#------------------------------------------------------------------------------ #$Date: 2016-03-26 16:33:12 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180342 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/11/7201153.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7201153 loop_ _publ_author_name 'Nauha, Elisa' 'Saxell, Heidi' 'Nissinen, Maija' 'Kolehmainen, Erkki' 'Sch\"afer, Ansgar' 'Schlecker, Rainer' _publ_section_title ; Polymorphism and versatile solvate formation of thiophanate-methyl ; _journal_issue 11 _journal_name_full CrystEngComm _journal_page_first 2536 _journal_paper_doi 10.1039/b905511h _journal_volume 11 _journal_year 2009 _chemical_formula_moiety 'C12 H14 N4 O4 S2' _chemical_formula_sum 'C12 H14 N4 O4 S2' _chemical_formula_weight 342.39 _chemical_name_common thiophanate-methyl _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 132.593(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.7149(5) _cell_length_b 11.8405(5) _cell_length_c 15.6861(6) _cell_measurement_temperature 103(2) _cell_volume 1465.07(12) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 103(2) _diffrn_measured_fraction_theta_full 0.952 _diffrn_measured_fraction_theta_max 0.952 _diffrn_measurement_device_type 'Bruker AXS CCD Detector' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0572 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 9506 _diffrn_reflns_theta_full 54.86 _diffrn_reflns_theta_max 54.86 _diffrn_reflns_theta_min 5.35 _exptl_absorpt_coefficient_mu 3.532 _exptl_absorpt_correction_T_max 0.5385 _exptl_absorpt_correction_T_min 0.5385 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'R.H. Blessing, Acta Cryst. A 1995, 51, 33' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 712 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.375 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.078 _refine_ls_extinction_coef 0.0067(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.187 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 214 _refine_ls_number_reflns 1744 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.186 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0402 _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^)+(0.0483P)^2^+3.0780P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1128 _refine_ls_wR_factor_ref 0.1199 _reflns_number_gt 1620 _reflns_number_total 1744 _reflns_threshold_expression >2sigma(I) _cod_data_source_file b905511h.txt _cod_data_source_block TM_formI _cod_original_cell_volume 1465.06(11) _cod_original_sg_symbol_H-M P21/c _cod_database_code 7201153 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.05783(12) 0.97077(8) 0.38905(8) 0.0222(4) Uani 1 1 d . . . S2 S 0.81503(12) 0.86570(8) 0.74422(8) 0.0252(4) Uani 1 1 d . . . O1 O 0.0845(3) 0.6392(2) 0.5512(2) 0.0222(7) Uani 1 1 d . . . O2 O -0.1068(3) 0.7291(2) 0.5459(2) 0.0256(7) Uani 1 1 d . . . O3 O 0.3561(3) 1.0053(2) 0.6746(2) 0.0268(7) Uani 1 1 d . . . O4 O 0.5598(3) 1.0563(2) 0.8618(2) 0.0251(7) Uani 1 1 d . . . N1 N -0.0054(4) 0.8212(3) 0.4813(3) 0.0195(8) Uani 1 1 d D . . H1 H -0.062(4) 0.879(2) 0.479(3) 0.023 Uiso 1 1 d D . . N2 N 0.1878(4) 0.7649(3) 0.4684(3) 0.0180(8) Uani 1 1 d D . . H2 H 0.189(5) 0.696(2) 0.495(3) 0.022 Uiso 1 1 d D . . N3 N 0.4772(4) 0.8990(3) 0.5933(3) 0.0198(8) Uani 1 1 d D . . H3 H 0.392(4) 0.933(3) 0.581(3) 0.024 Uiso 1 1 d D . . N4 N 0.6380(4) 0.9786(3) 0.7753(3) 0.0213(8) Uani 1 1 d D . . H4 H 0.744(3) 0.992(3) 0.842(2) 0.026 Uiso 1 1 d D . . C1 C -0.1115(6) 0.6312(3) 0.6000(4) 0.0288(10) Uani 1 1 d . . . H1A H -0.1624 0.5672 0.5462 0.043 Uiso 1 1 calc R . . H1B H -0.1793 0.6490 0.6192 0.043 Uiso 1 1 calc R . . H1C H 0.0042 0.6117 0.6708 0.043 Uiso 1 1 calc R . . C2 C -0.0018(5) 0.7206(4) 0.5285(3) 0.0213(10) Uani 1 1 d . . . C3 C 0.0833(5) 0.8455(3) 0.4486(3) 0.0194(9) Uani 1 1 d . . . C4 C 0.2815(5) 0.7729(3) 0.4333(3) 0.0197(9) Uani 1 1 d . . . C5 C 0.2291(5) 0.7100(3) 0.3393(3) 0.0231(10) Uani 1 1 d . . . H5 H 0.1275 0.6671 0.2957 0.028 Uiso 1 1 calc R . . C6 C 0.3235(5) 0.7092(3) 0.3086(3) 0.0251(10) Uani 1 1 d . . . H6 H 0.2867 0.6664 0.2438 0.030 Uiso 1 1 calc R . . C7 C 0.4733(5) 0.7718(3) 0.3737(3) 0.0237(10) Uani 1 1 d . . . H7 H 0.5398 0.7705 0.3539 0.028 Uiso 1 1 calc R . . C8 C 0.5251(5) 0.8356(3) 0.4668(3) 0.0215(9) Uani 1 1 d . . . H8 H 0.6257 0.8794 0.5096 0.026 Uiso 1 1 calc R . . C9 C 0.4309(5) 0.8361(3) 0.4984(3) 0.0196(9) Uani 1 1 d . . . C10 C 0.6334(5) 0.9148(3) 0.6974(3) 0.0202(9) Uani 1 1 d . . . C11 C 0.5039(5) 1.0131(3) 0.7618(3) 0.0216(9) Uani 1 1 d . . . C12 C 0.4236(5) 1.0903(4) 0.8565(4) 0.0275(10) Uani 1 1 d . . . H12A H 0.3682 1.1583 0.8086 0.041 Uiso 1 1 calc R . . H12B H 0.4709 1.1063 0.9349 0.041 Uiso 1 1 calc R . . H12C H 0.3403 1.0292 0.8225 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0248(6) 0.0212(6) 0.0217(6) 0.0030(4) 0.0162(5) 0.0019(4) S2 0.0222(6) 0.0284(6) 0.0226(6) 0.0006(4) 0.0142(5) 0.0022(5) O1 0.0225(15) 0.0234(16) 0.0242(15) 0.0022(12) 0.0172(13) 0.0041(13) O2 0.0289(16) 0.0267(16) 0.0303(15) 0.0047(12) 0.0238(14) 0.0038(13) O3 0.0196(17) 0.0367(17) 0.0192(15) -0.0039(13) 0.0111(15) -0.0012(13) O4 0.0230(15) 0.0276(16) 0.0227(15) -0.0073(13) 0.0146(13) -0.0055(12) N1 0.0252(19) 0.0167(18) 0.0240(18) 0.0025(15) 0.0197(16) 0.0025(15) N2 0.0232(18) 0.0121(17) 0.0204(17) 0.0014(14) 0.0155(16) 0.0018(15) N3 0.0162(19) 0.0215(18) 0.0192(18) -0.0016(14) 0.0111(17) 0.0022(14) N4 0.0184(18) 0.0217(19) 0.0182(18) -0.0003(15) 0.0102(15) 0.0000(15) C1 0.037(3) 0.024(2) 0.034(2) 0.0056(19) 0.028(2) 0.001(2) C2 0.018(2) 0.029(3) 0.014(2) -0.0075(18) 0.0098(18) -0.003(2) C3 0.019(2) 0.023(2) 0.0107(19) -0.0029(16) 0.0076(17) 0.0002(18) C4 0.019(2) 0.019(2) 0.023(2) 0.0018(18) 0.0143(19) 0.0032(18) C5 0.023(2) 0.019(2) 0.021(2) 0.0003(17) 0.0124(19) 0.0000(18) C6 0.030(2) 0.027(2) 0.021(2) 0.0020(18) 0.019(2) 0.005(2) C7 0.029(2) 0.029(2) 0.024(2) 0.0048(19) 0.022(2) 0.006(2) C8 0.017(2) 0.022(2) 0.025(2) 0.0050(18) 0.0140(19) 0.0041(18) C9 0.016(2) 0.017(2) 0.019(2) 0.0020(17) 0.0090(18) 0.0027(18) C10 0.026(2) 0.018(2) 0.022(2) 0.0036(18) 0.018(2) -0.0002(18) C11 0.028(3) 0.020(2) 0.022(2) -0.0017(18) 0.019(2) 0.0005(19) C12 0.028(2) 0.030(2) 0.030(2) -0.0065(19) 0.022(2) -0.002(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 C1 115.3(3) . . ? C11 O4 C12 113.5(3) . . ? C3 N1 C2 126.7(3) . . ? C3 N1 H1 116(3) . . ? C2 N1 H1 117(3) . . ? C3 N2 C4 123.7(3) . . ? C3 N2 H2 120(2) . . ? C4 N2 H2 115(2) . . ? C10 N3 C9 127.7(3) . . ? C10 N3 H3 117(3) . . ? C9 N3 H3 116(3) . . ? C11 N4 C10 127.6(3) . . ? C11 N4 H4 120(3) . . ? C10 N4 H4 112(3) . . ? O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 O2 125.7(4) . . ? O1 C2 N1 125.5(3) . . ? O2 C2 N1 108.8(3) . . ? N2 C3 N1 116.3(3) . . ? N2 C3 S1 123.8(3) . . ? N1 C3 S1 119.9(3) . . ? C5 C4 C9 120.2(3) . . ? C5 C4 N2 119.1(3) . . ? C9 C4 N2 120.5(3) . . ? C6 C5 C4 120.6(4) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 119.4(4) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C8 C7 C6 120.2(4) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 120.5(4) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C4 119.1(3) . . ? C8 C9 N3 123.5(3) . . ? C4 C9 N3 117.4(3) . . ? N3 C10 N4 114.4(3) . . ? N3 C10 S2 128.0(3) . . ? N4 C10 S2 117.6(3) . . ? O3 C11 O4 123.9(4) . . ? O3 C11 N4 126.1(3) . . ? O4 C11 N4 110.0(3) . . ? O4 C12 H12A 109.5 . . ? O4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C3 1.674(4) . ? S2 C10 1.652(4) . ? O1 C2 1.210(5) . ? O2 C2 1.329(5) . ? O2 C1 1.457(5) . ? O3 C11 1.207(5) . ? O4 C11 1.345(5) . ? O4 C12 1.462(5) . ? N1 C3 1.382(5) . ? N1 C2 1.389(5) . ? N1 H1 0.900(19) . ? N2 C3 1.339(5) . ? N2 C4 1.437(5) . ? N2 H2 0.903(19) . ? N3 C10 1.343(5) . ? N3 C9 1.420(5) . ? N3 H3 0.896(19) . ? N4 C11 1.365(5) . ? N4 C10 1.409(5) . ? N4 H4 0.90(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C4 C5 1.387(5) . ? C4 C9 1.397(5) . ? C5 C6 1.384(5) . ? C5 H5 0.9500 . ? C6 C7 1.397(6) . ? C6 H6 0.9500 . ? C7 C8 1.385(5) . ? C7 H7 0.9500 . ? C8 C9 1.394(5) . ? C8 H8 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S1 0.900(19) 2.70(3) 3.473(3) 144(3) 3_576 N2 H2 O1 0.903(19) 1.97(3) 2.660(4) 132(3) . N2 H2 O4 0.903(19) 2.62(3) 3.280(4) 131(3) 2_646 N3 H3 O3 0.896(19) 1.94(3) 2.671(4) 137(3) . N3 H3 S1 0.896(19) 2.74(3) 3.419(3) 134(3) . N4 H4 O1 0.90(2) 2.25(3) 2.985(4) 139(3) 2_656 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 O2 C2 O1 1.7(5) . . . . ? C1 O2 C2 N1 -177.5(3) . . . . ? C3 N1 C2 O1 2.2(6) . . . . ? C3 N1 C2 O2 -178.6(3) . . . . ? C4 N2 C3 N1 175.9(3) . . . . ? C4 N2 C3 S1 -4.6(5) . . . . ? C2 N1 C3 N2 -2.5(5) . . . . ? C2 N1 C3 S1 178.0(3) . . . . ? C3 N2 C4 C5 -105.5(4) . . . . ? C3 N2 C4 C9 79.6(5) . . . . ? C9 C4 C5 C6 -0.2(6) . . . . ? N2 C4 C5 C6 -175.1(3) . . . . ? C4 C5 C6 C7 0.4(6) . . . . ? C5 C6 C7 C8 -1.1(6) . . . . ? C6 C7 C8 C9 1.5(6) . . . . ? C7 C8 C9 C4 -1.2(5) . . . . ? C7 C8 C9 N3 179.6(3) . . . . ? C5 C4 C9 C8 0.5(5) . . . . ? N2 C4 C9 C8 175.4(3) . . . . ? C5 C4 C9 N3 179.8(3) . . . . ? N2 C4 C9 N3 -5.3(5) . . . . ? C10 N3 C9 C8 -39.2(6) . . . . ? C10 N3 C9 C4 141.6(4) . . . . ? C9 N3 C10 N4 -178.0(3) . . . . ? C9 N3 C10 S2 -0.1(6) . . . . ? C11 N4 C10 N3 8.4(5) . . . . ? C11 N4 C10 S2 -169.7(3) . . . . ? C12 O4 C11 O3 1.8(5) . . . . ? C12 O4 C11 N4 -177.1(3) . . . . ? C10 N4 C11 O3 -8.7(6) . . . . ? C10 N4 C11 O4 170.2(3) . . . . ?