#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/69/2006968.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_2006968 loop_ _publ_author_name ' William H. Ojala' ' William B. Gleason' _publ_section_title ; Cyclopentanone Tosylhydrazone and Cyclohexanone Tosylhydrazone ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 63 _journal_page_last 66 _journal_paper_doi 10.1107/S0108270197011682 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety 'C12 H16 N2 O2 S ' _chemical_formula_sum 'C12 H16 N2 O2 S' _chemical_formula_weight 252.33 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method 'from TEXRAY.INF file' _cell_angle_alpha 108.85(2) _cell_angle_beta 101.33(2) _cell_angle_gamma 111.430(10) _cell_formula_units_Z 2 _cell_length_a 8.2680(10) _cell_length_b 8.4830(10) _cell_length_c 10.802(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 173 _cell_measurement_theta_max 50.0 _cell_measurement_theta_min 41.0 _cell_volume 623.4(2) _computing_cell_refinement 'CAD4 software' _computing_data_collection 'CAD4 software (Enraf-Nonius, 1989)' _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1985)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 173 _diffrn_measurement_device CAD4 _diffrn_measurement_method '\w/2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 3683 _diffrn_reflns_theta_max 69.94 _diffrn_standards_decay_% 5.11 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.202 _exptl_absorpt_correction_T_max 0.768 _exptl_absorpt_correction_T_min 0.667 _exptl_absorpt_correction_type '\y scans (North, Phillips & Mathews, 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 268.00 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.75 _refine_diff_density_min -0.60 _refine_ls_extinction_coef 0.3421E-04 _refine_ls_extinction_method Zachariasen_(1963)_type_2_Gaussian_isotropic _refine_ls_goodness_of_fit_obs 2.656 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 203 _refine_ls_number_reflns 2225 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs .0453 _refine_ls_shift/esd_max 0.0005 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 4Fo^2^/\s^2^(Fo^2^)' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs .0583 _reflns_number_observed 2225 _reflns_number_total 2352 _reflns_observed_criterion 'I > 3\s(I)' _cod_data_source_file sx1033.cif _cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: '_atom_site_thermal_displace_type' tag value 'Uij' was replaced with 'Uani' value 33 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not determined' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = 4Fo^2^/\s^2^(Fo^2^)' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 4Fo^2^/\s^2^(Fo^2^)'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 623.4(5) _cod_original_sg_symbol_H-M 'P -1 ' _cod_original_formula_sum 'C12 H16 N2 O2 S ' _cod_database_code 2006968 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' 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 .0220(2) .0220(2) .0241(3) .0121(2) .0106(2) .0096(2) O1 .0297(6) .0370(6) .0329(6) .0218(5) .0169(5) .0141(5) O2 .0347(6) .0288(6) .0303(6) .0177(5) .0143(5) .0163(5) N1 .0248(7) .0235(7) .0248(7) .0080(5) .0086(5) .0097(5) N2 .0236(6) .0222(7) .0230(7) .0087(5) .0086(5) .0082(5) C1 .0203(7) .0255(7) .0249(8) .0083(6) .0073(6) .0096(6) C2 .0347(9) .0253(8) .0271(8) .0088(7) .0083(7) .0104(7) C3 .0237(8) .0230(8) .0347(9) .0063(6) .0058(7) .0106(7) C4 .0388(9) .0256(8) .0288(9) .0130(7) .0071(7) .0069(7) C5 .0328(9) .0261(8) .0232(8) .0111(7) .0073(7) .0073(6) C6 .0211(7) .0199(7) .0232(8) .0085(5) .0083(6) .0065(6) C7 .0272(8) .0362(8) .0277(8) .0154(7) .0139(7) .0143(7) C8 .0236(8) .0349(9) .0316(9) .0127(7) .0136(7) .0124(7) C9 .0232(8) .0285(8) .0267(8) .0097(6) .0063(6) .0053(6) C10 .0299(9) .0460(10) .0215(8) .0156(8) .0091(7) .0077(7) C11 .0247(8) .0344(9) .0249(8) .0119(7) .0121(6) .0078(7) C12 .0262(9) .0510(10) .0321(10) .0157(8) .0041(7) .0063(9) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom S1 .02644(5) .40090(5) .27969(4) .02170(10) Uani ? ? O1 .1345(2) .3619(2) .19700(10) .0304(3) Uani ? ? O2 -.0012(2) .3179(2) .37640(10) .0287(3) Uani ? ? N1 .1544(2) .7371(2) .3061(2) .0257(3) Uani ? ? N2 .1316(2) .6276(2) .38130(10) .0240(3) Uani ? ? C1 .2121(2) .9120(2) .3791(2) .0248(4) Uani ? ? C2 .2471(3) 1.0477(2) .3139(2) .0314(4) Uani ? ? C3 .3819(2) 1.2371(2) .4386(2) .0300(4) Uani ? ? C4 .3205(3) 1.2211(2) .5601(2) .0340(4) Uani ? ? C5 .2637(3) 1.0161(2) .5351(2) .0296(4) Uani ? ? C6 -.1911(2) .3451(2) .1675(2) .0225(4) Uani ? ? C7 -.3339(2) .3322(3) .2205(2) .0293(4) Uani ? ? C8 -.5050(2) .2908(3) .1332(2) .0302(4) Uani ? ? C9 -.5366(2) .2624(2) -.0054(2) .0292(4) Uani ? ? C10 -.3900(3) .2794(3) -.0550(2) .0352(4) Uani ? ? C11 -.2174(2) .3207(2) .0304(2) .0295(4) Uani ? ? C12 -.7261(3) .2123(3) -.0990(2) .0416(5) Uani ? ? H2N .083(3) .650(3) .444(2) .0270 Uani ? ? H2A .138(3) 1.048(3) .276(3) .0366 Uani ? ? H2B .288(3) 1.013(3) .241(3) .0366 Uani ? ? H3A .381(3) 1.337(3) .420(3) .0352 Uani ? ? H3B .506(3) 1.256(3) .459(3) .0352 Uani ? ? H4A .210(3) 1.244(3) .553(3) .0398 Uani ? ? H4B .412(3) 1.307(3) .648(3) .0398 Uani ? ? H5A .166(3) .959(3) .567(3) .0347 Uani ? ? H5B .363(3) 1.008(3) .577(3) .0347 Uani ? ? H7 -.304(3) .347(3) .322(3) .0341 Uani ? ? H8 -.603(3) .278(3) .168(3) .0352 Uani ? ? H10 -.410(3) .262(3) -.143(3) .0411 Uani ? ? H11 -.118(3) .341(3) -.004(3) .0344 Uani ? ? H12A -.721(4) .288(4) -.158(3) .0489 Uani ? ? H12B -.804(4) .232(4) -.048(3) .0489 Uani ? ? H12C -.793(4) .085(4) -.175(3) .0489 Uani ? ? loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.018 0.009 'International Tables' H 0.000 0.000 'International Tables' N 0.031 0.018 'International Tables' O 0.049 0.032 'International Tables' S 0.333 0.557 'International Tables' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 0 3 -6 -1 2 -2 -2 3 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 O1 S1 O2 119.44(7) yes O1 S1 N2 108.14(7) yes O1 S1 C6 108.59(8) yes O2 S1 N2 103.41(7) yes O2 S1 C6 108.99(7) yes N2 S1 C6 107.66(7) yes N2 N1 C1 115.10(10) yes S1 N2 N1 113.00(10) yes S1 N2 H2N 109.0(10) no N1 N2 H2N 118.0(10) no N1 C1 C2 121.3(2) yes N1 C1 C5 128.6(2) yes C2 C1 C5 110.10(10) yes C1 C2 C3 103.20(10) yes C1 C2 H2A 109.0(10) no C1 C2 H2B 111.0(10) no C3 C2 H2A 110.0(10) no C3 C2 H2B 115.0(10) no H2A C2 H2B 105(2) no C2 C3 C4 104.00(10) yes C2 C3 H3A 111.0(10) no C2 C3 H3B 111.0(10) no C4 C3 H3A 115.0(10) no C4 C3 H3B 109.0(10) no H3A C3 H3B 105.0(10) no C3 C4 C5 104.70(10) yes C3 C4 H4A 107.0(10) no C3 C4 H4B 113.0(10) no C5 C4 H4A 109.0(10) no C5 C4 H4B 112.0(10) no H4A C4 H4B 108.0(10) no C1 C5 C4 104.10(10) yes C1 C5 H5A 112.0(10) no C1 C5 H5B 107.0(10) no C4 C5 H5A 116.0(10) no C4 C5 H5B 109.0(10) no H5A C5 H5B 107(2) no S1 C6 C7 118.60(10) yes S1 C6 C11 120.30(10) yes C7 C6 C11 121.1(2) yes C6 C7 C8 118.9(2) yes C6 C7 H7 115.0(10) no C8 C7 H7 125.0(10) no C7 C8 C9 121.3(2) yes C7 C8 H8 118.0(10) no C9 C8 H8 119.0(10) no C8 C9 C10 118.6(2) yes C8 C9 C12 120.0(2) yes C10 C9 C12 121.4(2) yes C9 C10 C11 121.2(2) yes C9 C10 H10 118.0(10) no C11 C10 H10 120.0(10) no C6 C11 C10 118.9(2) yes C6 C11 H11 121.0(10) no C10 C11 H11 119.0(10) no C9 C12 H12A 112.0(10) no C9 C12 H12B 112.0(10) no C9 C12 H12C 115.0(10) no H12A C12 H12B 107(2) no H12A C12 H12C 99(2) no H12B C12 H12C 108(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O1 ? ? 1.4290(10) yes S1 O2 ? ? 1.4460(10) yes S1 N2 ? ? 1.6430(10) yes S1 C6 ? ? 1.755(2) yes N1 N2 ? ? 1.406(2) yes N1 C1 ? ? 1.277(2) yes N2 H2N ? ? .86(2) no C1 C2 ? ? 1.506(2) yes C1 C5 ? ? 1.511(2) yes C2 C3 ? ? 1.530(2) yes C2 H2A ? ? .91(3) no C2 H2B ? ? .92(2) no C3 C4 ? ? 1.525(3) yes C3 H3A ? ? .94(3) no C3 H3B ? ? .95(2) no C4 C5 ? ? 1.538(2) yes C4 H4A ? ? 1.00(2) no C4 H4B ? ? .93(3) no C5 H5A ? ? .97(2) no C5 H5B ? ? .89(3) no C6 C7 ? ? 1.395(2) yes C6 C11 ? ? 1.387(2) yes C7 C8 ? ? 1.383(3) yes C7 H7 ? ? 1.03(3) no C8 C9 ? ? 1.391(3) yes C8 H8 ? ? .95(2) no C9 C10 ? ? 1.398(2) yes C9 C12 ? ? 1.507(2) yes C10 C11 ? ? 1.386(3) yes C10 H10 ? ? .88(3) no C11 H11 ? ? .95(2) no C12 H12A ? ? 1.03(3) no C12 H12B ? ? .95(3) no C12 H12C ? ? .98(3) 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 N2 H2N O2 2_566 0.86(2) 2.14(3) 2.986(2) 167(3) 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 S1 N2 N1 C1 170.90(10) yes O1 S1 N2 N1 58.90(10) yes O1 S1 C6 C7 166.10(10) yes O1 S1 C6 C11 -16.1(2) yes O2 S1 N2 N1 -173.50(10) yes O2 S1 C6 C7 34.40(10) yes O2 S1 C6 C11 -147.70(10) yes N1 N2 S1 C6 -58.30(10) yes N1 C1 C2 C3 -158.10(10) yes N1 C1 C5 C4 -179.5(2) yes N2 S1 C6 C7 -77.10(10) yes N2 S1 C6 C11 100.80(10) yes N2 N1 C1 C2 178.70(10) yes N2 N1 C1 C5 1.9(2) yes C1 C2 C3 C4 -34.4(2) yes C1 C5 C4 C3 -24.9(2) yes C2 C1 C5 C4 3.4(2) yes C2 C3 C4 C5 37.2(2) yes C3 C2 C1 C5 19.2(2) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 277894