# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global #TrackingRef '2010mw0001.txt' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Gale, Philip' _publ_contact_author_email philip.gale@soton.ac.uk _publ_section_title ; Thiourea isosteres as transmembrane anion transporters ; _chemical_compound_source 'Marco Wenzel' loop_ _publ_author_name P.Gale M.Wenzel M.Light A.Davis data_2010mw0001 _database_code_depnum_ccdc_archive 'CCDC 821666' #TrackingRef '2010mw0001.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H20 N4' _chemical_formula_sum 'C14 H20 N4' _chemical_formula_weight 244.34 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.2071(2) _cell_length_b 11.2105(3) _cell_length_c 24.2602(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2776.01(11) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3561 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_min 0.1 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_max 0.6 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5971 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \\k-goniostat' _diffrn_measurement_method '\\f & \\w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27023 _diffrn_reflns_av_R_equivalents 0.0712 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3585 _reflns_number_gt 2806 _reflns_threshold_expression >2\\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\\s(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 w=1/[\\s^2^(Fo^2^)+(0.0549P)^2^+1.7032P] 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 SHELXL _refine_ls_extinction_coef 0.0099(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^ _refine_ls_number_reflns 3585 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0775 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1379 _refine_ls_wR_factor_gt 0.1256 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 C1 C 0.6250(3) 0.6891(3) -0.02772(12) 0.0215(6) Uani 1 1 d . . . C2 C 0.5003(3) 0.6563(3) -0.04543(13) 0.0251(7) Uani 1 1 d . . . H2 H 0.4621 0.5867 -0.0321 0.030 Uiso 1 1 calc R . . C3 C 0.4327(3) 0.7268(3) -0.08278(13) 0.0278(7) Uani 1 1 d . . . H3 H 0.3488 0.7053 -0.0940 0.033 Uiso 1 1 calc R . . C4 C 0.4901(3) 0.8295(3) -0.10343(13) 0.0289(7) Uani 1 1 d . . . H4 H 0.4456 0.8761 -0.1290 0.035 Uiso 1 1 calc R . . C5 C 0.6137(3) 0.8624(3) -0.08597(13) 0.0270(7) Uani 1 1 d . . . H5 H 0.6517 0.9318 -0.0996 0.032 Uiso 1 1 calc R . . C6 C 0.6815(3) 0.7930(3) -0.04826(13) 0.0258(7) Uani 1 1 d . . . H6 H 0.7646 0.8158 -0.0367 0.031 Uiso 1 1 calc R . . C7 C 0.6560(3) 0.5785(3) 0.05912(12) 0.0215(6) Uani 1 1 d . . . C8 C 0.8146(3) 0.4363(3) 0.06534(12) 0.0219(6) Uani 1 1 d . . . C9 C 0.4941(3) 0.5979(3) 0.13465(13) 0.0305(7) Uani 1 1 d . . . H9A H 0.5335 0.5237 0.1468 0.037 Uiso 1 1 calc R . . H9B H 0.4008 0.5841 0.1304 0.037 Uiso 1 1 calc R . . C10 C 0.5142(4) 0.6902(4) 0.17825(16) 0.0481(10) Uani 1 1 d . . . H10A H 0.4776 0.7650 0.1653 0.058 Uiso 1 1 calc R . . H10B H 0.4655 0.6667 0.2108 0.058 Uiso 1 1 calc R . . C11 C 0.6502(4) 0.7101(4) 0.19392(18) 0.0528(11) Uani 1 1 d . . . H11A H 0.6999 0.7301 0.1611 0.063 Uiso 1 1 calc R . . H11B H 0.6856 0.6364 0.2086 0.063 Uiso 1 1 calc R . . C12 C 0.6702(4) 0.8106(4) 0.23738(17) 0.0490(10) Uani 1 1 d . . . H12A H 0.6365 0.8850 0.2227 0.059 Uiso 1 1 calc R . . H12B H 0.6201 0.7915 0.2702 0.059 Uiso 1 1 calc R . . C13 C 0.8099(4) 0.8271(4) 0.25285(16) 0.0465(10) Uani 1 1 d . . . H13A H 0.8589 0.8483 0.2200 0.056 Uiso 1 1 calc R . . H13B H 0.8438 0.7516 0.2661 0.056 Uiso 1 1 calc R . . C14 C 0.8342(4) 0.9212(4) 0.29633(17) 0.0456(10) Uani 1 1 d . . . H14A H 0.9263 0.9260 0.3039 0.068 Uiso 1 1 calc R . . H14B H 0.7882 0.9002 0.3295 0.068 Uiso 1 1 calc R . . H14C H 0.8034 0.9970 0.2833 0.068 Uiso 1 1 calc R . . C15 C 0.2326(3) 0.3198(3) 0.03230(12) 0.0224(7) Uani 1 1 d . . . C16 C 0.3525(3) 0.3587(3) 0.05259(13) 0.0249(7) Uani 1 1 d . . . H16 H 0.3855 0.4326 0.0420 0.030 Uiso 1 1 calc R . . C17 C 0.4230(3) 0.2872(3) 0.08875(14) 0.0301(7) Uani 1 1 d . . . H17 H 0.5043 0.3124 0.1016 0.036 Uiso 1 1 calc R . . C18 C 0.3727(3) 0.1788(3) 0.10574(13) 0.0319(8) Uani 1 1 d . . . H18 H 0.4196 0.1315 0.1303 0.038 Uiso 1 1 calc R . . C19 C 0.2524(4) 0.1409(3) 0.08603(14) 0.0335(8) Uani 1 1 d . . . H19 H 0.2184 0.0681 0.0976 0.040 Uiso 1 1 calc R . . C20 C 0.1822(3) 0.2106(3) 0.04924(14) 0.0273(7) Uani 1 1 d . . . H20 H 0.1018 0.1845 0.0359 0.033 Uiso 1 1 calc R . . C21 C 0.2051(3) 0.4305(3) -0.05437(12) 0.0212(6) Uani 1 1 d . . . C22 C 0.0375(3) 0.5633(3) -0.06521(12) 0.0224(6) Uani 1 1 d . . . C23 C 0.3791(3) 0.4208(3) -0.12522(12) 0.0251(7) Uani 1 1 d . . . H23A H 0.4683 0.4467 -0.1185 0.030 Uiso 1 1 calc R . . H23B H 0.3312 0.4877 -0.1406 0.030 Uiso 1 1 calc R . . C24 C 0.3804(3) 0.3191(3) -0.16685(13) 0.0259(7) Uani 1 1 d . . . H24A H 0.4286 0.2524 -0.1514 0.031 Uiso 1 1 calc R . . H24B H 0.4261 0.3451 -0.1998 0.031 Uiso 1 1 calc R . . C25 C 0.2426(3) 0.2770(3) -0.18279(14) 0.0318(8) Uani 1 1 d . . . H25A H 0.1948 0.2564 -0.1496 0.038 Uiso 1 1 calc R . . H25B H 0.1966 0.3421 -0.2006 0.038 Uiso 1 1 calc R . . C26 C 0.2444(4) 0.1692(3) -0.22148(13) 0.0319(8) Uani 1 1 d . . . H26A H 0.2896 0.1041 -0.2033 0.038 Uiso 1 1 calc R . . H26B H 0.1549 0.1439 -0.2280 0.038 Uiso 1 1 calc R . . C27 C 0.3098(3) 0.1921(3) -0.27661(13) 0.0314(8) Uani 1 1 d . . . H27A H 0.2681 0.2601 -0.2940 0.038 Uiso 1 1 calc R . . H27B H 0.4010 0.2125 -0.2704 0.038 Uiso 1 1 calc R . . C28 C 0.3030(4) 0.0865(3) -0.31524(16) 0.0437(10) Uani 1 1 d . . . H28A H 0.3464 0.1059 -0.3492 0.066 Uiso 1 1 calc R . . H28B H 0.2130 0.0674 -0.3226 0.066 Uiso 1 1 calc R . . H28C H 0.3454 0.0191 -0.2985 0.066 Uiso 1 1 calc R . . N1 N 0.6965(2) 0.6145(2) 0.00877(10) 0.0223(5) Uani 1 1 d . . . H1 H 0.7720 0.5900 -0.0021 0.027 Uiso 1 1 calc R . . N2 N 0.5491(2) 0.6296(2) 0.08099(10) 0.0239(6) Uani 1 1 d . . . H7 H 0.5105 0.6845 0.0623 0.029 Uiso 1 1 calc R . . N3 N 0.7165(2) 0.4936(2) 0.08830(10) 0.0245(6) Uani 1 1 d . . . N4 N 0.9024(3) 0.3779(2) 0.05000(11) 0.0270(6) Uani 1 1 d . . . N5 N 0.1597(2) 0.3918(2) -0.00503(10) 0.0230(6) Uani 1 1 d . . . H15 H 0.0816 0.4121 0.0044 0.028 Uiso 1 1 calc R . . N6 N 0.3187(2) 0.3858(2) -0.07281(10) 0.0227(6) Uani 1 1 d . . . H21 H 0.3583 0.3338 -0.0528 0.027 Uiso 1 1 calc R . . N7 N 0.1426(3) 0.5109(2) -0.08504(10) 0.0243(6) Uani 1 1 d . . . N8 N -0.0553(3) 0.6162(2) -0.05204(11) 0.0277(6) Uani 1 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 C1 0.0241(15) 0.0192(14) 0.0212(14) -0.0013(12) 0.0017(12) 0.0036(13) C2 0.0268(16) 0.0226(15) 0.0259(15) -0.0006(13) 0.0009(13) -0.0011(13) C3 0.0249(15) 0.0338(17) 0.0249(16) -0.0041(14) -0.0038(13) 0.0043(14) C4 0.0342(18) 0.0278(17) 0.0248(16) 0.0023(14) 0.0016(14) 0.0072(15) C5 0.0298(16) 0.0247(16) 0.0266(16) 0.0049(14) 0.0043(14) 0.0026(14) C6 0.0257(16) 0.0226(15) 0.0290(16) 0.0014(13) 0.0010(14) -0.0028(13) C7 0.0213(15) 0.0186(14) 0.0247(15) -0.0017(12) -0.0021(12) -0.0005(12) C8 0.0242(16) 0.0182(14) 0.0233(15) 0.0052(12) -0.0031(13) -0.0027(13) C9 0.0278(17) 0.0392(19) 0.0245(16) 0.0033(15) 0.0031(14) 0.0051(15) C10 0.056(2) 0.051(2) 0.037(2) -0.0015(19) 0.0116(19) -0.003(2) C11 0.052(3) 0.058(3) 0.048(2) -0.004(2) 0.012(2) 0.003(2) C12 0.052(2) 0.051(2) 0.044(2) -0.001(2) -0.0038(19) -0.014(2) C13 0.054(2) 0.042(2) 0.043(2) -0.0087(19) -0.0033(19) -0.003(2) C14 0.043(2) 0.046(2) 0.048(2) -0.0069(19) -0.0093(19) -0.0059(19) C15 0.0239(16) 0.0209(15) 0.0225(15) -0.0012(12) 0.0024(12) 0.0040(13) C16 0.0263(16) 0.0230(15) 0.0253(16) -0.0006(13) 0.0004(13) -0.0011(13) C17 0.0266(16) 0.0341(18) 0.0296(17) -0.0015(15) -0.0028(14) 0.0055(14) C18 0.0339(18) 0.0345(18) 0.0272(16) 0.0044(15) 0.0005(15) 0.0114(16) C19 0.0347(18) 0.0268(17) 0.0391(19) 0.0126(15) 0.0076(16) 0.0018(15) C20 0.0239(16) 0.0245(16) 0.0335(17) 0.0017(14) 0.0036(14) 0.0019(14) C21 0.0220(15) 0.0172(13) 0.0243(15) -0.0011(12) 0.0013(12) -0.0024(12) C22 0.0243(16) 0.0213(14) 0.0218(15) 0.0035(13) -0.0010(12) -0.0018(13) C23 0.0249(15) 0.0257(16) 0.0245(15) 0.0011(13) 0.0058(13) -0.0020(13) C24 0.0233(15) 0.0288(16) 0.0254(15) -0.0024(14) 0.0041(13) -0.0002(14) C25 0.0299(17) 0.0365(18) 0.0290(17) -0.0068(15) 0.0063(14) -0.0059(16) C26 0.0355(18) 0.0316(18) 0.0286(17) -0.0043(14) 0.0035(15) -0.0080(15) C27 0.0347(18) 0.0307(18) 0.0289(17) -0.0081(14) -0.0008(15) -0.0023(15) C28 0.053(2) 0.039(2) 0.039(2) -0.0163(17) 0.0065(19) -0.0023(19) N1 0.0178(12) 0.0237(12) 0.0255(13) 0.0048(11) 0.0031(11) 0.0037(11) N2 0.0257(13) 0.0226(13) 0.0235(13) 0.0018(11) 0.0008(11) 0.0041(11) N3 0.0248(14) 0.0216(13) 0.0270(13) 0.0019(11) 0.0001(11) 0.0032(11) N4 0.0247(14) 0.0232(13) 0.0332(15) 0.0011(12) 0.0007(12) 0.0010(12) N5 0.0196(12) 0.0243(12) 0.0251(13) 0.0020(11) 0.0026(10) 0.0042(11) N6 0.0230(13) 0.0243(13) 0.0208(13) 0.0006(11) 0.0018(11) 0.0023(11) N7 0.0252(14) 0.0236(13) 0.0241(13) 0.0031(11) 0.0017(11) 0.0025(11) N8 0.0291(14) 0.0232(13) 0.0308(14) 0.0042(12) 0.0004(12) 0.0022(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C6 1.392(4) . ? C1 C2 1.393(4) . ? C1 N1 1.420(4) . ? C2 C3 1.387(4) . ? C3 C4 1.385(5) . ? C4 C5 1.381(5) . ? C5 C6 1.386(4) . ? C7 N3 1.337(4) . ? C7 N2 1.342(4) . ? C7 N1 1.351(4) . ? C8 N4 1.171(4) . ? C8 N3 1.314(4) . ? C9 N2 1.462(4) . ? C9 C10 1.494(5) . ? C10 C11 1.457(6) . ? C11 C12 1.557(6) . ? C12 C13 1.486(6) . ? C13 C14 1.512(5) . ? C15 C16 1.389(4) . ? C15 C20 1.390(4) . ? C15 N5 1.423(4) . ? C16 C17 1.389(4) . ? C17 C18 1.382(5) . ? C18 C19 1.385(5) . ? C19 C20 1.385(5) . ? C21 N7 1.332(4) . ? C21 N6 1.339(4) . ? C21 N5 1.355(4) . ? C22 N8 1.162(4) . ? C22 N7 1.315(4) . ? C23 N6 1.467(4) . ? C23 C24 1.523(4) . ? C24 C25 1.533(4) . ? C25 C26 1.531(4) . ? C26 C27 1.517(5) . ? C27 C28 1.512(5) . ? 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 C6 C1 C2 119.3(3) . . ? C6 C1 N1 120.2(3) . . ? C2 C1 N1 120.4(3) . . ? C3 C2 C1 120.4(3) . . ? C4 C3 C2 120.0(3) . . ? C5 C4 C3 119.9(3) . . ? C4 C5 C6 120.5(3) . . ? C5 C6 C1 120.0(3) . . ? N3 C7 N2 118.0(3) . . ? N3 C7 N1 123.3(3) . . ? N2 C7 N1 118.6(3) . . ? N4 C8 N3 172.7(3) . . ? N2 C9 C10 114.1(3) . . ? C11 C10 C9 114.9(4) . . ? C10 C11 C12 114.4(4) . . ? C13 C12 C11 112.8(4) . . ? C12 C13 C14 114.9(4) . . ? C16 C15 C20 119.8(3) . . ? C16 C15 N5 120.5(3) . . ? C20 C15 N5 119.6(3) . . ? C17 C16 C15 119.9(3) . . ? C18 C17 C16 120.2(3) . . ? C17 C18 C19 119.7(3) . . ? C18 C19 C20 120.5(3) . . ? C19 C20 C15 119.7(3) . . ? N7 C21 N6 118.7(3) . . ? N7 C21 N5 123.1(3) . . ? N6 C21 N5 118.1(3) . . ? N8 C22 N7 173.6(3) . . ? N6 C23 C24 112.2(3) . . ? C23 C24 C25 112.9(3) . . ? C26 C25 C24 112.8(3) . . ? C27 C26 C25 114.3(3) . . ? C28 C27 C26 113.2(3) . . ? C7 N1 C1 125.6(3) . . ? C7 N2 C9 124.1(3) . . ? C8 N3 C7 118.4(3) . . ? C21 N5 C15 124.4(3) . . ? C21 N6 C23 123.6(3) . . ? C22 N7 C21 119.3(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.544 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.053 # Attachment '2010mw0012.txt' data_2010mw0012a _database_code_depnum_ccdc_archive 'CCDC 821667' #TrackingRef '2010mw0012.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 F5 N4' _chemical_formula_sum 'C14 H15 F5 N4' _chemical_formula_weight 334.30 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 13.6862(9) _cell_length_b 10.6669(7) _cell_length_c 11.3955(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.570(4) _cell_angle_gamma 90.00 _cell_volume 1567.52(17) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3176 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5936 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \\k-goniostat' _diffrn_measurement_method '\\f & \\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25328 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 27.79 _reflns_number_total 3614 _reflns_number_gt 2773 _reflns_threshold_expression >2\\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\\s(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 w=1/[\\s^2^(Fo^2^)+(0.1023P)^2^+1.1004P] 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 SHELXL _refine_ls_extinction_coef 0.074(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^ _refine_ls_number_reflns 3614 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0916 _refine_ls_R_factor_gt 0.0706 _refine_ls_wR_factor_ref 0.2081 _refine_ls_wR_factor_gt 0.1804 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _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 C1 C 0.83839(17) 0.3043(2) 0.2129(2) 0.0348(5) Uani 1 1 d . . . C2 C 0.77434(19) 0.3478(2) 0.0982(2) 0.0394(5) Uani 1 1 d . . . C3 C 0.68646(19) 0.2842(3) 0.0303(2) 0.0446(6) Uani 1 1 d . . . C4 C 0.65789(19) 0.1768(3) 0.0783(2) 0.0457(6) Uani 1 1 d . . . C5 C 0.71870(19) 0.1326(2) 0.1930(2) 0.0412(5) Uani 1 1 d . . . C6 C 0.80810(18) 0.1957(2) 0.2584(2) 0.0371(5) Uani 1 1 d . . . C7 C 1.01534(18) 0.3767(2) 0.2483(2) 0.0347(5) Uani 1 1 d . . . C8 C 1.09338(17) 0.5164(2) 0.4033(2) 0.0343(5) Uani 1 1 d . . . C9 C 1.10652(19) 0.3183(2) 0.1039(2) 0.0421(6) Uani 1 1 d . . . H9A H 1.1373 0.4013 0.1177 0.050 Uiso 1 1 calc R . . H9B H 1.0824 0.3024 0.0150 0.050 Uiso 1 1 calc R . . C10 C 1.1884(2) 0.2226(3) 0.1684(3) 0.0514(7) Uani 1 1 d . D . H10A H 1.1570 0.1400 0.1584 0.062 Uiso 1 1 calc R . . H10B H 1.2154 0.2412 0.2568 0.062 Uiso 1 1 calc R . . C11 C 1.2777(2) 0.2219(3) 0.1160(3) 0.0535(7) Uani 1 1 d . . . H11A H 1.2500 0.2333 0.0264 0.064 Uiso 0.50 1 calc PR A 1 H11B H 1.3236 0.2918 0.1509 0.064 Uiso 0.50 1 calc PR A 1 H11C H 1.303(5) 0.308(7) 0.108(6) 0.064 Uiso 0.50 1 d P B 2 H11D H 1.254(5) 0.192(7) 0.024(6) 0.064 Uiso 0.50 1 d P C 2 C12 C 1.3402(6) 0.1000(8) 0.1450(8) 0.0690(18) Uani 0.50 1 d P D 1 H12A H 1.2953 0.0311 0.1043 0.083 Uiso 0.50 1 calc PR D 1 H12B H 1.3956 0.1050 0.1100 0.083 Uiso 0.50 1 calc PR D 1 C13 C 1.3861(6) 0.0717(8) 0.2807(8) 0.0707(18) Uani 0.50 1 d P D 1 H13A H 1.3316 0.0590 0.3162 0.085 Uiso 0.50 1 calc PR D 1 H13B H 1.4292 0.1409 0.3238 0.085 Uiso 0.50 1 calc PR D 1 C12A C 1.3784(4) 0.1528(5) 0.1994(6) 0.0448(12) Uani 0.50 1 d P D 2 H12C H 1.4317 0.1592 0.1610 0.054 Uiso 0.50 1 calc PR D 2 H12D H 1.4041 0.1929 0.2804 0.054 Uiso 0.50 1 calc PR D 2 C13A C 1.3556(4) 0.0131(5) 0.2157(7) 0.0493(12) Uani 0.50 1 d P D 2 H13C H 1.3032 0.0065 0.2553 0.059 Uiso 0.50 1 calc PR D 2 H13D H 1.3291 -0.0269 0.1347 0.059 Uiso 0.50 1 calc PR D 2 C14 C 1.4545(3) -0.0531(3) 0.2953(4) 0.0710(9) Uani 1 1 d . . . H14A H 1.4440 -0.1056 0.3584 0.106 Uiso 1 1 calc R D 1 H14B H 1.5265 -0.0309 0.3186 0.106 Uiso 1 1 calc R D 1 H14C H 1.4340 -0.0975 0.2175 0.106 Uiso 1 1 calc R D 1 N1 N 0.92923(15) 0.36918(17) 0.28270(17) 0.0356(4) Uani 1 1 d . . . H1 H 0.9303 0.4058 0.3503 0.043 Uiso 1 1 calc R . . N2 N 1.01733(15) 0.31576(19) 0.14856(17) 0.0378(5) Uani 1 1 d . . . H2 H 0.9639 0.2724 0.1075 0.045 Uiso 1 1 calc R . . N3 N 1.09806(15) 0.44291(19) 0.31344(17) 0.0378(5) Uani 1 1 d . . . N4 N 1.09744(15) 0.58706(18) 0.48256(17) 0.0374(5) Uani 1 1 d . . . F1 F 0.79875(12) 0.45498(14) 0.05319(13) 0.0481(4) Uani 1 1 d . . . F2 F 0.62689(13) 0.32709(19) -0.08052(15) 0.0621(5) Uani 1 1 d . . . F3 F 0.57055(12) 0.11653(18) 0.01461(16) 0.0604(5) Uani 1 1 d . . . F4 F 0.69157(12) 0.02784(15) 0.23902(15) 0.0512(4) Uani 1 1 d . . . F5 F 0.86805(12) 0.15070(13) 0.36911(12) 0.0437(4) Uani 1 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 C1 0.0397(11) 0.0360(11) 0.0329(10) -0.0029(8) 0.0175(9) 0.0014(9) C2 0.0437(12) 0.0408(12) 0.0376(11) 0.0037(9) 0.0188(10) 0.0050(10) C3 0.0391(12) 0.0563(15) 0.0380(12) 0.0025(10) 0.0123(10) 0.0095(11) C4 0.0365(12) 0.0564(15) 0.0459(13) -0.0078(11) 0.0159(10) -0.0033(11) C5 0.0444(13) 0.0404(12) 0.0458(13) -0.0024(10) 0.0241(11) -0.0019(10) C6 0.0435(12) 0.0380(12) 0.0333(10) -0.0012(9) 0.0176(9) 0.0033(9) C7 0.0432(12) 0.0308(10) 0.0330(10) 0.0014(8) 0.0165(9) 0.0006(9) C8 0.0404(11) 0.0321(11) 0.0327(10) 0.0019(8) 0.0152(9) -0.0032(9) C9 0.0449(13) 0.0483(13) 0.0387(12) -0.0108(10) 0.0215(10) -0.0065(10) C10 0.0552(15) 0.0491(15) 0.0600(16) -0.0020(12) 0.0324(13) 0.0009(12) C11 0.0524(15) 0.0551(16) 0.0622(17) -0.0044(13) 0.0312(13) -0.0017(13) C12 0.054(4) 0.073(5) 0.092(5) -0.010(4) 0.040(4) -0.004(3) C13 0.056(4) 0.067(4) 0.094(5) -0.002(4) 0.032(4) 0.001(3) C12A 0.040(3) 0.043(3) 0.055(3) -0.011(2) 0.020(2) -0.013(2) C13A 0.047(3) 0.039(3) 0.069(4) -0.008(3) 0.029(3) -0.008(2) C14 0.0544(17) 0.066(2) 0.097(3) 0.0160(18) 0.0299(17) 0.0028(15) N1 0.0437(10) 0.0354(9) 0.0317(9) -0.0050(7) 0.0179(8) -0.0018(8) N2 0.0402(10) 0.0406(10) 0.0363(9) -0.0080(8) 0.0177(8) -0.0060(8) N3 0.0438(10) 0.0392(10) 0.0344(9) -0.0066(8) 0.0182(8) -0.0025(8) N4 0.0450(10) 0.0371(10) 0.0344(9) -0.0026(8) 0.0190(8) -0.0051(8) F1 0.0601(9) 0.0441(8) 0.0444(8) 0.0101(6) 0.0233(7) 0.0058(7) F2 0.0505(9) 0.0819(13) 0.0444(9) 0.0109(8) 0.0036(7) 0.0074(8) F3 0.0405(8) 0.0802(12) 0.0587(10) -0.0102(8) 0.0143(7) -0.0123(8) F4 0.0575(9) 0.0459(9) 0.0587(9) -0.0022(7) 0.0306(7) -0.0107(7) F5 0.0560(9) 0.0418(8) 0.0334(7) 0.0025(5) 0.0149(6) -0.0021(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C2 1.388(3) . ? C1 C6 1.388(3) . ? C1 N1 1.413(3) . ? C2 F1 1.340(3) . ? C2 C3 1.371(4) . ? C3 F2 1.334(3) . ? C3 C4 1.382(4) . ? C4 F3 1.337(3) . ? C4 C5 1.377(4) . ? C5 F4 1.339(3) . ? C5 C6 1.376(3) . ? C6 F5 1.342(3) . ? C7 N2 1.317(3) . ? C7 N3 1.330(3) . ? C7 N1 1.363(3) . ? C8 N4 1.163(3) . ? C8 N3 1.308(3) . ? C9 N2 1.471(3) . ? C9 C10 1.512(4) . ? C10 C11 1.530(4) . ? C11 C12 1.530(8) . ? C11 C12A 1.570(6) . ? C12 C13 1.492(12) . ? C13 C14 1.603(8) . ? C12A C13A 1.546(8) . ? C13A C14 1.527(7) . ? 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 C1 C6 117.2(2) . . ? C2 C1 N1 121.7(2) . . ? C6 C1 N1 121.0(2) . . ? F1 C2 C3 119.3(2) . . ? F1 C2 C1 119.1(2) . . ? C3 C2 C1 121.6(2) . . ? F2 C3 C2 120.5(2) . . ? F2 C3 C4 119.7(2) . . ? C2 C3 C4 119.8(2) . . ? F3 C4 C5 119.8(2) . . ? F3 C4 C3 120.3(2) . . ? C5 C4 C3 119.9(2) . . ? F4 C5 C6 120.6(2) . . ? F4 C5 C4 119.9(2) . . ? C6 C5 C4 119.5(2) . . ? F5 C6 C5 119.1(2) . . ? F5 C6 C1 119.0(2) . . ? C5 C6 C1 121.9(2) . . ? N2 C7 N3 118.9(2) . . ? N2 C7 N1 119.3(2) . . ? N3 C7 N1 121.79(19) . . ? N4 C8 N3 173.7(2) . . ? N2 C9 C10 112.6(2) . . ? C9 C10 C11 111.9(2) . . ? C12 C11 C10 112.4(3) . . ? C12 C11 C12A 32.6(3) . . ? C10 C11 C12A 114.9(3) . . ? C13 C12 C11 114.0(6) . . ? C12 C13 C14 107.7(6) . . ? C13A C12A C11 110.7(4) . . ? C14 C13A C12A 110.0(4) . . ? C13A C14 C13 35.3(3) . . ? C7 N1 C1 123.33(18) . . ? C7 N2 C9 123.3(2) . . ? C8 N3 C7 119.97(19) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.476 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.137 # Attachment '2011mw0006.txt' data_2010mw0006 _database_code_depnum_ccdc_archive 'CCDC 821668' #TrackingRef '2011mw0006.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H20 N2 S' _chemical_formula_sum 'C13 H20 N2 S' _chemical_formula_weight 236.37 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.5794(2) _cell_length_b 10.2955(2) _cell_length_c 15.2141(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1343.85(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1749 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.168 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.218 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5976 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \\k-goniostat' _diffrn_measurement_method '\\f & \\w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10129 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3059 _reflns_number_gt 2871 _reflns_threshold_expression >2\\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\\s(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 w=1/[\\s^2^(Fo^2^)+(0.0000P)^2^+0.4023P] 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 0.00(6) _refine_ls_number_reflns 3059 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0769 _refine_ls_wR_factor_gt 0.0749 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.001 _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 C1 C 0.93306(19) 0.20915(16) 1.15362(9) 0.0179(3) Uani 1 1 d . . . C2 C 0.86297(19) 0.09576(16) 1.18371(10) 0.0198(3) Uani 1 1 d . . . H2A H 0.8554 0.0236 1.1471 0.024 Uiso 1 1 calc R . . C3 C 0.8042(2) 0.09095(16) 1.26902(9) 0.0222(3) Uani 1 1 d . . . H3 H 0.7550 0.0158 1.2886 0.027 Uiso 1 1 calc R . . C4 C 0.8178(2) 0.19629(17) 1.32521(10) 0.0232(4) Uani 1 1 d . . . H4 H 0.7793 0.1916 1.3823 0.028 Uiso 1 1 calc R . . C5 C 0.8896(2) 0.30888(18) 1.29539(10) 0.0252(4) Uani 1 1 d . . . H5 H 0.8999 0.3799 1.3327 0.030 Uiso 1 1 calc R . . C6 C 0.9462(2) 0.31544(17) 1.20961(10) 0.0214(3) Uani 1 1 d . . . H6 H 0.9930 0.3914 1.1897 0.026 Uiso 1 1 calc R . . C7 C 0.95120(19) 0.17951(15) 0.98937(9) 0.0175(3) Uani 1 1 d . . . C8 C 1.0029(2) 0.20040(17) 0.82899(9) 0.0209(4) Uani 1 1 d . . . H8A H 0.9555 0.1153 0.8233 0.025 Uiso 1 1 calc R . . H8B H 1.1009 0.1989 0.7972 0.025 Uiso 1 1 calc R . . C9 C 0.8962(2) 0.30063(17) 0.78714(10) 0.0228(4) Uani 1 1 d . . . H9A H 0.9423 0.3862 0.7933 0.027 Uiso 1 1 calc R . . H9B H 0.7970 0.3010 0.8177 0.027 Uiso 1 1 calc R . . C10 C 0.8685(2) 0.27241(17) 0.68961(10) 0.0232(4) Uani 1 1 d . . . H10A H 0.9683 0.2694 0.6597 0.028 Uiso 1 1 calc R . . H10B H 0.8205 0.1875 0.6839 0.028 Uiso 1 1 calc R . . C11 C 0.7653(2) 0.37251(16) 0.64448(10) 0.0226(4) Uani 1 1 d . . . H11A H 0.8121 0.4577 0.6510 0.027 Uiso 1 1 calc R . . H11B H 0.6646 0.3742 0.6734 0.027 Uiso 1 1 calc R . . C12 C 0.7415(2) 0.34475(18) 0.54705(10) 0.0301(4) Uani 1 1 d . . . H12A H 0.8424 0.3398 0.5185 0.036 Uiso 1 1 calc R . . H12B H 0.6913 0.2609 0.5406 0.036 Uiso 1 1 calc R . . C13 C 0.6432(3) 0.44719(19) 0.50089(11) 0.0372(5) Uani 1 1 d . . . H13A H 0.6311 0.4242 0.4401 0.056 Uiso 1 1 calc R . . H13B H 0.6940 0.5300 0.5051 0.056 Uiso 1 1 calc R . . H13C H 0.5426 0.4520 0.5283 0.056 Uiso 1 1 calc R . . N1 N 1.00146(17) 0.22265(14) 1.06918(8) 0.0204(3) Uani 1 1 d . . . H1 H 1.0881 0.2646 1.0682 0.024 Uiso 1 1 calc R . . N2 N 1.03433(17) 0.22563(14) 0.92178(8) 0.0214(3) Uani 1 1 d . . . H2 H 1.1129 0.2742 0.9340 0.026 Uiso 1 1 calc R . . S1 S 0.79950(5) 0.07550(4) 0.97535(2) 0.01949(10) Uani 1 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 C1 0.0136(8) 0.0234(8) 0.0168(7) 0.0016(6) -0.0019(6) 0.0027(7) C2 0.0192(8) 0.0204(8) 0.0199(7) 0.0012(6) -0.0020(6) 0.0007(7) C3 0.0209(8) 0.0256(8) 0.0202(7) 0.0061(6) -0.0009(6) -0.0013(8) C4 0.0214(9) 0.0326(9) 0.0155(6) 0.0026(6) 0.0007(6) 0.0017(8) C5 0.0268(10) 0.0281(9) 0.0208(7) -0.0050(7) -0.0006(7) -0.0004(8) C6 0.0209(9) 0.0225(8) 0.0208(7) 0.0008(6) -0.0010(6) -0.0035(7) C7 0.0163(8) 0.0189(7) 0.0172(7) -0.0003(6) -0.0001(6) 0.0031(7) C8 0.0192(8) 0.0285(9) 0.0150(7) -0.0014(6) 0.0017(6) -0.0011(7) C9 0.0204(9) 0.0283(9) 0.0197(7) -0.0016(7) 0.0005(6) -0.0004(7) C10 0.0250(9) 0.0267(8) 0.0180(7) -0.0022(7) -0.0005(7) 0.0012(8) C11 0.0233(9) 0.0236(8) 0.0209(7) -0.0015(6) -0.0017(6) -0.0018(7) C12 0.0371(11) 0.0331(10) 0.0202(7) -0.0018(7) -0.0052(7) 0.0053(8) C13 0.0439(12) 0.0411(11) 0.0268(9) 0.0030(8) -0.0087(8) 0.0091(10) N1 0.0179(7) 0.0279(7) 0.0153(6) -0.0003(6) 0.0003(5) -0.0046(6) N2 0.0182(7) 0.0303(8) 0.0156(6) 0.0009(6) -0.0002(5) -0.0061(6) S1 0.0181(2) 0.02165(19) 0.01870(17) -0.00167(15) -0.00052(15) -0.00260(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C2 1.391(2) . ? C1 C6 1.391(2) . ? C1 N1 1.4192(19) . ? C2 C3 1.393(2) . ? C3 C4 1.386(2) . ? C4 C5 1.389(3) . ? C5 C6 1.394(2) . ? C7 N2 1.339(2) . ? C7 N1 1.3629(18) . ? C7 S1 1.6988(17) . ? C8 N2 1.4606(18) . ? C8 C9 1.519(2) . ? C9 C10 1.531(2) . ? C10 C11 1.522(2) . ? C11 C12 1.523(2) . ? C12 C13 1.522(3) . ? 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 C1 C6 119.58(14) . . ? C2 C1 N1 123.99(14) . . ? C6 C1 N1 116.34(14) . . ? C1 C2 C3 119.54(15) . . ? C4 C3 C2 121.09(16) . . ? C3 C4 C5 119.27(14) . . ? C4 C5 C6 120.04(15) . . ? C1 C6 C5 120.46(16) . . ? N2 C7 N1 113.59(14) . . ? N2 C7 S1 122.37(12) . . ? N1 C7 S1 124.04(11) . . ? N2 C8 C9 113.30(13) . . ? C8 C9 C10 111.77(13) . . ? C11 C10 C9 113.52(14) . . ? C10 C11 C12 112.96(14) . . ? C13 C12 C11 113.17(15) . . ? C7 N1 C1 130.06(14) . . ? C7 N2 C8 125.52(15) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.162 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.044