#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/51/2205195.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_2205195 loop_ _publ_author_name 'Alvarez, Ricardo G.' 'Kennedy, Alan R.' 'Khalaf, Abedawn I.' 'Suckling, Colin J.' 'Waigh, Roger D.' _publ_section_title ; 2-(1-Piperidinyl)-1,3-benzothiazole ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o569 _journal_page_last o570 _journal_paper_doi 10.1107/S160053680500320X _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C12 H14 N2 S' _chemical_formula_moiety 'C12 H14 N2 S' _chemical_formula_sum 'C12 H14 N2 S' _chemical_formula_weight 218.31 _chemical_name_systematic ; 2-(1-Piperidinyl)-1,3-benzothiazole ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 15.3509(6) _cell_length_b 11.6315(4) _cell_length_c 5.9802(2) _cell_measurement_reflns_used 1447 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 1.00 _cell_volume 1067.79(7) _computing_cell_refinement 'DENZO and COLLECT' _computing_data_collection ; DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1988) ; _computing_data_reduction DENZO _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 123(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \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 0.039 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 11594 _diffrn_reflns_theta_full 27.54 _diffrn_reflns_theta_max 27.54 _diffrn_reflns_theta_min 2.20 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'cut needle' _exptl_crystal_F_000 464 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.172 _refine_diff_density_min -0.186 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 1341 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.070 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0284 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0312P)^2^+0.2439P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.0647 _reflns_number_gt 1208 _reflns_number_total 1341 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ac6153.cif _cod_data_source_block I _cod_database_code 2205195 _cod_database_fobs_code 2205195 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' 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_type_symbol S1 0.39332(3) 0.01583(4) 0.40617(11) 0.01893(14) Uani d . 1 S N1 0.36236(11) 0.11262(14) 0.0187(3) 0.0175(4) Uani d . 1 N N2 0.47092(11) 0.20489(14) 0.2309(3) 0.0164(4) Uani d . 1 N C1 0.31266(14) -0.04382(17) 0.2381(4) 0.0187(5) Uani d . 1 C C2 0.30605(13) 0.01905(17) 0.0379(4) 0.0169(4) Uani d . 1 C C3 0.24705(13) -0.01615(17) -0.1252(4) 0.0210(5) Uani d . 1 C H3 0.2406 0.0264 -0.2597 0.025 Uiso calc R 1 H C4 0.19756(13) -0.11476(17) -0.0881(5) 0.0247(5) Uani d . 1 C H4 0.1586 -0.1407 -0.2008 0.030 Uiso calc R 1 H C5 0.20427(15) -0.17589(18) 0.1112(4) 0.0248(5) Uani d . 1 C H5 0.1691 -0.2421 0.1337 0.030 Uiso calc R 1 H C6 0.26155(14) -0.14147(18) 0.2774(4) 0.0217(5) Uani d . 1 C H6 0.2660 -0.1829 0.4138 0.026 Uiso calc R 1 H C7 0.41108(13) 0.12077(16) 0.1966(4) 0.0160(4) Uani d . 1 C C8 0.49943(14) 0.27153(18) 0.0350(4) 0.0197(5) Uani d . 1 C H8A 0.4498 0.2817 -0.0688 0.024 Uiso calc R 1 H H8B 0.5457 0.2287 -0.0449 0.024 Uiso calc R 1 H C9 0.53401(15) 0.38887(17) 0.1046(4) 0.0205(5) Uani d . 1 C H9A 0.5589 0.4281 -0.0276 0.025 Uiso calc R 1 H H9B 0.4852 0.4363 0.1612 0.025 Uiso calc R 1 H C10 0.60356(14) 0.37909(19) 0.2851(4) 0.0234(5) Uani d . 1 C H10A 0.6553 0.3391 0.2243 0.028 Uiso calc R 1 H H10B 0.6216 0.4568 0.3341 0.028 Uiso calc R 1 H C11 0.56756(14) 0.31233(18) 0.4830(4) 0.0212(5) Uani d . 1 C H11A 0.5188 0.3557 0.5507 0.025 Uiso calc R 1 H H11B 0.6136 0.3034 0.5976 0.025 Uiso calc R 1 H C12 0.53554(13) 0.19401(14) 0.4101(4) 0.0190(4) Uani d . 1 C H12A 0.5854 0.1476 0.3568 0.023 Uiso calc R 1 H H12B 0.5092 0.1538 0.5394 0.023 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 S1 0.0234(3) 0.0157(2) 0.0176(2) -0.00208(19) -0.0005(3) 0.0037(3) N1 0.0180(8) 0.0155(8) 0.0189(9) 0.0001(7) 0.0009(8) 0.0004(8) N2 0.0195(9) 0.0149(8) 0.0147(9) -0.0022(7) -0.0014(8) 0.0031(7) C1 0.0172(10) 0.0185(10) 0.0203(11) 0.0020(8) 0.0018(9) -0.0023(9) C2 0.0161(10) 0.0166(9) 0.0182(11) 0.0022(8) 0.0019(9) -0.0018(9) C3 0.0177(10) 0.0238(10) 0.0214(13) 0.0030(8) 0.0008(10) -0.0036(10) C4 0.0177(10) 0.0254(10) 0.0311(12) -0.0013(8) 0.0012(13) -0.0076(15) C5 0.0201(12) 0.0188(10) 0.0355(14) -0.0034(9) 0.0057(11) -0.0045(10) C6 0.0227(11) 0.0173(10) 0.0253(13) 0.0013(9) 0.0059(10) 0.0015(9) C7 0.0209(10) 0.0118(9) 0.0153(10) 0.0028(8) 0.0027(9) -0.0001(9) C8 0.0241(11) 0.0173(10) 0.0178(11) -0.0012(9) 0.0020(10) 0.0042(9) C9 0.0255(12) 0.0172(10) 0.0186(11) -0.0031(9) 0.0014(9) 0.0021(10) C10 0.0237(12) 0.0208(11) 0.0256(13) -0.0075(9) 0.0004(10) 0.0006(10) C11 0.0230(12) 0.0214(11) 0.0192(11) -0.0038(9) -0.0024(10) 0.0005(9) C12 0.0221(10) 0.0169(9) 0.0179(10) 0.0004(7) -0.0036(11) 0.0018(12) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' 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' 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 S1 C7 88.60(10) y C7 N1 C2 110.18(18) y C7 N2 C12 120.40(17) ? C7 N2 C8 117.44(18) ? C12 N2 C8 115.24(16) ? C6 C1 C2 121.6(2) ? C6 C1 S1 128.72(18) y C2 C1 S1 109.62(15) y C3 C2 N1 125.1(2) y C3 C2 C1 119.35(19) ? N1 C2 C1 115.55(19) y C2 C3 C4 119.0(2) ? C2 C3 H3 120.5 ? C4 C3 H3 120.5 ? C5 C4 C3 121.1(2) ? C5 C4 H4 119.5 ? C3 C4 H4 119.5 ? C6 C5 C4 120.9(2) ? C6 C5 H5 119.5 ? C4 C5 H5 119.5 ? C5 C6 C1 118.0(2) ? C5 C6 H6 121.0 ? C1 C6 H6 121.0 ? N1 C7 N2 124.30(19) y N1 C7 S1 116.05(15) y N2 C7 S1 119.62(16) y N2 C8 C9 110.99(18) ? N2 C8 H8A 109.4 ? C9 C8 H8A 109.4 ? N2 C8 H8B 109.4 ? C9 C8 H8B 109.4 ? H8A C8 H8B 108.0 ? C10 C9 C8 111.80(18) ? C10 C9 H9A 109.3 ? C8 C9 H9A 109.3 ? C10 C9 H9B 109.3 ? C8 C9 H9B 109.3 ? H9A C9 H9B 107.9 ? C11 C10 C9 109.59(17) ? C11 C10 H10A 109.8 ? C9 C10 H10A 109.8 ? C11 C10 H10B 109.8 ? C9 C10 H10B 109.8 ? H10A C10 H10B 108.2 ? C10 C11 C12 110.86(19) ? C10 C11 H11A 109.5 ? C12 C11 H11A 109.5 ? C10 C11 H11B 109.5 ? C12 C11 H11B 109.5 ? H11A C11 H11B 108.1 ? N2 C12 C11 110.43(16) ? N2 C12 H12A 109.6 ? C11 C12 H12A 109.6 ? N2 C12 H12B 109.6 ? C11 C12 H12B 109.6 ? H12A C12 H12B 108.1 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C1 1.739(2) y S1 C7 1.771(2) y N1 C7 1.304(3) y N1 C2 1.395(3) y N2 C7 1.358(3) y N2 C12 1.466(3) y N2 C8 1.471(3) y C1 C6 1.400(3) ? C1 C2 1.406(3) ? C2 C3 1.393(3) ? C3 C4 1.394(3) ? C3 H3 0.9500 ? C4 C5 1.392(4) ? C4 H4 0.9500 ? C5 C6 1.386(3) ? C5 H5 0.9500 ? C6 H6 0.9500 ? C8 C9 1.523(3) ? C8 H8A 0.9900 ? C8 H8B 0.9900 ? C9 C10 1.522(3) ? C9 H9A 0.9900 ? C9 H9B 0.9900 ? C10 C11 1.519(3) ? C10 H10A 0.9900 ? C10 H10B 0.9900 ? C11 C12 1.525(3) ? C11 H11A 0.9900 ? C11 H11B 0.9900 ? C12 H12A 0.9900 ? C12 H12B 0.9900 ? 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 C7 S1 C1 C6 178.0(2) C7 S1 C1 C2 0.49(15) C7 N1 C2 C3 -178.02(19) C7 N1 C2 C1 0.6(2) C6 C1 C2 C3 0.3(3) S1 C1 C2 C3 177.97(16) C6 C1 C2 N1 -178.43(19) S1 C1 C2 N1 -0.7(2) N1 C2 C3 C4 176.92(19) C1 C2 C3 C4 -1.6(3) C2 C3 C4 C5 2.1(3) C3 C4 C5 C6 -1.1(3) C4 C5 C6 C1 -0.3(3) C2 C1 C6 C5 0.7(3) S1 C1 C6 C5 -176.51(17) C2 N1 C7 N2 -178.20(19) C2 N1 C7 S1 -0.2(2) C12 N2 C7 N1 -166.66(19) C8 N2 C7 N1 -17.2(3) C12 N2 C7 S1 15.4(3) C8 N2 C7 S1 164.88(14) C1 S1 C7 N1 -0.19(17) C1 S1 C7 N2 177.93(17) C7 N2 C8 C9 156.20(18) C12 N2 C8 C9 -52.7(2) N2 C8 C9 C10 52.5(2) C8 C9 C10 C11 -55.4(2) C9 C10 C11 C12 56.9(2) C7 N2 C12 C11 -155.42(19) C8 N2 C12 C11 54.5(2) C10 C11 C12 N2 -55.8(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 68591 2 PubChem 76105