#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2200071.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_2200071 loop_ _publ_author_name 'Lynch, Daniel E.' 'McClenaghan, Ian' _publ_section_title ; 2-Amino-5-(4-methoxybenzyl)-4-methyl-1,3-thiazolium chloride ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o24 _journal_page_last o25 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C12 H15 Cl N2 O S' _chemical_formula_moiety 'C12 H15 Cl N2 O S' _chemical_formula_sum 'C12 H15 Cl N2 O S' _chemical_formula_weight 270.77 _chemical_melting_point 491(2) _chemical_name_systematic ; 2-Amino-5-(4-methoxybenzyl)-4-methyl-1,3-thiazolium chloride ; _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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 100.47(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.5746(15) _cell_length_b 11.878(2) _cell_length_c 14.519(3) _cell_measurement_reflns_used 10172 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 1.00 _cell_volume 1284.5(4) _computing_cell_refinement 'DENZO and COLLECT' _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZOand COLLECT ' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 9.091 _diffrn_measured_fraction_theta_full .950 _diffrn_measured_fraction_theta_max .950 _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .073 _diffrn_reflns_av_sigmaI/netI .0812 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 6971 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 2.23 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .445 _exptl_absorpt_correction_T_max .974 _exptl_absorpt_correction_T_min .916 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 568 _exptl_crystal_size_max .20 _exptl_crystal_size_mid .08 _exptl_crystal_size_min .06 _refine_diff_density_max .401 _refine_diff_density_min -.545 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 168 _refine_ls_number_reflns 2796 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.009 _refine_ls_R_factor_all .071 _refine_ls_R_factor_gt .050 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0691P)^2^+0.1620P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .136 _reflns_number_gt 2125 _reflns_number_total 2796 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ob6000.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '489 - 493 K' was changed to '491(2)' - the average value was taken and precision was estimated. '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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_cell_volume 1284.6(4) _cod_database_code 2200071 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_type_symbol Cl1 .20074(8) .56421(5) .90658(4) .0323(2) Uani d . 1 Cl S1 .02394(8) .15154(5) .75439(4) .0270(2) Uani d . 1 S C2 -.1444(3) .09324(19) .67277(15) .0240(5) Uani d . 1 C N21 -.1131(3) .02602(18) .60550(15) .0293(5) Uani d . 1 N H21 -.198(4) .014(2) .5597(18) .033(7) Uiso d . 1 H H22 .003(4) .026(2) .5980(19) .044(8) Uiso d . 1 H N3 -.3039(3) .12351(18) .68956(14) .0261(5) Uani d . 1 N H3 -.402(4) .098(3) .660(2) .040(8) Uiso d . 1 H C4 -.2999(3) .1947(2) .76714(16) .0265(5) Uani d . 1 C C5 -.1334(3) .2181(2) .81063(16) .0267(5) Uani d . 1 C C6 -.0676(3) .2906(2) .89428(16) .0302(6) Uani d . 1 C H61 -.1705 .3123 .9238 .038 Uiso calc R 1 H H62 -.0148 .3604 .8736 .038 Uiso calc R 1 H C7 .0710(3) .2316(2) .96556(15) .0272(5) Uani d . 1 C C8 .2520(3) .2491(2) .96837(16) .0302(6) Uani d . 1 C H8 .2886 .3012 .9259 .038 Uiso calc R 1 H C9 .3825(3) .1929(2) 1.03128(16) .0315(6) Uani d . 1 C H9 .5063 .2064 1.0317 .039 Uiso calc R 1 H C10 .3299(3) .1171(2) 1.09339(17) .0309(6) Uani d . 1 C O1 .4440(3) .05801(15) 1.16006(13) .0414(5) Uani d . 1 O C11 .1490(4) .0980(2) 1.09124(18) .0364(6) Uani d . 1 C H11 .1125 .0459 1.1337 .045 Uiso calc R 1 H C12 .0218(4) .1539(2) 1.02825(18) .0346(6) Uani d . 1 C H12 -.1018 .1393 1.0274 .043 Uiso calc R 1 H C13 -.4737(3) .2328(2) .79016(18) .0364(6) Uani d . 1 C H131 -.5296 .1706 .8186 .046 Uiso calc R 1 H H132 -.5536 .2571 .7327 .046 Uiso calc R 1 H H133 -.4525 .2959 .8343 .046 Uiso calc R 1 H C14 .6315(4) .0671(3) 1.1596(2) .0446(7) Uani d . 1 C H141 .6593 .0294 1.1039 .056 Uiso calc R 1 H H142 .6992 .0314 1.2159 .056 Uiso calc R 1 H H143 .6649 .1467 1.1585 .056 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 Cl1 .0237(3) .0452(4) .0281(3) .0040(3) .0048(2) .0053(3) S1 .0204(3) .0343(4) .0261(3) .0002(2) .0039(2) -.0042(2) C2 .0217(12) .0260(12) .0248(12) -.0010(10) .0056(9) .0029(9) N21 .0242(12) .0387(13) .0256(11) -.0035(10) .0060(9) -.0064(9) N3 .0194(10) .0348(11) .0239(10) .0005(9) .0037(8) -.0014(9) C4 .0258(12) .0302(13) .0243(12) -.0013(10) .0067(9) -.0002(10) C5 .0256(12) .0292(13) .0265(12) .0007(10) .0074(9) .0009(10) C6 .0281(13) .0342(14) .0281(12) .0012(11) .0044(10) -.0051(10) C7 .0286(13) .0302(13) .0233(12) .0003(10) .0059(9) -.0059(10) C8 .0304(13) .0353(14) .0257(12) -.0027(11) .0073(10) -.0011(10) C9 .0253(13) .0397(14) .0307(13) -.0018(11) .0080(10) -.0036(11) C10 .0334(14) .0315(13) .0267(12) -.0003(11) .0027(10) -.0035(10) O1 .0364(11) .0451(11) .0412(11) .0050(9) .0029(8) .0116(9) C11 .0378(15) .0368(15) .0353(14) -.0065(12) .0089(12) .0048(12) C12 .0284(14) .0414(16) .0344(14) -.0052(12) .0069(11) -.0019(11) C13 .0257(13) .0481(16) .0373(14) .0004(12) .0106(11) -.0074(12) C14 .0371(16) .0478(18) .0460(16) .0068(13) -.0002(13) .0042(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .1484 .1585 '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 C2 S1 C5 91.19(11) N21 C2 N3 126.5(2) N21 C2 S1 122.97(19) N3 C2 S1 110.52(17) C2 N21 H21 118.4(18) C2 N21 H22 113.4(18) H21 N21 H22 121(3) C2 N3 C4 115.1(2) C2 N3 H3 124(2) C4 N3 H3 120(2) C5 C4 N3 112.7(2) C5 C4 C13 129.1(2) N3 C4 C13 118.2(2) C4 C5 C6 130.6(2) C4 C5 S1 110.50(18) C6 C5 S1 118.88(17) C5 C6 C7 112.1(2) C5 C6 H61 109.2 C7 C6 H61 109.2 C5 C6 H62 109.2 C7 C6 H62 109.2 H61 C6 H62 107.9 C8 C7 C12 117.5(2) C8 C7 C6 121.0(2) C12 C7 C6 121.4(2) C7 C8 C9 122.1(2) C7 C8 H8 118.9 C9 C8 H8 118.9 C10 C9 C8 119.1(2) C10 C9 H9 120.4 C8 C9 H9 120.4 O1 C10 C11 115.3(2) O1 C10 C9 125.1(2) C11 C10 C9 119.5(2) C10 O1 C14 117.3(2) C12 C11 C10 120.6(2) C12 C11 H11 119.7 C10 C11 H11 119.7 C11 C12 C7 121.1(2) C11 C12 H12 119.5 C7 C12 H12 119.5 C4 C13 H131 109.5 C4 C13 H132 109.5 H131 C13 H132 109.5 C4 C13 H133 109.5 H131 C13 H133 109.5 H132 C13 H133 109.5 O1 C14 H141 109.5 O1 C14 H142 109.5 H141 C14 H142 109.5 O1 C14 H143 109.5 H141 C14 H143 109.5 H142 C14 H143 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C2 1.721(2) S1 C5 1.751(2) C2 N21 1.316(3) C2 N3 1.324(3) N21 H21 .85(3) N21 H22 .91(3) N3 C4 1.404(3) N3 H3 .84(3) C4 C5 1.333(3) C4 C13 1.487(3) C5 C6 1.499(3) C6 C7 1.507(3) C6 H61 .9900 C6 H62 .9900 C7 C8 1.380(3) C7 C12 1.394(3) C8 C9 1.388(3) C8 H8 .9500 C9 C10 1.383(4) C9 H9 .9500 C10 O1 1.368(3) C10 C11 1.384(4) O1 C14 1.426(3) C11 C12 1.373(4) C11 H11 .9500 C12 H12 .9500 C13 H131 .9800 C13 H132 .9800 C13 H133 .9800 C14 H141 .9800 C14 H142 .9800 C14 H143 .9800 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 N3 H3 Cl1 2_446 .84(3) 2.33(3) 3.155(2) 167(3) yes N21 H21 Cl1 4_565 .85(3) 2.40(3) 3.162(2) 150(2) yes N21 H22 Cl1 2_546 .91(3) 2.30(3) 3.193(2) 168(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 C5 S1 C2 N21 -178.6(2) C5 S1 C2 N3 -.21(18) N21 C2 N3 C4 178.8(2) S1 C2 N3 C4 .5(3) C2 N3 C4 C5 -.5(3) C2 N3 C4 C13 179.7(2) N3 C4 C5 C6 179.1(2) C13 C4 C5 C6 -1.2(5) N3 C4 C5 S1 .3(3) C13 C4 C5 S1 -179.9(2) C2 S1 C5 C4 -.09(19) C2 S1 C5 C6 -179.0(2) C4 C5 C6 C7 131.3(3) S1 C5 C6 C7 -50.1(3) C5 C6 C7 C8 97.2(3) C5 C6 C7 C12 -80.0(3) C12 C7 C8 C9 -.5(4) C6 C7 C8 C9 -177.8(2) C7 C8 C9 C10 -.1(4) C8 C9 C10 O1 -178.6(2) C8 C9 C10 C11 .5(4) C11 C10 O1 C14 174.5(2) C9 C10 O1 C14 -6.4(4) O1 C10 C11 C12 179.0(2) C9 C10 C11 C12 -.1(4) C10 C11 C12 C7 -.5(4) C8 C7 C12 C11 .9(4) C6 C7 C12 C11 178.1(2)