#------------------------------------------------------------------------------ #$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $ #$Revision: 176432 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/25/2012573.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_2012573 loop_ _publ_author_name 'Bern\`es, Sylvain' 'Berros, Martha I.' 'Rodr\'iguez de Barbar\'in, Cecilia' 'S\'anchez-Viesca, Francisco' _publ_section_title ; Flat versus twisted rotamers of 2,4-disubstituted thiazoles: the effect of intermolecular hydrogen bonds ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o151 _journal_page_last o153 _journal_paper_doi 10.1107/S0108270102000598 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C11 H11 Cl N2 O2 S' _chemical_formula_moiety 'C11 H11 Cl N2 O2 S' _chemical_formula_sum 'C11 H11 Cl N2 O2 S' _chemical_formula_weight 270.73 _chemical_name_systematic ; 2-amino-4-(2-chloro-4,5-dimethoxyphenyl)-1,3-thiazole ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 107.840(12) _cell_angle_beta 106.719(13) _cell_angle_gamma 97.729(11) _cell_formula_units_Z 2 _cell_length_a 7.2398(11) _cell_length_b 8.6611(12) _cell_length_c 11.0585(18) _cell_measurement_reflns_used 50 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 11.93 _cell_measurement_theta_min 3.47 _cell_volume 613.04(18) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1991)' _computing_data_reduction XSCANS _computing_molecular_graphics SHELXTL _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXTL (Sheldrick, 1995)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .975 _diffrn_measured_fraction_theta_max .975 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .033 _diffrn_reflns_av_sigmaI/netI .063 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 3417 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 2.06 _diffrn_standards_decay_% 4.49 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .472 _exptl_absorpt_correction_T_max .954 _exptl_absorpt_correction_T_min .929 _exptl_absorpt_correction_type \y-scan _exptl_absorpt_process_details '(XSCANS; Siemens, 1991)' _exptl_crystal_colour 'pale pink' _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 280 _exptl_crystal_size_max .5 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .1 _refine_diff_density_max .24 _refine_diff_density_min -.29 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 165 _refine_ls_number_reflns 2756 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all .089 _refine_ls_R_factor_gt .051 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0329P)^2^+0.2732P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .098 _refine_ls_wR_factor_ref .113 _reflns_number_gt 1831 _reflns_number_total 2756 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gd1182.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' 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 ; _cod_original_sg_symbol_Hall -P1 _cod_original_sg_symbol_H-M P-1 _cod_database_code 2012573 _cod_database_fobs_code 2012573 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S1 .09030(13) .06850(10) .37593(8) .0433(2) Uani d . 1 . . S C2 .0576(4) .0218(3) .2053(3) .0352(6) Uani d . 1 . . C N3 .1366(3) .1458(3) .1776(2) .0336(5) Uani d . 1 . . N C4 .2268(4) .2874(3) .2951(3) .0325(6) Uani d . 1 . . C C5 .2158(4) .2687(4) .4089(3) .0401(7) Uani d . 1 . . C H5A .2690 .3528 .4943 .049(9) Uiso calc R 1 . . H N6 -.0370(4) -.1329(3) .1120(3) .0508(7) Uani d . 1 . . N H6A -.0479 -.1543 .0286 .069(12) Uiso calc R 1 . . H H6B -.0862 -.2098 .1360 .077(12) Uiso calc R 1 . . H Cl1 .13559(13) .63211(10) .42450(9) .0564(3) Uani d . 1 . . Cl C1' .3283(4) .4390(3) .2831(3) .0331(6) Uani d . 1 . . C C2' .2978(4) .5965(3) .3347(3) .0365(6) Uani d . 1 . . C C3' .3931(4) .7341(3) .3166(3) .0394(7) Uani d . 1 . . C H3'A .3673 .8381 .3505 .046(9) Uiso calc R 1 . . H C4' .5253(4) .7159(3) .2484(3) .0376(7) Uani d . 1 . . C C5' .5658(4) .5597(3) .1989(3) .0350(6) Uani d . 1 . . C C6' .4656(4) .4241(3) .2146(3) .0346(6) Uani d . 1 . . C H6'A .4894 .3198 .1789 .034(7) Uiso calc R 1 . . H O7' .6256(3) .8414(2) .2239(2) .0489(6) Uani d . 1 . . O C8' .5666(6) .9950(4) .2510(5) .0711(12) Uani d . 1 . . C H8'A .6481 1.0723 .2297 .098(14) Uiso calc R 1 . . H H8'B .5820 1.0411 .3451 .14(2) Uiso calc R 1 . . H H8'C .4298 .9753 .1964 .088(14) Uiso calc R 1 . . H O9' .7022(3) .5550(2) .1350(2) .0446(5) Uani d . 1 . . O C10' .7624(5) .4029(4) .0938(4) .0534(9) Uani d . 1 . . C H10A .8576 .4161 .0505 .083(12) Uiso calc R 1 . . H H10B .6485 .3145 .0314 .061(10) Uiso calc R 1 . . H H10C .8214 .3757 .1718 .053(10) 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 .0524(5) .0434(4) .0397(4) .0067(4) .0222(4) .0189(3) C2 .0363(16) .0331(15) .0387(15) .0054(12) .0181(13) .0129(12) N3 .0379(13) .0297(12) .0339(12) .0041(10) .0157(11) .0113(10) C4 .0306(15) .0316(14) .0335(14) .0068(11) .0129(12) .0082(11) C5 .0428(17) .0386(16) .0322(14) .0010(13) .0107(13) .0100(12) N6 .0698(19) .0330(14) .0437(15) -.0076(13) .0258(14) .0091(11) Cl1 .0604(6) .0458(5) .0697(6) .0141(4) .0424(5) .0110(4) C1' .0346(15) .0289(14) .0291(13) .0034(12) .0075(12) .0067(11) C2' .0326(15) .0347(15) .0389(15) .0054(12) .0155(13) .0071(12) C3' .0371(16) .0286(15) .0476(17) .0079(12) .0143(14) .0077(12) C4' .0333(16) .0288(14) .0462(16) .0023(12) .0103(13) .0134(12) C5' .0318(15) .0364(15) .0350(14) .0051(12) .0109(12) .0127(12) C6' .0393(16) .0265(14) .0374(15) .0073(12) .0145(13) .0101(11) O7' .0447(13) .0332(11) .0757(15) .0087(10) .0257(12) .0250(11) C8' .062(3) .0383(19) .128(4) .0170(18) .042(3) .041(2) O9' .0468(13) .0412(12) .0584(13) .0133(10) .0309(11) .0222(10) C10' .054(2) .053(2) .063(2) .0211(18) .0336(19) .0181(18) 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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 0 -4 2 -2 0 2 3 -2 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 C5 S1 C2 88.73(13) n N3 C2 N6 123.9(3) n N3 C2 S1 114.6(2) n N6 C2 S1 121.4(2) n C2 N3 C4 110.3(2) n C5 C4 N3 115.3(2) n C5 C4 C1' 126.9(2) n N3 C4 C1' 117.7(2) n C4 C5 S1 111.0(2) n C4 C5 H5A 124.5 n S1 C5 H5A 124.5 n C2 N6 H6A 120.0 n C2 N6 H6B 120.0 n H6A N6 H6B 120.0 n C2' C1' C6' 117.0(2) n C2' C1' C4 124.4(3) n C6' C1' C4 118.6(2) n C1' C2' C3' 121.9(3) n C1' C2' Cl1 121.5(2) n C3' C2' Cl1 116.6(2) n C4' C3' C2' 119.9(3) n C4' C3' H3'A 120.1 n C2' C3' H3'A 120.1 n O7' C4' C3' 124.8(3) n O7' C4' C5' 115.2(3) n C3' C4' C5' 120.0(3) n O9' C5' C6' 125.2(3) n O9' C5' C4' 115.6(2) n C6' C5' C4' 119.2(3) n C5' C6' C1' 122.0(3) n C5' C6' H6'A 119.0 n C1' C6' H6'A 119.0 n C4' O7' C8' 117.7(3) n O7' C8' H8'A 109.5 n O7' C8' H8'B 109.5 n H8'A C8' H8'B 109.5 n O7' C8' H8'C 109.5 n H8'A C8' H8'C 109.5 n H8'B C8' H8'C 109.5 n C5' O9' C10' 117.8(2) n O9' C10' H10A 109.5 n O9' C10' H10B 109.5 n H10A C10' H10B 109.5 n O9' C10' H10C 109.5 n H10A C10' H10C 109.5 n H10B C10' H10C 109.5 n 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 C5 . 1.722(3) n S1 C2 . 1.740(3) n C2 N3 . 1.309(3) n C2 N6 . 1.352(3) n N3 C4 . 1.393(3) n C4 C5 . 1.339(4) n C4 C1' . 1.478(4) n C5 H5A . .9300 n N6 H6A . .8600 n N6 H6B . .8600 n Cl1 C2' . 1.744(3) n C1' C2' . 1.382(4) n C1' C6' . 1.410(4) n C2' C3' . 1.394(4) n C3' C4' . 1.376(4) n C3' H3'A . .9300 n C4' O7' . 1.365(3) n C4' C5' . 1.400(4) n C5' O9' . 1.368(3) n C5' C6' . 1.379(4) n C6' H6'A . .9300 n O7' C8' . 1.423(4) n C8' H8'A . .9600 n C8' H8'B . .9600 n C8' H8'C . .9600 n O9' C10' . 1.426(4) n C10' H10A . .9600 n C10' H10B . .9600 n C10' H10C . .9600 n 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 N6 H6B O7' 1_445 .86 2.58 3.051(3) 116 y N6 H6B O9' 1_445 .86 2.37 3.204(3) 162 y N6 H6A N3 2_555 .86 2.21 3.035(3) 161 y C5 H5A Cl1 1_555 .93 2.95 3.239(3) 99 n C6' H6'A N3 1_555 .93 2.78 2.990(3) 94 n 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 S1 C2 N3 .7(2) n C5 S1 C2 N6 178.7(3) n N6 C2 N3 C4 -178.6(3) n S1 C2 N3 C4 -.7(3) n C2 N3 C4 C5 .3(4) n C2 N3 C4 C1' 178.6(2) n N3 C4 C5 S1 .3(3) n C1' C4 C5 S1 -177.9(2) n C2 S1 C5 C4 -.5(2) n C5 C4 C1' C2' -52.2(4) n N3 C4 C1' C2' 129.7(3) n C5 C4 C1' C6' 127.9(3) n N3 C4 C1' C6' -50.2(4) n C6' C1' C2' C3' 2.0(4) n C4 C1' C2' C3' -177.9(3) n C6' C1' C2' Cl1 -178.7(2) n C4 C1' C2' Cl1 1.4(4) n C1' C2' C3' C4' -1.6(4) n Cl1 C2' C3' C4' 179.1(2) n C2' C3' C4' O7' 179.5(3) n C2' C3' C4' C5' -.8(4) n O7' C4' C5' O9' 1.0(4) n C3' C4' C5' O9' -178.7(2) n O7' C4' C5' C6' -177.6(2) n C3' C4' C5' C6' 2.7(4) n O9' C5' C6' C1' 179.3(3) n C4' C5' C6' C1' -2.2(4) n C2' C1' C6' C5' -.1(4) n C4 C1' C6' C5' 179.8(3) n C3' C4' O7' C8' -10.6(5) n C5' C4' O7' C8' 169.6(3) n C6' C5' O9' C10' -7.1(4) n C4' C5' O9' C10' 174.4(3) n