#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/16/2011648.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_2011648 loop_ _publ_author_name 'Lynch, Daniel E.' 'McClenaghan, Ian' _publ_section_title ; Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e586 _journal_page_last e586 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C12 H12 N2 O2 S' _chemical_formula_weight 248.30 _chemical_melting_point 444.5(15) _chemical_name_systematic ; Ethyl-2-amino-4-phenyl-1,3-thiazole-5-carboxylate ; _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 SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 97.2427(15) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.3124(2) _cell_length_b 8.6888(3) _cell_length_c 13.3156(3) _cell_measurement_reflns_used 3395 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _cell_volume 1183.59(5) _computing_cell_refinement 'DENZO and COLLECT' _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO and 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 .964 _diffrn_measured_fraction_theta_max .964 _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area-detector' _diffrn_measurement_method '\f and \w scans' _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 .0417 _diffrn_reflns_av_sigmaI/netI .0427 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 7275 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 3.08 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .264 _exptl_absorpt_correction_T_max .961 _exptl_absorpt_correction_T_min .949 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 520 _exptl_crystal_size_max .20 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .15 _refine_diff_density_max .230 _refine_diff_density_min -.337 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 2633 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.013 _refine_ls_R_factor_all .043 _refine_ls_R_factor_gt .037 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0579P)^2^+0.3670P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .102 _reflns_number_gt 2361 _reflns_number_total 2633 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file qa0444.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 '443-446 K' was changed to '444.5(15)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '443-446 K' was changed to '444.5(15)' - 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_database_code 2011648 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 S1 .24807(3) .18693(4) .84455(2) .02280(13) Uani d . 1 . . S C2 .13295(13) .09723(16) .90882(10) .0218(3) Uani d . 1 . . C N21 .07800(13) -.03581(15) .87752(10) .0282(3) Uani d . 1 . . N H21 .021(2) -.078(3) .9142(15) .045(5) Uiso d . 1 . . H H22 .0804(18) -.064(2) .8175(15) .036(5) Uiso d . 1 . . H N3 .11005(11) .16755(13) .99316(8) .0211(3) Uani d . 1 . . N C4 .26216(13) .33128(15) .93581(10) .0203(3) Uani d . 1 . . C C41 .33249(12) .46830(16) .91062(9) .0212(3) Uani d . 1 . . C O40 .39483(10) .47402(13) .83881(7) .0295(3) Uani d . 1 . . O O41 .31899(10) .58702(12) .97100(8) .0286(2) Uani d . 1 . . O C42 .38210(15) .73012(18) .94991(11) .0290(3) Uani d . 1 . . C H421 .3399 .7754 .8858 .036 Uiso calc R 1 . . H H422 .4757 .7126 .9440 .036 Uiso calc R 1 . . H C43 .36748(19) .83485(19) 1.03686(13) .0378(4) Uani d . 1 . . C H431 .2748 .8440 1.0453 .047 Uiso calc R 1 . . H H432 .4024 .9367 1.0235 .047 Uiso calc R 1 . . H H433 .4157 .7925 1.0988 .047 Uiso calc R 1 . . H C5 .18140(12) .30015(15) 1.00820(9) .0187(3) Uani d . 1 . . C C51 .16088(13) .39469(15) 1.09692(9) .0195(3) Uani d . 1 . . C C52 .26394(13) .46232(17) 1.15876(9) .0239(3) Uani d . 1 . . C H52 .3512 .4457 1.1454 .030 Uiso calc R 1 . . H C53 .24025(15) .55370(19) 1.23964(11) .0303(3) Uani d . 1 . . C H53 .3111 .6010 1.2808 .038 Uiso calc R 1 . . H C54 .11377(15) .57624(19) 1.26067(11) .0309(3) Uani d . 1 . . C H54 .0976 .6401 1.3157 .039 Uiso calc R 1 . . H C55 .01093(14) .50597(18) 1.20168(10) .0267(3) Uani d . 1 . . C H55 -.0758 .5197 1.2171 .033 Uiso calc R 1 . . H C56 .03374(13) .41541(16) 1.11991(10) .0225(3) Uani d . 1 . . C H56 -.0374 .3674 1.0795 .028 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 .0254(2) .0238(2) .02088(19) -.00260(12) .00964(13) -.00198(12) C2 .0227(7) .0233(7) .0202(6) -.0009(5) .0056(5) .0008(5) N21 .0367(7) .0279(7) .0222(6) -.0103(5) .0119(5) -.0061(5) N3 .0230(6) .0223(6) .0190(5) -.0028(4) .0061(4) -.0007(4) C4 .0211(7) .0221(7) .0183(6) -.0008(5) .0047(5) -.0007(5) C41 .0187(6) .0251(7) .0199(6) -.0013(5) .0033(5) .0014(5) O40 .0345(6) .0313(6) .0256(5) -.0049(4) .0149(4) .0012(4) O41 .0357(6) .0228(5) .0300(5) -.0098(4) .0149(4) -.0028(4) C42 .0337(8) .0230(7) .0309(7) -.0083(6) .0068(6) .0033(6) C43 .0485(10) .0276(8) .0373(9) -.0093(7) .0050(7) -.0040(7) C5 .0177(6) .0208(7) .0179(6) -.0002(5) .0030(5) .0018(5) C51 .0228(7) .0188(6) .0175(6) -.0004(5) .0055(5) .0027(5) C52 .0221(7) .0284(8) .0215(6) -.0014(5) .0045(5) -.0007(5) C53 .0322(8) .0342(8) .0243(7) -.0038(6) .0030(5) -.0064(6) C54 .0402(8) .0308(8) .0231(7) .0022(6) .0094(6) -.0048(6) C55 .0264(7) .0297(8) .0258(7) .0048(6) .0108(5) .0019(6) C56 .0228(7) .0234(7) .0216(6) .0000(5) .0045(5) .0026(5) 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 S1 C2 . 1.7336(14) ? S1 C4 . 1.7396(13) ? C2 N3 . 1.3256(17) ? C2 N21 . 1.3310(19) ? N21 H21 . .89(2) ? N21 H22 . .838(19) ? N3 C5 . 1.3681(18) ? C4 C5 . 1.3779(18) ? C4 C41 . 1.4550(19) ? C41 O40 . 1.2188(16) ? C41 O41 . 1.3259(17) ? O41 C42 . 1.4472(17) ? C42 C43 . 1.495(2) ? C42 H421 . .9900 ? C42 H422 . .9900 ? C43 H431 . .9800 ? C43 H432 . .9800 ? C43 H433 . .9800 ? C5 C51 . 1.4758(18) ? C51 C52 . 1.3900(18) ? C51 C56 . 1.3952(19) ? C52 C53 . 1.384(2) ? C52 H52 . .9500 ? C53 C54 . 1.382(2) ? C53 H53 . .9500 ? C54 C55 . 1.380(2) ? C54 H54 . .9500 ? C55 C56 . 1.387(2) ? C55 H55 . .9500 ? C56 H56 . .9500 ? 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 S1 C4 88.94(6) N3 C2 N21 123.46(12) N3 C2 S1 114.65(10) N21 C2 S1 121.79(10) C2 N21 H21 118.3(14) C2 N21 H22 119.1(13) H21 N21 H22 120.2(19) C2 N3 C5 111.24(11) C5 C4 C41 133.21(13) C5 C4 S1 110.03(10) C41 C4 S1 115.41(9) O40 C41 O41 123.37(13) O40 C41 C4 122.80(13) O41 C41 C4 113.79(11) C41 O41 C42 117.82(11) O41 C42 C43 106.32(12) O41 C42 H421 110.5 C43 C42 H421 110.5 O41 C42 H422 110.5 C43 C42 H422 110.5 H421 C42 H422 108.7 C42 C43 H431 109.5 C42 C43 H432 109.5 H431 C43 H432 109.5 C42 C43 H433 109.5 H431 C43 H433 109.5 H432 C43 H433 109.5 N3 C5 C4 115.10(12) N3 C5 C51 117.21(11) C4 C5 C51 127.66(12) C52 C51 C56 119.01(12) C52 C51 C5 122.24(12) C56 C51 C5 118.75(12) C53 C52 C51 120.44(13) C53 C52 H52 119.8 C51 C52 H52 119.8 C54 C53 C52 120.17(14) C54 C53 H53 119.9 C52 C53 H53 119.9 C55 C54 C53 119.94(13) C55 C54 H54 120.0 C53 C54 H54 120.0 C54 C55 C56 120.23(13) C54 C55 H55 119.9 C56 C55 H55 119.9 C55 C56 C51 120.16(13) C55 C56 H56 119.9 C51 C56 H56 119.9 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 N21 H21 N3 3_557 .89(2) 2.09(2) 2.9797(17) 176.4(19) yes N21 H22 O40 2_546 .838(19) 2.15(2) 2.9302(16) 154.0(18) 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 C4 S1 C2 N3 -1.73(11) C4 S1 C2 N21 -178.45(12) N21 C2 N3 C5 178.63(13) S1 C2 N3 C5 1.98(15) C2 S1 C4 C5 .98(10) C2 S1 C4 C41 -167.54(11) C5 C4 C41 O40 -176.12(14) S1 C4 C41 O40 -10.98(18) C5 C4 C41 O41 1.9(2) S1 C4 C41 O41 167.04(9) O40 C41 O41 C42 -.1(2) C4 C41 O41 C42 -178.10(12) C41 O41 C42 C43 -171.97(13) C2 N3 C5 C4 -1.19(17) C2 N3 C5 C51 177.10(11) C41 C4 C5 N3 165.62(14) S1 C4 C5 N3 -.11(15) C41 C4 C5 C51 -12.5(2) S1 C4 C5 C51 -178.18(11) N3 C5 C51 C52 137.62(13) C4 C5 C51 C52 -44.3(2) N3 C5 C51 C56 -41.71(17) C4 C5 C51 C56 136.33(14) C56 C51 C52 C53 -2.5(2) C5 C51 C52 C53 178.20(13) C51 C52 C53 C54 1.2(2) C52 C53 C54 C55 .8(2) C53 C54 C55 C56 -1.4(2) C54 C55 C56 C51 .1(2) C52 C51 C56 C55 1.8(2) C5 C51 C56 C55 -178.80(12)