426(5) 0.344(4) -0.1543(12) 0.093(10) Uiso d . 1 H H10C 0.615(5) 0.375(4) -0.1879(12) 0.096(9) Uiso d . 1 H H3 0.375(4) 0.210(3) 0.0532(10) 0.054(7) Uiso d . 1 H H4 0.261(4) 0.327(3) 0.0205(10) 0.064(7) Uiso d . 1 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 S1 0.0568(3) 0.0872(4) 0.0332(3) 0.0112(3) 0.0069(2) -0.0078(2) N1 0.0335(6) 0.0469(7) 0.0256(6) 0.0043(6) -0.0004(5) 0.0002(6) N2 0.0428(7) 0.0371(7) 0.0262(6) -0.0009(6) -0.0025(5) -0.0018(5) O1 0.0340(6) 0.0745(9) 0.0364(6) 0.0005(6) 0.0022(5) -0.0027(6) O2 0.0644(8) 0.0380(6) 0.0392(6) -0.0027(6) -0.0043(6) 0.0000(5) C1 0.0401(8) 0.0401(8) 0.0248(7) 0.0004(6) 0.0027(6) 0.0027(6) C2 0.0392(9) 0.0543(10) 0.0282(8) -0.0023(7) -0.0002(6) 0.0034(7) C3 0.0506(11) 0.0732(13) 0.0378(10) -0.0087(10) -0.0098(8) 0.0061(9) C4 0.0738(15) 0.0779(15) 0.0300(9) -0.0049(11) -0.0045(9) -0.0052(9) C5 0.0347(8) 0.0351(7) 0.0289(7) 0.0010(6) 0.0017(6) 0.0025(6) C6 0.0366(8) 0.0415(8) 0.0263(7) -0.0013(6) 0.0031(6) 0.0008(6) C7 0.0453(10) 0.0540(10) 0.0277(8) -0.0046(8) -0.0028(7) 0.0016(7) C8 0.0697(12) 0.0411(9) 0.0301(8) 0.0038(8) 0.0039(8) 0.0010(7) O3 0.0354(6) 0.0389(6) 0.0378(6) -0.0016(5) 0.0009(5) -0.0010(5) C9 0.0687(14) 0.0740(15) 0.0538(13) -0.0077(12) 0.0191(11) -0.0054(12) C10 0.093(2) 0.0873(18) 0.0314(10) 0.0056(15) -0.0071(11) 0.0036(11) 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 C4 S1 C1 91.77(10) yes C5 N1 N2 120.11(13) yes C5 N1 H1A 119.9 ? N2 N1 H1A 119.9 ? C6 N2 N1 119.57(13) ? C6 N2 H2B 120.2 ? N1 N2 H2B 120.2 ? C2 C1 C5 130.92(15) yes C2 C1 S1 111.41(12) yes C5 C1 S1 117.65(12) yes C1 C2 C3 110.95(16) ? C1 C2 H2A 124.5 ? C3 C2 H2A 124.5 ? C4 C3 C2 113.15(18) ? C4 C3 H3A 126.2(15) ? C2 C3 H3A 120.5(15) ? C3 C4 S1 112.71(16) ? C3 C4 H4A 128.9(17) ? S1 C4 H4A 118.2(17) ? O1 C5 N1 123.64(15) ? O1 C5 C1 121.31(15) ? N1 C5 C1 115.02(13) ? O2 C6 N2 121.14(14) ? O2 C6 C7 124.16(15) ? N2 C6 C7 114.69(14) ? C6 C7 C8 114.11(15) ? C6 C7 H7A 110.2(13) ? C8 C7 H7A 109.1(14) ? C6 C7 H7B 106.1(18) ? C8 C7 H7B 108.3(17) ? H7A C7 H7B 109(2) ? C9 C8 C10 111.6(2) ? C9 C8 C7 112.47(18) ? C10 C8 C7 108.98(19) ? C9 C8 H8A 106.7(13) ? C10 C8 H8A 108.1(13) ? C7 C8 H8A 108.9(13) ? H3 O3 H4 107(2) ? C8 C9 H9A 109.1(18) ? C8 C9 H9B 109(2) ? H9A C9 H9B 102(3) ? C8 C9 H9C 114(2) ? H9A C9 H9C 110(3) ? H9B C9 H9C 112(3) ? C8 C10 H10A 108.5(16) ? C8 C10 H10B 106.6(19) ? H10A C10 H10B 109(2) ? C8 C10 H10C 111.1(17) ? H10A C10 H10C 110(2) ? H10B C10 H10C 111(3) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C4 1.695(2) ? S1 C1 1.7110(16) ? N1 C5 1.349(2) yes N1 N2 1.3883(17) yes N1 H1A 0.8600 ? N2 C6 1.354(2) yes N2 H2B 0.8600 ? O1 C5 1.228(2) yes O2 C6 1.222(2) yes C1 C2 1.387(2) ? C1 C5 1.474(2) yes C2 C3 1.422(2) ? C2 H2A 0.9300 ? C3 C4 1.339(3) ? C3 H3A 0.95(3) ? C4 H4A 0.93(3) ? C6 C7 1.507(2) ? C7 C8 1.525(3) ? C7 H7A 0.99(3) ? C7 H7B 0.92(3) ? C8 C9 1.511(3) ? C8 C10 1.524(3) ? C8 H8A 1.02(3) ? O3 H3 0.80(3) ? O3 H4 0.90(3) ? C9 H9A 0.98(3) ? C9 H9B 0.91(3) ? C9 H9C 1.02(4) ? C10 H10A 1.00(3) ? C10 H10B 0.94(3) ? C10 H10C 1.01(3) ? 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 H1A O3 1_655 0.86 2.08 2.8173(18) 143.2 yes N2 H2B O3 3_655 0.86 2.08 2.9147(18) 162.0 yes O3 H3 O1 . 0.80(3) 1.95(3) 2.7416(18) 171(2) yes O3 H4 O2 3_665 0.90(3) 1.83(3) 2.7355(17) 178(2) yes 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_publ_flag C5 N1 N2 C6 83.78(19) ? C4 S1 C1 C2 0.11(15) yes C4 S1 C1 C5 -178.45(14) yes C5 C1 C2 C3 178.30(17) yes S1 C1 C2 C3 0.0(2) yes C1 C2 C3 C4 -0.1(3) yes C2 C3 C4 S1 0.2(3) yes C1 S1 C4 C3 -0.2(2) yes N2 N1 C5 O1 7.2(2) yes N2 N1 C5 C1 -174.48(13) ? C2 C1 C5 O1 172.76(17) ? S1 C1 C5 O1 -9.0(2) ? C2 C1 C5 N1 -5.6(3) ? S1 C1 C5 N1 172.61(12) ? N1 N2 C6 O2 -4.0(2) yes N1 N2 C6 C7 177.00(14) ? O2 C6 C7 C8 52.8(2) ? N2 C6 C7 C8 -128.14(17) ? C6 C7 C8 C9 55.0(2) ? C6 C7 C8 C10 179.19(19) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21124073 2 PubChem 139072563