#------------------------------------------------------------------------------ #$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/10/54/2105482.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_2105482 loop_ _publ_author_name 'Jones, Peter G.' 'Taouss, Christina' 'Teschmit, Nicole' 'Thomas, Lena' _publ_section_title ; Methylthioureas and their morpholine and dioxane adducts; hydrogen-bonding patterns ; _journal_coeditor_code GP5065 _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 405 _journal_page_last 413 _journal_paper_doi 10.1107/S2052519213013481 _journal_volume 69 _journal_year 2013 _chemical_formula_sum 'C5 H12 N2 O S' _chemical_formula_weight 148.23 _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 92.982(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.4979(2) _cell_length_b 7.0116(3) _cell_length_c 16.7097(6) _cell_measurement_reflns_used 7968 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.7573 _cell_measurement_theta_min 2.4361 _cell_volume 760.27(5) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 16.1419 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.960 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Eos' _diffrn_measurement_method \w-scan _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 26635 _diffrn_reflns_theta_full 30.50 _diffrn_reflns_theta_max 30.83 _diffrn_reflns_theta_min 2.44 _exptl_absorpt_coefficient_mu 0.352 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.89914 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_description tablet _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.373 _refine_diff_density_min -0.343 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 92 _refine_ls_number_reflns 2295 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0297 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0335P)^2^+0.3101P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0713 _refine_ls_wR_factor_ref 0.0749 _reflns_number_gt 2020 _reflns_number_total 2295 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL Kirsche in P2(1)/c CELL 0.71073 6.497912 7.011558 16.709723 90.0000 92.9824 90.0000 ZERR 4.00 0.0002 0.00026 0.0006 0.0000 0.004 0.0000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N S O UNIT 20 48 8 4 4 FMAP 2 PLAN 10 L.S. 4 TEMP -173 SIZE 0.4 0.34 0.07 EQIV $1 -x+1, -y+1, -z HTAB N3 S1_$1 HTAB N3 O1 ACTA 61 CONF WGHT 0.033500 0.310100 FVAR 8.07764 S1 4 0.595612 0.362198 0.114934 11.00000 0.01565 0.01862 = 0.01421 -0.00031 0.00191 0.00477 N3 3 0.282982 0.593597 0.078869 11.00000 0.02069 0.02362 = 0.01304 0.00260 0.00324 0.00936 H02 2 0.333650 0.600045 0.031882 11.00000 0.02866 H01 2 0.183671 0.665134 0.086422 11.00000 0.02620 N1 3 0.292069 0.475573 0.206942 11.00000 0.01536 0.01418 = 0.01246 0.00063 0.00179 0.00224 C2 1 0.376828 0.484527 0.135654 11.00000 0.01399 0.01173 = 0.01336 -0.00196 0.00037 -0.00026 C11 1 0.387706 0.369803 0.274530 11.00000 0.02300 0.02187 = 0.01517 0.00512 0.00339 0.00629 AFIX 137 H11A 2 0.307146 0.254560 0.283968 11.00000 -1.50000 H11B 2 0.391652 0.450115 0.322585 11.00000 -1.50000 H11C 2 0.528409 0.333853 0.262329 11.00000 -1.50000 AFIX 0 C12 1 0.101380 0.578910 0.221208 11.00000 0.01463 0.01947 = 0.01655 -0.00052 0.00343 0.00223 AFIX 137 H12A 2 0.124927 0.716250 0.215775 11.00000 -1.50000 H12B 2 0.058924 0.551189 0.275417 11.00000 -1.50000 H12C 2 -0.007221 0.538393 0.181971 11.00000 -1.50000 AFIX 0 O1 5 -0.011878 0.917009 0.077068 11.00000 0.01846 0.01745 = 0.01526 0.00183 0.00023 0.00012 C4 1 0.099442 1.091072 0.065506 11.00000 0.01914 0.01859 = 0.01570 -0.00259 0.00054 -0.00164 AFIX 23 H4A 2 0.216586 1.099340 0.105674 11.00000 -1.20000 H4B 2 0.007558 1.201278 0.073571 11.00000 -1.20000 AFIX 0 C3 1 -0.179441 0.900513 0.017939 11.00000 0.01529 0.01853 = 0.01789 -0.00057 0.00174 -0.00072 AFIX 23 H3A 2 -0.278811 1.005522 0.024846 11.00000 -1.20000 H3B 2 -0.252258 0.778193 0.025190 11.00000 -1.20000 HKLF 4 ; _cod_data_source_file gp5065.cif _cod_data_source_block kirsche _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2105482 _cod_database_fobs_code 2105482 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_type_symbol _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_symmetry_multiplicity S S1 0.59561(4) 0.36220(4) 0.114934(15) 0.01612(8) Uani d . 1 1 N N3 0.28298(16) 0.59360(15) 0.07887(6) 0.0190(2) Uani d . 1 1 H H02 0.334(3) 0.600(2) 0.0319(10) 0.029(4) Uiso d . 1 1 H H01 0.184(3) 0.665(2) 0.0864(9) 0.026(4) Uiso d . 1 1 N N1 0.29207(13) 0.47557(13) 0.20694(5) 0.01396(17) Uani d . 1 1 C C2 0.37683(15) 0.48453(14) 0.13565(6) 0.01304(19) Uani d . 1 1 C C11 0.38771(18) 0.36980(17) 0.27453(7) 0.0199(2) Uani d . 1 1 H H11A 0.3071 0.2546 0.2840 0.030 Uiso calc R 1 1 H H11B 0.3917 0.4501 0.3226 0.030 Uiso calc R 1 1 H H11C 0.5284 0.3339 0.2623 0.030 Uiso calc R 1 1 C C12 0.10138(16) 0.57891(16) 0.22121(7) 0.0168(2) Uani d . 1 1 H H12A 0.1249 0.7162 0.2158 0.025 Uiso calc R 1 1 H H12B 0.0589 0.5512 0.2754 0.025 Uiso calc R 1 1 H H12C -0.0072 0.5384 0.1820 0.025 Uiso calc R 1 1 O O1 -0.01188(12) 0.91701(11) 0.07707(5) 0.01708(16) Uani d . 1 1 C C4 0.09944(17) 1.09107(16) 0.06551(6) 0.0178(2) Uani d . 1 1 H H4A 0.2166 1.0993 0.1057 0.021 Uiso calc R 1 1 H H4B 0.0076 1.2013 0.0736 0.021 Uiso calc R 1 1 C C3 -0.17944(16) 0.90051(16) 0.01794(6) 0.0172(2) Uani d . 1 1 H H3A -0.2788 1.0055 0.0248 0.021 Uiso calc R 1 1 H H3B -0.2523 0.7782 0.0252 0.021 Uiso calc R 1 1 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 0.01565(13) 0.01862(14) 0.01421(13) 0.00477(9) 0.00191(9) -0.00031(9) N3 0.0207(5) 0.0236(5) 0.0130(4) 0.0094(4) 0.0032(3) 0.0026(4) N1 0.0154(4) 0.0142(4) 0.0125(4) 0.0022(3) 0.0018(3) 0.0006(3) C2 0.0140(4) 0.0117(4) 0.0134(4) -0.0003(3) 0.0004(3) -0.0020(3) C11 0.0230(5) 0.0219(5) 0.0152(5) 0.0063(4) 0.0034(4) 0.0051(4) C12 0.0146(5) 0.0195(5) 0.0165(5) 0.0022(4) 0.0034(4) -0.0005(4) O1 0.0185(4) 0.0174(4) 0.0153(4) 0.0001(3) 0.0002(3) 0.0018(3) C4 0.0191(5) 0.0186(5) 0.0157(5) -0.0016(4) 0.0005(4) -0.0026(4) C3 0.0153(5) 0.0185(5) 0.0179(5) -0.0007(4) 0.0017(4) -0.0006(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle C2 N1 C11 . . 122.18(9) C2 N1 C12 . . 120.77(9) C11 N1 C12 . . 117.00(8) N1 C2 N3 . . 117.60(9) N1 C2 S1 . . 122.74(8) N3 C2 S1 . . 119.66(8) C3 O1 C4 . . 110.17(8) O1 C4 C3 . 3_575 110.87(9) O1 C3 C4 . 3_575 110.24(9) C2 N3 H02 . . 119.3(11) C2 N3 H01 . . 124.4(11) H02 N3 H01 . . 116.1(15) N1 C11 H11A . . 109.5 N1 C11 H11B . . 109.5 H11A C11 H11B . . 109.5 N1 C11 H11C . . 109.5 H11A C11 H11C . . 109.5 H11B C11 H11C . . 109.5 N1 C12 H12A . . 109.5 N1 C12 H12B . . 109.5 H12A C12 H12B . . 109.5 N1 C12 H12C . . 109.5 H12A C12 H12C . . 109.5 H12B C12 H12C . . 109.5 O1 C4 H4A . . 109.5 C3 C4 H4A 3_575 . 109.5 O1 C4 H4B . . 109.5 C3 C4 H4B 3_575 . 109.5 H4A C4 H4B . . 108.1 O1 C3 H3A . . 109.6 C4 C3 H3A 3_575 . 109.6 O1 C3 H3B . . 109.6 C4 C3 H3B 3_575 . 109.6 H3A C3 H3B . . 108.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance S1 C2 . 1.7111(10) N3 C2 . 1.3405(14) N1 C2 . 1.3396(13) N1 C11 . 1.4624(14) N1 C12 . 1.4656(13) O1 C3 . 1.4364(13) O1 C4 . 1.4369(13) C4 C3 3_575 1.5143(15) C3 C4 3_575 1.5143(15) N3 H02 . 0.868(17) N3 H01 . 0.832(17) C11 H11A . 0.9800 C11 H11B . 0.9800 C11 H11C . 0.9800 C12 H12A . 0.9800 C12 H12B . 0.9800 C12 H12C . 0.9800 C4 H4A . 0.9900 C4 H4B . 0.9900 C3 H3A . 0.9900 C3 H3B . 0.9900 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 N3 H02 S1 3_665 0.868(17) 2.533(17) 3.3870(10) 167.9(14) N3 H01 O1 . 0.832(17) 2.177(17) 2.9678(13) 158.9(15) 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_site_symmetry_4 _geom_torsion C11 N1 C2 N3 . -176.46(10) C12 N1 C2 N3 . 1.16(15) C11 N1 C2 S1 . 4.04(15) C12 N1 C2 S1 . -178.35(8) C3 O1 C4 C3 3_575 -57.69(12) C4 O1 C3 C4 3_575 57.32(12)