data_b2dpub _database_code_CSD 164615 _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'da Silva, luis C. M.' 'Damas, Ana M.' 'Dietze, Fran' 'Hoyer, Eberhard' 'Liebman, Joel' 'Ribeiro da Silva, Manuel A. V.' 'Ribeiro da Silva, Maria D. M. C.' 'Schroder, Bernd' _publ_contact_author_name 'Prof Manuel A V Ribeiro da Silva' _publ_contact_author_address ; Prof Manuel A V Ribeiro da Silva Departamento de Quimica, Faculdade de Ciencias Universidade do Porto Rua do Campo Alegre, 687 Porto P-4169-007 PORTUGAL ; _publ_contact_author_email 'RISILVA@FC.UP.PT' _publ_section_title ; Synthesis, characterization and thermochemical properties of N-acyl-N',N'-diethylthioureas ; _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H20 N2 O S' _chemical_formula_weight 216.34 _chemical_melting_point ? _chemical_compound_source ? 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' 'O' 'O' 0.0106 0.0060 '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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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' _cell_length_a 12.402(8) _cell_length_b 9.568(4) _cell_length_c 13.150(6) _cell_angle_alpha 90.00 _cell_angle_beta 124.59(6) _cell_angle_gamma 90.00 _cell_volume 1284.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.119 _exptl_crystal_density_method ? _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12055 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.17 _diffrn_reflns_theta_max 28.17 _reflns_number_total 2924 _reflns_number_observed 2369 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0665P)^2^+0.3090P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2924 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_obs 0.0460 _refine_ls_wR_factor_all 0.1380 _refine_ls_wR_factor_obs 0.1229 _refine_ls_goodness_of_fit_all 1.067 _refine_ls_goodness_of_fit_obs 1.064 _refine_ls_restrained_S_all 1.067 _refine_ls_restrained_S_obs 1.064 _refine_ls_shift/esd_max 0.159 _refine_ls_shift/esd_mean 0.012 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.20877(4) 0.05323(5) 0.17443(4) 0.0583(2) Uani 1 d . . O11' O 0.45604(11) 0.33268(10) 0.20393(12) 0.0519(3) Uani 1 d . . N1 N 0.42600(12) 0.09879(13) 0.18288(12) 0.0417(3) Uani 1 d . . N2 N 0.22942(13) 0.15477(15) -0.00319(13) 0.0490(3) Uani 1 d . . C1 C 0.28594(14) 0.10697(14) 0.11064(14) 0.0412(3) Uani 1 d . . C2 C 0.3002(2) 0.1912(2) -0.0598(2) 0.0592(5) Uani 1 d . . C11' C 0.50200(14) 0.21436(14) 0.23504(14) 0.0398(3) Uani 1 d . . C1' C 0.6454(2) 0.1898(2) 0.3334(2) 0.0466(4) Uani 1 d . . C2' C 0.6801(2) 0.2335(2) 0.4598(2) 0.0574(5) Uani 1 d . . C4 C 0.0863(2) 0.1763(3) -0.0823(2) 0.0690(6) Uani 1 d . . C4' C 0.8284(3) 0.2390(4) 0.5537(3) 0.0913(9) Uani 1 d . . C3 C 0.2930(5) 0.0794(4) -0.1429(4) 0.1045(12) Uani 1 d . . C5 C 0.0498(3) 0.3228(4) -0.0736(5) 0.1088(11) Uani 1 d . . C3' C 0.6124(3) 0.1377(4) 0.5005(3) 0.0868(8) Uani 1 d . . H11' H 0.6694(18) 0.0932(22) 0.3336(18) 0.052(5) Uiso 1 d . . H12' H 0.6986(21) 0.2433(24) 0.3151(21) 0.066(6) Uiso 1 d . . H1 H 0.4572(19) 0.0223(22) 0.2201(20) 0.055(5) Uiso 1 d . . H2' H 0.6450(22) 0.3310(24) 0.4466(23) 0.071(6) Uiso 1 d . . H41 H 0.0574(26) 0.1561(30) -0.1710(29) 0.096(9) Uiso 1 d . . H42 H 0.0474(24) 0.1093(28) -0.0596(25) 0.082(7) Uiso 1 d . . H21 H 0.3865(27) 0.2214(27) 0.0025(27) 0.087(8) Uiso 1 d . . H22 H 0.2593(24) 0.2824(27) -0.1039(26) 0.083(7) Uiso 1 d . . H31' H 0.6455(31) 0.0398(36) 0.5092(30) 0.109(10) Uiso 1 d . . H32' H 0.5108(35) 0.1395(35) 0.4419(33) 0.114(10) Uiso 1 d . . H33' H 0.6290(30) 0.1695(32) 0.5713(34) 0.104(10) Uiso 1 d . . H31 H 0.3277(33) 0.1095(38) -0.1860(34) 0.122(11) Uiso 1 d . . H32 H 0.3289(49) -0.0009(57) -0.0985(51) 0.176(19) Uiso 1 d . . H33 H 0.1886(56) 0.0610(55) -0.2145(53) 0.190(21) Uiso 1 d . . H51 H -0.0555(39) 0.3342(39) -0.1337(38) 0.137(12) Uiso 1 d . . H52 H 0.0771(29) 0.3426(31) 0.0071(32) 0.090(10) Uiso 1 d . . H53 H 0.0943(35) 0.3845(42) -0.1082(37) 0.131(13) Uiso 1 d . . H41' H 0.8627(30) 0.1538(37) 0.5652(31) 0.105(10) Uiso 1 d . . H42' H 0.8822(51) 0.2958(60) 0.5355(53) 0.207(24) Uiso 1 d . . H43' H 0.8548(38) 0.2639(40) 0.6421(45) 0.140(13) Uiso 1 d . . 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 0.0579(3) 0.0688(3) 0.0545(3) -0.0008(2) 0.0357(2) -0.0085(2) O11' 0.0506(6) 0.0332(5) 0.0539(7) -0.0014(4) 0.0190(5) -0.0018(4) N1 0.0420(6) 0.0333(6) 0.0414(7) 0.0003(5) 0.0186(5) -0.0005(5) N2 0.0453(7) 0.0521(7) 0.0386(7) 0.0025(5) 0.0173(6) -0.0068(5) C1 0.0420(7) 0.0363(7) 0.0381(8) -0.0048(5) 0.0185(6) -0.0039(5) C2 0.0672(11) 0.0637(11) 0.0433(10) 0.0023(8) 0.0294(9) -0.0127(9) C11' 0.0433(7) 0.0355(7) 0.0383(8) -0.0018(5) 0.0217(6) -0.0023(5) C1' 0.0420(8) 0.0478(8) 0.0438(9) -0.0014(6) 0.0205(7) -0.0011(6) C2' 0.0623(10) 0.0500(9) 0.0401(9) 0.0007(7) 0.0172(8) 0.0096(7) C4 0.0461(9) 0.0816(14) 0.0514(12) 0.0100(9) 0.0110(8) -0.0040(9) C4' 0.0720(15) 0.088(2) 0.0556(14) -0.0070(12) 0.0013(12) 0.0084(13) C3 0.174(4) 0.081(2) 0.115(3) -0.014(2) 0.116(3) -0.025(2) C5 0.079(2) 0.105(2) 0.114(3) 0.019(2) 0.037(2) 0.030(2) C3' 0.104(2) 0.104(2) 0.061(2) 0.0190(14) 0.0520(15) 0.018(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 1.672(2) . ? O11' C11' 1.228(2) . ? N1 C11' 1.359(2) . ? N1 C1 1.433(2) . ? N2 C1 1.323(2) . ? N2 C4 1.476(3) . ? N2 C2 1.480(2) . ? C2 C3 1.495(4) . ? C11' C1' 1.510(3) . ? C1' C2' 1.520(3) . ? C2' C4' 1.527(4) . ? C2' C3' 1.530(4) . ? C4 C5 1.497(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 C11' N1 C1 121.50(13) . . ? C1 N2 C4 119.9(2) . . ? C1 N2 C2 124.51(15) . . ? C4 N2 C2 115.6(2) . . ? N2 C1 N1 115.68(15) . . ? N2 C1 S1 125.98(13) . . ? N1 C1 S1 118.33(12) . . ? N2 C2 C3 113.1(2) . . ? O11' C11' N1 121.60(15) . . ? O11' C11' C1' 121.79(13) . . ? N1 C11' C1' 116.61(13) . . ? C11' C1' C2' 111.0(2) . . ? C1' C2' C4' 110.9(2) . . ? C1' C2' C3' 110.3(2) . . ? C4' C2' C3' 112.7(2) . . ? N2 C4 C5 111.8(2) . . ? _refine_diff_density_max 0.171 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.036