# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1i _database_code_depnum_ccdc_archive 'CCDC 883638' #TrackingRef '- deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(4-methoxyphenyl)-N'-(piperidino)thiourea ; _chemical_name_common N-(4-methoxyphenyl)-N'-(piperidino)thiourea _chemical_melting_point ? _chemical_formula_moiety 'C13 H18 N2 O S' _chemical_formula_sum 'C13 H18 N2 O S' _chemical_formula_weight 250.35 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 monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 10.4930(2) _cell_length_b 14.6391(4) _cell_length_c 9.0779(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.0210(10) _cell_angle_gamma 90.00 _cell_volume 1283.39(5) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5902 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 33.73 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.238 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.909 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 10115 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0568 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 33.77 _reflns_number_total 4498 _reflns_number_gt 3579 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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. All non-hydrogen atoms were refined acoording to the anisotropic model. Hydrogen atoms were placed in positions calculated from the expected hybridization state of the parent nitrogen or carbon atom. The H5A to H2 distance was maximized during the refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.13(8) _refine_ls_number_reflns 4498 _refine_ls_number_parameters 155 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1198 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.330 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.33310(6) 0.10264(4) 0.69303(6) 0.02586(13) Uani 1 1 d . . . O1 O 0.8678(2) -0.15726(13) 0.9927(2) 0.0359(4) Uani 1 1 d . . . N1 N 0.2775(2) 0.13584(14) 0.3851(2) 0.0258(4) Uani 1 1 d . . . N2 N 0.4550(2) 0.03309(13) 0.5080(2) 0.0262(4) Uani 1 1 d . . . H2 H 0.4522 0.0230 0.4113 0.031 Uiso 1 1 calc RD . . C1 C 0.1581(3) 0.19086(17) 0.3772(3) 0.0303(5) Uani 1 1 d . . . H1A H 0.1830 0.2564 0.3861 0.036 Uiso 1 1 calc R . . H1B H 0.1322 0.1748 0.4678 0.036 Uiso 1 1 calc R . . C2 C 0.0363(3) 0.1738(2) 0.2207(3) 0.0395(6) Uani 1 1 d . . . H2B H -0.0417 0.2138 0.2148 0.047 Uiso 1 1 calc R . . H2C H 0.0057 0.1096 0.2175 0.047 Uiso 1 1 calc R . . C3 C 0.0727(3) 0.1921(2) 0.0765(3) 0.0417(7) Uani 1 1 d . . . H3A H 0.0923 0.2579 0.0716 0.050 Uiso 1 1 calc R . . H3B H -0.0067 0.1756 -0.0230 0.050 Uiso 1 1 calc R . . C4 C 0.1993(3) 0.1361(2) 0.0897(3) 0.0361(6) Uani 1 1 d . . . H4A H 0.1760 0.0702 0.0816 0.043 Uiso 1 1 calc R . . H4B H 0.2273 0.1520 0.0006 0.043 Uiso 1 1 calc R . . C5 C 0.3169(3) 0.15491(18) 0.2468(3) 0.0309(5) Uani 1 1 d . . . H5A H 0.3972 0.1164 0.2559 0.037 Uiso 1 1 calc RD . . H5B H 0.3451 0.2197 0.2503 0.037 Uiso 1 1 calc R . . C6 C 0.3571(2) 0.09062(14) 0.5191(2) 0.0212(4) Uani 1 1 d . . . C7 C 0.5602(2) -0.01200(14) 0.6346(2) 0.0221(4) Uani 1 1 d . . . C8 C 0.5821(2) -0.10493(15) 0.6182(3) 0.0247(4) Uani 1 1 d . . . H8 H 0.5253 -0.1366 0.5240 0.030 Uiso 1 1 calc R . . C9 C 0.6871(2) -0.15114(16) 0.7398(3) 0.0278(4) Uani 1 1 d . . . H9 H 0.7024 -0.2142 0.7279 0.033 Uiso 1 1 calc R . . C10 C 0.7699(2) -0.10510(16) 0.8788(3) 0.0253(4) Uani 1 1 d . . . C11 C 0.7502(2) -0.01237(17) 0.8941(3) 0.0278(5) Uani 1 1 d . . . H11 H 0.8071 0.0195 0.9881 0.033 Uiso 1 1 calc R . . C12 C 0.6462(2) 0.03376(16) 0.7705(3) 0.0263(4) Uani 1 1 d . . . H12 H 0.6343 0.0975 0.7798 0.032 Uiso 1 1 calc R . . C13 C 0.9542(3) -0.1126(2) 1.1361(3) 0.0375(6) Uani 1 1 d . . . H13A H 1.0202 -0.1566 1.2070 0.056 Uiso 1 1 calc R . . H13B H 0.8971 -0.0873 1.1897 0.056 Uiso 1 1 calc R . . H13C H 1.0049 -0.0630 1.1103 0.056 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 0.0323(3) 0.0278(2) 0.0184(2) 0.0026(2) 0.01086(18) 0.0063(2) O1 0.0343(9) 0.0352(9) 0.0287(9) 0.0045(7) 0.0020(7) 0.0100(8) N1 0.0275(9) 0.0297(10) 0.0196(8) 0.0059(7) 0.0086(7) 0.0080(8) N2 0.0288(9) 0.0310(10) 0.0163(8) -0.0014(7) 0.0062(7) 0.0082(7) C1 0.0353(12) 0.0309(11) 0.0247(10) 0.0054(9) 0.0119(9) 0.0128(10) C2 0.0331(12) 0.0454(15) 0.0357(14) 0.0048(12) 0.0087(11) 0.0153(11) C3 0.0442(15) 0.0503(16) 0.0228(11) 0.0019(11) 0.0045(10) 0.0168(13) C4 0.0452(14) 0.0384(13) 0.0219(10) 0.0022(10) 0.0102(10) 0.0096(11) C5 0.0323(12) 0.0396(13) 0.0231(10) 0.0069(10) 0.0133(9) 0.0038(10) C6 0.0232(9) 0.0209(9) 0.0180(9) 0.0006(7) 0.0065(7) 0.0008(7) C7 0.0233(9) 0.0246(10) 0.0186(8) 0.0010(8) 0.0083(7) 0.0038(8) C8 0.0245(10) 0.0267(10) 0.0217(10) -0.0036(8) 0.0077(8) 0.0021(8) C9 0.0281(11) 0.0262(10) 0.0274(11) -0.0006(9) 0.0090(9) 0.0031(9) C10 0.0229(10) 0.0299(11) 0.0215(9) 0.0038(9) 0.0068(8) 0.0037(9) C11 0.0255(10) 0.0307(12) 0.0227(9) -0.0025(9) 0.0047(8) 0.0013(8) C12 0.0272(10) 0.0254(10) 0.0236(10) -0.0021(8) 0.0068(8) 0.0010(8) C13 0.0304(12) 0.0510(16) 0.0245(11) 0.0044(11) 0.0035(9) 0.0071(11) _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 C6 1.703(2) . ? O1 C10 1.370(3) . ? O1 C13 1.422(3) . ? N1 C6 1.349(3) . ? N1 C1 1.467(3) . ? N1 C5 1.494(3) . ? N2 C6 1.362(3) . ? N2 C7 1.408(3) . ? N2 H2 0.8800 . ? C1 C2 1.514(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.524(4) . ? C2 H2B 0.9900 . ? C2 H2C 0.9900 . ? C3 C4 1.526(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.502(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C7 C12 1.383(3) . ? C7 C8 1.397(3) . ? C8 C9 1.392(3) . ? C8 H8 0.9500 . ? C9 C10 1.395(3) . ? C9 H9 0.9500 . ? C10 C11 1.388(3) . ? C11 C12 1.396(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? 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 C10 O1 C13 117.1(2) . . ? C6 N1 C1 121.98(19) . . ? C6 N1 C5 124.87(19) . . ? C1 N1 C5 111.58(18) . . ? C6 N2 C7 127.09(18) . . ? C6 N2 H2 116.5 . . ? C7 N2 H2 116.5 . . ? N1 C1 C2 110.3(2) . . ? N1 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.1 . . ? C1 C2 C3 111.9(3) . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? C1 C2 H2C 109.2 . . ? C3 C2 H2C 109.2 . . ? H2B C2 H2C 107.9 . . ? C2 C3 C4 109.9(2) . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3B 109.7 . . ? C4 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C5 C4 C3 110.0(2) . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? N1 C5 C4 111.7(2) . . ? N1 C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? N1 C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? N1 C6 N2 117.13(19) . . ? N1 C6 S1 121.40(17) . . ? N2 C6 S1 121.44(16) . . ? C12 C7 C8 119.3(2) . . ? C12 C7 N2 122.0(2) . . ? C8 C7 N2 118.59(19) . . ? C9 C8 C7 120.0(2) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 120.2(2) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? O1 C10 C11 124.5(2) . . ? O1 C10 C9 115.6(2) . . ? C11 C10 C9 119.9(2) . . ? C10 C11 C12 119.5(2) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C7 C12 C11 121.0(2) . . ? C7 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 33.77 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.397 _refine_diff_density_min -0.570 _refine_diff_density_rms 0.105 data_2k _database_code_depnum_ccdc_archive 'CCDC 883639' #TrackingRef '- deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-phenyl-N'-(thiomorpholino)thiourea ; _chemical_name_common N-phenyl-N'-(thiomorpholino)thiourea _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 N2 S2' _chemical_formula_sum 'C11 H14 N2 S2' _chemical_formula_weight 238.36 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c 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 11.5813(3) _cell_length_b 9.3856(3) _cell_length_c 10.8926(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.21(3) _cell_angle_gamma 90.00 _cell_volume 1161.40(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 14080 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.427 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.881 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 14713 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 30.05 _reflns_number_total 3390 _reflns_number_gt 2445 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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. All non-hydrogen atoms were refined acoording to the anisotropic model. Hydrogen atoms were placed in positions calculated from the expected hybridization state of the parent nitrogen or carbon atom. The intramolecular hydrogen...hydrogen separation H2...H4A was constrained to be over 1.80 A or during refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+0.8600P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3390 _refine_ls_number_parameters 136 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1109 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.305 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.10691(6) 0.38058(8) 0.58833(7) 0.0389(2) Uani 1 1 d . . . S2 S 0.48464(5) 0.18559(7) 0.92423(6) 0.02845(17) Uani 1 1 d . . . N1 N 0.33462(17) 0.3786(2) 0.80123(19) 0.0260(4) Uani 1 1 d . . . N2 N 0.53090(17) 0.4095(2) 0.79004(19) 0.0270(4) Uani 1 1 d . . . H2 H 0.5052 0.4778 0.7362 0.032 Uiso 1 1 calc RD . . C1 C 0.2351(2) 0.2896(3) 0.8178(3) 0.0346(6) Uani 1 1 d . . . H1A H 0.1820 0.3451 0.8608 0.042 Uiso 1 1 calc R . . H1B H 0.2643 0.2066 0.8710 0.042 Uiso 1 1 calc R . . C2 C 0.1673(2) 0.2380(3) 0.6922(3) 0.0402(7) Uani 1 1 d . . . H2B H 0.1022 0.1756 0.7065 0.048 Uiso 1 1 calc R . . H2C H 0.2204 0.1800 0.6512 0.048 Uiso 1 1 calc R . . C3 C 0.2403(2) 0.4843(3) 0.5988(2) 0.0311(6) Uani 1 1 d . . . H3A H 0.2966 0.4321 0.5576 0.037 Uiso 1 1 calc R . . H3B H 0.2216 0.5760 0.5545 0.037 Uiso 1 1 calc R . . C4 C 0.2962(2) 0.5126(3) 0.7343(2) 0.0261(5) Uani 1 1 d . . . H4A H 0.3649 0.5763 0.7378 0.031 Uiso 1 1 calc RD . . H4B H 0.2388 0.5616 0.7762 0.031 Uiso 1 1 calc R . . C5 C 0.4471(2) 0.3324(2) 0.8335(2) 0.0230(5) Uani 1 1 d . . . C6 C 0.6537(2) 0.3916(2) 0.8220(2) 0.0244(5) Uani 1 1 d . . . C7 C 0.7157(2) 0.3818(3) 0.7256(2) 0.0277(5) Uani 1 1 d . . . H7 H 0.6750 0.3829 0.6410 0.033 Uiso 1 1 calc R . . C8 C 0.8377(2) 0.3703(3) 0.7530(3) 0.0327(6) Uani 1 1 d . . . H8 H 0.8805 0.3642 0.6871 0.039 Uiso 1 1 calc R . . C9 C 0.8968(2) 0.3679(3) 0.8761(3) 0.0344(6) Uani 1 1 d . . . H9 H 0.9800 0.3585 0.8949 0.041 Uiso 1 1 calc R . . C10 C 0.8345(2) 0.3789(3) 0.9720(3) 0.0340(6) Uani 1 1 d . . . H10 H 0.8754 0.3773 1.0566 0.041 Uiso 1 1 calc R . . C11 C 0.7129(2) 0.3924(3) 0.9456(2) 0.0299(5) Uani 1 1 d . . . H11 H 0.6706 0.4021 1.0116 0.036 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 0.0283(3) 0.0402(4) 0.0441(4) 0.0018(3) -0.0029(3) -0.0006(3) S2 0.0256(3) 0.0286(3) 0.0306(3) 0.0054(3) 0.0041(2) 0.0020(2) N1 0.0218(10) 0.0253(10) 0.0310(11) 0.0060(9) 0.0056(8) 0.0002(8) N2 0.0213(9) 0.0311(11) 0.0276(10) 0.0069(9) 0.0027(8) -0.0001(8) C1 0.0213(12) 0.0365(15) 0.0471(16) 0.0147(13) 0.0092(11) 0.0002(10) C2 0.0274(13) 0.0258(13) 0.065(2) 0.0036(13) 0.0019(13) -0.0021(11) C3 0.0301(13) 0.0336(14) 0.0304(13) 0.0039(11) 0.0075(10) 0.0038(11) C4 0.0248(12) 0.0224(11) 0.0315(13) 0.0013(10) 0.0062(10) 0.0013(9) C5 0.0219(11) 0.0256(11) 0.0218(11) -0.0029(9) 0.0053(8) -0.0010(9) C6 0.0211(11) 0.0226(11) 0.0290(12) 0.0000(10) 0.0034(9) -0.0014(9) C7 0.0280(12) 0.0283(13) 0.0265(12) -0.0014(10) 0.0050(10) -0.0024(10) C8 0.0279(13) 0.0331(14) 0.0399(15) -0.0036(12) 0.0139(11) -0.0004(10) C9 0.0215(12) 0.0317(13) 0.0493(17) 0.0011(12) 0.0050(11) 0.0020(10) C10 0.0272(13) 0.0370(15) 0.0344(14) 0.0014(12) -0.0026(10) -0.0028(11) C11 0.0281(12) 0.0342(14) 0.0275(12) -0.0025(11) 0.0052(10) -0.0025(10) _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 C2 1.804(3) . ? S1 C3 1.811(3) . ? S2 C5 1.702(2) . ? N1 C5 1.354(3) . ? N1 C1 1.463(3) . ? N1 C4 1.478(3) . ? N2 C5 1.367(3) . ? N2 C6 1.407(3) . ? N2 H2 0.8800 . ? C1 C2 1.519(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2B 0.9900 . ? C2 H2C 0.9900 . ? C3 C4 1.515(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C6 C7 1.386(3) . ? C6 C11 1.388(3) . ? C7 C8 1.390(3) . ? C7 H7 0.9500 . ? C8 C9 1.382(4) . ? C8 H8 0.9500 . ? C9 C10 1.384(4) . ? C9 H9 0.9500 . ? C10 C11 1.388(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? 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 S1 C3 97.91(12) . . ? C5 N1 C1 121.8(2) . . ? C5 N1 C4 125.7(2) . . ? C1 N1 C4 112.24(19) . . ? C5 N2 C6 127.1(2) . . ? C5 N2 H2 116.5 . . ? C6 N2 H2 116.5 . . ? N1 C1 C2 110.7(2) . . ? N1 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? C1 C2 S1 113.5(2) . . ? C1 C2 H2B 108.9 . . ? S1 C2 H2B 108.9 . . ? C1 C2 H2C 108.9 . . ? S1 C2 H2C 108.9 . . ? H2B C2 H2C 107.7 . . ? C4 C3 S1 110.71(18) . . ? C4 C3 H3A 109.5 . . ? S1 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? S1 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N1 C4 C3 111.2(2) . . ? N1 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? N1 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? N1 C5 N2 116.9(2) . . ? N1 C5 S2 122.32(18) . . ? N2 C5 S2 120.78(17) . . ? C7 C6 C11 120.3(2) . . ? C7 C6 N2 118.0(2) . . ? C11 C6 N2 121.6(2) . . ? C6 C7 C8 119.9(2) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C9 C8 C7 120.0(2) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 120.0(2) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C11 120.5(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C6 119.4(2) . . ? C10 C11 H11 120.3 . . ? C6 C11 H11 120.3 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.05 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.590 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.065 data_3d _database_code_depnum_ccdc_archive 'CCDC 883640' #TrackingRef '- deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(4-fluorophenyl)thiourea ; _chemical_name_common N,N'-bis(4-fluorophenyl)thiourea _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 F2 N2 S' _chemical_formula_sum 'C13 H10 F2 N2 S' _chemical_formula_weight 264.29 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' F F 0.0171 0.0103 '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 orthorhombic _symmetry_space_group_name_H-M Pnma _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 8.3457(1) _cell_length_b 26.4224(2) _cell_length_c 5.3071(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1170.29(13) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7898 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 31.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.284 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.891 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 8268 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.92 _diffrn_reflns_theta_max 31.00 _reflns_number_total 1882 _reflns_number_gt 1417 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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. ll non-hydrogen atoms were refined acoording to the anisotropic model. Hydrogen atoms were placed in positions calculated from the expected hybridization state of the parent nitrogen or carbon atom. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0369P)^2^+0.2593P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1882 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0924 _refine_ls_wR_factor_gt 0.0856 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.61594(5) 0.2500 0.11976(9) 0.02864(14) Uani 1 2 d S . . F1 F 0.65735(11) 0.48590(3) 0.10741(17) 0.0425(2) Uani 1 1 d . . . N1 N 0.84548(13) 0.29290(4) -0.1583(2) 0.0291(3) Uani 1 1 d . . . H1N H 0.9216(18) 0.2902(6) -0.267(3) 0.043(4) Uiso 1 1 d . . . C0 C 0.7766(2) 0.2500 -0.0746(3) 0.0243(3) Uani 1 2 d S . . C1 C 0.79470(14) 0.34259(4) -0.0864(2) 0.0256(3) Uani 1 1 d . . . C2 C 0.85549(15) 0.36466(5) 0.1302(3) 0.0285(3) Uani 1 1 d . . . H2 H 0.9280 0.3464 0.2342 0.034 Uiso 1 1 calc R . . C3 C 0.80994(15) 0.41358(5) 0.1947(3) 0.0305(3) Uani 1 1 d . . . H3 H 0.8514 0.4295 0.3415 0.037 Uiso 1 1 calc R . . C4 C 0.70343(15) 0.43836(5) 0.0406(3) 0.0293(3) Uani 1 1 d . . . C5 C 0.64133(16) 0.41756(5) -0.1747(3) 0.0324(3) Uani 1 1 d . . . H5 H 0.5679 0.4359 -0.2768 0.039 Uiso 1 1 calc R . . C6 C 0.68908(15) 0.36879(5) -0.2393(3) 0.0293(3) Uani 1 1 d . . . H6 H 0.6491 0.3535 -0.3885 0.035 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 0.0288(2) 0.0234(2) 0.0337(3) 0.000 0.00785(18) 0.000 F1 0.0517(5) 0.0220(4) 0.0538(6) -0.0048(4) -0.0031(4) 0.0088(3) N1 0.0303(5) 0.0214(5) 0.0357(6) 0.0005(4) 0.0100(5) -0.0001(4) C0 0.0252(8) 0.0213(7) 0.0265(9) 0.000 -0.0015(7) 0.000 C1 0.0257(5) 0.0201(5) 0.0310(7) 0.0017(5) 0.0056(5) -0.0013(4) C2 0.0308(6) 0.0260(6) 0.0286(7) 0.0035(5) -0.0002(5) 0.0034(5) C3 0.0334(6) 0.0277(6) 0.0305(7) -0.0016(5) 0.0000(5) 0.0003(5) C4 0.0320(6) 0.0190(5) 0.0370(7) 0.0011(5) 0.0041(6) 0.0018(5) C5 0.0313(6) 0.0274(6) 0.0385(8) 0.0054(6) -0.0043(6) 0.0026(5) C6 0.0284(6) 0.0280(6) 0.0314(7) 0.0002(5) -0.0017(5) -0.0044(5) _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 C0 1.6917(18) . ? F1 C4 1.3605(14) . ? N1 C0 1.3463(14) . ? N1 C1 1.4316(15) . ? N1 H1N 0.861(17) . ? C0 N1 1.3463(14) 7_565 ? C1 C6 1.3836(18) . ? C1 C2 1.3854(18) . ? C2 C3 1.3901(17) . ? C2 H2 0.9500 . ? C3 C4 1.3741(19) . ? C3 H3 0.9500 . ? C4 C5 1.370(2) . ? C5 C6 1.3918(18) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? 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 C0 N1 C1 123.90(11) . . ? C0 N1 H1N 117.8(11) . . ? C1 N1 H1N 118.2(11) . . ? N1 C0 N1 114.68(15) . 7_565 ? N1 C0 S1 122.66(8) . . ? N1 C0 S1 122.66(8) 7_565 . ? C6 C1 C2 120.62(11) . . ? C6 C1 N1 119.42(12) . . ? C2 C1 N1 119.93(11) . . ? C1 C2 C3 119.71(12) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 118.26(13) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? F1 C4 C5 118.74(12) . . ? F1 C4 C3 117.88(13) . . ? C5 C4 C3 123.37(12) . . ? C4 C5 C6 117.95(12) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C1 C6 C5 120.08(13) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.196 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.053 data_4j-form1 _database_code_depnum_ccdc_archive 'CCDC 883641' #TrackingRef '- deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(4-nitrophenyl)-N'-(morpholino)thiourea ; _chemical_name_common N-(4-nitrophenyl)-N'-(morpholino)thiourea _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N3 O3 S' _chemical_formula_sum 'C11 H13 N3 O3 S' _chemical_formula_weight 267.30 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 monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' 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' _cell_length_a 10.2252(2) _cell_length_b 10.5172(3) _cell_length_c 11.1949(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.788(2) _cell_angle_gamma 90.00 _cell_volume 1203.79(5) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5406 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 32.03 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.273 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.865 _exptl_absorpt_correction_T_max 0.953 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 11967 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 32.00 _reflns_number_total 4139 _reflns_number_gt 2986 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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. ll non-hydrogen atoms were refined acoording to the anisotropic model. Hydrogen atoms were placed in positions calculated from the expected hybridization state of the parent nitrogen or carbon atom. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4139 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.08124(3) 0.18288(3) 0.02280(2) 0.02646(9) Uani 1 1 d . . . O3 O -0.19432(7) 0.01785(8) 0.35947(6) 0.02758(18) Uani 1 1 d . . . N1 N -0.13737(8) 0.32202(8) 0.03140(7) 0.02131(19) Uani 1 1 d . . . H1 H -0.1980 0.3570 0.0757 0.026 Uiso 1 1 calc R . . N2 N -0.14387(9) 0.48606(10) -0.44652(7) 0.0269(2) Uani 1 1 d . . . O1 O -0.11795(8) 0.40917(9) -0.52547(6) 0.0331(2) Uani 1 1 d . . . O2 O -0.17488(9) 0.59696(9) -0.46653(7) 0.0383(2) Uani 1 1 d . . . N3 N -0.09474(8) 0.19933(9) 0.19623(8) 0.0247(2) Uani 1 1 d . . . C1 C -0.05671(10) 0.23526(10) 0.08586(8) 0.0206(2) Uani 1 1 d . . . C2 C -0.13255(9) 0.36066(10) -0.08904(8) 0.0198(2) Uani 1 1 d . . . C3 C -0.14783(10) 0.48931(11) -0.11457(8) 0.0234(2) Uani 1 1 d . . . H3 H -0.1567 0.5486 -0.0511 0.028 Uiso 1 1 calc R . . C4 C -0.15018(10) 0.53182(11) -0.23213(9) 0.0240(2) Uani 1 1 d . . . H4 H -0.1605 0.6196 -0.2501 0.029 Uiso 1 1 calc R . . C5 C -0.13710(10) 0.44272(11) -0.32248(8) 0.0219(2) Uani 1 1 d . . . C6 C -0.12165(10) 0.31461(11) -0.29938(9) 0.0233(2) Uani 1 1 d . . . H6 H -0.1124 0.2559 -0.3632 0.028 Uiso 1 1 calc R . . C7 C -0.11974(10) 0.27267(11) -0.18183(9) 0.0222(2) Uani 1 1 d . . . H7 H -0.1098 0.1847 -0.1645 0.027 Uiso 1 1 calc R . . C8 C -0.22741(10) 0.21298(11) 0.24383(9) 0.0251(2) Uani 1 1 d . . . H8A H -0.2855 0.2524 0.1828 0.030 Uiso 1 1 calc R . . H8B H -0.2252 0.2689 0.3150 0.030 Uiso 1 1 calc R . . C9 C -0.27939(10) 0.08392(11) 0.27742(9) 0.0259(2) Uani 1 1 d . . . H9A H -0.3663 0.0942 0.3141 0.031 Uiso 1 1 calc R . . H9B H -0.2908 0.0321 0.2042 0.031 Uiso 1 1 calc R . . C10 C -0.06757(11) 0.00283(12) 0.30836(10) 0.0310(3) Uani 1 1 d . . . H10A H -0.0751 -0.0488 0.2347 0.037 Uiso 1 1 calc R . . H10B H -0.0096 -0.0429 0.3654 0.037 Uiso 1 1 calc R . . C11 C -0.00853(11) 0.13015(12) 0.27913(9) 0.0293(3) Uani 1 1 d . . . H11A H 0.0039 0.1802 0.3533 0.035 Uiso 1 1 calc R . . H11B H 0.0781 0.1178 0.2425 0.035 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 0.02307(14) 0.03064(17) 0.02574(14) 0.00133(10) 0.00286(9) 0.00420(11) O3 0.0287(4) 0.0274(4) 0.0268(4) 0.0081(3) 0.0055(3) 0.0018(3) N1 0.0250(4) 0.0209(5) 0.0181(4) 0.0013(3) 0.0038(3) 0.0040(4) N2 0.0230(4) 0.0366(6) 0.0212(4) 0.0043(4) -0.0005(3) 0.0000(4) O1 0.0379(5) 0.0420(5) 0.0193(4) -0.0027(3) 0.0014(3) -0.0027(4) O2 0.0472(5) 0.0397(5) 0.0282(4) 0.0122(4) 0.0022(3) 0.0134(4) N3 0.0210(4) 0.0294(5) 0.0237(4) 0.0081(4) 0.0012(3) 0.0011(4) C1 0.0225(5) 0.0184(5) 0.0208(4) 0.0002(4) -0.0005(3) -0.0024(4) C2 0.0187(5) 0.0216(5) 0.0190(4) 0.0010(4) -0.0001(3) -0.0005(4) C3 0.0270(5) 0.0223(5) 0.0208(4) -0.0006(4) 0.0012(4) 0.0009(4) C4 0.0261(5) 0.0217(5) 0.0242(5) 0.0034(4) -0.0008(4) 0.0009(4) C5 0.0194(5) 0.0294(6) 0.0169(4) 0.0028(4) -0.0007(3) -0.0006(4) C6 0.0228(5) 0.0268(6) 0.0202(5) -0.0036(4) -0.0001(4) 0.0004(4) C7 0.0234(5) 0.0207(5) 0.0225(5) -0.0003(4) -0.0005(4) -0.0002(4) C8 0.0253(5) 0.0269(6) 0.0231(5) 0.0029(4) 0.0052(4) 0.0036(4) C9 0.0261(5) 0.0287(6) 0.0230(5) 0.0023(4) 0.0031(4) -0.0014(5) C10 0.0317(6) 0.0312(7) 0.0303(5) 0.0071(5) 0.0053(4) 0.0071(5) C11 0.0250(5) 0.0366(7) 0.0261(5) 0.0113(5) -0.0011(4) 0.0011(5) _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 1.6790(11) . ? O3 C10 1.4326(13) . ? O3 C9 1.4357(12) . ? N1 C1 1.3677(13) . ? N1 C2 1.4097(12) . ? N1 H1 0.8800 . ? N2 O2 1.2285(13) . ? N2 O1 1.2296(13) . ? N2 C5 1.4623(12) . ? N3 C1 1.3542(13) . ? N3 C11 1.4646(13) . ? N3 C8 1.4713(13) . ? C2 C3 1.3913(15) . ? C2 C7 1.3986(14) . ? C3 C4 1.3899(13) . ? C3 H3 0.9500 . ? C4 C5 1.3866(15) . ? C4 H4 0.9500 . ? C5 C6 1.3807(15) . ? C6 C7 1.3878(14) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.5073(16) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5067(17) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? 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 C10 O3 C9 109.96(8) . . ? C1 N1 C2 126.15(9) . . ? C1 N1 H1 116.9 . . ? C2 N1 H1 116.9 . . ? O2 N2 O1 123.44(9) . . ? O2 N2 C5 118.54(9) . . ? O1 N2 C5 118.02(10) . . ? C1 N3 C11 122.61(9) . . ? C1 N3 C8 125.52(9) . . ? C11 N3 C8 111.65(8) . . ? N3 C1 N1 114.45(9) . . ? N3 C1 S1 123.06(8) . . ? N1 C1 S1 122.44(7) . . ? C3 C2 C7 120.16(9) . . ? C3 C2 N1 118.13(9) . . ? C7 C2 N1 121.63(10) . . ? C4 C3 C2 120.51(10) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 118.22(10) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? C6 C5 C4 122.33(9) . . ? C6 C5 N2 119.07(9) . . ? C4 C5 N2 118.57(10) . . ? C5 C6 C7 119.20(10) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C6 C7 C2 119.58(10) . . ? C6 C7 H7 120.2 . . ? C2 C7 H7 120.2 . . ? N3 C8 C9 109.42(9) . . ? N3 C8 H8A 109.8 . . ? C9 C8 H8A 109.8 . . ? N3 C8 H8B 109.8 . . ? C9 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? O3 C9 C8 112.51(9) . . ? O3 C9 H9A 109.1 . . ? C8 C9 H9A 109.1 . . ? O3 C9 H9B 109.1 . . ? C8 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? O3 C10 C11 110.86(10) . . ? O3 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? O3 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? N3 C11 C10 109.86(9) . . ? N3 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? N3 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 32.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.258 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.053 data_4j-form2 _database_code_depnum_ccdc_archive 'CCDC 883642' #TrackingRef '- deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(4-nitrophenyl)-N'-(morpholino)thiourea ; _chemical_formula_moiety 'C11 H13 N3 O3 S1' _chemical_formula_sum 'C11 H13 N3 O3 S1' _chemical_formula_weight 267.30 _cell_formula_units_Z 16 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 21.2213(10) _cell_length_b 8.0908(4) _cell_length_c 28.6471(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4918.6(4) _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2240 _exptl_absorpt_coefficient_mu 0.268 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The crystal, even with very long exposure time for each frame, diffracted very poorly at higher resolution. This is the cause of slightly unrealistic thermal behaviour of neighbouring atoms. ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35514 _diffrn_reflns_av_R_equivalents 0.1164 _diffrn_reflns_av_sigmaI/netI 0.1907 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 26.00 _reflns_number_total 9571 _reflns_number_gt 3615 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution SHELXS-97 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details ; calc [0.00000+1.00000exp(4.00(sin\q/\l)^2^)]/ [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0417P)^2^+0.0000sin\q/\l] where P = 0.33333Fo^2^ + 0.66667Fc^2^ ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.49(11) _refine_ls_number_reflns 9571 _refine_ls_number_parameters 650 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1498 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1249 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean <0.001 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 H2 H 0.0351 0.0382 0.4061 0.050 Uiso 1 1 d D . . H22 H 0.3033 0.9829 0.1183 0.050 Uiso 1 1 d D . . H42 H -0.2934 -0.4576 0.6237 0.050 Uiso 1 1 d D . . H62 H 0.0388 -0.4953 0.3975 0.050 Uiso 1 1 d D . . S1 S 0.07185(8) 0.3484(2) 0.47700(7) 0.0435(4) Uani 1 1 d . . . S6 S -0.04829(8) -0.1501(2) 0.37100(7) 0.0487(5) Uani 1 1 d . . . S4 S -0.20561(8) -0.1342(2) 0.65470(7) 0.0498(5) Uani 1 1 d . . . C1 C 0.0558(3) 0.1510(8) 0.4616(3) 0.0385(19) Uani 1 1 d . . . N41 N -0.1812(2) -0.4442(8) 0.6322(2) 0.0364(15) Uani 1 1 d . . . N61 N -0.0757(3) -0.4617(8) 0.3949(3) 0.0394(16) Uani 1 1 d . . . O1 O -0.0345(2) -0.1805(5) 0.54954(17) 0.0542(14) Uani 1 1 d . . . N1 N 0.0332(3) 0.0384(7) 0.4915(2) 0.0360(16) Uani 1 1 d . . . N62 N 0.0302(2) -0.4038(5) 0.38589(18) 0.0391(14) Uani 1 1 d D . . O61 O -0.1633(2) -0.6771(6) 0.4370(2) 0.0585(14) Uani 1 1 d . . . N2 N 0.0646(2) 0.0952(6) 0.41666(19) 0.0355(13) Uani 1 1 d D . . O41 O -0.0922(2) -0.6738(6) 0.5946(2) 0.0599(15) Uani 1 1 d . . . C2 C 0.0370(3) -0.1398(8) 0.4850(3) 0.0412(19) Uani 1 1 d . . . H2A H 0.0726 -0.1835 0.5023 0.049 Uiso 1 1 calc R . . H2B H 0.0433 -0.1648 0.4522 0.049 Uiso 1 1 calc R . . C9 C 0.1679(3) 0.3262(8) 0.3123(3) 0.0410(17) Uani 1 1 d . . . N42 N -0.2850(2) -0.3853(6) 0.64343(18) 0.0399(14) Uani 1 1 d D . . C65 C -0.0668(4) -0.6393(8) 0.3936(3) 0.046(2) Uani 1 1 d . . . H65A H -0.0221 -0.6646 0.3938 0.055 Uiso 1 1 calc R . . H65B H -0.0848 -0.6836 0.3651 0.055 Uiso 1 1 calc R . . C41 C -0.2244(3) -0.3321(7) 0.6440(2) 0.0312(16) Uani 1 1 d . . . C67 C 0.1387(3) -0.3201(8) 0.3915(2) 0.0360(17) Uani 1 1 d . . . H67 H 0.1394 -0.3648 0.4214 0.043 Uiso 1 1 calc R . . C6 C 0.1011(3) 0.1759(7) 0.3818(2) 0.0305(15) Uani 1 1 d . . . C11 C 0.1605(4) 0.2340(10) 0.3912(3) 0.048(2) Uani 1 1 d . . . H11 H 0.1777 0.2234 0.4210 0.058 Uiso 1 1 calc R . . C42 C -0.1895(3) -0.6226(9) 0.6370(3) 0.045(2) Uani 1 1 d . . . H42A H -0.2341 -0.6486 0.6367 0.053 Uiso 1 1 calc R . . H42B H -0.1722 -0.6586 0.6666 0.053 Uiso 1 1 calc R . . C66 C 0.0838(3) -0.3246(7) 0.3661(2) 0.0335(15) Uani 1 1 d D . . C47 C -0.3955(3) -0.3055(8) 0.6374(3) 0.042(2) Uani 1 1 d . . . H47 H -0.3972 -0.3561 0.6083 0.050 Uiso 1 1 calc R . . C61 C -0.0313(3) -0.3471(8) 0.3842(2) 0.0371(18) Uani 1 1 d D . . O2 O 0.2528(4) 0.4737(9) 0.2870(4) 0.106(3) Uani 1 1 d . . . N63 N 0.2471(4) -0.0978(9) 0.3115(3) 0.067(2) Uani 1 1 d . . . C69 C 0.1899(3) -0.1826(8) 0.3299(2) 0.0412(17) Uani 1 1 d . . . C49 C -0.4447(3) -0.1575(8) 0.6973(3) 0.0471(19) Uani 1 1 d . . . C7 C 0.0757(3) 0.1888(9) 0.3373(3) 0.0383(19) Uani 1 1 d . . . H7 H 0.0357 0.1478 0.3310 0.046 Uiso 1 1 calc R . . C4 C -0.0422(4) -0.0065(8) 0.5530(4) 0.043(2) Uani 1 1 d . . . H4A H -0.0538 0.0221 0.5847 0.051 Uiso 1 1 calc R . . H4B H -0.0761 0.0283 0.5325 0.051 Uiso 1 1 calc R . . C50 C -0.3902(3) -0.1546(9) 0.7242(3) 0.055(2) Uani 1 1 d . . . H50 H -0.3897 -0.1039 0.7533 0.065 Uiso 1 1 calc R . . N43 N -0.5001(4) -0.0751(11) 0.7168(4) 0.076(2) Uani 1 1 d . . . C46 C -0.3387(3) -0.3035(8) 0.6623(3) 0.0401(17) Uani 1 1 d . . . C44 C -0.0866(4) -0.5012(8) 0.5890(4) 0.041(3) Uani 1 1 d . . . H44A H -0.1073 -0.4694 0.5602 0.049 Uiso 1 1 calc R . . H44B H -0.0423 -0.4737 0.5859 0.049 Uiso 1 1 calc R . . N3 N 0.2033(4) 0.4206(9) 0.2766(3) 0.066(2) Uani 1 1 d . . . C62 C -0.1420(3) -0.4162(9) 0.3985(3) 0.050(2) Uani 1 1 d . . . H62A H -0.1638 -0.4474 0.3701 0.061 Uiso 1 1 calc R . . H62B H -0.1457 -0.2974 0.4022 0.061 Uiso 1 1 calc R . . C63 C -0.1722(4) -0.5024(7) 0.4400(5) 0.052(3) Uani 1 1 d . . . H63A H -0.1535 -0.4614 0.4687 0.062 Uiso 1 1 calc R . . H63B H -0.2169 -0.4777 0.4407 0.062 Uiso 1 1 calc R . . C5 C 0.0171(4) 0.0832(8) 0.5400(2) 0.0494(19) Uani 1 1 d . . . H5A H 0.0108 0.2016 0.5424 0.059 Uiso 1 1 calc R . . H5B H 0.0511 0.0519 0.5608 0.059 Uiso 1 1 calc R . . C8 C 0.1104(4) 0.2627(9) 0.3026(3) 0.048(2) Uani 1 1 d . . . H8 H 0.0944 0.2691 0.2724 0.058 Uiso 1 1 calc R . . C68 C 0.1929(4) -0.2506(9) 0.3735(3) 0.048(2) Uani 1 1 d . . . H68 H 0.2303 -0.2501 0.3904 0.057 Uiso 1 1 calc R . . O63 O 0.2434(4) -0.0376(9) 0.2732(3) 0.089(3) Uani 1 1 d . . . C45 C -0.1136(3) -0.4024(9) 0.6279(3) 0.054(2) Uani 1 1 d . . . H45A H -0.0919 -0.4278 0.6569 0.064 Uiso 1 1 calc R . . H45B H -0.1087 -0.2853 0.6216 0.064 Uiso 1 1 calc R . . C64 C -0.0980(3) -0.7186(9) 0.4352(3) 0.058(2) Uani 1 1 d . . . H64A H -0.0934 -0.8377 0.4333 0.069 Uiso 1 1 calc R . . H64B H -0.0774 -0.6815 0.4636 0.069 Uiso 1 1 calc R . . O3 O 0.1754(4) 0.4475(11) 0.2397(3) 0.106(3) Uani 1 1 d . . . C71 C 0.0831(4) -0.2582(9) 0.3221(3) 0.046(2) Uani 1 1 d . . . H71 H 0.0461 -0.2607 0.3047 0.055 Uiso 1 1 calc R . . C48 C -0.4463(3) -0.2368(9) 0.6547(3) 0.0397(19) Uani 1 1 d . . . H48 H -0.4839 -0.2415 0.6381 0.048 Uiso 1 1 calc R . . C70 C 0.1355(4) -0.1892(9) 0.3039(3) 0.051(2) Uani 1 1 d . . . H70 H 0.1348 -0.1462 0.2738 0.061 Uiso 1 1 calc R . . O43 O -0.4956(5) 0.0068(8) 0.7523(4) 0.092(3) Uani 1 1 d . . . C51 C -0.3369(4) -0.2293(9) 0.7062(3) 0.042(2) Uani 1 1 d . . . H51 H -0.2997 -0.2301 0.7235 0.050 Uiso 1 1 calc R . . O42 O -0.5485(4) -0.0877(13) 0.6952(3) 0.131(3) Uani 1 1 d . . . C10 C 0.1945(3) 0.3087(9) 0.3557(3) 0.048(2) Uani 1 1 d . . . H10 H 0.2352 0.3469 0.3612 0.057 Uiso 1 1 calc R . . O62 O 0.2945(3) -0.1011(12) 0.3352(3) 0.121(3) Uani 1 1 d . . . C3 C -0.0234(4) -0.2200(9) 0.5020(3) 0.053(2) Uani 1 1 d . . . H3A H -0.0585 -0.1817 0.4832 0.064 Uiso 1 1 calc R . . H3B H -0.0203 -0.3389 0.4985 0.064 Uiso 1 1 calc R . . C43 C -0.1573(4) -0.7139(9) 0.5978(3) 0.065(2) Uani 1 1 d . . . H43A H -0.1617 -0.8319 0.6028 0.078 Uiso 1 1 calc R . . H43B H -0.1778 -0.6867 0.5685 0.078 Uiso 1 1 calc R . . S2 S 0.32661(8) 0.6415(2) 0.05036(7) 0.0440(4) Uani 1 1 d . . . C21 C 0.3122(3) 0.8376(8) 0.0659(2) 0.0283(15) Uani 1 1 d . . . N21 N 0.2893(3) 0.9528(8) 0.0360(2) 0.0351(15) Uani 1 1 d . . . C22 C 0.2942(3) 1.1305(8) 0.0434(3) 0.040(2) Uani 1 1 d . . . H22A H 0.3308 1.1730 0.0271 0.048 Uiso 1 1 calc R . . H22B H 0.2994 1.1530 0.0765 0.048 Uiso 1 1 calc R . . O21 O 0.2251(2) 1.1783(5) -0.02203(18) 0.0557(13) Uani 1 1 d . . . C29 C 0.4220(4) 0.6525(8) 0.2147(3) 0.0466(18) Uani 1 1 d . . . N22 N 0.3205(2) 0.8936(6) 0.11078(19) 0.0410(15) Uani 1 1 d D . . C27 C 0.3296(3) 0.7886(9) 0.1908(3) 0.043(2) Uani 1 1 d . . . H27 H 0.2897 0.8301 0.1973 0.052 Uiso 1 1 calc R . . C25 C 0.2732(3) 0.9089(8) -0.0127(2) 0.0416(17) Uani 1 1 d . . . H25A H 0.2637 0.7918 -0.0145 0.050 Uiso 1 1 calc R . . H25B H 0.3091 0.9308 -0.0327 0.050 Uiso 1 1 calc R . . C31 C 0.4161(3) 0.7541(9) 0.1382(3) 0.041(2) Uani 1 1 d . . . H31 H 0.4343 0.7710 0.1090 0.049 Uiso 1 1 calc R . . O23 O 0.5111(4) 0.5047(7) 0.2407(3) 0.075(2) Uani 1 1 d . . . C24 C 0.2182(4) 1.0050(6) -0.0294(4) 0.040(2) Uani 1 1 d . . . H24A H 0.2123 0.9845 -0.0625 0.048 Uiso 1 1 calc R . . H24B H 0.1807 0.9670 -0.0133 0.048 Uiso 1 1 calc R . . C26 C 0.3552(3) 0.8095(8) 0.1459(2) 0.0362(16) Uani 1 1 d . . . N23 N 0.4577(4) 0.5599(10) 0.2509(3) 0.070(2) Uani 1 1 d . . . C30 C 0.4500(3) 0.6765(9) 0.1715(3) 0.050(2) Uani 1 1 d . . . H30 H 0.4908 0.6403 0.1656 0.059 Uiso 1 1 calc R . . O22 O 0.4360(4) 0.5424(11) 0.2889(3) 0.113(3) Uani 1 1 d . . . C28 C 0.3621(4) 0.7092(10) 0.2246(3) 0.051(2) Uani 1 1 d . . . H28 H 0.3445 0.6932 0.2540 0.062 Uiso 1 1 calc R . . C23 C 0.2354(4) 1.2156(8) 0.0256(3) 0.054(2) Uani 1 1 d . . . H23A H 0.1994 1.1799 0.0438 0.065 Uiso 1 1 calc R . . H23B H 0.2398 1.3342 0.0294 0.065 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 0.0531(10) 0.0343(9) 0.0429(11) 0.0010(10) -0.0018(9) -0.0047(9) S6 0.0460(10) 0.0373(9) 0.0628(13) 0.0080(10) -0.0052(10) 0.0007(9) S4 0.0460(10) 0.0360(9) 0.0673(13) -0.0058(10) -0.0007(10) -0.0007(8) C1 0.034(4) 0.034(4) 0.047(5) -0.003(4) -0.014(4) -0.004(3) N41 0.024(3) 0.042(3) 0.044(4) 0.006(4) -0.002(3) 0.002(3) N61 0.020(3) 0.041(3) 0.057(5) 0.007(3) 0.003(3) 0.003(3) O1 0.074(4) 0.039(3) 0.049(3) 0.002(3) 0.028(3) -0.018(2) N1 0.042(4) 0.035(3) 0.031(4) -0.004(3) 0.014(3) -0.004(3) N62 0.032(3) 0.032(3) 0.054(4) 0.007(3) 0.001(3) -0.003(2) O61 0.043(3) 0.045(3) 0.088(4) 0.004(3) 0.015(3) -0.004(2) N2 0.042(3) 0.034(3) 0.031(3) -0.002(3) 0.007(3) -0.009(3) O41 0.039(3) 0.041(3) 0.100(4) 0.003(3) 0.018(3) 0.000(2) C2 0.054(5) 0.039(4) 0.031(5) 0.004(4) 0.004(4) 0.005(4) C9 0.047(4) 0.039(4) 0.037(4) -0.005(3) 0.013(4) 0.000(3) N42 0.026(3) 0.041(3) 0.053(4) -0.012(3) -0.005(3) -0.003(2) C65 0.048(4) 0.032(4) 0.057(5) -0.005(4) 0.012(4) -0.005(4) C41 0.031(3) 0.029(4) 0.033(4) 0.005(3) -0.001(3) 0.000(3) C67 0.038(4) 0.041(4) 0.029(4) 0.001(3) -0.002(3) 0.001(3) C6 0.031(3) 0.030(4) 0.031(4) 0.000(3) 0.000(3) 0.005(3) C11 0.046(5) 0.057(5) 0.042(5) 0.001(4) 0.007(4) -0.011(4) C42 0.038(4) 0.045(5) 0.050(5) -0.001(4) 0.003(4) 0.001(4) C66 0.040(4) 0.031(4) 0.029(4) -0.007(3) 0.003(3) 0.000(3) C47 0.040(4) 0.042(4) 0.043(5) -0.001(4) -0.007(4) -0.009(4) C61 0.042(4) 0.039(4) 0.030(4) -0.003(3) -0.012(3) 0.010(4) O2 0.076(5) 0.123(6) 0.118(8) 0.012(5) 0.043(5) -0.052(5) N63 0.066(5) 0.079(6) 0.056(5) 0.001(4) 0.020(5) -0.003(4) C69 0.042(4) 0.044(4) 0.037(4) -0.003(3) 0.015(4) -0.001(3) C49 0.038(4) 0.042(4) 0.061(5) 0.014(4) 0.012(4) 0.016(4) C7 0.040(4) 0.044(4) 0.031(5) 0.002(4) 0.002(3) 0.000(3) C4 0.038(4) 0.051(5) 0.038(6) -0.006(3) 0.024(4) 0.002(3) C50 0.063(5) 0.053(5) 0.047(5) -0.005(4) 0.017(4) 0.003(4) N43 0.044(5) 0.088(6) 0.096(7) 0.021(5) 0.026(5) 0.024(4) C46 0.031(4) 0.040(4) 0.049(5) 0.004(4) 0.010(4) -0.004(3) C44 0.022(4) 0.044(5) 0.057(8) 0.003(3) 0.001(4) 0.002(3) N3 0.084(6) 0.053(5) 0.060(6) -0.010(4) 0.034(5) -0.007(4) C62 0.044(4) 0.040(4) 0.067(6) 0.005(4) -0.007(4) 0.011(3) C63 0.048(5) 0.033(5) 0.075(9) -0.007(4) 0.021(5) 0.005(3) C5 0.075(5) 0.038(4) 0.035(5) 0.004(4) -0.005(4) -0.003(4) C8 0.056(5) 0.060(5) 0.029(5) -0.001(4) -0.002(4) -0.003(4) C68 0.024(4) 0.050(5) 0.069(7) 0.003(5) 0.002(4) 0.006(3) O63 0.093(6) 0.115(5) 0.060(6) 0.029(5) 0.036(5) -0.004(4) C45 0.029(4) 0.058(5) 0.074(6) -0.016(5) 0.006(4) 0.002(3) C64 0.041(4) 0.041(4) 0.091(6) 0.026(4) 0.019(4) 0.007(3) O3 0.134(7) 0.130(6) 0.055(6) 0.022(5) 0.019(5) -0.039(5) C71 0.040(5) 0.055(5) 0.042(6) 0.005(4) -0.009(4) -0.005(4) C48 0.033(4) 0.054(5) 0.032(5) 0.004(4) -0.006(4) 0.005(3) C70 0.059(5) 0.067(5) 0.026(4) 0.000(4) 0.017(4) 0.002(4) O43 0.104(6) 0.088(5) 0.083(7) -0.015(4) 0.045(6) 0.023(4) C51 0.046(5) 0.045(4) 0.036(6) -0.007(4) -0.009(4) -0.005(4) O42 0.071(5) 0.194(8) 0.128(7) -0.033(7) 0.017(5) 0.068(6) C10 0.041(4) 0.053(5) 0.048(6) -0.006(4) 0.001(4) -0.017(4) O62 0.058(4) 0.195(9) 0.109(6) 0.040(6) -0.004(4) -0.038(5) C3 0.075(5) 0.033(4) 0.052(5) -0.006(4) 0.019(4) -0.011(4) C43 0.054(5) 0.039(4) 0.102(7) 0.003(4) 0.022(5) -0.005(4) S2 0.0564(11) 0.0316(9) 0.0439(11) 0.0002(9) 0.0028(9) 0.0079(9) C21 0.026(3) 0.033(4) 0.026(4) 0.000(3) -0.002(3) -0.008(3) N21 0.039(4) 0.042(3) 0.025(4) 0.004(3) 0.004(3) 0.005(3) C22 0.042(4) 0.032(4) 0.046(5) 0.006(4) 0.004(4) 0.003(3) O21 0.079(4) 0.039(3) 0.049(3) -0.004(3) -0.007(3) 0.002(3) C29 0.057(5) 0.038(4) 0.046(5) -0.002(4) -0.017(4) 0.002(4) N22 0.052(4) 0.040(3) 0.031(3) -0.003(3) -0.002(3) 0.010(3) C27 0.031(4) 0.050(4) 0.050(6) -0.012(4) 0.009(4) 0.009(3) C25 0.050(4) 0.042(4) 0.033(4) -0.006(3) -0.009(4) 0.004(3) C31 0.034(4) 0.058(5) 0.031(5) 0.007(4) 0.023(4) 0.009(4) O23 0.065(4) 0.095(5) 0.064(6) 0.002(3) -0.025(4) 0.024(3) C24 0.051(5) 0.026(4) 0.041(6) 0.001(3) 0.008(4) 0.003(3) C26 0.035(4) 0.034(4) 0.039(4) -0.002(3) -0.012(3) 0.000(3) N23 0.081(6) 0.073(5) 0.054(6) 0.004(4) -0.032(5) 0.000(5) C30 0.025(4) 0.061(5) 0.063(6) -0.001(5) -0.009(4) 0.005(4) O22 0.128(7) 0.178(7) 0.032(5) 0.022(5) -0.008(5) 0.032(5) C28 0.062(6) 0.059(5) 0.033(5) -0.002(4) -0.007(4) 0.000(4) C23 0.077(6) 0.037(4) 0.048(5) -0.010(4) -0.011(5) 0.019(4) _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 1.692(7) . ? S6 C61 1.677(7) . ? S4 C41 1.678(6) . ? C1 N1 1.339(9) . ? C1 N2 1.377(8) . ? N41 C41 1.334(8) . ? N41 C42 1.461(9) . ? N41 C45 1.478(8) . ? N61 C61 1.356(9) . ? N61 C65 1.450(8) . ? N61 C62 1.459(8) . ? O1 C3 1.419(8) . ? O1 C4 1.421(7) . ? N1 C2 1.456(8) . ? N1 C5 1.475(9) . ? N62 C61 1.386(8) . ? N62 C66 1.423(7) . ? O61 C64 1.427(7) . ? O61 C63 1.428(7) . ? N2 C6 1.422(8) . ? O41 C44 1.411(8) . ? O41 C43 1.421(8) . ? C2 C3 1.517(9) . ? C9 C8 1.351(9) . ? C9 C10 1.374(10) . ? C9 N3 1.480(9) . ? N42 C41 1.356(7) . ? N42 C46 1.424(8) . ? C65 C64 1.507(10) . ? C67 C66 1.374(8) . ? C67 C68 1.380(10) . ? C6 C11 1.374(9) . ? C6 C7 1.389(9) . ? C11 C10 1.387(10) . ? C42 C43 1.507(11) . ? C66 C71 1.369(10) . ? C47 C48 1.310(10) . ? C47 C46 1.401(9) . ? O2 N3 1.173(11) . ? N63 O63 1.204(11) . ? N63 O62 1.213(8) . ? N63 C69 1.489(9) . ? C69 C68 1.367(11) . ? C69 C70 1.374(9) . ? C49 C48 1.380(10) . ? C49 C50 1.387(9) . ? C49 N43 1.463(9) . ? C7 C8 1.374(10) . ? C4 C5 1.500(10) . ? C50 C51 1.383(10) . ? N43 O42 1.205(10) . ? N43 O43 1.217(12) . ? C46 C51 1.394(10) . ? C44 C45 1.488(12) . ? N3 O3 1.232(11) . ? C62 C63 1.519(14) . ? C71 C70 1.349(10) . ? S2 C21 1.676(6) . ? C21 N21 1.357(8) . ? C21 N22 1.375(8) . ? N21 C22 1.457(8) . ? N21 C25 1.479(9) . ? C22 C23 1.513(9) . ? O21 C23 1.415(8) . ? O21 C24 1.426(7) . ? C29 C28 1.381(11) . ? C29 C30 1.386(10) . ? C29 N23 1.487(10) . ? N22 C26 1.419(8) . ? C27 C28 1.353(10) . ? C27 C26 1.406(10) . ? C25 C24 1.482(10) . ? C31 C30 1.349(10) . ? C31 C26 1.386(9) . ? O23 N23 1.253(10) . ? N23 O22 1.191(11) . ? 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 N1 C1 N2 115.0(6) . . ? N1 C1 S1 123.2(6) . . ? N2 C1 S1 121.8(6) . . ? C41 N41 C42 124.4(5) . . ? C41 N41 C45 122.2(6) . . ? C42 N41 C45 110.6(6) . . ? C61 N61 C65 125.6(6) . . ? C61 N61 C62 120.8(6) . . ? C65 N61 C62 112.2(6) . . ? C3 O1 C4 108.0(6) . . ? C1 N1 C2 124.8(6) . . ? C1 N1 C5 121.2(6) . . ? C2 N1 C5 112.1(6) . . ? C61 N62 C66 126.2(5) . . ? C64 O61 C63 111.3(6) . . ? C1 N2 C6 125.4(5) . . ? C44 O41 C43 108.4(5) . . ? N1 C2 C3 109.6(6) . . ? C8 C9 C10 121.2(7) . . ? C8 C9 N3 120.9(8) . . ? C10 C9 N3 117.9(7) . . ? C41 N42 C46 127.3(5) . . ? N61 C65 C64 110.2(6) . . ? N41 C41 N42 115.7(5) . . ? N41 C41 S4 122.1(5) . . ? N42 C41 S4 122.1(5) . . ? C66 C67 C68 121.3(7) . . ? C11 C6 C7 120.7(7) . . ? C11 C6 N2 121.3(6) . . ? C7 C6 N2 118.0(6) . . ? C6 C11 C10 118.8(8) . . ? N41 C42 C43 111.1(6) . . ? C71 C66 C67 119.1(6) . . ? C71 C66 N62 122.3(6) . . ? C67 C66 N62 118.6(6) . . ? C48 C47 C46 120.8(7) . . ? N61 C61 N62 114.8(6) . . ? N61 C61 S6 123.5(5) . . ? N62 C61 S6 121.7(5) . . ? O63 N63 O62 124.9(8) . . ? O63 N63 C69 117.1(8) . . ? O62 N63 C69 117.9(8) . . ? C68 C69 C70 121.1(7) . . ? C68 C69 N63 118.0(7) . . ? C70 C69 N63 120.8(7) . . ? C48 C49 C50 121.3(6) . . ? C48 C49 N43 122.0(8) . . ? C50 C49 N43 116.8(8) . . ? C8 C7 C6 119.3(7) . . ? O1 C4 C5 111.5(6) . . ? C51 C50 C49 117.9(7) . . ? O42 N43 O43 122.9(9) . . ? O42 N43 C49 116.8(10) . . ? O43 N43 C49 120.2(9) . . ? C51 C46 C47 119.2(7) . . ? C51 C46 N42 121.4(6) . . ? C47 C46 N42 119.3(6) . . ? O41 C44 C45 114.5(8) . . ? O2 N3 O3 125.6(9) . . ? O2 N3 C9 118.0(10) . . ? O3 N3 C9 116.1(9) . . ? N61 C62 C63 110.2(6) . . ? O61 C63 C62 110.6(8) . . ? N1 C5 C4 108.0(6) . . ? C9 C8 C7 120.0(8) . . ? C69 C68 C67 117.8(8) . . ? N41 C45 C44 108.2(6) . . ? O61 C64 C65 110.8(6) . . ? C70 C71 C66 120.5(7) . . ? C47 C48 C49 120.7(7) . . ? C71 C70 C69 120.0(7) . . ? C50 C51 C46 120.1(7) . . ? C9 C10 C11 119.7(7) . . ? O1 C3 C2 110.7(6) . . ? O41 C43 C42 112.2(7) . . ? N21 C21 N22 114.2(6) . . ? N21 C21 S2 123.2(5) . . ? N22 C21 S2 122.5(5) . . ? C21 N21 C22 124.1(6) . . ? C21 N21 C25 120.9(6) . . ? C22 N21 C25 113.0(6) . . ? N21 C22 C23 109.9(6) . . ? C23 O21 C24 111.6(6) . . ? C28 C29 C30 122.1(7) . . ? C28 C29 N23 119.5(8) . . ? C30 C29 N23 118.4(7) . . ? C21 N22 C26 124.8(5) . . ? C28 C27 C26 121.1(7) . . ? N21 C25 C24 111.1(6) . . ? C30 C31 C26 122.3(7) . . ? O21 C24 C25 112.8(7) . . ? C31 C26 C27 117.8(7) . . ? C31 C26 N22 121.7(6) . . ? C27 C26 N22 120.4(6) . . ? O22 N23 O23 121.4(9) . . ? O22 N23 C29 120.0(9) . . ? O23 N23 C29 118.5(9) . . ? C31 C30 C29 118.0(7) . . ? C27 C28 C29 118.6(8) . . ? O21 C23 C22 110.8(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.585 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.049 _vrf_PLAT340_4j-form2 ; PROBLEM: Low Bond Precision on C-C Bonds ............... 0.0110 Ang RESPONSE: The crystal diffracted very poorly at higher diffraction angles. ; _vrf_PLAT026_4j-form2 ; PROBLEM: Ratio Observed / Unique Reflections too Low .... 38 Perc. RESPONSE: The crystal diffracted very poorly at higher diffraction angles. ; _chemical_name_common N-(4-nitrophenyl)-N'-(morpholino)thiourea data_2m _database_code_depnum_ccdc_archive 'CCDC 883643' #TrackingRef '- deposit.cif' _chemical_formula_sum 'C15 H16 N2 S1' _chemical_formula_weight 256.37 _chemical_formula_moiety 'C15 H16 N2 S1' _cell_formula_units_Z 4 _cell_length_a 12.67213(25) _cell_length_b 9.79731(27) _cell_length_c 12.10093(31) _cell_angle_alpha 90 _cell_angle_beta 115.2231(14) _cell_angle_gamma 90 _cell_volume 1359.122(61) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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' _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Cu K\a_1' _diffrn_radiation_wavelength 1.54059 _exptl_crystal_density_diffrn 1.253 _refine_ls_hydrogen_treatment mixed _refine_ls_shift/su_max <0.01 _refine_ls_number_parameters 141 _pd_proc_ls_prof_R_factor 0.0293 _pd_proc_ls_prof_wR_factor 0.0406 _refine_ls_R_Fsqd_factor 0.0123 _refine_ls_goodness_of_fit_all 0.571 _cell_measurement_temperature 293 _exptl_crystal_colour ? _refine_ls_structure_factor_coef Fsqd _computing_data_collection PAnalytical _computing_data_reduction none _computing_cell_refinement Topas _computing_structure_solution 'simulated annealing in DASH and Topas' _computing_structure_refinement Topas _refine_special_details ; The patterns was collected on a flat sample in Bragg-Brentano geometry giving slight prefered orientation which was modelled with spherical harmonics intensity correction of the 4th order. The crystal structure (all atoms) was refined with restraints on bond lenghts and angles as well as planarity restraints. ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv H1 H 4 0.0636(11) 0.3810(11) -0.0594(12) 1 3.76(14) C2 C 4 0.13982(29) 0.38153(18) 0.01077(36) 1 3.76(14) C3 C 4 0.19531(25) 0.50705(23) 0.05471(32) 1 3.76(14) H4 H 4 0.15820(73) 0.5947(11) 0.01660(95) 1 3.76(14) C5 C 4 0.30140(26) 0.50964(22) 0.15406(32) 1 3.76(14) H6 H 4 0.34053(74) 0.5979(11) 0.18295(83) 1 3.76(14) C7 C 4 0.35167(34) 0.38836(22) 0.21197(36) 1 3.76(14) H8 H 4 0.4281(11) 0.3908(12) 0.2805(10) 1 3.76(14) C9 C 4 0.29903(22) 0.26517(23) 0.17046(29) 1 3.76(14) H10 H 4 0.33710(74) 0.1819(12) 0.21139(91) 1 3.76(14) C11 C 4 0.19148(22) 0.25992(20) 0.07027(28) 1 3.76(14) N12 N 4 0.13474(18) 0.13322(20) 0.02870(13) 1 3.76(14) C13 C 4 0.17362(17) 0.02030(19) -0.01726(18) 1 3.76(14) N14 N 4 0.28642(15) 0.03799(26) -0.00410(23) 1 3.76(14) S15 S 4 0.11416(21) -0.13397(22) -0.04471(24) 1 3.76(14) H16 H 4 0.41384(70) -0.2381(12) -0.22501(87) 1 3.76(14) C17 C 4 0.41613(23) -0.21433(24) -0.14643(18) 1 3.76(14) C18 C 4 0.35015(24) -0.10507(25) -0.13306(22) 1 3.76(14) C19 C 4 0.27388(21) -0.02013(26) -0.24468(19) 1 3.76(14) C20 C 4 0.35935(27) -0.06922(32) -0.01482(20) 1 3.76(14) C21 C 4 0.42771(21) -0.14855(25) 0.08723(19) 1 3.76(14) C22 C 4 0.44179(18) -0.10803(22) 0.21405(16) 1 3.76(14) C23 C 4 0.49295(24) -0.25758(28) 0.07145(18) 1 3.76(14) H24 H 4 0.54549(74) -0.3116(11) 0.14294(83) 1 3.76(14) C25 C 4 0.48841(28) -0.28843(30) -0.04498(19) 1 3.76(14) H26 H 4 0.53303(86) -0.3631(10) -0.05490(78) 1 3.76(14) H27 H 4 0.29198(79) -0.0400(10) -0.31308(76) 1 3.76(14) H28 H 4 0.19096(74) -0.0413(11) -0.26958(73) 1 3.76(14) H29 H 4 0.28657(80) 0.0784(11) -0.22764(77) 1 3.76(14) H32 H 4 0.38189(76) -0.0451(12) 0.21129(75) 1 3.76(14) H33 H 4 0.43499(68) -0.1881(13) 0.25935(78) 1 3.76(14) H34 H 4 0.51870(69) -0.0653(13) 0.26112(72) 1 3.76(14) H30 H 4 0.31897(68) 0.1293(10) 0.01311(80) 1 3.76(14) H31 H 4 0.06855(74) 0.1174(10) 0.04447(90) 1 3.76(14) _vrf_ATOM006_2m ; PROBLEM: _atom_site_U_iso_or_equiv is missing RESPONSE: Displacement parameters are reported as Biso. ; _vrf_GEOM001_2m ; PROBLEM: _geom_bond_atom_site_label_1 is missing RESPONSE: Bonds and angles not calculated. ; _vrf_GEOM003_2m ; PROBLEM: _geom_bond_distance is missing RESPONSE: Bonds and angles not calculated. ; _vrf_GEOM006_2m ; PROBLEM: _geom_angle_atom_site_label_2 is missing RESPONSE: Bonds and angles not calculated. ; _vrf_GEOM007_2m ; PROBLEM: _geom_angle_atom_site_label_3 is missing RESPONSE: Bonds and angles not calculated. ; _vrf_PLAT762_2m ; PROBLEM: CIF Contains no X-Y-H or H-Y-H Angles RESPONSE: Bonds and angles not calculated. ; data_1c _database_code_depnum_ccdc_archive 'CCDC 883644' #TrackingRef '- deposit.cif' _chemical_formula_sum 'C14 H14 N2 O1 S1' _chemical_formula_weight 258.34 _chemical_formula_moiety 'C14 H14 N2 O1 S1' _cell_formula_units_Z 4 _cell_length_a 28.4936(24) _cell_length_b 5.55569(33) _cell_length_c 8.14303(38) _cell_angle_alpha 90 _cell_angle_beta 90.7479(43) _cell_angle_gamma 90 _cell_volume 1288.95(14) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz '-x, -y, -z' '-x, y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' 'x, y, z' _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Cu K\a_1' _diffrn_radiation_wavelength 1.54059 _exptl_crystal_density_diffrn 1.331 _refine_ls_hydrogen_treatment mixed _refine_ls_shift/su_max <0.01 _refine_ls_number_parameters 130 _pd_proc_ls_prof_R_factor 0.0395 _pd_proc_ls_prof_wR_factor 0.0522 _refine_ls_R_Fsqd_factor 0.0202 _refine_ls_goodness_of_fit_all 0.975 _cell_measurement_temperature 293 _exptl_crystal_colour ? _refine_ls_structure_factor_coef Fsqd _computing_data_collection PAnalytical _computing_data_reduction none _computing_cell_refinement Topas _computing_structure_solution 'simulated annealing in DASH and Topas' _computing_structure_refinement Topas _refine_special_details ; The crystal structure (all atoms) was refined with restraints on bond lenghts and angles as well as planarity restraints. ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv H1 H 4 0.36215(24) 0.2345(21) 0.3818(12) 1 8.00(21) C2 C 4 0.382009(71) 0.12461(42) 0.31710(42) 1 8.00(21) C3 C 4 0.426910(90) 0.19134(52) 0.28497(43) 1 8.00(21) H4 H 4 0.43953(26) 0.3433(22) 0.3304(12) 1 8.00(21) C5 C 4 0.455100(94) 0.04505(42) 0.19098(43) 1 8.00(21) H6 H 4 0.48744(37) 0.0963(27) 0.1662(13) 1 8.00(21) C7 C 4 0.437110(72) -0.17477(43) 0.12864(48) 1 8.00(21) H8 H 4 0.45785(28) -0.2841(22) 0.0620(12) 1 8.00(21) C9 C 4 0.391870(72) -0.24099(52) 0.15834(43) 1 8.00(21) H10 H 4 0.38135(25) -0.3921(17) 0.1130(12) 1 8.00(21) C11 C 4 0.362750(93) -0.09387(54) 0.25219(44) 1 8.00(21) N12 N 4 0.314720(61) -0.15729(48) 0.29593(32) 1 8.00(21) H13 H 4 0.09469(25) -0.2932(17) 0.0385(13) 1 8.00(21) C14 C 4 0.113044(70) -0.18151(49) 0.10590(41) 1 8.00(21) C15 C 4 0.157735(91) -0.23560(52) 0.14596(43) 1 8.00(21) H16 H 4 0.17106(27) -0.3837(16) 0.1038(13) 1 8.00(21) C17 C 4 0.185280(94) -0.07983(55) 0.24842(43) 1 8.00(21) N18 N 4 0.233809(61) -0.15221(48) 0.29383(32) 1 8.00(21) C19 C 4 0.164329(72) 0.12972(42) 0.30304(47) 1 8.00(21) H20 H 4 0.18145(25) 0.2514(19) 0.3700(13) 1 8.00(21) C21 C 4 0.120278(70) 0.18120(45) 0.26132(40) 1 8.00(21) H22 H 4 0.10611(24) 0.3299(19) 0.3021(12) 1 8.00(21) C23 C 4 0.093252(87) 0.02380(43) 0.16377(44) 1 8.00(21) O24 O 4 0.04811(14) 0.09054(64) 0.12478(52) 1 8.00(21) C25 C 4 0.274530(59) -0.07564(26) 0.22903(21) 1 8.00(21) H26 H 4 0.31130(26) -0.2662(17) 0.3869(12) 1 8.00(21) H27 H 4 0.23678(35) -0.2614(16) 0.3852(13) 1 8.00(21) S28 S 4 0.27572(13) 0.11661(39) 0.06750(24) 1 8.00(21) C29 C 4 0.028779(70) 0.32485(37) 0.16155(30) 1 8.00(21) H30 H 4 0.02978(30) 0.3565(28) 0.2838(14) 1 8.00(21) H31 H 4 -0.00492(38) 0.3276(24) 0.1233(14) 1 8.00(21) H32 H 4 0.04697(26) 0.4607(18) 0.1002(17) 1 8.00(21) _vrf_ATOM006_1c ; PROBLEM: _atom_site_U_iso_or_equiv is missing RESPONSE: Displacement parameters are reported as Biso. ; _vrf_GEOM001_1c ; PROBLEM: _geom_bond_atom_site_label_1 is missing RESPONSE: Bonds and angles not calculated. ; _vrf_GEOM003_1c ; PROBLEM: _geom_bond_distance is missing RESPONSE: Bonds and angles not calculated. ; _vrf_GEOM006_1c ; PROBLEM: _geom_angle_atom_site_label_2 is missing RESPONSE: Bonds and angles not calculated. ; _vrf_GEOM007_1c ; PROBLEM: _geom_angle_atom_site_label_3 is missing RESPONSE: Bonds and angles not calculated. ; _vrf_PLAT762_1c ; PROBLEM: CIF Contains no X-Y-H or H-Y-H Angles RESPONSE: Bonds and angles not calculated. ; data_4b _database_code_depnum_ccdc_archive 'CCDC 883645' #TrackingRef '- deposit.cif' _chemical_formula_sum 'C14 H13 N3 O2 S1' _chemical_formula_weight 287.34 _chemical_formula_moiety 'C14 H13 N3 O2 S1' _cell_formula_units_Z 4 _cell_length_a 14.50439(92) _cell_length_b 13.62318(93) _cell_length_c 7.14076(26) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1410.99(14) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna21 _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Cu K\a_1' _diffrn_radiation_wavelength 1.54059 _exptl_crystal_density_diffrn 1.353 _refine_ls_hydrogen_treatment mixed _refine_ls_shift/su_max <0.01 _refine_ls_number_parameters 139 _pd_proc_ls_prof_R_factor 0.0400 _pd_proc_ls_prof_wR_factor 0.0530 _refine_ls_R_Fsqd_factor 0.0174 _refine_ls_goodness_of_fit_all 0.732 _cell_measurement_temperature 293 _exptl_crystal_colour ? _refine_ls_structure_factor_coef Fsqd _computing_data_collection PAnalytical _computing_data_reduction none _computing_cell_refinement Topas _computing_structure_solution 'simulated annealing in DASH and Topas' _computing_structure_refinement Topas _refine_special_details ; The crystal structure (all atoms) was refined with restraints on bond lenghts and angles as well as planarity restraints. ; loop_ _symmetry_equiv_pos_as_xyz '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x, y, z' 'x+1/2, -y+1/2, z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv H1 H 4 -0.00067(93) -0.2490(10) -0.0125(31) 1 3.66(21) C2 C 4 0.06661(24) -0.24302(25) -0.0050(12) 1 3.66(21) C3 C 4 0.11737(22) -0.32437(26) 0.0447(12) 1 3.66(21) H4 H 4 0.08511(97) -0.3861(11) 0.0621(33) 1 3.66(21) C5 C 4 0.21021(24) -0.32024(25) 0.0589(12) 1 3.66(21) N6 N 4 0.25920(24) -0.40842(26) 0.0987(13) 1 3.66(21) C7 C 4 0.25694(26) -0.23115(22) 0.02796(98) 1 3.66(21) H8 H 4 0.32366(93) -0.2258(11) 0.0349(37) 1 3.66(21) C9 C 4 0.20811(24) -0.14924(22) -0.0216(12) 1 3.66(21) H10 H 4 0.24424(91) -0.0895(13) -0.0360(30) 1 3.66(21) C11 C 4 0.11078(24) -0.15265(26) -0.0336(12) 1 3.66(21) N12 N 4 0.05042(27) -0.06928(25) -0.07155(73) 1 3.66(21) H13 H 4 -0.19658(92) 0.3516(13) 0.0497(30) 1 3.66(21) C14 C 4 -0.13389(26) 0.33008(25) 0.0346(13) 1 3.66(21) C15 C 4 -0.11776(20) 0.23144(31) 0.0047(13) 1 3.66(21) H16 H 4 -0.17005(91) 0.1862(12) -0.0047(30) 1 3.66(21) C17 C 4 -0.02327(23) 0.19772(33) -0.0197(14) 1 3.66(21) N18 N 4 -0.01215(27) 0.09116(23) -0.05516(78) 1 3.66(21) C19 C 4 0.04360(28) 0.26648(30) -0.0050(12) 1 3.66(21) H20 H 4 0.10865(93) 0.24781(96) -0.0162(30) 1 3.66(21) C21 C 4 0.02591(23) 0.36535(25) 0.0271(13) 1 3.66(21) H22 H 4 0.0779(10) 0.4109(10) 0.0380(30) 1 3.66(21) C23 C 4 -0.06169(26) 0.39932(26) 0.04992(97) 1 3.66(21) C24 C 4 -0.07933(19) 0.50956(19) 0.09194(49) 1 3.66(21) C25 C 4 0.05713(23) 0.02607(27) 0.00509(57) 1 3.66(21) H26 H 4 0.0003(12) -0.0831(15) -0.1554(27) 1 3.66(21) H27 H 4 -0.0568(12) 0.0653(14) -0.1372(24) 1 3.66(21) S28 S 4 0.14204(30) 0.05735(40) 0.15126(72) 1 3.66(21) O29 O 4 0.21852(41) -0.48780(53) 0.1000(19) 1 3.66(21) O30 O 4 0.33865(58) -0.40664(46) 0.1240(21) 1 3.66(21) H31 H 4 -0.14569(82) 0.5207(11) 0.1058(26) 1 3.66(21) H32 H 4 -0.0558(11) 0.5523(13) -0.0098(28) 1 3.66(21) H33 H 4 -0.0493(12) 0.5280(18) 0.2110(25) 1 3.66(21) _vrf_ATOM006_4b ; PROBLEM: _atom_site_U_iso_or_equiv is missing RESPONSE: Displacement parameters are reported as Biso. ; _vrf_GEOM001_4b ; PROBLEM: _geom_bond_atom_site_label_1 is missing RESPONSE: Bonds and angles not calculated. ; _vrf_GEOM003_4b ; PROBLEM: _geom_bond_distance is missing RESPONSE: Bonds and angles not calculated. ; _vrf_GEOM006_4b ; PROBLEM: _geom_angle_atom_site_label_2 is missing RESPONSE: Bonds and angles not calculated. ; _vrf_GEOM007_4b ; PROBLEM: _geom_angle_atom_site_label_3 is missing RESPONSE: Bonds and angles not calculated. ; _vrf_PLAT762_4b ; PROBLEM: CIF Contains no X-Y-H or H-Y-H Angles RESPONSE: Bonds and angles not calculated. ; #############################################################################