#------------------------------------------------------------------------------ #$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/10/54/2105481.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_2105481 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 'C6 H15 N3 O S' _chemical_formula_weight 177.27 _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' _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 96.964(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.56953(19) _cell_length_b 8.7346(3) _cell_length_c 16.2322(5) _cell_measurement_reflns_used 8511 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.7462 _cell_measurement_theta_min 2.3270 _cell_volume 924.57(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 0.988 _diffrn_measured_fraction_theta_max 0.953 _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 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0128 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 24602 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.81 _diffrn_reflns_theta_min 2.53 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.93017 _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 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 384 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.424 _refine_diff_density_min -0.217 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 117 _refine_ls_number_reflns 2766 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0246 _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^)+(0.0279P)^2^+0.2877P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.0648 _reflns_number_gt 2481 _reflns_number_total 2766 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL Buche in P2(1)/n CELL 0.71073 6.569535 8.734650 16.232207 90.0000 96.9638 90.0000 ZERR 4.00 0.00019 0.00026 0.00046 0.0000 0.0026 0.0000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N S O UNIT 24 60 12 4 4 FMAP 2 PLAN 5 ACTA 60 CONF EQIV $1 -x+1, -y, -z+1 EQIV $2 -x+1, -y+1, -z+1 EQIV $3 -x-0.5, y-0.5, -z+0.5 HTAB N1 S_$1 HTAB N3 N4 HTAB N3 S1_$2 HTAB N4 O1_$3 OMIT -3 3 5 SIZE 0.6 0.3 0.2 TEMP -173 L.S. 4 WGHT 0.027900 0.287700 FVAR 5.92390 S1 4 0.592787 0.251499 0.516867 11.00000 0.01197 0.01029 = 0.01869 0.00048 -0.00278 0.00015 N1 3 0.261080 0.112996 0.442832 11.00000 0.01344 0.00881 = 0.01799 0.00037 -0.00210 0.00026 H01 2 0.322703 0.034106 0.458474 11.00000 0.02161 C2 1 0.355933 0.246546 0.459092 11.00000 0.01207 0.01114 = 0.01075 -0.00056 0.00190 0.00045 N3 3 0.262594 0.374626 0.430363 11.00000 0.01454 0.00931 = 0.01785 0.00030 -0.00338 -0.00005 H02 2 0.146888 0.373800 0.397807 11.00000 0.02962 H03 2 0.319691 0.459827 0.443724 11.00000 0.02306 C11 1 0.056837 0.096537 0.397966 11.00000 0.01420 0.01328 = 0.02450 -0.00067 -0.00344 -0.00187 AFIX 137 H11A 2 -0.041553 0.154230 0.426586 11.00000 -1.50000 H11B 2 0.018306 -0.011906 0.395620 11.00000 -1.50000 H11C 2 0.056111 0.136194 0.341454 11.00000 -1.50000 AFIX 0 O1 5 -0.056548 0.757670 0.297407 11.00000 0.02387 0.01288 = 0.01802 0.00272 0.00607 0.00275 C3 1 0.084242 0.660437 0.261735 11.00000 0.01892 0.01823 = 0.01686 0.00155 0.00573 0.00089 AFIX 23 H3A 2 0.203385 0.638645 0.303516 11.00000 -1.20000 H3B 2 0.134966 0.713317 0.214276 11.00000 -1.20000 AFIX 0 C4 1 -0.017758 0.511386 0.232319 11.00000 0.02253 0.01868 = 0.01532 -0.00234 0.00030 0.00302 AFIX 23 H4A 2 -0.132551 0.532064 0.188355 11.00000 -1.20000 H4B 2 0.082343 0.444478 0.208835 11.00000 -1.20000 AFIX 0 N4 3 -0.095315 0.434516 0.303027 11.00000 0.01907 0.01278 = 0.01952 -0.00029 -0.00287 -0.00236 H04 2 -0.161672 0.358404 0.286477 11.00000 0.03227 C5 1 -0.239707 0.535431 0.339798 11.00000 0.01489 0.02153 = 0.01833 0.00337 0.00070 -0.00173 AFIX 23 H5A 2 -0.288141 0.484702 0.388373 11.00000 -1.20000 H5B 2 -0.360235 0.556634 0.298599 11.00000 -1.20000 AFIX 0 C6 1 -0.132372 0.683634 0.366379 11.00000 0.02002 0.01847 = 0.01426 0.00044 0.00414 0.00154 AFIX 23 H6A 2 -0.229386 0.752621 0.390302 11.00000 -1.20000 H6B 2 -0.016775 0.662255 0.409877 11.00000 -1.20000 HKLF 4 ; _cod_data_source_file gp5065.cif _cod_data_source_block buche _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2105481 _cod_database_fobs_code 2105481 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_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 0.59279(3) 0.25150(2) 0.516867(12) 0.01403(6) Uani d . 1 1 N N1 0.26108(10) 0.11300(8) 0.44283(4) 0.01374(13) Uani d . 1 1 H H01 0.3227(18) 0.0341(14) 0.4585(7) 0.022(3) Uiso d . 1 1 C C2 0.35593(12) 0.24655(8) 0.45909(5) 0.01128(14) Uani d . 1 1 N N3 0.26259(11) 0.37463(8) 0.43036(4) 0.01434(13) Uani d . 1 1 H H02 0.147(2) 0.3738(15) 0.3978(8) 0.030(3) Uiso d . 1 1 H H03 0.3197(18) 0.4598(14) 0.4437(7) 0.023(3) Uiso d . 1 1 C C11 0.05684(12) 0.09654(10) 0.39797(5) 0.01780(16) Uani d . 1 1 H H11A -0.0416 0.1542 0.4266 0.027 Uiso calc R 1 1 H H11B 0.0183 -0.0119 0.3956 0.027 Uiso calc R 1 1 H H11C 0.0561 0.1362 0.3415 0.027 Uiso calc R 1 1 O O1 -0.05655(10) 0.75767(7) 0.29741(4) 0.01797(13) Uani d . 1 1 C C3 0.08424(13) 0.66044(10) 0.26173(5) 0.01771(16) Uani d . 1 1 H H3A 0.2034 0.6386 0.3035 0.021 Uiso calc R 1 1 H H3B 0.1350 0.7133 0.2143 0.021 Uiso calc R 1 1 C C4 -0.01776(14) 0.51139(10) 0.23232(5) 0.01901(17) Uani d . 1 1 H H4A -0.1326 0.5321 0.1884 0.023 Uiso calc R 1 1 H H4B 0.0823 0.4445 0.2088 0.023 Uiso calc R 1 1 N N4 -0.09532(11) 0.43452(8) 0.30303(5) 0.01755(15) Uani d . 1 1 H H04 -0.162(2) 0.3584(16) 0.2865(8) 0.032(3) Uiso d . 1 1 C C5 -0.23971(13) 0.53543(10) 0.33980(5) 0.01836(17) Uani d . 1 1 H H5A -0.2881 0.4847 0.3884 0.022 Uiso calc R 1 1 H H5B -0.3602 0.5566 0.2986 0.022 Uiso calc R 1 1 C C6 -0.13237(13) 0.68363(10) 0.36638(5) 0.01742(16) Uani d . 1 1 H H6A -0.2294 0.7526 0.3903 0.021 Uiso calc R 1 1 H H6B -0.0168 0.6623 0.4099 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 0.01197(10) 0.01029(10) 0.01869(11) 0.00015(6) -0.00278(7) 0.00048(6) N1 0.0134(3) 0.0088(3) 0.0180(3) 0.0003(2) -0.0021(2) 0.0004(2) C2 0.0121(3) 0.0111(3) 0.0107(3) 0.0005(2) 0.0019(3) -0.0006(2) N3 0.0145(3) 0.0093(3) 0.0179(3) 0.0000(2) -0.0034(2) 0.0003(2) C11 0.0142(3) 0.0133(4) 0.0245(4) -0.0019(3) -0.0034(3) -0.0007(3) O1 0.0239(3) 0.0129(3) 0.0180(3) 0.0028(2) 0.0061(2) 0.0027(2) C3 0.0189(4) 0.0182(4) 0.0169(4) 0.0009(3) 0.0057(3) 0.0016(3) C4 0.0225(4) 0.0187(4) 0.0153(4) 0.0030(3) 0.0003(3) -0.0023(3) N4 0.0191(3) 0.0128(3) 0.0195(3) -0.0024(3) -0.0029(3) -0.0003(3) C5 0.0149(4) 0.0215(4) 0.0183(4) -0.0017(3) 0.0007(3) 0.0034(3) C6 0.0200(4) 0.0185(4) 0.0143(3) 0.0015(3) 0.0041(3) 0.0004(3) 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 C2 N1 C11 124.48(7) N3 C2 N1 118.74(7) N3 C2 S1 121.20(6) N1 C2 S1 120.05(6) C3 O1 C6 110.59(6) O1 C3 C4 110.81(7) N4 C4 C3 109.13(7) C4 N4 C5 110.09(7) N4 C5 C6 109.09(7) O1 C6 C5 110.95(7) C2 N1 H01 118.1(8) C11 N1 H01 117.4(8) C2 N3 H02 122.4(9) C2 N3 H03 118.4(8) H02 N3 H03 119.2(12) 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 O1 C3 H3A 109.5 C4 C3 H3A 109.5 O1 C3 H3B 109.5 C4 C3 H3B 109.5 H3A C3 H3B 108.1 N4 C4 H4A 109.9 C3 C4 H4A 109.9 N4 C4 H4B 109.9 C3 C4 H4B 109.9 H4A C4 H4B 108.3 C4 N4 H04 109.5(9) C5 N4 H04 105.9(9) N4 C5 H5A 109.9 C6 C5 H5A 109.9 N4 C5 H5B 109.9 C6 C5 H5B 109.9 H5A C5 H5B 108.3 O1 C6 H6A 109.4 C5 C6 H6A 109.4 O1 C6 H6B 109.4 C5 C6 H6B 109.4 H6A C6 H6B 108.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C2 1.7172(8) N1 C2 1.3337(10) N1 C11 1.4541(10) C2 N3 1.3326(10) O1 C3 1.4290(10) O1 C6 1.4335(10) C3 C4 1.5147(12) C4 N4 1.4729(11) N4 C5 1.4732(11) C5 C6 1.5117(12) N1 H01 0.824(12) N3 H02 0.872(13) N3 H03 0.850(13) C11 H11A 0.9800 C11 H11B 0.9800 C11 H11C 0.9800 C3 H3A 0.9900 C3 H3B 0.9900 C4 H4A 0.9900 C4 H4B 0.9900 N4 H04 0.822(14) C5 H5A 0.9900 C5 H5B 0.9900 C6 H6A 0.9900 C6 H6B 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 N1 H01 S1 3_656 0.824(12) 2.576(13) 3.3665(7) 161.2(11) N3 H02 N4 . 0.872(13) 2.142(13) 2.9826(10) 162.0(12) N3 H03 S1 3_666 0.850(13) 2.647(13) 3.4790(7) 166.5(10) N4 H04 O1 2_445 0.822(14) 2.333(14) 3.0611(10) 147.9(12) 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 C11 N1 C2 N3 -2.40(12) C11 N1 C2 S1 177.00(6) C6 O1 C3 C4 59.15(9) O1 C3 C4 N4 -58.36(9) C3 C4 N4 C5 57.82(9) C4 N4 C5 C6 -57.74(9) C3 O1 C6 C5 -59.18(9) N4 C5 C6 O1 58.19(9)